Shemales Porn Stories
Page 66

My First Time as a Girl

I was hoping to hook up with a straight guy.

I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a big disappointment. My dad accepts me for what I am now. My mom always stands up for me when my dad criticizes me for acting like a girl.

My b*****rs look on me more as a s****r than a b*****r. Weird as it sounds I am more fem in a way than my s****r. I like to dress up in my s****r’s clothes and... Continue»
Posted by kbking70 7 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 2909  |  
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How I Became a Tranny Whore

First time as a Tranny whore!

When I was 30 with c***dren at home I would get dressed in the bedroom. When it was time to leave the wife would take the c***dren off for ice cream and as soon as they were out of the drive way I would head for my car. Of course when I returned home the c***dren would be a sl**p. The plan worked for years. The wife had it much easier. She would get dressed for a night out with the girls, and then meet her boy toys for a night of fucking.
On this night I wore a black lacy bra, black rubber thong panties (they always hide my package so well), tan thigh hi... Continue»
Posted by littleoralvee 2 years ago  |  Categories: Shemales  |  Views: 2132  |  
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My ts fuck

Patong beach thailand a few years ago, a few drinhs at a bar with some friends on going to toilet at public loo which was next door to ladyboy bar. Standing and relieving myself in runs two lovely ladyboys from next door. Who proceed to do there make up and have a good look at my cock for good measure! Now at this point I hadn't any feelings one way or another, but now I was very curious indeed!
So I made my way back to my friends at the bar finished my drink and with a lame excuse left in the direction of the ladyboy bar, feeling nervous as hell I entered. It was dark with loud music a... Continue»
Posted by kawa696969 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 1081  |  
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Tranny's First BBC

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big muscular type African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him a little smile. When I could see him coming down the hall the next time, I got up and slowly walked around the corner into the next hallway so he... Continue»
Posted by kbking64 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1530  |  
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Glory Hole Orgy

Glory Hole Orgy
Driving down the street I spied my destination. A big yellow building with “Adult XXX” written on the marquee in front was on my right. I turn into the parking lot and drove to the back behind the building and park in the darkest spot I could find. Another crossdresser had told me that they welcomed our kind and even let gurls like us in the back where the video booths were located.
I sat in my car and lit a cigarette, thinking I would see who was going in and out of the store. Half an hour later I had witnessed four men and one couple enter and two men and the couple lea... Continue»
Posted by littleoralvee 2 years ago  |  Categories: Shemales  |  Views: 1735  |  
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cinema fun

Cinema fun
i love all sex, anything is good sex as long as everyone involved is happy.
Many years ago while working in Berlin i took my car into a garage to have some work done, i was told it would take a couple of hours to complete, not really wanting to take a taxi home for such a short wait i decided to go for a walk and see what shops i could find. I walked for maybe ten minutes and made my mind up there were no quality shops in the area, it was quite run down and seedy. It wasn’t long before i came to a adult sex shop, i walked past and glanced in ,unable to see a thing i walked on f... Continue»
Posted by sean1000 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3346  |  
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Weekend with my s****r - part 1

Continued from sunbathing with my s****r.

The week went so slowly, my mind always wandering back to our day together....stroking my cock endlessly replaying each and every kiss, touch and stroke. We stuck to our agreement of not talking about it when anyone else was in the house, not touching or staring was the hardest part, the sexual tension between us was incredible, I can't believe our parents didn't sense anything. We did leave bedroom and bathroom doors open just enough it was safe. Each morning when Jane left for work she'd leave some underwear on her bed for me.....twice it was e... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 5955  |  
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Boston Surprise

Boston Surprise by FRSWRITER
It had been weeks since I saw the gurls, their memory burned deep in my brain.

Hanging around the house with not much to do didn't help either. I had been trying to call Jill for a few days, but she would not answer. About now I was thinking it was a dream and never happened.

It was getting late and I was contemplating going out and trying to score, headed for the shower to get cleaned up and go. The water felt good and I was getting hard just thinking about what tonight may bring. When I was all soaped up the fucking doorbell rang, I yelled but I guess they... Continue»
Posted by frswriter 1 year ago  |  Categories: Shemales  |  Views: 1540  |  
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MATTHEW'S RETURN part 2

I awoke early the next morning with the sensation of my cock being sucked. I opened my sl**p fogged eyes and saw Matthew's bobbing head slowly coming into focus. I exhaled a deep sigh. He was a great cocksucker.
Standing nearby was Kayla looking a little less forelorn than last night. Her fingers were absentmindedly stroking her little pink slit. She smiiled down at me before settling down on my face. The sweet perfume of her cunt overwhelmed me as she began to ride my face. I eagerly licked her pussy. She didn't have Mom's freakishly large clit but it was still quite prominent and sensativ... Continue»
Posted by slappywag64 2 years ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 1289  |  
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lucky guy (part 1)

Ive been with my girlfreind may for around 3 years now,she was my fuck buddy until we decided we wanted a realationship.
Although we dont live together as i like to keep my apartment for a bit of space now and then.
After a while the sex dried up and we were more freinds than lovers which was nobodys fault it just turned out that way.
May had a daughter,a very spoilt daughter who was growing up quite quickly,Raynor was 21.
I had never thought of her sexually,that is until May asked me to decorate Rays room while she was on holiday as a suprise for her.
Then it happened.
I had to move Ray... Continue»
Posted by wankersoffagain 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 845  |  
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3 Teen Cross Dressers Misadventure - Part 2

Here are 4 men all at least 6" taller than us with athletic builds; we really thought we were about to get our asses kicked and robbed. One man got up an opened my duffel bag and of course found all of my crossing clothes. "We have us a couple of fags don't we." He said, opening the other bags finding more of the same. We were silent until Sean said that we just do it to get a kick from people and that we weren't gay. They all stood up and one put the chain lock on the door. "You are tonight boys" Craig said. Yep we were fucked; way too d***k and no exit.Plus they started to swig the liquor we... Continue»
Posted by ClaireCD 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 479  |  
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Tonia...

