Halloween Cheerleader Fantasy free porn video

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Halloween is supposedly a good time to be a TGirl, a time of year when society seems OK with a guy dressing and acting like a girl. Several times on or around Halloween I have walked through Macys or a mall and had salesladies call out "Nice Costume". Or, I as I go into a 7-11 or supermarket, and a couple walks by, the woman will smile and say to her boyfriend, "Hey, next year, let's dress you up as a girl". What's that all about? On the other hand, if my wife and I are invited to a Halloween party, she will definitely not want me to go as a girl. Something about looking too good, or more like looking too practiced at it. When I first started to go to Halloween parties in drag, I would just "dress as a girl". Over the years, I have figured out that it is much better to wear a girl's halloween outfit than just to dress as a girl. Last year, I decided to go to a more mainstream party for Halloween. A family (that I don't know) lives about 3-4 streets away from my house. Every year they have a large party on the Friday night before Halloween. They have several kids in high school and college and usually there is a large crowd of people of all ages at the party. I figured with people in costumes I could crash the party. Friday morning I started to get ready. I took a shower and shaved my chest and underarms. Then I shaved my face as closely as I could. I then took a bath and shaved my legs and arms. After the bath, I rubbed perfumed lotion all over my legs, arms, and chest. I quickly put on some makeup, threw on a miniskirt, a top, and some flip-flops and went to my local nail place for a mani-pedi. This nail place is run by a Vietnamese family. I have been in there 2-3 times before for pedicures and sometimes manicures. I walked into the shop and smiled. One of the girls asked me to pick out my polish and wait a few minutes. So, I browsed through their polishes and picked the darkest & reddest red I could find. I sat in the pedicure chair and the older woman started to get the foot bath ready. A cute young Asian boy was going to do my pedicure. I asked for a French manicure style pedicure. It was the first time a guy had given me the pedicure - before, it had always been the old woman. Was it my imagination or did he rub the lotion into my calves longer, deeper, and higher than the woman had done previously. I enjoyed the attention and smiled down at him. When my pedicure was done, I moved over to the nail station. I sat down for the manicure. A younger girl in her twenties was going to do it. I asked for acrylic nails and said make them long when she asked about the length. I am always amazed how long it takes to get acrylic nails done, but just enjoyed my time in the shop as other girls came in and out for their pedicures and polish applications. At one point, the girl doing my nails smiled and laughed a bit as she talked in Vietnamese to the nail girl at the next station. I smiled too and thought I was channeling Elaine Benis from the Seinfeld episode where she brought George's father to the nail store to spy on what the Korean ladies were saying behind her back. She asked me to pay before she applied the polish, so I wouldn't smudge the nails while getting money from my purse. I paid and gave her a large tip. She then applied the pretty red polish. Then, I moved to the front of the shop with my hands under the drier and smiled at the customers as they came in and out. When my nails were dry, I went home and later in the afternoon got ready for the party. I did my boobs/cleavage in the usual way: I pulled my chest fat together and applied 2 pieces of NexCare 3M Flexible clear tape (it doesn't tear the skin), put on a two-sizes too small strapless bra and put my Fredericks of Hollywood falsies in them to push up the boobs a bit more, then I put on my regular Victoria Secret's bra with my PALS fake boobs (I bought on the internet.) I put some blush around the cleavage and the look is pretty nice. Then, I put on my latex vagina, that I bought at some Canadian internet site - same place I bought the PALS. The latex pussy ties around the back and I like the look it gives me when I look at myself in the mirror with my bra on and my pussy. I bought the version of the vagina with an opening for a guy's penis. I have never tried it and doubt it would work very well, but tonight I threw a tube of K-Y jelly into my purse just in case the occasion arises. I then put on my sexy cheerleader outfit (from trashy.com) and my highest heels and my largest CZ stud earrings. I put on my makeup, perfume, and a long blond wig that I styled into a pony tail. While getting ready, I had a couple of glasses of wine. The wine makes me feel good and a bit relaxed