[MF][Cheating] How I lost my virginity with my hot married older boss/coworker.

This story happened about 3 years ago, but really starts about a year before that. I’ll note the sexy part with *’s for those who just want that. But I feel like the background of how this came to pass is at least as good as what actually came of it.

I was in a rough point in my life: I’d lost my job, lost my place to live after my roommates threw me out, and was recovering from a bad bout of mental illness and substance abuse problems. Simply put, I was a wreck of a human being, and at the lowest point that I’d ever been in. So I’d been forced to move back home and was living with my parents until I could get back on my feet. A few months after I’d moved in, I was a bit better put together and started looking for a job, and got accepted at a local restaurant. I was still a bit of a mess internally, but I put on a nice looking exterior at least. I had always been extremely shy, closed off, and kind of aloof, and I was resolved to try and be a bit more…charismatic, I guess would be the only word to describe it. And on that first day of my orientation at my new job, that’s when I met her. We’ll call her Sharon.

​

Sharon was, in every definition of the word, a MILF, and I had the hots for her pretty much from day one. She was short, and she was stacked. Huge tits, and a really big ass, which gave her an unmistakable hourglass, even if she did have the lovehandles to go with it. Long red hair that she always had tied up in a tight little bun. Blue eyes that were just so incredibly blue, the deep dark blue that is more seductive than piercing, and the effect was only exaggerated by the dark makeup that she wore. She dressed like a rock chick on a trip to the cattle ranch, always jeans and a leather jacket, but at work she always wore the same uniform as everyone else (thank you, whoever designs those uniforms). She introduced herself on my first day, and that’s how I found out that she was going to be my boss. I introduced myself and said that I was looking forward to working with her too. And the way that she said “I’m sure we’re gonna have a lot of fun working together.” pretty much sealed it. I knew that one day, somehow, we were gonna fuck. Her eyes said it all, the way she tilted her head and gave me that smoky gaze, chewing her gum and half-smirking. She was in her mid 40s. I was in my early 20s. And she was checking all my boxes.

​

We worked together almost every night. She was my supervisor, I was her subordinate, on a team of about 6. I ended up working the night shift until the store closed. And she, as the supervisor, always worked til close. Since it always got slow after 8 PM, people would simply be scheduled to go home before then, such that by the time the store closed, there were only 2 people there. And lucky me, I got to be the one that worked with Sharon. Sharon loved dirty jokes, and always had at least a dozen of them on hand at any given time. “What’s the cheapest part of a deer? The testicles, cause they’re under a buck!” I had accumulated my own library of those, and in time, our nightly banter to cut through the evening was largely a potent mix of innuendo, euphemisms, jokes and just generally gutter-minded behavior. I plotted in my head a way to get her alone for some quality time, but such an opportunity didn’t seem able to manifest itself. She had a husband waiting for her at home, and a family to boot. I was living on a couch in my parent’s living room. It seemed destined to be an unfulfilled fantasy, and I spent several long weeks pondering the way her butt looked when she bent over to get something out the fridge, and how she stood so close that she’d often be resting her tits on my arm while I cleaned counters. And then I hatched a plan. A plan that could have gone wrong but ended up going OH SO RIGHT.

​

Usually I got a ride in and out of work from my parents, since I didn’t have enough money for my own vehicle yet. She had her own pickup truck to drive. So one night I casually asked if she could do me a favor and give me a ride back home. She said sure, no problem. We didn’t even flirt about it, no cheesy “Oh I’m sure YOU’LL be the one giving ME a ride!” banter. Just a genuine request for assistance. I made a sneaky call to my family, telling them not to come get me at the usual time, that I’d be working late and getting a ride after. So we finish up, and start to head out. My family lives on a deserted backwoods country road. The kind of road that is 6 miles long and has like 5 people living on it. It’s filled with farmer fields and empty lots where houses should exist but don’t anymore. Lots of woods, lots of trees, and never any traffic. Extremely secluded. And I know that just up my road there used to be a house that burned down and was demolished years ago. The lot was left to overgrow and the trees formed basically a perfect square. All that ever let you know that there used to be a house there was the driveway.

​

I tell her to pull into the lot as we’re coming up to it. She pulls in and looks around, a little bit confused as I said “Thanks. This is good.” She looked around outside and asked, laughing, if I really lived here. Oh no, I tell her, I live just over there. My house is maybe 5ish minutes walk from this empty lot, but with all the trees, you can’t see a thing. I reach over and tell her that she can turn off the engine. She chuckles and says “Oh, really?” but, she does it. The engine sputters off. The lights are on in the cabin for a few seconds, and then they slowly fade out. Leaving just me, and her, the object of all my naughty fantasies sitting in the front seat. I scooted over towards her, and put my hand on her thigh.

​

​

********** SEX STARTS HERE ********

​

“I thought maybe we could take some time to get to know eachother a bit better.”

​

Yes, that is what I actually said to her. I was a total retard when it came to women, and I knew it. But I was trying to be charismatic, and confident at the very least. So, we started to get to know each other better.

​

It started with a blowjob. My idea.

