Ashley's Boyfriend Makes a Bet

I was back in Niagara. I'd spent two years here attending Niagara College studying international business. It had been a few years, but I was back for the week as part of a convention for my internship employment. The internship is the key part of my Bachelor of Commerce in Honours Business Administration minoring in Modern Languages- Spanish. (Yup, that's a mouthful) I was getting the opportunity to gain some experience in the purchasing department of a major grocery chain, which will help me start my career in purchasing when I graduate in just under two years.

The day had been spent listening to seminars put on by the Fruit Growers Association of Ontario, learning about the challenges they were expecting in the upcoming year, as well as learning about the direction the industry expected to go in the next year. Important stuff when you are buying produce for a grocery store; but after a full day of it, I was ready to let loose.

I had plans to meet up with my old friend Ashley and her boyfriend to play some pool that night so I went back to the hotel. I changed out of my suit and into my much more comfortable sandals, jeans, and my navy blue Windsor baseball t-shirt; before heading down to the hotel bar to grab a quick meal.

Ashley and I hadn't hung out in a few years, but had been chatting again lately on MSN, and trading messages on Facebook, much like we did years ago when we first met. She had told me she was bored with her life, not really doing anything other than working at a yoga studio, and then heading back home to Rob, her boyfriend. We agreed to hang out should I ever get back to Niagara, so when this convention came up, we made plans to get together for a few drinks and play some pool. With both of them having to get up early the next morning for work, we decided to meet at 7, allowing us a lot of time to hang out before they had to head back home.

After my meal I made my way over to the pub Ashley had picked. I don't think I had ever been there before, but it was a cosy little pub with a nice ambiance, and a couple of pool tables in the back. I scanned the room and spotted them at a table near the pool tables. Ashley was as sexy as ever, wearing sandals, a short denim skirt, and a shiny red shirt with a bit of a plunging neckline to show just a hint of cleavage. She smiled as she saw me, and waved me over.

I approached their table, hugged Ashley, and looked at Rob to say hi. Two blank, blood-shot eyes looked back at me as he greeted me with just the slightest smile on his face. I never understood what she saw in the guy. She was smart, worldly, and ambitious. And he was a tradesman who I had never once seen when he was not baked out of his mind. It's like he needed weed to exist. She was better than him.

Yes, there is more than a bit of jealousy in my words. The feelings I had for her never completely went away. But she chose him, and then respected his wishes and created some distance between myself and her, when his insecurity acted up. I'm not completely blameless in that I know. Flirting with a girl in front of her boyfriend at a "School's Out" pub night only fed his insecurity. But that was water under the bridge now.

We ordered a pitcher of beer, then went to the pool table to play a few games. We decided that Rob and Ashley would play as a team against me. The games were close, I lost the first one, then won the next two as the drinks started to add up and Ashley and I caught up on our lives.

She enjoyed hearing about my work, since she was considering doing something similar as a career and actually using her international business education. I asked her about what she did as the assistant manager of a yoga studio. I joked about all that yoga being good for her flexibility, following it up with my trademark mischievous smile. I got a dirty look from Rob for that, but I was feeling good, so didn't really care.

As the night went on, the flirting continued. We talked about my experience playing varsity baseball with the university, and she commented about how the workouts had really paid off for me. I thanked her, and agreed. When she knew me, I was a pudgy 185 pounds. Now, my 5'9 frame was a trim, 170 pounds of toned muscle, and I told her that my goal was 175 pounds, and I expected to be there in a few months.

"Easy guys" Rob commented, trying to remind his girlfriend that he was still there. She and I always had this connection; we could talk for hours about anything. And since he didn't really care about the intellectual subjects, he was feeling like the third wheel, while I held his girlfriend's attention.

Ashley tried to include him in the conversation, but he and I just didn't have that much in common, and she already knew everything about him, so soon enough, the conversation was back to me, and my life.

Rob was getting frustrated at the lack of attention paid to him, or maybe the extra attention he thought I was getting, either way he started to do something about it. He flagged the waitress and ordered another pitcher, and when it arrived he quickly downed an entire glass.

