Life Redone (Part 6 of 10)

[Thanks for reading! Enjoy.]

That was the halfway point. The most incredible device in the world only had five marks remaining. I knew from this point forward I would have to make sure that I did the most regrettable moments. If I didn’t do something during this opportunity, I would regret things even more, knowing I had the perfect chance to live out anything right here.

I had a couple of girls that I was definitely going to include, perhaps even saving them for the end. I really only had one or two chances left that I didn’t already have mentally filled. Thinking about how satisfying my last trip back had been, I decided to focus on remembering any major crushes I had. If I could live out one of my long term crushes, I might be able to fulfill just about everything in the end.

College had already provided me with some great inspiration, so I started to think back towards high school. I had only lived out a couple from that time period, and I know I had at least a few crushes back then.

Suddenly, the thought came back to me. I had very few “major league” crushes during my youth, but one of them was definitely during my freshman year of college. There was a girl, Kaylee, who was in a few of my classes that year. The next year, she moved, and I remember being devastated. I was very shy back then, and never made anything resembling a move. All I did was do anything silly during class time to try to make her laugh. That and I tried to avoid blushing any time she said something back to me.

The funny thing is, I found her much more attractive back then than I did now, which is probably why I almost forgot about her. Granted, all I saw were pictures these days, but she seemed to stand out more back then. She was a short, athletic girl with a fit body, black curly hair, green eyes, some freckles, and tan skin. I can’t even communicate what it was that drew me to her back then, and I’m completely serious when I say that I wouldn’t even make a play for her now if I could. But I was head over heels for a year, and I’m not sure I ever liked anyone more than her from a stupid young lust crush point of view.

The tricky thing was going to be even thinking of a time where I could potentially make a move. We had nearly our entire interaction at school, and even though I had the opportunity to go back at any time during the visit, that seemed like a losing proposition. I had no problem risking a failed experiment when it came to a girl like Kaylee, but I needed to at least give myself a chance.

I laid back on my bed for probably ten minutes trying to think back to those days. Had we ever hung out outside of school? No, it’s embarrassing to say we never hung out once. Had there been a going away party? There might have been, but I wasn’t sure that I was invited. I made her laugh a lot by being consistently silly, but I don’t know if we were ever really genuine friends. But I was remembering my only possible chance, as a picture came back into my mind. I remember there was a picture of her in a bikini from a pool party that year. I had, of course, looked at that picture a lot.

It was either at one of our mutual friend’s birthday parties, or perhaps it had been her going away party. I know I was at that one, though. I was pretty confident that if I could think of the picture, I could go back to the right moment.

I grabbed the device, thought of that memory, and hit the button. I was trapped in white light for a long time. This time I was going back over a decade. Just when I started to get a little worried, I appeared in the backyard of my friend’s old house, with music blasting and seemingly dozens of people running around and jumping into the pool. I looked down at my body and almost fainted at how much smaller I was back then, body wise. Still, I had done most of my growing at that point, both height related and where it mattered, too.

I didn’t want to stand out as looking too weird as I adjusted to the surroundings, so I went over to the snack table and poured myself some soda. I used this opportunity to look around the backyard. I had to hold in a few laughs as some people that I still considered friends were running around as their freshman selves. We were all such losers, myself included, and I knew this was probably going to be my most difficult attempt to pull off.

I had just agreed to jump into the pool with one of my friends when I froze. I cursed to myself when I remember the device had to be in my swim trunks. I wasn’t about to take my chances getting that thing wet. I quickly ran inside the house to where people had left various items of clothing. I found my pile and stashed my device in my shorts. Then I ran back outside and jumped in. This was the first time that I allowed myself to experience a little bit more of the past. I played volleyball in the pool, snacked on some junk food, and joked around with old friends. On the occasion, I fumbled with some old knowledge of who was relevant in sports and on television, but I made it through.

