Crossdress Fun free porn video

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We have all had those experiences of meeting someone on-line and chatting and things really get hot and exciting and then the huge let down when the person leaves you hanging with a hard-on or even worse when the time comes to meet they don’t show.

Well this story is one with a happy ending.

I met Paul (not his real name), on line and we chatted for ages. He was from a town about an hour away so on-line chatting was really our only safe way of communicating. When he found out I was into cross-dressing, our on-line chatting became really sexy and exciting for both of us. We chatted whenever we could and we both starting to explore our fantasies with each other, which in turn led to many an orgasm on both sides. I wear panties to work just about every day and whenever I could, I would also cam for Paul. These sessions were especially exciting as I would wear the panties of Paul’s choice and then go about doing what he would like to see which always ended with an explosion on my side. More often than not it would be in my panties and as I would later discover this was all part of what turned him on the most.

After nearly a year of chatting and exploring our fantasies on-line, we eventually agreed to meet. We arranged to meet at a hotel midway between us for a drink and a chat. I still remember being so nervous when the day arrived. I had met other men and women over the years but this time it just seemed different as it had taken so long and we had chatted about so much. When I arrived at the hotel he was already there seated out front with a drink and watching the ocean. I walked up and as soon as he saw me he stood up, smiled and took my hand. There was no one else within earshot and the first words out of his mouth were, “Hi Samantha, it is an absolute pleasure darling.” Just seeing him, feeling his hand holding mine and calling me Samantha, had me almost explode in my panties right there and then. He must have seen the effect as he smiled and invited me to quickly sit before my legs gave way.

We sat and chatted over a couple of drinks and it was obvious from our hushed conversations that we were both really enjoying the meeting. By now I was exceptionally wet in my panties. Paul wanted to see what I was wearing and we agreed to meet in the toilet. I left before him and a couple of minutes later he arrived. He coughed to let me know it was him. I opened the cubicle door and let him in and then locked it again. He moved up against me as I leaned against the wall. With him whispering in my ear how much he had been dreaming about this moment, I could feel his hand between my legs. Finding my hardness, he gently rubbed it through my trousers as his lips found mine and then his tongue was probing and soon our tongues were tasting each other. We kissed passionately, my breath catching as his hand was now unbuckling my belt. Then my trousers were falling to the floor and he stopped, stood back and stared at me in all my glory. Standing there in my panties, stockings and suspenders.

Then he is leaning in again, telling me that I look so damn sexy. Kissing me again as his hand finds it way between my legs again and he began gently rubbing my hardness through the silky panty material. By now I was oozing precum in my panties and he could feel how wet he was making me. I wanted to touch him but he would not let me. He told me to just go with the moment. I was so excited and soon without warning I was suddenly exploding right there and then in my panties. My finger nails digging into Paul’s shoulders and back as I lost control and succumbed to the pleasures of release. Paul continued to gently stroke me in my panties and the feeling was so intense that it felt like I was cumming for ages. We stood there kissing long after the orgasm was finished and Paul just continued to spread my cum all over my panties. Eventually he lifted his hand and offered it to me. He whispered in my ear that I should taste. I licked his fingers ever so gently to start with and then sucked each one wanting to get every drop but the most amazing thing was that I found it so erotic. Then he is telling me how sexy and exciting this was and I have just made his day. I wanted to touch him so desperately but he would not let me. He then said he was going to have to go but that he wanted to meet at a hotel for an extended private session. Driving out of there that day with cum soaked panties left me looking so forward to our next meeting.

We stayed in touch and enjoyed a few more sexy cyber and cam sessions and then about 5 weeks after the 1st encounter he told me he was brining his car to the city for a service and would be in town all day while he waited for it. We arranged to meet at a hotel for the day. This time I was there before he got there and was dressed as requested. Black satin and lace corset, silky panties with lace front, thigh high stockings, heels, full make-up, painted nails and wig. A knock on the door and I am opening it to find a smiling lustfull looking Paul. No sooner is the door closed and he is kissing me passionately. He stops long enough to take a step back, look me up and down, he takes my hand and has me twirl to give him the 360º view and then leads me to couch in the lounge. He sits and then has me sit on his lap. He tells me how much he has been dreaming of this and then our lips meet again. This time he is so gentle and slow. Kissing me so softly yet so erotically, then moving to my neck and gently kissing up to my ear and then I can feel his tongue teasing my ear lobe, then a little nibble. God by now my hormones are raging.

