I cheated on my wife with a coworker

I cheated on my wife with a coworker. It happened two months ago and I can’t stop thinking about it. I’m going to tell it as I remember, though I’m sure some details are missing or partially forgotten (or else I might embellish a moment or two, but even if I do the essence of what happened and how it happened is true). And forgive me if this is long. The truth is, this is the hottest thing that has ever happened to me and I want to savor it again in the retelling. I hope it gives you a thrill as well (and if it does, I hope you tell me).

Believe it or not, my wife and I actually have a great relationship, with a lot of love, happiness, and great sex. Yet, this is not the first time I stepped out on her. We’ve been together going on 15 years, and in that time things have come up. Most of it was drunken flirting with a few, exciting connections that led to kissing and touching. Shortly after we got together, though, I hooked up with a female friend (we had been circling each other for a long time; long before I met my wife) and ended up maintaining a years-long affair. But that’s a whole other story to tell (and maybe I will tell it in another post). After that ended I was a good boy for a long time. Eventually, though, I got bored, I guess, and went online. I never met any of the women in person but I made a few connections that lead to the usual (sexting and sharing pics).

But I had stopped that a while ago and hadn’t even really thought about being with another woman in years. Until two months ago, that is.

My work is fully remote, so I don’t see my colleagues in person very often. A lot of Slack and email. I’m friendly with a lot of them, but noticed about a year ago our COO (f35ish), LS, started messaging me things unrelated to work. Casual and friendly at first. But as time went, the tone of her messages became a lot more flirty. Still very innocent, but flirty nevertheless. For my part, I flirted back, careful to keep it in line with the tone she was setting.

Innocent as it was, I still got a huge thrill out of seeing a message from her and was all to eager to keep the flirting going. Not least of all because she’s incredibly hot. A mom of two but still incredibly fit, with a tight ass and small tits. And gorgeous - a smile and eyes to melt anyone.

So when our annual all staff retreat was getting near and LS started messaging me out of nowhere that we should get a drink some night, I couldn’t really believe it was true. I was sure I had to be reading into things. I’m no slouch my any means, but I had a hard time believing this married mom of two who was also my COO would risk any of that for a workplace affair.

We never pinned anything down ahead of the retreat so I flew out not expecting much. It was a four day retreat with three nights in a hotel. The first night was casual, with a dinner and remarks from leadership, including LS, who looked so sexy in her dark dress with a low neck line. Though I was hoping she’d bring up getting a drink again I wasn’t going to hold my breath or push it. Besides, she looked pretty busy that night, running around helping to keep things organized and talking to staff. We did say hi briefly, and hugged, but just as soon as we came together she was pulled aside to see to something. I ended up going to my room early and jerked off, coming hard to the thought of LS.

The next day was a series of boring training sessions and various activities for staff. Seemed it was going to be the usual retreat routine. Then LS Slacked me. “Omg, I’m so ready for this day to end. Drinks after?”

Sitting at a table full of colleagues, talking about our personality types, I felt myself get hard. She was a few tables away, and though I didn’t look in her direction I felt like she might be watching. So I smiled and replied, “yes please.” She suggest we meet at a bar a few blocks around 8pm.

The rest of the day’s sessions were a blur. As soon as the day was done I went to my room and got ready, trying to look nice without being too obvious. At a quarter tell I walked to the bar, thinking where would be the best place to sit. I decided sitting at the bar would be best because there would be no table between us and we’d have to turn toward each other to speak, bringing our legs close together. It seemed way more intimate. I picked up my pace to get there before her. But it didn’t matter. She was already there, sitting at the bar.

She smiled as I walked up, and stood to give me a hug. She had changed, too, into another dress. This one hitting above the knee with a neckline that revealed her cleavage anytime she leaned forward. My cock was already swelling in my pants.

She already had a glass of wine in front of her so I ordered my usual martini and we started chatting. Talking with her was easy. We joked about the retreat, and she laughed lightly at everything. The talk became a bit more personal, though I noticed she avoided anything to do with our spouses.

We finished our first round and ordered another. With each sip we seemed to get closer to each other; our legs touching at times. She even started to touch me lightly when she laughed. First my shoulder. Then arm. Then knee. I did the same.

