Childhood Sweethearts All Grown Up

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A guy reconnects with his childhood sweetheart, all grown up.
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Part 1 of the 2 part series

Updated 11/01/2022
Created 09/19/2011
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This story is based on actual events. The names have been changed to protect the innocent.

I always say that I have the movie Forrest Gump to thank for one of the greatest nights of my life.

Sounds like a crazy thing to say, right? Let me explain.

I'm sure most people had a childhood sweetheart growing up. Mine was named Jenny. No, just kidding. Her name was Nancy. She was the daughter of one of my family's friends. She was born about 10 months after I was, and her mother always (jokingly, I think) referred to me as her 'future son-in-law'.

She was in some of my earliest memories, play-dates and parties and the like. Then, when I was 5, my parents moved us an hour away. End of story, right? No, not really. I would come and stay with my family during summer and holiday breaks, and my grandmother would always be sure to include Nancy in whatever was going on. Trips to amusement parks, zoos, toy stores. It was some of my happiest childhood memories and Nancy was there too. I remember one night that Nancy stayed over my grandmother's house with me. We pulled a second bed into the back bedroom and stayed up half the night playing with our new toys and talking. Ahh, the innocence of childhood.

Her family came to my elementary school graduation party. We had a pool in our yard, with a big blow-up boat. We flipped the boat over and hid underneath it, enjoying the echo effect of the enclosed space under the water. We just stood there talking with just our heads over the water for what seemed like forever. It felt like we were the only two people in the world.

Sadly, that summer her parents moved an hour in the opposite direction, so now we lived two hours away from each other. We were able to see each other about once a year over the next few years when they were invited to our more major family events, but to my dismay our families had a minor falling out and eventually drifted apart. A visit to her house when I was 14 was the last time I saw her or heard from her for quite some time. I'm sure things like that happen to everyone. But I was never able to forget her.

It didn't help that she was the 'it' girl when puberty hit me. She became the star of every budding sexual fantasy I had. I would just lie in bed and let my mind wander from fantasy to fantasy for hours, wherever my inexperienced teenage mind could take me. Maybe that's why it became ingrained in me that somehow we'd be together again.

I was home for winter break during my sophomore year of college when I watched Forrest Gump. Watching Jenny flit in and out of Forrest's life brought back vivid memories of Nancy. I knew she was out there, somewhere, and the desire to speak to her again suddenly became overwhelming.

Still, I hemmed and hawed over it for another couple of months. It didn't help that I was having an awful semester in college. I wasn't doing well in my classes or my social life. Eventually, Nancy's birthday was approaching, and I finally made the decision to get her address and send her a birthday card. I wasn't really expecting anything to happen, especially since my life was going so awfully, it just didn't seem like anything positive could come out of this, either. As much as I hoped things would turn out okay, I took to calling it 'operation banging my head against the wall'. Still, I dropped the card in the mail and tried not to wonder if anything would come of it.

I'll never forget the day I got her letter. I had gone out to a club with a couple of friends the night before and didn't get back to the dorm until 2am. I don't know why I did it. I really had no interest in clubbing and had never gone before. I guess in my depression I started feeling like doing unusual things. Of course, I had a miserable time. I tried dancing for a while but hated the music and the crowds. I ended up sitting in a chair in a corner, zoned out while I waited for my friends to get their fill and take me home.

I ended up sleeping through my Friday morning classes, but those were the ones that I was flunking, anyway. What good would being there do me? I eventually got out of bed and ate breakfast, then went to the student union to check my mailbox. There was a letter from Nancy in there! I was so happy, I was like, jumping up and down happy. I raced back up to the dorm to read it. She said she was surprised but glad to hear from me and she hoped that we could get to know each other again.

But first, I had a second 'night out' to go through. A guy a sort of knew was pressing me to go out with him because he wanted to 'corrupt me'. And in the worst of my self-destructive doldrums I had agreed to let him give it his best shot Saturday night. Unfortunately, I didn't feel self-destructive anymore. Another long, uncomfortable night of going to seedy bars and clubs followed, after which I was so happy to make it home unscathed that I got on my hands and knees and kissed the floor of my dorm.

