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: Sex Story, cuckold, strap on, cross dressing
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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.
Cuckold Husband Forced to Feminize Sex Story April 20, 2008
Posted by sexstory in Black Sex Stories, Cheating Wife Stories, Cockold stories, Crossdressing Sex Stories, Crossdressing Stories, Cuckold Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Interracial Sex Stories, Kinky Sex Stories, Role Play Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Taboo Sex Stories, Three Some Sex Stories.Tags: Forced to Feminize, Cuckold Stories, cuckold story, cuckold sex story, forced feminization, Crossdressing Sex Stories
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Cuckold Husband Forced To Feminize Sex Story
Cuckold Husband Forced to Feminize Sex Story written by Stephanie.
This is the sex story of how I forced to feminize my cuckold husband into allowing me to have sex with a black man while he watched.
I married my husband for his money. He hired me as his secretary and he began to try and get me to bed soon after. Tim was a sweet man and I was very attracted to his wealth so I began to sleep with him and hoped he would fall in love with me. From early on, I rarely enjoyed having sex with him. He had a small penis and a very fragile and feminine body. I was taller than him and had a larger build as well. It began to turn me on when I would take control of him during sex and before long I would dress him as a sissy slut.
Tim enjoyed being my sex toy in the bedroom, and I enjoyed spending all Tim’s money on sexy clothes and whatever I wanted. I had dominated him in a short period of time and although this pleased me a great deal, he was unable to satisfy me sexually in bed. I began to cheat on him with many of his employees until one day he caught me with a black man and was furious.
I told Timothy that he could no longer satisfy me and if he didn’t want me to divorce him, he was going to have to allow me to cuckold him. A cuckolded husband is one that is dominated by his wife so much, that she forces him to watch as she is fucked by other men. This has been a fantasy of mine since early on in our marriage. Timmy did not like the idea at all but I explained that I would divorce him and get half of everything he owned so he better do what I said.
I dressed my sissy slut husband in a pretty baby blue lace frilly and dressed my sissy husband in white sheer stockings and added a nice pair of smart blue shoes. My cuckolded husband is actually a few sizes smaller than me and it’s like dressing up a doll. I always love it.
I tied his wrists behind his back so that even if he became upset while watching me take a large black cock, there was nothing that he could do about it.
The first time my husband watched me get fucked by another man, he cried and sobbed like a little girl. Since he was dressed like one, it didn’t seem so pathetic, and in fact turned me one a great deal. But after awhile it began to bother the black stud fucking me. So I did what any caring wife would do, I found a nice big black cock for my husband to suck on while I was being fucked. I thought it was rather generous of me.
So now, twice a week, Byron the black stud comes over to the bedroom and brings a friend. I dress my cuckolded husband up as the little sissy slut that he is and I make him watch me get fucked in every position I can think of while I scream and moan and cum all over the place. And when I am feeling generous, I allow him to suck the cock of Bryon’s friend until his sissy mouth is filled with cum and he cries.
Whenever my husband puts up a fight about it, I simply tell him that I will expose the cross dresser that his is to his employees and then divorce him and get half his company. He seems to understand the logic in this and allows me to continue this.
So in the end, I got the wealth I wanted, and all the black cock I can find. And my cuckolded husband made it all happen.
Cuckold Husband Forced to Feminize Sex Story written by Stephanie
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
Sexual Labels Prevent Sexual Satisfaction April 2, 2008
Posted by sexstory in Kinky Sex Stories, Role Play Sex Stories, Romantic Sex Stories, Sex Fantasies, Sex Stories, Sex Story, Sexual Health, Straight Sex Stories, Taboo Sex Stories, True Sex Stories.Tags: Sexual Health, sexuality, labels, satisfaction, role play, submissive, man, dominant, woman
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Breaking through sexual labels and finding more sexual pleasure by Ian
I realized I was kinky when I was very young and going through puberty. I found myself masturbating to various kinds of scenarios that did not just involve guy (me) on top and girl on bottom. I would feel submissive and sometimes raise my legs in the air and fantasized about being taken from behind by a man. Yet I was never sexually attracted to men, and still am not today. It was just the act of being submissive that turned me on, and still does today.