One night I went to a different club to check things out. By now, I
knew what I was looking for and where to find it. I was cruising the
area with several bars for people with my kind of preferences you
know women with more to offer a man.

I parked out in the lot and began to walk in as I did I noticed this
beautiful brunette with long legs. I was very interested in
following her into the bar. I rushed to open the door for her as she
just politely blushed and smiled at me. I tipped my head to her in
respect trying hard not to blush too. She smelled very beautiful,
the sweet smell of... Continue»
Posted by NaughtyNshy 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 470  |  
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World of Confusion

I first fell in love with transexuals when i first stumbled on a video called world of confusion, at first i was like oh yeah! this is gonna be a good porn one guy and three girls awesome, so then at first the guy is jerking off then all of a sudden these three females come out i was like about time now suck his cock, so this one female goes down on him then the other female start playing with the other females ass fingering it i was like oh yea! this is getting hot then out of nowhere he grabs one of the females by her g-string and starts pulling her panties down and then starts licking her p... Continue»
Posted by Ray3 2 years ago  |  Categories: First Time, Sex Humor, Shemales  |  Views: 983  |  
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my first tranny pt. 2

it felt so good to cum in her mouth. that wasn't planned. her mouth just felt so good. nice & wet. told her what really got me off so fast was having her cock in my mouth.

"in that case, come here & suck it some more."

she laid down with her legs open & her dick in the air. without hesitation, I got between those nice long legs & put her dick in my mouth. she was moanig as I sucked her cock. she was about a good 6 inches. I just sucked & sucked. she put her hands on my head & was making me go up & down. I got her cock nice & wet.

I never told anyone this but, I loved sucking her coc... Continue»
Posted by radec_24 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1124  |  
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in public

here are the usual disclaimers this story is for adults only if you are viewing this and
are not 18 years of age or older please close this page immediatly.

there is no cross dressing in the story but this is how I began my transformation from
regular boy into cock suckking teenage crossdresser.

we were having a really hot heat wave here in philadelphia; my mom wanted me to get out
of the house and off the computer so she suggested a movie. I felt wierd going to the
movies by myself but I really did want to see that inception movie. I looked up when they
the theater opens up ... Continue»
Posted by kellyblue66abc 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2016  |  
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He or she? It did not matter to me!

I was sitting in my small apartment watching TV and having a few pipes when I heard a ruckus in the hallway. It was my room mate Joel and some of his friends retuning from the pub. When they knocked on the door I answered and there he was with some girls he knew but who were all strangers to me. As they entered I noticed Candy, a tall (obviously) male dressed in a bright yellow top and skirt, black stockings, high heels and the most outlandish purple eye shadow I have ever seen. As she passed me she smiled and asked where the bathroom was.

A short time later we were sharing some lines and ... Continue»
Posted by sydguy 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 2045  |  
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Sissy crossdresser and her Black Daddy Part 2

After nearly a week of almost nonstop creampies, facials,deepthroating blowjobs and bareback anal fuckings, my black daddy and I were sad to know we had one more night in which to have our nasty, kinky fun before our respective f****y remembers return. I had dressed in all manner of nasty lingerie and costumes for his black cock to use and I loved every second in which he entered my holes. This being our last night together my daddy told me to "take a shower white slut, and make yoself pretty. I got a surprise for dat ass babygirl". My cock could hardly get any harder I was so excited. I enter... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3049  |  
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How i became a sissy/my first blowjob

I'm a 17 year old sissy now but i started crossdressing 4 years ago when i was 13 :).This is the story. One day my parents went to our lake house for the weekend with my s****r but i was feeling sick so they left me with my grandparents. They were taking care of me for a day or two and i got better so they left and i was home alone.I had 5 more days until my parents were back.One day i was feeling very bored so i opened my s****rs closet and looked at her stuff. I noticed thongs,i never knew she wore them (she was 17 back then). I wondered how they would feel so i put them on. I never felt sex... Continue»
Posted by sissygirl1988 8 months ago  |  Categories: Fetish, Shemales  |  Views: 3122  |  
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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 3 years ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 1684  |  
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An amazing true story

okay never done this before but here goes =) So i had just broken up with a girlfriend a couple months ago, and had been feeling pretty down and unhappy. I had a friend of my f****y invite me over to hang out and play some video games and eat some dinner. When i got to their house Jan and Ted, they have been married as long as i can remember about my parents age, were glad to see me and felt some relaxing fun would take my mind off things and everyone could have a good time. So we started playing some video games and drinking some wine when ted had to get up to do a little work and left Jan an... Continue»
Posted by xnotclspamx 11 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 3589  |  
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