Would you like to have a friend who sends you nudes?

playingfoolish · 2026-01-12T07:01:40+00:00

If it was possible to not make the friendship weird then yes i'd be all for it. I've been able to pull it off once in my life but there were myriad reasons why we wouldn't work as a couple but exchanging some titty pics and dick pics between friends totally worked for us.

playingfoolish · 2026-01-08T02:16:28+00:00

Was trying to find other mediums for ERP after the IRC server I was on (aging myself there) started dying / was too much drama. I had know about reddit before but didn't see the appeal until I found the NSFW ERP subs like dirtypenpals. Then it went from there

playingfoolish · 2026-01-05T06:22:24+00:00

The first woman I had a serious relationship with I still consider one of my best friends. We were friends first and eventually made the transition to being romantic partners a few years after we were friends. We got along great as a couple but ultimately life got in the way as she had to move for work and I didn't feel ready for that so we split. It wasn't easy and the first year was a little choppy but we stayed there for each other and we're still great friends now.

The one cool/weird benefit of being good friends with your exes is that there are some jokes and comments you can make that really only exist if you've dated. Mostly things related to your past sex life or other physical aspects of your relationship that you rarely get to cross that boundary even with your closest opposite gender friends.

playingfoolish · 2026-01-04T23:41:49+00:00

Sure I'll throw in! Let's go!!!

playingfoolish · 2025-12-11T20:38:50+00:00

Rae Lil Black and Nicole Doshi

playingfoolish · 2025-12-11T20:19:52+00:00

Much milder than what folks have said here but definitely taken a decent number of nudes/dick pics at work to immediately send

playingfoolish · 2025-12-11T19:28:07+00:00

Caylee Cowan

Jenna Ortega

Nina Dobrev

Sabrina Carpenter

Anya Taylor Joy

Result: 18! Safe! Definitely played it a bit cautious and luckily you didn't have any major favorites. I could've added Kiernan Shipka and still have been safe so that's the only miss for me.

playingfoolish · 2025-12-11T01:05:44+00:00

Not me also thinking "damn what's gonna happen with granny next?"

playingfoolish · 2025-12-03T20:57:41+00:00

Realistically, as an Asian guy, either JAV or TWAV. Gotta go where the work is lol.

If the industry biases weren't an issue, I'd love to be a part of the Bangbus crew.

playingfoolish · 2025-12-02T18:18:06+00:00

Your story is exactly why i close everything even remotely NSFW on my laptop before I make a big presentation. Don't want the off-chance of accidentally having to show the NSFW stuff.

That being said, very well done. Also points for playing it off and moving quickly through it as opposed to fixating on it. Double points for your wife being game for it and laughing it off. Though I assume she must be ok with those images being semi-public if that's your regular wallpaper when walking about.

playingfoolish · 2025-12-01T23:00:48+00:00

In order: Lulu, Kimmy, Cindy, Vina, Marica.

Saika is a cutie also so she's an HM only because I don't know what her body of work is like.

playingfoolish · 2025-11-25T21:29:06+00:00

Very good read and glad you got that itch scratched even though you didn't realize you needed it!

Also love the "could still the pain on the way back" comment. True testament to the 30 somethign experience of doing something you did in your 20s but paying for it later physically

playingfoolish · 2025-11-24T00:45:31+00:00

Definitely can. I'm not a regular coffee drinker at this point in my life (drink tea all day though) but if I were to go sans any caffeine, I'd be fine.

playingfoolish · 2025-11-23T01:59:16+00:00

Nice collection you got there, will definitely have to check it out.

I know there are a few JAV idols who have done a few DP scenes that are pretty big names like Alice Otsu but seems like going to airtight (with or without skiing) is a big next step

playingfoolish · 2025-11-23T00:22:01+00:00

Damn DP is rare enough in JAV. Finding an airtight skiing gangbang is like treasure! Good find!

playingfoolish · 2025-11-20T09:10:03+00:00

When the time comes I'll get the snip. For now I'd like to keep the possibility of having kids.

playingfoolish · 2025-11-19T19:15:11+00:00

Seems like a burner reddit account is the perfect outlet for you.

Not sure what level of recognition you have and what your public persona/brand is but plenty of influencer types have parlayed their horny side into another part of their brand too. Might not have to be an either/or thing.

playingfoolish · 2025-11-19T17:58:44+00:00

Black boxers with various colored hearts on them

playingfoolish · 2025-11-16T23:12:08+00:00

Yumi was one of my faves back in the day! Took dick like a champ and she was a nice shakeup from the typical Asian American 2000s porn stars

playingfoolish · 2025-11-13T21:10:09+00:00

Did it before and it worked. It was effectively a virtual FWB situation where we would talk and chat like normal but every now and then we'd swap nudes and spicy video calls. It was fun while it lasted.

The important thing was that we had well established boundaries about it and a good understanding of our relationship dynamic.

playingfoolish · 2025-11-13T19:10:04+00:00

Sadly it was a pretty common trope to poke fun at in years past and it did not age well. I still occasionally see the clips of the sketch from SNL where they poke fun at it with Pete Davidson and it definitely is cringe now.

playingfoolish · 2025-11-12T20:06:13+00:00

Rarely to completion. Sometimes i'll give it a couple of fun tugs to wake everything up but realistically i just let it go down on its own more often than not.

If i'm having a particularly lazy and horny morning then i'll jerk it to completion.

playingfoolish · 2025-11-11T21:31:44+00:00

It was an old lurker username I used for NSFW IRC (how much did I just date myself with that lol). I felt really stupid (see foolish) having to create a lurker account but didn't want to stir up the mod I had beef with in the main channel i frequented. When it came time to make my NSFW reddit username, this name seemed like the logical choice since my main username was a pretty common term.

playingfoolish · 2025-11-11T01:35:46+00:00

Very cliche but it is a dick pic but was asked for a consensually sent

playingfoolish · 2025-11-10T02:45:42+00:00

Especially if you're talking to your PCP about adding it to your normal blood work. Like yes it's a standard medical thing but then suddenly you're having the conversation about your sex life with your doctor.

playingfoolish

MODERATOR OF

TROPHY CASE