Cheating with the boss’ secretary [mf]

*Disclaimer: If you want to judge me in this story for cheating or anything else, please send me a detailed direct message explaining your issues. (That way you can waste your time and I can laugh while I ignore it.) In all seriousness, I was in a weird place at this time in my life, had a drinking problem, and as a result did a lot of bad, destructive, unkind and risky things. I’ve since cleaned up my life (for the most part) and have tried my best to be a better person and make amends. And as you’ll see in this story, I experienced at least a little bit of karma as a result of this incident anyway. Anyway, here goes.*

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This is a story about loneliness, desperation, bad decisions, and karma. But it’s a story of, objectively, one of the more erotic experiences of my life. So I thought I’d share it here.

At the time this story happened, I was in my mid-20’s and working at a small startup company in New York City. My job was in marketing and general operations, but it was small enough that everybody knew each other, even across departments. And, as happens often in startups, we developed a nice camaraderie with each other over time.

On the one hand, I was enjoying the prime of my life: I was successful in my job, I had a great group of friends with whom I would drink and cavort around NYC until all hours of the night, and I was living in a small, crowded, and overprisced but somehow still great apartment in the East Village with two of my best friends. But on the other hand, I found myself freqently missing feminine companionship. I was in a long-distance relationship with a great girl, Melissa (Melly for short), and, because our jobs kept us both very busy, we didn’t get to see each other nearly often enough. While my friends were enjoying their single 20’s in NYC, I would frequently find myself horny and alone late at night as they all went their separate ways to hook up. Sometimes I would push the limits–flirt with girls at bars a bit too much without letting them know I was in a relationship–but I would always end the night by heading home and jerking off at what might have been rather than doing anything that would hurt Melly. Put simply, I was sexually frustrated.

To describe me: At the time of this story, I was 24, 5’10”, 160lb with brown hair and eyes. I was fit and athletic (I run, lift, and play rec/intramural sports regularly) but not super jacked or anything.

[Here’s a photo from around that time for context](https://imgur.com/a/GFpxqVp) (slightly nsfw).

One day I walked in to the office early–I was usually the first one there–to find that I wasn’t alone as usual. A short, brunette young woman wearing a navy dress with red polka dots was standing next to the desk at the cubicle where my boss’ secretary usually sat, holding the phone receiver with a look of panic in her eye. “Um, I’m SO sorry but do you know how to transfer a call to a cell phone?” she asked me. She smiled sarcastically. “It’s apparently really urgent.”

I leaned over to show her how to work the phone, and as I did so, she moved to the side to make room for me in the cubicle. Two things happened when she moved. First, I caught the scent of her hair, which had that freshly showered shampoo smell that girls’ hair has and that, at least for me, always reminds me of my first romantic experiences with my high school girlfriend. And second, her breasts–which were about B cups if I had to guess, and perky in her dress–brushed my arm as she moved aside. I felt fleeting attraction toward her in that moment, and even moreso when she finished transferring the call, let out a big sign of relief, cracked a big dimpled smile and stuck out her hand. “Thanks, you’re a life saver! I’m Sarah, John’s new assistant. It’s my first day.” John was my boss, the CEO.

I introduced myself and went about my day, but I couldn’t help but steal glances at her from time to time. She was fit, about 5’3”, with shoulder-length straight hair that she kept tied back in a ponytail a lot of the time. And she had this great, wry, sarcastic energy about her. From that point on she became my work crush.

As far as I knew, though, it was just a silent, one-way crush. For the next few weeks we would cross paths from time to time in our small office, but we didn’t have occasion to talk much. She became friends with a few of my coworkers, but for whatever reason seemed to keep me at arm’s length.

