Boy Toy For Mature Woman Femdom Sex Story September 6, 2008
Posted by sexstory in Domination Sex Stories, Femdom Sex Stories, Kinky Sex Stories, Older Women Sex Stories, Romantic Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Straight Sex Stories, Taboo Sex Stories, True Sex Stories.Tags: boy, boy toy, domination, female, female domination, femdom, free sex stories, Kinky Sex Stories, mature, older, Sex Stories, Sex Stories For Women, toy, woman
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Boy Toy For Mature Woman Femdom Sex Story. A mature woman builds the perfect boy toy for sexual pleasure.
A mature woman and her boy toy femdom sex story written by Miss Scarlet for
kinkysexstories.org.
Sex Story
Hello, I am a 45 year old mature woman who runs a very successful company. I love my job and have worked hard to get where I am. But in order to get to the position of power and wealth that I have, I had to make some difficult sacrifices along the way. One of those was to forgo intimate relationships. Working 10 hour days and traveling as often as I do, it’s proven impossible to maintain close relationships with lovers. 
Sure, I have had many flings along the way, but I always wanted more. Someone to love and love me back. But I learned that most men either feel threatened by my position, or simply require a more submissive woman that could be there for support
But one day I was reading a sex story about an older mature woman who had transformed a young boy into her sex slave and I was struck at how perfect that idea might work for me. So, I set out in search of finding a sexy hot young stud to mold into the perfect boy toy for my active and demanding lifestyle. I called up the human resource department of my company.
“What kind of worker are you looking for ma’am?” They asked.
“I’m looking for a young male 18 to 23 years old to be my personal assistant. He does not need previous work experience but he must be available 24/7. ” I told the HR department and the next day during my lunch hour I interviewed 4 different young boys.
Each day I would interview about 4 or 5 young men and ask them a multitude of questions. During this process, I began to get a better idea about what I was looking for and why. I realized I was looking for a boy who was young, dumb, and full of cum. I used to only like smart men, but I have learned that they give me trouble. I used to like tall muscle men, but they also have given me trouble. And there was something else rather personal. I used to want a well hung man, but I have a very compact pussy and the big boys only hurt me and dry me up. So perhaps I should try a man with an average or below average size penis. Of course it was impossible for me to screen the applicants for that, but I did my best to size each young cuttie up.
After several weeks of interviewing all these young men, I finally came across one boy who stuck out in my mind. He had the cutest butt of them all, a soft and kind voice, he smiled and giggled and was a little shy around me. He was from the country and totally naive in the dealings of the city and cut throat business. I liked him immediately and began to fantasize about how jealous all the other powerful women executives would be when they saw him with me.
“Just a couple of more questions for you Barry ok?” I asked during the interview. “Do you have a girlfriend?”
“No ma’am.” He said.
“Do you have family or friends near by?” I asked.
“No, I just moved to the city and don’t know anyone yet.” He said.
“Ok Barry, you did very well today, I’ll let you know shortly.” I said.
After he left my office, I took out my dildo from the desk drawer and masturbated while thinking about owning that gorgeous ass of his.
I hired Barry, who was 19 years old, and told him that I would pay him a small salary of 20k a year with the chance of a raise but I needed him to be on call 24/7. Barry, who was unsure about what he wanted to do with his future, was all too willing to be at my beckon call. He was young, full of energy and had a strong desire to please and be accepted. I set out immediately on building him and molding him into my perfect dream boy toy.
The first thing we did was go shopping.
“Barry honey, your duties for me are going to include a wide range of activities, from escorting me at formal social engagements, to working in the garden, to days at the beach. Your appearance will reflect upon me so I need to make sure you look good. Do you understand?”
“Yes ma;am.” He said.
“From now on, just call me Miss Scarlet.” I said.
“Yes Miss Scarlet.” He whispered.
I could not wait to see how my new boy toy looked in a pair of tight fitting jeans so off we went. I picked out several pairs and then took Barry by the hand to the dressing room where I waited outside and peeked through the crack to watch him undress. He was so young, and so cute, and had a butt that simply begged to be squeezed.
