Crossdressing Meeting A Guy Chat Room free porn video

2 years ago

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Crossdressing Hooker and the Creampie

I've always had a feminine body, slim but some female curves so I've been able to pull of being woman in public a few times already. I started by placing an ad in the local erotic escort guide with some of my best pictures and immediately got replies from interested men. I decided to call one of them who wanted to bring a buddy and we set a date at a local hotel for 8 pm. I wanted to look amazing for the first time so I started by shaving and making sure I had no body hair...

3 years ago

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Crossdressing Karte Hue Pakad Liya

Hello indian sex stories dot net friends , my name is preeti(fake name) age 20. Ye baat kafi purani hai lagbhag 3 saal pehle ki . Mai ek part time crossdresser tha aur mujhe meri chachi bahut pasand thi aur hain . To mai jab vo aur ya koi b ghar pe nahi hota tha to mai unke room mai jake unke innerwear pehnta tha . Aur jaise ki mujhe bondage bahut pasand hai to chachi ke kapde pehnke self bondage karta tha jab ghar pe koi ni hota tha . Isi tarah ek din ghar pe koi ni tha aur mai chachi k room...

2 years ago

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Crossdressing Charlie Episode 11 Under His Thumb

CROSSDRESSING CHARLIE Episode 11 UNDER HIS THUMB Prue watched him get into the car from the top of the steps. Dave, who was still standing outside of his car, stared at Prue maliciously. She returned the gesture, glaring intently with apprehension before watching him swing into the car. Dave was quieter than usual as he settled himself at the wheel. He looked unnerved, doubtful, and even a little irritated. He turned the key in the ignition and the engine revved up like a vicious...

3 years ago

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Crossdressing Domina gets a new slave

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

4 years ago

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Crossdressing for sex

The act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock...

3 years ago

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Crossdressing at the truck stop

Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...

4 years ago

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Crossdressing at the cinema

I placed an advert on Craigslist as I fancied something new. I'd been crossdressing for a while and had met a few people for fun but wanted to try something a bit more exciting. My advert was looking for someone to meet in public for sex with me dressed in lingerie. A few replies came but the one that caught my eye wanted to meet in an adult cinema in London near city road. I heard of this place and fancied trying it out. We agreed to meet at 11am in a coffee shop nearby and go to the cinema...

2 years ago

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Crossdressing internet ad part 1

I have been crossdressing for several years mostly at home going to the theaters some and to local bars. I was on my way to the Theater one night and stop at a service station and was being hit on by a couple different guys. I flirted back a little then one guy came up to me at the gas pump and said I would love to eat that pussy. I smiled and said maybe next time. When I got home it got me thinking that maybe I should go on a CD date. I looked on a couple dating and personal sites and one...

2 years ago

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Crossdressing with my Girlfriend and Boyfriend Part 3

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 3 At the rehearsal on Friday night Mrs Cartwright asked me how my mother was getting on with the dresses for the show. "She has just about finished two dresses for me, including the wedding dress," I said. "I'm sure they will be very pretty, she did so well with your costume for Dorothy last time I can't wait to see them," replied Mrs Cartwright. I...

4 years ago

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Crossdressing with my Girlfriend and Boyfriend Part 4

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 4 Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn't understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave. I sat with my own thoughts for a while and then I noticed we were not driving home. "Where are we...

2 years ago

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Crossdressing Charlie Episode 2 High Waisted Skirt

CROSSDRESSING CHARLIE Episode 2 HIGH WAISTED SKIRT "Oh Charlie, you're burning up!" said Mom. She took her hand off of his forehead and read the thermometer. She then left the room to get some medicine. Charlie took the thermometer out of his mouth, held it up against the lamp on the bedside locker, grabbed his hot water bottle and placed it on his face. He left it there for a few seconds before he heard approaching footsteps echoing from the hallway. He slipped the hot water...

2 years ago

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Crossdressing Charlie Episode 3 Relinquishment

CROSSDRESSING CHARLIE Episode 3 RELINQUISHMENT Charlie stared at the door as if it were a wave of fire rapidly heading toward him. His eyes watered and his hands trembled with shock. His could hear his mother's heels clicking against the shiny wooden floor getting louder and louder as she approached her bedroom door. Then, something electric shocked Charlie's brain which broke him free from his frozen state as adrenaline pumped through his body. He jumped to his feet and turned for...

