Shemales Porn Stories
Page 69

I Knew Her Secret

I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. Her name was Marla. Obviously, she wore the whole postal get-up with the blue shorter than usual shorts on a daily basis. Usually the post ladies when they wore shorts they would come to the knee, Marla’s came to the mid thigh and were very tight and revealing. She was African-American and had sugar brown... Continue»
Posted by 1234spence 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 2497  |  
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Last night I drank my own cum

Once upon a time...

There was a regular boy, who was always fascinated by women, but one day (casually) discovered the dirty and horny world of the "third way" of sex, the fantastic shemale-ladyboy-tranny universe, and it was like a shock for him, a very sweet shock, he never believed or thought in exciting himself by watching a girl with a cock, but instead that new world electrified him, and made himself very curious about these she-males, widening his love above women and becoming a real sex pig and an orgasm addict.


Well, that regular boy was me. I consider myself as ... Continue»
Posted by Porcellone 3 years ago  |  Categories: Masturbation, Shemales  |  Views: 1663  |  
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A LadyBoy For My Wife

I have been happily married to my sexy Thai wife Lisa
for three years now. My wife is Thai is petite (5'1")
with a stunning figure, a tight ass and long waist
length black hair. We had met in a bar in Thailand and
subsequently we were married back here in the UK. She
was very loving with me but not very sexually
adventurous.

My attractive wife and I have sex often as we watch
porno movies. Often we role play and we fantasize about
my wife fucking other guys. Since my visit to Thailand I
often dreamed of a beautiful Thai Ladyboy chick joining
us for a fuck too.

When ... Continue»
Posted by sanpeesua 2 years ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 2585  |  
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How I became a GURL

So how did you become a gurl?

That's the question almost everyone I meet or chat with asks me... how did you become such a sexy transvestite, when did you figure it out, when did you learn you liked cock.

I actually love the question, because it turns me on to answer it.

When I was 15 or 16 I used to sneak into my parents room, find my dad's stash of Playboys and jack off to them. The girls were sooooo beauitful, I just couldn't believe it. I wanted to see and touch one, which led -- I guess this is common among us gurls -- to digging into my Mom's stuff.

When I was left alone I w... Continue»
Posted by jenn1 3 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  Views: 1863  |  
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getting panties

So, after my first time wearing panties I had to do it again and again. I only had the one pair that I had gotten fromn the neighbor girl and wanted more. When I saw her the next day she ask me what I had done with her panties, I had hand washed them in my bathroom sink and hid them to dry. I did not wear them again hopeing she would give me another pair. I told her I had forgotten all about them but since all of my boxers were in the laundry I did not have any underwear on. She blushed and said she would just have to loan me another pair of her panties. I think she just wanted to see me witho... Continue»
Posted by peggyacd 2 years ago  |  Categories: Masturbation, Shemales  |  Views: 1255  |  
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Caught!

Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed when this happened. But more and more I kept fantasizing about one of my male friends. He's very good looking and keeps in shape by jogging every day. Several of the times we've gone out boating him and I ended up skinny dipping, so I've got to see his cock several times and have secretly wished I could get him to screw Kristy. He's been divorced for about 5 years and doesn't go out much, and several times he's told me he hasn't been with a... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  Views: 3226  |  
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crossdressers first time

i first started to wear tights when i was 18,i was shocked when i first realised i loved tight panties and sheer tights. i was staying with my friends mother who was 65 at the time,she wore the sexiest lingerie i had ever seen,especially on a woman that age,but i felt drawn to the sheer stockings. the next day i was taking a bath when i noticed them on the wash basket,i had an urge to wear them,i was very shocked by this desire but had to!i slipped them on taking care not to rip them,they were hold ups and as soon as they were on my cock stood to attention like never before. to my horror my fr... Continue»
Posted by nylonfiona 4 years ago  |  Categories: Mature, Shemales  |  Views: 1016  |  
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Shemale snapped

(A story written by a friend) Hope you like it!

Camilla took a few steps out the door of her balcony to get a feel for the temperature. Thankfully it was cool out. It had been a hot day, which meant a cool night was welcomed.

She closed the door and pulled out a pair of gold hoop earrings. She was suffering from a mild case of the jitters. There was a date on the agenda tonight with a guy she'd been seeing for a couple months now. Camilla kicked a pair of high heels out of her closet while fastening the earrings.

A date was a big deal for Camilla. Even though she'd been out of schoo... Continue»
Posted by Ankakalle 2 years ago  |  Categories: Shemales  |  Views: 1031  |  
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What If My Mom Part 2

Peggy and Me

We all lay together for a while until Mom told us she had to get up, it was lunch time. We had not heard from Bobby or Dad and I was getting hungry. "You two just stay here, I will make some sandwiches. Back in a minute"

Just as Mom left Peggy rolled onto her side facing me, "That was so nice kissing your Mom.........., will you kiss me, down there?".

My feelings were still mixed up, but I did want to. I could show her what Mom had taught me. When I moved to get between her legs she stopped me. "No together, I want to suck your cock at the same time, you know".

