Shemales Porn Stories
Page 119

older man fucks younger guy

I was 16,when I first move out from home,renting a traler,that look like the trailer from urban cowboy.well the traler needed ssome repairs,and I went to see my landlord ,ed was his name,who also own a motel,as I was talking with him at his home which was part of the motel,I sorted got the hint that he was into guys,he kept on hitting on me,said if want me to stop I will,told no,kinda like it.well from there we went to the bedroom,said would i like to watch a video?yea sure,in my closet and pick one out,as i was looking thru his videos,I notice a box that had some womens clothes,said whats up... Continue»
Posted by blonde68 3 years ago  |  Categories: Shemales  |  
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Weekend i will never forget(Part 1)

I hadn’t seen Cindy for nearly 2 years, other than a quick lunch as She passed through town last year. We text or IM almost every day and talk on the phone every few weeks. We had been coworkers for many years and remained very good friends to this day. I would say that She is my best friend as I have been able to confide in Her about things I have never told anyone. In addition to being a very trusted and loyal friend, Cindy is beautiful and very desirable. I still can’t figure out why some man hasn’t swept Her off Her feet and married Her. She is truly amazing.
As I said earlier, I ... Continue»
Posted by wannabesubformt 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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More Dirty Sex with Tania. Part Two Looking for Pr

Part Two. On the hunt for Sex in the Red-Light Area

Luckily most of the guests at the Premier Inn had now checked in so when we both went down through the reception area it was again deserted except for the receptionist who only acknowledged the door key being placed on the counter. There were a couple of people in the car park but most were only interested in heading for the Beefeater restaurant. One young couple did take a second glance, the guy’s eyes nearly pooping out his head. It’s not often that you see two trannies, dressed as whores walking across a car park in rural Gloucestersh... Continue»
Posted by joannacd1 4 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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State Park Night Life ...

I was honey as all get out and showed up at the State Park in Quincy Ma, ready for some man on man action. All cumers were welcome. No rules on age, color, or size. I wanted dick. Stiff hard dick. And yes a creamy facial was on my list. The sun was just going down, and some old guy drove by my car and gave me the look. I didn't think anything of it at the time. So I got out of my car and walked out into the park. Almost dark now. Sat down on a bench and waited to see what would walk by. Maybe a talk stud or a young guy. Then I saw him coming from a distance. I could see him having problems wit... Continue»
Posted by brianswallow 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Young Sissy Ch. 01

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.

*

I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a... Continue»
Posted by bi_hengst 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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T-Girl at the bus stop

The radio was loud and the top was down when I first saw her.
She looked so beautiful sitting there at the bus stop.I remember her legs, they were long and tan and clad in silky smooth thigh highs. Her skirt shifted when she crossed her legs and I could see the garters clinging to her tan skin. She turned her head and smiled at me while I waited for the light. Her eyes were so bright. I think they were green, maybe blue. Every movement she made seemed to beckon me. As if she was calling me to her.

I couldn't help but stare at her tits - they were fabulous. A car behind me honked. shatterin... Continue»
Posted by shemalefckn 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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My first encounter

I started dressing in my s****r's clothes when I was about 11, she would have been around 13 then. It was wonderful, just Mother, s****r and me at home so when I got a little older, I promoted myself to Mother's clothes. She was a real fashionista back in the 1950s to 1970s, always very elegant and very sexy.

The inevitable happened and one day my s****r caught me. I was wearing some of Mother's clothes, with a lovely slim fitting skirt pulled up above her panties and stockings and my cock so hard in my hand, midway through a delicious wank.

My s****r didn't say a thing, simply walked... Continue»
Posted by antoniaf 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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helping friend in need

It was a quite normal saturday I just got home from getting my nails filled and eyebrows waxed,till a female friend of mine came by very upset and crying.I asked her what was wrong and she showed me a letter that she got in mail saying she had to pay $2800.00 dollars by Monday 4:00 pm or go to jail for 6 months. Her exboyfriend got some tickets in her car and never told her or payed them. Since they were all on her car she was the who had to pay them.
I told her if I had money I would lend it to her but I just payed off my house to get out of the interst rate I had.I said to her if she coul... Continue»
Posted by cdpaula 3 years ago  |  Categories: First Time, Shemales, Taboo  |  
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shemale sex slave

BDSM JOURNEY.

Let me first say i am no writer by any means.

This story starts 5 years ago. I was looking to move up in the mountains off grid with a homestead. I was a single man and wanted a parnter who could share with the daily chores and have for sexual gratification. Finding some one to leave everything the city offered to move to a rural area was a quest in itself. I knew I wanted a completely submissive woman ant my feet.
So I put a ad on craigslist and it went a lil something like this" tall single white dominate male iso single submissive woman to move to a homestead in a very ... Continue»
Posted by bigfranks36 1 year ago  |  Categories: BDSM, Fetish, 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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My Wife My Mommie part4 con

About two block from the house Ann stated "Tom's Home". It was
then that Tami noticed the pacifier around his neck and in his
mouth. He took it out immediately and saw the two girls in the car
next to them at the stop light smiling.

