[pball2295]

Disclaimer to start: Until discovering this site, I never planned to share this story with anyone (except my friend, obviously, ha). So I started writing it up, intending for it to be a paragraph or two. Personally, I hate reading long, overly descriptive stories. But I felt I needed to set the stage to contextualize why it ended up being such a hot event in my life. Take it or leave it.

My buddy (let's call him Tim) and I are in our mid-thirties now. When we were in college, we played a lot of ping pong together. We played a few times a week and were pretty competitive, but it was always in good fun. Midway through our freshmen year, we both started dating superrr cute girls. Smart, successful, confident girls. (I'd say women, but we were all 18 or 19 at the time). We met them a few months apart, and the girls quickly became friendly too. At some point midway through the year, while Tim and I played ping pong matches, we started jokingly betting "free nights" with our girlfriends, depending on who emerged victorious by the end of the session.

The ongoing joke went..."Alright Tim...Best of 7, games to 21. You win, you get Julia for the night." Or he'd say, "everything is on the line Will, you win, you get to bang Jess. Julia was a 5'5 beautiful Italian girl (as in, New York Italian), with lovely C cup tits. Jess was a tall, athletic brunette. Small tits but just a bombshell. She played tennis at the college.

Spoiler alert — we weren't ever actually going to bang each other's girlfriends. We were both to inexperienced and lovestruck for that level of kinkiness — unlike the some of you freaky users of this site, lol. But it was definitely fun to joke about, as evidenced by the fact that it was an ongoing theme. The fact is, we were all attracted to each other. Me to Jess. Jess to me. Julia to Will, Will to Julia.

Anyway, eventually, Julia and Jess started playing doubles with us. One time, after Tim and Julia lost a match, Tim jokingly said, "well shit Will, I guess this means you get Jess tonight!"

What!? The girls yelled.

We laughed and explained the joke. They giggled it off as and called us pervy, immature boys. "Yep, that about sums it up!" we said. The joke continued the next few times we played doubles together. Somewhere around the 5th time it came up, Jess finally said..."well we aren't going to swing with you perverts... so you might as well bet something more realistic!" Julia laughed and nodded.

On a whim, I responded, "like what Julia...the nudes you send me?"

Julia whipped her hair towards me and made a pretend 'how dare you!" face. (Meanwhile, I noticed a strange twinkle in her eye). Tim and Jess cracked up. Tim was intrigued and laughing, Jess, the most conservative among us, was embarrassed but still laughing.

This is where things got interesting.

Julia responded, "Psh, I don't even care...you can bet those nudes of me! I have faith in your game babes!"

I shrugged my shoulders at Tim, and he cheered her on, laughing. In truth, it didn't surprise me that Julia said this..but it definitely suprised me that she wasn't hedging on the statement, or taking it back. (Editors note: that's only because she and I had only been together for a few months...turns out this kind of thing wasn't out of character for Julia at all. At that point, Jess exclaimed, "Uh oh, I'm out...all three of you are pervs!" We all laughed and kept playing.

For the next several months, Tim occasionally brought it up while we played. Always "jokingly." of course. But the sheer amount of times he reverted to the joke indicated to me he was hoping I'd oblige. My position all along was that I'd do it (the idea was beginning to turn me on too), but only if he would share some equally naughty pics of Jess. Tim would say...ah...I wish I could man, but Jess isn't comfortable with that stuff. She wouldn't even consider letting me take nudes of her. Being the refined 18 year old gentlemen I was, I said, "Tim I completely respect your decision to not pressure Jess on this, and therefore...no deal."

In time, it became clear to Tim that I wasn't going to show him Julia in the buff without a fair deal.

Fast forward to the end of our Junior year now, some 2-2.5 years later. Julia and I had broken up a few months prior. It was a mutual split, and it was for the best. She was a wild Italian girl. Smart as a whip, but studied hard and partied hard kinda girl. Today, she's a lab-scientist. I was a bit more reserved. Play sports, go the movies kinda guy. We were too different. Anyway it was a bit touch and go for a few months after we broke up, but eventually Julia and I reconnected as friends with benefits (great decision by me). In the meantime, I knew she was sleeping around too. It didn't bother me, and so was I. College...damn, good times.

Anyway, a few months after Julia and I split up, Jess broke up with Tim. Cheated on him, actually. (Whoulda thunk, Ms. Conservative!).

Tim was completely crushed. He thought he and Jess would last forever. For the next few weeks, the guy was an absolute shell of himself. So I thought about it, and decided to use some of my savings to rent a house at the beach...boys weekend, just me and Tim.

