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.
Dominant Wife Seduces Sissy Crossdressing Husband Into Cuckold Threesome Love Triangle July 13, 2007
Posted by sexstory in Cheating Wife Stories, Cockold stories, Crossdressing Stories, Cuckold Stories, Domination Sex Stories, Femdom Sex Stories, Group Sex Stories, Kinky Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Three Some Sex Stories, True Sex Stories.1 comment so far
Dominant Wife Seduces Sissy Crossdressing Husband Into Cuckhold three some love triangle. The sex story of a dominant wife and her need for a cuckold husband to live out her ultimate sex fantasy. Written by Misstress Diane.
Hello, my name is Diane and I am a dominant wife married to a sissy crossdressing huband. I want to tell you the true sex story about how I managed to dominant my husband so much, that be agreed willingly to be my cuckold husband. Meaning that I place him in bondage and force him to watch me have sex with other men from time to time. And sometimes, I force him to have sex with other men too. Here is how it all started.
When I married my husband, I already knew that he was in the closet and liked to crossdress as a women during sex and before and after too. This fact actually made him more attractive to me because my nature is to be in control and very dominant. I have learned from the mistakes of my past and knew that this type of man worked best for me. He allowed me to dominate him, and he even enjoyed it. We started our role play sex slowly, and in time, he began to ask me to use a strapon dildo, as well as other anal devices for him. He loved it and I enjoyed the power of it. I also enjoyed having so much control over him.
I don’t know if all men enjoy anal sex as much as my sissy cuckold husband, but I can tell you that the day I used the strapon on my husband was the day that everything changed. He became completley submissive to me and doted on me constantly. He explained that all his life his sex fantasy was to be fucked with a strapon by a dominant women but he was always too afraid to tell anyone. And now that I was doing it to him, and we were both enjoying it, he felt totally at my mercy. In short, he had become a slave to my strapon and the taboo pleasure it gave him.
Our marriage was better than ever. There were no more power struggles. I mean none. He became a genius at making me happy and doing anything I wanted within reason. For awhile, I had thought I found the perfect husband, and I really think I did. The perfect cuckold husband for me anyway.
But I noticed something else after I started dominating with my dildo. I noticed that I began to lose a little respect for him. I mean I had him in every type of vulnerable position a man can be in. I had my way with him everywhere. And he would also bother me from time to time by being so perfect. I started thinking less of him and his sissy slut ass. I still loved him, and enjoyed our unique relationship, but I felt I needed something more. I needed a real man. But how would I get the sissy husband to understand.
Finally one day, we had a talk.
“Listen baby, I want to tell you something. I think it’s wonderful that you enjoy crossdressing, and how you are so feminine, and that you take my strapon each and every night. But I feel as though I need to be with a real man right now. ” I said as I watched my husbands heart break and he burst into tears like the little sissy that he is.
“Please no Amy. Please don’t say that to me. You know I am not a physically strong man, but I love you so much.” He said. “It would kill me if you had sex with another man. Especially a stronger man perhaps with a larger dick.”
“Well dear, you know how I dislike it when you challenge me in anyway. If you do not agree to this, I will divorce you. You can cry all you want but I AM going to have sex with another man. A real man. ” I said and I walked off and made him sleep on the couch for several days.
Eventually my husband came to me with an idea.
“I know I can’t stop you from being with another man. But at least allow me to watch you cheat on me. This way, I will at least know what you are doing and not feel so badly about what I don’t know.” He said.
He had a wonderful idea. I thought about it and said, “Ok dear. I will let you watch me have sex with another man but only if he says it’s ok. Otherwise, I will make you wait in another room and you can listen if you want but that’s all.” I said.
“Oh thank you. But I am worried that perhaps you will want to get divorced and be with the other man if the sex is good.” He asked me puzzled.
“Don’t worry my sissy slave. I prefer your little sissy ass and little sissy penis and little sissy brain to be married to. But from time to time, I need fresh meat to throw me around and make me feel like a real women. Whomever I will find, it will just be sex. I want you to understand this.” I said.
