Shemales Porn Stories
Page 4

My Wife's Affair With The Shemale

My wife Tracy were not married for that long when she had her first affair. I met Tracy in high school and we dated for years before we got married when we were twenty two. I hit the jackpot with Tracy because she is absolutely gorgous and just an all around sweetheart. She has long blonde hair with brown streaks, hazel eyes, long legs, large tits and a tight ass. Tracy has always loved taunting her body wearing cloths like short jean shorts to show off her legs and tank top shirts to show off her stomach and belly button ring. I have always thought of it as a double edged sword because I lov... Continue»
Posted by anonymouspervert69 9 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 6351  |  
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Start of a new life

One day I got a text massage on my mobile while I was at work, it was from an unknown number, it said come home now. So as I only work down the road from where I lived and also I was just going on lunch so I made the 5 min drive home. When I got there, there was a man standing in my door with a box in his hand. When I got to him he said do you live here and is your name Lucie, I said yes but a bit puzzled as I only use Lucie when I am dressed as a girl. He said good now open the door and let me in. After we got in he gave me the box and a letter. I read the letter it was from my master, it sai... Continue»
Posted by dallasrose 6 months ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 6324  |  
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Holloween with a surprise

I read this story on literotica and just had to share it with my Xhamster friends.
Here goes.

Halloween my favorite holiday of the season. If you think a twenty five year old does not like going to costume parties, you've' got no idea what goes on in my life. Everyone I hang out with likes to enjoy themselves to the best of their advantage, and Halloween is one of the best ways we can accomplish that. This year, like the last four years in a row, I was hosting a Halloween party at my apartment with a number of friends coming over and naturally, it was a costume party. There was Jessie who... Continue»
Posted by miguym4m 9 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 6310  |  
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Becoming a Black studs ultimate fuck toy

It all started the day I laid my eyes on my first BIG BLACK COCK ,I had been dressing up as a girl since the age of about 12 wearing my mums panties and pantyhose around the house getting turned on by the feel of the pantyhose and panties . At the age of 15 I realized that I loved pretending to be a girl as much as being a boy ,one day I approached my mum to tell her of my sexual orientation. My mum so supportive and helpful I was really surprised with how she reacted . Son you will always b... Continue»
Posted by foxxiroxxi 2 months ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 6309  |  
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My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.

In August 2007 I was 24 years old and was constantly masturbating to shemale porn. My best friend was getting married and ... Continue»
Posted by feinor11 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 6310  |  
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mom teaches son to be a slut

I loved women. A lot. My obsession with women later became a desire to wear women clothing. One day, three months after my 18th birthday, I could not hold back any longer, and I put on the the most accessible lingerie I could find - that of my mother.

Since then, I frequently visited my mom's wardrobe whenever she was out. I would wear her clothes, and it would make me feel sexy. I would pretend I am a woman, and take sexy pictures of myself. I realized how much I liked this, and this led to me realizing my bisexuality. I wanted a man to make me his woman.

Because I wanted a man so badl... Continue»
Posted by momandboys 2 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 6277  |  
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Cum hungry paper boy sissy

Cum hungry paper boy sissy



When I was thirteen our next door neighbor Pat offered me a summer job
helping him deliver papers and magazines. I quickly said yes and my
foster parents agreed. I liked Pat a lot as he always patted my ass when
Vance and Liz were doing something when he came over for dinner as he
smiled and winked. I loved the way it felt and smiled back as my cock got
hard.

I was light build and kept my long blonde hair in a pony tail and always
wore cut off jean shorts. I had also been jerking off and eating my
creamy delicious cum loads for over a year as I loved... Continue»
Posted by jayymie 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 6274  |  
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He transformed me to his bitch

This happened during summertime. Just after the end of school period, last summer before college. All of my friends had left the city for a beach house they rented. I was to go several days later. So I was alone in an empty city, since everybody was away for the summer holidays.
I was waiting at the bus station when a stranger came and asked me if I knew some decent place to have a beer. I suggested him a few pubs that were close when he asked me to join him. I was surprised and a bit scared, so I kindly declined saying that my friends were waiting for me. He insisted suggesting to meet for ... Continue»
Posted by georgette32hk 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 6240  |  
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Shopping with my s****r - Part 2

Continued...

We drove along chatting freely, laughing when we saw guys checking out the two hot babes in the car next to them. Jane told me what purchases she planned for me, practically a whole new wardrobe I thought to myself, but hey who am I to complain. Jane pulled up in a quiet corner of the carpark and leant over and kissed me gently on the lips, her tongue probing mine. "Come on Dannii, lets go shop!" she giggles.

I climbed out of the car as ladylike as I possibly could, feeling the fresh air up my skirt and flow over my balls felt amazing, a nervous excitement building in... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 6116  |  
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My First Time

when i was 18 i first started to dress up when my mom was out and i loved it. well this is a story of my first time and i would like to share it with everyone. me and my mom live alone and she used to always bring guys back to the house and i used to always hear them having sex and it really turned me on so i tried to peek into the doorway each time and one time a guy left is underwear in the hallway so i picked them up and smelt them and it made me really horny. however this guy turned out to be my moms boyfriend so he came to our house on a daily basis but one time when my mom was out and i ... Continue»
Posted by MegCD 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 6080  |  
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Caught By My Black Stepdaddy

I was 19 and had just finished my first year of college and I couldn't wait to get home. It's not that I didn't have fun, I did. But I wasn't able to do my favorite thing. You see, I have a little secret... I like to wear...BLACK PANTYHOSE AND RED SPIKED HIGH HEELS WITH ANKLESTRAPS and dress up as a girl. And after nearly a year without doing so, I was just a few hours away from being able to feel like the sexy girl I knew I was born to be. What made things even better was that my stepfather Marcus, a big and sexy black man who I've found very attractive ever since my mother started dating him... Continue»
Posted by whawha1976 7 months ago  |  Categories: Sex Humor, Shemales  |  Views: 6053  |  
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Tranny teacher

Hi Al, how is your house sitting summer going ? Pretty good Tim a little boring but the beach is nice. By the way, I didn't mean to but I saw you last night through my window... you were wearing woman's underwear. OH I hope I didn't disturb you Al. Actually I was totally turned on, especially when you pulled out your hard cock.

