Winning An Unexpected Bet

I was twenty five when this story happened, but still working on an undergraduate degree at university. I'd made some bad decisions right after high school, flunked out, taken a few years off to get my shit together and finally gone back.

I was living with my girlfriend and she was working full time to support me, but I had a part time job at a bookstore in the mall to help out with the bills.

That's where I met Rebecca. She was eighteen and working part time at the bookstore while she finished her last year of high school. We hit it off right away, but in a platonic way. She called me her "work big brother" and we talked a lot while we worked, and texted outside of work too.

My girlfriend hated her. At first it annoyed me, because nothing was going on between Becca and me. I mean, of course I had noticed she was cute and she had fantastic big tits, but I wasn't planning for anything to happen. And that's the honest truth. I couldn't risk a breakup because I literally couldn't afford to live on my own.

But things can certainly happen even when you don't plan for them...

It was Friday morning, my girlfriend was at work - and would be until 5 that night - and I was bored. For once I was caught up on my homework, and my shift at the bookstore wasn't until late in the afternoon. I got to texting Becca and she suggested that we finally get together and play video games, something we'd been talking about doing for a long time.

I didn't have a car, but Becca could borrow her dad's truck and swing by my place. She even offered to drop me off at work later, which was great because taking the bus sucks.

She showed up soon after, wearing sweat pants and an extra-large hoodie with the logos from my school.

"You like them?" she asked, spinning around to show them off for me when I commented. "I made up my mind that's where I'm going in the fall."

I congratulated her, we talked school stuff for a while, and then we got down to serious business. She took her shoes off, tossing them aside, and curled her feet up under her on the couch in that boneless way that only girls seem able to manage.

We decided to start with a racing kart game, one that she had bragged to me about her skills with since we first started talking games.

The first few games I took it easy on her, trying to get a sense of how good she was. She wasn't bad at all, but it seemed like I could take her if I tried.

She was pretty free with the trash talk too, especially when she won the second game. So I decided to get back at her and tease her a little. That's all I meant to have happen, honest...

"Okay, how about we make it interesting?" I said.

"What do you have in mind?" she said.

"Let's make a bet on the next race," I said. "You win, and I'll give you all my notes for the introductory courses you'll have to take next fall."

"And if you win?" she said.

"I get your hoodie," I said.

"My hoodie? Why would you want that?"

"Hey I go there too, and it looks like it would fit me." I was really kidding. If I won I had no intention of actually keeping her hoodie, I wasn't that much of a dick.

"Deal," she said. We shook on it, and then the race was on.

I stepped up my game a bit. Still not going as hard as I could, but definitely giving more of a challenge. In the end I beat her by a few seconds. Before I could say I was kidding, she stood up, took off her hoodie and threw it at me.

"Here you go," she said, "but I want a chance to win it back."

She was wearing a white tank top under the hoodie, one that hugged her ample curves quite closely. I could see the bright color of her bra showing through the white fabric.

I mentally licked my lips and then made an effort to keep things pure.

"Okay, double or nothing, your socks against my new hoodie."

Okay...maybe that wasn't totally pure. I figured she'd have cute feet, and I've always had a bit of a thing for cute girl feet, but it was the most harmless option I could think of.

She agreed and we raced again. I played the same level of intensity as before, and it looked like I was going to lose until she took a corner just a little too sharp and I passed her in the last instant while she was recovering.

She cursed a bunch, but she was laughing in between as she pulled her socks off and threw them at me. "I hope you choke on them," she said. She did have cute feet by the way, and her nails were painted in orange polish.

"Well thanks for playing," I said with a laugh. "I hope your drive home won't be too chilly without your hoodie and socks but let that be a lesson to you about the dangers of gambling."

"Oh we're not done," she said, shaking her head. "I have to win my stuff back. I'll bet my tank top against the hoody."

"Um..." I said, totally at a loss for words for a second. "I think our contest might be getting a little too PG-13 here, don't you?"

"Oh please," she said. "Don't be a prude. You've seen me in a bathing suit before." I had, it was true, at a birthday party for one of the staff. "And besides," she continued, "I'm not going to lose again anyway."

