Cross Dressing Sissy Slut Transformed Into Shemale By Dominant Strap On Lesbian August 30, 2008
Posted by sexstory in Bi Sexual Sex stories, Crossdressing Sex Stories, Crossdressing Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Gay Sex Stories, Group Sex Stories, Kinky Sex Stories, Lesbian Sex Stories, Older Women Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Shemale Erotica, Straight Sex Stories, Strap On Dildo Stories, Taboo Sex Stories, Three Some Sex Stories, True Sex Stories.Tags: cross, cross dressing, dominant lesbian, domination, dressing, forced, forced fay, Forced to Feminize, gay, lebsbian, sex, shemale, sissy, sissy slut, slut, stap on, stories, transformed
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Cross Dressing Sissy Slut Transformed Into Shemale By Dominant Strap On Lesbian.
A young cross dressing sissy is forced and transformed into a shemale by the mature and dominant hands of two strap on dido yielding lesbians. Written by Donna for kinkysexstories.org
1
My name is Donna and I have been bi-sexual ever since I was old enough to have interest in sex. I realized early in my life that I have a dominant personality and I also learned what turns me on most is to take something beautiful and submissive and transform them into my personal toy. I still recall my very first boyfriend. He was a jock and very masculine and I liked him a lot. When we were making out, my instincts told me to wrestle him to the ground and force myself on him. It got me so hot that I had to go further and I tied him up and then put make up on him and then a bra and panties. Then I fingered his asshole until he came. After a year of dating him, I had transformed him into a flaming homosexual and I still masturbate about doing so today.
These days, I am mostly a lesbian and prefer to fuck women. But sometimes I spot a sweet young and innocent boy and bring him into my lesbian affairs and eventually transform the sweet little sissy into a gay twink boy. But if I really like him, and his transformation makes me really hot, I try to go all the way and transform him into a shemale, getting him breast implants and if I am lucky, he becomes a sweet bride to a massive stud.
I am 42 years old and my girlfriend Misty is 22. We like to go out to bars and wait for men to hit on us, and then shoot them down so badly that they cry. It’s a little game we play sometimes. One night we were out and a very young and sweet boy began to hit on Misty. She toyed with him for awhile and we both could tell he was very submissive, just the way we like it. While at the bar, he allowed Misty to apply some lipstick on him. That’s the test we give a boy. If he passes it, he comes home with us and we give him a night he never forgets.
Well Timmy agreed to come home with us and while driving him home, I put more lipstick on him and put two fingers in his mouth and told him to suck. He was a natural and my pussy got so wet. It was then that I knew Timmy was special.
“I think we have a little sissy boy here Misty.” I said to my girlfriend. “Look at how eager he is to suck. We won’t have to do too much work to transform him. He’s already half way there. Timmy, are you sure you aren’t gay?” I asked.
“No. I’m not gay.” He said.
“Well, I bet you have tried on a pair of women’s panties before haven’t you? It’s ok to tell us. We enjoy and appreciate that in a young man. In fact, it really turns us on. You want to turn us on now don’t you?” I teased him.
“Well, I do have a pair of my ex girlfriends panties that sometimes I put on.” He admitted as he blushed.
“And have you ever had a man’s cock in your mouth sweetie?” I teased.
“No, of course not. I’m not gay.” He said.
“Well, there’s nothing wrong with it. And there’s nothing wrong with being gay. Misty and I are gay, but we like boys too. Especially cute boys who wear panties sometimes. ” I said and held him close to my chest until we got home.
Misty and I undressed Timmy in front of the mirror and began to caress and nurture his sweet and sexy little sissy body. It was already very feminine with almost no body hair or muscles. Misty kissed him as I stroked his little sissy cock until it was hard.
“Your cock is not very big sweetie, ” I whispered in his ear, “but your ass is a work of art. Most women would kill to have an ass like yours. ” I said as I played with his butt cheeks like puddy.
“Now Misty is going to apply some make up to you while I put these panties on you and you can show us how much you like to wear them. ” I said. Timmy said nothing and let us completely play with him. My pussy was soaked already watching this young sissy submit to us. He had no clue what he had gotten into.
Timmy’s mouth looked fantastic with the heavy red lipstick and I picked out a bra for him and placed it onto his soft and barren chest. I looked down and saw his tiny penis sticking out of his panties and gave it a little tug.
“Looks like somebody likes all this attention. Your little girly clit is very excited isn’t it?” I asked.
“YEs.” He said whimpering.
“Don’t be scared Timmy. You are very lucky to have found us. We are going to bring you to heights of pleasure you never even dreamed of. Now lift up your foot so I can put this stocking on you.” I instructed him.
After Misty and I had cross dressed Timmy into a beautiful little sissy slut, we paraded him around our place and teased him and tickled him and tortured him.
“Timmy, you are absolutely beautiful. All of our lesbian friends would love to have a sweet sexy girl like you. Don’t you feel beautiful? Your lips look fabulous. Don’t you feel so soft and feminine? Like a ripe blossom that needs to be plucked. Doesn’t it feel wonderful to let go of all your masculinity and allow yourself to be free and beautiful? Now it’s time for your reward for letting us dress you up and sissfy you” I said.
I took Timmy by his soft and feminine hand and led him to the bed. I lay him on top of me and could feel his small erect cock sticking out of his panty and rubbing against my stocking. I could smell the slutty purfume we sprayed on his neck. My pussy was drenched in wetness now and I longed to feel his sissy prick inside me.
I grabbed the sissy’s ass cheeks and plunged his dick into my pussy. Ahhhh. I very gently and softly rocked his hips back and forth into my pussy. Slow enough that he wouldn’t cum.
“Now this is the way you should fuck a woman.” I said. “Soft and slow and gentle.” I reached behind him and stuck my finger deep into his ass and watched his eyes light up and his painted mouth open wide. “Now just relax and enjoy it.” I said.
Meanwhile my girlfriend Misty had straped on a large black strap on dildo. She had grabbed some anal lube as well and inserted her lubricated finger into his virgin ass hole right next to mine. Timmy moaned and squirmed and struggled as I held his sissy arms tightly.
“Very good sissy boy. You can take 2 fingers up there. That’s what we like to see. Now just relax and don’t cum yet.” I said.
Misty put the head of the large black strap on cock against Timmy’s ass cheeks as he continued to sweetly move in and out of my pussy.
“Now Timmy look at me. I want to see your face as you get fucked for the first time.” I said and laughed at him. Misty slowly inserted the massive black cock into his virgin ass and because it was so tight, his entire body began to shudder and shake. “Just relax Timmy and keep fucking me. You are doing a very good job.
“It hurts.” He whimpered.
“I know it does sweety. But it feels good too doesn’t it? It’s ok. You can tell me. I won’t tell anyone. ” I said.
“Yes, it feels good too.” He admitted.
“Well don’t cum just yet. Let Misty fuck you and take it like a man. She can fuck you better than you can fuck me I bet.” I said laughing.
Every time Misty thrust into Timmy’s ass, his little dick thrust into my pussy. I began to cum and climax as I watched the look on Timmy’s face as he took it in the ass for the very first time. His painted face looked so sexy as he allowed Misty to violate him. He was so tight that even the smalest of movement of the strap on caused all of his skin to move. It was so tight and so sexy to watch.
“Now do you feel your ass pussy begin to stretch and welcom the big cock?” I asked.
“mmmmmmmm”, was all Timmy could say.
Misty and I began to feel his little sissy ass muscles tighten up and we knew he was about to cum.
“Looks like you are starting to enjoy this my little sissy slut. But don’t come just yet, we have much more for you.” I said. But just then Timmy’s ass cheeks gripped down on the large cock that was violating him and I had to take him out of my pussy before he exploded. “My sweet little Timmy. I knew you were going to enjoy that. You did a very good job for your first time. I am proud of you.” I said.
Timmy was shaken, embarrassed, and stipped of all his dignity. We had broken him and he was confused by the pleasure of it.
Misty and I undressed Timmy and gave him a hot bath. We shaved his pubic hair and his other body hair and he let us. He was loving all the attention. We then dried him off and dressed him in a frilly teddy negligee. We told him that from now on, he must wear our panties at all times.
We brought Timmy into our bed that night and he slept between us as we stroked, fondled, and fingered him. The next morning we tied him up and took turns fucking him with an even bigger strap on, stretching his sissy ass pussy to accept our cocks easily . This time we had to put a cock ring on small penis to keep from coming. Timmy was starting to enjoy being fucked in the ass as much as we enjoyed fucking him.
We made a deal with Timmy that if he wanted to be part of our love triangle, he had to be dressed up as a woman when he came over. Since poor Timmy couldn’t seem to get sex anywhere else, he agreed. We took Timmy shopping and bought him clothes. And when he came over to see us, he came over dressed in these sexy and often slutty clothes. It was a thrill to see him so nervous and scared at the door, and then to take him inside and have our way with him. We had almost completely transformed him into a shemale and he was totally unaware.
One day I told Timmy that Misty and I wanted to take him out to a bar dressed like a woman. Timmy didn’t like the idea at first, but we he was so whipped, that we knew we could get him to do anything we wanted. We dressed him in a wig and a sexy red top with black gloves to cover his arm hair and hands. He looked fantastic.
“Are you ready for your big night out on the town with the girls?” I asked.
“”Yes but I am very nervous.” He siad.
“Oh don’t be. You look great. I think it’s about time the whole world saw how sexy we have made you. We want to show you off Timmy.” I said.
We took our little sissy slut boy toy out to a gay bar. He was the new bitch on the block and all the gay bears were making eye contact with our new little sissy.
“Now Timmy, I think it’s about time we found you a boyfriend. After all, Misty and I can’t fuck you all the time. ” I explained.
“No, please. I don’t want to be with anyone else. I love you guys. Please don’t make me be with a man.” He begged us.
“Stop bitching. We will keep fucking you in your little sissy ass until we can find you a real man that you like ok?” I said.
“Well, I guess so.” Timmy said crying.
Just then as massive muscle stud approached Timmy and asked to buy him a drink. We nodded yes and we all talked awhile.
“Why don’t you and this stud go dance a little while. Now Timmy, I want you do do whatever he wants ok?” I said sending Timmy away. Misty and I watched as our submissive sissy held his frist real man close and creamed our panties as he was fondled and then kissed for the first time.
As the bar closed we asked the stud to come home with us and he agreed. He was a gorgeous masculine man and he held Timmy in the back seat sneaking his hands into Timmys panties as the two kissed in silence.
Back at our place, Timmy was getting turned on by this aggressive gay bear and it took no coaching from us to get him to suck his cock. In fact it was Timmy who went for it first. Placing the huge shaft into his sissy virgin mouth and sucking like a pro. Timmy cupped his giant ball sack and we watched as his painted lips sucked up and down until the gay stud began to convulse and exploded all over Timmy’s sissy face.
“Very good Timmy. We have taught you well. Now that wasn’t so bad now was it?” We said as we applauded his first blow job. After the stud had emptied his cum all over our sweet little sissy’s face, he went home and we took Timmy to bed and fucked his ass good and hard.
Misty and I asked Timmy to move in with us and told him that if he did, he must be dressed in drag as often as possible. To our surprise, Timmy agreed and after a few months, Timmy was dressing as a woman full time. We took pleasure in making him as feminine as possible and stripping away any sense of masculinity he once had. We stopped letting him fuck us and now, we only fucked him with strap ons. But of course we made him perform oral sex for us sometimes twice a day.
We took Timmy out shopping dressed as a woman, we took him out to eat dressed as a woman, and slowly, Timmy stopped wearing his boy clothes altogether. We even had all our lesbian friends over and allowed them to take turns dressing up our boy toy and then fucking him. But one lesbian friend tried to use am extra large steel dildo on Timmy that stretched our his ass pussy so far, it took weeks for it to shrink, so we had to stop the parties.
One night, we tied Timmy up and teased him with his favorite strap on dildo.
“You want this cock don’t you, you little sissy.” I said.
“Yes, you know I do.” He begged me.
“Timmy, I know what else you want. Even if you don’t know you want it yet. You want to be a woman. You want to have breasts and be our little shemale sissy slut don’t you? You want to do whatever it takes to please us. It’s your nature. It’s what you were born to do. ” I said.
Timmy began to cry and sob. “I don’t want to lose you and Misty. But I don’t want to have tits either.” He cried.
“Now deep down you have always wanted this. To be a real woman, to be our special little toy. To serve and please us forever. Timmy you will make us very happy by doing this. We can no longer continue to fuck you unless you take the next step. It’s time you got breasts and became a real woman for us.” I said.
Timmy cried uncontrollably and I held him in my arms and kissed him untill he calmed down and said, “ok, I will do it.”
