Q: Dear Holly. Most of my life I’ve been pretty vanilla. But don’t think I don’t have kinky fantasies I’d like to try. I’m single right now and use online dating to meet women for hookups. I’m not interested in a serious relationship and prefer casual sex.
My number one fantasy is to tie a woman up and tease her to the verge of orgasm before intercourse. When is the best time to share this with a woman I’ve met online? – Patrick
A: Hi Patrick. It’s not usual to discover and want to explore your sexual kinks and fantasies as you get older. I too, was much more vanilla when I was younger.
When you’re with a long-term partner, the trust is there to open up about your darker desires, but it’s a bit more tricky if you’re in living in hookupland.
To me, and I’m sure many women, your fantasy sounds very tantalizing—a woman’s dream come true!
Do I think you should mention your fantasy in your first message to a woman on a dating site? Definitely not. Should you bring it up on your first date? Probably not. Is it a good idea to share your desire during your first hookup? Maybe not.
It’s impossible to know how someone is on the vanilla-kink spectrum until you get between the sheets. My advice is to wait until you’re with someone a few times and know that they are going to be a regular hookup partner.
That’s not to say it might just happen naturally on your first night together. But the truth is, most women need a trust bond with someone before they will allow themselves to be put in such a vulnerable position. There’s just too many weirdos out there!
One other suggestion: join a niche dating site like BDSMdate.com that caters to kinky folk. This is where it would be okay to share your fantasies from the get-go. It doesn’t guarantee a woman will let you tie her up right away, but you’re more likely to meet a women who are into bondage than on a mainstream dating site.
Enjoy your search, and don’t get down when sexual rejection happens. Believe me, there are plenty of women out there who would love to be tied up and played with.
Hookup Help is a Q&A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex… we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter. -xo Holly