Shemales Porn Stories
Page 75

My sister, my first, the tranny

A little something different to spice up your lives

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It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go on a honeymoon, so they wanted to take one now. Jack, my stepdad, told me they were going to... Continue»
Posted by 6270daniel 10 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 11250  |  
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How I became a GURL part II

So I'm in college now, I've learned to love and use porn in all its forms, I've learned to be a great cock sucker and to have my ass fucked. I've learned to tie myself up -- as best as possible -- to pee all over myself to get that humiliating feeling. I'd spread the porn mags all over the floor and spend the entire night playing, trying to shoot my cum onto a photo of a cock so that I could lick it up.

The feeling of release whenever I gave in to all of those instincts was fantastic!

I loved cock! But I was a horny 20 something and still chasing pussy. Eventually the girlfriends star... Continue»
Posted by jenn1 3 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  Views: 900  |  
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3 Teen Cross Dressers Misadventure - Part 3 Final

I was with two of them on the bed. One of them spread my legs and began to rub his cock up and down my stockings, I could feel him growing hard. The other sat over my chest and told me to open my pretty mouth. I did but no way could I take it all, he must have been around 8". He shoved his cock into my mouth and down my throat thrusting as I gagged. Although I couldn't see, I heard pleasurable moaning from the man on the bed with Sean. Craig, on the couch with Brett said "I’m gonna screw that pretty little hole of yours and make you scream like the bitch you are." No words came from his mouth,... Continue»
Posted by ClaireCD 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 751  |  
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Tranny Gas Station Attendant

This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intimate, but I consider it just sex. When I say I'm not intimate with other guys, I mean I don't kiss or cuddle or anything like that. It's always just sex, with no strings attached.......usually! There are exceptions to any rule, and this experience is one of them!

... Continue»
Posted by panteeluvr 4 years ago  |  Categories: Shemales  |  Views: 1938  |  
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I posted a craigslist ad.

8 years ago I began crossdressing again and playing with toys. After playing one day while watching videos online I decided I wanted to take the next step and be with a man again. My holes craved it but the butterflies in my stomach had stopped me before. Afraid they would do it again this time I got dressed as slutty as possible and put up an ad on craigslist with a photo of me dressed and spitroasting myself with toys. Pic required I put in the posting. I was amazed at the responses and how many people couldn't read or just saw the photo and replied without reading. I didn't think it w... Continue»
Posted by bibottomboi 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1111  |  
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Baby Sitters Secret


The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated on my wife, I had never lied to a friend, and I had certainly never slept with a girl that young before. All of that changed within a matter of hours. But you know what? I wouldn't change what happened for the world.

Years ago, I moved to the small town of Emberton, Rhode Island to take a job ... Continue»
Posted by drew1207 20 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 8913  |  
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My first threesome.

My lover and I just finished sucking each off and were laying next to each just talking and he ask if I had any fantasy's and I said I like dressing in lingerie. He went to his closet and came out with a black bra and panty set along with a full black slip. He asked if I would put these on and I was up so fast I tripped and fell to the floor. I didn't think I made any noise and started to get dressed. He went into his bath while I was dressing and then his bedroom door open and in step his step mother. I didn't know what to do but stand there in the lingerie. She just smiled at me and wa... Continue»
Posted by billieearls 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 2544  |  
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A recent dream

The following is a note that I sent to my girlfriend of 20 years about a dream that I recently had:

My dream started out with you kissing me goodbye as I left in the car for some conference in a big city. I wasn't fully aware of where I was going other than that I was going away for a couple of days. When I arrived at the hotel and checked into my room, I put two suitcases up on the bed, which was strange. I stood there wondering why I had two pieces of luggage. I quickly opened the suitcase that I remembered packing which had my toothbrush and change of clothes for the day. It had bee... Continue»
Posted by sleeplessone4u 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 662  |  
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My shemale boss part 2

Friday 12pm was here, I nervously knocked at my bosses door part excitement part apprehension ran through my body.

A clear come in could be heard from within by my boss Miss Jones so I went in. Ahh Rob right on time, take a seat and I'll be with you in a minute, she said.

I sat down opposite her desk whilst she continued to study her paperwork. Her black rimmed glasses were on the tip of her nose and with her finger, she curled her long black shoulder length hair. Through her glass desk I could see her tight black leather trousers she had on and black 5" heals. She had walked through my... Continue»
Posted by big_rob49 2 years ago  |  Categories: Shemales  |  Views: 3261  |  
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Sissy Emma is Turned Chapter 3

There in front of me stood my ex wife.

This was the woman I had fought for years to get away from due to her vindictive and bullying ways. After years of trying I had finally left her and moved away, but things had deteriorated as we fought over my rights to see my c***dren. She had used any means possible to ensure I would not be granted access.

