Thursday was Lewis’s. The week prior we went to a formal event together (which was awesome) and he came over to my place afterwards to let off the sexual tension building all night. Before he left, we agreed to meet this past Thursday. He also promised to take me dancing at some point this summer and I hope that can happen. I would love to be on a darkened dance floor with him.
Thursday was just going to be the two of us, but at some point during the day when my phone pinged with a new text message I looked down to see: “Clark said he’s free too…”
Gulp.I joked it was my lucky day to get a bonus dude, and it’s sincerely how I felt.
We texted about whether I thought I could take both of them at the same time (vaginal and anal double penetration). I’d done it once before with Andrew and Jason (by the way if you haven’t read those posts and you want to read something really mortifying that happened to me during sex, you’ll enjoy them), and again at a sex club, but these two guys have big dicks.
I told him I’d be willing to try as long as he took his time and was gentle.
A couple of hours before we were to meet, Lewis texted that Clark had to cancel but the woman who joined us during our foursome was free. He said he was working on another friend who has a “huge” cock.
Now Lewis is huge in my books, so I’m having trouble imagining bigger. I get admittedly wet at the thought. But I wasn’t feeling up to a FMF threesome – it would be my first. I wanted Lewis to myself, I didn’t particularly want to share him with another woman, and I wasn’t feeling all that brave.
I told him I wasn’t comfortable if it was just us and her, and he was fine with it.
He came over just before 10pm, got some drinks, chatted for a bit, and put on a sporting event he really wanted to watch. It didn’t take long before we’d gotten each other worked up and naked in my living room, so we went upstairs.
I’m going to write more about the sex in another post, but it was technically great as always. The sheets were soaked from sweat when we decided to take a break and go downstairs to check the score. I took a moment for my legs to get their strength back, and when I joined him he was naked sitting on an ottoman watching the game.
It struck me as such a comfortable thing. Kind of an intimate thing. But we don’t really have that kind of relationship. It was just a nice moment I guess. I was chastised for putting on a long tank top. A few minutes later he pulled me into my kitchen where we proceeded to have marathon standing up sex.
I asked him how it was possible he could last so long without cumming and he said “years of practice with masturbation.” We had a good laugh about that.
And in the middle of pounding me from behind, he said “Oh, by the way, Clark asked if he could have your number since he missed out on this tonight.” Giggling and moaning at the same time, I asked him if we could talk about it later.
I slept incredibly well that night and finally managed to not wake up at 5am thinking about things, as I’ve done for a couple of weeks now. Lewis successfully quieted my brain, albeit briefly.
Friday – Jake
So. Jake is a new name to this blog, but not new to me. A little more than two years ago Jake and I met on OK Cupid. I’d not had much of a good dating run at the time, but I liked his intelligent profile and his openness. Jake was #64 of the men I’ve had sex with.
At the time, I wasn’t particularly discerning in the men I fucked. I looked at my calendar from back then and it’s filled with the names of some men long forgotten (but their stories are still here!) – the crazy Russian, the too-young ladies man, the personal trainer who bailed on me twice. Others were more prominent – Naked Ironing Man (who I still think about on occasion since our ending was unresolved in my mind), Jason, Shenanigans.
Jake and I went out for a drink, I took him back to my place, I liked his aggressiveness. The sex was fine.
I went on vacation the next day and never saw him again. He reached out and I just faded away. There was nothing particularly wrong, but looking back I recognize now the signs of being engaged with too many men at the same time, and the fatigue of dealing with too much bullshit and rejection.
When I went back on OK Cupid last summer, Jake was there. We were an 86% match.
He reached out to me but didn’t reference we’d met, so I asked him if he remembered. He remembered I went on vacation, we didn’t reconnect, and that we’d had a good time together. He said “So what happened? Why did we not continue. We worked well together. I think it could have been a fun start.”
I never responded. I’d met Fox and shut down my profile.
When I went back on the site in January after breaking up with Tony, Jake was there. He reached out again: “Hey sexy. You’re back. How’s it going?”
I responded this time. He said “I think we should get a bottle of wine, hang out and try again. We spent one great night together then you were gone for two weeks. Never got a chance to explore the possibilities. ”
I told him I wasn’t leading with sex anymore but I’d be open to drinks and conversation. He didn’t push, but he said he knew we were both sexual people. He then sent me this:
“I really want to lay you belly down on the bed and give you a slow massage. Working from your shoulders, upper back, down your spine, out to your hips and then down your hamstrings. Backs of the knees and calves. Digging my thumbs and palms into the muscles. Slow deep massage as I work back up your legs, slippery oil all over my hands and your body. As I start to massage your glutes, your breath gets heavier. You feel your muscles being separated and warmed from my hands. Every time my hands slide down your hips, your cheeks part exposing yourself. You rise to meet my hands. Hoping for some friction in the hot spot you feel pulsing more and more…”
I didn’t respond. I wasn’t sure what to say. I was slammed with work and HWSNBN and I had my son for a couple of weeks in a row. He asked me if I didn’t like it and I told him I did but was simply busy. I also wasn’t sure about engaging with him in a sexual conversation.
We texted back and forth a little and he said “well if you want to get a quiet late night glass of wine and have some company let me know. I know how those long strings of being with the kid can get.”
I said “I will for sure. I can’t say it will be any time soon. But I will get in touch if the stars align!”
You know what happened with my January relationship and how bad it went. I had hidden my profile and didn’t get back to Jake.
But when I unhid it two weeks ago, I saw our message exchange and figured there was no harm in reaching out. This time, I said hello first, told him I was back, and apologized for flaking.
We soon had a second date set, two years after the first.
[Image from the movie “I Walk Alone”]