My Sexual Bucket List

These are the fantasies I want to turn into realities

When I was in my late teens, I simultaneously couldn’t wait to have sex and also hoped to avoid it for as long as possible. I was insatiably curious about sex, yet I also carried so much shame around my sexuality that I couldn’t imagine letting a man see me naked, let alone experiencing the intimacy of him being inside me.

Sex with my first partner was not great, but not terrible, either. And over time, and a couple partners later, I began to shed more and more shame and inhibitions.

But there are still some hang-ups I wasn’t able to overcome before the end of my last relationship. And of course, my partners were not always interested in experimenting with the same sexual activities that I wanted to try.

So there are still a few things I would like to experience someday. I admit, this is probably the most vanilla sexual bucket list you’ll ever read. But hey, I’m a realist. I’d rather aim for things I think I can make happen someday, rather than items so aspirational or outside my comfort zone that I’ll probably never get around to checking them off.

Vanilla or not, here we go:

1. Shameless cowgirl

One of my greatest sexual regrets is that I was never able to fully allow myself to enjoy the cowgirl position. I have always loved this position, but because of the shame I’ve held about expressing sexual pleasure and my body image issues, I’ve typically frozen like a deer in the headlights once I’ve climbed on top of my man.

Most of the time, in this position, I ended up doing a “rocking horse” (fun but no dynamite), or bracing my knees alongside my partner and hovering over him while he did all the thrusting.

What I’ve really always wanted was to be able to move up and down, back and forth, and basically enjoy every sensation of my partner’s penis moving inside me.

I feel like I’ll know I’ve made great strides in the “no shame department” when I’m able to check this one off the list.

2. Fulfilling oral sex

I’ve never been a huge fan of having a man go down on me, believe it or not. I mean, it feels great, don’t get me wrong. But it often leaves my clit feeling smothered.

It’s hard for me to handle direct stimulation on my clit — it gets numb or overworked so easily unless the pressure is constantly changing and the area of stimulation shifts from time to time. Add to that the heat, heaviness, and moisture of the tongue, and it just overwhelms my senses, though not in a good way.

To be honest, I wonder if maybe I would have enjoyed it more if I could have communicated better about what I like and don’t like. Asking a partner to constantly change what he’s doing feels like it might come off as nagging or criticism. I’ve had partners get angry or sensitive over just one, “Could you please lighten the pressure there?”

I’m grateful when a man makes an effort to try to please me and I want him to feel confident in his expertise as a lover. I’ve just never been able to figure out how to accomplish the relaying of specific and ongoing instructions involving the stimulation of my clit while simultaneously making him feel confident about what he’s doing.

Also…to this day, I find oral sex a little bit scary and incredibly vulnerable. So there’s a lot of stuff going through my head when a man is doing that for me and it’s hard to focus on just letting go and enjoying myself.

I hope one day, though, to be able to totally relax and to have a partner who is deeply secure in himself who can handle me whispering, “A little to the left…softer…harder…a bit faster…right there…move down…yes, just like that…now up again…”

3. Period sex

Truthfully, this one feels pretty aspirational to me, considering how my exes have felt about my period.

Also, this one surprised me. Even five years ago, period sex wouldn’t have been on my list, due to my own hangups around menstruation and the painful cramps that I typically experience. But as I’ve gotten older and have less period-related pain, I find that I’ve become incredibly horny during my period.

I’ve never been with a man who wasn’t disgusted by my period, so this has also become an issue of love and acceptance for me. I want to know what it feels like for a man to want me every day of the month. I want to know what it feels like to have someone who loves me and desires me for everything that I am as a woman.

The thought of being with a man who would still desire me when I’m bleeding turns me on more than I can say.

4. Sex in the spa

In general, I actually don’t like sex in water. It sounds great, in theory, but I’ve found that water washes away my natural lubrication and makes for very difficult and painful penetration and thrusting. I have never been able to achieve an orgasm in the shower for this reason (with the exception of my solo fun with the shower head).

However, I remember one summer day when my partner and I were dog-sitting for my mother at her house. We got into the spa. He started rubbing my feet. I moved to straddle his lap. We kissed. He pulled my breasts out of my bathing suit. Sucked on my nipples. Slid a finger inside me.

I wanted to have sex so badly in that moment, with all the warm water around us, the delicious way my breasts feel in the water, so round and weightless, the jets making the hairs on my arms tingle… But we stopped, worried that my mother would arrive home at any moment.

At the time, I figured it wouldn’t have worked out well, anyways, because of the problems we’d always had with lubrication in the shower. But I realized later that there were other ways we could have given each other orgasms if penetration was a problem.

Now, every time I see a spa, I think about what I want to do with a future lover…

5. Masturbating in front of him

Before my last partner, no one had ever asked me to masturbate in front of them. And in fact, if they had, I would have been mortified.

By the time I was in my thirties, I was a bit more open to this. I could make all the motions, but I just couldn’t get into the right headspace. Old patterns of sexual shame would creep in, dulling my senses, making me dissociate from my body, and I would end up feeling no more aroused than if I had been stroking my thigh.

Now that I have a little more confidence, and a little less shame, I fantasize about touching myself in front of a lover, being able to look him in the eye as I did this, maybe — preferably — with his hand on my breast, thumb against my nipple. Maybe as he drops a deep kiss or two on my lips. I want to be able to experience orgasm like this, shamelessly, as he watches me.

This isn’t an exhaustive list, by any means. I have other things I want to try: lubing up with body oil (though I suspect this might have some humorous and un-sexy results), sex in semi-public places, sex without using the hands, blindfolded sex, sex in the outdoors, eating food off each other… I could go on, but you get the idea.

Things notably not on my list:

BDSM (other than the blindfold thing, which apparently falls into this category). I never read Fifty Shades of Grey, believe it or not. My sister said its 20-something-year-old virgin protagonist falling for a wealthy man would upset my feminist sensibilities. So yeah, I guess I missed the BDSM train.

Anal sex. This one is just too far outside my comfort zone. Though who knows — like period sex, it might make an appearance on this list one day. (Incidentally, and perhaps illogically, I would have no objection to giving my partner certain types of anal stimulation.)

Exotic sexual positions. My last partner and I tried countless different positions, and honestly, I only ever crave four simple, classic poses.

Threesomes. Until someone can prove to me that one person in a threesome isn’t, at some point, just going to be hovering somewhere awkwardly, then I’m not interested. Because let’s face it — I’d be the one sitting there, watching, trying to figure out where to insert myself. This just doesn’t seem the slightest bit sexy to me outside of my fantasies.

I have no idea what the future holds for my bucket list. I might meet a man who has a tongue like a Pendleton blanket that sends my clit scurrying back into the safety of my vulvar folds. (Though I imagine the kissing would be hot as fuck. I love a hot and heavy tongue kiss.) Or maybe I’ll never find a guy who can handle a menstruating woman in the bedroom (gods, please say it ain’t so). Or maybe he’s had so much spa sex that the idea completely bores him.

I don’t know if I’ll get to check these items off my list, but I’m excited to see what comes of it. (No pun intended.)

© Yael Wolfe 2019