Shemales Porn Stories
Page 65

Straight, to Bi, to Gay, to Trans, to Straight (Pa

I don't want you to think we simply lived happily ever after. Nothing is that simple.

We've had our ups and our downs, and our ins and outs. We've had three major hurdles, so far. The first was me freaking out over the idea of having a boyfriend. As natural as it seemed to be with him, and as mind-blowing as the sex was, it was still a huge shift in thinking for me. The second hurdle was coming out.

The third was his affair. But more on that in a minute. As I want to talk first about coming out. Friends and f****y may say they support gay rights and all, and they may be fans of... Continue»
Posted by TransContinental 2 years ago  |  Categories: Gay Male, Shemales  |  
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Jeremy's School Bully

Jeremy hopped off the bus in front of his new school. He lived close enough to walk, but had decided to ride the bus instead. He wanted to see what it was like, because he'd never rode the bus at his last school, he had always walked. The school was a hulking sandstone building that loomed over the small front lawn like some mid-evil wyvern, gobbling up c***dren every morning only to puke them back out onto the lawn in the afternoon. Over the years acid rain made long dark streaks of black and brown down its façade making it look as if Mother Nature had raked it with her claws. It was a post w... Continue»
Posted by test2012 2 years ago  |  Categories: Shemales  |  
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Portuguese Summer part3

After that night with Alan and the girl back at the villa i was very nervous about going back into work the next night , i was just not sure how much he had felt while he was fucking the girl with me under her or even if he was aware of what happened. When he turned up for work at the bar about 20mins after me he pulled me to one side and just grinned at me and asked if i had enjoyed it
I sighed with relief and said "yeah it was great fun,he just grinned again and said ok ...well if we ever get the chance lets do it,ohhh and i saw her give you her thong as she was leaving and i saw you puttin... Continue»
Posted by julieanneff 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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Portuguese Summer part2

I have been in Portugal now for 2 weeks Paul has phone to say he wont be coming out for the rest of the summer as his dad is in a bad way , His mum has asked if i will stay in the villa and look after it for them until the end of august, of course i said yes, but i was getting bored and needed to get some work as the little money i had was not going to last long.
Since Paul went back home i have discovered that i love to dress up in his s****rs clothing that she has left here , and boy has she left a lot of stuff, I have full shaved my body and have started to become quite good at putting on ... Continue»
Posted by julieanneff 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Portuguese Summer part 1

i`m not tall, in fact for a guy i am quite short at just 5ft6in and very slim for a guy as well weighing in at just over 8 stone, so girls friends have been a little hard to come by but i have had a few over the years, 2 in fact but one of those was when i was 14 the next one came 3 years later.
So now at 18 years old i am jobless and without a girlfriend and its just coming to the summer.
Paul is my best friend he is from a well off f****y and he turned up at my house one day in June and asked if i wanted to head out to Portugal with him for the summer, His parents had a 2 bedroom villa out... Continue»
Posted by julieanneff 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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First Time - Surprise Shemale

I'm an eternal masturbator. I've always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so many things to see and do. One day I discovered the true beauty of the shemale. Wow. Gorgeous women, with cocks. Prior to this it had been women with strapons that got my attention, but this? Perfection. Then cam the webcam. I found a couple of sites where you could interact with such beauties and c... Continue»
Posted by hungrymanx 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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Poker Night Part 3

Everything was black. I couldn't see a thing, but I heard everything. ""Obey! Suck cock! You are a sissy! Worship cock! Obey your master! Obey!" over and over again. Every time 'cock' was mentioned a giant one flashed before me. And every time 'master' was said I saw an image of Craig. I didn't know what was happening, but after a while I accepted it. I woke up dizzy, my mouth open and dry. Sweat covering my body. "What was that all about?" I thought. It was morning. I got out and made breakfast for myself and Craig. "Goooooood morning" Craig said from behind me. I turned around to say good mo... Continue»
Posted by ConvertedGirl914 2 years ago  |  Categories: Gay Male, Shemales  |  
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Horse-Cock Girl Part 3

Transsexuals & CrossdressersHorse-cock Girl Ch. 03
Horse-cock Girl Ch. 03
Author's Note: This story isn't the end of Horse-cock Girl. I've got another in mind which is why this one ends rather suddenly: the next chapter will follow on directly from this one.

