Shemales Porn Stories
Page 71

Peaches And Cream #1

Prositutes – lingerie – hookers – transsexual first time – butt plugs

I have a little problem.

Well, to be honest, it's more than just a little problem. Some might consider it to be a huge problem.

I am addicted to prostitutes.

I have been pretty much all of my adult life, since I first walked out of the front gate at Lackland Air f***e Base in Texas and saw a pretty young girl sitting on the hood of a car in front of a massage parlor. When I glanced over at her she had slipped her shorts aside and exposed her hairy vagina, and I had followed her into the massage parlor and ... Continue»
Posted by naughty_bi_interest 9 months ago  |  Categories: First Time, Fetish, Shemales  |  
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PANTYHOSE SANTA and LYCRA POLLY


They didn’t need to advertise the job for Santa’s helper. I already offered my services. Since I was fairly popular and I could provide my own costume, a skintight green catsuit, my copper wig and boots, my supervisor went for it. I must admit that my main motivation was that I would be paid to wear a skintight costume, and hopefully get a few curious glances at my ass and body in the shimmery material!
The Santa for the job was some retired security guard called Alfred who used to work at our store, who a few times I served pantyhose to in the pretext that they were for his wife. In fact ... Continue»
Posted by leotardlust 9 months ago  |  Categories: Fetish, Shemales  |  
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sl**ping With The Enemy

sl**ping With The Enemy
The present day…

The wedding party was in full swing now and I anxiously scanned the guests to see if everybody was enjoying themselves. The noise levels had risen in line with the amount of drink being consumed, so I guess that was a good enough proxy for enjoyment. I was holding a glass of champagne in my perfectly manicured fingers and as I took a sip I caught the eye of my new husband who had been buttonholed by two of my aged relatives. His eyes pleaded at me to rescue him but I simply grinned and raised my glass to him; I would leave him there for a while to t... Continue»
Posted by nikkiesilk 9 months ago  |  Categories: Gay Male, Shemales  |  
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The secret exchange (Sarah)

"Your wife told me you were a crossdresser 12 years ago, still doing it?" Sarah asked me.

Very calm, I sip my coffee and answer, "Yes."

This is how this story got to this point. Sarah has been friend with my wife for about 14 years, out of college they met in the bank they both used to work. They became very good friends. Thirteen years ago I met my wife, she did not know about Iliana, back then I was just trying to be myself with my then girlfriend and one day I decided to let her know about my closet life style.

To my surprised she reacted very well, she asked tons of questions ... Continue»
Posted by ilialenyc 9 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
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The Biograph Cinema

I visited the Biograph Cinema in Victoria London in the 70’s as a fairly naïve teenager, who ended up m*****ed. Shame the place closed, I was enjoying being fiddled with by dirty old men.


The Biograph was clearly the haunt of the Dirty Mac Brigade, and all of those sorts of men my Mother had told me to watch out for. Aged 18 I’d never even kissed a girl let alone had someone else make me cum. So, I was drawn back to the place. Like any teenager I wanked at least daily, but the previous episodes had become my favourite wanking material and I just had to go back for more.

A week after m... Continue»
Posted by Vikkinylons 9 months ago  |  Categories: First Time, Mature, Shemales  |  
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DADDY AT THE TRUCKSTOP - 4

Daddy at the Truckstop - 4

The van didn't have many windows, but there wasn't a lot to see anyway where I was. Tucked neatly in a cage, my wrists and ankles were chained to the bars, and a ring gag kept my mouth open, at first drooling a bit, but over time my mouth started to become dry. The vibrating plug in my asspussy didn't slow at all. I could feel the bumps of the concrete as Daddy sped down the freeway, and I had no way of knowing how far he was taking me from the truckstop. Was it 30 minutes? 45? It was hard to say. At first I was filled with shame and fear after Daddy made m... Continue»
Posted by StaceyDeprave 9 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
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A Reluctant Gang Bang

byTonyaTV69©

This story was stolen and posted here by a LIAR claiming it was theirs but I am the real author and they were just a cheap barely literate FAKE!!!

Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang **** at an adult arcade. I was dressed up in a white flowered sundress panty hose and white strap on high heeled sandals all borrowed from my older s****r. I had my make up done up just ri... Continue»
Posted by Tonyatv69 9 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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Tranny Motel

Tyrone and Kimberly Woods kissed as all of the guests at their house party cheered them on. It was their first anniversary and they were celebrating this night with f****y and friends. There were close to forty people in attendance – most of whom had brought some form of alcohol and all of whom had brought a gift. There was great music and excellent barbecue as Kimberly’s dad and Tyrone’s uncle manned the grill. Folks were laughing, dancing, and having a great time. In one corner of the yard, there was a game of dominoes transpiring. Next to it, a foursome was playing Spades.

Several minute... Continue»
Posted by faggyboi 9 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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A Very New Year

Sometimes things happen unexpectedly. Those words describe my entire New Year's Eve. My night started with me downtown. Now ordinarily I wouldn't step foot downtown on New Year's Eve if I could at all avoid it. The place becomes a zoo of d***ken bafoons and desperate revelers. But through an unfortunate series of events I found myself behind virtual enemies lines too late into the day this New Year's Eve. Many of the roads had already been blocked off and those that weren't were highly congested with the other like minded people that would give anything to be out of here before things got too ... Continue»
Posted by rhyze 9 months ago  |  Categories: First Time, Shemales  |  
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Cockatoo Part 1

Cockatoo


Nikkie Silk


It’s a cliché, isn’t it? Man comes home early and finds his wife in bed
with someone else. Only slightly less of a cliché in my case, as the
‘someone else’ was my wife’s closest girlfriend - closest in every sense
of the word.


It was a quick divorce; no k**s, only a rented flat, so the only
squabbles were about books and cds. In the end I told her to keep the
lot. I wanted to make it a clean break. I managed to fit all I owned
into the boot of my small car. I was 28 years old, fit, healthy and with
a good but frankly boring job in a software company j... Continue»
Posted by nikkiesilk 9 months ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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Friends with benefits Part TWO (Edith)

this is the second part of my fantasy....

It took me about 3 minutes to decide what matching set I was going to wear for the night out with my friend. I found a very sexy Simone Pêrele satin demi bra with its matching thong, that was my choice, I turned around to my friend which was in her "born suit" and "I CHOOSE THIS ONE... you sexy bitch!"

She gave me the ok look, "lets get dress first and then I am going to put you make up, I have couple of ideas, do you mine if I take pictures.....hahahahah whom I am k**ding, I am going to take tons of pictures, my sexy friend.

I ... Continue»
Posted by ilialenyc 8 months ago  |  Categories: Fetish, Sex Humor, Shemales  |  
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Old man fantasy Part 3

He told me that i was not ready to take his cock on,but deep inside i felt ready and i could not help myself anymore,it was the only thing that I was thinking of,but i could not order him around because i could not take another dildo punishment anymore,that time will come...
After 3 hours of merciless pounding he tells me to stand up and kneel in front of him,my heart was pounding rapidly,i thought that he will finally give me that glorious present that i was waiting for all this time.
He told me to stroke his penis gently through his pants while he relaxed on the chair.As soon as i touched ... Continue»
Posted by cutecdkiss 8 months ago  |  Categories: Gay Male, Mature, Shemales  |  
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Cockatoo Part 2


I had no idea how long I had spent under water but I could see a bright
light above me and I thought it must be the sun shining through the
water as I clawed myself towards the surface. But, I thought, ‘No, that
can’t be. It was dark when I fell in.’ The light grew brighter and
brighter and I wondered ‘Maybe I’m dead’. I tried to open my eyes but it
was so bright I couldn’t f***e my eyelids open. I heard sounds from a
long way off and it sounded like voices, but they were muffled and I
strained to hear but couldn’t quite make anything out.


I tried to move my arms to cover my eyes... Continue»
Posted by nikkiesilk 8 months ago  |  Categories: Lesbian Sex, Shemales  |  
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Baking a loving cake

The following letter I just wrote to a couple seeking horn toad letters about fucking them. When I get inspired I like to write, and for whatever reason this couple did it. OK, well, their sex was the reason!

