Forced Sissy Slut For Girlfriend’s Mom Sex Story October 30, 2006
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Forced Sissy Slut For Girlfriend’s Mom Sex Story
Written by Sherry Wilson
My daughter was dating a very cute young 18 year old boy during her senior year in high school. He was very sweet and extremely good-looking. I was recently divorced at the time and found myself constantly fantasizing about him and making him my love slave. But of course he was my daughter’s boyfriend. He had very feminine traits and I would try to impose that he was gay and that my daughter should find a real man. But secretly I did this only in hopes that they would break up, and I could have him.
Amanda, my daughter, was a very voluptuous young woman. Her breasts had developed to a very large size at an early age and she always attracted all the shy and sweet boys in her class. She was built like her father. Big boned and she even had a very dominate personality. She would bring the boys over and seduce them, turning many young virgins into non-virgins and thus making her very popular. She always threw parties at our house and there was a steady stream of young boys around.
Amanda had chose Brandon as one of her favorites, as he was mine too. I would listen to them in her bedroom as my daughter easily took control of him and seduced him into her bed. Brandon was so sexual, he was so beautiful for a man, and seemed to have such amazing female mannerisms, that you could not resist wanting to make him your lover. At least I couldn’t.
I had a plan to steal my daughter’s boyfriend away from her. I kept telling her that I was sure he was gay and gave her some ideas to find out for sure. I began to buy Amanda sexy lingerie, and I instructed her to begin to model it for Brandon after school in her room. She did so and I listened through the door of her bedroom.
Amanda would make Brandon dress her up in her sluttly outfits, and he learned how to apply her makeup on, what perfume to apply, and how to put on stockings. Once dressed, Amanda would tease Brandon until eventually they would have sex.
Then Amanda began dressing up Brandon in her sexy slutty lingerie and you could tell by the tone of his voice that he loved it. He would apply makeup and sometimes they would go shopping for him and buy him girly clothers. I suggested to my daughter that she begin to make him look at porn of naked men from Playgirl with her before they had sex. She said Brandon would do anything for her and he seemed to even talking about how sexy the studs were.
One day after school while Amanda was dressing up Brandon into his sissy slut clothes, I opened the door to the bedroom and caught him.
“Well, don’t you make a beautiful woman!” I told Brandon.
He blushed and said, “Umm, Miss Creegar, you caught me. I feel a little silly right now. Please don’t tell anyone you saw me like this ok?”
“Don’t worry, I think you look fantastic. Amanda has done a wonderful job with you. Any man would be lucky to have you. “I said and laughed at him.
“Thank you Miss Creegar, but please don’t tell anyone.” He begged.
“Amanda, can I help you to make Brandon even more beautiful?” I asked.
“Sure mom, I still have not finished with his hair and makeup yet. But don’t you think he has great legs?” My daughter asked.
I stood behind Brandon facing the mirror and began to add pig tails to his hair and applied red lipstick to his full lips. I put too much mascara on him and he reall did look like a first class hooker. He was suck a beautiful man. I told him how to hold his wrists, limp. And both Amanda and I walked him around the room letting him get used to his high heels. He seemed to completely enjoy all the attention and played the role like a pro. My pussy was so wet. All I could think about was taking him up to my room and watching him suck my 1o inch black dildo.
“I’ll leave you too alone now, but Brandon honey, you look fantastic and if you ever want to go shopping with me, I would be thrilled to take you.” I said.
“Thanks Miss Creegar.” Brandon said sheepishly.
I listened through the door as Brandon the sissy slut fucked my daughter. He was so submissive in the way he fucked her. Asking her to put his cock in when he was ready and making sure she came as many times as she wanted before allowing him to cum. When she was ready, she inserted a small dildo into his virgin ass and he came instantly. She was training him well for me and neither of them knew it.
One day Brandon came over the house when Amanda wasn’t home. I offered him some wine and told him that I needed to go shopping and wanted him to join me. I took him to Victoria’s secret picked out a few outfits for me and made him wait while I tried them on. Then called him into the dressing room to tell me how I looked.
“Brandon, since my daughters birthday is coming up, why don’t we buy something nice for you to wear for her. You know how much she likes to see you in lace and panties.” I said.
I picked out some white lace panties, a white satin bra, a mini skirt, some pink stockings and a teddy. I forced him into the dressing room with me and I stripped him down.
He was not a very well endowed young boy but he did have a very sexy body. He also had a fantastic butt that I could not keep my eyes off. I slipped Brandon into his sissy clothes, spun him around, felt him up and down, and got him very horny.
“What do you think Brandon? Do you think Amanda will like you in this?” I asked.
“Very much.” He said.
We went home and I dressed him up again in my bedroom putting on lots of makeup and giving him some red high heel shoes to wear. I told him that Amanda would be home shortly and we would surprise her for her birthday.
I took out some porn of naked men and told him to read this while he was waiting and locked him in my room. Just then Amanda called and told me she was going to be home very late because she had gone over to a boys house that she had just met. I told her to take her time and enjoy herself with her new guy.
I left Brandon alone in my room for a while looking at pictures of hung and muscular naked me. When I returned I asked him which one he liked the most. He blushed deep red and pointed out a very strong and extremely hung man dressed in a lumberjacks uniform. He giggled as I stroked his long hair and began to message his neck.
“Would you like to watch a movie while you wait?” I said.
“Sure. Thank you.” Brandon said.
I picked out a prono movie about a woman dressing up a man in sissy clothing and then turning him into a neighborhood slut. It was one of my favorites. I lay next to Brandon stroking his pink stocking thighs and making sure his penis became very erect while watching the movie. He became so horny he began to squirm and moan softly.
“You like this movie don’t you sweetie?” I asked.
“Yes, I do. But I don’t think I should.” He said.
“It’s ok my sweet sweet boy. You should not be ashamed of being excited. I love that you like this movie because it excites me also.” I said.
I took him and began to kiss him. He tried to resist at first but soon began to kiss me back. He kissed so sweetly and gently. I began to stroke his cock in his white lace panties.
I stopped and asked him to go to my dresser drawer and take out what was in there. Brandon got up and walked in his high heels, making his ass look just like a woman’s. He took out the 3 dildos I had in my drawer and brought them over.
“Now which one do you like the most?” I asked.
Brandon chose the largest dildo. It was black and shaped exactly like a perfect cock with balls.
I gave it to him to hold while I picked up the strap on dildo.
“Now do exactly what I do!” I said.
I began to suck the dildo and watch as Brandon repeated my moves. He was able to take it only half way down his small throat. Just like a young virgin would. I almost came in my panties just watching him. You could swear he was a girl.
“Very good Brandon. From now on I am going to call you Brandy ok?” I said.
“I don’t know Miss Creegar, I am starting to feel a little uncomfortable. I don’t want to upset your daughter.” He said.
I told Brandon that if he did not do exactly as I said, I would tell all his friends that he liked to dress as a girl. And I also told him that Amanda had been having sex with other boys for a long time, and was just using him to play with him. Brandon began to cry and sob. I held him in my arms and forced the dildo back into his small pretty mouth. This stopped his crying. I then slid my finger into his ass and he began to moan and squirm in my arms.
“See Brandon. You are in good hands. I am going to make you much happier than my daughter ever could. I have wanted you to be my lover since I met you.” I said and kissed him deeply and I fingered his ass.
“It’s going to be fine.” I said. “Are you horny?”
“Yes, I am very horny.”
“Are you willing to do anything I ask?” I said.
“Yes ma’am. I will do anything you ask. Just don’t tell anyone ok?” He begged me.
I told Brandon to practice sucking on his favorite dildo and I left the room and called 2 of my neighbors, whom were gay and would love to have a go at this fresh young sissy slut. I told them they would have to pay me $200 each. I explained that Brandon was 18 and was a virgin and had never had sex with a man. I told them to come over immediately.
When John And Dave arrived I told them to wait as I went into my bedroom and found Brandon sucking on his favorite black dildo. I handcuffed Brandon and put a chastity belt around his small penis. I told him that I had a surprise for him. I explained that before I would fuck him, he had to do me a favor. And if he did me this favor, I would be very good to him from now on. But he had to prove he was worthy. He was so horny that he was more than happy to do anything I asked.
I got up and let John and Dave in the room. Brandon looked a little nervous and I reassured him that everything would be ok and that he would enjoy this very much.
John and Dave took off their pants and lay down next to Brandon on the bed. John forced his cock into Brandon’s mouth while Dave began to lubricate his ass. Brandon looked very nervous as he began to suck the giant cock and he seemed even more concerned about the huge dick being worked into his ass.
I sat on the chair and began to fuck myself with the black dildo Brandon had been sucking earlier. Brandon was whimpering as he began to be rammed from being. I must admit that John and Dave were being very gentle with this virgin sissy slut and soon Brandon began to relax a little.
John came first into Brandon’s mouth and I instructed him to suck it all down like the good little sissy that he was now. He swallowed all the cum and then John began to kiss Brandon as Dave continued to try and get his entire cock inside of Bandon’s ass. Soon Dave pulled out and began to spew come all over Brandon’s bra.
When the boys were done with my sissy, they got up and walked out of the room and left $400 plus a tip on the kitchen table.
I held Brandon in my arms as he cried and whimpered a little bit and then took off the chastity belt on his small penis. I then told him he had done very well and that from now on, I would take very good care of him.
I placed Brandon on top of me and took his penis and slid it into my soaked pussy. I grabbed his delicious butt and began to move him in and out of my pussy at the rhythm that I liked best. I came and came all over his small dick as I thought about what had just happened. I kissed him and then inserted 2 fingers in his ass and he came all over my stomach.
Brandon, you may not realize this but you one very lucky little sissy.
“I love you so much Miss Creegar. I only want to make you happy.” Brandon said softly.
“That’s a very good sissy slut. Now go to sleep and get your rest because tomorrow there will be more visitors.” I said.
My First Time With A Gay Man Sex Story October 29, 2006
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My First Time With A Gay Man
Written by Ian
My wife and I had just been married and bought some property in the country. It was a very secluded farm and we would often walk around naked and have sex out in the yard. My wife was a reporter for a major network and often traveled and was gone for long periods of time. During this absences, I would often masturbate outside in the hammock looking up at the stars or in broad daylight.
My nearest neighbor lived several acres away and we would only see each other when we needed help with large projects. Byron was very muscular and in excellent shape and although he was single, I figured he got all the ladies.
