dating rule breaker

Breaking rules like the dating badass I am.

Previous Post | Yes, I’m a rule breaker sometimes, even when the rules are my own. But this time, it paid off.

We had planned to go out – I wanted to take him to a great river walk a few minutes from my house. If we were getting along, I knew we would have dinner. And we’d already talked about our views on first date sex.

He was running a little behind and I was so nervous I started pacing. I was so hoping it was good in person because it had been lovely talking to him on the phone.

I’d wondered if he’d show up empty handed like so many men before him. 


He arrived with a small gift bag. Knowing my son was away for two weeks and we’d just said our goodbyes earlier that day, he brought me a selection of chocolates for stress release. I was impressed. A bottle of wine or flowers is nice for sure, but standard. This showed he’d been thinking about me. 

I offered him a drink and he wanted what I was drinking. “Are you sure?” I said, “it’s a rosé wine that’s too sweet for me but I hate to waste it.”

He insisted. He’s not a big drinker and he didn’t even finish a glass all afternoon.

We sat on my couch and talked. He was affectionate, putting a hand on my leg. I liked it. When we kissed, it was good but not great. I’m not going to write this post comparing him to others but it wasn’t in my top kisses list. However nor was it beyond redemption. It was just a little too rhythmic, for lack of a better term. He did the same thing over and over, but even throughout the day, I managed to change up his pace a little.

We realized there was a sporting event on TV that we were both interested in, so we turned it on. Something again I would never normally do on a sixth date, let alone a first. We weren’t glued to the the television, but instead we’d talk and turn our attention only when something exciting happened.

We continued to make out and it got progressively more heated. He would stroke my leg or inner wrist and enjoy watching me stumble with my words as I tried to concentrate. His hand eventually moved farther up my skirt, pushed apart my thighs and my lace panties, and one of his long fingers started to explore. When he added another finger he quickly had me writhing on my couch.

Shortly afterwards, when I went to get another glass of wine, he followed me to my kitchen, where he deftly did it again. This time, within maybe fifteen seconds, I squirted. In my kitchen. On my floor, and down my leg.

It was a first. Sure, a few men have made me squirt – Andrew (with his cock, even more rare), Jake, and a few others. But not so quickly, not before sex, and definitely not while standing in my kitchen.

We went back to my couch and soon I realized I was getting a migraine. I’m lucky to get an aura about thirty minutes before the pain kicks in. Saying nothing, I went to my purse and took the pill that prevents most of the pain. I gathered my thoughts – it’s hard to focus on anything as I gradually lose my vision in my left eye and worry whether I’ve taken the pill in time. I told him what was happening.

Once I established I’d avoided the excruciating pain, but the nausea, light and sound sensitivity, and residual pain kicked in, I sheepishly asked him if I could take him upstairs, since sex increases blood flow which sometimes helps. At the very least, it would distract me. All of my first date rules guidelines were thrown out the window and he was happy to oblige.

I didn’t leave my bed for hours.

The sex was good, he proved to be insanely capable with his fingers, hitting my g-spot right away and making me squirt many times. He also fisted me. He took breaks so as not to cum, so we could have several rounds. Between them, I’d put my head on his chest and rest.

Although I lose my appetite during a migraine, I knew he was hungry. I was in no condition to leave my house so he offered to pick something for us. I ordered from my favorite Italian restaurant and he picked it up and paid.

All in all, it was nothing like what I expected nor what I’m used to. But it was good nonetheless. I don’t think I made a mistake in letting things play out the way they did, but only time will tell.

7 thoughts on “Breaking rules like the dating badass I am.

      • 😂
        Sorry, your blog seems to not want me to comment, and my phone isn’t helping.
        Considering how late it was, I decided I’d better give up and sleep…
        I’m wondering why you’re worrying.
        About the rules? Oh, well, you had good reasons to break them.
        My feeling is, if having a migraine on the first date doesn’t push him away, then… it was worth breaking the rules!
        Only time will tell at this point, and that’s how it will always be 😉

  1. I have a new name suggestion for this new prospect.
    How about Doc? If nothing comes of this, at least he helped your migraine.

What do you think?