My first girlfriend developed my inner cuckold in my freshman year of college. In high school I was a pimply geek, and never had any luck getting a date. If it hadn't been for a friend's sister who made out with me a few times, I'd have gone to college without ever being kissed.
In the summer before college I grew out of the acne. Though my physical appearance was better I still had the self-esteem of a high school loser. In the first month of my first semester I couldn't believe my luck. Not only was a girl interested in me, (I'll call her Sarah) but she was also one of the most attractive girls on campus. Long shiny black hair, olive skin, deep brown eyes, and a curvy bottom.
She was a bit of an exhibitionist, always dressed in short shorts and tight tops. She was also a major flirt, hopping from lap to lap of the guys in the room, drawing the interest of all the boys and the enmity of the girls.
We shared common interests (role-playing games) and a couple of classes and from socializing with her I knew she had a boyfriend back in her hometown, about two hours away, and that she was seeing two other guys on campus occasionally, both seniors, neither of whom ran in our social circles.
I'd inherited a little bit of money when my mother passed away a few years earlier, so I had something none of her other boyfriends possessed at the time ... a reliable ride and a shopping budget.
I'd take her to one of the malls, usually with other friends, but I'd always find an excuse to buy her a little something. Eventually we were going to movies together and I was hanging out with her late into the evening in her room (always with her roommate around and often with other friends) on days when she wasn't going out with one of her other boyfriends.
We didn't really take our relationship farther than "just friends" until the Halloween party. I had dressed as Sir Galahad from Monty Python and the Holy Grail. She had dressed as a cat, black leotard, black nylons and black pumps, with little eyeliner whiskers drawn on her cheeks, and a hairband with velvet ears.
Sarah was the aggressor; she wanted to play out the scene where Galahad is seduced by the sisters of Castle Anthrax. She pinned me against a wall in a dark corner and started going to town with her mouth on my ears, while digging her nails hard into my ass through my costume and pants, and rubbing her black nylon-covered thigh between my legs.
My lack of experience showed, as I came in my pants after only a couple of minutes of her sexual aggression. She giggled and reached around to feel my crotch, noticing the copious amount of spunk I had released and also noticing that my dick was still hard after I came.
"You enjoyed that, didn't you? Well now you owe me. Keep those pants on and if I'm still horny later I'll let you lick this little pussy cat..." She walked away, wiggling her ass for effect.
After I regained my composure, I went all around the party, throughout the three adjoining blocks of dorms and the central courtyard, and couldn't locate her. I tried to avoid my other friends because I was sure everyone could smell the cum on my pants.
After a couple hours I gave up looking and just went to hang out on the benches in the courtyard in front of her dorm room, hoping I'd catch her on her way back.
After what seemed like another hour, it must have been close to 3am, Sarah came stumbling into the courtyard. Her hair was a mess, her whiskers were smeared, and she was bare-legged and unsteady on the heels. Even though she was a disheveled, hot mess, the prospect of going down on her had me instantly hard again. "Hey, Sir Galahad ... you here to protect my honor?"
"Ah, sure..." I mumbled, standing up. She tripped into my arms and looked up at me, her breath smelling strongly of what I thought was some exotic mixed drink, or maybe something she had smoked.
"Too late ... I lost that a long time ago" she giggled. Sarah lifted the front of my costume to look at my pants. "Good boy! You still have those pants on!" She reached down and grabbed my crotch, gripping my stiff dick firmly. "Pants are a bit crunchy, but your dick is all hard for me, isn't it? Hey, if you can be really quiet and not wake up Debbie, you can clean me up for bed."
Debbie was her roommate, fat unattractive and obnoxious. Sarah used Debbie's presence to scrape unwanted guys off the bottom of her shoes.
Her room opened directly onto the courtyard, as many of the rooms in that block did. She had dismantled the overhead for a little private, dark space by the door. As she fumbled with her key in the lock, she whispered back to me, "Get your costume off ... strip down to your undies out here."
"I'm not wearing any."
She frowned, "Then leave your jeans on. Don't want to scare poor Debbie if she catches us. Be really quiet, okay?"
She got the door open and slipped into the bathroom behind it. I was still fumbling with my costume ... she was right, if I tried to do this in the confines of the bathroom I would have made a lot of noise. By the time I got into her bathroom she had already lit a candle and wiped off her makeup ... maybe she had run a brush through her hair.
She spun around and leaned against the bathroom counter as I approached cautiously. I didn't want to do anything to spook her ... to tell the truth I was a nervous wreck. I would have done anything she wanted just to see her naked, and maybe even literally given my left nut to fuck her, if she asked sweetly.
"Help me get this undone," she whispered. Sarah had undone the clasps on the collar but was having trouble getting the zipper down on the back of her leotard. I stood in front of her, in my bare feet shorter than her in her heels.
.... There is more of this story ...