There were times I thought I was gay, or bi sexual and even experimented with a man once or twice. However afterwards, I just wanted women even more. But I noticed I was very attracted to she males and dominant transsexuals. So clearly I am attracted to females and not males. Does that make me straight? Well, I am attracted to females who have strap on dildos or cocks. So does that make me gay?
And as you can see, the concept of gay and straight becomes blurred. I don’t think we can help what we are attracted to and what turns us on. I feel that whatever fetish we have, whatever brings us the most pleasure, should be pursued. Life is short and often difficult and our sexual pleasure helps us through it all. To label it can be a mistake.
My own sexuality has forced me to be open minded about others and life itself. For whatever reason, I become aroused at the power play of a submissive male with a dominant women. Male and female are the poles that often govern our life and being male carries a lot of pressure with it. I have discovered that my sexuality and submissive side allows me to explore the feminine side of life, thus making me a more rounded person. If society needs labels, which we all know it does, than I must conform on the outside to one of these poles. I chose male. But in the bedroom, and during my spare time, playing the more submissive role allows me to relax, let go, and enjoy the human experience that much more.
I choose to label myself a sexual person. There is nothing like the smell of a women and the softness and kindness she carries. And to have a cock and thrust it into her while she moans with joy, is truly a wonderful gift. And the opposite of that is also wonderful. To be dressed as a women and be on the receiving end of a cock is something I think most men should experience. I know I learned a lot about what it’s like to receive and I think it has made me a better lover. Sex is sex and if you and your partner enjoy it, than that’s at least one thing in life you really enjoy. Let the world label what they have to, we can’t change that. But don’t let is stop you from enjoying yourself sexually during your free time and in the bedroom.
Sexual Labels Prevent Sexual Satisfaction article written by Ian More.
Forced Faggot From friend Feels Fabulously Fruity March 30, 2008
Posted by sexstory in Bi Sexual Sex stories, Crossdressing Sex Stories, Crossdressing Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Gay Sex Stories, Group Sex Stories, Interracial Sex Stories, Kinky Sex Stories, Role Play Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, Three Some Sex Stories, True Sex Stories.Tags: forced, fag, femm, femme, feminization, Forced to Feminize, Sex Story, kinky
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This forced fag sex story written by Sarah Smith.
Forced Faggot Sex Story
Hello and thank you for letting me share this free true sex story about how I forced my male roommate into being a fag. I didn’t know it at the time but this was how I began my obsession with turning men into fags. Nothing gives me an orgasm more quickly than to watch a straight guy being taken by a stud for the first time.
I was living in Hawaii barely making a living as a surf instructor. I had a beautiful apartment overlooking the Pacific Ocean but could not afford it so I placed an ad for a roommate. Since I am a woman, I didn’t want to live with some over testosterone male chasing me around the place. Rather I looked for a nice and kind roommate and found a very cute guy named Peter. He was thin and very sweet and I felt safe with him sharing my beautiful apartment.
Peter and I grew to be fast friends and we would talk every night about everything while sharing a bottle of wine. He had a very sensitive side and at times I felt like he was one of my girlfriends. I began to grow very attached to him and found myself feeling jealous when he would bring a female date home. He was such a wonderful and sweet guy and I didn’t want any other woman to have him or take advantage of him. I began to get very possessive of him and one night I took him to bed with me.
Peter was a very submissive lover and allowed me to be on top the entire time. He held me very gently as I came to a climax on top of him and then he obeyed me without question when I asked him to eat my pussy afterwards. As I looked down at him caressing my clit with his tongue, an image popped into my head that turned me on so much I couldn’t stand it. I imagined my sweet roommate Peter going down on a very masculine man while I watched. I couldn’t shake this fantasy and the next day began to conceive of a way to make this happen.
One of the surf instructors I worked with a Hawaiian stud named Lamar. He was a huge man and all the women wanted lessons from him. His skin was dark, his arms were large, and his butt looked like a rock in that tight black wetsuit. Lamar was openly gay and I approached him about my devious sexual intentions. Lamar was excited about the idea of being Peter’s first boyfriend but warned me that most straight men need a little coaxing from their female lovers to attempt being with a man. And I would need to train sweet Peter with a strap on first. I just about came in my panties when I hear him say that and quickly went to work on the plan.
That night I took Peter to bed and while I was riding him I reached around and under his cute and tight butt and began to slowly ease a finger into his sweet ass. He moaned, closed his eyes and came almost instantly.