"Come on man, drink up." He urged me as he held the pitcher waiting for me to hand him my glass. Mine was still half full, so I was in no hurry for a refill and shook my head, continuing my conversation with his girlfriend.

We kept playing, and it seemed like after every shot Rob was offering to fill my glass. But soon enough the second pitcher was gone. Once again Rob tried to goad me.

"I'm ordering another pitcher, are you going to take your balls out of your purse and have another drink?" He asked me. I just smiled at him, and after the waitress took his order for the third pitcher, I ordered a glass of water.

"Fucking pussy. Are you not man enough to drink?" He cursed. Ashley told him to shut up, but I just smiled.

"I actually enjoy the taste of my beer. I drink it for that, not to get drunk." I told him.

Not knowing what to say, he decided to head out for a smoke, and expected Ashley to go with him.

"I'm happy here." She told him. "Besides, you know I want you to quit. We'll finish this game without you. Go have your smoke by yourself if you really need it."

Just as Ashley had said, we kept playing. We were joking around, having fun remembering stories from our two years of school together. I was reminding her about the time I woke up one morning to find that my roommates had "stolen" a lawnmower from the neighbours down the street. Only in the light of day, and now sober, they had realized that the reason it was out on the front lawn was because it didn't work, and the neighbours were probably going to put it out for trash collection. Ashley was laughing hard as the thoughts of their drunken exploits came back, and just then Rob came back in.

Already in a bad mood, seeing Ashley laughing with me and looking happy did not help his insecurity. Making matters worse, he reeked of weed. Now Ashley smoked weed regularly with him, and I used to smoke on occasion before making the baseball team, but him getting high right then was the wrong move.

"You stink of weed!" Ashley complained as he leaned in for a kiss. "Did you really need to smoke that after all the beers you've had?"

"Fuck this" Rob replied, ignoring Ashley, as he started to rack the next game of pool. "I'm sick of you guys flirting. Jeremy, I'll make you a deal. We play this game just me against you. You win, I go home, and the two of you can hang out and catch up. But if I win, you leave, and don't see her again this week."

I looked at Ashley, who shrugged, and then I smiled as I accepted the challenge, fondly remembering the last pool bet I had about Ashley. Back then, she and Rob had been dating for about 2 months. She, our friend Tony, and I had been hanging out in her parents' basement playing pool. She was beating Tony by a couple of balls, and was getting cocky.

I knew how to push her buttons, so I suggested that she put her money where her mouth was. That if she truly thought she could beat him, she should bet her shirt. She was hesitant, because Rob was planning on stopping by after work, and she didn't want him to catch her. She sunk another ball as she thought about it, and then agreed to bet her shirt and her pants, but if she won, then Tony and I had to strip down to our boxers. It was a risk I was willing to take, but Tony was now the one to hesitate. He wanted me to finish the game for him. She looked at me for a second, then agreed.

At that point, I knew she wanted to shock Tony by prancing around in her underwear. When Ashley and I had our little involvement we had played pool a few times a week. She only beat me a few times, and that was with our 2 for 1 rule, where she got two shots for every one I took. It wasn't long before I sunk the 8-ball, and Ashley locked the door before undressing.

Tony was in shock, loving every minute of it. I think he even got to slap her naked ass cheeks as she stuck her panty-clad ass in his face. I even took a few pictures with her digital camera before the fun ended and she got dressed before Rob showed up, and I ended up playing him in a few games of pool, all the time trading smiles with Tony about what went on earlier.

So when I took the bet with Rob this time, I was pretty sure I could win. He was better now, and I was a little rusty, but I was starting to get into a zone. He was going to be heading home, and his girlfriend was going to stay. The game was tight, he had one ball left on the table when I sunk my last one, and faced a difficult shot to sink the 8-ball.

My only chance was to bank it all the way back the length of the table into the bottom corner pocket. I called my shot and he laughed. I'm pretty good at bank shots. Maybe it's from being good at math, angle of incidence equalling angle of reflection, given a true bank, and the absence of spin, and all that shit; but I don't really do calculations for these shots. I just rely on my gut.