When Barry was dressed, I told him to come out so I could see and he spun around as I looked closely at his perfect butt in those tight jeans.
“Not bad. But lets see if we can find something a little tighter for you sweetie.” I said.
I was dying to get a closer view of his cock. I didn’t want anything too large, but something very cute.
“Do you have a swimsuit?” I asked.
“No Miss Scarlet.” He said.
I took Barry by the hand to buy him a thong. I love men in thongs. Especially 19 year old boys with bubble butts. I picked out several thongs for Barry that were a size or 2 too small and told him to try them on. He was very shy at first but I assured him that he needed the thong for pool parties and beach events and he had nothing to be shy about.
“Everything ok in there?” I yelled through the dressing room door.
“Yes, almost done.” He said.
“Don’t be shy, let’s take a good look at you.” I said. Barry meekishly opened the door and revealed his thong that I had picked out for him. The suit was a little too tight and smashed his cock and balls a little but I liked it. But what I liked most was that he was not a very well endowed boy. He was the perfect size for me. I looked down at his manhood, then up at him and smiled which put him at ease.
“How do they look?” He asked curiously.
“They are very sexy. Come here and let me fix them for you.” I said as I grabbed him by the hips and forced him over to me. He watched as I placed my finger inside the elastic band and fit them snugly around his waist. I watched as his cock began to swell with blood. I quickly stretched the band out and took a peek at his growing package, then snapped the band back.
“Yes, this will do nicely. Perfect. Now that I know your size, I’ll go pick out some more and bring them back for you to try on.” I said.
After buying my new toy several nice suits, the bill came to a couple of thousand dollars for his new wardrobe.
“Miss Scarlet, this is too much. How can I ever pay you back?” He asked.
“I’m sure we can come up with something.” I said. “Now let me show you where I live and you can try on all your new clothes for me ok?”
The next aspect of my plan for building the perfect boy toy was to build the perfect boy toy body. Barry already had a fine young body. After all, he was 26 years younger than me and I was was old enough to be his mother. But my hormones didn’t know that. Anyway, I figured Barry should have a personal trainer to spend an hour or two a day working out with, but I didn’t want him to be with a woman, so I sought out the biggest and scariest muscle man I could find for Barry to work out with.
Rick was a humongous Jamaican muscle stud and I hoped he would keep Barry in line when needed.
“Barry say hello to Rick. He will be your personal trainer. Each day, Rick will come here to the office and you two can work out in the weight room. As you can see, Rick is huge. He is very strong, very strict, and very black, and I want you to do everything he tells you to do ok, or he will kick your ass do you understand?”
“Yes Miss Scarlet. Hello Rick. I’m Barry.” HE said.
“Well from now on, for an hour a day, your ass is mine kid. Do you get me?” Rick said scaring poor Barry.
“Yes.” He said.
“YEs what?”
“Yes sir.” Barry said.
“Much better. Now lets get you started. Drop and give me 20.” Rick said.
I watched through the window as the black muscle stud molded and shaped my boy toy. Rick manhandled Barry and put his ego check, and put him in his proper place every day for an hour, and it turned me on so much to watch. I began to spy on them and massage my clit to an orgasm while they worked out and sweat in spandex.
Over the next week, I began to train Barry to perform the tasks I needed done. Everything from answering the phone and making appointments for me, to cooking me dinner and cutting the grass. I decided to give him a company car and he would pick me up at 7am, and take me to work, then drive me home at night at 9pm. Cook me dinner, do some household chores, and then stay at my home until I fell asleep. I wanted to own his time and his life. I wanted the only thing in his life was to be me.
It was time to take the next step.
“Barry, it makes more sense for you to just spend the night over here on the weekdays so you don’t have to drive back and forth. You can sleep in the guest bedroom. I insist.” I told him and he seemed a little uncomfortable but I had been working him hard and he agreed.
Now I began to tease this boy who was 26 years my junior. Each night I would strut around in next to nothing and watch his eyes follow me around the room. I would get into the shower and call out for Barry to come into the bathroom. I would tell him what clothes to get for me. Sexy panties, teddies, stockings, and he would go to my closet and get them, lay them out on the bathroom sink. I would dress in them, say goodnight, and listen to him in the guest bedroom while he masturbated.