It seemed like it was all leading directly to
where I had hoped. But before we had finished our second round she went to the restroom and came back a little different. We still laughed, and our legs touched, but I noticed she would look away and avoided eye contact. And when our legs did touch she’d pull hers back again. I got the impression she was feeling nervous and assumed she was getting cold feet. I decided not to push it.

But still, I didn’t want to give up completely, so I figured I’d see if she wanted another round. That’d give her a little more time think and maybe lose the cold feet.

There was a silence in the conversation where she looked away to take a drink. Then she met my eyes and smiled. I wanted her so bad and was about to ask if she wanted another round when her eyes left mine. She sat up straight and pulled her legs forward.

I didn’t have time to process because she then flashed a smile past me as she looked over my shoulder at JK, another colleague, walking up.

Feeling like a caught school boy I also sat up and tried my best to present like nothing bad was going on (not that anything bad had gone on, really).

LS put on a good face but I could tell she was also feeling caught. JK stood by us and said she didn’t want to interrupt. It was all a bit awkward and LS said she was just needing to head back and hastened to close out.

I was smiling but in that moment I hated JK with a passion. I stood to give LS a hug goodbye and felt dizzy trying to figure out how to keep our night going. I had nothing so was left to watch helpless as LS left. JK smiled down at me, asking if she could join me. I still had some of my drink left and with LS gone I figured why not. So I smiled and helped her push out the stool.

JK is around 60-65 and had been with the company for a long time. We work in different departments so don’t really interact with each other all that often. She had always been nice, and vibed like a cool older woman. But in that moment I was still mad at her for interrupting my night with LS. Not that I was all that sure anything was going to happen. But still…

I was thinking about what I could message LS that would be innocent enough while opening the door for more to happen that night. I was a bit lost in this thought when the bartender took JK’s order, and I absentmindedly said that I’d do one more. Figuring the night with LS was lost I decided to let it go. I smiled at JK and we cheersed when we got our drinks.

As easy as it was to talk to LS, JK was even easier. She was casually confident with no nervous ticks. And unlike LS she talked openly about her life and husband. They had been together forever, no kids (and never wanted any). She said they were happy but,
“you know…” I opened up a bit about my marriage (happy, but, “you know”) and was genuinely having a great time talking to her.

I didn’t even realize, until she gently pushed my knee during a laugh, that our legs were touching. And that’s when I noticed just how sexy she is.

She has long, thick red hair that falls in loose curls. Her skin is pale, with bright pink features covered in freckles. That night she wore a white Oxford, tucked into a high-waisted pleated skirt. The shirt was unbuttoned enough to expose her freckled chest that anticipated the large breasts filling out the shirt. When she went to the restroom I got a good look at the rest of her body and was amazed at how curvy she was; with a large ass that her skirt draped over in a way that outlined it perfectly as she walked. I felt myself get hard and thought that I’d jerk off to her in my room when I got back.

When she came back she held my shoulder as she sat, letting it linger a moment. Just as she did when she tocued my leg a little while later. Just as I did when I touched hers a little after that.

Already buzzed when she showed up unexpectedly, I had been nursing my third drink. She was already nearing the end of her second when she said it was getting late. She was right, and we had an early morning, but I still didn’t want the night to end. With better judgment, we closed our tab and walked back to the hotel.

It was a quiet walk. Apropos of nothing she said that she liked staying up late because it made her feel bad and being bad made her feel young. I wasn’t quite sure what to make of that comment but I said something a little awkward about her not being old. She politely laughed but said nothing.

We rounded a corner and she walked ahead of me for a moment and I stole another look at her body. I wanted so badly to take hold of her. To dig my hands into that ass and tell her just how sexy I thought she was. But I said nothing.

We made it back to the hotel and took the elevator. I was on a lower floor than her, so would get off first. My cock was already getting hard thinking about jerking it to JK when I got back. I stole another quick glance at her large, full breast as we got to my floor.

When the elevator open there was a moment when I thought of saying goodnight and walking on with the door closing behind me. Instead I asked “do you want a night cap?” Our company had booked us at one of those trendy boutique hotels that cater to younger, hipper guests and each room had a wet bar with a few bottles of pretty nice liquor and wine. Without missing a beat she said “would love one.”

