LOST BET – POPSICKLE UP A***!
Male, 40’s, have a naughty 50-something female neighbor. I was over hanging out by pool. She had two girlfriends over. They were reading girls magazines articles about s*** dares to cool off for the summer. Running through sprinkler naked, skinny dipping, etc. The list got kinkier as it went on. So they posed the question to me – would I let someone put a popsicle in my a-hole? I said yes, but just briefly because I read that ice can damage the delicate tissue in the a***/r*****. So one thing led to another and yeah, I let them do it.

I laid on a lounge chair, face down at first, and they pulled my swim suit down to my knees and spread my cheeks apart to see my a***. They dripped some baby oil on my a*** and rubbed it in with their fingers. They got a popsicle out, one of those red/white/blue ones. I was getting nervous but having fun, though awkward and exposed like that. Then, I felt the tip of the popsicle on the opening of my a***. brrr, it was cold. I clenched up. They laughed and told me to relax. I could hear their cell phones taking pictures! They were having problems reaching me and holding my cheeks apart and asked me to remove my swim suit completely and turn over and spread my legs up on the arm chair rests! I felt like a girl at the gynecologist, spread wide with everything out there in the sun for them to see! I did as I was asked, it was hard to say no, they were all having so much fun. And I admit, although awkward and naked, I was enjoying it, too. So I scooted on the lounge chair so my a** was available/accessible to them and opened my cheeks and got ready for them to penetrate me with the popsicle. My neighbor put it in her mouth first to make it slippery. The other girls said “ew, you know where that’s been!” to which she said “well, he’s been in the pool, he’s clean, look at it, that’s the pinkest a-hole I’ve ever seen as she slipped a warm finger inside me! Then, slipped the ice cold popsicle in me inch by inch until it was all the way in me! She let go and I kept it in me for as long as I could before it was too cold to take, and I used my a*** muscles to push it out onto the lounge chair. The girls yelled/cheered “next” – and the next girl grabbed it and started moving it toward my a***, which was dipping with melted purple popsicle juice. “Wait, one girl” yelled, “you’ve gotta lick it!” And they all laughed. She basically deep throated the popsicle before slipping into my a***! I held it for as long as I could but it was so cold! Then the last girl knelt at the foot of the lounge chair, between my raised legs, cell phones clicking away. And instead of licking the popsicle, she spread my cheeks and licked my a***! Her warm tongue felt GREAT on my cold flesh. But before long, she slid the ice cold popsicle inside me for my last and final popsicle penetration, and slipped it in and out and in and out, as they all cheered!

I wasn’t going to include this last part but the reality was – my a*** had obviously had gotten some melted popsicle in it and they started thinking that might not be good to have inside me. So they spread my cheeks wide open, so wide my a*** “gaped” and they poured a warm glass of water in me to rinse me out! They washed the popsicle off my cheeks too. But they laughed and took pictures of how my a*** was purple from the red/white/blue popsicle – kind of like how children’s tongues would turn blue/purple after eating a popsicle. The next day, when I was walking my dog down a wooded bike path nearby, I ran into one of the women. She apologized for things getting out of hand, but said she had a really good time and everyone had fun, and then added “and I got good pictures, too!” and whipped out her cell phone and proceeded to show me! How embarrassing. But I did want to see how I looked! My a*** was really blue-ish purple!