One night as I was masturbating in the hammock, I could here someone walking up the driveway. I was totally naked and by the time I would have gotten back to the house, I would have been seen by whoever was walking up to my yard. So, I stayed still and watched and was relieved to see it was only Byron. He knocked on the door and I yelled, “I’m over here”.
Byron came over to the hammock and asked me why I was naked. I told him I was just enjoying being natural. But I assumed he knew I was jerking off cause my penis was hard.
“Is this a bad time?” he asked.
“Well, kind of. Can I help you with anything?” I said.
“Actually, I need some help in my barn with the horses, I’ll come back over in a few days?” He said.
“Ok, will do. Have a good night.” I said.
And Byron walked away. I finished jerking off and got the feeling I was being watched by someone but figured it was just my imagination.
The next morning, I walked out naked to the hammock and in the morning sun began to stroke my penis until I came all over myself. I heard something in the bushes as I began to spew cum all over my stomach and I turned my head to see what it was but could not make it out.
I worked all that day and was very tired and hot by the evening. And so horny too. I went back to my hammock and pulled my shorts down and jerked off under the starry evening. I then drifted off to sleep and when I awoke in the morning, Byron was standing over me. I had a morning hard on and felt very embarrassed.
“Good morning” He said.
“Hi Byron, you seem to have caught me sleeping.” I blushed.
Byron stared at my body for a long time. He looked me up and down and smiled.
“Are you ready to do some work today?” He asked.
“Sure.” I said and walked over to his barn.
Byron told me that we were going to do some messy work and that perhaps I should wear some of his old clothes. I agreed and he found me a very tight pair of white shorts and a tank top. He watched as I undressed in front of him and it made me feel a little creepy. Perhaps Byron was attracted to me.
I thought about that for awhile. You know, Byron was a very good looking man. I am usually not attracted to men but I have always been a little curious about what it would be like to suck a man’s cock. Sometimes, I would even fantasize about that. But I would never act on it. I was married after all.
But as we worked that day, I began to notice Byron’s hard body. His legs were very powerful and his tight shorts hinted to a rather large cock. Certainly larger than mine.
Byron was one of those people that like to always touch you when they talk to you. He kept touching my stomach all day and giving me motivational talks to keep on working. I didn’t mind it at all. After lunch, he actually spanked me like a baseball player does, and I rather enjoyed the playful nature of it. I spanked him back and said, “Come on now stud, let’s get her done.”
It became very hot and we took off our shirts. He was ripped and in better shape than I. He put some sun tan lotion on my back and arms and I returned the favor. Feeling his huge biceps and back muscles actually turned me on a little. And my shorts were so tight that anyone could tell I was excited. I caught him looking at my crotch and he smiled to himself.
“So how long is your wife away this time?” He asked.
“She’s been gone a month now and won’t return for another few weeks.” I said.
“Do you miss having sex?” He asked.
“Yes, I do. I am constantly horny.” I explained.
“I caught you masturbating the other day didn’t I?” He asked.
I blushed and said, “Yes you caught me, I really enjoy the hammock.”
“I know you do.” He said. “You look hot, do you want to cool down?”
And Byron turned on the hose and sprayed me down, soaking my shorts, socks and shoes. I did not expect it but it was fun and it did cool me down. I raced over to him and struggled to take it away from him but he was too strong. As we wrestled we were laughing and grabbing each other and he began to spank me playfully. Then tackled me to the ground and pinned me.
“I give up, you win Byron.” I said. “Now can I get up?”
Byron let go of the hose and I grabbed it from him and put it down his pants. It was so much fun. We were laughing so hard. He stood up and took off his shorts and I could see just how big his cock was. It was half hard and I could tell the play exited him. He told me to take off my short too and I said I was shy but really I was embarrassed because I was fully erect.
“Come on now, off with the shorts. I have seen you naked before.” Byron said.
I took off my shorts and reveled my hard on.
“Come on now, lets go dry out on the sun.” He said.
We walked naked to an open field and lay down next to each other in the warm sun.
“You have a nice body.” He said.
“Thanks. You do too. Your dick is huge and you are really in shape. I am glad my wife doesn’t know that.” I said.
“You don’t have to worry about that. I’m gay.” He said.
“I would have never thought that about you. You seem so masculine.” I said.
“Well, I prefer to be on top, you know. I like to be in control.” He said. “There is nothing I love more than watching my cock penetrate a man’s mouth or ass. Have you ever been with a man before?”
“No, I am usually attracted to females only but I have fantasized and wondered about what it would be like.” I admitted.
“I think everyone does at some point. Did you know that for most of mankind’s history, it was quite common for men to be lovers during periods without women. And women have always been allowed to be lovers with each other. Even today.” He explained.
My cock began to swell again as I listening to Byron talk. I began to think about his beautiful cock and wonder what it would be like to suck on it.
Byron told me to close my eyes for a second. I did and the next thing I knew was he was sucking my swollen cock. It didn’t feel much different than a women, and I could not help but enjoy the sensation.
He then moved his body around and positioned his hips above my face. And pryed open my mouth and inserted his huge penis. I began to suck slowly. It felt huge in my mouth as Byron began to hump my throat. He stopped sucking my cock and just watched me sucking his.
He then knelt next to me and lifted my head up to his penis and I cupped his ball sack and began to suck his cock more. I was totally turned on by this as he just watched me sucking his cock and moaning a little.
“You are very good at this neighbor. I hope you are enjoying it as much as I am.” He said.
“Now I am going to cum and I want you to swallow it.” He gripped the back of my head and forced his huge cock down my throat as it pulsated to an enormous size and I could feel ropes of cum being shot down my throat. When he was don, he pulled out of my mouth and told me to lick him clean. I did and just looked at his magnificent penis.
“Well, did you enjoy that?” He asked.
I had to think about it. I knew I was not supposed to enjoy sucking a man’s cock. But it did turn me on. I was not used to being on the submissive end of things but found it very pleasurable. I thought that what I was feeling must be similar to how my wife feels. And I began to have a whole new respect for her and thought that the next time she blows me, I will know what she is feeling.
“Yes.” I said. “I enjoyed it very much. Your cock is amazing Byron. It’s much bigger than mine and honestly; it makes me feel good to make you cum. I never would have thought that.”
Byron stood me up, took my hand and led me into the barn. I was walking with a raging hard on that would not quite and was so horny that I was somewhat delirious.
Byron spread a blanket over the hay and laid me down on my back. He took my legs and bent them and then spread them wide. He began to stoke my erect penis. His cock started to get hard and he rubbed it against mine. He took my arms and put them over my head and gripped me by the hips. He then took out some Vaseline and started to finger my ass hole.
It felt amazingly wonderful. I almost came with his finger inside of me. Then he put another finger from his other hand inside my mouth to suck on.
“You have sexy lips. You have cock-sucking lips. They are full and pouty just like a woman’s. I could watch them suck on anything all day.” He said.
I kept sucking on his finger and he slowly opened my ass with the head of his erect cock. He inched it further and further inside of me until there was no more room for him to go.
“Well, you can’t take all on my cock but we can work on that. We will have to stretch you out a little. I will give you a butt plug and a dildo to practice at home with. I am going to cum very fast because you are so tight.” He said.
Byron began to ram me slowly. My ass was incredibly tight and he could not go very fast. I began to cum almost immediately. As I came my muscles tightened and he came into the condom he was wearing. It was a wonderful sensation. I could feel his balls on my ass cheeks. I felt so exposed and helpless and close to him while his cock was in me. It was also interesting to know how it felt to be on the receiving end of a penis. I had learned a few things and felt sure that I would be a better lover because of this experience.
Byron leaned down and kissed me with his tongue. He then lifted me up in his strong arms and carried me to the shower in his bedroom. He then bathed me in the shower and I fondled his balls and cock and felt all over his body.
“Do you think I am gay?” I asked Byron.
“Well, there is only one way to find out. You have to have a gay lover. So until your wife gets back, I would like for you to sleep in my bed. That way, you can make a educated choice. Do you understand?” He said.
“Yes. I would like that.” I said.
Shemale Neighbor Sex Story October 29, 2006
Posted by sexstory in Bi Sexual Sex stories, Big Tits Sex Stories, Black Sex Stories, Crossdressing Sex Stories, Domination Sex Stories, Forced to Feminize, Gay Sex Stories, Group Sex Stories, Interracial Sex Stories, Kinky Sex Stories, Lesbian Sex Stories, Role Play Sex Stories, Sex Story, Shemale Erotica, Shemale Sex Stories, Three Some Sex Stories.add a comment
Shemale Neighbor Sex Story
written by Ian
I moved into my new apartment down by the beach and the neighborhood was known for being somewhat gay friendly. I am not gay but the neighborhood is the only safe one in the area so it was either that or nothing. At first I didn’t even notice who was gay and who wasn’t but over time it became clear that I was one of the few single men in my building. There were lots of gorgeous women but they all assumed I was gay.
My neighbor that shared our balcony was a transsexual and she scared me at first. She was very forward with me from the start.
Hello neighbor, why don’t you come over and suck my cock so we can get to know each other”. Was the first thing Tonya said.
I told Tonya, the shemale, that I was straight but she thought I was just shy. She would love to sunbath her body out on the balcony and flaunt herself in her sting bikini. Then try and get me to come out and talk with her. I brushed her off at first but she was very persistent. I had to give her credit for that.
On a warm Saturday afternoon I checked to see if Tonya was on the balcony and when the coast was clear, I put on a towel and began to sunbath. I must have fallen asleep cause the next thing I knew was Tonya was rubbing sun tan lotion on my bare ass and back and legs. She was humming something about sleep baby boy sleep.
I was surprised to find that I had an erection.
“What are doing?” I asked Tonya.
“I am trying to make you horny so you will want to suck my big cock like you know you want to sexy neighbor.” Tonya said bluntly. “Is it working?”
“I thought shemales were supposed to me submissive and ladylike. “I said.
“Well sweety, I am a top. I like cut boys like yourself. I like to watch as they worship my body and most of all I like to……” she said
“Ok, ok, I get the picture here.”I said while stalling her so she didn’t find out about my hard on.
“Come on, you know you want to suck my cock sweet boy. It’s just a matter of time. I know you masturbate about me but your afraid. I like that. It’s very sweet and nice.” Tonya said.
