Sex Stories - Shemale - PAGE 4

Jogging

With my 39th birthday fast-approaching, I realized my body was not in the physical shape it once was. I had never been a fan of jogging, but seeing scores of men and women jogging at lunch time told me it was something I would have to try for own self. I work in a business complex near a large residential area that has a variety of parks and greenbelts. I asked a couple guys from my office where they jog and they gave me a few options in the area. I bought myself a good pair of running shoes over the weekend and brought my running clothes to work. The first few days were a little warm and lack of fitness made the jogs brutal on my body. The two saving graces were the being outside in a beautiful area and the significant number of attractive women walking and ... Read More»

Caught by my cousin

I'll never forget the first time I tried my mothers pantyhose and high heels on. I slid a pair of tan nylons on and became instantly erect She had these gorgeous two tone brown heels that i'll never forget. They were made with perforated leather. A thing of beauty really. My legs were thin supple and toned so I looked great in them. I remember having the most incredible orgasm that day. The first of many in heels. One day at school they had an auction to raise money for the the seniors grad trip. They had the boys and girls behind a chalkboard. And as I think about it now I am thinking it was maybe a little inappropriate. They had them roll up their pants or they had shorts on. Their legs were smooth so I'm assuming the boys shaved prior to this. Baby oil covered ... Read More»

My sexy Shemale Cousin

This is 100% True and whyim cumming in my pants while writing it This weekend on my birthday My sexy ass cousin came over I Loved my cousin From the first day i saw her And that was also the first time i beat my dick to her And i Knew she loved me cause i always saw her hold her crotch every time i was near her just like i did when she was near me and this weekend Was the first she was spending the night It was late at night and i was up doing a paper for school I was 14 and she was 21 Now that might seem wrong But If you had seen my cousin You wouldn't care She was Triple E With a 25in waste in circumfrance With An ass like nicki minaj except it was all real!!!!!!!!!!! With long latina hair And a face unlike any other she was the most beautiful ... Read More»

I Sucked My Ex on the Public Bus -TRUE STORY-

I had been dating M., a 21 y/o straight boy for almost 3 weeks when this hot, sexy event took place...I met M. through an online chatroom, and i was his 2nd T-girl experience..He was both studying and working with a very tight schedule and we were hardly seeing each other, despite dating for 3 weeks, he fucked me just twice since we met and i was not happy with that..I was taking advantage of every opportunity to see my new boyfriend, like waking up early in the morning in order to accompany him to his university - Love is willing self-sacrifice! He didn't have a car, so we were taking a bus to school and usually sitting in the back row to cuddle and play when there were some passengers sitting in the front row. The driver and passengers couldn't see us and ... Read More»

Escapade

I'll never forget Homecoming this year. My boyfriend, Blake, came by my dorm to pick me up around 6 pm. He was in a very excited state and I could tell something was in the works. I asked him why he was so hyper and he told me that he was about to win the sex escapades, which was an annual challenge his fraternity put up each year to its members. There was a $2500 prize for the winner, which was determined by a committee of seven senior members. The way it worked any member that wanted to contest for the prize arranged a sexual escapade for the committee. At the end of the school year the committee voted on the best escapade and the winner got the prize money. Members of the fraternity could buy tickets to watch the escapade on the fraternity's closed circuit TV ... Read More»

Three for Fun

I was on my way home from the bar one night when I noticed a group of ladies standing on the corner talking. As I approached one yelled, “hey sexy looking for the time of your life?” I stop for a minute and stare at the three beauties in front of me. “Well the time of my life does sound appealing”, I reply. So we head towards my place, which is only a few blocks away. When we arrive I tell the girls to go upstairs and undress in the bedroom. I enter the room with a bottle of vodka, which we then pass around until it’s about half empty. I ask the ladies their names, to which the reply, Jessica, Julianne, and Kristen. Jessica has blond hair, 36DD tits and is wearing white thigh highs with a matching garter belt. Julianne, who has the largest titties of the three ... Read More»

The Shemale Wife 2

“The minister is fresh out of the seminary and welcomes any practice he can get,” my wife said. “mel is going to be the best man, and Carla is going to be your attendant. I couldn’t believe she had told our friends about my crossdressing. How could I ever face Mel again? Especially as a hot ass tranny. The night of the wedding, Lulu came in to see how I was doing getting dressed. I was surprised to see Carla and her wearing matching dresses. “Gee, I thought you’d be wearing a tux,” I said, “not dressed like the maid of honor.” “Oh, no,” Lulu laughed. “I said Carla was your attendant I’m your maid of honor.” “But you are the groom!” I exclaimed. “I can’t very well marry another woman. Remember you’re the hot ass tranny crossdresser in this ... Read More»