Peggy p... Continue»
Posted by chchboy 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 3784  |  
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Cum drenched afternoon

I was anticipating Marla's return from her work related trip out of town for a week. She was due to arrive around four in the afternoon. I wanted to make sure I was ready, so I spent the day preparing myself. I took a long hot bubble bath and made sure I was completely shaved. I sprayed on body spray and applied my make up and fixed my hair. Next I picked out my outfit, tonight would be my catholic school girl uniform. It starts with my white satin crochless panties with rows of little pink ruffles on the back. Marla always likes it when we have our love sessions in panties, and the cro... Continue»
Posted by slipn2panties 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1484  |  
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f***ed feminisation


It all started as just a game. i logged into a f***ed feminization chat room and portrayed myself as a slave being punished by my Mistress. Saying She had instructed me to enter this room for 5 minutes and obey any command given to me. It seemed harmless and exciting. How stupid could i have been. Instantly i began getting messages for me to strip and show my ass and my face in various poses. There was one in particular who led the show. He f***ed me to put on lots of makeup and lingerie and pose myself as a sissy slut begging for cocks to serve. Everything was done on cam. i was naked sprea... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3034  |  
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Office Fun

ee had worked in the office for just over 6 months, and couldn’t stand the job. It was tedious data analysis type work which bored the hell out of him, and he had to do it eight hours a day, five days a week. The only thing that got him through his long days was Marcia. Marcia was a stunning woman who had started at the office about two weeks after Lee and worked at the station opposite him. Lee was wild with desire for her, and would be distracted for what seemed like hours at a time fantasising about the things he would do to her if he ever had the chance.

He watched her now from across h... Continue»
Posted by gellid 3 years ago  |  Categories: Shemales  |  Views: 746  |  
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A threesome to remember

After a few cocktails I was relaxed in the chair as I watched Annie unbutton Jeff's shirt and kiss his chest. Her ass was right in front of me as I watched her black nylon covered legs run up to her tight skirt that just covering her full ass. She knows how much I love tight skirts and nylons and for this special night she was dressed as a full on hot slut for the night. After three years together I had always fantasized in sharing her in a threesome. The sight of her lipstick stains on his chest, and hearing her light kisses across his body made my cock so hard. I knew Annie’s little cock mus... Continue»
Posted by Zeffer 3 years ago  |  Categories: Shemales  |  Views: 912  |  
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cumsquirter

Spent another night at my girlfriends house, she is straight, hot body, 32c tits, juicy shaved pussy, tight assole, great lips to suck my 7 inch shemale cock, which she likes to. I thought we were alone, sitting in the den when her uncle walks in, hot body and i always fantasied about sucking his cock and fucking him in the ass, but had to jackoff and cum instead. this time, he sits next to me and asked me if i like him, well, i said yes, but i had a surprise for him, at which time a took off my jeans and wet panties, and my 7 inch cock sprang out, so i stroked it for a while, until he decides... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 643  |  
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Beginnings

The Intimate Liaison
You would think being at home all day while the wife works would give me all the time in the world to indulge myself as Michaella but not so. Being a closet crossdresser with a f****y and home to look after is OK but a great number of friends and f****y call in knowing I’m at home and always good for a cup of coffee and a chat. Take this morning for instance my friend Steve phoned and warned me that he may be calling in on his way home from the town, but he did ask if I was busy. It is always good to see him, we go back a long way and even if I were busy I would always fi... Continue»
Posted by michaella_cd 3 years ago  |  Categories: Shemales  |  Views: 596  |  
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markie dunlap Kansas city sissy for all black Mast

I am a Sissy Faggot! I have been programed by hypnosis to write (beg) to be owned and femenized by a black Master in Kansas City Mo. For months I have watched repetedly sissy hypnoses videos and black cock worship videos. My girl freind set it all in play when she found me dressed in her panties bra and stockings. She has comanded me to tell all who read this that the phrase (black cock sissy) will in fact make me your sissy cock slave to dress me and use me as you wish. She has also instruced me to make it more intresting and let you know I live in Lees Summit and that Since I will not rememb... Continue»
Posted by markie2269 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1152  |  
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Leona'

Note: ——I am NOT the author!so plz Don't ask me about part two,am simply sharing

this lovely story with all of you because I have not seen it on here

I think of myself as resolutely straight. I look at a lot of porn although I have plenty of girls to fuck. Steven, an old college buddy, dropped by and proposed that we go to a shemale bar that night. I was shocked and refused. But Steven retorted that if I was sure about my sexuality, I should have no problems being there. I could just have a few drinks, take in the scenery, and after we left we could pick up a couple of hookers fo... Continue»
Posted by adel5000 3 years ago  |  Categories: Shemales  |  Views: 774  |  
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strap on gang bang....

Well hello boi's and gurl's,
Just had a evening of bliss and really wanted to tell the world...
I am tall, slim, sexy CD. Have been X dressing now for over a year.
Never new it but after attending a Halloween Wedding as a female I
was hooked...

I have had sexual experience with male's and couple's in my past,
and am very kinky too...
I also tend to be more submissive when dressed up.
Love to please others before myself type...

So I had set up a meeting with a very nice member of the military and
his wife.He was bi BBC, She was white and very dominant. Both where very sexy, and ... Continue»
Posted by dawncd1 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 993  |  
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Becoming Amy

Becoming Amy

By [user]Alhana Escher[/user]


I had been dressing up in women’s clothes since I was a k**. Started with my s****r’s clothes, I loved her school uniform. I used to prance around in it when I was lucky enough to have the house to myself, which wasn’t often. I loved pretending I was a school girl, and a rather naughty one at that. I’d pretend I was flirting to a guy, usually an older guy. I’d slip my hand up those pleated skirts and rub myself through her cotton knickers while imagining it was his hand until I was about ready to cum. I’d then dash to the toilet take my... Continue»
Posted by AlhanaCD 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 2174  |  
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Clara Bow's Academy For Would-Be Ladies: Part

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she’d also chosen for his first day. His stepmother had allowed his soft ginger hair to grow to shoulder length already, and his dosage of hormones had been already been increased. He had been suitably attired in a gingham dress with pink socks and red... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 966  |  
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