I Lost a Bet

It was the kind of warm August night where you don't even want to move. My friend and I were just lying on the couches in my living room playing a baseball video game. We had just started a new game and it was still scoreless.

My phone buzzed soon after we began play so I paused the game to fish it out of my pocket. It was rather late and I was wondering who it was during the retrieval. When the phone's screen met my eyes I could see a text message from my girlfriend was the cause of the buzz.

"Hey babe, I just got off work and am super tired, I don't want to bike home and was wondering if I could crash at your place tonight."

I typed out and sent the message, "Sure, Gregg and I are just lying around playing video games."

"Who was that?" Gregg asked me.

"Linda, she just got off work and is going to crash here tonight." I replied.

"Cool." Gregg said, "hey we just started this game, why not take a break to get something to drink and wait for Linda to show?"

I agreed with his suggestion and led the way to my kitchen. I opened the fridge and pulled out two beers, handing one to Gregg.

"A nice cold drink will feel great tonight, it is so freaking hot!" Gregg accepted the beer.

We sat at my kitchen table enjoying the cool beverages. Soon I heard the familiar sound of a bike rolling down my gravel driveway

"Sounds like Linda has arrived." Gregg said.

I had always allowed Gregg to go on about how hot he thought my girl was, but his excitement at her arrival was a little uncomfortable. Linda was a sweet eighteen year old, tough for any twenty-one year old guy to resist and Gregg was a member of the latter category.

"Hey babe." Linda came through the door greeting me with a kiss. "What's up Gregg?"

Linda elaborated on her tiered state, noting a long shift and the ridiculous heat/humidity, saying she could only hang out for a bit, but needed to go to sleep soon. She stayed for a beer, the three of us chatted for a bit, but after the one drink she announced her retirement. She moved to go to my room upstairs, I told her Gregg and I had a game to finish and I would join her after it was done.

"Let's get back to work." Gregg said as he finished his beer.

I agreed and we made our way to my living room.

"Hey how about we make this game a little more interesting? You win you get $50, but if I win...I get Linda." Gregg said.

This caused me to finally break down, "dude! Don't talk like that about my girl! Besides you'd have no chance with her."

"That doesn't matter, she's in a dark room, if we don't hit the lights she'll just think I'm you."

"So you solved one problem, but she's still my girl and I don't want my friends dick in her mouth!"

"You got nine innings to make sure that doesn't happen...$50 buys a lot of beer."" He tried to convince me to accept.

I was pretty good at this game, and having a pretty good night. Gregg and I had played four games so far and I had won three, I figured my chances of winning the fifth were pretty good.

"Fine, but only because I know you're going to lose." I said.

"Whatever. Let's wait until after the game to choose a winner" Gregg returned.

The further terms of my agreement included that I would be able to choose my team first. I had a favourite team for this game, it had a line-up of sluggers that could belt out home runs at a tremendous clip. My team's starting pitching sucked, but it was a one off game, they had one good pitcher I would always select in similar situations.

I chose to be the away team, any notion of home field advantage really doesn't exist in video game sports. I liked to bat first, in the past I figured out if I could score a few runs early on I could affect my opponent's confidence for the rest of the game. This demoralization, I found, would cause the opposite player to make stupid mistakes and if I was really on my game, I was able to turn the match into a blowout.

My strategy did not work this particular time however, Gregg controlled the pitcher with tremendous expertise. He turned the first inning into a one two three affair. He repeated his domination in the second, the third, and so on until we found ourselves in a scoreless ninth.

Somehow I managed to string together three base hits, only allowing Gregg to get one out.

:You really screwed up this time!" I gloated. "All I have to do is hit a ball to the outfield and I'll be winning."

"Don't count your eggs jerk, I just have to make the right pitch to make you ground out to get the double-play." Gregg retorted.

The bet added heat to our friendly rivalry, I was finding myself becoming quite competitive. The last thing in the world I wanted was to share my girl, take away the innocent version my mind had created of her. I would have done almost anything to win.

Sure enough Gregg made a double-play pitch, ending my threat.

"Looks like I'll be walking you off." Gregg said.

"I will win it in extras easy." I responded with confidence.

