Meeting up with my high school sweetheart years later [MF]

In high school I had a semi-girlfriend named Kelly who I was crazy about. Puppy love. We never really went out technically. I was too shy and timid and kind of chickened out of formally going out with her. We both knew we liked each other a ton, and flirted all the time, but other than one week of walking around school holding hands, we never went anywhere with it, but we were always very good friends.

She was a year younger than me, so when I went to college we slowly drifted apart. An email here or there, but we mostly lost contact as the years went by. After having not seen each other for 4 years, she emailed me telling me she was coming into town to visit a university she was considering for her masters. She was staying at a hotel nearby and asked if I wanted to meet up for dinner. I jumped at the opportunity.

I’d be lying if I said I didn’t still have feelings for her. In my mind she was always my high school puppy love that was a big “what if?” in my head. But we were just meeting up as old friends, so I never let my hopes get up.

Anyways, we met up in the lobby of her hotel. She looked really excited to see me and gave me a big tight hug. I drove us to a sandwich shop nearby for a quick and easy dinner. We had a great time catching up. Some of our old flirting was coming through too, joking about how this was technically our first date.

After eating we went across the street for coffee. I told her I’d offer her my arm as we walked, but according to the teen shows I watched as a kid, that would make this a date, and we can’t do that. She laughed and grabbed my arm anyways.

When I took her back to the hotel about an hour later, I started to feel a bit of nervous energy from her. I walked her to her room door and gave her a hug goodbye, but she looked up at me and asked if I can just stay a few more minutes for us to hang out.

I didn’t know when I’d see her again, so of course I went for it, still thinking nothing was going to happen (I was pretty slow about these types of things).

Her hotel room was small. Just a queen sized bed and an armchair. I plopped down in the chair as she sat on the bed. Despite talking for hours, now we were silent, with both of us probably nervous.

She broke the silence. “Awkwaaaaard,” she said with a laugh.

I laughed and said, “Never thought we’d ever be in a hotel room together. If only 17 year old me can see us now!”

“Yeah, if I knew all I had to do was book a hotel room near you, I would have done it years ago!”

“Yeah right, you were such an innocent girl back in high school. You never thought anything like that,” I teased.

She laughed and her voice got really low. “Maybe that innocent me was just a front. I used to fantasize about things like this all the time.”

“Fantasize about us awkwardly talking across a hotel room? So scandalous.”

She giggled. “Shut up, you know what I mean.”

I finally built up the courage to go sit next to her. We sat on the edge of the bed and I wrapped my arm around her, the way I used to years ago. She looked up at me and we both knew we wanted to finally kiss.

I pressed my lips into hers and pulled her closer to me. Years of passion flowed between us. We held each other for what felt like forever. Finally we broke our kiss and I looked deep into her eyes. I slowly pushed her back onto the bed. We both knew what we wanted.

She was wearing tight jeans and a loose fitting shirt. As she laid down her shirt lifted a bit. I put my hand on her torso. She flinched for a second, but relaxed. As I went in for another kiss I moved my hand slowly under her shirt, up to her bra. I took my time, giving her time to stop me. After waiting a second, I grabbed her right boob over her bra. She quickly inhaled deeply.

“I’ve been waiting years for you to do that.”

I couldn’t believe how lucky I was, and wanted to see how far I can push it. I broke our kiss and pulled her shirt up and over her head. She lay there in her jeans, and then reached behind her and took her bra off. Her beautiful breasts right there for me, after years of yearning for them. I went back to kissing her, this time with both my hands massaging her boobs. She reached up, pulling my shirt off of me, then pulling me close on top of her. Our bodies pressed up against each other as we passionately kissed.

She slightly spread her legs, giving me room to lay between them on top of her. My dick was rock hard by now, and pressing right up against her crotch. She could definitely feel how hard I am as she slowly grinded up against me. She started to softly moan. At this point I knew there was no going back. I broke our kiss so I can undo her pants. As soon as I started to do that, she furiously reached for my belt, undoing it and pulling my pants down. Within seconds we were both naked.

I looked down at her, a sight I always imagined but had never seen before. She reached for my dick, holding it with her right hand and lightly stroking it while looking in my eyes. “I need you” she whispered.

She pulled my hard dick down to her pussy, rubbing it up and down her lips a couple times. She positioned me right at her opening and I pushed forward, slowly getting my entire 8 inch length deep inside her. She moaned a deep, loud moan as I went in. Her pussy was tight and warm around my dick. She wrapped her legs around my back and slowly ground against me. I knew I wouldn’t last long, so I tried to limit my movement, barely pushing in and out of her.

“Please,” she whispered, “give it to me. I need it.”

“I won’t last long,” I replied.

“That’s ok, I’ll cum with you.”

I pulled out further and pushed back in. She grabbed my face and kissed me. With my dick deep inside her and her tongue playing with mine, I knew it was time. I started fucking her harder and harder, rocking with the motion of her body. Her moans became faster and more intense, when suddenly she orgasmed, her pussy clenching tight on me. That took me over the edge and I came too, hard, deep inside her pussy, filling her up. I held myself deep inside of her, letting her milk every last drop out.

“I’ve waited a long long time for that,” I said, catching my breath.

“It was everything I hoped it would be,” she replied.

Source: reddit.com/r/gonewildstories/comments/peabpt/meeting_up_with_my_high_school_sweetheart_years