Shemales Porn Stories
Page 113

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 4 years ago  |  Categories: Gay Male, Shemales  |  
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The Apartment!!

I had been given notice to quit my flat and was having trouble finding one to suit. Rents were way to high and the flats were to small. In desperation I appealed on facebook if anyone knew of a flat for rent that was not to expensive. I was amazed to receive a reply from a friend of a friend! I knew him a little but had never had much to do with him. He was leaving his flat and needed to find someone to take it over. He told me that he thought it would suit me. As it was just a message I was not able to ask him what he meant. I applied to the address that he gave me and got an e-mail that eve... Continue»
Posted by dasilva1672 3 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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First time glory hole part2

...... I woke up and the lights were now on so I was guessing it was night and they close this place at 12 so was hoping that the man who closes it down let's me go so I looked at my watch it was 11 so was hoping someone would come soon.

Someone came in I guessed it was the cleaner cos he went into the other stall and sounded like he was cleaning so I was hoping he will let me go he had finished cleaning the other stall and then open the door to the stall I was in he looked in shock to see me sat there with no trousers on after being shocked he looked round went to the main door and shut it... Continue»
Posted by briggs123 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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FUCKED BY MAN'S WORKMATES

I live with a very handsome guy who works the night shift from 10pm to 6am at a local factory, he leaves for work at 9pm so i am on my own from the time he leaves. He left to go to work one night last week as usual so before he left i was dressed in a sexy g string panty lace bra and i was looking real hot so he could think about me all night at work. About ten minutes after he left i heard a knock on the door so i thought he had forgot something so i opened it without thinking that it was his two workmates that wanted a lift to work as there car had broken down. I stood there in my lace bra ... Continue»
Posted by hotbitch5 4 months ago  |  Categories: Shemales  |  
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Sissy For My Flatmate, Chapter 1 – Caught In

My heart was racing as I gazed up at my flatmate, there was an something of an evil gleam in his eyes as he looked down at me and my mind kept jumping back to the events that lead to this moment.

I'm a closet crossdresser, yet now my flatmate (whom I managed to hide my “hobby” from for the past six months) had me on my knees, wearing what I can only describe as the sluttiest clothes I own, hands cuffed behind my back, waiting for the “surprise” he had planned.

The previous night:

Work can get pretty stressful, I'm not complaining – I enjoy my job and I have my own ways of dealing with... Continue»
Posted by Yosho 4 years ago  |  Categories: First Time, Shemales, Taboo  |  
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Chrissie Learns A Harsh Lesson PT 1

Chrissie's Gets A Harsh Lesson Part 1

This is a story I've been wanting to write for a while but I only recently got the gentleman involved to tell me it
would be okay to write about our encounter. Normally it wouldn't bother me to write about any experience I've had but
this gentleman is a special friend and I didn't feel right about relating the story without his knowledge. As you probably
guessed, with exception of Kelly, I generally change the names, dates, and locations mentioned in my stories. Even though
I won't be using his name or telling you any personal ... Continue»
Posted by chrissieCD 4 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Shemale Next Door Pt. I

(Note: This is an excerpt from "The Shemale Next Door" on sale on Amazon now)

It was a warm Saturday afternoon, one of the first really hot days near the end of spring and right before the beginning of summer and Ken was waking up late like he always did on the weekends and found the trashcan in their house completely full. He sighed to himself and was going to call to Roger to take care of it until he remembered that Roger had gone away for a week to visit his f****y and that he had left this morning. This one was all on him. He sighed as he cinched the plastic handles up, tied them... Continue»
Posted by rehumanize 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Night With A HOT Sissy!

June 28th, 2009. End of senior year of high school. I, Angus Corleon, actualy graduated. I wasn't a model student. I've been a leather jacket wearing, rebel rousin, beer drinkin, hell raisin son of a bitch since middle school. My parents didnt care about me, after all my b*****r is a cop and my s****r is a lawyer, and im the law breaker. Anyways, enough about who i am. My buddies johnny, brandon, timmy, and danny have a hell of a party planned for tonight. Big bon fire out in the back woods of where we live. Must be 200 people were expecting. We set everything up, fire pit, band equipment, cha... Continue»
Posted by CDboy9097 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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the real me part two

I took the mail in the house and mom was on the phone.She got off the phone and said we need to do something now. I said what she said go to my bathroom were she had me lift up my dress and take off my thong an bend over. I felt something cool and wet on my hole.Then felt her slide something warm inside me i moaned a little the felt warm liquid flowing in me,she ladies must douche and be clean and fresh.Then right in front she did her self her pussy was smooth with long lips.
Well it was close to 9 pm and she asked me if I would drive to the next town and get some stuff at the store.I grabb... Continue»
Posted by cdpaula 4 years ago  |  Categories: Shemales, Taboo  |  
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Amy The Tranny Chapter 2

I couldn't stop checking Amy out all through dinner. She was dressed in a skin tight mini skirt, her perky little tits standing out from her tiny frame, and long hairless legs cast in nylon fishnet stockings, and 6" stilettoe heels. I wasn't the only one gawking at her! Every guy and even some girls were checking her out as well. I was surprised a little when she excused herself and went to the restroom, and walked into the ladies! I mean, it did make sense, but my sore ass made me think she should do into the mens! Anyways, after a nice meal and some small talk, we headed back to my place fo... Continue»
Posted by panteeluvr 4 years ago  |  Categories: Fetish, Shemales  |  
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Selene and the Shemale


I had been friends with Selene for six years - we had met in our first year at university - at a film society party. I was a science major specialsing in partying. She was a music student. She had a sultry, sexy singing voice that was perfect for jazz and blues and even back then, she was earning a little money singing at parties. That was why we were both at the party that night, and why we ended up being friends with benefits during our college career, though never more than that. We stayed in touch after college but mainly on email as I left to work in Australia while she went to London.
... Continue»
Posted by Hangdog90 4 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
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Blackmailed Crossdresser , part II

A few weeks after that first incident with Stefan where he had blackmailed me into having sex with him, I got a text message off him. I was a bit surprised, as we had managed to ignore each other in work. I was growing optimistic that this incident was behind me. Even though it was left me feeling violated and with lots of confused feelings about myself.

