First Time Shemale Surprise free porn video

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It was pretty late and I was well into my drink. God knows where my pals had gone off too. I was sat in a bar nursing a bottle of beer when this tall, sexy lady sauntered towards me, her black wavy hair bobbing with each step and her dress shimmering purple and gold as the dim light reflected off it.

She rested her hand on my leg and without taking her bold eyes off me said, 'Hi. I'm Jess. Drink?'

I was still fairly lit, but completely taken aback by her directness, I still managed to mutter, 'Sure.'

'Bobby – Two whiskies.'

We clinked glasses and she downed hers in one. Not wanting to be left out I did the same, feeling the burn stretch from my stomach to my throat. Again, she got two more and led me to a booth.

'So, first time in Blackpool?

'Yeah. Out with my pals, but ended up losing them.'

'Aw,' She said, dropping her hand to my groin.

I flinched. What a girl! If only all chicks were so free and easy. My mind was already reeling off image after image of being with her and I soon got an erection.

'Your cute.' She said, as her hand grasped my cock through my trousers. 'How about we go back to mine and you can fuck my arse?'

Jesus! My cock was popping harder than ever. 'Yeah okay.'

She smiled and huskily said, 'Drink up.'

I followed her up the stairs, watching her great behind swing left and right. We entered the bedroom and she dimmed the lights, turned and started french kissing me. I was pretty wasted, but so turned on by this powerful woman, as she thrust her tongue deep into my mouth exploring as far as it would go. She then sucked on my lip as she deftly undid my shirt buttons, belt and dropped my trousers. I kicked them off, eager to bury my cock inside her.

She pushed me back on the bed and deep throated my cock straight away. 'God!' I cried out, as she thrust her throat down on my cock, getting faster and faster.

Jess pulled off with a big sigh, 'You ever done poppers baby? It makes it so much better.' She held the bottle under my nose and told me to sniff deeply.

Soon my head was throbbing and all my inhibitions seemed to melt. She went back down on my cock, this time sucking it harder, whilst her other hand played with my balls and arse crack. I grabbed her head and started fucking her face off my cock as my need to cum was building and building.

Pulling off, she hiked up her skirt and climbed on me, guiding my cock with her hand to her waiting arse.

'Condom?' I managed to say.

She just smiled and lowered herself fully down on my cock, moaning as she did. She obviously needed more as she was slamming down harder and harder on to my cock, panting and moaning as she did. There was nothing soft about this girl. She seemed full on, flying at 110%. She grabbed my nipples and started tweaking them hard, but it was all too much too soon.

'I'm gonna cum!' I shouted, thrusting and pushing her down at the same time.

She pulled off quickly and wrapped her lips around my cock. What a dirty bitch, I thought, as I grabbed her by the hair.

'Yeah! Suck that cock!' I said, my whole body tensing as I thrust it deep into her throat, over and over again, until I came, shooting my load into her mouth.

She never spilled a drop and squeezed my cock from the hilt, pushing the last remaining drops into her mouth.

Exhausted, I sagged into the bed.

Like a panther, she clawed her way up me, her nails biting the skin of my shoulders as she pressed her mouth onto mine. We kissed and as we did, I could taste her, but also my salty cum. We stayed like that for a while, her controlling the kissing, her lips and tongue spilling over my mouth, my lips and my chin.

She giggled, 'Your a mess! Go clean up and I'll get us drinks. Bathroom is second on the left.

The lower half of my face was covered in her lipstick. I washed my face and headed back to the bedroom.

Another whisky was waiting. We clinked glasses and downed them. Then another. Damn, she is one wild bitch – drinks like a trooper.

'You look tired baby.' She said, as she played with my flaccid cock. 'How about a massage?'

She sat on my butt and worked my shoulders and my back, rubbing muscles I didn't know I had. I'd never had it this good.

'Such a cute arse!' She said, as she started rubbing it and spreading it open.

I didn't know what to say, so said, 'Thanks,' As her fingernails travelled down my crack and grabbed my balls and cock.

'Looks like you like it!' She said, as her nails glided over my balls. 'Have some more poppers.'

Sitting up on my shoulders, I took a few sniffs until all my sensations were heightened. Her hands spread my cheeks and she started flicking and circling her tongue against my arsehole. I moaned in delight at this new found feeling and I was soon holding my cheeks apart as her tongue got deeper and deeper into my hole.

'Oh Yes!' I managed as I undid the poppers and sniffed longer and deeper than before. 'That feels so fucking good.'

She moaned a yes into my hole and soon she stealthily replaced her tongue with a finger. 'You like that baby?'

'Yes!' I managed.

Soon it was two and then three. The more she did it, the more I was getting lost in my own desires and I soon had my arse pointing upwards. Pressing her fingers against my prostate she flicked them rhythmically against it until I was cumming in a way I didn't know possible. Stream after stream seemed to leak out of my cock into her waiting hand. Hell, it wasn't even hard anymore.

