Waiting for a Friend

A little history...

When I was 18, I saw an older man, must have been in his forties, fuck my sister, who was nineteen. I came home from school early one day and there they were, in the living room, going at it.

Ellen, that was her name, made me promise not to tell our parents. I promised and we never spoke of it again. I did however, think about it, on and off during the following years, if you know what I mean.

I celebrated my forty-second birthday about two weeks ago and still occasionally think about that. I've never married, but I have had many girlfriends. Some were my age, but mostly they've been younger than me. For some unknown reason, younger women seem to like me. I'm not particularly good looking. I'm balding and I have what can best be described as a mildly brash personality. I'm kind of loud and my mouth tends to have a mind of its own. Or, rather, it tends to speak my mind without going through any sort of filters.

Why did I tell you about that afternoon in my younger years? Probably because it has been a bit of a sexual obsession of mine since then, if you haven't figured that out yet. The idea of an older man having sex with a younger woman turns me the fuck on, and now I finally am that older man.

Depending on your own age while reading this, at forty-two I either reached "older man" status a long time ago, or I'm not even close to being "older". That doesn't really matter. What mattesrs is how I feel about it and I feel that I have now reached the age that I always imagined that hairy dude who was fucking my sister was.

In my mind, that means that I now need to fuck as many eighteen year old women as possible. To be truthful, though, while eighteen would be nice, at this point in my life, anyone between eighteen and about thirty will do.

My story...

This brings me to the beginning of my story, which happened last weekend. I'm a disc jockey at a rock radio station and once a month I work weekends. This was one of those weekends, and by the time I got out of the station, I was exhausted. I just wanted to go home, but a buddy of mine called and said he really needed to talk. He asked if we could hit the Lion and Whistle pub downtown, a place we'd been in the past, but not recently.

This particular friend has had a history of relationship problems and he's been there when I've needed him, so I agreed.

I walked in and looked around. He wasn't there yet, so I ordered myself a Jameson. That was usually my starting drink. I don't have many of them, but I like to start with a whiskey.

By the time I had my second Ketel One (vodka always followed Whiskey), I had an inkling that perhaps he wasn't going to be showing up and I started to get a little ticked off. That was when I noticed her. It was hard not to.

She looked to be about eighteen or nineteen and she had bright pink and purple hair. She was alone, and my mind instantly went places the minds of forty-two year old men shouldn't go when they see a girl of that age. Why was she alone, I thought? Was she, too, waiting for someone?

She noticed me at that point. Our eyes met and we gave each other a polite smile and nod. I felt a little awkward so I turned away and ordered another vodka. I downed it pretty quickly and looked back. Her eyes were still on me, as if they had never left.

By vodka number four, I had gathered up the courage to walk over.

"You seem to be alone", I yelled over the music. "Are you waiting for someone?"

"I was, but my bitch girlfriend seems to be taking her sweet, fucking time," she said. "We were supposed to meet at 8:30".

I looked at my phone. It was 9:12.

"Same here," I yelled. "A buddy of mine was supposed to meet me here at about 8:00."

Nightmare by Avenged Sevenfold started playing and her head began bobbing when the drums fired up.

"Like this song?", I asked. It was a couple of years old, but was in our current rotation at the station. In fact, I'm pretty sure that on weeknights, when the deejay is off, this bar has our radio station on.

"Fuck, yeah"

"Me too. You a metal head?"

"Pretty much. I like other shit like dubstep 'n' stuff, but I'm mostly into metal. All kinds of metal."

"Nice," I said.

"'Disturbed' is my current favorite," she said. A band we play on a regular basis.

As she said that, I felt her foot touching mine. My face got a little inquisitive.

"Fuck, they let me in the bar so I'm at least eighteen," she said.

"No, no," I said. "I was just ... oh I don't know what I was..."

Her foot moved up to my calf.

"I'm twenty-three. Does that make you feel any better."

"License and registration, ma'am," I said, jokingly.

Despite my joking tone, she pulled out her driver's license. I looked at it and then at her, as if I was a cop. She was indeed twenty-three. In fact her birthday was last week.

