$50.00 Bet Cross-dresser free porn video

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My friend Cristina and I were just sitting around watching porn. It's something we do for fun now and then. Believe it or not, it has never led to anything. A scene came on where a guy was put in a wig and satin nightgown and fucked by a beautiful blond dominatrix with a strap on. We laughed at what an ugly girl he made and somehow it came up that I had a girlish look to me. She said that I would look much more like a girl in the wig and nightgown than the guy from the movie. I just smiled.

Later that day out of nowhere, she told me that she'd like to test that theory. She wondered if I'd let her dress me up. Though about it for a moment and figured what the hell. It won't hurt anybody. Always been interested in cross dressers but never took the time to try it myself.

It's amazing how quickly she was able to apply my makeup. The hair was the easy part. I've been growing my hair out a little while so a wig really wasn't necessary. It gave me a more real look.

"So, what am I going to wear? I don't think your clothes will fit me."

" I think my sisters clothes might though, one second," she replied as she rummaged through the closet looking through her sisters large quantity of clothing.

"Wait, isn't your sister a stripper? I'm going to be dressed like a skank," I laughed.

"Yeah she is but that's ok. Here try this on," she yelled to me as she tossed clothing my way.

I looked at what she had thrown me. It was a pair of tight black leather pants and a black tank top that said "Slut" across the chest.

The pants were tight but they were suppose to be and the tank fit just right. Cristina just stared at me. I looked into the mirror to get a glimpse of the woman I had become.

"Wow, I look hot. You were definitely right, I do look a lot like a chick."

"Yeah...you really do look...good. I do a good job! I bet you could even fool people in the streets or at the bar," she smiled.

"Maybe, but I don't think I look that much like a girl to fool people," I replied.

"I bet you 50 dollars that you could fool people at the bar into thinking you were a girl. Hell, you might even get picked up by some guy. Want to take that bet?"

I froze. Stared at the mirror for a few seconds before finally saying, "Sure, I could use the cash"

It didn't take long for me to find a nice pair of boots that fit and for us to get down to the nearest bar. The moment I walked in I saw all eyes turn to me. That moment made me think this bet was going to be lost and I couldn't be more right.

Cristina sat down a few seats away so as not to interfere with what I was trying to do. Within the first minute, a tall dark haired man sat down next to me and asked if I wanted a drink, his treat. Figured that was harmless so I agreed. I couldn't believe that this was working, It was starting to turn me on.

I pulled out a cigarette and couldn't find my lighter. I must had forgotten it at home. Luckily the man offered me a light. Exhaling smoke into my lungs, we both smiled.

"Ill be right back, I've got to use the bathroom," I whispered to him as I finished my last inhale of the cigarette.

I couldn't seem to find the bathroom, the halls seemed never ending with too many turns. All of a sudden I felt a hand on my shoulder. I turned around to see the man who bought me the drink.

"Baby, you are looking real good. Getting me excited," he said as he grabbed my hand and rubbed it against his jeans before unzipping and pulling them down. I was a bit shocked and wasn't sure what to do. I told myself, go with the flow. I rubbed his large cock with my hand as he moaned softly.

"Be my little cock sucker honey, suck my big dick. You got sexy lips that are made for sucking."

Closing my eyes, I moved my head forward and let his penis enter my mouth. It was atleast 7 inches. I've watched enough porn to have an idea of what to do. Following what I've seen, I deep throated him. Every time I took him deeper I gagged but he loved it. Every moan he let out made my cock jump, pressing hard against the tight leather that wrapped my lower body..

Without thinking, I started rubbing myself through the leather and the feeling was incredible. He started to fuck my mouth fast and hard. My saliva dripped off his cock and all over my face. His hand grasped my hair, pulling it, to let me know he was in control. I didn't mind at all.

My mascara started to run a bit when he grew bigger as he got closer. He wanted every last inch in my wet mouth and I was trying to give him his wish. Sucked every inch as I rubbed his balls.

I couldn't hold on any longer, and I knew it as my cock exploded inside the leather pants. I felt the warm cum all over. I screamed in ecstasy which drove him to the edge. He shot a huge load of hot semen inside my mouth. It must have been awhile cause it felt like it wouldn't stop shoot his hot cum. His cum flooded my mouth and dripped out. My lips shined with it as it dripped down my chin and hung until hitting my shirt that appropriately said "Slut."

"Oh baby that was amazing," he barely got out as he panted. Zipped up his pants and walked off. I sat there wondering how I ended up here. I smiled.

Once I finally came out, Cristina followed me out of the bar smiling all the way.

"You definitely lost that bet. Not only did he buy you a drink, You still have cum on your lips!"

All I could do was smile as we walked back to her place.

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Betsy was more than ready for the best chapter of her life story. Her journey seemed like an eternity until she met Mr. Right. Danny was 6'3", very good looking and he had a very athletic physique. He played various sports during his college days and excelled in football. He was even drafted, as a safety, but chose Med School to become a shrink instead. It was Danny's eyes that Betsy first noticed about him. He had dark, mystic eyes that were a combination of blue and green, which she...

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Beths Big Night

Introduction: This is 99.9% true, the only thing changed is Bills name to protect his privacy. Beths Big Night. The night started like any other. When Jim got home, he asked his wife if they could get a sitter for the evening. His wife Beth told him she might be able to get someone, and wanted to know what he had in mind. He told here he wanted to take the bike out, and if she could find a sitter they could go riding together. She made some calls and told him her mom would watch them. A few...

