Three Times In One Night free porn video

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It had always been a fantasy of mine.Cross dressing and getting screwed.
I have very feminine features and long natural straight brown hair. Which recently I had shortened to shin length.
I have been dressing in womens clothing now for many months and had decided that this was the night in which I get made up totally and head out into public.
It took me a while to get ready because I wanted my look to be perfect.
I chose my favorite black lace hipsters with the matching garter belt. My stockings were new, silk and black with lace trim.
They felt do good against my freshly shaved legs and trimmed pubes.
I finished the underwear off with a black lace bra I had just bought because it matched the panties, garter and hose. I felt so good after taking a long hot bath and shaving everything I needed to. My make up turned out wonderfully with mascara accentuating my long lashes and earth tone eye shadow highlighting my coffee brown eyes and of coarse ruby red lipstick making my lips look full and juicy. My skirt came just below the knee and was a deep red colour made more red by the black stockings and hugged my little ass nicely. I put on a silk top that was two tones of blue and it was tight enough you could see the bra outline underneath. The neck line was modest but if I bent the right way you saw the lacey bra. My outfit was completed when I put on high heeled black leather boots that came to my knees and had brass buckles up the sides. A small hand bag was all I needed to hold money and house keys. A dab of a nice flowery perfume and I was in character.
The cab dropped me in front of a local bar where I was sure I could be seen but not by anyone I knew. I swear the whole ride the cabby stared at my legs.
So far so good.
I went in and sat at a table and ordered a white wine and watched the people float around the bar. As I finished my first glass the waitress brought over another and said it was from the man at the bar in the grey suit. I accepted and waved him over to sit down. He was very attractive with a chiseled jaw and salt and pepper hair. He was tall and dressed like he just came from a board meeting and introduced himself as Derrick. I shook his had and we had a drink and flirted and he did not seem to realize I was a man until we got out on the dance floor and he held me close and I let his hand wander all over my ass and it was making me a little hard knowing this man wanted to have sex with me. Although I had been fantasizing about having sex with another man I had not followed through yet but the point of no return was here and I felt this was the time to do it.
He felt the bulge beginning in my skirt and all of a sudden had this look of fear on his face.
“are you a man?”
“Not tonight I am Ruby”
“you are a freak”
“if you say so but I would still suck your cock in the bathroom if you wanted” I walked him back to the table and we ordered another drink round. He sat quietly for a few minutes and finished his martini and leaned in and told me he was going to the washroom and if I wnted to earn a hundred dollars to follow him into the stall and get on my knees. I licked my red lips and followed at a discreet distance. He checked and there was no one in the first stall so I quickly went in and he followed locking the door as I began unzipping his pants. He stopped me at first and told me not to speak. He found me very sexy but did not want to think about the fact I was a man and all he wanted was a quick hummer and he was going to get a cab home to his fiance. I just shrugged and told him to show me the money. If I was going to do this for money I wanted to see the money first. He reached into his inner pocket as I took his cock out (all four inches of it) and began jerking him slowly. He fumbled at first but produced five twenty dollar bills. I had him stuff them in my bra and sank slowly to my knees. My first blow job was going to be for money. What a night to become a whore. I licked all down his shaft and sucked his balls a little but I could tell he just wanted me to blow him so I took all of him in my mouth and as his balls tapped my chin I sucked him hard and slow. He soon has his hands on my head and was guiding my rhythm as I coated his skinny little dick with my spit, so much in fact it dribbled out of my mouth and left little strings on the end of him when I came out for air. I grabbed the base of his shaft and continued shallow sucking him as I jerked him off. It only took about two minutes to make him come in my mouth. He twitched as I drained his cock of come and licked him clean before tucking him back into his trousers and standing up.
“how was that hmm?”
“holy shit that was hot”
“glad you liked it now on your way little man”
I left the stall first checking to make sure there was no semen hanging off my face and made my way to the front door. I was about to call it a night and call a cab when I stepped outside but there was this big burley looking guy with a beard and wearing plaid shirt and blue jeans. He was smoking a cigarette by the parked cars and called out to me.
He introduced himself as Claude but I suspect that was made up. I told him my name was Ruby. He laughed and told me that he knew I was a guy. I just smiled and assured him I was anything he wanted me to be.
He smiled as I took his cigarette and took a long drag and handed it back exhaling slowly. I smiled at him and he looked me up and down before telling me he thought I was dead sexy and wanted to know what the rest of my evening held. I simply told him that I was up for anything. He was staying at a motel for a while as his wife had kicked him out because he was sleeping around with trannies. He invited me back to his hotel for a night cap and if I was interested he liked it when cross dressers fucked him in the ass. I smiled at him as hw stepped on his cigarette but.
“how ‘bout it Miss Ruby you like being a top for me?” he smiled and offered his hand.
