This happened when I was 15 years old. I grew up in a small town the son of strict parents and anything to do with sex was a taboo subject in our house. One summer afternoon I has been out playing football with some friends and was walking home when I met Denis. Denis was a few years older than me but as my parents owned a store in town I knew him from coming in to the store. We got talking and I don't remember exactly how it happened but we ended up back in his house. I was wearing shorts and a tee-shirt having just come from football. He took out a porno magazine and we started looking through it. I was nervous and excited at the same time as I had never seen anything like this before.
Denis nodded towards my crotch and said I can see you are liking what you see. I went red from embarrassment at the bulge in the front of my shorts but he said not to worry. He asked me how big my penis was. I stammered 'I don't know, I never measured it.' He told me to drop my shorts and underwear and he took out a measuring tape. When he took hold of my cock to measure it I came. I was scared as this had never happened before but in some strange way it felt good. He laughed, said that was quick and gave me a tissue to wipe up. 'That never happened to me before I said'. 'You mean you've never jerked off before?' he asked. 'No' I replied. Well if you want to do it again I'm here most afternoons around this time. That night I lay in bed and thought about what had happened and decided I'd like to have that feeling again.
Next day I called around to Denis' house. He opened the door with a grin and said 'c'mon in'. This time we went up to his bedroom. He stood in front of me and without saying anything he lifted my tee-shirt over my head and his hands were all over my chest, rubbing my nipples and he said that he loved my hairy chest. I was getting hard by now. Then he opened my jeans and, put his hands down the back and massage my butt cheeks and then pushed by jeans down. I was standing there in just a pair of blue briefs with a nice bulge. 'Love your underwear' he said 'I love a nice bulge in a pair of briefs.' Now your turn.
So I slowly undressed him in the same way as he had done to me until he stood in front of me in a pair of bright red briefs. I has always liked looking at the lads underwear in the changing rooms at sports but this was the first time I was this close. I reached out and brushed his bulge. We lay on the bed and hugged, massaged each other. He slid off my jocks and my 5.5 inch dick sprung up from a thick bush of black pubes which Denis loved. I removed his red briefs and put them over my face getting the lovely musky man smell. Denis' dick was bigger than mine, about 6 inches with a lovely bush of light brown hair. Taking each others cocks in hand he said 'just do as I do' and we slowly jerked each other off. When I got that strange feeling again I said 'it's happening again' and Denis pumped my dick harder until I shot a hot creamy load all over my chest and it felt great. I kept jerking his dick until he followed and shot his load all over my hand and his chest. We lay back on the bed feeling spent but happy. Denis wiped the cum of our chest with his briefs which he then put back on
'I love the moist feeling from cum in my jocks' he said which I thought sounded good and that night I jerked off at home in my briefs and went to sleep wearing just the cum soaked underwear and it did feel good.
I visited Denis many more times during that summer for some afternoon delight. He had some men's underwear catalogs which I loved looking at and I also loved going through his underwear drawer which was full of briefs of every color. We shared a love of underwear especially brightly colored briefs.
On day when I was opening his jeans Denis said that he had something new to show me. I pulled down his jeans and he was wearing a bright pink thong which really got me turned on. He left the thong on for our jerk off session and the cum oozed thru it. He then took it off and gave it to me. 'Think of the fun we've had together when you wear it' he said with a grin. I filled that pouch many times.
We had many more experiences that summer which I will relate at a later date.