“I found something you like didn’t I Peter?” I asked.
“Yes, I am surprised at how good that feels.” Peter said.
I led Peter by the hand and into the bathroom where I drew a nice hot bath. Then I laid him down and washed him slowly and gently in the tub with a moist washcloth. He began to relax and then his cock began to get larger and harder again.
“I see my baby is all ready for more? Doesn’t this feel good?” I asked.
“Yes. It feels wonderful. I’ve never had a woman give me this kind of attention before.” Sweet Peter said gushinly.
With one hand I began to stroke Peter’s swollen cock and with the other hand I forced a finger into his asshole again. He began to moan and his eyes rolled back. Then I slowly forced a second finger into his tight virgin ass. I could tell he was about to cum again stopped and gripped his cock tightly. His gentle eyes opened up and looked up at me very submissively.
“You can’t cum Peter unless you allow me to do something to you that I very much want to do.” I said.
“What’s that?” He asked.
“Peter, this may sound kinda silly but I want to shave your legs. You have such beautiful legs and I want to see them better.” I said.
“What? That is a strange thing to ask.” He protested.
“Well, you can’t cum until you let me do this. I promise it will be fun and erotic and when I am done shaving you, I will give you the best orgasm of your life.” I promised.
“I guess I can’t argue with that.” Peter said sheepishly.
And I took out my razor and tilted Peter’s head back and went to work shaving him bald. When I got to his crotch and began to shave his pubic hair, he did not protest one bit.
“Very good boy Peter. You look fabulous. Now are you ready for a very special orgasm?” I asked.
“I can’t wait” He said.
“That’s a good boy.” I said. I began to stroke his rock hard penis with one hand, and slipped a finger into his ass with the other hand. Then 2, then I secretly submerged a small dildo into the tub and slowly worked that into his ass. When Peter began to realize what it was he opened his eyes wide and I immediately pressed my lips over his before he could protest and forced my tongue deep into his mouth.
Peter came hard and his butt cheeks tightened around the dildo I had forced into his virgin butt.
“Now wasn’t that simply wonderful?” I asked Peter and his freshly shaved bottom.
I was obsessed with the idea of taking this sweet straight boy Peter, and turning him into a cock sucker and bottom boy. I wanted to see if I could have him sucking another man’s cock within a week. It was a very exciting challenge to me. The next night I climbed on top of Peter’s penis and quietly slip a butt plug into his ass. This time he did not resist and I left it in the entire time we made love. After I had several orgasms I stopped. Led Peter to my closet and slipped my pink silk robe over his naked body sat him down at my computer. The whole time while his butt plug was inside his ass. It was such turn on for me.
We began to shop for lingerie for me online, and then I suggested that I would like to see him in some sexy sweet nothings as well since he had such nice shaved legs. Peter did not resist, I imagine because he had my butt plug buried in his ass and was very eager to cum.
After we bought sexy feminine outfits for both of us to wear, I led him back to the bed, and placed him on his front. I slip a pillow under his ass propping it up and slowly removed his butt plug. I then tied his writs to the bedpost and took out my 6 inch black dildo and teased his butt crack.
“What are you doing to me?” Peter asked helplessly.
“I am taking advantage of you sweet Peter and it is driving me wild. You have no idea how much this turns me on to see you so submissive. You do want to please me don’t you Peter?” I asked.
“Umm hmm” Peter moaned as I worked the head of the large black dildo into his tight little ass. It made me so wet to think that only the third night Peter and I had been lovers, he was allowing his ass to be violated for my pleasure. I began to cum in my panties as I watched the black cock go in and out of Peter’s cut little ass. I plunged the dildo as far as it would go into Peter and then untied him and turned him on his front as I rode his throbbing cock to a climax.
The next day the lingerie arrived and we unwrapped the boxes together. I had Peter undress me and then dress me up in his favorite sexy lingerie. Then I undressed him and began putting on stockings over his shaved legs, then a garter, then my favorite part was the white lace training bra.
“Arms up princess.” I said as I slid the bra onto his chest. “Now turn around and let me fasten it. Good boy. Can’t you just imagine that you are a sweet innocent little girl with new breast in this lace bra?” I tugged and tightened Peter’s first bra and my pussy became soaked from the power of this exchange.