Then back to kissing and now he can feel and hear the effects he is having on me. I am battling to prevent the little moans of pleasure from escaping. We both love kissing, my one arm around his neck, my one hand on his face as I can’t get enough of him. Then his hand is exploring my body, feeling me through my satin corset. My nipples are erect and he slips his hand inside to discover them and to gently tease them with the tips of his fingers. First one and then the other. My body is responding to every little touch now. Then his hand is exploring further south now, finally arriving at my silky and lace panties. My hardness is tucked between my legs and soon his hand discovers the wet patch of panty covering my hard cock. I breathe a deep moan and like before he gently proceeds to touch, tease and rub my harness through my panties. I moan to him that I so want to feel him. I can feel his hardness pressing against my panty cover arse. He just tells me to be patient.

I lost track of all sense of time as we sat there kissing while Paul went about touching, teasing and rubbing and each time I thought I was going to explode he would suddenly stop touching me and just kiss me. I kept telling him he was driving me crazy and he would just say, “I know. I will let you cum when the time is right” He would run his hands up and down my stockings and then always come back to my now soaked panties. He had me oozing precum in them and he kept telling me how wet I was getting and how much he liked it. I am not sure how long it took but eventually I reached the point of no return. My back arched and I felt his hand really apply pressure between my legs as he pressed down on my hard throbbing cock and suddenly I was exploding in my panties. He kept his hand in place and continued to apply pressure with a little stoking movement up and down my hard cock in my panties as I continued to fill them. I was so caught up in the throes of pleasure and could not prevent the a****l sounds escaping me. Like before he did not stop and once my body had finally stopped with the shaking he very gently continued to stroke my panties and tell me how amazing that orgasm was to watch and to experience.

I lay off to one side on the couch trying to recover but the sensations just kept coming. My legs were over his legs, slightly parted with his hand still gently rubbing all the cum through my panties. I could feel I was still pretty hard. He was looking at me and smiling and all I could think of was his hard cock. I told him I so needed to feel and touch him but still I was told to wait. Then he lifted my legs, extracted himself from beneath them, knelt, had me lift my bum and then he proceeded to remove my panties. He inspected them and then revealed to me just how much cum I had just produced. He then offered the panties to my lips and had me taste my juices. I was so turned on that when he asked me to lick and suck them I was almost like a little slut on heat who could not get enough of my own cum. I sucked those panties like they contained the last drop of cum on this earth. He sat there with the biggest smile on his face watching me.

Then he stood, walked into the bedroom and returned with my little vibrator and some lube. God I could not believe this. This time he knelt on the couch and spread my knees. His lips were on my stockings and worked his way up my legs to my thighs and then eventually to my semi hard cock. Then he was licking, teasing, gently stroking and then I was in his mouth. Oh my god I was in heaven. Then I felt his finger probing my tight hole. I could feel the lubricant being applied and then his finger finding its way inside. He started to gently finger my tight hole while his lips, tongue and mouth worked my now throbbing cock. I was back in that space of pleasure that just takes hold of you. Then I heard the vibrator and felt it probing and then it was inside me. He worked it ever so slowly in and out. Then he was slowly fucking my tight hole with it as he really worked my cock with his mouth. I could feel the orgasm building, almost as if it was coming from my toes and working its way up. I don’t think I lasted another 5 minutes and I was cumming for a 2nd time, back arched again but this time the orgasm was from deep within me and not just cum oozing from my cock. I could feel my muscles clinching around the vibrator, not wanting to let go as my whole body shook with spasms which seemed to last forever.

I just lay there, totally spent, not wanting the moment to end. Paul got up, fetched me some water and then sat there with me as I recovered. He proceeded to tell me that we had just lived out his fantasy. He had always wanted to do that and to watch as the person lost total control for him. I told him that I needed to feel him and to satisfy him and he informed me that I had just done that by allowing him to have his way with me. I almost begged him to let me touch him and he told me I would soon. When Paul was happy that I was not going to pass out on him, he finally stood in front of me. He proceeded to tell me that he hoped that I would not be disappointed but that he was rather embarrassed as his cock was not very big. I have never been one to judge a guy by his cock size and told him so. I was also quick to point out that I liked small to average size cocks and when he eventually unzipped and revealed his cock I could see it was quite small. However it was beautiful. Cut and with such a beautiful head. I looked up at Paul and I think he could see the desire in my eyes.