Feeling relived, and almost prideful of my kind words, my sissy husband agreed and held me tightly.
“Now, I want you to help me to pick him out. We are going to go and sign up at the country club and look for him there. I want someone who works out a lot. I would prefer a young muscle stud. A real stallion that I can ride all night while you watch. This is turning me on just thinking about it. Drop your panties sissy boy, momma is getting excited.” I said.
My submissive husband and I began going to our local country club looking for the perfect stud. We would drink at the outdoor bar and I would point out hot men for me to fuck and get his opinion on it. The power and control I had doing that was intoxicating and thrilling.
“Dear, what about that young sex stud there? Do you see him? No, not him silly. Look, there, the dark skined man playing tennis with the huge bulge in his shorts. Do you see him now? Yes, that’s the one. Look at the rock of an ass he has on him. Now that is a real man. I can just imagine placing my hands on his tight ass and thrusting his hips into my pussy. He is so rugged. Like the Marlboro man.” I would tell my husband who would be more than happy to listen. I think the men were getting my husband hot too.
Finally, there was one man that I wanted, and my husband was ok with. He was incredibly sexy and surely had many girlfriends. He was tall, very muscular, and had a mustache. I asked my husband to follow him into the mens room to check out the size of his cock. My husband came back and said,
“It’s three times the size of my cock.”
“Well, sweetie we both know that is not saying very much.” I laughed.
“Don’t worry, that man is hung like a race horse.” He said.
I found the courage to walk up to him and ask him his name. Tyrone. I asked him if he was married and he was not but he said he was seeing someone. I asked him if he was interesting in seeing me right now, and I grabbed him and kissed him forcing my tongue into his mouth. I slid my hand up his legs and took hold of his gigantic horse cock and squeezed a little. He started to become erect and I could feel that monster in his pants grow. He couldn’t help himself and grabbed my hips with his large and powerful hands and thrusted me towards him. It was all chemistry and I knew he would be coming home with me.
“I really shouldn’t” Tyrone managed to say.
“Look sexy boy, I don’t want to marry you, or ruin what you have going with someone else. But I need a man like you very badly right now. You will not be sorry, I promise. It will be just this one time, unless you chose to continue. Just call me in two hours if you still interested. I will be waiting for you.” I said, gave him my card, and went home.
Part 2 of dominant wife seduces sissy crossdressing husband into cuckold threesome love triangle coming soon.
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
Sissy Slut Training, Crossdressing For Sissies Lesson One. July 10, 2007
Posted by sexstory in Crossdressing Sex Stories, Crossdressing Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Kinky Sex Stories, Role Play Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Taboo Sex Stories, True Sex Stories.8 comments
Sissy Slut Training and Crossdressing For Sissies. Mistress Ivy Gives A Free Lesson In Sissy Slut Training and Crossdressing for Sissies.
Welcome to the world of sissy slut training and crossdressing for sissies. I am Mistress Ivy and am thrilled to be your guide into the kinky world of femdom.
Perhaps you are a submissive male who fantasizes about being turned into a sissy slut and crossdressing. If you are, there is no reason to feel ashamed for these naughty and taboo desires. You may be surprised to find that there are plenty of dominant women out there who share your desires and secretly fantasize about playing with a submissive sissy boy, just as bad as you secretly long to be her sissy slut. You are not alone. The world of femdom and female domination, and the need for a man to surrender to a strong women in the bedroom is as old as civilization itself.
Where does one begin?
How does one take the deep plunge into the sexual fantasy world?
Well, I am Mistress Ivy and have been a dominatrix mistress for the sissy slut in the world of femdom for almost 20 years now. And there is still nothing that gets me hotter than to take a man, show him his more feminine side, and transform him into my personal sissy slut.
The first lesson to learn in your sissy slut training is how to shake off your fears and concerns about what people might think of you, and what society feels about a man who has these desires. The reason why being a sissy slut is just your fantasy is because of fear. And although it is true that society treats the male sissy slut as a taboo subject, it’s also true that your sissy slut urges could bring a world of pleasure and enjoyment to more than a few women out there.
