Shemales Porn Stories
Page 77

Fantasy Cum True

I have always had a "thing" for she-males, but growing up where I have and hanging with the crowd I hung with, it was taboo to express this thought. I used to go home d***k and pull up shemale sex videos on my computer after hanging with the fellas and I would be so horny watching these creatures that looked like women, with curves and all, but nice juicy cocks to go along with it. I would often fantasize about an abrupt meeting with a shemale and for whatever reason, we would talk and become cool. In my fantasies i knew what I was meeting and wanted it. We would talk and everyone around u... Continue»
Posted by heater31 2 years ago  |  Categories: First Time, Shemales  |  Views: 667  |  
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mature crossdresser & 18 year old PART 2

After we sat on the couch a few minutes kissing he whispered in my ear he wanted try licking my boy pussy.I said yes an postion myself so he could, for a boy that never done anything sexual before he speard my cheecks and started to lick and kiss my hole.Then he buried his face and tongue deep in my hole as he did that I love and made finger me at the same time.After a good ten minutes of him eating me I told to lay down on the floor he had me so horny I wanted his cock in me.
He got on his back I put just a little lube on his hard cock he had my hole wet with his spit from eating didnt nee... Continue»
Posted by cdpaula 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 1114  |  
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mature crossdresser & 18 year old PART 1

Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels.
A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother her that i was a cd/tv she said nope. Well after couple weeks we became good friends and found out her son was shy and kind of a nerd. One day she came over to me and was little upset over something she found in his room.I said what did you find d**gs or what? She said no,and handed me a note book t... Continue»
Posted by cdpaula 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 1566  |  
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Riding the Lakefront-Chapter3

August 13,2008...6:30pm...Chicago Lakefront Bike Path--Irving Park rec lot...8:30pm

My life changed that night!

The silence of the car...sitting there...thinking about the call I had just experienced...was deafening! What began as my usual bike ride ended in a catostrophic state of affairs. What began as just this innocent ride ended with the creation of a black mailed sex slave about to embark on an unbelievable series of escapades with no end in sight. I lost interest in the radio. I lost interest in stopping at the gym to clean up. I lost interest in getting something to... Continue»
Posted by titsR4abuse 2 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 604  |  
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I slept with Joanne, who had a dark secret

What is the weirdest sex I have had, I thought about is for all of thirty seconds, the night Joanne slipped inside me, on a f***ed stopover.
Now before you cry Lesbian or Bi-Sexual, you would be wrong, because Joanne was neither, she was a transsexual, something I did not know at the time, nor was she, him about to admit to, especially since I had offered to share my hotel room and not leave her stranded without.
We both worked for the same airline, which I shall not mention, due to legal obligations, but I knew Joanne from our first meeting her on a photo shoot, which was an advertisement a... Continue»
Posted by MarieL 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 2205  |  
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Riding the Lakefront-Chapter 2

August 13, 2008...8pm....Rec lot...Irving Park Rd...Chicago lakefront bike path

The event that actually changed my life began when I needed to piss about 6:30pm while on my bikeride. Tightfitting bike shorts were worn because of the padding in the ass area. But had I worn a pair of shorts with a zipper, none of this would have happened. Had I not worn a zippered tight biker shirt with my 48D tits showing, this might not have happened. But, it also was extremely hot and to be zipped up would have been ridiculous. 95 degrees, humid...typical August summer late afternoon/evening. Even a... Continue»
Posted by titsR4abuse 2 years ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 882  |  
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College cumming out party!

Aaaaaahhhhhh...where to begin? I guess it all really started in my teens, when I discovered the joy of dressing with one of my close friends. Like many others we started off slow, wearing panties and giving one another hand jobs and feeling at least a little bit like we were doing something we shouldn't be. After a few months of fooling around like this I arrived at his house one summer morning to find him dressed completely from head to toe in his s****rs clothes. Tight, short, sexy little miniskirt barely concealing a tiny pink thong, strappy stilletto sandals, skimpy camisole over a lace b... Continue»
Posted by sweetsashacd 2 years ago  |  Categories: Shemales  |  Views: 962  |  
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my new flat (part 2)

After putting the phone down i started to panic a little , i had just accepted a date from a guy who i had just met a couple of hours before, and whats more he did not know i was not a real girl, what the hell was i going to do, could i bluff my way through this.
Mark was his name he was a nice looking guy i would say he was about 30 at the most quite tall with dark hair and we did seem to get on well when we chatted so i decided i would keep the date i had made with him for that night , my plan was also to tell him i was not a real girl and hope for the best.
Mark was due to pick me up at 8... Continue»
Posted by julieanneff 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1399  |  
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My Girfriends Friend Shayla

I walk up to the door of my girlfriend’s apartment. As I start to slide the key into the lock, I can hear slight muffled noises from inside. As the door slowly opens, I am met by the sight of my girlfriend laying with her legs spread wide open on the couch and her super sexy friend Shayla, who I’ve always wanted to see naked, on her knees eating my girlfriend out. Shayla’s tight ass looks so incredibly sexy with that hot pink thong on.

I shut the door behind me and walk up to the couch as I get nice wide smiles from both of these sexy beauties. Shayla slides her tongue back into my girlfrie... Continue»
Posted by Vesper2069 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 2291  |  
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Riding the Lakefront

I finished my training session and went to my car to get my bike. I always worked out and then rode the lakefront in Chicago. This was routine..Wednesdays and Saturdays. Wednesday, I finished my workout and headed to the path. It was 6:00pm and I rode from the Hollywood curve to 71st Street and back. I am usually able to do it in about 2 hours. August 13th, it was a hot night but I liked riding when it was that way. Joints all felt loose. Rode well. Carried some water bottles with me.