She followed me down the hall and though it was late I felt a little nervous that a colleague might come out of their room and catch us. If JK felt the same she didn’t let on. She seemed as confident and calm as ever.

I opened the door to my room and stepped in, holding the door for her. She took a few steps in and stopped. I closed the door then turned to her and without a moment’s hesitation we both stepped into each other, our mouths meeting in an explosion.

She sucked my tongue into her mouth as I pushed her against the wall, her pressing back into my hard cock. With one hand I held onto the side of her face, letting it move back along her head and into her hair, while the other grabbed her ass and pulled her a part. With this she leaned her head back, letting out a moan. I lowered my mouth to her exposed neck, kissing and licking all along her freckled chest. Keeping my one hand in her hair I moved the other from her ass and buried in between her crotch. Even through the fabric of her skirt I could feel the warmth of her pussy. She let out another moan as she closed her fist in my hair. Her other hand gripped my cock through my pants and tugged greedily.

I brought my mouth back to hers; this time she slid her tongue into mine. She still tasted faintly of her cocktail. While we kissed I felt her breasts with both of my hands. They were fuller and firmer than I was expecting and I could feel her nipples poking hard through her shirt. While we made out we unbuttoned her shirt together, letting it fall to the floor. She wore a white, sheer bra that exposed her nipples. They were a soft pink color and firm in my mouth as I sucked on them through the fabric.

One hand held her breast to my mouth while my other moved to her ass. With it, I lifted up her skirt and slid my hand under her panties, coming up from behind her. Her panties felt soft and lacy and I remember wondering what color they were.

While biting one nipple through her bra, her hands in my hair, my hand came through the back of her panties to find her soaking wet pussy. It slid smoothly across it and my finger tip found her clit, swollen and slick. My fingers already lubricated from the pool between her legs, I fingered her clit easily. She bit my ear and moan loudly as I kissed up along her chest and neck.

I slid one finger insider her, keeping another on her clit. She moaned louder. I slid another finger into her. She moaned louder, asking me not to stop. I pressed them in deeper, moving my other hand to her hair, which I gripped tight to bring her head back. She was so wet it was easy to slide my fingers in and out, but I could feel her pussy contracting, pulling tight around my fingers as she came.

She had pulled me into her as she came, holding me tight, shaking as she continued to feel the waves of her orgasm. Finally, and a little out of breath, she relaxed a bit and said, “I want you in my mouth.”

I kicked off my shoes and helped her out of her heels, taking a moment to squeeze her hips and ass while I kissed and licked her legs. Being so close to her pussy, I was temped to lift her skirt and finally taste her (I had wanted to put my mouth on her the moment I closed the door). But my cock was throbbing, ready for her mouth.

So I took her by the hand and led her into the room, stopping next to the bed. Except for my shoes I was still fully clothed. She was now in her bra and skirt. We kissed for a moment while she pawed at my hard cock through my pants. She whispered again that she wanted me in her mouth and I had a moment of clarity and thought, “I can’t believe this is happening.”

I took off my shirt as she dropped to her knees and expertly undid my pants in one fluid motion. She pulled my pants down a little and peeled back my underwear, taking my cock in her warm hand to remove it fully. I had never seen my cock so hard. The head was swollen and shining wet from the precum already flowing from the tip of it. She stroked it a few times and then lowered my pants more to let my aching balls free. With one hand on my cock and the other holding my balls, she paused and looked up at me with a smile. Her face was flush, making her freckles burn a little brighter. I remember thinking how sexy her eyes were.

And then she said, “you have a beautiful cock” before licking the precum off the tip of it. She then put it in her soft, warm mouth. Keeping one hand on my balls, she sucked on the tip, using the other hand to stroke the shaft. Her tongue playing with the head made me go a little weak in the knees. I actually had to shift my weight to stay upright. Then she brought the whole thing into her mouth. She was all over it. In one moment she’d lick the shaft, in the next she’d bury it down her throat, placing her lips around the base of it. Then the next moment she’d have her lips around my balls while she used her hand to stimulate the head of my cock. Everything she did made me feel drunk in the best possible way. It was, in no exaggeration, the best head I have ever gotten.

