n2underwear's fantasies

Part II

Shortly after that day, Jeff and I were at a friend Carrie’s house one afternoon after school. We were listening to music and just hanging out. They were laughing and talking about something and I was reading the liner notes on the album we were listening to when Jeff said to Carrie “Let’s pants him!” They were laughing and pulled me out of chair to the floor. They were tickling me and trying to get my pants off. I was horrified! I was wearing Jeff’s boxers that day! I fought back as hard as I could with strength I didn’t even know I had. They didn’t get my pants off, but I’m pretty sure Jeff saw the waistband of his own underwear when they were tugging and pulling. He stopped and said they probably shouldn’t do it. He smiled and looked at me and said “You’re pretty strong”. I thought if Carrie wasn’t there, I would have gladly let you take my pants off.

We graduated that summer. A married couple I was friends with asked me to stay at their house for 3 weeks while they went on vacation. Jeff asked if he could stay too. They knew Jeff and said yes. I was looking forward to living with him for 3 weeks. Maybe something would happen!

After a few days, he was bringing girls over and I could hear them having sex in the other room. Like I said, he was a ladies man. I would jerk off listening to them having sex. I had the master bedroom with the only shower in the house. A couple of times I’d wake up and hear him in the shower in the mornings. I’d go in and pee while he was in there. Dammit though, it was frosted glass so I didn’t really get to see much. He’d come out with a towel wrapped around his waist, and sit on the bed and talk to me. I tried to see up inside the towel, trying to get a look at his cock.

One day, he asked the girl that was there if she would give him a haircut. She was going to cosmetology school. She said sure. He took a shower and then sat in a towel on the toilet facing the bed I was sitting on. I lay on my stomach with my head at the foot of the bed to watch. Teasing him she was going to fuck up his hair bad. We were laughing about it. Then, Jeff spread his legs a bit and I was able to see everything hidden under the towel. I couldn’t take my eyes off his cock, balls and yes, blond pubes. I was memorizing everything, taking mental pictures of the shape of the head, the length and girth of the shaft, and the size of the balls. My mouth was dry and my hard on was pressing into the mattress. He wasn’t hard at all, but I don’t think he was completely flaccid either He just sat there smiling, giving me a free show while she cut his hair. I’m pretty sure he knew I was checking him out. Thinking back, he must have wanted me to the way he had his legs spread nice and wide in my direction. I couldn’t wait for them to go out for the day. I had to jack-off bad!

After my friends got back from vacation, they wanted to take their son to Knott’s Berry Farm which was not too far away. They took Jeff and me as a thank you for watching their house. They had a place where you could get “married” for like $3 and they gave each person a nail twisted in the shape of a wedding ring and a marriage certificate. It was the “Old West”. Jeff decided that he and I should get “hitched” at the Hitching Post. Our friends thought it was hilarious and said do it. So he and I got “hitched” that day. Unfortunately, we never had a honeymoon. I still do have pictures of that day with Jeff wearing his nail/ring.

As the summer wore on, we got jobs and were getting ready for college. We had busy schedules and didn’t get to spend much time together. I lost track of Jeff when his Mom and stepdad got a divorce and they moved away. I can still see those pale yellow boxers, that blond arm and leg hair and those pubes, cock and balls under that towel to this day. It started something I still do to this day. I will see a guy and check for those tell-tale signs of what kind/style of underwear they are wearing. The visible briefs lines under the butt cheeks, or the outline of the leg of the boxers under their shorts or pants. And then there’s the peek at the waistband. One of my all-time favorites is getting a peek at something you weren’t meant to see. Seeing up the leg of some hot guys shorts, getting to see what kind of underwear he’s wearing, etc.  Don’t get me started! Oh, and jockstraps. One of the guys I worked with for a few years used to wear white see thru cotton slacks and would sometimes wear a jockstrap underneath. I lived for those days at work!

After all those missed opportunities with Jeff, left me wishing I wasn’t so shy and had enough guts to make the first move. That’s something that plagues me to this day. Lots of missed opportunities over the years.

Part 1 It started with a friend in high school. His name was Jeff. He was blond, on the thin side but with a little muscle definition and a great butt. His arms and legs had thick blond hair. We were friends and I had a crush on him big time.  I’d often wonder if his pubes were as blond as him arm and leg hair. He was a ladies man. He had his pick of girls. Funny though, we hung out together a lot. Our third musketeer was Greg. Greg and I were a lot alike. Not popular with the girls, not exactly part of the “in” crowd at school. Jeff was though. But the three of us spent most nights hanging out, cruising or doing stuff. Greg was a year ahead of us in school; Jeff and I were in the same grade. I don’t remember how or when it happened. I think it was senior year. Jeff ended up spending the night at my house. I think it was his idea. We’d gone out with Greg as usual, dropped him off and headed to my parents’ house. I had twin beds in my room. I was nervous as a cat. There was Jeff, three feet away, stripped to his underwear and in the other bed in my room. I remember us talking for a long time in the dark. There was some talk about what he wanted to do with some girls we both knew and then he started asking me if I had ever done anything with anyone. I told him no. He said you don’t know what you’re missing. At that point, I couldn’t stay awake anymore. I think there was a pause in the conversation and I fell asleep. The next morning, we woke up and he said something like “You fell asleep on me last night”. I thought how I wish that were literal. We go up, got dressed and spent the better part of the day together. But nothing more was said about the previous night. Later that night when I got home, I sat on the other twin bed in my room (the one Jeff slept in). I kicked my shoes off and lay down. I was about to reach over to turn off the lamp between the beds when I saw it…under my bed…I reached down and grabbed it…a pair of Jeff’s boxer shorts. I thought how did they get there? I picked them up and studied them. They were pale yellow boxers with white piping around the bottoms of the legs and up the sides. I sniffed them right where his cock would have been. I was hard as a rock! Did he drop them? Did he leave them on purpose? I stripped down and put them on. I was a little heavier than he was, but they fit. I laid there and rubbed my hard dick inside his underwear until I couldn’t stand it anymore and pulled my cock out and shot all over the place. I didn’t want to come in them. I had other plans. I slept in them and probably had a hard-on all night. I wore them to school the next day. I could barely contain my erection all day, especially being around Jeff while wearing his underwear. I had to carry my books in front of my crotch all day. I didn’t say anything to him, and he never mentioned anything about them to me. I treasured those boxers for a long time and wore them frequently. I wore white briefs all the time. Boxers or briefs were just about the only choices back then. When I went in to the locker room to change for PE, the guy with the locker next to mine always wore boxers. He had curly brown hair and the most amazing blue eyes. His name was Max. I was in love with his eyes..but that’s a story for later. When we changed into our gym gear, he noticed I was wearing boxers. I saw him stop, look and then smile. “Those are much more comfortable, aren’t they?” he said. “They sure are”, I replied. If he only knew they belonged to Jeff and I was having one hell of a time controlling my constant erection while wearing them! I asked my Mom to pick me up some boxers the next time she went shopping.

Part II coming soon