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99-3 diaryofapussyboy; Becoming a Pussyboy, Step #3

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  • 99-3 diaryofapussyboy; Becoming a Pussyboy, Step #3
By Robert | 10:31 AM EDT, Thu July 17, 2025
  • 1 November 2016
Becoming a Pussyboy, Step #3: Advanced plug training.
So, you’ve spent some time starting to explore your pussy both physically, through exploration of toys, and mentally, through reflecting on these physical explorations and beginning to reduce your...

Becoming a Pussyboy, Step #3: Advanced plug training.

So, you’ve spent some time starting to explore your pussy both physically, through exploration of toys, and mentally, through reflecting on these physical explorations and beginning to reduce your pre-conditioned reliance on your cock.

If you’ve been successful with these first steps, you’ve gained some sense of control over the sensations associated with anal play. What feels good, what doesn’t, how to make it feel good. When to back off, when to take a deep breath and keep taking it. Let’s build off of that and further train your hole into a full-fledged cunt.

Most, if not all, pussyboys get a rush from pleasing and impressing a top. On the flipside, one of the worst things is having to tap out or ask the top not to fuck as hard or as deep as he wants to. You may not care to advance to fisting, but we would all benefit from training to help learn to relax the pussy on command.

Being a good bottom is all about muscle control. Taking and holding a plug in is a study in muscle control. The bigger you go, the more your muscles will fight against you, and the deeper your learning will be.

Size really does matter here. If you’re training to take decent-sized cock with ease, then a 2″ diameter plug (e.g. this one) will probably do the trick. If you’re more of a size guy and want to give those real big ones a run for their money, then a 2.5″ diameter plug (e.g.) is a decent goal. If you’re going for fisting, a 3″ plug (e.g., as worn by yours truly in the above picture) will get you in the door but you’ll want to work up as big as you can go for the best experience.

Plug-fucking, as with a dildo, is a very stimulating experience and great for training your hole, but the goal here is long-term wear. Once again, being a good bottom is about muscle control, and if you can go for a whole hour or even a whole day with a decent-sized plug inside, then you’ve already learned a degree of muscle control you didn’t know you had. Every time the plug gets a bit uncomfortable and you manage to work through it and keep going, that’s one less time he’s had to stop fucking you for your own sake.

Start with half an hour. This should be do-able if your plug is at the right size for how much training you’ve done thus far, although you may break a sweat if you haven’t been training much until now. Work up to an hour. If you can manage an hour, you can probably go much longer with a bit of effort. Now, see if you can wear it ‘til your lunch break. Or, for your whole night out. Challenge yourself, and do it often. You are the master of your own cunt.
 

Over time, the feeling of a full pussy will become quite familiar: stimulating and erotic at best, and mildly uncomfortable at worst. You will begin to understand how to identify tension in your pussy muscles and how to dissipate it through your posture, your breathing and muscle control, and you’ll be a much better bottom for it. Plus, your pussy will look better than ever.
 

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Retrieved from archive.org July 17. 2025 https://web.archive.org/web/20170426045222/http://diaryofapussyboy.tumblr.com:80/post/152602988024/becoming-a-pussyboy-step-3-advanced-plug

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