Shemales Porn Stories
Page 121

bookstore sissy slut

My name is dollie I love to be a girl and being very petite and pretty long black haired its easy for me too feminize. And until now I wouldn't go out, dressed up, sometimes a quick walk around or a short drive but nothing real. And one time in college I walked around the campus. Anyway I ignored all the signs being overly sensitive for a boy It should of clicked when I was diagnosed with disphoria. I knew I liked being girly but I really thought all teen age boys were like me. Always being a pretty-boy girls always came my way but they all end the same I get hurt because just like a girl ... Continue»
Posted by dcdollie 3 years ago  |  Categories: 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 2 years ago  |  Categories: Gay Male, Shemales  |  
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working at a house

I'm fitting a kitchen at a couples house right now. They are both in their thirties. as I arrived in the morning they were waiting for me, they needed to go out and would be most of the day, to which I agreed to be fine on my own.
After about an hour or so I decided to look around in her bedroom. she had lots of sexy dresses, suspenders and stockings. I also found some lovely slightly soiled knickers in her washbasket. After sniffing and licking the gusset, I was getting very hot. I decided to dress up in her sexy gear. I put on her stockings, suspenders and bra along with the knickers I'd b... Continue»
Posted by tarajenkins53 5 years ago  |  Categories: Shemales, Voyeur  |  
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Oh,,,,,,,, so helpless

The ankle straps of her five inch heels connected by a short chain and secured in place with tiny padlocks. A virtually unnoticeable black cable secured around her waist held the shiny steel handcuffs that pulled her silken gloved hands behind her, leaving white glossy fingers resting on the very large white satin bow that in turn hung across and down the short black silky smooth skirts and numerous frilly petticoat layers of her French maid uniform. Zipped to the neck and edged in brilliant white lace frills, the locked bodice of her dress was clinging tightly over the uplifted bosom and cor... Continue»
Posted by maidtracie 4 years ago  |  Categories: Shemales  |  
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First time with a shemale

I must have been 16 back in the day, but I always looked older so it didn't really affect anyone's judgement in the sex world that I had loved since I can remember jerking off for the first time.
I was walking the streets of Amsterdam that day, the Red light Disctrict looked like paradise on earth, all those hot hot girls smiling and telling you to come in...I don't even know how much they wanted, I didn't care, just walking in those tiny streets and seeing those creatures was more than enough.

There pretty much everything there, from the porn starlet straight from Poland to the big Colomb... Continue»
Posted by joelo 4 years ago  |  Categories: Shemales  |  
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Sex in the Bar

Being a old Ex sailor it is no surprize to me that I am not shy.
I live in Thailand and worked there a couple of time over the years.
Down south near the Malay border there is a great little town where a lot of expats work and live.
I am a sociable guy and love a few beers with the boys/girls/ anybody who wants a drink.
We have a bar in one of the darkside of town where anything goes.
After dark or even during the day you can do anything in the bar.
Lady boys sucking you, young girls sucking you in teh bar besides your mates when their drinking. No shame no problems.

One day I was the... Continue»
Posted by xmas69 4 years ago  |  Categories: Shemales  |  
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Duty Bound Part 1

Ever since c***dhood it had been that way; delicate in the extreme and a want of soft bright things. School had proved to be difficult; not being like the others. A fondness for the stricter teachers irked the boys; patently apparent differences alienated the girls. The developmental teenage years were no easier, though liberally minded parents allowed chosen apparel to be worn at weekends, making the desired route in life that little easier. The tortuous journey through to adulthood now accomplished, and independence achieved, indulgence in a preferred lifestyle beckoned.

Hannah glanced a... Continue»
Posted by midsummerman 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
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TV/CD adventures - going for ice, remember ID

It's amazing what high heels, wig, makeup, nylons, mini, etc can do for ya when going out in public.

Couple months ago I got me a room at Imperial Palace on the strip and I think the front desk caught on I was using the room for casual sex. I put up an ad on craigslist and gave out the room number. But setting up times and availability was difficult because I didn't have a computer in the room. So the front desk constantly was connecting me to "different" guys. After being drilled deep by 2 guys I decided to go for ice in my fishnet no panties slut outfit. My ass was gaped and sloppy... Continue»
Posted by vegasjful 4 years ago  |  Categories: Shemales  |  
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A date with a straight college student

I had been chatting with this boy for a while when he finally told me his parents were out of town and he had his father's car. So we set up a date in the evening. I told him to pick me up by his car from somewhere. I was pretty excited, this jock was a very good looking guy with a slender athletic body type, brown hair/blue eyes. I always had a thing for blue-eyed boys. I was thinking about those whilst putting on make-up in front of the mirror and combing my hair.
I was a lil bit nervous when he picked me. He looked even much more handsome than his photos. Because he was lacking a web cam, ... Continue»
Posted by Slave4str8twinks 4 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Jenny, Melissa and Me

I’m watching you on the screen, Jenny, as you pull down your pretty nylon panties with the floral prints and spread your legs. Your brunette hair hangs down around your lovely eighteen year old face, smiling as your labia open wide and you begin to rub your clitoris, all the while smiling, and gazing at me with yearning through your computer camera.
In front of my camera, so you can see me, I put on a pair of sexy pink panties over yellow nylon stockings and a pink garter belt. I put my hand under a sheer negligee and stroke my shaved cock and silky smooth shaved balls for you to see. I... Continue»
Posted by pantyboykristin 3 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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Nice Sunday to worst sunday

Hello guys
Hope everyone doing great and enjoy my true story
Sorry again guys not very good English so grammar its not their

We all enjoy our Sunday especially now it’s NFL Playoff guys into games so am I
I just buy new big screen TV and love watching games at my on place.