“Gary, could you come in here please.” I asked. He came in my room wearing a very tight pair of boxer briefs. I was spread out on the bed looking very sexy. “Honey, I know you want to come to bed with me don’t you?”
“Yes Miss Scarlet. You are all I can think about.” He said.
“Well come over here.” I said. Gary walked over to me and I slowly slid down his tight briefs and unfolded his cute cock. I stroked it until it was erect and inspected his balls too. “Are you ready to learn how to please me?”
“Yes Miss Scarlet. What would you like me to do?”
“I want you to turn around so I can spank that beautiful behind of yours. That’s good. Now bend over a little for me and spread your legs a little. Oh that’s lovely.” I said as I began to spank his 19 year old bottom and watched it shake in front of my face. “now Barry, I want you to get on your hands and knees and begin to kiss my pussy.”
I watched as this boys eyes looked up at me so submissively as he nervously began to lick my clit. He was actually very good but I didn’t want him to get an ego. I began to instruct him to how I liked it. I made it difficult for him but I began to cum very shortly. I kept him down there until I came 3 times, all over his beautiful boyish face.
“You can add that to your daily duties Barry. Now go on back to bed and finish masturbating. I need to get some sleep.” I said as I rolled over. I wanted to feel my new boy toy inside of me so badly, and grip his gorgeous butt cheeks and plunge his cute cock into my tight pussy, but I knew that I had to time it right or else Barry but get an ego about it, or start thinking he owned me, like most naturally do. But it was I who needed to feel that I owned him. Which of course I did.
I began to increase the amount of demands I had on Barry at work. I worked him hard all day long. If he finished early, I made up more stuff for him to do. I needed to break down his spirit and keep him busy. This way it was easier to control him and keep him out of trouble. I was the cause of his pain in life, but also his pleasure.
Each night I would make him perform oral sex for me and when I was fully satisfied, I would allow him to masturbate in front of me. One night I was feeling very kinky and lubbed up his young virgin ass and slipped a dildo in there while he masturbated. He seemed to be overcome with ecstasy as I turned on the vibrator while inserted in his ass. He became addicted to this and asked for it every night. It became a little treat I would give him.
Finally, Barry;s desire to fuck me was overwhelming for him and he became obsessed about it. I told him that although I was 45 years old, my biggest fear was that I would get pregnant. So I told him the only way I would have sex with him was if he got a visectamy. Barry refused the idea at first and I didn’t blame him because he was only 19 and had his entire life ahead of him. But if he truly was going to be mine, this would demonstrate it for me.
It was torture for him. I teased him constantly at work now. Wore the sexiest clothes, and flirted with everyone while he watched. He knew he could have me, but to get me, he had to have the surgery. I stopped using the dildo with him and refused to let him masturbate in front of me for 3 days. And on the 4th day, Barry told me he wanted to have the visectamy.
I will never forget picking him up at the doctors office and the look on his face. He looked like he had just been castrated. He cried on my shoulder as I held him and comforted him. He cried all the way home. And he was a real mess until his balls finally healed and I took him to bed for the first time.
“My sweet Barry. You have demonstrated to me the level of commitment you have to servicing me and my pleasure. You have been very loyal and done everything I asked of you. And now, I am going to give you a raise. But first, I am going fuck you.”
I slowly unwrapped my boy toy. I laid him on top of me and slowly sunk his cute little cock into my throbbing cum soaked pussy. I began to cum uncontrollably as I moved Barry’s hips in the motion that I prefered. When he began to go at his own speed, I stopped and slapped his face gently and told him, “NO” just like a dog. And in no time, he learned to take cues from me. And he began to get off on my pleasure only and we began to cum at the same time, every time.
I had never had sex this good. I mean he didn’t have a large penis, or lots of muscles. He didn’t even have a lot of skills in bed either. But there was something about he dedication to me and my pleasure that got me off harder and faster than I thought possible. He didn’t cause static or have motives other than to please me. It was pure, the way it should be.