As it almost always seems to play out, I had to retire the top of Gregg's lineup if I wanted to force free baseball. His lead off hitter worked me for a walk, but his number two promptly swung at the first pitch, grounding out allowing me to erase both. I only needed one more out, but I had to work my way through his number three, the most talented offensive player on his chosen team.

When facing this batter I made sure to nibble at the corners of the strike-zone. I didn't want to throw him anything he could hurt me with. Gregg was able to take until the count was full. If I was able to make my pitcher throw one more strike he would be out, but if I just lobbed one in there Gregg would get a hit for sure. I had to take a second to think about what I should do. I figured it best to throw a breaking pitch, a ball that would look like a strike but then right before it reached the plate would drop, bouncing in the dirt. Hopefully this would induce a swing and miss, but worse case he would be able to react holding his swing. It was a bigger deal that his current batter would get a hit than he would walk.

This seemed like a foolproof strategy, my high confidence caused me to deliver the pitch with ease. I guess I forgot about the third outcome though. I made my guy throw the pitch, but I was too slow in hitting the right buttons, causing me to miss my intended location. What resulted was a slow moving lob that was in Gregg's sweet spot. He didn't make a mistake crushing my offering the other direction. It did not take long for his rocket to clank off the animated stands behind centre field. As I watched his player trot around the bases I wanted to call off the bet, I can't believe I lost.

Gregg made a hissing noise, "and the crowd goes wild!" He continued to imitate the announcer, "down at field level our roaming reporter caught the hero just after he hit the game winner."

Pretending now to be the player he controlled, "I'd like to thank my mom, my dad, my brother... but most of all our lord for blessing me with these talents."

Gregg was rubbing it in, he was far from a gracious winner. I mean I was excited before my first time with Linda too. Linda, I almost forgot, I had bet my lovely girlfriend., As much as I liked Gregg, I still hated the idea of him enjoying Lina's mouth.

I panicked and tried to back out,

"A bet's a bet, don't be a sore loser bro." Gregg argued. "I would have given you the $50 with no words if you had won."

I hated this, he had me cornered. What is a man without his word? I guess I would rather have Linda be with a friend than a total stranger. At least I knew, beneath his rough exterior, Gregg was one of the good guys.

Reluctantly I admitted defeat, it was just a BJ after all, "be quick about it."

Gregg smiled, "I'll make sure to give my nut to Linda as soon as I can!"

Man he was really being a dick about this. He told me I had to go in the room with him, use my voice to convince Linda he and I were one in the same.

"The lights will be off, you wont see anything." Gregg pleaded his case.

I actually liked the idea of being there with him. I did not suddenly warm to the idea of him and Linda, but I figured at least I could play police man, making sure he didn't push his luck.

We went up the stairs to my room, I pushed open the door. Without the aid of sight I was able to navigate us to my bed side pretty easily.

Gregg unzipped, "Linda babe, how bout a goodnight kiss?" I asked.

Half asleep she responded, "Another time, I'm too tiered for that."

Gregg nudged me, urging me to make sure he could collect, "You don't have to do much, just open your mouth for me."

Regretfully my pleading succeeded. I could hear the unmistakable sounds of lips wrapping around a cock.

"Geez baby, you seem bigger than normal, and you taste so good!" Linda moaned before she went back to sucking.

I guess she had woken up a bit, it certainly sounded like she was doing her part. I could hear her moaning and slobbering. Lips smacking together as she worked my friend. Despite the low light, I could see my bed sheets moving up and down.

"Baby your cock is so hard tonight!" I could hear Linda moan.

I noticed the sheets over her crotch moving up and down even more now.

She must have removed Gregg from her mouth, "fuck yes I'm about to cum!"

I knew my girl to be very proper, she was never this vocal when sucking me. I had to scan my brain to even remember hearing her swear, it would have been more likely of her to say frick or fudge when she was with me. Gregg had barely done anything, and he had totally modified my girl's behaviour!

I gathered she put him back into her mouth as she came, I could hear her moans of pleasure were muffled by Gregg's cock. Biting my tongue, so as not to ruin the bet. I wanted to say to Gregg that her cumming was not part of our original deal.

