One of the trashiest things I’ve ever done [FM]

One of the summers I was in college, I was the one responsible for taking my younger sibling to softball practice and games. Mom was a single mother, and while we could afford his equipment and everything, she didn’t have the free time. I didn’t mind clearing space for him in my life, I never played any sports growing up and kinda wish I had, so I wanted him to have that. A lot of the parents in this league came as couples, so being the 22 year old sitting there with them, I was kind of on the outside looking in socially. The husbands were friendly enough, so I spent most of my time chatting with them. That culminated in some of the wives being openly bitchy toward me. Keep in mind, I wasn’t being flirty at all. Honestly, I wasn’t even interested in these guys. They were just friendly, and I was there anyway. I got flirtier once their wives iced me out though, I guess I’m too petty. My sibling is autistic as well, the league did an amazing job adjusting to all levels, but there were several snide remarks that really pissed me off. I would have fought these women in a cage match, honestly.

The league had this registry where everybody put in their phone number. They did it so people on the team could call around to ask for rides if someone was unable to drive their kid. My phone number was on that list, and one of the husbands who I’ll call Kevin pulled my name off of it to send me some pictures he had snapped during one of the games. I thanked him, and we chatted for a little while. That turned into banter and joking around, which turned into him mentioning that he was going for drinks with two of the other Dads that night, and inviting me to tag along. I think Kevin knew what he was doing here, at the very least he was enjoying the attention from a younger woman. I was free though, and enjoying the attention as well so I agreed to come out.

There was definitely a healthy (or unhealthy, depending on your perspective) dose of pettiness in my agreement to go out with them. It showed a little bit when I got dressed for the evening. My outfit wasn’t slutty per se, but I also made no effort to be especially modest. A clingy orange spaghetti strap dress that only came a few inches down my thighs was paired with a strappy pair of wedge heels. I neglected to wear a bra, which allowed my nipples to poke through a bit, the straps caused a fair amount of bounce from my 34D chest as I walked too. With the final additions of lip gloss, and a small amount of sparkles to my cheeks, I was basically a walking “I’m more fun than she is” sign by the time I left the house. Seriously, I literally got a raised eyebrow from my Mom as I was walking out the door.

The sports bar they had chosen to drink at wasn’t far from my house, so I embarked on the short walk a few blocks away to meet them. I spotted Kevin sitting at a round table near the back of the bar. Kevin stood with a wave, coming to greet me near the door. Kevin was taller than me, though not by a ton in my heels. He had his blonde hair pulled atop his head in a bun. He was in great shape, I used to see him running around the neighbourhood regularly. I opened my arms to give him a greeting hug, and caught a whiff of aftershave on him as we separated. He told me I looked great, and I placed a hand on his bicep while thanking him. I was laying it on thick, and I knew it. But he was eating it up, and I liked the idea of his mind wandering away from his absolute bitch of a wife.

Kevin showed me to the table where the other Dads Marco and Paul were waiting for us. Marco was an Italian man, tall and lanky with a goatee and short black hair around brush cut length. Paul was closer to Kevin’s height. Somewhere around 6ft, or slightly under. He had dark brown hair, and a full beard. It’s a weird comparison to make, but in my head Paul is a more attractive Seth Rogan (He’s also extremely funny, had me in giggle fits all night.)

The guys had apparently been debating baseball statistics prior to my arrival, but the conversation shifted once I sat down to questions about me. They asked me about my major, what I did for work, my dating life, really anything they could think of. I answered all of their questions with a big smile, and laughed at all their jokes. These guys really were fun to spend an evening drinking with, I’d have enjoyed my time hanging out with them regardless of my petty motivations for doing so.

