High school sweethearts meeting up years later [MF]

Kelly and I were a typical case of puppy love. We had some classes together in high school, got along really well, and were both too shy to do much about it. We “dated” for a couple of weeks, during which the furthest we ever got was holding hands, hugging, and tiny peck kisses on the cheek. It didn’t work out and we kind of knew it never would. We quickly went back to being very good friends with no long-term ill effects of our two week “relationship”.

After high school we went to different colleges. I stayed in the area while she went to a school a few hours away. We tried to stay in touch, but as is natural, we slowly drifted apart. During our senior year I got a surprise email from her saying she’s visiting grad schools and was going to be in town for a couple of days. I was of course very excited to see her again and we made plans to have dinner one day after my classes.

We met up in the lobby of the hotel she was staying at. She beamed up at me as we hugged hello for the first time in years. Feelings are a funny thing, and in that moment I felt very much like a high schooler again and it was like no time had passed.

We went out to eat something simple at a sandwich place down the street. I joked that this was technically our first real date. “Yeah, you were always too chicken back in high school,” she teased back.

We had a great time catching up. Recounting relationships, studies, etc. that we’ve missed for the past few years. After dinner we crossed the street to get some coffee. I held out my arm for her to hold onto. When she took it I said “ah, see! Now we’re on a real date!”

She laughed, “As corny as you’ve ever been, I see.”

We had some coffee and dessert and walked back to her hotel. We were so caught up in conversation that I wasn’t really thinking about saying goodbye in the lobby. We went up in the elevator together and I walked her to her room. I hugged her as she opened her door and said I hope to see her again when she’s in town. “Just come in for a few minutes,” she said. “Do you have anywhere to be?”

Now, to be clear, I can be very dense. And Kelly may very well be the only person on the planet as oblivious as I am. Neither one of us thought of the implications of us being in a room alone together. I followed her in and sat in an armchair in the corner, the only actual seating in the small room. She sat on the edge of the bed and an uncomfortable silence fell over us.

“Awkwaaaaard,” she finally said, breaking the silence.

I laughed, feeling a bit more relaxed and remembering how many strange, socially awkward moments we shared in high school.

“High school me probably dreamt about being in a hotel with you countless times,” I said, feeling a bit more comfortable.

“Too bad those days are behind us,” she said.

“Yeah, too bad,” I replied.

Another uncomfortable silence, but something inside of me figured I should stop being chicken and at least sit next to her. I got up from the armchair and sat next to her on the bed. I willed myself to look at her and her eyes met mine with a nervous smile and giggle. I put my arm around her shoulder and she melted into me. It brought me back to when we were in high school and attended a homecoming football game together. We spent the entire 4th quarter cuddled up in the same exact position.

She finally broke the silence and turned to me to say, “You know, I’ve always regretted that we never had a proper kiss when we were together.”

He smile betrayed a bit of nerves, but also her desire to push past it. I replied by leaning forward and kissing her on the lips. 5 years overdue and it felt incredible. I pulled away after a few seconds and she was beaming. “That was totally worth the wait,” she said.

“Let’s not wait another 5 years for the next one,” I said, suddenly finding the confidence of a 90s teen movie football player. I leaned in and kissed her again, more passionately this time.

I held her face in my hands as she wrapped her arms around my back. Years of longing were bursting through and neither one of us was going to hit the brakes. After a few minutes of our hands roaming over each other I rested my hands on her sides, just a few inches below her breasts. We had taken a breather and she looked down at my hands and said, “Careful where your hands are,” with a smirk.

Not wanting to be disrespectful, I pulled my hands away. She put them back on her sides, a bit higher. She bit her lip and looked up at me and said, “I meant the opposite, actually.”

At this point even my dense self knew I had the green light. I leaned in and kissed her again, with my hands moving up to cup her perfectly sized boobs. She was wearing a sweater and after a few seconds she held my hands and slipped them under the hem of her sweater, letting me feeling her breasts with only her bra covering them. I was in heaven.

She eventually pushed me back onto the bed, with my head propped up against the headrest and she straddled my lap. The nervous grin on her face was gone, replaced with a naughty one. She lifted her sweater up and over her head. She looked incredible in just her bra and jeans. I reached behind her, undid her bra strap, and for the first time saw her boobs. I couldn’t believe what was happening. Needless to say, I was hard as a rock at this point, which I’m sure she could tell since she was sitting right on it.

I reached up and cupped her boobs, flicking my fingers across her nipples, which got a small moan out of her lips. The anticipation was killing me and I took my shirt off and she collapsed onto me, our skin pressed against each other as we kissed in only our pants.

Neither one of us was trying to waste any time, and after a few minutes she got off me and slipped her pants and panties off her legs in one movement. I did the same and my hard dick sprung out for her. She reached out to grab it, teasing my head with her thumb. She looked at me and said, “I’ve been wanting to feel you inside of me for so long.”

“Let’s not wait any longer,” I replied.

She straddled me again and, with my dick still in her hands, rubbed it up and down her pussy lips. I could feel how dripping wet she was. I lifted myself up onto my elbows so I could kiss her again. After pulling away I whispered in her ear, “I need you right now.”

She lifted her hips a bit and positioned me at her eager hole. She slid my head inside her and held it there. I later found out her only experience prior to this was with dildos, and she needed a minute to adjust to the size and feeling. She slowly slid down my cock, inch by inch until I was fully inside of her. She was incredibly tight and I had never felt such pleasure on my dick before.

When she started to ride me she went slow at first, getting used to the feeling. But she eventually picked up the pace. She laid herself flat on my chest, only moving her hips up and down, which also allowed her clit to rub up against me slightly. I don’t know how I managed it, but I held off on cumming as I wanted her to be satisfied too. Eventually I couldn’t help it (it felt like hours, but I’m sure was no more than 10 minutes tops) and whispered in her ear that I was close. “Me too,” she replied, between deep breaths and moans.

“Cum with me,” I moaned.

That was all it took as her body began to shake. Her legs tightened around my sides and I felt her pussy convulse as she rode out the orgasm. The feeling was incredible and I couldn’t hold off any longer, grabbing her ass in my hands as I pushed as deep into her as I could and emptied myself into her.

She stopped moving and laid still on top of me, her curly hair forming a veil over my eyes as I came back to earth after such a powerful orgasm. When we finally caught our breath, I was almost worried now that the passion had found its outlet, she would feel regret, shame, or awkwardness about what just occurred.

She eventually lifted her head up, looked me in the eyes, and kissed me. A passionate, but light and fun kiss. She pulled away and had a giant smile on her face. “That was totally worth the wait,” she whispered, breathless.

Source: reddit.com/r/gonewildstories/comments/y354wi/high_school_sweethearts_meeting_up_years_later_mf