“What about your boyfriend? Wouldn’t he be upset if he knew you were trying to seduce me?” I asked.
“Never mind him. He is not here but you are my beautiful little boy. Let’s make the most of our time together and give me a little kiss.” Tonya said.
Tonya leaned in to kiss me and I turned my head to the other side.
“What a bad boy you are. Making momma chase you so much.” Tonya said and gave me a spank on my naked butt.
“Ok, enough is enough Tonya. I’m straight and have a girlfriend and you are gay and have a boyfriend. And I’m not going to suck your dick ok? Now hand me my towel and let me go inside.” I said.
“Well aren’t we feisty? I tell you what sweetie, I am going to finish putting on your suntan lotion and then I will leave you alone if you want me to ok? There is no need to hurt my feelings. We are neighbors after all. Can I have a make up hug?”
“No Tonya, just finish what you were doing and then go alright?”
“Now that’s more like it.” Tonya said.
Tonya’s large strong hands began to work up and down my naked legs, thighs, ass, and back. I found myself oddly turned on by all this and it made me a little confused. I wasn’t gay, but I was turned on. It was a warm summer afternoon and Tonya had me very relaxed. I began to fantasize about what it would be like to suck her dick. And the more I thought about it, and the more she rubbed my back, the harder and harder my penis became until it was obvious that I was aroused my what Tonya was doing.
“See, I knew you would like it. But you hurt my feelings. I’m not going to let you suck my cock now. I am finished and you can go.” Tonya said.
“I am sorry I hurt your feelings Tonya. Thank you for the back rub. It was wonderful really. “ I said as Tonya left me there with my hard on.
The next day I saw Tonya sunbathing on the balcony and went out to talk to her. She asked me to put lotion on her and I rubbed her back and all over her body. She was really well built. She could have kicked my ass for sure. She was dark skinned and had a wonderful ass that I admit I would have like to fuck if it wasn’t attached to a cock and balls.
“Have you ever been with a man before?” She asked.
“No”
“Have you ever fantasized about being with a man?”
“No”
“Have you ever been attracted to a transsexual before?”
“Well, yes. One night in a bar I kissed a person who turned out to be a man.”
“Did you like it honey?”
“It was a little strange. I was surprised and scared by it. But I did find her attractive.” I explained.
Tonya turned over and said, “Be a good boy and do mammas front now.”
I tuned her over and saw her cock sticking out of her sting bikini. It was very large. Bigger than mine. I couldn’t help but stare at it for a few moments.
“I know you want to suck my play pole, but I am not going to let you. You are being nice to Tonya now but still, no matter how much you beg, you can’t suck my cock. So just forget about it.” Tonya said.
I laughed and continued to rub lotion all over her front. She had large breasts and her nipples were hard. I was fascinated by her and could not stop looking at her cock. She watched me and grinned.
Tonya invited me inside her apartment and sat me down and made some cocktails.
“Have you ever worn women’s clothes?” She asked.
“Maybe” I said.
“You should let momma dress you up. I can make you a beautiful little girl. It will be fun.”
“Maybe later.” I said.
Tonya and I had several drinks and talked about sex. All the sex talk was making me horny and then she led me upstairs to her bedroom and picked out some of her clothes for me to wear. I debated letting her dress me and figured what the hell. She stripped me down and then began to put panties, a bra, a skirt, a tight little blouse and stocking on. Then a pair of red high heels. Then she took me to her make up table and began to apply makeup and lipstick to my face.
I could see her 9 inch cock was erect under her sweat pants and began to stare at it.
“Now stand up pretty girl and lets walk about to get used to the shoes.”
I stood up and had a difficult time walking. I admit it was fun to be dressed in this way. She led me by the hand as we walked around the bedroom and I began checking out myself in the mirror.
“Now it’s your turn to dress momma as a man.”
I stripped off Tonya’s shirt, and then her tight sweat pants and then her panties. Her cock was huge. I then dressed her in my clothes. It was fun. We were laughing very hard trying to talk like each other. As we laughed, we embraced and our faces met. She learned forward and kissed ramming her tongue in my mouth. She grabbed my hips and held me like a woman. I was completely turned on and our cocks rubbed together. Both fully hard. It was a strange sensation. I was all mixed up on the inside.
Tonya took my quivering hand and led me to the bed and laid me down. She lifted up my skirt and pulled down my panties and began to suck my cock until I was about to cum. Then she lifted her hips over my face and inserted her large cock in my mouth. I sucked and sucked and sucked and soon she began to pump large amounts of cum into my mouth. I swallowed it all and then she inserted her finger in my ass and I came in her mouth.
What had I just done? I just sucked a cock. Sure, it was attached to a beautiful woman, but still. I was confused.
Tonya held me and started kissing me again. And again I became hard as she did too.
“What a good little girl you are. If you keep making me so horny, I am going to have to fuck you sweet little virgin ass. I know you want me to. But you have to ask me like a good girl.” Tonya said.
“Please fuck me. Oh pretty please. I will do anything you want. I need you to fuck me.” I said in my best girly voice.
Tonya took off my panties and lifted my legs with my high heels on them into the air and spread my legs. She rested her large cock on mine and kissed me deeply.
She inserted her finger in my ass and then the head of her cock. She began to fuck my ass and kiss me. She was fucking me better than I have ever fucked any girl. I was learning new things.
I came immediately. It felt amazingly good.
“Well, somebody really likes this. See I knew you were not straight, and just shy. I love my boys that way.” She said.
She kept fucking me until she was about to cum and pulled out and came all over my face. Ropes of cum on my makeup. I licked and sucked it all off.
We fell asleep together in the bed and in the morning she woke me up by inserting her cock in my mouth. I sucked her off and then she ran a nice warm bath for me and bathed me, dried me off, and put a string bikini bottom on me.
“Go out to the balcony and I will cook you breakfast and meet you there.”
I bathed in the warm morning sun contemplating what I had just done. Was I gay now? Perhaps it was just a one-time thing. Did I enjoy it? I think I did. Do I want more?
Tonya came outside with breakfast and champagne and placed me in-between her legs and spoon fed me. I was totally enjoying it. She was treating me better than any women ever had.
She began to kiss me and stoke my stomach until I was hard again. She undid the sting on my bikini bottom and bent me over and inserted her cock in my ass again. She began pumping and I came almost immediately again.
“I’m sorry Tonya. I am new at this and have not learned how to control myself.” I said.
“That’s ok sweetie, just let momma do all the work.” Tonya said.
Tonya fucked my ass until I became sore. Then she pulled out and came all over my back and rubbed her cum in.
“I have to go to work now sweetie, but when I come home, I want you in my bed and waiting for me wearing something from my closet. Do you understand?”
“Yes” I said.
Over the next month, I was Tonya’s bottom boy lover on a regular basis. I met her boyfriend a few times and he never suspected anything cause I had a girlfriend. My girlfriend met Tonya and they got along very well. Nobody suspected a thing. But we fucked and sucked each other as much as we could. I began to enjoy being fucked in the ass as much as fucking pussy. I also learned how to fuck Tonya in the ass too but she usually preferred to fuck me in the ass.
One day, My girlfriend came over without warning me and caught me on the balcony being bent up and fucked in the ass dressed like a woman. She got very upset and left. Later she called me and we talked.
“Are you gay?” She asked me?
“No. I am not attracted to men in anyway.”
“Well, why were you being fucked in the ass then?” Said asked.
“Well, it actually feels good.” I said.
“Why didn’t you tell me that and let me do that to you?” She asked.
“I am worried that you would think less of me.” I explained.
“No silly, I would have enjoyed it very much. Have you been sleeping with any other women?” She asked.
“No baby. You are the only women in my life and the thing with Tonya was just a one time thing.” I said.
“I have thought about this a lot. And I am going to try to forgive you. Actually, I am not that hurt by it because it’s not like I can ever give you what Tonya can. And I can understand that if anal sex turns you on, and you were afraid to ask me, then you would have to get it somewhere else. But now I know and I will give it to you. But you must promise to not sleep with Tonya again.”
I agreed and thanked her for her understanding. But soon Tonya seduced me again and I began to wake up with her cock in my mouth every morning.
Then Tonya’s boyfriend caught we one day. I was asleep in her bed when he came over and found me there dressed in panties and a teddy. He became very upset but also forgave Tonya if she promised never to do it again.
My girlfriend and I were having fantastic sex. She would sometimes use a strap on and sometimes dress me up. She loved it as much as I did. Then I would go home and suck Tonya’s cock and sleep with her. This went on for months until I began to feel guilty.
I told my girlfriend the truth and that I was sleeping with Tonya and I was feeling guilty. To my surprise, she told me that she fantasized about watching me being fucked by Tonya and asked if she could watch.
I asked Tonya and she agreed and asked if she could bring a friend to watch too. Why not?
Tonya’s friend turned out to be a handsome large black man named James. This made me very uncomfortable at first. Why had she brought James?
“You will see.” Tonya said.
So as Tonya began to bend me over and fuck my ass, and my girlfriend and James watched, James began to kiss my girlfriend. Tonya held me down so I could not get up. James started to undress my girlfriend and he slid his fingers inside her pussy. She was moaning, as my ass was getting hammered by Tonya’s beautiful cock. At first it bothered me but then it began to turn me on.
He bent her over next to me and we kissed side my side as James fucked my girlfriend in the ass, just like Tonya was doing to me. Tonya and James began to kiss. And soon, people were cumin all over the place.
First I unloaded as Tonya reached around and jerked me off. Then Tonya unloaded on my back. Then My girlfriend began to have multiple orgasms. Then James unloaded on my girlfriends back.
And then we all switched partners. It was like some kind of game of musical chairs. I fucked my girlfriend and Tonya and James began to suck each other off. More orgasms.
Finally, we all collapsed out of exhaustion. Tonya took my girlfriend upstairs for a shower and James and I sat on the couch. James began to message my back and shoulders and then started to rub my crotch. He turned my head to kiss him. I didn’t really want to kiss him but it was not so bad. He then pulled out his cock and told me to suck it. I did. I was not very good at giving head and James came in my mouth in under 5 minutes. Upstairs I could hear my girlfriend being fucked my Tonya. This made me very angry but James told me to calm down and relax and that it was ok.
