Shemales Porn Stories
Page 71

First time...part 2

After lying on the bed for some time enjoying the wonderful ass I had just had she went to refill our drinks. The rum and coke had been flowing at this point and she felt that I was ready for her. As I was lying on the bed I noticed her get on her knees next to and to my surprise her hard cock was now 3 inches from my mouth. She didn't say a word, she just began to tease my lips with it. Having not had a cock in my mouth before, I was unsure what to do although heated in the moment I gave it my best.

I took her hard cock in my mouth and began to suck it while stroking it. From what I c... Continue»
Posted by tom69su 2 years ago  |  Categories: First Time, Shemales  |  Views: 800  |  
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First BJ

Coming home one day a school bully caught me in an area of trees and bushes. He often tormented me and others, being a stupid bully. On this day he ran at me telling me to freeze where I was. I turned and ran. Which set him to cursing me and demanding I stop. He caught up with me and grabbed me by the shoulders. He got in my face and called me names. Fag boy because I was slight and feminine looking, wimp, pussy etc. I begged him to let me go home but my pleading only seemed to increase his pleasure in over powering me. Then he told me since I ran, he was going to de-pants me and make me wal... Continue»
Posted by Celine-Fache 1 year ago  |  Categories: First Time, Shemales  |  Views: 2420  |  
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Nancy finds out...

However, Nancy’s stay with us that summer was going to prove even more eventful than ever I could have imagined. Even after having been caught wearing her things by the neighbour’s son, Lesley, which led to a whole new dimension in our friendship, as you’ll know if you’ve read “Caught in the Act…”

Once again I found myself alone in the house. Dad was at work and Mom had gone to her Bridge Club and wouldn’t be back for ages. As you’ll know if you’ve read “Caught in the Act…” Nancy was really hot stuff and didn’t care who knew it. At 18 she’s a couple of years older than me, in the full bloom... Continue»
Posted by caroletv31 3 years ago  |  Categories: Lesbian Sex, Masturbation, Shemales  |  Views: 1775  |  
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Tranny and Me Meet The MILF

This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the weekend at my place. She said that was a great idea and that she would be over in a few hours. When Chandra got to my place she was horney as hell. She dropped her overnight bag, dropped to her knees and opened my pants. She pulled out my cock and began to suck it really good. She was licking my balls, ... Continue»
Posted by adw276 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1785  |  
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Cruising and Swinging 3

Blackmailed
It was about an hour after dawn on the third day of our Mediterranean cruise. I’d left my wife Melissa, asl**p with our neighbour Roger in his cabin. We’d spent the previous day fucking with Roger in the ship’s sauna and in his port-side cabin. I awoke to watch Roger and Mel making love, but once they went back to sl**p I was wide awake and slipped out to go for a swim.
I had swum about half a mile and was looking forward to the rest of the day as I walked back to our cabin. When I got there, our Brazilian maid, Maria, approached me looking concerned.
“Meester Jac... Continue»
Posted by lankybacon 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2568  |  
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Chatroom trick

I couldn’t believe I was doing this, as I stood by her front door I struggle to find breath on a surprisingly clear day. It had started some months ago, and internet chatroom, boy those things can be dangerous. I had spoke to Mary almost every night, soon chats turned to sex then to fantasies. The difference was she only lived in the next town so when she asked to meet I jumped at the idea, she was so sexy in her pictures. Admittedly Mary was 41 and I was 26, but still. She stood at 5ft10, long straight red hair, a body most twenty one year old girls would be jealous of. Stunning was the word.... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1343  |  
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The trannt from work

I've always had a thing about trannies. Just something. Never sure what or why. I loved looking at them. Seeing their huge tits. Their nice asses. Then seeing a dick between their legs. Now I'm not gay but, was always interseted. I would look up e****ts here in town just to see how far I would go. Finally one day, I got the nerve to do it.

