Halloween Surprise Pt1 free porn video

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Its been a while since this happened but I remember it like it was yesterday.

I had just turned 17a few days before my favorite holiday. Im a good looking guy, 56 maybe 140 lbs. Not the biggest guy in HS but not the smallest either. I have what I call camouflage colored eyes. Sometimes their brown, others green depending on what Im wearing. I have a nice slim toned body from track and always loved being outdoors.

Yep, Halloween was right around the corner. Trying to come up with a good costume was always a tough thing to do. I needed help coming up with a good idea or two, asking my friends and family, easily discarding their ideas of zombies, bums or a football player&hellip, I asked a few teachers at school. My English teacher, Mrs. Roberts laughingly suggested I dress up as a cheerleader. Itd be different but I dont see myself doing it for obvious reasons. But after telling my girlfriend, she was all over it and decided to make this her thing to do! I couldnt argue with her as excited as she was so I went with it. We had plans to go to her older sisters Halloween party at her Dorm upstate so no one would know me and it was all for fun anyway.

So the morning of the party came. Sherry, my girlfriend, brought the costume over along with hers. She told me last minute she was going as a Vampiress. I couldnt wait to see her in her costume. We fooled around a little then about 2 we got down to business of getting dressed up. She had me shave my legs and the little bit of hair on my arms and face, armpits came next, which I argued about but eventually lost. Oh well, get into character right?

Once all that was done, it was time to get dressed. First, satin panties, then cheerleader knickers, short white and blue skirt. Bra and some silicone breast forms. Well, the forms kept moving around so Sherry decided to glue them in place. After that was done, the bra went back on, followed by the tightest sweater I ever wore. I have somewhat short hair, so she pinned a black wig on my head. She followed that up with some knee high socks that went above my knees and finally some uncomfortable high heel shoes. Thinking I was done, I went to look in the mirror, thats when she tackled me&hellip, literally! Not until Im done! she said. Sherry sat me down in front of her and went to work putting make up on me. After what seemed like forever, she said I was done. But I was not to look until she got dressed. It took her about an hour, where I had time to take a few shots and drank a beer. By this time, the satin panties and the weight of the breast forms were making me incredibly horny. Finally, she said lets look in the mirror. I gotta say&hellip, she looked hot, kinda like a blonde Elvira. Surprisingly, I looked passable&hellip, even cute. A little slutty but I was kinda buzzed so it was all good.

I took a few more shots and we were off. I brought a 12 pack along for the ride and only had a few more left when we got to the party. Once there, I was extremely nervous but thanks to the alcohol, got into character. Sherry was playing her part too and we were both having a good time. A few times I seen guys talking to her, doing jelly shots with her, even grabbing her ass. I was not happy about that but was having my own good time to do anything about it. About half-way thru the party I noticed I pretty much always had a small crowd around me and guys handing me drinks. A little later my crowd grew quite a bit. Sherry also noticed this and got extremely jealous and decided it was time to go before something happened.

Once we were in the car, she was yelling at me for being such a slut. What? I thought, no one grabbed my ass or tried anything. I mistakenly told her she was jealous because I looked so much better than her. After that I got the silent treatment. Fine I thought and finished the last few beers. We needed to stop for gas and she told me to do it. So I got out, went in to pay for the gas and realized I didnt have any money. I went back out to the car, but she was gone! The bitch left me there! And I was dressed up as a slutty cheerleader!

I wanted to call someone but couldnt. Wtf am I supposed to do&hellip, I went back inside, sat down and drunkenly tried to figure out my options, which werent many. I sat there for a few minutes, head down when this big truck driver said to me, It looks like your friend left you, want a ride?

Are you kidding? Of course I do. Thank you so much!

We walked over to his big rig, he opened the passenger door for me and helped me climb into the cab, squeezing my ass at the same time. Honestly, I kinda like it. Being treated like a woman by this huge man. He climbed in and we started rolling. He kept sweet talking me, telling me how beautiful I looked. How hot I was making him! I didnt know what to say, I think all I did was blush.

We were about halfway to my house, a good 45 minute drive left to go, when Joe, the truck driver said he had to take care of some business and pulled over. I thought he was gonna get out and water the plants. You can imagine how surprised I was when he jumped back into the sleeper and yanked his pants down, pulled out an enormous cock and start stroking it. What the hell is happening? Even more shocking was the fact that I couldnt keep my eyes off of it or the fact that I was pinching the nipples on the breast forms and rubbing my crotch like I had a clit!

So heres this guy stroking his HUGE cock while I watched with all the interest in the world. After a few minutes he said his arm was sore and could I take over? I think I jumped in the sleeper and had his cock in my hand in less than a second. What the hell was I doing? This cock had to easily be 10 inches with the largest mushroom head and here I was stroking it, mesmerized by the size, the feel and the girth of it.

Without know what I was doing, the next thing I know, Im tasting it and enjoying it. I slowly start taking more and more of his cock into my mouth and loving it. Im drooling all over his knob and using that spit to lube the rest of his shaft. I was so into what was in my mouth, I didnt notice he was playing with my asshole, squeezing my fake tits or even noticed I had a very erect cock of my own. Hes oohing and aahing, fingering my tight asshole, which was feeling amazing, no pain or uncomfortableness, it even seems like my asshole was drawing more of his fingers into me.

