A steamy affair [m/f] with a married coworker: How it started

My secret adventures with Isabella began when we were both 27 years old and working for a medium-sized company in a large US city. I had been employed there about 2 years, Isabella about 4 years, with her informally serving as one of my supervisors. We had a closer friendship than most others in the office, but she was married and I was in a long term (and long distance) relationship.

To provide a mental image on our appearances – Isabella is a hardcore runner and workout freak, which is obvious at first glance: she’s slender and with a muscular hint, about 5 foot 6 inches tall, dark skin, dark hair, tone legs, and DD breasts. She’s very sexy, and has a look that she can give you that sends a shock through your stomach and gets your libido going. I’m 6’1, mostly in shape, on the skinnier side, and generally told that I’m a good looking guy. I’m usually labeled the “nice guy” but have always had an insatiable sex drive – which always surprises and impresses girls when they experience it.

Isabella and I enjoyed a purely platonic friendship for several years, and I genuinely didn’t even look at her in a sexual way. That is, until the office Christmas party. The boss gave us a half day on a Thursday, and rented out the private back room of an upscale restaurant for lunch. We had a four-course lunch followed by a three-hour open bar. (Thursday open bar lunch is definitely an odd choice but he didn’t want to pony up for a dinner.) Isabella, unlike myself, isn’t a big drinker and everyone noticed she was the drunkest one at the party before it was half over. At one point, she interrupts a conversation I’m having with a colleague while sitting at the bar, nudges her way in and sits in my lap. I’d had a few drinks but wasn’t drunk, and her outward flirting was testing the boundary of harmless and inappropriate. Either way, I knew at that moment that she was attracted to me, but I highly doubted we would ever act upon it. Other coworkers started making jokes, and telling me to watch out for her. Finally, she made a comment in my ear about us finding somewhere private to talk, and I decided to call her an Uber. It was only around 5pm and she was definitely embarrassing herself. The Uber arrives, and I walk her to her car and say goodnight. I spend the next hour at the party dispelling accusations that she was hitting on me.

The next morning, I arrive to work to find a $20 bill on my keyboard and a post-it note with the message “Thanks for the taxi” written on it. When I walk down to Isabella’s office, she buries her face in her hands in embarrassment. We discuss the events of the night and she apologizes for any inappropriate behavior. I ensure her there’s no ill will and that all is well.

As Isabella and I (as well as most others in the office) used gchat daily to discuss both work and non-work related issues, we spent much of that Friday hungover and gchatting about blasé things. At one point, I brought back up the topic of the night before, and the conversations surrounding her advances toward me. Her response and attitude to it was along the lines of “haha…oops.”

And it was from this conversation on that our entire friendship would explore new terrain and take on a deeper meaning. We opened up about the most intimate aspects of her marriage and my relationship, particularly our similar dissatisfaction with our sex life with our respective partners. We each craved more and better sex, but our partners were not on the same page. We discussed our mutual love for oral sex, and she bragged about her skills at giving blowjobs, but that her husband didn’t appreciate them so she didn’t give them that often. I said I had received mind blowing blowjobs in the past, and where does she think she would rank. She remained confident that she would be at the top of the list, but I was flirtatiously skeptical. This sexually charged banter really turned me on, and it continued for the course of day, to the point where I could feel the precum on my leg when I stood up.

We accomplished next to nothing at work the rest of the day, but both ended up staying late because the conversation was just too hot.

The following Monday was a little awkward, and we could both feel it. We walked to pick up lunch together, as we often do, and our conversations reverted to an innocent and platonic nature. I thought maybe last week’s sex convo was a one-time thing, but I wanted to find out. When we returned to our desks and were both on gchat, I broached the subject and tested the boundaries:

Me: so, I gotta say, last week’s convo really got me going…

Her: oh yeah?

Me: very much so

Her: me too

Me: like to the point that I went straight home and took care of it…

Her: haha, well I’m glad you found some relief

Me: yeah, but not exactly the relief I was hoping for. Who knows if we’ll ever be able to reach a verdict on your skills

Her: I told you I was down but I know you’d chicken out

Me: we both know that’s not true

Her: do we?

Me: for sure. I actually think you’d be the one to back out

Her: hmm. Well if the circumstances were different, I definitely think we could make it happen, but I don’t think we’ll ever even have the opportunity

Me: you can blame it on a lack of opportunity if you want, but that’s bull. We can definitely make it happen

Her: and how’s that?

Me: I’ve run through a few scenarios in my head that I’m confident could work

Her: like what?