“I would love to fuck you Claude” I said taking his hand and we walked to the taxi stand.
As luck would have it I got the same cabby that dropped me at the bar, all the way to the hotel he watched as Claude and I made out and fondled each other in the back of the cab. At one point I looked at the driver and told him if he wanted to give us free ride to pull over and I would blow him he just blushed and turned back to watching the road.
The hotel was nice and he had a room with a big bed. He tossed the keys on the table and told me to make myself comfortable while he went into the bathroom. I took off my skirt and shirt but left the underwear on and sat in a kitten pose on the bed as he came out completely naked and ready for action. We skipped the drink and went right to the sex.
I stood up and we kissed some and he rubbed me till I was as hard as a rock then crouched down and peeled off my panties before sucking my cock to its full eight inches. He moved to the end of the bed and got onto all fours.
“I believe you know what I want” he said as he wiggled his ass in the air.
I stepped up behind him and quickly drove my cock into his gaping ass. He groaned in delight as I began pumping deep into his well plowed ass. I grabbed his ass cheeks as I fucked him hard and deep the whole time he growled and urged me on. Eventually my thrusting became so forceful he was flat on his stomach as I pushed on his shoulders driving deep inside him.
“jesus Ruby you’re fucking fantastic, just keep giving it to me fuck!”
I spun him over on his back and lifted his right leg over my shoulder and put his left leg between my knees and re-entered him going at it hard and slow as I began to jerk his hard hairless cock.
The sweat on his chest and face told me he was totally about to loose it.
“c’mon stud come for me, shoot all over the place” I commanded. “don’t I turn you on hunh?”
He as if on cue threw his head back and shot giant loads of come all over the bed and my bra as he grasped the bed spread. It was so fucking hot I lost it too and came deep in his hungry anus.
I collected myself and cleaned up a bit and got dressed again by this time it was midnight and Claude was passed out naked on his bed. I left quietly and thought my night was over until I realized i left my phone at home and needed to call a taxi. The room locked behind me and the only light around was in the motel office, so I went in to see if I could use a phone.
The black guy behind the desk was tall and bald with a diamond in his right ear. He smiled knowingly at me as I entered the room and he asked what I needed. He was not worried about me seeing him checking me out as I walked to the desk. He asked me if I came from the room at the end of the complex and when I said I did he came around the desk and asked if I was a man in a skirt. When I said how did you know he explained that I was not the first one to need a phone after a quickie with Claude. He then said I was by far the most attractive and put his hand on my ass.
“you like dark meat baby?” he asked as he ran his hand up the small of my back and back down to my ass again. “cause you sure do something for me” he put both hands on my hips and I felt his warm breath on the nape of my neck. I could not believe how well the night had been it seems guys liked the sexy new me! He was wearing only a pair of basketball shorts and a tank top and I could feel his dick pressing on my ass as he freely ran his hands over my tummy and down my crotch. I suppose his aggressive approach should have scared me away but it was turning me on but I wanted him to work for it so I just pushed him away and asked him if he did that to efery girl that came in. He just put a hand on his junk and played with it as he laughed and said I was no lady just a fag in a hot girl disguise and I should be flattered a guy like him was interested.
His cock was tenting the shorts nicely and I got a look at the screen he was watching when I came in they were hidden cameras in the rooms the main screen was Claude sound asleep. He had been watching us fuck the whole time.
“thats my nightly entertainment” he said. He went around and clicked on a different screen and a Hispanic man and woman having sex popped on the big screen.
“I jerk off constantly here at night” he bragged as he took off his shorts. He bent me over the desk and pushed the skirt up as he rubbed my dick through the lace panties. I just watched as the chubby woman rode her chubby husband and this dark skinned hunk pulled my panties down and licked my asshole. I was powerless to resist as he took up position behind me and entered my ass with his huge dick. My first taste of cock in my ass hurt so good as he grabbed my hair with both hands and drove deeper and deeper into me as I watched th couple on the screen. His grip was strong but passionate and he said nothing just fucked me deep and well I reached down and began jerking myself in time with his thrusts. I was so turned on I came all over his desk and the screen where the couple was now spooning after having finished themselves.
“ah fuck baby yyou got me ready to pop” he said breathlessly as he emptied out into my no longer virgin ass. He slapped my ass as he pulled out and pulled my panties back up. He picked up the phone and dialed.
“yea I need a cab at the Northway Motel, yes thanks” he put his shorts back on and with a smile licked my come off the screen.
“see you around” I blew him a kiss as I got outside and into the taxi.
I got home sore, exhausted and ready for bed. I took off the nights attire and threw it in the hamper and cleaned the make up off and brushed my hair before slipping into bed. Just as I was drifting off to sleep my wife rolled over and put her arm over me and kissed my back.
“how did it go baby? did you like being a little whore tonight?” she said sleepily.
“mhm darling I did. Thanks for letting me do it”
“you are welcome, you’ll tell me all about it over breakfast.”
“okay”
“you must have had fun, you smell like rough trade” she giggled and went back to sleep. I drifted off feeling like a new man.

