Shemales Porn Stories
Page 15

My girlie fantasy part 1

On a Halloween night I dress up in my sexy devil costume with my wig & some makeup & go to a local bar sitting alone. A guy ends up sitting next to me & flirts a little before I ask if he wants to go to the restroom with me to which he eagerly agrees. After getting in a stall we makeout for a little as he fondles my small breasts before I go down on my knees & pull his average size snake out & get to work. Shortly after starting he rewards me with my first taste & runs out embarrassed at how quick he finished leaving me wanting more. I sit back down at the bar & eventually another guy takes a ... Continue»
Posted by multiplierx 1 year ago  |  Categories: Anal, First Time, Shemales  |  
4601
  |  
100%
  |  3

My Life as a Shemale Part1

In this story, many will find what happened to me socially unacceptable. But since this has happened to me, I get to tell it and if you like, listen.

I was very young when I found myself on the streets and it seems long ago that some things I do not remember but its the important stuff that I do. And yes, like so many other stories start, here is how I looked. 4 foot nothing, skinny, long blond hair and even then had more angelic features then not. I do believe that now, that I was a woman even then but as nature would have it she would have a sense of humor and endowed me with a large peni... Continue»
Posted by gigi750 1 year ago  |  Categories: Hardcore, Shemales, Taboo  |  
4596
  |  
100%
  |  3

Moms Trannie

It was Saturday night and my friends had told me about a new club. It was about an hour out of here and had an older crowd. This sparked my interest some what having a fondness for older women.

I walked into the place and looked around, not much going on so I wandered over to the bar and ordered up a beer. A little while later the crowd picked up and things started to get moving.

The women were defineatly older here, I asked a few to dance and had a few takers but couldn't seem to lock in with them.

While I was dancing I must have missed the two that came in, a blonde and brunette wit... Continue»
Posted by frswriter 3 years ago  |  Categories: Shemales  |  
4581
  |  
97%
  |  36

My Shemale Mom and Aunt chapter 2

When we three got home Mom told to me go to my room and wait for her, about 5 minutes later I was sitting on my bed. She walked in with one of the bags of goodies we bought, Mom said I think you should call me "Jenna don't you Timmy".

Jenna started to strip so I went to her and got down on my knees, she said later Timmy hop in the shower NOW!. Mom/Jenna undressed and joined me in the shower she grabbed the the shaving lotion and her pink razor, she shaved every thing except my testicles, she dried me off and said lay on the bed while I finish, I laid on my back and pushed my knees to my ch... Continue»
Posted by sissytimmy 2 years ago  |  Categories: Anal, Shemales, Taboo  |  
4633
  |  
96%
  |  2

Four (4) in 3 days, no wonder my jaws ache

Yesterday was Sunday and I hoped it would be a day of rest. I went into the local market in drab, did a little shopping, decided I had the start of a cold and took my time doing very little.

My nipples were still sore from Saturday evening's little escapade and my jaws were aching a little, I seemed to have sucked a lot of cock in a very short time.

I spent a very quiet afternoon, rinsed out my collection of stockings, put off washing my lingerie until today and settled down for an online session without much hope of getting a date. By 6.00 pm I decided I did have a cold and was going ... Continue»
Posted by antoniaf 2 years ago  |  Categories: Anal, Mature, Shemales  |  
4570
  |  
100%
  |  1

The office girl

Tamsin was the new girl in the office and she was clearly shy. Unlike the other girls who splattered make up all over their faces and spent hours on deciding which dress to wear, Tamsin was rather plain. Her typical outfit was a smart suit. It became very clear very quickly that she felt very awkward in the new environment, so I thought I'd try and help her settle in.

Over the next few weeks we quickly became close friends, often laughing at each others jokes while our co workers were still trying to work out the punchline.

Out of the blue a office night out was arranged. I asked Tamsin ... Continue»
Posted by kinkymister 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
4568
  |  
92%
  |  6

Charlotte and her sister go swimming

I did not write this story.

