Shemales Porn Stories
Page 68

My step mom turned me into a sissy slut for dad

When I was in High school I would spend the summers with my dad and step mom. She was so hot and always dressed sexy, They were always very playful about sex, not like my mom and step dad. I loved the atmosphere.
During the week they would work all day and I would have the place to myself. I would always go into their room and see what I could get into. I found some picture of the 2 of them nude. Well after that I was always in their room jacking off to the pictures of my step mother naked. Little by little I would find other thing to help with my fantasies. I got into her dressed and wou... Continue»
Posted by firstknightd 2 years ago  |  Categories: Shemales, Taboo  |  Views: 24399  |  
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Str8 Guy Seduced By A Tranny (ch1)

Str8 Guy Seduced By A Tranny (ch1)

For a str8 friend here at xHamster... who is a fan of my writing and when I told him I would write a story with him in it... I'm not sure he knew what he was getting into..

Chapter 1

~~~~~~~~~~~~~~~~~~~~~~~~~

To say I was nervous was a bit of an understatement... but I was also very, very excited. This was my first time putting it out there in a big way.

Back home, I had gone out a few times and was completely passable... I guess I should explain more...

I am Lexi, that is my girl name... I was born a boy, or I should say... Continue»
Posted by TomStone90045 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1529  |  
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Ladyboy orgy in Thailand

During one of my many nights in the sleaze capital of the world Pattaya, Thailand I was at a certain ladyboy bar all dressed up in my sexiest outfit that the “girls” had ask me to wear in as I had shown them some pics of me dressed. Not that I could ever hope to compete with any of them!

Chatting away with one of the girls a German guy came over to us and said that he having a “party” up stairs and if we would like to join him and his friend. I assumed he just meant the girl from the bar and told them to have fun and she went off with the German guy. Just as they went threw the door lead... Continue»
Posted by toniparr 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 2267  |  
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Chronicles of Amy, Episode 1: The Beginning

Amy is a part time transvestite who enjoys to dress very sexy and go out and have some fun. So a few years ago, on a Thursday evening, she was sitting in her favourite cafe, looking at the poeple passing by, flirting with some attractive males, who were charmed by her appearance. She was wearing black fishnet stockings, 4 inch black leather high heels, a miniskirt that was barely covering her perfect ass and a white, very tight top. The cafe was quite full and so basically the only free seat was the one next to Amy. She was enjoying another bit of the chocolate cake she had ordered before, so ... Continue»
Posted by SweetAmy 4 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 1012  |  
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Daddy's lil bitch

As a young boy growing up I always had a fetish for dressing up like a girl. When I was 20yo I had my first experience with an older man, Tony a man in his 70s. I met him through a phone chat line and we seemed to hit it off right away. He told me that he would buy me some clothes and lingerie to wear for him when we met. So after a couple weeks of phone chat I mustarded up enough courage to meet him face to face.

When I arrived at Tony’s house he greeted me with a warm hug and kiss. Tony was a very handsome man, stood about 6’ tall and clearly looked like he took good care of his body. He ... Continue»
Posted by aznfemboi 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 3060  |  
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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 9 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 6771  |  
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Meeting A Guy on line part #2

We arrived at his hotel going in his room and just as we got in the door he turned taking me in his arms holding me tight around my waist, mine went around his neck and we stared in each others eyes smiling then I felt his hand sliding down from my waist putting both of them on my cheeks under the back of my skirt.
I didn't say a word at first just stood there letting him fondling them squeezing each lobe tight "dam you have a round soft ass" he said I just smiled more putting my lips to his and we embraced in a long wet kiss using lots of tongue.
I could feel his cock starting to get ha... Continue»
Posted by MonicaBond 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 1038  |  
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The Making of a Sissy - Part Eight

The girls sat cross legged sipping orange juice as the day warmed up around them. Roberts’ house had extensive lush lawns beyond the pool which shimmered in the hot sun; the pool looked very inviting to Bella and Roberts looked at the pretty sissy, his mouth watering as his cock pulsed.

“Just go in whenever you want; it’s nice to see you free from your usual routine, I know how strict your Aunt Jane is with you; swim naked if you wish, no need for a bikini here. Sandy and the others never bother with swimsuits when they’re here.” Bella was a little shy at first, but Roberts had seen her v... Continue»
Posted by midsummerman 2 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 401  |  
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Trip

"Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and her lips were painted a reddish-brown colour. As she looked at the card I watched the long dark lashes on her lids closely slowly over her huge, sparkling eyes. She slowly opened her eyes again, and reached for a box of cardboard cards sitting off beside her computer.

"Yes, Mr. James. I have your reservation here," her voice was low and gravely. She sou... Continue»
Posted by pau10s 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2480  |  
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Crazy dreams

I met Dave about 2 years ago at a swingers party. I had just turned 18 and he was 43. I remember thinking that it was hot that he was exactly 25 years older than me. I was dressed in drag and he was into t-gurls and he was married and hung like a horse and I happened to be into partying naked with big dicked married guys ;-) I always acted masculine around his wife, but whenever she wasn't around, I put on stockings and heels, makeup and wigs, and pranced around like a sissy little pantyhose cumslut!

One time me, Dave and his wife were hanging out, drinking. Dave and I were playin... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Group Sex, Sex Humor, Shemales  |  Views: 986  |  
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Halloween fun