I squeezed him tightly and placed my black dildo into his mouth to suck which stopped his sobbing. The next day Misty and I took him in for his breast implants. When we picked him up, he was gorgeous. Almost as sexy as Misty. Poor Timmy was crying and his mascara was running all over his pretty white blouse.
“Timmy, you look wonderful. Don’t be sad. This is your first day as a real woman. Lets get you home and break you in. Misty and I have bought a whole set of new bras for you. But from now on, we are going to have to call you Tina.”
Our sissy slut Timmy, who was now Tina, began to really take to his forced womanhood. In fact, he was much happier with breasts and was definitely much sexier. His transformation had been complete. Misty and I were so pleased how we transformed our sweet sissy slut Timmy into a gorgeous submissive shemale, that we couldn’t keep it to ourselves. I began to seek out gay play mates for our new shemale Tina.
I took a picture of Tina and placed an ad in the online personals.
“Newly transformed shemale looking for studs to suck and fuck for free.”
The answers poured in. I was very selective and finally choose a very tall and muscular older gay man to be Tina’s first. When he arrived at the door I told Tina to hug him and let him kiss her. Well once they started to kiss, there was no stopping the raw sexual power of those two. The stud picked up our shemale and placed her gently on the couch with her legs in the air and quickly tore off her panties and thrust his massive cock into Tina’s ass. Misty and I got naked and began to suck each others pussy as we watched Tina get man handled. Soon Misty and I began to orgasm. Then Tina began to cum in her panties but the stud was far from done and continued to put Tina in every position he could think of. Misty and I watched Tina’s limp tiny penis get bounced around as the giant cock when in and out until finally, cum spewed out of Tina’s ass pussy and ran down her crack.
Tina turned to us and said, “Oh my god, you have made me so gay. I just love cock in my ass” I came in my panties instantly.
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Misty and I began to set up more play dates for our shemale Tina. We began to even charge money for men to spend time with her. Fat men, old men, gay men, straight men, big men, small men, all men. Tina began to become a pro and took it all. Deep in her sweet submissive pussy ass.
Now Misty and I are looking for a new sissy slut to transform into a shemale.
Are you man enough for two dominant stap on lesbians?
Sissy slut transformed into shemale by dominant strap on lesbians sex story.
Lesbian Fantasy Sex Story August 25, 2008
Posted by sexstory in Bi Sexual Sex stories, Cheating Wife Stories, Domination Sex Stories, Gay Sex Stories, Group Sex Stories, Kinky Sex Stories, Lesbian Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, Three Some Sex Stories.Tags: lesbian, lesbian fantasy, lesbian lust, lesbian sex, Lesbian Sex Stories, lesbian sex story, lesbian sex story fantasy
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Lesbian Fantasy Sex Story
Lesbian fantasy sex story. Cheating on my husband with a lesbian. Dominant lesbian seduces housewife.
This lesbian sex story was written by Lily for kinkysexstories.org
I have been married for 7 years now and most of that time I stayed at home and was a housewife. But last year I became restless and needed to find something to do so I took a part time job as a legal secretary at a female ran and operated law firm. My husband approved of this because he said that since there were no men in the office, he didn’t have to worry about me cheating on him. Plus, I looked forward to spending time with women and perhaps making new friends.
I worked directly under the owner and chief attorney Miss Crawford. She was a very striking statuesque blond who radiated confidence and power. I was drawn to her immediately and enjoyed watching all the interesting people coming in and out of her office. I began to notice that it was all women. There were no men in that office ever which was very comforting.
One day, Miss Crawford told me that we were going shopping together because she had a very important business trip coming up. She also said that she would buy me a business suit since I didn’t seem to have any good ones. She took me to a very classy and expensive shop where they only sold women’s business attire and then she picked out things to try on and would ask my opinion. I couldn’t believe I was getting paid for this. I watched Miss Crawford try on many different things and began to envy her. She was a very sexy and smart women and I wondered why she was not married.
Miss Crawford asked me into her dressing room to help her with the zippers. I helped my boss into a sexy white suit and zipped her up. I couldn’t help but admire her.
After she was satisfied, she began to pick things out for me to try on and she undressed me, then dressed me again, over and over in the dressing room until she was satisfied with my appearance. She was very gentle and complimented me on my figure and grace.
It was a wonderful afternoon and as we headed back to her office in her BMW, she told me she had to run to her flat and pick up some documents. When we arrived at her apartment I was astounded at how beautiful and large it was. There were very expensive items everywhere and the place was oozing with class.
“This is a marvelous place Miss Crawford.” I said. “Do you live here all alone?”
“Why of course. But sometimes I let a friend stay with me if she needs to for awhile. Hey, let me show you the best part.” My boss said and led me over to the large window over looking the city. Underneath the window was a gigantic jacuzzi. “This thing is a miracle worker. I would never survive my life without it. ” She turned it on and began to undress in front of me.
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“Come help me with the zippers darling.” She said and I gently undressed her. “Can you get my bra too?” I unhooked her bra and two beautiful full breasts full out. I must admit I was a little jealous to see how endowed my boss was. When she was totally nude, she began to undress me. It was starting to make me feel a little uncomfortable but it was also exciting to be spending time and bonding with the powerful and attractive woman who was my boss.
“Do you always do this naked?” I asked in a quivering voice.
“Oh don’t be so silly. Of course. Now lets melt the stress away shall we.” My boss said and took me by the hand as we both dipped ourselves in the bubbling warm water.
As we sat there looking out at the city skyline and talking, my boss begin to massage my back. She placed me in front of her with her legs around by butt. I could feel her pubic hair rubbing against my sensitive ass and it made me rather excited. She was talking to me very close to my ear in a calm voice that was almost a whisper. Her hands moving softly over my shoulder blades guiding me towards a heightened state of peace. Then she worked my neck muscles and I drifted even further into the land of Bliss.
Then she tilted my head sideways and the next thing I knew, her full lips were covering mine. I was so relaxed and lost in a dream that it took me several moments to realize what was going on. All I knew was that I was involved in an extremely sensual situation and was enjoying it. It felt as though her kiss was absolutely necessary. And then I began to think. My thought was, “this is my boss, I am married, and what the hell is going on here?”
I detached from my boss’s clutches and moved a foot over.
“Didn’t you enjoy that?” My boss asked.
“I’m not sure I can do that.” I said at a loss for words.
“Well, I don’t want you to feel uncomfortable. In fact, I want you to feel like you can share anything with me. I really like you, and feel very lucky to have you working for me. I would like to get to know you better.” She told me.
“Well, thanks, I enjoy working for you and have had a wonderful day but I am married and don’t feel very comfortable with kissing.” I said.
“That’s fine. Don’t worry, I understand. I don’t want you to feel uncomfortable.” She said. “But did you enjoy the massage?”
“Yes, that was great.” I said.
My boss and I continued to soak and both pretended like nothing had happened but all I could think about now was our kiss and how excited it had made me and how sexy she was and how hot I was feeling. Finally we both got out of the Jacuzzi, got dressed and she asked to drive me home. When we arrived at my house she said, “I want you to know that if you need anything, anything at all, I am here for you ok? I want to be your close friend. “
I thanked her and got out. Later that night, I asked my husband for oral sex. As he was pleasing me, I began to fantisze about the sexy kiss I had had with my boss earlier. I thought about what it would like to like another woman’s pussy, and to bring her to a climax. And what it might be like for her to lick mine. I had a gigantic orgasm fantasizing about Miss Crawford and came all over my husbands lips.
The next day I put on the new business suit Miss Crawford had bought for me and I began to think about how she dressed me in it the day before. I was starting to realize I had a big crush on my boss and worse, she seemed to have a crush on me. I could feel myself go flush like a teenager. When I arrived to work Miss Crawford kissed me on the cheek good morning and it actually made me a little wet. She smelled so good and had a very large and luscious smile. Her eyes sparkled at me.
“I’ve got some very good news for you. My business trip this week is going to be very lucrative and I need you to come with me. We will be flying to New York first class and be gone a week. You will be paid double. How does that sound?” She asked.
I was very excited. The first thing I could think of was the all the possibilities there would be to spend time with this amazing women. I had never been with a women sexually before and although I had fantasized about it from time to time, I never felt the need to act on it. But Miss Crawford had awakened something in me. I began to see women differently and as sexual pots of gold. I was falling in love with my boss and it was feeling wonderful. The only problem was that I was married. But somehow I felt like exploring my feelings for Miss Crawford was not actually cheating on my husband. Yes, it was a lie, but there was no danger of getting pregnant, and he would still be the only cock in my life. So after a quick gut check, I made the decision to follow my crush on my boss and go to NYC with her.
We flew first class the whole way and got tipsy on Champagne. I asked her if she had a boyfriend and she explained that she was a lesbian. She had been with men before but she preferred women now. I found her and her lifestyle to be extremly interesting and was falling head over heels with her.
After checking into the hotel, we checked into our separate rooms and my boss knocked on my door.
“How about one more cocktail to cap off the day?” She asked and I was more than thrilled to submit. We went to fancy bar in the hotel lobby and as we stoked our buzz even further, I found it thrilling to be in a different city, with a lesbian, and knowing that in a short while, I was going to sleep with a woman for the first time. When we finished the drink we headed up to our rooms.
“Would you like to take a jaccuzi in my room before you sleep?” She asked me.
“I was thinking you would never ask.” I said and she beamed me a smile that lit up the hallway. She started the water and then slowly walked over to me looking at me like I was a deer and she was a tiger. She ran her hands down my arms and then held both of my hands and she moved in and pressed her lips against mine. Immediately I was swimming in a sea of sensuality and soft feminine ethos. I began to kiss her back and the momentum kicked up a gear. We began to kiss and undress each other until our nude bodies touched electrifying my pubic hairs.
My lesbian boss gently laid me on the bed and pulled out a vibrator from her suitcase. As she kissed me, she went to work on my clit with the vibrator and sent me to the land of orgasm where I climaxed. I let my hand run up the thigh of my boss and slowly slipped it into her cum soaked pussy. It was so strange to be inside another woman’s pussy. It was just like mine and I knew exactly where to go and what to do. I began to massage her clit as I kissed her and soon she was moaning and sighing and quivering in my arms. I opened my eyes and watched myself as I led this gorgeous women to pleasure. It made me feel more powerful than I had ever felt to know that I was making this beautiful creature happy. I began to kiss her breasts and and sweetly suck on her erect nipples. It was so wonderful to have her tit in my mouth. I felt like a teenager having sex for the first time. Why had I never done this before?
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I began to kiss her navel and slowly worked my lips down to her wet pussy. Then I went to work on her clit with my tongue. Having a clit myself, I knew just what to do and in no time my boss was having her second orgasm. I watched as her milky thighs squirmed around my head as she contorted and let lose her feminine lust.
“You are very good at this.” She said. “Are you sure you have never done this before?” She asked. I blushed and told her I was only good because she had inspired me.
We erupted in more passion and my boss lay me down and got on top of my in the 69 position. As she started to lick my clit, I was launched into the heavens. Oh my god. All these years I thought I knew was it was to have my pussy licked, well I hadn’t. When done properly, it’s the most pleasurable thing I’ve ever known. I instantly went into uncontrollable multiple orgasms. My body was out of control. I was throbbing so violently that I was unable to lick her pussy any more and could only tilt my head back and breath. Uncontrollable noises came from deep within me.
I’m not sure how long we were making love but it seemed like half of the night. When we bother were completely exhausted and our muscles couldn’t take another orgasm, we finally got into the jacuzzi and held each other and talked.
If this was being a lesbian was like, perhaps I had been missing out. That was incredible pleasure. It was a different kind of sex than with a man. There was a closeness about it that was very special. A bonding like no other.
I slept with my boss in her bed that night, and every night after that while on our business trip. We made love at every chance we could, exploring each other, perfecting four play, and trying to bring each other to higher and higher states of lustful bliss. We used strap on dildos, anal plug, toys of all kinds and shapes and sizes. And on the plane ride home, we made love in the bathroom for over an hour.
When I arrived back home and saw my husband he asked, “so honey, how was your trip.”
“Completely exhausting but extremly satisfying.” I said. That night my husband made love to me and I found myself reborn with a new thrust for pleasure.
“Wow baby, you must have really missed me. I haven’t seen you this way since our honeymoon.” He told me.
I had a new appreciation for his cock, and had been awakened to my own capacity for physical pleasure. I felt like a queen of all things sensual and brought my husband to the best orgasm of his life.
The following week, I arrived to work and was called into Miss Crawford’s office to meet a perspective client. When I walked into her office, I found my boss wearing a strap on dildo, and I found the perspective client bent over the desk.
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“Say hello to Miss Cummings.” My boss said. I said hello and my boss begin to kiss me and undress me in front of the potential client. “I want you to show Miss Cummings what this law firm is capable of. It’s important that we give her the full treatment because she is a very powerful woman ok?”
