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31 Days, 31 Orgasms: My Journey as A S*x Toy Novice Revealed

May 22, 2023

31 Days, 31 Orgasms: My Journey as A S*x Toy Novice Revealed

I masturbated every day for a month in honor of Masturbation May

Let me set the scene for you. It was 11 am on a random Monday, and my team and I were on a call talking about what we could do for Masturbation May. We were going through a list of ideas, and someone brought up doing a 31-day big “O” challenge. Then I had a “hold up, wait a minute, Mr. Postman” moment if Mr. Postman were to collaborate with Carrie Bradshaw.

I begrudgingly* (*by begrudgingly, I mean embarrassingly eagerly) suggested, “Well, what if we did an op-ed about what it’s actually like to masturbate every day for a month?” And it was met with so much enthusiasm that our Head of Marketing asked our Head of Sales if she could get me a box of sex toys ASAP in the comment section of a Google Doc. Was that the peak of my career? I think it might’ve been. 

Flash forward to that following Tuesday. Things were in motion, and we decided I should start that day so the article would be ready by mid-May. I was hit with a moment of realizing that this was happening and in full swing, which meant I had to come up with a plan and address the elephant in the room. My Colombian grandparents would probably share the link to my self-pleasure marathon in WhatsApp chats across Latin America without fully realizing what it was, saying, “bendiciones!” 

So I did what any grown and mature adult would do: I called my mom and asked her to dissuade them from reading this one. Like the saint she is, she agreed — and it was time to get started. 

Si llegaron a este punto y son mis abuelos, por favor, se los suplico… paren de leer!

Getting started is actually not always the hardest part

I went into this with a big ego because I saw it as an opportunity to deepen my ability to ground myself in my body through sensuality, and self-pleasure.

Before this experiment, I was fairly indifferent to the impact and importance of masturbation. It wasn’t something I really thought about — just something I did when the urge came up. Sometimes, a few times per week, other times once per month. It was a means to an end, and though there were times when I liked drawing it out — I was usually in and out in less than 3 minutes. Not very romantic or mindful, I know. But I wanted that to change.

I loved the idea of becoming more in tune and aware of my body and the many places where pleasure can live within it. And in full transparency, I was especially curious about translating this knowledge into my sex life. I wanted to develop a kind of affinity for my desires and preferences that I could use to help guide others and feel more confident and outspoken about what I wanted. 

So, in true Type A fashion, I thought the best thing I could do was set a few goals for myself going into everything. Intentions, if you will. 

The Cumming Manifesto:

  • Try new kinds of sex toys.
  • Experiment with masturbating at different times. 
  • Switch up the inspiration.
  • Figure out how to incorporate more self-pleasure into my sex life.

I told myself that if I incorporated these elements at least once, I’d consider it a win. And this is how it went.

Week 1

The first week was the easiest and the most curated. There was an underlying sense of excitement surrounding the fact that I would be taking the time to orgasm each day for a month. Sure, most people in my life were aware of it — but strangers weren’t! I walked a little taller like I was hiding a secret. I felt like the main character in an old-school erotica novel.

Some nights, I’d pour myself a glass of wine, light my Trader Joe’s candle, and read slow-burn romances. Others, I’d bathe while listening to music to set the mood. Build out little fantasies in my head, allowing myself to get lost and carried away in the lightness of yearning when yearning is vague. 

I tried to pace myself and think about self-touch more mindfully. At first, a few moments of hyper-awareness made me feel awkward. It felt kind of funny and uncomfortable to touch myself with the same patience and softness I would someone else. Like I was breaking the fourth wall or trying to hack my sex life by giving myself a thorough experience. Made a note to unpack that in therapy, don’t worry. 

But, the more I allowed myself to focus on the matter at hand (literally), the less sense my initial hesitancy made. 

As cringe-worthy as it is to write, I felt the same kind of giddiness that’d only ever emerged at the thought of getting to know a new partner. Only this time, I was taking that energy and curiosity and getting to know myself in a different way. 

By day 4, it started to feel more natural and easy. By day 5, I started to feel excited about the prospect of spending more time exploring and discovering new things about myself than I was about reaching orgasm. 

I noticed a big shift in my mood — but not so much because I was orgasming routinely (though I’m sure that helped). I think there was just something fundamentally empowering about this new approach to masturbation. 

As cringe-worthy as it is to write, I felt the same kind of giddiness that’d only ever emerged at the thought of getting to know a new partner. Only this time, I was taking that energy and curiosity and getting to know myself in a different way. 

I felt like I was thriving. There was just one little thing. I was leaving on a company trip to Spain the next day.

Week 2

My bags were packed, and I had to be at the airport at 12. We were set to land in Madrid at around 3 pm (GMT+2) and wouldn’t be getting to the hotel until 6. This was my first time meeting everyone on the team in person, our schedules were busy, and I knew the jetlag would hit me like a dump truck.