It was Sunday afternoon when I wrote her back. I remember camping out on my bed in front of a spring training baseball game. It was 1995, when the strike was still on and they had brought in replacement players, building teams full of has-beens and never-weres that only a serious baseball buff like me would recognize. I found it endlessly amusing. Also, since it was 1995 we were writing each other actual letters, not e-mails. I actually had a school-issued e-mail account in those days but I wasn't quite sure what to do with it yet. I wrote Nancy a long, happy letter. She had asked me to enclose a picture of myself, so I found a picture of myself in a tuxedo from one of the school concerts that was lying around, in which I looked dapper, but scruffy. I asked her to send one back.

Nancy's reply came back a week or so later. Nancy was an aspiring singer/actress, so she enclosed a 'head shot'. She had grown into a very pretty young woman, with long brown hair and brown eyes. She was smiling in the picture with her chin resting on her hand. She actually brought up the possibility of getting together sometime. It seemed unlikely at the time because we were states away, but fate was on my side.

My aunt and uncle had recently moved to the same town as Nancy's family and, as luck would have it, that's where we were going during the Easter holidays for a night. I wrote her back and told her (it was 1995, not 1895, lord knows why we didn't just start talking on the phone at this point), and she responded that that would be great.

Life was changing rapidly for me in those days. I had had an amazing epiphany that led me to change my educational track so starting next semester I would have a new major, and this one I would perform well in, thankfully. I knew I only had to suffer through the rest of this semester and then I would be okay.

Finally, Easter break rolled around. I arrived at my aunt and uncle's house, and called Nancy. My grandparents of all people were going to drop me off at her house for the afternoon (I did actually have a driver's license, so lord knows why I didn't just borrow my parents' car, I think the problem was that I didn't know where I was going, and before GPS or cell phones, getting lost would be a problem).

I knocked on the door, my heart pounding in my chest. Nancy opened the door. She was wearing glasses, a tight sweater and jeans. Glasses might be a turnoff for some people, but for me glasses make a woman look smart and sexy. She was about 5' 6" and thin. After some pleasantries, my grandparents left us alone. Nancy was alone in her house. Her family went to Las Vegas during the break, but she stayed behind. I got a brief tour of the house, and then we settled into her kitchen. Nancy pulled out an amazing picture of the two of us as toddlers standing up in her playpen. It was incredible to think that we had known each other practically all of our lives, and here we were, all grown up.

Conversation flowed easily between us. It always had, even as children. We talked about our families, our friends, our interests, and our schools, as the afternoon flew by. I was the one who could recall the most of our times together. I had a much better memory than she did. I kept glancing at the clock because I knew by 6pm I'd have to be back with my family for dinner. The time went by all-too-fast. Nancy gave me a ride back to my aunt and uncle's house, and when we got there she suggested that maybe I could come back later and we could watch a movie or something. I said that sounded like a great idea. The phone number that I had called her on before (I got it from my family) was her parents' phone. She gave me her own phone number by writing it in lipstick on the back of a business card. That card stayed in my wallet until the wallet itself fell apart years later. Nancy came inside to say hello, but declined an invitation to stay for dinner.

My family's dinners were always agonizingly slow and boring affairs, so you could imagine how time dragged by this particular evening. Finally, the cleanup began and I ran to the phone to call Nancy. She came back and picked me up, with my aunt handing me a key and telling me not to worry about how late I came back.

Nancy drove us to a Blockbuster, and we set out looking for a movie to watch. We decided we wanted to see something neither of us had seen before. Somehow we eventually settled on The Mask, with Jim Carrey and Cameron Diaz. Well, it was something neither of us had seen before, at least. We went back to Nancy's house and settled on the couch in her living room to watch it. We sat reclining on opposite sides of the couch.

We were maybe halfway through the movie when it happened. I happened to look over and saw that Nancy had started rubbing the back of her neck with her hand. "I have a stiff neck," she said, "Can you rub it?"