I stood there naked as my boss fingered my pussy until it was wet. Miss Cummings watched as she fingered her pussy. When I was at a heightened state of arousal, my boss led me by the hand and bent my head down to the client’s pussy. Instinct took over and I began to suck and lick her clit as she held my head in place the way she liked it. Meanwhile, my boss had taken her strap on dildo around to my ass and began to insert it as I was bent over working on sending Miss Cummings to the stars.
I was so turned on at servicing this women whom I had never even met before and so excited to be part of this taboo office sex, that I began to cum all over the dildo inserted inside me by my lesbian boss. We spent the rest of the afternoon in there licking and sucking and throbbing that before we knew it, it was time to go home.
“Well, Miss Cummings, do you think our law firm is good enough to service you?” My boss asked.
“YEs, quite good, but I am going to need further close examination from her.” The potential client said pointing at me.
“That can be arranged.” My boss said with a smile. “When shall I send her over.”
And that’s my lesbian fantasy sex story. I hope you enjoyed it as much as I did.
Lesbian Fantasy Sex Story written my Lily for kinkysexstories.org.
Cuckold Strap On Cross Dressing Sex Story August 19, 2008
Posted by sexstory in Cheating Wife Stories, Cockold stories, Crossdressing Sex Stories, Crossdressing Stories, Cuckold Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Kinky Sex Stories, Older Women Sex Stories, Role Play Sex Stories, Romantic Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Straight Sex Stories, Strap On Dildo Stories, Taboo Sex Stories.Tags: cross dressing, cuckold, Sex Story, strap on
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Cuckold Strap On Cross Dressing Sex Story
Cuckold Strap On Cross Dressing Sex Story – Mother in law with strap on dildo turns husband into cuckold cross dressing sissy slut.
Written my Bob for kinkysexstories.org
I began cross-dressing when I was a teenager. I just enjoyed the way the soft and frilly things felt against my body. I was never gay or attracted to me, but I loved women so much that I wanted to be more like them. So although I was a closet cross-dresser, that’s as far as it went.
When I met my wife Brandy, I told her about my lingerie desires and after awhile she understood that it didn’t threaten our relationship, but in fact drew us closer and allowed us to share something very special. Since my wife accepted my cross-dressing, I knew she was the girl to marry.
My wife’s mother Alice was a very dominant woman and never liked me from the start. My wife told her mother everything we did, even our secret about my cross-dressing fetish. I was hurt by this breech of trust but what could I do? For a wedding present, my mother in law bought me a blond wig, pink panties, and red pumps to match. I was completely embarrassed and humiliated when I opened the gift while my mother in law just smirked at me and my wife giggled.
What was worse was when I discovered that my mother in law would be going with us to Miami on our honeymoon.
“You know mom. She does what she wants to do and no one can stop her.” My wife said.
The first day we arrived, my mother in law informed me that she had bought my wife a day at the spa and that would giver my mother in law and I a chance to bond and go shopping together.
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“Oh stop putting up a fuss.” My mother in law said. “If you come with me and are a good boy, I just might by you some more sexy outfits for your honeymoon.
Both my mother in law and my wife laughed at me but she had a point. The idea of buying women’s clothes for me to use on my honeymoon did kinda turn me on. So I went along with it.
I was taken directly to Victoria’s Secret and led in my the hand of my mother in law. She marched me right up to the counter where a beautiful young blond was standing.
“Hi, this is my sissy son in law and he loves to dress up like a sexy woman. He is on his honeymoon so can you help us find something fabulous for him to wear tonight?” My mother in law said.
I was so embarrassed as the two women smiled at me. After the sales girl picked out a few items, my mother in law escorted me into the dressing room and began to strip me naked.
“I can do this alone.” I said.
“Oh stop your sissy fuss. You know you enjoy this so shut up.” She said.
I kept quiet as she took off all my clothes.
“Now turn around and let me look at you.” She said as she spun me around to look at my ass. “Bend forward just a little and stick out your butt. Very nice. Your not hung very well, but that’s ok, I doubt you will be needing that equipment much anymore. But I love your ass. It’s very inviting.”
“What about your daughter. How would she feel if she knew you were looking at me in this way?” I asked my mother in law.
“Well my sweet thing, it’s going to be our little secret for now. But after all, mommy knows best. Don’t you worry about that. I’m doing this for her anyway. She is going to be very excited about the wedding gift for her.”
My mother in law spanked me gently and then told me to step into the sexy outfit she had picked out for me. After I tried it on she stood behind me and we looked in the mirror together at how sexy she had made me.
“There, now that is nice isn’t it? Tell mommy how much you like her attention and how lucky you are that she can do this special thing for you.” My mother in law said.
“Yes, it’s true. I do look very sexy and pretty in this outfit. Thank you Alice.” I said respectfully.
To my surprise, Alice took my face in her hands and kissed me on the lips using her tongue. My cock began to grow out on my panties and she reached down and stroked it.
I skrimed back and said, “Hey, what are you doing to me?”
“Just warming you up sweetie, that’s all. Now shut up. We need to buy you some make up don’t we? And maybe some perfume as well.”
My mother in law undressed me, then purchased the sexy lingerie for me, then took me to buy make up and perfume. The whole time I was thinking about our kiss in the dressing room. It had really turned me on but was it cheating or just flirting? Perhaps it was ok because it was my mother in law. Would my wife be upset? Like she said, Alice is going to do whatever she wants and there’s not much you can do about it.
Back at the hotel, my mother in law unwrapped the sexy clothes we had bought while we waited for my new bride to return from the spa.
“I’m going to run you a nice warm bubble bath, then wash you, then lay out your outfit for this evening.” She said.
My mother in law kneeled next to me while I soaked in the tub then she carefully stroked me with a sponge inspecting every inch of my body. My cock began to grow as she watched it. There was no way of hiding from her how much this was turning me on. I felt totally exposed and at the same time, totally hot. She was really turning me on.
“Ok sweetie. Time to get dried off and dressed up in your new sexy things.” My mother in law said as she patted down my body with a towel. I stood there with a raging hard on and said nothing.
My mother in law began to dress me up. First pink panties, then the pink bra, then the white stockings over my legs, then the teddy over the bra. Then she strapped on my red high heels, then placed a blond wig on me. Then she began to apply make up and lipstick. And finally perfume.
“You look gorgeous. Simply fabulous. You turned out much better than I thought you would darling. Don’t your feel great now?” She asked.
“Yes, you did a good job. Thank you.” I said.
“Now stand up and lets get a better look.” She said.
I stood up and my hard on was sticking out of my panties. My mother in law quickly grabbed my thobbing cock and said, “We must do something about that. It doesn’t look right no does it? Not very girly.” She said and led me to the bed, bent me over her thigh and began to spank my pantied ass. “Maybe this will help.”
After spanking me for awhile, she turned me over to find my cock was every harder now. There was no hiding how turned on I was.
“Well, that didn’t work at all. But I know something that might do the trick.” She said.
The next thing I knew, my mother in law had tired my hands together. Then she reached into her purse and took out a large strap on dildo and strapped it on.
I began to protest. “What are you doing?” I asked.
“Hush sweetie, you know exactly what I am going to do to you, and you know how much you want me to do it to you. So just relax now.” She said as she slipped two lubricated fingers into my virgin ass.”
“I;ve never done this before. Don’t you think your daughter is going to be upset? What if she finds up like this?” I asked.
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“I’m going to have to break you in first. This way, when my daughter does this, you will have some experience and not be so skittish.” She said.
My mother in law bent me over and inserted her large strap on into my ass. It was very painful at first but as began to thrust into me, it began to feel much better. Then it began to feel wonderful. I looked into the mirror and saw my mother in law fucking me and it was too much.
“I’m going to cum now.” I said as I shot my load out of my panties and onto my pumps.
“Did the little sissy like it when mommy put her cock in your ass?” She asked me. “Come on, tell me how much you enjoyed that.”
“Yes, it felt very nice. I liked it very much.” I said.
“That’s a good little sissy slut. And we finally got rid of that hard on of yours too.”
“Just don’t tell my wife what we did ok?” I pleaded.
“Why not? Don’t you think she should know what a little sissy slut you really are? And how much you like it in the ass? I’ve been recording the whole thing so I can show all my friends what a little sissy my daughter married. I can’t wait to show them.” She laughed.
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“You recorded it?” I was horrified. “Please don’t show it to anyone.
“I bet your boss would love to see it and show it all around your office.” My mother in law threatened.
“Why would you do that? What do you want from me? I’ll do anything, just please don’t show anyone that tape.” I begged her.
“I am going to make you a cuckold sissy slut husband for my daughter. And you will also be my own personal sex slave. I’m going to pimp you out to my friends. And then make you watch your wife get fucked by a real man.” My mother in law said as she began to take off her skirt and panties. I was shocked. As it began to sink in, I realized there was nothing I could do. She had me over a barrel. If I didn’t do what she wanted, she would send that tape to my office, or even my parents. I would have to go along with her until I could think of some way to get out of it.
“From now on, you are not allowed to fuck my daughter. That;s going to be reserved for real men. I don’t want some little sissy slut to get her pregnant. We will find a stud for her and you will raise their children. If I find out you have fucked my daughter, I will send this tape to everyone you know, is that understood?” She said.
“Yes” I said helplessly.
My mother in law slapped me across the face several times and then looked at me as I began to cry little a baby.
“There there now. It’s going to be ok. In fact, you may even start to enjoy our new role as my sex slave. ” My mother in law said and then kissed me until I stopped crying. She began to stoke my cock and get me hard again. Then my mother in law forced me down to her mature and soaked pussy and told me to lick her until she came all over my sissy face.
It was very difficult for me NOT to fuck my new bride. She was a very sexy woman and I loved her very much. I bought her a dildo and explained that I was having difficulties in that department and was sorry. Meanwhile, my mother in law would secretly come over while my wife was at work and dress me up as a woman and fuck me in the ass. I must admit that I enjoyed it very much and I would cum very quickly.
My mother in law had arranged for my wife to get bi-weekly massages from a big stud. My mother in law would gag me and force me to watch as this mans giant hands rubbed my wife’s horny body all over. Sometimes my mother in law would insert her strap on while I was forced to watch.
“You are learning how to be a cuckold husband. And you are doing very well. Soon, you will no longer crave pussy at all. Only my strap on.” She instructed me.
After several months of not fucking my wife, one day while watching my wife get her massage from the stud, she rolled over and took out his gigantic cock and began to suck it. I began to get upset and cried so my mother in law took me away from the door and into the bedroom to listen.
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“Now listen to your wife sucking that real man off. Listen to how she moans, and how happy he is making her. I’ want you to lay on your back and stick you legs in the air like a good little sissy slut girl. It will help take the sting out of listening to your wife get her pussy properly fucked by a real man” She said.
I lay on my back submissively as my mother in law mounted me with her strap on. I began to hear my wife whimper and moan as she received that massive cock from her new stud. She was loving it and having multiple orgasms.
“You know he can do a much better job at pleasing your wife than you ever could. Just give into it and be glad that she is being pleased. And focus on how well you are being fucked by me.” My mother in law said.
I began to spurt cum all over my stomach as I listened to my wife climax in the next room.
“That’s a good cuckold sissy slut. Mommy has trained you well. Soon you will be allowed to watch your wife cheating on you as you wife watches you take it in the ass. Then we will all be one happy family.” My mother in law said.
Cuckold Strap On Cross-dressing sex story.
Cuckold Stories August 7, 2008
Posted by sexstory in Bi Sexual Sex stories, Cheating Wife Stories, Cockold stories, Crossdressing Sex Stories, Crossdressing Stories, Cuckold Stories, Domination Sex Stories, Femdom Sex Stories, Group Sex Stories, Kinky Sex Stories, Older Women Sex Stories, Role Play Sex Stories, Romantic Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, Three Some Sex Stories, True Sex Stories.Tags: Cuckold Stories, Kinky Sex Stories
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Cuckold Stories. Submissive Cuckold for Dominant Older Woman Sex Story Stories.
True Cuckold Stories written by Ian Moore.
This cuckold story begins very innocently wanting to please my new bride. I met and fell in love with a beautiful woman who happened to be 9 years older than me. She was very sophisticated and had a great job and lived very well. When I met her, I was still struggling with my own career and was easily seduced by her higher level of lifestyle. She also had gorgeous friends that always hung around who were rich and powerful themselves. At times I felt a little like a boy toy but I was very well taken care of for the first time in my life.
Although Julie and I were several years apart, we had the best sex I had ever had. She made me feel very comfortable and seemed to know exactly what I liked and how I liked it. She would always make sure I was satisfied first, then she would instruct me on how she wanted to be pleased and in what way for that day. Julie was a sensual powerhouse of seduction and I felt honored to be the center of her attentions.
