How I started hooking up with [M]y manager [F]

Years ago, I worked at a department store. My manager (technically an assistant manager) was this girl named Stacey. We’d flirt pretty much daily, not because we were especially attracted to each other but because it helped fill our shifts.

For reference, Stacey is pretty close to your classic punk rock chick. Short, pink hair, lots of piercings & tattoos. Almost my height, but very petite; she had this tiny waist and toned stomach that used to drive me crazy.

Stacey had a girlfriend, but would drop hints all the time that she’d be open to straying. We’d be killing time at the end of a shift and she’d ask something like, “Would you cheat, if it was guaranteed you wouldn’t get caught?” She wasn’t blatant about it, but she wasn’t especially vague either.

One night, before close, I told her I had a date. It seemed to flip a switch inside her. “You should come over, when it’s done. Tell me about it.” We’d only ever hung out twice outside of work, and that was with other people around. But I agreed. And at the end of a ho-hum first date, I ended up at her place.

It may not sound like it, but Stacey was shy. And so we ended up in her tiny rented room, watching Netflix, a blanket thrown overtop of us. And rather than lay her head on my shoulder, or put a hand on my leg, she proposed that we play truth or dare.

She went first, and I dared her to lose the boxer shorts she’d had on since I got there. She then dared me to lose my jeans. With all pretense out the window, I was given my next dare: “Play with me.”

I moved to take the blanket off her lap, but she murmured a No. And so with her leaning back against the wall, I reached under the blanket and between her legs. I groped her thigh, at first, wanting to make her wait. With each squeeze of my hand I inched my fingers further up her leg, and I was still inches away from her now-bare pussy when I felt it: the wetness that had leaked between her thighs already, and was now slick against my fingers.

I was a lot less experienced with dirty talk back then, but I couldn’t help it.

“You want this, don’t you?”
“Mhm,” she murmured.
“How long have you been thinking about it?”
“Fuck, since the first day you started,” she groaned, and reached for my cock.

It had been a while since she’d been with a guy, so her stroking my cock was… not elegant. But she was hungry for it — she had forgotten all about me playing with her pussy — and she’d sigh with deep satisfaction each time my cock throbbed in her hand.

This went on for all of a minute before she lay down on her side, and told me to get in behind her. I was naive, and figured that maybe she was having second thoughts and wanted to cuddle. But as soon as I was pressed into her ass, I felt her reach between her legs and guide my cock to her now soaking-wet opening. She was pressing me right between her lips, stroking me as best she could, and just holding me at the point of no return.

“You can’t fuck me,” she said. “But I want to feel you cum.”

I reached down and took over for her, stroking my cock as she played with her clit… her fingers teasing the head of cock now and then, and making sure we hadn’t gone too far.

Her moans — little whimpers, really — were driving me crazy, as was the feeling of sliding back and forth against her dripping pussy. I told her I was going to finish.

“Fuck, cum against my pussy. I want to feel it,” she gasped, and reach down to press my cock against her opening again. The feeling of my fingers sliding over hers as she gripped my cock was enough to send me over the edge. She nearly came as rope after rope of cum flooded her pussy, sending a mini shockwave through her body. And as good as it felt to (almost) cum inside her, the feeling of her stroking my cock afterward — running her fingers through my cum, feeling the mess we’d made underneath her blanket — might have been the best part.

I could tell she felt guilty after the fact, and and we were really just work friends, so I was out the door fairly quickly after that. As I left, she gave me an awkward hug and smiled: “See you on Monday.”

Source: reddit.com/r/gonewildstories/comments/ymtdza/how_i_started_hooking_up_with_my_manager_f