Life Redone (Parts 3 & 4 of 10)

[Wanted to make sure this whole series was posted again. This story was written a couple of years ago.]

I guess this was one unwanted side effect from the device.

Although I now had the power to go back and re-do just about every moment of my life where I had blown an opportunity with a girl, it didn’t stop me from thinking about things after the fact. In nearly every single one of these moments, there was very little preventing what I went back to do. So, if any of these moments had actually happened, my life could have been completely different.

As I mentioned earlier, I didn’t regret where I was at now. But I couldn’t help being distracted by thoughts of how Amanda and Madison could have been, long term.

It had probably happened because I went back to re-do moments with two of my really good friends. In order to get my mind away from this emotional stuff, I needed to pick a moment with a girl I had never thought of as being more than a good time.

I started to think back to all of the prettiest girls I had ever known, and tried to think if there had ever been a chance with any of them. There were never many girls that I hung out with that I didn’t consider a good friend. However, there was one moment that came back to me when I thought about my best looking friends.

There was a girl, Brittany, who was pretty famous and popular at my high school. She was a model and had dreams of making it big. She had dirty blonde hair and blue eyes, with a tan body, and a wonderful figure. She was just gorgeous, the type of girl who you would definitely call a ‘ten’, and was very sought after. I guessed she had about mid C cups, and all of her assets were pretty perfect.

She actually came over to my house one time to study for a test. I guess she considered me smart enough that she wanted to study with me. Unfortunately, when I say we studied, I really mean we studied. I was single at the time, too, so I had no excuse, other than the thought that she would probably have no interest. We never left my kitchen and she left after an hour or two with just a hug.

This one was going to be a bit trickier. The previous two girls were both great friends of mine, who flirted with me constantly and were obviously very open to things. How would I get to the point where sexual acts became a possibility with my high school friend who I only talked to during class on occasion?

Force was obviously an option. If anything happened, like her escaping or somebody hearing, I could just immediately hit the button and everything would be wiped out. I suppose this could be the last resort option, but I didn’t want to waste a trip if it probably wasn’t going to work.

The first thing I was going to have to do on this trip back was get rid of my parents. I remember they had been home that night and probably had an eye on the situation from time to time. Once I got them to leave, I had to try to seduce Brittany as best I could, or at least make sure something good came of things. If I could even get a little bit of action with a girl like that, the trip probably would have been worth it, just to live out that fantasy.

I focused myself, happy to not be thinking about anything relationship connected with this one. I grabbed the device and thought about a few minutes before she arrived that night. Then I took a deep breath and hit the button.

A long flash of light. This time it seemed like nearly a minute. I was going back probably about a decade.

Finally, I appeared in my old kitchen. My mom was in the next room and my dad was in the living room. I looked at the clock and saw it was 6:55, probably meaning she was going to arrive around 7:00. I took another breath and went into my act.

“Mom, dad, you’re never going to believe this” I said with some conviction. They both came into the room rather fast asking what was going on.

“Tom is stuck downtown with no ride in a bad area” I continued. “He’s really nervous and his parents aren’t in town. Can you please get him?”

I was lucky that my parents were very caring people. Tom was a good friend and they rushed out without hesitating. Downtown was far enough away that I wouldn’t have to worry about them finding out he wasn’t there. By the time they got there, I was planning to be back in the present.

I looked in the mirror and barely recognized myself. I wasn’t tiny, thanks to the sports I played growing up, but I looked so young and small. As I was looking myself over, the door bell rang. I opened the door and there she was.

Brittany was dressed in a white tank top and a jean skirt that went about halfway down her tan, shaped thighs. She was totally made up, as she always was, and flashed me a gorgeous, white smile as I invited her inside.

“You’re a life saver” she said and hugged me. “I was going to fail this test tomorrow.”

“No problem” I laughed and hugged her back tightly, feeling her busty chest press against mine through our clothes.

“So where do you want to set up?” she asked with a smile.

“How about my room?” I suggested. All that time ago we just went right to the kitchen.

