A story about a singular moment of boldness on [m]y part, leading to getting [f]risky with my manager

I was 22, fairly attractive in my own narcissistic opinion. She was a fairly short lady, around 5′, not exactly my type, kind of nerdy, average looking, extremely neurotic and always stressed out and looking disheveled. Just all over the fucking place. The one thing she had going for her was just a ridiculously thick lower half, my girl would straight up look like a centaur when she walked because her butt and thighs just overpowered the rest of her tiny body.

I know I’m not painting a pretty picture here, but her personality, coupled with her incredible ass just did things to me at times. She would get on my nerves by stressing out and would just never shut up and it would almost always turn me on. It was the position of power she had over me. I would just daydream of shutting her up by shoving my dick inside her mouth when she would talk sometimes.

Anyway, we would go on week-long business trips every couple of months. Nothing to speak of, we’d be with clients during the day, go back to the hotel each to his room, maybe have dinner. We’d often work late in preparation for the next day, but always in the hotel lobby or by the pool or whatever.

The story begins on one of those trips. She called me after we came back from a long fucking day and I was just thinking I’d rub one out and crash, wanting to discuss some presentation. I sighed and said alright meet you downstairs.

“Actually can you just come over to my room, I’m really fucking exhausted.”

I didn’t think much of it, just thought “me fucking too so why are we doing this,” and went up to her room. She was still in her work clothes, sitting cross legged on the bed and typing away. It was kind of weird seeing her in that setting, on a bed, if that makes sense. It instantly gave me ideas. I just wanted to get this over with quickly so I could go back to my room and deal with those ideas.

We worked for like half an hour, won’t bore you with the details. We started both just spacing out at one moment because we were too tired.

“Do you just wanna call it a night? I genuinely don’t think we’re productive at all right now,” I said.

“Come on, you know we don’t have much of a choice, we gotta be there at 9, this shit has to be perfect.”

We were legit “harmonizing” colors and formatting shit nobody would even notice at that point and I just had no patience left.

“Let’s just take a break alright? Just 5 minutes.” And I just laid down on her bed, I was sitting on the edge up until that point, so I laid there, legs hanging out the end of the bed. She looked at me from above for a couple of seconds, expressionless, I figured she was maybe pissed at me giving up but I didn’t care and I was too distracted by her ass a mere inches from where my hand was laying.

She laid down next to me, on her side, looking towards me, I turned my head to face her and immediately the whole situation just felt strange. Like, I wish it was as easy as some porno where she’d just jump on me to unzip my pants, but we just looked at each other for what felt like too long.

“What?” I just blurted out, “disappointed at me?”

She didn’t answer. So I just kept looking, and I felt myself getting harder, I was wearing sweatpants so this just, couldn’t happen. I shifted slightly and her eyes went down. She knew. I knew she knew. She knew I knew she knew. I kept looking at her. Her lack of reaction and the frustration I felt at not being left alone for the evening just burst out in a moment of boldness I still can’t explain, and I kissed her.

I couldn’t believe it, this was actually happening, my boner was welcome in this realm. Still, we were just kissing, but I cannot put into words the insane sexual feelings this short neurotic woman raised in me. I wanted to ravage her. My hands were running all over her already, after a couple of minutes of this I kept kissing her while moving on top of her, propping myself up with one hand while pushing her legs apart with the other. I placed myself in between her legs and pushed my dick against her as we kept kissing.

I still couldn’t help myself, as incredibly turned on as I was, I pulled back and asked her if she was okay, she just nodded and pulled me back in. I just wanted to dominate her and wanted to know whether this was a… welcome development to her.

She wasn’t speaking anymore and it was fucking bliss, the moment I realized that I took her hand and put it on my erection through my pants, she pulled her hand back and slid it inside my waistband instead, fucking fair enough, I thought. I knew I could not withstand much foreplay so I slid my pants off as fast as I could and stood next to the bed and led her head towards my dick.

I could tell my feelings were reciprocated as she just took it all instantly, usually girls would give a bit of a tease beforehand but nope, she was instantly game. I still had my hands on either side of her head and held it still so I could fuck her mouth. She was unbuttoning her shirt and her pants as I did. She was always a great at multitasking, that’s for sure.

She grabbed my hands and moved them off her head, laying back on the bed and struggling to remove her pants, I helped her slide them off but stopped her as she tried to remove her panties. I positioned myself between her legs again and lead my dick against the wet spot on her panties, grabbing an ass cheek with one hand and a boob with the other, kissing her deeply, I wanted everything. She slid a hand under her panties and started rubbing herself, pushing her panties to the side so my dick could slide against her opening. We stayed like that for a few minutes, taking in what was happening, feeling every inch of each other. Until she closed her eyes and I could see her concentrate, reaching orgasm. I sort of stopped rubbing against her and just pressed my dick against her clit as she orgasmed.

Her hand still under her panties, she grabbed my dick and directed it inside of her. Still the hottest way I’ve ever penetrated any woman, hands down. I know this is gonna sound like some bad women’s anatomy, but the fact that she was so tight just felt, right? It just fit her personality, I know that’s ridiculous. But she was incredibly tight. Entering her was smooth as she was dripping wet, and my dick was too from rubbing against her.

I put my hands under her shoulders, grabbing them and fucked her, letting months of frustration out. I knew I didn’t have much longer in me, and I desperately wanted more of that ass, so I slid out and turned her around, laid her down and spread her ass, taking in the view, and slid back inside of her.

“Don’t cum inside me,” she said. A bit disappointing, but most reasonable. Surely that kind of clear-headed thinking is what got her into a manager position so young. Still, a bit annoying. I grabbed her ass harder (it genuinely made my hands look tiny) as I got closer and got my dick out. I knew how I wanted this to end, I sandwiched my dick between her buttcheeks and she put her hands on them, closing them tighter on it as I finished myself off, watching it drip on her pussy, exhausted.

I have to say what followed was a bit disappointing. We cleaned ourselves off and put our clothes back on not knowing much of what to say to each other, the sexual tension gone, it was just a bit awkward. She kissed me again and asked me if we could just enjoy what just happened and not talk about it right now. We laid back in bed and fell asleep together.

Didn’t finish polishing that presentation if you do care, and no, the clients didn’t give a shit. We talked in the morning and agreed that we were just tired and both needed an outlet and sometimes you can’t repress basic human urges, and agreed to never talk about it again, stressing the point that it mustn’t let our work dynamic change (I mean, that’s the whole reason I had those urges anyway).

It happened once more after that, a few months after, if you care to hear about it, I’ll oblige. Good times. Hot times.

Source: reddit.com/r/gonewildstories/comments/fe4wpk/a_story_about_a_singular_moment_of_boldness_on_my