What I Learned from Attempting to Conquer My Sexual Bucket List

I wouldn't necessarily say I consider myself unattractive, but I've never really felt desirable, either—a sensation that likely stems from some not-so-great formative sexual experiences in my adolescence. I always seemed to like my romantic interests more than they liked me, and the first few guys I was with subscribed to the "vaginas are gross" stance that's weirdly pervasive among teenage boys.

By the time I entered healthy, reciprocal relationships, the damage to my self-esteem was already done.

When I found myself single for the first time in more than three years, I was nervous. I ended things with my boyfriend in large part because I had never gotten the chance to date casually and explore, and I couldn't help but wonder if that had been a mistake. But now I wondered if I wouldn't attract enough people to have the libertine adventure I envisioned.

This fear was quickly put to rest after a few weeks on r/r4r, Reddit's digital equivalent of a personals section, and a handful of subsequent encounters with men who I would have previously considered out of my league. Thus, my sexual renaissance began.

These rendezvous emboldened me, and I eventually began to think about taking my experiment to the next level. What if, instead of just random hookups, I used my newfound momentum as an opportunity to get really adventurous? Exhilarated, I drafted a post with a list of fantasies and a call for anyone interested in helping me achieve them. It wasn't long before I had a roster lined up.

The threesome

Ah, the threesome. Is there a more iconic sexual bucket-list entry? I think not.

I had a few couples reach out to me and I later found out I was what people in that community called a unicorn: a single woman interested in joining a male/female couple in bed. I ultimately met up with a couple in their 30s. He was tall and macho; she was short and sweet.

We got drinks at a cocktail bar that was equal parts retro, hipster and new age. I had no idea what to expect on a three-person date, but it was surprisingly natural. It felt like I was meeting up with a couple of friends I hadn't seen in a while. As we drank, laughed and got to know each other, I wondered if anyone at the bar could tell what was going on. If they did, they made no indication of it.

Afterward, we headed back to their place, a sprawling flat in a trendy neighborhood that I was shocked they could afford. I expected we would go to their bedroom, but instead, they invited me into a surreal, "Alice in Wonderland"-themed den. There was a tall, red wingback chair, a defunct fireplace and, most noticeably, a 10-foot-wide trampoline. (You can probably guess what they used that for.)

I was again surprised at how naturally events unfolded, but it didn't take long before I realized I wasn't into it. The girl was a bit too femme for my taste, and the guy sucked on my neck so hard that he left bruises. I appreciated the novelty of the experience, but I was ready for it to end pretty early on. The best part was chilling on the trampoline and sharing a joint after everything was over. The weirdest part was realizing their across-the-street neighbor was standing at the window watching us.

They invited me to stay the night, but I told them I had to go back home to let out my dog, which was true. I realized on the Lyft ride home that I had left my earrings and sunglasses at their home, but I decided that was a price I was willing to pay. I was glad I could cross "threesome" off my list, but I wasn't eager to go back anytime soon.

Deflowering a virgin

The only time I took a guy's virginity was when I was a virgin myself, but I've always found the idea of a more experienced lover guiding somebody through their first time to be superhot—so I decided to try the role of sex sage myself.

There were more volunteers for this list item than any other. Dozens of men responded, each longing to shed the title of virgin once and for all. Some were guys in college who had little luck in the past. Some were older, held back by conservative religious or cultural backgrounds. Others struggled with anxiety or hadn't found the right person yet.

In the end, I went with a guy in his late 20s who was kind and cute but painfully shy. We talked quite a bit before we actually met in person. I wanted to make sure he was ready and wouldn't catch feelings, and he wanted to get to know me a little better.

When we met for drinks, he was timid but could carry a conversation perfectly well. I've always been good at drawing shy guys out of their shell, and we ended up having a fun time.

I invited him back to my place, where we took things slow but steady. I was honestly pretty impressed. If I hadn't been told otherwise, I doubt I would've known he was a virgin. I briefly wondered if he had been lying just to get laid, but the sincerity on his face quickly dissuaded me. He was both psyched and relieved to have swiped his v-card, and I felt good about making it a positive experience for him—not in a charity case kind of way, but a wholesome, I'm-so-glad-this-worked-out kind of way.

We got together once more afterward, but I realized it was time to push the baby bird out of the nest. He was looking for something a little more intimate than I was, and at the time, I didn't really have the emotional bandwidth to accommodate that. In the end, we wished each other well and parted ways.