'You want me to fuck you more?' She said, as she let my cum drip onto my hole and started massaging it in.

'Christ yeah!' I said, all taken over by moment of clarity, not caring about this complete role reversal.

'Take some more poppers and I'll fuck you.'

Looking back, I know she planned all this, that she picked up straight guys and introduced them to new found pleasures from the dark side of life. Pleasures that society sees as a transgression. But I don't care. I still like pussy, but these beautiful creatures I love and I keep going back for more and more.

A spasm rippled from my arsehole throughout my body as her cock head penetrated me. I tried to push away, but got as far as the mattress and she just gripped me by the hips and leaned into me with her weight, until I was filled by what I now know is her nine inch cock. Damn was it big.

My screams into the pillow soon turned into moans of pleasure. I was lost. Lost in the decadent pleasure of this shemale's cock as it sent ripples and vibrations through my body. I was soon slamming back to meet her thrusts and as soon as I thought I'd got the measure of her, she would change up a gear.

She pulled out and I mewled like a kitten, empty and in need of her milk. The emptiness didn't last long and her fingers were soon stretching me wider than before, until she had her cock inside me and three fingers. It was like starting over again; that stretching feeling of confusion – was it pain or pleasure. It must have been pleasure as I didn't try and stop it and let her have her way with me. Hell, I'd been a submissive bottom without even knowing it.

'You want my cum.'

It wasn't a question. She knew I wanted it. In staggered breaths I said, 'Yes Jess. I want your cum.'

She pulled out, grabbed me by the hair and turned me to face her.

A glorious shiny cock was before my face, her hand wanking it slowly, peeling the foreskin back of her angry glans. She stuffed it in my mouth, grasping me by the back of my head and pushed it as deep as it would go. With short, sharp thrusts she gagged me on her cock until she was ready to cum. Pulling out, she wanked it onto my waiting tongue and fired her seed over my face.

She rubbed her cock over my face, smearing her cum all over and that had me suck it whilst it softened.

'Such a good little slut,' She said, rubbing my hair.

With her cock still in my mouth I said yes in agreement.

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She had to make it good. It couldn't be just another gift wrapped cologne set, or a gift card to Ulta. She wanted this Christmas to celebrate her newfound lust with her k**s. She wanted David and Dana's presents to be fun, kinky and perverted. That's why, after a few weeks of thinking about it and a little searching, she had finally found David's gift.David had very open tastes. He was very in touch with his sexuality; he knew what he liked, and he was willing to explore new things to keep...

2 years ago
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Shemale Surprise

This is 100% true, I know it may sound difficult to believe and I know if I read what is detailed below I’d struggle to believe it but this is what happened to me on Wednesday.I needed to take Wednesday off from work as a holiday to get some work done to my home, as the day wore on I had planned to get a tribute made, but I felt too horny to tribute I’d been to Northwich Sauna before (Which I’ve posted about before) and seen that they run a TV/TS day on Wednesdays, all are welcome to dress how...

2 years ago
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A tale of male seduced by shemalefrom rohitraj

Hi I am Rohit,I am young,very fair and handsome,well educated decent person age 26 years almost 6 feet tall living in Hyderabad,India.I am a great fan of Indiansexstories.net site and always read the sexual stories.....and compliment the people who write so long stories......i always wanted to share my encounters......but alas i dint met a single encounter.....but recently.....met an exciting one....which i am going to reveal to you people......This is my first story and i request you people...

1 year ago
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London Mein Indian Shemale Se Fuck Hua

Hi dosto, mera naam Azim hai. Meri age 23 hai aur main ek bisexual mard hun. Mujhe sex ka bohut craze hai chahe aurat ke sath ya aadmi ke sath. . Aur yeh meri pehli story ek shemale ke sath hai jo kuch saalon pehle ki hai. Agar aap logon ko meri gay stories aur maid ke sath stories pasand hai toh zaroor yeh story bhi aap logon ko bohut pasand aaye gi. Yeh kahani 2 saal pehle ki hai jab main London mein padhai kar raha tha. Meri age uss waqt 21 thi aur yeh meri birthday ke kuch dinon baad ki...

3 years ago
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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...

3 years ago
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My Sister8217s A Shemale

We are a family of four. Me, my parents and my sister. I am 23 years and my sister is 18 years old. She is very beautiful, fair and very sweet looking with small perky boobs and a very petite slender body. I, on the other, am a regular gym goer and have a very good physique, but the thing with me was that I was gay and loved gay and shemale sex. I have done gay sex a couple of times but have never been with a shemale. I always knew there was something different about my sister as I often...

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1 year ago
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Sherry got fucked by the Shemale hairdresser Shemale Sex Stories

Living in the poshest parts of New York, Sherry was perfectly happy with every aspect of her life. She was ambitious and had a great job. She earned enough to lead a luxurious life in this part of the city. The only trouble was her hectic lifestyle and how it left her with no time to date. Her last breakup was rather messy. It has been three months since she broke up with her boyfriend. The only thing she misses now is the sex. She was not much into flings and one-night-stands so finding a...