Being intersexed with big tits, I always wore a bra. This night was no exception. I had a zippered shirt ... Continue»
Posted by titsR4abuse 2 years ago  |  Categories: Shemales  |  Views: 619  |  
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My sissy son by his dad and lover Part 5

Well...what a few months it's been since i/we last spoke to you.Many things
have happened,some of them great,some fantastic..some not so good,best tell you!

Lucy and i are in love,no two ways about it,we found out how to change her name by deed poll(to legally change your name in the UK)So she's now,legally..Lucy Alice Andrews and she wears a matching wedding band and engagement ring like mine.I wear just the band when we go out together,as i said..she passes for a woman no problem.So people just think i'm a guy with a younger/sexier trophy wife,(which in a way is right!) She dresses as Lu... Continue»
Posted by chocandres 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1237  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 769  |  
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My Week last Week

So it was pretty good. I never met a guy this fucking horny before, literally came three times.
So I was wearing my black wig, awesome makeup, plad miniskirt, thigh highs/w knee high gogo boots, and cute top with my forms in.
So I start sucking this guy who is rock hard when i step out of the bathroom of the hotel room. He has a nice 7 inch dick, but he is young and athletic.
Im enjoying myself and he grabs the back of my head and starts forcing his dick down my throat, so im like ok, he wants it like that. And like that he did!
He told me he wanted to fuck me and put me on the bed. I... Continue»
Posted by dani_b 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1038  |  
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Halloween fun

Here's an interesting story that happened to me last Halloween, hope you like it. Last October, a local bar had a Halloween costume contest. Since I had nothing better to do (I'm too old for trick or treat) I decided having a beer and checking out all the silly costumes would be fun. I sat near the bar and almost immediately a sexy, slinky brunette caught my eye. She was wearing a light blue dress, black seamed stockings, and dark brown "fuck-me" pumps. After a short time I went over and said hello. She was smart and funny, and we really seemed to get along nicely, but with the loud musi... Continue»
Posted by throbbinghardboner 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 2394  |  
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More of my Sweet

I was really becoming attached to this person. From the waist up a she, from the waist down completely a man. In the past, I had given thought to the attraction I often felt toward men, but I would never have taken it any further than the dark corners of the peep shows. I would never have openly dated another guy. It was always completely sexual. I enjoy sex, always have since an early age, and always will till I hit my grave.

Now, along comes this person that is satisfing both sides of my sexual desires. Someone who wanted to be with me and it was confusing to say the least. After ... Continue»
Posted by milkmanj 2 years ago  |  Categories: Fetish, Shemales  |  Views: 516  |  
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My CD friend

This story is fiction.

~~~~~~~~~~~~~~~~~~~~~~~

I had been chatting to people on a ts chat room as I had recently become accustomed to do, when I received a private message from a local cross dresser. She asked me where I was from, how old I was etc and we found out we lived a few towns away from each other, both young guys and both really loved wearing women's clothes.

Admittedly she was much more experienced at it than me, having access to girlfriends, s****rs and mothers clothes and had even ventured out fully dressed once!

Eventually after some light chat, swapping dressing up s... Continue»
Posted by shyadam89 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 546  |  
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The Ebony TS of my dreams


This story is about one of the most memorable piece of cocks I've ever experienced in my 30 plus years of getting fucking. I just thought I'd write it down and share it simply because I'll never forget it and because I'm a married man and it most likely will never happen again.

It happened about three days ago with TS Dominique I met through the internet(EROS). She was 23, but she easily looked 20. She kept her body pretty fit. She was about 5'11 and 135 lbs. I love tall women because I'm physically a big myself--6', 245lbs. It's hard to be fucked by a woman bigger than yourself. Plus, I... Continue»
Posted by yesamwilling2 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1564  |  
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A Quickie For Jemima

I checked my make-up and adjusted my brunette, bob cut, wig in the bathroom mirror. Pleased with the results I then ensured that my clothing was right. I was a vision of darkness: black G-string under black thin denier tights, 3 inch heels, black satin vest top and black mini skirt. I was sure Simon would approve.

I walked slowly yet purposefully to the bedroom. Simon was sitting on the edge of my bed naked stroking his cock looking at me “mmmmmmmm,” he said seeming to approve “ Why don’t you cum and join me the doors open?”

Out of habit I shut the door as I enter in case we made a lot ... Continue»
Posted by JemC 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 829  |  
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How it all Started....

Back in 1997 I was living in my dads place a condo on the beach.In the summers I had a friend come down from new york with her f****y. She was 3 yrs older then i was.I loved going to the jacuzzi the building had by the pool. one day I was seating in there and her grandfather and she came in. we where all in the hot water and i feel as where talking my foot being played with. after a while the foot got higher un till it was almost at my thigh inside my trunks. I got hard. I must of been twelve or so....As my friend get up to go to her towel. I figure out that It wasnt her, that was doing it.. ... Continue»
Posted by lucifer696 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2053  |  
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A Pleasant Surprise 


I really do enjoy my swing life style. Here is an example of one of those times. 
My lady has this friend, "G" and I wasn't to keen on her. But thank god she lives 4 hours away. I usually bail out on my lady's visits and she is cool with it. But then once my lady begged me to go with her on the next visit. I declined. 
A few days later she asked me again but said she would make it worth my while. Besides it was a huge cook out that we were going too. 
-fast forward to the weekend-
My lady and I took Friday off so we drove out to her friends Thursday after work. After that 3 hour drive, w... Continue»
Posted by rogue-1966 2 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 2282  |  
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