The morning we slept in and had brunch (Date #4, Part Deux)

For part one of this date, go to this post.

Tony also has a section in my About my Lovers page, if you want the back story. And while I think about it, I also split my Lovers pages into two… there is now one called Quick & Dirty which has the one-offs or unsatisfying encounters. The main Lovers page has those I would consider relationships (or extended F*ck Buddies).


I completely forgot to mention my footwear. Tony had said in an earlier date that he really liked heels, in response to a question I casually asked him about fetishes. Trying to suss things out, you see.

So I brought a pair of high heeled boots to his house. I have had them for almost a decade and they are crazy sexy. Since I am in the northern hemisphere it’s winter, so I figured I would remove my winter boots and put these boots on when I got to his place.

Well, I never bothered doing that, BUT when we went upstairs for the night, he told me to bring the boots with me. For quite a while, I was naked except for my boots. He thought it was super hot and I was happy to oblige him. I just had to be careful not to dig a heel into his thigh or temple.

The next morning, we woke up, had sex (I know, yawn) and chatted and generally just enjoyed being naked together in his huge king bed. Soon we realized we needed coffee. Tony LOVES espresso and was keen to make me some. He gave me a t-shirt and a pair of his gym shorts (yes, I had stuff to wear, but I liked the thought of skulking around in something of his) and we padded downstairs to make coffee and we cuddled on the couch.

But we were on a schedule of sorts. My only deadline was I had to pick up my son from Will’s house at 4pm. But Tony had to drop off his car at noon to his ex, who was borrowing it for the day.

As seems to happen with him, time evaporated and although we had planned to go for brunch, we realized we couldn’t do that before he had to drop off his car. So we made a plan – he’d drive to his former house, I would follow him in my car, then we’d go for brunch. As we got dressed I picked up the yoga pants he’d been wearing the night before. I guess when I was naked and he was on top of me with pants still on, his crotch pressed into mine, I smeared my wetness all over him.

I just said “um, you can’t wear these pants again. I’m all over the outside of them.” I know he said something cute and funny in response but I can’t remember it exactly… something along the lines of he loved it, that it was a great reminder.

It was odd to wait in my car outside his ex’s house. It made me wonder whether his ex noticed he was getting picked up, or asked if he needed a ride and he had to explain why he didn’t. I didn’t want to watch the house to see if I could get a peek, although I was curious. He came out after a few minutes and I told him the story of getting the “date report” from my son oh-so-long-ago when I first became aware that Will was dating.

We went for brunch. He picked the area and the restaurant and I had one of my favorite breakfasts, Eggs Benedict with Smoked Salmon. Yum. More coffee (pretty damn tired) and lots of conversation. Gosh, he’s easy to hang out with. Ironically we were dining on the street that Shenanigans’ store is on (the one he owns) and I half expected him to show up. It would have figured.

I paid for brunch, as he has paid for all of our other outings so far. He was quite willing to pay but I insisted. Figured it was just a good idea…I definitely don’t want him to think I take that kind of thing for granted.

We knew we had to be back to his house by 2pm so I could leave at 3… he joked that we seem to spend endless amounts of time making out so an hour would be tight. As we walked back to my car we popped into an antique store that had some very cool things, including a lot of vintage Playboy magazines. Next to them were magazines in paper bags – I said “oh I bet those are Hustler”… Bingo.

When he said he would need to come back to look at those, and I told him I was totally cool with checking them out in front of me, he simply said “yes, I am getting that impression”. It wasn’t a criticism but all I could think was that he didn’t know the half of it.

It was nice to just wander with him, look at the old stuff, and talk about how we both are making our places our own. He’s affectionate in public, which I really like. Not embarrassingly so, but holding hands or stopping for a kiss. That kind of thing.

We went back to his place and this time, we tested out the height of his bed. He pulled me to the edge and flipped me over… his half wall is the perfect distance for my legs and I can get some pretty good traction with my feet on it. From his perspective, the bed is the right height for him to enter me without having to bend down too much, as usually happens on lower beds.

I need his cock to be more responsive, get harder, and stay that way. So it’s a new mission. I don’t leave my encounters with him orgasm free – hardly – but I want it to be better. I have faith it can be.

While it was technically our fourth date, I’m starting to think I should count them based on waking hours spent together. I managed to drag myself away from him just after 3pm. We had no concrete plans for the next week so it was hard to say goodbye.

I’d had a 17 hour long date and I still wanted more.

It’s a very good sign, no?

I made it to Will’s house with 3 minutes to spare. When I texted Tony to tell him, he said “damn, I could have kissed you for another 3 minutes?”

0 thoughts on “The morning we slept in and had brunch (Date #4, Part Deux)

    • Yes, it’s a good thing so far. No drama really since that early drop-off-the-earth thing he did. I’m keeping my emotions in check for the most part, although it’s hard to not be all gooey when I’m with him.

      I need more, and I do know that. More and better sex, and more communication. But I also completely understand the place he’s in with regard to his breakup… so pushing isn’t going to end well.

      Thank you for being happy for me. That makes me more happy πŸ™‚

  1. Good for you! I am happy that you seem to have someone that you enjoy and seems to enjoy you. Enjoy it for as long as it lasts, however long that is!
    On the penis front…I have no idea how old he is/health condition, but unless he is secretly gay (and just with women in denial) he either has a past trauma, or far more likely a medical issue. From all that you write and say, you are plenty hot enough in many ways to keep a man hard. He’s got a physiological problem and will probably benefit from Viagra or something like that. Not that he won’t enjoy your extended attention to get and keep him hard πŸ™‚

    • He is around 38 and in great shape. Things seem to be getting a little better but I agree it’s medical or mental. I’m thinking yes, medication would be a great thing and need to figure out how to broach the topic.

      What bothers me the most is I can give him what I know is a fantastic blow job and he doesn’t get really hard. Now that, my friend, is an anomaly.

      • Right, which is why it is either a psych issue or a medical issue he could use help with. Being 39, I have seen my erection not always be there in the middle of foreplay, but it comes back immediately, and while I’m being stimulated it is always rock hard. That said, in my experience with other men I have seen lots of them have issues keeping an erection during the middle of oral sex and or in the process of trying to have anal. I have attributed some of that to the fact that guys have issues and hang ups about what they are doing that makes them go soft. Others are on medication that affects their dicks. And I think some guys just have trouble staying hard. And I give a pretty good blowjob too, lol.

      • I’ve missed being here too. I hadn’t realized how long it had been until I went to log-in and couldn’t remember my password. doh

        Working, vacationing and working have fried my brain. lol

What do you think?