I lined up the shot, figuring on a bank of this length, I had about a 50/50 chance of sinking it. I knew that the cue ball would end up back down the table leaving him with a long shot too, so I wasn't worried about leaving the 8 set up for him. I pulled back my cue, and took the shot. The cue struck the 8, which hit the bank, and rolled back down the table at a steady pace. It started to slow as it neared the corner pocket, slowing more and more until it reached the lip of the pocket, seemed to pause, and then dropped in.

Rob's mouth hung open at the sight. It took him a moment to recover.

"Fluke!" he complained. "That was complete luck, you could never do that again. I want a rematch. Double or nothing."

"I'm not an ass." I told him as I looked at Ashley. "I'll give you a chance to redeem yourself. But what do I get out of double or nothing? If I win, I get what I already deserve. You'll have to do better than that."

At this point, I think the combination of desperation, alcohol and weed clouded his judgement. Plus, I think he truly believed that I couldn't beat him two times in a row.

"How about if I win, you go home now, and if you win, Ashley goes with you, just for the night." He offered.

I've read stories about situations like this, and always thought it would be fun to talk someone into betting his girlfriend or wife. But I knew the reality of this too. It really doesn't matter what he bets, if she isn't going to go through with it. So I looked at Ashley, who looked at Rob with a combination of surprise and anger.

"You really want to risk me having sex with him?" She asked.

"I can win this, baby." was his reply.

"Go for it." She finally told me. I turned, smiling to Rob, and accepted the bet.

The fact I don't drink much really helped me out too. I had stopped after 3 beers despite Rob's goading, while he was downing yet another drink he had just ordered, and was starting to slur his words. In the end, this game wasn't even close. I was down to the 8-ball again, and he still had 5 balls left on the table. I knew I had the game. But I wanted to make sure Ashley wasn't going to back out, so I started to subtly taunt Rob, for Ashley's benefit.

"Better start sinking them, Bud. If you don't, Ashley's spending the night with me. Was that what you had in mind when you bet your girlfriend?"

He paused as he lined up his shot, staring dangers my way, but saying nothing.

"Is she just a possession to you? A disposable one, you risk against someone you know you can't beat."

I was pushing his buttons, but I was also pushing hers. This was his idea. He had risked her. She might back out if it was my idea, something that just went too far. But if she remembered that it was his idea, this could end up being a very good grudge fuck.

He missed his shot. I took my time, and sunk the 8, finishing the game. Rob protested, but Ashley wouldn't hear it.

"You made the bet. Live with it." She told him as she turned, grabbed my hand, and started to lead me out the door.

"Hold on a second." I told her. "Give him your bra. You won't need it tonight."

She started to head to the washroom to obey my instructions, but I stopped her again.

"No. Right here. I know you can take it off without taking off your shirt. Do it just like you did in the middle of math class that one time. Hell, there's less chance of you being seen here, than back then."

She looked stunned that I would bring that up. But she obeyed. That was the last button I had pushed before she decided she and Rob were too serious to tease other guys anymore; and probably the start of us drifting apart when I think back. She knew I would keep pushing her, despite her boyfriend.

And she was right, of course. They say power corrupts, and with the power over the submissive Ashley, and her idiot boyfriend, I went for the jugular.

"Now the panties," I commanded.

With that simple statement, the fight left Rob. I watched the shock and anger on his face slowly turn to despair. His fists clenched at my words, and I readied myself for his blow; but just as quickly he reflexively relaxed again. He knew he was beat. He watched with a defeated look as his live in girlfriend of 3 years pulled her skirt up, reached under, and pulled her thong down off her body in the dark and still rather empty pub.

"Ok, NOW we can leave." I told her, and led her out the door.

"You look beautiful tonight." I told her as we got in my car. "Rob's an idiot for making that bet."

We listened to the music on the radio like we did so many times so long ago. In my mind she was back where she belonged. I tried to keep my eyes on the road, but couldn't help glancing over at her as we continued our conversation. Every time I looked at her she was smiling back at me. It was almost as if Rob didn't exist. I took my hand off the gear shift and rested it on her naked thigh. I kept my hand on her until I needed to shift down as I pulled into the hotel parking lot.

