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I was dating this kid, this 5'7" college sophomore who was a fucking hot little crossdresser. A perfect-10 trap body--trim, flat stomach, smooth, rockin' legs that led straight up to his tight, round ass, not to mention his delicate face made up bewitchingly in lipstick and eyeliner.
To make it even better, he fucked like a minx. He would come up from UCLA and spend the whole weekend bouncing on my dick.
Legally he was Leo, but with my cock in his pussy he was Lissa.
Lissa was a bit of a slut: I knew she had a couple of other boyfriends besides me. When you're 20, you need a steady supply of dick. I was happy to have her around when I got her--I couldn't complain if she spread it around a little.
In fact, I could understand perfectly: I used to be a slutty little crossdresser myself. From the time I was 18 until I was about 25, I fooled around with any guy who would treat me like a sexy girl. One handsome man in his 50s became my sugar daddy. He bought me sexy clothesÑskirts, dresses, bras, panties, lingerieÑto wear for him. I sucked his dick at least a hundred times, always wearing something he picked out for me.
But time's gone on. I'm 33 now. I'm not as trim as I used to be, not the perfect trap I once was. I still have the impulse to dress now and again, but my desire had shifted to fucking younger sissies. And I was happy like that--until the last night of the Santa Barbara County Fair.
Leo would drive up to visit me in Buellton. In school, he lived as a boy, but he went all the way when he was with me: he shaved his legs, his armpits, and his crotch--except for a trim strip pointing straight up from his cock. He called it a Brazilian, which suited him with his jet-black hair and smooth, tan complexion.
I invited him to visit me on Saturday--we'd go to the barn dance at the county fair, a country line dance type of thing. I wanted to see him in that cowgirl look: rhinestone boots, short denim shorts, a flannel tied under his small tits to reveal his flat midsection, a cowboy hat.
He was dressed when he arrived. His denim shorts rode up his smooth legs so high I could have cum just from looking at him. Sure enough, he had the plaid shirt tied above his tight tummy. He'd done his makeup already too--a light coat of shimmering eye shadow, some shiny lip gloss.
Top that off with a white cowboy hat and some rhinestone-and-turquoise covered boots, and you've got one cowgirl who is going to be very popular at the barn dance.
"Jesus, baby... you look hot."
"I know, right?" She smirked. "Tell you what: I'm gonna blow you right now so you don't get a wet spot."
"I'm ready when you are, baby."
We walked around the side of my house. I don't have any neighbors to that side, so we could fuck around outside as loud as we wanted.
She pressed my back up against the wall and wrenched my pants down to my knees.
Inhaling my already semi-hard cock like a professional, she gave the most toe-curling blowjob she'd ever given me. Maybe the sluttiest blowjob ever given. My knees were buckling within two minutes. She tugged roughly on my balls.
She slid my cock out of her mouth momentarily, rolled her hand down it sensually.
From her knees: "I've got a surprise for you, baby."
"Oh yeah? What is it?" I managed.
"I invited one of my boyfriends to the dance too." She worked my cock back in her mouth, trying to balance out my confusion with pure carnal pleasure.
She went on. "But don't worry... he's bringing someone for you too."
"Oh yeah?"
This turned me on. I'd get to see my girlfriend with her boyfriend, a bit of a dark fantasy for guys like me. Plus, I'd be fucking one of her friends, a new hottie. I could try to make her jealous with how well I fucked her friend, how much I made her moan.
As I started to fantasize, I slipped closer to orgasm.
"Just one more thing..."
She worked me deep in her mouth, using her mouth, hand, and throat to give me access to one insanely long and responsive fuckhole.
"What is it, baby?"
She slipped my dick out of her mouth again.
"You're going as his girlfriend."
As she devoured my cock again, she stared upward ravenously, studying my eyes for a reaction.
I felt like I'd just been neutered. Some guy was going to show up, and I was going to be his girl? Because my slutty college girlfriend made that decision for me?
She took me out of her mouth, stroked me with her right hand while she slid her left index finger over my asshole.
"You've been sweet, honey--you've really been the nicest boyfriend. But I think you know and I know that you'd rather be down here doing this than up there with a girl."
I fought against the fact that she was right. My boner swelled as I imagined myself looking up against a man's firm cock.
She slid her left index finger inside my butthole and pressed firmly against my prostate.
"Don't tell me you don't wish this was a cock pressing inside your pussy right now, baby."
I made an involuntary gasp. She pressed harder inside my ass, tugged hard on my balls with her other hand.
"UnnnggggghhHHHHH!!!"
I shot my load out of my dick like I fired a pistol, without any stimulation other than inside my ass.
My brain could not process what was happening--this emasculating moment alongside the explosive, delirious orgasm I was having.
When I finally came down, I crashed back against the wall, spent but somehow still horny. I opened my eyes and saw Lissa still on her knees smiling up at me.
"That's what I thought, baby girl. They're on their way, so it's time to get you ready."
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