Dear Jane, <– Ask me anything! No, really, ANYTHING. It is totally anonymous.
My boyfriend loves the strap-on, and it gives me some great feelings of control. How do I approach him of my fantasy of him with a hot she-male (if they exist outside of porn) while he licks me?
Its cool that you brought up porn, because if you mix that with “hey, I had this dream that such and such happened, and it was arousing… I mean… if I had a real cock, that’s pretty much what we’re doing” … which could work in your situation.
But, there are people, possibly your boyfriend, who don’t follow female pegging to a she-male experience. They’ve fetishized the strap-on itself, what it is, and who exactly is wearing it.
Find out why he enjoys being pegged, instead of just you holding a prostate specific toy and prodding his prostate with it. This part of the conversation can easily lead into your fantasy since you’re being so honest with each other. It is a good idea to have this conversation before you bring up checking out your local gay bar for a hot threesome with a she-male because it is a good idea to find out where he is at first.
He could just enjoy that it is you with the power and the feeling of the pegging… but… he could also be hiding that he is into she-males and you’re doing an ok job at the fantasy.
Thing is, since you’ve started pegging him, you’ve had your own fantasies so it isn’t just about him… so going back to what I said in the beginning… ease it to him using porn/dream that you stumbled upon/had while sleeping. It takes the edge off being in the spot light. Its not a far leap from one idea to this one, and he should be able to follow it. I don’t see any freak outs happening if you strike at the right opportunity.
You know him better than I do, you’ll know when you have your moment… just don’t be chicken, and take it! Talking about fantasies should be a fun part of any relationship and can bring couples closer if done respectfully.
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