Free Shemale sex stories. Shemale erotic stories post.

A guy stays in the hotel and picks up a sexy chick in the bar, when he finally takes her to his room there’s a surprise waiting for him…

It started very simply. I was on vacation in Miami, and stayed the hotel, overlooking a nice sunny beach, with dozens of various palms around. Once I saw an attractive woman at the hotel bar and offered her a drink. She accepted and we conversed. I was not planning to pick this girl up and make it out with her, just normal decent chatting. She appeared to be a very good listener and glib, it was very interesting with her. Soon, we were laughing and joking like very close friends. She recommended that we should take the conversation and drinks to her room, and I agreed. She was walking upstairs first, I was following her. I let her walk ahead not only because she was leading a way to her room, but also I could admire that great ass of hers. Extremely good and big ass of hers. I think she knew about it, and made her way wiggling her ass very sexily. The sight of her ass cheeks provocative sway enticed me a lot, and I feel a familiar stir down my crotch. She stopped at her door, gave me a sensual glance, then opened it and entered. I followed her like enchanted. She looked at me and grinned. She had noticed the large bulge at my crotch. Before I could speak, she approached and rubbed the front of my pants.

“Let me take some of this: she whispered.

She placed one hand on my chest and began unbuttoning my shirt and pushing me backward. Without ceasing to rub my hardening cock beneath my pants she continued stripping me off. She seemed like a master of her job, so skillfully and masterly she was getting me nude. I started submitting myself to her. Her hand slid down my chest to undo my belt, then my pants, which fell to my feet. (more…)

A guy gets picked up by a girl in the bar but later he finds out that this girl is not really a girl…

I was tired. I was tired with daily boring routine. I really needed to change something. My life had become boring and my sex life was expressionless. All women I knew proved to be untrustworthy, light-headed and superficial. I really wanted to take a break from the world. I just wanted to live my life sitting in the lovely bar on the Salmon Str, drinking heavy beer and smoking Cuban cigar…. Listening to the Bob Sinclair and inhale heavy puff of smoke. This bar was a place-to-sit for various types of people: sailors, street musicians, biker, hauler, clerks, who spend their time in boring office routine, first-time singers etc… When she came in and sat at the bar stool next to me, I didn’t pay much attention to her, just another client of this place. She was raven haired sun tanned slim long legged bitch, (yeahh, no women, but bitch, as I got used to calling all females this way). She was beautiful and her eyes were bright what made her look like Kim Kardashian, then she was not. I dropped a look at her tits, just a couple of nice humps playing on her breast and moving teasingly from side to side. “Damn, great boobies!” flitted across my mind, but I tried to let out this thought. I inhaled more. Nice long and slightly muscular legs were crossed down, as she sat on the stool.

I puffed on my cigar making more smoke wishing she would move away. She was hot, yeahh, but I was in no mood for any adventure this night. Moreover, I considered this chick as one of those who visit bars pursuing one aim: drain pockets of idiots. I watched her with a corner of my eye and saw her reach into her bag and draw out a cigarette. Of course (as it usually happens in Hollywood films) she couldn’t find a match and turned to me with cigarette dangling between her fingers. (more…)

A guy wants to extend thanks to one of his colleagues and finds out that this sexy chick is actually a tranny…

It’s been 3 years since I got my first experience. I mean sexual intercourse with someone who determined my further life. I still remember my first time with a shemale. She was a tall slim sexy legged blonde that once came into the office of our company. I knew she was an assistant of one of our VIP clients. I thought her boss would send her to extend thanks for one deal we helped them to work out. That was juts a matter of courtesy and good manners.

