Shemales Porn Stories
Page 71

Crazy dreams

I met Dave about 2 years ago at a swingers party. I had just turned 18 and he was 43. I remember thinking that it was hot that he was exactly 25 years older than me. I was dressed in drag and he was into t-gurls and he was married and hung like a horse and I happened to be into partying naked with big dicked married guys ;-) I always acted masculine around his wife, but whenever she wasn't around, I put on stockings and heels, makeup and wigs, and pranced around like a sissy little pantyhose cumslut!

One time me, Dave and his wife were hanging out, drinking. Dave and I were playin... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Group Sex, Sex Humor, Shemales  |  Views: 987  |  
97%
  |  6

Halloween fun

Here's an interesting story that happened to me last Halloween, hope you like it. Last October, a local bar had a Halloween costume contest. Since I had nothing better to do (I'm too old for trick or treat) I decided having a beer and checking out all the silly costumes would be fun. I sat near the bar and almost immediately a sexy, slinky brunette caught my eye. She was wearing a light blue dress, black seamed stockings, and dark brown "fuck-me" pumps. After a short time I went over and said hello. She was smart and funny, and we really seemed to get along nicely, but with the loud musi... Continue»
Posted by throbbinghardboner 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 2394  |  
97%
  |  9

POP GOES THE CHERRY

POP GOES THE CHERRY

I recently read a delightful account of a young gurl loosing her virginity to a f****y friend. Got me thinking about loosing my own virginity.

First, you should know, my mother made me a sissy. She took great delight in dressing me as a little girl, thinking back I can not remember when she did not. We lived in the country and most of the time growing up I played outside with my dolls in dresses. The only time I wore little boy’s clothing was when f****y visited or I went to school.

Everyone in town knew I was a very sissy acting little boy. I was bullied a ... Continue»
Posted by littleoralvee 3 years ago  |  Categories: Shemales  |  Views: 1222  |  
97%
  |  7

Cheri

My name is Cheri, I live my life in lace and satin. I have always loved the way those materials feel against my soft skin. I have shoulder length red hair and bright green eyes. My friends used to call me Charles but about 12 years ago i had this epiphany that i felt out of place as a man and one night while I was out at a club with some friends, I realized that being a woman felt... I don't know, right,
to me I guess. It's been a long road but I'm so much happier now.

The first time anyone ever found out I had a dick after that was about 10 years ago. I went to a new doctor for some ant... Continue»
Posted by LadyShi 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1475  |  
97%
  |  6

So you know women...

I was in another state in an extended stay motel for spring break. The girls were hot and the guys were hotter, I did not know which way I would go on this trip.

I had noticed two females that seemed to be daughter and mother, they would come in early morn and stay in their room. The young girl was close to my age and very light skinned, the one I thought was her mother was some what darker and had a heavier build.

One morning I was returning from an all night party and was just a little bit d***k. I saw them as they pulled in and the elder of the two ran from the car saying someth... Continue»
Posted by d4david 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1689  |  
97%
  |  3

Meeting with the Boss

I arrived to work to find out that my boss wanted a meeting to discuss my future with the company. I wasn't sure if this was good or bad. My boss, Erica, is a very beautiful woman. She is hispanic with bronze skin. She resembles Eva Mendes and is about 5'7" tall, 130 lbs with great curves. She always wears tight skirts and blouses. I entered her office and she told me to sit. After talking for about 20 minutes I was thinking this is good because I would have been fired immediately.

She then asked me how dedicated was I to her and the company. I said very dedicated and that I love working he... Continue»
Posted by swordlvr69 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 3733  |  
97%
  |  16

My night of first times!!!

