What to wear?

[sebbie]

So, here is the puzzle. Randall realizes that he is going to be spending a college year of his life in rather close quarters. He has only met his roommate for the year, Shawn, and he certainly doesn’t know what he will learn over the coming year on a host of different issues. The two of them seem well matched, both academically inclined and both maybe a little on the nerdy side. Everyone knows that there are a lot of college guys who seem to be primarily using their personal charm with others, both male and female, as a means of avoiding doing serious academics. If you have a lot of personal charm, there is no reason to do that well academically, because your personal charm will always pull you through in a situation where having better academic skills might have worked.

But both Shawn and Randall seem quite serious about why they are there and what they plan to do in college. Generally double rooms often do not work very well if one of the guys is a serious academic and the other believes that personal charm is all that matters in a host of different ways. Interestingly enough, it is usually the serious guys who seem to get the most enjoyment out of masturbating frequently. The guys who run on personal charm make everything sexual about having a relationship with another person. But is one of these two approaches somehow superior to the other? That question is not easily answered.

Then there is the subject of tighty whiteys, a type of underwear that has been attacked on a number of fronts over the years. At some point, young teens purportedly moved away from wearing tighty whiteys and everyone purportedly moved to loose-fitting boxers. But that was the same point in time where really oversized and loose-fitting jeans were all the rage.

Then I guess as jeans started to get skinnier, the idea of stuffing a loose fitting boxer into a narrow-cut jean became more and more difficult. The first move was back to what are called boxer briefs, snugger fitting than boxer shorts and made of the same material as tighty whitey. But soon the thighs of the skinny jeans have gotten so form fitting that stuffing even a boxer brief in them became increasingly difficult, and somehow we are back around to a tighty whitey as a good choice to pair with some skinny jeans. They are cheap and readily available in a variety of sizes.

To, a lot of guys have glued in their heads very early experiences they had masturbating. For a lot of guys, maybe most of them, there was probably a most interesting experience ejaculating into a pair of tighty whiteys. If a guy has only a few options, you go with what is readily available! The exact circumstances under which this happens varies a lot from one guy to another, of course.

Two points: First, tighty whiteys can be a useful masturbation aid, and second, a pair of tighty whiteys can be useful in solving a nagging “problem” Randall faces living in the dorm room.

Ejaculating is a lot of fun. But if done under the covers in the dark of night, a powerful orgasm can also create a very messy situation not to mention having to deal with the stained sheets for the laundry people to deal with.

When I was much younger than I am now, I used to masturbate to ejaculation under the covers at night. This in turn would create horrendous looking wet spots, which if I were lucky enough to have sufficient time to dry, the ejaculate always left randomly-shaped starchy stains on my pajama bottoms. And I always assumed that if I was wandering around others would immediately notice the wet spots on my pajamas or the starchy stains, and immediately realize what I had been doing by, with and to myself.

I presume nowadays pajamas are out and most guys wear loose fitting boxers for sleeping in warmer weather transitioning to a sleep pants as the weather turns colder. A basic problem facing both Randall and Shawn is the problem that has haunted them since just past puberty. The problem is how do you pull off masturbating to ejaculation in the dark under the covers without tipping off to your roommate as to what you have been doing to and with yourself. If you get up in the morning wearing cum-stained boxers or sleep pants you are going to face much the same issues I faced as a young lad, plus the additional problem of cum-stained sheets that might not get swapped out for a week!

That is where the pairs of tighty whitey come in. Conveniently, the cotton in the tighty whitey should be quite absorbent, and cum, being quite viscous, the tighty whitey should catch most of it. Shawn is going to see Randall putting on boxer shorts OVER a pair of tighty whiteys before going to bed, and he may wonder a bit about this. Now if Randall practices a bit, he can probably learn how to remove the boxer shorts after he ejaculates while still under the covers and in the dark, tossing the cum-stained tighty whiteys into a convenient location next to the bed. Randall awakens wearing only the boxer shorts he was wearing when he went to bed, and the cum-stained tighty whiteys are quickly tossed into Randall’s pillowcase laundry bag.

Then too, I have been discussing the possibility of having ready access to tighty whiteys available in a number of sizes, from a guy’s “normal” waist size to seriously undersized versions from the boy’s department. This has a way of playing with a guy the same way undersizing a swim brief can. The waist bands and the cloth stretches a lot, and the only recommendation is not to undersize to the point where the stretched waist band is not sufficiently large to be able to get in at all. But other than that, an undersized tighty whitey will fit much like a skimpier brief in your correct size would fit. Of course, as you undersize, the pouch will keep getting smaller and tighter. The solution here is the same as for an undersized swim brief, that is, the solution is to point yourself up not down, and with the snug fit that will be much easier to do with the undersized brief. The cotton will be coarser textured than the Lycra-blend swim brief, but many guys might actually like that.

What you are doing is setting yourself up for some great fun in the darkness under the covers, and right there a few feet away from your roommate. And this is accomplished without creating an impossible mess to attempt to deal with the next morning. I can’t assure you that the boxer shorts or sleeping pants will be completely free of damp spots or stains, or that the sheets will be completely stain free, but this should go a long way toward minimizing the problem.

For now, Shawn the roommate is none the wiser. But what if Shawn should ask you why you wear tighty whiteys under your boxer shots or sleep pants? You could just toss the question off and say “I’ve always done that!” Will Shawn eventually catch on to the scheme and want to try it himself?

Good Question!

To be continued…