Here we go!
My story ends in 1978, many years ago.
I was a senior at a prestigious prep/boarding school in New England, the sons of the elite of the elite. Old world money, and Brahmin society. Some of the wealthiest folks on the east Coast sent their boys here to "prep".
Prior to this I was schooled at another venerable elite school for you boys. My family was first generation of successful, but NOT a family of historic prestigious wealth, but of Irish immigrant total poverty past. But My dad busted out and became a wealthy guy.
At the middle school, white jockey briefs were worn by every boy. The gym was a feast of Jockey briefs or Jockey ‘shorts’ as we called them, sleep overs were all of us hanging in "jockey shorts" with the black dotted waistbands. Slowly it became a fetish. Seeing the waistband with boys bending over, lifting T-shirts and exposing stomach with treasure trails to a Jockey waistband. I was a fanatic!
I was LUCKY to be accepted to the next level of this educational program for high school as were several of my fellow students in 1974. ‘Yahoo’ here we go! we all shouted, all in our Jockey shorts.
So the first locker room experience in the new high school proved to be a shocker. The older boys all worn baggy boxers, and I actually witnessed a bud who stripped to his Jockeys be hung by the waistband giving him one hell of a wedgie.
I returned home and reported to Mom I needed boxers shorts immediately. I hated the bulk and sorely missed my Jockeys. BUT, I wasn't a fool. The school had a heavy sports program, and we were all naked in gang showers, and stripping down regularly. So I followed the crowd. But kept my Jockeys for times I knew I didn't have to strip at school. I also whacked off in them more and more.
Fast forward 4 years to senior year. College hunting with my best bud, a soccer star, muscled, smooth, dark hair, incredibly masculine, HUGE dick, and massive balls. He always wore ‘Jockey shorts’ (Jockey Briefs), despite the teasing no one would fuck with him, he was a total ladies man, popular, super star athlete, plus he played in a rock band as the lead singer and had girls just hanging on him. He was a total horn dog always talking dirty and always trying to get laid.
He had this huge thick dick, but it looked even bigger while he strutted around the locker room because he had the bull balls in a TIGHT sack, that made his dick stick out straight from his body. The biggest sack and almost bizarrely tight, he always looked like he was about to explode. When he wore his jockeys his dick stuck straight out always, stretching the fabric into a tent. I always admired him both getting dressed and in the shower.
We decided to go college hunting together, traveling around the east coast, and staying in various hotels. When I packed, and I got to underwear, I thought, hmmmmmm, I’m going to only bring Jockeys. We interview all day and returned to various hotels and usually stripped to our undies and hung out and had a few beers.
I found myself salivating, brushing our teeth side by side, drinking coffee in morning, having a few beers, with HIM. I was really loving it. The last night we could only find a hotel room with ONE queen bed. we had been sleeping in the same room, but never in the same bed.
We hopped into bed a bit playful, and he jumped across the bed in his ‘Jockey Shorts’ and started wrestling with me saying he was so horny he was going to explode. We wrestled actually pretty violently, playful but rough. As we rubbed our bare chests and white briefs against each other I started to feel my cock get hard, his smell, his skin against mine, the rough beard against my face, his sexy cool demeanour, teasing me. I started to panic about a boner, but to my delight he pinned me down and I could feel that I wasn't the only one getting hard.
It was clear to both of us that we were both getting hard, and the roughness subsided a bit and his lips touched my neck and then he began to kiss my neck, and started to rub his now fully engorged dick stretching the fabric of his white ‘Jockey Shorts’ as taunt as it could go. He moved his lips to mine and a short glance into each others eyes, we both closed and I opened my mouth and kissed him back.
to be continued ...
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