and, I admit, sometimes the more I drink, the better I look in the mirror. I grabbed my pom-poms and I'm ready to go off to the party! I parked a few houses away from the party house. I waited for a large group of people about to go in and followed them into the house, pretending I was with that group. I quickly headed to the kitchen/dining room area, got a glass of wine, and some hor d'ouerves, being careful to eat them without smudging my lipgloss. A guy across the room dressed as a vampire smiled at me and started to walk towards me. I recognized him as someone else in the neighborhood. I have never met him or talked to him before, but I sometimes see him working in his yard, while I walk my dog. He introduced himself as Doug and I told him my name was Angela. He motioned to the next room where music was playing and people were dancing. I put my wine glass and purse down and we started dancing. After a few fast songs, a slow song played and he pulled me close to him. I could feel his hand on my ass and his hard-on pressed against me. I smiled up at him and let him nibble my neck as he pretended to be the vampire and I played along as the cheerleader victim. This went on for a few minutes and I enjoyed the feelings, until suddenly he bolted as if he had seen a ghost. I figured out his wife must have just come into the room, as a woman dressed as a witch gave me the evil eye. I just smiled back. I then noticed the host and hostess' son in a group of other college students, too cool to wear a costume, all wearing jeans and football uniform tops and drinking beer from longneck bottles. I smiled at the son and he came over to me and asked me to dance. I said: "Sure, if you get me a beer." He handed me his beer bottle and I looked at him while I suggestively put my lips on the top of the bottle and took a swig. We started to dance. Within seconds, he whispered in my ear: "Hey cheerleader! I like to fuck cheerleaders. Wanna fuck?" I pulled close to him, nibbled his ear a bit, and whispered back, "I wanna fuck you so bad, I am getting wet just thinking about it. Where can we do it?" He grabbed my wrist and I followed him as he pulled me along up the stairs, my high heels clicking on the wood steps. He tried his bedroom, but the door was locked and we heard voices within. I followed him down the hall to another bedroom, lit only by a nightlight, but visible enough to see this must be his sister's room - stuffed animals on the bed, cosmetics on the vanity, girl's clothes lying around. He locked the door. I said "Let's do it standing up, against the door", where I could see my reflection in the vanity. He pulled his shirt off. I pulled down his pants, then lifted my skirt and pulled down my panties. I saw him steal a glance at my pubic hair and pussy and smile. I said: "Sometimes, I am pretty tight", as I removed the K-J jelly from my purse. His penis was swollen, but on the small side, which is good as I was afraid my vagina opening was too small. I slathered some K-Y jelly onto his cock, and said "Let me guide it in." I stood on my tiptoes, as he was tall, guided his penis with my left hand, as I grabbed hard on his shoulder with my right hand. He was soon inside me and he quickly started to move in and out. I grabbed his shoulders with both hands and rocked with his motions. I stole a glance of myself in the vanity mirror and was overcome by the various feelings and thoughts: standing on my high heels, with my stud earrings in the holes in my ears, his tongue in my mouth, my taped up boobs, my long fingernails holding his strong muscles, and of course, his penis inside me, barely rubbing against my tucked-back penis. And in my mind in my fantasy I am the prettiest and most popular girl in school, captain of the cheerleaders, in my own bedroom, being poked by my boyfriend, the quarterback of the football team. While the moment seemed to last forever, in seconds he came, a bit premature I would say. He quickly asked me the usual guy questions: "How was I? Did you come?" In the split second, as he started to come, I had done my best Meg Ryan impression (from When Harry Met Sally) of a fake orgasm, and lied, "Yes, I did! You were great!" I quickly pulled up my panties and we collapsed onto the bed and started to neck. Within minutes, he was getting hard again. This time, I went down on him, and slowly sucked him off until he came in my mouth. He said, "That was the best blowjob I ever had! I wish my girlfriend was that good at it." I said that I have a lot of experience in that area and would be happy to teach his girlfriend if he wanted to do a threesome. He didn't think that would be a good idea. So, I found a bathroom to clean up and fix my makeup, then went down the stairs, went out to have a cigarette, then got in my car and headed home.

