Shemales Porn Stories
Page 7

First Time - Surprise Shemale

I'm an eternal masturbator. I've always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so many things to see and do. One day I discovered the true beauty of the shemale. Wow. Gorgeous women, with cocks. Prior to this it had been women with strapons that got my attention, but this? Perfection. Then cam the webcam. I found a couple of sites where you could interact with such beauties and c... Continue»
Posted by hungrymanx 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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MY GAY PRISON SISSY ****


I'm sure many of you have seen a number of movies or television programs based on prison life behind bars. Having recently spent some 29 months in an undisclosed New England State Pen, I'll now share with you first hand, some of the wildest and most unbelievable sexual experiences one could ever imagine.

While still on parole now, I will change my name here and not mention the state facility involved. Other than to substitute a few names for some of the real ones involved, all of what I'm disclosing here actually happened between late July of 2007 and Dec. of 2009. My work... Continue»
Posted by cddixie 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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mom teaches son to be a slut

I loved women. A lot. My obsession with women later became a desire to wear women clothing. One day, three months after my 18th birthday, I could not hold back any longer, and I put on the the most accessible lingerie I could find - that of my mother.

Since then, I frequently visited my mom's wardrobe whenever she was out. I would wear her clothes, and it would make me feel sexy. I would pretend I am a woman, and take sexy pictures of myself. I realized how much I liked this, and this led to me realizing my bisexuality. I wanted a man to make me his woman.

Because I wanted a man so badl... Continue»
Posted by momandboys 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Changing Rooms

Being a 'girl of a certain kind', I always use the women's changing rooms in stores when I am out trying and buying clothes. I tend to avoid the 'communal' type, where we are all stripping off together, as I'm quite shy and you also never know if someone may pick up on the fact that not everything about me is female - and make a complaint!
So I aim for those individual booths, where you can safely strip off and try things without being observed.

I was in one branch of a big national chain that sells a whole range of clothes within my budget and had gathered an armful of things to try on. T... Continue»
Posted by mica_d 1 month ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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The Postman Always Rings Twice

After I moved away from home, I felt pretty good. No one could tell me what to do. I missed only one thing: The closet of my big s****r. Since I was 13, I regularly wore her clothes, especially the underwear. As soon as I was home alone, I went to her room, and started to try on her thongs, bras and stockings. At the same time I played with my little clit and sometimes I slid some vegetables into my boypussy.
I really missed these little dress-ups, so one evening I decided to buy some own lingerie. For the beginning I ordered a cute bra with a matching thong and a pair of thigh highs. I could... Continue»
Posted by notgeile_fickstute 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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My b*****r's Lover

I was eighteen and in high school when it happened, my b*****r was twenty and still living at home. I had to borrow my b*****r's computer one day to do some work for school and I guess maybe I let my curiosity get the better of me a little as I found myself instead of writing the essay I was supposed to be working on, looking through what files he had saved on his computer. I was pretty interested in particular by a very full folder hidden away in a place that you would not expect to find it. Now, I'd been a teenage boy for long enough to know that I had probably just stumbled across my b*****... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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My shemale mother!!!!!!!!

I know there is a similar story similar to these but be assured, the other story only served its purpose as a catalyst for this one. This is a pure fantasy, the top fantasy that has been lingering in my mind for several years..here it is....


I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I am not sure of the reasons but I do know that my mother is an average looking woman with nice looks and a not so fantastic body. Her pear shaped figure is a norm for any woman with Indian origin and what I do know best is her mammary g... Continue»
Posted by yarracuda 4 years ago  |  Categories: Fetish, Mature, Shemales  |  
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First time fucked by a shemale

I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon.

I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.

Her hair was dirty blond and loosely curled, and her face was quite beautiful. She was wearing makeup, but it was und... Continue»
Posted by surferboy_ibiza 10 months ago  |  Categories: Anal, First Time, Shemales  |  
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Sissy picked up in hotel

...
you are having a drink at the hotel lobby bar, another night in a hotel working away, sipping your drink thinking how you are becoming sick of the same boring hotel routine and looking around at the people checking in and out, the bar is relatively quiet for this time of night.

A girl walks up to the bar next to you and asks for a drink, you glance over and the first think you notice is her bobbed blonde hair, down to just below her jaw line, she catches your eye and you become more interested. You give her a quick look up and down, not really caring if she catches you out as you are ... Continue»
Posted by JasmineSissyCD 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.

In August 2007 I was 24 years old and was constantly masturbating to shemale porn. My best friend was getting married and ... Continue»
Posted by feinor11 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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peeping

Peeping

I was sitting on the bed in my room. I was reading Penthouse Forum and
read a letter about a peeping tom who became a sex slave after being
caught when I began to hear voices coming from next door. My house is
only 5 steps away from our next door neighbour's so in my room I could
hear anything from loud music to sex. To investigate the noises I ran up
to the window and moved the curtain slightly to see what was going on
through the next door neighbour's window. To my shock I saw a man and a
woman having sex. The man happened to be my neighbour, Dan. He is tall
man about 6'... Continue»
Posted by aimen72 2 years ago  |  Categories: Shemales  |  
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Halloween..

