Blow to pop in pants?

[wildheart]

I do it in my pj's. The balloon can reach almost full size and it doesn't really hurt. Done it with 11 inch up to 17.

[Mutaloon]

I've pumped up balloons in my boxers plenty of times. I have also blown up balloons in some old pajamas (Which seem to stretch quite a bit). It did stung the first few times I did that to myself, but depending on the quality of the balloon it may not sting that much. I've done an inflatable once in my teen years. It felt really good, but the excitement of something getting bigger in your undergarments is not there.

[homesparky]

-tied spread eagle to the bed
-partner attaches balloon to electric pump
-inserts balloon down you pants
-partner stares directly into your eyes, and tells you, "once I turn this pump on, I am NOT turning it off"
-partner gives you their best evil smile

Sounds like fun, love someone to do that to me.

[Nopops4me]

Just come across this post with the last contribution five months ago. Those who have someone blow up the balloon for you in boxers or stretch briefs, do they enter the balloon in the top (by the waistband) up a leg or maybe in the 'fly hole' so that the drip point is fighting against your dick?