Shemales Porn Stories
Page 111

My first time with a shemale

This is a true story, probably the wildest thing that ever happened to me. It happened when I was about 19 years old and lived in Hamburg, Germany. At the time I was one of those willowy, thin guys, little body hair and a healthy appetite for sex but not much experience yet. At a young age I discovered how exciting it is when I fondled and fingered my ass while masturbating and I developed a real fascination with anal sex.

At the time I used to visit a club ("disco" in those days) somewhere off the Reeperbahn, the famous red light district in Hamburg. One such Saturday I left the club in ... Continue»
Posted by HOLY-SMOKE 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 5471  |  
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The Bondage Whore, Chapter 13

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 13 - Unbelted

As Joe released Rachel that night, he informed her that Jimmy wanted to see her. Then Joe did not put Rachel's chastity belt on her, which thrilled Rachel. Rachel strolled into Jimmy's office, wondering what was up. Jimmy rarely conducted business after hours. "Rach, babe, have a seat. I have some good news for you!"

Rachel sat, and Jimmy continued. "Congratulations on your third year anniversary sweetie! Do you know what that means?"

Rachel was clueless. "No, not really", was all she could manage.... Continue»
Posted by thongcutoffs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 738  |  
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im back

well im back from our aniversary holiday. on the last post someone put tell us more about your wife so i dug around a bit. well start of with the basics she has long black hair, a beautiful face with beautiful blue eyes. she has large breasts im not sure how big im not good in the bra size department. shes petite and has a large cock and she shaves all her pubic region. she owns two houses i only found out when we went there for our anniversary. i was shocked to see what was in the house it was full of sex toys, latex clothing and lots of other things. well we started the week off fun. she had... Continue»
Posted by xxjamiexx 3 years ago  |  Categories: Shemales  |  Views: 388  |  
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first time public

My First Time In Crowded Place As Cross Dresser

about 2 months ago, i got up the courage to go to a crowded public place dressed for the first time
i put a post on craigslist saying where i was going and what i was wearing
then i drove to shopping center parking lot and dressed up in the car, make up, red lip stick, red finger and toe nail polish, blond wig, ear rings, necklace, rings, watch bracelets, thigh high stocking and gatrer belt, black 5" heels, black mid thigh dress
i drove to a closer parking spot and took a breath, put on sunglasses, grabbed my purse and stepped out into publ... Continue»
Posted by cdamanda 3 years ago  |  Categories: First Time, Shemales, Voyeur  |  Views: 1359  |  
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My sissy son,by his dad and lover. Part 2

Hi,thought it was about time i let you know about my son and me.

This is Part 2.

So...there i was,on my knees staring at my son's beautifull cock. Not big,only 4" long..but sweet with a nice head and completely shaved..(or waxed). "Oh Jack...suck me please...pleeease...been ages since a handsome older gentleman touched me there." Pre-cum was leaking from it...and i licked the end...and gently took him into my mouth! He moaned and slowly made his hips go forward and back...gentle movements like he was fucking my mouth.I was sooo horny at this point i would have done anything...so i did...... Continue»
Posted by chocandres 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1657  |  
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Book store cock slut..

I would like to confess somthing that happend over the holiday weekend.
It was a saturday night and so hot and boring that i had 2 get out of the
the house and have some fun.I decided to grab some things from the
closet and head out the door for the evening.I drove out to a very peaceful
forrest preserve on the way 2 my favorite adult book store.
The cool breeze felt good on my shaved legs and body.
I drove for about 3o min and arrived at my favorite spot.
I smoked some bud and watched some sexy bitch getting
gang banged on my portable.I started to carress my b cup
tittties and brush... Continue»
Posted by rudedog69 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 584  |  
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MY SHEMALE WEEKEND

As I told you in my last story, I met a shemale who wound up spending the night at my place. I told you that we arranged to spend the weekend together with her roommate and that is exactly what we all did.

