Strapon Questions and Help

It's perfectly normal for air to get stuffed up there, happens to girls all the time too (in the vagina I mean). When it hurts, just have her stop for a second so you can fart it out.
 
All kinds of strapon play can be lots of fun for both boys and girls, but, like any other sexual fun, it is always best to communicate well with each other even (or especially) when playing out our special fantasies. The most important thing is to let her know what works for you, tell her just what it is you want and tell her when things are feeling good and when not so good, let her know what works for you on your own and talk it over, then she can give you just what you want (of course, it's important too for you to be sure of just exactly what works for her and be damn sure to give her what she wants and the likelihood is that'll help her return the favour). Basically, good communication is key to exploring new kinks. Don't be ashamed to talk it over in however much detail it takes. The best person to ask for advice is always your partner (rather than us on here!).
 
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