Me: you know how the doors in the stairwell don’t open from the inside? So people can only go down them?

Her: yeah

Me: well the two floors above us are currently vacant…

Her: ahhhh. This is very interesting

Me: yes it is. and people rarely use that stairwell anyway, and NO ONE uses it from above us. Just something I’ve been thinking about

Her: yes you’ve clearly thought this through

Me: well it’s always been a fantasy of mine

Her: mine as well

Then there was very long pause, at least 5 minutes. I was rock hard, and I was battling the moral issues in my head with simply having this conversation, much less the possibility of cheating on my girlfriend with my married coworker. But I wanted it. And badly. I was so horny and hadn’t gotten a blowjob in months.

The conversation resumes:

Her: let’s do it
Me: yes
Her: you go first. Walk to the stairs and go up a flight to the 5th floor. I’ll meet you there in 5 minutes
Me: ok. Leaving now

I stand up, tuck my erection up into the top of my pants, and walk toward the front door of my office. I smile at the receptionist, and walk to the stairwell. My stomach is in knots and I’m breathing heavily. I think to myself how Isabella and I have never even kissed. I’m acutely aware of how strange this situation is while I listen intently for the sound of Isabella opening the door of the stairwell one flight below me. I wonder if she’s going to back out, and notice that my erection is gone as a result of the nervousness.

Finally, I hear the reverberations of a door shutting in the concrete shaft of a space, and hear footsteps on the stairs. When I see Isabella walking up the second half of the staircase, she’s giving me this hungry, devilish smile. She reaches the 5th floor platform area and stands close to me. We look at each other with a tad bit of awkwardness and a whole lot of horniness, and I shrug my shoulders and say “well…” I reach around her waist and place my hand on her ass, squeezing it tight and pulling her closer to me. She pushes her faces into my neck and breathes deeply while placing her open palm on the bulge in my pants. She kisses me neck and I notice that my cock is mostly hard now. I tell her I lost my boner due to the nervousness, but that I bet she could bring it back. As I reach down to unzip my pants, pulling my cock out for her to see, she drops to her knees with a huge smile on her face. She wraps her fingers around my dick and looks up at me with that devilish grin, gently stroking me as my dick rests inches from her face. She first twirls her tongue around the tip, and I comment that I will probably not be able to last very long. She keeps staring at my dick, then sticks her tongue all the way out and give my shaft a long lick from base to tip.

In her kneeled position, the palm of her right hand is on the left side of cock as I’m looking down, and she uses her right thumb to massage the sensitive area on the underside below the tip, while she’s back to licking the tip. I’m thinking how I want this to last longer, but my body is already aching for a release soon. I give a deep exhale and shake my head, and I place my right hand on the back of her head. As I do that, she opens her mouth and takes me in as she continues to massage with her hand. I let out a “fuuuuuck yes,” and she responds with an eager moan that sends vibrations through my dick.

She takes about 3 inches of my 7 inch cock into mouth, while twisting her right hand around my shaft and using her thumb to massage the underside. I get a fistful of her hair and gently direct her to pick up speed as the sensation inside my body become more and more powerful. After no more than two minutes in total of her sucking my dick, I say “I’m gonna cum soon.” This obviously turns her on even more and she somehow increases her enthusiasm level as she worships my cock. Seconds later, I explode inside her mouth. She sucks even harder as I’m cumming and matches the rhythm of my body convulsions with the stroking of her hand and movement of her lips along my shaft as she nurses the last drop of cum out of me. I’m breathing deeply at this point and nearly fall over as I find my back is almost touching the concrete wall. She waits until I’m completely finished, takes me out of her mouth, and wipes her lips in the sexiest way as if she were a ravenous animal who just enjoyed a satisfying meal.

I’m still catching my breath as she stands up, and I mumble “wow” in a slow and dramatic fashion. She gives me a look of confidence and satisfaction, an eyebrow raise, and that same damn devilish grin. A grin that would lead us to visit this stairwell at least 25 times over the next few months, as well as other promiscuous behavior and adventures.

This took a long time to write, but if it’s well received then I’m happy to share more stories from this six-month long intense affair, including more than blowjobs, tons of very hot gchats that always culminated in stairwell visits, hookups in my car parked on the street, and me getting her to wear short skirts and no underwear to work and then flash me in the middle of the office.

Source: reddit.com/r/gonewildstories/comments/4ux7lt/a_steamy_affair_mf_with_a_married_coworker_how_it