"Happy birthday," I said.

"Fuck off."

We smiled at each other and her leg rose from my calf to my thigh. I was starting to get a bit of a boner.

"Do you want another drink," I asked, my eyes pointing at her empty beer glass.

Her hand moved to her blouse and she traced a finger from just below her throat down into her cleavage. She had smallish breasts, but from my vantage point they'd fit nicely into my hands.

"No, but I do want to taste your cum."

That turned my 'bit of a boner' into a full-fledged, raging hard-on.

The next five minutes were a bit of a blur, but we ended up in an alley not far from the bar. There was a streetlamp about 20 yards away. It cast a little bit of light our way, enough to barely see each other, but not enough to let anyone else know we were there. Not unless they were within whispering distance anyway.

It was a cool fall evening but even so, without speaking, she unzipped her jeans, wriggled them down to her ankles, hiked up her blouse and leaned forward slightly against the brick wall, offering herself to me from behind.

Without saying a word, I unzipped my fly, got my cock out through my underwear and quickly slipped on a condom.

I put my hand between her legs, sliding my index and middle fingers from the bottom of her pussy to her clit, to determine her level of 'readiness'. She was 'ready' all right. Fuck, she was nearly dripping.

I slipped my fingers inside of her cunt and felt her welcome me, nearly pulling my hand inside. I finger fucked her for a few seconds and she let out soft moans as I did.

"Mmmmm," as I slid two fingers inside her pussy.

"Nghhhhh," as I slid my fingers out.

She pushed her ass towards me as I removed my fingers, wanting me to slip them back inside. I obliged.

"Your cock," she breathed. "Inside me. Now."

I spread her pussy lips with my fingers and inserted myself into her. Even through the condom, her pussy warmed my penis, which, unused to the outdoors, was a bit chilled.

I slowly began to thrust into her, both my hands on her beautiful round, young ass to steady myself.

"Unhhhh," she groaned as I slowly increased the pace.

Suddenly, I realized I needed to feel her with my hand. I positioned one hand on the wall we were fucking against to steady myself and with the other I began to explore. I went to her pubic area and realized she was completely clean shaven.

I took a break from thrusting and instead pushed my cock deep inside and wriggled around a little as I felt her mound and went for her clit. She seemed to like this. I stimulated her clit while wriggling my cock inside her for a while, but soon it became clear that she needed to have have my hard shaft go in and out of her pussy again.

I fucked her and moved my hand up her belly to her chest. Her tits felt good. They were, as I'd imagined earlier in the bar, a perfect handful. What I hadn't imagined was how firm and pert they'd feel... and her nipple, oh her nipple. It was hard and it was perfect.

I moved my hand from breast to breast, cupping them and taking her nipples between my thumb and index finger, which still had a little pussy juice on it.

I was about at the tipping point and she seemed to be as well.

"Fuck me hard," she half-whispered, half-grunted.

She began letting out short, sharp "uh" sounds and I could tell I was about to make her cum.

"Uh. Fuck. Uh. Fuck. Uh. Fuck," she let out.

"Mmmmm, yeah. Fuck. Ahhh. Oh. Fuck. Me. Har. Der."

"I'm. Going. To. Cum," she said rhythmically.

Then, she did.

"Fuuuuuuuuuuuuuuuuuuuuuuuuuck. Oh, fuck. Fuck. Fuck. Fuck. Fuck. Nghhhhhhhhhhhhhhhhhhhh."

And, with that, I couldn't hold it in any longer.

My first spurt came inside the condom, inside her cunt. Then I quickly pulled out and pulled off the condom and finished cumming on her ass.

Using my cock I rubbed my semen into her ass cheeks, then with my hands I spread my warm creamy cum up under her blouse and around her back.

"Fuck, that was nice," I said.

"Yeah," she agreed.

Then, she stood up, pulled up her jeans, straightened her blouse and walked away. I stood there stunned for a few seconds before zipping myself up.

That was the last time I ever saw her. Although, I have thought about her since, if you know what I mean.