A Bet to Beat the Pants Off Me

Hi my name is Jack and I am a horny 19 year-old guy. I love women, I love their bodies, their minds, their emotions; I love every single aspect of women. I think about them all the time and I masturbate to them constantly. I look at their bodies, I surf porn, I hang bikini-girl pictures on my wall, I have posters of women in all sorts of provocative positions and clothing (or lack thereof). In summary I like chicks!

Now that we got that out of the way let me give you some background.

A single mother and an older sister raised me; I have two grandmothers and a dog that, of course, is female. Women rule my life and have since I was born. I really don't have much of a male influence in my life other than action movie heroes, comic books heroes, and possibly a sports hero or two—though most of them are jerks so I stick to mainly fictional heroes.

I realize that I have a chauvinistic view of women and their hot sexy bodies, but I can't help it. I have no outlet! (By the way, I had to look up how to spell chauvinistic!)

I have no girlfriend at the moment although there are at least 3 girls I know that I want to go out with. The main girl is one of my Sister's best friends—Jenny Drake. She's my age. I guess my Sister, whose name is Lori, is really better friends with Jenny's Sister Karen, but whatever. Jenny used to come to my house and have sleepovers with my Sister Lori and I just about died a thousand deaths knowing Jenny was in her slinky PJs just down the hall from where I was lying in bed playing with myself.

So are we all on the same page? My Sister is Lori, her friend is Karen and Karen's Sister (Lori's other friend) is Jenny and I want Jenny—BAD!!!!!

One more character to introduce and we're on our way—my Aunt Amy. She isn't really my Aunt; she is my Mom's hot younger friend from high school that has been around since I was a kid. We call her Aunt Amy as an honorary title and not as a blood relative at all. This is NOT a story of incest so let's get that straight right now.

Aunt Amy is hotness unbound! She used to be a model and I have seen a few pictures of her scantily clad that almost made me blow my own pants off! She has a body that I NEED to SEE! Do you understand how fucking horny I am! I actually physically NEED to see this woman naked in order to survive!

Now onto the actual story:

I take a lot of heat from my Mom and Sister as well as Aunt Amy about my testosterone issues. They kid me a lot and make references to my manhood that are tasteful in a family setting, but also secretly kind of make me feel a little strange. I guess if I wasn't flowing with desire to fuck everything that moves I would probably feel a little like an outcast, but I end up just laughing off their jibes.

One day in mid summer when it was sweltering out Aunt Amy stopped by for a visit. We were all hanging out in the backyard when the conversation came around to me.

"How's everything going, Jack? Got a girl yet?" Aunt Amy asked.

"No. Just hanging out for the summer." I said

"Why don't you ever have a girl? You're a hot young stud, you should have girls hanging off you constantly, especially in this heat."

"I guess."

"He's too shy!" Lori said. "He doesn't know how to talk to girls."

"I do too."

"Then why do you always lust after Jenny and never talk to her? She knows you like her, we all know you like her." Lori asked.

"Yeah, Jack, why don't you talk to her?" Aunt Amy added.

"I don't know, I just . . . I don't know."

Did I mention what a wordsmith I am?

Then Mom chimed in; "I know why he doesn't know how to talk to girls. It's because all he thinks about are their bodies. He isn't interested in them at all."

"That's not true." I protested.

"Face it Jack, you're so obsessed with sex you can't concentrate long enough to talk to a girl like a human being. You're way too horny and shy. If you could get over that you'd be a big hit with the girls." Mom said.

"Yeah and then you could look at them like people to be respected, not like talking boobies." Lori said.

"I have an idea, let's talk about something else!" I suggested.

"Too horny and too shy! Ahh, to be 19 again!" Aunt Amy said.

This peaked my curiosity, "We're you, you know, horny when you were 19?" I asked stuttering on the word HORNY.

"No more than usual, I guess. I know I really wanted Bill Stanton Captain of the Basketball team. That boy could fill out a pair of shorts like nobody's business!" she said and everyone laughed.

Then I made my fatal mistake; "You filled out some shorts back then too, right?" I said and my face almost burst into flames when the laughter stopped and they all looked at me.

"What's that supposed to mean?" Aunt Amy said.

"I just mean, that's when you used to model, isn't it?"

"Yeah. Are you suggesting I can't fill out a pair of shorts now?"

"No, you're still . . . I mean you look . . ."

Then the laughter returned much to my embarrassment.

"Well thanks Jack. I appreciate a guy like you complimenting me. I try to keep in shape. I like guys checking me out." "And they do!" My Sister added.

