[sebbie]

In many respects, Randall’s teenage years were all but ideal. His parent’s house was large enough that he was able to have his own private bedroom as he worked his way toward becoming a young adult. With this privacy, of course, emerged opportunities to try some things that he might not have been able to do if he were constantly with a sibling who was occupying the same room. This has its advantages.

Randall quickly learned that there were specific clothing items that could perhaps make him feel good “down there”. The only problem was how to obtain these items with his parents watching over what he was doing constantly. Still, situations did come up that led to opportunities, and Randall quickly became very good at convincing his parents that he “needed” a particular item for a school-related activity.

Not that Randall was an outstanding athlete at that point in his life, which would have potentially made the stories he made up easier to believe, nor even a mediocre athlete. But you can see the “product” of Randall’s “work” in this regard in the dresser drawer of that little college dorm room. Let’s see, a package or two of tighty whiteys that seem, well, maybe right now maybe a bit undersized (OK then, a lot undersized) for Randall, a couple pair of loose-fitting boxer shorts, A couple pair of sweat pants, a compression tee and a pair of compression shorts, two swimming briefs, one in black and one in navy blue, and, perhaps most surprisingly, an old-school athletic supporter (aka “jock strap”) with the 3-inch elastic waistband, rough-textured pouch, and an open rear with elastic leg straps that keep the pouch in place.

These are the exact same items Randall had in his room when he was living at home, items that he had accumulated and enjoyed wearing without raising a red flag with his parents as to what exactly he was doing with them. That could have been embarrassing if he had gotten himself into a situation where he would need to explain what he was doing with some of this stuff to his parents.

But still, off to college and living on his on more or less (but with a roommate) Randall was not about to head off without taking along the items that were so important to who he was and is. The tricky part was going to be figuring out a way to still enjoy himself without his roommate wondering about him and who he was, sexually and emotionally.

There is a story behind how Randall somehow managed to accumulate each of these items without causing his parents to ask uncomfortable questions as to why he “needed” each one. Of the items, the undersized tighty whiteys were the easiest to make the case for owning. Randall had worn tighty whiteys as just normal underwear since long before puberty. It was after puberty that it occurred to Randall that undersized tighty whiteys were still quite wearable as the waistband stretched quite a bit but that he often “felt better (down there) if they fit a little “too snug”. The only trick was to convince his mom to keep buying him now “the same size as he was wearing a year or two ago.”

Gradually, Randall accumulated unopened 6-pack packages of tighty whiteys that somehow just got stuck in the back of his dresser drawer in his bedroom at the house. Of course, Randall was “using” some of these too, and these ended up stretched out in the wash. It turns out that when Randall went off to college some of these unopened packages “just happened” to end up in the pile of clothes he brought long.

Randall made the case of the black and navy swim briefs because he also had unlined athletic style shorts the other guys his age were using for running and maybe even for going in the water. “These would make an excellent liner for my shorts” was the plea Randall made when he saw these in one of those big-box sporting goods stores. Of course, Randall also picked up a couple pair of unlined loose-fitting shorts at the same time and dreamed up on the spot the story about how he would always be wearing the swim briefs simply as an undergarment with the loose fitting, unlined shorts. Somehow, his parents bought the creative story line and let him do this.

The compression gear was a little trickier to justify, but the loose-fitting shorts played a role in that too. One strategy is to tell your parents that you need this because “that’s what my male buddies are wearing”. Parents like to keep current on what guys their son’s age are doing and not have son’s somehow look different from their peers. So it wasn’t long before Randall had nabbed a silver grey compression tee and a pair of compression shorts in the same color that fit nearly to his knees, and thus were quite visible when he slipped those loose-fitting shorts over the top. With this combination, Randall looked like any other student athlete even though he was not that at all.

Getting the final item, that interesting and coarse-textured old-school strap with the 3-inch waistband was trickier, and the only item Randall managed to buy on his own without having to think up a storyline to feed his parents first. Fortunately, a basic strap (the ones without a cup) only costs $3 or so. The really difficult part was finding one in a store and being on his own so he could make the purchase without his parents even being aware of what he was doing. But as Randall got older his parents would often let him wander off on his own at the shopping mall. What better to do than check out the strap aisle at the big box sporting goods store. And there it was! Exactly what Randall coveted in size Youth (Large). Randall pulled it off the rack and quickly took it to the checkout—a checkout where there is always a female waiting to take his $3.48. Randall wondered what she might be thinking about this given that this was his one purchase, but he paid for the item and quickly exited the store.

Randall then had the problem of getting it to his room without his parent’s knowledge, but fortunately the package is small. While the item might be fun to “try on” and “observe” how his body reacts to the “new situation” but he realized that it could be quite embarrassing should his parents wander in on him at an “inopportune time”. So the strap had mostly stayed in its little clear plastic box in the back of his dresser drawer but somehow got tossed in with the other items Randall was taking with him to college. (Oh yah, he did try it on once on a day when everyone else was out of the house, but that was it.)

Randall has been having a bit of fun wearing the undersized tighty whiteys under boxer shorts as sleepwear, and Shawn might be starting to figure out a few things. Randall got to thinking that maybe he should try a combination that might prove still more difficult to cope with and maybe mess a bit with his roommate Shawn as well. Why not first crawl into the tighty whiteys as a first layer, as Shawn had gotten “used” to seeing him do at bedtime, but then slip on the little strap over, and then on top of that, why not put on the compression shorts instead of the loose-fitting boxers? Sleep in that gear and see if he can make it through the night without “voiding semen”. An interesting “challenge” for mind and body and one Randall has not ever tried before. Plus, just seeing Randall wearing this combination to bed could “affect” Shawn in ways Shawn did not realize were possible until now.

To be continued…