Shemales Porn Stories
Page 122

A Halloween Hoodie story

*crossdress story*
This is the story of my first time going out dressed; it was halloween last year (2009). I figured i'd have less to worry about walking around dressed in a gothic tartan corset, spider-web mini-skirt, fencenet tights and about 10 armbands and bangles. It wasn't exactly brilliant but it was the excitement that spurred me on.

Of course i was scared of seeing someone i knew, like a neighbour or a friend, but it was about 22:00ish, so i figured it was dark enough and late enough to avoid those kinds of people.

It was a lovely feeling as i stepped outside, the wind rushing... Continue»
Posted by KitsuneTV 3 years ago  |  Categories: Shemales  |  Views: 586  |  
99%
  |  16

You Just Never Know... ya know?

I was out on the road, On my way to Montreal at the end of my stint behind the wheel. I pulled into a roadside rest area, or lay-by... or in this case a 'pickle park', a cruising area for local and tranient gay and bi-men looking for a quick NSA hook-up. Hell, so was I.

I was all nice and clean from the shower I'd had an hour ago at a fuel stop, and I was ready for almost anything now. I waited for a bit and sure enough, a girl walked up beside my truck from out of the shadows, and asked me for a light for her cig. Her voice gave him/her away, and we chatted for a little while.

Short... Continue»
Posted by crochetteDave 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1052  |  
9%
  |  9

Lucky Afternoon Part 3

I was awakened by Nikki turning over so that now her little butt was pressed to my groin. In this position, of course my cock rested between the cheeks of her butt. I pulled her closer and found that she was awake also and she sexily wiggled her butt to excite me. She turned to face me and suggested that we need some condoms and lubricant. I agreed and she suggested we run out to get these items and possibly grab a pizza or something to bring back to the room. I thought for a moment and then ask if she would like a steak dinner? She admitted that she loved steak but was unsure about us g... Continue»
Posted by rcpeters 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 982  |  
19%
  |  6

my transformation

is fiction


It is strange where one’s desires can lead one. Take me as an example. Always entirely enamored of, infatuated with and completely submissive to all things feminine, a true devotee of Female Supremacy, my lifelong fantasy has always, since before I can remember, been to find a position as the submissive sissy maid and sex slave of a commandingly beautiful, dominant Goddess, spending virtually all of my time that was not devoted to domestic duties with my sissy face, mouth, and tongue smothered by and buried in the delicate, sweet, pungent pussy and ass of my Owner/Mistress and/... Continue»
Posted by elisatv 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 937  |  
98%
  |  6

What I do best

I lick my lips and taste the gorgeous deep red lipstick applied so carefully; I glance at my image reflected in the minicab windows and gaze at the evening revellers as they make their way to the clubs and bars in London’s West End. I am amazed that here I am dressed as a complete slut in an off-the-shoulder asymmetric short pink dress, showing a yard of chocolate coloured, fully fashioned seamed stockinged legs, killer 5” heels and ankle chain. The transformation having occurred just a few hours before; this was in London’s East End at a dressing service that exists for only for us ‘special... Continue»
Posted by angyqtv 3 years ago  |  Categories: Anal, Shemales  |  Views: 527  |  
6%
  |  8

Porn shop slut

I walked into the booth excited to use my new toy, while dressed in garters and sexy panties under my loose fitting jeans. I had just purchased a lovely new butt plug and could not wait to try it out on my pretend pussy.
Taking my jeans down I deposited a token into the slot and got out my lube and started pretending my tight boi pussy was that of the woman on the screen masturbating. I commenced rubbing the oily lube all over the rather large plug, while running my free hand all over my stockings and sheer back see through black panties.
I started sitting down on the plug, and gently ea... Continue»
Posted by hotjizz 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2392  |  
96%
  |  16

womanly experience 7 - busted

This happened quite recently. I was reminded by a video I saw here on the site because it's very similar to what happened to me. It's about a girl that was turned on by spanking and received even harder punishment. I'm a trans so the things were more obvious.

