Shemales Porn Stories
Page 59

A little job on the side

A work of fiction

By Carole ( crticism only please
Don’t be scared to e-mail me with details of stories or your experiences.
If you are u******e please GO AWAY;

A friend of mine Brian ran a small guest house mostly for travelling reps etc: One evening he rang me and asked if I could do some urgent repair work for him as his usual guy had let him down because of illness. I replied that I could help and would be round first thing in the morning. “That’s great I’ll see you tomorrow” he replied.
The next morning I turned up, and was told what the ... Continue»
Posted by hottvcarole 1 year ago  |  Categories: Group Sex, Shemales  |  
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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 1 year ago  |  Categories: Fetish, Group Sex, Shemales  |  
  |  2

.......Mt Frist Train

My First Train
There are so many sex terms used today it is mind boggling and each term has different meanings to different people. For example, “Gang Bang.” To me it means a women or a transsexual whom of their own free will copulates with three or more men. When a woman or a transsexual services seven or more strangers, she is having a train pulled on her. This is the story of my very first train.
A year after my wife found out I was a male-to-female transgender and I became her cuckold we both had a few new lovers. One of the guys I was fucking pretty regular call me up one evening an... Continue»
Posted by littleoralvee 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  9

My Visits to Sex Shops in Coppenhagen

Chapter one
I was visiting Copenhagen as a student and staying in a room
My landlady was a mature blonde who opened the door to me
Hello darling come in you are very welcome have you been here before?
No mam I have not but am looking forward to enjoying it over the weekend
As she took me to my bedroom she said she would give me any info I needed
The room had a lovely double bed and a tv set
You can get adult films on channel 900 I know you young boys like to watch
sexy movies she said with a wicked smile
Thank you I will ask you for directions after I get ready to go out
I op... Continue»
Posted by juicypantys 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
  |  2

My b*****r's Lover

I was eighteen and in high school when it happened, my b*****r was twenty and still living at home. I had to borrow my b*****r's computer one day to do some work for school and I guess maybe I let my curiosity get the better of me a little as I found myself instead of writing the essay I was supposed to be working on, looking through what files he had saved on his computer. I was pretty interested in particular by a very full folder hidden away in a place that you would not expect to find it. Now, I'd been a teenage boy for long enough to know that I had probably just stumbled across my b*****... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
  |  8

b*****rly Desires

James heard the doorbell go, and opened it to find his neighbour standing there with a smile.

"Hi James, I'm wondering if I could ask a favour? My broadband's down and I have some urgent emails to send. Would I be able to use your computer for half an hour?"

"Sure Dave, come on in and I can help you out!"

Dave grinned at him as he squeezed past. James had had a crush on his hunky older neighbour forever. Everything about him was delicious, and he thought he'd even caught Dave watching James getting dressing up in his bedroom; when she peered out the window, she'd noticed movement from... Continue»
Posted by sparkyking 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  
  |  5

Presurgery fun

So. I had back surgery the 2nd of May, was supposed to be there that day but my dr called me and had me come in the night before.

I forgot i was wearing my black baby doll under my clothes, what follows is my last sexual encounter in over a month now.

i got to the hospital and they took me into the surgery prep area to start with, and it was then and there i remembered i had my black baby doll on, and nowhere to hide it so i just went with it. and by that i mean i stripped down to it right in front of the sexy little nurse who looked at me kinda funny then said that's cute. She said here... Continue»
Posted by Caryli 1 year ago  |  Categories: Anal, Shemales  |  

My Job in a Lingerie Shop

Chapter 1 Getting The Job

As a student I applied for a job in a lingerie shop in London.
Having being dressing for years in my s****rs lacy pantys stockings suspender belts
and mini dresses and short skirts and blouses and high heeled shoes
I was really excited when I got a text to come for a job interview at the lingerie shop
I decided to wear my black lacy pantys and matching lacy bra under my shirt and
tight jeans. I tucked my big cock between my legs so as not to bulge too much

I arrived at the shop and as I entered went in and noticed there were a couple of old guys
longingl... Continue»
Posted by juicypantys 1 year ago  |  Categories: Anal, Mature, Shemales  |  
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The Transformation part V

Mistress Anna walked me down the hall. "Are you ready to have your little sissy purpose fulfilled?" she asked me.

My heart raced. What did she mean. I could hear someone in the kitchen but I knew it wasn't Mistress Heather or Mistress Anna because they had helped me get dressed. My voice shook as I nervously answered, "yes mistress." With my reply came a firm slap to my thong clad ass.

"Good girl!" mistress Anna exclaimed. She brought me into the dining room and helped me down to my knees. The blindfold felt like it was soaking wet because of the sweet and heat from my face. I fe... Continue»
Posted by fictiong 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  3

Grad school rommie

So I had just started grad school, and moved in with this guy to share rent, his name was Brett, nice guy mild mannered. At that time I was bi-curious at best, but nobody had a clue, or so I thought. Brett was gay, or at least I thought he was, I never really gave him a sexual thought none the less, after about a month of living together, I walked home from this party, and I was trashed, this girl walked me home, and we hung out in the living room with Brett, me and her made out a little bit, and I felt like Brett was watching us, but I wasn't sure, either way the girl rubbed on my cock throug... Continue»
Posted by smonkeys32 1 year ago  |  Categories: Anal, First Time, Shemales  |  
  |  4

"Game" Over???

I had not had any Barb time since returning from Kansas City. School was to start up in a week ending summer break and I needed to dress. The folks were at work and I was going to play.

I put on the open bottom girdle dad had bought me, tan nylons, a white lacy bra and my breast froms, and 4" black pumps. I went into the folks bedroom turned on the stereo and sat down at mom's vanity to do my makeup.