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He was late coming home — later than usual. Sondra fell asleep on the couch, waiting up for him. She didn’t hear the engine, or even the door opening. Lionel awakened her with a soft kiss. ‘You waited up for me.’ ‘Oh, baby,’ she yawned and stretched, then sat up and hugged him tightly. ‘Welcome home. Are you hungry? You want me to fix you something?’ ‘I’ll get it. Why don’t you go on to bed? I’ll be in in a little bit.’ ‘Okay,’ she sleepily agreed and swayed off down the hall. Lionel was...

1 year ago
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Sunny Leone

Sunny Leone porn, sex, and nudes! Pornstar Sunny Leone is one of few Indian actresses whose career has been very successful. She has also succeeded in founding her mainstream with plenty of works in Desi porn. She has also managed to convince a few of her friends to upload content on her site. Walk with and let’s find out what Leone has in store for us.To start with ThePornDude was very impressed with the fabulous layout, the colors, sexy pictures of Leone on the background and colorful...

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4 years ago
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Fucked by George Clooney

I awoke in a lavishly appointed bedroom with talk windows overlooking the ocean. The sand was white, the water was a gorgeous deep blue, and the coconut palms were waving in the gentle breeze.But, where am I? How did I get here and why am I here? All I remember is being in my own bed in Brentwood. Now I’m here!Then there was a brief knock at the door and in walked George Clooney! I had swooned over him for years and now here he was in this room…alone with me!"Hi, Arianna. I'm George Clooney,"...

2 years ago
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Pelle the CollierChapter 17 How the Baroness Lieselotte Climbs a Secret Staircase

They returned to Pelle's clearing and to an amply laid table. As attested by Luise's fawning around Tjark their marriage had started well. They all sat and ate their supper. Matthias and Tjark were both getting their share of good-natured teasing which they received in good humour. Afterwards plans were made for the week. They had to hurry with their latest kiln before it was too cold to dig up the clay for the coating. It was decided that both young women would help out to add more hands...

2 years ago
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Part 2 ndash The Crone The girls and the two brothers

The Crone is always the ruse, the black magic woman who attracts the young, pretty teens to help her with her ‘disability’ and her ‘plight.’ She is obese, appears ‘sickly’, ‘helpless’, ‘depressed’. The girls often have pity on her, with all her ‘homeless things’ weighing down her wheel chair. “Push me somewhere safe dearies, there are bad men always stealing my things.” The girls comply; bring her somewhere ‘safer,’ sometimes, to the ‘safe house’ where she pretends to be staying. A dilapidated...