* * * * *

I was close to 22 when one day my father decided I have to go to church (probably hoping that will get me back to being male). I didn't want to argue too much so I went to my room, dressed up, and headed for the church. When he spotted me in my clothes (that was quite short) he got angry and decided to give me a spanking b... Continue»
Posted by p1llow 3 years ago  |  Categories: BDSM, Shemales  |  Views: 380  |  
20%

new boyfriend and first sex with him

Turns out the guy I sucked in the faculty (college) toilet actually suspected I was a trans and that turns him on. And not only he's into trans he also told me he loves BDSM. I don't have to tell you how great this is, but let's start at the beginning.

The other day after the "toilet incident" I met the guy again. I had white leg warmers, a schoolgirl skirt (I wear these as much as I can), a black tank-top, and a gray hoodie. I heard a voice behind me telling me how beautiful I am today. As I turned around he kissed me. Deep. And with his tongue. My heart raced and I instantly felt an erect... Continue»
Posted by p1llow 3 years ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1043  |  
13%
  |  3

womanly experience 6 - self bondage pt. 2

During the night I woke up because I had to pee. As I love humiliation and I had diapers on me anyway I just let it go. I felt the warmness spreading and shortly fell asl**p.

When I woke up in the morning the first thing that was to be done is punishment. How could I pissed into my diapers? Shame on me. I got up and removed the diapers, got on all four on the bed, and paddled my ass hard until it got red and sore. Then I measured my rectal temperature (I really hate that) and gave myself an enema three times.

It was almost noon when I was finally done and felt quite humiliated and bad ab... Continue»
Posted by p1llow 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 253  |  
25%
  |  2

womanly experience 5 - self bondage

I was around 18 or 19. Still in high school. My father went out of the town for thee weekend and I found an interesting blog on the Internet about a self-bondage girl. I knew that I had to try this while I had a chance.

It was summer so I prepared everything I needed and left it in the tool-shed in our yard. I buried two pairs of keys on different sides of the yard - one is to the inside of the house and the other for some handcuffs.

Then I got all naked and went out into the yard, locked the door behind me, and threw the key in trough the small bathroom window. I then ran into the shed ... Continue»
Posted by p1llow 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 232  |  
93%
  |  1

Being helplessly exposed

This is a true story about my adventure into being exposed as a sissy.
I am terribly ashamed at the thought of being seen sissified especially since my face is clearly visible. My shame is greatly magnified when I am being exposed on the Internet. I am terrified someone will recognize me. The first time it happened I created an account and posted many very embarrassing and humiliating pictures of me to it. I was so aroused as I did this. After a while I removed my pictures. Then I reposted my pics. A Dom wanted to take control of the account so that I would be powerless to remove the i... Continue»
Posted by jerrywhore 3 years ago  |  Categories: Shemales, Voyeur  |  Views: 897  |  
50%
  |  5

womanly experience 4 - first fully naked punishmen

In high school I wore schoolgirl and similar skirts every single day. On my legs I always had either tights, knee- or thigh-high socks, or nothing (when it was hot). I almost never were thongs to school because I couldn't risk for someone to find out that I'm on hormone therapy.

My father was buying me all the clothes so I had to be careful with them because he needed the slightest excuse to punish me. The boys were going crazy for me but I never allowed them to touch me. On the last year of high school I did allow some breast touching but that was all. One day one of the buys couldn't bear... Continue»
Posted by p1llow 3 years ago  |  Categories: BDSM, Masturbation, Shemales  |  Views: 1486  |  
84%
  |  1

One Wild Night!

Not long after my wife and i split i was feeling ready down and lonely. So i went out with some friends to just have some fun and party. After going to dinner and really pissing of the waiter we went to this party at some place i didn't know. When we got their it was a really cool party alot of women and loud music. I was just hanging out and talking to a few people when this really cute girl comes up to me and asked if i knew were the bathroom was i said i have no idea and laughed. She looked a little sad so i said let me help you find it. She said thank you i feel so strange walking around a... Continue»
Posted by clarkbrian82 3 years ago  |  Categories: Fetish, Shemales  |  Views: 1027  |  
11%
  |  2

Missed My Chance, But Never Again.