2 years ago

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Crossdressing Charlie Episode 4 Lust

CROSSDRESSING CHARLIE Episode 4 Lust The sky was blue. Yes, just blue, not a cloud to be seen. Every so often a light sliver jet could be seen, trailing white smoke behind it. The sun hung over the city like a warm light bulb, belting its warm rays unto the necks of people within the hustle and bustle of the packed streets. People wore shorts, t-shirts, sunglasses and sun cream, making the most of the rarely seen good weather. The sounds of construction workers banging and drilling...

4 years ago

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Crossdressing Charlie Episode 5 Rachels Date

CROSSDRESSING CHARLIE Episode 5 RACHEL'S DATE Rachel sat in front of her makeup station brushing her hair whilst humming a soft happy tune. She had just dried her hair after getting out of the shower. She was dressed only her in bathrobe as she wasn't in the least bit cold because outside the sun was splitting the rocks and melting the tar on the roads. As soon as she was done brushing her hair into a silky shiny doo she walked over to her chest of drawers and began to put on her...

3 years ago

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Crossdressing Charlie Episode 6 The Tennis Uniform

CROSSDRESSING CHARLIE Episode 6 THE TENNIS UNIFORM Since Charlie and Rachel's day of sorrow three weeks ago, much has been altered in their lives. For a brief time they became closer than ever as they shared their feelings with each other. Emotions of pain, jealousy, hurt; anger and betrayal were common occurrences of feeling in their deep immersive conversations. Despite the fact that their mother felt alienated and that she was alone in the universe she still felt a glimmer...

2 years ago

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Crossdressing Charlie Episode 8 Family and Nightmares

CROSSDRESSING CHARLIE Episode 8 FAMILY AND NIGHTMARES His eyes opened quickly. The first thing that came into view was his bedroom door. His heart slowed down as he exhaled into his pillow. It was just a dream. He thought. Well of course it was! His eye's swirled about in their sockets like a startled animals as he rolled over onto his back and licked the inside of his mouth. That usual morning taste was in his mouth and he couldn't wait to get his hands on his toothbrush. He...

4 years ago

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Crossdressing Charlie Episode 9 Everybodys Crazy

CROSSDRESSING CHARLIE Episode 9 EVERYBODY'S CRAZY "What are we going to do now?" Charlie yelled over the loud rush of passing cars. "I don't know!" cried Rachel, tears streaming down her face. "Well we can't just hang around the streets all night!" shouted Charlie. Rachel didn't say anything back. She continued to walk briskly ahead of Charlie as if she knew where she was going. Dusk was rapidly descending into night and the skyline of the distant city buildings was...

4 years ago

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Crossdressing Charlie Episode 10 Prudence Svahnstrom

CROSSDRESSING CHARLIE Episode 10 PRUDENCE SVAHNSTROM The moment that Charlie was told that he would be moving out of his current home he could not help but feel a little sad at first. However, the more he thought about the prospect the more it made him feel hopeful for a brighter future. For so long he had been stuck in a never-ending chasm of darkness and now there was a light at the end of the tunnel. It was something to look forward to, something to root for and above all else a...

3 years ago

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Crossdressing Charlie Episode 12 Seventeen

CROSSDRESSING CHARLIE Episode 12 SEVENTEEN It is the 12th June, ten days after the shopping/cinema date and Charlie has not heard from Dave. He sits in the back garden on his deck chair, staring out into the dusk sky as the sun slowly sank down behind the distant housing estate. It is a warm mid-Junes evening and the sky is painted with pinks, reds and oranges across the dark blue canvas. Even the stars were beginning to protrude through the blackest parts of the sky. It is truly...

4 years ago

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Crossdressing Charlie Episode 13 Hide and Seek

CROSSDRESSING CHARLIE Episode 13 HIDE AND SEEK TWO YEARS AGO... Dave watched the raindrops roll down the windowpane and morph into one another before they dripped away. Outside, it was pelting down so hard that it looked like the rain was coming up from beneath. He watched people scurry down the street with umbrellas, newspapers, and briefcases over their heads to protect their precious haircuts. It was dreadful weather. However, he was safely inside a nice warm caf? with a cup of t...