2 years ago
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Nurse Demoness Chapter 4

Mina swooped onto the balcony of her apartment, soaked form the rain. The balcony was on the top floor, the fifth floor, and located at one of the corners of the building. Always left unlocked, the screen door provided a way to avoid her annoying self-righteous neighbor. The man had a crush on her and Mina would have eaten him already had he not been her neighbor. She tired to avoid any demonic actions that would cause alarm near where she lived. The screen slid open, and an assault of rotten...

3 years ago
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Contractual ObligationsChapter 11 Lionelrsquos Session

Lionel Fairbrother was standing in the doorway of the room, looking uncertainly from June to Allison and back again. Allison, anonymous behind her mask and wig was sitting in an armchair watching him. June was standing beside her. “I think you know what’s expected,” June said quietly. “Please don’t be concerned by my guest.” “No, of course, no Mistress,” Lionel’s stuttered response betrayed the way in which his expectations of the evening session had already been disturbed. Allison watched...

1 year ago
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Simone The Schoolgirl Part One

I looked at her with new eyes. Her hair was hanging forwards and her sweet face looked so soft. I looked at her perfectly straight legs, slightly tanned. He thighs were full and her calves had a lovely roundness to them. She had a woman’s legs - not those of a typical skinny schoolgirl. I felt my cock starting to twitch and decided the best thing would be to get this over with a.s.a.p. I moved behind her, holding the ruler poised above her glorious behind. Simone The Schoolgirl (Part One) A...

Straight
2 years ago
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Wishbone LITE

Wishbone LITE By TwoSpiritsTG ----------------------------------------------------------------------- This was a short story I entered into a TG fiction competition a few years back with a 1000 word maximum (This story is 1010 words). For the record, I did win first place. I originally wasn't going to upload it here because of how short it is, but decided otherwise and here we are. If there is demand to expand it to something more I'll gladly do...

3 years ago
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Wishbone Student TeachingChapter 5

"Mount up, babydoll!" he said. At last understanding, Christine squealed and leapt to her feet. She pulled up her skirt and wiggled her hungry red beaver at him. She needed a trim. With a wish, all her pubes fell out, then an arrow-shaped landing strip grew in their place. "Are you really going to fuck me Mr. Phillips?" she asked eagerly. "You bet your sweet ass I'm going to fuck you, Christine!' he exclaimed, reaching around to grab said ass. "It really is your only hope of...

4 years ago
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Honeys After the HoneymoonChapter 2 Back at Home

After the honeymoon was over, Jill and Joyce again picked us up. “Us”, in this case, included Vanessa, Molly Anne, and I. We went to the crew area and picked up Rachel, and Scarlett, her friend that had retrieved her toybox and lost vibrator. Honeymoons end, but ideally, they prepare for the next phase of life. In summer 1961, Rose-Marie Egger became my wife, and her stabilizing influence has kept me on an even keel ever since. Our honeymoon trip led us to the United States where I spent...

4 years ago
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Persephone

Sometimes I loved being a professor. Most of the time, really. My class is such that usually students don't take it if they aren't serious about it. Classical Mythology is not on the general education list so there are no general education credits for taking it. Teaching a specialized subject typically meant mature and dedicated students.This semester, however, my Thursday evening class had a handful of miscreants in it, one miscreant more troubling than the others. It seemed Blake...

Lesbian
3 years ago
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Hermione the Shiteater

Hermione the Shiteater Interview with Hermione Granger taken by Rita Skeeter in Hogwarts, 1st June 1998. Wizarding Wireless broadcast. RITA SKEETER. Good morning, my dear listeners. I'm Rita Skeeter, your favorite journalist, and I'm visiting Hogwarts School today. Make your wizarding wireless louder, because you'll hear the most mind-blowing interview in my career. Of course you know how our glorious and mighty Dark Lord banned all the mudbloods and blood-traitors from attending...

