Shemales Porn Stories
Page 119

Crossdressing Fun

The meeting had been arranged for Friday morning, this would be the first time anyone had seen me dressed. I felt nervous and excited at the same time, I planned to wear a pair of nude sheer tight, black satin thong, black high heels and a shimmering silver, figure hugging, long dress with a split up to the thigh.
Friday arrived and after getting up, I slipped on my tights and thong beneath my work clothes. I set of on the short drive to Antonia's, upon arriving I was greeted by her dressed in a mini skirt, blouse, high heels and black hold-ups.
I quickly slipped on my dress and heels, then ... Continue»
Posted by KirstyNylonlover 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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A threesome to remember

After a few cocktails I was relaxed in the chair as I watched Annie unbutton Jeff's shirt and kiss his chest. Her ass was right in front of me as I watched her black nylon covered legs run up to her tight skirt that just covering her full ass. She knows how much I love tight skirts and nylons and for this special night she was dressed as a full on hot slut for the night. After three years together I had always fantasized in sharing her in a threesome. The sight of her lipstick stains on his chest, and hearing her light kisses across his body made my cock so hard. I knew Annie’s little cock mus... Continue»
Posted by Zeffer 4 years ago  |  Categories: Shemales  |  
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The Walk After the Busted Date -- Part 1 of _? or

The Walk after the Busted Date, Part 1 of _? or My First Job as a Hooker Part 1 of _?

It was a Friday evening about eight just before the sun was about to set on a pleasantly cool evening. The brisk air kept me comfortable since my body was a little warm from being nervous with the coming scenario. I was going to meet Phil, my date, as a hooker. We have been planning on this for a few weeks and our schedules finally matched enough to make it happen.

The club I was going to served a very eclectic clientele and right now, there were free line dancing lessons with the 70's ... Continue»
Posted by LeslieStone 2 years ago  |  Categories: First Time, Hardcore, Shemales  |  
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How I became a GURL part II

So I'm in college now, I've learned to love and use porn in all its forms, I've learned to be a great cock sucker and to have my ass fucked. I've learned to tie myself up -- as best as possible -- to pee all over myself to get that humiliating feeling. I'd spread the porn mags all over the floor and spend the entire night playing, trying to shoot my cum onto a photo of a cock so that I could lick it up.

The feeling of release whenever I gave in to all of those instincts was fantastic!

I loved cock! But I was a horny 20 something and still chasing pussy. Eventually the girlfriends star... Continue»
Posted by jenn1 4 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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Feminization Fantasy

My wife has been dating around for years. She loves the feel of different cocks and I enjoy watching her with other men.
Recently, she decided it would be fun to put me in a chastity. She said it was only temporary and if I didn't like it, she'd take it off. After a couple of days, I decided, I'd had enough. She didn't. She said she liked having me locked up and know I couldn't get hard or jerk off. "I'll let you know when you can cum again." She wore the key around he neck like a trophy. Her boyfriends would come over and she would have sex with them in front of me, only I wasn't able to je... Continue»
Posted by ForcedSissyGurl 1 year ago  |  Categories: Shemales  |  
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Pounded to submission CH.2

CH. 2

Two days ago Joesph was checking out porn like he usually did at his favorite site xhamster. A couple of BBW vids here some interracial there, the usual. Then he saw a just viewed picture with a Brazilian She-male and couldn't stop looking. With his curiosity getting the better of him he clicked on it. She was gorgeous! Her face appeared to be as feminine as feminine could get, her tits were remarkable. And then he saw it, she had at least an eight inch cock that seemed to defy gravity itself. It was curved upward and pointing towards her belly button. He felt his cock twitch and real... Continue»
Posted by james_jones_03 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Mistress Cunt's two fairies



Mistress Cunt's two fairies

By Taffy, the little sissy fairy girl



My, my what a wonderfully gay time Angela and I had with our slut friend Lauren and her Mistress Cunt! Here’s a little story about that faggy time and how fairy we were for her.