​

“Oh my god…I can’t believe you.” She said. But her hands were already on my belt, undoing it. It jangled quietly as she undid my fly and reached inside my pants, her fingers pressing against my already growing cock. I hooked my fingers into my waistband and pushed the whole cumbersome ensemble to the floor of the truck, boxers and everything. She had her lips around my tip almost immediately. I had watched plenty of blowjob porn videos, but it didn’t compare to this at all. So I just sat there for a few minutes, and took it all in. The dim light from the radio said 11:42. The song was “Hell’s Bells” by AC/DC. She had wrapped her lips around me just as the intro was fading, and I had my eyes drift shut as I quietly murmured “Fuck…” when she took me all the way to the back of her throat just in time for the chorus.

​

She blew me for the whole song, and as the next song started up (“Afraid” by the Neighborhood), her fist was skimming up and down wetly, as she took a break. I confessed that I was a virgin, and that -that- was my first ever blowjob. She giggled and asked if I was serious. I asked what did she think of my cock. She said she thinks it should get used properly. FUCK.

​

By the end of the next song, the doors are open, the seats tilted forward, all of our clothes are scattered on the floor of the pickup truck, and we’re two naked bodies in the backseat of her husbands (she told me after) pick up truck. I did everything to her. Everything. Yes, even that. Ok, maybe not that. As soon as her bra hit the floor, I had her nipples in her mouth. They were pale, like the rest of her milky skin, and her nipples were tiny, but I sucked them like they were going out of fashion, and she had her fingers in my hair and on my back, telling me “Yeah, that’s it.” or “Bite it…like that.” Encouraging me. I was so turned on, it felt like time itself had slowed down just for me to cherish each second for longer than a second could be. I kissed her soft stomach and she pushed my head down between her legs. She smelled amazing, even after a day of work. So fresh and clean and I was chin deep in her crotch, my unfamiliarity with vaginas overcome by sheer lust and desire to perform. Two fingers in her tightness, and god was she tight. Pistoning in and out of her while I licked her clit like a mad man. “Eye of the Tiger” was just starting up when she came for the first time, her hips rising up against my face as I held my fingers in her, tongue warm on her clit as I felt her pussy crush my fingers. Shit, but she came like closing my hand in a vice. But it was so hot I didn’t even care.

​

Her chest was heaving as she pushed her hair out of her face. I don’t know when she took it out of the bun but it was sprayed out behind and across her chest as she caught her breath. I kneeled between her legs, a foot on the floor. I thought car sex would be a lot more ergonomical, but I didn’t say that cause she told me that she wanted that big cock inside of her. And thats when I said I didn’t have a condom.

​

“You don’t need one. Fill me up.”

​

Ho-lee-fucking-shit. It hit me just as AC/DC was firing up again. “You’ve been…THUNDERSTRUCK.” I was gonna bareback this hot, cheating, married milf. And I didn’t feel bad about it at all.

​

I scooted closer and kind of ungainly managed to line myself up with her soaked slit. By now the radio had ticked over and it was like 12:25. Vaguely, I wondered if my parents would be wondering where I was. As I slid inside of her, I vaguely wondered if her husband would be wondering where she was. But as soon as I was there, balls deep in this gorgeous milf pussy that I had been fantasizing about fucking for months, her legs wrapping around my hips as her arms pulled me down, I stopped caring about all of that. My first pussy, and it was better than any wank session ever. She was tight, warm, wet, and I could swear she came almost as soon as I started fucking her. “Go slow…” She whispered into my ear. So I did. I savored each pull out, and each drive forward. I fucked her gently. I fucked her rough. I pounded her. I teased her with just the first few inches. I practiced and experimented, and watched her face (no kissing! her rule not mine) for her reaction. I felt her cum as I was taking her in long, slow, deep thrusts, her nails in my back and her legs tight against my sides. And I was getting close too. I steadily picked up steam, like an old-school ships engine. The truck was rocking, the suspension squeaking as I took her harder and harder. The windows were foggy and starting to drip from our efforts, the radio read 12:39 and Kansas were singing something about peace of mind, and I could feel my cumshot building.

​

“Give it to me.” Fuck, she knew. Ask and you shall receive. I gave it to her. Every last drop. I pushed to the hilt inside of her, and I felt her go tight. Her nails were sharp and her legs locked around my lower back holding me in close. It felt like every cumshot I’d ever knocked out while sitting in bed from highschool to this moment was channeled through my cock right to her cervix at that moment. It felt like I was cumming for years, though in reality it was probably like 5 seconds. 5 of the greatest seconds of my life. I slumped on top of her, my sweaty body against hers. She tenderly pushed some of my hair out of my face. We wrapped our arms around each other, listening to each others breathing, our warm, sweaty bodies mashed and tangled together. She gave a start and reached between us, and then put her hand back. Just making sure the blanket caught our cum. She didn’t want to deal with her husband bitching that she’d made a mess in the truck.

​

We talked for a few minutes, enjoying our little post orgasm glow. But the clock was 12:56 now, Boston was singing about Maryanne walking away and she still had to drive home and I had to work tomorrow. We put our clothes back on, and wished each other good night. I walked home as she drove off. We saw eachother again the next day, and we joked and flirted again like nothing had ever happened. We continued to hook up for a while after that.

Source: reddit.com/r/gonewildstories/comments/b9oi6s/mfcheating_how_i_lost_my_virginity_with_my_hot