The Bet

Kelly and I arrived at our friend Darren's place. We was having a small party that we arrived fashionably late to. They had just finished several rounds of poker when we arrived.

"Hey Darren sorry we're late. What did we miss?" I asked.

"Dave! Kelly! I'm so happy you made it! And not much other than Eric over there taking us all to the cleaners in poker." Darren was already tipsy and slurring his words.

As we mingled Eric came by and took notice of Kelly. We were acquainted with Eric, but didn't know him well. Kelly also knew someone that dated him for a short time. He was tall, muscular build and a generally good-looking guy. He also had the talent of being able to talk to anyone. But he was known to be a little full of himself and cocky.

"Kelly! It's been awhile. I must say you look great tonight."

"Thanks," Kelly replied. "How have you been?"

"Wonderful, just won 250 bucks tonight. And how are you? Still seeing that one guy?"

Kelly rolled her eyes, "You mean Dave, my boyfriend and the guy standing right next to me? Yes I'm still with him."

"Hey Eric how's it going man?" I asked. I wasn't surprised to be honest. It didn't offend me one bit he didn't remember me.

Eric apologized, "Sorry bro, no hard feelings right?"

"No worries it's fine." I said accepting his apology.

Eric wandered off for a while. The host Darren continued to get more drunk and guests started to depart as the night wore on.

Eventually we found ourselves talking to Eric again. The other guests had departed and a heavily inebriated Darren was passed out.

We were talking about leaving when Kelly said to Eric, "You know I'm honestly surprised you didn't take one of the girls from this party home tonight."

Eric laughed and admitted, "Yeah things don't always go according to plan. But the night isn't over yet so you never know!"

Kelly giggled, "except it kinda is over because all the girls already left."

"Well not all the girls," Eric replied suggestively.

"You aren't enough man to handle me buddy," Kelly teased Eric.

"I bet I'm more man than Dave! At least where it counts," Eric said with a wink.

Kelly quickly came to my defense, "no way. Trust me I am perfectly satisfied with what my boyfriend has. Besides, you're so full of yourself you probably don't even know you've got a micro dick!"

I was so thankful for my awesome girlfriend standing up for me. She just made me feel like the biggest guy in the world.

"If you really are so confident why don't we make a bet on it? If your boyfriend really has a bigger dick then I'll admit I'm the lesser man and give you the 250 bucks I made playing poker today. But if I have a bigger dick then you get naked for me and give me a hand job to completion." Eric said with unwavering confidence. What a prick I thought, Kelly would never agree to that.

"Deal!" Kelly responded assertively.

"Wait... what?!" I asked in shock.

Kelly whispered, "Don't worry hun you've got this no doubt. He's bluffing I can tell. Beisdes he's got a micro-dick for sure. Becky even told me so when they broke up."

"Great, Darren has to have a tape measure around here somewhere," Eric said as he searched drawers.

"What about Darren?" I asked. I'm sure he didn't want us whipping our dicks out in his apartment.

"What about him?" Kelly answered. "He's passed out! Eric you find that tape measure yet? I want my 250 dollars!"

"Yup, I've got one right here," Eric replied.

"Ok great! Dave come here, it's time to get you hard!" Kelly guided me to nearby chair and began to undo my pants. "Eric you are on your own for this part." She laughed.

Kelly pulled my dick out and started sucking. Damn she was good at giving head. I leaned back losing myself in the blow job. It sounded like Eric was playing with himself to get hard, but I was in too much ecstasy to look.

It didn't take to long to get completely hard. Kelly pulled away and put the tape measure to my dick. "Five inches! Ok Eric time to lose!"

Eric stepped up next to Kelly still on her knees in front of me. We both looked at him at the same time. I heard Kelly gasp and my heart felt like it stopped beating. Eric was hung like a porn star. A cocky grin grew on Eric's face as he said, " We clearly don't need to measure to see that I've won, but I know you've got to be curious. Why don't you be a doll and hold up that tape measure to see for yourself."

What a cocky prick! But there wasn't anything I could do because of Kelly's stupid bet!

