Shemales Porn Stories
Page 62

My introduction and first "real" meet

Well to start off, I’m 6’, good looking, masculine and athletic, 40yoa. I’m very much opened minded and I use to dress some few years ago. I got married and it pretty much had to stay a secret. When I did dress, I dressed fully and was quite passable. It was a shame I had to get rid of all the sexy lingerie, heels, stockings, make-up and wigs. Yeah I threw a lot of stuff away knowing if I got caught it was over but now I don’t have that worry anymore. Thank goodness that relationship ended, but it was for the good. I met a few cross dressers, before the marriage, from the Colorado Springs and ... Continue»
Posted by stormietv 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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my 2015 dr visit

Every year I have my annual Dr's appointment and it seems it is getting a little different each year. like in the past years I've been seeing the same Dr. and nurse. I make my appointment and as usual I show up wearing panties and a a/b size bra. I only own panties and since they have seen me in them in previous years it is no big deal. I do wear pretty panties with lace around the waist and leg bands.

When I was called back by the nurse as usual she had me take off my shorts and top and put on a gown and commented on my pretty bra and panties and told me to keep them on since they were... Continue»
Posted by sissygirl 1 year ago  |  Categories: Gay Male, Shemales  |  
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The Club and The Morning After

As we were leaving for the club I couldn't help but notice how sexy Linda and Kathy were dressed. Kathy was wearing a short black dress that seemed molded to her figure and nearly exposed her ass it was so short. Linda had on a pink, glittery looking dress that was flowing, short but not as short as Kathy's dress. Linda's nipples were visibly hard and both ladies were wearing high heels.

When we arrived at the club the doorman greeted Linda and Kathy like old friends, hugging and kissing both, then nodding to me and Henry. One could hear the music outside, but when the doorman opened the do... Continue»
Posted by trisexual69lvbbc 1 year ago  |  Categories: Fetish, Group Sex, Shemales  |  
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New beginng

Here was I, Nick Beaumont skulking around like some common thief, but
needs must I thought. I crept through the undergrowth at the side of
the house. I had hurt my ankle when I had jumped down from the wall
that surrounded it and was limping slightly. At least no one had seen
me and for that I had to be grateful. Should the mob that I was trying
to avoid get hold of me I was a dead man and they would not make my
demise pleasant. My stomach churned at the thought of what they would
do to me. I owed them £50,000 at an interest rate that meant it was
growing by £2000 a day. The gambling b... Continue»
Posted by klammer 1 year ago  |  Categories: First Time, Shemales  |  
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At what age it can be definitely classed as that, is for lawmakers and
judges to decide. UK law is clear but not always a realistic guide. For
reasons of shame or guilt many gay or trans youngsters have found that
casual sex with much older adults was the only discreet way of exploring
their own sexuality, before they felt ready to step into the more
familiar minefield of emotional relationships with people nearer their
own age.

An age-limit there must undoubtedly be, and obviously for the protection
of vulnerable young teenagers it has to be rather a blunt tool. But many
adults (an... Continue»
Posted by klammer 1 year ago  |  Categories: BDSM, Gay Male, Shemales  |  
  |  1

Lust, Desire and Intrigue

I knocked on the door for the first time and a woman answered. She was
dressed like any other person you might see shopping at the mall. Like
she could be anyone's mother or aunt.

She softly told me to undress and to fold my clothes, then turned to
walk out of the room. I am uncomfortable and ponder if I am even at the
right place. I did imagine a six-foot stiletto-heeled vixen with
leather and whips hanging from her corset.

"Now!" I heard and I was slapped back to reality. I stripped, folded my
clothes and looked for a place to lay them. But awkwardly I just stood
there not k... Continue»
Posted by klammer 1 year ago  |  Categories: BDSM, Gay Male, Shemales  |  
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It really wasn’t my fault. My wife had f***ed the situation on us. Despite
knowing that neither of us knew the streets of Chicago, she insisted that
we get a rental car instead of a taxi. So why do I get the blame and have
to feel ashamed?

