Shemales Porn Stories
Page 13

Sissy Emma is turned

I had been a crossdresser all my life but completely in the closet and hidden from all my friends and f****y. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.
I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean I talked of having implants, of being tattooed, hair permanently removed etc but did I really want that? I also talked ... Continue»
Posted by emmahighheels 2 years ago  |  Categories: Shemales  |  Views: 4253  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 4250  |  
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Black Mamba -

Most of the following is true. I'll leave it to the reader to judge what is
fact and what is fantasy. Until six months ago I was known as John Evers.
Blonde, five foot seven, slightly built and heterosexual, I had just gone
through divorce after a stormy six year marriage. Not into the bar scene and
at loose ends for things to do in my spare time, I decided to redecorate the
house the way I wanted it. The first order of business was to completely
repaint the interior which I proceeded to do. After prepping and painting
every night for two weeks, I was ready for a break from the tedium ... Continue»
Posted by germanboi4bbc 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 4240  |  
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During the divorce 15 years ago

I am older maybe wiser but still a k** at heart and love to pretend. I get home Saturday around dinner time, after horrible (He’s Cheating, Has other women) things are said by my supposed loving wife of 15 years about how I mentally abuse her or the he doesn’t love me anymore innuendos. A Saturday meeting with attorneys because she cannot meet during the week due her job, this won’t be cheap. The divorce is painfully slow, meetings about this and that are beginning to feel like a hot sweaty day covered in glue rolling through broken glass! I get home and pretend that my c***dren are st... Continue»
Posted by Chartless 1 month ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 4201  |  
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My brief stab at prostitution

This happened when I was 22, I was broke and hanging out in my hometown, a large eastern New England city of about 500,000. I was hanging out on what was the main drag looking to see if i could get picked up by a guy for sex. I got a lot of interest but no one was stopping. after about 90 minutes I said "fuck this" and decided to go to a diner about a block away. I cut down a covered alley that cut through a huge department store and started walking up toward the diner. it was chilly and the wind was gusting as i crossed the street. I sort of noticed a van following me on the left. I figured t... Continue»
Posted by aurora_dream 4 months ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 4168  |  
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Senator's "Daughter"

Some things about life are much better and easier when your father's a rich and successful senator, you don't really need to work for one thing, you have all the time and money you could ever want to indulge in whatever fun you want, others are less good, like being an only c***d in a household where your parents were never around. I was nineteen when the events of this story happened. My father, Senator Mark Feldman, had just been re-elected and was very busy all the time, some times spending days away from home when he had important business to attend to in the city. My mother, Madeleine Fel... Continue»
Posted by drew1207 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 4159  |  
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Baby's Surprise

Baby's Surprise

After a long hard Stressfull month at work I came home Friday and Lisa was not home and had left a note
(Hey Baby unwind and take a shower I left somethings on the bed for you wink wink, See you in an hour xoxo Lisa)

I sit down turn on the stereo and get loaded, I get up and go to start the shower and take a shower and shave
all over and clean out. Lisa's wink wink is a hint to shave and clean out back there she wants to play.

Back Story 10 years ago Lisa and I ventured into Strapon's and then one night as she was using the Strapon
in Me she said Hey Baby I want yo... Continue»
Posted by Bi_Norfolk_cd 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 4157  |  
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Fist visit to my sexy new female doctor

Yesterday I went to the doctor because i felt like i was peeing too much, i'm sitting in the waiting room and the doctor calls me, and she is the hottest woman i have ever seen. Late 20s/early 30s, gorgeous middle-eastern face, nice curvy lips, big dark eyes. She's very friendly with a thick Persian accent which i find very sexy. i explained to her my situation, and then she asked if i was sexually active, and i said no a bit too quickly, and she looked surprised for a second. She got me to pee in a jar, dipped the testing strip, and came over to show me the results. She got me to hold one end... Continue»
Posted by wet20 1 year ago  |  Categories: Sex Humor, Shemales  |  Views: 4150  |  
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Finding a Great Roomate

I had just moved to the Great NorthWest and was lucky enough to land a job as a convenience store clerk working a shift from 8pm to 4am. Money was tight so I went to the classified to look for an apartment to share. I found one that was fairly cheap and close to my job. It was a two bedroom apt. and I would share the kitchen and common area with my roommate. I gave the guy a call and set up an appointment to see the apartment and be interviewed by him. I went to the address and rang the bell. The door was opened and there stood huge guy, well over 6' tall and I would say around 260lbs. H... Continue»
Posted by rikki50 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 4148  |  
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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 7 months ago  |  Categories: Fetish, Sex Humor, Shemales  |  Views: 4142  |  
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My First Cock

I always knew I really was meant to be a girl. For a while I thought I was simply gay, but I loved wearing thongs and bras. I loved masturbating while pretending my asshole was a vagina. I never made it a secret. I'm very flamboyant and girly. I still managed to have lots of friends in high school. Several of them knew I wished I was a girl.

