A chance to redo ten moments of your life. What would you choose?
[Love hearing from my readers. Thanks and enjoy!]
Only nine more opportunities.
That was my thought process right now. I had gone from debating even using the device and wondering if it was really legitimate, to planning out how to use it perfectly. I’m sure there were more than ten girls that I wanted a second chance with, and I wanted to make sure I didn’t forget anything that I would later regret. After all, this was pretty much my last chance at youth and fantasies of this proportion.
I tried everything that I could think of to make sure I left no stone unturned. I went through my social media friends, even breaking into my old Myspace account to see who I could recall from earlier times. I looked at old yearbooks, photos, and saved conversations.
“That’s a definite” I said, scrolling over a girl from high school.
“That would be really interesting” I chuckled as I saw a face from nearly ten years ago.
“That night…” I said, shaking my head as I came across another college friend.
As I said, having a long term relationship in college was probably not the best idea. I don’t regret where I am today, but as this device had helped to uncover already, there were a ton of opportunities that I had blown. Another one of the biggest failures happened early on in my college life. I had made a lot of friends early, the large majority of whom were girls, and I spent extra time at school hanging with all of them. Though there was plenty of flirting, virtually nothing of note happened with any of them.
The closest time came on a night where I stayed over one of the girl’s dorm rooms. I used the excuse that I had to be there early the next morning (which was true), and that I wanted to stay closer to the event. Of course, I never mentioned to anybody that I was staying with a girl, which wasn’t even legal at the college. We rented a movie, hung out late, and even slept in the same tiny dorm bed. There may have been the random quick cuddle, and our lips possibly brushed at one point in the middle of half consciousness. I wish I could tell you a more interesting story, but that was the end of it.
Madison was the girl that I stayed with. She was a pretty blonde with curly hair, just over medium in length. She had nice blue and gray eyes and very nice straight, white teeth. Hey body type was pretty much average, with what appeared to be firm “B” cups and a good body. Her most impressive feature was definitely her ass, which most of the group had caught onto and teased her a lot for (and she definitely didn’t mind). Despite being cute enough, I had heard whispers that she had very little sexual experience. Candidly, I heard this because our friends knew that we flirted a lot and all wanted us to be dating.
“She doesn’t have a ton of experience” I remember our friend saying to me one night. “But she wouldn’t mind doing a lot with you.”
So there I was, stuck again with no good options. If I could share some advice with people who hadn’t hit college yet, I would probably tell them this much. If you are in a great relationship, that’s fine. Just do yourself a favor and avoid making a lot of female friends, especially early on. The temptation is not fun.
Was this my logical next choice? Aside from the previous event that I had just re-lived, this was definitely up there on my list of regrets. At some point, I was going to have to write down all of my options, to make sure that I didn’t run out of chances and end up missing an obvious moment later on. But I still had nine left, and I knew there wasn’t going to be nine moments that I wanted to re-do over this one.
I stood up off of my bed and began to pace around the room. The cool wood roused my senses even a little higher than they had been, and I stared down at the box on my bed. I closed my eyes and thought about all the girls in my prior experiences, and tried to see what came to mind first. Sure enough, the Madison night continued to enter my thoughts, again and again. I picked up the box, gave a firm nod, and pressed the button.
A longer flash of light than the first time, but after a few seconds, I was in the middle of walking up to the dorm rooms. Perhaps the light takes longer when you go back further in time. My first adventure had probably been about three of four years back. This one was closer to seven years.
I had a small backpack slung over my shoulder. I looked at my arm and noticed it was a little skinnier than even my first venture back. I really should have gone to the gym more when I was younger. I looked to the ground and noticed my old shoes. And did I really think those socks that disappeared before the top of the shoe were necessary? Uncomfortable, at best, at this point.
I held the box for a few more minutes, and tried to decide where to put it. If I threw it into my bag, I ran the risk of an accidental push. For now, I stashed it in my pants pocket and continued my walk towards the dorms. It was already night time, but not late enough that I would draw major attention for entering the girls dorm rooms. Still, I blushed a little when I saw the RA’s giving me an extra look as I came near the main door.
Wait a second. I had forgotten that these doors were obviously locked. Nobody was going to let a random guy into the elevator area. I scrambled into my pockets and pulled out my old hilarious looking phone. I scrolled through the names, seeing a mix of familiar ones and getting a big laugh out of a few old names. Finally, I hit Madison’s name and punched the call button.