So, the best way to concur your fear and anxiety about being transformed into a dominant woman’s sissy slut is to get your pretty little sissy penis into a pretty pair of pretty little pink panties. Chances are you might already have a pair of panties stashed around your place. But it’s important to actually purchase new pink panties for yourself as a first step towards making your fantasies and sex stories into reality and shared pleasure.
Shop for your sissy panties online. It saves a little time, and you don’t have to feel so embarrassed at Victoria’s secret. You may want to go out shopping with your future kinky partner, but we are getting ahead of ourselves.
Your first lesson in your sissy slut training is to buy panties. Pretty pink panties. When they arrive, take off all your clothes and place your pretty pink panties over your sweet butt cheeks, and your sissy cock. Then return here kinkysexstories.org and you will find your second lesson in your sissy slut training.
Happy panty shopping you little sissy slut. I am waiting
Sissy Slut Training, Crossdressing For Sissies. Mistress Ivy Gives A Free Lesson In Sissy Slut Training and Crossdressing for Sissies.
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.
Forced To Feminize. Crossdressing With My Step Mother part two. July 8, 2007
Posted by sexstory in Crossdressing Sex Stories, Crossdressing Stories, Cuckold Stories, Femdom Sex Stories, Forced to Feminize, Incest Sex Stories, Kinky Sex Stories, Older Women Sex Stories, Role Play Sex Stories, Sex Fantasies, Sex Stories, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, True Sex Stories.5 comments
Forced To Feminize. Crossdressing with my step mother part two.
This is the second crossdressing story about how I was forced to feminize and began crossdressing with my step mother.
After the night I feel asleep with my step mother in her bed wearing her panties and bra and lace teddy, we woke up and she finished washing my regular clothes and dressed me back as a boy.
“Today we are going shopping.” My step mother announced.
As we were driving in her car to the shopping mall, my step mom asked me to find her lipstick in her purse.
“Now watch closely how I do this.” She said. “Now I want you to put a little lipstick on your lips too.” She said.
“No way.” I said. “ I’m going to look like a girl at the mall and everyone will see me.”
“Now listen, every movie you have ever seen, the actors are wearing lipstick and lots of make up. Just rub the pretty lipstick on your pretty mouth and accent your full luscious lips. Don’t be shy.” She said.
I did as I was told but felt funny about it. However it tasted pretty good and smelled good too but it made me feel very self conscious at the mall.
My step mother began buying clothes for herself and I was forced to watch as she dressed up in different outfits. I must admit she was a very sexy woman. She had curves in all the right places. She had an air of dominance about her and I always felt very safe around her. She also was good with people. I loved her deep and sexy voice. It almost seemed like each work out of her mouth was actually saying, “I want to do naughty things to do little boy.” I was young and a virgin and enjoyed each moment of her attention
She began to pick out lingerie for me, having me try it on and then showing it to her. She even asked one of the pretty young clerks for her opinion.
“Now how do you think my pretty young sissy girl looks in this one….and this one…..and this one?” She would ask the clerk who giggled at me and looked me over.
After buying skirts, blouses, panties, bras, shoes, and even girl lingerie, my step mother dragged me by the hand into what appeared to be a homosexual clothing store. She handed me over to a clerk and said, “find lot’s of tight and white for my sissy boy.” And then she left me there for about an hour while this large muscle stud dressed me in tight white clothes. When she came back, we hauled all our stuff to the car and went back to our house for a fashion show.
“Now my little sissy boy, I want you to dress me up first. I want you to pick out your favorite outfit and dress me up. And if you are lucky, I will do the same to you.” She said.
I undressed her and her big tits spilled out. I could not keep my hands off them and was slapped across the face for it. I stuck to the task and dressed her in my favorite outfit. It was a tight fitting dress, with leather boots and a large cleavage area. I choose white lace panties for my step mom and a big white bra for her big tits.
“Perfect. You have choosen well my little sissy boy. Now it’s your turn.” She said and she picked out very slutty clothes for me to wear that evening. She seduced me into the bathroom and applied lipstick and makeup to my face and then put me over her lap for my evening spanking.