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A Saturday of Cheerleader Pleasure Ch 07

It was a sunny and beautiful Saturday morning when I arrived at the airport with my beautiful girlfriend, Becca. Normally, it was difficult to find parking near the airport. However, luck was on our side today. There was an available parking spot that was relatively close to the airport doors. “We're here,” I told Becca, as I parked the van that I recently rented. “Thanks again for the ride, dear,” Becca said, as she unbuckled her seatbelt. “You're quite welcome,” I told her. Becca was heading...

Group Sex
4 years ago
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A Saturday of Cheerleader Pleasure Ch 07

It was a sunny and beautiful Saturday morning when I arrived at the airport with my beautiful girlfriend, Becca. Normally, it was difficult to find parking near the airport. However, luck was on our side today. There was an available parking spot that was relatively close to the airport doors. “We're here,” I told Becca, as I parked the van that I recently rented. “Thanks again for the ride, dear,” Becca said, as she unbuckled her seatbelt. “You're quite welcome,” I told her. Becca was heading...

4 years ago
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Cheerleader Slaves Chapter 7 and 8

Cheerleader Slaves By Heather2837 Chapter 7 - The Cheerleading Squad "Welcome girls. Christy told me you would be the most beautiful cheerleaders that I have ever seen. She did not exaggerate. You are all going to be the most exquisite and beautiful harem of slaves that anyone can imagine. Welcome to your new life. You may all call me Master Bob!" The look on the five girls was priceless. This had to be one of the prettiest and sexiest cheerleading teams Bob had ever seen. Every...

2 years ago
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The Young Cherry Cheerleader Pt 3 The Young Cherry Cheerleader Cums of Age

CHAPTER 1 As Jennifer Wilson rolled out of bed on that Friday morning in early December to get ready for school, she did so with unusual enthusiasm. It was her sixteenth birthday – "age of consent" in her home state. Her best friend, Angie Walker, had pointed out the significance of the event. It meant that she could now legally have sex with anybody she wanted. All of those men, who had backed away from the thought of having sex...

4 years ago
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Halloween Bash

Hey group, I thought this one up on the fly after my wife and I came back from a ghost hunt at an abandoned insane asylum. Now you know why I write what I do… Wanted to give you all a flash story just for the fun of it. I hope you enjoy it. _________________________________________________ HALLOWEEN BASH There is one holiday I like more than any other. Halloween. The fun of decorating your yard, kids running around collecting candy and wearing costumes is better than the other holiday...

2 years ago
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Halloween Surprise

I have to say that I firmly believed all of the above just a few short years back as summer ended and September led into October. At the time, if you recall, I was recently divorced and living in the city. I was doing fairly well in a managerial position at a small company my boss John had founded. It probably didn't hurt that I was seeing his wife on the side while he was working long hours at the office. It also didn't hurt that I was going out with a hot looking 23-year-old named Joyce....

2 years ago
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Halloween Personalities

"I should have followed my instinct and not attend that party," I said to myself as I entered my room and removed my Halloween costume.As I undressed I had to concentrate to clear the image of the full red lips and tiny pink tongue of the Corpse Bride licking and kissing the head of my cock. Just thinking about it caused my groin to stir."How did this happen?" I asked myself.It had not been a good end of summer. First, I lost my job and struggled to find another. By the time I did, I was broke...

Incest
4 years ago
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Halloween Personalities

"I should have followed my instinct and not attend that party," I said to myself as I entered my room and removed my Halloween costume.As I undressed I had to concentrate to clear the image of the full red lips and tiny pink tongue of the Corpse Bride licking and kissing the head of my cock. Just thinking about it caused my groin to stir."How did this happen?" I asked myself.It had not been a good end of summer. First, I lost my job and struggled to find another. By the time I did, I was broke...

Incest
3 years ago
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Halloween at Work

Halloween at Work This is a true story...sort of. It is also a completely original work by me, and should be remembered as such. Thank you. Laura _________________________________________________________ Almost a year ago, just after Halloween I was in search of a job. It just so happened that a former manager, and personal friend of mine was looking for another person to work for her at the store she...