"We sure do!" I said.

"Oh really? You like looking at my body?" as she said that she lifted her hair and arched her back for me.

"Look at him he is about to blow!" Lori said. "Anymore of this and he is going to have to run to his bedroom of self-abuse!"

They all laughed again. I was humiliated again!

"He's going to have to go shoot some hoops to blow off some steam now. That's all he does all summer is shoot hoops." Mom said trying to save me by changing the subject.

Aunt Amy looked me over, "I can tell, you look pretty fit, but I could take you in a game." She said.

"Oh please, I would destroy you." I replied.

"Why? Because you're a big strong man and I'm just a helpless little girl? I'll have you know I played basketball in high school and I haven't missed a beat!" Aunt Amy said.

I was smiling ear-to-ear "Okay, yeah, yeah, whatever."

"Okay, let's go Hot-Stuff. I'll whoop you right now!"

"It's too hot." I said.

"Scared you'll get beat by a girl?" Aunt Amy taunted.

"No."

"Yes he is look at him!" Lori said laughing.

"I'll play, I'm not scared. How about a nice game of H-O-R-S-E?" I said.

"What are the stakes?" she asked.

"I don't know. Five bucks?" I said.

"Oh come on you can do better than that. I have a good one. How about if I win you have to ask Jenny out and go out on a nice date with her." Aunt Amy said.

"No, that's not how I want to do it." I said no longer wanting to play.

"You are scared!" Aunt Amy said. "Okay, I'll sweeten the deal, you win and I'll strip down to my underwear and you can take a photo of me that you to jerk-off to! How about that big guy?"

I froze. Every part of my body short-circuited. I couldn't respond or move. I was helpless.

"What!" was all I could say.

"You heard me. And believe me I am wearing some sexy lingerie right now—you won't want to miss this!" Aunt Amy said.

"There's no way! There's no way Mom will allow that." I said and we all looked over at Mom.

"Why not?" Mom said shocking the hell out of me. "You've seen her bikini pictures before and besides I think it will force you to ask Jenny out because you're going to lose!" she said.

"You're on!" I said and tried to hide my erection thankfully I was wearing jeans even though it was hot and I wasn't about to switch to shorts now.

We made our way over the paved driveway / basketball court. I wasn't playing that well today (probably because Aunt Amy's attempts of doing something sexy every time it was my turn constantly distracted me.)

It finally came down to me with H-O-R and Aunt Amy with H-O-R-S when I delivered the final blow. I made my patented hook from half court shot and sank it beautifully. She tried her best but missed by a lot.

The girls were all disappointed. I didn't make a spectacle or anything; I was very respectful. I wasn't sure how this would play out and I was truthfully a little nervous.

My Mom being the arbiter of fair play went into the house and got the camera.

When she returned Aunt Amy gracefully slipped out of her clothes and revealed a female form right out Maxim. She had on a silky black lacy bra and panties and I actually made a slight gasping sound as I saw her. She looked me right in the eye and asked, "How do you like your trophy?"

"I love it." I said with quiet sobriety. She walked over to me and wrapped her arms around me and kissed me on the cheek while pushing her boobs on the front of my chest so they would be in the picture. She also straddled her legs around me. I was surprised at how erotic she was behaving in front of my Mom and Sister. I knew I would be rubbing myself raw over these photos!

"Now, Jack, these are for you only! Remember that, I don't want these online ever!" She said.

"No. I wouldn't share these with anyone no matter how they tortured me."

"Man, I don't want to be home tonight. He's going to be cranking it so hard he'll tear the walls down!" my Sister said.

"You bet your butt I am and I don't even care if everyone knows it!" I said feeling like I wasn't even myself anymore but some supernatural being of power and male strength.

"Well look at Mr. Confident. Talking to a girl in her sexy underwear about how he will be masturbating later. Suddenly you're not the shy little guy anymore!" Aunt Amy said.

"I'm surprised at you Jack. You don't usually talk like that." Mom said.

"I'm sorry."

"No, no it's okay. We all know you do it, but I've never heard you talk so openly about it before today. Maybe this is the confidence boost you need." Mom said.

"So are you going to ask Jenny out anyway?" Lori asked.

"I don't know. Why do we have to talk about this during my big victory?"

"Well his confidence didn't last long." Aunt Amy said.