“You are my good little crossdresser aren’t you?” My step mother said. “From now on, you are going to wear what I want you to wear each day, and that includes all those tight clothes for boys I bought you. The boys and girls are going to love you at school. You trust me don’t you, and I know you love all the attention mom is giving you lately.”
That night, we ate dinner as I was dressed like a little sissy slut girl. In some ways, I enjoyed it, but I also felt a little strange at first.
“In time my sweet sissy, you are going to enjoy wearing girls clothes. In fact you are going to enjoy it so much, you may even decide to be a girl. But never mind that now, mother has plans for you this evening.” She said and led me into the bedroom again.
My step mother tied my hands behind my back and knelt me on my knees. “It’s time I introduce you to my very special friend. It’s called cock. This is my cock and you and it are going to get along just perfect, I know it. But you are not allowed to touch it yet because you have not learned respect from it. So we are going to watch a movie that will explain to you all about cock, and what to do with it.” My step mother said and she left me on my knees, with her cock in my face, as we watched a porno about a woman who learns to suck cock for the first time.
The cock sucking porno movie made me hard. It was beautiful to watch the woman place her virgin lips on the large cock. My penis was not as large as his and I felt insecure.
“I’m not as big as him.” I told my step mother.
She laughed at me as said, “Silly girl, you don’t need your cock. All you need is that little clitty between your legs, and your sexy little butt as well as your pretty painted mouth. That big cock will do the rest. I want you to keep watching how she sucks that large penis because you are going to suck mine now.” She said.
My step mother plunged her cock into my mouth as I tried to stop her but because my hands were tied, there was little I could do.
“Oh stop fighting it. I know you like it, I can see your little girl clitty getting hard. Just take the cock into your mouth. You may find it a wonderful and peaceful experience. It’s very important to train you right from the start. That’s good sissy, just like that, nice and slow and back and forth, just imagine how you would want someone to suck on your dick.” She said as I took the cock as deep into my mouth as I could.
“I have forced you to feminize quite well in such as short time. It’s time for us to go to bed now, we will have company over tomorrow and you can show them what you have learned today my sweet little sissy.” My step mother said.
And as usual, she forced me to sleep in her bed with her. She began to leave my hands tied up as we sleep and occasionally during the night and in the morning, I would feel her hands dig into my panties and play with my cock until it was hard. Sometimes she would tease and play with my asshole too which would only make me more excited.
Yes, I had been forced to feminize, and crossdressing with my step mother was opening up new worlds to me.
Forced To Feminize, Crossdressing With My Step Mom. July 7, 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, Sex Stories For Women, Taboo Sex Stories, True Sex Stories, Underage Sex Stories.15 comments
Forced To Feminize. Crossdressing With My Step Mom. Part One.
By Tyronne Wilson.
This is a real and true story about how I was forced to feminize and began crossdressing with my step mom. I have wanted to share this for a long time.
It all started when I was a teenager. My father remarried a beautiful blond woman named Suz. Shortly after that, my father died and I was left with my step mother to raise me. My step mother was a very powerful and strong dominant woman who was a bit of a feminist. She was a large and voluptuous woman in her mid 40’s and although I know she loved me, she would often tell me that she wished she could have had a daughter before my father died, but instead she was stuck with me. My step mom and I lived in a large house in Seattle overlooking the city and she was very active in women’s organizations so there were always social gatherings, parties going on, and beautiful strong women in our house.
My step mother pulled me out of all of the sports I was involved in and began to take me to the women’s groups and social functions instead. Soon, all my friends were older woman who were always telling me how cute and sweet I was.
Looking back, I can see now that my crossdressing started the day my step mother gave me a pink thing panty to wear as a bathing suit. It was summer, and we had a nice pool in our backyard and all the women were over swimming and sun bathing. I remember I got to put sun tan lotion on them all and it gave me a huge hard on.
“Sweetie,” my step mother said. “Your bathing suit is ugly. Let’s go inside and get you a better one.”
We went into her bedroom and she abruptly yanked down my swim suit.