I wanted to run upstairs but James grabbed me, pinned me down, and began to fuck me in the ass to shut me up. It worked. He was even bigger than Tonya. It was painful and I had to concentrate on relaxing my ass muscles to allow for his gigantic cock to penetrate me.
His cock was so big, I could not cum because each time I tried, my ass muscles tensed up and he just pumped me harder. It was starting to make me delirious, and then it began to make me feel incredible. It was like I was having multiple orgasms but unable to actually cum. I could hear my girlfriend moaning upstairs. Tonya was fucking her good. I began to hope they would continue so I could keep being fucked.
Soon, they came downstairs and found James pounding my ass. I was enjoying it so much that I couldn’t care less if anyone saw me or what. My girlfriend sat down to watch and gave me small kissed as I was being fucked. She also kissed James while he was inside me. Finally James came all over me and as he pulled out, I came too. Loads and loads of cum spewed out of my penis. I had never had an orgasm like that before.
Tonya made us drinks as we all relaxed.
“We have something to confess to you.” Tonya addressed me.
“Your girlfriend and I have been fucking each other for several months now and we wanted to tell you but we didn’t know how. We have fallen in love and wanted to have sex with you one last time before we told you.” Tonya said.
I was shocked. “You mean you are both breaking up with me?”
“Yes, I am sorry.” Tonya said.
“Well, I would have never guessed that.” I said.
“It’s just that I want to be with someone else for awhile. Watching you and James made me certain of it. I think you should be with a man.” My girlfriend said.
“I agree.” Tonya said. “Watching James fuck you, I could tell how much you enjoyed it. It’s ok baby. Sex is sex. As long as you enjoy it, then it doesn’t matter who it’s with.”
James leaned over and kissed me. I thought all this was very strange. On the one hand, I was being dumped and told I was gay. But on the other hand, they were right. James gave me the best orgasm of my life.
“Why don’t you just try if for awhile and think about it.” Tonya said.
James took my hand and led me upstairs into Tonya’s bedroom. He gently laid me down began to caress me and kiss me. It wasn’t so bad. He began to put a finger in my ass. I began to get hard. He began to put baby oil all over me and then he inserted he cock again. And just like last time, I could not cum because he was so large. I kept having multiple orgasms and began to moan and almost black out.
My girlfriend and Tonya opened the door and said, “I see you are in good hands now.”
Shemale neighbor sex story written by Ian.
My First Time Anal Sex Story October 28, 2006
Posted by sexstory in Bi Sexual Sex stories, Domination Sex Stories, Gay Sex Stories, Group Sex Stories, Kinky Sex Stories, Lesbian Sex Stories, Role Play Sex Stories, Sex Stories For Women, Sex Story, Straight Sex Stories, Strap On Dildo Stories, Three Some Sex Stories.1 comment so far
My First Time Anal Sex Story by Jewels Reveda
When I was a teenager, I was often overlooked by the guys at school. I was a nerd and a little bit of a free thinker. Guys usually made fun of my short hair and glasses. They were sometimes quite cruel to me. So when I went to college and found myself in bed with a woman one night and really getting off on it, I was not surprised to discover that I was a lesbian. In fact I was more surprised just recently to discover how much I enjoyed being under the strong and forceful hands of a man. Which has led me to some internal confusion about my sexuality, as well as countless orgasms.
Let me explain. Up until recently, I have only been with three different lovers and they were all women. Fantastic, caring and nurturing lovers who showed me myself and whom, I will love forever. My last girlfriend, Yamila, was very kinky and liked to experiment with all kinds of dominance and submission styles. We had the best sex I ever had at that point and I was completely fulfilled all night and all day. In fact my awareness of sex increased to almost an addiction. If I wasn’t being fucked by one of her large strap on dildos, I was wearing a vibrating egg all day and having orgasm after orgasm.
One drunken night, Yamila and I were out at a college bar to see a great dance band. Turns out that Yamila had slept with the bass player once in a 3way with her old lesbian lover. She told me that usually she is not attracted to men but since he had long wavy hair and was very feminine, she found him a little attractive. She said it was the only man she had every fucked and that he was magnificent for a guy. I found him intriguing too and pursued Yamila to talk to him after the show.
The bass player, Shawn, was very handsome for a man and you might think he was gay because he was so feminine. He had deep brown eyes and reeked of sensuality. However the thought of cheating on my girlfriend never crossed my mind. I just enjoyed talking to guy.
Yamila and Shawn began doing shots of tequila and then they started talking about the one time that they had a 3some long ago during college. They laughed and joked and I began to get very jealous. Yamila asked me to follow her to the bathroom which always meant a “girls meeting”.
Yamila asked me how I felt about Shawn and I admitted I found him attractive but I had no plans to cheat on her much less have sex with a guy. She gave me a big kiss, slid her hands up my skirt and fingered me in the bathroom until I came on her finger. Then she made me lick it clean. We went back out to the bar to say goodbye to Shawn and went home and fucked like we normally did every night. For several hours until we slept.
About a month later I came home from work early and as I entered our apartment I opened the door to my girlfriend Yamila getting fucked up the ass against the wall and making so much noise that she never heard me come in. I stopped in shock and watched for a minute before I began to cry. Shawn and Yamila stopped fucking and Yamila tried to comfort me. She said it was a one time thing and that she was drunk and was terribly sorry. Shawn left and I cried all night feeling very sad and jealous.
In a few days I decided to forgive Yamila. I loved her very much and tried to understand her point of view. I was very interested in what it was like to be with a man and kept asking her questions about it.
Finally she said, “Listen, how would you feel if the three of us got together for just one night?”
Inside I felt very upset by this because it would mean my girlfriend would be cheating on me. But my curiosity won over and I gave in to the idea.
The next night, Yamila and I went out for a bite to eat and some wine and when we returned to our apartment, we found Shawn waiting for us naked and on the bed. I must admit that I was initially turned on by his naked body because I prefer women. But he did have a beautiful cock even if it was not as large as Yamila’s dildo I was accustomed to.
“Hello ladies.” He said. “I am honored to be here to serve you and your every desire.”
“Oh shut up Shawn and start sucking pussy.” Yamila ordered.
Yamila put a blindfold over my eyes and then someone undressed me and placed me over Shawn’s mouth. He began to suck my pussy and my clit until I was numb and so horny I didn’t care who was doing it.
Then Yamila bent me over and slipped in her favorite dildo up my pussy. Someone placed my mouth over Shawn’s erect cock and he told me to suck. And I did. It was a wonderful warm feeling to have a real cock on my mouth vs. a plastic dildo. I began to have multiple orgasms as I was sucking and being fucked. What more could a girl ask for.
“I am so sorry sweetie.” Yamila told me. “I never meant to hurt you. This is for you in hopes you will forgive me. Do you forgive me?” Yamila asked me as I was getting my brains fucked out.
“Almost” I said.
“Please don’t make me watch your pretty pussy get fucked my a man.” Yamila cried.
“Why not?” I said. “I watched you getting your pretty ass fucked my a man.”
Yamila finally gave in and allowed Shawn to have his way with me. He crawled on top of me and sank his thick cock into my soaked pussy and began to sink it deeper and deeper using motions I have never known before. He was very talented with his hips. He was an excellent lover and better than any women I had been with. I was enjoying it far too much for being a lesbian and began to moan and cry out and smile without even realizing it. Shawn began to kiss my neck very sweetly and then sank his tongue into my mouth.
“No kissing!” Yamila told us. “Anything but that ok?”
“Yes ma’am” Shawn said while he continued to pump my pussy. He fucked me until my juices ran dry after 45 minuets or so. Yamila was watching me and fucking herself with a dildo that she occasionally shoved inside my mouth.
“Yamila, can you get the lubricant out?” I asked.
“No sweetie, time is up. Shawn, it’s time to cum, I can’t stand to watch this anymore.” Yamila said.
Shawn pulled out his hot cock and came all over my small tits as I rubbed it all around just like a slut. And I felt like one too. It was a wonderful sensation to get fucked by a guy under my girlfriends supervision. It was more than worth it to catch them fucking and get this in return. I had a wonderful girlfriend.
Shawn showered off, got dressed, and said goodbye. When Yamila wasn’t looking he kissed me and handed me his phone number secretly and whispered,
“Call me anytime. I am crazy about you.”
I went to bed that night confused. On the one hand I was more in love with Yamila than ever for allowing me the chance to even the score. And on the other hand, all I could do was think about Shawn and his warm cock, long hair, soft brown eyes, and his cum all over my body. I kept these thoughts to myself.
That next weekend I went alone to a bar where Shawn’s band was playing and secretly watched him move on stage. He was beautiful for a man and so darn sexy too. I wished I would not have been blind folded while he was fucking me. And it was at that instant, that I knew I would fuck him again.
After the band finished, I bought 2 shots of tequila and approached Shawn. He immediately gave me a long loving and gentle kiss and held me for a moment. I blushed. The guy really did like me. We did the two shots of tequila and he took my hand and we walked down the street to his apartment saying very little. There was little that needed to be said.
He undressed me tenderly, savoring every inch of my body, licking various crucial soft spots and got me wet and ready in no time. I must have played with cock for 2o minutes. Like a little girl with a new toy. I had never held a real cock before and I was 25 years old. It was wonderful and so well formed. He ball sack was also a fascination for me and I played with them and licked them until Shawn was fully ready to go.
Shawn and I fucked like wild animals for about an hour and I had countless orgasms. I never felt guilty once. How could something that felt so good be so wrong? If anything, I knew why Yamila had succumbed to the forbidden fruit.
Shawn took the lubricant and began to finger my ass. I began to get nervous about it what would be next and started to squirm. He forced himself on me and his weight kept me still. I pleaded with him not to fuck me up the ass but this only excited him more and his showed his huge cock inside of my ass.
It felt surprisingly wonderful and I started to relax. He began to fuck me violently and I began to cum over and over again. He stood me up against the wall and we hand anal sex for more while he reached around and massaged my clit.
I have never known sex could feel so good. I had never thought I would enjoy anal sex. Especially from a man. But as it turns out, I loved it and became addicted to it.
From then on Shawn and I would secretly have anal sex every chance we could. Yamila never found out and I am still her lesbian lover. I seem to be making up now for all those years I never had sex at all.
I suppose I should ask Yamila if she would like to join me and Shawn but I don’t want to chance loosing him.