"I don't think it's his confidence, I think its just typical male bull crap!" Lori said. "He doesn't want to ask her out because right now she's the perfect woman—she's sexy, attractive, nice body and he doesn't have to know her as a person. He can just yank on himself while thinking about her boobs and not have to be involved emotionally."

"That's not true!" I argued knowing it was probably true.

"Then what is it?" Mom asked.

"I just . . . I don't know. It's . . ."

"It is that. You have a real problem with the way you look at women." Lori said.

Just then, and to my complete horror, I saw Jenny and her Mom walking up our driveway.

"Hey!" Lori said. I could feel Mom and Aunt Amy's eyes on me and I looked at the ground for the lack of a better place.

"Well what's going on here?" Mrs. Drake asked with a huge grin. Jenny was also smiling.

"You got my text?" Lori said. I shot her a glance of pure malice. But she just smiled back at me.

"Yup." Jenny said. "Hi Jack."

"Hi, Jenny." "Lori told me what you guys were up to and asked me to come over." She said looking more radiant than ever.

"What?" I looked at Lori.

She just shrugged, "I thought it would make things easier—and I thought you were going to lose. It's no big deal she already knows you like her. Everyone knows you like her."

They all giggled at me and I finally grew some balls, "Okay, I like you Jenny. And I do want to go out with you." I blurted out.

"Ask her more nicely, Jack!" Mom said in a slightly disappointed way. "Be a gentleman for God's sake!"

I despazzed long enough to ask her more like I meant to the first time, "Jenny, I really like you a lot. I have for a long time. And I'd really like to go out with you."

"Hold that thought!" Aunt Amy said.

"Oh come on!" I yelled and they all laughed again.

"Before you answer Jenny, we have one major problem with our boy Jack here." Aunt Amy said. "He only likes women for their bodies. And that is not the way he was raised was it?"

"Certainly not." Mom said.

"That's not true. I love women. And I respect them. Yes, I like looking at their bodies—is that so wrong?" I pleaded.

"No, it's not wrong, but it can be unhealthy." Mom said.

"Jack a lot of guys these days just look at porn and play video games and have no time to be with a real girl and learn to treat women as if they are real people. We all love you and we don't want you to be like that. That's all." Lori said.

"I know and I'm not like that. None of you know what it's like to be a guy! We think about sex ALL the time. It's just how we are wired. I know the difference between porn and real women. I would never in my life treat a girl poorly. But that doesn't mean I don't want to see them naked, because I do! The female body is magnificent! Just look at it!" I said motioning to Aunt Amy still in her underwear. "You are gorgeous and I can't take my eyes off you. And I mean that with the greatest respect."

"Thank you, Jack. That means a lot. But I think it might be helpful to you if you could understand what it is like to be objectified by the opposite sex. And besides women like looking at sexy guys as much as guys like looking at sexy women." She said and I was about to argue before she followed with, "And I can prove it. Maybe we need to go a little further with our wager."

"What does that mean?" I asked.

"How about this? How about we play another round of H-O-R-S-E. If you win I will show you my boobs, but if I win . . ." an enormous smile spread across her face. "If I win you have to strip right here in front of all of us completely naked!"

"WHAT! NO WAY!" I yelled. "I'm not going to get naked!"

"Then don't lose, Tiger!" Aunt Amy winked.

There was a strange sinking in my stomach. I was horrified at the suggestion, aroused at the proposal of seeing her magnificent boobies, and somewhat exhilarated by the thought of being nude in front of everyone.

There was a long silence.

"Jack." Jenny said. And I looked over at her and met her eyes for possibly the first time. "I like you too and I've been waiting for you to ask me out. If you take this bet I'll go out with you. Win or lose." She said with the sexiest smile I have ever seen on a girl.

"Mom, you can't be okay with this!" I said. "Are you really going to let Aunt Amy show me her boobs?" I asked unsure of how I wanted her to answer.

"What makes you think she will be the one showing anything? Maybe it will be you who has to show the goods." Mom said smirking.

"You would really want me to do that? Here!" I was shocked.

"It might not be such a bad idea to be objectified by women for a change and see what it's all about. I say make the bet—and for once in my life I hope you lose!" Mom said.

I was flabbergasted. I didn't know what to do. I had confidence that I could win, but I also thought I might screw it up under the pressure. Plus Aunt Amy was much better at basketball than I thought possible.

I looked over at Jenny—she was beaming. The sun was reflecting off her sundress, her skin was silky with slight perspiration. Her lips were parted with a smile and I could only imagine how soft and warm they must feel.

I panicked.