“Mom, I’m naked. I’m not a little boy any more.” I told my step mom.
“Quit your wining. I have seen your penis before. Now stand there and let me put this cut little swimsuit on you.” She said as she spread my legs apart and I stepped into the pink thong bikini.
“It’s a good thing you are not too hung. If your penis was any bigger it would be coming out of your thong. Now turn around and let mom look at you. Very nice. Your butt looks good in that pink bikini. All the ladies are going to love you in it.” My step mom said and she took me by the hand and led me into the backyard where all the ladies were swimming and sun bathing.
“Ladies,” my step mom announced, “my sweet pretty boy here has found a wonderful pink bikini to wear for you today. I am going to pass him around so he can put sun tan lotion on all of you and you can put lotion on him too if you like. Think of him as your personal assistant and if he does not do as you wish, you have my permission to spank him.”
“Now honey, I want you to do me a favor today and do anything the ladies ask of you ok?” My step mother told me and gave me a good spank which turned my bottom red.
My step mother was all I had and at that moment, I didn’t think much about her behavior towards me. To be honest, I enjoyed all the attention of those beautiful older and mature women whom I got to rub lotion on, and they rubbed it on me. Some women spanked me, one even took me over her lap and spanked me hard many times, then spun me around to show everyone how red my bottom became.
But it was my step mother’s friend June that I remember the most. She threw me into the pool and jumped in after me. She chased me in the pool and when she caught me, I tried to get away but she was too strong for me. She held me there for several minuets just laughing at me.
“Your not so strong are you?” June said. “Your more like a little sissy. A young boy like you can’t even get away from me.” June reached into my pink bikini and grabbed my cock and balls. “You won’t be needing these anymore little sissy. And it’s a good thing too cause your penis is not very big. From now on, your penis is going to be your clit.” June said as she squeezed my ball sack a little.
I remember that it turned me on a little bit to be man handled in this way. I was still a virgin and any contact with women turned me on.
June held my cock and balls and stood behind me in the pool. We were in deep enough water that no one could really see what she was doing to me. June stood behind me and then began to slid her finger up my ass.
“Now hush little sissy, don’t say a word. I am going to give you a very special treat right now.” June said as she slid her finger up my ass as far as it would go.
“Relax, yes, that’s nice, very good, I can feel your sissy penis getting hard. Your boy clit is very hard because you like it don’t you?” June said.
After fingering my asshole for awhile, June dragged me out of the pool and then showed all of my step mothers friends my hard on that was poking out of my little pink bikini.
“Look what the sissy has to show us.” June announced to everyone. I was completely humiliated as they laughed at me. I ran inside and cried on the bed.
Shortly after the pool incident, my step mother began to crossdress me. It all started one night after I took a shower. She came into the bathroom and too my clothes and said that she had to wash them and would leave me other clothes to wear laying on the bed. The clothes she left me were girly clothes. Panties, a bra, a slip, stocking, and a little teddy.
“I can’t wear these girl clothes mom.” I said.
“Oh don’t worry. No one is here to see you except me, and I think it would be fun to dress you up as a girl. Besides all your clothes are in the washer and if you don’t wear these, you will have to walk around naked all night. No come here and let me dress you up.” My mom said.
My step mom first slid the lace panties up my legs. Then she fastened the bra which felt strange. Then she slowly slid the stockings up my legs, and finally added the lace teddy.
“Now stand up and turn around for mom. Very good. You make such a lovely young girl. You look very innocent and submissive. Lets finish you off with a little make up from mom’s make up.” My step mother said as she took me by the hand and forced me into womanhood.
I stood in the bathroom with my step mother applying my make up. After she put red lip stick on my lips she stuck her finger in my mouth.
“Now show me what those beautiful red lips of yours can do. Suck on mamma’s finger little sissy.” She said while I sucked.
“Oh you look just fabulous. Lets go into the kitchen and talk until your clothes are done.” My step mother said.
We walked into the kitchen and then my step mother took lots of pictures of me. Asking me to pose in various positions. It felt a little strange but it was kinda fun to be dressed up as a girl. Just this once I thought.