As I got up from my chair to welcome her, she shut the door, approached me close and pushed me back down on my chair. After that’s he started opening her cloak. She had nothing on underneath her cloak except one thing that amazed me so much that I even opened my mouth with astonishment. There was a big giant like cock with fat head! I knew her before but I had no idea she was a shemale! Motherfucker! I would never admit a mere thought she would turn out to be a tranny! She looked like a real woman, with soft white skin and with strawberry lips! (more…)

A guy who longs for his ass to be fucked is afraid of realizing that he is gay, he goes to the transsexual bar and meets a girl who later turns into a shemale, this is when his dream is coming true…

Andrew was a very simple guy. He was not aggressive, very quiet and nice. Actually he was not quarrelsome, just a man of peace. But we all know that still waters run deep. Over the past few years, Andrew had longed for being penetrated. Vehemently. He needed to be bent over something and fucked thoroughly. He didn’t consider himself a gay, but anyway he felt the hard need for some anal penetration. He first discovered his longings when he was masturbating. One day, while jerking off he placed a finger in his arse. The orgasm was terrific, it was like heaven swim. This orgasm turned to be far more intense than usual. From this day onward, Andrew had entered the world of anal pleasure.

After many months of experimenting, sometimes with dildos or vibrators, Andrew decided that he really needed a real cock inside. As he wasn’t a gay, he would not certainly dare ask any man’s cock penetrate him. But then he realized that a shemale would be the best solution! From time to time Andrew watched some shemale porn and enjoyed greatly seeing a chick with a dick taking a large member inside her rectum. (more…)

A tourist goes to Italy and picks up a local hooker there, he can’t even imagine what is waiting for him….

Verona is a nice city. Here, a motherland of Shakespeare’s “Romeo and Juliet”, there are lots of places of interest to see and enjoy. Verona has much more to offer. The city, also known as Urbs Nobilissima, is the second biggest city in Veneto (after Venice). It is one of the cities that has better preserved its artistic heritage for Italy. By visiting Verona it’s highly important to know its most famous monuments in town, for example the Roman Amphitheater, commonly known as The Arena. It was constructed in the first century outside the city walls, but in the third century the walls were extended to include this arena.

I checked in a nice place, a big red brick house, two-storied building. This house was built and designed in best ways of baroque style. I lived on the second floor, with windows overlooking the stone paved street that remembered old time of wars between greedy feudal lords and townsmen fighting for their rights and freedom. Well, the whole area was inspiring holy antiquity and the dark middle ages. The landlady, who rented this apartment to me, was a well built sexy still beautiful widow, who looked very hot and exciting for her ages. It was tall black haired lustful Italian woman, with everything to turn on. She was glad to accommodate me, a young tall, good looking son of a bitch, but I thought it would be wrong to have any intercourse with her. (more…)

A guy meets a girl in college and he thinks this is his love, well, maybe it is but this girl later turns out a hot shemale with a fat cock…

Hi! Here I am with my own story! I’m a young white guy, a good looking son of a bitch! When I was a college student, one of those numerous young people who always rush for something, then I was a focus of interest for lots of chicks around! But then something changed. Changed a lot. As I remember, from some period of my life I got to liking trannies. I mean chicks with dicks! Well, if I like shemales that doesn’t mean I’m a very perverted bustard yet! There’s something about a sexy babe with perfect makeup and a cock that just turns me on. Maybe that makes me look a bit pervert - I don’t give a fuck!

I remember now, I was just out of college when I made it with a tranny for the first time. She was very beautiful and gorgeous - a hot raven haired black eyed long legged with great fucking hot ass and big boobies slut! I saw her at the store. She had long black hair and long Fashion TV model’s legs. I was nervous, but I went over to her and introduced myself. After she smiled that looked a good sign for me, I also told her I thought she was beautiful. I was still nervous and anxious about what I was supposed to do next. I think at that moment she thought my shyness was cute. The next thing I remember very well – we appeared at her apartment. (more…)

How does it feel, to be sexy, long-legged with painted nails and with a dick in your pants? That must be pretty exciting to discover it for someone who thought he was dealing with a woman?

I don’t know where those thoughts come from but I was starting to get them more and more often. I so wished a guy to take me. But for sure I wanted to be wearing stocking, lacy bra, a short silk rob and may be a wig… I was also so much into painting my nails and putting a lipstick on my lips… and then I would be ready for him.

