Shemales Porn Stories
Page 17

New Rapper & Femme Bottom

Lachelle Green hung up the phone with the video producer and checked her youngest two c***dren’s math homework. The woman in her early 30s was not only a single mom & homeschool teacher, but she was also the manager for her oldest son’s increasingly successful rap career and a powerhouse negotiator. She had her first when she was s*******n. While most would have written her off, she went about arranging for daycare provided by her grandmother and graduating as her high school class’s salutatorian. From there, she had a full ride scholarship to Cal State – Fresno and obtained a degree in busine... Continue»
Posted by faggyboi 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Mature Extreme Tranny Prostitute Part 2

"Yes, but I'm not messing about. If you would like to come then follow me now. I will explain what will happen when we get outside. "
The folder was quickly passed around the five of them, each of them looking at each other- silently asking - should we or shouldn't we?
Dave stood by his car knowing that at least some of them would come.
Eventually, one by one they emerged and started to walk over to Daves car.
I moved the sofa into the centre of the room. It was now facing directly away from the entrance door to my front room. Just as Dave had requested. Everything was in position, I j... Continue»
Posted by SexyTinaTV 5 months ago  |  Categories: Anal, Shemales, Taboo  |  
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My beginning

I have been a closet cross dresser since my early teens seeking my mother's panty hose and underwear I thought I had kept it well hidden when I turned twenty I got a place of my own I found it very hard to get my women's clothing since I didn't have the courage to go out in public which brings me to my story . a friend of moms named Sherri was bag ng problems with her old man and they had spot up she came to me and asked if she could move in and help with the rent I was all for it Sherri wes a tall red head very pretty and we'll built a couple of weeks went by she was gone one evening a pair o... Continue»
Posted by mike63bear 5 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Tranny Surprise Part 2

Things were off to a good start with Dani. We have been texting each other throughout the week just talking and setting up another date. We decided to go to the local fair I picked her up around 530 and she wasnt quite ready yet so she let me in hugged me and went back to finish her hair. I sat on the couch and played with her cats for a minute, she was back in no time and she looked great!

"Wow Dani you look really pretty in that sun dress." I said. "Thank you" she replied with a big smile.
We got to the fair and we went in we wa... Continue»
Posted by Entities 5 months ago  |  Categories: Shemales  |  
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I Knew I Was A Sissy (Part II)

For the next months I kept serving Nick at his will, usually every Saturday morning. It was convenient as his parents would go at the Super Market for shopping and I could use studying as an excuse.
We would meet at his place (not the garage anymore but his room) and I would give him a blowjob and let him fuck me. He kept his part of the deal (not spreading the news about me) and I kept mine.
I was enjoying it to be honest. At the same time on every chance I would go over my s****r’s room and “borrow” some of her thongs and stockings and dress up. My cock was getting hard every single time... Continue»
Posted by georgette32hk 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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My first time. Please excuse the grammar.

The phone rang out it's message tone, shrill but welcoming at the same time. I picked it up and looked at it. It was from him. I thought about ignoring it, my nerves getting the better of me at last, as I was a nervous wreck about this whole adventure.
Several weeks ago I had met a man who suggested that I should sell my body for much needed cash. I laughed at first but the seed of the thought grew with every passing day. Should I do it? Well, I put an advert in a website specializing in e****ts from all walks of life. Shit! What was I thinking? My advert wasn't very good and I hoped nothing... Continue»
Posted by ambu99977 5 months ago  |  Categories: Anal, First Time, Shemales  |  
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Confessions of a tgirl slut


When the day started, I had no dates, no arrangements of any kind. But I was feeling horny. I needed cock. I'd gone over a week without sex and I am one cock hungry sissy slut. I'm getting on a bit but I know how to dress and do my makeup. I like to think I can embody a straight guy's fantasies and give him the sex his wife won't and dress in a way genetic women generally can't be bothered to do. So I never wear tights - always seamed stockings, generally with a Cuban heel. I'm also crazy about garter belts with multiple straps, the more, the better. Heels - no less than six inches. A corset... Continue»
Posted by NancyBerlin 5 months ago  |  Categories: BDSM, Mature, 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 5 months ago  |  Categories: First Time, Lesbian Sex, 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 5 months ago  |  Categories: Lesbian Sex, 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 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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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 5 months ago  |  Categories: Gay Male, Mature, Shemales  |  
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I Knew I Was A Sissy (Part 1)

I was on my early teens when I saw my first porn movie. It happened during a weekend, one Saturday afternoon. All the boys gathered at the house of one of our friends as his parents were to be away for several hours to attend a wedding. One of the bravest of the “gang” had managed to get a porn movie and we were all excited.
Movie was inserted on VCR (yes, I am that old) and the action started. Everybody was commenting on the gorgeous girls and after a few minutes (possibly seconds) we were all erected. It didn’t took long before everyone started to jerk off. Ten erected teens seeing porn fo... Continue»
Posted by georgette32hk 5 months ago  |  Categories: First Time, 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 5 months ago  |  Categories: Anal, Shemales, Taboo  |  
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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 5 months ago  |  Categories: BDSM, Gay Male, 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 5 months ago  |  Categories: Anal, 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 5 months ago  |  Categories: Lesbian Sex, Shemales  |  
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Returning Home

Jeffrey Powell could not believe he caught the football. His teammates urged him to move. “Run,” they shouted. “The other way, dummy,” they corrected his misguided footsteps. He did as he was told he ran as fast as he could towards the trash can that marked the goal line. He was only a few inches away, at least in his mind, when Corbin Stewart lunged at him from behind. Jeffrey went down hard as the guy who was three-and-a-half years older fell on top of him.

“Mane, come on! This ‘posed to be touch and you tacklin’ folks,” complained one of Jeffrey’s teammates.
“Yeah, nigga,” another sneer... Continue»
Posted by faggyboi 6 months ago  |  Categories: Anal, Gay Male, 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 6 months ago  |  Categories: Gay Male, Mature, Shemales  |  
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Summer transformation Part 1

My jaw hit the floor as I read the first email I ever received from John. My mind twisted, heart raised, and my pussy pulsed repeatedly.

A week earlier I had posted an ad on craigslist... One of those late night d***ken fantasy ads where you spill your darkest desires, wake up the next morning and think "wow... I really am a pervert!" My ad was placed M4M, M4MM, M4MW, and T4M. I wrote:

" 18 year old looking to experiment. 5'5", 170, naturally smooth. School is out so I have lots of free time, super horny all the time, looking to learn. Discretion is a must, can`t host, love mature ... Continue»
Posted by archerfan88 6 months ago  |  Categories: First Time, Shemales, Taboo  |  
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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 6 months ago  |  Categories: Fetish, Sex Humor, Shemales  |  
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