Shemales Porn Stories
Page 73

Job Interview with an e****t Service

On my 18th birthday, I had a job interview with a local e****t service. It was actually my 16th birthday but I had managed to get a fake ID ;-) I had a female cousin that was e****ting for this service and when she told them that she had a crossdressing bisexual male cousin, they wanted to meet me!

I showed up to the interview completely in drag: black stockings, garter belt, stiletto heels, black miniskirt, red blouse, wig, face painted like a fucking whore! It wasn't long into the interview when I was informed that the job would involve getting naked with mostly male clients and asked ... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 2211  |  
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him again :)

Since my roommate has moved out Ive taken it upon myself to begin exploring my Transgender tendencies. I shaved my legs, cock, chest everything. As I walked through work the first day, just feeling my jeans against my smooth shaven skin was a huge turn on, I felt my little sissy clit getting harder and harder as the day went on, tugging my panties tighter and tighter against my little bitty pussy ass, as they get stretched out. Its so erotic knowing that I am such a slut, that underneath my dirty grungy work clothes is a sexy soft girly sissy begging to be abused by cocks. mmmm. Spending all d... Continue»
Posted by Chubby_Decatur_Sissy 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1128  |  
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Summers of Love (Part 1)



A couple of weeks ago my wife hosted an Ann Summers party. I had hoped to sneak away for the evening as, though I would have been more than interested in the lingerie on display, I didn't fancy listening to the constant cackling common to "women only" parties and also the inevitable anti-partner jibes such as: "I ask are you in yet and he says I'm finished", "he picks his nose and farts afterwards" and "you'd think he was rodding a drain the way he goes about it" etc. The wife had other ideas however and I was drafted in to prepare the nibbles, pour the drinks and answer the door, the latt... Continue»
Posted by MichaelaCD 3 years ago  |  Categories: Shemales  |  Views: 972  |  
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becoming Rachel

I was about 15 when i found a bounty of porn magazines and female lingerie in the park near my parents house. Without thinking at all i grabbed it and took it home. that night after getting horny reading some of the porn magazines I tried on some of the stockings and silky lingerie. it was the sexiest feeling i had ever felt. they seemed like a natural fit for me, as i had a slim and somewhat girlish figure.

Over the next few months i regularly played with myself while dressed up and reading the mags. but after a while, without the magazines, imagining I was a girl, with my legs spread wi... Continue»
Posted by rachel_cd 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3644  |  
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t gurl at the bus stop

The radio was loud and the top was down when I first saw her.
She looked so beautiful sitting there at the bus stop.I remember her legs, they were long and tan and clad in silky smooth thigh highs. Her skirt shifted when she crossed her legs and I could see the garters clinging to her tan skin. She turned her head and smiled at me while I waited for the light. Her eyes were so bright. I think they were green, maybe blue. Every movement she made seemed to beckon me. As if she was calling me to her.

I couldn't help but stare at her tits - they were fabulous. A car behind me honked. shatterin... Continue»
Posted by allflavors 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 2362  |  
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school teen gay crossdresser first time sex

A young cross dresser's first gay experience
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my new bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I w... Continue»
Posted by allisontranny 16 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4401  |  
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Business Trip

My boss had sent me to Brighton at short notice as she decided at the last minute that she didn’t want to go. Apparently she had something better to do. The fact that it was my birthday didn’t seem to bother her too much. I usually liked the chance to get away for a couple of days as I’d sneak in some of the wife’s sexier things in my bags and spend my evenings in my room all dressed up and nowhere to go. But this time I would be missing out on spending quality time with Suzy. We’d only been married three years so we still made the effort when it came to birthdays. I had thought of bringing Su... Continue»
Posted by annav 7 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 4473  |  
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He has made me the town slut

We live in a very very small town, and now I am the town slut. This is the story of how my obsession with one mans cock turned me into the town slut.
I had been sneaking over to see Phillip every chance I could after he had fucked me and let me suck him. I couldn't get enough of his cock. I tried to see him at least once a week. I would usually blow him, but sometimes he would have the time to fuck me good and hard. I get off work hours before my wife and Phillips wife works later so this gives me time after work to dress up and head over to their house for some sissy fun.
One part... Continue»
Posted by firstknightd 1 year ago  |  Categories: Group Sex, Shemales  |  Views: 3132  |  
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First time...part 2

After lying on the bed for some time enjoying the wonderful ass I had just had she went to refill our drinks. The rum and coke had been flowing at this point and she felt that I was ready for her. As I was lying on the bed I noticed her get on her knees next to and to my surprise her hard cock was now 3 inches from my mouth. She didn't say a word, she just began to tease my lips with it. Having not had a cock in my mouth before, I was unsure what to do although heated in the moment I gave it my best.

I took her hard cock in my mouth and began to suck it while stroking it. From what I c... Continue»
Posted by tom69su 2 years ago  |  Categories: First Time, Shemales  |  Views: 800  |  
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Nancy finds out...