Really, if you like I can arrange for a private show ... interested ? I don't know I have never seen a man up close before. Ah.. well if you pretend I'm a lady I can walk you through some fun. So you will put on your stockings and the silky things. OH yes and a wig ... Continue»
Posted by TenderLoins 5 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 6005  |  
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My First Time

It must have been 4 years ago.
I was alone and curious, and had been for a while now. I had plenty of girlfriends and knew I was not gay. I just never had feelings for guys, only women. But sex..... sex is sex I thought.
Looking at pictures, watching videos, toying with myself while dressing up in panties and other girly things, had kept me amused up until now. But my desires had grown too strong.

I had frequented a few chat sites, getting into kinky conversations with guys, loving the way they all hit on me and tried to seduce me. It drove me wild and gave me more confidence all the whil... Continue»
Posted by MissieUK 9 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5987  |  
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The Neighbor...

My next door neighbor had never shown any interest in me before. He was married and straight, as far as I could tell.
One night, however, there was a knock at my door. I looked through the peephole and saw my neighbor standing there. He was tall and stocky, with a beer gut that I found sexy.
I answered, not knowing what to expect.
"Hi. I'm sorry to bother you so late." He said.
"Its ok. Is there something wrong?"
"Look, I don't really know how to do this... so I'm just going to be blunt. I know that your gay. My wife and I have seen several different men coming and going at all... Continue»
Posted by bttmblw 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 5983  |  
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Weekend with my s****r - part 1

Continued from sunbathing with my s****r.

The week went so slowly, my mind always wandering back to our day together....stroking my cock endlessly replaying each and every kiss, touch and stroke. We stuck to our agreement of not talking about it when anyone else was in the house, not touching or staring was the hardest part, the sexual tension between us was incredible, I can't believe our parents didn't sense anything. We did leave bedroom and bathroom doors open just enough it was safe. Each morning when Jane left for work she'd leave some underwear on her bed for me.....twice it was e... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 5955  |  
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A Friend's Treat

had recently split with my wife and was feeling very down.

I was invited to spend a few days with my old friend Dave and his wife Tracey.

The first night I was there Tracey turned to Dave and said that we needed a boys' night out and why not go to his club. Dave agreed it was a good idea and within minutes Tracey was dropping us outside what appeared too be a Georgian townhouse.

I hadn’t known that Dave was in a club and was surprised to find he was a member of one. He had refused to reveal what type of club we were going to.

The door opened as we approached and a dinner suited do... Continue»
Posted by maninnylons 2 months ago  |  Categories: Gay Male, Shemales  |  Views: 5889  |  
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Made my hubby crossdress and get fucked by bbc!

Finally convinced me husband to stop watching me take big cocks and to put on a pair of heels and to get fucked while its my turn to watch him!

ive always loved being a cuckold wife, meeting new people, having fun wherever it happens to be at, it really improved our marriage, finally i took it to the next step.

i spend alot of time at nights checking out mostly pics on xhamster and few videos. ive always been turned on by crossdressers, cumshots, and a few others fetishes im into. this time i finally got to see a live crossdresser fucked, my cuckold husband!

so we arranged to meet a f... Continue»
Posted by discreet4rmlanc 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 5886  |  
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First time getting caught wearing Pantyhose

When I was 16 years old, I babysat for my moms best friend. I had know Joanne (my moms bff) all my life, she was my second mother. and a single mother at that. And Joanne was smokin hot! Had thee biggest crush on her since i can remember. Joanne always wore pantyhose or stockings, and i mean always, one night i slept over at her house, i peeked in her bedroom and she was wearing a teddy and pantyhose, and ofcourse i had to masturbate, because like i said, she's a woman who gives an instant boner at first sight. Anyways, she had asked me to babysit her 2 boys on a friday night. Not a big deal e... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 5866  |  
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Happy Birthday to Me

So last month, I was lucky enough to experience one of my favoritest annual events ever: my birthday party!!! Now, for those that don't know, I take my birthday VERY seriously. You see, I was only 12 years old the first time I played with a pecker...and I've been lickin' 'em and suckin' 'em and bouncin' up and down on 'em ever since :-) I suppose my love of being gangbanged and making guys cum on my birthday all began on the eve of my 14th...

It was a hot night in June and I had invited about 20 friends to a backyard birthday party sl**pover. 14 of my best buddies showed up. I had blown... Continue»
Posted by cdsexslut 1 month ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 5872  |  
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My Big Sister

I must say I never pictured this event happening to me in my lifetime, I mean I'm a pretty well rounded k** living in a quiet suburban town. Nothing big happens here, and I'm not some guy that's always finding himself in trouble, so getting bent over and fucked in my ass was the last thing I really worried about, unless I was gay of course, which I'm not.

But no, here I am at eighteen years old, a grown man feeling his ass burning as I try my best to sit comfortably at my desk. As the instructor goes on and on I find my eyes darting back and forth around the room, making sure no one looked... Continue»
Posted by sparkyking 6 months ago  |  Categories: Shemales  |  Views: 5807  |  
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