Shemales Porn Stories
Page 73

Daddy's Popper Challenge

Since I've been enjoying the users’ stories here so much I thought I'd share one.
I'm a pretty good looking guy, love girls and pussy, but I am a closet tranny chasers. I love hooking up with crossdressers and transgender. I dressed a little in high school and college; I left behind the clothes but not the lust for the femme bois.

Last week when work was tough I needed a five minute distraction to clear my head so I called up Craigslist and browsed the Casual Encounters T4M. This was around 2:00 in the afternoon, a very hit and miss time. The ad that peaked my interest was "Mature Crossd... Continue»
Posted by gypsy61 2 years ago  |  Categories: Mature, Shemales  |  
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The Developing of Emma Part Four

Emma awoke in the softness of her silk sheets and wondered what the day would bring; her sissy cock bulged and dribbled sticky pre-cum through the outlet of her cage as she thought of sucking Kurt’s cock; her tight little anus clenched and released at the plug, which acted like a comforter. Elaine was right, Emma was beginning to enjoy the plug and as she tried to rub her confined cock, she imagined the plug to be Kurt’s cock; how she wanted to cum! The blue pill she had been given would keep her little cock hard in the cage and make her yearn to orgasm. This would make her extra obedient a... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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First Public Experience

From my previous stories you’ll know I love to dress up in lingerie. After a small number of sexual encounters with men I decided it was time to take things to the next level. I told a lesbian friend of my cross-dressing and asked her to take me to a gay nightclub dressed as lady. I didn’t want to go on my own. She seemed surprised but agreed. All week I wondered what to wear. By Friday I settled on a skin tight white dress with matching high-heel shoes. I spent the previous evening waxing and plunking my eye brows. I wanted to be as feminine as possible. Friday evening i began to get ready. I... Continue»
Posted by monkeynuts0 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Panty Boys

By Fred Gingerman

Chapter One - Nerds United
My name is Mickey Donaldson. For most of my 16 years, the k**s have called me Mickey Mouse, because of my size and because of my shyness. I was only 5'3" and at 115 pounds, very skinny. My best friend Jeremy Haskins and I were always the oddballs. Jeremy was a little bigger at 5'4" and 120, but we weren't being recruited for our high school football team. Chess team was more like it.
We were pretty much classic nerds. Shy. Picked on. Ostracized. Intelligent.
But we were still 16-year-old boys and our hormones were stirring. Boiling actually. ... Continue»
Posted by BeeJay69 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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My highschool girlfriend 2

It had been a week and me and my girlfriend had not done anything else, but ofcourse we talked about it. Her mostly, saying "I was so sure you were so strait, im so happy your okay with my cock" all I would say was "I was so sure I was strait too, but being with you, just changed that I guess but I love it, you make me hornier than a girl with a vagina ever could." She also brought up another point, that the anal can go both ways, and ask if she could be on top next time. I was kinda scared it would hurt, but thought it may be fun, and told her that and she said she would make it painless, by ... Continue»
Posted by suckmedry69 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Shemale Whore and Arab Pimp

HERMAPHRODITE WHORE

It had been over a year since Johnny threw that tantrum that
ruined me and got him excommunicated from mom.

Holding me down when mom walked through the door with
her friends, colleagues, whatever and they all gasped and
screamed as my big b*****r finished doing me.
We had ample warning, we could have all vanished when
we heard them at the door.
Bobby ran away and got dressed. The chickenshit
denied any knowledge of the event.
Smart but chickenshit.

Mom severed all ties between me and our doctor's
little perv ring, so I had no more money coming in.
I di
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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She wanted to Watch!

Everyone knows I'm bi and a Transvestite. I don't dress as much as I wish but I do go out two or three times a week. When I'm not dressed up I tend to hang at a straight redneck bar thats about two blocks from my house. They all know both mark and Kristy there and most are nice to me and respect me because of the respect I give to them.

Well yesterday I was in after work for a couple beers and Cindy the bartender and Lisa wanted me to do some drinks with them. Orange Crushes, wow I didn't want to get d***k cause I had plans for Kristy to go out clubbing. But after encou... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  
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How I became a sissy

So it all started from answering a random craigslist posting that didn't even have a picture. I was off work and horny so I was cruising the ads and I came across a Cross dressing married dom and his wife looking for a sub. I was no stranger to the lifestyle and it intrigued me so I began to write an email. We exchanged back and forth for several weeks and then began talking on the phone. The day had come and they invited me over. I was nervous. I am a married guy. My wife knows all about my past experiences but had no knowledge of this relationship. I got my things together and put them in a ... Continue»
Posted by tg2027 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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My First Gangbang

For as long as I can remember, I have always enjoyed wearing women's clothing. When I was in fifth grade, I started wearing pantyhose under my pants during the winter. By the time I was going into the seventh grade, I had learned that, not only did I enjoy wearing pantyhose, I also liked playing with peckers too ;-)

As you may imagine, I became VERY popular! Pretty soon, there wasn't a sl**pover in the neighborhood that I wasn't invited to ;-)

I quickly developed what would be a lifelong obsession: semen. And no matter how much I got, I still wanted more! The feel of it squirting into my... Continue»
Posted by cdsexslut 3 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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my fun at the glory hole

without any girl outfits still ive always been sad that i cant go out as Ana and find some nice boy or girl to go home with and have them fuck me.. but today i found somewhere that had a glory hole near by..i was so excited to hear this because i could do everything i loved to do before.. i arrived around 8 seeking in and once i was in the room it wasn't long before i heard someone next door.. i was so nervous to say the least.. i hadn't had sex or sucked dick for three years could i do all the things i did before as well as i use to.. well anyways i heard someone walk into the room next to me... Continue»
Posted by drewcd 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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SISSIES TRAINING PART 1

