A chance to redo ten moments of your life. What would you choose?
[Love hearing from my readers. Enjoy!]
Though the device had been guilty of making me question a few moments in my life, it was really giving me a great opportunity to get some things out of my system. There were too many moments that I had passed on throughout my youth, and getting the chance to re-live some was definitely going to be important in settling down into a monogamous lifestyle.
This next encounter was going to mark the halfway point. This was going to be trip number five, leaving me with just five more. I had to be careful to not waste any. So far, all of my trips back had been pretty perfect, and I had no regrets. I decided to go through all of my social media accounts and write down every girl that was even in contention at this point.
As I tried to narrow things down, I stopped on my friend Allie. As I mentioned, I made a lot of great female friends during college, but never got to act on any of them. Allie and I had a lot of the same classes together, and during one of our final semesters, it was announced that we’d be learning at a center far away from campus. We decided to car pool together to save on gas, so we ended up spending a good amount of time together.
Allie was the kind of girl I probably would have had no chance with. You’ve probably met a lot of people in your life who nod, laugh, and agree with everything you say. She was the type that called you out for anything if she disagreed or thought you were bullshitting. She was gorgeous too. She was a little taller than average for a girl, with dark brown long hair, model eyebrows, and light gray eyes. She had tan skin and, though she didn’t show off much, had large breasts which I gathered were in the C range.
I volunteered to drive us often, and was funny enough that she seemed to enjoy my company. There was one day in particular where we were talking about how broke she was that I wanted to try something, but held back because of my relationship. I laughed a little as I remembered some of the questions that ran through my head that day. That would be fun to go back to, just to see what might happen. She was sexy enough that it was worth it, even if it didn’t go perfectly.
I thought back to that day in particular and pressed the button on the device. A short flash of light went up as I went back probably four years. Sure enough, there I was, driving my car with Allie in the passenger seat. It appeared as though the drive had just started, which meant we probably had almost an hour until we arrived.
“Yeah, it sucks being a broke college student” she laughed from my right side. I looked over and saw she was wearing a tight green shirt, outlining her large breasts, and jeans.
“Yeah” I laughed. “You know, I actually read something online last night that I have a lot of trouble believing.”
“What’s that?” she asked, her curiosity piqued.
“The author actually claimed…” I said, still chuckling. “That after interviewing hundreds of college girls, over half said that they would flash a random stranger for five bucks.”
“Hell why not?” she said, laughing with me. “Five bucks to show someone my tits? As long as they don’t take a picture for the internet, why not? Not like it hurts me or anything. Free money.”
“Guess you have a point” I laughed a little awkwardly. “The author wasn’t making it up then.”
“Hell no” she said. “When you’re in college, quick money is the best thing that can happen to you.”
“If you would flash a stranger, what about a friend?” I asked, looking over at her.
She returned my glance, a little curiously at first. “You know you could have just asked, instead of making up a story.”
“What?” I protested, laughing more. “That’s totally a real article.”
“Uh huh” she giggled. “I’ll totally look it up when I get home.”
She was right. It wasn’t a real article, but luckily she would never get to the point of finding out before I returned home, and then the situation would be gone. I could say whatever I wanted at this point to get what I was looking for.
“So you’ll really give me five bucks?” she laughed again.
“Yeah, I admit I’ve wanted to see for a long time” I confessed.
“At least now you’re being real with me” she said. “Don’t crash the car.” She winked and grabbed the bottom hem of her t-shirt, pulling it up over her head. Then she reached behind her back and unhooked her bra, letting it fall and then turning towards me. I tried to keep an eye on the road as I stared at her incredible breasts, which were even fuller than I thought and kept the tan appearance of the rest of her body. I would spend a second looking at the road and then two seconds looking at her breasts. She laughed and shook them at me before turning away.
“Okay, don’t kill us” she laughed again, covering herself with her arms folded over her chest. I could feel myself getting aroused but I was able to hide it for now.
“Would you let me touch for another five?” I pressed my luck.
“Easy now” she said, but she still giggled. “I’m not a prostitute. I don’t mind flashing since all you get is a mental image. I don’t know about going to touch for money.”
“Twenty” I said, flatly.
“Do it” she replied quickly. “Wait, show me some first.”
I swallowed hard, praying that I had a good amount of money in my wallet. I pulled it out of my pocket and glanced inside, seeing three twenties. I pulled one out and gave it to her. She smiled and turned back towards me, removing her arms. I took one hand off of the wheel and lightly squeezed her right breast. I bounced it and massaged it before changing to the other.
“I honestly don’t get why you guys like boobs so much” she laughed.
“I don’t get it either” I laughed too, but kept squeezing. I grazed over her nipple, and heard a small gasp.
“Easy big guy” she laughed and looked down, catching sight of my obvious erection. “Wow, impressive. Didn’t think you were packing.” She said looking at it and I could feel my face getting hot. There was some brief silence.
“Tell you what, this one is on the house” she smiled and started to rub me against my shorts. After a few seconds of this, she unzipped me and took me out of my boxers. “Wow, even better than it looked before” she smiled and bent down to take me into her mouth.
I had received road head once before, but it was from a young, inexperienced girlfriend and it wasn’t much. This was a whole different experience, as she expertly worked my cock in her mouth. She took it out, licked all the way up and down and then plunged back down on my length. I kept one hand on the steering wheel, put one hand back on her breasts and did everything I could not to crash. I certainly didn’t want to die in the past.