“Hey, I’m by the entrance” I said, hoping I hadn’t forgotten any of the details of that night.
“I thought you said you were going to text” she laughed.
“Oops” I laughed in return. “Just come get me.”
A few minutes later, the main door swung open and Madison was there. She was wearing a light blue tank top and white shorts that stopped less than halfway down her thighs.
“Moving in?” she winked and nodded towards my bag.
“There’s barely anything in there” I laughed in protest.
“Just teasing” she smiled. “Did you want to come up or did you still want to go out and rent stuff?”
“You can pretty much watch anything online these days” I laughed. “Let’s just head up.” I figured I should have as much time as possible to get in everything that needed to be done tonight. She nodded and held the door open for me to enter the main part of the building. We finally hugged as we waited for the elevator to come down, and then rode up to her place on the third floor. We walked around the corner of the floor and finally made our way into her dorm.
“At least this way, we don’t have to come back after hours” she said. “I’m sure no one will check but it’s always good to be safe.” She opened the door and let me inside her tiny space. It was basically made up of nothing more than two beds, perpendicular to each other, a small bathroom (at least it had a shower) and a small area to walk into.
“The roomie is gone for the night” she laughed, seeing me looking around. “She said we were too awkward to be around.”
“She isn’t wrong” I laughed. I looked up at her and felt my face go a little red. She blushed a little too and then turned to set up her computer on the table she put next to her bed.
“You don’t have to sleep on her bed if you don’t want to” she said at once. “The mattress is bigger than it looks.”
“Thanks” I smiled and sat down on the bed beside her.
“Think Superbad will be available yet?” she asked, searching around online. I had already seen it, but didn’t mind having a goofy type movie on that I didn’t have to pay much attention to. Finally, she found a sketchy looking website, but after closing a number of advertisements and pop-ups, was able to start streaming it. She laid down on the bed, closer to the edge, and invited me to climb over her against the wall. We both went under her cover and I put my arm over her side, putting us into a spoon position. If my memory had any value, I was pretty sure we had done this a few times before. And if the device was still working, it probably had her convinced that I was single in this situation, opening up all possibilities.
My lower body was lined up with her gorgeous ass, which looked full in her shorts. As the movie got going, I rubbed my hand on the smooth and cool skin of her arm. I felt some goose bumps as I continued, and she giggled a little. After a little bit more of this, my hand made its way underneath the bottom hem of her tank top, taking in the smooth skin of her stomach. I could feel her breathing a little quicker than usual, and I knew this was stepping passed the line we usually drew on these occasions. I left my hand there, under her tank top, until her breathing started to return to normal. We had a few laughs from the movie and the distraction was a good thing.
Finally, I let my hand continue its trip north, and I brought it to a stop on the outside of her bra. I cupped her perky breasts against the material and I could tell she was breathing even quicker this time. There was absolutely no resistance in her though, and it seemed our friend had been accurate that she was ready to have some fun with me.
“We may as well get dressed for bed” she turned towards me and smiled. “Hope you don’t mind that I sleep in my underwear” she continued, the smile never leaving her face. She pulled her tank top off and showed me her light blue bra, matching the top she took off. She then unbuttoned her shorts and pulled those down, showing me her blue and black striped boy shorts. I grinned as I saw more of her exposed than I had to that point, and followed suit by removing my shirt. I pulled off my pants next, being careful to leave them within reach, leaving myself in just green and black plaid boxers. She gave my body a long look over, and then turned her attention back to the movie. My hand returned to her body, cupping her chest again. Following a few more grabs, I went lower, trailing my hand over her body, before stopping on her underwear.
Finally, she turned her attention fully away from the computer screen and turned towards me excitedly. I pulled her closer to me and finally went in for a kiss. She eagerly returned my advances, and I pulled her body so that she was on top of me as we kissed. I put my hands on her ass, against her boy shorts, and grabbed her firmly. It wasn’t long before my arousal became evident, and I grinded myself between her legs. I saw her eyes grow wide when she felt me between her legs.
“It’s so…” she started and reached down before she finished her thought. I saw her jaw fall open a little with a smirk as she felt my length in her hands. I smiled at her and ramped up the kissing again, moving to her neck as I started to grind between her legs again. My hands returned to her ass, but this time they disappeared underneath her underwear, feeling her bare ass for the first time.