My wife wasn’t always so mean or domineering. We were, at one time,
close friends and partners. My ideas and her ability brought us together in
a business partnership. We opened a startup computer software company
together. After the initial struggle, we were able to get venture money and
had some modest success. Tha... Continue»
Posted by klammer 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  2

Meeting Mr Mac Muffin

Meeting Mr Mac-Muffin

Now it was like 11.30 pm Saturday night when I had finish work and was one my way home when i saw my old gurlfriend Loraine at the bus stop. Its like two years since we last saw each other so i figure hell why not an the bus would leave the terminal an 12 sharp . Since I always have a stash of clothes in the car, I pull into a park an pull out my girl clothes.
In less that 10 minutes I was a girl, my brunet wig was a little ruffle an some red lip stick made up my face . My homemade breast and pussy with my black lace panties took care of m... Continue»
Posted by hellpuss 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Introducing Jessica

Say hello to Jessica, she's 19 (at the time of this story) and very friendly.

The name I chose when becoming more and more of a sissy.

It was a quiet weeknight, and I was alone at home. Fresh out of the shower and sitting naked at my computer, online and chatting to lots of horny people.

After a while of chatting a while, some private chats were going on and getting hot and heavy. Some with new people, some with same people I've chatted before.

In this instance was someone I'd chatted to many times, henceforth known as John. We chatted often and about many topics, but mostly about ... Continue»
Posted by Want2BeTrans 1 year ago  |  Categories: First Time, Shemales  |  
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Sissies Feminization and Hormonal Transformation t

I was 39 years old and I have been a female inside a mans body. I've dreamed of changing into a full woman. Yet I got married, and had a wonderful boy. I asked my wife one night what she thought of being with another man, & was very upset. I continued to explain how I fantasized about being her cuckold an being feminized completely including hormones, body modifications, and living as a female on our Jamaican vacations were she could fuck, suck, and eventually be impregnated by a BBC. She said I was disgusting, and shed never do BBC. So I continued with a very WEWC, and detailed his thickness... Continue»
Posted by briannasissycuck69 1 year ago  |  Categories: Interracial Sex, Shemales, Voyeur  |  
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Serving the Mistress

The phone rang four times.

Hello can I speak to Igrid please.

This is Ingrid, a well modulated sexy voice replied.

Ingrid, you have a bridal gown advertised in the newspaper, can you tell me
something about it.

Yes, its very beautiful; The top is satin and quite tight to mould to your
figure. The sleeves are very puffy at the top and can be worn on or off the
shoulder. They have a little ruffle tied with ribbon that hangs down. I wore
the gown with tight elbow length gloves, cut away at the fingers and
trimmed with lace.

How about the skirt, He asked consulting... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  

Made me a woman pt.2: Degradation

I'm regaining my senses... im on my back, in my bed, im naked, i feel an around me, and heavy breathing next to me. My big black man was sweating and panting. im sweating, my body is shivering, and my ass is raw and leaking out his cum. His hands start running all over my body groping my tit, rubbing my phat ass. i can feel myself getting excited again and getting hard. he notices that so he spits in his hand and grabs me by the crotch. again his massive hand completely takes me and he starts rubbing me. i start moaning and gyrating my hips on his hand. he leans over and whispers in my ear "yo... Continue»
Posted by alexismorel 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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The real me..

Finding the real me

I live in Perth, Western Australia and go to a place called Perth Steam
Works. It's a small building down a side street and not much to look at.
It's a place where Gay men can go, it's clean, discreet and unobtrusive.
I don't consider myself gay as I have no interest in men that is until I
am dressed. Is this the same for all like us?