Her name was Angelina. She was about 5'4". Say 125 with some hugh tits. Say 38 D or so. I had seen her where I worked. Would of never thought she was a tranny. Just always saw this hot chick with a huge rack & a hot ass. Everytime she came in the store, p... Continue»
Posted by radec_24 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2655  |  
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ALL MY SINS REMEMBER'D part 3

After numerous flutes of wine Kathy Lee was becoming very vocal despite Hoda's vain attempts to silence her proved to be. The only think that silenced her was when she was sucking my cock. She held it in her hands and then cast glance over at Hoda and a mischievious smile smile across her face.
"Reminds of that visit to the farm," she said. "Remember, Hoda. The stables?"
Hoda's face tightened and reddened and she gave Kathy Lee a solid punch on the arm and pushed her head downward and filled her mouth with my engorged prick. She cast a nervous glance over at me, which I responded with an... Continue»
Posted by slappywag64 2 years ago  |  Categories: Celebrities, Sex Humor, Shemales  |  Views: 461  |  
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Horse Cock Girl Part 2


Amy woke up around dusk, based on the amount of light coming through her bedroom window. She'd fallen asl**p, her new horse-cock still hard and inside her best friend, Lucy.

Lucy was awake, watching Amy sl**p, and apparently enjoying the cock that was still inside her and hard again. Lucy was bouncing slowly and gently on Amy's cock and smiled when she noticed her friend had awoken.

"Good evening, sl**ping Beauty," Lucy said, in a slightly strained voice. She couldn't keep her pleasure out of her voice.

Amy smiled and pushed Lucy off of her, rolling on top of her and kissing her nec... Continue»
Posted by drew1207 1 month ago  |  Categories: Fetish, Sex Humor, Shemales  |  Views: 3280  |  
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MY GIRLFRIEND HAS A PENIS???

I met Gina at a club she was by herself at the bar and when I looked at her I was smitten I knows that sounds cliche but it was like that for me! I sat down a few seats down and ordered a drink a whiskey sour I believe it was took a few pulls to get up my courage then I offered to buy her a drink and she looked over at me with these incredible sea green eyes and actually smiled at me "Ok " she said and ordered white wine which she sipped so sexily I asked her if I could sit beside her and she patted the seat next to her I couldn't believe my good luck to find such a babe here and she likes ... Continue»
Posted by laceysgirl 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 4122  |  
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He has made me the town slut

We live in a very very small town, and now I am the town slut. This is the story of how my obsession with one mans cock turned me into the town slut.
I had been sneaking over to see Phillip every chance I could after he had fucked me and let me suck him. I couldn't get enough of his cock. I tried to see him at least once a week. I would usually blow him, but sometimes he would have the time to fuck me good and hard. I get off work hours before my wife and Phillips wife works later so this gives me time after work to dress up and head over to their house for some sissy fun.
One part... Continue»
Posted by firstknightd 1 year ago  |  Categories: Group Sex, Shemales  |  Views: 3122  |  
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first time crossdressing exp

well this hapened a few years back,ive always been into wearing lacy underwear etc so i put an add in for anther knicker wearer for fun in an adult contact site,and was amazed at the replys,anyway i met a guy and we got on so we arranged a meet later that week at his house,i got there had a couple of drinks as it was our first bi experience, so he went upstairs to get changed and i got changed downstairs i put on black see through lacy knickers sockings and matching bra and mini skirt white blouse and a wig,dave came down wearing a very sexy outfit which was similar to mine also complete with ... Continue»
Posted by mumlover1960 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 873  |  
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Charlotte and her sister go swimming

I did not write this story.

I am 18, I have a younger sibling who is 2 years younger than me called Emily. Even though she is younger than me and we both come from the same parents, she has a better body than me. She is curvy, taller than me, wider hips, small waist, amazing big round ass and huge tits. I'm a D but she is an E, almost F. She turns me on a lot, I know it's wrong but I get horny thinking of her naked.