This is a true story. I was on a 3 day business trip and
settled into my motel room that evening after my
business meeting. It had been several months since I had
the opportunity to dress up. I showered, shaved and put on
my make-up and wig. I went to my dresser drawer and pulled
out my 6 strap black garterbelt and stockings. I sat down on the
bed and slowly put them on. My hands trembled as I attached my
garters to my stockings. Next I carefully and sensually pulled on my black nylon panties. Next I put on my black bra and leaned forward to insert my breast enhancers. Next came... Continue»
Posted by Shadyterri 3 years ago  |  Categories: Shemales  |  Views: 530  |  
25%
  |  9

CD Driving While Dressed

I was making a 400 mile trip going south. I was driving
alone and wanted to dress up in my favorite outfit for my
day trip. After leaving home, so my wife would not know of
my traveling attire, I went to a nearby shopping center to
change into my outfit. I parked my truck in the parking
lot in an area that was not too busy with traffic. I
hurriedly removed my male clothes and reached into my
travel case to get my wig and black bra which I put on. I
then inserted my breast enhancers and looked down at my
chest to admire my large breasts. Next I slipped on my
black 6 strap g... Continue»
Posted by Shadyterri 3 years ago  |  Categories: Shemales  |  Views: 650  |  
36%
  |  6

womanly experience 3 - NYE

It's not a secret that I have a fetish for pads. By my 22th birthday my father gave up on punishing me for menstruation simulation so I "had" my period each month. I still have the menstruation calendar I use to track my periods so I know when will the next come. And buying tampons and pads also helps keeping my sex change more real and believable.

It was spring and I just passed 22 years that winter so I was really enthusiastic about my newly earned freedom (at least in this). It was Friday and my girl friends and I planned on going out. It was also my period time and I just ran out of bot... Continue»
Posted by p1llow 3 years ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 418  |  
50%
  |  1

xmas pet

Please see my first blog for background info: http://xhamster.com/user/p1llow/posts/18252.html

* * * * *

I never got anything from my father for xmas or bday since I started leaning toward my feminine side. I knew something is strange when I got up on xmas morning and saw some presents. He does buy me clothes he sometimes wants me to wear at home but that's never a gift - more like a strange punishment (or at least he thinks he's punishing me most of the time). I was too afraid to open them before he wakes up, they might not be for me after all, so I did my chores around the house until ... Continue»
Posted by p1llow 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1143  |  
90%
  |  5

womanly experience 2

In high school everybody thought I was a girl. I was just approved hormone replacement therapy and people thought it was just a late development of tits. I was mocked for that but I never really cared. My tits did grow to a formidable size later. I was pretty much disgusted at that time with my penis so I tried to not to touch except when I really needed to. And when I talked with the girls about girly things I always referred to my ass as my vagina. It was fun times.
At least until I went home. Even though I was officially approved for sex change my father hated the fact and tried to humilia... Continue»
Posted by p1llow 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1067  |  
21%
  |  3

Loving TS Sex

living in a medium size city 30 years ago, it was necessary to stay into the closet. That way of live is really still the reason why I never outed myself, even after years living in different bigger cities and several countries.

I had acquired a taste for transsexuals, considering them the best of two worlds. Never could resist the view of a beautiful girl knowing that there were a certain something between her legs.

When I felt the urge inside me I cruised into the night looking for the zones were the TS used to hunt. I always made sure to pick up a girl when no other cars were aroun... Continue»
Posted by bloodyhugo 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1405  |  
4%
  |  4

Dominated

I was dominated by a older woman yesterday on cam she made me do so many naughty things dressed like a little girl. And I loved it! ;)... Continue»
Posted by Glov 3 years ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 995  |  
50%
  |  1