How to Choose a Strap On Dildo

My Strap-On Shopping Adventure

I’ve gotten several questions in the past about using and buying Strap-On Dildos over at Allsexadvice.com, so I thought that it would be fun to teach through my very personal experience with strap on harness shopping for the first time. So, what follows is a detailed account of my experience. Enjoy!

My boyfriend and I have been seeing this very special woman for a couple of years now. She does live a bit of a distance so we only get together to play about once or twice a year, although lately it we’re trying to get together even more often. Anyway, she’s been really great, the first woman I’ve ever really been sexually involved with. I haven’t tried a quarter as much with her as with any other woman prior. And she’s real easy going and willing to try new things so it’s been one hell of a ride and a great one at that!

I have for quite some time now wondered what it would be like to fuck a woman. Now the whole idea of a strap on kind of turned me off because I felt as though it would make me look too masculine (I was quite the tomboy growing up and would hate to have to visit that time of my life again). My girlfriend is real feminine and totally girly, so the last thing I want to do, especially in the eyes of my boyfriend, is look manly…yuck! Well, yet another meeting has been planned, but the urge to fuck her is really on my mind. I think this is the time to do it.

I started shopping online to see what’s out there. Everything is kind of boring and somewhat ugly, all these black harnesses, none really looking like a thong…until I saw it. A pink or purple and silver harness and it’s sparkly too. It’s got style and it doesn’t look as bulky as all the others, but a harness has to fit really well if the whole activity is going to be successful. Besides, I’d hate to start the job and have the harness slide down or fall off right in the middle.

I have a great sense of humor during sex, but still embarking on this activity will have me a little anxious and that’s one thing I don’t want to have to worry about or deal with. Luckily, I live close to New York City where I can actually visit quality sex toys shops to feel, see and even try on a harness. So that’s my next step, physically handling a harness and finding one that doesn’t make me feel masculine, is comfortable to wear and works well for me.

That’s what I physically have to do. Emotionally, I’ve already done a lot of communicating. My boyfriend and I have been together for almost 14 years now and we love each other very much. We’re best friends and the reason this threesome arrangement works so well is because of the trust and very open communication that we have. But I wanted to make sure I wouldn’t freak anybody out, although at this point that would be very difficult to do.

So I shared this desire with my boyfriend and he was more than turned on to say the least. Great, he’s not frightened, now I just have to run it by her. So I shared this desire with her and she was really excited and actually said she’d like to fuck me after I fuck her. What more could a girl ask for. So, no one’s frightened by it, but I’m definitely feeling a little anxious about it. For some reason, I’m thinking it’s not as easy as it looks. Just find the hole and thrust right? Oh boy, this is going to be quite an experience…

Okay, I’m ready to go out and purchase my strap-on. I’ve done all my online window shopping and I’m ready to go pick one out, so my boyfriend and I were off with our kinky friends. I brought them along because I figured they’d enjoy helping me pick one out too. Besides, they’re a kinky couple and they’d understand. I have never been to the sex toys shops in NYC before.  I found the strap-on harnesses displayed on the back wall. As I walked past all the vibrators on display, I could feel them pulling me in, but I ignored my urge to play with them and continued to the back wall. I had to stay focused.

First, I noticed a pink and purple sparkly harness, it was rather stylish and had personality, but then I took it off the wall and realized that it was made of vinyl and was really kind of stiff. With the way the harness is made, the vinyl straps that go around your waist and legs is folded, and on the side that touches your skin, the seam is not sewn down. It’s just the two sides of the fabric meet and I couldn’t see that feeling comfortable up against my skin. So there were 2 negatives about that one: the fabric was stiff and the open seams on the underside would not be comfortable rubbing against my skin. With great disappointment, my search continued.

There were a ton of black leather harnesses, most too bulky for me. There was a red leather one, but I’m on the pale side, even with a tan and I just couldn’t see the red flattering me. So I stuck to non-bulky and black, which narrowed my choices down for me. One harness seemed really cool, it had leather snaps on the front which would allow me to use different size O’rings, then I really have a large choice of dildos to choose from at any time, but there was a drawback…This made the harness a little bulky in front for me, not what I was looking for.

I kept that one in mind, but moved on. After feeling and perusing the whole wall of harnesses, two stuck out to me. One wasn’t too bulky, just a little black triangle in front with a pocket for a little vibe, made of soft leather and had one strap (meaning it’s worn like a thong) and came with an O’ring attached. I know you’re probably wondering what the importance of this O’ring is and I shall explain before I continue, so we’re all on the same page.

Definition of an O’Ring:

An O’ring is attached to the front of the harness to help keep the dildo in place. With leather harnesses especially, the fabric around the hole that the dildo fits through may stretch over time  making the hole in the harness much bigger than the dildo. When that happens, the dildo will not stay securely in place, making it very difficult to use. With an O’ring attached to the harness, the hole will always remain that size and even if it does, for some reason, stretch, you can always purchase another O’ring instead of another harness.

The other harness looked somewhat the same, in the front, as a one strap but had two. Let me explain:

Two strap harnesses, like this one, fit like a jock strap, the straps go through the legs, around the butt cheeks and up to the waist strap on top. In my initial research I saw mixed reviews about this type. Some said that it was great for women because it left your vagina exposed for stimulation without needing to remove the harness; and others said that if you bend forward, the leg straps slide down your legs which gives you less control over the dildo.

