Shemales Porn Stories
Page 6

Night out

My wife knew that I liked to dress and would often help me. Usually it just consisted of dressing up and watching TV or maybe having hot sex. Once she had me dress and took me for a drive to the park where she made me walk around and pose for pictures. She’d also take me to the local thrift stores where we’d buy new things for Michelle. In bed we’d often talk about me dressing up and going someplace in public like a club or show. It seemed to make us both hot and the sex we had afterwards was fantastic.
One weekend we had to go to Providence for a friends wedding. My wife told me she w... Continue»
Posted by MichelleSEmass 4 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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first time cumming

When I was 12 I began secretly stealing my s****rs pills and clothing and make up, I was dressed up as a girl when I was younger and enjoyed the feeling so growing up I have always had a time to connect with my femme side, when I started stealing her clothes and make up I would look up videos online to see where all the make up went and what was good colors for my complexion, I've always been pretty skinny but the last year I let myself go and put on a few extra pounds and began to fill in the bras and panties a lot better than usual. After noticing how great it felt I began to diet again but ... Continue»
Posted by reefermcrevolver 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did.

I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite another woman to join us. She also knew I liked to dress up. We’d often go to the local thrift sto... Continue»
Posted by MichelleSEmass 4 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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My Sissy Fantsy pt 001

Chapter 1

I reach the campsite just as the sun is going down and the clear sky is bright orange as if in memory to the beautifully warm day it has been. The campsite is popular yet set on secluded farmland and as the season is just over it is practically deserted. The whole camp is surrounded by woodland and a stream lined with more trees cuts through the campsite, dividing it into unequal sections. Walking through the larger first section I can see only ten other pitches occupied by either tents or caravans and I hurry past them. Crossing the rickety bridge I enter the second smaller secti... Continue»
Posted by monalottanow 4 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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My sissy Fantasy pt 003

We come to another set of double doors, though these are glass paned in Victorian iron work painted white, as is the wall which it I set in. But due to the humidity all the glass is misted, including the dome and I can’t see where they lead outside. Jake opens one of the doors and we step into the rain that has subsided only a little to find myself standing in front of a large infinity pool that seems to drop off the rear edge of the building into that amazing view of the valley. Either side of the pool is a large patio that must run the entire wide of the house before simply dropping away to ... Continue»
Posted by monalottanow 4 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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From Andy to Amy


Story codes: CD TV mf voy mast nosex

If you are looking for serious one handed reading, then you are in the wrong place. I hpe you like this. It's the stopry of a young man's first venture into cross dressing. Any similarity to me is entirely coincidental!

Title: Andy to Amy

"Why are you staring at my knickers?"

I jerked upright. God, I really had been staring at her knickers - not the ones she was wearing, sadly, but a pair on the floor, presumably yesterday's pair. They were perfectly normal white knickers with little pink flowers on them and a tiny satin bow on the front - ... Continue»
Posted by justpeekinout 4 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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More of my Sweet

I was really becoming attached to this person. From the waist up a she, from the waist down completely a man. In the past, I had given thought to the attraction I often felt toward men, but I would never have taken it any further than the dark corners of the peep shows. I would never have openly dated another guy. It was always completely sexual. I enjoy sex, always have since an early age, and always will till I hit my grave.

Now, along comes this person that is satisfing both sides of my sexual desires. Someone who wanted to be with me and it was confusing to say the least. After ... Continue»
Posted by milkmanj 4 years ago  |  Categories: Fetish, Shemales  |  
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my new flat (part 2)

After putting the phone down i started to panic a little , i had just accepted a date from a guy who i had just met a couple of hours before, and whats more he did not know i was not a real girl, what the hell was i going to do, could i bluff my way through this.
Mark was his name he was a nice looking guy i would say he was about 30 at the most quite tall with dark hair and we did seem to get on well when we chatted so i decided i would keep the date i had made with him for that night , my plan was also to tell him i was not a real girl and hope for the best.
Mark was due to pick me up at 8... Continue»
Posted by julieanneff 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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College cumming out party!

Aaaaaahhhhhh...where to begin? I guess it all really started in my teens, when I discovered the joy of dressing with one of my close friends. Like many others we started off slow, wearing panties and giving one another hand jobs and feeling at least a little bit like we were doing something we shouldn't be. After a few months of fooling around like this I arrived at his house one summer morning to find him dressed completely from head to toe in his s****rs clothes. Tight, short, sexy little miniskirt barely concealing a tiny pink thong, strappy stilletto sandals, skimpy camisole over a lace b... Continue»
Posted by sweetsashacd 4 years ago  |  Categories: Shemales  |  
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Riding the Lakefront-Chapter3

August 13,2008...6:30pm...Chicago Lakefront Bike Path--Irving Park rec lot...8:30pm

My life changed that night!

The silence of the car...sitting there...thinking about the call I had just experienced...was deafening! What began as my usual bike ride ended in a catostrophic state of affairs. What began as just this innocent ride ended with the creation of a black mailed sex slave about to embark on an unbelievable series of escapades with no end in sight. I lost interest in the radio. I lost interest in stopping at the gym to clean up. I lost interest in getting something to... Continue»
Posted by titsR4abuse 4 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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Delilah and the Deep Blue Sea (part three)


One day (I suppose it must have been after I’d spent about two months on the island) I was down along the shoreline collecting driftwood. On these occasions I always kept my eye open for anything else that might be of any use and this day I had a real find. Washed up against some rocks a few yards off the beach was a large plastic garbage bin. An old discarded garbage bin might not seem anything to get excited about but it was as good as treasure from King Solomon’s mines as far as I was concerned. There were literally dozens of uses we could put such a large receptacle to. My mistress was b... Continue»
Posted by Mikebasil 4 years ago  |  Categories: Lesbian Sex, Shemales  |  
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Superbowl Party

I was very surprised when my b*****r-in-law Tom invited me to watch the super bowl with some of his friends. The only reason he would “invite” me over was to be his little sex sissy, since he had enough pictures of me dressed as a girl sucking and being fucked by him I had no choice but to do as told.

