I’ve written this post three times now. Turns out when you write a post on WordPress on an unconnected iPad then connect it, it deletes. This is not the first time it’s happened to me. Sigh. I’d like to think the first two drafts were better writing with more nuances. Oh well. At this point I just needed to hammer it out. Enjoy the bluntness.
If you haven’t read any of the posts about him, you can start here.
I hadn’t seen P/Shenanigans in 10 months or so. The game playing was too much for me to bear. I’ve told him goodbye more than any other man I’ve slept with.
Why? I wrote a lot about it. He was, in some ways, a perfect “Friend” with Benefits. I didn’t see any relationship potential with him at all – and therefore was able to simply enjoy the moments and the sex. When it came to the sex, was he the best? No, not by a long shot. That award still goes to NIM, unfortunately. Why is it always the emotionally unavailable ones? But the sex with him was good.
I stopped writing about all the times he reached out to me, and the brief dance back and forth we would do, before one of us said “mercy” and we stopped again.
I unhid my dating profiles on Plenty of Fish and OK Cupid a few weeks ago, and put up some new pictures. Shortly afterwards I heard from him on POF: “Your new pics look great btw, wow. Very nice :)”
I simply responded “thank you”.
To which he countered “are you free tonight?”
I paused, and sighed. And thought for a while how I was going to respond. Prior to his calling me to tell me about his failed date, the last thing I’d said to him was to not bother reaching out until he learned something.
Asking directly if I was free was different for him. The reality was, I was free. I had no plans. I’d had a great experience with Jason the day before. I had no dates and no real prospects, other than the crazy Italian who I knew only wanted sex. I said:
Yes, I happen to be free – why?
Him: I have to see you again, Ann. It’s been too long.
Every time prior, the moment I said I would see him, he would then turn around and pretend he was thinking about it, and would ask why I wanted to see him. He needed that ego boost and it was exhausting.
And of course there was the infamous discussion about never bringing wine because I wasn’t his girlfriend. Frankly I’m tired of men who won’t bring a bottle of wine if I host, or who won’t take me out for a drink or – gasp – dinner. I was curious whether he would be consistent with his past behaviour, so I asked “what were you thinking for tonight?”
Him: A glass of wine and a catch up chat.
Me: Sure let’s do that. What time and where?
Him: Your place at 6?
On the one hand, an earlier date was new and I liked it. But there was no damn way he was coming to my place as a starting point. So I said “how about this newish bar near my house that I’ve been meaning to try?”
And miracle of miracles, he said yes.
Our date was on.
We sat for more than 2 hours over drinks and dinner. I had forgotten how young he was, and how occasionally uncomfortable in his own skin he seemed. I had forgotten the insecurity he manifests and that he doesn’t command a conversation. But I can have a conversation with all but the most reticent participants.
It was an alright dinner date, all things considered. I invited him back to my place. We sat on the couch and I waited for him to make a move. Finally I asked him why he hadn’t, and he responded that he sometimes liked an aggressive woman. Right. Feeling magnanimous I proceeded to give him a blow job that he will hopefully remember forever, given the touching and other things that went along with it.
When I couldn’t stand it anymore I took off my lace panties and mounted him on the couch where he sat. I forgot how big and hard his cock was. The reality is that he’s very tall, very good-looking, has the stamina of youth, and a great cock. He’s not a particularly giving or talented lover otherwise – and he’s gotten by on those other assets.
I was able to make myself cum rather quickly – and the muscle memory kicked in for him and he remembered what I liked and tilted his pelvis that certain way. It felt fantastic. I then turned myself around – he loves my ass – and rode him that way as well.
He then took me over to a side chair and told me he wanted to fuck me over the chair, which we did. Then he said he wanted to take me on my stairs, so we did that too. It was almost as if he’d had fantasies about both those things and he had been waiting for the opportunity.
Then we went upstairs and had sex every which way for about an hour – including anal, which he had wanted to try for a while and definitely didn’t have much experience with. As I was riding him again he suddenly said “oh god Ann I have to cum” – which was bad timing on my part as I was working my way toward an exquisite orgasm but I figured hey, why be selfish. He then asked to cum on my face.
It’s worth noting if I haven’t already, that I have NEVER let a man do that to me. I told him so and also mentioned I hear it can sting. He suggested I close my eyes and he’d aim lower.
I honestly don’t know what made me agree, but I did. I certainly have no issue saying no to things I don’t want to do. Perhaps it was the innocent and hesitant way he asked. Perhaps it was also knowing that he hadn’t done it before but he wanted to explore, and I liked being the one to let him do that.
So the next thing I had my face hanging off the end of my bed as he stood before me. When he came, I started to laugh because there was so much of it, everywhere – we both giggled about that as I went to my bathroom and towelled myself off. And yeah, the cum in my eye stung.
In response to my inquiry whether he liked it, he said he did, but he also felt it was degrading to me and he didn’t like that part. It’s probably the most honest thing he’s ever said to me.
I wasn’t quite finished so asked him if he would lend me a hand. He said no – and I remembered the selfish lover part again. He suggested and toy and then told me he didn’t have much experience with toys. So I showed him some vibrators and dildos – picking the Hitachi Magic Wand and my favourite dildo. He wanted to watch. I can bring myself to orgasm that way very quickly, especially after having so many already.
But he got bored and after watching me for a while, went to my bathroom to clean up. Although I felt great, I really didn’t want to continue while he couldn’t be bothered to hang out or even participate.
When I told him such, he said that he felt since I was insatiable it wasn’t like I would ever be satisfied.
I explained to him that my pretty much always wanting more didn’t mean I wasn’t satisfied. It occurred to me that it was likely one of his issues – he’s used to women who blindly do what he wants, don’t challenge him, and who he can best in bed.
We wrapped up our evening and I asked him what he wanted of me – he said to hang out on occasion. I told him I would think about it.
Sometimes, I just want to know exactly what I’m getting, even if I know I can have better.