Panting in recovery I could tell she freed up her mouth again, "shit, I'm not sure I've ever cum that hard before...I bet you would feel awesome inside me tonight?"

Whoa, whoa, whoa, my mind screamed. Gregg just bet me for a BJ, all pf a sudden my little girl was wanting to fuck? The jealousy of her enjoying my friend so much was coursing through my veins and about to reach my brain, I had to do something to stop this. I guess I could have calmly declined her offer, saying I just wanted her mouth tonight, but I was not calm.

I reached for my light switch, flicking it up to expose the situation.

Her eyes adjusted to see Gregg standing before her, "What the hell is this!?" She screamed after she spit his cock out of her mouth.

In the new light I could see what she was groaning about. My eyes did not linger for very long, but it was difficult to not notice the huge cock affixed to my friend. It was even bigger than some of the ones I'd seen porn stars fawn over millions of times. It certainly dwarfed my six inches.

As I thought it through I found myself wondering how Linda could have mistook this beast as belonging to me?

"Gregg won a bet, he won a BJ from you." I explained.

"A bet!? What gives you the right to treat my mouth like currency!? Currency you own!?" Linda shouted at me.

Damn she was mad, I'd never seen her like this, but I guess I'd never provoked her in this manner before. She had a right, I mean if she bet one of her friends and I had to eat their pussy...okay that's not the same thing, I'd love that. Let's try again. If I was in her position, and some random guy tricked me into sucking his cock, I would be pretty pissed off.

The whole time we argued back and fourth Gregg did not move. His cock just hung there in front of Linda's face. I did not enjoy the picture, but the thoughts it provoked gave me some relief. If she was really all that angry she would have moved further away from Gregg, even now knowing its true owner, I think she still liked the cock enough to keep it close by.

"Maybe I should." Linda started at me. "To teach you a lesson." She went on. "If I let your friend fuck me, you'd think twice about making a stupid bet like this ever again."

As true as her words were, the punishment did not fit the crime in my opinion. Foolishly I'd let her form the idea though, there was little I could say to make her mind change now.

She grabbed Gregg and shot me an evil grin, stroking away at him to make the cock hard once more. With a second glance I figured Gregg was at least nine or ten inches long, and tremendously thick. I wondered how he was able to find pants that even fit, storing that monster must have required tremendous effort on his part.

In one motion she pushed my bed sheets away exposing her perfect teen form. My girl's beautiful tanned skin curved with her body in just the right way. She had amazing perky C cups, topped with even more awe inspiring nipples. From her previous stimulation they were rock hard.

My gaze returned to her face. She moved the fat cock across her rose tinted cheeks, I could see her big blue eyes open wide as the cock pursed her full lips. She sucked it in again, even though she could easily see it was not her man's, she made sure to hold the eye contact she and I had established, still continuing to blow Gregg.

I wanted to turn around a run out the door but my body froze. Allowing this image to be etched in my brain was bad enough, but they would no doubt continue if I left. I would drive myself crazy playing out the unknown scenarios in my mind.

Releasing me from her stare, she closed her eyes and focused her efforts on Gregg. I could tell he was enjoying Linda's mouth as he let out several moans. He wasn't the only one who found enjoyment in the sucking, I could see Linda's hand returning to her crotch. She began rubbing her clit, probing her index and middle finger into her hole. I saw the stream of moisture emanating from her little pink cunt as I heard those familiar muffled moans. Gregg slipped out of her mouth as she scrunched her face.

"Oh shit! I'm..." The rest of her speech was a loud moan made up of gibberish.

When she came to her hand immediately latched on to Gregg once more. Stroking the huge dick she looked up at him and asked,

"So stud, are you ready to fuck me yet?"

Gregg half nodded as he scrambled to position himself between my girl's wide spread legs. She rocked her ass raising her legs, helping him to rest her ankles on his broad shoulders. He hovered on top of her stroking his meat in front of her awaiting hole.

For a moment he showed me slight remorse, looking back in my direction to say,

"Sorry dude."

He quickly turned back to Linda. They locked eyes as he began to push himself in.

"Hmph!" Linda let out a symphony of howls.

