So, I can’t say that this is a story I’m proud of, or ever expected to share, but perhaps it belongs here.
Several years ago, I was in a long distance relationship. Maybe it would’ve lasted, maybe it wouldn’t have, but I know I killed it dead.
This is the story of the one and only time I’ve ever cheated.
It was spring, and I had one of my best friend’s weddings to attend (be in), so I flew home. I spent a couple days with my girlfriend, and then, because she had to work, went off to the wedding alone (a couple hours away). That night was the rehearsal dinner, and the next day would be the wedding.
Within an hour of getting to the rehearsal, I knew what would happen that night.
I was matched up to a bridesmaid that was a firecracker. She was cute (5’8″, nice big ass, small breasts, red hair), but her personality is what drew me in. She had attitude. She was confident. And she didn’t give a shit. We immediately started cracking jokes.
The rehearsal turned into a night of drinking, with the guys and girls going separate directions, which I thought was a great idea, to keep myself out of trouble. The guys stayed at a dive bar drinking beer and playing pool, but eventually we ended up at the shot bar next door. We took one shot for every groomsman plus the groom. Nine shots, each, and then we got kicked out. Needless to say, I was good and fucked up shortly after that.
So, we went back to the dive bar, and all was well and good until a couple guys went to find their wives (either bridesmaids or with them), and I ended up tagging along with another good friend. There, we found the bride and her crew playing lawn games (horseshoes, washers, etc.), and of course, there was Red.
I spent a bit talking to the bride (she’s one of my favorite people), and at some point she decided she wanted to go to a club, and grabbed my arm and said I had to go with them (she always tries to make me dance because I’m the quiet type). We got there and it was pretty empty. I sat on the edge of the stage (not being used) and just watched the crowd (mostly the girls). This is where the night started to turn.
As the club got busier, a couple of the bridesmaids climbed up on the stage, dragging the bride with them. They wanted to dance and be there center of attention. In her drunkenness, at some point the bride decided to dance next to me and basically shook her ass in my face and on my head. This was followed by a parade of bridesmaids (and then strange hot women) grinding or shaking their asses and crotches on me or in my face.
Needless to say, I started sporting wood.
I tried to sit and keep my hands to myself and just enjoy, but eventually a couple bridesmaids came down and started to dance in front of me, rubbing their asses on my crotch. More than one, single or not, grabbed one or both of my hands and put them on their hips or ass.
Through all of this, the girls have continued plying me with drinks. Several beers, and a couple glasses of bourbon. I was staying pretty solidly drunk, but was well aware of my surroundings and the temptations I was subjecting myself too. Eventually it was time to go to the next bar.
Here, I had a parade of the girls trading places sitting in my lap. I was still in heaven, and pretty certain that I’d be saved before the devil had his way, but oh was I wrong.
We finished the night on a rooftop bar, and slowly the girls shrank away. All of my friends were drunk, all were driving, and they all wanted me to drive, so I turned them all down. And once they were all gone… There was Red. We’d cut up together, we’d bullshitted, she’d rubbed her ass on me, and I knew that given the opportunity, we’d both take it.
And she asked if she could give me a ride to my car where I could sleep off some booze. I accepted. And instead… She drove to her apartment, telling me that the police might bust me for sleeping in my car, and that I could sober up at her house. We weren’t fooling anyone. I was still fully cognizant, albeit fucked halfway out of my mind with as drunk as I was. But I still remember nearly every moment of that night, from dinner to the end.
I couldn’t stay upright on the couch, and ended up leaning against Red. She laughed at me and called me a lightweight, but I don’t think she’d drank as much.
At some point she took me to her room and told me to lie down. She took off my shoes and brought me a glass of water, and then sat on the edge of the bed talking to me. Eventually her hand was resting on my leg. Then my hand was resting on hers. This was followed by her lying down next to me and putting my arm around her, where my hand draped over one of her breasts. She kept a hand high on my leg. Every time my hand moved, so did hers.
Eventually I was holding her little breast in my hand and she was holding my dick in hers, and she apologized for having little boobs. Being a gentlemen, and honest, I told her that more than a mouthful was a waste, to which she said, not if you know where else to use it, and she squeezed my cock.
From there my hand went under her shirt, and her shirt came off. Her hands fumbled with my belt, as I pulled her jeans, and then her thong down and off. Within seconds my fingers were dripping with her juices, and within seconds more, she’d swallowed most of my shaft and was moaning with enjoyment.
I was too.
When she pulled her head up, she looked me in the eyes and said, “that’s more than a mouthful”, to which I asked, “are you going to let the rest go to waste?”
She answered by straddling my thighs and rubbing me against her (literally) dripping slit. She leaned down and nipped at my ear and whispered, “I hope I’m better than your girlfriend”, and she then slammed down on me, taking me fully in one motion.
We fucked for hours, until it was dawn. She was a squirter and a screamer, and we were drunk enough that we didn’t use condoms? We were skin to skin and glorious, and in the end, both of our cum was everywhere.
I went to the wedding thoroughly exhausted and still half drunk. Unfortunately, coming down from the alcohol, I was overcome with shame, because my girlfriend deserved better, no matter our already likely end. I muted my mind with extra antidepressants, and kept moving. Red asked if I wanted to go for round two that night, but I couldn’t do it. We left with a hug and friendly terms.
I never slept with my girlfriend again. I went to get tested for consequences (and again at 3 and 6 months, but when I got back to her place after the wedding, she just told me she couldn’t do kind distance anymore. It broke my heart, but I deserved it, and I’d known it was coming. She deserved better than what I’d done anyway.
So, that was the one and only time I’ve cheated, and I hope to never do so again. But I’ll always remember that night and the taboo of it, and the drunken, sloppy sex that blew what little was left of my mind.
Source: reddit.com/r/gonewildstories/comments/75c02v/i_knew_it_from_the_start