All of this to say, I had one chance and one chance only to masturbate, and it was at 7 am. I reached into my nightstand to grab my one and only sex toy, a vibrating wand and had the least mindful, most bland self-pleasure session I’d had in a long time. And this is where I started messing with a good thing. 

The thought of my coworkers hearing a subtle, persistent buzz through the walls made me decide to leave the toy in New York. I tried to fake-sell it to myself by saying that going analog would help me truly get in touch with myself. 

For context, I have been happily frying off the nerve endings in my clitoris for the past decade. A trip where I knew I’d already feel self-conscious about everyone knowing I was working on this article was not the time to go rogue. 

Admittedly, this wasn’t my strongest week. I was jetlagged, socializing from 7 am to the wee hours of the morning, meeting my coworkers face to face, and exploring a new city — masturbation wasn’t really at the top of my mental to-do list. 

I was very unromantic, and honestly, I did skip a day or two when I crawled into bed at 3 am. It all felt uninspiring, especially compared to the first week when I felt like a mystical nymph. 

And that’s when my fairy godmother stepped in. You might remember me saying that our Head of Sales had been asked to see if she could get me a box of sex toys when I first pitched it. Well, being the icon that she is — made it happen. She told me I’d be getting a package from LoveHoney, and all I needed to do was pick out the toys I wanted. 

In honor of the Cumming Manifesto and wanting to try new things — I opted for toys I hadn’t tried before and some that felt a bit intimidating.

I picked out my favorites, and when I asked for four, she looked at me and said, “Say no more, it’s done.” (Creative liberties were taken, she definitely said something more professional). 

Our trip came to an end, and I boarded the plane back home. Waiting at my front door was a brown box about the size of a microwave oven. 

Week 3

The LoveHoney package couldn’t have come at a better time. I was ready to get back to main character mode after my week of mediocre masturbation, and what better way than with a box of curated sex toys? 

I did what anyone in my position would have done, unboxed everything at once, and lined them up to charge like ducks in a row. 

Here’s what I ordered: 

  • Fifty Shades of Grey Black Rose Silicone Clitoral Suction Stimulator
  • Lovehoney Deluxe Rechargeable Mini Metallic Massage Wand Vibrator
  • Happy Rabbit Realistic Rechargeable Rabbit Vibrator
  • We-Vibe Touch X Rechargeable Clitoral Vibrator

For context — I’ve been a one-toy-wonder since the start. I’ve always just had a silicone wand and never cared for insertable sex toys, mainly because they looked intimidating. I went into this thinking that I knew what my favorites would be and what would underwhelm me — I was surprised at the final outcome. 

So, let’s get into it because it was exciting. 

Fifty Shades of Grey Black Rose Silicone Clitoral Suction Stimulator

After years of reading about its almost supernatural powers, it only made sense to start by trying out the rose suction stimulator. 

First things first — it’s sleek, light, quiet, chic in a dom sort of way — all things I associate with a quality sex toy. That being said, I’ll say it if no one else will, it’s not exactly intuitive. 

I mean, yes, looking at it, I could tell you what was supposed to go where. But in terms of how I was supposed to position it to get the most out of it and the ideal suction intensity… it took a bit of getting used to. 

Personally, I didn’t think this necessarily mimicked the sensation of a tongue, but it was definitely an attractive relative. The first time I used it, I swapped it for a wand when I was ready to wrap things up — but I enjoyed the build-up and specific sort of pleasure it created. I’ve heard similar reviews from people with penises in regard to using strokers.

Throughout the week, I ended up using it to set the mood before going in with one of the more vibration-focused toys — and thought it was perfect for that. To me, it felt like the kind of toy that gets better the more comfortable you get with it and the more you use it — so I’m excited to see how my use of it evolves.

Lovehoney Deluxe Rechargeable Mini Metallic Massage Wand Vibrator

As a self-proclaimed wand expert, I decided to try the LoveHoney wand the same day I tried the rose to climax. I wanted to see how it compared to the wand I’d used for years and didn’t expect much difference. I was wrong! It had a way better and wider range of patterns and vibration intensities.

I love wands because they’re great beginner-friendly toys and (in my experience) the least intimidating to use with a partner. Since the silicone head is the main event, it’s super easy to hold (or guide someone else’s hand) and find the exact spot, motion, and pressure that works for you. 

It was my emotional support sex toy this week as I tried different toys, and was a quick favorite. 

We-Vibe Touch X Rechargeable Clitoral Vibrator

I was super excited to try this perfectly palm-sized vibrator. I loved the fit of it, the size, the intensity settings, and the color — this would definitely be another first sex toy recommendation. 

Overall, this felt like another great daily-use sex toy that doesn’t need any mental or physical prep. And something that could add extra pleasure during sex. This and a strap-on? A done deal. 

I used this vibe and the wand the most this week, sort of interchangeably, even though the actual sensations are a bit different. This felt like a more general and diffused sort of stimulation, whereas the wand was more intense and focused. 

So, it’s something that I realized was nicer for when I wanted to draw things out a little more and wanted a more sensual and tender experience. 

