New Person Sex Feels Weird
It’s like learning on the job.
Sean refills my wine glass. It’s Easter Sunday and he doesn’t have the kids so we opted for me to hang out at his place. He knows my house is packed with my kids, my quasi-ex-husband, his nephew, and his nephew’s wife.
Not ideal when you’ve had no solitude for 13 months.
Fortunately, Sean lives in a swank-ass house in a ritzy neighborhood. With his kids at his ex-wife’s house, the place would be silent if not for the whole-house speaker system playing music.
I’ve never visited a gated community for anything other than baby showers in some community hall. Giving his name and my name to the guard, I felt nervous. Like I was doing something shady and the guard would reject my request to go in.
Sean uses a ten-step system to open the fancy doors leading to his backyard while we talk and drink. At times, the conversation is a little difficult for me. He’s social but he’s not overly chatty. It’s definitely on me to keep the conversation going; I naturally entertain by conversation but being a hermit for over a year limits my topics. I’m not on my A-game like before.
I know we’re going to have sex. We didn’t rush into it since we had all afternoon. I know how to look effortlessly sexy for a guy which, for the record, takes a lot of effort. The Oh-This-Is-How-I-Look-Normally-On-Weekends is a façade, gentleman. Camo-green tank top with no bra, my tightest jeans, and I take my heels off when I arrive so that I’m shorter. Sean’s a foot taller than I am and I’ve sensed that he likes how small I am compared to him. Pretty sure he knows how much I like it when guys are significantly larger than myself.
He pulls me up on his lap to straddle him while he’s on a stool facing the open doorway. It’s Go Time. Thank the lord, I like kissing him. Occasionally he repositions so that we’re tilting our heads left. Isn’t there an unspoken rule that we all tilt our heads right? Like we drive on the right side of the road, the majority of people are right-handed…c’mon, I can’t be the only one who thinks the default is tilting your head to the right.
We move to the couch. The last time I was over, I was surfing the crimson wave, and everything but my thong came off. On the border of buzzed and drunk, I rip off his clothes and he tears mine off.
Everything onward is new. I remember when discovering someone’s body was exciting. Why do I feel all this pressure to “perform”?
Sean stands up and says, “Going to close the doors. I want to hear how loud you can get”. Fuck, that’s a sexy statement. At least that proves he knows what he’s doing with his fingers if he’s concerned about the neighbors hearing us.
More making out. He digs into his shorts on the floor and pulls out a condom. “Were you a boy scout or something? That’s being seriously prepared,” I tease him. I’m still on the fence if I think he’s good-looking or not (it’s like that Seinfeld episode where Jerry didn’t know if his date was attractive, based on the lighting) but I have no complaints about his body. His bicep is the size of my frickin’ thigh. Sean whispers that he wants me to put on the condom.
“Oh hell no,” I reply. “I’ve never done that in my life. I should have learned on a banana or something in high school. I definitely shouldn’t be trusted to do that.”
Sean gets it on his cock and I get on top, his hands gliding me up and down (add a plus to his scoresheet, I love when guys do that). But…then the condom gets all weird, he’s not hard anymore, and I’m confused as to what is going on. I ask him the last time he was tested. “I’m not doing this without a condom,” he says. Argh, did I make myself look like a total whore by being okay with doing it bareback if he tells me he’s been tested clean? (I’m writing this a day later and I’m still cringing.)
He carries me upstairs with some magical move that had one arm carrying my body, the other hand inside of me the whole time. I’ve never had a guy lift me with one arm, let alone all the way upstairs (add another plus).
We get to his room and Sean throws me on the bed (another plus…this is redeeming his score with the wonky dick and condom downstairs). Loads more kissing, pinning my arm down while he puts his fingers in me again (yes, another plus to the scorecard). After I go down on him for a while, which was hard because my mouth was dry as hell from all the moaning and screaming, he goes for another condom.
It goes amazing and then…same deal. He and the condom have issues. When guys have dick issues it’s on the chick to play it off as no big deal. I mean, it’s not a big deal to an extent. You have to strategize your moves because you don’t want him to feel pressured about his lack of a hard cock. That just adds to the weirdness and then you’ll never get that thing hard again.