Here's an interesting story that happened to me last Halloween, hope you like it. Last October, a local bar had a Halloween costume contest. Since I had nothing better to do (I'm too old for trick or treat) I decided having a beer and checking out all the silly costumes would be fun. I sat near the bar and almost immediately a sexy, slinky brunette caught my eye. She was wearing a light blue dress, black seamed stockings, and dark brown "fuck-me" pumps. After a short time I went over and said hello. She was smart and funny, and we really seemed to get along nicely, but with the loud musi... Continue»
Posted by throbbinghardboner 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 2392  |  
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POP GOES THE CHERRY

POP GOES THE CHERRY

I recently read a delightful account of a young gurl loosing her virginity to a f****y friend. Got me thinking about loosing my own virginity.

First, you should know, my mother made me a sissy. She took great delight in dressing me as a little girl, thinking back I can not remember when she did not. We lived in the country and most of the time growing up I played outside with my dolls in dresses. The only time I wore little boy’s clothing was when f****y visited or I went to school.

Everyone in town knew I was a very sissy acting little boy. I was bullied a ... Continue»
Posted by littleoralvee 3 years ago  |  Categories: Shemales  |  Views: 1218  |  
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Cheri

My name is Cheri, I live my life in lace and satin. I have always loved the way those materials feel against my soft skin. I have shoulder length red hair and bright green eyes. My friends used to call me Charles but about 12 years ago i had this epiphany that i felt out of place as a man and one night while I was out at a club with some friends, I realized that being a woman felt... I don't know, right,
to me I guess. It's been a long road but I'm so much happier now.

The first time anyone ever found out I had a dick after that was about 10 years ago. I went to a new doctor for some ant... Continue»
Posted by LadyShi 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1474  |  
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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 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1689  |  
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Meeting with the Boss

I arrived to work to find out that my boss wanted a meeting to discuss my future with the company. I wasn't sure if this was good or bad. My boss, Erica, is a very beautiful woman. She is hispanic with bronze skin. She resembles Eva Mendes and is about 5'7" tall, 130 lbs with great curves. She always wears tight skirts and blouses. I entered her office and she told me to sit. After talking for about 20 minutes I was thinking this is good because I would have been fired immediately.

She then asked me how dedicated was I to her and the company. I said very dedicated and that I love working he... Continue»
Posted by swordlvr69 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 3732  |  
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TV loving cock

Sorry I didn't keep you posted on Saturday night, but I was sorta busy being my usual slutty self. Story to follow:

I talked to a guy on megaphone. He works as a night security guard at a big office building on the edge of town. He is there all by himself in this huge, mostly vacant building, in a safe area, so there really isn't anything for him to do but set around and be horny. So he was looking for someone to come over to his job and get nasty.

Naturally I was just the girl!

I'm all dressed up in one of my hottest outfits and looks, so I jump in the car and race over. It takes m... Continue»
Posted by jenn1 3 years ago  |  Categories: Shemales  |  Views: 1315  |  
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Once upon a time, I dated a Co-Worker...

It was summer and Dad had asked me to help him around his car insurance agency. Mainly I answered phones and typed in reports on the computer. Couple of nights a week, I would also vacuum, clean up and straighten the office a bit. Had the weekends left to go to the beach and hang out with my friends. Robert and Mayra still worked there, they had been with Dad for years. Both were appraisers, and were in and out of the office constantly. There was a new part-time clerk. Her name was Natalie, in her mid-twenties, a tall girl with long brown hair and hazel eyes. Chatty and friendly, I felt... Continue»
Posted by latinCharm 1 year ago  |  Categories: Anal, Shemales  |  Views: 3255  |  
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Sometimes, mistakes do happen but they can be real

A few weeks ago I was wandering round some of the nice tv/gay sites for this area of France when I got a message from a guy asking me if I would like to meet. Well, I was very horny at the time, so nothing new there, was aching to do something to somebody or have them do something to me, you know the feeling, when you ache to feel something nice and long in your mouth or being slipped in your pussy.

I thought to myself why ever not, he seemed like a nice guy, he wanted to meet on his way home from work so we arranged to meet in a quite well known gay rest area between his destination and t... Continue»
Posted by antoniaf 1 year ago  |  Categories: Masturbation, Mature, Shemales  |  Views: 1440  |  
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Chrissie and the Professor

Possibly the after hours engagement with an English Literature professor at college may have been the thing that convinced me that older
men might be more to my liking.
It was during my Junior year at the university when we were discussing the poetry of Arthur Rimbaud, the French poet, that I became infatuated with my professor. He was a typical scholarly gentleman one would expect to encounter at a major university. He was in his mid fifties, and still in remarkable condition for his age. He was about just under 6 feet tall, blue eyes with salt and pepper hair. In class he was charming, w... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Shemales  |  Views: 907  |  
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Atrip to the dentist

My wife thought I was at the dentist but I was really with my special friend Sandy. It had been over a month since I could sneak away to see Sandy. My cock was wet and hard just from the ride thinking about what she would be wearing and how we would please each other. When She met me at the door I almost exploded just looking at her. She had blonde hair today in a long braid d****d over the front of her shoulder. Her eyebrows were dark thin lines followed by different shades blue all the way to her eyelashes. Her cheeks were painted a blush color and her lips a dark crimson. She wore a black ... Continue»
Posted by Zeffer1 2 years ago  |  Categories: Shemales  |  Views: 1197  |  
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