Shemales Porn Stories

my first time with a shemale

I was looking for a new girlfriend last spring. I usually just select "female" and in the age range I select from 25 to 55 (I am 43). But on the dating app, they had a "transsexual" category listed. I've always been attracted to shemales, so I selected that category in addition to "female" just to see who was out there in the immediate 10 mile range.

A transsexual woman popped up in the search results. She was 53 and only lives a few miles away. I looked at her pics, and she was beautiful -- long dark hair, nice face, sexy dress, heels, etc.. I really couldn't tell any difference betw... Continue»
Posted by bbwlover1138 22 hours ago  |  Categories: Shemales  |  
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Mistress Jennifer

My training as a she-male servant began when I rang the doorbell of my
lady's home. She greeted me wearing along, tight fitting red leather gown,
which covered her from neck to foot except that it exposed her prominent
and luscious breasts; her long auburn hair flowed over her shoulders. She
was also wearing 6" spike heels and black stockings. The dress had a slit
from her thigh to her ankles, which showed off her stocking clad legs when
she walked. She demanded that I call her nothing but Mistress Dominique and
that I would speak only when she allowed me to do so. She informed me that
... Continue»
Posted by klammer 1 day ago  |  Categories: BDSM, Fetish, Shemales  |  
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Day in the life of a Cuckold Part 2

My look who we have here says a deep black voice and my wife startled turns around to see me...my little clitty locked in a cage and my sexy lingerie and heels giving me away for what I am; a very naughty slutty girly boy. Oh my god she says you silly little slut I thought you would be in bed by now having wanked yourself silly; no Miss, sorry Miss.

Well you can just watch David here take me like a really man should, come and have a look at the size of this man cock, come on stand up now and come here. With shaky legs I cross the room and into view comes a monster black cock, not even fully... Continue»
Posted by Stephaanielust 1 day ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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Master and Apprentice E.1: Introduction. WoW Gnome

Self-entitled Mistress Glitchcog eagerly awaits her newest apprentice, Triss Blastbolt.

All of this was done in /e and /s.

Glitchcog-MoonGuard smiles brightly, looking up to the new gnome with wide eyes. She stood up straight, hands on her hips and showing off her borderline-nude body, with an obvious bulge potruding out of her spandex panties. "So!" She'd exclaim, "You must be the apprentice I was assigned>"

Blastboltrix-MoonGuard nodded her head, bowing before her new teacher, taking note of how barel... Continue»
Posted by rivvit 2 days ago  |  Categories: Anal, First Time, Shemales  |  
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Day After Liquor Store Booty

Geneva Campbell put on her small silver hoop earrings and walked to the kitchen. She said to her husband, “I’m going out now.”
“Alright,” replied Barry Campbell. “I’m going to watch the game this afternoon at Phil’s. So I’ll be gone when you get back from church.”
“Okay. I’ll see you tonight,” she offered as she walked out of their house and got into her white 2014 Lexus LS 460.

Barry continued watching ESPN. He picked up his phone and made a call.

“Hello,” answered the sweet angelic accented voice.
“Hey, sissy!”
“Hi, papi,” Mateo Rivas beamed.
“My wife just left. You ready for me?”... Continue»
Posted by faggyboi 4 days ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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The Cop & The Chubby

-Wyd?
-Watching TV. You?
-Laying in bed dick hard thinking bout your fag pussi hole.
-Oh wow!
-Come over tonite. My wife is getting ready for work. k**s are sl**p.
-What time?
-Be here at 11:30. You can stay til morn.
-OK.
-You know the drill. Park at the Krogers on Wynnton. Text me and I’ll come pick you up.
-OK Daddy. See you soon.

Russell Jones put his phone back on the nightstand. His wife of nine years exited the bathroom fully dressed in her scrubs. She kissed him before heading out of their two-story Dutch Colonial style four-bedroom house. She was on her way to the hospital... Continue»
Posted by faggyboi 5 days ago  |  Categories: Anal, Gay Male, Shemales  |  
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Crossdressed Pigslut Takes a Cottage Assault

my sexual deviance is based largely around the high heel... of course with the females who wear them but also the nastiness i can get up to when wearing them myself..
i wont meet anybody for sex unless i'm wearing a pair of fuckme heels which are of a certain standard , the idea of wearing just stockings revolts me , as does wearing a pair of heels that i deem un-sexy.
the next obvious step up from wearing heels and lingerie and little black dresses is to be presented to somebody else who appreciates this sort of presentation. these somebodys are easily found online , however they can al... Continue»
Posted by THE-HEELS-STAY-ON 5 days ago  |  Categories: Anal, Group Sex, Shemales  |  
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The Party ( Part 1 )

Hello Folks,

In my blog I had mentioned that I may tell the story of the night I dressed as a lady and went out in public. Please remember that I was only 20 years old at this time and of course it was not exactly accepted back then. At 55 now, I still look back on this evening with joy.