I think he had three? four? condom vs. dick battles. Sean comments that he got tested on Friday so that he won’t have to deal with this. Eventually, he concedes to using his fingers, which is my parlor trick for new guys I sleep with: I’m multi-orgasmic and if you hit the right spot, it’ll happen repeatedly. Until the novelty wears off, it’s like someone hitting a jackpot every time they pull the lever on a slot machine.
I have no complaints but my forever gripe with sex is that you don’t know if it’s over until the guy cums.
Ultimately, he stops and we lay there, sweaty, and suddenly he’s Chatty Cathy (don’t know the male version of the expression). Oh cool, now you’re capable of yapping. Where was this talking when I needed it hours earlier?
Sean asks me how many times I came. It’s part of the aforementioned parlor trick. Guys want me to provide a number. “I don’t know, am I supposed to count?” I coyly reply. “I’m not going to lie, seeing the barn door to your closet and your kitchen island, I may have cum from those visuals.”
“I have no problems with that, I’ll take the assist,” Sean says. I guess former football players figured out how to use game terms in their everyday lexicon. He gets up and starts laughing while standing in front of the mirror to the adjacent bathroom. “You need to see my back.”
Eek. I clawed the shit out of it. “I’m so sorry!” I exclaim. “My nails are short!” Sean brushes it off and tells me he thinks it’s hot. I was so used to watching my nails when I was with my ex-boyfriend Jon (in fear of his wife catching us) that it never crossed my mind that a single bachelor would like that.
He lays back down and we chat some more. Maybe the secret to getting this guy talking is to get him naked.
Suddenly, Sean climbs over me and starts passionately kissing me. It’s Go Time again. At this point, I have no idea what’s going to happen given that condoms are, ironically, cockblocking me.
I go down on him for a while, he slaps on a condom, gets on top, and gets his thrusting on. Finally, condom number four? five? is the lucky number. Sean gives that faint mumble of, “I’m going to cum” which is a universal statement across all men. I would be blown away if a guy ever mixed it up with something like “cumming is what I shall do”.
Giving women a heads up is highly appreciated. Plus, I love the sound guys make when they cum. Like snowflakes, no two sounds are unique. Except for Cory, the guy with a microdick who stayed silent and never told me he was done until he pulled out.
Laying back exhausted, Sean resumes his chatty bed talk. Like dude, why couldn’t you have been this talkative before? I use the moment to ask him things on my mind, like whether he was nervous the first time he kissed me and if it bugged him for me to be all up in his nuts when I text (my life revolves around the written word in all formats except spoken these days).
“Do I seem like I’m annoyed when you text?” he asks.
“Well…no…” I stammer.
“Welllllll,” he mimics my voice indicating that the answer is clearly “yes”. I explain that it seems like he picks up the phone, answers the text, then tosses the phone back down and goes back to watching sports. Sean assures me that’s not the case. The dude is just really bad at texting.
Eventually, it’s time for me to head back to the chaos that is my house. Driving home, thoughts of Jon creep into my mind. I can’t help but feel angry. All the feelings that I’m slowly building with Sean are what Jon felt for his new girlfriend while I was at home in absolute agony over our breakup. I feel dumb for feeling such intense pain while he was bonding with someone else with things like making new inside jokes like I’m making now with Sean.
There is no way I would have been half as devastated over the breakup if I had set Sean up to be the next guy in line. It hurts to know you weren’t worth fully grieving over. Don’t get me wrong, Jon was within his rights to do whatever he wanted (although I think it’s fucked up that he already looked for his “second choice” while still with me). It just sucks that I felt he, and what we had, was worth the full cycle of grief after a breakup. He didn’t feel the same about me.
Reminding myself that I just had a wonderful afternoon with a great guy, I re-center my brain. While driving home, Sean texts me “That Sunday is tough to top :) Thanks for the visit!”
And that, right there, makes my entire night.
Part two of our attempt at sex can be found here.