One day Julie spilled wine on my shirt and told me she would wash it immediately.
“I’m so sorry sugar, you must take off your clothes and go take a shower why I wash them.” Julie said.
I sheepishly did as she said and while in the shower Julie came into the bathroom.
“DId you clean my shirt Julie?” I asked.
“Not yet sweet pee, but soon. In the meantime I am laying out some of my clothes for you to wear ok?” She said.
“Thanks” I said. When I exited the shower I found a pink silk bathroom that was short cut. It was the very same bathrobe Julie was wearing when I had sex with her the first time. I also found a pair of white panties, knee high black stockings, and a bra. I was a little confused so I stuck my head out of the bathroom door.
“Julie, where are the clothes you want me to wear?” I asked.
“Right there sugar plumb.”
“You mean your clothes? ” I asked
“Of course sweetie” and she came into the bathroom. “Now my love, I want you to wear these for now ok? It’s not too much to ask after all I do for you is it? Besides, haven’t you ever fantasized about wearing my clothes?” She asked.
“Well, maybe, but I’m not sure.” I said.
“Oh don’t be so silly, just put them on. Do you need my help putting them on?” She asked?
“Well……..I guess so.” I said.
“That’s better sugar. Trust me, you are going to enjoy this as much as I am. Now come here and let me slip my panties on you. Haven’t you always wanted to feel the pleasure of silk around that beautiful sweet cock of yours? ” My finance said.
Julie dressed me up in all her lingerie and then even put makeup on me and bright red lipstick on my lips.
“I have always wanted to put lipstick on those luscious full lips of yours. You have very feminine lips sweetie. They are sensual and deserve lipstick. Don’t you like how pretty I’ve made you?” Julie said.
“I feel a little silly Julie. I mean this feels kinda strange. Are you sure you enjoy doing this?” I asked.
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“Oh yes, seeing you like this only brings us closer and it is really turning me on to see you so pretty and pink. It’s ok if it feels good to you. It should. It feels good to me and you want to please me and make me happy don’t you sugar?” My finance asked.
“Yes Julie. You know I love you.” I said.
“Well then let yourself be spoiled and allow the soft feminine things you have on to envelope you completely until you are relaxed and unguarded. Do you understand?” She said.
It did feel good once I relaxed. And I could tell that Julie was getting really hot because she began to massage her clit with her finger and then she stuck her other finger in my mouth as I watched her. I began to get hard and could feel my penis swelling with blood in my girlfriends white panties. Julie noticed it.
“Very good my sweet boy. You are finally enjoying this as much as me. Would you like to follow me to the bedroom?” She asked.
Julie gently took my hand and led me towards the bedroom. She lay down and placed me on top of her and reached down and slid my throbbing dick out of the panty. Then slowly inserted my cock into her soaked pussy and began to moan. She kissed my painted lips very very softly and and the asked me to close my eyes and open my mouth.
then my finance slowly inserted a black rubber dildo into my mouth which cause me to open my eyes very wide, which caused her to laugh , but because the rather large cock was in my mouth I was unable to protest.
“Now don’t fight it sweet boy. This is exactly what those painted lips of yours are made for. Sucking cock. Try to relax and take it deeply. Show me how you would want your cock sucked to perfection.” She said.
I did as my lover instructed and soon found that the act of sucking the rather large black dildo in my mouth began to relax me and turn me on knowing I was being watched.
“Oh that’s lovely. Your pretty red lips look wonderful as they move up and down on my cock. I am going to cum now.” And I felt as my lover began to climax all over my cock that was thrust deeply inside of her.
“Keep sucking my baby, this is driving me crazy.” She said.
After Julie had cum several times, she pulled my penis out of her and laid me on my back. She slowly took off my panties and and began to lube up my virgin ass hole.
“You have been so good baby that I am going to give you a special treat.” She said and I moaned as she spread my cheeks and gently pushed her black dildo into my virgin ass. “Yes, mommy likes that very much.”
Just as she said that I came all over the bed.”Sorry Julie, I couldn’t help myself. It just felt so fantastic.”
“Well, I see my pretty pink girl likes this a little too much. We are going to have to work on you so that you don’t come so quickly. Perhaps a cock ring will do the trick. For next time my darling.” Julie said.
Over the course of the next 3 months, Julie would dress me up and fuck me. We still had regular sex as well and it all kinda mixed together. I began to get worried because I enjoyed her dressing me in her lingerie and panties so much, and then her using the strap on too, but we were having great sex every single day and I figured that was what was important.
Then one day Julie dressed me up and then tied me to the bed for my daily strap on training. She put a blindfold over my eyes and began inserting her strap on dildo into my mouth. The next thing I new, I was sucking what seemed to be a real man’s cock. I began to gag a little but Julie stroked my head and whispered into my ear, “calm down baby calm down. This is your birthday present. Open up and suck it all down. There is a surprise waiting at the end of it all.”
Then this strange cock that was in my mouth began to spew cum down my throat and I began to gag but realized it was much easier to just swallow it which I did.
“Very good boy my sweet pee. Very good boy.” Julie took my blindfold off and I saw a very buff older man smiling down at me. “Say hello to Jason.” She said.
“Hello Jason” I said.
“Jason is your big birthday surprise. I want you to do whatever he asks of you ok sweet cheeks?” She asked me.
Julie walked over to the other side of the room and began to insert her favorite sex toys as she watched Jason have his way with me. Jason threw me around the room like a little bitch and Julie smiled at me the whole time.
“Now don’t forget to take notes about how a real man should fuck. You can always learn something from everyone.” She said.
Jason first bent me over the bed and as soon as he inserted his very large cock into my ass, I came. Julie was not happy.
“I thought I trained you not to do that. We are going to have to get the cock ring out so Jason can have his pleasure, and I can have mine too. Next time, I’ll make sure you come before Jason fucks you.” Julie said.
“Next time?” I cried as Julie placed the tight fitting cock ring over my penis.
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Jason fucked me in every position I knew of and some I didn’t know of too. Julie watched and came over and over again and giggled. She took a picture of me too. Being my first time with a real man.
When Jason was ready to come, he pulled out and took off his condom and placed his hand on my jaw and opened it. He then shot another load into my mouth.
I was exhausted.
“Now come here sweet boy and take my seat with my dildo and I’m going to take your seat with Jason.” Julie said.
“Wait a minute Julie, I never agreed to this.” I said.
“Well fair is fair, I let you get fucked didn;t I? Now you have to let me! I’ll let you play with my dildo and you can masturbate too. I’m not that mean. ” Julie said.
I sat back in the chair as I watch a very muscular man with a bigger cock than me fuck my soon to be wife. It was very very difficult. Then it started to turn me on. Then I saw Julie getting rammed hard and fast, then I got even more excited. Then I watched her cum, then Jason came, then I came again.
After Jason left that first night, Julie took me to bed and began to kiss me and rub my cock.
“That was a very good boy today. I loved watching that cock go in and out of you. Didn’t you enjoy the same?” she said as she reached down and placed my hard cock inside her moist pussy.
“My sweet little boy, I can barely feel your cock in my pussy after Jason stretched it out so much. I bet your ass must be the same.”
Cuckold Stories. How my wife turned me into a cuckold. Storied of Cuckold and kinky sex stories.
Sissy Fetish April 3, 2008
Posted by sexstory in Crossdressing Sex Stories, Crossdressing Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Kinky Sex Stories, Older Women Sex Stories, Role Play Sex Stories, Romantic Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Straight Sex Stories, Strap On Dildo Stories, Taboo Sex Stories, True Sex Stories.12 comments
Sissy Fetish Sex Story written by Ian More
My name is Ian and I have a large sissy fetish. I am a straight man who loves to explore his feminine side by dressing up as a sissy in my spare time. Or better still, having a beautiful and strong women dress me up as a sissy. This fantasy turns me on more than anything else and I can’t get enough of it. I am writing this sex story in a white cotton body suit with little white bows and lace.
This is the true sex story of the first time I had the courage to tell a women of my sissy fetish.
I was on a business trip in Miami to close a deal with a client and had a free day and night to sightsee. I browsed the sex shops and ended up buying some white stockings, pink frilly panties, lip gloss, and a white lace bra. I went back to the hotel room and tried on my new sissy uniform and masturbated until my hot sissy cum filled my new frilly panties. Then I put on my swimsuit and headed out to the courtyard pool where I ordered a drink.
There was a woman about 15 years older than me with very large breasts at the bar and I stuck up a conversation with her. We talked about her ex husband and how after 5 years of marriage he left her for another man. She said that although he was gay, they still had the best relationship she had known. And then she abruptly asked me if I was gay too.
“No, I’m not gay. I am very attracted to women. But I enjoy getting in touch with my feminine side from time to time.” I said.
“Well you are a very good listener for a straight man. What do you mean about your feminine side?” She asked.
Usually when I tell a woman I enjoy cross dressing, they run away or assume I am gay, which is why I keep it to myself. But older women seem to accept this better and since I was on a trip, I figured why not.
“I am rather embarrassed to admit this, but sometimes I enjoy dressing up as a sissy. I find it relaxes me and I can have multiple orgasms.” I said shyly.
The older woman then looked deeply into my eyes and took my hand in hers and said, “I find that wonderful that you can share that with me. You know, my ex husband enjoyed that as well and it was one of the things I loved most about our marriage. I miss not being able to do that. I used to love to dress him up in my wedding gown, and I would dress in a man’s suit. And we would pretend to walk down the isle together and then have a honey moon where I was the man, and he was the women. I always thought this strengthened our marriage and bonded us even closer.”
“Wow, that is wonderful. I think very few women are that open minded.” I added.
“Listen”, she said, “I know we just met, but would you like to come upstairs to my room for awhile?”
“Umm, I think I would really enjoy that” I said and the older woman took me by the hand and led me through the hotel and up to her room. I was hard the entire time. I knew that I could really let myself go with this woman and was excited to do so.
“I am going to run you a nice hot bath and then I am going to cover your body with soaps and oils, and pamper you.” She said and looked down at my erection under my swimsuit. “Looks like you are already to go.”
This beautiful mature women slowly removed my swimsuit and my swollen cock popped right out. She eased me into the hot water and began to wash my entire body with soap. She had the caressing fingers of a nurse and I was hers entirely.
“Now stand up sugar and let me dry your bottom off.” She said. “Now stick your butt out a little so I can wash it better. My goodness, your penis just won’t stop looking at me.”
“Now, come into the bedroom here and let’s see what mommy has in her suitcase that might fit her sweetie. Ahh yes. This is very sissy and will look very nice on you.” She said and she took out a pink lace bra and lifted up my arms and slip it down and strapped it on. “Now for panties for my pretty pink sissy. Let’s try on a few of these so I can see which one makes your bottom look the best.” She said as she slipped one pair of panties on me after another. I was completely erect the entire time, just waiting to burst. It was a wonderful torture.
Once she had found a panty that she thought made my ass look good, she began to apply makeup on me.
“There, do you like how pretty mommy has made you?” She asked.
“Yes, very much. You did a wonderful job. Now what can I do to please you?” I asked ready to do anything she wanted.
“Well my pretty pink little sissy. Mommy is very wet in her panties and needs to be serviced. I want you to take those pretty pink sissy lips of yours and go downtown to mommies wet spot and show mommy how much you like being in her sissy things.” She said and she lowered my head to her hot pussy and guided my tongue in circles for her pleasure.
“Now stick you pretty sissy bottom up into the air so mommy can see it while you please me. That’s it, very good, very nice. What a pretty round little sissy bottom you have. All dressed in mommy’s frillies. You love to please mommy don’t you?”
I moaned a yes as I continued to suck on this older woman’s clit. She began to moan too and began to cum all over my face as she held it to her throbbing pussy.
“Oh that’s very good. My new sissy is excellent at pleasing his mommy isn’t he? Now that you have shown you can please me, I think it’s time I get to play with my new sissy toy don’t you? The first thing I need to do is to see how red my sissy’s pink bottom will get when I spank it. Come and lay across mommy’s lap, like you know you have been dying to do.” She said.
I laid my lace stocking thighs across her lace stocking thighs and they glided next to each other in a very sensual and feminine way. I placed my ass up in the air and she began to softly spank me, very gently, and very sweetly.
“You are a very good sissy,” she whispered to me as she spanked me. “You remind me of my ex husband and how much I used to love dressing him up as a sissy. Your pretty pink butt is turning a nice shade of red for me as I spank it. I know how much you like this. I know how much you want to give yourself up to my pleasure and allow me to expose your most secret desire of being feminine. You simply love the feeling of silk and satin and lace as it clings to your muscles. You love being at my mercy and not having to think or make any decisions at all don’t you sweet pink sissy?”