We both love our swimming. Even though this is an awkward sport for me as I am tiny and it is hard for me to hide a big 8 inch cock. I usually tuck it between my legs pushing... Continue»
Posted by drew1207 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 4548  |  
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A Special Girl - Birth of a Special Girl

A Special Girl - Chapter 1

By Alhana Escher

Birth of a Special Girl


James’ world had been turned upside down. Just moments before he had been getting off with, in his opinion, the cutest and sexiest girl in school. Now though, his was totally freaked out sitting on his living room floor having just discovered his girlfriend Alice wasn’t actually a girl at all. He had found out when his hand, that had been slowly making it’s way up her legs underneath her dress had reached the silkiness of her knickers to find a unexpected surprise waiting within. A small, but definitely hard ... Continue»
Posted by AlhanaCD 2 years ago  |  Categories: Shemales, Taboo  |  Views: 2329  |  
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Daddy's whore

I had always been fascinated by the feel of womens clothes against my skin, and today was no different. Mom was away on a business trip to Canada, and dad was away at work for the next couple of hours.

I had always had an effeminate look to me, with me being 6’1” and thin as a twig at 19, I was scrawny. I had bought a black wig to go with the outfit that I had picked out. It was black 6” heels, black pantyhose, a black garter belt and panties, with a short black skirt and a little black tube top. I was hard just thinking about what I would look like.

I took a shower and completely shaved... Continue»
Posted by vince01 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 4377  |  
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Sissy Slut Amanda Part 1: The Beginning

The Story of Sissy Slut Amanda

This is a story of fiction

Part 1: The Beginning


When I was twenty-three I meet my Sissy Slut Amanda for the first time. Now he was only eleven at the time and it would be many years before I would know him as Sissy Slut Amanda, but still funny to look back at now. The first time I met my future sissy slut, he was Mark, son of the woman I was dating. He seemed like a nice k**, very shy and timid but sweet nonetheless. It’s wasn’t too long after our first meeting that I would be asking his mother to marry me. We had a good marriage and although I nev... Continue»
Posted by TheSissyFucker 1 year ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2496  |  
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A true story: me and a transvestite man - part 1

This isn't a 'story' at all, in the sense that it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.

There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.

OK, about 10 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale is a casual term for transsexual men, that is, they were born with a male body, male genitals, but for whatever reason, don't want to live as men. Today,... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1081  |  
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A Slut is born


There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends.
I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town,
dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?
It had all started a few months ago. I was locked out of my house in the pouring rain,
and I went over to our neighbor’s to see if I could hang out with him until my parents got home.
He was a cool guy... Continue»
Posted by vosmou_vrot 9 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 4243  |  
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cruisin the park for sex

when I started crossdressing,I was bout 15,a few later I got my own place,and was able to do more,except getting in clubs.I was 19yrs old when I got my first appartment,and was not able to get in,cause at the time,the drinking age was 21.and the club,Call club park avenue,hottest gay cub in town,well it was the only one.well I would crise the park where the club was,which was uptown in a very nice setting.so on fridays,and sats nights,I drive around the park looking for hot guys to have sex withI would all way wear a short sexy skirt,and a low cut top,under that a bra,panties,matching gartbel... Continue»
Posted by blonde68 2 years ago  |  Categories: Shemales  |  Views: 623  |  
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Morning Routine at the Mansion of My Misstress


My eyes open with the gentle humming of my small alarm clock. I quickly shut it off so as not to disturb anyone else in the room. Its 4:30am, well before light creeps into the day and the room is now pitch black. Very quietly I rise up on my hands and knees and crawl off of the small doggy bed on the floor next to the big bed. It‘s embroidered with my name “Heather” in pink because it’s my bed and I’m the pet of my Mistress.

I’m silent when I move because I have done this so many times before. On all fours I make my way to the master bathroom and gently close the door behind me. I then st... Continue»
Posted by heatherlingerie 3 years ago  |  Categories: Fetish, Shemales  |  Views: 1142  |  
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