A+ Sex Diary: Masturbation Challenge Accepted

Welcome to A+ Sex Diaries, an A+ feature in which we publish seven days in our sex lives. This week: A single femme trying to get back in touch with herself. Literally. Queer, 31, hailing from the Midwest.


Day One

5:00 a.m.: I’ve been struggling with a low libido lately, for a lot of reasons — I don’t have a romantic partner at the moment, living with roommates leaves me with very little alone time, I’ve been stressed with work, I’m always dealing with depression. Still, I don’t like that I’m losing the parts of myself that are fun, body confident, and sexy. I can feel myself growing more shy and disconnected with my body every day.

I recently spent some time thinking about how to better tap into my body and desires. I’ve heard about “masturbation challenges” in the past, so that’s what I’m going to do! I’ve decided to challenge myself to masturbate at least once a day for the next week.

It’s 5:00 a.m. on the first day of the challenge, and I have a bit of performance anxiety. I woke up to use the bathroom anyway, but decide to spend an hour reading porn before I fall back asleep. I’ve always preferred reading porn to watching it, I feel like it leaves more room for my imagination. I’m not yet ready to masturbate, but hopefully filling my brain with sexy thoughts will help rev up the engine.

11:15 a.m.: My middle of the night porn session totally messed up my body clock! I overslept by hours! My roommates are gone for most of the day today. I want to make the most of it. But first I have to wake up — right now everything’s a sleep fog.

12:38 p.m.: Ok, I’ve also cleaned all my old toys and my hands. I clipped my nails yesterday. It’s time.

I try not to put too much effort or focus on orgasming; I know that a lot sex experts say that focusing on an orgasm will shortchange you from enjoying other parts of your sex experience (the touching, the exploration, the playing, etc.). It also can ramp up your anxiety. Still, when I masturbate and don’t orgasm, it kind of feels like I wasted my time. I know it’s not true, but there’s some ingrained part of me that I can’t shake.

Anyway, I do eventually orgasm, but it takes a lot longer than I would have liked, and I didn’t feel very satisfied. I want to make use of having the entire apartment alone and try again later.

2:23 p.m.: After taking a break for my writing and texting with friends, I’m back at it. I never put back on clothes, I figure getting comfortable with myself naked again is part of this whole project. I’ve gained quite a bit of weight since I last felt sexy. I keep noticing how my belly fits my body in this new, kind of protruding way. I’m not sure how I feel about it. I definitely don’t hate it, but it’s…. different.

When I start masturbating again, I am shocked by how fast I come! It threw me completely off guard! It was fast, and strong, and over before I could adjust to what was happening. It felt getting blindsided by a train. That’s new for me! I wish I had more time to explore or bask in what just happened, but it’s getting late.

I reluctantly get dressed and get about doing my normal Sunday routine — chores, cooking, laundry.

Day Two

8:45 a.m.: Last night I made the effort to put on sleepwear that make me feel confident and sexy. For me, that’s an oversized cut off sweatshirt that flatters my curves and my soft cotton flannel pants. The outfit is a cozy kind of sexy that feels like me. I catch myself in the mirror while finishing my morning routine — I look hot. I don’t feel like having sex with myself yet, but it’s still fun to appreciate my body.

Day Three

10:11 a.m.: I had terrible stomach pains that kept me up all night on Monday. I’ve already dropped the ball and it’s only two days in to my masturbation challenge!

I’m so disappointed! I already have a tendency to be too hard on myself, and this doesn’t help. AT ALL. I wake up Tuesday morning with a slightly better outlook. I can’t control my body or illness. I decide that if I masturbate before getting out of bed, it can technically still count in Monday’s tally.

I stretch out and read some of my favorite erotic fanfic on my iPhone. It involves a threesome of three television characters who have never shared a screen in real life. It takes a while for my mind to focus on the task at hand. My brain keeps wanting to anxiously go over my to-do list for the day, but the story I’m reading helps. By the time the characters reach their grand finale orgasm, I am working towards my own. I’m surprised that I am able to get there using just my fingers. Usually I need some kind of hard friction against my clit (either from a vibrator, or rubbing against a surface or partner) to come. This morning the comparatively gentle stroke of my fingers is enough.

6:00 p.m.: Got home from work and discovered that my new sex toys had been delivered!

Last week, in anticipation of my challenge, I ordered two new toys. The Lelo Gigi 2 is my longest-running, most-trusted vibrator. It was a steadfast companion for most of my 20s, but I lost it over a year ago in a move and I’ve been too cheap to replace it until now. It’s the kind of toy that I can always depend on for a strong orgasm, but $100+ vibrators are not always in my budget. I also treated myself to the Lelo Sona, which is supposed to be Lelo’s answer to the Womanizer or Satisfyer suction-based vibrators that everyone’s been raving about. My understanding about the sonic toys is that they “suck the air around,” rather than rumble directly on, your clitoris? I have no idea, honestly. But I do know that at least four of my friends have sworn that this style of toy has given them near-immediate orgasms. It sounds too good to be true, but their stories definitely piqued my interest. I originally wanted a Satisfyer, but the Sona was on sale.

