Soccer training embarrassment

When I was in high school I played soccer in a team with a few of my friends. We would train on a Tuesday night at my school about half an hour after school ended, so I would bring my uniform to school, change in the bathroom after classes and wait until practice started. Most the team would do the same, except for a couple of boys on the team who went to a different school, one of whom was named Matt.

I always wear briefs, and if I wore dark colored underwear they were very visible through the white shorts that my team were made to wear. Matt liked to make fun of me whenever my underwear was visible, saying things like "I think I had those undies when I was 5!" or "nice panties!"

We would occasionally play dumb pranks on each other like pantsing, or make funny bets that would result in an embarrassing forfeit like having a penalty shootout where the loser had strip down to their underwear and do laps of the field.

Our coach never encouraged this behavior, but he never really cared enough to stop it.

I had seen Matt's underwear a few times because of this and he always wore the same pair of underwear: a pair of black boxer briefs.

Very rarely another teammate would be caught wearing a pair of briefs and they would be made fun of for the day, but for almost 2 years of playing on the same team Matt had never worn briefs.

Each practice I would check to see if he was wearing briefs for a chance to embarrass, but I would always see the dark outline of his boxer briefs through his white soccer shorts.

One practice Matt arrived only 5 minutes before practice started, much later than he normally would. He was still wearing his school uniform and had his school bag on his back, which was weird because he always showed up in his uniform.

"Mum was busy and was late picking me up, so I didn't have time to go home and change like normal" Matt explained, "so she brought my uniform from home and now I have to get changed here." He walked off to the toilets and came back just as practice was starting in his uniform, but also wearing his school jumper over top. We occasionally did this if the weather was too cold, but it was a relatively warm night and the jumper was not necessary.

I thought it was weird, but didn't mention it. We started practicing and mucking around, but Matt seemed more timid than usual, staying away from the pranks. I also noticed that wearing his jumper meant that I couldn't see his underwear through his shorts.

I decided to mess with Matt, making sure that he was the one who got the ball as often as possible and chasing him around when he got it. Eventually my plan worked and he got too hot. He took off his jumper and I saw a flash of red fabric on his hip. This was the first time I had seen him in any underwear that wasn't black.

About 15 minutes later our coach received a phone call and told us to take a break before walking out of sight.

We all walked over to the taps and had a drink of water. As we were walking back to the field I decided to trick Matt into exposing his underwear.

"Hey Matt," I said. "I bet I can climb that fence faster than you!"

He looked at me slightly confused. "Bullshit" he replied.

I smirked at him, "prove it."

I could tell that he was confident in his ability to beat me, but he was still cautious.

"What do I have to do if I lose?" He asked me.

I thought for a second, before replying. "Nothing, I just want to prove that I'm faster. But if you beat me, I'll do the rest of this training session in my underwear"

That had convinced him. We looked at each other for a second before both sprinting towards the 8 foot tall chain link fence.

He was a faster runner than me, so he reached the fence first and started climbing it. He was already half way up before I started climbing.

I hurried up the fence but by the time I reached the top Matt was already sitting there with a big grin on his face. I sat up next to him, looking embarrassed.

I pretended to lose my balance and swung my hand wildly, pulling on the back of his shirt to keep balance, resting my hand on his back to stay stable.

I snuck my hand down his back and as he was about to jump off the fence I pulled his underwear and slipped his waistband over the fence.

He jumped off the fence but instead of hitting the ground he swung, suspended by his underwear.

Matt yelled in shock while the rest of the team roared with laughter. The legholes of his bright red underwear were very visible, stretching out of the top of his white soccer shorts.

My suspicions had been confirmed, he was definitely wearing briefs!

I climbed down from the fence and joined the rest of the team, laughing at Matt hanging in his briefs. His face had turned almost as red as his underwear.

"Nice panties" I said.

Our teammates pulled on his legs to worsen the wedgie, and even yanked his shorts down to his ankles, embarrassing him further.

I had never seen Matt so embarrassed, I laughed so hard I could barely stand.

Unfortunately that didn't last long before my teammates turned to me. I had forgotten that I lost the race and I had a forfeit to fulfill, but the others had not