This was the start of an ongoing interest in men and their underwear.
I grew up in a small town, the only son of strict parents. I was 15 and I only wore the white y-fronts that my mother still bought for me. They were baggy and not very comfortable but I had never known anything else. When I went swimming at the pool I always showered in my swimming togs and always wrapped a towel around myself when changing as my parents always told me too. I was very shy and always kept my eyes down in the changing rooms and so avoided seeing the other lads naked or in various states of undress..
I had started having erections at night time but never did anything with them.
That summer my cousin came from Canada for a three week. He was a year older than me and my parents set up a second bed in my room for him.
I had never shared a room with anyone before and felt uncomfortable at the idea but knew better than to say anything.
The evening he arrived we hit it off pretty well and when the time came we went up to my room to go to bed.
He was tired from the flight and he left his bags unpacked saying he would take care of them the next day.
As usual I took off my tee-shirt and jeans and put on my pyjamas leaving my underpants on underneath and got into bed. Des had gone to the bathroom and when he came back into the room, he just took off his tee-shirt and jeans and got into bed wearing only a pair of bright red underpants that looked like swimming togs and which I had never seen before. He kept talking to me as he got into bed and I couldn't not look at him.
He was about 5'11', well built as he played a lot of sports back home. He had a light covering of hair on his chest between his nipples and more around his belly button and a trail running down to the waistband of his underpants. Watching him getting ready for bed I got a weird feeling in the pit of my stomach which I hadn't felt before.
He was asleep almost as soon as his head hot the pillow.
The next day I got up first, got dressed and went down for breakfast while Des slept in. Eventually he appeared and had breakfast. By this time my parents had left for work so it was just the two of us. Des was still a bit worn out from the journey so he went back up to the room. I went up after a while and he was lying on the bed watching tv.
He asked me to give him a hand unpacking so we put his bags on the bed and opened them. As I said I had only known the white y-fronts that both my father and I wore and when I opened his bag there were a number of differently coloured underpants stacked neatly side by side. Seeing them I got that weird feeling in my stomach again but just carried on helping unpack and put his stuff away in the drawers and in the wardrobe.
Des then said he was going to take a shower to try waken himself up. I went to the press to get him some towels and when I returned to the bedroom he was getting undressed. He stripped down to his underwear, took the towels and went to the bathroom.
I lay on my bed and watched tv and after a while he came back with a towel over his shoulder and his underpants in his hand and standing there naked he finished drying his hair with the towel. I kept watching the tv but couldn't help stealing a look at his naked body. The trail of hair led from his belly button down to a good bush of light brown pubes from which hung a 4' penis. and nice sagging balls.
He put on a clean pair of light blue briefs, got dressed and we headed into town for the afternoon.
That night we went to bed at the same time and when I took off my jeans and was about to pull on my pyjama bottoms Des laughed and asked 'dude, what are you wearing, your old man's pants?' I blushed and said 'no, they are mine, my mam buys them for me'. 'God, they are so old style, no one back home would be seen dead wearing them'. 'And pyjamas too, no one under 60 wears them unless they are in hospital' he said laughing at me while I just stood there blushing. 'My mam gets me pyjamas so I have to wear them' I said. 'How will she know if you wear them or not? You need to get with the times and stop being an old man'.
Not wanting to seem like a jerk I left off my pj's and got into bed in just my boring old man underpants. It felt weird but good not having pj's bunching up when I moved in the bed.
The next morning Des went for a shower as before and while he was gone I took his red jocks out of the wash basket and put them on. It felt goof having the tight jocks cupping my cock and balls and while I was standing looking at myself in the mirror my penis started to harden and created a nice bulge in the front of the briefs.
I hadn't noticed Des had come back from his shower and was standing in the door looking at me. 'See, aren't they much better than your baggy ones? he asked. I nearly dropped from the fright and the embarrassment of him catching me in his jocks. 'Sorry' I stammered turning all shades of red. 'Hey dude, not a problem, you can keep them if you want, I brought plenty more with me'. 'And I can see that you are enjoying wearing them' he said pointing at the bulge tenting in the front, grinning. Again I started to go bright red and apologised once more. 'What's your problem Mike, there's no need to be embarrassed we all get hard ons'. He was naked with just a towel over his shoulder and when I glanced at his crotch I could see that he too was getting a bit hard. 'Looks like you are enjoying looking at me in your jocks' I said nodding in the direction of his crotch.
'Are you saying I'm gay?' he said. 'No' I stammered, 'I was just joking'. 'Well I'm not' he said 'but I sometimes like to jack off with my friends'. I didn't know what he meant and when he saw the blank expression on my face he said, 'don't tell me you don't jack off'. 'Don't know what you're talking about' I said. 'Masturbation, wanking,jacking or jerking off, spanking the monkey? No' 'I've heard of masturbation but don't know what it is' I said. 'Oh man you have a lot to learn but don't worry I'll show you what to do'.
With that he jumped at me and pushed me onto my bed where we wrestled, laughing. He was bigger than me and pinned me down with my arms held down with his knees. He was kneeling on top of me naked and his penis was now fully hard and about 51/2 inches long. He reached back and pushed my briefs down and my penis which was about the same size as his sprung out. He got off me and lay down beside me, his penis rubbing against my thigh. 'Now just lay back and enjoy' he said and then wrapped his hand around my throbbing penis. I was a mess of emotions feeling that what we were doing was wrong but his hand on my penis felt good. He started moving his hand up and down, pulling back my foreskin but it hurt when he did so he said that it would get looser the more I jacked it. He continued stroking without rolling back the foreskin and in no time I got this feeling like I needed to piss but he said that it wasn't a piss that I needed and stroked faster. Then an amazing feeling came over me and white liquid shot out of my penis all over his hand and on my chest. 'What the hell is that?' I asked. 'Jesus dude don't you know anything?' 'that's semen, cum jizz, there are different names for it' he said 'but its all good'. I felt kind of ashamed but it felt great at the same time. Des picked up the jocks and wiped the cum off his hand and off my chest, lay back and jerked himself with the underpants wrapped around his cock and after a while he groaned and let loose a load of cum. 'Well, how did that feel?' he asked. 'Incredible' I said.
That was the first of many jerk off sessions we had during his trip. Sometimes we slept in the same bed, our arms wrapped around each other. He left me some pairs of his briefs when he went home and when I got a part time job I added to this collection.
From that visit I love to see a guy in a nice tight pair of briefs, loose boxers favoured by so many now don't do anything for me at all.
I also had other jerk off friends in school after that summer and I enjoyed each experience but have never forgotten my introduction to the joys of wanking.
I'd love to hear other guys underwear stories.