[sebbie]

Part CII

I have written any number of times about my experiences in sleeping in thongs, straps with cups and other snug-fitting garb, but last night I was playing around by and with myself once again, and I ended up having a wonderful night. I got to thinking that maybe my readers would like to hear the details of exactly what I did to and with myself that made for so much fun all night long, with the idea that maybe there would be some things my readers might wish to do as well.

Both physically and psychologically, what I do ends up being way fun. Doing this successfully combines a mix of the psychological and the physical. I love wearing thongs—always have—it’s the combination of the elastic cord or band that cuts snuggly between my glutes and the idea of getting my penis and balls all positioned inside a pouch that never seems to have quite an adequate amount of room. For a lot of guys who like to wear thong underwear and swimwear The whole idea of just getting into one with everything in place becomes an erotic experience given the attention a guy needs to place on making certain that all parts of the male anatomy is where it should be.

Last night, as my “challenge” I picked out an old black swim thong from Koala Swim. These are the ones with a very narrow front pouch and a really tight fitting rear band that has to fit between the glutes. Getting into the thong posed a fun challenge for me. A proper fit pushes the penis and balls upward and forward even as the thong back disappears between the glutes. Keep in mind that I am going to be wearing this through the entire night if all goes as planned. Great fit and feel once everything is in.

Next up, I am going to be wearing a strap with a cup over the thong. And, of course, I am an old school strap guy. I like the flat cups like the guys wore in the 1960s, not the roomier “Banana Style” cups. Now keep in mind that the thong is pushing a guy forward and upward into the strap cup, even as the cup itself is putting pressure downward. Think about this. Two opposing forces providing tension in opposite directions with my penis stuck between the opposing forces.

I’ve said this before, but the best straps and cups are the ones that fit so snug that they can only fully contain a flaccid penis. Penises and jock cups have an interesting relationship. Somehow, penises seem to know when they are about to get crammed into a space that leaves almost no room for expansion. Invariably, they take advantage of whatever space is there right up to the walls of the cup. In the process, with the cup containing the expansion, penises are capable of generating some marvelous sensations in that limited space. Sensations that can drive a guy bonkers if he just thinks about it for very long.

I have often wondered about how much of this is physical and how much is linked to the fact that the guy psychologically knows that his penis is going to be cramped for space. Sexual sensations always seem to be this goofy mix of the two. The uncertainty about what will happen only adds to both the psychological and physical enjoyment. It is this same mix of feelings that sometimes makes guys very wary about wearing straps with cups for the very first time. But this is also an extraordinarily fun place to be.

So I am in my black Koala swim thong, and have my TruFit old-school strap and cup over. What Next? Why a Dolphin Swim brief, of course. The Dolphin is black with red on the sides—classic old school swim brief that covers the thong, strap and cup and holds the cup firmly in place. This looks neat and feels even neater.

By now, I’m feeling, well, more than a little horny. The thong is squeezing itself between my glutes, and my penis feels like it is in another place entirely. Is it the thong pouch that is doing this to me, the firmly positioned cup, or some of both? Can’t tell! Who cares! Whatever is happening I am feeling absolutely great down there. The cup is pressing down on me and my penis knows that space to expand is really limited. Can I fall asleep this way? Good question.

I tap on the cup and my penis notices. I press harder on the cup with my hand. My penis likes that a lot. But in this situation it is impossible to have an orgasm while still in the cup. It’s frustrating, but, at the same time I am savoring my predicament moment by moment. This is why the phrase “delicious agony” was invented I guess. I try to adjust the cup a bit, but that only seems to make matters worse, or maybe better. My penis is absolutely loving the situation it is in. Goofy, wonderful fun. Delicious! Delicious!

So I do soon fall asleep thinking to myself that other guys need to experience what is happening to me . My body is great. It’s letting me drift off still in delicious agony.

I awaken but not till 5 AM. Still feeling great down there. I made it through the night without awakening at 2 AM to tear everything off. I finally get up at 6:30 and tear everything off. My black thong has some really neat wet precum stains in the pouch, about quarter-dollar sized. I still have not had an orgasm. I get up and start writing this.


A great part about all of this is that if I can avoid having an orgasm today I will be even hornier tonight and I can repeat the process once again. This is great technique for learning the nuances of how to edge. The pressure and need to ejaculate keeps building night after night. Some guys are able to go for a week or longer without ejaculating but this keeps getting tougher and tougher to do. But testing yourself this way is part of the fun. At some point I will break too, but not for now! Not now!

I like it! I like it! Enjoy yourself! I always do.