The bar also had skeeball, and a few other arcade style games. As the night wore on, we headed over to those and played a little bit. I’m terrible at skeeball, but the guys cheered for me regardless. I made a little bit of a show out of bending over as I made my shots, letting my dress ride up my thighs just a bit before quickly adjusting it once I straightened. We had another round of drinks, before it was decided that the guys wanted to have a skeeball tournament between us. I teased that since I’m worthless at the game, I’d be in charge of the prize instead, which caused momentary silence at the table before Paul, with a tentative smirk on his face, asked me what exactly I had meant.

I hadn’t really put any thought into the offer before I made it, so I didn’t have a prize in mind at all. I was on my fourth drink by that time, and I’m a bit of a lightweight so I was buzzing. What came to mind was a prize I had actually used for a fwb of mine when we were playing video games in his apartment: The winner got to look through my camera roll. More specifically, the gallery of explicit pictures of me on my phone. None of the guys said a word once I made the offer for a couple of moments. There were glances around the table as they all looked between each other to see if any of them would take the lead. They came to their senses when I stood from my seat, and walked back over to the skeeball machines, following me over.

During the game, I devoted most of my attention to whichever of them was playing. Kevin was first up to play, and I ran my hand up their arms, and blew on their balls (the skee balls, you perv the dirty part hasn’t started yet) for good luck. I won’t bore you with the full details, but Marco was out the first round. Not by a little bit either, he had only made a couple of his shots. He threw up his hands, and asked if there was any consolation prize for third place. I told him that in this case, third place was just the first place loser, then kissed him on the cheek despite that. He was tipsy enough that he put his hand low on my hip when I leaned in for the kiss. I stood next to him, and let him keep it there while Kevin and Paul battled it out on the skee ball machine.

When the game ended, Paul had emerged victorious. I fished my phone out of my purse and opened it to my nudes gallery. Marco still had his arm around me, and got a quick glimpse before I handed the phone to Paul and warned him not to show anybody, and to shield his screen. I stepped away from Marco so I could lean into Paul and see which pictures he was looking at specifically. As I did, Marco stealthily gave my ass a slight squeeze. Bold on his part, especially for the loser, but I didn’t mind.

Paul swiped far enough back in the image gallery, that there were pictures of me actually bent over my bed by my last boyfriend. I heard a small noise in his throat as he looked through a few more, then closed out of the app and handed the phone back to me. I was blushing heavily as I took the phone, and suggested that we all take a shot to celebrate Paul’s win, also my treat. Marco bowed out, needing to head home, as did Paul. Kevin was down to stick around a little bit longer.

He didn’t actually let me pay for the shots, and I rolled my eyes at Him for not letting me spend any money. I teasingly asked how his wife would feel about him spending money on another woman, and he was quiet for a moment before Kevin admitted that he hadn’t told his wife I was coming along. In my alcohol induced haze, that turned me on. I liked the fact that he had hidden me from his wife, it told me he knew exactly how much she disliked me, and I liked that too. Kevin was misbehaving by even spending time with me. I decided then I was going to offer him something, but I hadn’t decided what I wanted completely by the time we sat back down at a table, so I sat in his lap to buy myself some deliberation time.

Without missing a beat, Kevin wrapped his arms around me, and pulled me a little bit closer. He was into this now. I wondered if it was the first time he’d had a night like this during the course of his marriage, but pushed those thoughts to the back of my mind. I wanted to be special, despite the fact that looking back, I was not special in any way. In fact, I was engaging in something that had been done countless times before: The temptation of a married man.

I ended up confessing to Kevin that I enjoy a cigarette sometimes when I drink, and he laughed before telling me that he had a pack in his car for the same reason. We left the bar, and stopped at his car to grab the pack of cigarettes before we each lit one as we walked around the neighbourhood and chatted. The conversation turned to his marriage. From his account, his wife was a bitch in more places than the softball field. I was being drunk, and vulgar so I said something along the lines of “At least she’s hot though, the sex must be good.” which is when he launched into a few minute long rant about the lack of intimacy in their marriage. They used to be wild, he told me. She had lost most of her interest in sex after having their second child.