Crossdressing Sex Story With Aunt Joan October 25, 2006
Posted by sexstory in Bi Sexual Sex stories, Big Tits Sex Stories, Crossdressing Sex Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Kinky Sex Stories, Older Women Sex Stories, Role Play Sex Stories, Sex Story, Strap On Dildo Stories.2 comments
Cross Dressing Sex Story With Aunt Joan
When I was in high school, my parents used to go away on vacation to exotic and far off places every summer. I was an only child and for them a vacation was without the kid. So they dropped me off at my father’s sister, my Aunt Joan. Aunt Joan was adopted at a young age by my grandparents and Joan was famous for always being a wild woman. She married a man once who was 40 years older than her and filthy rich. He died suddenly and Aunt Joan received millions. She was my favorite Aunt and during puberty I always used to masturbate about her.
As I got older, my summers with Aunt Joan became more and more fun and interesting. She took me around all day doing errands and hanging out with her interesting friends. Most of them were either gay, bi sexual or just plain good looking and as a teenager, the whole scene fascinated me. Such a different world from my conservative uptight parents.
The summer I turned 15, my folks went to Barbados for 3 months and off to Aunt Joan’s I went. But this year was different. Joan had moved into a huge house on the beach and there were at least 4 guest rooms to choose from. Joan took my hand and led me to the PINK room. She explained to me that this room was the only room that was finished and although it was intended for a girl, she was sure I would find it more than comfortable. And indeed it was. A large soft fluffy bed with a large mattress. A huge walk in closet, and a bay window plus a private bathroom with hot tub. Thank you Aunt Joan.
Joan and I would run her errands and go to posh shopping malls as well as fancy restaurants and she would even buy me wine for lunch. She easily won me over and I looked forward to seeing her everyday. Usually she would try on clothes all morning and I would sit near the dressing room and tell her how she looked. She looked great. She was of German decent and a large and full figured blonde bombshell type woman although not fat. She had powerful legs and butt muscles and the largest breasts I had seen up close. She could have been a porn star and she was in my mind. Everything she tried on was a size too small and she spilled out of it like milk from a glass pitcher. I had a constant hard on all summer long.
One early summer morning I woke up and began to get dressed. I noticed all the lingerie in the closet and dresser drawers in my girly pink room and decided to dress up a little bit before breakfast. I found some white thong panties with lace around the elastic edges, I slipped them on and turned around and looked at my ass in the mirror. I stuck it out just like a little slut and it turned me on a bit. Then I put on some white stockings over my legs and found some white garders to attach to them. Then I put on a small white lace bra. Just then, Aunt Joan opened the door to my room and caught me all dressed up.
“My, you look delicious” she said. “Come here and let me help you”.
My face turned red and I knew I had been caught. I just stood there.
“Now look sissy boy. If you don’t do as I tell you, I am going to tell your father that you like to dress up in panties and frillies.” Aunt Joan said.
She had me over a barrel so to speak and I did what she told me. And actually, I really enjoyed it. The thought of being my Aunt Joan’s sex slave was a dream come true for me. However I never imagined it would take this form. She had caught me in her panties and that was not the masculine image I was trying to portray. But I was just happy the relationship was turning sexual.
“I don’t like those white panties on you. White is not your color. Lets try baby blue. Come here and let me take off your panties.” Joan said.
“Aunt Joan, I don’t want you to see my penis. Can I put on the blue panties in the bathroom?” I asked.
“Of course not silly” she said. Joan grabbed me by the hair and pulled me over to her large bosom and quickly yanked down my white lace panties and took a good look at my dick. She spanked my bare bottom twice and told me never to sass her again.
“You have rather large balls for a young boy your age but your penis is not very big. I am going to call it your clit from now on. Don’t worry; from now on it will sever only as your clit. You won’t be fucking anyone with it anymore. It’s just as well sissy boy.” She instructed me.
Joan massaged my clit until it was it’s full throbbing size. Then she put on the silk baby blue panties that felt amazing as they hugged my penis and balls.
“Today we will be going shopping to buy some sexy clothes for my new sissy slut. I don’t want you stretching out my good lingerie with your oversized clit. But for now you can keep the girly clothes on and we will go shopping as women together. Won’t that be fun?” She said.
“Please Aunt Joan, I don’t want to go out looking like this. Please, I beg you. I will do anything you ask. Anything you want. But don’t make me go outside dressed like a girl.” I pleaded.
“Well, I understand that you are shy and I may not take you out today but sooner or later you are going out with me dressed like your sissy self and we are going shopping. You know you secretly want to and you know you will enjoy it so stop trying to lie to me.” She said.
“Please, not today, I will do anything.” I begged her.
“Well little sissy, there is one thing I want to do to you. I think it needs to be done to straighten out your attitude. From now on I don’t want any macho masculinity coming from you what so ever. I am going to strip you of the stupid social training you have received and make you soft, gentle, light, and as sweet as the nicest girl in town do you understand?” she said.
“I will do anything you want me to do. I promise.” I said.
“Good girl. That’s the right attitude from now on.” She said.
Aunt Joan took me gently by the hand and bent me over the side of the bed and told me to wait there in that position for her to return. I waited in that position for 10 minutes wondering what she was going to do to me. I began to hope that she was going to fuck me. Whatever she was going to do, I hoped she would let me cum. I was dying of my constant hard on.
Joan returned wearing black stockings and block high heel shoes with white panties and no bra. Her breasts were gigantic. She was also wearing a huge strap on dildo and I immediately had the urge to suck it.
“From now on little sissy, your mouth is going to be my personal vacuum. I am going to train you to suck whatever I command you to put your lips on. Let’s start with my tits.” She said.
I placed Joan’s left breast in my mouth and gently sucked on her nipple for 5 minutes until it was fully erect.
“You are excellent at that. Very good. You have got Aunties tits very hard. And my pussy is also very wet.” She exclaimed.
As I was sucking her tit, she slipped her nipple out of my mouth and gently slid her 8 inch dildo into my mouth. I opened my throat wide and began to suck on it just like my ex girlfriend sucked on my cock last year.
“Take it all inside little sissy boy. Make that cock feel nice and warm and wet. Use your tongue to gently massage it up and down and cup the balls with your little sissy hand.” She said.
I did as I was told and began to fall into a rhythm. I looked up at Joan as much as possible as I sucked her plastic cock.
“You still need lots of practice sucking on a real man cock sissy boy. But we have the whole summer for that.” She told me.
Joan pulled the dildo out of my mouth and walked around behind me. She spread my legs apart just a little and pulled my balls out from under me. Without warning, Joan put the head of the dildo against my blue panties and pushed in into my ass with my panty going first. She pushed it as deep into my ass as I could take it and held it there. It hurt at first and I moaned and whimpered despite myself. She pulled it out and pushed it in again, keeping it inside me. I whimpered again. She did this at least 10 times until my cries subsided and I began to feel the pleasure of it. Now I moaned in joy as the dildo entered my ass along with my silk panties.
“From now on sissy slut, the only pleasure you are allowed is in this way. With a cock in your ass. Only with a cock in your ass are you allowed to cum. Do you understand?” she asked.
“Yes, I understand.”
“That’s a good girl.” Joan said. She put her hands on my back and began to fuck me gently pushing my body back and forth on the bed that caused friction to my cock and then she told me to cum for her in my silk soft panties. I easily came all over myself in those wonderful panties.
“Now that you have had your pleasure, it’s my turn. You must learn to be selfless with your body and to give pleasure to others above all.” She said.
Aunt Joan tuned me over on my back, stripped off my cum soaked baby blue silk panties and lifted my legs into the air exposing my now limp penis. She splashed baby oil all over my crotch and her dildo and began easily slipped her strap on into my ass again.
“You must be able to take my entire cock in your ass without any thought of your own pleasure.” She told me.
She slammed the dildo as far as it would go inside of me and I cried out. She quickly pulled it out and slammed it in again. I was in great pain. Over and over she did this and faster and faster. I almost blacked out it was so painful. I began to cry and she began to fuck me harder. It felt like she was trying to dig a hole in my ass. I kept crying and sobbing. She stopped and slapped my face and told me to stop being such a pussy. I lay there crying as she left the room and then came back with a double headed dildo that she placed in my mouth.
“I want you to hold on to this to keep from crying so much. When you feel like crying, just keep sucking.” She told me.
I did as she said and she returned to ramming my ass. I sobbed constantly as I sucked the double-headed dildo. After about 45 minutes, my ass was numb and I no longer felt the pain. The muscles in my mouth were sore and I took out the dildo and just laid there while she continued to fuck my tight ass. And then she stopped.
“Well my little sissy, I have fucked the manhood out of you and from now on, you will be my sex slave. Don’t worry, I know you have always secretly wanted to be my sex slave. Just as I have always wanted you to be my sex slave. I have always secretly wanted to fuck your ass. I have fantasized about it since you were 12 years old. It was only a matter of time. I own you now and you are owned by me. From now on you will sleep in my bed at night with me dressed as a woman. You will come with me everywhere I go dressed as a woman. You will be my own personal shemale. Now I know that excites you as it excite me. It’s what we both want.” Aunt Joan said.
And Joan then got on the bed and spread her legs over my face and told me to suck her pussy and lick her clit. I did so with a fever and she came on my face several times. Her juices ran down my chin and neck and I just kept sucking her beautiful pussy. I felt a sense of peace being owned by her now. It was a relief in a way. I knew she would take care of my sexual needs and I would take care of hers. To be a teenager and get the chance to sleep with such an amazing woman was more than I could hope for.
Crossdressing sex story with Aunt Joan written by Ian. Unauthorized reproduction is prohibited without expressed permission. Contact sexstory@postinbox.com for permission.
A Black Personal Trainer Gay Sex Story October 23, 2006
Posted by sexstory in Bi Sexual Sex stories, Black Sex Stories, Gay Sex Stories, Interracial Sex Stories, Kinky Sex Stories, Sex Story.1 comment so far
The Black Personal Trainer Gay Sex Story
I had been a software engineer for 3 years and spent most of that time sitting down at a computer. I had become very out of shape and needed to loose about 30 pounds. When I was laid off from the job, I wanted to take some time to get back in shape and healthy. So I began to ask some of my neighbors for a recommendation for a personal trainer.
One name kept coming up. “Paul the Stud”. Now I am very attracted to women, and can sometimes be a little macho and the idea of going to a “stud” did not seem very masculine at first. But after more people kept talking about him I began to think that I stud personal trainer was probably exactly what I needed.
