The Work Fling [MF]

I had the biggest crush on a woman that I had zero chance with. I’ll call her Samantha for the sake of this story. She was heart-stoppingly beautiful, insanely smart, incredibly ambitious, fit and sexy as hell, and — in the circles that I traveled in — a celebrity of the industry. From the first time I saw her I was in deep crush-from-a-distance and so were all of my industry peers. I interacted with her occasionally at conferences and she was usually pleasant if not overly cocky about her awesomeness. She had a glib tongue and a sardonic personality — which, honestly, made me like her even more.

Well, after one of the conferences she invited my peers and I to join her and the other executives for dinner — which was normal — and then to have beers with them back at their hotel before they left the next day. I was eager to ingratiate myself to her so I bought the beer, went to their hotel, and had the most awkward conversation of my life with people who could fire my ass in 10 seconds if they so choose. My peers never showed up — they probably knew it would be weird — and very quickly it was just Samantha and I sitting in the lobby having a beer and listening to John Mayer on her phone. When it was just the two of us I was a little more natural, but she was intimidating as fuck be around. I don’t remember the conversation, but it was perfectly normal and very casual. She asked for my cell phone number, said she would text me sometime, then told me she was transferring to this area in the next month or so.

‘Cool’ I thought; ‘I can show her around, maybe work my way up the ladder. Maybe trick her into falling in love with me or something.’

Well, she did move to town shortly thereafter with her boyfriend of a few years who I didn’t know existed. She showed up to the job once in a while and asserted her authority while she was there. A few weeks in and she started to text me out of the blue and asked what I was up to. I chatted with her a bit thinking it was a work thing — it was — she needed a ride somewhere. I offered to do it and she was grateful. A few days later she texted me again and didn’t want anything per se. A few days later the same thing.

“You should come over to my place tonight, I’ll make tacos, you bring beer.” It was a Wednesday night and I was normally busy with my martial arts classes, but… fuck yeah I’ll do beer and tacos with this bad ass b**** who scares the shit out of me. So I picked up some Tecate, a few limes, and drove to her apartment. She let me in, put the beer in the fridge, and sat me down on the couch. I took in the scene and things were pretty sparse and nothing worth remarking about save free weights on the floor in front of the TV and the Glock on her side-table partially disassembled in the state of being cleaned.

We had dinner in her kitchen, cracked some beers, and got to talking. She told me she had broken up with her boyfriend a few weeks after they moved to town and he moved back home leaving her all alone here. She said she was glad, they had been together for years and he just wasn’t as ambitious as she was. He had been the first — and only — person she had ever been with and she wasn’t sure that she wanted to start dating yet. She was horny though, and really wanted to fuck, but she needed someone safe. Someone who would be at her beck-and-call. Someone that would keep their mouth shut at the office.

Holy fucking shit.

I can read between the goddamn lines.

This is my dream come true.

We went to her living room and she put on a movie. She finished cleaning and reassembling her gun while we talked. As soon as she was done she got on her knees, pulled out my cock and began to suck me off. I was as startled, happy, confused, and afraid as I had ever been. She took off her top — she wasn’t wearing a bra — and her breasts were perfect. This woman was exactly as sexy as I had fantasized she would be — probably even more.

“You’re so hot.” She whispered to me as she licked the head of my dick.

“You’re so hot. I have had the biggest crush on you for years.”

“Mmm, I know. You aren’t good at hiding it.” She was so cocky and I loved how she was turning the tables on me, “I’ve wanted to fuck you for a long time.”

‘ARE YOU SERIOUS?’ I was screaming this in my head while I watched my crush getting my dick sloppy wet.

“You can never tell anyone. You know that right? This is our little secret.” I was losing my mind and struggling to keep my dick hard. For as hot as this was I was so worried that I was going to fuck it up. She started to notice that I wasn’t up-to-task and she got really disappointed but didn’t give up. She took off the rest of her clothes and so did I. Her body was flawless. I was fit, but flabby, and feeling self-conscious. ‘Don’t ruin this!’ I was screaming at myself again as I began to concentrate on being a man and getting hard for her.

She started to blow me again while she rubbed her pussy and I still wasn’t manning up. I realized that the problem was me and I needed to take control. I was way too intimidated by her — so much so that I had never really been myself around her — that had to change. So I stopped her, held her face in my hands, and planted a kiss. Our tongues flitted in and out of one another’s mouths and it was exquisite. I kissed her neck and she grabbed my ass and I could feel myself start to get hard. She grabbed my hand and led me back to her bedroom where I proceeded to sit her down and started to lick her pussy. Now I was throbbing hard.

I slipped a finger inside of her as I played with her clit and tasted her sex. She began to writhe and move her hips in rhythm to my tongue as she moaned and panted her satisfaction. She grabbed the back of my head and held it where she wanted it until I finally made her cum and then she demanded I fuck her.

She handed me a condom which I slipped on diligently; worried that if I didn’t do it fast enough I might start to lose my hard-on. Something like that had never happened before, so I was freaking out that it had happened the one time it shouldn’t have. She pulled me toward her as soon as it was on and guided me into her perfect pussy. There had been no greater satisfaction for me throughout my sexual history to that point than watching my fat cock push inside this woman.

“You’re so big. Go slow. You’re so much bigger than my ex.”

I took my time with her, getting her used to me, enjoying the show and grateful that I had gotten over my earlier dysfunction. The sex was fine, technically, she was clearly not that experienced and I was having a crazy emotionally distressing day in my own mind so I was nowhere near at my best. When I was ready I pulled out and came on her tits; kneeling there next to her in triumph.

She cleaned herself off, we got dressed, then she started to kick me out. I kissed her again — a sexy goodbye kiss — and that started things all over. I got hard right away, we stripped down, and then we fucked again. The second time was better than the first and she let me cum on her ass after fucking in doggy style to finish up. I left, completely flabbergasted and wildly unsure of how to proceed.

We hooked up a few more times over the next few weeks, but I was a dumb ass and talked about it to a few of my peers at the office. I had to let them know. It was too good not to share and I am, by my very nature, a story teller. I was honest with her about it and she cut me off. She didn’t come by the office very often after that, but she was still a presence. Every time I saw her from then on she was an absolute raging bitch to me. I suppose that was fair. Fortunately, it didn’t cost me my job; but it did cost me a few friendships at the office; the guys were jealous at my dumb luck. They all wanted her, but only I got to have her… that I know of. Everyone else was probably smart enough not to talk about it.

Source: reddit.com/r/gonewildstories/comments/mld1kw/the_work_fling_mf