A Friendly Bet

BRRRRIIIIIINNNNG!

"Shit," I muttered to myself. "It never fails! Every time I get in the shower!"

With that, I jumped out of the shower and grabbed a towel, heading for the phone.

"Hello," I panted after running half naked through my house, picking up the phone, and dripping water all over the floor in the process.

"Hey. What's up?" a feminine voice asked.

"Oh, hey Jen. I'm just about to have a shower."

"What are you doing tonight?"

"Uh, nothing. Why?

"I'm bored. You up for some foozeball?"

"Sure. If you're up for getting your ass kicked again."

"Hey Mr. Cocky! You better watch out. I've been practicing."

"Sure, sure. Just remember to bring the case of beer you owe me from last time."

"Yah, yah. I'll be there around eight."

"Okay. See you then."

I hung up the phone and made my way back to the shower. Playing foozeball wasn't my idea of a good way to spend my Saturday night, but I didn't exactly have anything else to do. Besides, Jen and I always have fun.

As eight o'clock rolled around, I pulled the foozeball table out, put on some music and began to wait. I had known Jen for a couple years and I didn't remember her ever being on time.

True to form, as it neared nine o'clock, the doorbell rang. Before I could answer, the door opened and Jen marched in, pushing a case of beer into my arms.

"Here asshole!" she said jokingly. "This will be the last time I'll ever have to give you anything."

"Whatever you say princess," I answered sarcastically.

I had to admit Jen looked good. She was wearing a pair of low-riding jeans with a studded belt that allowed the crack of her ass to peak out over the top. The little black top she was wearing would have been more suited to a nightclub than a foozeball game but I wasn't complaining.

"You'd better put those in the fridge." Jen said with a wave of her hand. "We wouldn't want any warm beer would we?"

"We?" I asked. "Who said you're getting any bitch?"

Jen opened her mouth in mock surprise. We joked around like that all the time so it wasn't unusual for us to trade insults.

"You're the one that will be the bitch tonight," she countered. "My bitch!" "Dream on. Let's play."

I took out a couple beer and put the rest in the fridge before making my way over to the table. Jen was waiting, tapping her fingers impatiently and glaring at me with her dark, almond shaped eyes. I tossed her a beer and raised my own.

With a final "Good luck" we started to play.

Jen and I were starting to make our foozeball games a weekly tradition, with me winning every single time. We would always wager something which is why my fridge is usually well stocked with beer. In all fairness, however, it was my foozeball table.

I won the first two games easily and downed two beer in the process. Jen was taking it a little easier on the booze but was still drinking her fair share.

"I have to admit," I said after scoring the game winning goal in the second game. "You are getting better."

"Gee thanks," she drawled. "Just drop the ball."

"Are you sure you want to keep going? I usually get better as I drink more."

"Best of seven series bitch! It's not over yet!"

"I think so far, you've been MY bitch."

My final comment shut Jen up and we began our third game. Ten minutes later I was up 3-0 and Jen was head for the fridge to grab another beer. "So where's Carrie tonight?" Jen asked, speaking in a baby voice as she spoke my girlfriend's name.

It was no secret that Jen disliked Carrie, as she always seemed to dislike my girlfriends.

"She's out with her friends," I answered.

"Uh oh! I bet she's getting fucked right now!"

"Settle down," I said dryly. "Why would she go out to get fucked when she has this waiting at home?"

Jen let out a laugh.

"I'm just kidding," she giggled.

"By the way," I began. "Where's Kevin?" referring to her significant other.

"Same."

I gave her a look of concern in an attempt at teasing her in the way she had teased me.

"Don't even say it!" she blurted out. "He's not a cheater."

"What ever you say," I said with a smile.

"He's not."

"Okay."

"Fuck you!" Jen said, half laughing and tossing a bottle cap at me. "Let's play. I'm just getting warmed up."

I took it easy on her that game and she managed to squeak out a meager victory.

"Three to one, bitch!" she howled, dancing with excitement.

I could tell she was starting to get buzzed. Surprisingly it was making her play better however and after she grabbed another drink we jumped into our fifth game.

"Hey," I said halfway through the game. "How come we never hooked up?"

"What?"

"Why didn't we ever get together and... you know."

"Fucked?"

"Yeah."

I was always impressed my Jen's bluntness.

"Well," she said, cocking her head to the side as if in deep thought. "I guess I don't like ugly guys."

"Ouch!" I said cringing. "That hurt."