I made an appointment with Paul the Stud and went to his beautiful home for training. Paul was a large black man with a very soft demeanor. He was soft spoken, kind, gentle and caring. His perfectly cut body, and mustache and huge biceps did not match his warm personality. At first, I was scared to. Paul and his large frame. But he soon melted my fears and I felt his genuine interest in me as a person and getting my health back and body in shape.
After explaining to Paul what areas of my body I needed to work on he told me to take a shower and tell me when I was done. I undressed and took a hot shower and when I got out, I found him waiting for me with a towel.
“First, let me get a good look at your body to see what my work will entail.” He said. And as he dried me off, he took a long hard look at my rather out of shape body.
“Do not worry. I will not judge you. I think the human body is beautiful in all it’s forms.” He assured me.
I stood there naked, exposed and felt very comfortable with this professional checking me out. He was a stud. I began to check him out. His legs were enormous, he had no body fat, his chest was perfect, his neck was huge, and he had a gigantic cock from what I could tell by the bulge in his white body suit he was wearing. I began to feel a little self-conscious that his cock was so much larger than mine, and he was in such great shape, but I suppose that’s what you want in a personal trainer.
“Ok,” he said. “Let’s find something to wear for you to work out in.”
I followed Paul into his bedroom. He had a huge bed with black. Satin sheets. Everything was so clean and smelled great. Paul handed me a tight pair of white spandex bikini briefs that was basically a thong. Then found a white t-shirt that was very tight and cut off at the stomach.
Paul dressed me in is clothes and I felt the blood rush to my penis. It began to rise a little bit and I felt very embarrassed but could not hide it. Paul said nothing and continued to dress me.
Once dressed, I followed him outside by his pool. There was a mat there and he told me to lie down on my back.
Paul kneeled down at my feet and pushed my legs up and then put his knees on my feet. He spread my legs slightly and told me to do as many push ups as I could.
I did 20 and then began to get tired. Every time I lifted my head up, my face went to his crotch. Once again I was aware of just how large his cock was and began to think about that. This gave me extra energy and I was able to do a few more sit-ups. But it also gave me a raging hard on that was in full and complete view of Paul. Finally, I collapsed in exhaustion.
“Very good.” He said. “Now we will stretch out a little more”.
Paul lifted me up and stood behind me and held on to my hips. He pressed his cock against my ass and I could feel the size of his member. I was almost too erect to do anything but I pretended I wasn’t.
“Now I want you to bed over as far as you can. I will hold you from behind so you won’t fall over.” He said.
I bent down and he told me to hold that position. Then he told me to slowly rise up again. All the while he was holding my hips. We did this 5 times and each time I felt his cock getting bigger in his tight white body suit. I knew he was getting turned on by this, just like I was but I said nothing.
“Ok. Good. Now relax and turn around and face me.” He said.
I was afraid to do this cause I was so hard and my cock was coming out of my small thong. But I turned around to face Paul the Stud. He looked me in the eyes with his soft brown eyes for a while and spoke gently.
“It’s alright you know. This happens all the time.” He said.
“Paul, I am a little confused because I am not gay. And I can’t recall a man every turning me on the way I am turned on now.” I said.
“Well don’t be embarrassed. I am a professional and will keep this just between you and I.”
“But if I was gay, you would be the kind of man I would want to sleep with.” I said and blushed.
“That is very sweet. It’s actually a wonderful thing because I can motivate you much better if I turn you on. Do you understand?” He said.
“Yes” I said, “completely”.
Paul took me by the hand and led me into his bedroom and slowly undressed me. I felt like I could cum at any second. He put me in the doggy style position on the edge of the bed and placed his huge cock against my naked ass and grabbed a hold of my hips.
“Now we are going to do some exercises” he said. “Lean forward and then lean back slowly.”
We did this for several minutes very slowly and I became even more excited. Paul then took off his body suit and placed his 9 inch black cock in the crack of my ass.
“How does that feel?” He asked.
“Oh Paul” I said, “I think I am going to explode”
“I’m glad you like it. You are doing very very well.” He affirmed.
We continued to rock back and forth together with him holding my hips and his thick cock resting in the crack of my ass. Back and forth, back and forth. I wanted him to fuck me now. I had never wanted any man really. I was ashamed of my feelings and very confused. But all I knew was that I wanted his cock in my ass so bad that I was willing to do just about anything for it.
“Please Paul. Please fuck me now.” I quivered.
Paul took some lotion and began to message my ass hole with it. He fingered me and I almost came.
“You are very tight. Is this your first time?”
“Yes I said. I am a virgin.” I said
“Well, this is going to hurt you a little at first but just relax and stay still and soon you will start to enjoy it.”
The head of Paul’s cock was entering my ass and it felt like a fist. It spread me open and I felt a wonderful sensation of freedom. He kept pushing in slowly and it began to sting. Slowly he inched his 9 inches inside me. I closed my eyes and noticed how complete and full I felt. I could feel his large ball sack bump against mine.
Paul began to slowly and gently fuck my ass and I told him I was going to cum.
“Not yet. We still need to exercise a little here.” He said. And he reached around and grabbed my erect penis and squeezed it so I could not cum.
We moved back and forth and back and forth slowly together. I could feel my stomach muscles getting a good work out.
After 10 minutes of getting ass pumped, Paul stopped.
“How do you feel?” he said.
“I feel like I am going to cum as soon as you release my dick from your hand.” I said.
“Very good. You are doing well for your first time. You can take my entire cock. Good boy. We are done with our first session but I am not done with you yet. I am going to release your cock but do not cum just yet.”
Paul took his hand off my penis and pulled his cock out of my ass. He gently flipped me over on my back and raised my legs in the air. He pressed his weight on top of me and began to kiss me. His mustache felt funny against my upper lip. His tongue invaded my mouth and filled it as it met my tongue and we sucked each other’s lips.
Paul reached down to his cock and began to slip it inside my ass, which was now very stretched out and this time, as he entered, it felt wonderful.
As Paul kissed me he began to fuck me slowly. He rocked me with the springs of his mattress and I could feel his balls knocking against my ass.
“I am going to cum now.” I said. And as I came, the muscles in my ass began to tighten. And he began to swell to an enormous size and I could feel his muscles pulsating as he came in my ass.
We both moaned together until he collapsed on top of me and slowly pulled his cock out along with a huge amount of cum.
Paul held me and kissed me for a few moments.
“You did very well for your first day.” He said. “Would you like me to shower you off now?”
“Paul, you can do anything you want to me now.”
Kinky Girlfriend And The Therapist Sex Story October 22, 2006
Posted by sexstory in Bi Sexual Sex stories, Black Sex Stories, Crossdressing Sex Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Gay Sex Stories, Group Sex Stories, Kinky Sex Stories, Role Play Sex Stories, Romantic Sex Stories, Sex Stories For Women, Sex Story, Three Some Sex Stories.2 comments
Kinky girlfriend and the therapist sex story.
Julie and I had been dating for about a year and our sex life began to decline. We never had amazing sex but it was good sex for sure. I lost my job and she got a promotion at hers and I began to get depressed and a little jealous and did not always feel like I was pleasing her. It started to spiral downward until we only had sex once every 3 weeks. And it felt like effort. I began to think she was cheating on me and confronted her about it.
She admitted that she had been fantasizing about other men for some time although she had not been with another man. She also admitted there was a guy at work whom she had gone out with drinks a few times. And that they had kissed one night but she felt really guilty about it.
This made me even more depressed so Julie suggested that we go and see a therapist to repair our relationship and try to make things work. I was uncomfortable with that idea but suggested we become our own therapist. I suggested that we drink a few bottles of wine each night and pretend that one of us was the therapist and the other person was the patient.
On our first session, Julie was the patient and I was the sex therapist. I asked Julie what her sexual fantasy was that turned her on the most, or at least one that she was comfortable sharing. At first she was reluctant but after a few glasses of her favorite wine she began to spill it.
“I have a fantasy about being picked up in a posh hotel lobby by a total stranger who said only a few simple words to me. He takes me back up to his suite on the top floor and fucks me without mercy for over 2 hours without saying a word. When he is done with me, he allows me to sleep in his bed and he leaves me there with the keys. I take a nap and then leave.” She said.
Well, I thought, that is doable.
So a few days later I rented a posh hotel room downtown and also bought some sluttish outfits for Julie to wear. I returned home and placed the outfits on the bed with a note saying I would not be coming home tonight but I wanted her to go out and have a good time without me. And I had even bought her something nice to wear.
I arrived at the hotel and put on a Tuxedo and headed down to the lobby bar and bought a few drinks and waited for Julie to arrive.
I saw Julie walk into the bar wearing a see through dress I bought her and an extremely low cut blouse. All the guys stopped to look at her and I turned away so she would not see me.
After about 5 minutes, a guy approached her and asked to buy her a drink. She said yes and they talked for a few minutes and then Julies went to the bathroom. I got up and walked over the guy and said that she was my wife and to leave her alone. He apologized and said he didn’t know and then got up and left. I returned to my seat to spy on Julie some more.
Another guy, about half of my age, gave my girlfriend a shot. They laughed and talked for about 30 minutes and then Julie said something that made him walk off. Then another man, a very large and handsome man, approached Julie and bought her a vodka tonic. Julie kept staring at the man and I sensed she had the hots for him.
The man asked Julie to dance and I watched and they slow danced and slowly felt each others body. Then another man asked to cut in and Julie began dancing with more men. She became the life of the party.
Enough was enough and I got up and asked to cut in. Julie looked shocked to see me but I introduced myself as an alias. I took her in my arms and grinded slowly against her body. I could smell the cheap perfume of the previous men on her. It turned me on even more to think about it.
I said, “I have a suite upstairs and a bottle of champagne for you. Come now sweet princess and don’t say a word.”
She nodded and smiled and I took her hand and led her to the elevator. Once inside, I forced my tongue down her mouth and slammed her up against the corner of the elevator. I reached under her see through dress and felt her soaked thong. She had been having a very exciting night and now I get to reap the rewards. With doing only half the work.
I led her to my hotel suite and opened the door. She went to the window and said, “nice view”.
“Shh” I said. “ No talking”
I opened a bottle of bubbly and dimmed the lights and grabbed her before she could take a sip. I shoved my tongue her throat and ripped her dress off, destroying it in the process.