However, Nancy’s stay with us that summer was going to prove even more eventful than ever I could have imagined. Even after having been caught wearing her things by the neighbour’s son, Lesley, which led to a whole new dimension in our friendship, as you’ll know if you’ve read “Caught in the Act…”

Once again I found myself alone in the house. Dad was at work and Mom had gone to her Bridge Club and wouldn’t be back for ages. As you’ll know if you’ve read “Caught in the Act…” Nancy was really hot stuff and didn’t care who knew it. At 18 she’s a couple of years older than me, in the full bloom... Continue»
Posted by caroletv31 3 years ago  |  Categories: Lesbian Sex, Masturbation, Shemales  |  Views: 1778  |  
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Tranny and Me Meet The MILF

This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the weekend at my place. She said that was a great idea and that she would be over in a few hours. When Chandra got to my place she was horney as hell. She dropped her overnight bag, dropped to her knees and opened my pants. She pulled out my cock and began to suck it really good. She was licking my balls, ... Continue»
Posted by adw276 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1788  |  
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Cruising and Swinging 3

Blackmailed
It was about an hour after dawn on the third day of our Mediterranean cruise. I’d left my wife Melissa, asl**p with our neighbour Roger in his cabin. We’d spent the previous day fucking with Roger in the ship’s sauna and in his port-side cabin. I awoke to watch Roger and Mel making love, but once they went back to sl**p I was wide awake and slipped out to go for a swim.
I had swum about half a mile and was looking forward to the rest of the day as I walked back to our cabin. When I got there, our Brazilian maid, Maria, approached me looking concerned.
“Meester Jac... Continue»
Posted by lankybacon 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2568  |  
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Chatroom trick

I couldn’t believe I was doing this, as I stood by her front door I struggle to find breath on a surprisingly clear day. It had started some months ago, and internet chatroom, boy those things can be dangerous. I had spoke to Mary almost every night, soon chats turned to sex then to fantasies. The difference was she only lived in the next town so when she asked to meet I jumped at the idea, she was so sexy in her pictures. Admittedly Mary was 41 and I was 26, but still. She stood at 5ft10, long straight red hair, a body most twenty one year old girls would be jealous of. Stunning was the word.... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1342  |  
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The trannt from work

I've always had a thing about trannies. Just something. Never sure what or why. I loved looking at them. Seeing their huge tits. Their nice asses. Then seeing a dick between their legs. Now I'm not gay but, was always interseted. I would look up e****ts here in town just to see how far I would go. Finally one day, I got the nerve to do it.

Her name was Angelina. She was about 5'4". Say 125 with some hugh tits. Say 38 D or so. I had seen her where I worked. Would of never thought she was a tranny. Just always saw this hot chick with a huge rack & a hot ass. Everytime she came in the store, p... Continue»
Posted by radec_24 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2655  |  
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ALL MY SINS REMEMBER'D part 3

After numerous flutes of wine Kathy Lee was becoming very vocal despite Hoda's vain attempts to silence her proved to be. The only think that silenced her was when she was sucking my cock. She held it in her hands and then cast glance over at Hoda and a mischievious smile smile across her face.
"Reminds of that visit to the farm," she said. "Remember, Hoda. The stables?"
Hoda's face tightened and reddened and she gave Kathy Lee a solid punch on the arm and pushed her head downward and filled her mouth with my engorged prick. She cast a nervous glance over at me, which I responded with an... Continue»
Posted by slappywag64 2 years ago  |  Categories: Celebrities, Sex Humor, Shemales  |  Views: 463  |  
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Workout

Several times a week I go to the health club for a mild workout. I often see a guy named Mike. We chat as we workout. Now I am a secret TS so I'm totally clean shaven but also lots of guys who are into working out are also. Anyhow Mike is a real hunk! As most guys do Mike will make an occasional joke about the size of his penis. The bulge I secretely glance at looks pretty good but real size hard to tell. So last week we were done together so we were showering & boy was he right about the size of his cock. So he caught me looking & said "see told you it is pretty big". I said "yes it ... Continue»
Posted by nyloned1 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4910  |  
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MY GIRLFRIEND HAS A PENIS???

I met Gina at a club she was by herself at the bar and when I looked at her I was smitten I knows that sounds cliche but it was like that for me! I sat down a few seats down and ordered a drink a whiskey sour I believe it was took a few pulls to get up my courage then I offered to buy her a drink and she looked over at me with these incredible sea green eyes and actually smiled at me "Ok " she said and ordered white wine which she sipped so sexily I asked her if I could sit beside her and she patted the seat next to her I couldn't believe my good luck to find such a babe here and she likes ... Continue»
Posted by laceysgirl 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 4104  |  
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first time crossdressing exp

well this hapened a few years back,ive always been into wearing lacy underwear etc so i put an add in for anther knicker wearer for fun in an adult contact site,and was amazed at the replys,anyway i met a guy and we got on so we arranged a meet later that week at his house,i got there had a couple of drinks as it was our first bi experience, so he went upstairs to get changed and i got changed downstairs i put on black see through lacy knickers sockings and matching bra and mini skirt white blouse and a wig,dave came down wearing a very sexy outfit which was similar to mine also complete with ... Continue»
Posted by mumlover1960 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 873  |  
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Charlotte and her sister go swimming

I did not write this story.

I am 18, I have a younger sibling who is 2 years younger than me called Emily. Even though she is younger than me and we both come from the same parents, she has a better body than me. She is curvy, taller than me, wider hips, small waist, amazing big round ass and huge tits. I'm a D but she is an E, almost F. She turns me on a lot, I know it's wrong but I get horny thinking of her naked.

We both love our swimming. Even though this is an awkward sport for me as I am tiny and it is hard for me to hide a big 8 inch cock. I usually tuck it between my legs pushing... Continue»
Posted by drew1207 3 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 4577  |  
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A Special Girl - Birth of a Special Girl

A Special Girl - Chapter 1

By Alhana Escher

Birth of a Special Girl


James’ world had been turned upside down. Just moments before he had been getting off with, in his opinion, the cutest and sexiest girl in school. Now though, his was totally freaked out sitting on his living room floor having just discovered his girlfriend Alice wasn’t actually a girl at all. He had found out when his hand, that had been slowly making it’s way up her legs underneath her dress had reached the silkiness of her knickers to find a unexpected surprise waiting within. A small, but definitely hard ... Continue»
Posted by AlhanaCD 2 years ago  |  Categories: Shemales, Taboo  |  Views: 2321  |  
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