Or maybe it was the fact that I was 26 years older than him. I still don’t know for sure but I know that having that kind of amazing sex began to change my entire life. I laughed more, took myself less serious, felt more satisfied in general, and had an overall better outlook on life.
Well, I began to allow Barry to share my bed with me. Each morning he would wake up and cook breakfast for me while I slept in. When the food was done, he would begin to eat my pussy and I would wake up having an orgasm and looking at this beautiful boys body and face going to work on my snatch. Then I would eat, he would drive me to work, and I would give him a to do list. At night, he would cook me dinner and then we would fuck for at least an hour.
Folks, it doesn’t get much better than that.
T
he best part was going out to parties with him on my arm. All the women my age would stare, gossip, and ask me a million questions about him. They all wanted one of their own.
I would have pool parties and have Barry cook and serve us drinks in a thong. They would spank him as he bent over to serve them a margarita.
“How much are you paying him?” They would ask. “Is he your son?” “can we borrow him for a night?” “Oh come on, how much to borrow your boy toy?”
All powerful women should have a boy toy. I know that now Barry is perhaps the most valuable thing I own. I wish I had thought of this sooner.
Boy Toy For Mature Woman Femdom Sex Story written by Miss Scarlet.
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?
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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.
Dominant Domme Mistress Dominatrix Woman Loves To Dominant Submissive Sissy Sluts and Submissive Men, Boys, and the Like. April 3, 2008
Posted by sexstory in Black Sex Stories, Cheating Wife Stories, Crossdressing Sex Stories, Domination Sex Stories, Femdom Sex Stories, Kinky Sex Stories, Older Women Sex Stories, Sex Fantasies, Sex Stories For Women, Sex Story, Sexual Health, Straight Sex Stories, Taboo Sex Stories, True Sex Stories.Tags: submissive, man, dominant, woman, domme, mistress, dominatrix, male, submissive male
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Dominant Dominatrix, Mistress Domme, confesses why she loves a submissive sissy male, written by Mistress Domme.
Hello all you submissive sissy sluts, men, queers, fags, queens, and sex slaves, I am Mistress Domme, your dominant dominatrix and I am here to take control of your sexuality and unleash your inner sissy fag and fulfill her naughty little submissive desires.
But before we get into the action, I wanted to explain a little bit about why I love being a dominant dominatrix mistress, and more importantly, why I love you submissive men so much.
At an early age, I was fascinated with power and often fought with any powerful man in my life, including my own father. I seem to have just been made this way and looking back I feel sorry for these men because I was really just being a little bitch and didn’t deserve the power and control I sought. But over time, as I matured into a wise woman, I learned from powerful people and learned how to be submissive to become more powerful. Until I finally reached a point of understanding and appreciation of both roles.
I was born naturally dominant and nothing turns me on more than a submissive man who can suspend his masculinity and ego enough to turn over his power to me. If he was not a man in the first place, then there would be no excitement in the role play and power exchange. A submissive man needs to give up control and it turns him on. And a dominant woman needs to take control and it turns her on. We might be the minority in the world, but we do exist and we both know how exciting this can be.
If you are a submissive man and feel ashamed of your desire to be dominated, then I am here to tell you that you should never fell that way. It’s the ying to my yang, the salt to my pepper, and the missing piece to my puzzle. You are also in good company. Over the years I have had the joy of dominating ever type and class of man you could think of, from every race and culture as well.
In short, nature made me a dominant woman and I need a submissive male to find my ultimate pleasure. Just as you were created by the same nature, the submissive male, and crave the dominant female to release your secret and taboo fantasies. Together we make them all come true. Together we complete the puzzle, we make each other whole, and we get off, over and over and over from finding and enjoying each other. We need each other and I cherish you just as much as you do me.
That’s a little secret in the profession of a dominatrix but it’s very true for the natural domme woman. Another fact that I always find a little sad, is that so many married men have to find a professional dominatrix and go outside of often a good marriage simply because they are afraid to share their submissive longings with their partner. Or worse, they express their fantasies of being dominated and their partner does not understand. She may be offended or think they are gay and becomes threatened.