“Oh yes” I cried. “I love it very much.”
“You love being able to be completely submissive to my wise and gentle hands don’t you? You are now my little play toy. My boy toy. My little sexy sissy that I get to do anything I want to don’t you?” She said.
“Oh yes, yes, very much. You know everything. You are wonderful” I said in complete submission.
“And I bet you know what I want to do most to my new sissy toy don’t you?” She asked.
“No, what?” I said.
“Oh now stop lying to me sissy girly boy. We both know what sissy’s like most. You want to have your little sissy butt all full with mommies large strap on. Come on now, tell me what we both already know or else you won’t get it.” She said.
“Yes” I said submissively. “You are exactly right. I want to feel your large strap on buried deep in my sissy ass.”
“Now that’s a good sissy.” She said and stopped spanking me. She lifted me up and told me to go into her suitcase and find her strap on dildo and bring it back. Then she instructed me to assume the position on my hands and knees. She began putting lube on the strap on and then in my ass as she worked it in with a finger.
“I’m just going to move your pink panties to the side because they look so good on you.” She said. Then she began slowly inching her cock into my ass and I began to moan. Then she began to slowly work the large dildo back and forth as my butt muscles stretched for her more and more.
“Now don’t cum just yet sissy. I want to fuck you in many positions first. I want to see you ride my cock like a good sissy every way you can before having an orgasm.” She said.
It was very difficult not to cum as I lay bent on my hands and knees taking her strap on deep into my ass. I heard her moan and cum and then she turned me on my back.
“Now I want to see your face while I fill your sissy hole with my big man cock.” She said. And she bent down and kissed me deeply as she thrust her dildo in and out. Her tongue gouged by entire mouth. “Tell me who owns you now sissy? Tell me who you will always belong to.” She said.
“I’m all yours, now and forever,” I cried out. “I’m your little sissy slut”.
“What a lucky little sissy you are. Now I am going to lie down and I want you to climb on my strap on and show me how well you can fuck it by yourself.” She said.
As I mounted her large strap on, I began to bounce up and down on the cock while she looked deep into my eyes. Her hands rested on my shoulders and guided me up and down to a rhythm she enjoyed. I couldn’t take it anymore and told her I was going to cum.
She pressed her lips to mine and I came all over my panties. I felt incredible and totally relaxed.
“Now hold me and lay with me for awhile.” She said. “Mommy is not quite done with you.”
She stroked my hair and whispered nice and soft things into my ear as we held each other for awhile. Soon she led my mouth to her nipple and to suck on it slowly. And then she began to finger my asshole and in seconds I was hard as a rock again and ready to go.
“Now little sissy, you have earned the right to fuck me. I want you to fuck me just like I just fucked you.” She said and she rolled me on top of her and took my cock out of my panties and slipped it into her wet pussy. I kissed her deeply as I slowly began to fuck this older woman to several orgasms. She reached around and put several of her fingers in my ass and I came instantly.
“Well, it looks like I can fuck you better than you can fuck me sissy. But that’s ok, I am older than you and can teach you many things. Now go and run me a bath and then bath me as I bathed you. And then dress me as I dressed you, and then, if you are good, we can go shopping together and mommy will buy you some wonderful sissy clothes for this evening.” She said.
Sissy Fetish Sex Story Written by Ian for Kinkysexstories.org
Forced Faggot From friend Feels Fabulously Fruity March 30, 2008
Posted by sexstory in Bi Sexual Sex stories, Crossdressing Sex Stories, Crossdressing Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Gay Sex Stories, Group Sex Stories, Interracial Sex Stories, Kinky Sex Stories, Role Play Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, Three Some Sex Stories, True Sex Stories.Tags: forced, fag, femm, femme, feminization, Forced to Feminize, Sex Story, kinky
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This forced fag sex story written by Sarah Smith.
Forced Faggot Sex Story
Hello and thank you for letting me share this free true sex story about how I forced my male roommate into being a fag. I didn’t know it at the time but this was how I began my obsession with turning men into fags. Nothing gives me an orgasm more quickly than to watch a straight guy being taken by a stud for the first time.
I was living in Hawaii barely making a living as a surf instructor. I had a beautiful apartment overlooking the Pacific Ocean but could not afford it so I placed an ad for a roommate. Since I am a woman, I didn’t want to live with some over testosterone male chasing me around the place. Rather I looked for a nice and kind roommate and found a very cute guy named Peter. He was thin and very sweet and I felt safe with him sharing my beautiful apartment.
Peter and I grew to be fast friends and we would talk every night about everything while sharing a bottle of wine. He had a very sensitive side and at times I felt like he was one of my girlfriends. I began to grow very attached to him and found myself feeling jealous when he would bring a female date home. He was such a wonderful and sweet guy and I didn’t want any other woman to have him or take advantage of him. I began to get very possessive of him and one night I took him to bed with me.
Peter was a very submissive lover and allowed me to be on top the entire time. He held me very gently as I came to a climax on top of him and then he obeyed me without question when I asked him to eat my pussy afterwards. As I looked down at him caressing my clit with his tongue, an image popped into my head that turned me on so much I couldn’t stand it. I imagined my sweet roommate Peter going down on a very masculine man while I watched. I couldn’t shake this fantasy and the next day began to conceive of a way to make this happen.
One of the surf instructors I worked with a Hawaiian stud named Lamar. He was a huge man and all the women wanted lessons from him. His skin was dark, his arms were large, and his butt looked like a rock in that tight black wetsuit. Lamar was openly gay and I approached him about my devious sexual intentions. Lamar was excited about the idea of being Peter’s first boyfriend but warned me that most straight men need a little coaxing from their female lovers to attempt being with a man. And I would need to train sweet Peter with a strap on first. I just about came in my panties when I hear him say that and quickly went to work on the plan.
That night I took Peter to bed and while I was riding him I reached around and under his cute and tight butt and began to slowly ease a finger into his sweet ass. He moaned, closed his eyes and came almost instantly.
“I found something you like didn’t I Peter?” I asked.
“Yes, I am surprised at how good that feels.” Peter said.
I led Peter by the hand and into the bathroom where I drew a nice hot bath. Then I laid him down and washed him slowly and gently in the tub with a moist washcloth. He began to relax and then his cock began to get larger and harder again.
“I see my baby is all ready for more? Doesn’t this feel good?” I asked.
“Yes. It feels wonderful. I’ve never had a woman give me this kind of attention before.” Sweet Peter said gushinly.
With one hand I began to stroke Peter’s swollen cock and with the other hand I forced a finger into his asshole again. He began to moan and his eyes rolled back. Then I slowly forced a second finger into his tight virgin ass. I could tell he was about to cum again stopped and gripped his cock tightly. His gentle eyes opened up and looked up at me very submissively.
“You can’t cum Peter unless you allow me to do something to you that I very much want to do.” I said.
“What’s that?” He asked.
“Peter, this may sound kinda silly but I want to shave your legs. You have such beautiful legs and I want to see them better.” I said.
“What? That is a strange thing to ask.” He protested.
“Well, you can’t cum until you let me do this. I promise it will be fun and erotic and when I am done shaving you, I will give you the best orgasm of your life.” I promised.
“I guess I can’t argue with that.” Peter said sheepishly.
And I took out my razor and tilted Peter’s head back and went to work shaving him bald. When I got to his crotch and began to shave his pubic hair, he did not protest one bit.
“Very good boy Peter. You look fabulous. Now are you ready for a very special orgasm?” I asked.
“I can’t wait” He said.
“That’s a good boy.” I said. I began to stroke his rock hard penis with one hand, and slipped a finger into his ass with the other hand. Then 2, then I secretly submerged a small dildo into the tub and slowly worked that into his ass. When Peter began to realize what it was he opened his eyes wide and I immediately pressed my lips over his before he could protest and forced my tongue deep into his mouth.
Peter came hard and his butt cheeks tightened around the dildo I had forced into his virgin butt.
“Now wasn’t that simply wonderful?” I asked Peter and his freshly shaved bottom.
I was obsessed with the idea of taking this sweet straight boy Peter, and turning him into a cock sucker and bottom boy. I wanted to see if I could have him sucking another man’s cock within a week. It was a very exciting challenge to me. The next night I climbed on top of Peter’s penis and quietly slip a butt plug into his ass. This time he did not resist and I left it in the entire time we made love. After I had several orgasms I stopped. Led Peter to my closet and slipped my pink silk robe over his naked body sat him down at my computer. The whole time while his butt plug was inside his ass. It was such turn on for me.
We began to shop for lingerie for me online, and then I suggested that I would like to see him in some sexy sweet nothings as well since he had such nice shaved legs. Peter did not resist, I imagine because he had my butt plug buried in his ass and was very eager to cum.
After we bought sexy feminine outfits for both of us to wear, I led him back to the bed, and placed him on his front. I slip a pillow under his ass propping it up and slowly removed his butt plug. I then tied his writs to the bedpost and took out my 6 inch black dildo and teased his butt crack.
“What are you doing to me?” Peter asked helplessly.
“I am taking advantage of you sweet Peter and it is driving me wild. You have no idea how much this turns me on to see you so submissive. You do want to please me don’t you Peter?” I asked.
“Umm hmm” Peter moaned as I worked the head of the large black dildo into his tight little ass. It made me so wet to think that only the third night Peter and I had been lovers, he was allowing his ass to be violated for my pleasure. I began to cum in my panties as I watched the black cock go in and out of Peter’s cut little ass. I plunged the dildo as far as it would go into Peter and then untied him and turned him on his front as I rode his throbbing cock to a climax.
The next day the lingerie arrived and we unwrapped the boxes together. I had Peter undress me and then dress me up in his favorite sexy lingerie. Then I undressed him and began putting on stockings over his shaved legs, then a garter, then my favorite part was the white lace training bra.
“Arms up princess.” I said as I slid the bra onto his chest. “Now turn around and let me fasten it. Good boy. Can’t you just imagine that you are a sweet innocent little girl with new breast in this lace bra?” I tugged and tightened Peter’s first bra and my pussy became soaked from the power of this exchange.
I took sweet Peter to bed and we made love like two lesbians both dressed in sexy lingerie. I took out a double headed dildo and began sucking it while Peter watched and fucked me. It was all too much and I came over and over and was lost far from this world in pleasure.
“Will you suck this for me sweetie?” I asked Peter as I led his lips to the large plastic cock in from of his face. Peter took the dildo into his mouth without so much as a wimper and began to suck. I gave him some helpful hints about how to take it deep without gagging and watched as my sweet boy sucked on my plastic cock on our 4th night in bed together. I was feeling pleasure deep in my pussy that I had never felt before. It was almost like having sex for the first time again. I was having multiple orgasms all over Peter’s pantied cock. It was unbelievable bliss. Peter and I passed out together still dressed in out new sexy lingerie and when we woke up the next morning, we made love for two hours again and it was just as wonderful as the night before.
We both called sick into work that day and bathed each other in soft soaps and oils. I dried and dressed Peter in panties and a bra and then put on a very tight fitting pair of my shorts on him. Then I picked out a tight tee shit for him and you could see his bra through it. He was bulging out of my clothes. I then applied just a little lip gloss to his lips, and a bit of make up too.
“Let’s go shopping” I said. “There is something very special I want to buy for you.”
“I can’t go out dressed like this!” Peter exclaimed. “People will think I am gay.”
“Oh don’t be such a sissy.” I said giggling. “No one will think that because you will be with me and I will hold your hand. All the women will be jealous that I have such a good looking boyfriend and all the gay men will want you. Please Peter, if you do this for me you will be rewarded with a very special gift.”
Peter reluctantly agreed and I drove him to the local sex shop. I made him reapply his lip gloss at a stop light and watched as several construction workers looked curiously at him. It was SUCH a turn on!!!
I led Peter by the hand around the sex shop and picked out a large black strap on dildo. Peter paid for it and as we drove home I made Peter unwrap it and place it between my legs as I drove. I began to stroke it and then forced his head down to suck on it like he was giving me a blow job. I exploded into an orgasm and almost crashed the car.
At our apartment I forcefully took Peter into the bedroom and placed him on his knees as he watched me strap on my new black dildo in front of his face. I teased his mouth with the head of the cock and then took him by the back of the head and watched as my cock went in and out of his sweet glossy lips. This was the most excitingly erotic thing I had seen and wondered why I had not done this to a boy before. I told Peter to suck on my cock and to play with his man clit until he came all over himself. He did in under a minute.
That night I tied Peter to the bed post again on his back and lifted his legs into the air while I fucked his virgin ass with my cock. The fact that Peter was so willing to let me violate him for my own pleasure made me extremely hot. To know that I was taking his virginity was an absolute turn on and as I fucked him with my strap on and he moaned, I began to cum again. I think on that 5th day with Peter I managed to have almost 40 orgasms. That’s the truth.