We talked all night and then when it was time to go to bed my step mother said, “Listen, sweetie, your clothes are still not dry yet, you are going to have to sleep in your girl clothes tonight. But I want you to sleep in my bed because it makes me so happy to see you dressed up like a girl.”
My step mother took me by the hand and into her bedroom. She undid the bed and pulled me into it held me for a long time before we fell asleep.
“This is nice isn’t it? We should do this more often. Mommy likes it when her little girl sleeps with her at night. Mommy has been very lonely in bed for a long time.” My step mother said as she held me tightly and caressed my lace teddy and fondled my bra.
I was a virgin then, and the feeling of having big tits pressing against my back, her hands on my hips and rubbing my chest, and the smell of a woman was wonderful. I had a hard on and didn’t want my step mother to find it so I pushed my dick between my legs and soon feel asleep in my panties and bra laying next to my step mother.
Forced To feminize crossdressing with my step mom part one.
Cockold Stories. Cockold husband is forced to feminize sex story part two. July 7, 2007
Posted by sexstory in Cockold stories, Crossdressing Sex Stories, Crossdressing Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Kinky Sex Stories, Role Play Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, Three Some Sex Stories, True Sex Stories.11 comments
Cockold Stories. Cockold husband is forced to feminize sex story part two.
Written by Sheri Wilson
This is the true sex story about transforming my cockold husband into a cockold sissy slut.
After I forced my husband to wear the French Maids uniform and go around and suck on the dildos my friends and I had, I sent everyone home and they each spanked my husband as they left. My poor cockold husband was forced to lift up his skirt, bend over, and allow each one of my friends a good SMACK on his tight little pantied butt.
“You did a wonderful job at the party tonight sweet sissy, you looked so good in that French Maids uniform. Now I want you to clean up the house while wearing it, and while you are doing that, I am going to prepare a nice warm bubble bath for my sissy. Then I will give you that treat I promised you.” I told my husband.
I went upstairs and drew a nice bath, then I placed a new negligee, stockings, some high heels I found at a cross-dressing transsexual store, out on the bed. When my husband arrived in the bathroom, I stripped off his uniform and began to bath him.
“Doesn’t it feel wonderful to be part of the girls? It’s a side most men never get to see. It’s such a liberating feeling to be soft, and clean and to wear pretty things. Men are too worried about trying to be so strong and powerful. Most of the time, we as woman are attracted to that, but we also like a soft and sweet man too. It’s complicated. You are so lucky to be able to truly be one of the girls tonight and I hoped you learned a few things.” I told my husband as I washed his hair.
Then I began to shave his body hair. First his legs, and then his arms, and finally his pubic hair. My poor submissive husband had lost almost all his self respect by now, and it was getting easier to feminize him. I still had to force it a little. I would threaten to kick him out on the street, or to tell all of our friends that he liked to suck cock. We had witnesses now and I had some secret photos too. But mostly, he reluctantly when along with my wishes to feminize him and complete the cockhold husband training. After all, if he made it too easy, it wouldn’t be so fun.
“Now get out of the bath my shaved sissy. That’s good. Doesn’t that feel great? It’s going to feel so good in your panties and nightgown and stockings.” I said.
“My what?” He said.
“Now hush and let momma dress you up lovely and sweet. Step into these pretty pink stockings that I bought for you. Good. Now attach this garter belt to your wonderful sissy hips. That’s perfect. Your getting better. Now slip on thess high heels that I found. Lovely. You look wonderful. What man would not what to have you? “ I said.
“What are you talking about now? A man? No, I am going to draw the line when you speak about another man.” He protested.
“Now listen my sweet sissy pussy boy. If you don’t do exactly what I say, I am going to tell everyone we know that you suck my cock. And I will send the pictures I have to your family to prove it. You wouldn’t want that now would you?” I laughed.
“Well, no. So long as I don’t have to have sex with a man. Can you promise me that?” My husband asked.