I then went to mom's closet and started looking through her closes to see what I could wear. I felt something brush my hard cock and looked down to see a manicured hand gently holding it!! ... Continue»
Posted by Barb51 1 year ago  |  Categories: Mature, Shemales, Taboo  |  


It had been quite some time since I had tasted the flesh of a young buxom female. I needed to have a good-looking lady at my side and soon. I decided to go dancing in town at one of the local bars. I don't usually hang out at these kind of places; however, It may be time I started. It sure is hard to find a date now a days. I went to the Lighthouse Bar. It usually is happening all night until about 4:00 am.
I dressed in my tightest jeans and my best button up shirt. I looked for a lack of better words--tuff. All I had to do was get some chick on the rebound or something, buy her a fe... Continue»
Posted by freegre 1 year ago  |  Categories: Hardcore, Shemales  |  
  |  2

Transsexual Lust

This is not my story. I found it in a free site a long time ago and I wanted to share it with you. This is not a copyrighted story as far as I know.....

I was 23 when I had the only job I really liked. It was after I graduated from college in Philadelphia, and had just gotten a job in the fashion industry. Actually, it was really just a designer dress shop, but it was a start. At first, I wasn't too excited. After all, a dress shop isn't the most interesting place to work, right? Wrong!

My first day on the job started out as normal as could be expected. There was a note from the owne... Continue»
Posted by freegre 1 year ago  |  Categories: First Time, Hardcore, Shemales  |  
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Sissy for BBC use and a b u s e

My Dear little sissy s****r, lezzie lover and slutty confidant...

Thanksgiving saw me full of BIG BLACK mouth, my sissy pussy and my belly were full of so much BBC and SPERM from Big Black Daddy Dick (s) annnnd I was good little bitch in the Doggy position for the Black Daddys' and their DAWG POUND(ING). I finally hooked up with my own BBC GANGBANG SQUAD from the adult bookstore. They used me for well over 24 hours of serious sissy-slut abuse, degradation, domination, humiliation and more, much, much more! I can't wait to tell you about it. I wish you were with me so w... Continue»
Posted by santtxx 1 year ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
  |  5

The Sissy Gene: The Ceremony


The Ceremony
We waited back stage until the principal called us out. First he would talk about the school year, then introduce the Alphas, and then the Sissies last. I was so nervous and super cold, there must be no heater in the back, and wearing a micro bikini wasn't helping. Kevin had the smart idea to huddle together so we did. Our tight bulges would sometimes touch but it was worth it for the warmth. On the other end of the stage I could see the Alpha males. They were warring matching dre... Continue»
Posted by sissyslovebbc 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  6

The Sissy Gene: The Preparations


THE Preparations

As soon as I entered into my classroom, the teacher started clapping. Congratulated me on becoming a sissy. She was just catching the class up on how she was ending class early so she could help me and the other sissies be ready for the ceremony. After I followed her to the change rooms where the other 3 boys who had just become sissies should already be getting ready.
Mrs.... Continue»
Posted by sissyslovebbc 1 year ago  |  Categories: Gay Male, Group Sex, Shemales  |  
  |  1

Sissy and her Mistress

"Mistress, what are we doing tonight? I need to know what to wear" I pout.
"You'll see. Put on your slutty schoolgirl outfit with your white thigh high stockings, and your 4 inch heels. I'll be there in a half hour"
"Yay! I love that one!" I exclaim.
"Be waiting outfront" you command.
"But Mistress..."
"No butts sissy, this is what you want - and oh, yea, don't forget your plug. The large one"
"Yes mistress"

40 minutes later, I am outfront of my apartment complex trying to hide in the shadows. Given my height and the heels, I am attracting a bunch of attention. You chuckle as 3 black... Continue»
Posted by drew1207 1 year ago  |  Categories: Anal, Fetish, Shemales  |  

My 1st time having sex with a guy!!

I went out with a gay friend of mine hem was my hairdresser Rodney he is fine as hell ripped stomach sexy body big fat cut shaved cock,he. Be out for cocktails at a gay bar after about five drinks apiece we started dancing mingling with people I met a beautiful TS lady boy he look & acted just like a girl we was dancing dirty I was getting so turned on she was grabbing my dick kissing my neck talking dirty and it was working so we,went back to,the vip room and was making out she had just un button my pants was stroking my cock so,go... Continue»
Posted by Cockriider69 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  1

PartyPlanning Chp1. Pt1.


"This feels great. The sun is not to hot on my skin but it's a bright clear day, the ladies are running like clockwork and so am I. Ten, I think ten moms have strolled by, just like yesterday. I'm so glad I decided to workout in my garage. Chicks love to see a man workout, especially a single guy like me. Last minute of my work out and this new workout DVD "Get Slim 4 Fem" Has me in top shape. And the host, Princess!, her highness. What a bitch but if I could fuck her I'd never stop. Last minute gotta focus...

10 m... Continue»
Posted by cohonjames380 1 year ago  |  Categories: Sex Humor, Shemales, Taboo  |  
  |  1

My Girlie Fantasy part 3

Suddenly among the Eden of pleasure Ken was providing, the
doorbell rings like thunder as lightning strikes burning away the
sacred garden. Ken curses under his breath while he gets up to go
see who it is. I quickly sit up & fix my clothing as he walks to the
door, watching him as he goes. Almost as soon as he disappears
around the corner he returns proclaiming that it is his b*****r that
he hadn't seen in years then disappears again to let him in. I feel a
bit of a chill roll down my spine as I hear the door open & them
talking loudly. I stand up as Ken walks around the corner with... Continue»
Posted by multiplierx 1 year ago  |  Categories: Fetish, Hardcore, Shemales  |  
  |  1