With him standing there, I knelt in front of him, pulled his pants and underwear all the way down and helped him out of them. I then proceeded to slowly take his cock, all 4½ inches which was now very hard, in my mouth. I slowly licked, sucked and teased it hearing his moans of pleasure. He allowed me to alternate from teasing just the head and then taking all of him into my mouth. He would gently hold my head in place keeping all of his 4½ inches in my mouth for some time. I was so hungry for his cock by now and had other ideas of wanting to feel him inside another hole of mine. It was the perfect size for my tight hole.

With his hands on my head, holding my hair, he started to slowly thrust his cock into my mouth. I could almost feel his wanting to fuck my mouth. So I just relaxed and let him guide me. My mouth open, tongue flicking and teasing when I could, I slipped my hand up and took hold of his balls and gently squeezed. This brought another moan from him and his grip on my hair tightened. His thrusting movements got a little more intense and I could feel his balls start to tighten. Then he was saying he wants to cum in my mouth and suddenly without warning he is cumming. At first I was not sure and almost pulled away but then suddenly my hands were on his arse and I was pulling him into my mouth. I was so turned on too that I just wanted to feel and taste his man juices. He held me like that for a full minute or so as shuddered and filled my mouth. He did not cum as much as I thought he would but there was certainly enough for some of it to escape and run down my chin. When he was spent he sat down on the couch and pulled me up next to him. He leaned over and kissed me, tasting his juices, noticing the dribble down my chin, he used his finger to scoop it up and then presented it to me which I happily licked and sucked off his finger. Then he leaned in again and kissed me tasting his juices on my tongue.

We spent the next hour or so just chatting, recovering and enjoying each other’s company. I discovered that he was so nervous about me not liking his small cock and the fact that he liked to be in control. He was worried that I would not allow him to do what he had done to me. I let him know that I loved the way he made me cum, the way he did it, and that I always liked a man that knew what he wanted. I told him that what he had done to me was so damn exciting and hoped to be able to experience it again.

We parted company that day and we did meet another 3 times after that when the car needed servicing. Every time was pretty much like the first, with him having his way with me first and then allowing me to pleasure his cock. After that Paul left for another job and another city, so we have been left with only the net to keep our little sessions going. Just wanted to say thanks again for everything Paul.

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Hello everyone..I’m harsh aka ayesha..I’m a regular reader of Indian sex stories and always search for stories of gay crossdressers.Before starting my first real life gay experience let me introduce myself..I’m a 24-year-old boy who wants to be treated like a teenage girl..Wants to be pampered.Wanna be treated as a wife for my man at home.His girlfriend when we are outside and as his slut when we are in bed..   I come from ranchi..I am slim, fair and height 5’8″..I m very curious about sex.I...

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...

3 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...

4 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...

Transsexual
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 &...

Incest
3 years ago
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Crossdressing Fun

The meeting had been arranged for Friday morning, this would be the first time anyone had seen me dressed. I felt nervous and excited at the same time, I planned to wear a pair of nude sheer tight, black satin thong, black high heels and a shimmering silver, figure hugging, long dress with a split up to the thigh.Friday arrived and after getting up, I slipped on my tights and thong beneath my work clothes. I set of on the short drive to Antonia's, upon arriving I was greeted by her dressed in a...

3 years ago
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Fuck A Cheerleader Fundraiser

Fuck A Cheerleader Fundraiser Let’s have a “Fuck A Cheerleader Fundraiser.” It was a ridiculous idea to say the least but it certainly got everyone’s attention when I said it during the meeting. The ladies on the committee were appalled and called me a sexist pig…and that was the most polite thing that I had heard. The men laughed but I knew that they all wanted to fuck one of those amazing young ladies as much as I did. Anyway the meeting was a shamble after that and it broke up with...

3 years ago
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The F4F Fundraiser

The F4F Fundraiser Our university has a preschool on campus for the children of our older students and our younger professors. The annual “F4F” Fundraiser covers the expenses and there is no cost for the parents of those children. The “F4F” Fundraiser was started by our Sororities with the financial help of our Fraternities. “F4F” stands for “Fuck For Five.” The full name of the fundraiser is: “Fuck the Sorority Girl, Student, or Professor of your dreams for five hundred dollars…all...

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