The weekend started the night before with Angela and I at the hotel; I had already properly dressed in my sexiest outfit, a gold sequin mini skirt with black fish net stockings. It did not take Angela long to get herself prepared and we sat to chat. Chat turned to feel, feel to kissing. It wasn’t long before my panties were down and the... Continue»
Posted by Tigerpaw46 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Playtime Stories Ch 13 - Unbelievable Motel Reward

Ok, so this one is hot, but is mostly fantasy...I have 'earned' a few nights kinda like this though...
13.

I also fuck the hotel managers of another city. To be able to come and go all dressed up without anyone noticing is usually very important. Sometimes my company will have me stay at a premium ‘nice’ hotel. So I’ll get a slightly less nice motel on the side so I can do what I want without having it get back to my boss. A little caution and a few extra expenses go a long way.
One of the cities I go to on a quarterly basis can be a lot of fun. I’ve had some fairly hot times... Continue»
Posted by 6988slutty_rbckyy 3 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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my black lover

My black lover
After one year as a sissy whore and secret wife to my turkish Pascha, I felt the desire to look for a black man. I looked for ads online and put ads online myself. One day I saw an ad from a young black man looking for a crossdresser and wrote him an email. I actually thought I would never hear from him but within a few days I got a reply and two pictures. I couldn't believe it, he was 28 years old, very tall and slender and very handsome. He wrote he is a musician and that he travels to the city where I live a couple of times a month. He wrote he never had experience with a cr... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Interracial Sex, Shemales  |  
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S****r has a Secret part 3


Sarah was sat on her laptop, searching for something on the internet. She wanted to surprise Hope with something for her official leaving of school.

She'd been looking up the cheapest, quality flights she could get to take them both on holiday for a week or two, but she'd been hampered a lot by Hope wanting to hang out together. Hanging out normally involved sex, after which Sarah had little energy left to search.

Luckily, Sarah had the day off work while Hope was sitting her final exams for the year. She was looking through the normal travel agent websites while also looking on other ... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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Sissy Tranny Annie Slutty Fantasy

I have been dressing since an early age, dressing in my mothers stockings, suspender belt, bra, panties and heels. I used to feel my smooth legs and my cock would get hard straight away. I love how my cock looks when im dressed as a sissy slut and from that early age all ive ever wanted is to have a horny guy in front of me, with his cock hard knowing that he wants to fuck me.
My fantasy and dressing got a lot more sluttier when I first in with my first love. Her name was Claire and she loved wearing hold ups, thongs, and best of all she loved to wear really high heels and she was the same s... Continue»
Posted by danny241976 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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The Covert Operative

“I love fucking your faggot asshole,” the tall, slender career military man announced in French.
“I love that big African dick,” screamed the toned effeminate bottom.
“Take it, slut!”
“Yes sir! Fuck me good. Fuck me like a girl.”
“You are a girl. My girl. Ohhhh, baby!”
“Yes, daddy! I’m your sissy girl. Fuck my ass. Fuck it hard.”
“Bitch,” he roared. “This ass is all mine.”
“Oh yes sir!”

Colonel Rodolfo Urikob slammed his generous ten inch dick into his pussyboi’s asshole. The sweat from his forehead streamed onto the smooth caramel-skinned boy. He plowed feverishly nearing ejaculatio... Continue»
Posted by faggyboi 10 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Why I miss my ex

Why I Miss My Ex
I feel obligated to say that I am not a passable crossdresser, not even close. Even without my beard, I’m very masculine, large framed, and I have a very deep voice. All of these things aside, I love to dress up in sexy lingerie, panties, dresses, bras etc. While I’m dressed, I love to be verbally humiliated, although, I don’t think being called names like “sissy” or “fag” or “cuckold” is actually humiliating. For me, it’s a huge turn on, and I love to think about sucking cock while I’m being humiliated.
It’s quite a long story about how I got my ex-wife to play with ... Continue»
Posted by pbg732 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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sissy Meets her New Daddy Ch. 1

So I took the plunge and put out an ad on Craig’s List. I was travelling in a city about 120 miles from home and figured this was far enough to not be found and close enough to go back if I had success meeting a fuck buddy that could be longer term. I got myself all primped and wore a tight print dress, matching bra panty set subtle yet slutty makeup and my fave long blonde wig.

