a "missed opportunity"

Tonight I'm having dinner with a woman I started dating about two months ago after we met on OKCupid.

Her name also starts with S., so that may create confusion here given all my posts years back about S.  But since no one is actually reading this blog, it won't matter.  ; )

After I had been dating S. for about six weeks I left town for a 3-week trip to Europe, mostly for work but also to meet up with a friend who lives over there.  The timing was not the best, but I had planned the trip months back.  

The trip turned out be extremely intense (in good way) and I spent those three weeks very focused on the moment, and when I returned I was feeling a bit disconnected and badly jet-lagged.  And I was a bit worried about how things would pick up again with S.

In the event, our first night back together was wonderful and we picked up right where we had left off.  Except one thing was different....

During our time together before I left for Europe, sex with her had been almost entirely about me servicing her, almost all through oral sex.  That's how thing started from Day 1.

By the time I left for Europe I had only gotten to cum once with her, when she gave me a hand job.  

Of course with that kind of start, she was very curious about what was going on. In response I was pretty open about being submissive and preferring to serve.  All this didn't come out in just one conversation, partly because I didn't want to scare her off.  But come out it did.

Much to my surprise, it turned out that she was more happy to accept me that way and was interested in exploring taking up a dominant role - something she had never done before and really hadn't even thought of.  Still we only took very small steps in that direction.

Fast forward to my first night with her after I got back from Europe: I spent a long time going down on her.  (my favorite part was when she pushed me down and rode my face.)  

Then to my surprise, after she had cum and was very satisfied, she told me that she wanted me to have an orgasm.  I think she was taking care of me, knowing how hard my trip to Europe had been.  Of course, I should have said something like "thank you, how would you like me to cum?"  But I was an idiot, and I didn't say that.

Instead I told her that I would like to go down on her again.  

Dear Reader, if at this point you are saying "topping from the bottom!" you are correct.

However, she didn't say anything in that moment but consented. I went back down on her again.  After a while she was exhausted, had me stop, and we went to sleep cuddled together.

However, later that night I woke up and couldn't get back to sleep (jet lag).  To make matters worse I started thinking about what I did, and I realized how bad it was.  Here I was - six weeks into a new relationship and talking about my desire for a female-led relationship - yet when she tells me very directly what she wants  I respond with what I want, and I push for that, even though that for which she was asking would have been so insanely easy for me to do.    

I realized that I wasn't going to be able to get back to sleep. And I knew how important it was to get back onto a regular sleep schedule.  So, I took a risk and gently got out of bed to go to the bathroom (trying not to wake her), thinking that would help me sleep.  

However, she woke up and went to the bathroom, too.  

As we both cuddled back into bed, I asked her if i could talk to her.  She said yes, and I apologized for what had happened and acknowledged that I can't have it both ways: asking her to lead and then leading myself.  She was very gracious about it and accepted my apology.  And we both immediately went back to sleep.

However, the next morning I was still feeling bad.  After I got everything ready to leave for the day, I asked if I could talk to her and she said yes.  

We were in the bedroom and she sat down on the bed facing me.  There was no chair in the bedroom for me to sit in. Yet sitting next to her on the bed seemed a bit odd, as then we would not be facing each other.  

So I sank down to my knees in front of her. I was a bit worried that would come off too strong. But she immediately reached out her legs to draw me in tight and then put her feet down on the backs of my calves (which were extended out behind me as I was kneeling facing her) and gently pinned me in place (!).  

To make a long story a little bit shorter, I apologized again, in more detail.  And this time she responded a bit more.  

She told me something like.  "I know that you're feeling a bad about what you did.  But mistakes happen in all relationships especially in the beginning.  It's no big deal." 

I was so relieved to hear this, and I so happy to be talking openly about all this, that perhaps I wasn't paying as much attention as I should have when she went on to say something like "I would have thought you might be feeling bad because that was a missed opportunity."

In the moment I didn't clock the possible meaning of those words.  We had never discussed how often I might have an orgasm when i was with her.  And, later, when I thought back to that conversation and her words, a chill ran down my back as I realized that when I am with her I might be cumming only very rarely.

As of right now, I still don't know.  But I might learn more tonight.


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