"Just kidding," she returned. "We almost did. Don't you remember?"

"You mean...?"

"Yeah. Halloween. The night we met. I kind of wanted you."

"Really?" I asked as I scored another goal.

"Yeah. After we danced you probably could have taken me home."

Although I already knew everything she was telling me it was strange hearing her say it. The fact was that I wanted her that night as well.

"I guess I missed my chance." I said in a over the top, resigned tone.

"You sure did."

We had become friend soon after that night and stayed ever since. Except for the occasional flirting nothing had gone on between us.

"Oh well," I muttered. "I don't think you're dirty enough for me anyway."

"Excuse me?"

"You heard me."

"I think I could handle anything you could give me."

Our conversation was starting to turn me on but I let the subject drop. Jen ended up winning that game which brought our total to 3-2 in favor of me.

"So you really think I'm not dirty enough?"

It was obvious that Jen wasn't ready to let the subject drop.

"I didn't say that. I said you're not dirty enough for me!"

"I think you would be surprised."

Her response peaked my curiosity and I took the bait.

"Okay, what's the dirtiest thing you've done?"

"I'm not telling!"

"Oh come on! You can't say something like that and then not tell me."

I had to admit I was very curious as to what Jen had experienced. Although we joked around about sex all the time, we never really talked about it seriously.

"I'll tell you what." she said. "If I win this game I'll tell you."

That's not fair! I..."

Jen cut me off by raising her hand.

"That's the deal. Take it or leave it."

Needless to say I took a dive and we were soon tied at three games a piece.

"Okay, let's hear it." I said after admitting defeat for the third time that night. "And this better be good."

"Okay, okay, Jen said, fidgeting with the handles on the foozeball table. "Remember when I went to Mexico last year?"

"Yeah."

I leaned in closer, anxious to hear the story.

"Well I met a couple Australian guys. We hung out a few times and stuff.

"And..."

On my last night there I had sex with both of them.

"Wow," was all I could say.

After a few moments to collect my thoughts I began to drill her for details.

"Did they take turns or do you at the same time?" I asked, trying to hide my growing erection.

"Same time."

"You slut!" I said laughing. "I would never have guessed!"

"Hey!" Jen answered, trying to sound hurt. "I was really drunk!"

"So they spit roasted you?"

"Spit roasted? What the hell do you.... Oh I get it. Yes. They spit roasted me."

"Does Kevin know about this?" I asked, continuing my interrogation.

"Of course not. How would you feel if Carrie told you she got double teamed?"

I was still too shocked to think about anything other that my friend getting fucked like a cheap whore.

"Did they DP you as well?"

"DP?"

"Yeah. Double penetration. In the pussy and ass at the same time."

"In my ass!? Yuck. No, I don't do that!"

"What? Not at all?"

"Nope."

"So you'll get spit roasted like a dirty porn star but you won't even try it in the butt?"

"It just doesn't appeal to me."

"Have you ever tried it?"

"No."

"Then you never know. You might like it."

"I doubt it."

"I told you you're not dirty enough for me."

"Oh yeah? And how many girls have you fucked in the ass before?"

"A few."

"Really?"

"Yeah. It's the best."

"Maybe for you."

"Hey, the girls enjoyed it too!"

"Yeah, I'm sure they did."

I let the subject drop, but unfortunately my dick did not. As we started the next game I found myself staring at Jen, imagining her on her hands and knees sucking some guy's dick while she gets fucked from behind. In fact I was so distracted that she managed to score a few goals before I realized what the score was.

"You're looking a little shaky," she said after scoring her fifth goal of the game. "Did you drink a little too much?"

"I don't think that's it," I responded.

Jen tossed back her lustrous brown hair and flashed me a smile before scoring another goal.

I let go of the handles and began to rub my wrist which was starting to get a little sore.

"Oh, poor baby," Jen cooed. "It's probably all that jerking off you do."

Little did she know that she was going to be the subject of my masturbatory fantasies that night.

Although I tried my hardest, Jen scored a few more lucky goals and pretty soon I was down 9-0 and Jen was on the eve of her first victory ever.

"So by the way," she said in a overly confident manor. "What are we betting?"

"How about...If I win, I get to fuck you in the ass."

Jen stared at me with those sexy dark eyes, a crooked little smile forcing it's way on to her face."

"Sure."

I was taken aback.

"Really?"