Then, one day in October, it was our coworker Phil’s birthday–and so everyone in the office went out for drinks. Now Phil was a party-hard kind of guy, and as mentioned I had a bit of an alcohol problem myself (though I wouldn’t have described it that way at the time). When we went out, Phil and I were matching each other pickleback for pickleback as the night went on, and soon I was incredibly, stupidly, amazingly drunk. I was so drunk, in fact, that I didn’t notice that even as our group thinned out, Sarah remained and was keeping pretty good pace with us as we got wasted.

At some point I looked up and realized that it was just me, Phil, our buddy Greg, and Sarah left at the bar. I was about to head home when Sarah asked, “So where are we going next?” I did my best to casually agree without seeming too eager, and the others were in as well. Then Sarah said “what about Rick’s?” She was referring to Rick’s Cabaret, a strip club in midtown Manhattan. My jaw dropped, but I wasn’t going to say no at this point. So off we all went.

A few minutes later we were at Rick’s and had a table, and I was drinking a big glass of scotch on the rocks while a stripper sat on my lap pretending to like me. “You want a dance, baby?” she asked. I declined, but then Sarah said, “Oh, yes he does! I’ll buy it.” She was giggling drunkenly as the stripper straddled me and started grinding and gyrating. I started getting aroused and was a bit worried that my colleagues would see my boner through my work pants, which were a pretty thin material and didn’t hide much. But I was also a little too drunk to care.

Three dances later, Greg had left, Phil was in the back room, and I was out at our table with Sarah, horny as hell, watching her laughingly get her own dance from one of the strippers. I had finished my scotch and ordered another one.

The song ended and the dancer stepped away for a minute, leaving Sarah and I alone. She leaned over, took the scotch from my hand, and had a sip–our hands touching slightly as she did. I saw her eyes drift to the clear outline of my cock in my pants, and then to my eyes, and then to my lips.

There was a beat of silence. My heart skipped. I felt a surge of adrenaline.

Then she leaned over and kissed me.

I wrapped my hand around the back of her neck, pulled her closer, and we started making out. Her lips were soft and her tongue swirled with mine. She bit my lip lightly. Gasping for air as we kissed passionately, she moaned lightly as I slid my hand down her side and over the edge of her covered breast, teasing her. And then she climbed onto my chair.

We made out, oblivous to the world around us, Sarah on top of me grinding on my hard cock through my pants. She was wearing a sundress over a thin pair of panties, and I could feel her warm pussy rubbing against me as we ground together. Her breasts were pushing against my chest and sliding up and down as she ground against me. “Oh my god,” she said. I felt her body tighten, felt her quiver slightly on my cock, even through our clothes, and saw her face contort as she moaned again in my ear. Then her body loosened, and she pulled back, looking me in the eye. “Holy shit,” she said. “I just came.”

I smiled, and as I did I noticed a bright light in my eyes. It was the bouncer, with a small flashlight, kicking us out.

At some point, someone from the club had hurriedly shoved a bill on our table, so I paid for the scotches quickly, and then Sarah and I were ushered outside. When we got out to the curb, she turned to me, the passion and hunger in here eyes replaced with a fearful wariness.

“I don’t usually do that, you know,” she said hurriedly. “I don’t want you thinking–”

“No, of course not, me neither,” I said. “That was totally–”

“And you can’t tell anyone else at work,” she continued. “And this is a one-time thing. Okay?”

I nodded. “Okay.” I looked up the block to see if there was a cab I could hail for her. But as I did, she walked back toward me grabbed me by the hand, and pulled me toward her. Her hands wrapped around my neck and she pulled my head down toward hers and kissed me again. For the next few minutes we made out on the street, then against the wall of the club, and then against another wall. She was pressing her body against mine and my hands were sliding all over her torso, her ass, her firm tits. Finally she broke apart. “Can we go to your place?” she asked. I told her we couldn’t–my roommates had a bunch of friends visiting and it wouldn’t really have worked. Her apartment was far out in Brooklyn, so wasn’t a great option either.

She bit her lip. “Well, what about the office?”