I am 18, I have a younger sibling who is 2 years younger than me called Emily. Even though she is younger than me and we both come from the same parents, she has a better body than me. She is curvy, taller than me, wider hips, small waist, amazing big round ass and huge tits. I'm a D but she is an E, almost F. She turns me on a lot, I know it's wrong but I get horny thinking of her naked.

We both love our swimming. Even though this is an awkward sport for me as I am tiny and it is hard for me to hide a big 8 inch cock. I usually tuck it between my legs pushing... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
4568
  |  
93%
  |  1

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 3 years ago  |  Categories: Anal, First Time, Shemales  |  
4564
  |  
16%
  |  14

My First Tranny

Cheryl had really opened my desires to fuck. She was, and is totally uninhibited, and a total sex machine, doing whatever she desires at the moment. When I felt my cock enter her throat the first time, and felt her tongue slide up my cock to the balls, and she sucked the cum right out like my urethra was a straw, I knew I had a keeper. I was hoping I was able to satisfy her, and hoping she would keep me around, this was really the best sex ever. I would get no argument from my wife, she was getting all the cock, and later I would discover she was getting pussy also, she had the best of it ... Continue»
Posted by fishkiller 3 months ago  |  Categories: Fetish, Mature, Shemales  |  
4560
  |  
100%
  |  2

Corrupting Little B****r

DISCLAIMER: This story is solely a work of fiction. Any similarities between people living or dead is purely coincidental. No a****ls were harmed in the writing of this story.

I was s**n going on s**n when our m****rs moved in together (they would marry the following year). I had been living as a girl for a year and a half. He, my new little step-b****r, was f**n at the time. He had just started puberty, and was a bit shy around girls, it was kind of cute. He was also kind of cute, in that young, androgynous kind of way. We got along okay, sure we squabbled, and he, for whatever reason, w... Continue»
Posted by seityn 11 months ago  |  Categories: First Time, Shemales, Taboo  |  
4555
  |  
100%
  |  4

He caught me in his wife's cloths

I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of the job I showed up just before Tina left for work. Pillip was already gone. We chatted a while the she left for work. Tina is really very hot and I have wanted to fuck her for a long time. Sense i knew that was not going to happen I thought I would do the next best thing. I went stra... Continue»
Posted by firstknightd 5 years ago  |  Categories: Shemales  |  
4553
  |  
95%
  |  28

Frannie's Femboy

Gay - cross dressing – femboy - feminization – blow jobs – anal sex – hand job – lingerie

When I was finishing high school, I did a lot of different jobs to raise money. I mowed grass, worked part-time on a construction crew, and pumped gas, all to raise funds for college. I had been accepted to the college of my dreams on a partial wrestling scholarship, but my parents weren't going to be able to help with the other expenses. While I hoped to eventually turn the partial scholarship into a full one, I was doing everything I could to raise enough money to avoid missing a year.

In a... Continue»
Posted by naughty_bi_interest 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
4545
  |  
100%
  |  10

A young man's summer [full story]

MY BEGINNING

My name is Jason, and I am a typical teenaged young man; lean, horny all the time and really happy that I have reached the age where I can get a job that pays better than mowing lawns or delivering papers. My parents work all the time and me and my older b*****r John, have had the house to ourselves since I was 8 and he was 13, which meant no more getting up at 5:30 to go to a sitter who would either keep us all day or make sure we got on the bus for school.

I discovered the concept of sex early on; John would jerk off constantly if he thought no one was watching, this sta... Continue»
Posted by serious58 11 months ago  |  Categories: First Time, Masturbation, Shemales  |  
4538
  |  
100%
  |  3

Couple Uses Katie

So let me start off by giving you a bit of background here. This is a couple who I have played with a few times. They are really nice and understanding. They even allow me to come over and get all dressed there before we play. And yes they are an interracial couple. With that said.......