Happy Rabbit Realistic Rechargeable Rabbit Vibrator

I am going to be so bombastically for real with you right now. At first sight, looking at the rabbit scared the absolute life out of my body. 

It looks huge, it’s got bunny ears coming out of it, it’s curved, it thrusts — it was something that took some mental prep work to try.

I’d mentioned earlier that I wasn’t ever really an insertable sex toy kind of girl. But since I had certain goals I wanted to reach, and I was on this more-self-pleasure-new-me journey, I knew it was something I was at least willing to try once. 

I waited until the end of the week to bring it out after I felt like I was back in a good masturbation flow and headspace. Sort of by choice, sort of also because I didn’t realize how much time I’d spent using the other toys and not charging them. So when my palm vibrator died mid-masturbation, I felt like it was a sign. 

I felt the same awkwardness I did the first day or two when I was starting to be more mindful about tuning into my whole body when I turned it on. Except, instead of freezing up and rolling my eyes at myself, I was able just to let that feeling pass because I felt a lot closer to pleasure and openness after three weeks of self-exploration. 

It did what it needed to do — and I’m not exaggerating, here — in under 10 seconds. I was shocked. My jaw? On the floor. 

The moral of the rabbit? Keep an open, non-judgmental mind. Sometimes the most intimidating sex toys lead to the best orgasms. 

Week 4

During my last week, I naturally started shifting toward a routine and approach that felt more “me.” I didn’t start each time with an elaborate self-care routine or whip out the rabbit every day just because I could — but I also didn’t go back to my old ways.

I was more present, mindful, and intentional — all while still holding onto an element of openness and curiosity. It was kind of comforting to know that I’d be spending time focusing on myself, and pleasure.

There was a certain element of nostalgia (I’m a Scorpio, let me be dramatic) about this coming to an end. I think realizing that motivated me to prioritize being intentional about how I spent my solo-play time these final days, which didn’t feel as important before.

So, rather than curating elaborate experiences — looking to see how different rituals, settings, toys, and acts worked better with different moods I was feeling. I think this felt the most fulfilling throughout, especially because usually, if I was under a lot of stress or feeling down, masturbation was the last thing on my mind.

This brings me to… 

What I learned during my Masturbation Marathon

The key takeaways of this experience. 

I wanted to incorporate and work toward a few tangible goals when I started this experiment. 

The Cumming Manifesto:

  • Try new kinds of sex toys. 
  • Experiment with masturbating at different times. 
  • Switch up the inspiration.
  • Figure out how to incorporate more self-pleasure into my sex life.

How did I do? I tried new sex toys. Hit it out of the park with that one, actually. I experimented with masturbating at different times (though I definitely prefer evenings). I switched up the inspiration. And I feel like I picked up on things that I’ll definitely be bringing into my sex life.

Beyond just the sexual benefits, the biggest differences I noticed during this month had to do with my confidence, self-trust, and sleep habits.

I feel like I’ve always struggled with feeling a bit awkward and quiet in social situations. As someone with anxiety, I spend much of my time trying to get out of my own head — not tap into it. 

So spending this month trying to be so intentionally present with myself, even in the moments that made me feel self-conscious and awkward, was actually pretty revolutionary. I know it sounds a little funny, “How I masturbated myself confident!” But it’s true. 

I was able to give myself the gift of patience, to willingly put myself into situations where I knew there’d be small stutters, confusion, and clumsiness — and gave myself the gift of trying again. Of breathing through it and encouraging a continuation of exploration.

And that also helped create a sense of trust that I didn’t really think would be possible to unlock through this journey. Of saying, I trust you to use the scary-looking toy! I trust you to keep yourself safe! I trust you to know when something is worth exploring and when something doesn’t feel good! I trust you to find ways to make this something you’ll look back on and feel grateful to have done!

I also don’t think it’s a coincidence that this is around the same time I magically started waking up at 5:45 am every morning without being angry at it. I felt like the quality of my sleep improved significantly. In part, maybe because my brain started associating this routine as the last stop in my bedtime routine. 

It also helped replace the habit I had of doom-scrolling and laughing at TikToks in the darkness because both of those things didn’t really seem appealing after a routine that started to feel pretty sacred and gentle. 

Sure, there were a few roadblocks. I didn’t do the 31 days back to back exactly. But I think it’s human and okay. After all, I’m not about to bring guilt into something I did to grow my understanding of pleasure.

Though I don’t think it’s realistic or sustainable for me to masturbate every day of my life, I do feel like it’ll continue to be a more fleshed-out, holistic practice moving forward. 

I got to know myself a lot better (and thousands of strangers, friends, and relatives did, too), and hope that this has inspired you to try something new, no matter how small, in your own life. 

Daniela Ochoa-Bravo is a writer and creative based in Brooklyn, born in Bogotá. She is the Founder and Editor of Colectivo Tabú, a project dedicated to democratizing the publishing industry by creating a space where the works of emerging and established artists can seamlessly coexist alongside each other.

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