I was sitting in the bar with my friends when she walked in. Black short dress, low cut neckline. I can see the garter straps holding her stockings. I think that is what caught my attention first. I had seen garters and stockings in movies but never in real life and her legs looked great. I couldn't keep my eye off her all night. I had to seem like a stalker with my eye's, I wasn't paying much attention to the conversation at the table with my friends she was lust at first sight. I had to make a restroom trip and when I walked out she was standing there. My heart skipped a beat and my stomach ... Continue»
Posted by Trudru 3 years ago  |  Categories: Shemales  |  Views: 1977  |  
97%
  |  6

TV loving cock

Sorry I didn't keep you posted on Saturday night, but I was sorta busy being my usual slutty self. Story to follow:

I talked to a guy on megaphone. He works as a night security guard at a big office building on the edge of town. He is there all by himself in this huge, mostly vacant building, in a safe area, so there really isn't anything for him to do but set around and be horny. So he was looking for someone to come over to his job and get nasty.

Naturally I was just the girl!

I'm all dressed up in one of my hottest outfits and looks, so I jump in the car and race over. It takes m... Continue»
Posted by jenn1 3 years ago  |  Categories: Shemales  |  Views: 1323  |  
97%
  |  8

Once upon a time, I dated a Co-Worker...

It was summer and Dad had asked me to help him around his car insurance agency. Mainly I answered phones and typed in reports on the computer. Couple of nights a week, I would also vacuum, clean up and straighten the office a bit. Had the weekends left to go to the beach and hang out with my friends. Robert and Mayra still worked there, they had been with Dad for years. Both were appraisers, and were in and out of the office constantly. There was a new part-time clerk. Her name was Natalie, in her mid-twenties, a tall girl with long brown hair and hazel eyes. Chatty and friendly, I felt... Continue»
Posted by latinCharm 1 year ago  |  Categories: Anal, Shemales  |  Views: 3255  |  
97%
  |  9

Sometimes, mistakes do happen but they can be real

A few weeks ago I was wandering round some of the nice tv/gay sites for this area of France when I got a message from a guy asking me if I would like to meet. Well, I was very horny at the time, so nothing new there, was aching to do something to somebody or have them do something to me, you know the feeling, when you ache to feel something nice and long in your mouth or being slipped in your pussy.

I thought to myself why ever not, he seemed like a nice guy, he wanted to meet on his way home from work so we arranged to meet in a quite well known gay rest area between his destination and t... Continue»
Posted by antoniaf 1 year ago  |  Categories: Masturbation, Mature, Shemales  |  Views: 1440  |  
97%
  |  8

Chrissie and the Professor

Possibly the after hours engagement with an English Literature professor at college may have been the thing that convinced me that older
men might be more to my liking.
It was during my Junior year at the university when we were discussing the poetry of Arthur Rimbaud, the French poet, that I became infatuated with my professor. He was a typical scholarly gentleman one would expect to encounter at a major university. He was in his mid fifties, and still in remarkable condition for his age. He was about just under 6 feet tall, blue eyes with salt and pepper hair. In class he was charming, w... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Shemales  |  Views: 909  |  
97%
  |  7

Atrip to the dentist

My wife thought I was at the dentist but I was really with my special friend Sandy. It had been over a month since I could sneak away to see Sandy. My cock was wet and hard just from the ride thinking about what she would be wearing and how we would please each other. When She met me at the door I almost exploded just looking at her. She had blonde hair today in a long braid d****d over the front of her shoulder. Her eyebrows were dark thin lines followed by different shades blue all the way to her eyelashes. Her cheeks were painted a blush color and her lips a dark crimson. She wore a black ... Continue»
Posted by Zeffer1 3 years ago  |  Categories: Shemales  |  Views: 1197  |  
97%
  |  2

Transformation

This is a cross between real life and fantasy. A deep, dark desire which may never be fulfilled but I can't help a part of me wanting it anyway. I hope you enjoy.

----------

I was a usual guy. Or I had thought so anyway. I mean, I had worn some of the female members of my house' panties and swimsuits on occasion as a young boy but I always thought that was normal. I mean, apart from the silky smoothness of lace and satin massaging and teasing the penis, y-fronts are exactly the same really... just with less frills. It didn't last long though, I mean, how can a boy in a strict and straigh... Continue»
Posted by shyadam89 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1601  |  
97%
  |  6

caught spying

i would love to re act this with someone ;) any offers?


A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-).

Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pride and joys. Normally, this would help her relax and unwind, but tonight, and on several other nights, she found that remained tense. She couldn't get over the feeling that somebody was watching her, for several days, perhaps a week; when... Continue»
Posted by leadpencil21 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2492  |  
97%
  |  9

The fun part of stephons run in with sora

Ok, its going to be ok stephon. I think to myself as I reveal her cock. It turns out shemale cock isn't that different from regular cock. Or at least mine, I have never sucked off a guy so......

Anyway

Mouth, neck, upper chest, natural breast, chest, belly button, below belly button, shorts, panties. I stop, im still second guessing myself and then just nut up, expose her cock and lick it.

Umm.... This feeling is different than I expected. I think that I'm actually enjoying it. Like three minutes go by and im sucking on the head. sora is moaning so I guess I'm doing good. I was fuc... Continue»
Posted by cooler34 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 425  |  
97%
  |  1

Clara Bow's Academy for W-B Ladies Part 4

Greville Hambleton tried hard not to think of the ginger sissy; he was married to a fiercely independent woman who was very much in charge in the bedroom, and who knew all too well of Greville’s weakness for effeminate transgendered she-males. As he was often cuckolded, Tara his wife being partial to sampling cock, she turned a blind eye to his discretions. Like a lot of otherwise heterosexual males who enjoy the assertive control by the superior sex, he had a keen dominant streak which revealed itself with a preference for younger ladies, and even more so for sweet effeminate sissies. His ... Continue»
Posted by midsummerman 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 313  |  
97%
  |  3

Hedonistic Crossdressing, Part 3

The best way to describe Vince, probaly is that he was a socially functioning pervert. I had no idea just how varied, and intense, his sense of erotica was, but I was going to find out as time went on. Perhaps the worst thing is (or best perhaps, depending on your point of view), is that I became quite the little "apprentice", you might say.

I'd been his "guest" for only a few hours, and I'd experienced more than I'd ever dreamed. I've dressed, I've sucked my first ever cock, been fucked hard up the ass, taken cum, been made to cum like a girl, been made to take ass to mouth, w... Continue»
Posted by elainetgrl 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1410  |  
97%
  |  9

Massage parlor surprise

I have to admit one of my biggest turn ons are shemales/ladyboys. In all my little ventures to asian massage parlors for some relaxing relief only once did I get a total surprise. About a year ago I visited one of my favorit little places and Mama said I should try her new girl....I might like her. So I agreed to meet with her. Waiting in my little room in walks a very hot sexy little asian girl and we started our massage session. While getting my rub down I started letting my hands wander to her thighs and lower butt to rub and feel then and to let her know i was cool for some extra if on the... Continue»
Posted by longrod4u 2 years ago  |  Categories: Shemales  |  Views: 1717  |  
97%
  |  7

My First Tgirl Deepthroat.

Before I, start, I will tell something of myself.

My name is John, I am 48 Yrs old, I never thought I would attracted to Tgirls,

I am average built, 5ft 10in tall, 190 lbs, I am Hawaiian, Phillinino, Chinese
Nationality.

Well 2yrs ago I was cruising in town (Honolulu) and went to a bar to chill for awhile a had two beers just cruising, when this beautiful Asian girl sat down next to me, She was hot smoking hot, damn.

We started talked, simple confersation. I kept staring at her full lips and I was getting a hard on. I was hope she would not notice my fidgeting around on my chai... Continue»
Posted by jkain 1 year ago  |  Categories: First Time, Shemales  |  Views: 2307  |  
97%
  |  12

the train ride




The Train Ride

Has anyone taken a night train following a major event in an
Asian country? I have. If you think trains are crowded during
peak hours in New York, you must experience riding trains in
Asian countries. Then you may ask what is common between a
crowded train in Asia and a can of sardine.

The idea to see the festival was planted in our minds by George,
who was our bartender at the hotel. He stated that the Kandy
parade was a once in lifetime experience, two days before we were
to head back to Oslo. After hearing what we were about to miss,
we made plans to hit... Continue»
Posted by pcarter 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1711  |  
97%
  |  8