Had either of us been thinking rationally, we would have thought this was a bad idea. But in our drunken and horny state, it seemed like the only option. I hailed a cab, and within a few minutes we were back at our office building walking tothe elevator as the night security guard looked at us with a raised eyebrow. “I just need to grab some stuff I left here,” I told him.

When we got up to our floor, Sarah grabbed my hand, pulled me into my office, shut the door, and turned off the lights. “We have to be quiet, okay?” she said. Then she pulled me down onto the floor so that I was on top of her and started kissing me. In the darkness, my hands found her dress and pulled the straps down over her shoulders, and slid it down to her stomach. I felt her hands clumsily fumbling with my belt as I reached behind her and unhooked her bra. I slowly slid my hands over her breasts, feeling her hard nipples. She shivered as I caressed them, unzipping my pants and pulling them and my boxers down in one rough motion. She slid her hand over my

[rock](https://imgur.com/a/XDUo3UU) [hard](https://imgur.com/a/V07irtW) [cock](https://imgur.com/a/rD3GXMA). Then she reached down, pulled down her panties, and pulled my hips toward her in what seemed like one single motion. I felt myself enter her warm pussy and she gasped as a I filled her up. She was dripping wet, and I was as horny as I possibly ever have been after all the making out and griding. I thrust into her hard, deeply and slowly, and she let out whispered moans with each stroke. “Fuck me,” she said as I thrust into her. “Fuck me, fuck me, fuck me.” I pushed deeply into her and felt her tense as she neared climax. I pulled back and thrust again and she grabbed me around the back and bit into my shoulder, suppressing a moan. I thrust into her again, pushing all the way into her so that my pelivic bone was rubbing against her clit, and felt her warm vagina begin to pulse. She arched her back, moaned–not in a whisper this time–and wrapped her legs around my ass to pull me into her even deeper. I felt her climax, and as she did, I came as well, unleashing spurt after spurt of my hot cum into her pulsing pussy.

“Oh my fucking god,” she said, as I moaned too.

Then I collapsed on her, kissed her again, and rolled over. We lay there, panting together. The whole of our intercourse had probably lasted less than five minutes, but we were both completely satisfied and completely spent.

After that, we got dressed and cleaned up. We went down to the street, and with a reminder not to tell anyone, Sarah hopped in a cab.

I went to get another drink. And, being a bit of an alcoholic, then I got another one. By the time I was in a cab home myself, I was as drunk as I’ve ever been, and I looked at my phone and saw that I had missed several calls from Melly. I would call her back in the morning. I got out of the cab and went into my corner bodega deli to get a sandwich to sober me up a bit before bed.

And that’s the last thing I remember. Like I said, this is a story about karma and bad decisions. When I woke up, I was late for work. I had a dozen panicked texts from Sarah saying we shouldn’t have done that last night and what if somebody found out, and a dozen texts from Melly asking where I was and why I hadn’t returned her call. And, probably most troubling, my face hurt like a bitch and was swollen beyond recognition. Apparently I had bumped into another customer at the deli and, in my drunken stupor, somehow incited a fistfight, which I had badly lost. (The deli guy showed me the security footage later. Basically I got knocked out with the first punch.) I guess you could say karma literally punched me in the face for cheating on my girlfriend.

I spent a long time facing the consequences of this particular night–from the injured face to the bad work dynamics it created with Sarah to the eventual end of my relationship with Melly (who to this day is one of the nicest and most honest people I’ve ever dated). But it was also one of the most erotic experiences of my 20’s.

Source: reddit.com/r/gonewildstories/comments/a1lccy/cheating_with_the_boss_secretary_mf

5 comments on “Cheating with the boss’ secretary [mf]

  1. Amazing story, I love that you came inside Sarah!

    Like you, the hottest sex in my life was a case of cheating. After a week long seduction, I fucked a friend of a friend while we were (slightly less) drunk, and I came in her unprotected. Similarly, she ended things because I handled cheating with her poorly. We fucked several times over the next few days, and I got married 2 months later

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