One night I was very upset about God knows what. I was crying with a good friend of mine at his house. He was straight and had a girlfriend (another good friend of mine). I began venting to him about wanting to dress like a girl and be treate... Continue»
Posted by hotchickinchitown 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4138  |  
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Paying rent

I’ve always enjoyed getting dolled up like a sexy girl ever since I hit puberty. Doing my hair, wearing frilly panties, skirts, painting my nails and doing my makeup. But being a boy that isn’t viewed as proper behavior. Which is why I’ve always had to dress in private. But luckily with the power of the Internet I’m able to express my inner girl. I run a blog where I post dirty pics of myself dressed up, erotic stories of young crossdressers being used by older men, captioning dirty pictures and I do webcam shows just about every night. I even get tipped for my webcam shows and can use the mo... Continue»
Posted by ScarlettMaeBottom 5 months ago  |  Categories: First Time, Shemales  |  Views: 4138  |  
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Getting caught on purpose ( true )

I had gotting tired of my mother showing up at my house everyday with out notice.She always came in and whated to move stuff around and say something about a dish in sink or what I had cooked for dinner last nite.I love her but since her boyfriend past away she was driven me crazy.
So I woke this morning early and asked her if she wanted to go shopping with me.She said yes I bought some heels bras painties and we went got our nails done.She asked do you own any male clothes I told here no.Well I dropped her off at her house and left and 20 minutes later she showed up I tried to tell her cal... Continue»
Posted by cdpaula 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 4127  |  
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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 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 4111  |  
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Topped by a tranny: tiny anal virgin.

I was in college busy trying to get my degree like we are expected to now a days. I was working part time and other than that had a lot of free time. I was always horny. I jerked off almost any time I got free. One day I got tired of the alone action and wanted more fun. I always had a fantasy of being fucked so i decided to try and find someone to break my anal cherry. I wasnt very good with meeting people and trying to meet someone to do that to me was def hard to think of how to do. I turned towards craigslist. I sent out posts for women with strapons, guys... Guys were all fat or gross n n... Continue»
Posted by Fnhory04 25 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 4119  |  
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Wife turns white hubby into black cock cuckold s*s

"Oh my god!"

My wife looked up over the muscular shoulder of the huge black guy nailing her on our bed. Her long tanned legs wrapped around v-shaped torso. "Hi honey. What are you doing home early?"

"Kelli what the fuck's going on here?!"

At that, the black guy turned and shot me a nasty glance. "What's it look like we doing, genius? I'm dicking your old lady. Now get out of here fuckshit I ain't finished."

"Better go downstairs dear," Kelli said, smiling. "I'll be down later to explain."

Of course I was shocked, but what else could I do? I went downstairs poured myself a drink ... Continue»
Posted by whitewhores 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 4110  |  
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Slutty Sissy Used in a Cheap Motel Part 2

After being fucked and bred by the first 2 strangers and watching my sissy hypnosis videos I was definitely ready for at least one more deep fucking. It was around 10 p.m. when the next guy knocked on my door. I opened the door to find a very large black man about 6'8" and a smaller black man who was about 6 feet even. I invited them both in and was very excited that I was going to be tag teamed by 2 black cocks. These two guys were very demanding and knew exactly what they wanted. I knew that I would do whatever they told me to do, because every ounce of my male thought process was gone and m... Continue»
Posted by cumslutchloe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4087  |  
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Bondaged and fucked at a hospital: Pt 3

It's my third day at the hospital and I learned something new today. The pills they had been giving me to "ease the pain", were mixed with other ones and I hadn't known about it until this morning. These other pills had secret side effects which were only used for "different" medical needs and they seemed to slur my speech making it hard to understand what I was saying. At first I thought that it was for a short period of time but I after an hour of attempting to speak it only seemed to get worse. 

Another nurse walked in who wasn't Lisa and I wanted to ask her about my condition, but as I ... Continue»
Posted by adblman 1 month ago  |  Categories: BDSM, Hardcore, Shemales  |  Views: 4065  |  
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Losing my Cherry

Although l have been secretly cross dressing for years I have never took it beyond the confines of my bedroom or hotel room. Well I have been really wanting to take this to the next level. So as I was traveling on business this past week I answered an ad on Craigslist for a massage in my hotel room from a male masseur I made the appointment and waited with anticipation for my masseur to arrive. At promptly 8:00 there was a knock on the door and when I answered there was Chris a very handsome young man, I invited him in and he promptly set up his table..
As he was setting up his table and ... Continue»
Posted by mikkas72 8 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4063  |  
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becoming a slut

It all started when I was 13 and discovered the joys of wearing women's clothing. It started with my older s****rs panties then my highschool girlfriends things by the time I was 18 I had a pretty good collection of womens clothing even with never having the nerve to purchase any of them myself. Then came the urge for more when dressing up and masturbating wasnt enough I wanted more. I always considered myself straight despite my crossdressing but when dress would get the urge to please a man. So one day I got my s****rs 7 inc dildo. I got dressed up in some sexy thong panties some nylons and ... Continue»
Posted by RenoBoi 9 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4042  |  
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