Unlocking Past Desires: A Second Chance at Forbidden Encounters

[Started a new series, but this doesn't mean the Sisters By the Pool is done. As always, I welcome all comments here. Love hearing from readers. Thanks for reading everyone!]

One night I was on my way home after a long day at work. It was late and very dark out, but as I gazed out of my passenger window I noticed a broken down car with a dejected looking man sitting on the back bumper. I always considered myself a nice enough person, but I wasn’t usually the type that would do something like this. I was too cautious, and this seemed dangerous. But still, something caused me to slow down and pull off to the side. The man rose as I parked my car, and I noticed his face was partially veiled with some kind of clothing. Still, I was able to make out a worn smile with years of stubble surrounding it.

“Need any help?” I offered, as I walked towards his car.

“I think it just needs a jump” he responded in a weary voice. “Thank you so much for stopping. You wouldn’t believe how long I’ve been here.”

“Some people…” I started, though I knew how difficult it was for me to step up. I went into my trunk and found the jumper cables that I have stashed for just such an occasion. We lifted his hood and attached the cables in the right spots. It wasn’t long before the man’s engine turned over and he was back in business.

“Really, I can’t thank you enough” he said, as I returned the cables to my trunk.

“It’s no trouble” I replied with a smile. As I said this, the man went into his pocket and pulled something out. I felt a brief stop of my normal heart beat pattern, but didn’t think he would do something to harm someone who helped him. Still, he wasn’t the most normal looking person from what I could tell.

“Take this” he said and handed me an odd looking box of some sort. With that, he started back towards his car.

“What…what is it?” I asked, studying the strange object in my hand. The man laughed.

“Ever had a moment you wish you could go back and change?” he said, and I could see a smile form. “Congratulations. You have ten chances to think of a moment and re-live it. Afterwards, only you will remember it, and it will have no consequences on society. Of course, you won’t gain any physical benefits, only memories. So, choose wisely”

After the man had finished speaking, he drove off perpendicularly to the road, and quickly disappeared into a flash of darkness. I stared into the distance for a few seconds, clutched the box in my hands, and quickly got back into my car. As I continued my drive home, the man’s words echoed in my head and I tried to think what to make of it.

“What good is it?” I asked myself internally. “If I can’t make any physical gains, that means going back for money is out. I can’t change any future outcomes, so I can’t make any money for the future either. He said all I get are the memories of the event.

I continued to think things through. His tone was almost suggestive when he asked if there was anything I wanted to re-live. Perhaps, do over. Could he have meant, sexually? Of course, there were a ton of moments from my youth that I would have loved another shot at. He couldn’t have known this, but I was happily engaged with my long term girlfriend. We had been together for so long at this point, that I had started to lose memories of certain previous events. The way this machine was set up, though, meant that I could technically go back to any moment, whether I had a significant other or not, and see what things could have been like. And, yes, there were a few times I was tested, in this relationship and others, where I didn’t act the way I wanted to because of the commitment.

Technically, these events would never exist. I would have the memories of the events, but not even the other party would remember anything. It was truly an incredible opportunity to get a shot at some of the times I missed out on. I know it was somewhat terrible of me to want, but part of me felt like I needed this to make up for a relatively calm young life that was spent primarily in committed relationships.

I would certainly have time to think about things. My girlfriend was gone for the week on business, allowing me free thinking time. I pulled up to my house and made my way inside. I sat down on my bed and gently placed the machine on the bed. It had one button on it. Written in very small letters was ‘start’ and ‘finish’ next to that same button. I imagine one click started it, and one click ended it. I turned the box around and noticed ten small lines printed on the side. So, one click on, one click off, and one of those lines must disappear.

Could I really do this? Was it right? Is there even anything I wanted a shot to re-do, that badly? At first, I shook my head no and looked towards the television. I flipped the screen on and tried to ignore the lure, but soon my mind was racing with memories of opportunities I had blown in the past. There was that time I was single and got a chance to hang out with my very attractive female friend alone. We both wanted it, but we were young, shy, and stupid. We sat there half naked and made the occasional grope. An embarrassing display. I also had a crush for multiple years in school on a cheerleader and never did anything. And, of course…

My thoughts converged on one opportunity that was always painful to pass up. I was in a relationship during my entire college life, and that really put a damper on a lot of things. I remember one night, in particular, I was online bored and chatting with a bunch of friends. My best friend during college was a petite, blonde girl named Amanda. We flirted but we knew the boundaries due to my long term relationship. That night, she was babysitting for a friend, and wasn’t shy in letting me know the circumstances.