“Be easy with me, I don’t have a ton of experience with this stuff” she laughed as I could tell the sensations I was giving her were new and slightly overwhelming. As we continued, I could feel her getting wetter against me, and I figured it was time to try something more.
“Of course I’ll be easy with you” I smiled and got up from under her. I laid her down on her back and let my hand rub between her legs. She was really wet and I watched as she closed her eyes in soft pleasure. I let my finger toy with one of the bottom sides of her underwear, and I gently pulled the bottom part over to the side.
“Just trust me and have fun” I reassuringly smiled at her as I saw some nervousness in her face. She nodded and I gently rubbed a finger between her pussy lips against her clit. She gripped her covers as I rubbed a little faster, watching her body shake a little. Every so often, I would increase the speed and intensity a little bit, and she was quickly moaning and had her eyes shut in pleasure. I used my free hand to pull off her bra, and bent down to suck on her breasts, quickly taking a hard nipple into my mouth and flicking my tongue across it. I took as much of her breast into my mouth as possible, and rubbed harder circles on her clit.
“Fuck, fuck” she said, and muffled herself a bit with her covers, knowing dorms didn’t have a lot of space between each other. Her eyes shot open and her stomach started to ripple as she hit her climax, cumming from my touch on her clit and tongue on her nipples. I smiled at her and kissed her again, before kissing down her body. Without giving her any time to come down from her high, I buried my face between her legs, poking my tongue between her lips against her clit and flicking it roughly. I wrapped my lips around her clit and began to suck on it and I could feel her tense up, trying in vain to hold in her moans. I slid a finger into her tight pussy, feeling just how tight she was, as I continued my tongue lashing on her clit. I made sure to curl my finger against her g-spot and rub that in rhythm with her clit. I picked up the pace inside her and sucked her clit a little more, and she began to writhe underneath me.
“Oh my god, stop, it’s too much” she panted as I never slowed down. A few seconds later, her body tensed up completely and she squirted, coating my face in her cum as my dual stimulation brought her to new levels of ecstasy. I continued to roughly lick her clit as she rode out her orgasm, and then laid back, completely spent.
“That was incredible” she said, still breathless, as I played with her breasts more. “You definitely deserve a reward for that” she smiled, rising up enough to sit against the wall as she grabbed my obvious bulge against my boxers. She played with me for a few minutes and then helped me out of my boxers, giving me another look of anticipation when she saw me naked for the first time.
She seemed a little unsure of herself, but she helped me onto my back and started to pump my shaft up and down. I smiled up at her as her soft hands felt good. After a few more pumps, she got onto her knees and bent over, taking some of my cock into her mouth. She had some trouble with the size, but got better as she went on. Her lips went up and down over my head, and finally added her tongue against my sensitive underside. As my breathing intensified, she was encouraged enough to go faster and a little deeper. As the friction started to feel better and better, I reached up to play with her breasts again, bouncing them in my hands and sometimes rolling her nipples between my fingers.
She took my length out of her mouth and let her tongue run up and down the shaft. Then she plunged back down onto my cock, keeping her tongue in the right spots. As I started to feel myself slowly getting closer, I took her hand and put them on my balls. She rubbed them slowly as I felt myself starting to grow in her mouth.
“I’m gonna’ cum” I said quickly as my cock neared its thickest state. I saw her open her eyes nervously as I hit the edge, rapidly firing cum into her mouth. She took a few seconds of it and then pulled off, taking a few more blasts on her face. I couldn’t help but laugh a little as I covered her face with my seed.
“Sorry about that” I laughed, as she held onto my cock and looked around, looking unsure of what to do.
“That was fun” she giggled, swallowing the amount she had taken in her mouth and heading for the bathroom to wash her face. She came back out and sat down on the bed next to me. We kissed harder this time, exploring each other’s mouths and tongue wrestling a little.
“It got late” she laughed as she glanced over at the clock. “You have to leave in a while.”
“Yeah we should probably get a little bit of sleep” I agreed. We laid down together, back in the spoon position, though we both remained naked. I kept a firm grasp on her perky breasts as we laid there.
“I’m glad we finally took it to this level” she said happily. “I’m excited for what’s next.”
