Shemales Porn Stories
Page 74

unexpected

Well my mom knowing I was a crossdresser and hell all about me and more.I have only talked to her on the phone since her s****r Mary came for visit two weeks ago.Well aunt Mary didn't know that i was dressing as woman and living as one plus she didn't know at all about me and my mom being together.
I just got home from getting my nails filled and some shopping for sexy shoes and dress I wanted when the phone rang.I looked at the caller id and seen it was my mom.I answered it and said hello. To my surprise it was my aunt.
She said how are you? Good and you? She said well I been here to wee... Continue»
Posted by cdpaula 4 years ago  |  Categories: Mature, Shemales, Taboo  |  
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He NEEDED me!

I had gotten dolled up nice and slutty looking in my motel room, and had been internet chatting for a couple of hours, so I was feeling very sexy. All dressed up and nowhere to go in a small southern town. I peeked out my window and could see that the place looked pretty dead. No lights were on in the guest rooms; no cars on the street, nothing going on at all. Here I was, in platform shoes and a mini dress, face made up, and a very wet g-string from being horny and tucked for hours. I locked the room and strolled around the parking lot, then across a grassy area to where the highway bordered ... Continue»
Posted by dana213 5 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Pick-up truck abduction scenario

He led me out the back door where his pickup was parked behind the house, surrounded by tree cover with no other houses in view. It was a big truck, two door but very high off the ground and with a particularly long and high bed.
"Get in" he said. I headed toward the passenger door. He stopped me halfway.
"No, no darling. in the back. Get on in there, now."
I walked back and looked in the open tail gate at the seven foot-long bed, which was literally what it was now, a bed.
A mattress with a clean white sheet lay across the bottom. The truck was kinda jacked up so it sat very high in the... Continue»
Posted by subval79 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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surprise pick up

This is how I lost my virgin ass.

I got off work one day and on the way home I figure I'll stop by the adult book store to try see some peak show. The place was unusually packed. I usually go there an play with my dick.

So the place packed so I leave when I leave I notice two girls walk in across the street one had those short shorts and made me honey right away the notice me looking at them.

They waived hello and I drive past them and toght fuck it let me see if I can give them a ride. I drive my car in front of them open the passenger window and the girl with ahorts come up and say... Continue»
Posted by down4tgirls 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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becomiing a bitch


It was supposed to be simple. A blind date, set up online. A hot chick. Me getting laid for the first time
in a while. You know. Simple. And that's what actually happened. Sort of.
I get to the bar, I see Meghan across the way, sitting pretty in a short black dress, legs crossed,
sipping on a martini like she's sucking my cock already. Far as I'm concerned, I'm as good as fucked,
the way she's making herself out to be: smooth thighs, big, round tits, lips that could blow the cap off
a bottle of Bud, legs long as tomorrow and an ass as big as today. Fuck, I feel I'm in the bag already,
... Continue»
Posted by nicoleinberlin 3 years ago  |  Categories: Interracial Sex, Shemales  |  
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Aidans training

* Post Date - 4/17/2011
* PDF Download -


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Story posted with author's permission
Read User Comments (2)

I started out with a pretty happy life, but I screwed things up. I was the king of my castle, but now I'm not even the queen. More like the maid. So I guess you could call it a riches to rags story. How did it all happen, well let me back up and tell you.

My name is Aidan, and I started life with a plus, because my f****y was pretty well off. When I turned 21, I got my sh... Continue»
Posted by stig1963 5 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Sissy Sharon's Saturday

The day begins at 4:30 a.m.. I am awakened by the alarm next to my bed on the floor in my tiny cell. It’s barely big enough for the old mattress I have to sl**p on, but it has been my bedroom for the past 8 or 9 years (I’ve lost track). Every day is basically the same. I wake up and crawl from my room to the bathroom at the end of the hall in the basement. Cameras watch my every move, so trying to cheat by walking (ever) is a no-no. The punishment is far worse than the crime, so I am always obedient. In the bathroom I administer several enemas, being sure to expel all the nasty waste from my b... Continue»
Posted by scatpetsmaster 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Gloryhole

I have had a fantasy since college. I was in the adult viewing booth when I heard a tap. I loooked down at the hole and heard a womans voice asking if I wanted my dick sucked. Obviously I did, so I pulled it out and stuck it through the hole. At first it was just licked with some tugging on my balls. Once I was fully erect she took into her mouth. She sucked it with just her mouth at first. She then started working it with one hand while gently rubbing my balls with the other. I counldn't hold back any longer. I came with such intensity I thought I would pass out. It was the best blowjob I eve... Continue»
Posted by swordlvr69 4 years ago  |  Categories: First Time, Shemales  |  
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My First Time - part 2

Seems right that I talk about the second time Steve and I had sex. Don't worry I'm not going to talk about them all, just some of the kinkiest times we had. The second meet was notable not only for the sex but also I was sort of willingly pushed into a higher level of crossdressing. For a long time I had been wearing panties, tights, stocking etc under my male clothes, when I got the chance. I had worn dresses etc when home alone, but this was different.

I got a text message from Steve on the Sunday evening after our Saturday night, saying he had enjoyed himself and did I want to do it ... Continue»
Posted by uktransvestite 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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on my way to work

Hi
there I was driving along on my way to work in harlow listning to the stereo and watching for the occasional trafic cop and thier little trafic calming measure that they point at your car. There was a car with a puncture (itwas leaning to one side) at the side of the road just ahead of me, as i stopped to enquire and perhaps offer some assistance the lady stayed in the car with the window up high enough but just down enough to speak out of, she mentioned that she had a puncture and her jack was not where it should be and can only assume that her pertner had taken it from her car and not re... Continue»
Posted by natasha1975 3 years ago  |  Categories: Shemales  |  
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Fantasy Cums True part 2

This story is written by Tittie-baby for xhamster.com any reprint without permission is strictly prohibited.