SissyIndy©

I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often moving the same piece of furniture to what seemed like the same place it was originally. Finally he decided he liked the new arrangement, which wasn't that drastically different than how it looked when we started. Obviously exhausted, I sat down on the couch. He asked me if I'd like a Ga... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Chrissie Learns A Harsh Lesson The Conclusion

Chrissie Learns A Harsh Lesson (The Conclusion)

My arms were stretched straight up over my head, metal handcuffs circled my wrists and were tied to a metal ring that
had been embedded in the ceiling. The rope which was hoisting me up left me suspended from the ceiling in such a manner
that only the toes of my black 4 inch heels touched the floor. The hard metal of the handcuffs cut into the skin of my wrists and
a burning ache traveled through the muscles in my arms and shoulders. I felt totally helpless, totally vulnerable and yet
strangely aroused.
Standing ten feet... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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How I Became Vanessa Chapter 2

Hello dear readers,

I strongly encourage you to read the first chapter of this story to fully grasp the sudden changes which affected my life.

I dressed up with a very tight black long sleeves top and a black mini-skirt. I added a choker necklace like the one Elena used to wear. I chose a pair of black fence net thigh highs to show my beautiful legs and stiletto high heels. I also chose to wear my shorter blonde wig (jaw-length) and some heavy make up.

I didn't know I wasn't alone. I was starting to prepare my ass with some lubricant and to squeeze my big black dildo in when Elena cam... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Shemales  |  
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She tricked me & am I glad

My most frequent fantasy is to be dressed like a slut for black men. I think about it at least 3 times a day. The most recurring fantasy is when I meet this black woman that turns me on. We talk for awhile and it seems like we are hitting it off pretty good. Then out of the blue she asks me if I want to continue this conversation at her place. Could I be this lucky? This fine black woman was inviting me to her house? Yes I told her smiling from ear to ear. She smiled back and told me to follow her. We get to her house and she tells me to have a seat while she gets more comfortable. I am sittin... Continue»
Posted by iwannabeacumslut 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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Can i help you with that?

Yes being a shemale does present itself with certain unique situations for time to time, none so unique as the other day, in fact, when at the mall, i had to piss so bad, so i went into the ladies room, of course, dressed in a blouse and tight jeans. I found an empty stall, wnt in but had to go so bad, and you know what i mean, you lose track of all else, thus i left the stall door open, well it all worked out for the better! I was standing up and pissing when this hot MILF opens the door, sees my cock in my hand and asks me if i need any help! Help? I knew what she wanted so i asked her in an... Continue»
Posted by cumsquirter 4 years ago  |  Categories: Shemales  |  
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A Fantasy

For leannaxtsx

During the flight he had a hard time falling asl**p. He kept all her posted pics in his phone and went a few times to jerk off in the bathroom while looking at her body. When he found out he was about to go to a convention for 3 days and as it happens to be the convention was at New Orleans he arranged to stay for a few more days "to see the sites". Now he was on his way and he knew he had to wait for 3 days until he could meet her. He contacted her a week before, at first she wasn't very cooperative but he managed to convince her they should meet. He promised to... Continue»
Posted by mobi_dick 2 years ago  |  Categories: First Time, Shemales  |  
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the real me part three

Just then the phone rang and mom handed to me it was Mike he said that he couldn't belive it was me he seen at the store.I told him yes it was,then asked if he wanted to still be friends.He asked well you going to dress like that always now?I said well do you like the new real me,he said well I love the new you.Mike told me how he got hard thinking about me that way.Well what your mom say i asked. He said it was up to us what we wanted to do.I asked did your mom say anything to you about her and my mom being lesbain lovers? Yea she did he said, ok then we are cool with them.
He then asked m... Continue»
Posted by cdpaula 3 years ago  |  Categories: Gay Male, Shemales, Taboo  |  
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A true story: me and a transvestite man - part 3

This is the last part of my true story. I had expected it only to need two parts, but it seems that I'm quite a wordy writer, so it now spans 3 parts.

Where did I leave off last time? Oh yes; Toni, the gorgeous Brazilian TV was leaning forwards, dressed in her black lingerie, her firm arse towards me, ready for me to enter her. Read on...

I wasn't expecting this to go well, as I'd only had a little anal sex before, with a woman, and this had been on a bed, where I could jockey around for best position. However, thanks to my extra height (6'3" against Toni's 5'10" or so) we seemed a p... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Willows transformation 2

"Now the preliminaries are over, and it's time for the entertainment part of our evening!"

That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation.

Fern had found a magazine I'd left on the bedroom floor, showing a transvestite being tortured and humiliated by a couple. Although she had always known I liked to crossdress, she had never paid any attention to that side of me. Now she had ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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becoming Rachel 2 - A night out at a fetish party

So I had been Rogers trans-mistress for about 2 years. as he was also a p/t Tranny he had taken me on as his little teen (19 year old) apprentice tranny.

he was in his mid-40's, he taught me how to walk, how to sit, how to talk, how to suck cock and deepthroat, how to fuck. lately he had me taking some estrogen tablets which had made my skin softer, changed my voice and given me little cheery nipples. I liked all these changes and Roger told me that we would eb going to a 'party' i was very excited by this, as I hadnt been out dressed much and really liked it when I did. Roger bought me a h... Continue»
Posted by rachel_cd 2 years ago  |  Categories: BDSM, Group Sex, Shemales  |  
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