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!
 
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.
 
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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.
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.
 
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.
“Proper” support: men don’t need support, that’s just marketing blurb/a myth created by, funnily enough, a manufacturer of jock straps
 
“Proper” support: men don’t need support, that’s just marketing blurb/a myth created by, funnily enough, a manufacturer of jock straps
There's times I want support, and times I don't want/need it. Usually at work visiting client's offices I wear a jock to keep everything in place and under control. When I don't want or need support I wear boxers.
 
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For me personally, no. I have one thong. I hate it. I don't like the feeling of the strap going up my butt crack. It feels like a permanent wedgie.
I'm guessing that you have the either the wrong size thong or maybe the wrong style of thong for you.
Thongs shouldn't feel like that you've got a wedgie.
Unfortunately, it's trail and error with them though, and that's why a lot of people tend not to like them.
 
I'm guessing that you have the either the wrong size thong or maybe the wrong style of thong for you.
Thongs shouldn't feel like that you've got a wedgie.
Unfortunately, it's trail and error with them though, and that's why a lot of people tend not to like them.
Well, when I bought it off the TJ Maxx clearance rack for cheap, the package said it was a jock, but when I got home I found out that it is more of a jock inspired thong. If I had known I probably would have left it.
 
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Men have been so beaten down by marketing and 90s social taboos that wearing something that isn't a pair of shorts with a 10in-inseam that neglects the fact that you even have a cock and balls is seen as adventurous.
 
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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!
Dude I share your new found enthusiasm, there's ting like under garments that please the wearer. I'm a believer in small is great, nothing is better but big and baggy can sometimes be a turn on. So each day I decide how horny I mght want to feel - there are some items in my drawer which are only ever used as wank accessories. Depending on my day ahead my choice is made, weekends I even add a cock ring, ball harness and even a butt plug, but its the fabric holding my man junk that has to be pleasing.
Like now, a biker jock and rubber cock ring, and growing hardening penis while my balls are cupped in one hand, I glance in the mirror, like what I see, even my nipples respond, I might stroke more, longer, climax...
 
I share some of the OP's enthusiasm in trying new pairs of underwear that are skimpier than what I normally wear - it's fun! Every pair I've tried has had a unique feel that can be a bit arousing when experiencing it for the first time. I have relatively few pairs and rarely buy new types - partly because I don't buy a lot of things that aren't strictly necessary, but also so that the novelty of trying new ones doesn't wear off.
 
“Proper” support: men don’t need support, that’s just marketing blurb/a myth created by, funnily enough, a manufacturer of jock straps
I absolutely need support in certain situations. I'm a cyclist and my flaccid length can be over 5" - let's just say large downward hanging cocks and road bike saddles don't mix! That's why I position to the side in cycling kit (which is form-fitting but worn without underwear). As for the gym... if I did cardio or leg presses while freeballing I'd probably get reprimanded for indecent exposure lol!
 
I absolutely need support in certain situations. I'm a cyclist and my flaccid length can be over 5" - let's just say large downward hanging cocks and road bike saddles don't mix! That's why I position to the side in cycling kit (which is form-fitting but worn without underwear). As for the gym... if I did cardio or leg presses while freeballing I'd probably get reprimanded for indecent exposure lol!
When wearing compression or bicycle shorts I'll wear a jock underneath as they never keep my equipment where it should be.
 
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I absolutely need support in certain situations. I'm a cyclist and my flaccid length can be over 5" - let's just say large downward hanging cocks and road bike saddles don't mix! That's why I position to the side in cycling kit (which is form-fitting but worn without underwear).
I actually don’t know anything about saddles, let alone those in conjunction with cocks. So I don’t know what type of saddle you are referring to. I do have one mate who’s a cyclist too and a FT freeballer, and I believe he points his cock somewhat up in his chamois?

As for the gym... if I did cardio or leg presses while freeballing I'd probably get reprimanded for indecent exposure lol!
Not if you don’t wear a baggy short 🙂 Actually, I have a few friends in mind whose cocks are similar in flaccid size to yours and they do wear fairly loose shorts. I’ve never seen an unintended exposure. Sure, maybe a glimpse up a shorts’ leg but that’s up to the beholder, isn’t it? 🙂

What I meant was that it is always maintained that men ‘need support’ but in actuality, the ‘dangle’ is caused by life-long overheating and compression of the genitals. They have a natural damping and suspension mechanism that in most men doesn’t work properly because their genitalia are always coddled. But they can resume (or re-learn) that natural function even after a few weeks of lower temp and lack of suspension/compression by unnecessary layers.
 
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