She didn’t seem to think much of it and followed me over to my room. I swallowed hard as I entered and saw some mess, realizing maybe this was why I hadn’t suggested my room all of those years back.

“Sorry for the clutter” I laughed and tried to toss a few things out of the way. I made sure to clear off my bed.

“Don’t worry, mine is worse” she laughed and tossed her book down onto my bed.

I sat down on my bed and she joined me. I looked into her eyes for a second or two, to see if I could gauge a reaction. She didn’t seem to react much either way.

“So where do we get started?” she asked in a friendly tone.

“Well…” I started and opened the math book. I looked at everything and realized my mind was blank. While it was an advantage to have my experience sexually, it obviously put me in a rough spot, trying to remember things that I should have known back then. That meant I wasn’t going to be able to buy any time studying with her, since I would just make a fool of myself. My mind quickly scrambled trying to think of what to do. I felt the device pressing against my thigh in my pocket and it gave me an easier state of mind.

“Brittany” I started with slightly increased breath. “I promise you that I will help you study and pass this test. I also swear that I didn’t call you over here for anything else, but you just look so beautiful and I’m having trouble concentrating. I’ve always wanted to kiss you.”

She sort of laughed, almost as if she had heard similar statements before. But she also didn’t seem repelled, which was a good start. I figured if I could use my extra experience to turn her on, maybe I could do this the right way.

To my surprise, she moved in and gave me a strong kiss on my lips. I didn’t know if she found me attractive, or perhaps she was just thankful that I was going to help her with the studying. I knew this was going to be my only chance to do things without true force. I quickly kissed her back with extra force, startling her a little as I kissed her deep and guided her onto her back on my bed.

“Easy there…” she trailed off as I started to kiss to her jaw, then her neck. I sucked gently on her neck muscle and let my tongue trail up and down. She stopped talking and only sighed quietly as I continued to do this.

“I promise you’ll get a perfect score on the test” I smiled and went back to turning her on as much as I could by teasing her neck. I was firmly on top of her, with my legs spread out across hers lower body, as incentive to keep her from scrambling too much. I knew it was now or never, and that I was on a limited clock. My hand disappeared under Brittany’s skirt and started to rub her panties.

“What are you doing?” she said, but it wasn’t quite angry. In fact, it was with a mixture of moans. Shockingly, she was already wet, so I continued to let myself rub between her legs. I looked down at her gorgeous body and pretty face, and couldn’t believe I was getting this chance.

“Just let me pleasure you for a little bit, and I promise I’ll teach you everything I know” I smiled and kissed her neck harder. Now, I pulled up her tank top and saw a black bra housing a great pair of breasts. I saw her open her eyes and look down at me with an unsure look on her face, but I ignored it and pushed off the bra, revealing her incredible breasts. She must have spent some time tanning in a booth because her breasts were fully tanned, too. I took them into my mouth, sucking and flicking my tongue across her nipples, which hardened against my tongue. She began to moan, and I used the opportunity to continue to push the envelope, pulling her panties to the side and quickly shoving two fingers into her pussy. Before she could say anything, I was curled against her g-spot, and roughly rubbing over and over. My thumb rubbed over her clit and my mouth stayed against her nipples. Her moans quickly turned to panting and I felt her pussy tighten around my fingers as she came. Her nipples were rock hard against my tongue and her body shook from the sensations.

I glanced over at my clock while Brittany struggled to catch her breath. I really didn’t have a lot of time. If I was going to go for it, I may as well try to go for it all. I started up rubbing against her g-spot again, adding a third finger so that it filled her more. While I did this, I subtly yanked down my shorts and boxers, freeing my cock. With a very quick maneuver, I pulled my fingers out of her pussy and immediately pressed my cock inside her.

“What the fuck??” she moaned out as I entered her.

“It’s just my fingers” I lied. “I added more.” I leaned up and started to kiss her neck again while I slowly fucked her. I kept my hand down between her legs too, in case she bought my weak lie. I was banking that she didn’t have much experience, though her beauty probably had brought on a few incidents.

