A few months ago I saw my friend’s small penis during a dare. The story is on my profile. Since then, we’ve had a sexual tension between us and we’ve done some light sexting and I’ve teased him a bit about his size, but nothing physical. He’s been BEGGING me to let him see my boobs.

During the holidays, we’ve had to run on our own for our Cross Country team, but sometimes a few of us like to meet up and run together, just to hold each other accountable. A few days ago, my friend and I planned to go to this trail near my apartment to do our run. It being about 7 AM the day after Christmas, the trail was pretty much empty. A few people were always hiking around the first mile or so, but once you go deeper into the hills, it’s extremely rare to see anyone else. That’s why I like running there.

We met up in the parking lot and I could tell he was staring at my ass in my running shorts. We started our warmup, passing a few hikers here and there, and small-talked about our Christmases and all that good stuff. We pulled off the side of the trail to do some stretches, and it couldn’t have been more obvious that he was staring at me. I’m a bit of a free spirit, and I definitely wanted to see him naked again, so I got an idea.

I told him that I wanted to do a strip run. Each mile, we would take off an item of clothing until we were completely naked. Immediately I could tell he was interested.

“What if someone sees us?” he asked, kind of worried.

“You’ll just have to run faster so they don’t see your little dick.”

We both laughed and he agreed to do it. For the first mile, we remained fully clothed, just to get our bodies warmed up. After mile 1, we looked at each other and both pulled our shirts off and stuffed them in a small backpack I brought with me. He looked so sexy. He has a 6 pack and really nice arms. After the next mile, it was time for the shorts. We stopped for a second to strip. Soon I was in only my pink sports bra and black underwear. He was wearing a gray pair of boxer briefs and there was very little bulge to be seen.

Both laughing, we started running again. Every time I looked over I could see his penis bouncing. After mile 3, we stopped again.

“Time for you to get naked.” I said.

“We’re both getting naked,” he protested.

“I still have my bra and panties left.”

“You’re a fucking tease,” he said.

I watched as he yanked his underwear down. His soft dick in the cold winter air was easily under an inch. I told him it was cute and he turned totally red. I could tell he wanted to cover up with his hands. He kept fluffing it to “warm it up” too. After a minute of making him stand there, I took off my bra. He wouldn’t take his eyes off my tits and his dick got fully hard in just a few seconds. I could tell how embarrassed he was by his accidental boner and I started laughing. I told him that if he didn’t get hard I’d be offended. Fully hard, he was probably 3.5-4 inches. Honestly bigger than I thought it would be based on his tiny softie.

We started running the next mile, his boner bouncing wildly.

“I can’t believe I’m naked right now,” he said.

“I know! Showing that little thing off is pretty brave,” I said with a smile.

Finally, after the next mile, I took off my panties and stood in front of him.

“Holy fuck,” he muttered.

I could literally see his dick pulsing.

“Do you want me to touch it?” I asked.

“Fuck yes”

“I’ll give you a handjob if you swear to do something for me,” I said.

“I’ll do literally anything.”

If I give you a handjob you have to run all the way back to your car naked.

“Deal,” he said without hesitation.

I pulled him a bit off the trail where there was more tree coverage. He shuttered when I touched his small cock, and overall the handjob probably lasted about a minute. We kissed after and I gave him a second to clean up before we kept running. I did a mile fully naked, because I keep my word, but after we finished the 5th, I stopped to get dressed. He stood there naked while he waited for me. By this time, he was soft and tiny again. There was only a mile left on the trail, and we were getting towards the area where the trail would be more crowded.

“I’m gonna run so fucking fast,” he said.

Although the last mile was supposed to be our cooldown, we both started running a bit faster. Just to mess with him I reached down and put my hand on his junk for a second.

“Don’t do that, I’m gonna get hard again,” he laughed.

As he said that, I could see a hiker in the distance. It was one tall person, probably a guy. My friend saw him too and started to say “oh shit, oh shit, oh shit.”

“Can I put my boxers back on?”

“Absolutely not.”

As we got closer, my friend covered up his dick with one hand (that’s all he needs) and I made him take it back off. Soon the guy was within 30 feet and my friend started sprinting past him. When I passed the guy a few seconds later, he just looked shocked but didn’t say anything. I ran quicker to catch up and finally got back up with my friend when we were near the parking lot. As we ran off the trail, there were at least 5 people scattered around the parking lot.

“Fuck!” he yelled out.

I could not stop laughing and had to stop running while my friend sprinted to his car, only to realize that I had his car keys in my backpack. I took my time going over to him while he stood there mortified, one inch wiener on full display. One older lady would not stop staring at him. I finally walked up and got his keys out and burst out laughing as he got in the car. I followed him in and tried to give him his clothes so he could get dressed, but he was already starting to drive, still naked.

“Where are you going?”

“I gotta leave before someone calls the cops!”

Sitting down in the driver’s seat, his penis just looked like a nub. I flicked it and made us both laugh. After a couple minutes of driving, he pulled over so he could get dressed. He asked if he could kiss me again and I let him. I’m not sure exactly where we stand on a relationship level, but I’m sure we’ve been texting about it and I’m sure we’re gonna have some more fun.