I was in college in the North Carolina, I was a a skinny guy at 5'7" and only 140 lbs. I was trying to get in to a Fraternity on campus, but really had no chance since it was basically a jock frat. The only reason I wanted to join was because of a few friends that I had there.

I was at one of their pa... Continue»
Posted by JayDon1960 6 days ago  |  Categories: Gay Male, Shemales  |  
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Chastity Locked Midget

“Hey, E,” Shayla Fields greeted her baby daddy.
“Hey, sexy,” smiled the tall, slim former high school basketball star. “Wassup?”
“I gotta work over. Can you pick up Katelyn from my Uncle Lamar’s house,” she inquired referring to their ten-month old baby daughter.
“Yeah. What time?”
“As soon as you can go.”
“Aiight bet! I’ma head out in five.”
“Thanks!”
“Anytime!”

Errol Reynolds locked the door of his efficiency apartment and hopped into his black 2010 Ford Focus sedan. He sped down the highway eager to retrieve his youngest c***d. He had two others – both boys. He was a stereotypical... Continue»
Posted by faggyboi 6 days ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Weekend Party

I sat in Mrs. Myers’ senior English class. I was half nodding because I was up late playing Madden NFL 16 on my PS3 against my little b*****r. We split the wins one and one. I still can’t believe how he beat me. It was a lucky ass field goal attempt that went good. I lost by two points. I’m still kinda pissed if you can’t tell. Anyway, this old woman is going on and on about some shit I care nothing about. I winked at my girlfriend, Kara, who is across the room. Her smile can kill. She’s light-brown-skinned, tall for a girl, slim with a big booty. She’s gonna be class valedictorian and she’s t... Continue»
Posted by faggyboi 8 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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Busted

Busted
Nikkie Silk
“Happy is what happens when all your dreams come true," Stephen Schwartz
Sandy came into the bedroom where I was still dozing, holding a pair of tights in her hand.
‘Babe, I wouldn’t ask, but I’m so pushed for time and I’ve just laddered my last pair of clean tights. I desperately need some before I go to this client meeting.’
She held them up as if to prove what she was saying.
‘OK,’ I said, still half asl**p, ‘what can I do about it?’
‘Can I borrow a pair of yours, pretty please?’
My eyes snapped open. What did she just say? I rolled over to look at her and my hea... Continue»
Posted by nikkiesilk 8 days ago  |  Categories: Shemales  |  
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Rose 1

I was 14 and had discovered wanking and dressing in panties and nylons.
I don’t know what made me slip on panties and stockings the first time but one day at home alone I felt the urge to try on the white lace panties and suspender belt with sheer black fully fashioned stockings I found on my parents’ bedroom floor. Curiosity I guess but as soon as I felt that lace on my cock and the sheer nylon on my legs I was hooked and hard. I stroked my rock hard cock a couple of times and came quicker and more fully than ever before. After that day I wore whenever I could. I found I like tights and ot... Continue»
Posted by maninnylons 9 days ago  |  Categories: First Time, Mature, Shemales  |  
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INNOCENT BEGINNINGS

INNOCENT BEGINNINGS

"Did you take your vitamin, dear?" Ellen called from the
bathroom.
I rubbed sl**p from my eyes and picked up the pill bottle,
rolling a big tablet into my palm. "My horse pill? I'm doing it
now."
"Have you noticed any difference yet?"
"Nah. Vitamins are pretty much all alike." She'd gone on a
minor health kick a month before, insisting that I needed to lose
a little weight and take better care of myself. I hadn't
actually made it to the gym to work out like she was though.
"Where's my underwear honey?" I asked my wife, poking
th... Continue»
Posted by klammer 9 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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My Journey part 1.