I knew I should stop this. Or else, agree to the bet and lose on purpose to let her win her things back. I swear that's what I was going to do, but then right near the end of the next race I found my hands moving almost of their own accord to hit her with a green shell and swoop past her for the win.

Even then I could have said, "hey no worries let's call it quits."

But I didn't.

I watched her slip the tank top off and with every inch of flesh she revealed I could feel my cock getting harder.

When it was off she threw it playfully over my head and I let it fall on the floor as I tried not to stare too obviously.

Her bra was orange and lacy, and I could see her erect nipples tenting the fabric in the front. It did not look like a bathing suit, but I tried to pretend that it was no different than seeing her that way.

"Well you might get a few stares driving home like that," I said, trying to sound nonchalant.

"Pants against the tank top," she said, her tone matter of fact. She made the selections on screen to start another race.

I really didn't think I would win that one. Even though I made an effort to keep my eyes on the screen, I was hyper aware of the fact that she was sitting there with no top on, and just a bra.

But then I realized she had picked a track where there was a hidden shortcut, one that she didn't seem to know about, and without really thinking about why, I took it.

It made the difference, and next thing I knew she was standing up, and sliding those sweatpants down onto the floor.

Her panties were also orange, and tiny. So tiny that I thought she must shave or wax, or else there would be no way they could keep everything covered.

There was also just the slightest hint of a damp patch on her panties, as though maybe she was a little turned on by this slow strip tease too.

In retrospect I really should have wondered who was hustling who here.

I didn't say anything. I don't think I could think of anything to say.

"Bra against the sweatpants," she said. This time her voice had a hint of...I couldn't tell what exactly. Anticipation? Nervousness?

The races in this game take about three minutes or so to finish. This was the longest three minutes of my life. I couldn't decide what to do. I think I eventually convinced myself that she was bluffing, that I might just as well beat her and call her bluff. She would probably put her stuff back on and we'd laugh about this later.

I pulled out all the stops, using every trick I knew, every cheap shot with an item, and I beat her again.

I was already anticipating my polite acceptance of her refusal to take this any further, but it turned out she had other ideas. She turned to face me on the couch, slowly reached her hands around behind her back, undid her bra, slipped the straps off her shoulders and handed it to me.

Her breasts were spectacular. Full and firm, perky even without the support of the bra. I couldn't help picture what they would look like with my cock sliding between them. I wanted to taste them.

"Panties against the bra?" she said. This time it sounded like she was asking, like maybe she was giving me an out if I wanted to take it.

Not trusting myself to speak, I nodded.

I definitely should have lost the last game. I had no focus, I kept looking at her tits out of the corner of my eye. She was leading coming into the home stretch, but then suddenly ran into one of the little animated parts of the course we were on, and it bounced her off the side of the track. Playing it back in my head, I can't be sure if she hit it by accident or not, I only know she had avoided it successfully for the first two laps of the race, but then somehow ran into it on the last one.

It cost her enough time that I slipped across the finish line just moments ahead of her.

"Uh oh," she said with a soft giggle.

She stood up, stepped in front of me so that her panties were practically in front of my face and slowly slipped them down.

Her pussy was shaved bare, as I had suspected, and looked smooth and amazing. She was definitely wet, it was obvious this close up.

Then she sat down on the coffee table in front of me, with her legs spread wide. She gestured towards her naked body. "Well I clearly can't go home like this," she said.

"I think the neighbors would be upset if you did," I said.

"Maybe I can earn my clothes back some other way?"

"What did you have in mind?" I said.

She smiled, and then still sitting on the coffee table she lifted her feet off the floor and put them in my lap. By this point my cock was an iron bar and her smile got even bigger when she felt it under her toes.

With remarkable agility she undid the button of my jeans with her feet, and then pulled gently at the top to get the zipper undone.

I lifted my hips up off the couch, and she took the opportunity to slide my jeans and boxers down, freeing my cock completely.