I do not take pleasure in being the “other woman”. In fact, I often try to get my submissive males to open up and express their secret fantasies with their partners. And sometimes this does work. They needed me to tell them that it’s ok to do that and that perhaps other women will enjoy it as I do. But this is the exception.
But let me just say this. If you are a woman who is married to a man who has expressed some interest in being submissive during sex, or wants to try on your underwear, or anything kinky where his feminine side may be trying to expose itself to you, do not worry. In fact you are very lucky in many ways. Chances are your man is not gay, but more of a man than most. He is a whole human being that wants to experience both sides of the coin. And that can equal a better partner for you.
Even if he expresses an interest in being with another man, that rarely means he would rather be with a man than you. He is just a super sexual being and has a large appetite. Not all, but most adult men already know if they are straight or gay by the time they go through all the trouble to go to bed with you. Chances are if he fucks you once a month or more, he likes women and he likes you. Men can have very different sexual desires and needs than women, that is just how nature made us. It can scare a woman who does not fully understand this. But I promise every woman who reads this that if they go along for the kinky ride of their submissive men, they will enjoy it as much, if not more, than their kinky man. If you think you might have a submissive partner, ladies…….you have struck gold. GOLD!!!
But in the end, most women don’t understand, and most men are afraid to ask, and therefore I, as the dominant dominatrix mistress, stay in business and never run short of clients.
I am in my early 40’s now, and I have had some clients for 20 years. The need for the submissive man to let go of his power and control and submit to a dominant woman sexually who understands, does not go away. It’s like herpes. So if you are a submissive male and you are not getting your needs met, better find somewhere and someone and someway that you can. Either ask your partner, or find a new partner, or come find someone like me, or you will go through life always wishing and fantasizing about something you want. Life is far too short for that shit.
And if you happen to have a submissive man who has expressed these desires, and you have not explored them with him, or you have and you didn’t like it, then it may be time to go your separate ways or allow him to go outside the relationship to meet these natural born turn on’s.
So little boys and girls and little sissy sluts and closet dressers and wanna be queers and queens and fags, I just want you to know that if you have a penis, and you have submissive desires, that you are wanted and needed and appreciated. Even by a beautiful dominatrix and powerful dominant woman like myself.
We love you!!! And need you!!! And yes, even miss you!!!
Don’t change a thing!
Your Dominant Dominatrix,
Mistress Domme
Check back to this website (kinkysexstories.org) for kinky sex stories I have to share with those lucky submissive sissy boys out there who crave it.
You have my powerful permission to submit and submit fully to this article and post on kinkysexstories.com
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
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.
Sissy Slut Training Crossdressing For Sissies Lesson Part Two July 12, 2007
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, Sex Fantasies, Sex Stories For Women, Taboo Sex Stories.7 comments
Sissy Slut Training Crossdressing For Sissies Lesson Part Two.
Written by Miss Ivy for kinkysexstories.org.
Sissy slut training, crossdressing for sissies, free lesson part two.
Hello my pretty little sissy slut. I hope you have completed lesson one for crossdressing sissy sluts and you are wearing your pretty pink panties as I have instructed. Doesn’t it feel wonderful to be pinked and pantied and in frillies? How freeing and liberating for the sissy slut. Are you getting excited? You are ready to embark on a fabulous journey to make your sissy slut desires and fantasies come true. I am excited for you and it makes me wet thinking about you sitting there in your chair, wearing pink panties that I instructed you to buy.
Always remember that your mistress has both of your pleasures in mind. And that when she asks you to do something, it is because she wants to get you one step closer to living out your sissy slut cravings. There is simply nothing more wonderful to taking the hand of a submissive sissy, and guiding him to the world of womanhood. Each step along the way is a release and an orgasm for both parties involved. It is a very special relationship and your dominant mistress knows that better than anyone.
So, my pretty feminine sissy boy, today’s lesson will continue your slut training. Now you must take that next sissy step and reach out. You must find a dominant woman and admit your sissy slut desires. It is the only way to continue. As the saying goes, “ two heads are better than one.”
