Shemales Porn Stories
Page 63

#3 - Nikki in the Woods

About four days had past since my last fuck when I heard from the same guy again. I bumped into him at some local shops and we got talking and I could tell by the bulge growing in his jeans that my presence was having an effect on him. He hinted that he could go a quickie and luckily I had what I needed in my bag. I asked where we could go and he said he would drive me to a spot he knows is always quiet. I agreed and we went to his car and he drove me to the carpark at a local park. He said that if we walk a bit into the woods he has a spot he used to take an ex gf and its normally very quiet.... Continue»
Posted by Nikki_93 2 years ago  |  Categories: Anal, Shemales  |  Views: 1783  |  
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lesbian adventure

I had worked a day shift - I got off at about 5 and wanted to go do something. My two buddies, Niles and Will, were there and they asked me if I had ever been to this little bar in the same strip mall as the club I worked in. I hadn't. It looked dingy and dark from the outside, and since I didn't drink, there hadn't been much to tempt me in I thought. They told me I should check it out.

So we go into this place - it didn't even have a doorman! - and my eyes have to readjust to the dark. There's a stage, but no one is dancing. They order drinks - and a club soda for me - and tell me to relax... Continue»
Posted by leadpencil21 2 years ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  Views: 758  |  
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My First Cock

I always knew I really was meant to be a girl. For a while I thought I was simply gay, but I loved wearing thongs and bras. I loved masturbating while pretending my asshole was a vagina. I never made it a secret. I'm very flamboyant and girly. I still managed to have lots of friends in high school. Several of them knew I wished I was a girl.

One night I was very upset about God knows what. I was crying with a good friend of mine at his house. He was straight and had a girlfriend (another good friend of mine). I began venting to him about wanting to dress like a girl and be treate... Continue»
Posted by hotchickinchitown 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4139  |  
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Another time Another Place Finale

A NIGHT OUT

A taxi was waiting outside. I was ushered by Richard towards the rear door and he hissed, “Don’t forget you are a girl now Charlotte and you should have been taught how to get into a taxi” In a haze of nervousness I did as I had been told. I tried to follow Renata’s instructions but it was not so easy with a real car. Richard got in the other side and issued some instructions to the driver about the centre of Roma.

He sat close to me and was holding my hand down close to my left leg with my other hand I tried to pull my dress down but still there was a huge expanse of silk... Continue»
Posted by charlottekerscot 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 525  |  
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Willows transformation 1


Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, at best, 5 inches. My touch, or my tongue, on her clit seemed to be much better received than my cock inside her.

I've always been a cross dresser. I can remember being in first grade and wearing my older s****r's clothes and pretending I was on a date with a boy. Before we married I told Fern about this. She treated it as something that would go away once ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2078  |  
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How I Became Vanessa Chapter 1

PART I:

I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to our place with a beautiful daughter named Elena who was only 18. I was a handsome 22 year old blond boy, quite feminine in my features and certainly very shy with girls because of this very reason. My girlfriend, July, was actually my first one, and she did the first step towards me. I was not rea... Continue»
Posted by slutyvanessa 1 year ago  |  Categories: Shemales  |  Views: 1883  |  
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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 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1562  |  
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Gay Roommate crossdress

I have been cross-dressing since I was 7, always been a bit in the closet about my homosexuality and cross-dressing but I have always loved it and kept it close.

I had one roommate when I was living in Boston his name was James. he was a pretty good looking guy who seemed to always be doing well with the ladies and I always secretly watched him as he paraded around the apartment in his underwear always hoping one day he'd notice m little did I know he already had.

it was a typical Saturday morning I had gotten up and said hi to James on my way out for a jog, went out the door and st... Continue»
Posted by alex_boycd 4 years ago  |  Categories: Gay Male, Shemales  |  Views: 2739  |  
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Old trannie gets a boys virginity

Oh dear I’ve been a bad, bad old trannie. I let a teenage boy seduce me.

I normally only go with guys over 30 at least. But this teenager contacted me on a dating site. I gave him the normal “Thanks but I’m in my 40’s you’re a bit on the young side for me” reply. However he kept contacting me on the site. He was very curious and quite sweet. I chatted with him online and he said that he would really love to meet me.

I told him if he wanted to meet me that he could find me at my local sex club. He said he couldn’t go there. After a deep thought I said it would be O.K to come round on the... Continue»
Posted by toniparr 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4456  |  
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Caught by Neighbor

Caught by Neighbor


- 1 -

It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not for the first time, I stopped in front of a mirror and pulled my tracksuit pants down, admiring the bright pink, silky panties that I'd been walking around in all day.

