Shemales Porn Stories
Page 63

Hitch Hiking across Europe

I wanted to go visit my cousin in Germany but couldn't afford it really, but on a whim I decided to go for it, just pack a few essentials and hit the motorway with my thumb out. Anyway to cut a long story short I finally got a lift from a couple in a nice big Mercedes, and started chatting, like you do about everything and nothing, when we came to a service station and they had to fill up with petrol and have a bite to eat, explaining i was kinda broke, the wife says that is okay, we will buy your lunch in return for a favour, and nothing else ......we sat have a meal and coffee, and the... Continue»
Posted by gkaye1954 8 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Paying for my own birthday present!

My wife told me that she'd arranged for us to spend a weekend in London, see a show and do a bit of shopping for my Birthday.

Great I thought.

We got to London, from Wales, early evening on the Friday. Checked into a quite nice hotel in the west end and headed up to our room. When we got up there, my wife headed for the bathroom and told me to come with her. Knowing what to expect, I stripped off and laid in the bath. She climbed in, pulled up her skirt, moved her g-string to one side and pissed straight into my mouth. We'd been in the car for about 5 hours, so what I got was stale and b... Continue»
Posted by garyw 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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"My First Time"

I remember my first experience with a tgirl,i saw her ad on craigslist and was really turned on by how sexy and beautiful she was,i`ve always fantasized about fucking a tgirl and being fucked by one thats been my fantasy for a long time,so i finally decided she`s the one,it was her pictures on craigslist that finally made me wanna do this,i was so turned on by her beauty and knowing this girl had a cock.When i called her and she answered my heart was beating so fast,my cock was hard as a rock and my ass was twitching like crazy just wanting her cock in me,when she agreeded to meet me i was ner... Continue»
Posted by tgirllust 3 years ago  |  Categories: Anal, Shemales, Taboo  |  
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Afternoon Delight.

AFTERNOON DELIGHT.
Just a brief insight into my rather naughty afternoons.

I usually have a nice warm shower and shave my legs armpits and pubic area. With growing excitement I then I lock all the doors and close the curtains. Back in the bedroom I open my bedroom cupboard and pull out all of the boxes and bags containing my heels, hose and lingerie.
First I select a brand new pair of nude Aristoc Ultra Shine sheer to waist tights. I break the seal and slide out the plastic envelope containing the new unworn, ironed tights. I then break the inner seal and gently float out the new she... Continue»
Posted by pennypantyhosed 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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My Friends House part 2

The next morning, after I slept like a baby, after that great wank, I stood up from the bed and saw my friend was not there. I called on him, but no one responded. I went to the kitchen where I saw this note on the table.

Hi. Just wanted to let you know that I’ve already left for work. So when you leave, please lock the door after you.
And hide the key - you know where.

I saw the key on the table. And thought to myself, ‘Hmm...I'm alone in the whole house right now!’

His mom was a stewardess on a plane, so I knew she would not come home for at least 2 days again. Wow, this is great! ... Continue»
Posted by HosieryQueen 5 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
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LADY SUKI

It was my best friend who dragged to this little club downtown promising something I had never seen before. It turned out to be a little strip club. We found a seat right in front of the stage and we watched strippers of various shapes, sizes, and ages perform with a bored mechincalness.
"And now our feature attraction...." began the disembodied voice of the DJ.
"This is the one," my friend said, jabbing me in the ribs with his elbow.
"....let's have a big round of applause for Lady Suki."
From behind the curtain steps this amazing Asian girl whos... Continue»
Posted by slappywag64 6 years ago  |  Categories: First Time, Shemales, Taboo  |  
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The Transformation part III

Since Mistress Anna had left me to sl**p with a vibrator shoved in my sissy hole It took a great deal of time before I decided I had had enough of the pleasurable sensation. It was long after she left that I actually slept. Despite the handcuffs and lease I found I slept amazingly well. Surprisingly being locked away in chastity was far from my mind. Then I woke up.

I felt someone step onto the couch where I was laying. When I opened my eyes all I saw was black and realized my eyes were covered. My head was grabbed and I felt a hand guide me to a lowering pussy. The taste said it cle... Continue»
Posted by fictiong 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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TOTALLY DOMINATED

I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I met a very beautiful woman. She was tall and slender with bright red hair. She had a huge rack, at least a double D, and a tight sexy ass to match. Her name was Cherry. This has to be my lucky night I thought when she asked me if I wanted to hit the bars and so I agreed.

I spent the night going ... Continue»
Posted by LORDLONE 3 years ago  |  Categories: Group Sex, Shemales  |  
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My new carpool lover!

Good fortune smiled on me yet again this summer. If you keep your eyes and mind open, there’s no telling what you might find. At an office meeting a few months ago my company kicked off a carpool plan and the HR staff strongly encouraged participation. I figured I’d do my part by dropping my name & address into the pool database, but I had no intention of joining an actual carpool. After a few weeks I received an email from the pool organizer, saying that there was an opening in a pool group that lived in and around my neighborhood. Being the good guy that I am, I just ignored it of c... Continue»
Posted by ocmike 3 years ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Shemale Assassin


Sarah was lining up a shot with her bow, preparing to take down the deer she had been stalking for ten minutes when there was a loud cry from the North-East of her hunting blind. The cry startled the deer, causing it to flee from the noise that permeated the forest.