So, it’s up to you to seek out a pleasure partner in your community. If you are a married sissy slut, then you should tell you wife about your new pink panties. It may take her awhile to accept it, but you might be surprised at how much it turns her on. If it’s too scary to tell your wife that you want to be her little sissy slut, then you will need a mistress or a dominant woman. I have found that an older woman, and a younger man, make the best sex partners when dealing in the sissy slut world. It’s a natural combination and has worked for years.
The absolute best way to find a dominate woman to help you transform into a the sissy slut that you are, is by joining an online dating service. Here you can speak freely about your desires, and get the chance to try out a few different women. Also, you can let her know up front that you are a sissy slut and seek a mature and kind soft hand to help you with your sissy transformation. Perhaps you will find a dominant woman who lives near you, or perhaps you will choose to have an online relationship at first. Either way, the most important thing is that you admit to a woman that you are indeed a soft and sensitive sissy slut and seek to be trained and transformed. Just thinking about that makes me get excited, as I am sure it will do the same to a wide variety of other dominant women out there. Trust me. Sign up with an online dating service and in a short time, you will find your dominant mistress.
I also want to add that sometimes, a shemale or transsexual may be the preferred sex partner for your sissy slut training. Since most shemales began crossdressing and being a sissy slut at an early age, they can also help with your transformation. They can offer a firm, yet sensitive hand, as well as having the necessary hardware to train you properly. It’s your choice.
Here are three online dating services that I recommend for finding a mistress or play partner or older dominant women who would love to find a submissive sissy slut who wants to crossdress.
Recomendation for finding a kinky sex partner.
Recomendation for finding a dominant woman.
Tips to Find A dominant mistress to train a crossdressing sissy slut.
- Be able to communicate using the femdom language. Know what the terms and vocabulary is. One way to discover this better is to read sex stories dealing with a sissy slut and your fetishes.
- Know your limits. You should think through what you are willing to do for you play partner and what you are not. Yet be open to grow and try new things with your dominant lover.
- Think it through. Let’s pretend that you find a sex partner, and you finally meet with them and live out your role play fantasies. When it’s over, will you want to continue and are you in it for a relationship or just to have a kinky mistress. If you are not interested in having a relationship with a dominant woman, then perhaps you should find a local escort mistress for the one time experience.
- Be honest and direct about what fantasy you want to play out. Tell your potential mistress about your secret pink panties that you wear and your submissive needs. Explain to her that deep down you are a sissy slut trying to come out of the closet and that you want her help.
- Be ready to surrender yourself to a dominant woman. Know that she has needs too and will want you to be docile. This is a role reversal contrast to society. Therefore you may bring with you tendencies to dominate a woman. If she is good, she will be able to train that out of you and help you to discover how wonderful it is to surrender to a dominant woman. She will keep you coming back for more and you will have to trust her methods.
Finding a real mistress or kinky play partner is important. You only live once and living out your sissy slut fantasies will make you a more happy person. You may yourself very excited about your life and your new adventures. So do not hesitate or wait. Take the steps to live out your dreams and desires, no matter how taboo they may be. Chances are that if you do, you will find someone out there who is also excited about the same kinky things that you are and you could easily end up having the most erotic and sexual experiences of your life.
Happy hunting submissive sissy slut. There is a dominant lover out there waiting for your sweet submissive self right now.
Sissy Slut Training, Crossdressing For Sissies, Free Lesson Part Two.
This article was written by Miss Ivy for KinkSexStories.org
Bi Sexual Boyfriend Sex Story. First Time With Gay Muscle Stud. July 9, 2007
Posted by sexstory in Bi Sexual Sex stories, Gay Sex Stories, Group Sex Stories, Kinky Sex Stories, Older Women Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Three Some Sex Stories, True Sex Stories.3 comments
Bi Sexual Boyfriend Sex Story. First Time With Gay Muscle Stud.
I am a 45 year old woman and I am dating a 25 year old man. We men online at a good dating service and I was attracted to him because he was so cute, and a little feminine and very sexy. Our sex was incredible from the start and was for both of us, the best sex we ever had. We both shared a love for drinking red wine and watching movies and soon, I would find out we both shared a love for muscle studs.
