Shemales Porn Stories
Page 77

A Slut Is Born

There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?

It had all started a few months ago. I was locked out of my house in the pouring rain, and I went over to our neighbor’s to see if I could hang out with him until my parents got home. He was a cool guy, single, mid 30’s, worked for a software company, and drove a nice car. Had bought me... Continue»
Posted by MacDaddy714 2 years ago  |  Categories: Anal, Shemales  |  
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Sissy services her football player part 2

While my man was playing football, (never understood the fasination with kicking a ball about), I changed into my schoolgirl uniform. My 'Special' white satin panties with a lace frill. Why special? well they have a little lacy hole at the back for the pleasure of my man! Sheer satin hold up stockings, white knee socks with a heart pattern, sooooo cute! Black patent mary Janes and to finish off, a Japanese sailor top and blue pleated skirt.
Once dressed i would feel so good, prancing about in front of the mirror, waiting for my man to return. I would feel my sissy cock hardning against the sa... Continue»
Posted by igglepiggle 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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So you know women...

I was in another state in an extended stay motel for spring break. The girls were hot and the guys were hotter, I did not know which way I would go on this trip.

I had noticed two females that seemed to be daughter and mother, they would come in early morn and stay in their room. The young girl was close to my age and very light skinned, the one I thought was her mother was some what darker and had a heavier build.

One morning I was returning from an all night party and was just a little bit d***k. I saw them as they pulled in and the elder of the two ran from the car saying someth... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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My shemale girlfriend

I met Andrea out side a bar on the west end, she was outside smoking a cigarette, I started a coversation with something stupid like "you come here often?" she laughed and we started talking had a couple of drinks and exchanged numbers. Andrea is about 5"10", shoulder lenght dark red hair, nice green eyes, and full red lips.....our first date we met at her favorite resturant and she was dressed casual geans high heals and a tigh t-shirt, showing me her great ass, long legs and big round tits. we had a good date nothing happened but a small kiss out side her cab........Date number to we met a... Continue»
Posted by rockerroller 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Amazing Birthday

Best birthday ever

Hello every one hopes all u doing great and enjoys my story

We all get d***k on our birthday and enjoy every second and get those feeling next day hangover or sore well I was sore from sex and not a big drinker but had few

Friends took me to movie I was wearing one piece shorts top jumpsuit in white no panties and lace bra in white high heel scandal we were group of tranny and black guys
Always fun. Anyway after movie we get to one of friend home we were drinking guys drinking beer few us girls drinking wine its was getting late 11pm I decided to get home few guy f... Continue»
Posted by shawn777 2 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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Best Birthday Evening


Hello every one hopes all u doing great and enjoys my story

We all get d***k on our birthday and enjoy every second and get those feeling next day hangover or sore well I was sore from sex and not a big drinker but had few

Friends took me to movie I was wearing one piece shorts top jumpsuit in white no panties and lace bra in white high heel scandal we were group of tranny and black guys
Always fun. Anyway after movie we get to one of friend home we were drinking guys drinking beer few us girls drinking wine its was getting late 11pm I decided to get home few guy friends (JJ & Marc
... Continue»
Posted by shawn777 2 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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My shemale boss part 3

I was woken by the vibrating noise of my mobile and looked over at the time, the bedside clock said 1am. The caller I'D on the phone simply showed Bitch, naimly my boss Miss Jones, would she never leave me alone.

I answered the phone and still being half asl**p simply said 'yes'.
'Don't answer me with that tone Rob' she said. 'Sorry, but its one in the morning' I replied.
'Be a darling Rob and pick me up from the club, text me when your outside'. Before I could say anything she hung up.

I pulled my arse out of bed, slipped on some tracky bottoms and a t-shirt, jumped in the car and dr... Continue»
Posted by big_rob49 2 years ago  |  Categories: Shemales  |  
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One of my favourite experiences.

I don't know if anyone will read this or even enjoy it but I've not told it before and it gets me really... excited :P
This took place before I discovered my love for crossdressing and I suppose could also be the reason I started!

A few weeks after I turned 18 I got a girlfriend. She was bisexual but she didn't know that I was also bisexual. Her name was Lisa and she was also 18. After a few days of seeing each other we ended up having sex. It was your average, nothing exciting, foreplay followed by sex.
After a few weeks of our relationship we were getting on great... We'd learned so muc... Continue»
Posted by matttay 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Clara Bow's Academy for W-B Ladies Part 4

Greville Hambleton tried hard not to think of the ginger sissy; he was married to a fiercely independent woman who was very much in charge in the bedroom, and who knew all too well of Greville’s weakness for effeminate transgendered she-males. As he was often cuckolded, Tara his wife being partial to sampling cock, she turned a blind eye to his discretions. Like a lot of otherwise heterosexual males who enjoy the assertive control by the superior sex, he had a keen dominant streak which revealed itself with a preference for younger ladies, and even more so for sweet effeminate sissies. His ... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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My 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 b... Continue»
Posted by cute_girls_with_dick 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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For my Tgal Mistress

If one night You don't feel sl**py, that's the kind of thing i could do to help You with that:
You'd be laying on Your bed, in pyjamas, ready for bed, but not sl**p. i would take Your pants off.
First i'd put Your still soft cock in my mouth, feeling it grow bigger on my tongue and sucking it deep and fast. While i am stroking Your cock with the back of my throat i'll be playing with my ass, injecting some lube in it and then inserting a dildo, a long and large one. i would have one hand on the dildo, the other on one of my nipples, and my head bouncing fast and deep on Your pubis.
When You... Continue»
Posted by mouth2fill 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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The way i like to be treated...