The ad attracted immediate attention and I was sure to mention I was a sissy who wanted to be treated like a girl. I was NOT into topping a guy…no. So I finally chose this guy Rich, who happened to be black, becaus... Continue»
Posted by jamie_anne 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
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me and connor at the beach

well Connor always liked to parade me around and i loved it we would always be down by the beach together because he lived neat it one special night we decided we would have sex in as many places as we could all in public we went walking down the beach and he layed out a towel for us to lay on and as the sun went down Connor was sucking on my cock and nipples then he fucked me so gently it was amazing and everyone was staring at us but i loved it... Connor loved me to fuck him as well and i was a little taller then him but he was so cute to me i would love to embarrass him too but he wouldn't ... Continue»
Posted by drewcd 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Playtime Stories Ch 6 - BBC Oreo in a Mo-tel

6.


A lot of my playtime is at night. I start in the afternoon and get partially dressed in lingerie, heels, and makeup, and start to play around. I watch some porn get on an adult phone sex chatline on the female side and get nasty men and even a few freaky women off over the phone. Almost every time I am on a chatline I meet T-gurl lovers and occasionally I’ll put together a play-date. It’s a little risky, but it is very exciting to have a stranger knock on your door and expect nothing more than some nasty no-strings-attached free sex. I have been disappointed a quite a few time... Continue»
Posted by 6988slutty_rbckyy 1 year ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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Sindy meets Nina

As I landed in Berlin, I still wasn't sure whether the invite was 100% genuine. I was
a relatively innocent occasional cross-dresser in my 40s, I couldn't believe someone
as sexy as Nina would want to meet me.

I'd been chatting with Nina for a number of months now after we'd happened upon each other
doing simultaneous cam shows on a well known camming website. She was about the same age as me with
slim features, brown hair, a fit body plus a devilish sense of humour which became immediately apparent
from the first naughty comments we exchanged, intimately detailing what we'd do to e... Continue»
Posted by SindyBlondeCD 11 months ago  |  Categories: First Time, Shemales  |  
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Kelly gooes to college!

this is another installment of my life as a girl, im gonna flit around the different parts of my life so enjoy!

Wheni was eighteen i went off to college, no more sexy playtime with my best friend B (or nicole, which is what i will refere to her as) no more sl**ping in panties and a babydoll or short slip, or anything kinky! My first year i lived in a double and my roomate was a partier, constantly bringing home d***k girls and having loud, sloppy sex as i lay in my bed stroking my girlie cock and fingering my tight little whole, imagining it was me being a dirty slut and getting fucked goo... Continue»
Posted by dirtygurl4u 4 years ago  |  Categories: Shemales  |  
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godess sarita 3 (regular days)

mistress came home at evening got freashen up and came to me as there was a lot of water I could not finish all of it few remained may b 1 liter.. I was covered with crystal clear piss and my jaws hurt mistress checked the video released me let me took shower while she obserbed I wasnot allowed to touch my cock and balls after I was clean she made me sit on the toilet shaved my butt hole cock and balls usually she does this and I shave rest of my body I was arosed by her touch she digger her nail in my balls the pain was tremendous my cock got down immediately .. after that she putted lotion o... Continue»
Posted by mashroorr 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Gender bent - Somebody's Bitch

Gender bent – somebody’s bitch

I woke up to the humming from Kandi as I popped open one eye and canvased the room. I let out a load “Ughhh” and turned over. I noticed my butt hurt while Kandi came over to me wearing a lace bra and panties and smiled “Looks like the sluts awake” she then giggled as her cock was out just standing in the wind. “What happened last night?” as I removed the bobby pins that kept my wig in place. “Well we got really, really, and I mean Really wild last night with me and Dave.” Suddenly it hit me. Memories flood my head of the steamy night we had. I remember waking ... Continue»
Posted by youngprboi 6 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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