“The only promise I can make to you, is that if you do what I say, you can stay in our house and don’t have to work. You can continue to live like you do. And I promise that I will think about your pleasure from time to time. Now admit it, so far, everything we have done, you have secretly enjoyed it. I have seen your erection while sucking on the dildo, and I watched you get hard when you were sucking on my girlfriends dildo. So you can stop the acting.” I said and I slapped him across the face.
“Yes, that’s good. I like how red your face gets when I slap it.” I said and slapped him several more times. “That looks like a good sissy slut. Yummy. That red face of yours is going to look good all over my big strap on dildo.” I said.
I added lots of lipstick and eye shadow to my husbands face. He looked like a cheap hooker. I led him into the bed room and forced him to strap on my strapon dildo. Then he assumed a position to suck it and I slapped him across the face again.
“No no sissy. You have already had a mouth full of cock tonight. Now it’s time to get an ass full.” I said.
I went to the draw and found a ball gag and placed in into his mouth. He looked so submissive to me. I was getting wet thinking about fucking my husband in the ass. I placed him on his front on top of a few pillows so his virgin ass was sticking straight up in the air. I tied his hands to the bed, and then spread his ankles and tied them to the bed also.
“Look at you now little sissy. About to get fucking in the ass for the first time. Are you scared? I can’t hear you. Oh, that’s right, you have a ball gag in your mouth.” I laughed at him.
Then I squirted lube all over his ass crack. I pushed aside his pretty yellow panties and took the tip of the dildo and rubbed in up and down his ass several times. I reached around and sure enough, he had a hard on.
“Someone likes all this far more than they should. Perhaps all these years you were a little sissy slut just too afraid to come out of the closet. Well, now you can little cockhold husband of mine. It’s ok, I want you to. Don’t deny it. I can see how much you want me to fuck you in your tight little virgin ass.” I said.
I split his butt crack in two, and began to force the head of the cock into his virginity. He moaned, and that turned me on even more. I slowly shoved the dildo deep into his ass, deeper and deeper. He took almost all of it. Then I began to fuck him slowly, in and out, then faster, then I was fucking him hard. I could tell he was in a little pain but could also tell he was enjoying it. I began to finger my clit while I fucked him and had a few orgasms.
Then all of a sudden, that little cockold husband of mine came into his panties.
“Hey sissy, you came fast. You’re not suppose to enjoy that so much. I had no idea that all these years you would have cum so fast if I fucked you in the ass. Oh, I can’t wait to tell all of my girlfriends at work about this.” I said.
I pulled out the large strap on dildo, then I lay down next to my tied up husband. I took off his ball gag and kissed him. He kissed me passionately.
“Now that I have found out how much you enjoy being my sissy slut, and being fucked in the ass, we are going to do this a lot more often. You would like that now wouldn’t you? “ I said.
“Yes. Very much.” My husband said.
“Well, if you listen to me, and do as I say, then I will reward you with my large strap on and place it deep into your little sissy ass.” I giggled.
The next weekend I invited my one my closest friends from law school over. Jennifer is a tall blond with large breast with short hair. She is a strong and dominant woman and always wins her cases. My made my sissy cockhold husband make us dinner and drinks and then clean up. Then I made him dress both of us up in dominatrix costumes. She was wearing black leather boots that tied all the way up to her thighs. I was wearing black silk stocking and high heels. And both of us donned large 8 inch black dildos.
I set up the video camera without my husband knowing it, and we began to force him to suck out cocks. Then we both took turns fucking him in the ass. He came instantly but we just kept lubing his butt up and fucking him. His limp penis and balls shook back and forth as we forced him into womanhood.
“You are so lucky to have such as tall sexy blond fuck your tight ass. Most little sissies have to pay for it. But since you are my sex slave now, it’s one of the perks.” I said as I watched my best friend pound my husband’s ass.
“You know, I think your husband is almost ready for the real thing”. Jennifer said to me.
“Yes, I think you might be right.” I said.
And that is the end of part two of cockold stories. Cockold story forced to feminize husband sex story.
Look for more cockhold stories on kinkysexstories.org. Cockold husband forced to feminize sex story part three is coming soon.