One night, You call me on my phone and ask me to come to Your place. i feel excited, because every time i see You, i have a hell of a good time :-) So, i hurry to come to Your place as soon as i can.
Once at Your door, i knock. I can hear You say "come in", so i come. Without any other word, You say "Naked!". So i undress. "Quickly" You add. I undress as fast as i can. "Seems like you're horny. Good boy. Turn around" You say. So i turn around and my back is facing You. i can hear You come closer. Then, You firmly squeeze my ass cheeks. "I'm gonna have some fun these, you know? Very soon. But ... Continue»
Posted by mouth2fill 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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My first time with a BBW Shemale turned into a thr

I was at the club on a saturday night and didn't really expect anything different to happen that night oh boy was I wrong, happily wrong. I was sittin at the bar gettin d***k as hell and this voice from behind me and says " hey big daddy can I sit with u ? " I look up and I see this fine, phat, thick, lightskinned woman lookin right at me. Me bein' a BBW lover and partial to light skinned black women she was a wet dream cum true.

I said sure u can sit here baby if u tell me your name. She says " my name is passion, whats yours daddy ? I told her and we start to chat about things we like an... Continue»
Posted by Champdick 2 years ago  |  Categories: Shemales  |  
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Natural Ingredients for a crossdresser

It was still snowing outside and I wasn't going to be recieving any visitors today so I decided to treat myself and while the day dressed how I wanted.... I had set the heating up high at my place, so I could wear one of my sexy side tie bikinis which show off my sweet little ass so well. Having enjoyed the view in a full length mirror and got some self shot snaps, I found myself sitting at my dressing table wondering how to amuse myself next....
Looking at my face in the mirror I noted a little dryness (no doubt from my earlier shave, god how I hate that ritual, you girls don't know how luc... Continue»
Posted by MagicCarpet 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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A Cross-Dresser's tale

You may think of me as Fiona, and I am a cross-dresser.
A story by Erica inspired me to pen my saga of cross-dressing.

I am also a recovering alcoholic, with a few days over 19 years without a drink as I write this, and I suppose the two tales are intertwined to some extent.

Not that I am a saint by any means, a lot of people with a lot less time have a better sobriety than I. But I learned that alcohol is a poison to me, so I avoid it. I just do irrational things when I add alcohol to my system.

For a while, I blamed my cross-dressing on the booze. But I discovered that feelin... Continue»
Posted by prairieFreak13 2 years ago  |  Categories: Shemales  |  
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A wonderful experience


When I was 20 years I was a wonderful thing happened as I remember all my life.

With my best friend Dani and friend, we agreed that we are going to our dull and went around the city a bit. This was a great opportunity for me to be dressed as a woman and such a walk around town for all to see. From what I can remember is I enjoy women's clothes and the role of women. Although I had all the things women I asked a friend if I could borrow her things and be with her disguise, that would not be too suspicious that I'm a transvestite since time immemorial.
Dani and I have come to friend Suzi w... Continue»
Posted by maximatv 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Clara Bow's Academy For Would-Be Ladies Part

Pepper returned to the room and sat on her new bed as she unpacked her things; Marie helped her stow things in a wardrobe and chest of draws allocated to her. The blonde smirked at the new girl as she blew on the brunettes nails she’d just completed; she would enjoy painting Pepper’s nails. Pepper bounced softly on the large double bed; the plug felt so nice now, and she loved the way it teased her anus.

“Why such big beds? I’ve never had a double before and it feels so comfy.” The three girls glanced at each-other knowingly, and then giggled; Pepper’s jaw dropped as Marie let her fluff... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Going out as Leslie

A Short Story...

There was an unmistakable feeling of acute anticipation in my stomach leading out to my trembling hands. I knew where I was going tonight and the probable outcome.

Shaved, made-up sexy, dressed in a 3in heeled mini boot, fishnet stockings with a garter, black pleated short skirt, a white blouse with ¾ length arms exposing fishnet arm warmers to a stunning black straight haired wig, didn’t help the situation any.

Going dressed like this to a man’s lair and offering myself to him…I was quite apprehensive to say the least. Will he accept me? Will he go arm in arm with me... Continue»
Posted by LeslieStone 2 years ago  |  Categories: BDSM, First Time, Shemales  |  
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Clara Bow's Academy For would-be Ladies Part

The new sissy stood barefoot; naked but for the soft white gown. Though bewildered and a little scared, her little cock poked forward in the gown, partly through fear and partly through excitement as she felt the eyes of the stern woman upon her. Clara Bow rose slowly from the leather chair she sat in, cane in one hand, she wagged a finger summoning Pepper forward. She was accompanied by the buxom Nurse Wykett; her ample buttocks and breast bulging in her white uniform, her black stockings and stilettos a far cry from the usual sensible shoe preferred by most in her profession. Mistress Bow... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Pia's T-girl adventure

I met Pia a couple of years ago when I was out with friends at a transgendered night club in London. Originally she was born in Finland but she has lived in London now for several years. Her looks are typically Scandinavian with platinum blonde hair and a beautiful, friendly smile. Although I had never had sex with her or seen her naked, I could tell that she has a lovely, shapely body. After chatting with her I discovered that she is bisexual and really only interested in meeting other woman or couples after enduring, what she calls, too much ‘vanilla sex’ with straight men. I also discovered... Continue»
Posted by lightwave40 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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