Question

Hi Kara_Sutra

I’ve been going out with my girlfriend for about six months now and I’d really like to try some new things with her. I’m really into strap on/domination sex but I don’t know how to ask her about it or even how to introduce her to it. I’ve tried a few times to ask, but whenever I do I get really nervous and can’t go through with it. I’m not even sure I should ask her, because if she’s not into it, it would pretty much end the relationship, and be very awkward and embarrassing for a guy like me.

I hope you can help!

Answer

First off thanks for watching and supporting what I do!!

As for the question, there’s nothing wrong with strap-on or domination play and you are completely “normal”. In a world where exploring your sexual fantasies is becoming more mainstream, so too are new forms of sexual expression and experimentation.

That being said, bringing up the subject of anything sexually taboo with a partner can be challenging. It’s been my experience that when a person wants to try something new the best way to go about it is to ask questions and test the waters, start small and work up from there.

I’m sure the thought of asking her if she’s “ever done a guy up the butt?” is a bit too blunt and point blank for most people, so my suggestions to gain the info you need are these;

Find Common Ground

Find common areas where that type of play has been found in mainstream media and apply it to your situation. For instance, bondage and domination have been found in comic books, video games, movies, and TV (think of the female crusader in her tight leather outfit tying up bad guys and forcing their surrender).

To start the convo you might want to begin by saying something like “I’ve always thought women in stances of power like (Cat Woman/Electra/Silk Spectre/Laura Croft etc) were hot…”

By relating it to something mainstream you remove the “weird” or “perv” factor and create a general area for discussion that’s open ended and comfortable for both parties to explore.

Another reason that I suggest relating it to mainstream media and female hero’s/vixens is that as a female, playing dress up in boots, garters, masks and taking on a state of dominance can be a very empowering experience, one that leaves her feeling more secure in her femininity, comfortable in her own skin, powerful, and confident as well as safer with you.

*Side note: If you want a really cool harness that’s perfect for costume play, and pretty badass if I do say so myself, Tantus just came out with the Connoisseur harnesses. There’s five to choose from, all with exceptional detailing. This is the kind of stuff cosplayers dream of!

Open The Floor For Discussion: Question Time

Once you’ve brought up the subject, spent some time talking and can see she’s still comfortable, you might want to start relating it to sex by asking some questions that open the floor for discussion and wont leave her thinking your a perv (I hate using that word, but it’s something I hear from my readers all the time).

Some questions you might want to ask her are:

has she heard of bondage or domination before as it relates to sex?

what are her thoughts on it?

has she ever engaged in it?

would she be interested?

The answers you get to these questions will give you a pretty good idea of if she’s interested and how far she is willing to go.

Help Her Learn & Be Supportive

Over the last 7 years of giving sex advice I’ve had a lot of women confide that they don’t feel comfortable with pegging for two main reasons; they’re scared they’ll hurt their partner, or worse off (to them anyways), look like an idiot because they don’t know what they’re doing.

It’s no surprise that when it comes to inserting something in their partner (whether vaginally or anally), most women are at a loss… after all, they don’t have penises and haven’t grown up putting their dick in something, be it their hand, a mouth, masturbator, or otherwise. As such, they don’t know how to gauge things like how deep they’re going, how much is too much, when to stop, or how to thrust. Understandably, this can leave them feeling exposed, unsure, incompetent, overwhelmed, and confused.

The best thing I can suggest is to help ease any worries or fears by encouraging her, let her know you understand what she’s feeling/going through, and offer to go slow and let her learn. Maybe she starts by giving you a bj while fingering you anally. Perhaps you have her insert something small and guide her along the way. Maybe you both read up on the subject (Adventurous Couples Guide to Strap-On Sex and Anal Pleasure For Health are both excellent options), or watch an educational video, if so, I’d highly suggest watching Tristan Taorominos Guide To Pegging. Regardless of what you choose to do, this is an opportunity for you to teach her and be supportive. The more encouraged and accomplished she feels, the more willing she’ll be to take it to the next step.

Relax and Have Fun

Assuming that she is into it and wants to play, I suggest you begin with something simple and fun like furry handcuffs, a blindfold, a bottle of good lube, and a smaller anal toy. Let her cuff you to the bed, chair, door etc, blind fold you and have her way with you. When she feels more comfortable you can move onto things like tying with scarves ( I didn’t suggest this first because knots can be dangerous) ball gags, whips, paddles, playing dress up and more. For more advice in regard to Domination and the world of BDSM you might want to watch my video Spankings & Safe Words.

As for getting involved with Strap On play, my suggestion is to start with the domination and mild anal play for now (butt plugs, graduating to larger sizes over time). Allow her to learn, feel comfortable, confident, and safe in that kind of environment and eventually (in the same way as suggested above) see if she is interested in prostate stimulation.

Be Patient & Give It Some Time

If she’s not interested leave it alone for a little while. I say this because if a subject matter is continually brought up, it can cause the other person to feel like they’re being forced or pushed into it, leaving them defensive and even more uninterested. Once a month or so has passed, mention it again with very careful hinting.

Although I do understand your fear and nervousness, I hope that you’ll eventually get up the courage to ask her since it is something you are interested in – and in a relationship, both partners needs should be met.

Hopefully that helped in some way,

Kara_Sutra