The next day we both went back to work and I told Lamar all about my progress with Peter and Lamar was impressed. I invited him over to our apartment that night after work and snuck him in before Peter got home. When Peter arrived I led him into the bathroom and began to dress him up in his sexy lingerie again. I dressed him as a little virgin slut with white lace, pig tails, and red hot lipstick. I locked him in the bathroom as I went and got Lamar to undress and get into our bed.
I went back into the bathroom and could barely contain my excitement. “Sweetie, I have a big surprise for you.” I said as I opened the door and Peter saw the Hawaiian muscle stud laying on the bed waiting for him.
“What’s this?” Peter asked scared and confused.
“It’s my ultimate fantasy honey.” I said. “Now don’t be shy, just go over to Lamar and give him a nice big hug for me.”
“I don’t know about this.” Peter protested.
I stood behind Peter and grabbed his arms and slowly walked him over the bed with the gay stud waiting for him. I whispered soft sweet things into his ear and stroked his cock beneath his lace panties.
“It’s ok. Don’t be scared. I am here and will not let anything hurt you. This is going to make me very happy and excited. You want to please me don’t you? It’s going to feel fabulous. Haven’t you ever wondered what it might be like to be a girl and be taken? This is your chance sweet Peter. Please, do this for me. I promise you will enjoy it and if you don’t we can stop.” I coaxed him.
Peter, dressed in white lace and lipstick, reluctantly got into bed with Lamar and gave him a long hug on my instruction. Lorimar’s hands explored Peter’s soft and shaved body. I glanced down and noticed Peter’s penis was getting larger.
“Now that doesn’t feel so bad now does it? Let Lamar kiss you now Peter.” I instructed.
Lamar’s tongue invaded Peter’s mouth and he began to kiss my sweet boy passionately. I reached down and stroked Peter’s cock for awhile and then replaced my hand with Lamar’s. When Peter was more relaxed I took his hand and placed it on Lamar’s cock and he stroked it until it was huge.
“Ok now Peter, I want you to kiss Lamar’s cock for me” I said. Peter did as I told him now.
“Oh my goodness. His cock is huge!” Peter exclaimed. Much bigger than mine.
“Yes sweetie it is. But don’t be scared, that’s just more pleasure for you.” I said.
I held Peter’s head as it bobbed on Lamar’s gay cock. I was completely turned on and could not help fingering myself as I watched my boy toy going down on another man. And it had only taken me 6 days. I began to cum and moan and this made Peter suck harder faster and deeper.
Lamar began to moan too and I sensed he was going to explode. “Now Peter, I want you to swallow every drop of his cum for me like the sweet little girly boy that you are.”
Lamar began to orgasm into Peter’s sweet painted mouth and his cum shot down Peter’s throat. Peter swallowed and I turned his head to me and kissed him very gently.
“You are an absolute wonder cock sucker Peter. You have no idea how much this is turning me on.” I said. Before Peter could speak, I kissed him deeply and began to play with is hard cock. “Now be honest, was that so bad?” I asked.
“No.” Peter said shyly and rather embarrassed.
“Don’t worry, I won’t tell anyone about this. It will just our little secret. Now, what shall we do with that rock hard cock of yours?”
I laid down and spread my legs and took out Peter’s hard on from his panties. I placed him inside of me and gently let him fuck me. I told Lamar that when he was ready, he could fuck Peter’s ass.
Lamar wasted no time and applied lotion to his gorgeous cock and began to slip it into Peter’s butt as I spread his cheeks for him. As Peter was fucking me I watched his eyes grow large as he was evaded by a gay man’s cock. I began to have uncontrollable multiple orgasms as I watched my sweet boy being taken by a man for the first time. Peter began to cum and as his butt muscle tightened he cried out as Lamar’s enormous cock sunk deep into his love hole.
“I think you like this too don’t you sweetie?” I asked Peter. He nodded from utter pleasure. “Don’t be shy Peter. I know you secretly wonder what it would be like to be Lamar’s boyfriend don’t you?” I asked. “It’s ok. I want you to have a boyfriend. It really turns me on.”
Peter agreed to go out with Lamar a few times and before long, he was getting fucked by Lamar instead of me. And then they moved in together and I went searching for another sweet boy to force into a fag. It’s an addiction I still can’t put down.
Strapon Mom Sex Story. First Time With My Best Friend’s Mom And Her Strap On Sex Story. July 14, 2007
Posted by sexstory in Bi Sexual Sex stories, Crossdressing Sex Stories, Crossdressing Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Gay Sex Stories, Kinky Sex Stories, Older Women Sex Stories, Role Play Sex Stories, Romantic Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, True Sex Stories.9 comments
Strapon Mom Sex Story. First Time With My Best Friend’s Mom And Her Strap On Sex Story.
This is the true sex story of a strapon mom and me. Not just any old sexy strapon mom, but my best friend’s mom.
Written By Dave
My name is Dave and my friend’s name is Ed. We have been friends since we were in elementary school. Our parents only live one block away and we grew up together. Ed’s mother has always been a hottie. I recall that the first time i masturbated, I was thinking about her. Of course I was too shy to ever say anything, and I was not the only one who thought she was hot. But I am sure that she knew all along that I was attracted to her. She was always very nice to me, even more so than her son Ed.
Ed and I grew up and went to different colleges and sort of lost touch. During my sophomore year, I returned to my old neighborhood for Christmas vacation and went to Ed’s house to see if he was home. I rang the door bell, and sure enough, a vision of sexiness answered the door.
“Well hello Dave. It’s good to see you again. My, you have really filled out. I bet all the girls at college love you. But I remember when you were just a little boy. Cute and playful. Sweet as a cherry pie. Now turn around and let me take a look at you.” My best friend’s mother said.
I turned around and her eyes poured all over my ass. She took my shoulders and twirled me around again.
“Well, my goodness, you certainly have been growing up. Come here and give me a hug sweeite.” Ed’s mother said.
As I hugged the mature voluptuous women, I was reminded why I used to masturbate about her so much. She was a goddess of form. she had big tits, the kind that are firm and stick out and beacon to be sucked. It’s the first thing anyone, male or female, can think about. She has wide hips, but not too wide, and stands about 6 feet tall which is 2 inches taller than I do. Her lips are full and sensual and sort of have a devious grin to them. They speak of being filled with an excess of estergine and perhaps a side of testosterone. The older woman commands respect and you can sense that if you give it to her, she is going to know exactly what to do with it. She is a natural dominant and powerful woman and we men are but moths to the flame of her sensuality.
“Hi Miss Bowen, ” I said. “It’s nice to see you too. You haven’t changed a bit. You look great. I was just stopping by to see if Dave was home for the holidays.”
“No sugar, Dave is not here yet. He is expected to be home in a few days now. But please do come in and sit for a spell. I live alone now and enjoy company. Let me make you something to eat and perhaps you would like some wine to drink. We can catch up on all that has happened in the past few years. Please come in.” She said and took my hand and walked me through the house.
Ed’s mother made me a sandwich and opened a bottle of Pinot Noir and then got up.
strapon mom
“Llet me change into something more comfortable. It’s so wonderful to see you again. You know, you were always my favorite. You had the cutest little boy smile and you always looked up at me with those pretty little eyes of yours” Miss Bowen said as she went to change her clothes.
I drank several glasses and was getting tipsy when she returned. She was now wearing a silk long nightgown that was closed but underneath I could tell she was wearing a black stockings and a garter belt. Good god she looked sexy. I was starting to think she wanted to seduce me.
“Did Ed tell you his big news?” She said.
“I don’t think so, what news?” I said.
“Well, he finally came out of the closet this year. My son Ed is gay. I suppose I was a little too nurturing with him, and perhaps was too much of a strong woman. It didn’t help that he didn’t know his father very well either. But they say, that being gay is not a choice. He has a boyfriend now and is happy to have come out of the close. ” She said.
“Wow, I would have never known he was gay. He always seemed so masucline and strong to me. ” I said.
“Well, I think he is a top. Meaning that he likes to be on top. He likes the cute boys, the submissive ones you know. Much like yourself. I always thought that you might have been gay too and that you and my son were lovers.” She said.
“No, I never knew. He never made a pass at me. We were just friends.” I said.
“Well I knew he had a big crush on you when you were younger. But what about you? Do you have a girlfriend in college? ” She asked.
“Well, I did, but it didn’t work out. She slept with my room mate so we broke up. I have been lonely and alone for awhile now.” I said.
“That is a shame, such a nice boy like you deserves a good woman. Come here and let me give you a hug.” My best friend’s mom said.
I got up and hugged Miss Bowen and I felt her hand slip down to my ass. She turned her cheek and our lips meet and she kissed me deeply with her tongue. Her hands continued to explore my ass and legs while we kissed. It all happened so quickly I didn’t have time to think.
Then she stopped and said, “I always knew you liked me. I could tell by the way you looked at me. You would watch my every move and look me up and down. And you would do anything I told you to do. I liked you too and just kept waiting for you to grow up. And now, here you are my sweet cute boy. I am very happy that you came over to see me.” My best friends mom said.
I began to blush and could feel my dick swell.
“Miss Bowen, I’m a little confused right now.” I said.
“Well, don’t be. There is absolutely nothing to be confused about. What you are feeling is as natural as a spring rain.” Miss Bowen said as she began to unbutton my jeans and skid them down my legs exposing my growing cock.
“Now let’s get these tight pants off you baby and see what you are hiding under there for me.” She said as she pulled down my underwear and exposed my manhood.
Miss Bowen then grabbed me forcefully and laid me down over her knee with my exposed ass sticking up in the air.
“Before we go any further, you must be punished for all the bad things you did at my house when you were a little boy.” She said and she began to gently slap my ass which made very loud smaking noises.
“But I was a good boy Miss Bowen, I never did anything bad.” I said as she slapped my butt repeatedly.
“Well, what about all the naughty things you were thinking about? Now look at yourself in the mirror as I turn your bottom red as a race car.” She said.
Miss Bowen spanked me over and over and I watched her do it in the bedroom mirror. The same mirror I used to look at when I was a young boy staying over with her son.
“Very good, now stand up and let me take off your shirt.” She said and she raised my arms up and lifted my shirt. With my arms high and the shirt almost off she stopped and kissed me deeply. “You are going to be my favorite boy toy sweetie. I am going to teach you some very wonderful and sexy things. You want that don’t you?” She asked.
“Umm, yes I do” I said.
“From now on, you will call me ma’am. Understand?” She said.
I was so horny I would have called her anything. “Yes ma’am” I said.
“Oh that’s very good” she said.
My best friends mom then laid down on the bed and spread her legs and pointed to her pussy.
“Now my sweet young thing, come over here and I will teach you what every woman wants. Stick out your tonge honey and begin to clean out my pussy for me.” She said.
“Yes ma’am” I said and went to work. My best friend’s mom told me where to lick, how to lick, and how long to lick, and after she bursted into several orgasms, she then told me to mount her. She began to slowly insert my cock into her mature pussy and moved me back and forth in the motion that she liked the best.
“Now don’t cum ok? I have many more things I would like to do to you.” She said.
I did my best to refrain from ejaculating inside of her but when I got close, she would shove me out of her and talk me down. We made love for over an hour and she had many many orgasms. I had no idea women could have so many. It was a beautiful sight to see.
“Now sweet boy, I am going to show you how to fuck a woman properly. But the best way to do this is by getting fucked yourself.” She said as she tied my writs together, and then tied my ankles together and lifted my legs into the air.
“What are you doing?” I cried.
“If you ask any more questions, I will stick a gag in your mouth so shut up and keep your legs up, I’ll be right back.” Miss Bowen said.
She returned several minutes later wearing a very large strapon dildo. I was speechless. Was she going to use that on me? I didn’t even really understand what it was at first.
Miss Bowen began to put a cool jelly on my butt and then slipped a finger in my ass.
“Ma’am, what is going on?” I asked.
“Now I told you to keep your mouth shut. Since you can’t seem to shut it, I’m going to fill it with my strapon cock.” And she shoved her didlo into my mouth. “There, now that should keep you quiet. Suck on it until you realize that your mouth is only good for two things. Sucking my cunt, and sucking my cock. That’s all I want your mouth to do from now on.” She said as I sucked the giant cock as she fucked my mouth.
“That’s a good boy. A VERY good boy. Yes, momma likes to see her big cock going in and out of her sweet boy’s mouth.”
After awhile, she took the strapon out of my mouth and began to slowly insert it into my ass. It hurt at first and I moaned but tried very hard to keep my mouth shut.
“The best way to learn how to fuck a woman, is to get fucked yourself. I am going to show you how a real man fucks.” She explained. Miss Bowen began fucking me with her strapon and it began to make a noise just like when I was fucking her.
