[MF] The one and only time I cheated

Ok so this happened about 6 years ago…I’m 37 and have been married for 5. This is the one and only time I ever cheated on my wife…but I have to be honest…I don’t regret it.

It was about 6 months before our wedding. We live in the south but all of my family is from the Boston area. My brother was getting married and I was in the wedding. My wife (fiancé at the time) had to work so she wasn’t going to be making the trip up there with me. So off I go! I was staying at my parents house (same one I grew up in). Now my brother was marrying his high school sweetheart and they are only 2 years younger than me. So, naturally, I was going to know a lot of people at the wedding reception…I just want sure who.

It’s an open bar so immediately start drinking Jameson and I’m feeling pretty good. That’s when she tapped me on the shoulder…Heather!? She was my high school girlfriends best friend. I dated her BF for almost 3 years, so Heather and I had spent a lot of time together!! There was always a bit of flirting and some sexual tension between us but that’s as far as it went! It was her BF after all. She is a very small, thin, brunette. She probably weighed 90 lbs or so…I’m usually into more curvy girls but….DAMN if she didn’t have a KILLER body!!! Her tits were a little on the big side for her size…they perfect!!

Anyway…we start catching up. She is actually married now (her husband was out of town) and still talks to Julie (my ex) yada, yada….we continue talking and drinking for most of the night. Occasionally hanging out with old friends but mostly just talking to each other…she is flirting SO hard with me and I was having sooo much fun talking to her!! We continue drinking A LOT…as the reception dies down, I decided to invite her and a few other old friends back to my parents house to have some drinks and smoke a joint or 2. And we do just that! My parents have a large house with a pool table in the basement. It’s where we all hung out and got drunk as kids (not much has changed. Lol). Anyway….it’s getting late at this point (probably 1AM or so). The other guests all leave and Heather asks if I want to smoke some more when they left….of course I do! But at this point I’m getting a little more nervous…I had never cheated on my wife and never planned to!!!

So I walk everyone out to their car and when I come back she’s playing pool. She looks over at me with that look…that “fuck me now!” Look!! I cautiously walk over to her and begin rolling a joint. Well…she had different plans…she puts herself between me and the pool table, where I was breaking up the weed. She looks me dead in the eye and says “don’t you want to kiss me?” I tried to be strong and told her how much I wanted to and how I have secretly wanted her all through high school…I brought up my fiancé and that it wasn’t right etc but it was like she didn’t even hear me!? She leans in and kisses my bottom lip…unable to resist, I began kissing her back. Slow and sensual at first but quickly became more passionate and aggressive. I moved my hand over her breast on top of her shirt. She was grabbing and rubbing my dick though my suit pants and I was getting hard…but once again!! I tried to listen to that voice inside my head and do the “right” thing. I pulled away and told her I needed to needed to behave! I’m pretty sure I grunted and groaned with frustration. She smiled and said ok…but I could tell she had no intention of either of us behaving!

I go back to rolling the joint while she pours some more wine. We go outside and smoke and got REALLY high! We went back in and continued talking and flirting very heavily. She was playing pool and I was sitting on a barstool of to the side. We were being silly and laughing A LOT!! She told me about how my ex used to tell her how big my dick was. She asked me how big it was. Trying to be modest….I told her I didn’t really know (it’s about 8.5” and thick). She used the pool stick as an example and was like “is it this big?” And I would say “no, bigger”. Her mouth would open in shock a little and she’d try again. She eventually got close to the length and I told her that was about the length but I was MUCH thicker. She bit her lip and went back to shooting pool. Making sure she was facing away from me and bending over so I could see her amazing little ass. I was staring at it and biting my lip when she looked back at me. I didn’t try to hid that I REALLY liked what I was seeing!!! We talked for a few more min and when I looked back up, she had unbuttoned her tight pants and pulled them down below her ass. She was wearing black and silver thongs (I think they had some gemstones or whatever on them). She’s shooting pull, bent over, with her AMAZING ass hanging out of her pants….like 3 feet in front of me. I could see her mound between the little gap in her thighs….OMG I wanted her sooooo fucking bad!!! I was sooo conflicted!!! I gave into temptation yet again….I came up behind her, pulling her against me while I kissed her neck. She immediately started moaning and actually trembled a bit! She turned around and we start making out again….I slide my hands down the back of her pants and grab her tiny little ass in my hands. I remembered thinking “damn! She’s tiny!! I might break her”. I lift her shirt up and grab her breast over her bra and I can feel her nipples getting hard.