I have been there a few times with the sole purpose of getting it off
with men. Normally I take all my gear with me in a bag and change there
but it's difficult because there are no changing rooms, or none that I
have seen, an... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
  |  1

....just me being a slut

I whimper and moan with lust as your fat veiny cock slides in and out of my well trained slutwife asspussy.
i push my ass out to get as much of you into me as i possibly can, my cunt wants your whole cock.
you slap my ass with a loud smack "you lovely little whore, you cant get enough of my cock, can you?" you laugh while manhandling my body "NO, I want your cock all the time" I gasp from your hard and deep thrusts "I need to be filled all the time!" you yank my head back even further shove 3 fingers into my mouth and hold my mouth open not missing a beat plunging deep into my bowels. Your ... Continue»
Posted by bimbodollval 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Last weekend

I had arranged a meeting with a new gentleman lover.

I was excited about being naughty.

Knowing I was going to fulfill my craving with a big new cock to play with made me bulge in my panties as I drove to his place.

I arrived at my new friends place a little early.

He answered the door in a dark Tshirt and jeans that hugged him in all the right places.

There was a little chit chat, but we both knew what we wanted. He wanted to fuck me and I wanted to feel a hard cock fill me with why delay the fun!

After kissing me, his hands found my tits and pinched my nipples. ... Continue»
Posted by lornasababe69 1 year ago  |  Categories: Anal, Mature, Shemales  |  
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A Night At The Opera

I took my seat in the opera house looking...hoping...and aching to see if my companion was attending the opera that night. For the last two months, I and my wife had seats D2 and D3...and seated next to us were another couple. She was simply the most beautiful woman I had ever seen. Her beauty was amplified by my own dying marriage. My wife and I already had the divorce papers filed. Perhaps I was k**ding myself, but the woman seated next to us seemed to pay extra attention to me...and it was clear that her companion was bored and not interested in her. His loss...she had long blond hair...gre... Continue»
Posted by naughty_bi_interest 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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My Next Meeting with Master part 1

One day I received a text message from my Master, who had asked if I would be free in a week and half time, I text back to say yea I would be free and then he said good and asked if I would be free for at least two days. I replayed saying yes I would be free. So we had arranged to meet at his place at 830pm. He asked that I would bring with me the straight jacket, all my hoods, mitts, collar, whip and brand new padlocks that were still in a sealed case for him to open when I get there. Also that I need to wear my mini dress that is wet look and boots.
I could not wait for this day to come as ... Continue»
Posted by dallasrose 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  3

Chubby legal male hooker

I guess one day somebody figured out that if it was legal to pay people to make porn, but not just to have sex, that the easiest way to 'legalize' prostitution was to have a camera running or take at least one picture at some point during the act. Since I am interested in all sorts of men this seemed like an idea with potential.

I started posting on all the free bulletin boards about my new 'business', Versatile Services. Catering to discerning gentlemen it would provide playful companionship and diligent attention. How do you like it? Perverted married guy who likes 69ing with chubby m... Continue»
Posted by cumquarts 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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Made me a woman pt.1: intro (the first load)

My entire body is hairless now. Just finished shaving my long thick milky white legs. My toenails are painted black. My nails as well. I just shampooed my hair after dying blind for the first time. I had long hair, been growing it for over a year. It's below my shoulders, but now it's bleached blonde. Bimbo hair. It goes well with my green eyes. I admire them as I finish applying the whorish dark eyeliner and giving it that smokey eye look. Applying concealer, 3 different shades and contouring to leave no trace of a shadow after a close clean shave. Finally, the red slut lipstick. I look at ... Continue»
Posted by alexismorel 1 year ago  |  Categories: Interracial Sex, Shemales  |  
  |  8

Dinner for Two

Dinner for Two

What can I say? My girlfriend and I have a gratuitous and fortunate sex life. Above all I am honest with her and she is with me, so when I told her I wanted to be dressed like a two bit whore and fucked with the largest "strap on" she would dare use, I was scared she would leave me. Instead we went shopping. The saleswoman at Victoria Secret must have wondered why we were buying the same thing in two different sizes. And as I looked back while my girlfriend was paying I noticed them both look me up and down and smile.

As time passed, my kinks became mo... Continue»
Posted by keripinkpanty 1 year ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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