Leo enters an exclusive club

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I’m going to merge a few Leo visits into one post, otherwise I know a few of you will kill me for the “cliffhangers” I’m frequently accused of.

I saw him three times in the week before and after Christmas. The first time was a brief visit; he brought an orchid, sat next to me on my couch and cuddled. By the time he started to kiss me, hard, my son’s nanny showed up to take me to an appointment.

We giggled conspiratorially at almost being caught canoodling on the couch, and he promised to come see me later in the week when I would be alone.

The next time, he showed up with Prosecco for me for New Year’s Eve. We had almost an hour to ourselves, yet spent it talking. By the time things heated up between us, kissing with his hands down my pants, my Dad and son showed up.

And when Leo survived a conversation with my Father, he definitely went up in my estimation. I love my Dad, but one thing he loves to do is monologue. Add to it, he’s hard of hearing and can’t afford hearing aids, and he’s rather a challenge to talk to these days.

He had come to stay with me for a few days to help with childcare while my nanny was on vacation.

Leo and my Dad had a good chat about all sorts of things. I mostly listened and watched Leo. He was respectful but held his own. He asked interesting questions, and also knew when to let things go.

I was impressed.

He also met Liam, who wasn’t at all interested in the discussion as he was captivated by his iPad. In case anyone is wondering, Leo and I weren’t doing anything in front of Liam that would give him the impression he was anything other than a friend.

Leo told me that night he was going to start a diet in January; he had reached his highest weight ever, didn’t like it, and needed to make a change. He is definitely a big boy; he’s hoping to lose 100 lbs. I’m sure 50 will make a big difference.

That news made a difference to me as well. One thing that’s important to me in a partner is that they are relatively health-conscious. They don’t have to be buff – I hardly am – but I want someone who is active, eats well most of the time, and while confident, may be on a journey to get healthier. Like me.

And Leo had never mentioned anything about trying to lose the extra weight he had. Time would tell if he was all talk, but I liked that it was even something he wanted to do.

The next time Leo came over, we were completely alone, and it was at night.

All of the couch visits have melded in my brain, but this one was notably different – we left the couch and went upstairs.

Leo loves to kiss me. The feeling is mutual. Actually, there’s not much he doesn’t like to do to me. This is the man, after all, who said something like “I don’t know whether to kiss you, bite you, or hug you”.

It’s bloody awesome.

But despite having brief penetrative sex on one of our early dates (not the first), everything he’s ever done to me has been with his hands. In the past couple of weeks, I’ve realized it’s party because he penis doesn’t always work.

I’mΒ really careful about having these discussions with men. I asked a few different ways whether there was anything I could do for him, because it was feeling one-sided, and have come to the conclusion that his weight is a contributor to the hydraulics issue. Maybe associated medicines.

So I’m leaving it alone, for now.

I wanted you to have that context before I describe what happened on that pre-New Year’s Eve date: everything was with his hands and mouth.

We were naked on my bed, kissing, with his hands between my legs. He “finger fucked” me over and over and over again. At some point, I asked him how many fingers he had inside me; and asked him to add another. He just kept going. I asked him to add lube, so he did.

The next thing I knew, he was completely inside me, up to his wrist. At that point I completely lost myself in the sensation. He was on my left side, his left arm wrapped around my shoulders, holding me tight to him. My face was buried in his neck.

He would growl in my ear, or whisper “that’s it, baby…that’s it, Ann”.

And I rewarded him with squirting all over my bed. Multiple times.

Even in the haze of pleasure, the Virgo in me thinks “oh crap, had I know I would have put on the waterproof mattress pad” but I manage to put those thoughts away. Because getting back in my head will halt the pleasure.

He kept going and going until I’d had enough. I curled into the fetal position and he held me tight while the aftershocks coursed through my body.

And several minutes later, we had round two.

Leo, my 100th, is only the third man to ever “fist” me. My ex-husband Will was the first, a fellow blogger (who wrote about it) was the second, and now Leo.

I hope there is more to come with him.

All pictures from the Leo posts are from the 1962 film “Phaedra”

14 thoughts on “Leo enters an exclusive club

  1. Go Leo Go!! I hope Leo can get his “Head” around a solution for his hydraulics issue. I have been having to supplement my own chemical makeup in order to perform. I’m hoping that the medically monitored weight-loss program I’m starting will help also. I also have 100+ pounds to lose. Leo seems to have manual and oral skills to make up for his “issue”. If he can solve this he just might be the WHOLE package!!
    Good Luck, Leo!!

  2. Ah! I love it when he fists me. It is indeed one of those sensations you completely lose yourself into!

    Glad things are progressing gently with Leo. I’m looking forward to reading more about your adventures!

  3. Now that’s an experience I’ve never had. But I guess if children can come out of there than a fist entered the correct way can go in… πŸ™‚ Sounds like a great time Ann!

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