I got caught. He came in when I was dressed and had make up and all that. I screamed from the shock. Just imagine a man came in when I was dressed like a woman. He turned me around and started kissing my neck, my ears. I tried to escape his arms as much as I could but he squeezed me too tight. His hands went down on my bum; he caressed it and went further down. (more…)

A guy reads an ad in the newspaper and gets interested in the couple that is looking for a bisexual, he decides to try that couple and finds more than he wants…

I saw their ad at the site: “Couple looking for a bisexual guy.” I decided to call them I knew I had to hurry, there were always many people ready to try, I wanted to be the first. When I dialed the number I heard a nice voice, it was a man, he sounded like a beefy man. He turned out to be 48, she was 29. His name was Hayden, her name was Kerry.

“When will we meet?”

“What about tomorrow?” Hayden said.

I knocked on the door. A short beefy guy opened it (I was right about his build). He had a big head, thinnish hair turning grey, wrinkled hands, and a tattoo on one of his hands. Hayden really looked like 48 years of age but no much older. I thought I would probably look the same in some 10-15 years. My ex-partners were much younger, but I didn’t mind trying something new. (more…)

A guy feels really hot when he watches shemale porn on the Internet, he even dreams of getting fucked by a shemale, will that dream come true?

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You know, things, I’m gonna tell you about started when I was a teen. I was like every teen guy, I loved web porn, looked at porn on the internet, surfing porn sites through the web space and masturbated a lot. I loved and now love to watch lesbian porn: it was so hot watching girls having sex. Soon after that I got used to watching and enjoying anal sex, watching the girl having numerous orgasms while she has a huge cock right in her ass. Once I was hardly caught by my dad, but I managed to close the browser in time! Then, later that week, while surfing the web looking for something hardcore, I stumbled across some porn I had never seen before. It was shemale porn. I became fascinated with shemales. From now, every time I got a chance to watch porn I would go straight to the shemale sites and masturbate again and again. Couldn’t say why but for me it was so hard turn on! I loved watching shemales, I loved watching their balls and cocks hang up and down while getting rammed! For some reason they just turned me on so much.

Oh, by the way! You do have to know my name! My names David, I’m 20 and single, I live in New York. I’m not fat but muscular guy, because I work out every morning in a gym. I like my body, it’s well built! Then I go to work, in the end of the day I come home and have dinner, but sometimes I go to the bar down the street and have a few drinks for a couple of hours. About a week ago I noticed a new girl at the gym working out by herself and I couldn’t take my eyes from her. She was gorgeous, big boobs and sun tanned skin, 42 inches round ass, nice flat belly… (more…)

A guy is madly in love with the girl he met in Brazil, she is really hot and sweet but she wouldn’t allow to have sex with her, it’s only on a wedding night, so it comes and there is a big surprise waiting for the guy…

Tonight is our wedding night! It is the night when all my dreams should come true! Sativa and I had never had sex until this day. Many times I’ve tried to do sex, but she always said I needed to wait. I said OK coz I loved my sweetheart! Moreover, when I kept attempting to persuade her, she would say I didn’t love her. Sativa is a very sexy Brazilian chick; I met her during my vacation in Rio a couple of years ago. She has a slim, model body, she is also graced with a nice round ass, blue eyes and juicy lips resembling me that of Angelina Jolie’s. We’ve known each other for 2 wonderful and magic years and every time we kissed looked like it was our first one! Ever since I’ve known her, she has always been a mystery to me because I only knew some of her friends, but never met her family. She explained that her family told her that they rejected her and even didn’t want anything to do with her. I never knew why until this day. We had a private wedding because Sativa didn’t want to see many guests and she felt that was the right time for her to have sex and she was ready to lose her virginity. I loved her and she loved me. We both trusted each other. We had to go through various check ups and testing of all sorts to make sure that we were clean of all diseases. I was always looking forward for this day. (more…)