Shemales Porn Stories
Page 77

First Time By Transsexual

When I was 21, I spent a summer in a southern city doing a service project. I was engaged to a girl and excited about marriage, but I was also extremely curious about the male body. I was one of those k**s that masturbated constantly, and almost always about sex with a man or a transsexual. The summer before my senior year, I was down in this southern city living completely on my own for the first time. Since I was doing a service project, I only got one night a week off. I wasn't sure what to do with that night since I didn't know anyone, so I decided to get d***k. Several times, I just went ... Continue»
Posted by kbking64 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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CD And Trucker

CD Adventures Truckers Ch. 02a
Part 2A: Portland to Bakersfield
I turned....
At least four things went through my mind the moment I heard Hank ask me to go along with him.
- One my wife was gone for at least 2 weeks so that was no problem.
- Two, with wireless connection and my laptop I could take my job on the road.
- Three, I had hardly any clothes in my bag that I was carrying. All the clothes in the bag were girl
clothes; my boy clothes were in the back seat of my car.
- Four, my ass (oops, my pussy) was on fire and now stinging a bit from Hank's big cock taking my
virginity just ... Continue»
Posted by pr1456a 3 years ago  |  Categories: Shemales  |  
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The real me part one

Well let me began Iam not in the closet, I grew up in small town my mom raised me cuz my dad was not around. This town was dead and in my school days there was only myself and friend of mine that were the only k**s in town. It was summer and my friend had left to go spend the summer with his grandmother in other state.
My mom was a 5'9" 130 lbs d breast woman that raised me and worked her but off doing it as only hair stlies around for a 100 miles. She always wore dress and skirts and heels dolled up everyday. So oneday I was bored around the house when she was home taken a break. We were... Continue»
Posted by cdpaula 4 years ago  |  Categories: Gay Male, Shemales  |  
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xdresser foxxiroxxi fucked by daddies poker buddie

So I have finally got my men doing what ive wanted for a long time now and I have never been so horny . John is licking and fingering my ass while im getting marcuses tounge shoved in my mouth all the while my daddy and his buddies are outside . Fuck me im so fucking horny these guys could do anything they wanted to and I wouldn't stop them. Johns fingers start at one then two big black fingers slowly stretching my virgin ass then he slipped a third in and out licking and sticking his tounge in my ass then fingering me ,he kept the same pace making sure he didn't rip me so it would be a pleasu... Continue»
Posted by foxxiroxxi 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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Daddys whore


I had always been fascinated by the feel of womens clothes against my skin, and today was no different. Mom was away on a business trip to Canada, and dad was away at work for the next couple of hours.

I had always had an effeminate look to me, with me being 6’1” and thin as a twig at 19, I was scrawny. I had bought a black wig to go with the outfit that I had picked out. It was black 6” heels, black pantyhose, a black garter belt and panties, with a short black skirt and a little black tube top. I was hard just thinking about what I would look like.

I took a shower and completely shav... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Gay Male, Shemales  |  
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More Dirty Sex with Tania. Part One Hotel Sex

More Sex with Tania


Part One. Hotel Sex

It took quite some planning, after our last meet in the lay-by, but at long last we had both been able to get away at the same time. We, well actually Tania, had arranged our meet to be at the Premier Inn at Witcombe, just south of Cheltenham and just of the A46. Tania was arriving just after lunch and myself at about 3ish. We agreed it that way so it gave Tania time to dress and get ready, however it did mean that I would have to arrive dressed as Joanna. I have a lot of confidence when dressed, as Joanna but most of my forays have been either a... Continue»
Posted by joannacd1 4 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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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 4 years ago  |  Categories: Shemales  |  
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An unusual surprise

This storey is a bit different to anything I have written before. It was written for a friend as this was a scenario she wished to explore.

Sally contacted me and asked if I fancied some fun, never being one to turn down a good time I immediately agreed, she said she had a little surprise waiting and I was intrigued. I arrived on time and was stunned to see Sally sat with another beautiful lady at the bar, after greeting both ladies Sally suggested we head straight to the room as she could not wait to show me what the surprise was!

As the room door clicked shut behind us I watched as yo... Continue»
Posted by zibbles 5 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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my first time

this will be the last story i write unless someone asks me personally for more... as Andy i felt no one loved me and if i was a girl i could be that slut and try to feel some kind of love from someone. when i was Andy i dated 6 girls in the course of 2 or 3 years and 4 of the 6 cheated on me and the other two clearly hated me and made my life nothing but misery... Ana was my only way to feel any kind of love or happiness.. when i first dressed as Ana no one was interested in me i was shy and i was still trying to find the right look for me... one night i decided to go to a party and find the d... Continue»
Posted by drewcd 4 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Dawns Early Light

Almost closing time and I was enjoying a wicked high but not quite d***k. Looking around the Bar I saw almost nothing that would make my night any better and thought I'd simply head out for home. The other Bars were letting out and people were sorting out their options and pouring into their vehicles or making last ditch efforts to not go home alone. The Cops were out in f***e in the area watching for belligerent d***ks and last minute d**g deals. I knew I shouldn't be driving so I thought I'd stop at a local eatery for breakfast. It was a popular place and a lot of folks coming and ... Continue»
Posted by Keith_Walters 1 year ago  |  Categories: Shemales  |  
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Interstate Reas Area Whore