I had to turn some focus towards Kaylee as the sky darkened. She was there in the bikini from the picture, a blue and green two piece that showed off her tight, athletic body and developing perky breasts. Her curly hair was all wet and I had many memories of us laughing in class. I joked around with her a little, flirting as best I could and getting some laughs. However, it was becoming apparent that this was going to be a tough atmosphere to make a legitimate move. It was one thing, during my last experience, to fool around with a college car pool buddy in the car and get her in the mood. It was another to try to seduce an acquaintance in the middle of a pool party with all of our friends. I only had one option to do this the right way, and it would’ve possibly changed the course of history had this machine not been so good at wiping memories.

“How about seven minutes in heaven?” I proclaimed from the side of the pool. Yes, that’s right, one of the shy kids just said that during the middle of a pool party with a bunch of judgmental people. It’s funny how brave you can be when there are no risks involved.

I heard a number of different reactions. A few of my guy friends started to crack up and tease what I had just said. A couple of the prude girls said ‘ew‘ and I think one splashed water onto me. I saw a few girls pondering it. I decided to go for it all.

“Well, anyone who has the guts can follow me into Chelsea’s room” I said as I got up and out of the pool. I had learned that this was Chelsea’s birthday party, so my original thought was correct. I didn’t turn back as I dried off a little and walked confidently into Chelsea’s room, all the while holding my breath that Kaylee would follow.

Slowly, a few people started to trickle into her room. The majority of people coming were girls, which I guess was a good thing. Worst case scenario was I got to experience a few different girls. But too many guys and I might not get the chance I wanted. When all was said and done, ten people had come in. Six girls and four guys. One was Kaylee. I knew the odds weren’t good, though, so I made a declaration.

“I don’t know if you guys have had how this works” I started. “If you land on someone of the same sex, you get to choose who to go in with.”

There was a smattering of both positive and negative reactions, but I quickly grabbed a bottle and got the game going. I knew I had just given myself almost 50/50 odds. There were nine other people and three were free choices, along with Kaylee herself. So four out of nine. I grabbed the bottle, took a breath, and spun it around the room. I could feel each fiber of the carpeting scratch my knees as I waited for the bottle to slow. I looked in temporary horror as it slowed and skirted passed Kaylee. Just as it looked like it was going to stop on Chelsea, I lost my balance and fell to the floor, rocking the bottle into one of my best guy friends.

“Guess it’s your choice” he laughed, and luckily there was no argument after my fall.

“Kaylee” I said, quickly, firmly and I’m sure unlike my normal personality back then. I heard some ooh’s go up from a few girls and her eyes widened in apparent surprise. She blushed a little and got up, following me into Chelsea’s closet. I opened the closet door and closed it behind her, knowing I was going to have to do this in a hurry.

“Just relax and let me help you enjoy the next few minutes” I said softly to her and quickly kissed her. There was a small light on in the closet, giving me just enough of a view of her. I was thankful for that because this was one I really did want to see. She kissed me back a little, somewhat tentatively, and it was the first time that I had let myself think that she might be really inexperienced at this point.

“I promise this will be incredible, just let me take control” I said again and kissed her lips hard. Then I kissed down her neck and felt her body tense a bit. I rubbed my hand down her soft, still wet arm. I didn’t have time to draw this out, so after feeling her melt even slightly from my lips and tongue on her neck, I untied her bikini top and tossed it off. I started to suck on her small but perky breasts, feeling her nipples harden in my mouth. My hand cupped one breast as my tongue teased the other, poking her hard nipple with my tongue. I easily took the entire breast into my mouth and concentrated on her nipple. She had fallen over onto her back, and it was incredible to see her tight body in the bikini that I had so often gotten off to from that picture.

I was trying to keep time in my head. I had guessed that about two minutes had gone by and I knew I needed to hurry.

“Wait” she said when I untied her bikini bottoms. “I think you’re nice but this is a little much.” I didn’t slow down though and immediately buried my face in her tight, young pussy. I moved my face back and forth and let my tongue harshly brush against her clit.

