Shemales Porn Stories
Page 12

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 11 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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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  |  
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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 1 month ago  |  Categories: First Time, Shemales, Taboo  |  
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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 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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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 3 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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My First Girly Cock

It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. I don't consider myself being gay, but I always had that ardent lust to be with a transsexual woman. I just couldn't get them out of my mind.

This passion started a couple of years ago, while I was surfing on the Internet looking for hot stuff. Immediately I felt something. That first time, when ... Continue»
Posted by Asmarani 5 months ago  |  Categories: Anal, Shemales  |  
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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 1 year ago  |  Categories: Voyeur, Shemales  |  
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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 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 9 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Business Trip

My boss had sent me to Brighton at short notice as she decided at the last minute that she didn’t want to go. Apparently she had something better to do. The fact that it was my birthday didn’t seem to bother her too much. I usually liked the chance to get away for a couple of days as I’d sneak in some of the wife’s sexier things in my bags and spend my evenings in my room all dressed up and nowhere to go. But this time I would be missing out on spending quality time with Suzy. We’d only been married three years so we still made the effort when it came to birthdays. I had thought of bringing Su... Continue»
Posted by annav 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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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 5 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Life Changing Encounter

My name is Tony and I want to relate my story about a recent change in my sexual attitudes and preferences. When I was small my parents were divorced and my father never came back to visit me or even write a letter so I grew up with my working single mom.
During most of my life I was heterosexual. When I was twelve I came by some Playboy magazines, given to me by a friend, that displayed impossibly beautiful women in various suggestive positions. I had not had an orgasm yet but during the last few months I would wake up with a stiff cock which, at first, was disconcerting as I had no idea w... Continue»
Posted by johnny49r 8 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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Old trannie gets a boys virginity

Oh dear I’ve been a bad, bad old trannie. I let a teenage boy seduce me.

I normally only go with guys over 30 at least. But this teenager contacted me on a dating site. I gave him the normal “Thanks but I’m in my 40’s you’re a bit on the young side for me” reply. However he kept contacting me on the site. He was very curious and quite sweet. I chatted with him online and he said that he would really love to meet me.

I told him if he wanted to meet me that he could find me at my local sex club. He said he couldn’t go there. After a deep thought I said it would be O.K to come round on the... Continue»
Posted by toniparr 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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first time with a Tranny

My first tranny I had was back after I graduated from high school. I was working with her/him at a Wal-Mart store. We got along pretty good then we started to date, I was living on my own so we usually go to my apartment. I had no clue she had a cock, she was a very beautiful woman with size B tits. We dated for about a month when talk her into just taking her shirt off, after a while without her shirt off she finally took her bra off. I would make out with her and suck on her tits, lick her nipples. One day we were together I decide to change it up so I took my pants off in the bedroom and ... Continue»
Posted by theho_1 3 years ago  |  Categories: Anal, Shemales  |  
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Ladyboys: Moving to Thailand and my first Ladyboy


After living in the Netherlands for 33 years I was ready for a big change. I had been toying with
the idea of moving to another country to get away from the stress of it all for a while.
I had girlfriends in the Netherlands. Wives.
I had one nighters and 2 nighters. I wasn't doing bad for myself.
But, there was something missing on the girl side. I love variety. I think I've been with
every kind of girl I COULD be with in the Netherlands. I started thinking about other countries.
Other girls. Other types of girls...
I had seen shemales in Amsterdam. Emphasis on the boy part. And they ... Continue»
Posted by casinocock 1 year ago  |  Categories: First Time, Shemales  |  
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My First Gangbang

For as long as I can remember, I have always enjoyed wearing women's clothing. When I was in fifth grade, I started wearing pantyhose under my pants during the winter. By the time I was going into the seventh grade, I had learned that, not only did I enjoy wearing pantyhose, I also liked playing with peckers too ;-)

As you may imagine, I became VERY popular! Pretty soon, there wasn't a sl**pover in the neighborhood that I wasn't invited to ;-)

I quickly developed what would be a lifelong obsession: semen. And no matter how much I got, I still wanted more! The feel of it squirting into my... Continue»
Posted by cdsexslut 3 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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beautiful tranny

This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong?

Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s not that I should worry about! Men of my f****y have always been stocky, and thickset. So a big nose and stocky figure are not a trouble! I’m working in a Western City College as a tutor of English Literature. I teach student best masterpieces of Shakespeare and Charles Dickens, and so I am in my whole best! I ... Continue»
Posted by princessamyov 5 months ago  |  Categories: Anal, Shemales, Taboo  |  
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How I got started dressing my true story.

As far back as I can rememeber I have always gravitated towards fem things. As a young boy I played with whatever girls clothes I could get my hands on. Which wasn't much. At 12 y/o I had a few pairs a panties and bras stolen from my cousins. One thanksgiving after dinner the girls changed and one of them left behind a black knee length dress and white pantyhose in the guest bedroom. I was so excited when I found them...needless to say she never saw that dress again. With the bra and panties I alrady had from her and the new black dress and white pantyhose...I had my first total outfit. My tr... Continue»
Posted by Sarahaspencd 6 months ago  |  Categories: Masturbation, Shemales, Taboo  |  
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What is it about a womens bulge

A very attractive women once bumped into me in a very crowed club in Mexico City, I turned to say excuse me. I was speechless at her beauty. She was wearing a short skirt, garters below the skirt and knee high boots. She just stared at me and with out saying a word she bumped me again. I felt something different something firm and it moved it was very intriguing. I kept looking at her and without saying a word I couldn't move, I wanted to say something and I couldn't. She slowly put her arm around my waist and she slowly rub her crotch on my leg. I was frozen standing there looking at this gor... Continue»
Posted by ilgreek 2 months ago  |  Categories: First Time, Shemales, Taboo  |  
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New Neighbors

My first attempt at writing one of these. Let me know what you think.

My roommate Mike burst into the room grinning, “Dude, have you seen the two girls that just moved in down the hall?” That caught my attention, “Wait, that blonde and brunette are moving onto our floor?” I had indeed seen them earlier outside the building. They had stood, laughing and chatting with one another, while movers unloaded boxes under their supervision. I couldn’t help but notice them; the blonde in a slightly too short summer dress that showed off her strong legs, and a low neck-line that promised never-ending ... Continue»
Posted by slatemhor 6 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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