The [f]irst ti[m]e I ever cheated

This story is a bit older, from 2016. but I just love how naughty it is and love remembering it, so I finally decided that I’ll write it out here for you guys.

My boyfriend and I were together for just over 8 months and it was early June. People were celebrating the end of the school year, there were lots of parties and it was finally warm enough for swimming.

I was partying for a few days prior to this, so I decided to take things easy and invited and old friend John to go and relax with me near the river. I would’ve normally asked my boyfriend, but he was on a trip for 3 weeks at the time and there was another week before he’d come home. Even if he was home, he wouldn’t mind if I went with John because they knew each other and he knew how much John meant to me.

We decided to meet at 7pm, which was a bit late, but we agreed not to stay too long and get some rest. He said he’d bring something to drink and I had to bring snacks and cards, in case we got bored.

I’d usually wear traditional bikinis if I my boyfriend didn’t go with me, but I was good friends with John so I decided to go with what’s comfortable and got my red strapless top with brazilian bottoms for that night.

I was, and still am, a relatively skinny and petite girl. My breasts weren’t that big, so despite my bikini choice, they didn’t stick out too much. My butt however, was firm and round, albeit small, but it was showing nicely in my bottoms.

So we get there, get comfortable and start swimming. It wasn’t too long though before we got a bit bored and decided to play and have some fun. This usually meant some light wrestling and stuff like that, but somehow we’ve decided that I’m gonna go and jump from his shoulders in the water a few times.

That’s where the physical contact started which got me a bit excited. In order to jump, I had to sit on his shoulders everytime before I could stand up, and that meant that my butt which was pretty exposed was touching his naked skin, atleast a little bit.

After a while, we’ve gone out of the water and sat outside on the blanket to dry off and just talk. Now, it was normal that once we dried off and weren’t planning on going back in, we’d change to the clothes that we had over our bathing suits when we got here.

My bathing suit was still a bit wet, so I figured that there’s no harm in just taking it off and have my shirt and shorts on with nothing underneath.

So I put my shirt on, adjusted it and took my top off under it and threw it in my bag. Taking my panties off, however, was a bigger challenge. I’ve always loved to tease, but also figured there’s no harm since we’re such good friends, so I told John not to look while I take them off and put my shorts on.

Being a tease, I decided that if he wants to take a peek, he can. So, as I went to take them off, I turned away from him, that gave him a chance to look if he wanted ‘without me knowing’.

I grabbed my panties by the waistline and quickly lowered them down, leaving my exposed butt turned directly towards him, only a foot or two away. I quickly stepped out of them and started pulling my shorts up. They were tight, so I had to stop right beneath my butt which gave it a nice outline, before pulling them up.

I hoped he looked but couldn’t know. I sat back down and acted like nothing happened.

As the night went on, we talked about lots of stuff, one of them being my boyfriend and how I’ve missed him and intimacy for the past few weeks. We’ve talked about it for a while, when suddenly out of the blue John kissed me.

It was so unexpected, happened so fast and I had no time to react. It was just a quick kiss after which we both just kind of stared at each other. And after a few seconds, as if we both spoke with our eyes, we both leaned in and started kissing again.

I was getting turned on but didn’t know when I should stop this. I liked it, I missed it and I needed it. But I tried telling myself that it wouldn’t go any further than that. He placed his hand on the back of my head and between kisses, he told me how beautiful I was. That’s when I practically melted and actually started wanting things to go even further.

His other hand was resting on my back, but when he told me I was beautiful, I took it and placed it on my small breasts, letting him know everything’s fair game.

It was so different than with my boyfriend. Jack was so much more gentle. He didn’t squeeze, or grope or whatever. His hand was resting there, gently carressing them while we kissed. I loved every bit of it.

He then layed down and I climbed on top. We went back to kissing, except I could feel both of his hands going lower and lower down my back until they settled on my butt. Once again, I was expecting groping, slapping or something, but he just slowly moved them around and just feeling the shape of me.

I stopped kissing him and sat up, my back was arched and I took my shirt off over my head, giving him a view of my breasts for the first time. I asked him whether he liked what he saw, but before he even got a chance to reply, I started lowering myself towards his crotch. I grabbed his shorts by the waistline and pulled down.

He was the fifth guy whose cock I saw, and each time it felt like unwrapping a present, not knowing what you’re gonna get. I was glad with what I got however. He was average, but fully hard and really nicely built. As I went to put it in my mouth, he asked whether he can please me too.

I knew what he meant and wanted so I stood up, took my shorts off and asked whether he wanted to be on top or bottom. To my surprise, he chose top, so I layed down and waited for him to position himself.

I rarely had chances to be the bottom one in 69 and it was always a fun thing to do. I had my legs spread and my pussy waiting, hiding behind the small landing strip I had. As he was trying to position himself, his cock had sort of slapped me across the face a few times, which in all honesty was an even bigger turn on. I now had his precum spread across my cheeks and a bit on my nose.

It seemed that he’d never get settled and in that very moment, his cock perfectly pressed against my lips. I couldn’t have aimed it better myself. And as my lips parted, his cock just slid right in and I started sucking on it and playing with my tongue, making sure he enjoyed it. His balls were hanging low, practically touching my nose the entire time.

As good as he was at kissing though, he was bad at oral. He tried and was just as gentle and caring, maybe it was the position, but I felt nothing, so I gave it my best to satisfy him.

At one point, his cock exited my mouth as fast as it went in, he got off of me and asked if I wanted to go further to which I agreed. I didn’t change position one bit, he just positioned himself between my legs and I felt his cock slide right in. And it felt so good. He went back to kissing me and it made me so wet knowing that we’re exchanging our juices now.

After a few minutes of amazing, gentle and passionate sex he pulled out. We both looked at his cock and he started cumming. The first string of cum came literally flying out, hitting me from my chest and across the face. The second one hit below, on the mid and upper part of my stomach and the rest kind of got out above my pussy.

I stood up, gave him a kiss and went to clean myself up. Once I got back, we layed in each others arms for some time before finally heading home. I wanted to feel guilty, but he showed me how good sex can be with the right person and up until then, there were rare occasions when I enjoyed it so much and had so much fun.

Source: reddit.com/r/gonewildstories/comments/ab6ti6/the_first_time_i_ever_cheated

5 comments on “The [f]irst ti[m]e I ever cheated

  1. Beautiful story, I loved how comfortable he made you feel so this could happen. The cherry on top would have been if he finished inside you too.

  2. Pretty hot story babe! Love how you teased him and he gave you a great reward. Shows how passionate sex can be, that it’s not all about how hard and deep you can pound or get pounded. The art of the slow sensual session of love making can be truly amazing! I love to fuck, a lot, but sometimes I like to make love too. Very sexy story!

  3. Its a pitty he didn’t get a good score on the oral. Nice story . Did you live with the guilt ok?

Comments are closed.