Shemales Porn Stories
Page 68

A tribute to Joy

I had always loved women’s clothing. Well truth be told, I had always wanted to wear women’s clothing. I envied women’s ability to change their look with just a little effort, a tight skirt; that was so sexy in one way to a pair of jeans that was sexy in an entirely different way. Then there was the hair thing. I thought that it was so cool the way that women could change their entire look, even their personality by just wearing their hair differently. I really like women. If it wasn’t for that monthly thing I would want to be a woman. I would be a lesbian if I had my final sexual preference. ... Continue»
Posted by justluvtrans 4 months ago  |  Categories: Anal, First Time, Shemales  |  
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THE Sissy a*****ion

You are walking along, you feel a presence, a person quickly comes up behind you and chlorophyll you. You pass out but you catch a glimpse of his green army officer hat.


You wake up several hours later chained to a rack naked. Two identical women come out with a cart filled with cosmetics. First they take this special soap that when it touches your skin it makes your skin very sensitive and a sensation of pleasure takes over at the slightest touch, then the two women grab nail polish and paint your toes and the your fingers. Then, they grab a special foundation that they apply to your wh... Continue»
Posted by thegoods699 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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A Night on the Town

This is my first post, hope you enjoy. May continue the story if I get positive feedback.
It was my 21st birthday, and my friends were taking me out for a night on the town. We had been going from bar to bar, getting d***k and trying to pick up women. Finding no luck with the woman at the bar we were at, we decided that it was time to move on again. We wandered down the street, looking for the next bar. We found one called the Dollhouse, and decided to go in. We found a table and immediately ordered our drinks. I had the need to go to the restroom, and excused myself from my friends.
On my ... Continue»
Posted by thomas1927 2 years ago  |  Categories: 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 1 year ago  |  Categories: Gay Male, Shemales  |  
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Riverbank Tranny Fucktoy

Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river.

It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site.

I had been chatting to Fillipe for a couple of hours, and we were both getting hornier and hornier with each new message that we sent. It was me that asked if he would like to meet that night, and he of course said yes. There are a few cruising areas near around the closest city to me and we arranged to meet at one... Continue»
Posted by donnamarie09 1 year ago  |  Categories: Anal, Shemales, Voyeur  |  
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Crossdresser has cinema fun

It had been a few weeks since I'd had any action as Clara and was absolutely gagging for some cock. The girlfriend was away for the weekend so I planned a nice Sunday afternoon in a local-ish sex cinema. I got partially dressed at home wearing black hold-up stockings, black bra with inserts as well as see-through black panties, and a matching vest-top. I pulled on a pair of jogging bottoms and a sweatshirt, pulled on a pair of trainers, packed the rest of my stuff in a tote bag, and left in the car. The journey was uneventful apart from me feeling very lightheaded from being in a constant stat... Continue»
Posted by claracduk 4 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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A LITTLE HARD WORK NEVER HURT ANYONE.....ESPECIALL

A Little Hard Work Never Hurt Anyone......Especially not Chrissie!

It's hot and humid today and I'm sitting here in my a****l print bikini bathing suit sipping on the first glass from a pitcher of margaritas.
I'm not really certain why but I started thinking about something that happened back in my second year of college. My BFF since grade school
and I decided that in order to create a little extra income during the summer break we'd set up a little free-lance house cleaning business. We
placed an ad in a couple of the local weekly papers, mostly because they charged markedl... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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A slut is born.......

I've always had this magnetic attraction to slender pointy hi-heel stilettos for as long as I can remember. Even when I was just a little k** of around five years old, I used to get these stange feelings between my thighs every time I saw a young teenage girl strutting and teetering around on these fabulously erotic pointy heels - This was the 1950s era. The era "par excellence" for these gorgeous shoes that did so much to excite me but also to trouble me - Because I was only five, I didn't understand these wonderful sensations at all. All I knew was, that it must be "sinful" to have s... Continue»
Posted by caroletv31 5 years ago  |  Categories: First Time, Masturbation, Shemales  |  
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first time with a strap on

I think I can trace my new addiction back to a short fling I had with a girl a few months
back; I'm 22 years old slim; about 6', and fairly good looking. Not trying to be conceaded
but simply stating girls would be atracted to me however it would be difficult for me to
progress with them because I am so shy. Well back to the story; I Kristen at a local college
bar; very pretty but a bit on the rocker chic side. I lived on campus in a converted
victorian house with several room mates. We had several sexual encounters which were great
but on the last 2 occasions kristen let me fuck her ... Continue»
Posted by kellyblue66abc 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Massage parlor surprise

I have to admit one of my biggest turn ons are shemales/ladyboys. In all my little ventures to asian massage parlors for some relaxing relief only once did I get a total surprise. About a year ago I visited one of my favorit little places and Mama said I should try her new girl....I might like her. So I agreed to meet with her. Waiting in my little room in walks a very hot sexy little asian girl and we started our massage session. While getting my rub down I started letting my hands wander to her thighs and lower butt to rub and feel then and to let her know i was cool for some extra if on the... Continue»
Posted by longrod4u 4 years ago  |  Categories: Shemales  |  
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My First Meeting - A work of fiction

I had absolutely no idea what to expect as I rang the doorbell of Jane’s house. It was an extended bungalow on the outskirts of Edinburgh and it had taken me 30minutes to drive there, getting more nervous with each passing mile. Jane and I first contacted each other through as online transvestite networking site a couple of months previous. We had got on well, and often chatted in a private chatroom, and exchanged pictures of each other. While I was relatively new to being a tranny, Jane had been doing it for years, going on nights out and meeting people.