“The kid went to bed and I’m here for the next five hours alone” she mocked. “Too bad you have a girlfriend.”

What could I say in that situation? I could only laugh and pretend I wasn’t overly disappointed. In reality, I had many flashbacks to that night, and wondered how things could have gone had I been free. Did I really want to try this thing, though? I looked at the box again, turned it over a few times in my hands and pondered. I had no idea how this would exactly work, but I would be forever curious if I didn’t at least try it out. I could always stop midway through if it didn’t feel right.

There was no use making any special preparations. I decided to go for it, and whatever happened, happened. I didn’t exactly know what to do, so I thought hard about that night and held my breath as I pressed the button.

A burst of light. That was it but there I was, sitting in my old room on the computer. I looked up to the computer screen and saw an instant message.

“The kids went to bed and I’m here for the next five hours alone” it read. This time there was no too bad.

I looked at myself in the mirror, and I resembled just how I looked years ago. Mostly the same, with slightly less of a muscular build. I could only smile.

“What’s the address?” I asked her. And just like that, I was on my way. I had no worries about staying out late or doing anything crazy, as a simple button push would end the whole thing.

“Just stay alive” I thought to myself. I drove a little faster than usual, not fearing any tickets as I got onto the highway. The trip was about thirty minutes, and I laughed as the former top hits came onto the radio. I followed the directions and soon arrived at the house where Amanda was babysitting.

I got out of the car and rang the doorbell. She answered with a smile and offered the same hug that she normally gave me. She was dressed casually, in a gray t-shirt and jeans. She was a runner and had very fit, toned arms, legs, and body. From what I had seen over the years, she probably would have loved to call herself a “B” cup, as her smaller bust stuck out slightly under her shirts at school. She was a little tanned from running, but not overly. She had medium length blonde hair and nice blue eyes.

“So why has it taken so long for us to finally hang out?” she asked me as I followed her into the large house.

“You wouldn’t believe me if I told you” I laughed, and then shook her off when she shot me an inquisitive look. This device was incredible. It brought me back to the exact moment I wanted to re-live, and it convinced the other party that I was single, even though I hadn’t been at the time. I didn’t know if that was a built in feature or if my train of mind had done it.

“You know” she started. “They have a hot tub in the back.” She grinned at me and bit her bottom lip.

“You should have told me to bring a bathing suit” I laughed.

“Bathing suit, underwear, same thing” she winked and got up to head towards the backyard. She smiled back towards me and pulled her t-shirt up over her head, leaving me a view of her petite back with only a bra strap on it. I followed behind her and caught up to her as she lifted the top of the jacuzzi up. This was definitely the most skin I had ever seen on her, using the little bit of light to see a toned, flat stomach and smaller but perky breasts covered by her black bra. I was next to lose my shirt, and as I got it over my head, I caught her glancing at my body. She slowly undid the button of her jeans and slid them down her sexy legs without taking her eyes off of mine. I broke the gaze and took a look at her ass covered by her black panties. I yanked off my shorts, making sure to leave the device in the pocket, and left myself in just blue boxers.

She made her way into the hot tub and I quickly followed. I took a seat near her, our bodies completely covered by the veil of the water in the dark. I tried to think back to just how flirty we were, but struggled to remember. Obviously, it had to be a pretty extreme amount if a night like this could have come about so easily.

“Sometimes” she broke a small amount of silence. “After I’m done babysitting, I come in here myself. I take advantage of the jets” she giggled.

“I bet that is quite the scene” I laughed, excited by what could be coming soon.

“I’ll show you” she started with a grin. “If you help me.”

