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I slept with his friend a month after him and I broke up. We had matched on Tinder a while ago and finally found some time to see each other (we work opposite schedules). We spent the day together: a lovely coffee date with a game of chess, tacos, bakery, and went back to my room to just hang out. Nothing out of the realm of friends. I offered to friend cuddle (which is ordinary for both of us to cuddle our friends) because he got cold. We talked while cuddled up, and eventually after 2-3 hours of talking, I wondered he tried to kiss me, but I couldn’t tell if I was over thinking or accidentally rejected his advances. Either way, I worked up the guts to ask, he admitted it, and we kissed.

We had some breaks in between making out where we would talk and joke around, but at all times managed to go back to kissing. It got heated fast, and he ended up on top of me, fully clothed but feeling me up as we made out. Things calmed down a bit and we were talking again… and then I ended up on top of him, kissing him. My shirt eventually came off when he sat up so I was straddling his lap, and I was bare chested. We ended up laying back down, but I was still on top.
He whispered in my ear, “If you want me to take anything off, just let me know.”

I hesitated and said, “Whatever you’re comfortable with.”

He took my face in both his hands, looked me dead in the eyes, and said, “OP, I’m comfortable with everything. Don’t be shy.”

I slowly pushed up his shirt, he sat up and took it off. We held the kiss as he flipped me on my back, settling between my legs, grinding against each other as we kissed. He pulled away to kiss my neck.

I asked, “You aren’t feeling pressured, are you? You’re comfortable with all this?”

He replied, “Yes. Are you feeling pressured? I’m the one on top of you right now.” I shook my head no.
He kissed down my neck and gently bit my shoulder.

I whispered to him, “Sex is on the table… if you want it. If not, that’s cool too. Either way is fine with me.”

He looked me in the eyes again, like earlier, and said, “I kissed you first and I took off your shirt first. Of course I want you OP. Do you want to?”

“Yes, but… I have to tell you something ahead of time because I’m a responsible adult…. I have herpes.” I explained that I’m on medication and gave him the probability of him getting it from me. “If you’ve changed your mind now that you know that, I won’t be upset. I’d totally understand.”

Again, he took my face in his hands like before, and said, “Well, I always have sex with condoms anyway. So, I’m okay with that.” I guess I still looked a bit nervous, so he said, “OP, I’d be more upset if I got herpes but didn’t win the lottery in my lifetime.”

We laughed off how awkward it is to try to take off our pants and underwear, then he slowly, gently pushed into me as we kissed. His hands ran up and down my thighs and sides, and held my face as we made love. It was slow, sweet, and passionate–something I’ve never had with any of the other people I’ve slept with. It was amazing. Way better than all the sex I’ve had with my ex boyfriend. I loved it and I’m still thinking about it 24hrs later. I made a list of things he did that I liked and sent it to him.

NSFW: yes

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