That was the first time I felt extra conflicted about this device. While it allowed me to explore alternate realities for brief periods of time without consequence, it also showed me a glimpse into the long term possibilities of certain situations. If I hadn’t been in a relationship, and this night really happened all of those years ago, how different would my life be? Would Madison and I have had a future together? Would I be living in a different place, with a different job, and a completely different life? Surely, these thoughts weren’t the intention of the box.
As my mind raced, my thoughts wandered with regard to potentially ending this here. Obviously, I had no incentive to sleep and live out that next morning again. Still, I wasn’t quite ready to leave. And, if this scene, so to speak, had to come to its conclusion, there was no point in not living out a little more.
I could tell she was basically asleep beside me. I looked at the backside of her naked body, and took in that fantastic ass again. I felt myself becoming aroused again, and as I got hard, I gently poked my cock between her legs. There was no reaction from her as I clumsily tried to find her opening. The angle wasn’t good enough, so I decided to put myself in good position all around. I grabbed my pants and found the device, setting it just within reach on a nearby shelf. Next, I slowly wrapped my lower arm around her body from underneath her, hugging her to me. Finally, I grabbed her higher leg in our spoon position and lifted it up, ever so gently, spreading her enough to give me a target. She seemed to stir lightly, but perhaps wasn’t fully conscious. I didn’t have any hands to help guide me, so I still had some trouble finding my way to her entrance. Slowly, I got closer until I finally found her opening. With one quick adjustment, I thrust upward and I was inside her. She stirred a little more, but still wasn’t fully awake as I slowly started to fuck her, working a little deeper inside her each time.
“Wh-what’s going on?” she finally said, barely awake.
“Nothing” I smiled, tightening my grip around her body and kissing her neck from behind.
That was enough to calm her for a few seconds. I worked my way deeper inside her, and my big, underside vein began to hit her g-spot easily in our position. She started breathing heavier and started moaning.
“Are you inside me?!” she gasped, finally rousing enough to realize what was going on.
“Doesn’t it feel good?” I whispered, kissing her neck again. She squirmed against my mouth and grasp.
“Yeah, it’s amazing” she said between moans. “But I’m not sure I’m ready for this. I’ve never done this.”
I moaned as I felt her extremely tight pussy engulf my cock. Her warm walls closing in around my length as our most private areas met without any barriers.
“Really, we might want to stop” she said, though still moaning.
“Just give it a little more time” I said, my hand around her body now on her breast, twisting her nipple. I could feel her give in slightly and moan more. Soon, I felt her pussy go off in an orgasm, as my cock head rubbed against her g-spot over and over. I felt her liquid spray a little and her walls massage me in spasms. I watched her perfect ass jiggle nicely with each of my upward thrusts. I used my thigh to keep her leg propped up so I could get a free hand back. I used it to grab her ass and give her a playful spank, before moving around to the front of her body and rubbing her clit.
“Oh fuck, too much” she moaned loudly as the combination of my cock inside her and against her g-spot, along with my finger on her clit brought her to another new high. She orgasmed again and couldn’t possibly fight me as I felt all of her resistance go limp. At this point, she was just moaning and taking it all. Her pussy was basically in a constant state of orgasm now, as I continuously felt it squeezing and massaging my cock. I eyed the device on the shelf as I felt myself slowly starting to build towards my own orgasm. I don’t think she quite realized what was happening as my cock began getting stiffer inside her tight pussy.
“Oh shit, oh my god” she said as my cock erupted deep inside her pussy, warming the deepest insides of her pussy with my hot cum. “What are you doing?” she moaned as I continued to fill her up, feeling the big underside vein of my cock throbbing with each rope of cum that I fired off her cervix and deepest pussy walls. Her tight, spasming pussy only milked me, forcing out more shots of cum deep into her, until I felt it starting to flood back out. As I felt my last bit of cum ooze into Madison’s pussy, I pulled out and watched a ton flood back out onto the bed.
“Why did…” she started to question but I grabbed her face and kissed her passionately. A few seconds later, my hand reached the device and begrudgingly hit the button.
That familiar bright light hit for a few seconds, and then I was back in my room again. This time, instead of planning my next re-do, I sat on the bed and stared for a little while. From the corner of my eye, I saw the device light up and knew another mark had disappeared. I almost went onto the computer to see how Madison was doing these days. I stopped myself. That wasn’t what this device was meant to do.