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01-5 Diary of a Pussy Boy - FAQ - Q&A

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  • 01-5 Diary of a Pussy Boy - FAQ - Q&A
By Robert | 2:26 PM EDT, Thu July 17, 2025

 

Diary of a Pussy Boy

FAQ - Q&A

 

pussyboy

I am a pussyboy. This is my diary. If you liked
my blog, I’d love it if you dropped me a line.

HOLE WRECKER BUT NO ROSEBUD

no date - no pic for this entry

I JUST WANTED TO TELL YOU THAT YOU'VE INSPIRED ME TO WRECK MY HOLE. I'VE SPENT THE LAST YEAR TAKING LARGER AND LARGER TOYS AND FISTS. MY PROBLEM IS THAT I CAN'T SEEM TO ROSEBUD THE MOST I GET IS A DECENT GAPE. AND THIS IS EVEN AFTER SOME HEAVY PLAY. ANY TIPS?
My best advice is just to keep working at it. It’s rare to have a large rosebud so soon—just enjoy the journey. Keep stretching it wider and deeper, keep taking it harder, and with some time and patience you’ll see the results you want.

Also, push it out lots! Find yourself a fisting top who will push your limits, and push back against you when you are spasming to push him out. Pull it open and push it out. Pop out a huge plug and keep pushing out. Good ways to loosen up the rosebud.

I can just feel my balled-up fist easily sliding into his soft, velvety pussy, as he instinctively arches his back, sticking his ass out even more, moaning like a bitch in heat as he finally gets the pussy-punishment he’s been needing for ages.

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Archivist note: Retrieved July 17, 2025, from https://web.archive.org/web/20170421111228/http://diaryofapussyboy.tumblr.com/page/2 - index. Permalink [diaryofapussyboy.tumblr.com/post/159299114419/i-just-wanted-to-tell-you-that-youve-inspired-me] was not archived, but goes to the live site.

FISTING YOURSELF?

23 March 2015

slaveslutcunt asked: HEY, HOW DID YOU TRAIN TO FIST YOURSELF?

It’s easier than it probably looks. I’ve had some comments like “I wish I were flexible enough to do that!” but I find it hard to believe that flexibility is in any way a limiting factor… if you can grab your nuts from behind you should be able to fist yourself. If you can’t? You should probably do yoga or something.

Anyways, work yourself up first with some toys. I recommend a plug, something of a pretty good size at its widest, like the circumference of your wrist. Get really used to that, ‘til you can pop it in and out. Then grease up your hand real well (the thicker the lube, the better) and have at it. Don’t try to take a fist, per se, at first… put your fingers together and do the “duck hand” and just work it in there little by little. It shouldn’t hurt, though it will be uncomfortable at first. Poppers help, but be careful you don’t get too eager and force it, which you’re more likely to do when your head is swimming.

You might need to practice over a couple weeks with a toy or two before you’re at a point where you know what’s what, and whether you’re going too hard too fast. Have a little patience, and… Blam-o. You just fisted yourself.

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Archivist note: Retrieved July 19, 2025, from https://web.archive.org/web/20150512234301/http://diaryofapussyboy.tumblr.com/post/114449634859/hey-how-did-you-train-to-fist-yourself

HOW CAN I KEEP MY COCK SOFT

15 February 2017

Anonymous asked: HOW CAN I KEEP MY COCK SOFT WHEN I AM PLAYING WITH MY ASS OR GETTING FUCKED? I CANNOT HELP BUT BE ERECT AND CUM, I WANT TO GO FOR LONG SESSIONS AND BE FLACCID SO I KEEP GET FURTHER WITH MY ASS PLAY.

Chastity sounds like the thing for you. A cage for your cock, in short. I naturally lose any hard-on when my cunt is played with so I haven’t had to think too much about it, but if I did have a problem with pesky erections I’d lock it up, or at least wear a jockstrap with a tight pouch to keep it in.

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Archivist note: Retrieved July 19, 2025, from https://web.archive.org/web/20170221110158/http://diaryofapussyboy.tumblr.com/post/157285724739/how-can-i-keep-my-cock-soft-when-i-am-playing-with

 

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