A second chance after asking what if for 13 years...

In high school, my friend dated this girl who we'll call Mary. Mary was more experienced in a relationship than he was. She gave it a fair shot, but after about six or seven months, he wasn't really moving quickly enough for her and so she told him that she was unhappy and they broke up. I know this because she told me. We were also good friends. We occasionally walked home together along the same route when our schedules aligned, which was like once a week.

He was heartbroken. It was his first real relationship. And he was my bro. We were lab partners. Maybe a month went by and I'm talking with her on AOL messenger, as one does in 2007, and she tells me she's interested in another guy. He made her laugh a lot, she spends a lot of time with him, and he's a really good kisser from what she remembers. It wasn't hard for me to figure out she was talking about me. We had made out during Spin the Bottle at a party the year before, and it actually was a really great kiss. But what am I supposed to do here? She just dated my buddy and he's still a little fragile about it. I walked home with her the next day and said if the timing were different maybe it could've worked out. She asked if she could kiss me before we split for our houses and we did. One of those kisses that you think about for years wondering what if? What if I hadn't been a good friend? Would I have lost my virginity to this girl? Who knows?

Fast forward 13 years. Haven't thought about her or that friend in years. They weren't on social media anymore and we had simply lost touch after college. In fact, I hadn't really thought about other humans in months. It was Covid lockdown and I had moved back to my parents house because I was unemployed. I was living in their basement apartment. I had been there awhile. People were starting to not wear masks anymore. Businesses had started reopening. But still, people were cautious.

I went for a walk to get some fresh air and who do I bump into also out on a walk? Mary! We chatted as if no time had passed by. We talked about how we never talked to any of those choir kids anymore (that's how we got to know each other in the first place). She had moved states away but also came back during the pandemic. I had taken this walk dozens of times and never run into her before, and she said she kinda did the same thing. She said she wished we had bumped into each other earlier because she was gonna be moving back in about a month. She asked if I wanted to come over, have a few beers, maybe watch a movie or something, so I said sure. She gave me a kiss on the cheek and said "see you tonight!"

For the next few hours, all I could think about was all of those times I had thought about the what if? I had been wondering for years what a night together might've been like. I thought about that kiss. It was like a fantasy was coming true. Or was it? Maybe this was just a friendly get together.

I brought some beer over that night. When she opened the door, I could not believe how someone could look so good in such a simple outfit. She was about 5'2", short brown hair not even shoulder length. She was wearing tight jeans that made her ass look incredible. Her top was a loose fitting striped long sleeve. It left a little of her stomach showing, which immediately started driving me crazy. She kissed my cheek hello, and it was one of those cheek kisses that was dangerously close to the lips where you start to second guess which she was aiming for.

We sat on the couch and bullshitted over a beer, but that was enough. I had to know what was going on. So, I tested the waters and asked her straight out, "Hey, remember when you had a huge crush on me?"

"Oh my God. It was not a HUGE crush."

"I don't know. That kiss you gave me said differently."

"Oh really?"

"That's how I remember it."

She put her beer down and said, "Why don't you remind me?"

This was it. We re-created that kiss. It was slow. It was passionate. She tossed her leg over my lap and straddled me. Her soft hands on my face as she dry humped me. My hands went straight for her ass and I guided her to get us in rhythm. She took her own top off. She was not wearing a bra. Her erect nipples pointed right at my mouth so I took them. My tongue working its magic. It was everything I had imagined it would be and more. Her tits were C cups and fit perfectly in my hands.

She shimmied off the couch and took my hands off and put my cock in her mouth. I tilted my head back and told her I'd fantasized about this moment for a long time. She smiled and said she had too.

She knew her ass was her best feature. She stood up, turned around so that when she pulled her jeans and panties off she'd be bending her ass right toward me. I put on a condom and she sat right on my cock, ass still facing me. She had a neatly trimmed bush that I tickled with my fingers as I reached around her to finger her clit while she bounced her pussy on my cock. I lasted maybe five minutes before I announced I was about to cum. Hadn't had sex the entire pandemic until that point. Surprised I lasted as long as I did.

"One more round of beers and then round 2?" Mary said.