My girlfriend and I met in our first year of university and have been dating for almost two of the four years we’ve known each other. We decided that we want to be more adventurous in bed and explore the use of sex toys. Eventually we settled on a strap-on. We scoured the internet, looking for adult stores, reading about body safe materials and trying to figure out what size dildo and what kind of strap-on we should get.
So off we went to an adult store, both of us excited and nervous to finally step into this mystical place, hidden by the shame and taboo of society. When we finally walked into the store, it was empty except for the lone worker sorting out a section of toys on the shelves. To our surprise, we weren’t the most nervous or awkward people in the empty sex store: They were! The worker looked so nervous, which was surprising to me, considering that they worked in the shop. Despite the awkwardness under the surprisingly hospital-like fluorescent lighting, we got the strap-on we wanted and a bottle of water-based lube, before we were on our way, ready to explore.
And explore we did, although I can tell you now, it’s not as easy as it looks.
What we initially thought was going to be a night of sensual pleasure, was actually a night filled with laughter, intimacy, and—eventually—orgasms. In our extensive research and effort to figure out what toy would be best, we forgot to look for tips on how exactly to use a strap-on, like which techniques would work best with certain positions. We thought it would be easy enough as it certainly looked that way in movies and porn. Oh, how we were mistaken.
I mean, the putting on of the strap-on was fine, it was using it that got us. We did everything we thought we should do. My girlfriend put the toy on and secured it before we made sure we were safe—the condom was on, and the dildo lubed up. After this we decided to go to the next step: Sex.
‘Missionary’ was the easiest position; I was ready and there was barely any pain. Whatever pain there was went to the back of my mind as the pleasure started to grow. It felt amazing!
We didn’t stop there. We wanted to try quite a few positions.
Next up was the ‘cowgirl’ position. This one was a little harder, but oh so worth it. I was in control, and my girlfriend had the best view of my body. It was a win-win situation, if I do say so myself. It felt really good, but there was one position that I really wanted to try: ‘Doggy style’.
Everyone would go on about how ‘doggy style’ was one of, if not the best, sex position to try with a strap-on. So, we tried, but we failed. The dildo would always slip out or poke me in the butt.
All we could do was laugh. We tried it on the bed. We tried on the floor with me bent over the bed. We even tried it with me leant against a wall, a counter, and a couch. Nothing was working. So, all we could do was laugh and try, and laugh some more, and try some more.
We chalked our failure up to three things:
In the end we gave up on ‘doggy style’ and decided to go back to what worked for both of us. I can say that the positions that worked, worked really well for the both of us.
Although the night did end in pleasure, it was the laughter that stayed with of us. Sex, which is something that we assumed is always sexy and natural, became something funny and embarrassing. This moment helped to teach us that sex isn’t always going to be perfect, especially when experimenting with toys. Yet despite its imperfections, sex can be wonderful and intimate, even when funny and embarrassing. I discovered that the joy of sex didn’t only lie in the pleasure and the sexiness of it all, but in the intimacy, safety and trust between partners who are unafraid to be authentically themselves with one another.
This failure of successfully performing ‘doggy style’ only brought me and my girlfriend closer together. It taught us that we can’t take ourselves too seriously. Sometimes it’s okay to laugh at yourself and revel in the joy of failure, rather than dwelling in the negatives. This is something I carry with me beyond the bedroom.
Who knew failing a sex position could teach me so much about enjoying life, and myself?
We still haven’t completely figure out ‘doggy style’, so if anyone has any advice, we’re open to hearing it!