I nodded and she made her way down, a little lower into the jacuzzi. She motioned for me to come up behind her and support her back. I eagerly did, putting my hands on her petite body as she lined herself up with a strong jet. I saw her reach under the water, and her hands came back up with her panties, which she gave to me with a wink. Within a few seconds I heard a moan and she quickly started to shake slightly against me. I knew all reserved nature could go out the window at this point, and I allowed my hands to explore her body for the first time. I unhooked her bra and saw her perky breasts for the first time, reaching around and cupping them in my hands. I felt her nipples poke against my palms, before I dropped my hands to explore the rest of her. They roamed over her tight body, and then down to her slim legs. I gently rubbed the inside of her thighs before I stopped between them, feeling the blast of water against my hand as she pouted at me for taking away her pleasure. I let the jet resume its assault on her clit as my hands gripped her tight ass, propping her up closer to the jet.

“Fuck” she moaned as her body began to shake harder against me. I used one hand to keep a grip on her ass, which kept her closer to the jet of water, and the other went back to her breasts. Her nipples were rock hard as she spasmed against me.

“Fuck it’s too good” she said, and I felt her push back against me, trying to put some space between her and the jet. But I kept it right against her clit and she screamed and came hard, her body convulsing against me as her head rolled back against my shoulder. I turned her head towards me and kissed her for the first time, our lips pulling on each other’s as she continued to shake. I felt her vibrate into our kiss as she continued to cum hard. My hand went between her legs to block the jet briefly, before my fingers took the place of the jet and started to rub her clit. She went stiff against me and whimpered into our kiss as she came immediately again. I felt up her body and could feel her tight stomach rippling as she finished her orgasm. Finally, I let her back away from the jet and she backed into my very obviously erection.

“Holy shit, you weren’t lying” she said as I poked her back through my trunks. “It’s been a while since we talked about that. I almost forgot” she laughed and pulled the tie to my swim trunks. She pulled them off me and gripped my hard on, rubbing her smooth hands against the length.

“It’s only right that I return the favor” she smiled. “I bet I could make you cum so fast on one of these” she smirked and teased as her fingers explored me. “If I do, you have to eat me out after this” she made the bet without letting me respond, but I had no argument.

“Ready?” she smiled as she helped me down towards the lower part of the jacuzzi. I felt the strong jet of water plow against my thigh as she rubbed my back with her hands. After enough time without a reaction from me she became curious.

“What the heck is going on?” she said as her free hand plunged into the water and felt for the jet. “Oh you sneak, it’s not even on you.”

“Maybe you just can’t make me cum as fast as you think…” I teased her just as I felt her pull my cock against the jet.

“Not so talkative anymore huh?” she teased me back and bit down on my neck from behind me. I felt incredible pleasure wash over me as the water massaged the underside of my cock. She jerked my shaft and kept the head near the jet as I squirmed from the pleasure.

“I know you’ll never last” she continued to tease and bit down on my ear. “Why don’t you just cum for me now” she smiled and I felt her finger run up the big vein on the underside of my cock. I tried to push back as the pleasure completely overtook me.

“No, no, you’re not going anywhere until you cum” she flicked her tongue against my ear lobe as my orgasm rushed on. “That’s right” she cooed as my cock started to quickly stiffen in her hand against the jet. She continued to jerk me against it, and no matter how much I tried to hold back, it was only a matter of seconds until my cock erupted, blasting my seed throughout the hot tub water in quick, hard bursts. She mercifully pulled me away from the jet and slowly jerked me through the rest of my orgasm as the last of my cum shot through the water.

“Now back to your end of the deal” she smiled and climbed up on the side of the jacuzzi. She spread her gorgeous legs open wide and motioned for me to come towards her. I kissed up the insides of her thighs and finally found her gorgeous looking pussy. I wasted no time in flicking my tongue against her clit, finding it between her tight lips. She started to moan as I then began to suck on her clit, driving her wild as she played with her breasts. I wrapped my arms around her legs and brought her closer to me as I alternated sucking on her clit and flicking my tongue roughly across it. My hands climbed up her body and stopped on her breasts, taking over for her hands as I twisted her nipples. Her body began to buck against me and soon she came, a little liquid leaking from her pussy as she nearly squirted. Her hands ran through my hair, pulling it as I brought her over the edge and kept her there with my tongue still roughly flicking against her clit.