Gregg's size was obviously not what Linda's pussy was used to. She must have been experiencing some pain, although none was voiced. She was determined to experience the previously unknown pleasures only a cock this size could administer.

I was spectating Gregg slowly humping my girl, he continued to work his cock deeper and deeper into her. I could see the expression on her face turn to one of total pleasure.

"I've never been this full of cock before!" Linda shouted into the room.

Gregg continued to squish away. From the sounds I imagine Linda's pussy was sopping wet. Previously I had only seen her half this excited, and that was only on very special nights.

"You are some kind of fucking sex god!" Linda praised Gregg with her moans. "Fuck me! Fuck me! Fuck me!"

I could see Linda's little hands reach out and wrap around Gregg's waist. She pulled him even deeper. Once again I feel I must stress, never before had I seen this kind of behaviour out of my girl. She was so sweet and innocent, if I hadn't engaged her sexually I would not even guess she knew what a dick was!

Allowing herself to catch her breath after what seemed to be yet another orgasm she uttered the words that rocked my soul.

"Fuck me in the ass!"

This was something I pleaded with her to let me do, she never gave in. She would say she was too much of a good girl, and sodomy would remove her ability to make that claim. I had spent so much time trying to convince her to allow my exploration of her other hole, and here she was ready to give it up on a whim.

Gregg tossed her about, forming her into a doggy style position. He knelt behind her, rubbing her pussy juices onto her ass. I could see Gregg pressing forward into Linda's ass. Eventually he gained entry.

"Ouchee!" Linda screamed.

With this Gregg froze.

"Did I say stop?" Linda said to Gregg as she looked over her shoulder.

Gregg wore a rather dumbfounded expression as he continued his journey.

"You're fucking stretching me out so much!" Linda screamed.

Gregg gripped Linda's hips as he began a full assault on her ass. He opened up to a thrusting speed I thought would break my little girl, but from her moans apparently she liked this.

"Jesus Gregg! Your huge cock feels so amazing in my little ass!" Linda continued to moan.

"You're going to make me blow!" Gregg said.

"My face! My face! I want to feel your load on my face!" Linda shouted incessantly.

Yet another desire of mine Linda would never let me fulfill.

I watched as Gregg pulled out of Linda's ass rolling her over so she was on her back. He waddled forward until his knees were straddling her chest. He remained in this position stroking off in her face, occasionally pausing to dip his head in her mouth.

He tilted his head back, I could see his pupils as they began to disappear under his eyelids. At this point I focused my vision on my sweet girlfriend. Her mouth was wide open, her little tongue outstretched ready to accept the seed.

Gregg's body began to shake, soon I could see thick white ropes of cum shoot out of him into Linda's mouth. His load splashed on her tongue, splattering to her cheeks. He shot at least five gooey blasts, Linda swallowed as much as she could. The remaining sperm completely coated her face as Gregg jerked out the final drops.

"So was I worth the bet?" Linda asked Gregg as she wiped her eyes clear.

"And then some." Gregg replied with a smile.

He disembarked, his feet landing on the floor beside my bed.

"Get my clothes bro?" He asked me.

This pissed me off. Not only did he want to make my girl into his slut, he wanted to make me into his butler. Before I could react in anger, I considered the greater humiliation I had already felt that night. It wouldn't be any worse for me to fetch the man's pants? I did as I was asked, moving over to the corner of the room, picking up the pile of fabric he had discarded earlier. I forced a smile as I handed the man his things. After getting dressed he announced he had to leave.

Linda did not move from my bed, I could not bring myself to sleeping with her that night. After letting Gregg out I found the couch downstairs and made myself a place to sleep.

The next day I made it clear to Linda that our relationship had run its course. I guess technically I dumped her, but to say she forced my hand would be an understatement. I did not give Gregg the same tongue lashing as Linda, I just deleted his number from my phone. He seemed to get the message when I didn't call anymore.

To maintain the image she had cultivated between our mutual friends she never made anything concrete, but Linda and Gregg certainly became much closer after that night. It was hard for me to see them together, this probably played a role in my cross country move for college. I did visit my hometown every so often, but once I successfully removed myself from my circle of high school friends I tried to limit my returns.