I didn’t want it to end but knew if she kept going I was going to cum before we got to fuck. I told her as much and she said, taking my cock out of her mouth, but continuing to stroke it, “will you be able to keep going if you cum?” I told her I would, and knew it was true.

She didn’t say anything. She just put my cock back in her mouth and sucked on it even harder, one hand gripped to its shaft with the other wrapped around me, holding onto my ass.

I put my hands into her hair and I let myself cum down her throat. It was a big, pulsating orgasm, which she milked into her mouth, not pulling away until I had finished. When she did, she looked up at me and swallowed before going back to suck my cock dry.

Despite that massive orgasm my cock stayed rock hard. I brought her to her feet and we kissed. With a free hand I unclasped her bra and took her bare breasts in my hands as the bra fell to the floor. She said, “I want you inside me.” I told that she would, but first I wanted my mouth on her.

She unhooked her skirt and stepped out of before I sat her on the bed. Her panties were lacy and white and I remember thinking between her sheer bra and these sexy panties, I was sure she was hoping to show them to someone that night. I was so grateful that person was me.

I pulled her ass to the edge and she laid back. I ran my hand over panties, pressing against her pussy. The crotch was soaked through. I could smell her; faintly floral. I put my mouth on the gusset of her wet panties, feeling her swollen clit and labia through the fabric. I sucked and licked. She moaned. I slid a finger around the gusset and pulled it aside, revealing her glorious pussy.

It was bright pink, a little puffy, and capped with a patch of long, strawberry blonde hair, shaved bald around the sides. Her clit was visibly swollen and red. The whole amazing area glistened wet and a dab of fresh juice flowed from its entrance, down to her pink asshole.

I couldn’t wait any longer. I slid my tongue up her slit, stopping on her clit, which I sucked into my mouth. She tasted bright and floral. I brought my tongue to the opening and licked up her juices then retuned to her clit, tonguing and sucking it while I slid a finger into her.

She moaned and tightened her pale, freckled thighs around me. I spread her legs again and plunged my tongue inside her while my fingers pulled her open.

I returned my tongue to her clit and, without thinking, slid my finger across her wet asshole. She moaned louder so I continued to rub the tight, quivering hole before sliding my tongue down her pussy to it. As I licked her asshole I used one hand to keep her pussy spread apart, and the other to thumb her clit.

After a while I switched - put her clit in my mouth and rubbed around her asshole with my wet finger. She came again when I slid a finger into her ass while I tongued her clit. It was an orgasm that came in heavy waves and her body shuttered around me.

When she finished I stood and looked down at her. She had her eyes closed, head back, basking in the glow of her orgasm. She had one hand in her hair and the other pinching and playing with an erect nipple. Her panties were on but still pulled to the side, revealing her dripping wet and quivering pussy.

She was beautiful.

I didn’t want to interrupt her bliss but I looked down at the still hard cock sticking out of my open pants. It was eager to be inside of her.

She must’ve read my mind because she opened her eyes and said, “fuck me now please.”

I reached down and pulled off her panties, putting them to my mouth, taking a moment to savor the taste of her again. I dropped them and took off my pants.

Fully naked, I could see the shape of her better. She was curvy but relatively fit, thick in the hips and ass with large breasts. The weight she carried in her midsection was soft and filled her out in a way that made me want to kiss every inch of her.

I leaned over her; she still on her back at the edge of the bed. We kissed and she took hold of my cock. Together, we moved up the bed so we could fully lay out, me on top of her.

Between her legs I took my cock in my hands and brought it to her pussy. I first rubbed the shaft of it up and down, then pressed the head of it on her clit. As much as I wanted to plunge myself deep inside her I enjoyed watching the waves of euphoria ripple across her body as I teased her with my cock.

She whispered “please” and I brought the tip of my cock to her wet opening and thrust it in. She braced and let out a moan. Despite being 25 years older, her pussy was tighter than my wife’s. And wetter. I fucked her slow at first, one hand lifting up one of her legs from the thigh, with the other holding myself up over her so we could kiss. Eventually I started to thrust harder and when I did I started to kiss down her neck to her breasts. I sucked one nipple into my mouth and bit. She moan loud - loud enough I’m sure someone could have heard. I kept going. Thrusting my cock as deep as I could inside of her. At times coming out completely to rub her clit again. She screamed another orgasm into my ear as I fucked her hard. When she came down, she asked to be on top.