4 years ago

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Crossdressing Charlie Vol 1 Episode 1 The School Uniform

CROSSDRESSING CHARLIE Volume One Episode 1 THE SCHOOL UNIFORM The thump of the car door made Charlie open his eyes. The sound of a second door slamming made him sit upright in the bed like a startled squirrel. He listened carefully. The ignition jerked several times before the engine started up. He was still as a statue as he listened to the low rumble of the car reversing out of the driveway. He scurried across the blankets, jumped off the side of the bed and stumbled over a pile...

2 years ago

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Crossdressing Charlie Vol 1 Episode 15 Crime and Punishment

CROSSDRESSING CHARLIE Episode 15 CRIME AND PUNISHMENT Dave's long, golden hair hung gloriously down over his bosom, and down his back like an unrolled curtain of soft velvet. Covered with an explosive overdose of fake tan, his skin looked radiantly false yet hotly sensual. His face was painted like a dolls and his makeup was over the top and trampy. Like two fluttery butterfly wings, his lashes were thick, dark, and long. His lips appeared plumper as they were coated with neon-pink...

4 years ago

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Crossdressing Charlie Vol 1 Episode 16 The Greatest Change

CROSSDRESSING CHARLIE Episode 16 THE GREATEST CHANGE Everything in Charlie's life became slow and dreary after a period of unexpected escalation. Yes, he returned home to his family after nearly being kidnapped by a psychotic blackmailer. However, that did not mean everything would immediately return to normal. There were still a lot of unanswered questions pressing on the minds of those who loved Charlie and he knew they would start asking sooner rather than later. He had prepared...

4 years ago

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Crossdressing Vignettes 2 True Story

This is from the early 1990s, when I was in the occasional habit of crossdressing in lingerie and bottoming. I don't do that any more for several reasons, mainly because at my age I just don't have the body for it any more. About 20 miles from where my wife and I lived, on the outskirts of one of America's largest cities, there was an unofficial red light district. It was basically a very poor little village that had opened its boundaries to adult businesses in order to attract some kind of tax...

4 years ago

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Crossdressing in Highschool but oddly enough my friends are alright with it

Never in your life, you thought you will be entering my school walk-in crossdressing as a girl. If you told yourself this two years ago you will be laughing at your face. But here you are swallowing your guts down into your stomach and pray to God that today is the day you die. Facing the high school doors that separate you from the inevitable humiliation. You close my eyes and push the doors open, immediately multiple eyes lock onto you. Freeze Frame Record Scratch. Let's go back all the way...

1 year ago

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Crossdressing at grandmas Part 1

100% fiction! My brother & i boarded the train bound for grandma's. During the 3 hour journey we had plenty of time to talk about the good old days when we would get into trouble chasing her chickens & how she would bake for us. She was very lonley these days & had asked for us to pay her a visit. After getting off the train we made the short walk to her house. Grandma was delighted to see us & as usual had baked plenty for us. She was very elegantly dressed in blue satin blouse,black skirt &...

1 year ago

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Meeting a Rough Old Man from Chat

It happened a few years ago. I married young and 3 years in found me living like a middle aged woman at 23, with no sex life at all. Men think it's women who stop having sex after marriage...but its men too, my husband just stopped. So I began chatting again. It was the only bit of excitement I could look forward to in a day. Here is my story:I was up way to late one night, chatting with different men, looking for some sort of conversation that stirs something up inside me. That's...

2 years ago

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Meeting Jenna for a chat

A few months after Jen and I had our first 3some with my lover Nick, she met a guy at work. His name was Martin, he was 38 years old, 6 years older than Jen, he was married with two k**s and they started having an affair together. It was a Saturday morning when she called me while my husband, daughter and myself were having breakfast. She asked if I could meet her for lunch. I asked my husband if he could watch our daughter for a while that afternoon while I met up with Jenna, Which was fine...

2 years ago

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AOL and yahoo chat rooms

Many many years ago I used to like to go on chat rooms. Just goes to show my age right? Back then, there was no Facebook, even MySpace was in its infancy. Of you wanted find girls online back then, this was just how it was done. However, it wasn't always girls I was looking for.Anyone who has payed any attention to my wife and my page, I'm not 100% hedero. For many years and still to this day, I fantasize about sucking cock. I have never followed up on this urge and I likely never will but,...

