Logan's Embarrassing Situations

Logan's First Meet

Chapter 1

After months of messaging, my mystery master and I finally decided to meet up. We decided to meet up in two days, on Friday at noon. We agreed to meet at the empty baseball field in the park. The field was secluded, but still public enough if I needed to make a quick escape. He told me I could wear anything that I wanted, but I must wear tighty whities. I was fine with this because I usually only wear a pair of shorts and a T-shirt anyway. He told me to look for a guy that's wearing a red baseball cap and that would be him. I agreed and we said goodnight to each other.

The day finally arrived and I could not wait to finally meet the guy that's been giving me wedgie after wedgie every day. I got dressed in my white basket ball shorts, a grey Star Wars T-shirt and of course my Calvin Klein tighty whities and walked to the park. I didn't get to there until a little after noon. I looked for a guy wearing a red baseball cap. I spotted him at the far end of the bleacher, watching the baseball team practice. I walked up to him and introduced myself and was stunned by how amazing he looked. He had curly black hair, light almond brown eyes, smooth glossy skin, and a thick trimmed beard.

I reached out my hand, expecting a hand shake, but he pulled me in for a big bear hug. He squeezed me tightly and introduced himself as John. The hug wasn't too long, but when he let me go I felt my undies go with him. They immediately went up my ass and half way up my back. I didn't realize how tall he was until he stood up and had me dangling off the ground. John had to be at least 6'2! I couldn't help but blush and moan as I was flossed out in public with the baseball teams practice behind us. I was so embarrassed, but didn't want it to stop.

He carried me off the bleachers by my underwear and stood me in front of the fence, that separated us from the baseball players. He bounced me up and down before turning me around and hooking my underwear to the fence. With my full weight now against me, my tighty whities rode up to my neck. I felt the fabric slide between my cheeks, almost splitting me in half. My poor balls were crushed and cradled. I moaned and whimpered loudly and uncontrollably because of the pain, but also because of the pure pleasure of finally being wedgied by John.

Then to make it worse, John did the unthinkable and pantsed me! There I hung on the fence, pantsed and wedgied for all to see. I didn't think it could get any worse, until John screamed "NERD ALERT", to the guys on the field. Everyone turned and saw me hanging on the fence with my bare ass facing them. I was mortified, but wanted more!

To be continued...