Then it happens again!? I started feeling guilty and stopped it. ?. Now she might have gotten a little frustrated. Lol. She grabbed my dick through my pants again and asked if I was sure. I said “no! But I’m trying to be!” She said “I want you inside of me. I want your dick soooo bad!!!” I went to the bathroom to try to re-group a bit. I told her I would be right back. I went upstairs and when I came back down….she was on top of the pool table, on all fours….completely naked with her ass facing towards me. She looked back at me and said, rather aggressively, “I NEED YOU TO FUCK ME!!! YOU HAVE TO FUCK ME!!!”

Now, to be honest, I don’t remember exactly what I said in that moment but I’m pretty sure I stood and stared with my mouth wide open for a solid minute! She was perfect!!! Her skin!? Omg!? She is Puerto Rican and Italian will a perfect, dark complexion. Arching her back and sticking her tiny ass in the air.

I slowly walked over to her. I remember feeling a little intimidated!!! She was so intense and had this look in her eyes!! But I was also sooooo excited and nervous. I get to the pool table and put my hand on one of her ass cheeks. It fit perfectly in the palm of my hand. I squeezed it and pulled it to the side a bit, opening her tight light pussy a little. I was thinking ‘OMG! How would I even fit in there!’

She started to turn around to face me but I told her no. “Stay where you are.” Since she was up on the table, her ass and pussy were almost at eyes level…grabbed her other ass check spread her cheeks and slowly licked her pussy from behind. It was swollen hot to the touch…and It was so fucking tight!!! She was quivering and moaning like crazy every time I slid my tongue over her tight mound. She was pushing back into me harder and harder. She tasted so fucking good!! I slide the tip of my tongue between her tight lips, feeling the inside of her hot, wet pussy for the first time. I wanted to suck and lick every last drop of her. I slowly slide my tongue deeper inside her, until my face was pressed up hard against her ass as she pushed back into me. She was so into it!!! I was licking her off my lips as I slide my finger inside her…as far as it would go….keeping it there as she rocked back into me. Her body was perfect…right down to her asshole. I couldn’t resist…I collected saliva in my mouth and lick her tight little asshole with me my wet tongue. At that point she let out a small yelp and started grinding harder as my tongue began to push inside her ass. After a minute or 2 she stopped and turned around. Still with this really intense look in her eyes she says “I NEED YOUR FUCKING DICK INSIDE ME!!!” And starts grabbing wildly at my groin.

At this point she is completely naked and I still have ALL my clothes on (suit pants, white shirt, boxer briefs). So I unbutton my shirt while she rubs my cock through my pants with one hand and tries to undo my belt and unbutton my pants with the other. I get my shirt off and tell her to get off the pool table (I think I made a joke about how my dad would kill us if he saw her up there, like we were in high school again). She got down and walked over to the couch. I followed. I stood in front of her as she stared at the bulge in my pants. I undid the last button on my pants and let them fall to the floor. Sliding my thumbs inside the waistband of my underwear, I pulled them down, over my dick that wasn’t even fully hard at this point (I think it might have been nerves lol). My dick flops out and, I know this sounds cliche but….her jaw literally dropped. She genuinely looked REALLY nervous!!! After a few seconds she looked up at me and said (I will never forget this…she was pretty a funny girl) “ummmm, I’m not licensed to handle that type of machinery!!!” And I think for a minute there she was rethinking her decisions that night! But only for a min. Lol. Sitting on the couch, she leaned forward and grabbed my balls (which happen to be pretty big) and pulled me to her. Grabbing my shaft she put the head against her lips. It looked so big next to her tiny mouth….she put the tip in her mouth and began sucking on it while she squeezed my shaft, pushing all the blood to the head, making it swell in her mouth. I remember she sucked it really hard…like she was trying to give me a hickey. Before long I was ROCK hard…she licked up and down my shaft a few times, then put one of my balls in her mouth. It was so hot watching my cock lay across her face…then she tried to take as much of me as she could but I’d say she only made it about half way. She didn’t quite gag or anything and to be honest I remember, for just a moment, I was kinda bummed she didn’t try harder or stay down there longer! But she had other stuff on her mind!