4 years ago
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Hermiones New School

Hermione's New School[Contains fantasy ball-, tit- and cunt-busting, castration (many, some graphic) and big tit themes]HermioneHermione sat on the broken down school bus with her arms folded tightly across her budding breasts.“I bet I finger the new girl first.”“No way - I’ll have her stink on my fingers before home time.”A chill ran down her spine and she re-crossed her arms tighter over her tender young tits. It had been a month since she had been expelled from Hogwarts and a week since her...

2 years ago
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Nurse Demoness Chapter 3

Ashkrath was an even lesser succubus than Rathae, but she ruled one of the nine districts on the plane Vitae named Desert. The demon was not having a good day, and she was listening to one of her subordinates, an imp named Pu. He was sputtering on about the current problem she was facing. "M-m-master, I can't answer where all of the souls are going," Pu said. Ashkrath looked at the imp in disbelief. How did she ever employ such a thing? She knew the answer, which was that this far...

4 years ago
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Hermione and Ron finally together

Hermione's POV Ronald That name had been floating around in Hermione's head for the past weeks. He was the only thing she could think and dream about. She would spend hours and hours laying awake in bed at night just thinking about how it would be like if she had told him that she loved him all these time. She wasn't stupid. She knew that Ron has feelings for her. But why he hasn't said anything? Why is he so afraid? Is it the war? Is it that he still has feelings for Lavender? Or...

3 years ago
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Petra Private My Molly Malone 1

Precious Princess Petra meets Molly Mallone in Paris, who looks for hot help in ordering something very erotic.Petra reads her hot thoughts through her great green eyes, so she offers her hot help for some sexy solutions.Precious Princess Petra, see her private photo below, is an expert at erotic writing as her granddad, poet Peter!Petra in Paris: source of some sexy stories to seduce our dear readers into intimate extatic erotic 'dirty dreams':Precious Princess Petra hot & horny hosted...

3 years ago
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Sex With Indonesian Maid

Hi everyone! I am Vikram from Singapore. Simply love reading stories from here since I was 20. Now I am 28. Born and grew up in Singapore. I am about 1.75m and weigh 70kg. Now I have gathered my courage to share my sexual experience with a maid. This took place about 3 years ago I stay in Yishun estate. So one fine day I was at a shop near my house buying stuffs when I saw this maid looking at me. She was Indonesian and had a great figure. She was small built about 1.6m tall and slim but I...

3 years ago
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Summer heat Hermione and Ginny

It had to be the hottest summer in years. The heat was practically suffocating and seemed to leave everyone feeling lazy. There was also a warm stillness to the air that didn’t fade even with the best cooling charms. It produced a restless feeling that wasn’t helped by staying indoors where it was somewhat cool. For the last three weeks, Hermione had stayed inside with her books. She had charmed a Muggle fan to work along with the charms so the sitting room felt better than the rest of the...

2 years ago
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Harry listening to Hermione Ginny

It was going to the fifth year for Harry Potter at Hogwarts. Lord Voldemort was now alive again, and out there somewhere. The paper had been saying a lot of mean things about Harry, and the Wizengamot Court and the Minister of Magic had tried to get Harry expelled from Hogwarts except that Professor Dumbledore had come to his hearing and had gotten him cleared. Now Harry was sitting in the room that he was sharing with his best mate Ron at Grimwauld Place that his Godfather owned and the Order...

2 years ago
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Harry Potter the Sexaholic Part 1 Hermione Grange

Harry awoke abruptly. He was covered in sweat and was all wet. This was the second night in a row had these dreams and he knew he had to start acting on them or he’d go insane. These new dreams were wonderful and even stronger then his nightmares had every been but they also left him in frustrated mood. He carefully put his hand down his pants; it was a mess and his cock was still throbbing slightly.He smiled as he remembered the dream it had been nice and he could only imagine what it would be...

2 years ago
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Road to Tombstone

It was hot. Dust-eating, butt numbing hot as I rode the trail from California into the Arizona territory. Tombstone was planning a big Independence Day shindig that year since eighteen hundred and eighty two was a territorial anniversary. Even though I was still more than a hundred and fifty miles away I'd met up with slower moving groups heading in that direction. The trail was crowded with buckboards carrying weary families, with children whining about the heat. Big, clanking wagons loaded...

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