“Do you hear that? That’s your ass pussy eating up my large cock. Now take a look in the mirror and watch yourself losing your virginity.” She said.
I looked over and saw my legs up in the air and my sexy best friend’s mom fucking me deep. Although it hurt, I could not help but come and came all over my stomach.
“Did I tell you to come? It seems you like this a little too much. You might just be gay after all. I always suspected you were. It’s ok if you enjoy my cock in your ass. My son is gay and I still love him very much. Perhaps ever more so.” She said.
“Ma’am, I’m not gay, it’s just that………….well………I don’t know.” I said.
“Shhhh…..hush now sweetie. I won’t tell anyone. You see, I just gave you a gay test and you didn’t know it. You fucked me for over an hour and didn’t come. But you came in less than a minute with a cock in your ass. Do you know what that means?” She asked.
“um, no.” I said.
“It means you like a nice big cock in your ass more than your cock in a pussy.” She said. “Don’t be shy, and don’t be scared. I have known you almost your entire life and watched you grow up and I always had a sense that you might be gay.” She said.
“I’m not gay.” I said.
“Honey, I realize it may take some time to come to terms with it. I want you to spend the night with me tonight, and we will talk about this more in the morning.” She said.
Miss Bowen whipped my cum off my chest and untied me.
“Tonight you are going to wear my panties and silk teddy to bed sweetie. It’s to celebrate losing your virginity to me and my cock. Now come over here to my closet and let me dress you for bed.”
Miss Bowen dressed me in her lingerie and we got into bed together. She laid my head on her chest and I began to get hard again. She lifted up her bra and placed my lips onto her supple nipples.
“Does sweetie need to suck a little before he goes to sleep?” She said.
I moaned that indeed I did.
“I can feel your little girl clit getting hard in your panties” she said. “Now suck on this for awhile.”
Miss Bowen gently removed my mouth from her breast and inserted a small dildo between my lips instead.
“Oh that’s very nice. You are getting much better at this. Soon you will be an excellent cock sucker.” She said.
As I sucked on her dildo, she reached down into my panties and began to stoke my cock and I released my cum inside the panties almost immediately.
“Miss Bowen. You have made me very confused. Am I gay now? ” I asked.
“Hush little baby. It’s time for night night. now go to sleep with your panties full of cum and we will discover more wonderful things tomorrow.” She said.
I awoke the next morning to a wonderful sensation. I looked down and Miss Bowen was sucking my cock. I didn’t say anything but just moaned and enjoyed it. Miss Bowen sucked my cock for over a half an hour and then stopped.
“Good morning princess. Did the princess sleep well in her silk panties filled with cum?” She said.
“Yes ma’am.” I said.
“Well good, let’s take a shower together shall we? And get nice and clean.” She said.
We took a nice long shower together and she cleaned me throughly. Then she dried me off.
“From now on baby, I want you to wear panties. Once you have had my cock in your ass, you can no longer wear those dreadful boy underwear.” She said and slipped me into a new pair of her pink panties.
Miss Bowen led me into the bedroom again and told me to suck her pussy which I did for a very very long time. She came over and over and told me to keep licking and sucking just the way she liked it.
“Even if you are gay, I can still use you to please me in this way. You are getting to be very good at it and when I train you to perfection, I have some friends of mine that I will want you to meet.” She said.
“Now, lets see if you learned anything from when you had my cock in your ass pussy yesterday. Come up here and fuck me like I fucked you.” She demanded.
I began to fuck Miss Bowen hard and deep.
“You are a slow learner sweetie. But keep trying. Remember what I showed you with my strapon. That’s how mommy likes it.” She said.
I fucked her for almost two hours until she was satisfied enough. I was exhausted.
“Time for your second lesson. Now this time, I hope you can keep from cumming so quickly so I can teach you more.” Miss Bowen said.
She took out her strapon dildo and strapped it on again. Then she put a lubbed finger into my ass.
“We need to stretch your ass pussy out just a little bit more today so that it is not so painful for you.” She said as she worked several fingers into my ass. “There, that is much better.”
My best friend’s mom stacked 3 pillows in the center of the bed and laid me over them with my ass exposed into the air.
“NOw get comfy darling, and try to relax for your second lesson.” She said.
She gently worked the head of her strapon dildo into my ass and began to move it in and out. It didn’t hurt so bad this time and as I relaxed, it actually began to feel wonderful.
“That’s it sugar. You are doing very well. Not pay attention to how I do it.” She said.
Miss Bowen placed her hands on my hips and pushed them back and forth, back and forth as her strapon filled my ass.
strapon dildo mom
“Now push back on it in the same rhythm.” She said as I tried to move my hips in the guidance of her mature hands. “Oh excellent, you are doing a very good job.”
And with those words of encouragement, I exploded and came all over the stacked pillows I was bent over on.
Miss Bowen laughed and took out her strapon cock from my asshole. She rolled me over and held me closely on the bed.
“Honey, now do you see? You fucked me for two hours and didn’t come. But when you had my cock in your ass, you came in 2 minutes. I think it’s time for you to accept it. You prefer a cock in your ass don’t you?” She asked.
“Ma’am, I am very confused.” I said.
“Don’t be. It’s very clear. We need to find you a boyfriend. It’s the only way to know for sure if you are gay or now. My son is coming home today. You two have always been very close, I think you would be perfect for each other. Now why don’t you practice sucking my strapon so when he gets here, you can show him what I’ve taught you.”
Strapon Mom Sex Story. First Time With My Best Friend’s Mom and her Strapon dildo.
Forced Strapon by Dominant Women Sex Stories July 13, 2007
Posted by sexstory in Domination Sex Stories, Femdom Sex Stories, Group Sex Stories, Kinky Sex Stories, Lesbian Sex Stories, Older Women Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories.4 comments
Forced Strapon by Dominant Women Sex Story written by Ian. The story of how one man’s job interview leads to a jackpot of dominant women.
I had just turned 21 and left the cold callus streets of Chicago and headed for Key West in hopes to find fun in the sun and a new life. When I arrived, I found a place to live and went in search for a job. I tried my hand at waiting tables, and bartending but I didn’t like it. I saw a job for a tour guide and went to the interview. I was met by 2 older women who were very sexy and very dominant. They gave me a script to read and I must have done well because they took me into another room where more older women were and I was asked to read for them.
“Good job.” One of the mature ladies said. “Another part of your job is taking clients out on the town and entertaining them. Most of them will be older women in their 40’s or 50’s and you will have to show them a good time. Can you do that?”
I thought about it and didn’t see the harm. “Sure, sounds great.” I said.
“We need to test you once to see how well you can do this so we have arranged that you will come to my house tonight and pick the ladies up and show them a good time.”
“Oh, and one more thing, could you just turn around a few times so all the women here can get a good look at you?” She said.
Feeling like a piece of meat, I twilled a few times and felt the stares of the older women looking at my ass.
The older woman gave me her phone number and told me to call her at 8pm and she gave me a big hug and a kiss. I called her and met her and her friends at their large mansion overlooking the ocean. They were loaded. I took the women out and we had a great time drinking and dancing. They took turns dancing with me, flirting with me, and feeling my ass as we danced. I didn’t mind, it was all great fun.
We went back to their mansion on the ocean and they all begged me to stay for one last drink. I was getting excited about it and began to think there might be some sex involved but with who?
The older women that owned the mansion was named Sandra. She was almost 50, very sexy, and I could tell that she was a very dominant woman. Everyone else did as she said and treated her with respect, so I did the same, as well as hoping to get paid or perhaps tipped well.
“Listen, we are all going to get into the hot tub on the balcony. I want you to join us.” Sandra said.
“Ok, but I don’t have a swim suit.” I said. All the other women laughed at my remark.
“Well honey, we can take care of that. Follow me.” Sandra said and took me by the hand into her bedroom and left the door wide open. “Now take off your clothes so I can find you something more comfortable to wear.”
I was shy but curious too. I took off my shirt and pants and then stopped.
“Now don’t be shy sweetie. I have seen it all before. And there is something else you might want to know. I am gay. Sometimes bi sexual but mostly gay. I prefer women and all those women downstairs have been or currently are my lovers.” Sandra said.
I didn’t know what to think about all this. Why had they been flirting with me? Why choose me to entertain them and not a young good looking woman?
“Now do as momma says and take off you little underwear. That’s nice. Good boy. You have a nice tight butt. Turn around so I can take a better look. Good. Now bend over slightly. Oh how sweet. That is what momma likes. I had a feeling about you. You will do just fine. Now try on this bikini bottom with the ties on the side.” Sandra said as she slipped the bathing suit up my legs and attached it around my hips.
“Now turn around and let me see how your ass looks in it.” Sandra said as she spanked me. “Perfect, now lets go show the girls shall we?”
Sandra led me to the hot tub where there were 6 beautiful older and dominant women waiting for me to arrive. They asked me to show them my new swimsuit and I had to model it for them. It was all highly erotic and was turning me on.
As we say soaking in the hot tub, I was passed around and fondled by each mature woman. I sat on their lap and they played with my ass and would sometimes stroke my cock. One woman tried to stick a finger in my ass but I did not let her. Another woman tickled me and managed to pull the strings loose on my bikini bottom and threw my swimsuit out of the hot tub. Then I was naked and vulnerable. I also had a hard on and began to wonder just what they had planed for me.
Then, two women grabbed my arms and held me there next to them.
“Oh little sexy boy, you are going to be ours tonight. We’ve got you now and it’s up to you to decide if you are going to enjoy it, or fight it.” Sandra said.
“What are you going to do with me?” I asked a little scared.
“You will soon find out.” Sandra said.
The two women holding me down tied my wrists together and spread my legs apart in the hot tub. With all the other women there watching, I knew my resistance was futile. Plus, I was actually pretty excited by all the attention so I did as they said.
One of the dominant lesbians leaned over to me and stroked my hard cock and said, “That small little penis of yours will no longer be necessary. You’ve got a pussy now sissy boy.” I didn’t like the sound of that one bit.
One of the lesbians produced a large dildo and forced it into my mouth.
“Now show us how well you can suck a large cock, and you might get a tip.” She said.
I took the large dildo into my mouth and sucked on it. I was actually very turned on knowing that I was sitting helpless in a hot tub with 7 dominant mature women who were either lesbians or bisexual watching me suck a cock. Then I felt a large finger being forced into my ass. I clenched my butt cheeks but it was no use. So I tried to relax as I was sucking the large cock and having my asshole fingered. In fact, it was not so bad.
I watched as several of the older women began to finger themselves and even climax and orgasm. This turned me on and my penis was fully erect.
“Very good little boy. You have pleased us with your cock sucking abilities. And we can see that we have please you because you little clit if fully erect and hard isn’t it?” Sandra said.
The women raised me up, exposing my naked erect cock, and they led me by the arm into the living room. They escorted me to the center of the room and forced me down on my knees next to the coffee table. Then they bent me over the coffee table and untied my writs only to retie them to the coffee table legs. They also tied my thighs to the other side of the coffee table. I lay there completely exposed with my ass in the air at the mercy of the dominant lesbians. I was scared and vulnerable, as I am sure that is how they wanted it to be. I was their entertainment for the night.
One by one, each of the dominant older women began to strap on strapon dildos of various sizes and lengths. Some of the strapons were black and huge cocks. While others were pretty colors like pink and red. It was a little intimidating for me.
A tall and large dominant blonde woman walked over to my face and forced her strapon into my mouth. I almost choked on it as she took me by my scalp and forced fucked my face with her huge strapon cock. Then I was spanked and felt a wet feeling in the crack of my ass. I assumed and hoped it was some kind of lube so my virgin ass could handle the large strapon cock about to be forced into my butt.
Sure enough, slowly, and somewhat painfully, a felt a large strapon cock forcing it’s way into my ass. It was so large and so uncomfortable that I could not help but let out a small cry, then whimper, then a loud moan.
“Joanie, I think he likes that strapon forced into his ass. Perhaps you should fuck him a little harder.” One of the dominant women said.
So there I was, in the center of a mansion being forced fucked in the ass by a lesbians strapon dildo. One by one they all took turns fucking me in the ass and forced me to suck their cock. Their large strapons had no mercy as they worked me over. At first, it was painful, and then it began to feel good, but then it was uncomfortable again. With my hands and legs tied, I was unable to play with my cock, so it hung there limp, being banged around by the forced strapon action.
The women loved it. They were taking pictures of me and said they would post them on the internet if I ever told anyone about this. They also said that if they ever felt like it, they would have ask me over again to play with and if I said no, the pictures would go online.
