Sharing my experience wearing something fun for once

Annatarsauron

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Earlier today, I was feeling sad that I didn’t have gay friends I can share my experiences with. I have 2 gay friends, but we’re not at that level. Then I realized that I was wrong. I have you all! So, if you’ll indulge me…

Yesterday, I put on my last pair of clean underwear. I wasn’t feeling up to doing laundry and, besides, I wanted something a bit different. I’ve been wearing boxer briefs (more boxer than briefs) and wanted something more fun.

So, I stopped by Target because, surely, they should have a good selection. I was wrong. They had, overwhelmingly, briefs, boxers, trunks, and boxer briefs. None of them caught my fancy. I saw they had a few string bikinis and sport briefs. A long time ago, I used to wear string bikinis because there was something so sexy about wearing underwear with such little covering. I looked hard to find my size — or what I think might be my size — and found one box. I bought it.

Now, a long, long time ago, I remember going to Walmart and realizing that they had quite a variety of underwear, especially by a brand called Puritan (which was kind of ironic): along with usual, they had thongs, jockstraps, sports briefs, string bikinis, mini briefs. I got a thong. I remember that vividly because I was on my way to work. As soon as I got to work, I went to bathroom and switched out my boxer briefs for the thong. It really turned me on! Especially knowing what I’m wearing underneath my clothes that others haven’t got a clue about. It felt so naughty, and sexy.

Back to my narrative: I went to Walmart and ended up just as disappointed. Nothing other than boring types. There was one brand that had string bikinis (again), so I got a box. Ah well.

Flash forward to today. I put on a string bikini and, first, it felt amazing. It felt so, so sexy. The contrast between coverage before and now was so stark. It was like I wearing hardly anything.

As the morning progressed, I just felt sexier and sexier. With my boxer briefs, my package was nondescript. Now, I had a bulge, a pouch. My goods were cradled oh so softly. I was leaking precum almost all morning.

I took a break to see what other underwear I could order. I had a pair of 2(x)ist Y-back thong a long time ago and remembered how sexy that felt. Especially under a suit. Formal exterior, wild interior! I ordered a set from Amazon.

As I explored more, I was getting excited about the possibilities. Not to mention the smoking hot models. (I have a thing for models posing in revealing underwear. Or in sexy underwear. Yes, I have an underwear fetish.)
I just wanted to have a guy on his knees in front of me, push his mouth onto my crotch, and have him stimulate me with his mouth, hands, teeth, and tongue, before I slip my slacks down and he has access to my barely covered bulge. I would make him play with my cock and balls through the fabric, getting it wet with precum and his saliva. He’d rub his hands on my exposed sides — no panels there! — before grasping and kneading my ass. I would facefuck him with my erect cock still in my underwear until I came in his mouth through the fabric.

As I thought of what possibilities there could be, my nether regions began to tighten up and I still felt that dampness at the end of my cock as I continued to leak. I discovered I could squeeze my thighs together, and that squeezed my package. It felt exquisite, and soon I got to a situation I couldn’t stand up for fear of scandalizing any onlooker. I stilled my mind and stopped stimulating myself. But I realized I had to do something I swore I never would do again. I took my phone, found the men’s room, got into a stall and sat down, and began jerking off to the men in underwear. This wasn’t necessarily convenient because I had already jacked off in the morning — yes, the anticipation made me that horny — and that wasn’t entirely easy because I had jacked off vigorously the night before. (Last night, I was discovering toys. I found a website that is definitely XXX and doesn’t shy away from any display of the male form. The censored pictures found elsewhere really annoy me, as do depictions of sex toys without a delicious dick to demonstrate its use and appeal.) But, despite one interruption, I came. I enjoyed the wave of endorphins; I also appreciated what felt like a hungry beast being satiated.

The underwear felt sexy all day. And when I’d feel the sides of the back panel on my ass as I was sitting, it made me feel sexier: that was confirmation much less of me was covered by underwear than usual.

Right now, I’m in bed, in my string bikini. It feels like I’m wearing nothing. Yet I can also feel the front pouch gently holding my balls and growing staff of pleasure. It’s exquisite.

I’m looking forward to how the other types of underwear will fare. The y-back thong, a jockstrap, a sock (strapless jockstrap?), underwear with a built in cock ring. Wearing underwear can be a lot of fun and not just a daily requirement!
 
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1. Part of it is knowing I’m doing something naughty. If I wore jockstraps all the time, I’m sure the novelty for that will wear off.
2. Something needs to keep my equipment in order to avoid a scandalous scenario.
 
1. Part of it is knowing I’m doing something naughty. If I wore jockstraps all the time, I’m sure the novelty for that will wear off.
2. Something needs to keep my equipment in order to avoid a scandalous scenario.
2 is a sophism. Years of intense marketing have made us believe that men’s underwear is a must but there is no substantiable rationale behind it. You’d be absolutely fine.
 
1. Part of it is knowing I’m doing something naughty. If I wore jockstraps all the time, I’m sure the novelty for that will wear off.
2. Something needs to keep my equipment in order to avoid a scandalous scenario.
I've been wearing jocks almost exclusively for a couple of years now. No swamp ass, and proper support. I should probably throw out most of my boxer briefs. They very rarely get worn now.