[M]ore than just a summer [f]ling – Part 2 [Cheating]

Part 1: https://reddit.com/r/gonewildstories/comments/atgj55/more_than_just_a_summer_fling_cheating/

Olivia showed up at my place with a six pack and her backpack. We chatted for a bit; nothing too flirty, but not awkward either. She pointed to her bag.
“Oh, I was planning on staying the night if that’s okay, just since we’re drinking. I’ll take the couch?”
I gave her a look. I was pretty sure she didn’t want to sleep on the couch, but I played along.
“Of course, let me know if you need anything.”

We watched a movie and had a few drinks. Both of us almost subconsciously edged toward each other on the couch; I can’t say what she was thinking, but I was much more interested in thinking about the other night than watching the movie.

Inevitably, she ended up on top of me when we started making out. She took my shirt off and I did the same for her. I guided her hands to my chest as her hips slowly, instinctually grinded against me; she could definitely feel my dick get hard against her through her jeans.

We probably made out like this for 15 minutes, both of us a bit too apprehensive to make another move because of our conversation. After a bit we stopped and talked for at least an hour. It was dark by this time, so I could only grab glimpses of Olivia’s topless body lit by stray beams of moonlight while we spoke. She told me about the situation with her boyfriend, how they were going to break up soon (spoiler: they didn’t) and I told her about Sam (we broke up that week). We both decided we didn’t regret anything but I wasn’t sure if going further was a good idea yet. She flat out told me that she wanted to spend the night in my bed, and I told her that I wanted that too, but just sleep- no meaningless sex.

Luckily, we just ended up having really meaningful sex instead.

We undressed to get into bed together, her in a big black t shirt and blue panties, on which I commented.

“I thought about wearing a really slutty outfit,” she said, “but that would’ve just been unfair.”
“You think this is fair?” I replied.

We pretended to sleep for fifteen minutes or so before she started gently, almost imperceptibly grinding her ass against me. Through just my boxers and her panties, she must’ve felt my cock get hard, because it definitely encouraged her. We were laying on our sides spooning at this point. Before long my hands were on her, my lips on her neck, both of us breathing heavy as we moved against each other. We stopped and started doing this three or four times throughout the night, both conflicted between our conversation and the knowledge that I could be inside her within a few seconds.

Finally, I just gave in. As soon as I reached to pull her panties down, she was eager to assist. I pulled my dick out of my boxers and teased the outside of her pussy with my head; she was even wetter than the other night. I pushed just my very tip into her to tease her, but she wasn’t having any of that. She pushed her ass back into me and my dick slid deep inside her. She was tight but the last few hours of foreplay had gotten her very worked up. We both let out a gasp, adjusting to the reality of the situation. I wrapped my hand around her slender hip to pull her into me.

I fucked her slowly like this for only a minute or so before it was clear she wanted more. Still inside her, I rolled her so that she was on her stomach and I was on top of her. Olivia let out an “oh!” She spread her legs a bit and lifted her hips slightly so I could hit the best angle. I started to fuck her hard and my small room was filled with the sounds of our heavy breathing, her wet pussy taking my dick, and my hips snacking her ass at each stroke.

I started to get close before long just because this was so hot and (sort of) unexpected. She could tell and asked me softly how I was doing. I slowed down and fucked her in long, passionate strokes while we talked.
“Trying not to cum inside you,” I said, although I knew she had an IUD. “You? Do you want to stop?”

She paused, and a sense of guilt washed over us both.
“It feels so good…” She began, “but I think we should stop..”

I pulled out of her and caught my breath. We talked for a few minutes.

“I’m so sorry, your blue balls must be really bad,” she joked. “Want me to finish you in my mouth?”

I laughed. We both wanted that, but we also didn’t want more to regret. We spent the day together just talking. Nothing more to regret that day, but the rest of the summer had a few slip-ups..

I’m having fun writing these and it seems people are enjoying so there’s a part 3 with Olivia if anyone wants, and plenty of stories with Sam too

Source: reddit.com/r/gonewildstories/comments/atxce8/more_than_just_a_summer_fling_part_2_cheating