Most guys would have picked up on that subtle signal, but I was still young and naïve. I tentatively slid over to her side of the couch and started to rub the back of her neck with one of my hands. It probably seemed to Nancy that I wasn't interested in her, but, well, of course I was! I was just really nervous. Luckily for both of us, she had one more trick up her sleeve. "Don't worry, I won't attack you or anything," she said, turning to look me right in the eyes.

I don't know what it was, whether it was the way she said it or the way she was looking at me, but suddenly something clicked in the back of my mind. Nancy wanted me to kiss her! I was sure of it! Well, I was pretty sure of it. How could I know for sure without making an ass of myself? I had known this girl all of my life and I definitely didn't want to make a wrong move and ruin our newly-rekindled friendship. We were close to each other, face-to-face, and to test my theory I slowly started to move closer to her.

Nancy was closing the gap on her end. My heart started pounding so loudly I was sure that she heard it. I was right! It seemed like it took forever for us to close that small gap between us, like in one of those romantic movies. I felt my brain kick into overdrive, eager to remember every moment, every sensation of what was to come.

Finally, our lips met. We had kissed before, little chaste kisses on the lips, but this was different. We kissed slowly, lips seeking out lips. After a while we sunk a little more into each other, our mouths opening and our tongues beginning to probe. I slid my tongue between her teeth and tickled her tongue with mine.

I was rewarded with a moan from Nancy. She pressed forward until she wrapped her arms around me and pushed me gently backwards onto the couch. We settled in that way, with her lying on top of me on the couch, arms wrapped around each other and hands in each other's hair, kissing feverishly.

I could have stayed like that forever. Even kissing Nancy was beyond my wildest dreams. It was one of those life-altering experiences, where you knew that you would wake up in the morning and things would never be the same.

After what could have been days but was probably only several minutes Nancy lifted herself off of me and took off her glasses. She also surprised me by pulling her multi-colored sweater off of herself, revealing a tight white shirt underneath. It was then that I realized that I was also getting warm, and scooted into a sitting position underneath her to shrug off my denim button-down shirt that I was wearing unbuttoned over a t-shirt.

Once I was able to pull it down my arms and toss it aside, the kissing resumed. I could have kissed those lips forever, but Nancy broke away and began to kiss and suck on my neck. I took her cue and began to kiss her neck whenever it was within reach. I began to run my hands up and down her back, and then almost by accident slid them underneath her shirt. Now I was running my hands up and down her bare back. I was surprised when I realized that there was no bra strap. My desire to touch her breasts was almost overwhelming, but I wasn't sure how far Nancy wanted to take things.

Nancy finished kissing around my neck and shoulders, and moved back to my lips, pressing herself against me again. I took the initiative and slowly started maneuvering us on the couch until we were side-by-side. I'm not even sure what I was trying to accomplish. I think I just wanted my turn on top, you know? We wrestled around on our sides for a while, kissing while our free hands ran over our backs, our legs intertwining. Eventually I reached around her back and pulled her beneath me. I was tall but very thin in college, about 5' 11" and 125 pounds, so I wasn't heavy at all. I pressed my lips into hers roughly, like I was trying to consume her. I could feel her breasts crushed against my chest, and my crotch pressed up against hers. I pressed my whole body against her as if I was trying to merge with her.

It was Nancy's turn to slide her hands underneath my shirt and rub up and down my bare back, scratching me with her nails. She also began to slide her right leg up and down my left, which was also giving me better access to her crotch. I could feel my erection pressing into her, and I'm sure she could too. It obviously wasn't slowing us down. In fact Nancy had started slowly moving her hips against my erection.

We continued like that for a while, kissing and rubbing up against each other. We were probably both getting more and more turned on. Eventually Nancy broke the kiss and whispered in my ear, "Do you want to go to my room?"

"Sure," I said, and climbed off of her. I offered her a hand and pulled her off the couch and right back into me for another long kiss, our hands running all over our backs. By now the movie had ended and the TV had gone dark. Nancy broke away, took my hand and led me through her house. It was almost completely dark in her house, the only light coming from appliances and the glow from the street outside the windows, so I had to rely on Nancy to lead me around. I had taken a brief tour of the house when I first got there that afternoon but Nancy had whisked me by her bedroom pretty quickly. One thing I did remember was that Nancy had put a blanket up over her window so that her room was completely dark. She led me over to where I vaguely remembered seeing her bed and let go of my hand. I was standing in darkness and I didn't know what Nancy was doing. My heart was thumping before but now it started pounding again.