I slipped my finger inside her warm and wet pussy and her juices oozed down my wrist. I lifted my hand up and made her suck on my finger as I watched.
Then I pushed her down to her knees and made her unzip my large cock and stare at it. I tilted her head to just stare at it for a minute and then allowed her to begin to suck.
She began to suck my cock like she never had before. Bobbing up and down, back and forth, with complete abandon for her humility. She was consuming it and I was about to cum.
I raised her up and threw her face first down on the bed. I ripped her panties off and spread her legs apart wide. I put one hand on her head to force it into the pillow and the other on her ass.
I wasted no time and slide my cock in as far as it would go. Deeper and deeper until she moaned and whimpered and tried to break free. I held her down and began to fuck her, and keep driving deeper and deeper.
Julie began to cry in a way I had never heard. She was in pain but was having orgasms too.
I fucked her with all my weight. Letting my ass drive my shaft as deep as she could take it on her back.
I quickly flipped her over and put my hand over her mouth so she wouldn’t speak and then lifted her legs over my shoulders and sunk it as far as she could take it. Then began to use the springs of the bed to bounce her around on my cock. She was cumming and dripping all over the place and crying through my hand that covered her mouth.
Finally, I could hold out no longer. And pulled out and began to cum all over her face. I rubbed it around her face and slipped my cum soaked finger into her mouth and she sucked it clean.
I quickly got up and turned on the Jacuzzi. Then walked back and picked her up in my arms and carried her to the hot tub. I placed her in and then got in. She sat on my lap as I fondled her breasts making her nipples hard again.
This got me hard again and I lifted her up and put her down on my cock in the warm bubbling water. She bounced on my cock until we both came again.
Then I dried her off, carried her to the bed and tucked her in. I made her suck my cock one last time before she fell asleep. Then I left the key on the table and got in my car and drove home.
The next night I met Julie for dinner at our favorite restaurant and asked her what she had done the night before.
“I met my therapist and we had a fantastic session.” She said.
Older Woman Boss Sex Story, part 1 October 21, 2006
Posted by sexstory in Crossdressing Sex Stories, Domination Sex Stories, Forced to Feminize, Sex Stories For Women.1 comment so far
Older Woman Boss sex story, part 1
I was only 19 when I began working for Miss Jansen. She was an older woman in her 40’s and lived about a block away from me in a very nice apartment building. She had seen me in the local neighborhood grocery store a few times and one day asked me if I could help with her some things around her condo. Since I was a struggling musician, I needed all the odd jobs I could find. My hair was long and I was thin and it was not always easy to find work.
The first day I showed up at her apartment, she was wearing a sexy long white nightgown worn lose enough for me to catch an eyeful of her large and beckoning breasts. They were the kind of breasts that can distract a man so much, it’s difficult to have a conversation with the face that owns them.
Miss Jansen asked me to clean her kitchen from top to bottom. I went to work but all I could think about were her amazing breasts that seemed to stare at me and call my name. Miss Jansen came into the kitchen and said,
“I want you to bend down there, and get under the sink now. That’s good. Get under the facet and clean around there nice and good for me.”
My ass was up in the air and I was in a very submissive position and very aware of it. It felt good and I thought perhaps it was one step closer to being able to suck on her large perfectly formed nipples.
Once I finished the kitchen I went looking for her and heard her in her bedroom. She was moaning and I thought perhaps she was in pain so I knocked on the door and said,
“ Are you alright in there? I finished the kitchen.”
I heard some commotion and then she opened the door and was very upset.
“Don’t you ever bother me while I am in my bedroom do you understand?” she said.
I agreed and went out on the balcony to pot some plants. When I was finished there, she asked me to clean up her bedroom next.
While I was cleaning her bedroom, something caught my eye in her top draw. I knew I shouldn’t be looking in her stuff but I could not resist. I opened the draw slowly and saw a large collection of dildos and lotions. There were about 10 dildos of all sizes and shapes and I the curiosity got the better of me. I picked one up and just then I heard a loud voice behind me say,
“You like that one don’t you?”
“Um, I’m sorry,” I said and put down the dildo and closed the drawer.
“Don’t be shy she said, it’s ok if you like them, but they are mine, and you are not allowed to touch my things unless I say it is ok. Do you understand”
“Yes ma’am” I cooed.
“ I am going to have to teach you to be more respectful of my things. If you want to enjoy my things, you must earn that privilege first. Do you understand?
“Yes ma’am.” I said.
“Now come over to the bed and lay across my lap”
“Why?” I asked.
“I must punish you for taking without asking. Come here now if you want to keep your job boy.”
I went over to the bed and pay across her lap. She began to spank me very hard. It hurt at first but then I began to like it. I arched my ass and began to moan. I could feel my cock getting hard and she could too.
“I see you like this. The point is for you not to like this. I can feel your little hard on rubbing against my robe. That is a very very bad boy.”
She spanked me harder and harder and then asked me to stand up, spread my legs, and turn around.
“Now this is going to hurt a little. I want you to take it like a man. Do you understand?”
“Yes ma’am” I said.
And then she kneed me in my groin. I fell to the floor in pain. She took the dildo out of the draw and stood over me and said,
“Do you still want this?”
“No ma’am” I said.
She left me on the floor and when I felt better I got up to leave her apartment. As I left she told me to come back tomorrow at the same time. And that she hoped I had learned my lesson.
I debated on returning, but I figured that since the women had spanked me and hit my balls, that there was a good chance more sex would come. I was embarrassed about the dildo, and everything else, but I needed the sex, and the money badly.
The next day, she greeted me in tight sweat pants and a bra. Again, all I could do was stare at her large perfect breasts. She sent me in the kitchen again and asked me to clean her drain. I unscrewed the drain and all the gunk and garbage spilled out on my head, shirt and pants. Miss Jansen saw this and said,
“You idiot. You can’t walk around my apartment with all that crap on your clothes. Now go into the bathroom, take off your clothes and take a shower. I will wash your clothes for you. Now go!”
Ahh, things were getting good now. I undressed, left my dirty clothes on the toilet and got into a hot shower. Miss Jansen came in and took the clothes and said,
“Don’t worry. I am not going to spank you for that. It was an honest mistake. But don’t let it happen again.”
She took my clothes and left. 10 minutes later I got out of the shower and toweled off realizing I had no clothes to wear. Just then she came into the bathroom with a nightgown and panties and said,
“This is all I have for you to wear. Give me your dirty towel. Don’t worry; I have seen it all before. Give me your towel.”
I slowly took my towel off and she took it from my hand smiling.
“Here, now put the panties on first.”
I took the small thong pink panty and slowly inched it up my legs and thighs.
“It’s a perfect fit.” she said.
Now turn around and I will put this pretty night gown on you.
I turned around and she gave me a good slap on my butt.
“My dear, what a cute butt you have there. You look fantastic in those panties. Now come here and look at yourself in the mirror. Aren’t you pretty? I think your pretty. Now sit down and let me put something else on you.”
I was getting pretty hard by this point and would have done anything she asked me.
“Good boy.” She said and applied red-hot lipstick to my lips.
She stood me up and took me into the bed room and she laid down on the bed.
“Just because you are wearing my clothes, does not mean you are still not working. Reach in my drawer and take out the large dildo you were so interested in yesterday.” Miss Jansen said.
I took out the dildo and brought it over to her.
“Good boy. Now come lay down next to me.”
“Do you know what to do with a cock this big? I didn’t think so. So I am going to have to show you.” She said.
She began to suck it, taking it deep in her mouth, and then began licking it while holding the balls very lightly. It was turning me on so much.
“Now your turn bad boy.” She said.
I took it in my mouth and tried to suck it but I almost gagged. She told me to slow down and take it nice and slow. Once I got more comfortable with it, I began to enjoy watching her, watch me such on the dildo. She began to play with herself and exposed her pussy to me and placed my hand on top of hers and is rubbed and massaged her clit, as I kept sucking on the dildo.
She began to cum and climax and make wonderful noises and moans.
“Keep sucking on that cock. It is turning me on so much to see you do that. With your red lipstick, and pink panties. Keep sucking boy.”
Miss Jansen then slipped down my pink panties and began to suck my swollen cock which was fully erect. My mind was completely gone at this point and I came in less than 2 minutes into her mouth.
“Now, wasn’t that better than cleaning the bathroom”
“Yes ma’am” I said.
“Come back tomorrow at the same time. I have a very large friend I want you to meet. I have a feeling you are going to like him.” She said.
“Him?” I asked.
To be continued.
Shemale Birthday Sex Story October 18, 2006
Posted by sexstory in Bi Sexual Sex stories, Interracial Sex Stories, Shemale Sex Stories, Three Some Sex Stories.2 comments
Shemale Birthday Sex Story
As a joke, my girlfriend called a shemale escort service to come over and give me a message for my birthday. She asked for the biggest, blackest shemale who was hung like a horse to come over. But of course it was a surprise and I didn’t know about it until it was too late.
After my birthday cake my lovely girlfriend asked me to take a shower and come out only wearing a towel. Looking forward to a birthday orgasm, I did I was instructed quickly. When I entered our bedroom I saw a large black shemale standing next to my girlfriend with a smile.
“Now come lay down and get your birthday present.” My girlfriend chuckled.
I approached the shemale and she said, “happy birthday big boy. Now lay down on the bed face first” in a rather husky voice.
My girlfriend exploded in laughter and said, “I’m going to leave you two alone now but I will be back in an hour to check up on you.”
The shemale introduced herself as Tina and instructed me to give her a hug. Since she was much larger than I and could have easily kicked my ass, I did so. As we embraced I was surprised at how good she smelled and found myself a little turned on by the aroma.
Tina hugged be for a long time and let her hands explore all over my exposed back. I could feel the bulge in her rather tight sweat pants rub against the bulge underneath my towel. She felt rather hung and even more so than I.
“Now be a good birthday boy and lay down here sweetie.” Tina said.
After I lay flat on my back, Tina began to rub oil all over my back and slowly unwrapped my towel exposing my butt. She then placed a pillow under my pelvis, which arched my naked ass slightly in the air. I felt quite powerless but I was trying hard not to enjoy it and trying even harder not to get an erection.
Tina turned my skull to one side, the side of the bed she was standing at. I had a close up view of her tightly packed large cock in her spandex sweat pants. She was huge. I stared at her cock for a few minutes mostly out of curiosity.
