Pool Prank Turned into a Skinny Dipping Party

Adam sent in this story about a prank going good for once:

My old girlfriend used to love trying to get me into embarrassing situations. Most of the time it was harmless, like leaving our apartment window open and taking away my towel after I had gotten out of the shower. The chances of someone catching me in the nude in those instances were pretty slim.

But one time we were at a pool party with some of our friends, and she dared to go further. I was wearing board shorts, she was wearing a bikini, and while our friends were diving in the deep end, and the two of us were hanging out in the shallow end, she suddenly started tugging at my shorts, trying to get them off of me. She whispered “take them off, it’d be so funny!” But I wasn’t about to let her win in embarrassing me in front of our friends, so I tried as slyly as possible to keep my shorts up without anyone noticing. But she was persistent and wasn’t actively trying to hide what she was doing, so she rigorously pulled at the front of my trunks until they slipped through my fingers and fell to my ankles.

I desperately bent over to pull them back up, but she gave them one last pull, knocking me off my feet and pulling my shorts off completely. A look of astonishment immediately crossed her face at the success, and she immediately threw my shorts over a backyard fence. She gleefully looked down at my naked body, and then with a smirk openly suggested that we go diving next.

I immediately froze, completely naked in the water, with no way of getting to my suit without my friends seeing me completely in the buff. My girlfriend smugly got out of the water and walked over to the diving board, beckoning to me. I then realized that she had won, and I had no choice but to own it. I got out of the water and began walking proudly in the nude in the open air towards the diving board.

My friends immediately expressed their shock while my girlfriend laughed hysterically. One of them asked “umm, where’s your suit?” and I proudly stated “I just wanted to feel free!” Everyone laughed at that. I stood atop the diving board, my bare body to the world, and then dove the most perfect dive I had ever done. I came to the surface and everyone was either laughing with my girlfriend or just looking on in amazement.

I was determined to not let myself feel ashamed and yelled “it’s really refreshing!”, though I’m sure I was red in the face. Coming to my rescue from embarrassment, my best friend got onto the diving board, eagerly pulled off his own swim trunks, and canon-balled into the pool naked. I instantly felt better not being the only one in the nude.

But my best friend must have been full of adrenaline from taking the naked leap, because he immediately made the daring move to start encouraging his girlfriend to get naked too. She just laughed, but then everyone got caught up in the excitement of me and my friend getting naked, and we all started encouraging her, too. So she hesitantly got out of the pool, and we all started cheering her on. She got on the diving board, grabbed the top part of her bikini, and flashed us her boobs to more cheers and a wolf whistle from her boyfriend. She laughed, obviously enjoying herself. She pulled her top off completely and then pulled her bottoms down while wiggling her hips.

She jumped in, and then everyone else took their turn, stripping and using the diving board as their catwalk, even my girlfriend. It was so much fun! It ended up being one of the most fun times I ever had with my friends, all because my girlfriend tried to prank me.

Thanks for the story about success at getting new converts, Adam! But I wonder, is this why she’s your “old girlfriend”?!!?

-Jen