She was a big girl and now she stood in front of me looking like a vision of a bdsm fantasy. Her hair was tied back tightly in a pony tail and she had very heavy makeup on. She had a black PVC basque on which was pushing her ample breasts up to... Continue»
Posted by emmahighheels 2 years ago  |  Categories: Shemales  |  Views: 1140  |  
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My step mom turned me into a sissy slut for dad

When I was in High school I would spend the summers with my dad and step mom. She was so hot and always dressed sexy, They were always very playful about sex, not like my mom and step dad. I loved the atmosphere.
During the week they would work all day and I would have the place to myself. I would always go into their room and see what I could get into. I found some picture of the 2 of them nude. Well after that I was always in their room jacking off to the pictures of my step mother naked. Little by little I would find other thing to help with my fantasies. I got into her dressed and wou... Continue»
Posted by firstknightd 3 years ago  |  Categories: Shemales, Taboo  |  Views: 27419  |  
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The Making of a Gloryhole Gurl Part 3

Making of a Gloryhole Gurl! Part 3
By Kristy

I look back on some of the Pictures from my early days, going to the Adult Bookstores and the Park and can’t believe how bad badly I was at putting my makeup on and some of the things I wore. Although I still like to dress slutty!
I could sneak away for only so long before I had to change back and make it home without a trace. I made a major breakthrough soon and began going into the bookstores completely dressed and I was going more and more to the ABS’s and sucking as many cocks as their were, and if I got real lucky I would fi... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  Views: 1408  |  
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The ConVentioN part

2. Arrival
Pulling against the chains that secured her arms over her head, Sasha whimpered in frustraition
yet again. Her bonds hardly rattled at all as she shook and twisted her body to try and get free.
All she succeeded in doing though was making her heavy tits jiggle and bounce painfully. Alone
and naked save for the few cow patterned garments her mistress had allowed her, Sasha cried
softly in the darkened room. Her breasts were swollen with milk, now each one was larger than
her head! Pink bands had been tied to the base of her nipples, preventing any of her milk from
leaking out.... Continue»
Posted by peterbtrs 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 873  |  
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true story tv first dogging

I am a mature TV living in the north of the UK. I have been dressing since I was 7 and having nylon led sexual fun since my early teens. The result today I have a very large wardrobe of clothes and shoes, am 100% smooth apart from a landing strip and have manicured nails and shaped eyebrows and with killer legs in high heels. I am divorced and able to play a lot, but, I had this one desire to go dogging. The problem was safety for me. I did not want to go to a hugely popular place or one that was miles away from me. So after looking at different swinging sites I decided on a place that ... Continue»
Posted by jostwo 3 years ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 885  |  
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Str8 Guy Seduced By A Tranny (ch1)

Str8 Guy Seduced By A Tranny (ch1)

For a str8 friend here at xHamster... who is a fan of my writing and when I told him I would write a story with him in it... I'm not sure he knew what he was getting into..

Chapter 1

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To say I was nervous was a bit of an understatement... but I was also very, very excited. This was my first time putting it out there in a big way.

Back home, I had gone out a few times and was completely passable... I guess I should explain more...

I am Lexi, that is my girl name... I was born a boy, or I should say... Continue»
Posted by TomStone90045 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1858  |  
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Daddy's lil bitch

As a young boy growing up I always had a fetish for dressing up like a girl. When I was 20yo I had my first experience with an older man, Tony a man in his 70s. I met him through a phone chat line and we seemed to hit it off right away. He told me that he would buy me some clothes and lingerie to wear for him when we met. So after a couple weeks of phone chat I mustarded up enough courage to meet him face to face.

When I arrived at Tony’s house he greeted me with a warm hug and kiss. Tony was a very handsome man, stood about 6’ tall and clearly looked like he took good care of his body. He ... Continue»
Posted by aznfemboi 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 3062  |  
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So you know women...

I was in another state in an extended stay motel for spring break. The girls were hot and the guys were hotter, I did not know which way I would go on this trip.

I had noticed two females that seemed to be daughter and mother, they would come in early morn and stay in their room. The young girl was close to my age and very light skinned, the one I thought was her mother was some what darker and had a heavier build.

One morning I was returning from an all night party and was just a little bit d***k. I saw them as they pulled in and the elder of the two ran from the car saying someth... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1689  |  
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Ladyboy orgy in Thailand

During one of my many nights in the sleaze capital of the world Pattaya, Thailand I was at a certain ladyboy bar all dressed up in my sexiest outfit that the “girls” had ask me to wear in as I had shown them some pics of me dressed. Not that I could ever hope to compete with any of them!

Chatting away with one of the girls a German guy came over to us and said that he having a “party” up stairs and if we would like to join him and his friend. I assumed he just meant the girl from the bar and told them to have fun and she went off with the German guy. Just as they went threw the door lead... Continue»
Posted by toniparr 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 2276  |  
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TV loving cock

Sorry I didn't keep you posted on Saturday night, but I was sorta busy being my usual slutty self. Story to follow:

I talked to a guy on megaphone. He works as a night security guard at a big office building on the edge of town. He is there all by himself in this huge, mostly vacant building, in a safe area, so there really isn't anything for him to do but set around and be horny. So he was looking for someone to come over to his job and get nasty.

Naturally I was just the girl!

I'm all dressed up in one of my hottest outfits and looks, so I jump in the car and race over. It takes m... Continue»
Posted by jenn1 3 years ago  |  Categories: Shemales  |  Views: 1317  |  
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Chronicles of Amy, Episode 1: The Beginning

Amy is a part time transvestite who enjoys to dress very sexy and go out and have some fun. So a few years ago, on a Thursday evening, she was sitting in her favourite cafe, looking at the poeple passing by, flirting with some attractive males, who were charmed by her appearance. She was wearing black fishnet stockings, 4 inch black leather high heels, a miniskirt that was barely covering her perfect ass and a white, very tight top. The cafe was quite full and so basically the only free seat was the one next to Amy. She was enjoying another bit of the chocolate cake she had ordered before, so ... Continue»
Posted by SweetAmy 4 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 1017  |  
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