Shemales Porn Stories
Page 7

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 2 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 604  |  
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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 2 years ago  |  Categories: Lesbian Sex, Shemales  |  Views: 738  |  
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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 2 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 1417  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 567  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 1397  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 681  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 699  |  
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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 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2072  |  
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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 2 years ago  |  Categories: Anal, Shemales  |  Views: 2331  |  
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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 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1678  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 737  |  
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Date Coach from sissifyourself


Chapter 1


“So what brings you here today?”
Daniel looked at the date coach. He wasn’t sure of his height, taller than himself for sure, who stood at a paltry 5’ 4”, even though he was already 23 years old. He’d been made fun of his whole life for his height, but he still had a good bit of muscle, and some fat on him, as he weighed about 150 pounds, with nary a hair on his body. The doctor on the other hand, still looked athletic and muscular through his button down shirt, and didn’t look a day over 35. With his short clean cut hair and clean shaven face he could tell this guy was real ... Continue»
Posted by slim_krak 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1229  |  
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The Making of a Sissy - Part Nine

As they sat sipping drinks and discussing what shots would be done indoors or out; Bella’s little cock bulged in her sari as the mature redhead licked her lips as she discussed the ways in which Bella should be trussed, collared and leashed, amongst other things. Sandy stood up suddenly and ran across the patio when she saw a tall figure emerge from the house into the sunlight; this was her Carl. Bella looked on enviously as the two squeezed and kissed at length. She could only dream of being that way with Adam, and so yearned for such a moment with him. Sandy tugged Carl over to the others;... Continue»
Posted by midsummerman 2 years ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 466  |  
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Out of town, I broke free

So I was out of town on business, and I hadn't worn any female cloths out ever in my life, but this time I took some sexy cloths from my roommates girlfriend..and I had been chatting with this transgender girl in the city I was heading to for a few weeks, we would skype and get off together, and she would make me do things to please her..I'm a switch but for this girl I'm her sub slave. When I got to the hotel I took a shower and shaved myself..complete, then I call my Trans friend, for the sake of this story I'll call her Dana, so I called Dana, she told me to get dressed and meet her at this... Continue»
Posted by smonkeys32 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 349  |  
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The Making of a Sissy - Part Ten

Bella quickly gulped down her vodka and cherry, her bottom tingling with anticipation as her new mature friend gave her a commanding look; she had so enjoyed being submissive for her at the end of a leash, and now she knew she would be bound tightly on a soft inviting bed, and made completely helpless. Her cock stiffened sweetly at the thought; perhaps she would taste the cane again, she would love that. Ellen took Bella’s little hand and squeezed it tightly; though she had only just met this supreme example of a shemale, she knew instinctively she could trust her completely. The redhead smil... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 482  |  
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The Making of a Sissy - Part Eleven

Whilst Bella showered, Ellen and Sandy went down to the poolside to ready some ice and bottles for drinks later; there was Bella’s phone, Ellen tapped in the number to her own phone, and also took down someone else’s number. Ellen smiled wickedly.

“I have a very sweet idea, but I’ll need a week to arrange it; I have to put a proposal to that aunt of hers first. I’ll need your assistance at some point.” Sandy was willing to help out in any way, and the two chatted and giggled as they too went back upstairs to shower and prepare for the evening. Roberts worked swiftly to get the videos and ... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 457  |  
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Meeting a guy from online part #1

I had been talking to a guy Jim online for a few months he was white 47 and we got into some very erotic conversations on line and even had phone sex together a few time then we decided to meet,I was all too excited thinking about seeing him in anticipating what both of us knew what was going to happen.
I got into town showered getting cleaned up putting on a short brown skirt with a white top over my very little panties and padded bra finishing my outfit with a pair of three inch black pumps, looking at myself in the mirror I thought I looked cute thinking he was going to like what he sees... Continue»
Posted by MonicaBond 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 852  |  
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Sandy comes to visit me

If you have read any of my prior stories, you know that while I was born as a boy, I more closely resembled my mother and my older s****rs. I was the only boy in our f****y, and from a young age realized that I was destined to live as a girl. It started early in life, with me sneaking into my s****r’s rooms and admiring their pretty things. Later on, I actually began “borrowing” things from each of my s****rs. I lived in secret, ashamed that I was different.

When I graduated from high school, I moved to the big city to attend the University. I was fortunate, as my grandmother loved me dearl... Continue»
Posted by Rickicd 2 years ago  |  Categories: Shemales  |  Views: 1737  |  
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Click, click, click....

Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will the skirt be, how long the legs and what manner of hosiery will adorn the object of my desire? Sometimes you can anticipate the leg length by the quickness of the steps, short light steps equal a petite form, slightly slower, paced steps announce a graceful flowing creature.
Click, click, click…today it was an ex... Continue»
Posted by MichelleFaye 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 976  |  
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My real story



I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him.

It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willing to do anything."

Now what I had written was the following:
"Young 48 year old, looking for an older man, early to mid sixties, still sexually active willing to be my top. Would love to get together and decide what our roles would be and then keep them going whenever we meet. I am a submissive who lo... Continue»
Posted by lookin02 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 2104  |  
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