They pretty much had me over a barrel so to speak. After several hours of the forced strapon punishment, I was untied, and asked to dress. The sun was coming up while I put my clothes back on and the women looked tired. I had a difficult time walking because my ass was so sore from all the dominant women and their strapons. They laughed at me as I gathered my stuff and left the large mansion.
When I got home, I found a message on my machine from one of the dominant women that said I had got the job.
Forced Strapon by Dominant Women Sex Stories. The story of how one man’s job interview leads to a jackpot of dominant women.
Forced To Feminize. Crossdressing With My Step Mother part two. July 8, 2007
Posted by sexstory in Crossdressing Sex Stories, Crossdressing Stories, Cuckold Stories, Femdom Sex Stories, Forced to Feminize, Incest Sex Stories, Kinky Sex Stories, Older Women Sex Stories, Role Play Sex Stories, Sex Fantasies, Sex Stories, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, True Sex Stories.5 comments
Forced To Feminize. Crossdressing with my step mother part two.
This is the second crossdressing story about how I was forced to feminize and began crossdressing with my step mother.
After the night I feel asleep with my step mother in her bed wearing her panties and bra and lace teddy, we woke up and she finished washing my regular clothes and dressed me back as a boy.
“Today we are going shopping.” My step mother announced.
As we were driving in her car to the shopping mall, my step mom asked me to find her lipstick in her purse.
“Now watch closely how I do this.” She said. “Now I want you to put a little lipstick on your lips too.” She said.
“No way.” I said. “ I’m going to look like a girl at the mall and everyone will see me.”
“Now listen, every movie you have ever seen, the actors are wearing lipstick and lots of make up. Just rub the pretty lipstick on your pretty mouth and accent your full luscious lips. Don’t be shy.” She said.
I did as I was told but felt funny about it. However it tasted pretty good and smelled good too but it made me feel very self conscious at the mall.
My step mother began buying clothes for herself and I was forced to watch as she dressed up in different outfits. I must admit she was a very sexy woman. She had curves in all the right places. She had an air of dominance about her and I always felt very safe around her. She also was good with people. I loved her deep and sexy voice. It almost seemed like each work out of her mouth was actually saying, “I want to do naughty things to do little boy.” I was young and a virgin and enjoyed each moment of her attention
She began to pick out lingerie for me, having me try it on and then showing it to her. She even asked one of the pretty young clerks for her opinion.
“Now how do you think my pretty young sissy girl looks in this one….and this one…..and this one?” She would ask the clerk who giggled at me and looked me over.
After buying skirts, blouses, panties, bras, shoes, and even girl lingerie, my step mother dragged me by the hand into what appeared to be a homosexual clothing store. She handed me over to a clerk and said, “find lot’s of tight and white for my sissy boy.” And then she left me there for about an hour while this large muscle stud dressed me in tight white clothes. When she came back, we hauled all our stuff to the car and went back to our house for a fashion show.
“Now my little sissy boy, I want you to dress me up first. I want you to pick out your favorite outfit and dress me up. And if you are lucky, I will do the same to you.” She said.
I undressed her and her big tits spilled out. I could not keep my hands off them and was slapped across the face for it. I stuck to the task and dressed her in my favorite outfit. It was a tight fitting dress, with leather boots and a large cleavage area. I choose white lace panties for my step mom and a big white bra for her big tits.
“Perfect. You have choosen well my little sissy boy. Now it’s your turn.” She said and she picked out very slutty clothes for me to wear that evening. She seduced me into the bathroom and applied lipstick and makeup to my face and then put me over her lap for my evening spanking.
“You are my good little crossdresser aren’t you?” My step mother said. “From now on, you are going to wear what I want you to wear each day, and that includes all those tight clothes for boys I bought you. The boys and girls are going to love you at school. You trust me don’t you, and I know you love all the attention mom is giving you lately.”
That night, we ate dinner as I was dressed like a little sissy slut girl. In some ways, I enjoyed it, but I also felt a little strange at first.
“In time my sweet sissy, you are going to enjoy wearing girls clothes. In fact you are going to enjoy it so much, you may even decide to be a girl. But never mind that now, mother has plans for you this evening.” She said and led me into the bedroom again.
My step mother tied my hands behind my back and knelt me on my knees. “It’s time I introduce you to my very special friend. It’s called cock. This is my cock and you and it are going to get along just perfect, I know it. But you are not allowed to touch it yet because you have not learned respect from it. So we are going to watch a movie that will explain to you all about cock, and what to do with it.” My step mother said and she left me on my knees, with her cock in my face, as we watched a porno about a woman who learns to suck cock for the first time.
The cock sucking porno movie made me hard. It was beautiful to watch the woman place her virgin lips on the large cock. My penis was not as large as his and I felt insecure.
“I’m not as big as him.” I told my step mother.
She laughed at me as said, “Silly girl, you don’t need your cock. All you need is that little clitty between your legs, and your sexy little butt as well as your pretty painted mouth. That big cock will do the rest. I want you to keep watching how she sucks that large penis because you are going to suck mine now.” She said.
My step mother plunged her cock into my mouth as I tried to stop her but because my hands were tied, there was little I could do.
“Oh stop fighting it. I know you like it, I can see your little girl clitty getting hard. Just take the cock into your mouth. You may find it a wonderful and peaceful experience. It’s very important to train you right from the start. That’s good sissy, just like that, nice and slow and back and forth, just imagine how you would want someone to suck on your dick.” She said as I took the cock as deep into my mouth as I could.
“I have forced you to feminize quite well in such as short time. It’s time for us to go to bed now, we will have company over tomorrow and you can show them what you have learned today my sweet little sissy.” My step mother said.
And as usual, she forced me to sleep in her bed with her. She began to leave my hands tied up as we sleep and occasionally during the night and in the morning, I would feel her hands dig into my panties and play with my cock until it was hard. Sometimes she would tease and play with my asshole too which would only make me more excited.
Yes, I had been forced to feminize, and crossdressing with my step mother was opening up new worlds to me.
Cockold Stories. Cockold husband is forced to feminize sex story part two. July 7, 2007
Posted by sexstory in Cockold stories, Crossdressing Sex Stories, Crossdressing Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Kinky Sex Stories, Role Play Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, Three Some Sex Stories, True Sex Stories.11 comments
Cockold Stories. Cockold husband is forced to feminize sex story part two.
Written by Sheri Wilson
This is the true sex story about transforming my cockold husband into a cockold sissy slut.
After I forced my husband to wear the French Maids uniform and go around and suck on the dildos my friends and I had, I sent everyone home and they each spanked my husband as they left. My poor cockold husband was forced to lift up his skirt, bend over, and allow each one of my friends a good SMACK on his tight little pantied butt.
“You did a wonderful job at the party tonight sweet sissy, you looked so good in that French Maids uniform. Now I want you to clean up the house while wearing it, and while you are doing that, I am going to prepare a nice warm bubble bath for my sissy. Then I will give you that treat I promised you.” I told my husband.
I went upstairs and drew a nice bath, then I placed a new negligee, stockings, some high heels I found at a cross-dressing transsexual store, out on the bed. When my husband arrived in the bathroom, I stripped off his uniform and began to bath him.
“Doesn’t it feel wonderful to be part of the girls? It’s a side most men never get to see. It’s such a liberating feeling to be soft, and clean and to wear pretty things. Men are too worried about trying to be so strong and powerful. Most of the time, we as woman are attracted to that, but we also like a soft and sweet man too. It’s complicated. You are so lucky to be able to truly be one of the girls tonight and I hoped you learned a few things.” I told my husband as I washed his hair.
Then I began to shave his body hair. First his legs, and then his arms, and finally his pubic hair. My poor submissive husband had lost almost all his self respect by now, and it was getting easier to feminize him. I still had to force it a little. I would threaten to kick him out on the street, or to tell all of our friends that he liked to suck cock. We had witnesses now and I had some secret photos too. But mostly, he reluctantly when along with my wishes to feminize him and complete the cockhold husband training. After all, if he made it too easy, it wouldn’t be so fun.
“Now get out of the bath my shaved sissy. That’s good. Doesn’t that feel great? It’s going to feel so good in your panties and nightgown and stockings.” I said.
“My what?” He said.
“Now hush and let momma dress you up lovely and sweet. Step into these pretty pink stockings that I bought for you. Good. Now attach this garter belt to your wonderful sissy hips. That’s perfect. Your getting better. Now slip on thess high heels that I found. Lovely. You look wonderful. What man would not what to have you? “ I said.
“What are you talking about now? A man? No, I am going to draw the line when you speak about another man.” He protested.
“Now listen my sweet sissy pussy boy. If you don’t do exactly what I say, I am going to tell everyone we know that you suck my cock. And I will send the pictures I have to your family to prove it. You wouldn’t want that now would you?” I laughed.
“Well, no. So long as I don’t have to have sex with a man. Can you promise me that?” My husband asked.
“The only promise I can make to you, is that if you do what I say, you can stay in our house and don’t have to work. You can continue to live like you do. And I promise that I will think about your pleasure from time to time. Now admit it, so far, everything we have done, you have secretly enjoyed it. I have seen your erection while sucking on the dildo, and I watched you get hard when you were sucking on my girlfriends dildo. So you can stop the acting.” I said and I slapped him across the face.
“Yes, that’s good. I like how red your face gets when I slap it.” I said and slapped him several more times. “That looks like a good sissy slut. Yummy. That red face of yours is going to look good all over my big strap on dildo.” I said.
I added lots of lipstick and eye shadow to my husbands face. He looked like a cheap hooker. I led him into the bed room and forced him to strap on my strapon dildo. Then he assumed a position to suck it and I slapped him across the face again.
“No no sissy. You have already had a mouth full of cock tonight. Now it’s time to get an ass full.” I said.
I went to the draw and found a ball gag and placed in into his mouth. He looked so submissive to me. I was getting wet thinking about fucking my husband in the ass. I placed him on his front on top of a few pillows so his virgin ass was sticking straight up in the air. I tied his hands to the bed, and then spread his ankles and tied them to the bed also.
“Look at you now little sissy. About to get fucking in the ass for the first time. Are you scared? I can’t hear you. Oh, that’s right, you have a ball gag in your mouth.” I laughed at him.
Then I squirted lube all over his ass crack. I pushed aside his pretty yellow panties and took the tip of the dildo and rubbed in up and down his ass several times. I reached around and sure enough, he had a hard on.
“Someone likes all this far more than they should. Perhaps all these years you were a little sissy slut just too afraid to come out of the closet. Well, now you can little cockhold husband of mine. It’s ok, I want you to. Don’t deny it. I can see how much you want me to fuck you in your tight little virgin ass.” I said.
I split his butt crack in two, and began to force the head of the cock into his virginity. He moaned, and that turned me on even more. I slowly shoved the dildo deep into his ass, deeper and deeper. He took almost all of it. Then I began to fuck him slowly, in and out, then faster, then I was fucking him hard. I could tell he was in a little pain but could also tell he was enjoying it. I began to finger my clit while I fucked him and had a few orgasms.
Then all of a sudden, that little cockold husband of mine came into his panties.
“Hey sissy, you came fast. You’re not suppose to enjoy that so much. I had no idea that all these years you would have cum so fast if I fucked you in the ass. Oh, I can’t wait to tell all of my girlfriends at work about this.” I said.
I pulled out the large strap on dildo, then I lay down next to my tied up husband. I took off his ball gag and kissed him. He kissed me passionately.
“Now that I have found out how much you enjoy being my sissy slut, and being fucked in the ass, we are going to do this a lot more often. You would like that now wouldn’t you? “ I said.
“Yes. Very much.” My husband said.
“Well, if you listen to me, and do as I say, then I will reward you with my large strap on and place it deep into your little sissy ass.” I giggled.
The next weekend I invited my one my closest friends from law school over. Jennifer is a tall blond with large breast with short hair. She is a strong and dominant woman and always wins her cases. My made my sissy cockhold husband make us dinner and drinks and then clean up. Then I made him dress both of us up in dominatrix costumes. She was wearing black leather boots that tied all the way up to her thighs. I was wearing black silk stocking and high heels. And both of us donned large 8 inch black dildos.
I set up the video camera without my husband knowing it, and we began to force him to suck out cocks. Then we both took turns fucking him in the ass. He came instantly but we just kept lubing his butt up and fucking him. His limp penis and balls shook back and forth as we forced him into womanhood.
“You are so lucky to have such as tall sexy blond fuck your tight ass. Most little sissies have to pay for it. But since you are my sex slave now, it’s one of the perks.” I said as I watched my best friend pound my husband’s ass.
“You know, I think your husband is almost ready for the real thing”. Jennifer said to me.
“Yes, I think you might be right.” I said.
And that is the end of part two of cockold stories. Cockold story forced to feminize husband sex story.
Look for more cockhold stories on kinkysexstories.org. Cockold husband forced to feminize sex story part three is coming soon.