I took sweet Peter to bed and we made love like two lesbians both dressed in sexy lingerie. I took out a double headed dildo and began sucking it while Peter watched and fucked me. It was all too much and I came over and over and was lost far from this world in pleasure.
“Will you suck this for me sweetie?” I asked Peter as I led his lips to the large plastic cock in from of his face. Peter took the dildo into his mouth without so much as a wimper and began to suck. I gave him some helpful hints about how to take it deep without gagging and watched as my sweet boy sucked on my plastic cock on our 4th night in bed together. I was feeling pleasure deep in my pussy that I had never felt before. It was almost like having sex for the first time again. I was having multiple orgasms all over Peter’s pantied cock. It was unbelievable bliss. Peter and I passed out together still dressed in out new sexy lingerie and when we woke up the next morning, we made love for two hours again and it was just as wonderful as the night before.
We both called sick into work that day and bathed each other in soft soaps and oils. I dried and dressed Peter in panties and a bra and then put on a very tight fitting pair of my shorts on him. Then I picked out a tight tee shit for him and you could see his bra through it. He was bulging out of my clothes. I then applied just a little lip gloss to his lips, and a bit of make up too.
“Let’s go shopping” I said. “There is something very special I want to buy for you.”
“I can’t go out dressed like this!” Peter exclaimed. “People will think I am gay.”
“Oh don’t be such a sissy.” I said giggling. “No one will think that because you will be with me and I will hold your hand. All the women will be jealous that I have such a good looking boyfriend and all the gay men will want you. Please Peter, if you do this for me you will be rewarded with a very special gift.”
Peter reluctantly agreed and I drove him to the local sex shop. I made him reapply his lip gloss at a stop light and watched as several construction workers looked curiously at him. It was SUCH a turn on!!!
I led Peter by the hand around the sex shop and picked out a large black strap on dildo. Peter paid for it and as we drove home I made Peter unwrap it and place it between my legs as I drove. I began to stroke it and then forced his head down to suck on it like he was giving me a blow job. I exploded into an orgasm and almost crashed the car.
At our apartment I forcefully took Peter into the bedroom and placed him on his knees as he watched me strap on my new black dildo in front of his face. I teased his mouth with the head of the cock and then took him by the back of the head and watched as my cock went in and out of his sweet glossy lips. This was the most excitingly erotic thing I had seen and wondered why I had not done this to a boy before. I told Peter to suck on my cock and to play with his man clit until he came all over himself. He did in under a minute.
That night I tied Peter to the bed post again on his back and lifted his legs into the air while I fucked his virgin ass with my cock. The fact that Peter was so willing to let me violate him for my own pleasure made me extremely hot. To know that I was taking his virginity was an absolute turn on and as I fucked him with my strap on and he moaned, I began to cum again. I think on that 5th day with Peter I managed to have almost 40 orgasms. That’s the truth.
The next day we both went back to work and I told Lamar all about my progress with Peter and Lamar was impressed. I invited him over to our apartment that night after work and snuck him in before Peter got home. When Peter arrived I led him into the bathroom and began to dress him up in his sexy lingerie again. I dressed him as a little virgin slut with white lace, pig tails, and red hot lipstick. I locked him in the bathroom as I went and got Lamar to undress and get into our bed.
I went back into the bathroom and could barely contain my excitement. “Sweetie, I have a big surprise for you.” I said as I opened the door and Peter saw the Hawaiian muscle stud laying on the bed waiting for him.
“What’s this?” Peter asked scared and confused.
“It’s my ultimate fantasy honey.” I said. “Now don’t be shy, just go over to Lamar and give him a nice big hug for me.”
“I don’t know about this.” Peter protested.
I stood behind Peter and grabbed his arms and slowly walked him over the bed with the gay stud waiting for him. I whispered soft sweet things into his ear and stroked his cock beneath his lace panties.
“It’s ok. Don’t be scared. I am here and will not let anything hurt you. This is going to make me very happy and excited. You want to please me don’t you? It’s going to feel fabulous. Haven’t you ever wondered what it might be like to be a girl and be taken? This is your chance sweet Peter. Please, do this for me. I promise you will enjoy it and if you don’t we can stop.” I coaxed him.