I don't know where I was or what I was doing, but I was bored and horny and looking for some fun to occupy my mind. Come to think of it, I'm pretty sure I was just in my house on a typical Saturday afternoon. I put out an online post for BBCs. I'm sure if you know me, then you would understand I... Continue»
Posted by Ivygurl86 9 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
4540
  |  
97%
  |  17

Wedding Gift

Doug and I had been best friends since the first day at school. Who knows why you choose your first friend? It could be that your mothers push you together. It could be because you turned up at the school gates at the same time. Or it could be because on the first day you sat down next to each other. All I know is that Doug and I were friends from the first day to, well right up to today. Through the first few years we were always in the same classes. We spent holidays at each other’s houses and our parents got to know each other pretty well too.

And then we hit senior school.

As puberty... Continue»
Posted by annav 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
4526
  |  
100%
  |  6

Shooting with a tranny

I was bored one day so i decided to rent out a transsexual e****t. I called her up so we can do a special photo shoot together and needless to say, we ended up fucking. She came to my door with an all black dress on and the sides were transparent. She had 5 inch open toe heels on and a leather jacket that came to her waist. Her hair was long and curly and she was fair skinned and spanish about 5'8 with heels on. She walked in and asked me where i wanted to start. I pointed to the couch and she sat down. She immediately changed into a tank top for men and a very small lycra shorts. She was bare... Continue»
Posted by michneo 1 year ago  |  Categories: Fetish, Hardcore, Shemales  |  
4522
  |  
100%
  |  5

Best I ever had

I was at work one night closing up shop when my buddy Nick shows up and asks if I want to come over and party. I say sure. When we get there he tells me his girlfriend Nora might be interested in a little playtime. Now this might not happen again if it does happen he tells me. Well I'm certainly interested. You see we both met her about the same time and she was a hot little number. About 5'1" or so she claims. tight petite little dancer's body. Perky A nearly B cup breasts. Medium length honey blonde hair ang... Continue»
Posted by aladinane56 2 years ago  |  Categories: Voyeur, Shemales  |  
4518
  |  
100%

Josh and Lois

My name is Josh, six foot four and weighing in at two
hundred and eighty pounds. I am a big guy and did not
have trouble getting girls even though I was not as
handsome as most and the really pretty ones usually
went for the more handsome, financially secure guys.
This was never a problem as I was screwing regularly
with the girls telling their girlfriends about my
huge cock and most of them wanted to try it at least
once.

I am blessed with a ten inch fat cock measuring nine
inches in girth... about as thick as a beer can. I
never said no and made any takers scream and ... Continue»
Posted by griffen1 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
4519
  |  
100%
  |  2

gfs father round 2

Hey guys back again to tell you about me and Jim my girlfriends father and our hot sex relationship.

So last week after the football my girlfriends dad fucked me and now I can't wait to be his little sex toy again.

He messaged me the other night asking for round 2 and told me that there was a game of football on the tele he wanted to watch and his wife was away for a few nights on business. So if I wanted a piece of cock then he was up for giving me it.

I told him that I would get home after work Nd shave my ass and all that area so I was nice and smooth for him.

I told my girlf... Continue»
Posted by owensy100 27 days ago  |  Categories: Anal, Gay Male, Shemales  |  
4514
  |  
100%
  |  11

Workout

Several times a week I go to the health club for a mild workout. I often see a guy named Mike. We chat as we workout. Now I am a secret TS so I'm totally clean shaven but also lots of guys who are into working out are also. Anyhow Mike is a real hunk! As most guys do Mike will make an occasional joke about the size of his penis. The bulge I secretely glance at looks pretty good but real size hard to tell. So last week we were done together so we were showering & boy was he right about the size of his cock. So he caught me looking & said "see told you it is pretty big". I said "yes it ... Continue»
Posted by nyloned1 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
4511
  |  
96%
  |  7