However, the 1 strap, g-string style, like this, with the strap going up my butt, may give me more control over the dildo and the strap that runs between my legs may move a little, giving me some clitoral and overall vulva stimulation. The one that I really like with the pockets for the vibes was definitely going to me the clitoral and vulvar stimulation that I needed. Woo Hoo!

So, all were very valid points, but my main concern was “Will these straps around my butt cheeks make my butt look fat?” Remember, my biggest fear here is that I’m going to look manly or just plain ole unattractive and I can’t have that. I called a staff member over and told her of my dilemma because I basically knew what I was interested in, but was torn between one or two straps. Luckily, she told me I could use the restroom to try them both on, over my pants of course. Relived that I had this option, I went into the restroom and gave them a try.

First, I tried on the two strap. It felt okay, I bent down and the straps moved a little, but not too much. Then I turned around to see what my butt looked like. I wasn’t too thrilled. It wasn’t that my butt looked huge, I just wasn’t crazy about those straps running under my cheeks. Before making a final decision about it, I tried on the one strap. Not only did it look better from behind, but it felt much better. Since it fit like a pair of undies, I felt like I would have full control over my member. Before making a fast decision, I gave each another try, first the two strap then the one strap and the one strap was the winner!

So let’s review my options…

  • Vinyl/Patent Leather Harness was  too stiff and cold to feel comfortable for me, but very attractive and stylish.
  • Leather Harness with Exchangeable O’Ring was too bulky looking in the front for me and was a two strap, but does give you many possibilities for dildos.
  • Leather Harness without O’Ring  – You can’t attach an O’Ring, so once the leather stretches you have to buy another harness, either that or try to sew an O’ring around the hole, but who wants to do that. They were available in one and two strap, but at that time, I didn’t see the point.
  • **2009 WINNER**Leather Harness with Pockets for Bullet Vibrators  had a pocket for a bullet vibe in the front which made it a little bulky looking, but it also had a pocket in the crotch for a vibe too which would feel divine, maybe a little too divine, while penetrating my girlfriend. So the decision I had to make here was, would the vibrations be way to much excitement for me? Remember, I want to be able to do this for a little while. But this one does give me options so it was ultimately the winner because I liked the look and the style and it was a g-string style.
  •  Recently, Adam & Eve sent me a surprisingly good strap-on dildo kit, Bree Olson Glitter Glam Strap-On Harness & Dong Kit. I’ve had a handful of wonderful experiences with it. So for purposes of this article and recommending good strap on’s Bree Olson’s is a good starter  strap-on harness & dildo of choice! However, if you’re going to be using it with different partners, you need to make sure you use a condom on the dildo because it’s not silicone, so you can’t completely clean & disinfect it.
  • *** NEW 2011 WINNER***  I’ve used many strap-on harnesses throughout my lifetime and the Spare-parts Theo harness is not only the prettiest and most fashionable looking harness, but the most comfortable harness as well. While the initial adjusting took a bit of time and help, it was totally worth it because I have a strap-on harness that I can use with a variety of dildos that fits so well and so comfortably that makes the dildo feel like it’s a part of me.

UPDATE 2013: As of this time, I am STILL using the Spare-parts Theo harness exclusively. It’s so super comfortable, gives me great control, looks great, cleans easily and has lasted a long time. 2 years and it’s still looks brand new. While it’s a little pricey, it’s so worth it. You won’t need to buy another harness for a long time.

Now it was time to pick out a dildo.

My desires were that it couldn’t look like a real penis, it couldn’t be too long, it has to be able to be sanitized and if my harness is black, it has to be girly (whatever that means). So, with my friends chuckling at the huge deal I made over the harness, I was off to the section where the dildos were on display. Now, as I was picking out my harness, my boyfriend kind of helped me, but when I called the staff member over, he gave me some space to make my own decisions. My kinky friends perused the other toys, but when selecting a dildo, I needed some assistance from those dear to me.

The staff showed me which dildos were silicone, that way the dildo can be put on the top rack of the dishwasher to sanitize after use. There were handful that actually fit through my O’ring. There was a sparkly lavender and light blue dildo. Then there was this dildo with a curve on the end of it, but it reminded my kinky friends of a bowling ball, it had a marble type design on it, I liked the design and shape of it, but not the color. Then I saw the sign that said, “all dildos available in different colors, ask for assistance.” So I called over a staff member. She showed me that she had a pretty pink one in the curved style that I liked. So now I was torn between the sparkly lavender one and the pink one. So I called over my kinky friends to get their opinion. My boyfriend, the staff member and my kinky friends all agreed that the pink was their favorite, because it was pink and it had the little curve at the end of it, great for g-spot stimulation. So there I had it my way cool, simple, yet sexy and secure fitting black harness and purple dildo, I was all set, now I can go play with the vibrators…

I wasn’t seeing my girlfriend that night, but when I got home, I tried the whole thing on. The harness has friction buckles on it so I just put the strap through the buckle and have my b/f pull really tight so it’s on nice and securely. Once I did that, it felt as though it was a part of me. The dildo sat right above my pubic bone and it didn’t look frightening either. Since I wasn’t doing the fucking that night, I got out of the harness and my boyfriend tried the dildo out on me. I gave it a test drive and it felt really good. It’s not too fat, or too long and does hit the ole g-spot. So needless to say, I’m very happy with my purchase. Now, I just have to get my chick and try it out…I hope that my strap on harness shopping experience has shed some light to help you pick out that perfect harness for you!

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Ann Andriani
My name is Ann Andriani. Since 1999, I've helped millions of folks sort through their questions and curiosities about sex. I hope that you enjoy your stay with me and benefit from my thoughts and sex advice.

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