Shemales Porn Stories
Page 77

Sissy For My Flatmate, Chapter 2 – The Contr

If you've only just tuned in, here's what's going on in my life. Until recently I was a closet crossdresser trying to keep my hobby from my flatmate. When he caught me in the act, I found out that not only had he known about me for a long time but it was a turn on for him. I agreed to become his sissy slave and started the most incredible journey of my life.

Arriving home after from work, I threw my jacket down on the sofa and breathed a sigh of relief. It was Friday and I now had the weekend to look forward to. I slowly unbuttoned my short to reveal a short corset. It's been a few we... Continue»
Posted by Yosho 2 years ago  |  Categories: BDSM, Shemales  |  Views: 618  |  
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Airconditioner repairman laid some pipe

I was literally bored to death when my mom went on a vacation, i was hoping that i was gonna enjoy freedom when mom's away but things got worse as i found out the air-conditioner wasn't cooling the house, it was the dog days of summer and i really hate this muggy, hot weather. So i gave a call to the place where we bought it and asked them if they could send someone to fix it. Like i said, the weather was terribly hot, therefore i was wearing a micro-mini short which was showing of my curves in a very revealing way. It was almost 4.00 pm when the doorbell rang. I was expecting the same guy... Continue»
Posted by Slave4str8twinks 8 months ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3236  |  
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The continued adventures of Allison the cumsissy

The Continued adventures of Allison the cumsissy
This is a continuation of the same sissy slut’s story from my two previous works about Allison the sissy schoolgirl and her black daddy.

After the week long fuckfest, Allison the sixteen year old sissy schoolgirl boybitch had with her black daddy neighbor, she realized she was meant to a be a sissy cumwhore and decided to shop for as many sissy items as she could afford as soon as she could discreetly do so. As luck would have it, the following weekend her parents informed her that they would be going out of town yet again to visit his mothe... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1897  |  
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First time in Bangkok

If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floor of a 5 star hotel in Bangkok, which was pretty nice. I had just turned 39 and was looking forward to my first visit to Thailand and seeing my friend I had not seen in 4 years.

Now, I have travelled very much in Asia: PI, Hong Kong, Tokyo, Singapore, pacific islands, and Hawaii, but not Thai... Continue»
Posted by mahuluvr 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 2522  |  
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Teen Cross dressers First Man.

This is a true story that happened to me only a few monthe ago.

I just moved to a new town, I was an average 18yo male about 5'8 lean and athletic with a few female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about how great it would be to hook up with a shemale. I never thought it would happen of course, I didn't know where that stuff happened and I was always really shy.

One Friday after a grueling 4 hour study session at school one of my classmates, who I didn't know very well, invited me to have a few drinks... Continue»
Posted by ClaireCD 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2262  |  
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My firs time as a crossdrese

Hi,i am 19 and i have always liked wearing womens clothes.While wearin them i always imagined there was a nice older guy fucking me and cumming on my face. After a while i decided to try my fantasy for real. I got in contact with an older men and we decided to met. He said that he would come for me in a car and that we will go to his house and have a lot of fun. I was so nervous and could hardly wait to meet him. The next day i was waiting for him at a spot where we arranged to meet. He came in his big black suv and opened the door and said to get in. I got in and sat next to him. He had dark... Continue»
Posted by nikoletakurva 3 years ago  |  Categories: First Time, Mature, Shemales  |  Views: 1740  |  
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Tania

Tania was different! She looked and smelt so feminine. I'd been with other tgirls in the past but she was just different.

We'd been emailing and swapping sexy pics for some months now but now the day had finally arrived when we were at last going to meet. We'd arranged to meet in a lay-by just of the A46 just past a little village called Upton Crosby. I'd spent the last couple of days in a state of constant turmoil! What to wear? What would we talk about? What would we do? Would she like me? There were so many questions going through my mind. I so much wanted it all to be just right.

The... Continue»
Posted by joannacd1 3 years ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 1356  |  
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Turning my neighbour on in pantyhose

One of my neighbours whos in his early 50's and clearly a man of taste;) asked me recently had we got a cleaner in?! I said yes a couple of times a week. He seemed happy!
I know why..... My name is Lucy and I love strutting around in front of the window with sexy outfits on. I'm meant to be our new cleaner but I have to be honest, I don't do much, just a lot of bending over and stretching up high!
Yesterday I was dressed as 'Lucy the maid', shall we call her? I had 4 inch black leather heels on, which make my calves look fab!My favourite stocking patterned tights which are as equally shin... Continue»
Posted by lucyslegs 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1709  |  
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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 1 year ago  |  Categories: Anal, Fetish, Shemales  |  Views: 2051  |  
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my gardner plowed me

My wife and daughter had left to spend a week with my mother-in-law in Brazil. So it was time to breakout my secret wardrobe. Having two women in the house made it easy to keep a sexy supply of clothes. Add a wig and some makeup, I'll soon be lookin pretty hot.

I started by shaving my body and taking a long hot bath in some lovely smelling bath oils. Just the thought of dressing up was making me wet. I dried off and went to get dressed. Being in a wheelchair made it take a long time to get dressed. I wasn't even going out but I wanted to dress up and maybe video chat with some hung studs, ... Continue»
Posted by cdaisy1 2 years ago  |  Categories: Shemales  |  Views: 2099  |  
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Awakened by Candy

It was a Saturday and I was just strolling down the High Street, going nowhere in particular, when I noticed a commotion down a side alley. A largish male was pushing two girls around; they both looked pretty distressed. I grabbed the bloke as he slammed one of the girls into a door, and he went arse-over into the road, got up and took a swing at me. I dodged, and gifted him a right hook; his nose took the brunt and spurted bl**d instantaneously. He thought about coming again, but the bl**d was pouring from his nostrils; he staggered off, thinking better of it.