Some of you are disgusted with me right now, some of you are silently encouraging me to do what you all know comes next. I offered to let Kevin fuck me. It wasn’t coy, or sultry. I just bluntly offered to have sex with him. He stared at me in the dark before asking if I was serious. Rather than answer his question, I opened my purse and took out a single condom, handing it to him. (I keep a few in my purse because men are bad at planning things.) He turned the wrapped condom over in his hand, then said he had nowhere for us to go, his wife was at home with the kids. I reminded him about his car, parked in the parking lot of the bar. Far from the most secluded location, but he didn’t protest. Instead, he took my hand and started walking me briskly back in the direction of the bar’s parking lot.

Kevin drove an SUV. Not a particularly large one, but one with a decent amount of room in the backseat. We both slid into it when we thought nobody was looking, and started kissing the second the door closed. I climbed into his lap and tugged my dress up, grinding myself against him through the jeans he wore. He groped my ass, then tugged the top portion of my dress down so he could suck on my breasts. I absolutely love that, so I reached down and started rubbing his cock through his jeans while I moaned.

He slid himself down in the seat a little bit, allowing me to unbuckle his belt and ease off of his lap a little bit so we could slide his pants down. I dropped to my knees on the floor of his car and tugged his boxers down as well. Kevin’s cock was about average, maybe a little thicker than most. I found him quite manageable as I sucked him off. He groaned and ran his fingers through my hair when I swirled my tongue around the tip of his cock, and I smiled up at him before climbing back into his lap, and tugging my panties to the side.

I ground my slit against Kevin’s cock bare, grasping the base of his cock with my hand and using that for control as I massaged my clit with the head of Kevin’s cock. I then told him to hand me the condom. He fumbled with it before handing it to me. I tore the wrapping open with my teeth before rolling the latex over his cock and stroking him lightly afterwards. Then, with a slow motion, I lowered myself onto Kevin’s cock and started rocking my hips back and forth, riding him.

Kevin turned a little bit, laying back further on the seat so he was kind of propped up against the door. This gave me more room to begin riding him quicker. I placed one hand on the back of the seat, the other on his chest as I increased my speed. He pulled me down into him, wanting to suck my breasts again and it caused me to fall forward against his chest. We both laughed, and I kissed him again as I started riding him once more.

He followed instructions well, I raised Kevin’s hand to my clit as I rode him and he got the message quickly, massaging me in circles that matched my pace over him. With his free hand, he gave my ass a fairly rough smack which caused me to yelp in surprise, and bury my face in his neck, biting playfully at his skin. He warned me not to leave any marks, and I laughed, rolling my hips into him a little bit harder.

Kevin spanked me again, and called me a naughty little slut while picking up his speed slightly against my clit. That brought me to orgasm, and I whimpered before collapsing into his chest again while my lower body clenched around him. He moved his hips slowly underneath me as my climax subsided, I then slid back to my knees in front of him, and tugged the condom off of his cock, immediately licking up and down his shaft. The sudden change in sensational intensity made Kevin gasp, then swear. I bobbed my head quickly over him, attempting to choke myself each time I moved forwards.

He warned me before long that he was about to cum, and once again ran his fingers through my hair as he did. I didn’t pull back from him, instead continuing to suck him as he came in my mouth, swallowing with each throb of his cock. Kevin swore again, and panted heavily as he sat back up a little bit on the seat.

We both laughed again, and eventually stepped outside of the car to smoke another cigarette before I walked home on my own. Kevin’s wife never found out. Or at least, never said anything if she did. Paul and Marco were informed though, there were several allusions made to it later, when Kevin added me to a group chat with the two of them. So yeah, there it is. Impulsively screwing a middle aged Dad because I hated his wife is far from my finest moment. It is one of the memories that comes up a lot in my fantasies though, I had fun.

Source: reddit.com/r/gonewildstories/comments/y9f6tv/one_of_the_trashiest_things_ive_ever_done_fm