4 years ago

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The Rise of Jade ForceChapter 4 Colonel Nguyen Dies

May 1, 1975 Colonel Wynn finished assembling his rifle after having cleaned it. He had placed second in a shooting competition, right behind Sergeant Major Washington. They had tied in the regular round and had to go into a second and third round before a winner was declared. He now had a nice little second place trophy. After each competitor was eliminated, they had returned to the ready room to clean their weapons. Because of the extra competition rounds, he and the Sergeant Major been...

1 year ago

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Chaturbate Teen

Do I really have to explain Chaturbate to you? Something tells me that every dude on this planet has been to this site at least once. But why the fuck would you not? When you have access to live camgirls playing with their pussies, and you can watch them for free, why in the ever-living fuck would you want to stay away from that?!Chaturbate has a massive amount of camgirls that perform shows for you to jerk off to. That much is fucking true. So there is enough room for you to get picky. And if...

1 year ago

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Chaturbate Indian

If you are horny as fuck to see Indian camgirls and you don’t know where to turn, where the fuck have you been the last few years, you crazy mother fucker? For the few of you that have not heard by now, live cam shows have become all the rage. As COVID-19 buttfucks the planet and everyone has had to stay indoors to avoid its infectious jizz, more people than ever before are turning to camming to earn a living. Because most dudes don’t have anything to fucking do late at night; naturally, they...

2 years ago

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Chatting with Jack Chalker 3 PostChat

Post Jack Chalker Chat On Sunday December 5,1999 2:45PDT Edited by Anne-Mal Jack Chalker had just left and so... (*Anne-Mal) Now lets all go out and buy his new book!! (BillHart) Too late. I've already read it. (Stephanie) My copy is on order from Amazon! (Andrew) *Cheers* (TgDon) *Claps loudly* (sue) Thanks so much for putting this together, Anne! (Sapphire) Thanks Anne! (Darkside) Well done, Anne. A fantastic chat and you did a great job of keeping us in...

1 year ago

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Chaturbate

Who doesn't know Chaturbate, misspelled as "chaterbate" by a lot of you horny fucks! You don’t have to be old to remember when live sex shows could only be seen in the seediest joints in the worst parts of town. If you wanted to watch some girl spread her twat for you, you’d have to risk getting knifed by a crackhead on the way out. The Internet changed all that by bringing webcams to every exhibitionist slut in the world. Chaturbate.com is like a global directory of those cams.It takes some...

2 years ago

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Crossdressing Friends

I forgot about my dvd and took the picture. It was inspiration for several orgasms. A long black haired wig hung down to his shoulders and a black leather corset was squeezing his body tightly. I only wished that the picture went down further so I could see his cock. Part of me wanted to tell him that I knew. At least then, we would both have someone to share this interest with. I figured I’d talk to him about sexual interests and fetishes, see where it led. “So…Joe. What kind...

3 years ago

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Crossdressing Fun From A Womans Point of View

I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my ex boyfriend. It started one afternoon when he came back from playing basketball. I had just finished...

2 years ago

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Crossdressing With Walt pt2

Walt and I headed out to the living room and as i sat down, Walt went into the kitchen and came back with two beers. As he sat down next to me he handed me a beer and for the next several minutes we sat there quietly drinking our beers. Walt finished his first and after he put his empty can aside he looked over at me. "You were fuckin' great" he said as he moved his hand over and laid it on my crotch. We were both still had on our outfits and as he now started to caress my crotch, I looked at...

2 years ago

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Crossdressing Porn Story 2

Jack let himself in the front door. It had been a long day at the store. He’d noticed Ray’s Porsche in the garage. “Honey, I’m home.” From the kitchen came a sweet “Hi Janice how was your day.” “Pretty rough.” “Well just sit down on the couch and relax. I’ll have dinner ready in jiff.” They had divided up the house chores and Jack was glad that Ray had taken over the cooking. The meals were always delicious. Ray walked in...

1 year ago

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Chaturbate Mature

Chaturbate’s big-ass selection of Mature cams shouldn’t come as much of a surprise to anybody who ever spends their evenings, weekends or lunch breaks shaking their dicks at the site’s seemingly endless number of live camwhores. They’re one of the very biggest cam sites in the world, consistently drawing around 340 million visits a month. You’ll run into more than a MILF or two even if you’re just browsing the front-page hoes and never fucking with the filters.Today, I am fucking with those...