I arrived at Chandra's apartment about 2pm. She greeted me at the door wearing a pair of short gym shorts and a tube top. She kissed me and let me in. My cock grew hard immediately and all I did was walked into the apartment. Chandra led me into the livingroom whenre her roommate Jizelle was sitting. I was introduced and Jizelle told her that I was cute and now understood why she didn't ... Continue»
Posted by adw276 3 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 2277  |  
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I've dumped my boyfriend. Now he wants cock..

Me and Marc had been going out for 7 months. He's nothing that special to the eyes but he has a way with words. He could put a simple sentenced together and get any girl, any age, with any genitals?
I thought it was only a rumor going around that he was Bi-sexual so i ignored it completely because he was great in bed.

Tall strapping lad about 6'3", toned body, tanned skin and semi long hair about ear length. Long enough to twirl in your fingers while he's pushing himself into you.


After 7 months, he kinda gets boring. Like he lost interest in me and i lost interest in him. I actually ... Continue»
Posted by sophie101 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1984  |  
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Kits Adventures in the North

**Crossdress Story**

It had been about six months since I'd had any chance to dress, any chance to feel sexy and been even longer since I had any kind of sexual contact.
Work tends to do that; gets in the way and screws about with "me" time. Luckily, though, it was only a temporary job. It could have been permanent, but
I'd decided against it, I had plans to visit up north anyway and now I had the money, what better time?
I had all my things packed and was ready to go, sliding a jiffy bag full of condoms in my shoulder bag I was about to head off to catch the early train when I s... Continue»
Posted by KitsuneTV 3 years ago  |  Categories: Shemales  |  Views: 570  |  
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Bike time and BekkaCD

Well it was a warm July evening last year during Muskegon Bike time. I was feeling all warm and fuzzy from the few drinks that i had earlier in the day. I had chose to post a ad on craigslist seeking a couple harley riders that would be into having some fun with a gurl such as myself.Well to my surprise i had gotten such a good response that I had to figure out what i was going to do.Well after another drink or 2 i decided that i would get a local motel room.I responded to all the bikers and gave them my room number and told them to be there at about 4 pm.I got to the hotel and took my time ge... Continue»
Posted by bekkaCD1 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 675  |  
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A TV in the Shoe Store



I work at a ladies shoe store at a large metropolitan mall.
My name is Jillian, though my friends all call me Jilly.
Those same friends also say that I am blessed with a
beautiful face, and an athletic body! Pretty heady for a 30
year old woman whose ideas of athletics never got beyond
sports illustrated and Cosmo! But friends tend to flatter,
that is why we are still friends! I tend to dress with a
flare towards teasing. You see I always wear my skirts and
dresses a bit shorter than fashion demands, and I always
wear sheer reinf***ed heel and toe stockings. A habit
started by a ... Continue»
Posted by jillynylons 3 years ago  |  Categories: First Time, Shemales  |  Views: 1943  |  
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a great experience

in my last post i told you about how my wife is a shemale and how her and her shemale friends fuck me well the other day when we were having sex she for some reason put a large but plug in my ass. she stuck it so far up that i couldnt get it out. after an hour trying i decided to go to the hospital. so feeling a little embarassed i walk up to the desk and tell them what happened so they told me to take a seat. when they called my name i went to one of the rooms down the bottom of the hospital which i was confronted by a really hot nurse. they told me that she was new and that this was her firs... Continue»
Posted by xxjamiexx 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1269  |  
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How i became a sissy fuckslave pt2

Sometime later, i'm not really how much later since i seem to have dozed off, Sir came back in and woke me up by swatting my ass hard"Wake up slut".

Sir unlocked my cuffs, and my ankle restraints and said"Down the hall, second door on the right is the bathroom, go there, remove the corset, catsuit, boots and hood, remove the plug and clean it and yourself up.When your done I want you to put the corset on, and hood as well as the boots and then go to the room across from the bathroom.Don't worry about cinching up the corset, I'll do that when you get in the room.If you have to pee, your to... Continue»
Posted by analsubbieinmissouri 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1856  |  
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Finally, My First Tranny!!!