2 years ago
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Halloween Swing Night

Halloween Swing Night by Tanya Fly "For the hundredth time, yes, Tommy, you can pull this off," Gina said as she applied the final touches of makeup to her husband's face. "You'll look great and all the girls are going to love it! You'll be the hit of the party, and very popular." "I don't know, Gina. What woman wants to have sex with a someone dressed like a French Maid?" Tommy smiled as he realized what he had just said. He knew that lots of women liked having sex with...

2 years ago
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Halloween Party

Halloween Party by Suzi (Johnson) Thomas "Hi, dear," my wife said when I walked into the house, "how was work?" "Not bad," I replied, "we landed that new account, so the boss was thrilled. What's new?" "We're invited to a Halloween party, a costume party, at the Peterson's Saturday night. Do you want to go?" In truth, we hardly knew the Peterson's, having been introduced by a friend of a friend, and we usually didn't really celebrate Halloween. "I guess so, sure, why not," I...

3 years ago
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Halloween Delight Part One

Halloween Delight; Part one: When I was young, I was only allowed to play in the basement. The upstairs was off limits to me as a play area. I could play in my room, but that was it, other than the basement. This was fine with me, as I found a lot to play with down there, and it was all mine. When I was either 5 or 6, I found a box full of dresses. They were from the late 1800's or the early 1900's and made of silk. They had full skirts that flowed to the ground and long sleeves....

2 years ago
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Halloween Spirit

Halloween Spirit By Morpheus I stood in the middle of the office floor, looking over the cubicles and office walls which had all been covered with Halloween decorations. The company of Danner, Dyson, and Dexler...or DDD as most people called it, had always supported holiday cheer, almost regardless of which holiday it was. But since Halloween was Mr. Dyson's favorite holiday, it tended to get a little extra attention. Today was Halloween but most of the employees were thinking...

3 years ago
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Halloween For LIfe Part 2

Anna felt bad about abandoning Jordan like that. She did think that they would be able to have a spa day together. She had no clue they would separate them like this. As she walked with her stylist she confided in her. "My sister is just a little nervous about who works on her hair, and face. We're new around here and she just doesn't want anything real drastic done," Anna explained. "Could you just pass that information along to her stylist so that she'll feel a little more...

3 years ago
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One Shining Moment For A Spanked Cheerleader 1

*One Shining Moment for Her Cheering Bottom*The Female Fugitive #3 tonight’s Episode College Cheerleader: Basketball Fever has hit as March Madness is upon us. That's why I chose to make The Female Fugitive a college cheerleader found while flashing her panty clad bottom at the March Madness? fans.   The following is a continuation of The Female Fugitive Story I first wrote back in 1999.  It has been freshened up with a rework and update.  Nine months have passed since Beth since Mr. Deal...

4 years ago
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A Saturday of Cheerleader Pleasure Ch 03

It was Saturday. My favorite day of the week. I was thankful that I didn't have to go to class or work on Saturdays. That meant a lot more free time and a lot more time for fun. And no other day of the week allowed me to spend more time with my amazing girlfriend, Becca. Becca used to be a cheerleader for Rasington University, but her horniness and refusal to abide by school policies got her kicked off the squad. She refused to return her cheerleader uniform and was subsequently expelled....

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3 years ago
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A Saturday of Cheerleader Pleasure Ch 03

It was Saturday. My favorite day of the week. I was thankful that I didn't have to go to class or work on Saturdays. That meant a lot more free time and a lot more time for fun. And no other day of the week allowed me to spend more time with my amazing girlfriend, Becca.Becca used to be a cheerleader for Rasington University, but her horniness and refusal to abide by school policies got her kicked off the squad. She refused to return her cheerleader uniform and was subsequently expelled....

4 years ago
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A Saturday of Cheerleader Pleasure Ch 06

“We're here,” Becca announced, as she parked her car and unbuckled her seatbelt. I unbuckled my seatbelt and started to get out of the car, but Becca grabbed my left shoulder and motioned for me to remain in my seat. “Hold on,” Becca said. “There's something that we need to talk about first.” “A couple family rules?” I wondered. “For the most part, we don't have any rules,” Becca replied. “But there are some... boundaries.” “Boundaries?” I repeated. “What are you...

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