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Originally Posted by sebbie
1. How old were you when you first got to pick/out buy your own underwear?
2. Did you want to gravitate toward snug-fitting briefs?
3. Did your parents prefer that you wear something bigger, as in loose-fitting boxers?
4. If so, how did you deal with that?
5. How did you deal with all of this dressing for gym, as in PE class? Were you different from your friends?
Extra credit
What were the circumstances where you got to wear your first strap (as in athletic supporter)?
We may be discovering the roots for your love of swim briefs here.
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Right ... here goes ...
1. I guess I was around 13 when I started buying briefs and swimming trunks. It wasn't that easy in the 1970s because the shops where one could buy tight-fitting briefs and trunks weren't self-service. I remember going into one mens' outfitters when I was around 16, and there was a rack of what I was looking for on the front of the counter. I tried to look at ease as I flicked through the little boxes of HOM underwear, while the old man who ran the shop watched me like a hawk. 'Can I help you?' he said at last. I mumbled something and lifted a little box out of the stand. He pointed to a drawing on the box and said: "These will cover you just that much". I think I had selected a white nylon thong. Still trying to look nonchalant, I got out my money, handed it over, and left the shop as quickly as I could.
2. Yes of course.
3. I was an only child from an extremely repressed family, and my mother forced me to wear woollen underwear of a type not worn for a century. Yes, that is literally true. For swimming, I had to have royal blue nylon trunks, because it was a school requirement, but they were massively large, coming halfway up my chest. They were so large that it was like jumping into the pool with a balloon around my waist. I used to look enviously at the other boys, whose trunks weren't particularly small, but at least finished around the belly button. By this time I had found some old bodybuilding magazines and that really got me hooked on small, tight-fitting nylon trunks. I began to save up my pocket money to buy skimpy nylon briefs and swimming trunks, and would spend hours trying them on during the school holidays when my parents were out of the house.
4. See last question.
5. As I have said, I had to wear the most ridiculous long WOOLLEN pants and vests. It was massively embarassing in the changing room and at the annual medical. Most of the boys wore ordinary white y-fronts, which weren't that sexy but at least looked reasonably manly. One year, when I was nearly 18, we went to the medical as usual and for the first time I realised that I wasn't just interested in wearing speedos etc in private, but also had a liking for fit well-built men wearing them, and wanted to associate with such men, especially in sporting venues.
There was a guy in the waiting room already, a bit older than me, whom I had known most of my life - we played a lot of cricket at one time but I hadn't seen much of him for a couple of years. Well, I watched him strip off to the most AMAZING tiny royal blue nylon briefs! He had obviously been working out a lot in the gym, and his penis and balls were huge, weighing down the front of the unlined bodybuilder-style trunks. He seemed a bit on edge, flexing his muscles and adjusting the position of his cock in his pouch. I just couldn't believe what I was seeing, but I knew that I wanted to spend time with this guy - or someone like him - swimming, sunbathing and sweating our bodies in the gym.
I was also beginning to discover that I was bisexual. I really wanted sex with girls - I still do - but at the same time I was finding male athletes extremely attractive. As you can imagine from my upbringing, I was extremely shy. The other guy wasn't and I was green with envy at the way he behaved with the nurse. Before going into the doctor one had to go to the nurse's room to be weighed and measured. The nurse was a very sexy woman, probably around 30 - an unbelievable choice for a boys' school, but this is all absolutely true. Some of the guys used to banter about giving her 'a good seeing-to', daring each other to feel her up when we were in her office. But of course none of them had the balls to do it - except my old cricketing pal! I couldn't see what happened when she measured his height because the ruler thing was hidden by the door, but then he went and stood on the scales - one of those devices where you have to slide little weights to get the proper reading. The nurse had to get very close to do this, and I could see that he had his arm around her waist, as if he was steadying himself on the scales. She brushed him aside and went over to the desk to write down his weight. His bum looked amazing in the thin nylon trunks, as he followed her to the desk and looked over her shoulder, his hand again trying to grope her. His penis must have been extremely close to her bum, if not actually touching. Well, that was too much - the nurse spun round, pushed him aside and firmly shut the door. I don't know what happened after that - but what I do know is that the nurse left for good at half term!
EXTRA CREDIT At college, when I started playing rugby.