Sweaty and breathing hard we switched. She threw her leg over to straddle me, lifting my cock with her hand to glide it in. She sat heavy on it, her clit pressed hard against my pubic bone and began to grind.

She twisted her long red hard into a thick rope and held it out for me to take hold. I wrapped it around my hand and pushed my cock harder into her. My other hand held her ass, pulling her apart.

We fucked like that for a while. I liked looking up at her. Her heaving breast sweaty and flush. Her nipples hard. Her head pulled back, eyes closed, leaning into the tension I had on her hair. I brought the hand on her ass down, parting my fingers around my cock to feel it go in and out of her. The whole area was dripping wet from her and I took that hand and l put a finger in her ass.

She came again like that, screaming even louder. I didn’t care. I wanted everyone to hear. It made me hard thinking maybe a colleague could hear.

When she finished I got behind her, lifting her ass up. Before I put my cock back inside her I buried my face between her ass, talking her pussy and asshole into my mouth. She moaned and told me to keep going. She was rolling now. I gave her another orgasm with my tongue in her ass and a few fingers inside her.

Before she had settled from that orgasm I knelt over her and pushed my throbbing cock inside she, pulling apart her ass. I fucked her deep from behind and reached around to finger her clit while I let my other thumb rub her asshole.

I told her I was getting close to cumming again. She said she wanted to see me and flipped on to her back. I rushed to get inside of her again. While I fucked her she held onto my ass with one hand and my hair with the other, saying “please, I want your cum, please. Please cum inside me.”

I exploded inside of her, trembling and screaming. She said she was about to cum, to, so kept fucking, pulling her hair and sucking on her head tits.

We finished cumming and I collapsed on top of her, my throbbing, drooling cock still inside on her. Our bodies wet with sweat and cum. Panting, breathing fast and hard.

We both shuttered as I took my cock out and fell onto my back.

We laid there a moment, catching our breath.

Finally, she laughed and said, “holy shit.” I’ve never been fucked like that.” I told her I hadn’t either and we made out again, her body trembling at times.

We stayed in bed for a while. Cooling down, talking, running our hands over each others bodies. We mostly talked about the sex. She said she was amazed at the amount I came. I told her how sexy she was.

She was the one that brought up our spouses. She explained that her husband is a good lover but they hadn’t had a lot of sex in a while. I asked if she did this kind of thing often. She had once before and had just recently decided to do some exploring.

She said she had gone out that night hoping to meet someone (I knew it!) and when she saw me with LS she got jealous so decided to crash our date - she said she had had a crush on me for a while.

She asked if me and LS had something going. I was honest and said that we had been flirting but nothing had happened. She asked if I thought we would’ve hooked up if she hadn’t crashed. I honestly did know but said I was glad for how the night went. She said she was, too.

We took a shower together, kissing and feeling each other’s bodies. When we dried off we finally had that nightcap.

While we did we got real and agreed that while that was a lot of fun that it shouldn’t becoming an ongoing thing. Which would be easy since we didn’t live anywhere near each other. And we agreed that we should give each other space during the rest of the retreat and that we shouldn’t communicate any more than we used to, which was not often.

She dressed and we kissed again to say goodnight and goodbye. I didn’t want the night to end but it was late and it would be been dangerous to fall asleep together. So, after a quick glance to make sure the coast was clear, she snuck out of my room and down the hall.

I closed the door quietly and looked at the clock. It was almost 2am. I collapsed into bed and looked at my phone. I had several texts from my wife saying goodnight. And a Slack from LS, time stamped from shortly after she had left the bar. It said, “sorry I had to run. Had fun tonight. Again soon? Unless you’re having more fun with JK, that is (wink emoji)”

I did have more fun with JK. After my night with her, the thought of LS was no longer exciting. How could anything be as good as that?

I tossed my phone aside and laid out on top of our cum and sweat stained sheets. My cock and balls were aching. I passed out and woke in the morning with a hard on, thinking of JK - the smell of her still in the room.

That day… Well, I’ll save that for part two.