Shemales Porn Stories
Page 10

My Uncle Wally's Sissy Boy Wife

Penned by: Miss Deborah (Debi) Leigh Johnson



One



I did not know what I could expect, as the Greyhound pulled into the
bus station. I did not know a whole lot in fact, as I was a rebellious
know it all, fifteen year old brat.

My parents were pretty good as far as parents went. I had not locked a
roof over my head, or enough food on the table, but I had always
resented the fact that my parents were not rich enough to give me
everything that I wanted. I knew in the back of my mind that this was
a pretty immature attitude, but what the hell, it was the way I
felt. I also di... Continue»
Posted by jayymie 6 months ago  |  Categories: First Time, Shemales  |  Views: 4222  |  
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Sissyfied By A Big Black Bull

Last night my life changed forever. We have new neighbors move in next door ,they were two big strong very buff black guys that were drop dead sexy ,as soon as a saw them moving in I was perving at them through my window and my sissy little white dick was hard in an instant as I have been fantasizing about being with a black man for a while now . I decide to put on some sexy under garments and my ugly male clothes over the top to hide them and I went over and introduced myself ,man are these two the ultimate fucking hotties mmmmmm b... Continue»
Posted by foxxiroxxi 29 days ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 4202  |  
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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: 4145  |  
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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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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 9 months ago  |  Categories: Sex Humor, Shemales  |  Views: 4134  |  
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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 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 4126  |  
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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: 4111  |  
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My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the room. Like I said there were lots of beautiful ladys there but one caught my eye. She was not too ta... Continue»
Posted by wildbill975 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 4091  |  
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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: 4083  |  
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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 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4052  |  
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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 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4052  |  
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Sex with teacher(sissy)

I was the 2 year of high school back then. My grades werent going realy well moastly becuse i spent most of my freetime blowing guys,and sticking thing in my ass,then studying.My parents one day decided that i need some extra classes,so they hired a tutor. I wasn't realy up for that idea,but they somehow talked me into it. After a while it was the time for me to have my first class. My parents left for work,and i was home alone waiting my teacher.Then the dorbell rang , i felt so nervous as i opened the door. In walked a handsome 25-6 year old man,fresh out from college,in a very nice suit. We... Continue»
Posted by sissygirl1988 1 year ago  |  Categories: Anal, Shemales  |  Views: 4039  |  
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The Truckers Reststop

I had to work yesterday, it was Saturday,I had made plans to spend the day being the slutty little whore for the whole day, but work got in the way. I came home felt tried so I soaked in the tub, shaving my legs and puss yass and gurly clit. The weather was bad all day, when I finally decided to Fem myself up it was already 8pm, so I thought what the heck I'll drive up the Interstate just north of Seattle to a truckers rest stop I have gone too before. The weather had cleared up a bit, so I was hoping for some fun. I dressed in my short wrap around skirt, red thong panties, red Bra, and a shea... Continue»
Posted by cd_lorretta 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 4033  |  
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The Surprise Vacation



The Surprise Vacation


by an unknown author and Tristmegistus

1. Chapter - Innocent Beginnings

"Did you take your vitamin, dear?" Ellen called from the bathroom.

I rubbed sl**p from my eyes and picked up the pill bottle, rolling a big
tablet into my palm. "My horse pill? I'm doing it now."

"Have you noticed any difference yet?"

"Nah. Vitamins are pretty much all alike." She'd gone on a minor health
kick a month before, insisting that I needed to lose a little weight and
take better care of myself. I hadn't actually made it to the gym to wor... Continue»
Posted by klammer 10 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 4037  |  
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My first time being taken dressed as a woman

I'm a 42 year old married bisexual guy, slim built, average height and shaved below. Ive had a few encounters with other men but none dressed as a Woman.
Ive had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a few months ago.
As it turned out my wife would be away for 3 weeks and opportunity presented itself. I quickly got down to planning and slowly but surely a plan came together, well sort of anyway.

I went online and ordered some womens lingerie, wigs, panties, make up and a few slutty costumes, ... Continue»
Posted by jimbo70xyz 1 year ago  |  Categories: BDSM, First Time, Shemales  |  Views: 4020  |  
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Frank's Friend

Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a little d***k. Frank pulls up to this leggy blonde in a short skirt and fishnet hose and asks how much. She told us she would do us for free for a ride home. We said fuck yes. Frank had me drive to her house while he had her in his lap, kissing and groping her. We got to her house and went i... Continue»
Posted by biguy52x 1 year ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 4019  |  
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SOMETHING ABOUT DANNY

What was it about my daughter's boyfriend that turned me on so much? No one characteristic comes to mind. I suppose it was a combination of things. And perhaps a certain time in my life also. I was 52, divorced, alone and quite bored.

I had been divorced from my husband Jerry for 12 years and didn't really have a steady boyfriend. Jerry and I remained friends but he seemed to be turning into an old man. I was still young at heart, or so I felt. But the more men I met the more disappointed I became. It had been getting to the point where I would rather stay in my apartment and read than go o... Continue»
Posted by couple_kinky 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 4011  |  
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she trained me

I was sent to Aunt Fergie when my parents were killed. She is about 5'7"
and 200 lbs she was your stereotypical aunt with some fat and wide hips and
big breast. She picked me up at the bus station in her car.

She said," My household is different and special I have girls who you
will find are very unique. I too am unique and I will show you what I mean
when we go home."

We rode for a half-hour and we arrived to her big old which I would find
was an old Victorian with a widow's roost on top of the roof.

She e****ted me to the bedroom that would be mine and told me," Put your
... Continue»
Posted by pcarter 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 4009  |  
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Crossdressing - Teen fantasy with Panties to Cock

Confessions of a Crossdresser

I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to understand how I have evolved.

If I was a woman, I would be a cum dumpster: intelligent, attracti... Continue»
Posted by ericalace 2 months ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 4009  |  
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The Tgirl Hooker

All my stories are based on real life experiences.

I spent a few weeks looking at e****t sites, reading reviews, services, likes & dislikes, pictures... until Emma caught my eye.

Emma was Eastern European, had a tight slim body, blond hair, very fem and a nice cock. I wasted no time and contacted her to set up a visit and within a few hours she replied and we discussed what I wanted.

The day soon arrived and I was quite nervous through excitement. I had visited e****ts before but never a Tgirl. I pulled up to this house in a normal road and knocked on the door, and there stood Emma i... Continue»
Posted by dirtydisco99 4 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 4001  |  
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