Shemales Porn Stories
Page 6

Shemale Fantasy

He met Theresa in a gay club one night. He wasn't gay but he had always wanted to fuck a shemale and so had gone looking for one. She was perfect - tall, black, muscular, huge breasts and the slight bulge of her package pushing through her shimmering gold dress suggested she had a lot to offer. Her hair was black, long and curly and she wore bright make-up on her African features.

He couldn't believe his luck when she agreed to come back to his hotel. He could tell she was excited when, from beneath her dress, her hard penis brushed past him gently as they entered the room. Theresa sat on t... Continue»
Posted by strongerbuddy 1 month ago  |  Categories: Shemales  |  
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A young man's summer [full story]


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 1 month ago  |  Categories: First Time, Masturbation, Shemales  |  
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A Night at the Metro

Before the inevitability of gentrification set in, Toronto's Metro Theatre stood for many years as the city's last full-screen porn cinema. And while more recent innovations in pornography (such as home video and later, the internet) had taken their toll, the Metro had things to offer which could not be had elsewhere. Living on the other side of town, I was an infrequent visitor to this one-time temple to sleazy entertainment, but on the occasions that I did, I'd usually have myself a good time. This story is about one such occasion.

Exiting the subway at Christie station, I could feel the ... Continue»
Posted by sissymaidjanine 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
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Old man fantasy-Part 2

As i got home after i finished my job I got horny again,I have been thinking about the experience all the time since it has happened.I could not take off my chastity cage to masturbate..I did not know what to do I could not keep my mind off him so I called him and told him about this...i heard a lusty laughter for the first time and he sad "You will get addicted to me..I am gonna turn you into the best cum-dumpster,I will see you tomorrow".
I barely slept that night,he clearly succeeded in controlling was a big part of his plan,I was fingering myself without even noticing the reflex a... Continue»
Posted by cutecdkiss 1 month ago  |  Categories: Gay Male, Mature, Shemales  |  
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Becoming his girl (Sissy story by GirlyGay)

In the summer after my eighteenth birthday, I met Nick. He was a thirty-something who lived in our building. My parents had gone for their yearly European trip, and I had been left behind this year because I had college orientation during what would have been the last week of their trip.

Mooning and alone, with nothing to do for four whole weeks until my flight up west, I took to the pool to catch some sun. I had not bought new trunks in a while, and so my old ones were riding high on my legs.

Nick was already at pool, beer in hand, sitting back in a barca-lounger. His broad, smooth che... Continue»
Posted by sissyAlyna 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  
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The Rendezvous Pt1 (Sissy Story by CassidyCaine)

Nick looked at the email he'd received from his wife at lunch again as he got ready to leave work. It had been a month since he'd confessed to her his love of dressing up in women's clothing after he'd kept it hidden since they first met. But, Nikki was insistent so he had tried to share that part of him. She had worried he was gay or didn't want her anymore but he'd assured her that wasn't the case. Yet after all that worry, she had emailed him to tell him that tonight she wanted to play with his fantasy and role play a little to see if she could get into it. She had rented a motel room and w... Continue»
Posted by sissyAlyna 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  
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The Lady Inside by loyalsock

I looked at the sinuous curves of her body. The long legs, the curling hair. She was built like my fantasy, every inch of her in pale ivory and inky black. Her pumps hugged the delicate curve of her feet—the arch and the heel. Her dress matched in deep crimson and swung light and silky around her narrow hips and broad back. I stared, unsure if what I was seeing was real or just Hollywood smoke and mirrors. When she turned to me and smiled—lovely white teeth glistening behind her red, red lips—I almost fell backward. I was beginning to think she was a mirage brought on by the heat of the Mexica... Continue»
Posted by loyalsock 1 month ago  |  Categories: Anal, First Time, Shemales  |  

Nothing Else Matters 1 by loyalsock

About a week had passed since the incident with Casey coming by my work place, trying to blackmail me, by telling my friends I was dating a transsexual. I had talked with Christina about the whole situation, and she had been able to calm me down and help me relax. I had been so pissed off at first, that I couldn't even think clearly at the time. But with Christina's help, I was now seeing things a little more clearly than before, and I had even come to a decision of how I thought I could solve the problem without being f***ed to sl**p with Casey as she was demanding.

I would let everyone I... Continue»
Posted by loyalsock 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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summer vacation

hi my name is alex
and these is story is about, how i got my first taste of sperm.

it was the first week of summer holidays
i went to visit my grandmother, who lives in the north.
i took the train there, the cart was full first, but after several stops
i had it for myself.

i was really horny,so i looked around and saw i was really alone.
i took my dick out and started jerking it slowly.

as the time passed i got at my full size and i was pretty close to cumming.
the i heard a whisper behind me "hey boy, need any help"

i panicked and tried to hide my dick back into my pants .
... Continue»
Posted by readyCreampie 1 month ago  |  Categories: First Time, Shemales  |  
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Caught and made into a sissy slut

It was for real this time. No fantasy. Reality. I was dressed up in red: fishnet stockings, g-string, and a babydoll. I was wearing a metal chastity cage that was pulling my clit down, and it was a clit, it only half filled the cage. I had a new cock too - a black face dildo which was double-ended. In my new role, I had to jerk it as I was fucked in my pussy and I was being fucked. She had fucked me so hard that I was completely submissive to her, sucking on my gag with wild abandon, a true sissy slut.