I suddenly felt Nancy's hands groping around my waist. She latched onto my t-shirt and pulled it over my head. Once it was off Nancy kissed me again, pressing against me. I was shocked to feel her naked breasts against my naked skin. More turned on than ever, I grabbed her in a bear hug and kissed her as hard as I could.

Eventually I started feeling around for her bed with my left hand. I couldn't see anything in the darkness, but luckily it turned out that Nancy had stationed me right by the edge of her bed. Once I was sure of where it was, I grabbed Nancy and all but threw her down on the bed. I climbed on top of her and kissed her, but I was dying to get my hands on her breasts. I reached down and began to fondle them as I kissed her. Her breasts were soft but firm, and more than a handful. I would have loved to go slowly, gently touching every inch of her, but I was caught up in the passion and fondled them roughly, urgently, kneading them with my hands and pulling on her nipples with my fingers until they were hard. Nancy didn't seem to mind at all, in fact she grabbed my hands and held them to her breasts as encouragement for what I was doing.

Suddenly Nancy's hands were at my waist again, unbuttoning my jeans. She unbuttoned them and began to pull them down my hips. Once she realized she couldn't move them any further from her position, she rolled me off of her and onto my back. She stood up and pulled my jeans off of me. I could hear her unbuttoning and pulling off her own jeans. Nancy climbed back onto me, and now we were both reduced to our underwear. She pressed herself against me, breasts against my chest, crotch against my crotch, and kissed me again. We had been in that position before when we were dressed, but nearly naked was a completely different experience. There was much more skin-to-skin contact, and now I could feel the heat of her crotch as it pressed against mine, and I'm sure it made a difference in how she could feel my erection as well.

Our passion was getting the better of both of us now, and we started wrestling back and forth as we kissed each other hungrily and pressed our hips against each other. Whoever was on top would be grabbing the other's ass, helping to press our crotches together. Eventually I rolled on top of her, rubbing my erection against the warm spot between her legs. We were dry-humping with abandon, and I could feel myself getting more and more turned on by the stimulation. Suddenly I felt the unmistakable build of a pending climax, and I pulled away from Nancy.

"What's wrong?" She asked.

"I'm getting... umm... close," I replied.

"Oh," she said. I was still on top of her, hovering over her, and suddenly I felt one of her hands pressing against my crotch. "Lie back," she said.

I actually thought about protesting. In my crazy inexperienced 19-year-old mind it was perfectly fine to make out and take your clothes off and rub up against each other, but actually having an orgasm was crossing an invisible line. Luckily I was just so turned on by that point that my 'other head' prevailed and I obediently rolled onto my back. It turned out that Nancy wasn't going to try to get me off then anyway. Nancy grabbed my underwear and pulled it over my erection and down my legs. She took off my socks, too, for good measure, so now I was completely naked.

"I'll give you a few minutes to cool down," Nancy said, and lay down by my side, snuggling against me.

"I'm not going to be able to cool down like this," I whispered. I knew we were alone, but I couldn't help but whisper. Nancy started running a finger up and down my chest. I responded by taking my left hand and slowly tracing it down her stomach and onto her panties. I began to trace the outline of her pussy through her panties. Nancy responded by sliding her left leg over me, giving me better access. I touched her like that for a minute, feeling her wetness already seeping through, and then moved her panties aside and began to touch her naked pussy.

Nancy squirmed in response, and began sliding her leg up and down mine. I took my hand and slid it down the front of her panties instead of going from the side. I slowly explored my way through her pubic hair and all around the folds of her vagina. I took my time, trying to memorize every inch of her by feel. Not to be outdone, I took my right hand and began to touch and squeeze her left breast. Nancy reached out to my penis with her left hand and began to stroke me, but I was much further away from orgasm by this point. Nancy was lying against my ear, breathing and moaning. I began to slide my fingers up and down the length of her pussy.

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