You Need Help: Real Talk About Your First Strap-On

Do you know how many questions we get about sex? Formspring, emails – hell, I’ve even been facebooked! More than once! But at least the last time I answered a question via facebook, I figured that the answer could spark a potentially meaningful conversation about sex. Talking about sex is something that we don’t do enough, as a society. So we’re going to start answering a few more questions about what we do in bed. Welcome to You Need Help: Sex EDition. Disclaimer: not everyone answering questions will be a medical professional. These are our opinions. These articles about sex are to promote conversation, so if you agree or disagree with what we say, please feel free to leave it in the comments. Discussion, much like sex, is a healthy part of life. And as always, You Do You. Or someone else.


 

Help! I just got a strap-on and it turns out I’m not so skilled at using it (yet). How do I learn? Straight porn? Practice? (Don’t worry, we’re planning on practicing.) I’m also really in my head for strap-on sex; it’s all new. Any advice?

Congrats on the strap-on! I would say there’s nothing in the world I like better than strap-on sex, but I say that about every sex act I enjoy. It’s really really fun, though. And practicing with the new dick is fun.

It’s sometimes hard though, and not in the punny way. You’ve now got this appendage that you’ve never used before. It’s attached to your hips, which is unlike any other appendage you have, and it requires a specific muscle set to be able to control it the way you really want. This is a muscle set you really won’t have unless you’ve been fucking with something like a strap-on. You also can’t feel what you’re doing with it the same way you can feel with your other appendages. And, when you first strap-on, the act of it can feel a little silly because, as you mention, you get in your head. I had all these same issues with strap-ons when I first started using them – here’s how I counteracted all those thoughts and expectations I weighed myself down with.

Start by getting acquainted with your brand new dick by yourself, without anyone else (partner included) present. There’s a certain amount of comfort that just comes from having it on and knowing what that weight feels like, knowing how your movements affect where it goes. Wear it while cleaning the kitchen, for instance. If you have a waterproof harness, shower with it on.

And most importantly, masturbate while wearing it. There’s an element to this that isn’t just comfort, but mental connection. When one is mentally connected with one’s dick, one may experience a certain amount of feeling with it. Not the same way you can feel with your fingers or your mouth. It’s more of a brain feeling. And masturbating with it helps facilitate that mental connection. Grab some lube and see how you like it touched. See what about it turns you on. And it could be that you discover that you need a little extra stimulation – some harnesses have a place for a bullet vibrator right in the front. Check to see if you have one of those harnesses. If you do, see how that feels for you as well. Really the big thing about getting acquainted with your new friend is that you want to get as comfortable as possible while wearing it. Get down with your bad self.

Yes, porn helps in the inspiration department, but not as much as one would think in the practicality department. It’s nice to see what kind of sex acts or positions other people enjoy taking part in, but because everyone’s body is vastly different, you may not get the kind of how to you’re looking for. You also may not necessarily need to watch straight porn – I find that I don’t care for most mainstream straight porn. And for getting inspired with my strap-on, I’d rather see people who are actually using a strap-on. Try Crashpad. There are a few scenes that explicitly deal with strap-on sex – this one between Jake and Wilder, for instance.

Then, of course, there are the how-to’s and step-by-steps. Babeland has a ton of events in their Manhattan, Seattle and Brooklyn locations. Keep checking there for a strap-on-related workshop. Smitten Kitten paired up with Queer Porn TV (that’s Courtney Trouble, folks! Sexy!) to bring you two how-to videos. Sinclair Sexsmith has an entire tag on their site entitled “Butch Cock,” which is full of sexy stories and sex advice alike. These how-to’s can serve to make you more comfortable, but nothing is a substitute for good ole fashioned practice.

Please be super communicative when doing anything in bed, especially if you’re new at it and it’s your first time or first few times. One of the major things that jumped out at me was that you said you don’t seem to be skilled at it yet. How do you know? You could be rocking their world. When you’re using a strap-on with someone else, both parties have to be unabashed about what they like, how they like it, how fast, how hard, how deep, etc. While you may experience some sensation, you’re not going to be able to feel reactions the same way you would with your fingers and mouth. The best way to learn how to fuck your partner with a strap-on is from your partner. So let them know that it’s okay to say exactly what they want – it won’t hurt your feelings, it’ll just help you learn. Also know that you’ll probably be really sore after your first few times doing this: there are muscles you don’t have yet that you’ll be using to control where this dick goes. So even if you start out really, really slowly (recommended! Please start out really, really slowly) it still requires muscles you didn’t know you had.

Did I mention to start out really slowly? Please, insert slowly. Fuck slowly. Slow and steady wins the race.

A few more thoughts:

YOU NEED MORE LUBE THAN YOU THINK YOU DO.

Actually, so does everyone for almost every sex act ever. Use a water-based, glycerin-free lube. If you haven’t been using lube, go out and get some. I like Babelube, Maximus and Liquid Silk. Sometimes people think they aren’t good at something or that they can’t do some sex act when all they really need is moar lube.