“Do you like what you see birthday boy?” She whispered.
I shut my eyes and said, “ummm, it feels good. Thank you.”
Tina’s large and muscular hands felt incredible as they slowly messaged my back and slid down my legs and on top of my ass. She was very strong and I was quite relaxed.
I opened my eyes again to peak at her gigantic cock standing so near my face.
“I caught you peaking.” She said. “Would you like to see it?”
“See what?” I said.
She slid her hands over her spandex pants and began to massage her penis that was growing even bigger.
“Umm, I don’t know what you mean” I said.
“Don’t be shy, I know you are curious about what is under my pants. I will show you if you want me to.”
I lifted my head up slightly and just stared at her bulge. And before thinking I asked her,
“Can I kiss it?”
“Why of course you can kiss it.” she said.
I pressed my lips against her spandex pants and gave her large dick a little peck. Then another one. Then 2 more and rested my head back down on the beg. I was completely erect now and afraid.
“That was very very sweet birthday boy.” Tina said and continued my massage.
I closed my eyes and tried to relax but all I could think about was placing her large black cock in my mouth.
“Ok, your back in done, now turn over and let me do your front” Tina said.
“No, that’s ok. Just do my back ok?” I said nervously.
“Now come on, turn over. If you don’t I will turn you over myself.” Tina said. And she began to force me over on my stomach. Tina was very strong and forceful and I was helpless to resist. My fully erect penis was exposed now.
“I see that someone likes my message. Don’t be shy. I am very flattered. Now just try to relax while I do your front.” Tina said.
Tina turned my skull again to face her large budging cock as I lay helpless on my back fully erect and exposed. I stared at her large black cock for 5 minutes and could no longer control myself.
“Can I see it?” I whispered.
“Yes, you may” Tina said.
Tinas large hands unzipped her red spandex pants and she rolled them down over her 9 inch cock that was halfway erect.
“Do you want to touch it?” Tina asked?
I began to slide my hand up her thigh to her large ball sack and cupped her balls in my hand. The contrast of my small white hand on her rather large black balls turned me on despite myself.
I was amazed at the size of her cock. She was 9 inches long and 3 inches thick and not even fully erect. I wanted to see how big it could get so I began to stroke it up and down.
“You are very good at that. Momma likes that.” Tina said. “Do you want to kiss it again birthday boy?”
Without thinking I began to kiss her huge shaft and cupped her balls in my hands. Tina grabbed my jaw and forced it open and slowly entered my mouth with her black cock.
I began to move my head forward and back as I let my tongue slip along her shaft. I couldn’t believe what I was doing. I was sucking a shemale’s cock. And in my girlfriends bedroom. And even worse, I was totally enjoying it.
Tina’s large strong hands wrapped around my skull and she took control on the movement on her dick. I opened my mouth wide and tried to take her cock as deep as I could.
Just then, the bedroom door opened up and my girlfriend caught me with a large black shemale cock in my mouth.
“Well, I see you are enjoying your birthday message. Do you mind if I watch?” My girlfriend said.
I was shocked that she was not upset. I slipped Tina’s cock out of my mouth and said, “I’m sorry, I don’t know what came over me.”
My girlfriend said, “Honey, now you don’t have to hide from me, I don’t want there to be any secrets between us. It’s your birthday and you can do whatever you want.”
My girlfriend walked over to the bed and said, “My goodness that is a huge black cock you have Tina. When my boyfriend is finished with it, perhaps I can have a turn. Now go back to what you all were doing and don’t mind me.
Shyly, I took Tina’s cock back in my mouth and found a rhythm again with my sucking. My girlfriend began to give me tips on how to take it all down my throat.
“Now that’s better honey. You have a talent for this. You are really turning me on with that large black cock in your mouth. And you hold Tina’s balls so delicately. Almost like a girl. Almost better than me.”
My girlfriend got up and went into the closet and took out a large black 10 inch dildo that she had been hiding. She sat down on the chair next to the bed and lifted up her mini skirt and panties and began to fuck herself with the large dildo. Moaning and watching me as I sucked and sucked Tina’s cock like a chocolate Popsicle, she launched into several orgasms and screamed out,
“suck that big black cock baby, suck it like I showed you”
Tina lifted my legs up and began to finger my asshole. Her large fingers penetrated deep into me as I kept sucking her. I felt very vulnerable and submissive to Tina and kept sucking.
“I want you to come inside my boyfriends mouth Tina.” My girlfriend told the shemale.
And then Tina began to explode large ropes of cum into my hot mouth. She forced my head from retreating and I was amazed at the amount of cum that was shooting down my throat. It seemed like more than a mouth full.
“Now be a good boy and swallow Tina’s cum” My girlfriend instructed me.
I swallowed every last drop and felt a little humiliated. It tasted salty. I looked up at Tina and she smiled at me.
I was about to cum myself but Tina asked me not to cum just yet.
“My time is not up yet and since you are so good as sucking my cock, I want to let you do it again. But I want to suck yours too. Do you think your girlfriend would mind?”
“Not at all Tina, go ahead. I’ll just keep fucking myself with this dildo and watch.” My girlfriend said.
Tina lay me flat on my back on the bed and then got on top of me in the 69 position. She began to suck on my cock for awhile and then when she was erect again, she gently placed her huge black cock in my mouth again. She used her hips to slide her dick up and down in my mouth as I just lay there helpless and watching her balls bounce up and down on my nose.
“You look so cute in that position. I never thought it would turn me on so much to see you sucking a cock.” My girlfriend said in between her multiple orgasms.
Tina slipped her finger in my ass and I could not hold back anymore. Tina was giving me the best blowjob of my life. I began to explode in her mouth as she exploded in mine. Warm cum dripped down my throat and I moaned and bucked.
Tina pulled out her finger from my ass and licked my cock clean. Then I kissed hers gently again.
“Times up” Tina said.
Boy Toy 1 October 18, 2006
Posted by sexstory in Crossdressing Sex Stories, Domination Sex Stories, Forced to Feminize, Sex Stories For Women.2 comments
Boy Toy 1
Finding an apartment to rent with a private pool has always been a dream of mine but I rarely had the money so when I discovered that a mature woman was renting out her guest house on her large estate and there was free access to her pool, I jumped at the chance.
Joan was in her late 40′s and a very voluptious woman. When I filled out the rental application she asked me how I felt about lesbians.
“Well, I generally like them and find I have a lot in common with them. ” I said.
Joan explained that she was a lesbian and often had pool parties with her female friends. I became excited just at the possibility of that. Little did I know just how fun it would be and what my role at these parties would be.
Shortly after I moved into the guesthouse, Joan and I would sit up late at night drinking wine and talking by the oval shaped pool in her backyard. One night after a few too many glasses of Merlot, Joan began to ask me about my sexuality.
“Have you ever dressed up as a woman?” she asked.
“Well, maybe once or twice” I said.
“Did you enjoy delicious it made you feel?” she said.
“Well, just between you and me, I did enjoy the feeling of the tight panties around my waist. I am a submissive man and it felt very natural to wear woman’s clothing. But please keep my secret between you and me ok?”
“Come here and sit between my legs for a second.”
I shyly approached Joan and sat between her legs with my back to her large breasts that were pressed against me. She reached into her purse and brought out a roll of lip-gloss and applied it to my quivering lips.
“Now, how does that feel my little girly boy?”
“It feels very soft and smooth.” I said.
“You know, I think you would make a very beautiful woman. Come inside with me, I want to show you something. “ She said.
Joan took my hand and escorted me to her bedroom closet and asked me to pick out something to wear. I choose pick stockings, pink panties and a pink baby doll teddy
“Very nice choice my little sissy. I think you have done this before haven’t you? Now take off your boy clothes and I will pink you and pamper you my sweet boy”
I stripped off my clothes and Joan watched intensely and smiled. Once naked she asked me to turn around so she could get a good look. I was very erect and a little shy. She asked me to spread my legs slightly and bend over. I did so and this pleased her.
Then Joan began to dress me in her pink clothes. Once dressed she led me to her makeup table and applied makeup to my face. To finish it off, she found some red high heels and I slipped them on.
“You look much better like this don’t you think?” she said.
I was too shy to answer and just nodded my head a little.
“Let’s finish our wine outside now my sissy boy. “ Joan said.
Joan asked me lots of personal questions about my fantasies. I admitted to her that once my ex girlfriend had used a strap on dildo and I had the best orgasm of my life. And that I secretly thought about sucking cock sometimes.
“Come sit on my lap little sissy. Since you shared such personal information I want to give you something special now.”
I sat on Joan’s lap and she pressed her lips against my lips and our matching lip-gloss began to slide around and as her tongue invaded my mouth, I began to taste the sweetness of the lip-gloss and was engulfed in her purfume. Joan’s hand slipped down into the back of my pink panties and she began to massage my ass. I stopped kissing her and looked into her eyes.
“Oh don’t pretend that you don’t like this. Just relax my sweet boy or I will tell everyone your secret.”
I realized at that moment that I was completely under her control. I was her new boy toy and was forced to do anything she wanted with me. Secretly, this excited me so much that I almost had an orgasm.
Joan began to kiss me more as her finger worked it’s way into my tight hole. She moved it in and out and up and down and my pelvis began to buck back and forth.
“Ohh, the sissy likes this doesn’t he?”
Joan’s finger felt so wonderful inside of me and I felt so luscious in my pink clothes. Joan reached around and began to message my cock at the same time she was fingering my hole. I could feel the smoothness of the pink silk panties gently rubbing around my swollen cock. I began to cum inside my panties before I could even think about it.
“That’s a good girl, cum inside your pink panties for me sweet one. Oh you like that so much don’t you? From now on, I only want you to cum with me. You are my new boy toy to add to my stable. “
After I blew my load, Joan directed my head to her crotch and told me that now I must return the favor. I began to lick her clit through her pink panties until she began to moan and twitch. I pulled her panties off her and she pressed my head against her wet pussy and then began to cum all over my face, which cause my makeup to run.
When Joan was finished she said,
“That was a very good sissy. You have my juices all over your face now. You have pleased me very much.”
She embraced me and whispered in my ear.
“My sweet sweet sissy boy. I have many ways for you to please me. Now go to your room and sleep in your sissy clothes and meet me in the morning.”