I'd been cross-dressing for many years before I met Sam, but it really wasn't her thing. So I tended to ... Continue»
Posted by Femluver 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 9190  |  
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Part 7 my new lingerie

As rose walked me into the front of the store I was another girl standing behind the front desk. See saw us and looked at me. Rose than told me that she also worked at the store and that it was ok. We walked over the the desk and the other said "what do we have here rose ? A little play toy for you." I wanted to hide but rose would not let go of my hand.Rose told her that my uncle left me there to get my glirly clothes. The other girl said her name was Mary and asked me mine. I told her my name jay and she said "no what's your girl name?" I said that I did not have one. Rose said that I needed... Continue»
Posted by suecd58 2 years ago  |  Categories: Interracial Sex, Shemales  |  Views: 768  |  
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Adult Bookstore Dancer

Adult Bookstore Fun
At one time there were eight adult books in my city now there is only one. Makes me very sad as I loved dressing up like a twenty-five cent whore and visiting them on the weekends. I think I enjoy all the humiliating comments and condescending looks the customers would make about me in the front as much as I did sucking off cum filled cocks in the mini booths in the back.
One of stores had girls working in the front that would give you a privet dance, for a fee, in one of the many privet room available. I meant Ida there. I was in drab and looking at the BDSM magazine... Continue»
Posted by littleoralvee 2 years ago  |  Categories: Shemales  |  Views: 877  |  
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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 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1556  |  
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Ladyboy Secrets

LADYBOY DIARY
by utubeslut

forgive the misspellings but inocent words get sensored
by the auto censeless

Diaries can be dangerous and have unexpected
consequences if they fall into the wrong hands.
Or the right hands ….


Early Spring and that meant a visit from my
Aunt Becky and my cousin Susie.
I loved Susie but she was kinda weird.
She had mood swings like she had permanent
PMS, very unpredictable.
Otherwise she was very sweet.
Crazy bitch.

The neighborhood girls were drawn to Susie
like a magnet. Crazy peop
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: Lesbian Sex, Shemales, Voyeur  |  Views: 1208  |  
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The Arrangement





My wife and I have been married for 10 years and are very much in love but we do have our own little fantasies as we have learned over the years. She is 5'8" tall, blonde hair blue eyes, in my mind, quite a sexy body, with great legs, a nice ass, and ample breasts. She really looks pretty hot.......when she wants to. As for, me I am 5'10" about 165-170 lbs, and as her I have blonde hair and blue eyes. I have a fairly nice build, having been a collegiate athlete and still in ok shape.

That being said let me set the scene for what has taken place in our lives. Early in our marriage w... Continue»
Posted by lonicd 2 years ago  |  Categories: Fetish, Shemales  |  Views: 1845  |  
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How I became a GURL part II

So I'm in college now, I've learned to love and use porn in all its forms, I've learned to be a great cock sucker and to have my ass fucked. I've learned to tie myself up -- as best as possible -- to pee all over myself to get that humiliating feeling. I'd spread the porn mags all over the floor and spend the entire night playing, trying to shoot my cum onto a photo of a cock so that I could lick it up.

The feeling of release whenever I gave in to all of those instincts was fantastic!

I loved cock! But I was a horny 20 something and still chasing pussy. Eventually the girlfriends star... Continue»
Posted by jenn1 3 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  Views: 868  |  
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Lucky Afternoon Part 5

The day finally arrived whe I absolutely had to get my boat out of the water and fortunately it was a slow day at work so I asked a couple of my employees if they wanted to assist me? They eagerly agreed because they would still be on the clock and it was a very nice day. I had them drive one of my company trucks and I took my own truck and told them to meet me at the boat dock. I decided to stop and pick up some beer and ice and figured we could run around the lake for a few times to use up some of the fuel before it was parked for the winter.

I hadn't talked to Nikki for a couple of da... Continue»
Posted by rcpeters 3 years ago  |  Categories: First Time, Shemales  |  Views: 584  |  
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tranny hooker ( UK GUY SEEKING CONVINCING TV &

I was out late looking for a cheap hooker with £15 in my wallet I should at least get a blowjob. After 20 minutes of searching I see a young girl stood on the corner. I pull up along side her she tall long legs short skirt stockings m holdups long dark hair as she bends down I tell her how much for a bj. For u darling £10 for everything I m more than happy with that. Once in the car she tells me to drive down the road and take 2nd left. We end up down a dark alley at the end a quite car park. Once there I turn off the car she opens her legs grabs my hand and slides it down the inside of her th... Continue»
Posted by crbigboy 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 865  |  
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me and connor say goodbye..

Connor and i were f***ed to separate some time ago due to his f****y moving for work. he never specified where but when he told me this we only had a few days together before he had to leave.. we spent the next day trying to figure out if there was a way for us to have a long distance relationship, and we did our favorite thing to do which was to walk through sex shops together, and we saw some kit to clone a dick.. i got excited because i thought maybe i could give it to Connor as a piece of me so we would stay somewhat close... Connor didn't know i was making it but i had it ready the day be... Continue»
Posted by drewcd 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 242  |  
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The ConVentioN part

2. Arrival
Pulling against the chains that secured her arms over her head, Sasha whimpered in frustraition
yet again. Her bonds hardly rattled at all as she shook and twisted her body to try and get free.
All she succeeded in doing though was making her heavy tits jiggle and bounce painfully. Alone
and naked save for the few cow patterned garments her mistress had allowed her, Sasha cried
softly in the darkened room. Her breasts were swollen with milk, now each one was larger than
her head! Pink bands had been tied to the base of her nipples, preventing any of her milk from
leaking out.... Continue»
Posted by peterbtrs 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 865  |  
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