"Okay, I'm in!" I said and my hands began to shake. I swear the whole world shifted on its side for a moment and I almost fell over. I grabbed the basketball and began to dribble.

"One question Jenny," I said. "That text from my Sister, what did it say exactly?"

"That they were all planning on getting you to ask me out and then to get you naked." Jenny said.

"Why do you think I'm here?" Mrs. Drake said. "I want to see what my daughter is up against!" she added and the women all laughed.

I shook my head. "I thought something was off about this whole thing. It was a set-up!"

"You still agreed!" Aunt Amy said.

"I know."

"I'm going to beat the pants off you, Jack! Literally!" she said and my competitive side came out. "Prepare to strip."

"Let's do it!" I said with great confidence and the game began.

10 minutes later I lost.

I missed the shot and earned myself the final E.

The women erupted with delight.

"That's H-O-R-S-E!" Aunt Amy said. She finished the game with H-O-R-S and I lost!

I lost!

"You've gotta get naked! You've gotta get naked!" Aunt Amy taunted me.

"That's H-O-R-S-E now let's see that P-E-N-I-S!" Mrs. Drake sang to more laughter.

I looked over and my Mom was clapping her hands, my Sister was preparing the camera, Jenny was smiling brighter than ever, and Aunt Amy's eyes were saucers of delight.

I froze. Time stood still. My stomach felt like it was going to fall right out of my ass. I was sweating and not because of the heat.

"How about . . . just down to the underwear?" I pleaded.

There was a resounding "NO WAY!" from all of them.

"We want full-frontal male nudity! Right here, right now!" Aunt Amy said joyously.

"And no covering up, Jack." Mom added. "You have to show us EVERYTHING!" she said with great emphasis on the everything.

"I can't show all of you my . . . my . . . you know."

"It's a PENIS and you can show it to us. You have to—you took the bet." Lori said.

"I agreed to get naked, but nobody said anything about covering up or not."

Aunt Amy came over and put her arm around my shoulders "You are going to show us your bare chest, your bare back, your bare feet, bare legs, bare stomach, your bare ass . . ." with that she patted me on the butt and I jumped, " . . .and your bare penis, and your bare balls! That was the bet, you took it and you lost."

All the women lined up waiting with the biggest smiles imaginable.

"That was our deal, now you need to honor it." Aunt Amy said.

"She didn't protest when she lost, Jack." Mom said. "Now be a man and strip naked!"

They all started cheering me on and I gave in. To be honest I was kind of enjoying the attention. Suddenly it felt like a fun thing to do—it wasn't sexual, just a little naughty.

I pulled my shirt off to the exhilaration of the ladies. I got into character and flexed a few muscle-man poses. I'm not that muscular but I do have a pretty decent frame. I may have been stalling with the flexes because Mrs. Drake suddenly yelled "More Skin!"

I kicked off my shoes and pulled my socks off lying my bare feet on the burning asphalt. That's when I learned there really is no sexy way to pull your shoes and socks off, but the ladies politely encouraged my progress.

Them BAM—I opened the button of my jeans. My Aunt began humming The Stripper song. I slowly eased my zipper down and pealed open my jeans exposing a modest bulge. After a few deep breaths I dropped my pants around my ankles and pulled them tossing them in the driveway.

I was now only in my knit boxers.

The wolf calls and whistles would have had an entire neighborhood coming outside to see what was happening, but thankfully we lived in a fairly secluded area. I did my best to put on a show dancing and wriggling around. I knew I could only prolong this for so long, so I put my fingers in my waistband and slowly started to lower my underwear. Then I looked up and saw My Mom and Sister, my Aunt Amy (who wasn't really my Aunt) my soon-to-be girlfriend (I hoped) and her Mother all staring at my nearly bared body and I lost my nerve.

I pulled my underwear back up and waved them off.

"I can't do this—it's too weird!" I said apologizing.

The laughter at my embarrassment died down a little but those enormous grins stayed on every face.

"Oh come on! We want to see some wiener!" Mrs. Drake said.

"Mom!" Jenny scolded her.

"I'm sorry. I know I agreed to the bet, but it's just too weird. My Mom and Sister! Aunt Amy, Jenny's Mom, I just feel too bizarre." I argued.

"If you don't want to do it then don't, Jack. You've shown enough of your body to embarrass you—that was the point of the bet." Jenny said and I have never loved her more than in the moment—although she did sound a little disappointed.

"Alright Ladies, what do you say we let him off the hook? He's been a really good sport." Mom said coming to my defense.