Dear Jane, My BF and I Peg; we love it! But, How Do I Bring Up My Fantasy of a Threesome with a She-Male?

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?

Spareparts Joque Harness

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.

 

Share your thoughts

  • http://www.facebook.com/fragglera Rachel Kantstopdaphunk

    I’m pretty sure that trans folks don’t like that term, and while pre-op transwoman is a bit longer, it seems less likely to offend.

    • http://twitter.com/SexpertJaneBlow Jane Blow

      Which term? I tend to simplify or use the same words that the people asking the questions use bc these are the terms people are looking for regardless of not knowing which words offend.
      I’m glad to update and educate, thanks for this input :)

      • just a girl

        Another complication on their search may also be that— most transwomen are quickly unable to get sustainable erections once they start taking estrogen, so her fantasy of a trans girl doing both of them could be trouble. It could probably still happen, but sort of differently. Not to mention gender dysphoria, etc, in real life this dominant role would probably be very distasteful to a transgendered female. But hey, there’s all types. Most pornography where you see a “shemale” with an almost regularly male looking penis totally screwing somebody and coming is due to an unhealthy practice of using testosterone just for the duration of that film, to perform these acts. It’s actually kind of sad :(

  • anonymous user

    How come I can’t find porn like this? Only male-tranny, no m/f/t … does this not exist, or just extremely hard to find?

    • http://twitter.com/SexpertJaneBlow Jane Blow

      It exists, try the Rogue Adventures series that Nacho Vidal is a part of from time to time, I believe Evil Empire is the production company

  • NewSwingersWebsite

    Although they don’t have a lot of it, you can occasionally find some M/F/T on tsseduction.com

  • http://www.webcamporn.mobi/ save_me_from_iphone_porn

    Besides watching them on porn on your computer or iPhone or wherever, I assume you might have to head off to Asia for that…

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