This would be different, I thought because his friends would be there and he would never let them know he did any homosexual acts.

When I arrived Tom immediately hustled me into the bedroom. I saw right away the little French maid outfit on the bed and my heart sank. I protested, and said t... Continue»
Posted by pandys 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Bring the roof down…


It was the week preceding the weekend of my wedding to Eva, even though I am usually calm and collected I tend to catch some degree of anxiety prior to major events in my life. I had had quite a long day what with wedding preparations in their final stages and even after downing some beers to urge on some sl**p none was forthcoming and that’s when I thought to go up to the roof of the flat that I stayed in. The block of flats I stayed in had one of those old type roofs where only someone that had serious business on the roof bothered going there.
Anyhow so this idyllic moonlit Sunday eveni... Continue»
Posted by mobidix 4 years ago  |  Categories: Shemales  |  
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The Trip

I’d been seeing Joe for most of the summer and in that time I had starred in maybe a dozen or so of his private home movies. My hair had grown maybe another inch, I’d had my ears pierced and my eyebrows shaped, as far as my parents were aware it was because of a drama club I’d joined, where a part dictated the sacrifice, it was a poor excuse but they chose not to question it further.

One Sunday night I got a telephone call from Joe telling me to come over right away, I dropped everything and did as I was told. When I arrived at Joe’s he ushered me straight up to his bedroom.

“Were going ... Continue»
Posted by kara_zor_el 4 years ago  |  Categories: Shemales  |  
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The Trip part 4

The next day Joe told me to take it easy as I had a busy night ahead of me, so we lazed around the cabin, I cooked breakfast and lunch for Joe and Chris and spent the day tidying up and making sure the place was as good as it could be, I snuggled up with Chris on the sofa all afternoon as we watched bad movies and took the mickey of them, it was the closest it had come to being a holiday since we had arrived.

I cooked the guys a couple of steaks for dinner and as I started the washing up, Joe walked up behind me

“I’ve laid your outfit on the bed for you. This evening is important to me s... Continue»
Posted by kara_zor_el 4 years ago  |  Categories: Shemales  |  
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Tranny sex

I dressed in her bathroom. Comfortable nylon stockings and my black body with suspenders, black thong, my beautiful silicone breasts in C-cup and between blond wig with ponytail up on my left shoulder. High heels had to wait this time. Then I pulled on my red short dress in jersey. He who runs away from each other so good around my body and butt and let my tranny cock visible as a bulge in the front. Her breasts hung heavy and stuck out in the red dress.

She came out of the bedroom and met me with a warm hug and a nice kiss, tongue against tongue. She was really horny, my fair transvännina.... Continue»
Posted by sindy_trans 4 years ago  |  Categories: Shemales  |  
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Shemale on wheels tour

Being a sexy naughty city girl like myself…I get allot of attention from the boys. I always enjoy getting the attention of the small town boys that are not used to seeing a sexy bitch like me roll though town. They jerk off to girls like me online all the time. But having me right in front of them sometimes makes them overwhelmed and easy targets and my prey… lol.

For me, I love sex. I enjoy the attention of men and I love being used by a man. But the biggest turn on for me is finding some dumb straight boy and wooing him with my big tits and dropping to my knees and having him give me a go... Continue»
Posted by tashajones 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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My second time with Jake

The week after my first experience with Jake was amazing. I had finally sucked a real cock and I wanted to again. All that week Jake kept texting me pictures of his hard cock. I couldn’t believe that he was into a gurl like me. On Thursday of the week he texted me another pic of his cock and the message said, “Tomorrow night I want it again.” I immediately got excited. He called me Friday morning and said that he would be leaving his dorm at 7pm and would be back at 8pm. He said that he would leave his room unlocked and I should go in and change into something sexy.

So at 7 I did as he sai... Continue»
Posted by taylorbaby 4 years ago  |  Categories: Anal, Shemales  |  
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Jesse’s First Day

Jesse’s First Day


Jesse didn’t want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse had never had a tailored suit in his life, but now he knew why someone would pay so much for one. They made the guy wearing it look like a movie star. Antonio had worked his magic on the suite overnight and when Jesse had stopped by early this morning to pick it up Antonio had insis... Continue»
Posted by SCARFACE12 4 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Christine: Transgenderism.

Introductory notes; The following piece is an extract from my novel "Sarah's Garden". It is not a work of erotica as such so if you've come here looking for erotic stimulation then I apologise. Instead this piece is posted as a sort of exploratory discussion of transgenderism. Since I have been posting my work on this site I have had the privilege of meeting many kind people on here who have expressed an interest in transgendered people and why they are what they are. It became apparent that this is a greatly misunderstood subject and, since misunderstanding is frequently the source of prejud... Continue»
Posted by Mikebasil 4 years ago  |  Categories: Shemales  |  
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