3 years ago
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Betsys JourneyChapter 3

Betsy had something to eat and felt thoroughly refreshed. The weekend dream festival was progressing exactly as planned and she still had chapters of her life story to review. Her grad school relationship with Ron was over and thankfully she had gotten rid of a demon that had bothered her for many years. Then she remembered the promise to go over everything that happened in the SM chamber owned by Ron's boss. Now that she had rid herself of the nightmares from the experience, she looked...

3 years ago
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The Bet 2 All Bets Are Off

A week ago I made a devilish bet with my cousin Tony. The experience totally changed the way I saw him. Before that day, Tony was my cousin and my friend; now I saw him as fair game. I figured I could toy with him and see how far I could actually get him to go. First I wanted to figure out what he was thinking, what had persuaded him to make such a wager with me; I knew in my mind pursuing any type of sexual relationship with his was wrong, but I pushed that thought from my mind knowing Tony...

Incest
3 years ago
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Betsys Creampie chapter 4

As usual, a lonely night alone in a hotel room. He was in his underwear and had a t-shirt on. Through out the night, he’d been trading texts with friends. He longed for the phone calls with a real girl friend. It was years since he had a girl that was fun and sexually exciting. All the girls in the past 5 years were, by his definition, boring and slightly above prudish. Sex in bed, an occasional blowjob, never swallow and no excitement or experimenting. Where were the girls from his college...

1 year ago
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Elisabeth

"Elisabeth"By: EericBlog: abmwmw.blogspot.com***********************************************************************My name is John and I go to the West college, it's a rather small college. My girlfriend Elisabeth also goes to the same college.We met a little less than a year ago and have been dating ever since.I'm 22 years old.I am not what you would call an athlete, I have a rather skinny body.I'm really into computers so I help the teachers at the college withthe computer classes. I also...

3 years ago
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Elisabeth

My name is John and I go to the West college, it's a rather small college. My girlfriend Elisabeth also goes to the same college. We met a little less than a year ago and have been dating ever since.I'm 22 years old. I am not what you would call an athlete, I have a rather skinny body.I'm really into computers so I help the teachers at the college with the computer classes. I also help out with students who don't really care for computers and try to get them to use them more.My girlfriend...

3 years ago
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Survivor Stories Elisabeth Filarski

Standard Disclaimer: You must be 18 to read this story, be able to read erotica in your community, not be offended by the contents of it…blah blah, you know the rest. This story may be distributed freely, for commercial or non-commercial use, but PLEASE leave my email/name on it! That’s all I ask! Finally, CBS please don’t sue me – this is just fiction and I don’t mean to disparage Survivor (or Ms. Filarski’s) name in any way. This was a quickie written when I had a few hours of free...

3 years ago
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Bethanys Sins

Bethany's Sins (Pride and Greed in too great a measure) Bethany knew beyond doubt that she was the best. Today, she had waltzed outof her low-paid job with the DeMoeira Investments Company with a cool halfa billion dollars to her name (or rather, names, for she used several to claimit all), and to really prove how good she was, she even managed to carry tenmillion in notes right past the security men. Not all the hundreds of millionshad come from this one operation, of course: she had pulled...

3 years ago
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Elisabeth

Elisabeth - Part 2By: Eeric*********************************************************************It has now been a week since I saw Elisabeth doing those blackguys from the closet.And a few days ago I even caught her making out with Jamaal in the hallway at our college, right in the open.She told me that she was sorry, but I think that she wanted me to see it.I think it turns her on knowing that I'm watching her when she's with black guys.And even though I get very jealous, I really do love her...

1 year ago
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Love Lust For Bethesda Part 8211 6

Flashback of previous encounters. Bethesda : Do you always get aroused when a sex scene comes up? Me : Yeah. Bethesda : What is it you want? Sex? Me: I want you. Just feel the love for me. Flashback continues Bethesda : I’ll do it once. Bethesda : I’m sorry I lied. It’s all because I want to fuck you. Me: It’s OK. I’ll be there for your recovery. Bethesda : That was the best birthday I’ve ever had. Bethesda : You know if this goes out of hands our lives will get stir.. ed. Present day 23...

2 years ago
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Love Lust For My Aunt Bethesda Part 8211 4

Taboos have been broken a long time ago. It existed with the gods and ended with human beings. We may have intentions to a particular person. A woman perhaps. Precisely we wanted to know more about having an intercourse with a woman. Be it your sister, mother, MIL, SIL, step-sister, step-mother, Aunt, Relative, Cousins or girls who want to get fulfilled. There are at times women in brothels who intend the same but for money. I have an intention too. Bethesda. Well previously I told you how...

Incest
3 years ago
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Love Lust For My Aunt Bethesda Part 8211 3

Well, it was on January 7, 2017, on a perfect Saturday morning that Bethesda received a call from her colleague stating they found something new this time and want her to visit her office which is like a museum to me. She called me as I was in the bathroom brushing my teeth and told me to be alone for some time because she has to go to an urgent work in her office. I on the other hand, didn’t want to leave her and told her to give me 10 minutes to freshen up and that I too will be coming with...

Incest
3 years ago
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Bettina and the Picture Book

These are excerpts from my novella, The Pohlheim Chronicles.E mail me at [email protected] for the complete story..1...... The Baron was turning the page of the big book and as he did so his hand delved further, pushing her silk panties down to her thighs, his fingers moving closer to her secret place. The feeling that was circulating around her lower torso suddenly flared and filled that private place of hers with heat. She closed her eyes again as the rest of the world seemed to fade...

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