How I Finally Fucked an Old Acquaintance [MF] [Cheating]

(All names have been changed, because y’all pervs) :)

Right after I graduated college I met Megan one warm summer evening at a drunken music festival. At first glance, I kinda thought she was a little bit stockier than I normally go for and didn’t really take too much notice of her. But as the night went on and we got to drinking and talking I slowly started getting drawn to her playful smile, sharp wit and mostly, her sense of innocence that seemed genuine yet unbelievable at the same time. As the night progressed, and more beers we’re downed Megan and I ended up drinking a bit too much, and we moved from conversing to getting handsy with each other and giggling like school kids with crushes.

There were several problems with actually fucking Megan at that particular moment in time: she was drunker than I was comfortable with, I didn’t have a condom, she was five years my junior and a Freshman in college (legal, but it made me uncomfortable), and I had met her through one of my circles of friends who I didn’t want to piss off. Not to say that I didn’t entertain the thought of fucking her, I most certainly did. So I made the decision to go back to my tent before a difficult situation became unbearable. I announced this decision to the group, gave hugs and started walking. I made it two steps before Megan asked if I would “Walk her to her tent” because she was “tired and didn’t have a flashlight”. But what her drunken shit-kicking grin really said was “Don’t tell our friends, but I am going to rip your clothes off and ride you silly”.

This was when I had my first moment of weakness: seeing that my friends didn’t seem to object, I told her that yes, I would walk her back. After all I thought, I couldn’t just let her walk back alone through the dark concert grounds! She grabbed my arm and we were off. The tents were close to each other but about a mile away so we had a long walk ahead. As we were walking and she was holding on to me I noticed that what I had originally perceived as out-of-shape variety stockiness was actually very solid, she had defined arms and as I reached around her waist I found that her mid riff and stomach were more muscle than fluff (I would later find out that she was on the college rowing team). I couldn’t help it, my cock was at attention, pressing against my shorts. She noticed me adjusting and playfully asked if there was anything she could do to help, which only made me harder. I stuttered while trying to think of something to reply to her with, which just made her giggle. Eventually I settled on “I’ve managed to do it myself for a while now but thanks for the offer, no one has in a while”. This prompted her to reach down and rub my bulge while offering her sympathies for my “little guy”.

By the time we had got to the tent we had playfully explored all the naughty parts of each others bodies, my erection had not subsided and she actually reached down my pants and grabbed the shaft at one point. I was horny as hell but the walk back had sobered me up enough to remember that I had a good reason not to fuck her. When we got to her tent, she asked me if I was coming in and I broke the bad news to her. It didn’t phase her, I could tell that she wanted it as badly as I did. She grabbed my arm and pulled my head down so that she could whisper in my ear and said “I’m really wet, would you like to see?”. She then made a show of entering the tent, lying down and un-zipping her shorts to reveal some yellow cotton panties. Thus, I was tempted for the second time and had my second moment of weakness: I went into the tent and laid down with her. With my left hand I cupped the back of her neck while I slid my right down her front. She had a thick bush and when I reached her pussy it was like a sponge, holding in all of her wetness which had also soaked the bottom of her panties. I remember how wet it was to this day and I still have a wank from time to time just thinking of this moment. She spread her legs wider, inviting me to go deeper and I couldn’t stop myself. I plunged my index and middle fingers inside her while also bringing her face to mine and kissing her. I could hear the sloshing of her pussy as I continued to finger her, when I started rubbing her clit I was met with a groan that vibrated through her lips onto mine. With my last ounce of resolve, I pulled away from her, looked her in her still grinning face and told her again that we couldn’t do this. This time she took me seriously and begrudgingly told me that it was OK. I gave her one last kiss and left her tent for mine.

The next morning we didn’t talk to each other about what happened and there was some definite tension. But we managed to have a laugh and kept our story straight when people asked questions. We run into each other every once in a while still and are friendly. But when I see her I can’t help but wonder what it would have been like to bang her brains out that night. In the mean time I got married and have moved on with life, but the ache that my cock felt that night has persisted.

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8 Years later …

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I suppose that I should attempt to explain my relationship with my wife as, obviously, this story isn’t about me fucking her. June and I are very much in love and overall, have a good relationship. However, our sex life has slowly cooled down to the point where it feels like a chore to me. I suppose that this is natural, but I personally find it to be a challenging reality. I miss the days when I felt pure electricity in the act of finding someone new to make an intimate connection with. Pulling down a new pair of panties and having my boxers yanked off by someone who is excited to see what my cock looks like is one of the greatest joys I have ever experienced. I have been struggling with how to come to terms with knowing that I love the rush of a new partner and being in a relationship with someone who views marriage in very traditional terms. It was a conundrum and I had been having frequent fantasies about cheating.