Different 3some in Acapulco

My job in a large travel agency takes me every march to Acapulco for the Tianguis Turistico, (Mexico tourist fair) that takes place in this nice resort. I very much enjoy those trips, and especially the pole dancing bars, were I would hang out at least 2 or 3 times during my stay. Those places are so different to what you find in the USA that it's most enjoyable to spend time there. The pole dancing bars in Acapulco, and most parts of Mexico from what I have heard are very easy going. The girls are nice looking Latinas, in some upper joins you might find Europeans or north-Americans, but I enjoy the company of those small Latinas, with a round butt and perky tits. I will generally ask for a booth in the back of the place, and not a stool at the dancing bar. ... Read More»

Pounded Into Submission

"Oh shit, fuck my black ass with that thick white cock you fucking tranny." He moaned. "Harder, ram my tight fucking ass baby." He screamed "Quit screaming like a bitch and take it like a man, cock-slut!" She exclaimed. He could feel a growing sensation of pleasure in his taint, a feeling of unnatural pleasure building up inside his loins that had never been experienced before. He felt as if he was about to cum but his hands were handcuffed to the bedpost and the person assailing him was not touching his member. Neither was he. "Something is not right, I feel like I'm about to explode please stop!" He begged his captor. "Is that so, you're telling me that you are such a cock whore that you are about to cum from being ass fucked." She said coyly, ... Read More»

Lara & Skye

Skye shifted and made a contented sigh. Her lover, Lara, was spooned against her back like she always was, holding her firm and protecting her. Shaking off the wisps of slumber still clouding her mind, she sorted out where and when she was. She lay docilely on her side, Lara's arm folded under her arm and under her breasts clutching her tight. Skye was rather amazed that even in slumber, Lara's hold on her was so firm and capturing. Skye subtly shifted her legs, and felt her cock cage clutch on her swollen shaft. Skye was a shemale, a pre-op transsexual male-to-female. The genetic burp in the cosmos had cruelly placed her in a male body, so she had spent the majority of her 26 years on earth striving to correct the error that nature had made. The talents of a ... Read More»

Loaning me out to strangers

My wife and her friend Tina were going shopping in Kansas City for the week end. I knew this meant that I would be with Phillip. Tina's husband and the man I can't stay away from his cock. This meant I would be dressing up like a slut and servicing Phillips cock the whole time our wives were in KC. I started getting ready even before Phillip called. When he called I was already showered and shaved. Waiting for him to tell me how he wanted me dressed. Of course he said he wanted me dressed like a slut, but to dress for going out in public. This scared me. Public? What did he mean by that. I couldn't pass for public, could I? Knowing my face is my biggest give away, I tried to take attention away from my face. I wore a very short sexy Lycra black dress, who would ... Read More»

Discovering Panties - Week One of Summer Vacation

I was 12 years old & it was the middle of summer and like all my childhood summers I was staying with my cousins by the beach. My cousins are twins and I would be lying if I didn't admit I had a crush on them at the time, both of them are fun girls the same age as me. One day after we got back from the beach we all took turns taking showers and I was the last one to get to use the bathroom... I remember walking in and seeing there swimsuits and a thought that had never crossed my mind. Before I really had time to think about it I tried on both of them and then found myself wearing the pink/purple one piece swim suit, I loved how it felt and I decided to wear it while I showered. (at this point in my life I could get erections and not cum) After the ... Read More»

My First Girly Cock

It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. I don't consider myself being gay, but I always had that ardent lust to be with a transsexual woman. I just couldn't get them out of my mind. This passion started a couple of years ago, while I was surfing on the Internet looking for hot stuff. Immediately I felt something. That first time, when I saw a woman with a cock. It was a magnificent sight. Now I'm 20 years old. And I'm heading to Nickie's house. She lives a couple of blocks down the street. She is 22 and ... Read More»

My weekend with Kelly part 3

I slowly entered the jacuzzi tub with Kelly holding tightly on to me. Mt cock was still buried inside of her tight ass, her cock was hard and pressed tightly into my abdomen. I eased down into the water raising her off of my cock and placing her into the water. She sighed as her body was covered by the soothing water. Then I stood up and left the tub. She asked "where are you going?" I told her I would be right back. Leaving her to relax, going to the counter picking up the bottle of wine and the glasses. I poured the wine into the glasses and came back into the bathroom. She turned her head and smiled. I handed her one of the glasses and eased back into the tub. As I sat, she eased over to me, her cock pointing right at my face. I smiled, ... Read More»

Such a whore

I finnaly made this happen a few days ago ! i have been crossdressing for as long as i can remember.I still remember when i snathed a pair of my cousins panties when i was young i dont know theres is just something about womens clothes that just intrigies me . Any way growing up i always masterbated wearing panties and lingere and watching porn ,I always consider my self differnt han other people but i didnt know why , which ended up me turning in to a loner , never really enjoying sex with women i always considered it like a lot of work fucking them when i could just sit back and jack off ,enjoy that way better,i know werid lol. Any way i had kind off got to the point of wondering what it would be like to have sex with a man and me be the women, so i got brave ... Read More»