The older guy(s)

Up until that point, I had only dated men within a couple of years of my age. I wasn't necessarily against seeing older men, it just never really occurred to me since the vast majority of men in my social circle were close in age. But in the midst of my sexual renaissance, anything was on the table—including Gen X.

I met my first older gentleman friend through Tinder. He was in his early 40s, but could have easily passed for 10 years younger. I didn't have terribly high expectations, but he had a handsome, dorky hipster vibe going on and was pretty good at banter, so when he invited me out for drinks, I accepted. We met at a newspaper-themed bar downtown, where we drank fancy cocktails while he regaled me with stories about "real adult things" like his corporate job and his nostalgia for the 1980s. 

He continued to wow me with his maturity after I went home with him. A two-bedroom condo with a clean bathroom! Art on the walls and books about jazz pianists! I never would've admitted it, but I was smitten. He was the funny, Jewish nerd of my dreams with his life together to boot.

I was glued to my phone the next several days, hoping he would text again. After a week or so, I couldn't take it any longer and asked him what his schedule looked like over the next few days.

"Sorry, I'm in Chicago visiting my sister," he told me. I wanted to believe him, but the Tinder distance didn't lie—he was only a few miles away.

Hoping to recapture some magic, I went out with another man in his mid-40s a couple of weeks later. He was charming and handsome, although clearly not past his recent divorce. When he drove me back to my apartment after the bar, I had to squeeze past two child car seats.

"I just dropped my kids off at my ex's," he explained.

While it was blatantly obvious we were at two different stages in life—I was nearly burned out from taking care of my 1-year-old dog—I felt enough of a spark to invite him upstairs. We might have even gotten together a second time had our bodies not been so wildly incompatible. How can I put this delicately: My cervix felt like a punching bag.

"That was fun," he said at the end of the night. "We should hang out again."

"Definitely," I agreed, although I think we both knew we were lying.

Pegging

For those of you unfamiliar with the term pegging, let me direct you to the Savage Love column in which it was coined. I've always been fairly submissive in bed, so I thought pegging would represent a refreshing change of pace to flip the script and show some dominance.

The lucky guy, with a flair for adventure, was a no-nonsense, late-20-something in a long-distance, open relationship with a girlfriend of several years.

Before our date, I headed to a nearby sex shop for my pseudo-phallus of choice. I could've sworn I saw the cashier give an approving nod as he rang up the box containing a harness and a small, purple dildo.

I tried it on when I got home and was instantly mesmerized. Checking myself out in the mirror, I felt a surge of power and, to be honest, I looked fierce. I was eager to take it for a spin, but when I donned it in earnest later that night, I found out pegging was harder than it looked. Within a couple of minutes, I was pretty exhausted but I kept soldiering on.

By the end, I had a newfound appreciation for tops and their physical endurance. And while it was fun to shake things up for once, I realized I was much more comfortable in a submissive role; being a dom just isn't in my nature.

Next! Uh, about that…

With four items completed and none of them life-changing, I admit I was a little disappointed. I'm a big believer in there's value in trying new things, but nothing was sticking. In each case, the fantasy outpaced reality, and I wasn't quite sure why until later.

A few months after my great experiment began, I became pretty tired of going on dates. Getting all dolled up to meet strangers I may or may not have any connection with a few times a week became exhausting. While I like being around other people, I'm an introvert by nature, and it doesn't take long for social interactions with new folks to become draining, especially if we didn't click.

When I realized I had one more date scheduled, I decided it would be my last for a while. But, of course, life enjoys throwing curveballs at you.

I ended up having a ton of fun on the supposed last date, and we hung out again. And again. And again. And again. And a few more times until, to our mutual surprise, we made things official. Suddenly, my sex life no longer revolved around doing fantasies just to say I had done them. It was genuinely enjoyable.

It wasn't the list of fantasies that had disappointed me, but the people with whom I tried them. There's nothing wrong with casual sex or people who enjoy it‚ but I realized that if I don't have a connection with someone, I don't have a great time—and that's not something I can force.

I don't regret the time I spent trying to make my way through my bucket list. It was valuable to explore my sexuality and it resulted in some great stories. I'm not sad that it's over, though. Call me vanilla, but I'd rather try new exploits at a slow, steady and, most of all, organic pace than race to cross off as many items as possible as quickly as possible.

And I'm totally OK with that.