"Yep. If you win you can fuck my ass. But if I win, you have to wear a shirt that says "Jen's bitch" on it for a week."

"Are you sure you want to do this?" I asked.

"Absolutely. What are the chances you will win? I'm up nine to nothing!"

"Okay," I said. "You're on." With that I let the ball drop. Within five seconds I had a goal and Jen was giving me an evil smirk.

"Don't worry," I said. "I'll be gentle."

I scored three more quick goals and Jen was starting to look nervous.

"No backing out now," I warned.

"I know, I know."

After the next goal, the smile was gone from her face. She anxiously sipped down the remainder of her beer before concentrating back on the game.

"That's it," I joked. "The more you drink, the better it will feel."

"You still have five more to go asshole," she countered as she dropped the ball.

"It's funny that you used the term "asshole."" I stated, blasting in another goal. "Since soon, I'll be in yours!"

"Fuck," she cursed. "It's not fair. You keep distracting me."

"Don't cry about it," I laughed popping in yet another goal.

As much as I didn't want to wear a shirt that labeled me as anyone's bitch, it was the prospect of fucking my good friend in the ass that was driving me on.

"Fuck!!!!!!!!!!!" she yelled as I scored my seventh.

I just laughed and we continued. After I shot in number eight I expected Jen to continue ranting, but to my surprise she didn't say a word. She calmly retrieved the ball and dropped it back into the table. No sooner had the ball touched the surface then I had fired in the tying goal.

Jen dropped her head and banged it lightly on the table. My palms were sweaty with anticipation and I urged her to hurry up and drop the last ball. She looked up at me through her messy, but still sexy, hair and dropped the ball.

I fired it right away, but she caught a lucky bounce and saved what would have been the winning goal. She quickly shot it back and almost scored herself. I made the save and then waited, just holding on to possession of the ball as I looked at Jen and smiled.

"I bet your ass is so tight!"

With that, I fired the ball into the back of her net.

Jen stood there dazed for a moment before she spoke.

"Rematch?"

"I don't think so."

"Come on! I can't let you do that. I have a boyfriend!"

"You should have thought about that before you made the bet."

"But here was no way you could win!"

"Apparently," I stated with an air of sarcasm.

Jen walked over and slumped down on the couch, dropping her head into her hands. I finished my beer and then joined her. After about a minute of contemplation she looked up at me.

"I'll give you a blowjob," she suggested.

I just shook my head. As nice as it would be to have Jen suck my dick, I'm sure it would feel much better imprisoned in the confines of her beautiful ass.

"Fine." she resigned. "Let's get this over with."

"Let's go to the bedroom," I suggested.

Jen agreed and we made out way to my room. She looked nervous as she sat down on my bed.

"Do we need any lube?" she asked. "Aren't you supposed to use lube?"

"Sorry," I said. I don't have any. I guess you'll just have to suck it first."

"No way! You're not getting a blowjob too!"

"Okay then. What about condoms? Do you want me to wear one?"

Jen thought about it for a moment before answering.

"Nah. Just do it."

Suddenly I felt very uncomfortable. Jen took off her socks, tossing them to the side. As she started to undo her pants she looked up at me.

"Aren't you going to undress?"

"I thought I'd just watch you first," I answered wryly.

"Well, you thought wrong. Get 'em off!"

I let out a laugh as I pulled my shirt over my head. I wondered if I looked as nervous as Jen.

As I started to undo my pants, my eyes wandered back to my friend, who was sliding hers down her tanned, muscular legs. It wasn't the first time I had snuck a peak at Jen's body. She was the only person I knew who spent more time in the gym than me, and I could see it was paying off as I gawked at her legs and the tiny pair of black underwear adorning the area between them.

I slid my pants off and kicked them aside, trying hard to conceal the massive erection that was doing its best to pop out of the hole in the front of my boxer shorts. Jen was sitting on my bed, fidgeting nervously but looking cute in her little black panties.

"Aren't you going to take off your shirt?" I asked.

"I don't need to take my short off to get my ass fucked do I?" she snapped back.

The fact was, was that Jen was more than a little self conscious about her less than average sized breasts. I knew that was the case but didn't press the matter. Besides, it wasn't her tits that I was interested in.

We sat there for a moment, each not wanting to be the first to be completely exposed. Finally, without a word, Jen slipped off her panties and pulled her knees up to her chest as she sat there looking up at me. Taking her cue, I pulled down my boxers and stepped out of them to stand before her, completely naked.

