Swimwear for us modest guys?

Training Shorts or Jammers...

Training Shorts:

http://www.swimoutlet.com/Training_Suits_s/277.htm

Jammers:

http://www.swimoutlet.com/Swim_Jammers_s/213.htm

I perfer Training Shorts, they are like very conservative speedos but not completley baggy like trunks. You can get some non baggy versions for minimal drag.

Aren't you down to around 240-250 last I read? The XXL Desotos are for size 41-46...surely those fit you by now. Are you just self-conscious about them being tight? Because they're supposed to be. I mean, can you not pull them up at all or do you just think they look a little bit too tight?

From my experience (I'm bigger than you at this point), you're going to have a hard time finding any briefs, jammers, training suits, etc, that'll fit you...I can't find any that fit me. If nothing else, you could swim in bike shorts and let them dry on your ride...to me, that'd be preferable to wearing trunks.

They should fit tight. They will stretch just a little but the advantage to having them tight is that they will provide some compression for your legs. This will keep them from getting too fatigued too early. Another option is try and find a swim retailer who sells Speedo Polyester Jammers in their Grab Bag Size 38. They are oversized because poly doesn't stretch as much as lycra but they do offer more room. Also, Dolfin offers some mens jammers up to Size 40.

Wear the desoto under a regular pair of trunks during the swim. Then change at t1 by stripping down the trunks and you won't be exposed with the desoto tri shorts on, then put on a pair of dry shorts for the bike and run.

You will only be embarrased for a couple of seconds in t1, and I'm almost certain no one will look at you during that time, as everyone is worrying about themselves.

Not a clyde, but  I have to say, deal with the modesty issue, I was in the same boat and just said the hell with it and wore jammers for my swim on Sunday...I put a pair of shorts on over them for the bike and run.

I say get over your modest-ness and just wear 'em. Wear a T shirt that will hide the belly. No one there is judging what you look like and if they are, screw 'em! Now go knock 'em dead.

odds are the only people that would judge you are the ones sitting on the sidelines.
I have nothing but respect for anyone who attempts a tri and I don't care what they look like, if they're going to try  a tri, they are obviously in shape and take care of themselves

Exactly!

If I were you, that's what I would do. What's the use in buying a jammer or whatever when you got the tri shorts you need. You just need to lose a couple of lbs to fit it, and by the end of this tri and all the training you will put in for the next one, it will fit or even be too big.