1 year ago

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Chaturbate Asian Cams

Ever had an Asian girlfriend? I’m not talking about some waifu you chose out of a video game or an anime schoolgirl from a hentai dating simulator. I’m talking about a genuine Japanese chick or Chinese babe, a sweet Korean college girl, or a total slut from Thailand. Ever fantasized it? Ever even spoken to a girl? Probably not, but you can change your luck for the better in the Asian section over at Chaturbate.Chaturbate.com is one of the most popular webcam sex sites on the...

2 years ago

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Chatting with Jack Chalker 1 PreChat

Jack Chalker Pre-Chat On Sunday December 5, 1999 11:15AM PDT Edited by Anne-Mal (Jeff) Hi Anne! (*Anne-Mal) Hi! (Jeff) I wanted to make sure I was here this time! (*Anne-Mal) Getting in line early? (Jeff) Yep, how about you?? (*Anne-Mal) Yep, I'm getting in line early too! (Sir_Lee) Hi guys. Long time no see... (*Anne-Mal) Hello esteemed friend from Brazil! (Sir_Lee) You know, I probably only discovered Chalker because one of his books had "Brazil" on the...

1 year ago

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Chaturbate Ebony

Jungle fever is one of the most serious afflictions of the 21st century. The Internet is both a major contributor and cause of the situation, as well as one of the primary solutions. You’ve probably spanked it to some of the free and premium Black porn sites I’ve got listed on ThePornDude, but have you tried the Ebony cams at Chaturbate? They let you interact with beautiful, naked Nubians instead of just watching their flicks.Chaturbate’s the biggest webcam porn site out there, with thousands...

1 year ago

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Chaturbate Performer

Who’s your favorite CB Performer? I know that’s kind of a tricky question when it comes to any adult site, and Chaturbate is the giant of webcam sex sites. Hell, I have a hard enough time choosing my favorite camwhore performing on the platform at any given moment, let alone trying to name an all-time favorite. But, of course, it’s OK to have many, many favorites, as I do. The only time that might become a problem is if they’re all putting on live pussy-diddling and butthole-fingering shows at...

1 year ago

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Chaturbate BDSM

Chaturbate’s BDSM shows don’t always take center stage on the website. After all, most masturbators are looking for something that’s arguably a little more vanilla, like pretty girls flashing their tits, twerking, or diddling themselves for the webcam. Some perverts appreciate something a little bit kinkier, though, so I thought today might be a good day to dive into the cam giant’s live offerings in the world of bondage and discipline, dominance and submission, even sadism and masochism. Where...

1 year ago

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Meet In Chat

MeetInChat! Tired of jerking off to hot pictures of kinky babes by yourself? Are your friends sick of you cluttering up the Discord or group chat with slutty chicks? Well, first off, you need some new friends who appreciate good shit when they see it. Second, I get it. Fapping can be a lonely experience. Some of you fucks resort to anonymous cam sites. Others take to anonymous message boards. But I’ve got something a little different. A perfect mix of those kinds of sites. Like an incredibly...

1 year ago

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Chaturbate Cosplay

We all know about Chaturbate.com in general, but you haven’t had the opportunity to explore all the crazy categories and genres the platform offers. Specifically, one genre that caught my attention recently is cosplay cams. I mean, did you know that there are several girls out there with sexy-ass costumes they use to transform themselves into the chicks of your dreams? Well, in a matter of moments, by just putting on a piece of latex or an outfit, a girl can match the appearance of your...

1 year ago

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Chat Room

I found an anonymous chat room a few months ago. Some chat rooms were about hookups, and I chatted with a few women just for fun. I didn’t meet up with any of them since my sex life with Laura was excellent. Then I found a swingers chat room. I had talked with Laura about swinging. She didn’t like the idea of having sex with random men, but she didn’t drop the discussion right away and seemed somewhat open to the idea. We’d discussed having me watch her with one of my friends, Albert, but...

2 years ago

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Groomsman

(Inspired by a true story) Groomsman Kevin and Jessica had been dating for the last two years and had been engaged for the last six months. They were ready to get married, settle down, and have a family together. However, controversy soon arose as the wedding plans were being formulated. Upon given the list of groomsmen by Kevin, the always curious Jessica did a background check on them all. Nothing too serious, just an online program that looked through their criminal histories,...

4 years ago

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The Hot Chat Room

Several years ago, chatting in an online chat room was a nightly ritual for me. I never had any intention of ever meeting the people I talked to do to the fact that 98% of them were nowhere remotely close to me. I would spend maybe an hour or two every evening enjoying random conversation with whoever happened to be in the room at the time, I had my buddy list like everyone else but it was always fun to chat with somebody different occasionally. I spent most my time in one particular themed...