“No, pull out” she said, though she was moaning. I bent my head down and started to suck on her chest again, wildly sucking on her hard nipples, as her body told a different story than her words. I started to fuck her harder, as she knew anyway, my cock roughly hitting her g-spot with each thrust. She was lightly pushing against me, but when my fingers started to rub her clit, she wilted and her body shook violently. Her tight pussy clamped down on my cock hard, massaging me as I thrust in and out. As long as I kept my fingers on her clit, she didn’t have the strength to move.

“Cum for me” I teased as her pussy squeezed me in rhythm. She slapped me a little but kept taking it. I wasn’t sure whether or not she wanted it at this point. I continued to rub her clit in time with our fucking, and her body continued to shake. Again, I had to steal a long glance at her beautiful figure being taken to new heights by my cock. The situation was so arousing, and I had to get going anyway, so I didn’t fight the feeling when my orgasm slowly started to build. I started to pound her harder and faster as I got close.

“Don’t you dare” she said as her eyes shot open. I went back to sucking on her nipples, keeping her bouncing breasts in my face as my cock continued to stiffen inside her. With her gorgeous breasts bouncing in my face, I let myself release deep inside her tight pussy, rocketing load after load of hot sticky cum deep inside Brittany’s pussy. I felt her cum again from my constant rubbing of her clit, and her spasming pussy forced out a few extra shots. I let myself empty completely inside her and quickly pulled out and pressed the button at the same time, just as her face started to form a scowl.

The long flash of light and I was back home. This time, there was no emotional issue. I smiled as one of my bigger fantasies had been fulfilled. The only downside now was seeing the marks on the side of the box drop down to seven.

I was feeling pretty good, and wanted to use another trip before I really got into any planning. As my mind thought about all of the girls of my youth, I stopped on a couple of Latina sisters that I used to play sports with from time to time. One in particular, Marie, was very cute, with tan skin, long, brown curly hair, brown eyes and a very busty chest. Back then, she was at least a large C, despite being in pretty good shape, body type wise.

I thought back to one of our days playing soccer together. This trip back would be similar in length to my previous one. I hit the button and waited for the decent timed flash of light to give way.

This time, the light barely diminished, as I appeared in the middle of a bright, sunny grass field. I recognized a few people that I used to hang out with, and I looked at my own outfit, seeing an athletic red shirt and black gym shorts. I had on some of those higher, heavy socks with black soccer cleats. It seemed as though the game had just ended, and most of us had a noticeable layer of sweat. A few feet from me was Marie, wearing a blue t-shirt and black cheer short shorts, with blue knee high socks and cleats. Her chest pressed out obviously against her top, and I wondered if one sports bra could possibly keep her in place.

Luckily, we played at a park that contained multiple, large bathroom areas with showers inside. The group of people started to say their farewells, and then people dispersed in different directions. I decided to follow Marie.

“Pretty good workout today” I smiled as we walked toward the nearest bathroom area.

“Yeah well, we’ll beat you next time” she laughed. She had a noticeable Spanish accent. I guess we won that game.

I knew I didn’t have much time to work as we quickly approached the ladies side.

“Doesn’t matter, you still look better than me in knee high socks” I smiled somewhat suggestively and pulled my socks lower.

“Oh whatever” she giggled and playfully shoved me. She started to walk into the door and I followed her. “Where are you going?” she laughed again. Instead of answering her, I wrapped my arms around her from behind and kissed her neck. My lower body pushed against her nice ass as I walked her further into the luckily vacant room and towards the shower area. She moved her head to the other side to allow more room for my kisses on her neck as she started to sigh and moan. I brought her into one of the shower areas, and lifted her shirt up and off from behind her. Without any hesitation, I pulled off her sports bra, revealing her incredible breasts. Unable to resist, I quickly moved in and started to suck on them, taking a good amount into my mouth and running my tongue around her nipples. My mouth teased one and my hands bounced and played with the other, and then I switched back and forth.