"Hmm, one night with a submissive little slut, what should I do?" I teasingly asked her. I already had an idea forming in my mind. We made our way up to my room, and I kissed her passionately on the lips. My hand roamed her body before undoing her shirt, and exposing her perfectly shaped breasts. I pulled the shirt off her arms before sliding my hands lower, to undo her skirt, and slide it off to. Still fully dressed, I continued to kiss her as I pushed her back onto the bed. I stopped my kisses, told her to stay where she was, and got up. I grabbed a couple of my ties, and tied her hands above her head, securing them firmly to the headboard. Then, I took her shiny silk shirt, and tied it around her eyes, leaving her blind to what I was going to do next.

She heard me grab something off the counter in the bathroom, then leave the room. She lay there, helpless in darkness waiting for me to come back. Not knowing what I was planning. She wasn't sure how long she had been lying there waiting, when she finally heard the door open, and someone walk back in. She wasn't even sure it was me, until I whispered her name in her ear.

"Ashley, are you ready for this?" I asked, gave her a quick kiss on the lips. She strained against her bindings, wanting to prolong the kiss. "Patience baby, patience." I teased her.

She heard a rattle, then jumped at the cold sensation she suddenly felt on her left nipple.

"Fu-uck" she moaned as I circled her rapidly hardening nipples with the ice cube. I circled her nipple over and over, taking breaks to slide the ice cube down her breast, and then back to her nipple again. When I knew she couldn't take anymore, I slid down her left breast into the valley on her chest, and up her right breast. The cube was almost entirely melted, leaving its watery trail on her chest, so I grabbed another one, and applied the same treatment to her right breast, only stopping once the ice cube was melted again.

I grabbed yet another cube, and this time trailed it down her body, over her navel, toward her waiting, and very aroused clit. She couldn't see where I was going, and with her restraints, she couldn't have stopped me even if she could see. But she could feel, and she knew where I was going. Her body squirmed as she tried to fight the cold feeling, trying to stop my descent, while her sweet little pussy got wetter and wetter with the anticipation of the very thing she was fighting.

When the ice finally made contact with her very aroused clit, her body jumped at the cold. I pulled it away, waited for her to settle down, then touched the ice to her sensitive clit again. This time, the reaction wasn't as strong, and I held it against her through her bucking. When she calmed down again, getting comfortable with the feeling, I slid the ice down along the outside of her pussy. Down the right side, up the left, then down the left, up the right, before bringing it back to her clit, and teasing it again.

The third piece of ice was almost gone again. This time, instead of grabbing another from the bucket, I lowered my mouth and breathed gently over her cold clit. The sensation of the heat after the cold made her moan even louder. I took her clit into my mouth and sucked gently as I now brought my hand to her pussy and slid my fingers along the outside, getting them lubricated with her juices.

I sucked her hard into my mouth as I slid my fingers inside her. After all the lead up, she was ready, and with my mouth on her clit, and my fingers thrusting in and out, in and out, it didn't take long to push her over the top, and she was once again straining against her restraints, moaning in pleasure.

Now, I decided to finally undress, and fully enjoy the sexy submissive girl I had in front of me. Ashley heard the rustle of my clothes hitting the floor.

"Yes. Please. Fuck Meee!" She begged in a moan.

My uncut cock was hard, and more than ready to give her what she wanted. I climbed between her legs and ran my shaft along her lips, lubricating it with her sweet pussy juices. She was growing more and more impatient until I finally lined my cock up, and slid it in.

With my entire length sheathed within her hot body, I paused, savouring the feeling, and letting her adjust. Her moan as I entered let me know she was still riding high, and wouldn't take long to get off. I slowly began to thrust, my hips working a steady rhythm, in and out, in and out, in and out penetrating deep, pulling back, and then penetrating again.

Her moans grew steadily louder, and my groans escalated to match. My body was dripping sweat from my effort, and the once cold trails of ice water on hers were warming up to match.

As I neared my climax, I realized that I wasn't wearing a condom, but at that point, I really didn't care. In fact, if anything, that only spurred me on further. Excited by the thought of cumming in the pussy of another man's woman; my thrusts increased in both speed and intensity until I went over the top. I erupted deep inside her, sending strand after strand of hot cum into her waiting womb.