I have an unfinished draft about a crazy-good threesome but need to get the next update with Leo out.
He joined me for two nights at the tail end of a business trip to the East Coast. It was one month since Leo’s “give me another chance” conversation, and I knew it was a chance to see if anything had really changed in that time.
Leo had been slightly more communicative – meaning he whispered a few more things in my ear during sex – but other than a couple successful drug-free sexual encounters, things were essentially the same as before.
I had been clear with him on what I needed to change – although am inherently uncomfortable with such demands – and was hoping for a change. He’d insisted he wanted to make the same changes for himself.
A not insignificant part of me thought it was BS, but I really wanted it to work. He is a nice respite from the bullshit.
We met up after the business portion of my trip, he by train and me by rental car. I found myself mildly irritated by some of the text interactions in trying to meet up. Alone with my thoughts in the car I tried to figure out what I hoped he’d say and do instead, but I couldn’t put my finger on it.
But I knew what my expectation was the moment we got to the hotel room.
Or later that night, before sleep.
It didn’t happen.
Sure, when we checked in he kissed me and pulled me on top of him on the king-sized bed, but didn’t take it any farther. He’d had an overnight job for work and was tired. Despite saying he’d nap on the plane, he didn’t. Or the train. Nor did he try to arrive to the room early to nap before I arrived.
He hadn’t shaved, and his stubble destroys my skin. It’s not news.
There was no penetrative sex after dinner either, but he did go shave at least. I got a good nights sleep – so all was not lost – but it’s not what should happen when an expensive and romantic room is booked with a king bed, a private enclosed sunroom, a view of the ocean, and a history of famous guests including JFK.
I mean, really.
If the tables were turned and this was a second-chance vacation and I felt someone was perhaps judging our compatibility based on my actions, I would have been on fire. I’ve been in that place before, and I did everything in my power to do what my partner wanted and needed.
There was a failed attempt at morning sex. Leo stuck with his tried-and-true fisting with Hitachi which of course I like but it’s not as emotionally fulfilling as good penetrative sex. He hadn’t taken a Cialis – brought by me at his request because turns out his Viagra is through a friend and not his Doctor, because his Doctor refuses to prescribe it until he’s lost weight.
One of his fingernails was too rough and I bled from an internal scratch (he likes them long, so it’s an ongoing issue for me). When he went to wash his hands, I flipped over onto my stomach and put the wand underneath me, allowing my body weight to create enough pressure for a different kind of orgasm.
When he came out of the bathroom he told me to stay where I was, feet over the side of the bed, and he finger fucked me while I came, loudly, screaming into a pillow. One thing I like about Leo is he’s not afraid of toys.
“Don’t unplug the Hitachi, Ann, we’ll be using it later. I’m not done with you yet.”
We had a nice day poking around small towns and antique shops. We’d packed a blanket, lube, and a his remote control vibrator. The pouring rain meant it would have to be used inside the car; not a problem with the small SUV I’d rented.
We pulled onto a large concrete pier, empty except for us in the pouring rain, and Leo put the car in park. I expected him to lean in to kiss me and for us to get busy in the back seat.
And yes, I could have initiated but I wanted to see what he would do in the absence of my suggestion or kicking things off.
Disappointed, as he turned the car around I commented I was surprised he didn’t take advantage of the opportunity. Instead of turning back around he said “yeah you’re right that was dumb”.
My frustration levels increased steadily.
We managed to have brief sex that night but the Hitachi remained unused, plugged in behind the bed and resting under Leo’s pillow. Even when he can get an erection, and even with Cialis, it doesn’t last. I know he’s frustrated, and I haven’t said much about it because I don’t need to.
He woke up the next morning nauseated, so I went down for breakfast alone so he could sleep it off. We packed our things and to his credit, Leo demonstrated spontaneity and threw me down on the bed for some fun, well after our checkout time. We had the classic embarrassing situation with me orgasming loudly, being interrupted with a knock on the door and an inquiry as to when we were checking out. There was a brief good sex moment but again, it didn’t last.
By the time we got to the airport later that afternoon, I recognized I’d felt irritated most of the time I was with him. I hated the feeling, hated feeling like I was being a bitch (I wasn’t), hated the reactions I was having. He was bringing out a side of me I don’t like. He wasn’t doing anything wrong, but none of it felt quite right.
My head started to churn. I spent the entire plane ride home looking out the window, watching the plane chase the sunset and trying to figure out what to do.
Image from the 1955 movie “Stella”