The two girls were a litt... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2351  |  
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Trucker tales

The potato farmer and his wife (and a surprise bonus)


I recall this from memory to the best of my recall

It was a really hot day down in the panhandle of Texas My dispatcher had pushed me to get down here for a load of potatoes and I had been driving for about 10 hrs strait and I was running close on my 70 also so I just wanted to get to the farm and get the load on and then find a long shower and a hot meal and a cool beer cause I didn't have the hrs to go anywhere.
When I finally found the place it was out in the middle of nowhere I could see 2 other trucks in the ... Continue»
Posted by hotmedic 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 2473  |  
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The Shoe Store

The Shoe Store
By
L

Adam hated working Wednesdays. He works the entire day from opening to closing every Wednesday. His manager always takes Wednesday off. This was mostly a boring day for Adam. A few women came in the store before lunch which was a disappointment for Adam. Adam is a bit of a pervert. He likes to take a peak up a woman’s dress or skirt while he is putting on shoes for them. The morning customers all were wearing slacks.

A woman came into the store a little after lunch time. She was wearing a halter top with a short skirt, stockings and heels. Adam went over to her ... Continue»
Posted by Len1958 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 2241  |  
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Come as you are!

I was overnighting on a business trip and as was my kinky little habit, I crossdressed at night. My room, which was on the second floor, had a full sized sliding glass door and balcony. Another motel across the parking lot from mine had windows facing mine. I dolled up in my skimpiest black lingerie with high heels, wig, and full makeup and kept my lights off so that I could walk around on the balcony safely. All the curtains were drawn on the motel across the way, so after a while I got a bit careless about the lights and left them on after going in to fix another drink. As I stood out on the... Continue»
Posted by dana213 1 year ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1782  |  
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A date with a straight college student

I had been chatting with this boy for a while when he finally told me his parents were out of town and he had his father's car. So we set up a date in the evening. I told him to pick me up by his car from somewhere. I was pretty excited, this jock was a very good looking guy with a slender athletic body type, brown hair/blue eyes. I always had a thing for blue-eyed boys. I was thinking about those whilst putting on make-up in front of the mirror and combing my hair.
I was a lil bit nervous when he picked me. He looked even much more handsome than his photos. Because he was lacking a web cam, ... Continue»
Posted by Slave4str8twinks 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1809  |  
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Back to the shitty date which ended up not so shit

I straddled Ron, the black hung stallion and impaled myself on that huge cock. I slid the whole length of that massive shaft swallowed that shit up, til I felt it in my lungs. It must have felt good because his eyes got all googly watching me take that black dick all the up inside me! It felt soo deep pulsating inside me!

then WTF? Andre, starts to straddle his face and get rimmed by Ron! I knew these fuckers were fags, and that really fucking turn me on! Not because I'm into gay sex or anything. Just into the possibilities it presents!!!! I start to grab his balls and stroke dre's ... Continue»
Posted by sataori_fukame 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1140  |  
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Curiosity Part I

“Alright, Jason, that concludes your orientation. You can go ahead and get started,” said the chic manager of the retail clothing store that catered to juniors.
“Thanks, Melanie! I’ll talk to you soon.”

Shortly after she disappeared Jason was walking the perimeter of the store performing his security detail. Standing at just under six-feet-four-inches and weighing about two hundred forty pounds Jason Pitts, caught the attention of one of the sales associates.

“You gonna keep us safe from all the project chicks,” quizzed the short and slender chocolate employee.
“Yeah I guess. I doubt t... Continue»
Posted by faggyboi 7 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3030  |  
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Sweet Charity

You may have heard of the phrase sweet charity, well in my case it was certainly sweet to me. I have built up a large part of my CD wardrobe through judicious visits to charity shops wherever I may be in the country. In one of my local charity shops there's an assistant called Wendy who I would judge is in her mid fifties but looking well on it. She's always well turned out in neat blouses, always a just above the knee skirt, never bare legs and 3 to 4 inch heels of various kinds. I must admit that my fairly frequent visits to this particular shop engender a feeling of hornyness on two counts.... Continue»
Posted by MichaelaCD 2 years ago  |  Categories: Shemales  |  Views: 1060  |  
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The Trip part 3

I soaked in the tub for close to an hour, thinking about my predicament, it was only the second day of the trip, I figured if I was going to get through the week then I just had to resign myself and do whatever Joe asked of me, sex is just sex, I reasoned, it doesn’t matter who or how many people you have it with, it’s still just the same physical act, if I could get over the psychological aspect of what I was doing, then it would be a lot easier.

I mulled it over for a while, before getting out of the tub, brushing my teeth and swilling my mouth out with mouthwash, it still didn’t entirely... Continue»
Posted by kara_zor_el 2 years ago  |  Categories: Shemales  |  Views: 632  |  
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My shemale boss part 3

I was woken by the vibrating noise of my mobile and looked over at the time, the bedside clock said 1am. The caller I'D on the phone simply showed Bitch, naimly my boss Miss Jones, would she never leave me alone.

I answered the phone and still being half asl**p simply said 'yes'.
'Don't answer me with that tone Rob' she said. 'Sorry, but its one in the morning' I replied.
'Be a darling Rob and pick me up from the club, text me when your outside'. Before I could say anything she hung up.

I pulled my arse out of bed, slipped on some tracky bottoms and a t-shirt, jumped in the car and dr... Continue»
Posted by big_rob49 1 year ago  |  Categories: Shemales  |  Views: 1495  |  
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