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Heads-up: this is from the top's point-of-view, and it's quick and dirty. If you're a sissy with a horny little pussy, that might just turn you on.
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I was traveling for work over Halloween. I figured I'd stop into a college town, Charlottesville, Virginia, to see some students in costume.
I love the excuse that Halloween provides: it's just one night, everyone gets plastered, so whatever happens pretty much gets a free pass. One night only.
I especially love the boys, because, well, I love boys. Sissies, in particular. Aspiring crossdressers who go all out on Halloween, their one chance to flaunt their petite little asses without judgment or repercussion.
I walked the streets of Charlottesville and took in the young and beautiful crowd. They were alive with spirit, loosened by booze. A couple of girls flirted with me, titillated by the idea of seducing a 40 year old DILF like me. On another night, who knows? I might have taken one of them home with me.
But I was in the mood for a crossdresser. That sweet young man who could finally let his hair down tonight.
I was at the bar at Trinity Irish Pub when I saw him. Dressed in what looked to be a UVA cheerleader uniform, navy and orange, the hem of the dress riding up the side of his ass as he sat on a barstool.
He was in full makeup: a coat of foundation, eye shadow, eyeliner, bright red lipstick. His own long-ish blond hair was styled carefully to look like a girl's.
He had a Corona in front of him.
And he looked sad.
I worked my way through the boisterous crowd to get near him. I leaned into the bar to order. "Two shots of tequila--one for me, and one for the pretty girl." I pointed to him.
He looked up at me. He'd been oblivious to the whole room for the past five minutes.
"Thought you could use a tequila to go with your Mexican beer. The name's Tom."
I reached my hand out, shook his. He'd done his nails, or someone had done them for him.
"You look like you're not having as good a time as the rest of UVA is."
"Yeah, well, when your girlfriend ditches you for her ex-boyfriend..."
"No shit."
"She's upstairs dancing with him right now. You might recognize her--she's the one wearing the exact same outfit as me."
"I'm impressed you can fit into that thing. Not too many boys look that good in a cheerleader's uniform."
He looked up, surprised he felt honored by the compliment.
The bartender set down our shots. "To having a better rest-of-the-night." We slugged our tequilas down. The room was so loud I had to lean into his neck a bit to be heard.
"So... what made you decide to go out as a cheerleader tonight?"
"It was my girlfriend's idea. She's got a friend who's a UVA cheerleader, and we're all about the same size."
I took him in: probably about 5'7", 135 pounds soaking wet, with the kind of tight little midriff you can only have when you're 21.
"But what made you do it? Dress like a girl?"
"I told you, my girlfriend told me to."
"She sounds like she wears the pants, huh?"
We took a pause. He was a little pissed off by my insistence, a little embarrassed that I was pulling her personal shit into the light.
I signaled the bartender for another set of shots.
"I'll tell you a theory of mine," I started. "I think Halloween is a great time for people to express themselves. It's a night when anything goes--you can do what you want and not be judged for it."
He looked at me through his sad, made-up eyes. He looked curious, maybe a bit hopeful.
"You can be what you want to be. A pirate, a baseball player..." I nodded towards the young, masculine guys near us in those costumes. "...or a cheerleader."
The shots arrived. He grabbed his, slammed it back. He turned his stool to face me so that I was now between his thighs. Which were shaven. Hmm. This might just play out.
I took his hands into my hands, rested them down on top of his exposed thighs.
"Your `girlfriend' might be up there screwing you over, leaving you down here by yourself. But that doesn't mean she gets to have all the fun..."
I did my shot, leaned in close to his ear. I slid our hands further up his thigh, near his short hemline.
"Let me show you a good time tonight. I'm in room 411 at the hotel right next door. Knock on my door in five minutes."
I slapped $20 on the bar. I leaned in close and kissed him high up his neckline, then I walked out of the bar.
Five minutes later, I heard a quiet knock on my door.
There "she" was. I pulled him into the room, closed the door, pressed him against the wall.
"Have you ever done this before?"
"No," he/she whispered. I slipped my hand to his thigh, started making out on his neck. He writhed in my hands. I kissed him roughly. This was animal foreplay--we had only one thing in mind right now.
I smashed my body into his so he could feel my boner through his polyester cheerleading outfit. I picked him up, carried him to the bed. I reached under his skirt, ripped his panties down, pulled them over his black-and-pink Nikes. I reached into my pocket for the lube packets they'd had at the bar. I unbuckled my pants, squirted some lube onto my dick, worked some into her asshole roughly, then shoved my dick up inside her.
She gasped, surprised by the invasion, and maybe that we'd gotten here so quickly. I pressed against her inner muscles, knowing I had to wait a minute but impatient to give her a hard fuck.
I kept pressing until I could slide in, roughly. She cried at the top of the stroke, with five of my long seven inches inside her already.
"Oh god..." she cried.
"Mmmmm..." I replied.
I had to start fucking her whether she was all-the-way ready or not. I worked a little shallowly at first. After a minute or two until I was nearly buried inside her. Finally I leaned up against her bottom side, my thatch pressing against her shaven underside. I looked into her eyes as she felt it--felt a man all the way deep inside her.
"How does that feel, baby?"
"Ah... amazing."
"Do you know why you dressed like a cheerleader now?"
She nodded meekly. I fucked her properly, in and out, working the sides of her pussy, hitting her fuck-button, giving her the first--but probably not the last--hard fucking of her life.
She started panting, her own dick hard as a rock as it brushed against my lower stomach.
"Play with your clit. I want you to cum when I do."
She reached down, wrapped two fingers around her dick. She did not have to tug at it for long before she was ready to shoot.
I could feel her ass clenching up as she got ready to pop. That sent me over the edge.
"Baby, I'm gonna cum inside you."
"Unnnhhhh!" she said, as her first load shot up. It landed on her neck, streaked clear down the front of her cheerleading uniform. I began to let my load loose up her ass. God, it felt good, her snug virgin ass squeezing me as she came in the front. I kept pumping as we both kept shooting. She sprayed her load all over her front. I must have shot seven or eight times inside her before I finally passed out on top of her.
We rested like that for a few minutes, me still inside her, her covered in her own cum. I came to, and went to the shower for a rinse. When I came back, she was in just her panties and a bra, asleep and nestled in the bed. I nuzzled up behind her in just my boxer briefs and spooned her.
Guess she's spending the night, I thought.
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