What is something in your sexual past that you regret doing/not doing?

Richard: I regret not making a move on a guy I had a crush on when I was a teenager. I found out years later that he was bi and subby. 

Jayden: I regret not asking for what I wanted when I wanted it. There was one person I remember in particular who we both wanted to be respectful of the other one so we didn’t initiate sex, and ultimately, we both wanted it, but didn’t want the other to think that was all we were interested in. We could have been having great sex! 

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A related short story by Jayden:

The first time we’d hung out, we’d had amazing sex. The second time we hung out, we hadn’t even hinted at sex. I wanted it, but I didn’t want him to think that it was all I wanted. It wasn’t, honestly. I was enjoying hanging out with him. I mean, I was just 18, and he was in his 30s and had his own house with a built-in theater room and everything. And he treated me well. I had had several serious boyfriends, but this was different, somehow. He was more attentive to my needs in the bedroom than some of my other partners had been. And he was interested in me, really interested.

I didn’t think it would be a relationship, but it was still fun to be together. So now, the third time we were hanging out, I was really hoping it would end with us hooking up.

Like the last time, he ordered pizza, and we brought it back to his house. We ate, sitting side by side on the couch eating pizza. Nothing happened. I yearned for it, but I was too shy to say anything. The night ended, and again, no sex.

The fourth time we hung out was the same. I was starting to worry that he wasn’t as interested in me as I thought.

The fifth time started out like the others, and I was starting to feel discouraged. We were on the couch, eating our pizza. I set my plate down on the side table and stretched out, leaning against him a little. He put his plate down and made space for me in his lap. I hadn’t meant for him to do that, but I wasn’t complaining. I lay my head in his lap, and he ran one hand through my hair, his other hand caressing my side.

“How are you doing?” he asked.

“I’m good,” I said, smiling up at him. “How are you?”

He smirked down at me, “I have a beautiful woman’s head in my lap. I couldn’t be better.” His fingers wandered down to the hem of my shirt. He slid them inside so his fingers were on my bare skin.

My breath faltered.

“Your skin is so soft,” he breathed.

I moaned softly. “Touch me more?”

It seemed he took that almost passing comment as permission, and his hand slid up my shirt fully, coming up to cup my breast through my bra. “Do you want to go to the bedroom?”

“I thought you’d never ask,” I said.

“What?”

“I’ve wanted you since that first time.”

“You have?”

“Yeah,” I said.

“Me, too,” he replied, “but I didn’t want you to think that was all I was interested in.”

“But then,” I let my voice trail off. I wanted to smack myself in the forehead. We could have been having amazing sex this whole time?! And instead, we had both been dancing around the other’s feelings, trying not to let the other one think we just wanted sex. I felt like such an idiot. He was just trying to be respectful, and I could have just asked for what I wanted this whole time. “Well,” I said, “let’s not waste any more time then. Bedroom?”

He smiled at me and said, “Absolutely.”