[MF] The Beginning of My Affair With A Coworker: [Cheating] | 2016

Okay, where to begin with this... Honestly, typing this out is more cathartic than anything else for me as I still feel a hinge of guilt despite no longer being with my at-the-time girlfriend.

One summer, I worked a job that had an early and late shift, with about 5 hours in between. This was purely a summer venture for me, as I was currently in my third year of college, and I didn't really know what to expect. When I arrived on the first day, I met Jessica. Jessica was friendly, a little shy, but definitely the type of person I hoped to be working with for this. She had done this for a few years, and my time at work would probably be easy because of it.

This quickly turned out to be the case, and I quickly grew fond of Jessica because of the ease she brought work. My summer job was a piece of cake with her mostly taking care of everything, and the hours in between were nice for playing video games and other leisurely activities. My girlfriend, at the time, worked all day, a pretty typical 8 hour shift, and this 5 hours gave me some needed time away to do my own thing.

Working itself wasn't bad either, mostly because of spending time with Jessica. Her shyness steadily wore off, and as I got to know her more and more, we spend our shifts laughing with one another or having nice conversation. Of course, the catalyst to this story, in particular, is the fact that I realized I had an overwhelming attraction to her. She isn't the most conventionally beautiful, but she was cute and short (my type), and had medium-length dirty-blonde hair with a pleasant voice capable of calming and reassuring. Perhaps most importantly, she had an incredible ass. I mean this, too, as I never really had seen much like it before in person. It was an outstanding quality of her body, and I spend so much of each shift just checking her out in the leggings she wore every day.

As mentioned earlier, at the time of this event, I had a girlfriend. Naturally, I didn't want to do anything to infringe on that mostly good relationship, so the staring started as quick glances. But as the days went on, and conversations between Jessica and I got deeper and more meaningful, I felt my resistance slip away. I started staring for longer, almost hoping that she would notice how much I wanted to see her backside unclothed. It still remained mostly a fantasy, but there was a part of me that questioned whether or not I'd be able to resist fulfilling it if the opportunity arose. Worse yet for my integrity, I always felt as if I could sense a slight mutual interest. She didn't behave overtly flirty, but we always spent so much time talking about relationships and other personal stuff. She talked about her time on Tinder and what not, and we also had discussions that touched on where we currently saw ourselves, and the direction we wanted our life to take later.

Every once in a while, during our “in-between time,” I felt temptation to send her a text. I hadn’t communicated with her outside of the job yet, but the 5 hours between our shifts always gave me time to build up a mindless horniness. I genuinely felt as the only thing separating us from a mind-blowing release of sexual tension was a simple text message, but I still refrained from doing so out of a dedication to my girlfriend that still persisted. But day after day, I typed out a message, ready to send, only to chicken out. The idea of this girl wanting me bad enough to ignore my relationship turned me on, a lot. Jessica always found the time to mention that she lived on her own, about 20 minutes away from the job, and my brain always twisted that to a soft invite over to her place for a secluded session of unfaithful sex. Yet, our conversations never quite turned “that corner,” and all of my assumptions were still left to be just that, hopeful assumptions.

But one day, perhaps two weeks into our work experience, we started talking about how much we liked this particular show on Netflix. The conversation was entirely innocuous until a lightbulb went off in my head. Luckily I was seated at the time, because I almost got hard the second I thought about using this discussion as a launch off point to spend time at her place. Either way, what was there to lose? Either nothing happens and I keep my faithfulness, or I get a chance to release a load all over her enormous ass. I was thinking with my dick, if it wasn’t obvious, and I am ashamed to admit that at this point all concern about my relationship had went out the wayside. I was a broken man at the time, and the allure of seeing Jessica naked was too much to resist.

Long story short, I asked her if she wanted to spend our inbetween time watching this show, and she immediately accepted and invited me to her place. I figured she might ask if my girlfriend would be okay with this, but she didn’t mention anything and simply gave me her address. She told me to give her about an hour, and so I did before starting the drive over. At this point, a few thoughts of guilt crept over me - my relationship was relatively long term, after all - but my cock just got harder and harder as I got closer. When I finally arrived and parked, I gave a few seconds for my body to “calm down,” and then I went up the stairs and found her apartment.

I opened the door, and she greated. Her top was changed from our work shirt, but she had the same black leggings on. As she turned around to led me inside, my eyes instantly fixated onto her ass. I looked at the way it bounced, how tightly it pressed against that thin layer of black, and calmly told myself that it might be all mine within the hour.

There was a slight awkwardness to the beginning of this hangout, but she quickly started the show after offering me something to drink. We both took a seat on her couch, and stared at the TV. I’ve never been good at making moves, so my mind naturally avoided any concentration on the TV and instead begin devising how I’d do this. I figured transitioning away from the facade of watching the show was a good first step, so I asked Jessica how she spends the time in-between her shifts. She, somewhat embarrassed, told me that she mostly watches TV. To reassure her, I told her about the way that I spend my free time and how it wasn’t much better. After a quick awkward silence, I told her that we should hang out more between our shifts, and she happily agreed. We locked eyes for a brief moment, but then went back to watching the show. I had a chance there, but blew it, so I went for a move that would hopefully escalate us physically.