It had started earlier that day when I had been caught jerking off to a mixture of cuck... Continue»
Posted by andygone 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
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Dominant Sex Therapy

I had to go see a sex ther****t because I was addicted to jerking off. Little did I know she had a surprise waiting for me when i got there. I sat down and she got right to the questions. "So how long have you been jacking off" She asked. I said "about 20 years now" She nodded her head and asked " Do you watch porn when you jerk off?" I said "Yeah every time" She said "Good. How many times a day do you jack off" I said "all depends sometimes once, If i get a really good scene I try to break my mind from cumming too fast so it can be, 4-5 times a day." She said "Wow that's a lot of masturbat... Continue»
Posted by michneo 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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my date with jennycumslut part two

The second part of my story about my date with Jennycumslut. This memory will be burned in my mind forever and thinking about it drives me wild to know I did what I always fantasized about! Hopefully this will make you cum hard...

I left off that I had just made plans with Jenny to see her later that evening. I was out for a nice paced walk in the park close to my apartment at the time we had made plans so I hurried back home. After drenching of sweat from hurrying home since I was to meet her in less than a hour I quickly showered and didnt have time to shave my pubes down.

Me and her t... Continue»
Posted by redhotnailpolish 1 month ago  |  Categories: First Time, Shemales, Taboo  |  
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Fooled by a tranny

When I was 19 y/o and in the military I took a 2,000 mile motorcycle trip from my base to my home on the West Coast. Bad weather made me stop for a few days near Nashville, Tennessee, and I decided to go bar hopping. I ended up in a rather dark and smokey bar where there was a very bad four-person band, but it gave me a chance to have a few beers and dance with a couple of women. Shortly before closing a young lady came into the bar who was beautiful. She was short, a bit under 5', and very petite.She had very small breasts, which I like, and her mini skirt showed she had shapely legs, and... Continue»
Posted by 1kaboom1 1 month ago  |  Categories: Shemales, Taboo  |  
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Gary's Dressup Sissy

When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.

One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One mov... Continue»
Posted by palmorr 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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The last time I was a slut for cock

This is an account from my diary about the last time that I was a total slut for cock, before I realised that there was power in being dominant.

Went over to see Peter yesterday, it was about 8pm when I left his house but I didn’t have to worry about rushing home.
It was nice being with Peter again, he’s taught me so much the past year and he loves me in feminine clothes but he wouldn’t let me take the dress that I’d worn for him home. He let me go home wearing the bra, pants, stockings and suspenders though, it felt lovely wearing them when riding my bike. I felt so happy having spent th... Continue»
Posted by angelatvdom 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
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Old man fantasy

I have always been aroused by horny old men,I always wanted to be exploited by a group of old horny men until one day when i got this job that required me to take care of a 66 y.o gentleman.
He seemed so nice and since it has been my passion to serve other men i accepted the job without thinking twice.Things went well and we got along just fine..he was really funny and we became close friends very fast.
One day he called me and told me that he must speak with me face to face so that he can share a problem that he had for years with me,I rushed over to his place worried that something may hav... Continue»
Posted by cutecdkiss 1 month ago  |  Categories: First Time, Mature, Shemales  |  
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Vicky's Pink Diary 04

My head is spinning now, and as my uncle slowly pulls my panties down, I close my eyes dreading my fate!

I watch as he pulls my case out from under the bed. He takes a key out of his trouser pocket and unlocks the padlock.

"My god, how long have you had a key?!"

"Vicky, surely you remember losing a key a little while ago. It fell out of your jeans when your stepmother pulled them out of the washing machine. She didn't notice, but I did. Now I don't want to bring the other you up, but I did wonder why you would have a key in your jeans."

I knew I'd lost one of the keys, but I ne... Continue»
Posted by sparkyking 1 month ago  |  Categories: Gay Male, Shemales, Taboo  |  

Vicky's Pink Diary 03

So here I am waiting for my Uncle to come home for his tea, wearing Donna's knickers! Vicky's wardrobe is quite sparse, due to having just one locked suitcase hidden under my bed. I'm lucky that my stepmother is roughly the same size as me, and a total slut! Probably the only thing I like about Jenny is her clothes, she dresses like a girl half her age, and I know for a fact she shags around. I know my friend Sean has had a few narrow escapes from my stepmother. Then one day when I ask him about the way they smile at each other, he owned up. So I now know that they have fucked, I finally got i... Continue»
Posted by sparkyking 1 month ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Male to female transgender. Had no idea!

This is a true story. This was a time in my life where I was sort of a bitter person. This story is geared more about the things that led up to my encounter. This was a result of a series of events led up to this point in my life. Let's begin with the basics. I was in the military. I enlisted because I had one full time job and two part time jobs and still had trouble making ends meet. I was seriously overworked and my wife refused to get a job. So logically, I weighed out my options and decided to enlist into the military. It would be one full time job with a slew of benefits. Once I graduate... Continue»
Posted by fortworthfitness 1 month ago  |  Categories: Anal, Shemales, Taboo  |  
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Wife and Sissy invited to a party

My wife and I were invited to some friends’ house on a beautiful estate in TX for a weekend party. While we were both well aware of the debauchery that could occur at the event, we had no idea how much participation we would both play. We were just getting off the plane to meet our driver when my wife handed me a slutty little maid outfit, and told me to go into the bathroom in the airport and change before we got out of the terminal. I did as she asked and then tried to walk out without anyone noticing but too many people in the airport to hide from as I only attracted more attention.

When... Continue»
Posted by moeclitty 1 month ago  |  Categories: Fetish, Hardcore, Shemales  |  
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