Giving a Guy a Second Shot at Sex

Would it be a deal-breaker?

I used to think how excited I would be, being able to get dressed up and go on dates.

Yeah, fuck that noise. I’m over it.

It doesn’t help that I’m doing this during a global pandemic. I can’t even wear lip gloss because of masks. How am I supposed to impress a guy if my lips don’t look like they’re shellacked in glitter?

It started with my bar much too low because it matched my confidence level. Once I realized I needed to aim for only top-tier men, things changed. Because I switched to online dating (thanks Covid for making serendipitous meetings extinct), the odds were in my favor. One hundred men for every one woman kind of odds.

I’ve met up a few times with Sean, who in the grand scheme is wonderful. Until it came down to our first time having sex (I wrote about that disaster here).

We went through a handful of condoms because he couldn’t stay hard in them. I cut him slack because I assume when guys have two decades of no-condom sex with their wives, it’s hard to revert.

Yesterday, I went over to his house again. Sean knows his house is an oasis to me. It’s gorgeous. It belonged to a fancy-pants real estate agent and when he bought the place, he paid for her to leave her décor and furniture behind because it was so tastefully done. He also has a wine collection that is probably worth more than my kidney. In other words, he had no problems staying in and drinking.

I devised a new strategy: I’d get him to bone me before drinking if that affected the erection situation. My breast implants are getting a revision in a few days so I wore a slouchy top that highlighted them perfectly since they’ll be covered up for weeks during recovery. Tight jeans, a shit ton of makeup, and I was set.

The plan didn’t need that much thinking. As soon as I got there we kissed and it was on. Sean picked me up while kissing because he’s already learned that it drives me wild how he can pick me up like a feather.

He sits me down on his kitchen island where we make out like teenagers. Then Sean throws me on his couch and it’s Get Naked Time.

What would happen next? Would it be Condom Fiasco 2.0?

I straddle Sean and he makes the preliminary gonna-stick-my-stuff-in-your-stuff move. “I thought you wanted to only use condoms?” I asked.

“Have you been tested?” he asks. I reply yes.

“Great, so have I” and in slides the dick.

Condom Fiasco 2.0 was replaced by Holy Fucking Perfection 1.0. It’s cool if you, Dear Reader, want to high-five me.

Like last time, after sex is when Sean was ultra chatty. We drank two bottles of wine, we talked nonstop, and we had a second round of sex. We kicked back on the couch and laughed at how ridiculously large his feet were next to mine.

I told him how much it turns me on that he’s so much bigger than me and he said that likewise, my small frame turns him on. Sean flattered me with compliments, like how I’m “hot and funny”. I learned more about his childhood and college life. I was on Cloud 9.

We talked about our experiences online, about what the other gender does to ruin their profiles. “We’re going to sit down and see what kinds of profiles show up for the other person,” he said. Yes. That kind of shit is exactly up my alley. I’m dying to see the profiles of women who are theoretically my “competition”. Sean wanting to do that kind of experiment for laughs made me like him even more.

I was elated about how easily the conversation flowed. He admitted he was nervous on our first date after I teased him that he’s a VP of sales, smooth-talking should be his number one game when meeting strangers

Five hours into this date, I jumped up realizing he had to work the next day. Unlike my lazy ass that rolls out of bed at 10 am to grab my laptop and start work, Sean has an actual grown-up job that requires his presence each day. For the first time in ages, I had been so caught up in the moment that I didn’t even check the time.

He walks me to my car and opens the door. Small acts of chivalry will never get old. Sean insists that I text him to let him know that I got home safe.

“Oh, one last thing,” I say before getting in my car. “I appreciate how cool you are that I still live with Joseph until the housing market gets better. I don’t know if I could be if the roles were reversed. I promise you, it’s like living with a roommate who babysits my kids and drinks all my effing almond milk then puts the empty carton back in the fridge!”

Sean laughs and says, “Honestly, I find it comical. It’s like you’re living with a teenager.”

Yes. Being with Joseph for almost 20 years was like being with a teenager.

I adore Sean. He seems quite smitten by me. The problem? I still have other guys lingering around that I need to sort out. I have a date on Friday with someone else I chatted with.

My original thought was that I could easily date a handful of guys at once. I was on crack to think that was possible. Between work and my kids, it’s hard enough to squeeze in time for one guy. And I’m beginning to emotionally invest in Sean, which means I would rather stay home in sweats on Friday night if I’m not seeing him instead of going on a date with someone new.

I’ll honor my commitment to my Friday date but I’m not doing my usual Dog and Pony Show. I’m not going to wear an ultra-sexy outfit. If he orders food, I’ll actually eat it and not give a shit if I get all puffy and bloated from the salt. If homeboy wants to kiss at the end, great, but that’s as far as it goes.

I’m trying to keep an open mind but Jon and I broke up last June. My marriage was over years before that. I’ve done months and months of self-work to heal. After dipping my feet into the dating pool, I decided to start dating with intent. My days of going on random dates “just for fun” are over; they stopped being fun when the level of effort I put into getting ready exceeded the actual enjoyment of the date.

Are Sean and I headed towards something more serious? It looks that way. I slowly disclose all my red flags, like how I was on a fetish site while married. “How are you not horrified with any of this?” I ask him after I’ve delicately disclosed something. “Because I don’t think they’re red flags” he replies.

I tell him that my reasoning for telling him these things is that it's part of living an authentic life.

Last night, it paid off with some mind-blowingly good sex.