2 years ago

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The Mailroom

       Deidre Simmons gets a lot of attention in the office. A lot of . . . inappropriate attention. It's not uncommon for her to find a pair of amorous eyes zoned in on her tits or ass, or have a superior whisper something in her ear that would have him out on his ass faster than he could blink. But it doesn't bother her, either. In fact, she welcomes it—revels in it, and will even get a little piqued when someone ignores her.       Her friend, Samantha, chalked it up to the nasty divorce...

1 year ago

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Chaturbate Squirt

Remember hot and humid summers as a kid? Nobody had a pool in my neighborhood, so if you wanted to cool off with your friends, you had to find a hose. By attaching a sprinkler to it, you could turn the front yard into your own six flags water park. We would burn the day away, running back and forth all afternoon. Good times.Perhaps that’s why we love to be hosed down in pussy juice as adults. It’s nostalgic to a time of our lives we all cherish. Or perhaps we are all godless heathens bent on...

4 years ago

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chat rooms

Introduction: a fantasy we all think about, and i finally made it come true We start chatting via an internet chat room, out conversations become extremely heated and we both play with ourselves as we chat. Chatting about our sexual fantasies, giving and gaining great pleasure from detailing every sordid detail. After several chats, we know every detail of each others sexual tastes, while holding onto some secrecy with only knowing each others screen names&hellip, both secretly wanting more....

3 years ago

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crossdressing boy

I had seen porn mags and had learned to jerk off from a couple of friends at school. I loved it and would jerk off every time possible. My mom left for work later than my dad and I saw her often in just panties and bra coming out of the bathroom before she would dress and leave or work. She was about 5'5", just a little chubby with big breasts and big nipples. I had noticed her hard nipples when she was in a bathing suit. My mom was often in my mind when I jerked off. Not only did I think of...

2 years ago

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Crossdressing I Got Fist Fucked

I was feeling horny so I put on my blue satin dress with white polka dots, satin panties, my white satin gloves, garter belt & flesh colored stockings. Then I put on some deep red lipstick and lip gloss and topped it off with my blonde wig. When I looked in the mirror and saw the sweet hot girl looking back at me I knew I’d find a guy who wanted to fuck me tonight. I posted a picture of myself on Craiglist and within minutes I had half a dozen guys messaging me so I invited them all over. ...

3 years ago

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Crossdressing for sex Pt 2 Getting fucked

Expecting my lover to be sitting there impatiently waiting for me I am surprised to see him leaning against the wall calmly. He too has changed his outfit from when he first arrived. At the door he seemed rather plain and I was kind of disappointed. He wore a T-shirt and jeans with some fairly tired looking boots. I hadn’t noticed him carrying anything else so I assumed I was the only one to be in leather. As it turned out I was absolutely wrong.Before anything else what struck me was how hairy...

2 years ago

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Crossdressing with Walt

Carmen and Ann had taken off for a ladies day of shopping and such and just as soon as they had left, Walt called me up and after a bit let me know he was in the mood for a little kinky stuff. I finally got him to admit he was wanting to dress up in a nice sexy outfit and was wondering if i would like to too and come down for a little fun. I agreed and went into my closet and came out with a nice black lace bustier with straps, black stockings, panties and a pair of black, ankle strap high...

4 years ago

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Crossdressing and Jocks Part 1

what they don’t know is that I still dress in women’s clothes to this day.I always longed for my sister to leave the house so I could sneak into her room and wear her panties. My parents running on on me wasn’t a problem because my dad lived across the country and my mom had to work two jobs, so growing up, I pretty much raised myself. I was a year younger than my sister, and when she hit puberty, that’s when the fun really began when her wardrobe updated with bras, thongs, crop tops, short...

3 years ago

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Crossdressing Sissy Desires Part 1

I always knew that I was a submissive little sissy. Ever since I was little. I would raid my mother's panty drawer while she was away at work. I would always look for the pretty colored ones and ones with lace. They felt so soft against my smooth ass and sissy clit. I would run to the bathroom with my armswrapped around panties of different varieties. As I locked myself in the bathroom I could feel my sissy clit throb and drip pre cum. Quickly, the clothes of my pretend life would find their...