Peter, dressed in white lace and lipstick, reluctantly got into bed with Lamar and gave him a long hug on my instruction. Lorimar’s hands explored Peter’s soft and shaved body. I glanced down and noticed Peter’s penis was getting larger.
“Now that doesn’t feel so bad now does it? Let Lamar kiss you now Peter.” I instructed.
Lamar’s tongue invaded Peter’s mouth and he began to kiss my sweet boy passionately. I reached down and stroked Peter’s cock for awhile and then replaced my hand with Lamar’s. When Peter was more relaxed I took his hand and placed it on Lamar’s cock and he stroked it until it was huge.
“Ok now Peter, I want you to kiss Lamar’s cock for me” I said. Peter did as I told him now.
“Oh my goodness. His cock is huge!” Peter exclaimed. Much bigger than mine.
“Yes sweetie it is. But don’t be scared, that’s just more pleasure for you.” I said.
I held Peter’s head as it bobbed on Lamar’s gay cock. I was completely turned on and could not help fingering myself as I watched my boy toy going down on another man. And it had only taken me 6 days. I began to cum and moan and this made Peter suck harder faster and deeper.
Lamar began to moan too and I sensed he was going to explode. “Now Peter, I want you to swallow every drop of his cum for me like the sweet little girly boy that you are.”
Lamar began to orgasm into Peter’s sweet painted mouth and his cum shot down Peter’s throat. Peter swallowed and I turned his head to me and kissed him very gently.
“You are an absolute wonder cock sucker Peter. You have no idea how much this is turning me on.” I said. Before Peter could speak, I kissed him deeply and began to play with is hard cock. “Now be honest, was that so bad?” I asked.
“No.” Peter said shyly and rather embarrassed.
“Don’t worry, I won’t tell anyone about this. It will just our little secret. Now, what shall we do with that rock hard cock of yours?”
I laid down and spread my legs and took out Peter’s hard on from his panties. I placed him inside of me and gently let him fuck me. I told Lamar that when he was ready, he could fuck Peter’s ass.
Lamar wasted no time and applied lotion to his gorgeous cock and began to slip it into Peter’s butt as I spread his cheeks for him. As Peter was fucking me I watched his eyes grow large as he was evaded by a gay man’s cock. I began to have uncontrollable multiple orgasms as I watched my sweet boy being taken by a man for the first time. Peter began to cum and as his butt muscle tightened he cried out as Lamar’s enormous cock sunk deep into his love hole.
“I think you like this too don’t you sweetie?” I asked Peter. He nodded from utter pleasure. “Don’t be shy Peter. I know you secretly wonder what it would be like to be Lamar’s boyfriend don’t you?” I asked. “It’s ok. I want you to have a boyfriend. It really turns me on.”
Peter agreed to go out with Lamar a few times and before long, he was getting fucked by Lamar instead of me. And then they moved in together and I went searching for another sweet boy to force into a fag. It’s an addiction I still can’t put down.
Strapon Mom Sex Story. First Time With My Best Friend’s Mom And Her Strap On Sex Story. July 14, 2007
Posted by sexstory in Bi Sexual Sex stories, Crossdressing Sex Stories, Crossdressing Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Gay Sex Stories, Kinky Sex Stories, Older Women Sex Stories, Role Play Sex Stories, Romantic Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories, Taboo Sex Stories, True Sex Stories.9 comments
Strapon Mom Sex Story. First Time With My Best Friend’s Mom And Her Strap On Sex Story.
This is the true sex story of a strapon mom and me. Not just any old sexy strapon mom, but my best friend’s mom.
Written By Dave
My name is Dave and my friend’s name is Ed. We have been friends since we were in elementary school. Our parents only live one block away and we grew up together. Ed’s mother has always been a hottie. I recall that the first time i masturbated, I was thinking about her. Of course I was too shy to ever say anything, and I was not the only one who thought she was hot. But I am sure that she knew all along that I was attracted to her. She was always very nice to me, even more so than her son Ed.
Ed and I grew up and went to different colleges and sort of lost touch. During my sophomore year, I returned to my old neighborhood for Christmas vacation and went to Ed’s house to see if he was home. I rang the door bell, and sure enough, a vision of sexiness answered the door.
“Well hello Dave. It’s good to see you again. My, you have really filled out. I bet all the girls at college love you. But I remember when you were just a little boy. Cute and playful. Sweet as a cherry pie. Now turn around and let me take a look at you.” My best friend’s mother said.