And wouldn't you know it, we got to the house, they had a ping pong table in the basement! Tim was glad to take his mind off his broken heart, and on that Friday eve we had some epic battles. Nearing the end of the night, Tim was beating me handily in a game to 21. Bad day on the table for me, friends. I'm better than him, I swear. Just then, as Tim was about to put the nail in my coffin...an idea hit me - largely inspired by Tim's genral state of misery.

"Hey Tim, I said..."loser has to share his girlfriend."

Tim's eyes widened.

"Hahah, seriously?!" He said.

"Absolutely. But only if you win."

In his excitement, it took Tim a few points more than it should have to seal the deal. The game ended up being closer than it would have been...21-18 or something. But alas, I had been defeated, and as I said to Time...to the victor go the spoils.

This was a long time coming. By now, I was well over Julia emotionally, and she had made it perfectly clear that me sharing her nudes with Tim didn't bother her. Moreover, in the time since, I learned that she had been even more attracted to Tim that I thought— which might have explained the evident mutual horniness. Any, I knew Jess's nudes were off the table now, so I grabbed my cellphone and Tim and I took a stroll to the beach.

At this point, I was probably getting as excited as him. The thought of exposing Julia to Tim had turned me on since the fake betting days. Now, it was about to happen. We sat down near the water, and I slowly opened a locked folder on my phone.

"You sure you want to see Julia naked man?"

Tim laughed. "Yeah...pretty sure about it!"

I had perused these pictures many times, so I knew the drill. There were only three here. The first was of Julia, smiling at the camera in her underwear and bra. Such a cutie. I opened it and Tim and I huddled up.

Tim looked closely at the pic and said, "Je-sus."

But the truth is, he'd seen her in a bikini many time before. I'm sure the context was a turn-on, but at this point, it's nothing he hadn't seen before.

I said, "Really good...right"

Tim nodded and smiled.

Ready? I asked?

"Absolutely," he said.

One swipe to the right, and there was Julia. Smiling at the camera, cute as a button, proudly exposing her tits, as if she knew Tim was watching. He couldn't contain his joy. He said, "Holllyyy shitttt man!"

We high-fived like losers. (You could argue we were, lol).

Tim stared at her perky tits for at least 30 seconds. I zoomed in on her nipples, then up to her smile, her cameltoe underwear, and back out so he could get a full scope.

"Awesome man!"

"Ready for the money shot?" I asked.

"More than you know." He said.

Another swipe, and there she was. My wild, beautiful, naked Julia. Full frontal, smiling at the camera, completely naked. Tim didn't say a word. I laughed and gave him the phone so he could take in every inch of her. I had taken these shots right after she returned from the beach herself (said I wanted to "document her tan." lol)... so she was dark everywhere but her tits and the skin under her bikini bottoms.

Julia typically shaved her pussy and left a runway. For whatever reason, during this stretch, she decided to let her bush grow out just a bit. Tim didn't expect that, and he was mesmorized. He asked me questions like a kid in a candy shop. Did she always keep it like that? Did you like her shaved or with a little bush? I encouraged him to zoom in on her pussy. He gladly obliged. I was loving it...my best bud, starting at Julia's pussy. Unreal.

We went back to the rental house, grabbed a few more beers, and at Tim's request, I pulled up the same 3 pictures on my large laptop screen. We cracked open some beers and Tim continued his thorough inspection of her. At one point, I set Julia's naked body as a screensaver. She bounced around the screen naked, which was delightful. After 30 minutes of this, Tim asked the question I wondered he would.

"Shot in the dark man...do you have anything X rated of her?

Julia was... Julia, so the short answer was...of course I did! Even though I knew I'd show him, I wanted to make him earn it. So I said, "ahhhh I don't know man, they are pretty porn-ish...I'm not sure if she was talking about those pictures.

"Ohh come on man, I promise I'll never tell a soul... I've seen this much of her already, no point in stopping now!" "She didn't specify which one's you could show, did she!?"

"Haha, okay man...just don't tell anyone."

Within a few minutes, we were scrolling through pictures of Julia spreading her legs open wide, fingering herself, and Tim's personal favorite...Julia's back arched, head turned towards the camera, with her hands spreading her asshole as wide as her little hands could. Again, I was awestruck. My best friend zooming in on an 18 inch screen on Julias little asshole.

By now, it was probably 5 am. Predictably, Tim asked me if he would trust me with owning the pictures.

I told him that I didn't feel comfortable sharing the pornographic ones, but that I'd blur her face and send him the full frontals. He was endlessly grateful for this. Years later, he admitted that he STILL jerks off to Julia's nudes occasionally, and that it helped him get over Jess.

And hey, I may have ended up sending him one or two of those spread asshole pics afterall.

And that's the story of betting nudes with my friend.

There is some more to this story. It's a bit more graphic, and I dunno if it qualifies as "low key" I can follow up if people want to hear it.