Kelly lifted the tape measure to Eric's hard cock. Which stuck out only inches from her face. She pressed the end of the tape to the base of his cock and slowly pulled out the tape measure. Kelly gulped and said, "nine and a half inches."

"So that is almost twice as long as your boyfriend's? Not bad for a micro dick!" Eric chuckled. "Is it a bit thicker too?"

Kelly was staring at his cock completely mesmerized, "yes, much thicker." she shook her head to break out of the trance and turned to me, "sorry hun but a bet is a bet." Before turning back to Eric she looked down with a look of pity at my own dick.

Kelly began to reach up to the massive cock when Eric interrupted her, "nuh uh! Remember the bet, you've got to be naked."

"Oh right," Kelly chuckled. She began to disrobe while Eric sat down and watched. She paused when she got to her bra and panties. After taking a deep breath she removed her bra tossing it off to the side. Then pulled her panties down to the floor and stepped out of them. She started walking seductively towards Eric doing a little spin on the way to show her entire body. It looked like she was actually enjoying this! When she reached Eric she dropped to her knees and licked her lips.

Kelly looked up into Eric's eyes. "Go on." He said, "Don't keep it waiting."

Kelly reached up with her small hand and placed it on Eric's cock. Her hand failed to fully wrap around it due to its girth. She slowly moved her hand up and down it. She moved her hand to head of his cock and began exploring the entire surface with her fingers. She was in a complete trance. Finally, she raised her other hand and began to stroke the shaft quickly with both hands. Even then there were several inches of cock left beyond her two hands.

Without realizing it I found myself playing with my own hard member. Half of me was gut punched by the act before me and the other half incredibly turned on.

After five minutes of pumping I could tell Kelly was getting tired, "are you close?" she asked. "My arms are getting tired!"

Eric shook his head, "no sorry. You might be hot and this feels great, but I have a lot of stamina. It takes me a long time to get off especially from just a hand job. And you know the deal this needs to be to completion."

Kelly removed one hand from Eric's cock and used it to massage her opposite shoulder, "I'm not sure if I'm going to make it, but um" she looked back mouthed sorry, "can we still call it a done deal if I maybe get you off another way?"

"No way! That wasn't the deal!" I argued. However no one acknowledged me.

"I think we could compromise. What do you have in mind sweetheart." Eric looked down at Kelly as her hand continued massaging his cock. I really disliked his continued use of pet names with my girlfriend.

"I was thinking if I gave you a blowjob I could get you to cum quicker. What do you think?"

"You've got to be kidding!" I protested.

"Dave it's fine, the faster I get him to cum the faster this whole thing is over with!"

Eric feigned disappointment, "Ugh I don't know. I'm not big on changing parameters of bets on principle. But I know your arms are getting tired so in the spirit of compassion I will agree if you agree to swallow at the end."

"Yeah she doesn't even do that with me pal!" I said.

"It's fine I'll do it!" Kelly turned to me, "trust me Dave it's better to just finish this quickly!"

Kelly wasted no time and began to run her tongue along the underside of the cock. When she reached the tip she twirled her tongue around the head. Then began kissing it before wrapping her lips around taking several inches into her mouth.

I couldn't believe how much Kelly was into this! Then I noticed her left hand had slipped down between her legs. She was playing with her pussy!

"You like the taste of that dick baby?" Eric asked.

Keeping it her mouth Kelly gave a cheery, "mhm!" and a cute nod.

Eric's cock was so large she couldn't fit it entirely in her mouth and had to use her free hand on it as well. I don't know if I was more shocked that Kelly volunteered to give this guy a blow job or that I was jacking off while watching it.

Kelly pulled her mouth away for a moment to speak while still stroking it with one hand her other hand still between her own legs, "so what do you think of my blow job skills Eric?" Then she playfully slapped her tongue with his cock before wrapping her mouth back around it.

Eric groaned, "mmmm it feels amazing. Your boyfriend is a lucky guy." He turned and winked at me, that asshole. Then he leaned forward and whispered something into Kelly's ear.

Kelly giggled and said, "deal!"

