Shemales Porn Stories
Page 18

my little secret

Experimenting with girl clothes and cock. If you don't like it, don't read it. I always wanted to be a girl, or at least wear girls clothes. When I was ten I started acting upon it. I would occasionally steal some of my moms panties and wear them for a while. I thought the silky panties felt great as they rubbed on my ass and pressed on my little cock.
When I was thirteen, I took it a big step further. I had already been masturbating for months thinking about the time I could completely dress up in some of my moms slutty clothes she wore out with my stepdad.
One summer day, when I thought i... Continue»
Posted by ExampleUK 4 months ago  |  Categories: First Time, Shemales  |  Views: 2235  |  
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Discovering I Want to be a Girl

I'll never forget the first time I experienced being a girl.

I had been dating my girlfriend for some time, and she was very shy and quite sexually inhibited. I on the other hand was a raging deviant, and with time we had started to do more and more daring things.

Using toys was first. We bought her a 7 inch pink dildo, and watching her come as she laid on the bed was so horny. A beautiful redhead, with white skin and freckles, me watching her face as the cock slid in and out of her. Seeing her come was a treat. I got jealous, so it was my turn for a toy! I knew I liked having my ass f... Continue»
Posted by CD_CutieBoi 4 months ago  |  Categories: Shemales  |  Views: 1274  |  
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Dominant Female Teacher Makes Crossdresser Student

This is the second part of “Dominant Female Teacher Makes Cross dresser Student”. It explains why I am what I am.
I got called to see Miss Jones, the teacher in charge of discipline at my school.
"So you are back are you? What do you expect? Well you are wrong for I demand so much more. Understand me about that."
"Yes Miss Jones, I understand" I was back in her school office again. Again I was nervous and excited.
She put down the file and looked at me. "It’s not a game it’s for real"
I nodded.
Miss Jones, head of year, came from behind the desk, her black stilettoes tip tapping lik... Continue»
Posted by SapphireSomeday 4 months ago  |  Categories: BDSM, Shemales, Taboo  |  Views: 2298  |  
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THE TRAIN JOURNEY IN INDIA - PART I

Hi all

this is a true incident happened to me recently.

I had to go on a business trip to a small town in central India and there was no flights to the place so i booked a train ticket first class.

I had to take the train from New Delhi and be fore boarding i bought my self a nice bra with D cups a matching lace panty and thong, a pair of panty hose, transparent full length nighty with just a string to tie it in the front. I bought a cpl of packs of smokes and a bottle of whisky and got on the train. It was around 6 pm and as luck would dhave it i was alone in my compartment of the... Continue»
Posted by hornyboyind 4 months ago  |  Categories: Shemales  |  Views: 1476  |  
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THE TRAIN JOURNEY IN INDIA - PART I

Hi all

this is a true incident happened to me recently.

I had to go on a business trip to a small town in central India and there was no flights to the place so i booked a train ticket first class.

I had to take the train from New Delhi and be fore boarding i bought my self a nice bra with D cups a matching lace panty and thong, a pair of panty hose, transparent full length nighty with just a string to tie it in the front. I bought a cpl of packs of smokes and a bottle of whisky and got on the train. It was around 6 pm and as luck would dhave it i was alone in my compartment of the... Continue»
Posted by hornyboyind 4 months ago  |  Categories: Anal, Shemales  |  Views: 525  |  
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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 4 months ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 1048  |  
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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 4 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3528  |  
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Slave Life: Part 1

Prologue: My thick thighs quivered and shook as the man standing behind me, my Master, fucked my tight cunt into the bathroom wall. My loud moans filled the room as I shot a huge load all over my thighs and the floor. I had never been fucked like this before! I didn't care who heard my loud moans as they echoed across the tile filled bathroom, and I didn't care who heard the sound of my Master penetrating my ass with his enormous cock. Just then my Master moaned and shot his load deep into my tight, warm, and heavily fucked ass. When he had finished pumping his load into my ass, the warm and s... Continue»
Posted by Slave_Alice1389 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2784  |  
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Emo twink get 20 yrs hard time

So, here it is. The next 20 years of my life in California Institution for Men Correctional Facility, aka Chino State Pen. I had no idea what was to come, never the faintest idea. Personally I thought I would get killed within a week's time.

You see, I'm not really inmate material. I eventually did become one but not as you would think like into one big bulky muscled tattooed thug. Instead, when I first walked into prison I was a 19 year old, 5' 1", 130 lbs, fair skinned curly red haired Emo twink.

Now, what is a nice cute androgynous lace and fishnet wearing bi-sexual white boy Emo twin... Continue»
Posted by pat4tights 4 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 1471  |  
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Emo twink gets 20 years hard time

So, here it is. The next 20 years of my life in California Institution for Men Correctional Facility, aka Chino State Pen. I had no idea what was to come, never the faintest idea. Personally I thought I would get killed within a week's time.

You see, I'm not really inmate material. I eventually did become one but not as you would think like into one big bulky muscled tattooed thug. Instead, when I first walked into prison I was a 19 year old, 5' 1", 130 lbs, fair skinned curly red haired Emo twink.

