Shemales Porn Stories
Page 5

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 11 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6654  |  
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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 7 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6644  |  
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My Uncle Wally's Sissy Boy Wife

Penned by: Miss Deborah (Debi) Leigh Johnson



One



I did not know what I could expect, as the Greyhound pulled into the
bus station. I did not know a whole lot in fact, as I was a rebellious
know it all, fifteen year old brat.

My parents were pretty good as far as parents went. I had not locked a
roof over my head, or enough food on the table, but I had always
resented the fact that my parents were not rich enough to give me
everything that I wanted. I knew in the back of my mind that this was
a pretty immature attitude, but what the hell, it was the way I
felt. I also di... Continue»
Posted by jayymie 11 months ago  |  Categories: First Time, Shemales  |  Views: 6638  |  
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My first cock-turned me bi

Most of my life I have been extremely hetero. I mean, absolutely no interest whatsoever in men. I have always loved everything about women, their scent, their soft bodies, their boobs, their muffs, everything. I could go on and on about how much I love women. I never, ever saw myself being with a guy. It just didn't ever interest me.

About 3 years ago, I was on a business trip that took me to Chicago. I was by myself in the evenings for a week. Anyone who has been on a business trip should know that after the work is done during the day, at night there is something about being alone and out... Continue»
Posted by Dionysus2 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 6623  |  
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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 3 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 6611  |  
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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: 6587  |  
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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 29 days ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 6563  |  
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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 4 months ago  |  Categories: Shemales, Taboo  |  Views: 6553  |  
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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 9 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 6530  |  
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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 9 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6524  |  
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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 3 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 6512  |  
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Bondaged and fucked at a hospital: pt1

I was watching a baseball game with my cousin Jackie who was 15 and it was an unusually hot day for which I hadn't fully prepared for since I was young and head strong to say the least. It was half way through the game and I had run out of water but I didn't want to take my cousin's water or miss the game so I stayed in the intense heat without any water as Jackie continued to sip from her bottle of water. I didn't want to alarm her or miss the game but I was starting to feel dizzy. Sure enough, as I touched her shoulder to tell her I wasn't feeling so good I fainted and fell out of my seat la... Continue»
Posted by adblman 2 months ago  |  Categories: BDSM, First Time, Shemales  |  Views: 6508  |  
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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: 6490  |  
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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 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 6487  |  
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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: 6474  |  
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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 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 6405  |  
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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 1 year ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 6399  |  
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My Girlfriend's Mother Has a Secret

A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson.


Characters:
- Tim, 18, Student
- Susan, Tim's Girlfriend
- Julie, 44, Susan's Mother ;-)


Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pride and joys. Normally, this would help her relax and unwind, but tonight, and on several other nights, she found that remained tense. She couldn't get over the feeling that somebody was watching her, for several days, perhaps a week; when ... Continue»
Posted by Asmarani 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 6396  |  
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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 12 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 6370  |  
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