I did a bad thing yesterday. I jacked off twice. I’ve sort of (re)developed an underwear fetish. I remember even before I came out I used to get off on revealing underwear. I’d tan in the middle of campus at UT Austin in a bikini when all the other guys were wearing shorts.

When I moved to NYC I’d wear thongs and skimpy bikinis when I’d go sailing and on vacations with a john/friend of mine – after all, I had to give him what he was paying for. I actually had a bit of a thong tanline that summer and it didn’t look all that bad. A few years later I’d take vacations to Puerto Rico where I’d lay on the beach in the skimpiest of string bikinis – literally just a triangular bit to cover your dick and balls and two strings that looped around your legs/ass.

I really should have taken it further and been even more of an exhibitionist while I had a nice tight young body, but I kept getting in relationships…

Anyway, as I’ve been losing weight I’ve been thinking about what would be hot to wear when I’m thinner. I’ve gotta see what looks good on me when I get thinner (after all I’m 20+ years older and not nearly as tight and muscular), but in the meantime I’m cruising underwear sites sorta fantasizing that I can get the body to pull off some of the more daring stuff.

The first load yesterday came when I saw this pic…

It’s actually a pretty tame picture. I mean I can’t even imagine having sex with the model – he’s too pretty and probably pretty dull and boring in bed (If you saw his face you’d know what I mean). What got me was how much pubic hair was showing over the top of the bikini. The rather pronounced pouch for dick and balls is pretty hot too…

I could actually see wearing something like that. But it would be pushing it for me to pull it off – even when I’m thinner (I’m a bit big boned and wide even when I’m thin and the really skimpy stuff looks best on guys with little waists). I’m hoping next summer I can pull it off. That’s sorta the tanline I’d like next year.

This picture got me going too… Imagine a runner running down the street shirtless showing that much pubic hair. I bet his ass crack would be showing too… So fuckin’ hot… I wish we could mandate runners wear this type of stuff…

Today a jockstrap I had seen before sorta struck me in how hot it would be to wear… There’s the fabric version which seems to stretch and cover…

But then there’s a glossy black version that doesn’t look like it has much stretch to it at all… With the slightest stirring of your dick you’d be totally popping out of this one…

Personally I think both of them would be hotter with some trimmed pubes showing… I generally don’t like the plucked chicken look (except on teens – but that’s why they call them ‘chicken’) – men are supposed to have pubes. If you click on the pic of the yellow one you’ll see pics of the jockstrap with a guy who’s fairly hairy – it’s much better than the shaved guy, IMHO.

The problem that I encountered before is where do you wear this stuff? Back then I was too shy to wear the assless chaps I had made out to leather bars. I guess I could wear the jockstraps at sex parties, bathhouses, and on weekends like MAL/IML. But on a daily basis I’d rather wear boxers under my jeans – they’re just more comfortable (they let my PA hang properly). IMHO, when you wear stuff like this the point is to be seen…

The other day I bought a couple of jockstraps. I don’t have the body yet for the really skimpy ones, but got some that should look decent on a body like mine…

I got the Intyman enhanced jock (it has a piece of fabric in it that pushes out your dick and balls – appropriate for a top)…

I got the white one so over weekends like MAL I can soak it with piss and turn it a nice yellow color… As it gets old and the fabric starts to pill it’ll look like a slutty old jock – which will be totally cool. It’ll also be hot seeing the outline of my big PA ring through the fabric.

And then I got the Activeman vented jock. What I liked about this one was how the site said the pouch was cut smaller than normal and didn’t have much stretch. I like the idea that I’ll pop out when I start getting hard.

Once again, that will look good stained piss yellow… 😉  I can totally see letting guys piss on me in the right circumstances. Walking around a place like MAL, smelling a bit musty from the piss would be sorta hot.

Anyway, you can start to see why not being a bear suits me. I’m a bit of an exhibitionist when I’m thin. Problem is I seem stuck at 220 – been at that weight for a few weeks now. I really need to go thinner if I’m going to pull off these jockstraps. I ordered larges which might be too small (not sure). My goal is to get down to mediums. I’m hoping the larges at least fit by January when I go to MAL. I’m thinking it would be fun to run around the halls at night in nothing but a jockstrap and military jump boots seeing what trouble I can get into. But that requires me to lose more weight.

Speaking of MAL I’m going to go see David Menkes and have him cut down a leather jock he made for me years ago. I want it to barely cover my dick and balls and show some or all of my pubes…  (Can you tell I’m getting into a pretty slutty mindset lately – it’s fun.)

And yeah, I know wearing a jockstrap is like having a big sign on you saying “bottom”, but that’s why I went for the ones that accentuate my dick. And I’m also thinking of being a bit versatile after I get my ass healed up properly… Could be fun to experience loads dripping out of my hole every now and then 😉