The new character, Scarlet is devoted to a good fiend of mine who is a huge fan of this series. She created Scarlet and everything about her, all I did was write it down and turn it into a character.

I've been toying with the idea of a Q&A session with the characters of this series. If you would like me to write it, le... Continue»
Posted by drew1207 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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S****r has a Secret part 3

Sarah was sat on her laptop, searching for something on the internet. She wanted to surprise Hope with something for her official leaving of school.

She'd been looking up the cheapest, quality flights she could get to take them both on holiday for a week or two, but she'd been hampered a lot by Hope wanting to hang out together. Hanging out normally involved sex, after which Sarah had little energy left to search.

Luckily, Sarah had the day off work while Hope was sitting her final exams for the year. She was looking through the normal travel agent websites while also looking on other ... Continue»
Posted by drew1207 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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by Jennifer Lorissa-Leigh

"I tell you, Arnie, something's going on in there." Jeremy spoke as he and his friend looked upon the university's Institute for Human Sexual Studies. "I know Jerry went in there, and never came out."

"Maybe he just quit school and went home to Nebraska, like they said," Arnie suggested. "What could possibly be in there that would cause someone to disappear?"

"I don't know. Some kind of foul play's going on... maybe one of the professors is a serial killer, or something like that. I gotta get in there. I'm getting to the bottom of this."

"Why don't you c... Continue»
Posted by PaRiaH236 2 years ago  |  Categories: Sex Humor, Shemales, Taboo  |  
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The Transformation part IV

Mistress Anna woke me from my nap. Her hand was gently brushing my cheek and she was telling me, "what a good girl you are! You even crawled here and licked up your mess! This dried spunk on your face just won't do though. Go to the bathroom and wash it off then shower and we'll get you dressed and put your make-up on."

I rose from the floor, thankful that they had set me free of handcuffs. I still was locked away in my metal chastity cage so I suppose they didn't figure the handcuffs were necessary. Mistress Anna slapped my ass as I walked into the hallway. I could hear Mistress Heat... Continue»
Posted by fictiong 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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The neighborhood sex slaves Part 2

Jack and the girls had gone home about an hour ago and I was in the gym working out when I heard the front door open. Kelly came bounding in calling out my name.

I told her I was in the gym working out.

Kelly sauntered into the gym wearing my favorite little black skirt and red tube top with a "cheshire cat" grin on her face. My cock stiffened a little when I saw her. She came over to the bench where I was now sitting up, straddling my legs and sat down. She looked at me in my eyes and said "I've missed you honey", "Did you miss me?"

Wrapping my arms around her waist, smiling, I said ... Continue»
Posted by Bigrodtaz 2 years ago  |  Categories: Anal, Shemales  |  
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Appointment By Card Only. part six

His landlord was not best pleased when Bruce announced his immediate departure, but was happy to hand him a bill requesting three months rent in lieu of his vacation without notice. He packed his laptop and the few items of decent clothing and sparse possessions into a sports bag and slung it into his car, then drove back to the house, his mind racing; he could not believe what he was doing, his rational thinking telling him to turn away, but the draw of the magnificent controlling woman and a life which consisted of perpetual sexual excitement drew him to her. The plug teased his anus, remi... Continue»
Posted by midsummerman 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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My fucking f****y

I'm really proud of this would love some feedback

Why was I on all fours with my dad's cock in my ass and my s****r's pussy in my face? Well little did I know that my mom knew about my secret. She knew that I had been wearing her and my s****r's lingerie.

It started when one day I was home alone and wandered down to the garage to play around on the air hockey table. I got bored and looked around as we had a lot of stuff down there. Boxes were piled up on one side and I looked in a few of them and found something that made eyes pop open.

