Ask Jay: Non-monogamy, building confidence in the bedroom, finding comfortable butt plugs

Hello and welcome to another episode of Ask Jay. I'm Jay, a sex-positive fellow from Nova Scotia and today I'm going to respond to questions about butt plugs, non-monogamy, and how to get your mojo running in the bedroom.

More than two asks: I have fantasies about threesomes with my partner and maybe watching my girlfriend with someone else. I'm into the idea of us having sex with other people, but not separately. So I guess I'm not monogamous. A friend told me this is polyamory. What's the difference between being polyamorous and not monogamous?

Jay answers: You have some fun fantasies. I hope you and your partner get a chance to try them out someday.

Let's begin by defining some terms. Monogamy is the practice of having one sexual partner. It's the one-person-at-a-time approach to sex and relationships where two people agree they are going to have sex with each other and only each other.

Non-monogamy is a blanket term which refers to any relationship or dynamic where people are not monogamous. If you and your partner decide to have a threesome, or if you watch her have sex, or if you both decide to have sex with other people separately then those are all examples of non-monogamy.

There are a lot of different flavours of non-monogamy. When a couple seeks out a third person to have sex with them (or in front of them) and the couple intends to engage in this activity together, then that's usually called swinging. Swingers are often couples who want to spice up their sex lives by inviting the occasional other person (or another couple) to join them. They usually aren't "dating" the other people they have sex with romantically, just inviting other people to join in their fun. Swingers usually (though not always) go on these adventures together as a couple rather than separately. So I think what you're describing (the threesomes and watching another person with your partner while you're in the room) would be classified as swinging.
"We like Greek food and trading sex partners."

Polyamory is the act of loving (in the romantic or sexual sense) more than one person at a time. Polyamory (or simply "poly") typically refers to a situation where you and your partner have the opportunity to date and form romantic (and sexual) connections with other people. Sometimes couples do this together - setting up double dates - but more often they date new people separately. Poly relationships tend to be more romantic and involve more attachments than swinging where the encounters tend to focus on being more sexual and casual.

I'd like to mention that non-monogamy can take many forms and people can adjust and try various combinations of partners, relationship styles, and activities. You don't need to be one type of non-monogamous or another, there is a whole spectrum. You and your partner should talk about what you'd each like to try and why.

For more information on non-monogamy and the various types of relationships you might encounter on your journey, I'd like to suggest reading the book Opening Up. It's sort of a textbook on different relationship styles that talks about the benefits, challenges, and approaches to involving more people in your sex life.
You'll love what's between the covers.

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Working up to it asks: Any tips for building confidence in the bedroom?

Jay answers: I have a few suggestions for boosting your confidence in the bedroom. I'm going to share these in no particular order.

One of the things that works best for me is getting feedback from my partner. Ask him or her what they liked about sex with you, what turned them on, what would they like more of? Often times after sex there is no recap of what you did and how it made each person feel. Ask your partner "Did you like it when I ___?" "What's something you'd like to do more of?" "Oh, you like this? Got any tips for how I can make that better for you?"

There are two benefits to talking about the highlights of past sex sessions. One is that you get to hear all the hot things you did that your partner enjoyed. The other is it lets you know what you can focus on next time. Then you'll know what your partner feels you're good at and and you'll know you're doing what they enjoy.

Another thing you can focus on is having fun rather than being skilled. Some people worry about whether they're lasting long enough or if their partner is going to orgasm or if they're going to orgasm or how they look when on top or whether they're doing that thing with their tongue properly. Try to put those thoughts aside in the moment and focus on having fun, connecting with your partner. Banter, ask them what they like, laugh if one of you does something silly.
If she falls, yell "Five second rule!" and keep going.

Sex, in my opinion, should be fun. It should be a little silly, a little messy, and a chance to explore. Try not to worry too much about whether you're doing something right and focus on doing what feels good. I find when people focus on just enjoying each other and the moment, then they worry less and naturally feel more secure and more confident.

Try to surround yourself with sex-positive people. If you're in a social group where people regard sex as something taboo, unpleasant, or shameful then that attitude tends to seep into our thinking. On the other hand, if you're around people who are upbeat about sex - who talk about experimenting with new things, who swap tips with each other - then you're likely to gain a more positive outlook on sex and your experiences.

Act confident and confidence follows. Some people refer to this as the "fake it til you make it" approach. Are you worried about how your body looks? Send a naked picture to your partner anyway and ask them what they want to do to you. Worried about your oral skills? Dive down there anyway with enthusiasm. Worried about sounding silly during dirty talk? Say whatever feels right in the moment - just blurt it out! Are you shy about flirting? Try asking your partner questions to get steamy talk going, like asking about their hottest fantasy. Basically identify what makes you nervous or self-conscious and then do that thing. Keep trying it and it'll feel less scary.
Maybe give yourself a pep talk in the mirror too?

Try shopping for sexy toys and lingerie together. Nothing brings down the walls of inhibition and gets people open to experimenting like picking out a new toy together. Try browsing for toys or lingerie with your partner, either on-line or in a shop. Ask them what they'd like to use on you, or have you use on them. See which toys and outfits spark some desire. Knowing your partner is excited to see you in new lingerie or wants to try out a new toy with you is really hot and will probably be a confidence booster too!


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Stuffed like a turkey asks: I've been trying to get used to wearing butt plugs. My plug goes in okay, but then my cheeks clamp down on it and the edges of the base pinch my cheeks. How can I make keeping it in longer more comfortable?

Jay answers: It sounds as though you are currently using a plug with a firm, flared base, which is great. It's usually important to get a plug with a wide base to prevent it from working its way inside you and potentially getting stuck. However, as you've discovered, if the base is too wide (or too firm) then it pushes against the butt cheeks or pinches them.

The easiest solution I can offer for this situation is to find a plug that takes a different approach. For instance, instead of a wide, round base some plugs will offer a soft handle. You may find plugs with a long, narrow, hilt-like base preferable, like the one offered by the Prince Medium Plug.
It's soft, smooth, and easy to adjust.

Alternatively you might like to try the Satisfyer silicone plugs which don't have a flared base at all, but they do have a wide handle. The width of the handle prevents the plug from sliding inside your bottom too far and the handle makes removal easy. Because both of these plugs have a long, thin base rather than a perfectly round one, you can turn it to a position that feels more comfortable and less pinchy.
Three ways to pleasure your posterior.