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Butt plugs

When my bud comes over for a fuck night he always plugs me when he's done, when he's ready to gop again he removes, and so on. By morning when he's ready to leave I'm well and truly fulfilled and usually oozing.
 
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I had no idea so many men are walking around with a buttplug. Any tell-tale sign to spot those horny hoes?? Walking funny??
 
I love wearing a plug, I have wore plenty of them out. I was wearing them before I actually started to bottom,I was mostly top in my younger years but I loved the plug and I wore one many a time when I topped. Then I wisened up and allowed myself to start to enjoy being a bottom. I love wearing one in public and locked in chastity. Currently I can't wear it out in public because it will just fall out. Thats a side effect of working with bigger and bigger toys. I bought one awhile back because I figured this would happen but my eyes tend to be bigger than my hole and I am having trouble taking it. After a long session and being opened up I can almost get it but so far I haven't made it. I don't know if I should go a size down and continue to practice on the bigger one or just forget about buying another one and keep going for the one I have. My friend wants me plugged but I don't dare leave the house with the one I can Currently fit thats actually too small because it falls out and I don't even realize it until it's too late. No one prepared me for such difficult decisions in life!
 
Beginners often go for a small which is a mistake because you cab't really get to know how it feels and — more seriously — it pops out too easy. Go at least for a medium — it can be on the small side, but at least you know it's there. Even if you're a butt plug beginner you can still put it to hot use. Lube it up, slide it in, grab your hard cock and slowly jerk off. You'll be having pleasure sensations you didn't know were possible.
I had to get a bigger one for those reasons. Only we use it when we're fucking. When I used the small one, I'd cum in her and the plug would pop out! A little larger one took care of that. Feels better too.
 
Tips for sizing up from 2inch diameter to 2.5 inch diameter? I’ve had the 2.5 for a few years and have never been able to fully insert it.

I’ve tried sessions of playing with dildos and plugs of various sizes to warm up, and then trying for like 1 hour with the 2.5 but I’ve never inserted it all the way past the base.

But I love how it puts pressure on my prostate.

Help and tips please! I’m not into poppers
 
The problem I have with butt plugs is that the base gets painful digging into my cheeks after a while. I find Dildos more comfortable to keep in place for an extended period of time. Problem is, they work their way out if standing or walking. I bought a pair of underwear that are supposed to keep a toy in place, but while they're comfortable to wear, the cloth isn't firm enough to really keep the toy in place. Anyone have any suggestions for a comfortable product (underwear or harness) that will keep the dildo from slipping out?
 
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