Please go easy on me, as this is my first story. It wasn't originally intended to be a Literotica submission, so I understand it isn't the most cohesive of writings. If people end up liking the basic gist of it, I'll write more coherent stories in the future.
In my early twenties, I was wondering if it would ever come together. I'd dropped out of college, but had a good desk job that would certainly allow me to provide for a family in the future. Unfortunately, that future wasn't anywhere in sight. Most of my days were spent crunching numbers and pushing paper, and my nights were spent wondering how my friends could still be so excited for beer pong and trivia night.
I was losing touch with my friends interests, and as a consequence, losing the common interests I might have shared with most girls my age. Dressing in slacks and collared shirts seemed to put a damper on that too. At 6'3 with long dark hair and a defensive lineman's frame, work clothes tended to make me look...well uncomfortable all the time.
Perhaps it was loneliness, perhaps it was just the thing to do in 2006, but either way, I was there. Looking online for Mrs. Right.
What about her?
Too blonde.
What about her?
She's a smoker. I don't smoke anymore.
What about her?
She likes...NICKLEBACK...
What about her?
She was never going to be Mrs. Right.
Never.
She was twice my age, and almost certainly wouldn't be interested in having kids for the first time in her mid-40s. But perhaps, at the very least, she could provide some insight to what girls my age might want. At the very least, she'd be some fun company, and some quirky, but still respectable arm candy. She had short, brown hair and thick glasses, but she also had a very warm smile, lovely green eyes, and some pretty dangerous curves.
After exchanging messages, we went out to dinner, then went to the beach just to hang out and talk. Her outfit choice of a t-shirt, cardigan, and modest skirt led me to believe she had no idea what kind of brick house figure was floating under all of that cotton. Thank God I played it casual with jeans and a collared shirt.
It turned out she was dating an older guy, but it was a long distance type of thing, and according to her, he'd been looking to take a break for a while.
I'm a good guy...but even good guys (perhaps especially good guys) deserve to get laid once in a while. I put my good guy hat aside, and took that piece of info as my cue to start laying the groundwork for hooking up.
I asked her what her thoughts were on her and her man's break. She said it made her sad, because she thought they could have kept it going until one of them was ready to move (they both worked in similar fields, but were working on long term projects), and they were going to stay friends. I told her that I understood, as I'd done both the long distance thing and the ambiguous long term status thing, but to look on the bright side. Even if nothing worked out, when she talked to him next time, she could make him jealous by saying she'd gone out with someone half their age.
She said "Well there are bright sides too. You get to meet new people, pretend you're a twenty something and date again. Plus, you know, the bedroom stuff."
"Bedroom stuff?"
"You're just gonna make me come out and say it, aren't you? When guys get older...some of them...and they mean well, but some can't get as...you know...hard as they used to. Or...you know...for as long."
I answered back "Oh, haha. Yeah, I forgot about that. Well, younger guys, we have issues too. Sometimes we get a little too excited and things...you know...end sooner than they need to. We haven't exactly learned to take our time, and sometimes it could be over in like five or ten minutes. Then afterward you can't really ask for a do over."
"Five minutes? Man...I miss five minutes. And a do over? Sign me up."
It seemed as though the plan would be a go. I certainly wasn't out to use this poor girl as a one night stand, but I'll be damned if I was gonna miss out on this experience. If the connection was bad, she'd know. There wasn't anything in our conversation over dinner or afterward that led me to believe she wasn't realistic. We could both try it, and if we didn't like it, go our separate ways. But if it was good for both of us, that pussy was going to get a workout it hadn't seen in years.
I put on the adorable eyes and she asked if she could kiss me. I kissed her softly, then backed away.
"Why did you back away? That was fun."
Perfect set up.
"This is embarrassing...but I'm...kinda hard, and I didn't want to come off like I was reading too much into you kissing me..."
And thus, the flood gates were open.
She became a flustered school girl, like she had discovered sexual contact for the first time and didn't give a shit who knew she was out to get some dick that night.
She kept kissing me and making self justifying excuses about why she was doing what she was doing. They must have been for herself, because she knew I really could care less. Or maybe she was just giving me boner fodder, as though I had whispered the slut out of her.
We drove to the drug store and I picked up some condoms, then we went to literally the closest motel to the area, and she got a room.
She asked me to strip and lie back on the bed. So I complied. From there, she straddled me, took off her top, and apologized for having such big low hanging tits. I accepted her apology by sucking on her big round nipples and running my hands all over them.
Next she turned around, pulled up her skirt, pulled down her panties, and apologized for not having a bald pussy like a younger girl. I accepted that apology by leaning forward, taking a deep sniff of her musky bush, and then diving into her muff with a gusto that I can only assume she had never seen before.
It was then that the dirty talk started.
"Fuck yeah. Get my pussy juices all over that face. Lick my dirty little snatch...oooh you're gonna fuck it good tonight..."