I noticed she was occasionally getting on her phone, so in a relatively juvenile move, I playfully grabbed it from her when she wasn’t looking. She smiled and looked at me, asking me to give it to her back. I jokingly said that I wanted to see what she was up to, and she moved towards me to grab it back. I instead lifted the phone up out of her short reach, and she got even closer to me. She was laughing as she reached higher and higher, and her body quickly pressed up to mine. I was hard, but I doubt she noticed at this time. She kept pushing towards, and I then fell down onto her couch. Desperate to grab her phone back, she accidentally fell onto me and grabbed the phone. In the aftermath, though, I was laying down on her soft couch with her directly on top of me. Our faces were inches apart, and nothing but pure instinct brought our lips together in the next second. Our first kiss was an intense one, and quickly, we were making out. She was just an okay kisser, to tell you the truth, perhaps overly liberal in her use of tongue, but I was still so entranced in the moment. She was kissing me with the ferocity of an uncaged animal, and I was able to forgive some of the crazy kisses in light of the fact that she was clearly turned on. We exchanged deep, wet kisses for about 3 minutes until I started moving for her neck. As I started to kiss down her neck, she moaned surprisingly loud for a woman as quiet as she typically is. I was still lying back on her couch at that point, so I lifted her petite body and flipped it around so I was on top of her. I alternated between gentle licks and hard sucks on her neck, and her moans made it clear that this was only the beginning.

I got increasingly more handsy, and with every escalation she moaned louder. My hands were rubbing her breasts through her shirt, and she quickly helped me flip her shirt and bra off. Her breasts were nice - not quite her ass, but nice - and I started rolling my tongue around her nipples as each one got firmer and firmer. But speaking of firm, I was outrageously hard at this point. I could feel the precum building in my boxer drawers, and this was before I finally grabbed a handful of her ass. Believe it or not, it wildly exceeded my expectations. I grabbed handful after handful, unable to hold it all at once, mostly because of its size, but also because of its firmness. However, I kept massaging her butt as I kissed her neck and nipples, and I gradually made my way to her ear to whisper and tell her how long I waited to feel her ass. She quickly responded with an “I know,” and we both laughed.

Massaging her ass made it easy to transition to rubbing her pussy, and that’s what I did. The thin layer between my hand and her wet vagina was a nice tease, but she quickly let me pull those off as well. As I pulled her leggings off first, and then her thin panties, I got my first look at her perfect pussy. It glistened with wetness, and this caused my already erect cock to become astronomically more hard; I was going to fuck this beautiful girl, in her apartment, a void separate from my real world and responsibilities.

Before I got a chance to go down on her pussy, she flipped my shirt off and quickly started unbuttoning my pants. My cock was finally released from the confined prison of my jeans, and it popped out with a fierce intensity and bounced back and forth. Her eyes fixated on my cock for about 3 seconds afterwards. I could tell she was impressed with it, even though I’m not much larger than average. Regardless, she deeply kissed me and wrapped her hand around my dick. Dammit. I was already close to cumming. This is the one part of this whole thing that I feared, but I saved face by getting back on top of her and licking her pussy for a while. After about 5 minutes of that, i asked if she could go down on me. And she happily obliged.

As her tongue gently rolled up my cock, I suddenly realized the pandora’s box I had opened. What would stop us from doing this every day? Without a soul in the world knowing? We had the perfect set up for this passionate affair, and I would get chance after chance to explore her body and soul with many intimate encounters. In this moment, all regret washed away, because I was going to fuck this woman in every way known to man by the time summer was over.

The sloppiness of her kisses carried over to this blowjob, and my dick was a wet mess as she went up and down, pumping hard and then alternating to slow. Again, I felt like I was on the verge of cumming. Unfortunately. I wanted to slay Jessica’s pussy as long as I could, until we were both exhausted and could collapse into one another like the shameful lovers we just became. However, it simply wasn’t in the cards this time. I groaned louder than I usually do - with the physical intensity and the scandalousness of the occasion meeting each other so fiercely - and told Jessica I was moments from cumming.

She didn’t even respond, instead simply taking me deeper into her mouth. She increased her hand action, and all I could do is lay back in intense pleasure as she finished me off. The second before I came, I went dead silent, grabbing the couch cushion behind me in intense pleasure. Every last load went deep into Jessica’s mouth, and I bucked up and down as each pulsation sent me into erotic heaven. Afterwards, my vision was hazy from the intensity of what just happened, but Jessica quickly popped back up to my face level and planted another kiss on me. I kissed her back. And then we started making out again. And it was only about noon, several hours before our next shift. With a whole summer to go.

And believe me, we used the hell out of that summer. We ended up doing things that I never pictured myself doing. If there is interest, I’d be happy to share more of our time together.