Shemales Porn Stories
Page 74

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 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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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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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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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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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 3 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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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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My CD friend

This story is fiction.

~~~~~~~~~~~~~~~~~~~~~~~

I had been chatting to people on a ts chat room as I had recently become accustomed to do, when I received a private message from a local cross dresser. She asked me where I was from, how old I was etc and we found out we lived a few towns away from each other, both young guys and both really loved wearing women's clothes.

Admittedly she was much more experienced at it than me, having access to girlfriends, s****rs and mothers clothes and had even ventured out fully dressed once!

Eventually after some light chat, swapping dressing up s... Continue»
Posted by shyadam89 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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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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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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The Bondage Whore, Chapter 6

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.



Chapter 6 - A Visit from Randy


"Randy!"

Rachel was thrilled to see her friend and old streetwalking regular from days past, step around the stock. He immediately popped out the gag, and gave Rachel a friendly kiss. Rachel melted.

"So glad to see you Randy! Although I feel a little embarrassed to have you see me like this."

"Hey sweetie, c'mon, I know what you do. And I must say, WOW, what a view." Randy took a step back and around the stock, enjoying and taking in the entire picture. "Yup, wow! Don't know quite ... Continue»
Posted by thongcutoffs 4 years ago  |  Categories: BDSM, Fetish, 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 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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late night hotel halls

I am 46 years old and travel quite extensively for
businss. I dress in my hotel room at night when i travel.
I sometimes entertain in my room. Sometimes I get very bold and wander out to the soda machine dressed sexily. Its about as bold as I ever get. I am quite tall and do not pass in public. But i am very smoooth and try very hard to look fem.

Anyway, very recently i wandered into the hotel halls about 3 am at a business hotel I was staying in outside of
Indianapolis. The soda machine was at the end of the
hallway. I looked up and down and when i thought the coast was clear I... Continue»
Posted by cherylfabrizio 3 years ago  |  Categories: Shemales  |  
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Caught in the act

After my first encounter with John’s dick, I couldn’t get it out of my mind. Two weeks later we met at a friend’s party and we talked about it. He was worried his girl friend might find out. I told him he had noting to worry about as I had as much to lose as he had. But I also said it was the best sex I ever had & wanted a repeat performance. He agreed it was fun but felt to do it again would be risky. I said all we needed was an excuse to go away for the weekend. I told him to leave it to me.

I happen to mention to his girlfriend later that John & I were thinking of going away to see a ba... Continue»
Posted by monkeynuts0 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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My New Whore

Disclaimer: All characters portrayed are over the age of 18. Any similarities between persons living or dead is entirely coincidental and unintentional. These characters are entirely of my own creation, and thus don't belong to you. Don't use them or this story for your own purposes. There's a reason they belong to me.

Justin's body trembled, as he sat in his chair, his eyes glued to the floor. It was obvious from his reaction that he hadn't expected me, or anybody for that matter, to walk into his apartment that night. We had been friends for several years now, and though it ... Continue»
Posted by BigStevieAwesome 4 years ago  |  Categories: Anal, Shemales  |  
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My first time with a shemale(True Story)

This is a true story about my first experience with a shemale.

I was sitting around the house the other day horny as fuck. My usual girl that i call on when i get that way had f****y in town for christmas so she couldn't meet me. So i decided that i would look on craigslist and see if i couldn't find someone that wanted to fuck as much as i did. As i was looking through the ads and as usual not finding any women that were real on there i clicked on the T4M section. I had always been a bit curious about being with a shemale and decided that i would respond to a couple of the ads. The fir... Continue»
Posted by wild_wolf_03 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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