I just came out of the doctor's office in downtown Philly from my 3 month check-up. I was pretty horney since my doctor is a female and I had a complete physical so she and her nurse were in the room with me. I got to the train station to go back to Willow Grove and was standing on the platform when I saw this beautiful brunette haired woman about 10 feet from me. She was wearing jeans, and a spagetti top shirt. I could see that she had a real nice pair of tits and my cock started to get hard in my jeans. Being horney and looking to get laid, I walked over to her and introduced myself. There w... Continue»
Posted by adw276 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2930  |  
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The Bondage Whore, Chapter 10

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 10 - An Unwanted History Lesson


"Well, well, well... I do believe this just might be my worst student ever, little trouble-maker Rachel Wells."

"Oh no, Mr. Linebrink!" Rachel couldn't believe her horrible luck. Her old 6th grade US History teacher!

Mr. Linebrink stood there, with an ear to ear grin, looking straight down at Rachel's imprisoned face. "Yep, was I right! Wasn't I Rachel? You do remember that day in class, don't you? That day when I told you that you'd wind up a prostitute, or a stripper, or may... Continue»
Posted by thongcutoffs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 760  |  
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She became He

The day started as normal, wake up get dressed, have breakfast,but today was going to be anything but any normal day.

I decided that i would take the day off work and visit a local sex cinema,i had never been to one before and was a bit aprehensive but i thought sod it let's just do it.

Upon reaching the cinema i stopped as my heart started to race,after a minute or so i carried on in and paid my money and went inside.

I took my seat about 3 rows from the back there were a few people inside but not too busy,anyway after about 15 minutes of the film and with my cock starting to throb i... Continue»
Posted by carlosos 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1435  |  
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How i became a sissy fuckslave pt1

How i became a sissy fuckslave.

It all started after a series of failed relationships led me alone.Having always been a closet crossdresser, i started dressing more and more often and posting pics and vids of me on a website called xhamster.In time, i started posting vids of me toying my sissy ass, and also gradually building up my fem wardrobe.

After several months and many pics and vids, i met a man who offered to train me online.This was mustually pleasurable to both of us and as time went by he started having me cam for him.Toying my ass while he watched always turned me on, and he ... Continue»
Posted by analsubbieinmissouri 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 3065  |  
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Leona'

Note: ——I am NOT the author!so plz Don't ask me about part two,am simply sharing

this lovely story with all of you because I have not seen it on here

I think of myself as resolutely straight. I look at a lot of porn although I have plenty of girls to fuck. Steven, an old college buddy, dropped by and proposed that we go to a shemale bar that night. I was shocked and refused. But Steven retorted that if I was sure about my sexuality, I should have no problems being there. I could just have a few drinks, take in the scenery, and after we left we could pick up a couple of hookers fo... Continue»
Posted by adel5000 3 years ago  |  Categories: Shemales  |  Views: 772  |  
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"SpUnk coCK!"-LESLEY



when your a boy and your name is leslie-not female version ie lesley,
your first day at school is a real nightmare!-and it dont get any better
all the way through your school years.
boys are never gay but they sure get up to some strange games ,which if
any one else did would be "sooooo gay" i was teased and bullied a bit all
through my teen years,even though i soon learned too use my fists if things
got to "

crazy,i enjoyed hiding behind a "soft" image to see how far the guys
would go with "lesley anne" the S,punk rocker,yeah i was into punk... Continue»
Posted by spunkrokr 3 years ago  |  Categories: Sex Humor, Shemales  |  Views: 335  |  
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Sissy slaveboy gets trapped & blackmailed Pt 1

I had been a submissive with ever more disgusting fantasises for several years now and had acted out a fair few of them over that time.
I was a manly, muscular lad who everyone looked up to and would think was the textbook "normal man".
I held a professional job, steady girlfriend and a good standard of living, to the outside world, the perfect existence.
Behind closed doors i had harboured a strong, submissive streak which i could simply never satisfy and a desire to be controlled and humiliated that just grew day by day.
I love to serve Dominant women and adore total degradation, shame ... Continue»
Posted by kinkyandfun 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2256  |  
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