What had she just agreed to? I wasn't sure but Kelly was even more into Eric's cock. Going between licking his balls, stroking it, and furiously sucking on his hard dick. This sight was really turning me on. I stroked my own member faster until I unloaded my cum onto the floor in front of me.

Eric saw and chuckled. He stroked Kelly's bobbing head and said, "looks like I won again."

"What does that mean?" I asked. I received no answer, but whatever that meant it seemed to excite Kelly. She rubbed her clit even faster until she had an orgasm of her own. Her scream was muffled by Eric's large cock in her mouth. It must have felt good for Eric because it sent him over the edge too. He came in Kelly's mouth while holding the back of her head.

"That's it baby drink all that cum," Eric said still holding her head. Kelly responded simply with a moan.

After Eric was done cumming Kelly pulled back. "Wow," she said while trying to catch breath. "Thank you, Eric!"

Did my girlfriend just thank another guy for basically making her suck his dick?

"You're welcome Kelly. I think you'll enjoy what's next even more."

I was confused, "what is he talking about?"

Kelly turned towards me, "sorry Dave but while I was blowing him Eric and I made another bet."

This was completely ridiculous, "what kind of bet? And why?"

"Well it seemed like a fun idea. We all seemed to be enjoying ourselves, especially you." It embarrassed me that they had noticed. "So Eric bet that you would cum watching me blow him before he would cum. And if he won.. he'd get to fuck me."

My jaw dropped, I was completely speechless.

Seeing my reaction Kelly continued, "but it's ok you can watch again!"

Eric kissed Kelly, put one hand on her chest and the other down between her legs. Seeing him touch my girlfriends pussy started to reawaken my own cock.

"You're really wet for me. I like that." Eric said before kissing Kelly's neck.

Kelly moaned, "I think my kitty is just excited to meet a big new friend." She grabbed Eric's semi hard cock.

As Kelly started to stroke the growing cock Eric drove a finger into Kelly's pussy, she let out pleasurable moan.

Eric helped Kelly down onto a large couch. She moved her butt to the edge and pulled her legs wide apart. Her pussy looked to be dripping in anticipation. He leaned over her to kiss her and play with her tits. His cock pressed against her crotch. Kelly began moving her hips desperate for Eric to slip inside.

Eric enjoyed teasing her. He pressed the large head of his cock between Kelly's wet pussy lips. He rubbed it up and down causing Kelly to shudder as it moved over her clit.

"Ask me for it," Eric demanded. "You're going to need to ask for it."

"Please fuck me Eric," Kelly pleaded. "I want your big cock inside of me. Please."

Eric slowly sank himself into my girlfriend's pussy. She moaned in pleasure as it's full size penetrated her.

"Am I bigger than your boyfriend Kelly?" Eric asked.

"Oh y-yes much bigger. So much bigger!"

"Is it better Kelly? Does my cock inside of you feel better than Dave's?"

"It does. It feels so much better when you fuck me with your big dick Eric!"

Eric continued his questions, "You want to fuck me again after this don't you? Tell your boyfriend."

"Yes. I-I'm sorry Dave, but I love how his cock feels I have to.. Ohh! I have to fuck Eric more! A lot more! Oh fuck!!" Kelly barely got those last words out before having a massive orgasm.

Eric slowed down to let Kelly recover, slowly picking back up the pace. "I bet Dave has never made you cum like that."

Looking up at Eric as he continued to fuck her she replied shaking her head, "no never like that."

Eric smiled and picked up the pace, "I'm going to cum soon where do you want it?"

"I want you to cum in me, fill my pussy with your cum!" I couldn't believe she had just said that. She makes me pull out and cum in a towel!

The last comment put me over the edge and I came for the second time that night watching my girl with another guy.

Soon after Eric grunted and plunged deep into my girlfriends pussy to deposit his load.

After Eric pulled out Kelly started to giggle, "You know I lost both bets, but I think I still won." she said winking at Eric.

Eric laughed, "You want to lose another wager tomorrow?"

Kelly glanced at me and my still cum covered dick then over to Eric's large flaccid cock swaying in front of her. Finally, she looked Eric in the eye and replied, "You bet I do!"