Because I am a bartender even on Halloween, I had to work until 2:00am. Daniel works the total opposite; he came to visit me at work. All the staff was in costume. I was dressed as a witch, quite sexy I must say, it got me a few unsuspecting compliments. Apparently, I am rather passable as a witch. I was referred to as a girl a several times by people who aren't regulars, but who expects your bartender to be a 5'8", guy in a ruffled skirt, fishnets, corset, black lips and nails, covered in glitter.

Daniel hung around with me for a while then I lost him somewhere out in the party. He made a... Continue»
Posted by bisubtaylor92 5 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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camping with a giant ,part 3

the tall muscular Trevor had me in his powerful arms as he carried me over to his tent his massive long cock jutting out over twelve feet in front of us bobbing like a gigantic divining rod as if it was seeking ass/pussy ,as we walked along the road between the camp sites a large truck pulling a long trailer was approching us it slowed up and stopped and a huge black man rolled his window down and greeted himself ,saying that his name was Mandongo , we both said hello ,i could see that he was interested in both of us as i got out of the truck and walked around to meet us ,a huge powerful man a... Continue»
Posted by huge_cock_rules 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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sissy caught by daddy

I was so scared ,Dad had caught me several times dressed up in my s****rs clothes but the last time he told me that the next time he caught me the punishment would make me never disobey him ever again,and that was less than a week ago.Now here I sit on the foot of my bed wearring my s****rs satin lace panties and bra,her stockings,heels and her favorite slutty skirt and top.I had skipped school just so I could dress up and had just finished putting on my lipstick when dad walked in and caught me.He laughed and told me that the school called him because they didnt believe the lame story I told ... Continue»
Posted by sparkyking 9 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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My Wife's Affair With The Shemale

My wife Tracy were not married for that long when she had her first affair. I met Tracy in high school and we dated for years before we got married when we were twenty two. I hit the jackpot with Tracy because she is absolutely gorgous and just an all around sweetheart. She has long blonde hair with brown streaks, hazel eyes, long legs, large tits and a tight ass. Tracy has always loved taunting her body wearing cloths like short jean shorts to show off her legs and tank top shirts to show off her stomach and belly button ring. I have always thought of it as a double edged sword because I lov... Continue»
Posted by anonymouspervert69 2 years ago  |  Categories: First Time, Group Sex, Shemales  |  
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My mother, my lover

Wow
I have no idea where to begin with this story. My mom came by yesterday while the k**s were off fishing on the lake.
I knew when she got here that there was one thing on her mind, and she was not shy about letting me know either. I was painting our daughters room when she came in calling for me, I knew just by seeing how she was dressed that my implant was in for a workout.

She walked into my bedroom and starts calling out " Baby mommy wants to play".
I walked into the room and saw that she was only wearing a smile on her face, both nipple rings, her tongue piercing, and on her toes... Continue»
Posted by Taboo69 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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Male to Female Transformation

Male to Female Transformation

Genre : TG SOS or Surgery/Transformation Male to Female
Story : Cristine Carter
CH - 1

The last thing I could remember was walking out of the Bank
and crossing the road to my car. I had just been to see my
bank manager to discuss transferring some money from one of
my accounts into a high interest savings account.

I had won quite a bit of money on the Lottery, enough to
change my life. I was unaware just how much my life was
going to change.

I had just reached my car door when I felt someone bump
into me. Then everything went blank...
... Continue»
Posted by cristinestone7575 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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T-Girl University

Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for her from all those west-coast surfer dudes. He hoped she wouldn’t forget him and made a vow to himself to stay faithful no matter what. But there would plenty of temptation for him as well: Jason was going to a small northeastern college that, until recently, had been an all girls school. Jason’s in... Continue»
Posted by slatemhor 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Paying Mommy’s Mortgage

As long as I can remember I have had a penchant for wearing nylons and lingerie: pantyhose; stockings; silk, satin or nylon panties (not those horrible cotton things or G-strings that are like candyfloss in your arse crack -- I mean, full cut panties, cami-knickers, or boy leg panties); garter-belts; slips -- both half and full; basques and corsets.............I can go on but you get the picture.

I also have a fetish for high heel shoes: sandals, pumps, courts, stiletto heels, kitten heels, stacked heels, Cuban heels, platforms, open-toe, "Pilipino bar girl fuck-me shoes"; you name the hig... Continue»
Posted by sparkyking 2 years ago  |  Categories: Anal, Shemales, Taboo  |  
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He transformed me to his bitch

This happened during summertime. Just after the end of school period, last summer before college. All of my friends had left the city for a beach house they rented. I was to go several days later. So I was alone in an empty city, since everybody was away for the summer holidays.
I was waiting at the bus station when a stranger came and asked me if I knew some decent place to have a beer. I suggested him a few pubs that were close when he asked me to join him. I was surprised and a bit scared, so I kindly declined saying that my friends were waiting for me. He insisted suggesting to meet for ... Continue»
Posted by georgette32hk 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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