She drooled all over the head of my dick and quickly turned around. Kneeling backwards on the couch while grabbing the back with her hands. She stuck her ass out and DEMANDED “fuck me now! You HAVE TO FUCK ME NOW!!” She reached back and grabbed my dick. Pushing the head against her pussy. Wiggling it back and forth, trying to get it between her lips. Then I took over, grabbing the base of my dick, I push the head of my dick against her, spreading her tight lips…she quietly screamed…I begin pushing in further but…couldn’t. She started really sound like she was in pain. I asked if she was ok and she said she thought so then continued to tell me to fuck her. I pulled out for a sec, spit in my hand and covered her pussy in my spit, then did the same to the head of my dick. I slide the head back in and began pushing….harder and harder….I felt like I was really going go hurt her soon!!! She turned around and told me to sit. She stood over me on the couch, her feet on either side of me. She squatted down and grabbed my dick. Placing the head between her lips once again….at this point my dick is THROBBING!!!! I’m so fucking horny and excited and nervous that I’m already trying not to cum!!! She slowly starts lowering herself onto my dick…we start to get stuck at the same place so she lifts her feet up and uses all her weight too slide down my dick. As soon as she became unstuck she slide all the way down to the base of my dick!! We both stifled our screams and moaned really loudly. We immediately started kissing. I was soooo deep inside her!!! The tip of my dick was definitely hitting some organs or bones or something!!! We kissed for a min as she started grinding more and more against me while I was ALL the way inside her! Then she started sliding up and down my shaft….I couldn’t take it!!! I was gonna blow!!! I told her she needed to slow down or I was gonna cum. So she did…but it didn’t help! Lol. I didn’t want to cum so soon….but she was soooooo fucking tight!!!! I grabbed her ass and lift her off me and told her I needed a min. She was on top of me, her wet pussy lips were gripping the shaft of my dick. Even that was too much…the head of my dick was swollen and even one touch would have made me blow…I told her to lean back. She leaned back, with her legs spread on either side of me and began playing with her clit….it was so fucking hot to be so close-up and watch her cum. I could see her getting wetter. She used her other hand and slide 2 fingers inside her while I watched. She kept eye contact with me the entire time!! She told me she was about to cum so I moved her off me. We both moved to the floor. She got on all fours and looked back at me. I grabbed the base of my throbbing, swollen dick and pushed the head of my dick inside her. Slowly pushing all the way to the back and back out…after a min I began to go faster…and harder….it was kinda like…”well you asked for it. You wanted me to fuck you, right?” So kept pushing harder with every pump….my balls were slapping against her ass, I could feel them splashing in her wetness as she started to cum. She was burying her face in the couch to muffle her screams….her pussy clenched my cock even tighter. I pulled out as fast as I could (I might have been slightly late ?). I exploded a huge load of cum all over her ass!!

We both collapsed onto each other on the floor. We talked about how long we both had fantasized about this. We made out and played with each other’s bodies for a while. We both wanted a little more time to play! Lol. We didn’t fuck again but I sucked on her tits for a while and she put my soft dick in her mouth to see how much she could fit…Still not quite all of it. Lol.

So that’s my (LONG) story. I hope you enjoy!

Source: reddit.com/r/gonewildstories/comments/ah53fs/mf_the_one_and_only_time_i_cheated