Jane answered the door, wearing... Continue»
Posted by misssuzywhyte 2 years ago  |  Categories: First Time, Shemales  |  
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Forc to be Female2


f***ed to be Female

CHAPTER FIVE
The next few weeks seemed endless. I still did my exercises with Ann, though now it was to keep my figure in shape. I continued to learn all sorts of female pastimes, like knitting and flower arranging. They were all designed to make me as whole a woman as was possible.
I still used the dildo regularly and I had told Ann about my night with Eric and how much I had wanted him to really make love to me. She had smiled and said,
"Just a little longer, Susan. And then I am sure Dr Knowles will say you will be ready for full intercourse"
I had asked her sev... Continue»
Posted by hpm12 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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MY first time with a TS

Actually it was not intended that I should visit Fransheska.

I had in fact been looking at Iris Baby... her profile I had seen on e****t Guide a few weeks ago. When I finally decided me and got it all in place, it turned out that Iris was not in the country. But then (the other day) she showed up here on the wiki.

And THEN finally I got a dial tone! But after three calls without answer I stood there with my 1,500 burning in the pocket - and a bulge in my pants - and still no deal. Now what?

Got my mobile out of the pocket and then scrolled down... Fransheska... the two Tayras... Lore... Continue»
Posted by mazis2003 4 months ago  |  Categories: Anal, First Time, Shemales  |  
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Tranny suck me off (tv ts cd )

I have a new found love for trannys I love convincing polling tv,ts and cds. The other night i met a tv from Halifax a town close to my home town. Wed arranged a meet online I d agreed to pick her up on a street corner like a cheap street walker. I pulled up at the side of the curb and a woman stepped foward from the shadows tall long sexy legs blonde hair, short skirt, fishnets , high heels and a figure to die for. Leaning in the window she asks one question are u hard for me baby. My reply was.no shock she was hot so obviously yes. She got in the car that's when I noticed her xtra long legs ... Continue»
Posted by crbigboy 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Where it all started

I guess it all got started when I was a teenager and joined a swim team with Brian, who was my best friend and whose parents also happened to be my parents closest friends. We had to swim in skimpy little speedos which didn't conceal much from the imagination and hugged your every curve very tight when they got wet. One day after practice Brian and I were alone in the locker room when he looked at me in my suit and told me how sexy I looked. I was suprised by the comment, but even more surprised at how it turned me on. "You really think so?" I asked him, shocked at the excitement I felt a... Continue»
Posted by cdmelissaluv 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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The shemale and the studio part 2

We had been doing some group photgraphs of a f****y. I moved to the desk to write out an invoice! George was still very old fashioned about some things! As I dated the invoice I suddenly realised that i had been working for George for a year now! Later when we were alone I told him. He looked surprised. He nearly said something to me but changed his mind! Something was happening to George and I suspected his partner Robin was behind it all.
He suddenly asked me if I would be free later on, there was something he needed to discuss with me> I said yes of course I was free!
Things went very qu... Continue»
Posted by dasilva1672 4 months ago  |  Categories: Gay Male, Shemales  |  
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Career Path

“Welcome, Jordan,” smiled the middle-aged white man. “We’re real excited to have you on the team here at Wyatt Motors.”
“Thank you, Mr. Phillips! I’m happy to be here too.”
“Please…Call me Jim,” the finance manager informed him.
“Alright, Jim!”
“Let me show you to your desk so you can put your things down and then I’ll introduce you to everyone.”

Jordan sat down and dug a four photo frames out of his messenger bag. He set them up to his liking. He was the new senior accounting clerk for the successful used-car dealership. He adjusted his Stafford brand charcoal and red gingham tie as he... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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A video shoot - Part 2 of 2

Now there are even more guys on set. About half seem to be jacking off. I ask John what he has up his sleeve and what he needs me for.

It a Bukkake film. Damn, I get to see Tina covered in cum. My cock twitches at the thought. John tells me he needs a fluffer. I don't quite understand. After all Tina is just damn hot. Who would need a fluffer to cum on her? John says Tina is too girly. WTF? He says well some of the guys are gay and are having a hard time getting up. No pun intended. I now get what is happening. I protest weakly. But I am almost in pain from being horny as hell.... Continue»
Posted by nobodywashere 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Learning how to deep throat...

I was working the drive through window at the burger late one Friday night, this somewhat diminutive husky voice placed an order. My cock instantly begin to twitch as I heard the voice. I took the order and instructed the customer to pull up to the first window. As the car approached I observed that the driver was a shemale in full dress with a split up her right thigh to the waist.

I was so absorbed by the sight of that yellow thigh and leg that I fumbled through the rest of the proceeding. The driver looked up at me and whispered 'you'd do better if you looked at my face instead of my... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Jesse’s First Day

Jesse’s First Day


Jesse didn’t want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse had never had a tailored suit in his life, but now he knew why someone would pay so much for one. They made the guy wearing it look like a movie star. Antonio had worked his magic on the suite overnight and when Jesse had stopped by early this morning to pick it up Antonio had insis... Continue»
Posted by SCARFACE12 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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