Shemales Porn Stories
Page 82

late night hotel halls

I am 46 years old and travel quite extensively for
businss. I dress in my hotel room at night when i travel.
I sometimes entertain in my room. Sometimes I get very bold and wander out to the soda machine dressed sexily. Its about as bold as I ever get. I am quite tall and do not pass in public. But i am very smoooth and try very hard to look fem.

Anyway, very recently i wandered into the hotel halls about 3 am at a business hotel I was staying in outside of
Indianapolis. The soda machine was at the end of the
hallway. I looked up and down and when i thought the coast was clear I... Continue»
Posted by cherylfabrizio 2 years ago  |  Categories: Shemales  |  Views: 1533  |  
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diffrent, part 3

1 year later......
Rosa sat on the dildo, thinking it was her best freind in times like this. she had sucked more dicks than she could count and it was almost like a cycle now: suck, get fucked, move on to the next guy, repeat. it had continued non stop for a year now. she couldnt remember her c***dren, her beautifull c***dren. she couldnt remember tyree. all she knew was sucking and fucking. her masters walked in the doors, carrying a collar. her collar. she was put into it and walked out of her fuck room. "todays a big day for you, rosa" said curis, the black man. "today is the day you get ... Continue»
Posted by mj2397 2 years ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 466  |  
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The visit

It started out simply enough, I was visiting my s****r and
her husband for the week. They both work so I had the run of
her house and I took advantage of the opportunity to sl**p
in on my vacation. I woke late and assumed everyone had gone
for work. I took a nice long relaxing shower, s*s’s bathroom
was warm and cozy so I took my time.

When I went to put my towel in the hamper I noticed a very slinky
teddy and panty set on top. I had never thought of my s****r
wearing anything like that so I picked it up and looked it
over . It was pink silk and trimmed in lace. It felt so soft,
I ... Continue»
Posted by pandys 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2736  |  
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Delilah and the Deep Blue Sea (part three)


One day (I suppose it must have been after I’d spent about two months on the island) I was down along the shoreline collecting driftwood. On these occasions I always kept my eye open for anything else that might be of any use and this day I had a real find. Washed up against some rocks a few yards off the beach was a large plastic garbage bin. An old discarded garbage bin might not seem anything to get excited about but it was as good as treasure from King Solomon’s mines as far as I was concerned. There were literally dozens of uses we could put such a large receptacle to. My mistress was b... Continue»
Posted by Mikebasil 2 years ago  |  Categories: Lesbian Sex, Shemales  |  Views: 739  |  
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Riding the Lakefront--Chapter 4

Friday, August 15,2008....9pm....A Change is beginning....

Friday night, you are to go to a private party and you are going to be the guest of honor. You will come ready! Shaved. Hole greased. Clean. Arrive at 9pm. Side entrance.

These were my instructions....I would get a call and for the address. These bastards really had me over a barrel. No idea what they looked like. No names. Voices...was all. But distinct. They had done their research on me. But why me??? Like they said, a thing. That is what I was viewed as. A freak. What was the attraction? How had I 'wronged' them? Nothi... Continue»
Posted by titsR4abuse 2 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 554  |  
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my gardner plowed me

My wife and daughter had left to spend a week with my mother-in-law in Brazil. So it was time to breakout my secret wardrobe. Having two women in the house made it easy to keep a sexy supply of clothes. Add a wig and some makeup, I'll soon be lookin pretty hot.

I started by shaving my body and taking a long hot bath in some lovely smelling bath oils. Just the thought of dressing up was making me wet. I dried off and went to get dressed. Being in a wheelchair made it take a long time to get dressed. I wasn't even going out but I wanted to dress up and maybe video chat with some hung studs, ... Continue»
Posted by cdaisy1 2 years ago  |  Categories: Shemales  |  Views: 2099  |  
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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: 442  |  
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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: 666  |  
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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: 1562  |  
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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: 2207  |  
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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: 966  |  
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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: 761  |  
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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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