Question: I would like to use a strap on with my boyfriend. How do I get him to try something like this?
Hi Strap-on Curious,
That’s exciting you want to try strap-on sex with your boyfriend! Everyone has an anus, so any body has the potential to get pleasure from strap-on sex, if they desire to. Exploring a desire with a partner can sometimes be intimidating, we can wonder how they will react, what will they think of us and if it will change how they perceive us. So how do we approach this gently and curiously?
Reflect on what is sexy about strap-on sex for you.
When you talk to your partner, share the sexy activity you want to do, but also what turns you on about it, any aesthetics of your fantasy that are sexy. For example think about:
- How does strap-on sex make you feel to think about it?
- What fantasies have you imagine?
- How do you want your boyfriend to feel when you’re strapping it on for him?
For example, ‘Babe, I’ve been thinking about this fantasy lately, where I strap it on for you. It makes me feel so sexy to think I could be inside you while we kiss and look into each other’s eyes. The idea of wearing ‘my cock’ for you, makes me feel super powerful and like I could devour you. I think about you bent over while I admire that sexy butt’.
Sharing beyond just the physical activity of pegging can open up your partner’s imagination to find ways to connect and get turned on by your fantasy, the mood, the scene and the erotic intentions. Our mind is our biggest sex organ, so why not use it? He may even discover a new way to get turned on.
Make it a conversation.
Sharing fantasies can be intimidating because one person might feel compelled to oblige or immediately reject the proposed idea, but in reality might need more information, time to do research on their own or time to think about if they are into it or not. Ask questions like:
- What do you think about strap-on sex?
- Have you ever thought of what I’d look like wearing a strap-on?
- Has your butt ever been a sexy area for you? Have you explored anal pleasure?
- Do you have fantasies about anal play, penetration or sex toys being used on you?
- How does it make you feel to think about me wearing a strap-on?
- Do you have concerns about strap-on anal sex? Hygiene? Pain? Shame?
Discuss any stigma.
We socialize people with vulvas to be the receivers of penetration and people with penises to be the giver of penetration. So sometimes, penetration roles get tied to masculinity or femininity. There’s a lot of homophobia when we talk about cisgendered heterosexual men and receiving anal penetration. Your partner could feel it says something about his sexual orientation if he gets pegged or that he may perceive you as less feminine. Talking about these concerns helps you build empathy for each other as you try something new.
Go shopping for the dildo together.
Shop online at Secret Pleasures or in person and make the dildo purchase a flirty experience you do together. Talk about what sexy toy size, colour and shapes make you hot to think about. Keep in mind for first time strap-on sex, smaller is better – sometimes our eyes are bigger than our buttholes.
You can also shop for the harness together, but it’s important that the person wearing the harness feels comfortable with the style and size of it – so what may be visually attractive may not be the most functional. Here are tips for strap-on sex shopping.
Explore new sexy things during familiar sexy things.
If he’s open to exploring, make anal play integrated into the sexy things you already both like doing.
For example, if he loves blow jobs, ask if he’d like you to play with his anus externally (no penetration) while you give head. If he loves kissing, ask during a hot makeout session if he’d like you to massage his perineum (the space between his testicles and anus). If he loves to spoon, ask if it’s ok to thrust your pelvis against him while you cuddle and tell him how it makes you feel, invite him to tell you how he’s feeling.
If he ends up being ready for penetration, make sure he knows that it’s ok to need less and that you’ll honour by easing back. If there’s any burning sensations, he needs to let you know – we’re doing anal not pain-al. Here are 4 Tips for Better Butt Sex.
Just not that into it?
If he’s just not that into it, thank him for making it safe for you to share your fantasies and tell him you’d love to hear about his. Some people are completely turned off by strap-on sex, while others are just not turned on by it. You’ll have to peacefully accept that. No one is obligated to entertain or indulge in our fantasies. Be gentle, empathetic and supportive of each other’s sexiness.
Other Blog Posts To Checkout:
Ask A Sex Educator: First Time Anal
Secret Pleasures Boutique 
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