She took her free hand and scooped my balls out of my boxers next. She played with them a little as she worked up and down my shaft faster, her tongue playing with the sensitive underside of my cock head. I let my hand find one of her nipples and started to gently twist it. She didn’t stop me and instead added a few vibrations to the head in response. She bobbed up and down my shaft in a frenzy as I squeezed her breast and kept my fingers around her nipple. I was glad that we were on a highway and that I didn’t have to deal with traffic lights as she brought me closer to the edge. She brought her mouth off of my cock and took my balls in her mouth, sucking on them as her hand pumped my shaft. Then she popped back onto my cock with her mouth and sucked firmly and let her tongue run wild.
“Oh fuck” I moaned, squeezing her breast harder and twisting her nipple roughly as I felt my cock starting to stiffen. I felt more vibrations on me and she didn’t slow down as my climax rushed on. I didn’t know if I should warn her, but before I could decide, cum was shooting out of my cock uncontrollably. I felt my balls pump without any sign of stopping and my big underside vein contracted with each pleasure-filled spurt. After squeezing her breast more I put my hand on her head as I continued to rocket cum into her mouth. I heard her make a choking sound and I had to let her up. I had to give her credit though because she swallowed the copious load.
“Holy shit you cum a lot” she said breathlessly. “I can’t lie though. That was fun.”
The experience had actually taken up the whole drive, and soon I was exiting the highway and approaching our destination. I was wondering if this was as far as things were going to go.
“I feel bad” I started. “I really would like to return the favor.”
“You mean…oral?” she asked, seemingly weighing my proposition.
“I won’t charge either” I smiled at her and laughed.
“Okay, okay, you’re on” she said. “You better be good.”
We climbed into the backseat, fully aware that we would be late. She laid out in the back and I unzipped her jeans, pulling them off. She was left in just a black lace thong, which I admired before pulling it down her sexy legs. She was fully shaved and just as tan down there as everywhere else. She must have been one to frequent tanning beds. She spread her legs for me and I lowered myself between them. I started by spreading her lips with my fingers and letting my tongue slowly poke her clit, before rubbing it back and forth against her. My heart was beating a little bit fast, a mixture of arousal and nervousness after her intimidating challenge. Soon, I ramped up the pace with quick, rough tongue lashings against her clit and she started to respond. I saw her grabbing her breasts, playing with her nipples as my tongue went to work. I took her clit into my mouth and sucked on it and then slid a finger deep into her pussy. I angled it against her g-spot and went back to roughly licking her clit back and forth.
“Fuck, yes” she moaned and breathed hard as I increased the pressure. It was really turning me on to have such a sexy girl responding to my advances. I added a second finger into her pussy and it joined the first against her g-spot, rubbing quickly against it while my tongue never quit. I actually went faster and more animated than I probably ever had in my life. Her stomach started to heave up as she got more into it. Suddenly, her body tensed up and then stiffened, as she grabbed onto the seats. She had almost a frightened look on her face and before I knew it, she pushed out my fingers and squirted on my face. I sucked on her clit through her orgasm as she screamed, her juices coating my face.
“Holy…fucking…shit” she said, trying to calm down. “No one has ever made me squirt before.”
“Then it’s only fair I get a reward” I smiled and quickly climbed no top of her. My cock was rock hard again and she barely got to look up before I barreled my cock into her tight pussy.
“Oh fuck!” she screeched as I wasted no time getting into a good rhythm. Each time I reached the depths of her insides, I pulled right back out and thrusted all the way back in. I didn’t know if she wanted me to fuck her, but she wasn’t stopping me. She was still having trouble getting strength back from her squirting orgasm just minutes ago. I had my hands on her large breasts, sometimes letting them go to watch them jiggle, but mostly squeezing their fullness as I pounded her with everything I had. Sensing she was approaching another climax, I brought one hand to her clit and rubbed her furiously. Within seconds she was shrieking and gripping for the seats again as she came hard. Her pussy went off in a vice grip around my cock and I felt juices run all over my length.
There was something so incredibly arousing about taking a “ten” to the height of ecstasy and watching her writhe in pleasure under your body. I watched her gorgeous face twist in different positions as she experienced new sensations. I smiled as her perfect breasts bounced up and down with each thrust. And I was really turned on, watching my cock disappear completely inside her tight pussy every time I pressed in.
She attempted to run her hand up and down my chest as I slammed in and out, but her lack of strength meant her hand quickly fell back down to the seat. I scooped up her firm ass in my hands and used the new angle to slam into her more.
“Fucking fucking fuck!” she moaned and panted as she came again. Her pussy was massaging my cock in a wild orgasm as I finally felt myself starting to build. She was in far too much pleasure to even realize it as my cock got stiffer and firmer as it pulsed. I thrust into her harder and faster than before, a few more times, and then buried myself as far as I could inside her.
“Ahhhh!” she screamed as my hot cum quickly shot out, burrowing deep into her pussy, faster than I could ever remember. My body bucked against her as I grabbed onto her breasts again for support and in lust. It took at least ten seconds before my orgasm even slowed, and I could already feel my cum flooding her completely and starting to threaten to come back out around my cock. A few more thick shots of cum sprayed deep into her pussy before I collapsed on top of her. I gave her a hard kiss, forcing my tongue into her mouth and wrestling with hers, before I blindly grabbed my shorts, found the device and pressed the button.
A quick burst of light and I was back home. Now that was satisfying.