Shemales Porn Stories
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Boy gets Fucked by Shemale

This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when I was sixteen, I decided to see what it felt like to be a girl. I had never tried anal before (I could never bring it up to my girlfriend) but I knew I had to try something. So I gathered all the necessary tools and went into my room. I locked my door so my mom wouldn't accidentally walk in on me a... Continue»
Posted by ClassicCockx 11 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 7028  |  
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Loved it in my ass

Hi all
It all started very innocently but turned into an obsession.
Me and my girlfriend (Karen) at the time had a perfectly normal if slightly boring sex life, wow was that about to change. One night we were at it and in the heat of passion she wanted me to fuck her arse which is something i had never done previously, at the time it would not have mattered what she asked i said of course and dutifully filled her lovely arse with my hard cock, it felt so tight and good that within minutes i was spraying her arse with my hot cum. She smiled a looked at me and commented on how good that was an... Continue»
Posted by blueone71 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 6951  |  
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black man's sissy boy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The draw... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 6864  |  
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My Transformed Wife

"Sometimes I wish I just had a dick," my wife said, wincing and squeezing her heating pad into her abdomen. She said this at least once a month, when her period would bring on two or three days worth of cramps and bloating.

I grinned and rubbed her stomach, "If you had one, you would just spend all your time playing with it and peeing standing up."

She giggled and squeezed my cock through my pants, "That doesn't sound so bad."

We never said anything beyond this, but from the first time she had mentioned it, it sparked a desire within me that I had never known I wanted. I had always ... Continue»
Posted by drew1207 4 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 6863  |  
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FUCKING UNCLE BOBBY

The title of this story isn't really accurate as I wasn't fucking Uncle Bobby see Uncle Bobby was fucking me! He wasn't really my uncle he was just my mother's boyfriend but he lived with us so it was kind of like he was my Dad I really like him a lot he gave me lots of attention and took me places and gave me money for doing chores for him he really was a good guy! He had a boat and it was a nice one too he kept it docked at the Marina and one weekend he asked me if I wanted to go fishing with him well I loved to fish and I loved boats so hell yes was my response and we set out to go fishi... Continue»
Posted by laceysgirl 10 months ago  |  Categories: BDSM, First Time, Shemales  |  Views: 6707  |  
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my wife make me her sissy slut

I married Jen when I was a successful high earning bachelor at the age of 30. She
was 25 at that time. 5'4" same height as me, 120lbs, petite blonde with
blue eyes, a set of DD tits and an ass to die for. I was short, skinny yet she was
attracted to me when we first met in a bar down town. Later on I found out that it
was Laura her friend who had told her that the porsche parked outside was mine.
Now, after 5 years of marriage, things were quite different. Things had actually
started going down hill after the first few months when subsequently Jen had clearly
stated that my 3 inches coc... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 6674  |  
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A Lodger's Leanings

By - Lucy Roberts

A Lodger's Leanings

I was brought up by my Mum as my Dad left us when I was very small.

Mum and I had a good relationship and, only having a female role
model, perhaps it wasn't surprising that I got into wearing my Mum's
clothes. At least that was where it started but as I entered my
teens I used quite a bit of the money given to me at birthdays
and Christmas to buy my own clothes.

By the time I was about 13 I was used to having the house to myself
while my Mum was at work. As well as being able to have friends over,
it gave me plenty of opportunity to ... Continue»
Posted by jayymie 10 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6653  |  
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Daddy's Girlyboy

I was alone in the house so I was indulging in my fantasy of dressing up as a girl. I had my long hair all straightened, full make up and my skimpy sheer black thong on with black stockings and suspenders with a tight lycra dress which showed off my very girlish figure. This was finished off with a pair of killer heels which complemented my shapely, smooth legs. Dad wasn't due in for a while yet and mom was away on business. I put some music on and was enjoying being the real me for a while.

I was dancing to my music and looking at myself in the mirror when dad came bursting through the do... Continue»
Posted by sexycock3 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 6647  |  
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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 5 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6638  |  
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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 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 6586  |  
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How My Life Changed

How My Life Changed Chapter 1

My wife Mary and I had been married for over eight years and I thought
our life was very good. She was an attorney for an important law firm
and rapidly rising towards a partnership. She made a lot more money than
I did in my job as a fast food worker. That didn't bother me as much as
it might have many men. We had a nice house and lived well. Mary is 28,
5'6", 120 pounds and had 38D breasts. She is a beautiful brunette with
brown eyes. I am 5'8", 140 pounds and used to taking orders from the
people I work for. As my wife gained more power ... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 6579  |  
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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 2 months ago  |  Categories: Shemales, Taboo  |  Views: 6573  |  
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Cum Eating made easy (CEI guide with no acrobatics

This post is dedicated to all of those, like me, that have fantasized about eating their own cum. This kind of fetish is something really, really hot and kinky, and I know that most of you are already excited and in... mmmh tension, I guess. And I also know that most men who indulge in such a fantasy have often chickened out as soon as they experienced their orgasm. All lust gone, all desire of a thick load in their mouth gone. Of course there are already an awful lot of CEI videos out there that have methods to ease the balance between desire and the act itself.

[image]http://ep0.xhcdn.com... Continue»
Posted by sissyAlyna 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 6548  |  
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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 7 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 6527  |  
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It started w/the neighbors wife then her husband.

About 5 yrs. ago on new years I was invited over by the neighbors to party, they had some friends over; we were getting plastered and eating food celebrating the New Year. When out of the blue in front of her husband and friends the wife starts kissing me, I gently pushed her away not knowing how the hubby would react, much to my surprise, his reaction was almost as if he didn't mind to the point where it looked like he was turned on by it.
That night after everyone had gone, the husband had been long passed out, we went to my house next door, & I ended up fucking her. I remember her saying h... Continue»
Posted by MyaTranny 2 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 6461  |  
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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 1 year ago  |  Categories: Shemales  |  Views: 6459  |  
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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 month ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 6464  |  
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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 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 6447  |  
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Cum hungry paper boy sissy

Cum hungry paper boy sissy



When I was thirteen our next door neighbor Pat offered me a summer job
helping him deliver papers and magazines. I quickly said yes and my
foster parents agreed. I liked Pat a lot as he always patted my ass when
Vance and Liz were doing something when he came over for dinner as he
smiled and winked. I loved the way it felt and smiled back as my cock got
hard.

I was light build and kept my long blonde hair in a pony tail and always
wore cut off jean shorts. I had also been jerking off and eating my
creamy delicious cum loads for over a year as I loved... Continue»
Posted by jayymie 7 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6442  |  
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Crossdressing - Teen fantasy with Panties to Cock

Confessions of a Crossdresser

I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to understand how I have evolved.

If I was a woman, I would be a cum dumpster: intelligent, attracti... Continue»
Posted by ericalace 6 months ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 6421  |  
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