“Fuck that was so good” Amanda moaned and pulled me back up for a kiss, tasting her own juices. We kissed for a while and I explored her mouth with my tongue, before our tongues eventually wrestled each other. There had been so much sexual tension between us at school, and even though it had finally been achieved in a weird way, it was still being unleashed like it was really happening. Between making Amanda cum and our prolonged make out session, I was ready to go again and it didn’t take long for her to notice.

“Do you want to?” she asked me.

“So badly” I responded and looked at her with lust.

“I’m not on the pill and I’m sure you didn’t bring a condom…” she continued.

“Let’s just go for it” I encouraged, knowing there would be no consequences. She nodded and turned around, bending over the side of the tub. She turned around and winked as she presented her gorgeous, firm ass. I came up behind her and grabbed her ass for a while, and then kissed her back. I put my cock between her legs, and rubbed it against her clit. She squirmed with a mixture of nervousness and excitement as I teased her clit. My hands reached around and felt around her body and breasts again, before I finally found her opening and slowly slid myself inside.

“Ohhh fuck” she moaned as I entered her. She was very tight, matching the rest of her petite figure, and I struggled to enter completely. I felt myself pushing her tight walls apart as I worked my way deeper inside her. I felt myself rub against her g-spot, which drew a quick moan, as I finally got myself fully inside, against her cervix. I paused for a little bit, letting her adjust to my size, as I brought her head back around for another kiss. As we kissed a little harder, I withdrew a few inches and thrust it back home, making her vibrate in a deep moan into the kiss. My hands found her breasts again and pinched her already hard nipples. We kissed passionately as the slow fuck hit a nice rhythm. I dropped one of my hands down and started to rub her clit while I slowly fucked her deeply. I counted about five seconds in my head before goose bumps overtook her body and her pussy clenched down on my cock. It gripped me a few times tightly and convulsed for a few more seconds before she came down.

I gave her about a second to catch her breath before I grabbed her hips and started to pound her full speed. She began to scream as my cock pounded against her g-spot and cervix with each thrust. It wasn’t easy to hold back my own pleasure as her tight pussy felt incredible. As the pace picked up, water started to splash out of the hot tub. Amanda’s firm ass jiggled ever so slightly with each rough pound. The constant friction against her g-spot forced her to another, more powerful orgasm, as her body shook below me. She had to hold onto the side of the hot tub to stay upright as her orgasm rocked her body.

“You probably shouldn’t cum in me” she said as my cock slowly started to stiffen inside her tight pussy. I had tried to delay my orgasm, but her tight, orgasming pussy had just been too much to contend with. I didn’t say anything, and instead continued to pound her harder, faster, and deeper. My cock hardened more as my orgasm built stronger.

“Really, I’m not on the pill, remember?” she protested, but my body was firmly on top of hers and easily continued to pound into her without any resistance. Instead of pulling out, I started to rub her clit as my rock hard cock continuously rubbed her g-spot. Instead of any more reminders to pull out, I figured it would be more fun to have her orgasm cause mine. I held my own back as I rubbed her clit furiously, and soon she came again, shrieking as her pussy sprayed liquid against my cock this time and squeezed me over and over. Her massaging pussy brought me over the age, and with one final deep burying of my cock, I let loose rope after rope of hot, sticky cum deep insider her pussy. I felt it burst out in quick, thick shots, before slowing down but still rocketing more cum inside her. She moaned and had to accept my full load, as my entire cock remained out of sight deep inside her most sacred, unprotected area. It was so warm and inviting that it brought out one of my biggest orgasms ever, as I felt myself flood her pussy.

From this angle I could just get my hands on my clothes. Unsure of how she was going to take being creampied, and knowing I had gotten everything I wanted and more, I grabbed the device. I pulled my cock out, watched the extreme amount of cum start to pour out of her pussy, and forced myself to hit the button.

That same burst of light. And there I was, fully clothed and back in my bed where I had left. The device temporarily glowed, and one of the ten lines warped off. Then it went back to normal. My thoughts began to race again as I thought about the nine opportunities I had left. This was going to take some planning.