It was recently that I finally made the plunge into the fabulous world of leading a double life. It was Comic-con weekend and my friends and I tend to make a big deal out of it, we always dress up and have a big bash. Since my house was the only place walking distance from the convention center it was party central. People know that invites aren’t a thing at this party and that everyone who wants to come is welcome to do so. Frequently people show up who are friends of friends that I don’t even personally know. This year, June (who hates comic-con), made plans on leaving the city to stay with some friends out of town. I didn’t think much of it until, seemingly randomly, Megan made a showing at our party. I hadn’t seen her in maybe 2 years and my pulse heightened as I thought about our little excursion 8 years ago. She was just as fit now as she was then, but now carried herself with the extra confidence of a woman who had grown up and come in to her own. My mind started racing, “fuck it all” I thought to myself. Tonight I was going to attempt to finish the job that was started eight years ago, there was no way I could stop it, I wanted her. I walked up to her and gave her a big enthusiastic hello and a hug which, much to my relief was returned just as much enthusiasm and also with that mischievous grin that I remembered so well. I instantly felt the blood rush from my brain to my cock, ending any hope that I had of remaining faithful.

There were many people at the party and I was the host so I had to attempt keep everyone engaged, which meant that I couldn’t focus all my efforts on trying to convince Megan to let me touch her warm furry pussy again. In hind-sight, this was a good thing as that would probably not have worked very well. In the back of my mind I was still a man on a mission: get everyone else drunk and happy and then to strike up a conversation with Megan once everyone was to drunk to care. Luckily my plan went well and I don’t remember exactly what we talked about but eventually, feeling very bold I brought up THAT night. She didn’t miss a beat, all she said was “And you will forever be known as that guy who couldn’t finish the job” paired with her classic devilish grin. I replied “Will you ever find it in your heart to give me a shot to redeem myself?”. To which her reply was simply to mouth the word “Condom”. My heart started racing and a huge smile spread across my face, I ran to my bedroom, grabed two condoms and came back downstairs to where she was standing, she walked out the door non-nonchalantly and I followed.

She called a Lyft to her place and we held hands for what seemed like forever in the back seat. Not much was said because neither of us wanted to talk, rather we wanted to fuck and both of us were focused on what was going to happen the instant that we were alone. She had a cozy, slightly messy apartment with a pile of laundry sitting at the entrance, her roomate had gone to see her boyfriend and we had the place to ourselves. I knew what I wanted and that was to feel her wetness again, to see if it was still as good as I remembered. When we got to the bed we started making out and I instantly started unbuttoning her pants. She pulled them the rest of the way off and climbed into bed. I pulled her legs towards me and slowly spread them, it was glorious, I could see a wet spot on the fabric of her panties and smell the scent of her pussy. I was instantly rock hard. As I pulled off her underwear they stuck momentarily to the sticky area between her legs and then slid off nicely. She had thick pubic hair just like a remembered and a large protruding clit. I yanked my shirt off and then dove in, releasing the tension of years and finally tasting her juicy nethers. I she started moaning loudly as I started sucking and licking her clit, then she grabbed the back of my head and forcefully smashed my tongue inside her hole. When she finally released me I continued until I brought her to her first orgasm, after which she begged me to take of my pants. When I did she lunged at my cock and started sucking, it felt amazing, June had always been really bad at giving head, and I had forgotten what good head felt like. It didn’t take long until I was near climax, I had to tell her to stop because I wasn’t going to end this experience without fucking her.

I jumped in to bed with her, both of us completely naked at this point. She had small breasts with tiny, hard little nipples. Apparently they were sensitive too because when I rubbed them she moaned almost as loudly as when I was tonguing down her clit. We made out and fondled each other for a while until I was calm enough to enter her. I rolled on top of her, rolled on a condom then and pressed the head of my cock just below her engorged clitoral hood and rubbed it up and down the length of her labia to get a sense of how wet she was. I slid it up and down effortlessly a few times and every time I reached the top she inhaled sharply. My cock was so hard it hurt at this point and I started to enter her. I didn’t take much to get it in, I had to hold back a little bit to avoid slamming my cock into her on the first thrust. I watched as my cock got swallowed by her hairy mound and I couldn’t help but let out a loud “oh fuck!” as it watched it disappear. I grabbed her hips and started kissing her neck as I started thrusting away. It could feel her warmth enveloping my cock and I could feel and hear her wetness every time my balls slapped her ass. I felt feral and alive again after years of using cold lube with June. She was so wet it didn’t even feel like I was wearing a condom, and I had not worn one in a long time. We were both moaning like wild animals and I waited until I could hear her second orgasm coming at which point I picked up the pace. She went stiff and her legs started shaking after about 30 seconds, and thank god because I could not hold my load anymore. We both exploded into a loud, sweaty, teeth grinding double orgasm, I could feel her lady muscles tighten and squeeze and I was worried for a second that she would pull off the condom. Finally, after it subsided I collapsed on top of her and laid that way still inside her until we both came to our senses.

After cleaning up and getting dressed I told Megan that I had been thinking about what this experience would be like for a long time and that what just happened was way better than I could have ever imagined. She must have agreed because we hastily hatched a plan to meet up one more time before my wife got back from her trip. I then called a Lyft and hoped no one had looted my house while I was gone. After my wife got back I did feel some remorse, but honestly, it was mostly overridden by the life affirming experience that I had just had, which I feel actually improved my mental state about our marital bedroom situation. And to this day, no one is the wiser except me and Megan, who I haven’t seen in months.

Source: reddit.com/r/gonewildstories/comments/9xjkv8/how_i_finally_fucked_an_old_acquaintance_mf