I saw a naked girl on the cover of a magazine... Continue»
Posted by 6270daniel 2 years ago  |  Categories: First Time, Shemales, Taboo  |  
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my first encounter

i had been with my girlfriend for over a year now, and our sex life was amazing, but i wanted to try something new. i wanted to try role reversal. i had never mentioned this to her, and i wasnt sure on how she would take it. one night, i decided to bring it up to her.

" ummm, hunni..can i ask you something?' i said.

" sure, babe, what is it?" she replied.

"well, i wanna try something different. i want to try role reversal, where i dress up as a girl, you wear a strapon, and you fuck me in the ass. what do you think?:

: wow, really? know, i think i could be fun..umm... Continue»
Posted by SashaCD 2 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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S****r Has a Secret Part 2

Sarah moaned as Hope sucked her cock. Sarah's tongue was buried deeply in Hope's pussy, her moaning causing a vibration that caused Hope's own moans to vibrate her mouth around the cock inside it.

"Oh fuck," Hope moaned softly. "You're tongue feels so good."

"So does your mouth," Sarah replied.

Spurred on by the encouragement they gave each other, Hope and Sarah began to pleasure each other more feverishly. The sounds of the sucking and slurping filled the room loudly. It was almost deafening to the two girls causing the sounds.

Sarah started to feel a tingle welling up in her ba... Continue»
Posted by drew1207 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  

From Tony to Tonya part 2

Tony woke up on Saturday morning feeling excited without knowing exactly why. He tried to sit up, but his left arm was pinned down by Sarah's body. This was normal for a Saturday morning, since she tended to sl**p at Tony's house on Fridays.

The reason he was excited suddenly hit him. On Tuesday, Sarah had told him they were going shopping today. This had been right after a great fucking-session in which Tony had been dressed in Sarah's old school uniform and she'd fucked him with a strap-on dildo. It had been a very kinky evening.

Very carefully and gently, Tony extracted his arm from u... Continue»
Posted by drew1207 2 years ago  |  Categories: Anal, Sex Humor, Shemales  |  
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Horse Cock Girl Part 2

Amy woke up around dusk, based on the amount of light coming through her bedroom window. She'd fallen asl**p, her new horse-cock still hard and inside her best friend, Lucy.

Lucy was awake, watching Amy sl**p, and apparently enjoying the cock that was still inside her and hard again. Lucy was bouncing slowly and gently on Amy's cock and smiled when she noticed her friend had awoken.

"Good evening, sl**ping Beauty," Lucy said, in a slightly strained voice. She couldn't keep her pleasure out of her voice.

Amy smiled and pushed Lucy off of her, rolling on top of her and kissing her nec... Continue»
Posted by drew1207 2 years ago  |  Categories: Fetish, Sex Humor, Shemales  |  
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Poker Night Part 2

Over the next two weeks, I heard the static crackling each night. Never had any dreams however, and the static was always louder on Friday nights. I swear I could hear something coming from the walls, just couldn't make it out. " CC. r hip ok. O...hey ter...O...hey" Over and over again is what it sounded like. But I could not make it out clearly. I drifted off to sl**p each night. I resolved shortly after to see what was going on. I searched every corner of my room and found nothing. So I gave up. I thought I must just be hearing things, which was known to happen with me. S... Continue»
Posted by ConvertedGirl914 2 years ago  |  Categories: Gay Male, Shemales  |  
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Tgirl Playing With 2 Bi M/F Cpls Part 1

Playing With 2 Bi m/f Couples, (True Story) Part One,...

I was watching a straight porn movie a few years ago and after it ended the screen went blank, and I got up to pour myself another drink. When I came back in the room another movie was playing that totally blew me away.

This gorgeous young couple were sharing the well hung cock of another guy, and it was just amazing to see the look of pure lust in that womens eyes.
That was the start of my bi curiousity, and I set about finding myself a hot
bi couple.

Over the years I had met several attractive bi couples, but there was one ... Continue»
Posted by TgirlNikki 2 years ago  |  Categories: BDSM, Group Sex, Shemales  |  
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