Now, what is a nice cute androgynous lace and fishnet wearing bi-sexual white boy Emo twin... Continue»
Posted by pat4tights 4 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 1363  |  
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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 4 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3639  |  
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Busted

I know you're married and you have k**s and stuff, but sometimes I wish you didn't so that you and I could be together." I was speechless and unable to respond. "Do you ever think about me that way? I mean, what it would be like to be with me?"

"Yes," I finally admitted. "I do sometimes."

Jenny closed her eyes and lifted her face closer to mine. I knew I should push her away, tell her no, take her home and forget all of this had ever happened. But feeling this nubile teenager so close to me, knowing how badly she wanted me, I was powerless to do anything except close my eyes and lower my... Continue»
Posted by koolstuff 4 months ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 2861  |  
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Friends

Another story off the web. Enjoy

i have been friends with my next door neighbor for about 5 years now. he recently divorced his wife, but somehow managed to keep the house. So, we have been doing the bachelor thing together for the last few months... beer and cookouts on sundays while watching football, getting d***k, fixing cars, etc. my wife complains a little about this, but all in all, she puts up with it. she uses the weekends to visit her s****r (who is ill) and go out with the girls. i definitely make it up to her, above and beyond.

yesterday, our typical group of friends was una... Continue»
Posted by BeeJay69 4 months ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 1282  |  
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Will Work For Panties

Found these stories on the web. A bit of a long read, but if youre into panties, I'm sure you'll enjoy it.

Will Work for Panties Ch. 01
by Vincent E ©


Life is too short to go through it stupid and careless. I guess that you can be either one thing or the other and you will not inflict too much damage on yourself, but the combination of the two can prove tragic. For instance, if you are going to raid your aunt’s underwear hamper on a holiday visit – stupid – you should not leave the door to the bathroom unlocked – careless. Well, I learned first hand just how bad the combination of stu... Continue»
Posted by BeeJay69 4 months ago  |  Categories: Fetish, Shemales  |  Views: 1600  |  
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Fucked in a sling at an ABS

So there's a cruise place here in Canberra where mainly men go, it has a cinema and blowjob are downstairs and private rooms and some fetish rooms up top. Knowing of this place i decided to venture out all sexed up as Rachel.

At home I shaved and used hair removal cream to make my skinny body more feminine, then rubbed body lotion into my skin making me softer and sexier. My she cock is already half hard at this stage and I have a sissy trainer video on to remind me that I am a sissy slut who loves cock.

Clothes I wore a crotchless fishnet body stocking and a PVC teddy and gstring. I put... Continue»
Posted by rachel_cd 4 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 682  |  
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Would love a shemale like this !!

****d (sort of) by a Shemale!

I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon.

I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.

Her hair was dirty blond and loosely curled, and her face was quite beautiful. She w... Continue»
Posted by loverboydjinn 4 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1947  |  
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My first meeting with Henry - Story 2

Background: Me - Closet bi-crossdresser (Katie) - 48 yo 5'11" 185 fit; smooth all over; office manager. Quite passable except voice, sexy, attractive, submissive and horny. Only wear dresses, no jeans or skirts. Try to be a girly girl. Black lace thigh highs, red and black lace teddy, black lace panties, long auburn wig, black open toe heels, bright pink nails. Him (Henry) - 43yo construction worker 6'1" 195 toned 8 1/2" uncut muscular fat veiny cock groomed naked.

As Henry opened the door to his house, we said hi and I proceeded to walk away across the room, my short black dress, ... Continue»
Posted by hotcdsub 4 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 872  |  
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My first meeting with Henry - Story 1

Background: Me - Closet bi-crossdresser (Katie) - 48 yo 5'11" 185 fit; smooth all over; office manager. Quite passable except voice, sexy, attractive, submissive and horny. Only wear dresses, no jeans or skirts. Try to be a girly girl. Black lace thigh highs, red and black lace teddy, black lace panties, long auburn wig, black open toe heels, bright pink nails. Him (Henry) - 43yo construction worker 6'1" 195 toned 8 1/2" uncut muscular fat veiny cock groomed naked.

I met Henry while drinking in a local bar after work in late August. (I was dressed in normal work clothes since I on... Continue»
Posted by hotcdsub 4 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 790  |  
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Trip to LA

I was out in Los Angeles on business and as I would dress up every nite and see if there was anyone who wanted to play a bit. On Friday around 5 pm I decided to go all out and I dressed in a corset with garters, panties, bra, stockings, red heels and a black lace cocktail dress. I finished it off with a blond curly wig and some rhinestone earrings. I had taken my time with my makeup so I looked pretty hot.
I had some conversations with Tom during the week but they always ended up with just talk so I figured Friday’s conversation would be the same. I was chatting with a few guys as well and... Continue»
Posted by MichelleSEmass 4 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1239  |  
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Dominant Female Teacher Makes Crossdresser Student

Mistress said I should tell how I first became sub so here goes.
While I was still at school I was very thin, hairless body, high pitched voice and long hair in the most girly look I could get away with. I had started wearing panties under my trousers and I thought nobody knew. Well one day I was told to see the head of year immediately. She was terrifying to us boys, in her 30's, tall, thin, long brown hair in a severe style, she would wear heels with metal tips to announce she was coming from a distance. Very sharp manner and uncompromising.
In her office in front of her desk I stood ... Continue»
Posted by SapphireSomeday 4 months ago  |  Categories: BDSM, Shemales, Taboo  |  Views: 2286  |  
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