I was shocked to open the message on my phone and seen two pictures of him fucking me in the hotel! I was on all fours on he bed, in bustier, stockings and heels, with a wig on but visible to see.And he was behind me, obviously fucking me. ... Continue»
Posted by tricked-sissy 11 months ago  |  Categories: Shemales  |  
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June 3rd 2011, Dream Come True!

Friday June 3rd, 2011, I went out to a local bar. Not crossdressed, just the man in me. I am normal on the outside, beer drinker, hell raiser, party kinda of guy. So anyways, im sittin at the bar with my buddy sam, drinking coors light and shots of cuervo. well sam had to cut out early cause his wife was getting bitchy, so he left and i stayed and got d***k. at the other end of the bar i was eyeing this gorgous red head, id say, 5'3, slim body nice tits, drinkin beer, which is a turn on for me when women drink beer!! And she noticed i was lookin at her. So i got up with my beer and went outsid... Continue»
Posted by sissypantyhoseboy90 5 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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Back to School

Back To School
Nikkie Silk

I was so excited. This was going to be the first day at my new job. I had recently been appointed as the receptionist and administrative assistant at the local Elementary School. I set the alarm to wake me up early, so that I could get ready and make sure I would be on time. I was excited but also nervous. I had yet to meet my new boss, Mr Michaels, the Principal of the school. I had been hired by his deputy, so I would be meeting him for the first time today.

The State had just enacted an affirmative LGBT action hiring program. This meant that as a pre-op tr... Continue»
Posted by nikkiesilk 9 months ago  |  Categories: Anal, Shemales  |  
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How Nick became Nicki. A sissy story

This is the story of Nick. Nick was straight.
It was Friday night and she was getting ready to go out, she had something special planned tonight. She had her favourite pair of red and black lace lingerie on, the panties cupping her round smooth cheeks, her light blue pencil dress that hugged her figure and gave her a passable cleavage, white heels that make her look sexy even though they squeezed her toes and rubbed her heels and she had barely got the hang of walking in them. She had done her make up too, as well as she could, a little eye shadow and a cherry red lipstick. Her stomach was af... Continue»
Posted by ilgreturns 8 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Tranny orgy

You can live with someone and never really know them.
I was running a car wash in West Palm beach and every day I would take lunch at a cafe down the Blvd. The food was good, and cheap and I had the hots for Debbie, this built to the hilt redhead chick working there. She wasn't any great beauty but she had a body to die for. 36 DD tits. big hips and thick legs. Just my type. After a couple weeks I got the nerve to invite her to TGI Fridays for some drinks.
After a few, she started talking about her past. She was on parole from Ohio for cocaine trafficking. I found that interesting because a ... Continue»
Posted by kwhagie 11 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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Sissy crossdresser and her Black Daddy Part 2

After nearly a week of almost nonstop creampies, facials,deepthroating blowjobs and bareback anal fuckings, my black daddy and I were sad to know we had one more night in which to have our nasty, kinky fun before our respective f****y remembers return. I had dressed in all manner of nasty lingerie and costumes for his black cock to use and I loved every second in which he entered my holes. This being our last night together my daddy told me to "take a shower white slut, and make yoself pretty. I got a surprise for dat ass babygirl". My cock could hardly get any harder I was so excited. I enter... Continue»
Posted by AllisonCumms 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Gloryhole slut last night.

Well I was a horny slut last night and went to this little arcade in the city last night. Fully slutted out and in a new pair of silky nude hose I was hoping not to be disappointed....I was not!

I payed my fee and went into the back to the booths where there were a massive amounts of guys in the booths and just standing around. I was a little nervous waiting on a gloryhole booth to open but was catching the eyes of all the horny cocks also waiting for a turn in the boths. Finally after a few minutes 2 booths opened up and I went in hoping to get my hungry lips working right away. No soon... Continue»
Posted by luvpantyhose67 5 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Helping a friend

Anna has been working in my office for a year now. I have never heard her talk about a boy or girl firend. Anna is 5'7'', long legs, light brown hair almost to her waist, very pretty. I have always talked to her, had lunch, but she had never opened up until she needed some help.....

Anna had bought a house that needed work. A couple of months after she bought it, she was complaining that her sink leaked. I told her i had done odd jobs through out my life and i would be more than happy to check it before she called a plumbler. She told me to come over friday after work.

Friday came,... Continue»
Posted by edukateme 5 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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During the divorce 15 years ago

I am older maybe wiser but still a k** at heart and love to pretend. I get home Saturday around dinner time, after horrible (He’s Cheating, Has other women) things are said by my supposed loving wife of 15 years about how I mentally abuse her or the he doesn’t love me anymore innuendos. A Saturday meeting with attorneys because she cannot meet during the week due her job, this won’t be cheap. The divorce is painfully slow, meetings about this and that are beginning to feel like a hot sweaty day covered in glue rolling through broken glass! I get home and pretend that my c***dren are st... Continue»
Posted by Chartless 1 year ago  |  Categories: First Time, Masturbation, Shemales  |  
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