FANTASY CUM TRUE part 2

I woke up with Terri still sl**ping in my arms. God this woman was beautiful. She was so surprised that I didn't freak out when I found out she was a shemale. I have been with over a thousand women but Terri was my first shemale. Last night had been special for sure and I wanted to start the day off right too. I knew she would be getting up soon for work so I eased myself down the bed and took her limp cock in my mouth. I licked all around the head and the... Continue»
Posted by tittie-baby 2 years ago  |  Categories: Shemales  |  
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A Night on the Town

This is my first post, hope you enjoy. May continue the story if I get positive feedback.
It was my 21st birthday, and my friends were taking me out for a night on the town. We had been going from bar to bar, getting d***k and trying to pick up women. Finding no luck with the woman at the bar we were at, we decided that it was time to move on again. We wandered down the street, looking for the next bar. We found one called the Dollhouse, and decided to go in. We found a table and immediately ordered our drinks. I had the need to go to the restroom, and excused myself from my friends.
On my ... Continue»
Posted by thomas1927 3 years ago  |  Categories: Shemales  |  
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Yahoo instant messenger boi

I was about 22 or 23 and it was the summer time. I was already mega into cross dressing and web-chatting for older gentlemen, but only then for the internet. hungry for someone to touch or hold me for real, I began to search craigslist for older men hosting or looking for other men,. I would send them pictures of me dressed in thongs and stockings and await responses. One afternoon, I got this older dude, and he sent a yahoo link as well.,. so I promptly added him and began to video chat. He said he liked my outfit and wondered if I wanted to come over to his apartment, which wasn't far from w... Continue»
Posted by villelohne 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Riverbank Tranny Fucktoy

Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river.

It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site.

I had been chatting to Fillipe for a couple of hours, and we were both getting hornier and hornier with each new message that we sent. It was me that asked if he would like to meet that night, and he of course said yes. There are a few cruising areas near around the closest city to me and we arranged to meet at one... Continue»
Posted by donnamarie09 1 year ago  |  Categories: Anal, Shemales, Voyeur  |  
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Crossdresser's Rough Sex

To start things off there is something you need to understand. I am bi sexual, but when I am with a guy I am a submissive bottom. I love to pleasure other guys. That's how this experience came about.

I was out for a drink with a girlfriend, catching up on the latest gossip when a voice whispered in my ear

"I can see your knickers."

I spun round and saw a moun5ain of a man, he looked like a chubby lumberjack, all man and really butch. I blushed and panic as no one knew I was wearing panties or stockings. It turned out that when I sat down my pink panties were visible over the top of my... Continue»
Posted by MacDaddy714 2 years ago  |  Categories: Anal, Shemales  |  
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Pussy Fever




Pussy Fever


Joyce sat at the table in the bar waiting for her friends. She was upset and looked forward to having some drinks with her work friends to try and get her mind off of her worries. Last week things had been so different. Exactly a week ago, Frank, one of the hottest salesmen for the company had finally successfully talked his way into Joyce’s bed. He was amazing! His body was that of a greek God and he knew exactly how to please a woman. When they finally went back to her place he rocked her all night with his tongue playing her pussy like a harmonica. Joyce was in... Continue»
Posted by klammer 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Tracy's Transition Chapter 1

It was Halloween morning and I awoke pleasantly surprised in my pink panties. Today was the day, I had spent the last 3 weeks meticulously picking the outfit out under the disguise of the holiday it finally now was. What started off as curiosity in high school of occasionally wearing panties, stockings, and tights morphed into an over whelming desire to completely transform myself into my newly developed alter ego. Unlike most of my friends I wasn’t in college, I had lost my job AND girlfriend two months before. Had I the ability to go to the bar and meet new people I’m sure I would of lookin... Continue»
Posted by SissyXtina 2 years ago  |  Categories: BDSM, First Time, Shemales  |  
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Another Lawrence.

The other Lawrence

I was working on the top floor of a block of flats, it was a neglected old block that had a bad reputation. I knocked on the door of a flat that I had to repair a kitchen in. A guy anserd in his pants and let me in. The flat was dimly lit and unkeept ,it smet of smoke and musty sex. I had a few jobs to do so I got to work. I was on my knees in the kitchen working on the floor. It was so hot in this flat i was sweating. He walked in and put the kettle on. He stood with is crutch inches from my face. I noticed his cock getting bigger in his pants. I Couldn't take my eyes of... Continue»
Posted by ofluffy2 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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THE Sissy a*****ion

You are walking along, you feel a presence, a person quickly comes up behind you and chlorophyll you. You pass out but you catch a glimpse of his green army officer hat.


You wake up several hours later chained to a rack naked. Two identical women come out with a cart filled with cosmetics. First they take this special soap that when it touches your skin it makes your skin very sensitive and a sensation of pleasure takes over at the slightest touch, then the two women grab nail polish and paint your toes and the your fingers. Then, they grab a special foundation that they apply to your wh... Continue»
Posted by thegoods699 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Straight, to Bi, to Gay, to Trans, to Straight (Pa

I don't want you to think we simply lived happily ever after. Nothing is that simple.

We've had our ups and our downs, and our ins and outs. We've had three major hurdles, so far. The first was me freaking out over the idea of having a boyfriend. As natural as it seemed to be with him, and as mind-blowing as the sex was, it was still a huge shift in thinking for me. The second hurdle was coming out.

The third was his affair. But more on that in a minute. As I want to talk first about coming out. Friends and f****y may say they support gay rights and all, and they may be fans of... Continue»
Posted by TransContinental 1 year ago  |  Categories: Gay Male, Shemales  |  
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