After a few minutes of this he stands up and flips me around on my knees and lines that monster of a cock up with my ass. I realized what he was doing and tried to get out of his grip but was unable to, he was just too strong. As he slowly sunk inch of incredibly hard inch into my backdoor the more I felt like this is where I was supposed to be. Sounds weird, I know. But this just felt so much better to me than putting my slim 5 incher into Sherry. Once I could feel Joes massive balls resting against my silk panties, I knew I was his bitch. He took his time and let me adjust to being stretched so thoroughly then began to pick up his pace. Next thing I hear is me moaning like a whore while bucking my hips back to meet his, trying to get every part of his cock inside me that I could. He loved this and turned onto his back, pulling me on top of him so I could ride his cock for all I was worth. I took him deep and shallow, slow and fast. Whatever felt good, I did. Joe told me he couldnt take it anymore and pushed me off him, stood up and grabbed my face and blasted a huge load on my face, in my mouth, in my wig, the sweater. (which had so much cum on it, I had to was it 3 times to make sure it was all off.)

I laid in the sleeper for the rest of the way back, cum drying all over me, my ass felt like it was beyond empty. When the truck stopped again, I got up, Joe gave me his phone number and got out of the truck and Joe pulled off. Me still in a stupor, trying to figure out exactly what happened and why did I like it so much?
I had a moment of clarity and realized I never told Joe where to drop me off at. I looked around but couldnt figure out where I was. I noticed a seedy looking motel across the freeway and an odd looking shack of a building directly in front of me. No sign or anything, just a nondescript white building with 4 or 5 cars parked in the area and a lamp post&hellip,.

Hope you liked my story and want to read the rest. Leave comments, good or bad and if your interested Ill post more!

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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...

1 year 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...

1 year 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....

4 years ago
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Halloween Cheerleader Fantasy

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...

1 year 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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Motel Surprise pt1

Home for the holidays, I was lying up in my motel bed on Christmas Eve; sound asleep, when I thought I heard a knock on the door. I stirred slightly, but didn't respond. I was sure I was dreaming.I guess, while I slept, I'd kicked the covers partially off and my naked ass was pointed up in the air, my cock semi-erect and pressed against the bed, pointing down toward my feet. As I woke up, I slowly realized I wasn't alone in my room.I rolled over on to my back, wiping the sleep from my eyes with...

2 years ago
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Halloween Humor

I often read jokes that make me laugh. Then I think about what a good and humorous story they could make. So I decided to write about a few of them. I hope you get a chuckle out of it, or at least a smile. A big thank you goes to Mistress Lynn for taking of her time to edit this story. **** Roy and Martha Simmons had been married for over forty years. Even though they were still in love, Martha always considered Roy a cantankerous old fool. Of course, Roy always felt Martha was an airhead,...

2 years ago
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Halloween and Batman

Just a short non-erotic story for Halloween. If you’re looking for sex, it’s not here. For the rest of the readers I hope you enjoy it. A big ‘Thank You’ to Estragon for making it a much better read. * I’m what most people would call a normal, non-descript type guy. I’m 5′ 10′, weigh 160 lbs. I’m not overly smart, but not dumb either. I’ve always been on the somewhat quiet side when it came to girls. In school I was the guy you never remembered in class. You would have to look in your...

3 years ago
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Halloween cd crossdresser

TinkerbelleMy sister , Candy, and I were fraternal twins, but looked nearlyidentical. Pretty much the same height weight and build. In high school,she was always teased about having small tits and I was always teasedbecause I was small, thin and had a big ass for a guy. Because of this wewere extremely close. Best friends really. We spent nearly all our timetogether.After college she became a consultant and I became a math teacher. Becausewe were so close, I spent lots of time at her house...

3 years ago
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HALLOWEEN MOM

HALLOWEEN NIGHT - OCTOBER 31st 2007 It's hard to believe it's been a year since that fateful night. Almost impossible to comprehend the changes that have occurred in my life, in my outlook on life, on who I've become...on what I've become...on the horrible things I've done...I'm going to drink from her breasts tonight...those beautiful orbs that are filled with thick, delicious creamy milk that her body has manufactured for my sister. Then I'm going to make love with her...unmasked at last.I...

1 year ago
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Halloween Party

Spells 'R Us: Halloween Party By Bill Hart The Lambda's Halloween party was tonight. Just about everybody, who was anybody, on campus would be there. CeeJay Larson hadn't picked out a costume yet. But then, he hadn't figured on being invited at all. His fraternity was the butt of some really weird rumors, so he'd been almost shocked when he and a couple of his brothers received invitations. He was looking for something unique. What he seen so far rummaging through through...

2 years ago
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Halloween Flirt

Halloween Flirt By Alice Barry I was just going to stay home and have a quiet night by myself when I received an email from my friend Debbie to come to a birthday party at her home on Halloween. I had been to her birthday bash before. She goes all out encouraging outrageous costumes for her Halloween birthday. I think I was invited because of my reputation for fantastic desserts, not for my friendship. Debbie and I had dated for a while several years ago, but it never went anywhere....

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