Last night went completely sideways. Or, how I fu*ked the oldest guy ever.

My head hurts and I reek of sex and cologne.

I can’t drink like I used to. The one cocktail, one bottle of proscecco, two glasses of red wine, and tequila shot that I drank shockingly aren’t sitting well today.

Last night, I was supposed to see Naked Ironing Man. I know, I know, I should let sleeping dogs lie… but last Friday night, after a particularly frustrating exchange with the 30-year-old-shenanigan, I reached out to him via text. I told him that I would love to see him if he was available, and that I understood that he wasn’t prepared to give me a lot of his time. Turned out he was free.

He came over at 10 pm, we sat on my couch talking for two hours, sneaking kisses and touches along the way. We had the most extraordinary night together – as always – and I wish I could describe everything because it was incredible. But it’s a blur of hands and mouth and cock and penetration and what felt like a constant stream of orgasms.

I remember at one point thinking that he was relentless…as he had his tongue on my clit and his fingers in me and every time I thought I would get too sensitive from the stimulation, he would change it up and move and touch me in a different way. He gets almost more pleasure from pleasuring me than I do, if that’s possible.

Then sleep. Nestled in that soft spot on his arm. Awake, repeat. This is a guy who rarely cums…he just keeps going. So it’s always a mission of mine to find that right spot, that right sensation, that makes him release (after hours and hours of sex, of course). We had amazing simultaneous orgasms that left us sweaty and spent. He left at noon because I had to go to an appointment…otherwise we would have spent the day in bed, eating and drinking and talking and fucking. I know this because we’ve done that before, numerous times. It’s heaven.

I promised myself that this time, I would just take him when I can get him. One day at a time. Not pushing and being disappointed. He told me that Friday nights he usually catches up on sleep but that perhaps he could switch that to Thursday nights so he can see me next Friday (aka last night).

Well I’m sure by now, you know what’s coming.

At 5pm last night he told me he couldn’t come over, he had a horrible day at work and wasn’t in a sexy mind space at all. I told him I liked him for more than sex – just his company would be great. We could watch a movie, play Scrabble, talk, drink wine. He didn’t take me up on my offer. I was more disappointed in myself, I think. I’m truly torn. I sincerely believe that he likes me more than just as a fuck, but he certainly doesn’t act that way. The thought of never being in his arms again is unbearable.

So my friend Katherine (she of the “Why does he like her and not me”) also got bailed on last night, by the sloppy kisser. On her way back from a business trip, and feeling shitty, she suggested the two of us go out. Her criteria? Food, booze, and men. She runs her own communications and PR company and is very stylish and has a big personality. Like me, she’s 5’10” and blonde. We went to a luxury hotel bar. She wasn’t sure it was happening enough for her liking. Then a bunch of dudes started talking to us.

Fast forward through the drinking and conversations; it’s 2 am and there are the two of us and two men. One is a high-end real estate agent (The Agent) the other is a major investor city infrastructure projects (The Developer). While my friend and I are both in the top 1% of wage earners, these guys obviously eclipse us. They are both divorced. The Agent tells me that he’s paying his ex 10,000 a month in alimony.

The Developer lives in the hotel condos which are adjacent to the hotel. We decide to go there for another drink. It’s bizarre. Stunning apartment, but a mess. His two girls have a room that looks like barbies puked everywhere. He’s dog sitting for a friend and it’s this old, very ill Chihuahua who is 6 lbs if that. In his bedroom is a big cage with two guinea pigs and the floor has a mess of straw from the animals. We see this when he gives us a tour.

I sit on the edge of the bed with the Agent (real estate dude) to watch the guinea pigs, and the next thing I know he’s kissing me. It’s pretty good. Oh, forgot to mention…he’s probably close to 60. His face looks it but he’s handsome…long hair and beautiful blue eyes. He’s slender and muscular. Very well dressed. Smells great.

We don’t progress that far in the bedroom…just kissing. I forget what I said to him but remember his response…”oh don’t worry, I am taking you home with me tonight. I can’t wait to have you in my arms.” We sit on the couch while my friend is bossing the Developer around and getting him to get us food – they are heating up meatballs. We drink tequila – I give mine to him because I realize I’m at that point where I’m not feeling well. He says “are you sitting there thinking I forgot what I said earlier? Of course, I didn’t. I meant it.”

Katherine and the Developer disappear for a while and I realize this is our cue.

Part Two

0 thoughts on “Last night went completely sideways. Or, how I fu*ked the oldest guy ever.

    • It wasn’t that icky, per se..well, the straw strewn through the bedroom was irritating and the dog was bizarre. More that it was surprising for a dude with so much money…housekeeper, anyone?!

      • Well yes. If I had that much money I’d be hiring a house cleaner to come through once a week. Actually, I don’t earn that much money and I still do have one Lol best $60 I spend.

What do you think?