Logan's Embarrassing Situations

A New Adventure

It had been 2 months since John had to move away. He graduated from college and got a job overseas working as an assistant director at some tech company. We still keep in touch from time to time, but nothing was like our time together. It definitely was wild and fun while it lasted. I continued to be his friend's house slut from time to time, but I missed getting pushed to do more embarrassing and humiliating tasks. I posted a couple ads online looking for a new dominant bully, but there weren't any bites. So I took that as a sign that I needed a brake and that I should just enjoy life.

~The next morning~

It was a beautiful day and I just had to get outside and work on my tan. Maybe I'd even go for a swim, who knew where the day would take me. I rifled through my closet looking for my swimming trunks, but forgot that John made me rip them all up. He bought me some really cool anime speedos and bikini briefs style swimwear, but they were all two sizes too small. My junk, let alone my ass wouldn't fit into them. I thought about my options and figured not many people would see me in the private pools, so why not wear the tiny speedo. I picked out a Naruto themed pair that was yellow and orange, it had the nine tails fox on the front and his tails spread out over the back. I pulled the tiny speedo up my legs and shimmed them up my thighs, but when it got to the top it was a struggle. I pulled and pulled and pulled, hoping that they would finally fit over everything. After what seemed like forever I finally got them to roll over my ass and junk. The front pouch really smoothed out my bulge, like I know I'm not the biggest but damn I looked pathetic in those. The only thing that spilt was my ass. It looked like I was wearing a thong rather than a speedo. The tails spread out on the back couldn't even be seen because my massive ass devoured them, but they did make my ass pop. Like move over bubble butt and hello CAKES!

I admired myself in the mirror for a good 10 minutes before I finally grabbed my sunscreen, keys & towel. I put on a pair of shorts and didn't even bother with a shirt. As I was on my way out to the car I got an text from my friend Victor that the community pool and the private pool rooms were temporarily closed. I couldn't believe I broke a sweat putting on the world's tightest speedo/ thong and now I can't even enjoy a nice swim and tan. I turned to head back inside when my neighbor Mr. Johnson called out to me. He had the look of desire on his face and I could tell he was up to no good, but I crossed the yard up to his porch anyway.

Mr. Johnson: Hello Logan, Where are you off to this morning?
Logan: Hi Mr. Johnson, I was just headed to the community pool, but they're closed today.
Mr. Johnson: Oh if you need a pool you can use mine. I just had it cleaned yesterday.
Logan: Oh no, I couldn't..
Mr. Johnson: I won't take no for an answer. Go ahead and enjoy yourself, I'll bring you out some ice cold lemonade. Maybe you can meet my grandson Phillip when he comes by later on.

Mr. Johnson was very persistent and I did really want to take a swim, so I agreed and went around to his backyard. When I opened the gate I was astonished! He had an in-ground pool, tiki bar, fire pit, pool chairs and even a brick wood burning grill. It was like I stepped into a super fancy resort. I laid my stuff down and took the time to fix my wedgied speedo, which was no use, before diving into the pool. The water felt amazing in the summer heat. I took a couple laps before just floating on the pool bed. I knew Mr. Johnson was watching me from the kitchen window, but when wasn't that old man watching me. Since he let me use his pool I decided to give him a little show.

I jumped out of the pool and tried my best at the slow motion hair flip with the water glistening over my body as the sun shining over me. I just knew that he was taking in every inch of my body. Since my speedo was soaking wet it became see-through slightly. My cock didn't look as impressive, but when I turned around the speedo was none existent. The swimwear was so far up my ass that I could have swore my asshole had eaten them. As my back faced Mr. Johnson's back door I heard footsteps. He was probably on his way out with some lemonade. I knew that it was my moment to shine, so I bent over at the waist with my legs spread wide apart. I spread my cheeks and clinched the fabric of the speedo and peeled it out of my ass. I heard clapping, so I looked back thinking it was going to be Mr. Johnson, but it was his grandson Phillip! The fabric slipped out of my hands and they immediately snapped straight back between my bubble butt. The snap caused me to let out a loud and low moan, I was immediately so embarrassed.

Phillip was your basic surfer guy with the long blond hair and the washboard abs. He was so hot... wait hot was an understatement. The guy glowed like the damn sun! Apparently he was in town for the summer until he went back to college.

Phillip: Looks like you could use a little help there bro.
Logan: Who me? Oh no, I'm just stretching. You know after a good swim you have to stretch out. No need to get stiff.
Phillip: Maybe I should join you because I'm feeling kind of stiff. *winks*
Logan: Oh ummm... sure you can

I continued to pretend to stretch next to the hot college boy. My not so impressive cock had tented my very tight speedo, so I made a dash for the pool. When I jumped I was pulled back by my swimwear. Phillip gave me the biggest wedgie I've had in a long time. He dangled me over the pool and bounced me up and down. My toes would touch the water, but never submerge. I could hear Phillip laughing and it embarrassed me, but turned me on so much. The bouncing stopped, but what came next was completely unexpected. He threw me down on the lounge chair with my face towards the pool and my wedgied ass facing the house. I bet Mr. Johnson loved the scene that was played out in front of him. Phillip sat on my back and grabbed my ass. I struggled to free myself, but he was not budging. He squeezed my ass like two fluffy pillows before drawing his hand back and cracking them down on my cheeks. I couldn't see it, but I felt my ass ripple from the intense slap. He did that several more times leaving my ass a bright shade of red. He gave me one more spank before he tugged on my speedo and letting it snapback.

Phillip: Well that was fun! I think I'm going to like living here. I can't wait to play with this beautiful ass all summer long.
Logan: Yes Sir
Phillip: This looks like it's going to be a beautiful new adventure. Now get up and get me some lemonade inside.
Logan: Yes Sir

~To be continued~