Driving down the interstate the sign said Rest Area one mile. My heart skipped a beat and there was slight stiffing of my male meat in anticipation of events to unfold. This interstate rest area was always packed full of eighteen wheelers as many as forty. Surely one or two of these truck drivers would be horny enough to over look the fact that this slut had a little something extra a top her nylon covered legs.
I had a black merry widow corset on that pulled my waist in a nice four inches. Eight garters held up my coffee colored FF nylons. I had on five inch red stiletto pumps. My bla... Continue»
Posted by littleoralvee 4 years ago  |  Categories: Shemales  |  
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First night out as a sissy

Nervously, I came out of the restroom. I had never come out side fully dressed in my girly outfits. Rickey was about meet me in 15 minutes so I hurried. I found out what cross-dressing is when I was in high school and that was the time when I, with a slim and little frame started doing it. Inside house and at various encounters I had brought the dresses with me in bags. But outside among people dressed as a girl?! Now way, never…till now! I could not believe that I was outside wearing a tank top and hot pants! Every step I took gave me goosebumps. Every time Ilifted my head and saw any one loo... Continue»
Posted by CumLovingKitty 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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cross dressed cocks

I was looking forward to the fun I could have in my own place. I spent some time on the male chat line looking for someone to play with. he to liked to dress but like me was not at all passable . when he showed up at my place he hade on black thigh highs open toe heels and a corset ,he was taller then me and of average build . it was the bulge in his panties i was interested in. I was dressed in pink thigh highs red strappy heels pink panties and a light purple chemise with a pink bra under it.

we sat on the couch watching some porn he took out his semi erect cock and told me he wanted to s... Continue»
Posted by amitokinki 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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My shemale boss part 3

I was woken by the vibrating noise of my mobile and looked over at the time, the bedside clock said 1am. The caller I'D on the phone simply showed Bitch, naimly my boss Miss Jones, would she never leave me alone.

I answered the phone and still being half asl**p simply said 'yes'.
'Don't answer me with that tone Rob' she said. 'Sorry, but its one in the morning' I replied.
'Be a darling Rob and pick me up from the club, text me when your outside'. Before I could say anything she hung up.

I pulled my arse out of bed, slipped on some tracky bottoms and a t-shirt, jumped in the car and dr... Continue»
Posted by big_rob49 3 years ago  |  Categories: Shemales  |  
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THE BUSINEES TRIP - PART I

HI

This is another one of my real life experiences. All my cross dressing and sex experiences are on my work trips as that is the only time I am alone and I can indulge in my pleasures ( as I live in a joint f****y n India so cross dressing at home or in my home town is not possible).

So here I was getting ready to go on another work trip to Lucknow ( a big town in the state of UP in India). I reached there by train around noon and since the office was about 60 kilometers out of town I hired a cab as I would be staying there overnight. I contacted the travel agent at the rail station and... Continue»
Posted by hornyboyind 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Summer affair with a latina ts mmmm

So, we all are busy and have our jobs n all and not much time for fun...So i'd thought ill try craig's list for the hell of it-which was something I would never have tried in a millions years lol. Jokingly I was repulsed by what i saw under the casual encounters but decided, "what the hell." I put up an ad with a toss away email saying something along the lines of 'big black juicy cock for horny latinas and white.' Mind you in the small town of Chico California i doubt any one would even check it, even left my cell number on there as well lol. So far, tons of spam, a few responses but they wer... Continue»
Posted by iluvtgurl 2 years ago  |  Categories: First Time, Shemales, Taboo  |  
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Gender bent – Ch 9 – Lack of free will

Gender bent – Ch 9 – Lack of free will

“Nikki, he Nikki?, Wake up” I heard a voice as I opened my eyes. “What happened?” I muttered as all I could remember was being dolled up like a bimbo slut encased in pink latex looking like a flat chested girl with a bubble butt with a ton of fake tats on me. “The process finished” J said as Kandi stood right next to him. “Wow did It work?” Kandi said. “Did what work?” I replied. J looked at Kandi and then pressed a button on the watch and said “Looks like it, but let’s test, Nikki standup” I stood in a instant is if my legs had moved on their own. “Wh... Continue»
Posted by youngprboi 5 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Creole Nigga...Chocolate Bottom

"Class dismissed," remarked the professor.

The students filed out of the room in a decent order. Xan Brooks gathered his belongings and headed back to his office on the campus of the University of Texas - Health Science Center at Houston. On his way there the five-foot-eight-inch, dark-skinned man, pulled his cell phone from his messenger bag. He saw an email from 'Mr. Fantastic'.

Dr. Brooks had emailed a few times with this person who purported to be stationed overseas, but from the area. The message indicated the gentleman was back in Houstonfor two weeks. Specifically it said, 'I wann... Continue»
Posted by faggyboi 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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Whore For Two Mexicans

One night I came home from work and saw a old beat up truck from Texas parked in in spot next to my room. As I walk to my room I looked in truck and the back was full of tools and junk, then looking in the cab I could sdee it was a mess with trash everywhere. I thought who ever it belonged to must be slobs. As I got to my room I saw my guess was right as two mexican guys came out of room next to mine and they were a dirty mess. I looked at them and said hi and sort of smiled, they both had sort of nasty grins on there face as they looked at me.

That night I was standing outside having a bee... Continue»
Posted by sissy_gurl 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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caught masturbating & crossdressed living at a

This is the first story of a few that I was so lucky to be a part of and I would love to share them with you!

I had hired this woman as a delivery driver because the store I had just taken over had ruined the reputation of the business with terrible service. Her bubbly demeanor, bordering on ditzy was cute and she was herself a beautiful 40 year old woman and a milf for sure! She would be my best tool in the road to rebuilding the business. The customers will love her. She was tall with long slender legs and a real nice round ass, small titties with huge pinky size nipples. Her hair wa... Continue»
Posted by happytayls 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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