Shemales Porn Stories
Page 15

crossdressing with my moms friend

Mom opened my bedroom door. she stood there in the doorway and stared at me obviously repulsed. after 10 or so seconds she closed the door and walked away.
i was mortified. i was kneeling on my bed, with her clothing catalogue open at the lingerie section laying on the bed before me, hard cock in hand. But most embarrasing.....i was wearing my mom's black bra, suspender belt and black stockings....her black panties were thrown onto the bedroom floor, cast aside when the urge to cum had become too much.

for weeks after this incident, we barely spoke. as it was just the two of us since Dad h... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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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  |  
  |  28

Night With A HOT Sissy!

June 28th, 2009. End of senior year of high school. I, Angus Corleon, actualy graduated. I wasn't a model student. I've been a leather jacket wearing, rebel rousin, beer drinkin, hell raisin son of a bitch since middle school. My parents didnt care about me, after all my b*****r is a cop and my s****r is a lawyer, and im the law breaker. Anyways, enough about who i am. My buddies johnny, brandon, timmy, and danny have a hell of a party planned for tonight. Big bon fire out in the back woods of where we live. Must be 200 people were expecting. We set everything up, fire pit, band equipment, cha... Continue»
Posted by CDboy9097 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  4

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 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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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  |  
  |  3

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 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Uncle Bobs Lesson

I posted this story on another site years ago. I had some nice feedback, but not many views.

In '91' during my senior year of high school my folks split up just after my18th birthday late in the summer. The whole thing was a mess, with me being sent off to relatives while my mom took my younger siblings to the gulf coast to stay with her parents. They sold the house and Dad moved to be with his new future 'ex-wife' outside of Dallas.

Since I am older by about 7 years, and was in high school I did not want to leave town in my last year. No way did I want to be sent off to someplace I did... Continue»
Posted by Cuckarama 2 months ago  |  Categories: Gay Male, Shemales, Taboo  |  
  |  2

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 8 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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Hotel Adventure

A few months ago, I started a new job. The job took me around the country, often to locations far from home, where I would stay in some easily forgettable hotels, which usually, at least, were blessed with free WiFi. I would generally arrive the night before attending client meetings the next day.

This gave me many opportunities to enjoy my old hobby of cross dressing. Now, I am straight, but - for as long as I can remember - have enjoyed the thrill of dressing as a woman. I have never gone out in public, and my wife has no idea, so it is a very private hobby, except that recently I have t... Continue»
Posted by mallenwc 3 months ago  |  Categories: Fetish, First Time, Shemales  |  
  |  5

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 8 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  2

My First BBC

It was not long before I told my wife about who I really am, that I was having serious desires to be taken by a real man. I have / had no true preference, but something about getting pounded by a cocky and arrogant black guy really turned me on. But I wasn't looking for some thug or prick to just have me. I wanted a man!!! A black man.....a BBC man!!! One who had a hot bod, aggressive demeanor, and of course a huge cock. So I had my expectations, and I was anxious for this experience.

I had been dressing in full for a while at this point, but my wife wasn't actually aware. Porn was... Continue»
Posted by Ivygurl86 8 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  13

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 year ago  |  Categories: Fetish, Sex Humor, Shemales  |  
  |  10

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 11 months ago  |  Categories: Fetish, Group Sex, Shemales  |  
  |  2

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 9 months ago  |  Categories: Fetish, Shemales, Taboo  |  
  |  2

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  |  
  |  1

Gym Slut Pt 1

To start the story I need to give a little background on myself. I’m a fit, 25 year old guy that is known by most people as a guy’s guy. In high school and college I played sports and was always one of the team captains. I was a medium height guy that had a toned appearance; 5’8, 155 lbs, shoulder length hair, and sprinter thighs. While in public I play the tough athlete role I’ve always been a little shy with the ladies and even when with them have been a little on the submissive side. Somewhere along the way I started watching sissy videos and secretly wearing women’s panties. I’ve ne... Continue»
Posted by sissybitch2013 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  2

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 2 years ago  |  Categories: Gay Male, Shemales  |  
  |  6

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  |  
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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 1 year ago  |  Categories: First Time, Shemales  |  
  |  5

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 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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