I helped her pull my shirt off and it joined the growing pile of clothing on the ground. My erection pressed painfully and obviously against my shorts, so I decided to remove them and my boxers right then. I looked longfully at her breasts, and she was nice enough to catch on. We turned the water on to get a little lubrication and she got on her knees. She placed one of her massive breasts around one side of my cock, and the other wrapped around the other side. Not too many girls I knew could give a good tit fuck, but this was going to be the ultimate. She went up and down on my shaft, sometimes licking the tip with her tongue when I came up and through them. It was a pretty arousing sight to see my old friend with her big breasts around my cock. She let her breasts drop off me briefly, taking my cock into her mouth and sucking on me. Her tongue flicked around the head and the underside while she pumped me and coated me in spit. Then she put her breasts back around me and went faster. Sometimes she would hold me between them and suck on the head for a while. At last, she sucked me long enough to bring me to the edge, and then popped off and pumped hard with her breasts. My cock shot ropes of hot cum across her face from between her breasts, painting lines across her face and narrowly missing her eye.

I helped her back to her feet and pulled off her shorts, panties, and cleats, leaving her in just the knee socks. This time I got onto my knees and went between her legs. My tongue poked between her pussy lips and found her clit, which I started to lick quickly. I spread her lips with my fingers and started to suck on her clit, and her moans quickly echoed around the room. I slid two fingers into her pussy and pressed them against her g-spot, rubbing it consistently while my tongue flicked across her clit. This combination brought her to orgasm pretty fast, and I felt her pussy contract around my fingers as her stomach muscles rippled. I looked up and enjoyed the underside view of her large breasts. She struggled to stay on her feet while I continued to pleasure her. I stopped and kissed the insides of her thighs before returning to her clit. A few more minutes of this and she came again, squeezing my fingers with her tight pussy muscles. She muttered something in Spanish and backed away enough to regain her breath.

I had no intentions to stop here, though. I figured the best position with her would be doggy style. It would allow me a great view of her terrific ass, and I could grab her big breasts from behind. I took the liberty of helping her onto her hands and knees, and she was either too tired to question or had just decided to allow me to do whatever I wanted. Looking at her inviting position, I couldn’t help but immediately press my cock into her pussy from behind. I buried myself completely inside her and gave her a spank before I started to fuck her in a fast rhythm. I reached around and grabbed her swinging breasts, playing with their fullness in my hands and her nipples in my fingers as I fucked her faster and deeper. I felt myself hitting her g-spot with each deep thrust. I grabbed her hair and brought her face around back towards me, which I eagerly kissed, feeling her moan into my lips. I spanked her with my free hand and I felt her cum hard on my cock, squeezing me over and over as she vibrated against my mouth. After her orgasm finished, I let go of her hair and returned my hands to her breasts.

“Aye, fuck yeah” she moaned. I let myself fuck her harder, making her ass shake as I pounded in and out. I brought one of my hands back to grip and spank her firm ass, as the other continued to play with her breasts. She managed to gather up enough strength to reach back and rub my balls, making me fuck her faster. I felt her soft fingers and the tips of her long nails massage my balls softly, as that and her tight pussy brought me close to the edge. I wanted to keep going but sometimes a situation is too hot and feels too good. A few more thrusts and I buried myself. Her hands remained on my balls as my powerful orgasm hit. It was one of those orgasms where it builds up and takes longer than usual to actually hit, but then comes out uncontrollably and ridiculously fast. I had to hold onto her breasts to help keep me from falling as my body shook. My cock was lodged deep inside her and was rocketing out cum almost quicker than I could handle. I could feel myself completely flood her insides and felt it already start to come out even before I stopped filling her. As my orgasm finally slowed, I pulled myself out from inside her and watched a ton of cum pour out. She collapsed onto the floor of the room and I let myself enjoy the sight as I reached for the device in my shorts.

I pressed the button and the light brought me back to my room. I looked at the device and saw six marks left. It wasn’t going to be easy to narrow the rest down.

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