Since it was a warm day, Ann had the car windows open. Tami
looked at the girls, and now being himself, stated "I'm trying to
quit smoking."

"Sure you are," the driver of the other car said, as the light
turned green and she drove off laughing.

"Please Ann, don't do this to me. I'm sorry, I really am,"Tami
said.

"Now you know ... Continue»
Posted by alexwd0 4 years ago  |  Categories: Fetish, Shemales  |  
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the smoking rubber slut lodger

I'm now a prisoner of my own addictions and lust. only a month ago i moved into this new house as a lodger after my marriage failed. i soon discovered that my landlord was really a rubber tv landlady. her house had a rubber fetish playroom, full of huge heeled white platform boots, rubber dresses, hoods, dildos and glistening pvc macs. And of course there were cigarettes everywhere, long Rothman royals, black sobranies and Marlboro red 100s - perfect whore cigarettes.
Anne caught me one day wearing one of her rubber dresses and those thigh boots all made up in front of her full length mirror ... Continue»
Posted by jodiesmoke 4 years ago  |  Categories: Fetish, Shemales  |  
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Playing it straight

I had exchanged emails and photos with Jennifer. She quickly answered the door and I noticed her plus size shape peeking through a sexy black teddy as she guided me in the room. As I stepped in the suite I saw the focus of my attention, Alexia. She was sitting on the hotel couch I was floored by her beauty. She looked a little Hispanic and Asian with blonde hair and black roots peaking through. She looked to be in her upper 20’s with a smooth face covered in a bright orange tinted foundation, light pink lips, light charcoal colored eye shadow all the way around her eyes with dark black eye br... Continue»
Posted by Zeffer 3 years ago  |  Categories: Shemales  |  
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Forever like this

My wife wrote this and asked me to post it on Xhamster, wich I eagerly did!

It's late, and the night of dancing has left us exhilarated; tired in that way that makes you feel more alive than you do any other time. We wave goodnight to my housemates and shut my bedroom door.

Sam grins her impish grin at me. She'd gone for a goth look, this evening, ladling on heavy eye makeup and an old ripped denim jacket, before looking over at me and telling me there was no way I was going out in anything so dull - and made me up as her negative; her ghost in blue and white. She turns away, now, and s... Continue»
Posted by Ankakalle 3 years ago  |  Categories: 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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Riding the Lakefront

I finished my training session and went to my car to get my bike. I always worked out and then rode the lakefront in Chicago. This was routine..Wednesdays and Saturdays. Wednesday, I finished my workout and headed to the path. It was 6:00pm and I rode from the Hollywood curve to 71st Street and back. I am usually able to do it in about 2 hours. August 13th, it was a hot night but I liked riding when it was that way. Joints all felt loose. Rode well. Carried some water bottles with me.

Being intersexed with big tits, I always wore a bra. This night was no exception. I had a zippered shirt ... Continue»
Posted by titsR4abuse 3 years ago  |  Categories: Shemales  |  
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old tom part 3

since I had been at old toms place and enjoyed the part of me that enjoys lingerie and stockings, I had a mixture of excitment and nervousness as to when I was going to return to toms or knock it on the head due to guilt!.

When my day off finaly hapened yes I had a few chores to do which gave me time also to think about what to do next, yes I did know its just the thing any one would do given the choice.

I phoned old tom regarding his invitation since my last visit a week ago and he replied to pop over as he was a loose end and he would leave the front door on the latch.

The front do... Continue»
Posted by natasha1975 3 years ago  |  Categories: Gay Male, Shemales  |  
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Shemale boss fucking

God, I felt like it wasn´t my day.

I had been sent to the boss office one day and I tought that I was gonna gett fired or something like that.
When I came into her office I saw that she was dressed kinda sexy. She was wearing a suit that had a lot of cleavedge. When I got there she said:
-Do you know why I have called you here?
-No. I answered
-I wanted to ask you if you can come to my house tonight and have a litle chat. She said.
-Okay

When I got there I was a bit nervous. I knocked at the door and strangely her sexy secratery opened the door for me and asked me to come in. After ... Continue»
Posted by Ankakalle 4 years ago  |  Categories: Shemales  |  
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unnecessary roughness

Some years back, I was on an overnight business trip. I would often crossdress in my motel room to entertain myself and practice looking sexy. I could pass as a real woman from a distance but not so much up close. I'd been strutting around in a short a****l print dress and platform heels, admiring myself in the mirror and occasionally walking around outside my room in the motel parking lot. There was a convenience store/gas station next to the motel, and I kept walking over toward it, daring to be seen by people filling their tanks, etc. Late that night I decided that I just had to go over to ... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales  |  
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Master's Surprise For Me

Master called and told me to be ready at 5:00. He instructed me on what to wear, a blouse and skirt, and to wear my long hair in a ponytail. He told me to make sure my pussy was shaved and may nails done. He often likes to give instruction on my appearance when in his presence. I always love my time with Master and so it was with great anticipation I began to get ready. I was a little surprised that we were going out, since we usually play at my house. He told me this would be a very special evening, one i would not soon forget.

My pussy was getting wet thinking about his words...he... Continue»
Posted by ThyMastersBitch 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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