My Journey.


As I sat in a small bar in a pub I thought back on my life and how it had brought me a Fifty year old cross dresser to this place and time.
Back in the late 70s and early 80s all the top shelf magazines were full of “lipstick lesbians” dressed in sexy satin and lace lingerie in various poses so when I got hold of some of those magazines the connection was made between feminine beauty, kissing, tongues, sex, satin and same sex love so all that was to follow in my life seemed to follow on from that for me.
I had began to enjoy satin ling... Continue»
Posted by silknsatinxxxx 12 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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How My Husband Fell in Love With Me and Decided to

do you already have a personal cock-servant? i am looking for a man who would take me in as au-pair for the summer. i clean, cook, do your laundry - and suck your dick whenever you want and keep my ass ready to fuck for you - hopefully, you will soon be used to falling asl**p with your dick in my twitching asshole and never leave the bed with full balls in the morning. I keep near you over the day - follow you in a little distance or walk right next to you - until you feel the urge to grab my pants, pull them down quickly, and enjoy a quick and hard fuck into your little fuck sluts hot and oil... Continue»
Posted by spermmakesme 14 days ago  |  Categories: Interracial Sex, Gay Male, Shemales  |  
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The Tutor and Jenny (Part 4)

The Tutor and Jenny (Part 4)
by Claude van Feinbode


My knees were a little weak as Rachel walked out of the room. I realized that I was keeping my guest waiting and I quickly dressed in blue jeans, black button up shirt with French cuffs, jacket and comfortable shoes. I splashed some cologne and walked out of the master bedroom.

As I walked down the stair towards the main sitting room I heard Gina and Jenny talking while music was playing at a low volume. I smiled and marveled at how Gina had the ability to make anyone feel at home.

"Claude," Gina said. "Its a... Continue»
Posted by NiceGuyz4u 14 days ago  |  Categories: Group Sex, Shemales, Taboo  |  
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My First Tranny Experience

I was in my mid twenties when I first became attracted to trannys. This was before the internet and it was harder to meet people, but I found an advertisement in a local newspaper for a TV named Susie who offered a massage service. I phoned the number and she sounded nice so I made an appointment.
I arrived on time at a small apartment block near the city centre. I was extremely nervous as I knocked on the door and waited for a response. The door was quickly opened and I entered, not knowing what to expect. I was very relieved as I walked in to see that Susie looked lovely. She was tall... Continue»
Posted by mjam21 15 days ago  |  Categories: Fetish, First Time, Shemales  |  
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Crossdressing I Got Fist Fucked

I was feeling horny so I put on my blue satin dress with white polka dots, satin panties, my white satin gloves, garter belt & flesh colored stockings. Then I put on some deep red lipstick and lip gloss and topped it off with my blonde wig.

When I looked in the mirror and saw the sweet hot girl looking back at me I knew I'd find a guy who wanted to fuck me tonight.



I posted a picture of myself on Craiglist and within minutes I had half a dozen guys messaging me so I invited them all over.

The first guy who came to... Continue»
Posted by Doyoudeep 15 days ago  |  Categories: Shemales  |  
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We all shared the rent, and they shared me!

It was my Junior year of college, at that point I was mostly a closet cross dresser, with the exception of Halloween, and a few select occasions. I had been sharing a house with two other guys, and I they both knew I would dress, but we didn't speak of it, well until tonight. I was sitting around doing shots and watching tv with my two roomies, let's call them Jon, and Barry. Jon was a small skinny Korean k**, who was very much influenced by Barry, the all American boy, tall, blonde athletic. Back to our story, the three of us started talking girls, and fucking, and moved onto "would you if ... Continue»
Posted by smonkeys32 15 days ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Christy’s Awakening.

“And you said you didn’t think you could do it!” John sounded surprised and to be honest I couldn’t blame him. He had just released his load deep inside of me with a loud moan. He was panting and trying to regain his composure and all the time I could feel him pulsating inside of me.

After what felt like an eternity he finally pulled out of me and rolled over. His eyes closed, he had the look that told me he was totally satisfied. I had surprised him this far, I thought, but I wasn’t satisfied, I needed more. John had woken the a****l inside of me. As he lay there, I slowly moved my ... Continue»
Posted by chuntercd1 15 days ago  |  Categories: First Time, Shemales  |  
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