Shemales Porn Stories
Page 113

relic fort

so as usual i am horny and i figured i would try something new. so i go to a place i have heard about. it is an old bunker fort near me it has lots of dark bunkers and lots of gates oh and lots of poison ivy.

so i pull up it is raining and i had packed my nice latex skirt and top so i decided to check things out. out of the car i go heading to the woods which i was told i would find the over grown play fort. sure enough there it was, i hiked around for a few minutes all the while noticing more and more guys walking around looking at me. finally one guy gets brave enough and ask what a prett... Continue»
Posted by deveon4u 4 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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Daddy at the Truckstop - 1

--This was an encounter that almost happened with a Daddy a while back. We talked about doing this for a first meet to make up for other times that didn't work out, and while talking about it with him was undeniably hot, it ended up not happening for a few reasons, chief among them safety. I think about how hot it would have been to smash a lot of my boundaries this way, though. Enjoy, and comments welcum :) ----

I couldn't believe I agreed to this, but here I was. The truckstop is maybe an hour from my house, and I was pulling into it from the highway now, dressed in stockings, panties... Continue»
Posted by StaceyDeprave 8 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Deep throat Made Easy

Deep throat Made Easy -reposted fro menext


Here for the first time ever are simple and explicit instructions on how to deep throat a penis. Position is important; you'll want to in position where you can extend and straighten your neck by slightly tilting your head back. This helps line up your throat with your mouth allowing the penis to slide in deep. The best position for beginners is with the receiver lying on his back with the giver lying on the stomach along side. You can prop yourself up on your elbows.

The penis must be THOROUGHLY LUBRICATED! I can't stress this enough. An... Continue»
Posted by bigdaddycoolzz 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 4 years ago  |  Categories: Gay Male, 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 3 months ago  |  Categories: Shemales  |  
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Lodgers Surprise

I had started my first job after leaving university. Having moved to a small town where I knew no one I had taken lodgings with a couple who had a large house a short walk from my office.
The couple were called Jenny and Mike. They were both in their fifties and had retired early and took in the occasional lodger. Jenny was about 5 foot 2 and was plump and sexy. She had good tits and fine legs which I often admired when I thought she wasn’t looking. To my joy she always wore nylons either stockings (I could see the garter bumps) or tights when she was wearing tighter clothes.
Mike was 5’11” ... Continue»
Posted by maninnylons 1 year ago  |  Categories: First Time, Gay Male, 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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Dr. Visit.

I turned 50 and the Dr. called and said I needed to make an appointment for my birthday physical. Well my birthday fell on a Friday and my appointment was the doctors last one of the day.
I was sitting in the waiting room and saw all the employees left the office. I asked the last one exiting if I had been forgotten? She laugh and said no, then she said that I was the last one of the day and that the doctor was running just a few minutes lat. I thanked her as she was walking out the door.

About three minutes after the last employee left the building the doctor came out from the back and ... Continue»
Posted by scottyj53 4 years ago  |  Categories: Anal, Hardcore, 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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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 10 months ago  |  Categories: Shemales  |  
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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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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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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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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 8 months ago  |  Categories: Anal, Shemales  |  
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I Knew I Was A Sissy (Part II)

For the next months I kept serving Nick at his will, usually every Saturday morning. It was convenient as his parents would go at the Super Market for shopping and I could use studying as an excuse.
We would meet at his place (not the garage anymore but his room) and I would give him a blowjob and let him fuck me. He kept his part of the deal (not spreading the news about me) and I kept mine.
I was enjoying it to be honest. At the same time on every chance I would go over my s****r’s room and “borrow” some of her thongs and stockings and dress up. My cock was getting hard every single time... Continue»
Posted by georgette32hk 7 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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My First Time as a Girl

I was hoping to hook up with a straight guy.

I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a big disappointment. My dad accepts me for what I am now. My mom always stands up for me when my dad criticizes me for acting like a girl.

My b*****rs look on me more as a s****r than a b*****r. Weird as it sounds I am more fem in a way than my s****r. I like to dress up in my s****r’s clothes and... Continue»
Posted by kbking70 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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