“Holy shit” she moaned, obviously never experiencing anything like this before. I took her clit into my mouth and sucked on it before mashing my tongue against it more. Her tiny body began to heave up and down and her moans got louder. I wasn’t sure but I thought I heard one or two of my guy friends laugh and high five from outside. It didn’t take long to build her up and she quickly came hard, as my tongue mercilessly lapped against her clit over and over.

As I had hoped, this had taken a lot out of her. She laid on her back, panting and trying to catch her breath. Though I was short for time, I wanted to experience everything, so I turned her over briefly to see her tight, firm little ass, before letting her go back into her resting position. I imagined I had about three minutes left, so I stripped off my trunks.

“No wait” she said, still trying to recapture her breath as I climbed on top of her and moved my cock between her legs. “I’ve never done this be…oh my!!” she hadn’t before she started the sentence, but had by the end as I entered her tiny entrance. It was a struggle but I quickly pushed my way inside her. I looked down and it was hard to hold myself together, seeing the girl I lusted after for so long, stuck underneath me, impaled on my cock. I started to get into a nice rhythm and bent down to suck on her breasts, which jiggled softly which each thrust.

“Keep it down in there!” I heard Chelsea giggle and yell as Kaylee’s moans filled the closet. I’m sure they couldn’t exactly guess what was going on, and could only imagine their reactions. I was loving every second of this. She was so tight and I felt her walls barely give in to accommodate me on each thrust. I kissed her lips again and felt her moan into the kiss as I picked up the pace. As soon as I let my hand trail down to her clit, she came again, this time on my cock, and I felt her tight pussy go off in spasms. I actually had to slow down this time, as it was too tight to continue through. I held her petite body, feeling every inch of her soft skin, and then ran my hands through the curly hair which I had admired so many times in class. I sucked on her bottom lip as we kissed hard, and she whimpered in front of me as I my cock continued to burrow deeper into her pussy. I gripped her hair again and went forehead to forehead with her, using the small amount of light to look into her eyes, which quickly shut again as I fucked her harder. She was breathing wildly, all over my face, and the passion was incredible.

I dropped my fingers back down to her clit again and, with a few rubs, sent her into another strong orgasm. She opened her eyes and looked at me in bewilderment and with what looked like the equivalent of a “tapout” or “I can’t take it” face. Her mouth was wide open allowing her to breathe as fast and as hard as she needed to. The reality of that year in school was I would have given anything to kiss her. Now, here I was, taking her to heights she had obviously never experienced. The look on her face of ecstasy and amazement combined with her incredibly tight pussy to quickly bring on my orgasm.

It was one of those times where you start to feel it build and then it’s just there. Before either of us could even say anything, I impaled her pussy fully on my cock and felt my orgasm take over my body. My body shivered and hips bucked into her as I filled her up with more ropes of cum than I could count. Each time I thought I was done, I spasmed and another contraction of my big underside vein sent more cum deep into Kaylee’s pussy. I kissed her hard and grabbed her breasts as I finished filling her. I could tell she was too overtaken by the entire situation to even have a response.

“Times up lovebirds!” I heard from outside the closet. My heart missed a beat when I realized that I left the device in my shorts, outside of Chelsea’s room. This was going to be awkward, but at least no one would remember. In fact, I decided it might be fun to go out naked and show the girls what they missed out on.

“You have no idea how long I’ve wanted that Kaylee” I said, giving her one last set of kisses, first on her mouth and then down her tight, exhausted body. Again, I was extremely thankful for the amount of light I was granted, as I took one last look at her gorgeous body and creamed pussy before reaching for the knob.

“Ohhh!” I heard from my guy friends as they covered their eyes and looked away. A couple of the girls shrieked but I caught at least three of them staring in amazement when they saw me come out, still keeping most of my hardness. I’m pretty sure one girl licked her lips and looked to be planning out a future visit to the closet as I disappeared into Chelsea’s living room to get my clothes. I heard a few people leaving Chelsea’s room to try to talk to me as I pressed the button.

That very long flash of light, and finally I was back home. I returned extremely satisfied, but felt a twinge of nervousness as only four marks remained on the device.

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