Mild Anal Masturbation Dare

[imaprettyboy]

First, find something that fits comfortably in your ass. Nothing so small that you barely notice it, but don't push yourself too far. Remember not to use something without a flared base, some sort of stop like balls on a dildo, or at the very least plenty of un-inserted length lest you end with a very embarrassing ER visit. Your chosen item should fill you up enough that you're distinctly aware of it without moving, but shouldn't necessarily hurt.

Use as much lube as you need to insert your chosen item. If it's a buttplug, firmly seat it. If it's a dildo or dildo-like object, insert it just far enough that you begin to feel nice and full.

Once you have it in place, start a timer. You must now masturbate to orgasm (if you're not allowed to cum, edging would suffice). Watch porn, fuck yourself, whatever gets you off. The only rule is that your toy must never fully leave your ass.

Once you orgasm (or edge), stop the timer. However long it took you to reach orgasm is how long your toy must stay in your ass afterwards (so if it took you fifteen minutes to get off, the toy stays in for another fifteen minutes after orgasm). You can fuck yourself with it if you want, or you can just keep it there while you nap or watch videos or something. Once again, your toy must not fully leave your ass. In addition, you are not allowed to touch your clit or dick for this period.

Once the time is up you are allowed to remove the toy and/or masturbate once again, if you wish.

If your toy left your ass at any point, or if you touched yourself post-orgasm before your time was up, post a reply about it here and myself or another getdare member may give you a punishment.

If you want to leave a report about how it went that would be awesome, but isn't strictly required. The idea of this dare is to combat any post-orgasmic shame that would have you immediately clean up and move on after orgasm by forcing you to continue the pleasurable anal stimulus after you've gotten off. I'd be interested to hear how it made you feel.

[imaprettyboy]

Just did my own dare.

I used my plug, which is a bit of a stretch for me, so getting it in was a minor challenge. It hurt a bit going in but I took it slow, and once it was in I just felt nice and full.

Once I had it in securely I started the timer and played with the plug for a little bit, pushing in it and wiggling it around, before putting on some porn. I'd been browsing getdare for a while without so much as slipping a hand into my boxers, so getting off wasn't a challenge. I actually had to pause at one point because I didn't want to cum already when I was only about five minutes in. I let myself come after 12 minutes and 13 seconds.

Once I came it was a bit difficult to remember to pull my hand away immediately. Still turned on but not allowed to masturbate, I just kind of shuffled tabs for a couple minutes as I tried to decide what to do. I ended up watching Netflix; it was interesting trying to focus on the show with a plug in my ass. The stem of my plug isn't much smaller than the body of the plug so at one point, when I shifted positions in my chair, it almost came out. At first I thought it had actually slid out, but I still had the tip in. After that I sat directly upon it to make sure it didn't go anywhere.

I had thought that I'd go for round two as soon as the timer was up, but I kind of got into the show I was watching and didn't even pause it immediately when the timer went off. I thought about just leaving the plug in for a while while I watched some more, but I decided that the slippery thing trying to escape was a little annoying so I just cleaned up and typed up my report. I may need to find a smaller, differently-shaped plug for extended wear.

[In the end.]

Okay so i just did this and let me say, its not as easy as I thought it would be.

So first things first I grabbed my favourite plug lubed him up, slide down in my chair and slowly and carefully started pushing him in. It was a little painful at first but after 5 or so minutes of pushing him in pulling it all the way out and pushing him back in again it finally poped in. I started the timer up and sat with my back end hanging off the chair waiting for the pain to easy off, it didn't long 4 minutes in and the full ache in my bum was replaced with a very nice full feeling. So I sat up clicked on some porn and egded myself a few times before I gave in finished it. 22:43.

Now this was the hard part, normally when I cum I take my plug or toy out right away. But that option was out, so I flipped threw some tabs trying to take my mind off slowly building ache in my backside. 10:28 left I couldn't find a comfortable way to sit my backside didn't like my weight on the plug so truned my chair around and hung my butt off and leaned on the back rest. Now I thought the plug was seated in me very well, I'd never had this plug pop out without me helping pull it so I didn't think twice to sit this way. I was wrong my body started to push on its own at 2 ish minute mark , and at 1 :14 the plug dropped right out I tired to stop it but no luck it was fully out by the time I realised what was happening.

So close to I guess I should try it again later. Do it till I get it right.

Thank you this was fun!

[ishwbwimfa]

I'm going to be getting a glass dildo today, I'll do it with that. I'm not allowed to cum though, and you may increase my denial if you wish (just check my sig) thanks for the dare!

[SpankKitten]

I fell asleep so it fell out of my ass. Somebody give me a punishment.