"Hey man, you want to come to visit and stay with me a few days? My parents are taking my sister to Europe for two weeks and asked if I could house-sit while they're gone."
I first met Scott when we joined the same middle school softball team. We became best friends and hung out together all through middle school and high school. We were really bummed when his family moved to California two years ago, right before we started our senior year. It was sad to not graduate together, but we stayed in touch, even after we started college in different states. We chatted a lot online and often gamed online together, but I hadn't seen him since the move. Now after our first year of college, he was offering a chance for me to visit him.
"Sure! Sounds like fun."
I asked him about the dates and made arrangements at my summer job on campus, so I could have time off. I found the cheapest flight I could, and when I arrived, Scott met me at the airport.
"Great to see you, Bobby! Glad you could come."
Scott drove us back to his place, and huge house in the suburbs, with hilly landscape and winding roads. His dad was an executive and his mom spend a lot of her time on their house.
He showed me around and I teased him about living on an 'estate'. They had a beautiful pool area that was secluded and inviting, with a high fence and lots of plants.
We had a late lunch and got caught up on our lives. Afterwards, he took me to his bedroom, a converted loft.
"Wow, this is really nice!" I exclaimed. "You could live up here!"
The room was long with sloped a ceiling. One wall had huge windows, with two other windows on another wall. Scott had a large TV at the foot of his king-sized bed, hooked up to his Nintendo and Xbox controllers. There was a small refrigerator, a couple of dressers and couch. Off to the side I saw a bathroom.
"Thanks! I used to be in here all the time, but I don't spend as much time here now that I'm away at college. I enjoy the privacy and access to my gaming system. My parents asked if I could come home to watch the house while they were in Europe with my sister, and I thought it would be a fun opportunity to get together with you."
"You can sleep on the bed. I'll take the couch."
"Thanks, but the bed is huge. There's room for both of us, as long as you don't get too grabby", I teased.
"How about a game of Smash Bros?"
"Sure, set it up."
Scott got out the game and two controllers and stated it up. It was kind of warm in the room, so he opened the windows to let some breeze through.
"Mind if I get comfortable?" Scott asked.
"Sure, since I'm going to kick your ass, you might as well be comfortable."
Scott kicked off his tennis shoes and removed his socks. He stripped off his t-shirt, then dropped his cargo shorts, standing there in his Hanes tighty whities. He sat cross-legged on one corner of the bed and looked at me.
"Well, are you going to join me?"
I was a little surprised how comfortable Scott was stripping down to underwear, but we had been like that many times during our childhood, at sleepovers.
I removed my clothes, leaving on my loose light blue boxer shorts, and joined him cross-legged on the other corner at the foot of the bed.
"Nice boxers! When did you start wearing them?"
"For a while now. When my grandpa passed away, I was helping my grandma go through his stuff and I found an unopened pack of boxers, so I asked if I could have them. She said sure, and I just really liked the look and feel, so I gradually got more."
"Awesome! I've always wanted to try boxers, but my mom always buys me briefs."
"I love them. Want to try these on?"
I slipped the boxers off my hips, keeping my legs bent and together to hide my dick. I tossed them over to Scott.
He laughed and said, "Thanks. Here, let's swap."
Scott stood up and slipped off his briefs and tossed them to me. I had never seen him naked before, and I must have stared a little at his beautiful body and soft cock, because he laughed, "You like what you see?" and he gyrated his hips a bit to swing his cock around. He pulled on the boxer shorts and modeled for me.
"You're right! These feel great." I could see him tenting a little in the front as he sat back down on the bed.
I pulled on his white Hanes briefs, the kind I used to wear, and it took me back. I liked the feel of the soft cotton, and how they looked on me.
"I forgot how briefs feel like you have a hand holding your junk in place", I laughed.
"I'm enjoying the view. Come on, let's play so I can kick your ass!"
We started a marathon session and were pretty well matched. I was great hanging out with Scott again, laughing and talking as we played. It was also a little arousing being in our underwear (and each other's underwear at that) so close together. I caught Scott checking me out from time to time, and I enjoyed seeing his tent pole rise and fall in the blue boxers.
After a long while, Scott wanted to take a break. He said his shoulders were aching a bit and he needed to move around.
"Want a massage? Here, lay down and I'll work out those kinks."