I turned around and her eyes poured all over my ass. She took my shoulders and twirled me around again.
“Well, my goodness, you certainly have been growing up. Come here and give me a hug sweeite.” Ed’s mother said.
As I hugged the mature voluptuous women, I was reminded why I used to masturbate about her so much. She was a goddess of form. she had big tits, the kind that are firm and stick out and beacon to be sucked. It’s the first thing anyone, male or female, can think about. She has wide hips, but not too wide, and stands about 6 feet tall which is 2 inches taller than I do. Her lips are full and sensual and sort of have a devious grin to them. They speak of being filled with an excess of estergine and perhaps a side of testosterone. The older woman commands respect and you can sense that if you give it to her, she is going to know exactly what to do with it. She is a natural dominant and powerful woman and we men are but moths to the flame of her sensuality.
“Hi Miss Bowen, ” I said. “It’s nice to see you too. You haven’t changed a bit. You look great. I was just stopping by to see if Dave was home for the holidays.”
“No sugar, Dave is not here yet. He is expected to be home in a few days now. But please do come in and sit for a spell. I live alone now and enjoy company. Let me make you something to eat and perhaps you would like some wine to drink. We can catch up on all that has happened in the past few years. Please come in.” She said and took my hand and walked me through the house.
Ed’s mother made me a sandwich and opened a bottle of Pinot Noir and then got up.
strapon mom
“Llet me change into something more comfortable. It’s so wonderful to see you again. You know, you were always my favorite. You had the cutest little boy smile and you always looked up at me with those pretty little eyes of yours” Miss Bowen said as she went to change her clothes.
I drank several glasses and was getting tipsy when she returned. She was now wearing a silk long nightgown that was closed but underneath I could tell she was wearing a black stockings and a garter belt. Good god she looked sexy. I was starting to think she wanted to seduce me.
“Did Ed tell you his big news?” She said.
“I don’t think so, what news?” I said.
“Well, he finally came out of the closet this year. My son Ed is gay. I suppose I was a little too nurturing with him, and perhaps was too much of a strong woman. It didn’t help that he didn’t know his father very well either. But they say, that being gay is not a choice. He has a boyfriend now and is happy to have come out of the close. ” She said.
“Wow, I would have never known he was gay. He always seemed so masucline and strong to me. ” I said.
“Well, I think he is a top. Meaning that he likes to be on top. He likes the cute boys, the submissive ones you know. Much like yourself. I always thought that you might have been gay too and that you and my son were lovers.” She said.
“No, I never knew. He never made a pass at me. We were just friends.” I said.
“Well I knew he had a big crush on you when you were younger. But what about you? Do you have a girlfriend in college? ” She asked.
“Well, I did, but it didn’t work out. She slept with my room mate so we broke up. I have been lonely and alone for awhile now.” I said.
“That is a shame, such a nice boy like you deserves a good woman. Come here and let me give you a hug.” My best friend’s mom said.
I got up and hugged Miss Bowen and I felt her hand slip down to my ass. She turned her cheek and our lips meet and she kissed me deeply with her tongue. Her hands continued to explore my ass and legs while we kissed. It all happened so quickly I didn’t have time to think.
Then she stopped and said, “I always knew you liked me. I could tell by the way you looked at me. You would watch my every move and look me up and down. And you would do anything I told you to do. I liked you too and just kept waiting for you to grow up. And now, here you are my sweet cute boy. I am very happy that you came over to see me.” My best friends mom said.
I began to blush and could feel my dick swell.
“Miss Bowen, I’m a little confused right now.” I said.
“Well, don’t be. There is absolutely nothing to be confused about. What you are feeling is as natural as a spring rain.” Miss Bowen said as she began to unbutton my jeans and skid them down my legs exposing my growing cock.
“Now let’s get these tight pants off you baby and see what you are hiding under there for me.” She said as she pulled down my underwear and exposed my manhood.
Miss Bowen then grabbed me forcefully and laid me down over her knee with my exposed ass sticking up in the air.
“Before we go any further, you must be punished for all the bad things you did at my house when you were a little boy.” She said and she began to gently slap my ass which made very loud smaking noises.
“But I was a good boy Miss Bowen, I never did anything bad.” I said as she slapped my butt repeatedly.