SOMETIMES IT’S NOT YOU. IT’S THE HARNESS.

If you feel like you don’t have a tremendous amount of control even after a lot of practice, know that not all harnesses are created equal and that different people prefer different harnesses for their bodies. For instance, I love my RodeOH, but I get tons more control with my Spareparts. That could be different for you. And I’ve tried to use a broken harness at least once in my life and let me tell you, that shit does not work – check to make sure everything is connected as it should be. It could also be that your harness isn’t fitting you correctly – harnesses usually need to be tighter than one might think on their first go, and some harnesses do stretch a little during sex, so try tightening up and see how that feels.

BASIC POSITIONS ARE BEST FOR BEGINNERS

When you’re starting out, I wouldn’t go straight for the rockstar positions. Some that I find easier to work a dick with are:

– one partner on all fours, the dick-wearer on their knees behind them

– traditional missionary position

– both partners standing, one bent over the bed/desk/chair/dresser/other person, the dick-wearer fucking from behind

– any blow job position at all. Strap-on blow jobs are super hot.

– In any or all of these positions, try circling your hips instead of only pumping them straight in and out – try other motions, too. Mix it up.


Have a question about sex? Email me at ali [at] autostraddle.com
For 100% anonymity, contact me through Formspring.

Please keep your questions to around, at most, 100 words. Due to the high volume of questions and feelings, not every question or feeling will be answered or published on Autostraddle. We hope you know that we love you regardless.

A.E. Osworth is part-time Faculty at The New School, where they teach undergraduates the art of digital storytelling. Their novel, We Are Watching Eliza Bright, about a game developer dealing with harassment (and narrated collectively by a fictional subreddit), is forthcoming from Grand Central Publishing (April 2021) and is available for pre-order now. They have an eight-year freelancing career and you can find their work on Autostraddle (where they used to be the Geekery Editor), Guernica, Quartz, Electric Lit, Paper Darts, Mashable, and drDoctor, among others.

A.E. has written 545 articles for us.

55 Comments

  1. hi
    i have very small dick thats why my wife never satisfied with me now she tell me to buy a strap-on dildo to fuck her. pls give me suggestion which is best for me, sorry if i post this in wrong section.

  2. So… Yesterday my wife let me (um is the eff word appropriate here?) “do” her with the strap on. She’s the experienced lesbian and after our 7 years together this is the first time we reversed roles like that. Also the first time she ever let someone do that. I now understand how sexy it is when a woman is on top and to not feel insecure about my body when it’s me. In summation, there is no point except I I ally got to use a strap on and that’s not something you can really share with your regular social circle. Yay

  3. My girlfriend and I have been together for almost a year now and lately she has mentioned using a strap on couple times now. I haven’t been penetrated with anything since we started this relationship and she has never used one either. Any tips?

  4. We have tried the strap a couple of times and I have to confess that I am not loving it. It’s usually a little painful, I’m guessing she’s hitting my cervix which is essentially the “playtime over” button for me. And because of this I’m having a hard time getting aroused when we’re supposed to play, my body remembers it hurting and just won’t let me open up (and get that pesky cervix out of the way). No amount of manual or oral seems to get me properly fired up if the strap is in play.
    We also don’t seem to have the thrusting and rhythm figured out, and I feel bad because I know she’s not physically feeling anything when we’re at it. I don’t feel like I’m particularly attractive to her, so I honestly doubt the visual of my double chin and scrunched up face and stomach rolls is doing her any favors. So in the end I feel like we’re both disappointed by the experience.

    I don’t know, maybe we’re just not at a place where we should be using a strap on.

    • you won’t be enjoying any sex until you start to feel better about your body, and I’m not necessarily saying to get in shape. Even the most beautiful, stick thin girls can be self critical of their body, and even the biggest girl can be self loving of her body. Your partner is with you and loves you, and I doubt that during play she is thinking those things you are saying. Bottom line: you aren’t gong to enjoy any type of sex fully if you can’t learn to love yourself and accept your body.

  5. This article has been really helpful, I’m really nervous about having strap on sex with my girlfriend and she has only ever been with guys before me so I feel like I have a lot to live up to (though props to me because she is stunning) I’m nervous I’m not going to do it right or she will think I’m weird for enjoying a bj, I’m liking the advice of just wearing it too as that probably is the best way to get used to having a new attachment so thanks very much, loving these articles!
    Also to the guys that have wrote on here well done fellas it shows that it really isn’t just about you and that’s refreshing to see :)

  6. Great article thank you, I’m in my first sane sex relationship and tried a strap on (receiving) for the first time today. My girlfriend is more experienced so she was very gentle, lots of lube and asked me how it was etc..
    I’m dying to reciprocate next time snd this has given me more cobfidencd to try :)

  7. Hey,

    Me and my girlfriend is thinking about buying our first strap-on (so excited!) but having trouble knowing what kind of/brand that’s the best. Does anyone have any recommendations?

    Thanks!

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