"Okay, " she said. "How do we do this?"

"The easiest way is if you get on your hands and knees."

Jen moved to roll over but stopped and looked back at me.

"Do you think we could turn the light off?" she asked.

I shook my head.

"I like to see what I'm doing," I replied.

"Fine."

I expected her to put up more of a fight, but to my surprise she complied with my wishes and rolled over, propping herself up on her hands and knees. I took a moment to relish the sight of my best friend bent over naked on my bed before climbing down behind her.

Gently, I placed my hands on her taut ass cheeks and pried them apart to expose her asshole to my view.

"What the fuck are you doing?" Jen scolded, reaching back to swat my hands away.

"I'm just looking."

"Just do it."

"Are you sure you don't want to suck it first?" I asked hopefully.

"Just stick it in and get it over with."

"Okay, but I don't want to hear you whining that it hurts."

With that, I placed the head of my dick at the entrance of her puckered little rosebud and pushed.

"Owwwww," Jen yelped as the first couple inches disappeared inside her asshole. "Okay!okay!okay! I'll suck it! Just take it out."

I smiled to myself as I withdrew my cock from Jen's ass. With little hesitation and to my surprise she promptly spun around and grabbed my dick in her tiny hand. With a final, resigned look my way, she pushed my cock past her lips into her mouth.

I threw my head back and moaned as Jen's head bobbed back and forth on my dick, coating it with saliva. I wanted the blowjob to go on forever, but to my disappointment Jen backed off as soon as my shaft was good and wet, resuming the position on her hands and knees.

I spit in my hand for good measure and smeared it along her ass crack, rubbing my thumb into her hole for added lubrication. I then placed my newly glistening cock back at the entrance of her dark inviting hole and pushed.

"Relax," I suggested, as the head of my dick slipped inside her.

Jen put her head down and exhaled as I felt her asshole's grip on my shaft weaken considerably.

"Good girl."

My praise apparently went unnoticed as Jen remained silent. I pushed forward a little more, feeding more of my cock into her ass. Jen let out a quiet moan although I couldn't tell if it was from pain or pleasure. I was about halfway in when I reached down and pulled her ass apart, treating myself to exceptional site of my best friend's little pink butt hole hugging my dick. At that moment I only wished I had a camera.

"You.. can put it in... farther now," Jen wheezed, through clenched teeth.

I complied and thrusted my hips forward a little more, burying another couple inches of meat in her ass.

"Play with your clit," I suggested. "It will make it easier."

Jen took my advice and reached back between her legs as I bottomed out in her asshole. My balls were pressed against her pussy lips, which I noticed were a bit moist. As I began to gyrate slowly, moving my cock in and out in small increments, I could feel the pace of Jen's fingers increase.

"How does it feel?" I asked, picking up the pace.

"It's...okay," she stammered, obviously preoccupied with the area between her legs.

I was moving in and out with long, slow strokes as Jen became more comfortable. I gazed at her impossibly tight asshole as it repeatedly swallowed my cock. If not for my agonizingly slow pace I definitely would have cum already.

"Oh Fuck Jen," I moaned. "Your ass feels so good!"

"Your cock in my ass feels so good!" she returned, as her fingers increased to a frantic pace.

I was surprised to hear Jen talk like that, but it was definitely a turn on so I encouraged her to continue.

"Yeah, you like that?" I asked giving her a light slap on the ass. "You like getting your ass fucked?"

"Yes!" she moaned through labored breaths. "Yes! Fuck me! Fuck my tight ass! Oh! Oh my fucking god! I'm gonna cum! I'm gonna... Oh! Fuck! I'm cumming! I'm cumming with your cock in my ass..."

Jen's voice trailed off as her orgasm subsided. She raised her head from the bed and swept the hair from her face.

"That didn't take long," I commented, continuing to slide my dick in and out of her anus.

"Are you almost done?" she asked. "It's starting to hurt again."

"Just relax," I said. "I'm almost there."

I increased my pace even more as Jen dropped her head down and bit her arm to keep from howling in pain.

"Where are you going to cum?" she asked, her voice muffled by her own arm.

"In your ass," I replied bluntly.

"No, you can't do that!"

"Okay then. I'll cum in your face."

Jen was silent for a moment before answering back.

"Okay," she said quietly. "Do it."

"Where?" I goaded.

I could feel the beginnings of that unmistakable feeling arise in my balls.

"You know where!" she shot back.