"There goes a few meals." Sarah sighed with frustration.

Within seconds of shouldering her bow, Sarah noticed that the cry was actually a call for help and she made her way through the trees towards the screaming woman that was making it. In that area of the forest, it might have been a bear attack, bears being common enoug... Continue»
Posted by drew1207 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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I was Used








I Last night I went to an adult book and video store to mainly buy a new dildo to fuck my ass with.I found a nice 8" real looking one that had multiple vibrator settings and picked up a bottle of lube as well.I of course got sidetracked looking at gay videos and magazines as I held on to my new toy and lube.As I browsed the videos a buff looking obviously gay couple walked in.They were looking at videos and the different lubes.I would peek at them from time to time and smile....very hot....one was 6', blond, 30ish, without an ounce of fat on him...acted like the bott... Continue»
Posted by LSancho 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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The best s****r ever part 3

As always yes my s****r is a shemale and yes this is all true every word of it.

So since we have formed our new relationship we have been fucking not stop for about 4 years now so im 14 and my s****r is 16 years old. I have now a thick 6" hard cock and my s****r has a huge 7 1/2" cock and we are both familiar with each others bodies but her breasts were so perfect, they were 32DD cups for a shemale.

Well it was a Thursday and both mom and dad said they would be working late which gave my s****r the grin I loved to see and I just grinned bak at her. We heard the door close and the car lea... Continue»
Posted by horndogs 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Jake and sexy Tgirl Amanda were next on our "

So after we went out with Pete and Becky all day
Jet Ski's, Diving, and sneaking off for some impromptu blowjobs or a quicky, Alex and I decided that we'd ask Pete and Becky if they'd mind if we brought Jake and Amanda into our group. We described them to them, and they were hooked.

That evening at dinner Alex took it upon herself to make the first move. She sent over some drinks, and they came over to our table and that's where this story begins.


Amanda asked if we were swingers, when I spoke up and told her that even better than that, we're all bi swingers. Her jaw dropped and he... Continue»
Posted by SpicySide69 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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Gary's Dressup Sissy

When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.

One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One mov... Continue»
Posted by palmorr 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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double date fun

It was just normal saturday when the phone rang.I answered it an my mom was on other end.She said can I ask you to do favor for me? I depends on what it is.Well she said, you know Cathy (moms lez lover) she called me and ask me to go out on date tonite.I yea so go, she said want to but her son just moved back in with her.I said yea don't he know about you two?Yes he does but we were wondering if you go out with him with us.I said well let me think,she said he very tall handsome an 46 yrs old.I said but does he know I am fulltime crossdresser? Mom paused a minute and said yes he does.I said ok... Continue»
Posted by cdpaula 4 years ago  |  Categories: Mature, Shemales, Taboo  |  
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Becoming the girl i really am....

I guess I'll start from the beginning, I was in my early teens and my parents had friends in town who we did everything with, travelling, camping, holidays, the works. They had a daughter who was a couple years older, and a son who was my age who was pretty much my best friend.

We started masturbating together in our very early teens, and since we were such good friends we were together a lot. One night i was sl**ping ove rhis house and while we were masturbating he asked "have you ever gotten a blow job?" "No" i said, giggling nervously as he slid right up against me in bedand slowly r... Continue»
Posted by dirtygurl4u 5 years ago  |  Categories: First Time, Shemales  |  
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Crossdresser drinks cum

Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she wanted me to pop, she'd plunge her head all the way down my pole.

Less than three minutes into the BJ, my cock disappeared into her face. I shot my load. Nikki froze while I unloaded. She couldn't say a word, but the bemused look in her eyes told me she was loving every second of it. I must've d... Continue»
Posted by MasterDavidsslut 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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My New Lover!

I was still testing the waters a bit. I went out in my skinny jeans and just a t-shirt (I still don't crossdress in public at least not heavily, still uncomfortable), my slightly long hair makes me look very androgynous. I wear very subtle eye makeup as well, I am happy in my body, it suits being a guy for my job and a girl for my lover. I thought I liked him a little but by the time we made it back to my house, which was empty, an irregular occurrence, he had been very nice and hit on me a little. He complimented my body and my ass (not to stroke my ego but I love my ass, I get compliments on... Continue»
Posted by bisubtaylor92 11 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Met 2 s****rs with a secret part 2

Synopsis: This story is about a young man named Devon who is living abroad as he goes to college. In the previous installment, Devon meets Asha and Shanthi - two half-white, half-Sri Lankan s****rs who live in the apartment next to his, and they begin an immediate friendship. With Asha, that friendship becomes more after Devon discovers that she is a transsexual. After their first night of passionate sex, Asha tells Devon that they must keep their relationship a secret because her s****r Shanthi is in love with him, and Asha fears she has already betrayed her s****r by sl**ping with him. But D... Continue»
Posted by drew1207 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Never Going Back Again

feminize – feminization – transsexual – crossdresser – gay

To tell the truth, I never really figured out how to do the guy thing very well. I was always small for my age. People used to say that I'd shoot up someday, but it never happened. All through my school years, I looked about two years younger than my classmates. It didn't make for an adolescence filled with confidence, or even security. I was picked on mercilessly—teased, of course, but also actually beaten up from time to time.

It didn't help that I wasn't just small of stature but also small in the "manhood department"—s... Continue»
Posted by naughty_bi_interest 3 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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