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4 years ago
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First love with a shemale

This happened around 10 years back. I never had a chance to share my experience. After getting some free time at my work recently, i thought of sharing my erotic stories.I will cut the chase and jump into action. I had been browsing horny shemale videos for a long time but never had the opportunity to spend time with. The place where i stay does not have good transgenders and 80% of them are just fake and try to loot money. I searched the craigslist and from one of the websites luckily found an...

3 years ago
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A Shemale Fantasy and my Wife Part 2

About an hour later my phone vibrated once again. It was from Carol. This time she had send me a picture of a shemale. The text read "do you think she's hot?" I responded with a YES! And I meant it. This shemale had beautiful big tits and a pretty big dick. In fact it may have been a bit bigger then mine. This was really starting to get interesting, just like Carol had promised. She was texting me dirty pictures and being really naughty. I loved it. I wanted to be naughty just...

4 years ago
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A Shemale Fantasy and my Wife Part 2

Introduction: I didnt know what I was in for. But what a ride I arrived at work, walked into my office and settled in for the day. Just as I was checking emails on my computer my phone vibrated. I took a look. It was a text from Carol. In closed was a picture of her laying in bed totally nude with her legs spread. The text read, my tight wet pussy is waiting for you. I instantly got horny. I would never dreamed Carol would send me a picture like that. I texted back I cant wait to stick my dick...

4 years ago
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A Shemale Fantasy and my wife Part 4

A few hours later I was woken up by Carol. "Wake up baby this day is just getting started" she said. My eyes opened and I was like a kid on Christmas morning. I couldn't wait to see and "feel" what she had in store for me next. Carol instructed me to shower get dressed and leave the house for a few hours. My next surprise needed some set up. I did ask she told me. Before I left Carol came up to me grabbed my dick, kissed me and said "get ready for some fun". Having no...

4 years ago
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A Shemale Fantasy and my wife Part 4

Introduction: The Conclusion Basking in the glow of what just happened, I put my head back and just passed out from total bliss. I didnt know what else Carol had in store, but I knew I wanted to be well rested. A few hours later I was woken up by Carol. Wake up baby this day is just getting started she said. My eyes opened and I was like a kid on Christmas morning. I couldnt wait to see and feel what she had in store for me next. Carol instructed me to shower get dressed and leave the house...

2 years ago
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Shemale Stewardess Seduction

Please note that this story is not written by me! It was stored in my computer for a long time now and decided to share it with you. The author's name as well as the site I found the story are not known... My introduction into the sultry, steamy world of shemales came (and I mean came!) at 35,000 feet, on a plane flight to the Northwest. I had been working myself to the bone, staying until ten or eleven at night, coming back in at six o'clock in the morning, and I guess the stress...

2 years ago
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Beautiful Shemale Sex Fantasy 8211 Part 1

Hello people, Leviathan here with my first story. To describe me, I am an average looking guy with a pint of femme body and many have said I have a great ass. Jumping into the story, this is purely a work of fiction. I request you all forgive me for grammatical and spelling errors. I made up a story by mixing a few of my fantasies and pint of my imagination, and a lot of horniness! It was around 8 pm. I set off for a 16-hour long journey to native, my train just arrived. After a fuss, I managed...

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2 years ago
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Sweet Julie Birth of a Shemale

Sweet Julie Birth of a Shemale by Mistress Tawny Suede Chapter One Is It Just a Role? The dress rehearsal for the drama club's latest production was over. The curtain fell, the audience of excited parents applauded enthusiastically. The curtain rose and the performers stepped forward to take their bows. The curtain fell again and still the crowd applauded. The two stars, Troy and Julie, took their positions centre stage, holding hands as the curtain rose one more time. They...

1 year ago
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My Vivid Memory of Sex with a Shemale Free Sex Stories and Adult Erotica Stories

I am a lonely man in his forties. I love to travel, dine and explore new places by myself. But I often wish for a partner. I got divorced early, so the little chance of being with someone was also ruined in my memory. So, each morning I would go to work, do my mundane bank job and visit my nearest LGBT bar. I am sharing my memory of sex with a Shemale and how I found pleasure in it. I am not gay or have any element of pride in me but what really fascinates me is Shemales. I believe they have...

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4 years ago
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My first time with a BBW Shemale turned into a thr

I was at the club on a saturday night and didn't really expect anything different to happen that night oh boy was I wrong, happily wrong. I was sittin at the bar gettin drunk as hell and this voice from behind me and says " hey big daddy can I sit with u ? " I look up and I see this fine, phat, thick, lightskinned woman lookin right at me. Me bein' a BBW lover and partial to light skinned black women she was a wet dream cum true.I said sure u can sit here baby if u tell me your name. She says...

2 years ago
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shemale fantasy ive read before and dream

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...

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