“Well, what about all the naughty things you were thinking about? Now look at yourself in the mirror as I turn your bottom red as a race car.” She said.
Miss Bowen spanked me over and over and I watched her do it in the bedroom mirror. The same mirror I used to look at when I was a young boy staying over with her son.
“Very good, now stand up and let me take off your shirt.” She said and she raised my arms up and lifted my shirt. With my arms high and the shirt almost off she stopped and kissed me deeply. “You are going to be my favorite boy toy sweetie. I am going to teach you some very wonderful and sexy things. You want that don’t you?” She asked.
“Umm, yes I do” I said.
“From now on, you will call me ma’am. Understand?” She said.
I was so horny I would have called her anything. “Yes ma’am” I said.
“Oh that’s very good” she said.
My best friends mom then laid down on the bed and spread her legs and pointed to her pussy.
“Now my sweet young thing, come over here and I will teach you what every woman wants. Stick out your tonge honey and begin to clean out my pussy for me.” She said.
“Yes ma’am” I said and went to work. My best friend’s mom told me where to lick, how to lick, and how long to lick, and after she bursted into several orgasms, she then told me to mount her. She began to slowly insert my cock into her mature pussy and moved me back and forth in the motion that she liked the best.
“Now don’t cum ok? I have many more things I would like to do to you.” She said.
I did my best to refrain from ejaculating inside of her but when I got close, she would shove me out of her and talk me down. We made love for over an hour and she had many many orgasms. I had no idea women could have so many. It was a beautiful sight to see.
“Now sweet boy, I am going to show you how to fuck a woman properly. But the best way to do this is by getting fucked yourself.” She said as she tied my writs together, and then tied my ankles together and lifted my legs into the air.
“What are you doing?” I cried.
“If you ask any more questions, I will stick a gag in your mouth so shut up and keep your legs up, I’ll be right back.” Miss Bowen said.
She returned several minutes later wearing a very large strapon dildo. I was speechless. Was she going to use that on me? I didn’t even really understand what it was at first.
Miss Bowen began to put a cool jelly on my butt and then slipped a finger in my ass.
“Ma’am, what is going on?” I asked.
“Now I told you to keep your mouth shut. Since you can’t seem to shut it, I’m going to fill it with my strapon cock.” And she shoved her didlo into my mouth. “There, now that should keep you quiet. Suck on it until you realize that your mouth is only good for two things. Sucking my cunt, and sucking my cock. That’s all I want your mouth to do from now on.” She said as I sucked the giant cock as she fucked my mouth.
“That’s a good boy. A VERY good boy. Yes, momma likes to see her big cock going in and out of her sweet boy’s mouth.”
After awhile, she took the strapon out of my mouth and began to slowly insert it into my ass. It hurt at first and I moaned but tried very hard to keep my mouth shut.
“The best way to learn how to fuck a woman, is to get fucked yourself. I am going to show you how a real man fucks.” She explained. Miss Bowen began fucking me with her strapon and it began to make a noise just like when I was fucking her.
“Do you hear that? That’s your ass pussy eating up my large cock. Now take a look in the mirror and watch yourself losing your virginity.” She said.
I looked over and saw my legs up in the air and my sexy best friend’s mom fucking me deep. Although it hurt, I could not help but come and came all over my stomach.
“Did I tell you to come? It seems you like this a little too much. You might just be gay after all. I always suspected you were. It’s ok if you enjoy my cock in your ass. My son is gay and I still love him very much. Perhaps ever more so.” She said.
“Ma’am, I’m not gay, it’s just that………….well………I don’t know.” I said.
“Shhhh…..hush now sweetie. I won’t tell anyone. You see, I just gave you a gay test and you didn’t know it. You fucked me for over an hour and didn’t come. But you came in less than a minute with a cock in your ass. Do you know what that means?” She asked.
“um, no.” I said.
“It means you like a nice big cock in your ass more than your cock in a pussy.” She said. “Don’t be shy, and don’t be scared. I have known you almost your entire life and watched you grow up and I always had a sense that you might be gay.” She said.
“I’m not gay.” I said.
“Honey, I realize it may take some time to come to terms with it. I want you to spend the night with me tonight, and we will talk about this more in the morning.” She said.
Miss Bowen whipped my cum off my chest and untied me.