After about 3 months, my boyfriend kept asking me to dress him as a woman and at first I was a little concerned but we ended up having even better sex. It was wonderful how we would go shopping for clothes together and then come home, dress up, and have sex. I began to crave to dress him up as a little sissy slut. I made him look beautiful and any man would be lucky to be with him.
I began to rent gay porn for him and we would dress up as woman and then watch men having sex with each other and talk about how sexy they men were. I then bought some sex toys online. I bought a butt plug, a strap on dildo, and a double headed dildo. My boyfriends butt was very tight so I made him wear the butt plug around the house for a week until it stretched his ass out wide enough that I could use my strap on cock on him.
I was surprised at how much all this turned me on because I never used to be like this. I was so dominant and he was so submissive and sweet, and together we were perfect and having incredible sex. I couldn’t stop. I kept fantasizing about seeing him with another man. I made him look at gay porn all the time, and I made sure I trained him properly about how to suck a cock right. I also made sure I fucked him in his ass every night.
My sissy boyfriend craved to be fucked in the ass with my strap on. Even during regular sex he begged me to finger his butt which always made him cum so quickly. I knew that my boyfriend was bi sexual even if he didn’t know it but I wondered if he was gay. He had never been with a man before but he often fantasized about it. I thought about this a lot and devised a plan to find out if he was gay or not.
 I found a very sexy muscle stud at my gym who was a personal trainer. His name was Byron and we became friends. I suspected he was gay and I was right. Then I told him all about my sissy bi sexual boyfriend and how I was trying to find out if my boyfriend was gay. I asked him if he made house calls and he said he did. So one day, I dressed my boyfriend in a tight white bikini thong with tie strings on the side and then called the muscle stud over.
“Baby, I want you to meet Byron. He is going to be your personal trainer. This is my early birthday present for you. Twice a week, Byron will come to the house, and you two can work out together. Now run along and do whatever Byron wants you to do.” I said.
I secretly watched as my sissy boyfriend worked out with Byron in the backyard. Byron put my boyfriend in all kinds of sexual positions and was holding and touching him. I could tell Byron was enjoying it and that made me happy. The question was, was my boyfriend enjoying it.
I went into the backyard to have a closer look. Byron had my boyfriend laying down on his back doing sit ups with his legs spread wide open. Byron’s huge bulging cock was firmly up against my boyfriend’s ass while is muscular arms held down my boyfriends feet. If my boyfriend got a hard on, his penis would stick out of his white bikini bottoms. I figured it was a type of gay thermometer.
“How’s it coming boys?” I asked.
“We are almost done.” Byron said. “It’s time now for the rubdown.”
I watched as Byron began to apply lotion all over my boyfriends back. Byron positioned himself so that my boyfriends head was faced directly at Bryon’s large bulge in his tight black shorts. I watched as my boyfriend stared at the large bulge in front of him. Was he getting turned on? After a few minuets, I gave Byron a wink that meant it was time to find out what effect all this was having on my boyfriend.
“Ok, now your front. Lets roll you over.” He said.
And sure enough, when Byron rolled my boyfriend over, his penis was sticking out of his bikini thong, straight up in the air. He was very embarrassed.
“I see that you are enjoying your new personal trainer aren’t you?” I said. “Are you attracted to Byron sweetie? It’s ok, I want you to be.” I told my boyfriend.
“Yes, I am attracted to him.” My boyfriend admitted.
“Why are you attracted to him sugar? What do you like about him that is turning you on so much?” I asked.
“Well, he is very strong and big and his has a big bulge.” My boyfriend said shyly.
“Would you like to see what is beneath his bulge?” I asked.
“Yes I would.” My boyfriend said.
I reached over and pulled down Byron’s shorts and out popped a gigantic cock. It was at least 7 inches long and 3 inches wide. Byron’s cock was a work of art and would have turned any straight man gay.
I stroked the muscle studs cock, right in front of my boyfriends face, until his cock was almost completely erect.
“Would you like to know what this magnificent cock tastes like?” I asked my boyfriend.