6:15 p.m.: Go straight to my bedroom to unwrap my new toys like it’s Christmas morning! I’m so giddy. My Gigi is just as beautiful and smooth as I remember it. I delight in the ways it rumbles against the palm of my hand. Also, I can now guess why the Sona was on sale — it’s loud! Almost alarmingly so! I couldn’t get past the lowest setting, just laying it against my hand, before rushing to turn the toy off! This is definitely not roommate-proof. I’ll save it for the next time I’m really alone.

11:48 p.m.: Try as I might, I just can’t seem to get myself into the mood. My intent was there. I did all my usually dependable mood setting tricks. I got naked and enjoyed the feeling of my cotton sheets against my bare skin. I grazed, then pinched and rolled, my nipples. I reminisced about past sex highlights. I simply couldn’t make my body feel aroused. But, I think this still counts as masturbation? Even if it got me nowhere.

Day Four

3:03 p.m.: For the first time in MONTHS I’m spontaneously horny in the middle of the day! Maybe there is something to this masturbation challenge after all. My body is remembering that this side of me feels good, and is starting to crave it. In a major way.

The feeling is getting to the point of distraction, and I know I had extra time alone anyway, so I close my office door, and sneak in a middle of the day quickie. It’s awkward at first. Even though I know I’m safe from being walked in on, the idea of a mid-workday masturbation session is a lot to wrap my head around.

I guess it’s a little sexy in that exhibitionist way? But mostly it feels rushed. Still, 10 minutes later and the orgasm I was previously distracted by has finally arrived. My thoughts feel clearer and more sharp, and I’m ready to tackle the rest of the day.

I clean up a bit in the bathroom. Then I treat myself to a slice of blackberry pound cake and a tall glass of water before getting back to work.

7:35 p.m.: I research “Masturbation Challenges” on my phone while eating my dinner. I come across an old one from Refinery29 and a month-long “Masters of Sex Cure” from Autostraddle⁠.

I started my week long masturbation challenge a bit blindly — I wanted to get myself out of a rut and reconnect with my body. I didn’t think of any specific guidelines other than “masturbate once a day.” It turns out I could have been keeping a journal, focusing on trying out a new technique every day, or filling out reflection worksheets.

WHOOPS! It’s a little late for now, but I bookmark the websites anyway. This challenge has been going pretty well so far — maybe I’ll take some of their advice if I decide to do another week-long masturbation experiment in the future.

Day Five

1:00 a.m.: I finally have the chance to break in my new Gigi. It feels exactly as I remember it. The weight of the toy in my head, the velvet feel of the silicone, it turns me on almost instantly. It’s like getting reacquainted with an old lover. I start with toy buzzing low between my legs while I use a free hand to lightly stroke up and down my arms and breasts. I want to stretch this out before I come.

Day Six

10:45 a.m.: Saw this quote on twitter during my mid-morning break: “My alone feels so good. I’ll only have you if you’re sweeter than my solitude.” It’s from a Warsaw Shire poem.

I smile, “My alone feels so good.” That’s truer this week than it has been in very, very long time.

11:58 p.m.: I’m home, but slightly tipsy from happy hour and dinner with friends. I feel warm underneath my cheeks, a bit giggly and bouncy. In my bed, I decide to go without the toys for the night.

It always takes me longer to orgasm when I’m only using my fingers and the friction of my bed or pillows. I try to focus on enjoying the build up instead of being frustrated by it. I feel more free tonight, more willing to explore and indulge. It’s not the biggest orgasm I’ve had this week, but damn it’s satisfying.

Day Seven

1:14 p.m.: Alone in the apartment for the first time in a week, and I have two goals: First, I want to finally play around with my Lelo Sona. Second, I want to take a long luxurious shower with my lavender scented body scrub and honey-lavender face mask.

It takes a while for me to find the correct fit of the Sona against my clit. The whole process is much more awkward than I anticipated. It involves a lot of me attempting to painfully double myself over so that I can have a better direct view of my clit and place the toy just right on top of it. I think someone who’s more flexible might find this process a bit easier, but I am who I am and this is where we are. I try not to get upset and keep the mood light for myself. After some trial and error, I get the toy just where my body needs it.

I thought I was going to be more bothered by the toy’s noise, given how loud it was when I first unboxed the Sona earlier in the week. Turns out, I didn’t have a lot of time to think about that, because within seconds — literal seconds — of getting the seal just right, I was rocketing towards an orgasm.

I once had a friend who described the Womanizer as “stealing her orgasm” because it felt like she didn’t have a say in it. She just turned it on and then “ZOOM!” The memory makes laugh almost immediately after I come, because I feel exactly the same way.

Being able to have an orgasm that quickly is addictive! Almost as soon as I relax, I’m ready for a second. By 1:30, only 15 minutes after I first laid down, I’ve already had three orgasms.

2:30 p.m.: Fresh from my shower, my skin smells like lavender and is sooooo soft! I can’t stop touching my arms, my legs, the round swell of my stomach. I feel delicious. I put on my softest robe and settle into my face mask while I catch up with old Riverdale episodes.

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4 Comments

  1. This sex diary is so important, all the different types of sex we have is important!

    Thanks anon, and wow, I hope you continue to challenge yourself ;)

  2. Love thisssss and also a perfect capture of those suction vibes. they really do just yank the orgasm right out of ya

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