As I woke up on Sunday late morning around 11:30 am still im in my sweet bouquet layered baby doll (nitie) making coffee and doing dishes get my coffee sit on couch watching TV my cell phone ring one of good all Spanish she male friend (Rosie) who was about to go out back to Mexico her grand ma was sick and she a... Continue»
Posted by shawn777 3 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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One experience with two blak men!

Hello again this is EvA…I am a 40 year old tranny. I do not consider myself a cross dresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine lady boy. I have been taking also hormones for 4 years, on and off and I already saw many changes…my boobies are growing, becoming poutier and have sensitive nipples. My skin is sooo soft and my hips are getting bigger giving me a pear figure… I also see changes in my feelings, being more sensitive and sometimes I cry when I watch a romantic movie…haha. One of the biggest changes also is that I am alway... Continue»
Posted by transeva69 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Tgirl Jill's BBC pounding fantasy in casino s

A big black stud invited me up to his casino room when we were on the casino floor.

When I entered his top floor casino room he was watching an IR porn video with a bubble butt blonde BBC slut getting anally gangbanged by 12 BIG BLACK COCKS balls deep.

His BIG BLACK COCK was already rock hard and glistening with wonderful black precum.

I immediately dropped down to my knees and placed my hot pink shiny lipstick lips on the head of what had to be a BIG BLACK 12" COCK and it must have been 2" in diameter....at least.

This big black muscular stud started to tease me even more by dragg... Continue»
Posted by tgirljillforbbc 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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Daryl Wants Me Girly


Daryl is a black guy. He's everything for me. I simply adore him and we gel so well; the things we like and want to do are sublime.

Just being with him sets me apart from the guy in the street or the guy in the office, or the guy who uses to go out with girls and to what end? I guess I was just following the trend but girls soon suss you out and no way could I love nor have sex with a girl.

Sooner or later it just had to come out I was gay and when I met Daryl on that sweet Sunday when he had me over the bath full strength I realised then just what I was missing and where I should be g... Continue»
Posted by Yoav_Roth 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Daryl Wants Me Girly. Another story.

In my last story Daryl wanted me to be a slut for him. It was an awesome experience and Daryl was really great at making me feel the part, the way he swore and bossed me. And the way he shagged me like a rag doll.

But Daryl has many moods as I discovered when he said he would call me his girl Jackie - with the very tight ass and slender figure, wrapped in a hugging black silk dress which he pulled out of his role play wardrobe.

He wanted the whole caboose, the black and red underwear, suspender belt and black stockings which truly made me feel the part. Simply putting them on made me fee... Continue»
Posted by Yoav_Roth 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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fictional bookstore encounter

This is a completely fictional story of an encounter that I have thought about for some time. I use to masturbate a lot to porn magazines and in doing so got turned on by the thought of having sex with a shemale, since there are a lot of ads in the magazines concerning phone sex with shemales showing very nice pictures of shemales and their beautiful packages. Where I live there is only one place that I know of that have shemale magazines with stories and pictures to masturbate to. Everywhere else there are plenty of porn magazines but none pertaining strictly to shemales. It is a little drive... Continue»
Posted by 6finallybi9 1 year ago  |  Categories: Gay Male, Shemales  |  
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My Boss Tricked Me

I work for a cell phone company. Part of my job is to travel to cell phone towers and fix any problems they might have. I enjoy it but am on call most weekends. Now I consider myself a man in public but at home I love dressing up as a slutty tramp. I love the feel of lingerie on my body. I had a few experiences with a man but it was mostly mutual masturbation. My crossdressing is a secret to everyone except the few I have met online.

Most Friday nights me and the coworkers go out drinking. Just a bunch of guys out having a good time. One particular Friday I got really d***k and my superviso... Continue»
Posted by sissysadie 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Serving Waitress

This is the first “didi” story I ever wrote. It’s my deepest (and darkest?) fantasy. It probably needs to be rewritten at some stage because I think it’s been written too much by my male brain and not enough by my female side.

The story begins…..

My wife, Susan, one evening announced to me that we had been invited to a party at a new friend of hers. Victoria had inherited a fortune from her father and she lived in a mansion in the best part of town. It all sounded very exciting. Apparently she had these parties once a month. Susan said that we would go earlier as she had offered Victoria... Continue»
Posted by didi_galtier 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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The Mechanic

My name is Bruce, I am one of those mobile mechanic chaps you call out when something goes wrong with your car. You get to meet a nice variety of people, some good some not so, with some very good looking ladies thrown in as well, which make it nice. A lot of the clientele are people you see a couple of times a year for a car service so you get to know some of them quite well.

I hadn’t had that much in the way of action for a long time. I had split with my wife a few years before and now I always seemed to be working. Anyway it’s not the most attractive of looks when you hands are covered ... Continue»
Posted by domestique01 5 years ago  |  Categories: Shemales  |  
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Allison the pool slut part 2

After using and abusing Allison’s white asspussy, and giving her a refreshing and kinky golden shower, Jay informed her that they weren’t done being kinky yet. He was not lying…

Jay’s hand gently grabbed Allison’s and pulled her to the house. Their intense poolside fucking had left Allison’s teen butthole full of warm seed and as she followed him inside it began to run down her thighs and her strappy stripper heels. “Go on up to my b*****r’s room and put on some of yo sissy stockings babygirl.” Jay commanded. Like a good white whore, Allison’s heels clacked on the hardwood floors as she did... Continue»
Posted by AllisonCumms 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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