Dearest Make a Cake,
What a pleasant name! Do you bake love madly? Or love baking up some sex? Either sounds ever so wonderful!

As to the Bears I always have hope for them every year. In case you were wondering the reason I even asked that is because I noticed the slippers you were wearing, and that C is very distinct to a true Bears fan. I suppose I would have more fun ... Continue»
Posted by Tigerpaw46 8 months ago  |  Categories: Anal, Mature, Shemales  |  
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Brooke



I was 27 years old when I decided.

I had been married to a very pretty woman by the name of Mandy for 3
years. She was about 6 years older than me and very much into her
"career". She traveled a lot in her business and most of it took her to
the city her parents were retired in. What that meant was that there were
many times when she would go on a business trip and then spend the weekend
with her parents and then work in the same city the next week. It also
meant that I had about every third weekend to do whatever I wanted.

The Beginning

Ever since I could remember, I had fe... Continue»
Posted by klammer 8 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Becoming Madison_CDs daddy chapter 4

Becoming MadisonCds Daddy chapter Four.
The day after the tatooist
We are in the living room Madi was dressed in a new Balerina outfit a pair of pink knee socks a pink tutu balerina skirt and a small pink trainer bra for her flat
smooth chest . She was teasing me and doing a very good job of getting me hard.
" Do tell what you would want to do with me " Madi says
" your a beautiful girl " I say rubbing my cock.
Prancing around in her balerina uniform she explains to me her Girlfriend is coming round this afternoon and her girlfriend has absolutley no idea she crossdresses.
" Oh... in... Continue»
Posted by rabbit007 8 months ago  |  Categories: Anal, Shemales, Taboo  |  
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New year eve

First of all I need to put you in situation, you could see my profile but summarizing I'm a 28 old guy who crossdressed but stopped it because i felt ugly and manly, then i consider myself between gay and a woman and i have desires over men with me as a man but mostly as a woman. many months ago I met a guy chatting online in IRC's who's much older (he 65 me 28) and he gave me confidence enough to start a relationship with him, he has changed my whole world and we started dating 2 months ago but me as a guy, and for new years eve i planned a date for me as a woman. that's it.

Well, here i a... Continue»
Posted by Lindsey_cd 8 months ago  |  Categories: Gay Male, Mature, Shemales  |  
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He doesn't fuck me like you do.

"I'm so fucking horny right now. I can't bear it..."

Those are the kind of texts I get from you throughout the week. Every now and then just to remind me what you are looking forward to. What we are both looking forward to. Thursday nights can never come soon enough, it's a shame I can only get away that one night a week. It's fine though, the anticipation and all the secrecy only makes the experience that much more satisfying when we are in the moment. We tease ourselves, it's almost like torture, until we finally get our moment.

I walk in trying to contain my eagerness and excitement ... Continue»
Posted by virg0man 8 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Cockatoo Part 3

Maybe things could have been different, I don’t know, but I found myself
in a taxi on the way to Samui airport. I was struggling to come to terms
with what had happened and I felt physically sick at what I had heard. I
had to get the taxi driver to stop so I could retch at the side of the
road.


I managed to buy a ticket on the next flight to Bangkok and by mid
afternoon I was back in the city. I booked into a hotel close to Nana
Plaza and sent a couple of hours stewing in my room, drinking the gut
rot scotch from the mini bar. I was raging at Alex, at Kritsada and
above all at me ... Continue»
Posted by nikkiesilk 8 months ago  |  Categories: Lesbian Sex, Shemales  |  
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1994 New Year's (Keela)









This a story, and no more than that!

I could not go home for the winter break due to tons of things to do about my college thesis, so I stayed in my adopted town in the Pacific North west, so Keela my running teammate. She had the same problem, she was writing her thesis as well.

Christmas went by and I spent it in my apartment by myself and tons of papers everywhere, I had chinesse take out.

New Year's eve came along and I decided to call my friend to see what she was planing to do. It was a lot of snow on the ground and I really did not want to go downtown to cele... Continue»
Posted by ilialenyc 8 months ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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