“Yes but I am shy.” My sissy boyfriend said.
“Don’t be shy, I am here to help you. Just open your pretty sexy mouth and I will place it in there for you”. I said as my pussy began to get very wet.
I placed Byron’s cock inside my boyfriends sissy mouth and he looked up at Byron and I with very submissive eyes.
“Now show Byron how well I have trained you to suck a real mans cock.” I said.
I watched in ecstasy as my fantasy was coming true before my very eyes. My boyfriend’s mouth was engulfed by the super sized cock and he sucked Byron like a champ.
I placed one hand on Byron’s balls, holding his big cock for my boyfriend to suck. I placed my other hand on my boyfriends sissy penis and began to stroke it while he sucked the muscle stud off. I was so turned on by all this I forgot that I was supposed to be deciding if my boyfriend was gay or not. If he was gay, I think that only made me want him more.
“Now my little darling, my sweet sexy submissive boyfriend, Byron is about to cum. You have done an excellent job sucking his cock. I want you to swallow all his cum down your sissy throat until every last drop has spewed from his cock.” I instructed my boyfriend. And he did.
The three of us got into the shower and I insisted that my boyfriend wash Bryon’s body from head to toe. I watched as his hands explored all over the muscle studs perfect form. I began to play with myself and brought myself to several orgasms. My boyfriends cock had been consistently hard ever since he little rub down. I had never seen him so excited before.
We got out of the shower and I personally toweled the two boys down. They stood there naked and looking at each other.
“Now honey, I want you to let Byron kiss you. Don’t be shy.” I said as my boyfriend leaned into the muscle stud. Byron forced his tongue into my boyfriends mouth and grabbed him by the ass as my boyfriend’s hands explored all over the muscle studs back, legs, and chest.
Soon Byron’s wonderful cock was rock hard again. I started to stroke my boyfriends cock, and the cock of the muscle stud together while they kissed. I was about to have another orgasm.
“Ok my beautiful boys, it’s time to lie down on the bed.” I said. Byron and I each took my boyfriend’s hand and led him to the bed. I lay him down gently on his back, then positioned Bryon a the foot of the bed. I helped Byron lift my boyfriends legs into the air and took his big dick and began to tease my boyfriends ass with it. I was having way too much fun.
I got the lube tube and squirted a healthy dose of lube all over the gigantic cock, and the sweet virgin sissy ass of my boyfriend. Then I took Bryon’s cock and placed it into his ass.
“There honey, that’s what you have been wanting now for so long isn’t it?” I said.
“Oh yes.” My bisexual boyfriend replied. I then leaned down and began to kiss my boyfriend as Bryon began to thrust his cock deep into him. I pinned back my boyfriends arms while I kissed him gently and talked dirty to him.
“Doesn’t that feel good. Oh you like it up the ass so much don’t you?” I said.
And then suddenly, my boyfriend came all over his stomach without anyone, or anything even touching his penis.
“Aww sweetie, you came so fast. You love this don’t you. I knew you would. But now you are just going to have to lie there while Byron fucks you some more.” I said.
But within a minute, my bi sexual boyfriends cock was hard again.
“Baby, look how much you like this. I have never seen you get so hard, so quick after you come with me.” I said.
Byron turned my boyfriend over placed him on his hands and knees on the bed. He bend him over and began fucking him in that position. I took out a large vibrating dildo and shoved in into my pussy as I watched Byron thrust his gay cock faster and faster into my boyfriend’s tight ass. Byron reached around and began to stroke my boyfriend penis faster and faster. Then Byron came into my boyfriends ass, while my boyfriend came in Byron’s strong muscular hand. They both cried out in pleasure. Watching my bisexual boyfriend having his ass pounded for the first time with a gay muscle stud made me have an orgasm too. We all came together.
I kissed my bi sexual boyfriend deeply and rubbed his head and asked, “Well sexy, now that you have finally had sex with a man, which do you like better. Boys or girls?”
“Both.” he said.
Bi Sexual Boyfriend Sex Story. First Time With Gay Muscle Stud written by Cynthia.