“Tonight you are going to wear my panties and silk teddy to bed sweetie. It’s to celebrate losing your virginity to me and my cock. Now come over here to my closet and let me dress you for bed.”
Miss Bowen dressed me in her lingerie and we got into bed together. She laid my head on her chest and I began to get hard again. She lifted up her bra and placed my lips onto her supple nipples.
“Does sweetie need to suck a little before he goes to sleep?” She said.
I moaned that indeed I did.
“I can feel your little girl clit getting hard in your panties” she said. “Now suck on this for awhile.”
Miss Bowen gently removed my mouth from her breast and inserted a small dildo between my lips instead.
“Oh that’s very nice. You are getting much better at this. Soon you will be an excellent cock sucker.” She said.
As I sucked on her dildo, she reached down into my panties and began to stoke my cock and I released my cum inside the panties almost immediately.
“Miss Bowen. You have made me very confused. Am I gay now? ” I asked.
“Hush little baby. It’s time for night night. now go to sleep with your panties full of cum and we will discover more wonderful things tomorrow.” She said.
I awoke the next morning to a wonderful sensation. I looked down and Miss Bowen was sucking my cock. I didn’t say anything but just moaned and enjoyed it. Miss Bowen sucked my cock for over a half an hour and then stopped.
“Good morning princess. Did the princess sleep well in her silk panties filled with cum?” She said.
“Yes ma’am.” I said.
“Well good, let’s take a shower together shall we? And get nice and clean.” She said.
We took a nice long shower together and she cleaned me throughly. Then she dried me off.
“From now on baby, I want you to wear panties. Once you have had my cock in your ass, you can no longer wear those dreadful boy underwear.” She said and slipped me into a new pair of her pink panties.
Miss Bowen led me into the bedroom again and told me to suck her pussy which I did for a very very long time. She came over and over and told me to keep licking and sucking just the way she liked it.
“Even if you are gay, I can still use you to please me in this way. You are getting to be very good at it and when I train you to perfection, I have some friends of mine that I will want you to meet.” She said.
“Now, lets see if you learned anything from when you had my cock in your ass pussy yesterday. Come up here and fuck me like I fucked you.” She demanded.
I began to fuck Miss Bowen hard and deep.
“You are a slow learner sweetie. But keep trying. Remember what I showed you with my strapon. That’s how mommy likes it.” She said.
I fucked her for almost two hours until she was satisfied enough. I was exhausted.
“Time for your second lesson. Now this time, I hope you can keep from cumming so quickly so I can teach you more.” Miss Bowen said.
She took out her strapon dildo and strapped it on again. Then she put a lubbed finger into my ass.
“We need to stretch your ass pussy out just a little bit more today so that it is not so painful for you.” She said as she worked several fingers into my ass. “There, that is much better.”
My best friend’s mom stacked 3 pillows in the center of the bed and laid me over them with my ass exposed into the air.
“NOw get comfy darling, and try to relax for your second lesson.” She said.
She gently worked the head of her strapon dildo into my ass and began to move it in and out. It didn’t hurt so bad this time and as I relaxed, it actually began to feel wonderful.
“That’s it sugar. You are doing very well. Not pay attention to how I do it.” She said.
Miss Bowen placed her hands on my hips and pushed them back and forth, back and forth as her strapon filled my ass.
strapon dildo mom
“Now push back on it in the same rhythm.” She said as I tried to move my hips in the guidance of her mature hands. “Oh excellent, you are doing a very good job.”
And with those words of encouragement, I exploded and came all over the stacked pillows I was bent over on.
Miss Bowen laughed and took out her strapon cock from my asshole. She rolled me over and held me closely on the bed.
“Honey, now do you see? You fucked me for two hours and didn’t come. But when you had my cock in your ass, you came in 2 minutes. I think it’s time for you to accept it. You prefer a cock in your ass don’t you?” She asked.
“Ma’am, I am very confused.” I said.
“Don’t be. It’s very clear. We need to find you a boyfriend. It’s the only way to know for sure if you are gay or now. My son is coming home today. You two have always been very close, I think you would be perfect for each other. Now why don’t you practice sucking my strapon so when he gets here, you can show him what I’ve taught you.”
Strapon Mom Sex Story. First Time With My Best Friend’s Mom and her Strapon dildo.
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.
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.
