“How many dates before you bring out the strap-on?”
Lovely Fuckbucketeer, let me put one thing out there first: surprise strap-ons are never the way to go. Anything penetrative and/or dick-shaped is usually going to be a strongly individual preference or anti-preference, shall we call it. I’m sure you were speaking metaphorically, and not advocating slipping your detachable penis into the action without checking first. I just want to make sure that my readers understand this too.
Anyway, once we take stealth dick out of the equation, when you introduce your willy depends on two things:
- How do you define “dates”?
- How important is the strap-on to your sex life?
If by “dates,” you mean more traditional courtship, like coffee dates and dinner-and-a-movie dates, maybe a snog on the couch or whatever, then you would wait until you’re having one of those important conversations, about wanting to have sex with each other and oh, shit, that’s on the table now, we need to sort out a little about what we want to do to each other.
Whether you have sex on the first date or wait six months, you should still eventually have a conversation, either online or in person, about what kind of sex you want, ideally before you actually get down to fucking. This is the time to bring up your sweet, sweet harness of hotness. If strap-on sex is more of a sometimes treat for you—the frequency depending on how much your partner digs it, if at all—it’s okay to wait until you’re a little further along, but again, talk first, don’t just strut out of the bathroom wearing it.
Alternately, try the ol’ sex-toy tour approach, and include the harness and dildo(s) as part of that tour. Pour a couple of glasses of wine, or make up some lovely hot chocolate, get comfortable on the sofa, and take turns cracking open your toy boxes! (Obviously, you’ll have wanted to double-check that everything is clean and well-stored before you display it like that). Even if your partner doesn’t go straight for the strap-on, you’ll find that a little bit of show-and-tell with your toys makes it easier to talk about the options. Take turns telling anecdotes, maybe dry-demonstrating anything that the other person hasn’t seen. This is possibly the best way to share your strap-on proclivities, or really any proclivities that involve particular object: showing off the object itself, and not in action.
If the strap-on is extremely important to you, as in, you never have sex without it, your best bet for dating would be environments where it is acceptable and appropriate to mention your strap-on right up front: sex- or kink-focused dating apps or web sites, queer orgies, after-hours room parties at sex-ed conferences. Put it in your bio for those environments, hell, take some strap-on selfies so that you’re not even going to have to worry about counting dates before letting people know; people will just know. This way you can be sure that you are attracting only people who like to receive strap-on action, and you can avoid at least one potentially awkward conversation about your silicone shlong.
Strap me on, baby, I'm rocket-powered! And when you become a patron of mine over on Patreon, YOU ARE MY FUCKING FUEL.