Then she wrapped her feet around my cock and started stroking it. It was obvious she knew what she was doing. It felt fantastic, and I let it go on for long enough to memorize how she looked doing it. But eventually I wanted more and it was about time for me to take charge.

I reached forward and grabbed her by the waist. I pulled her forward towards me onto my lap, and she moved her feet aside to let me do it.

She ended up straddling my thighs, with her feet on the couch and her knees up in the air, her pussy just inches from my cock. With one hand I pushed the tip of my cock down and into her.

She was wet enough that the tip slipped right inside her. She gave a little gasp, but then she pushed her hips forward so that the rest of my cock slid into her all the way.

Then she started riding me, slowly at first, but then faster and faster.

My hands found her tits, and squeezed them, playing with her nipples, which made her moan. With one hand she started rubbing her clit as she rode me.

She looked amazing, so horny and so slutty, riding my cock like it was what she was born to do. The sight of my cock thrusting in and out of her tight little pussy is something I will never forget.

I have no idea how long we fucked for. Time seemed to have stopped completely, and I still couldn't really believe it was happening.

Eventually she started moaning "fuck yes, fuck yes" over and over and I knew we were both almost there. I held off as long as I could but then she screamed "I'm cumming" and I did too. I came hard inside her, balls deep in her, practically filling her up, or at least that's what it felt like.

She slid back a bit so that my cock slipped out of her, and I could see my cum leaking out of her. Her eyes were closed and she had a little smile on her sweaty face.

That was when reality set in. What had we just done? I was pretty sure this went farther than either of us was intending.

I had just fucked her raw. My girlfriend and I didn't use condoms, but she was on the pill so there was minimal risk. I had no idea if Becca was on any kind of birth control.

We could probably have had that conversation right then and there, but all of the sudden I heard the worst possible noise in the world.

I heard the sound of my apartment door opening.

"Hi honey," came my girlfriend's voice from down the hall.

Becca's eyes flew open and her expression became horrified.

With strength born from terror and adrenaline, I stood up, grabbing Becca as I did so, and then basically dropped her behind the couch. There was just enough space for someone to fit there as long as they didn't move around much. I heard her give a grunt of surprise, and I whispered "be quiet!"

Then I yanked up my jeans, did them up fast enough that I almost zipped my balls into them, and jammed Becca's clothes under the couch.

I managed to do this before my girlfriend made it down the hall to the spare room where all my gaming stuff was set up.

I met her at the door and gave her a quick kiss.

"I thought I'd come home for lunch and surprise you," she said.

"You definitely did," I said, with a smile that felt super fake.

"Did I catch you doing something bad?" she said, smiling.

"Just masturbating," I said.

"Oh too bad you wasted it, we could have had some fun."

"Maybe tonight," I said. She nodded and smiled again.

"Somebody's parked in our spot," she said, walking toward the bathroom. Probably Becca I thought, since I told her to park in our space. Luckily my girlfriend wouldn't recognize the truck.

"Can you call the super about them while I get cleaned up for lunch?" she asked.

"Absolutely, I'll go talk to them."

As soon as she shut the bathroom door behind her, I grabbed Becca's clothes - thankful that she had left her shoes in here instead of taking them off at the door where my girlfriend would have seen them. I whispered "let's go" and hustled Becca up and out of the room. I couldn't give her time to get dressed, although she managed to grab the hoody and yank it on while we booked it to the door. It was long enough that it mostly covered her, at least at a casual glance.

I lived in a basement apartment. From the hallway outside my door was a short flight of steps up to the back door out onto the parking lot. The stairs continued up to the upper floors as well. As we got out there we could both hear someone else coming down the stairs from higher up, so there was no time for her to stop and get dressed there either. I opened the door and said, "just go, I'm sorry!" and she nodded and hustled out, fumbling her car keys out of the pocket of the pants she was still awkwardly carrying in front of her.

I watched as she got to the truck, threw her stuff in and jump in, slamming the door behind her. She drove quickly out of the parking lot, shooting a final glance at me, but not waving. I couldn't tell what her expression was, but I had to guess she wasn't thrilled.

That was going to be an awkward conversation later.