Is it easing into a new relationship or not being that into someone?

Mr Fox and I had three dates in three days. We had not had sex although he’d given me an orgasm.

I completely forgot something important in my last post. When I asked him to come upstairs to my bedroom, I paused and realized I might have to explain my bruises. So I pulled away from our kissing, looked him in the eyes and said:

“If you come upstairs with me, you may see my ass. Which means I need to tell you about something you are going to see. I am very bruised. 

I’ve been exploring my sexuality and one thing I was curious about was my submission, in particular being “beaten” as it’s unfortunately called. So this past Friday night I met a Dom at this sex club and he had me on a St. Andrew’s Cross – do you know what that is? – and I was naked in front of an audience and he beat me. And I liked it.”

I paused and looked at him, questioning. He paused then said: “that is so fucking hot.” Continue reading

A third date with Mr. Fox in three days. 

I am so fucking behind in writing. My third date with Mr Fox was 12 days ago. I’m going to give some short versions of my stories so that I can get back to doing what I prefer – writing in real time.

Here goes:

We met again for our third date over lunch near my house didn’t have sex and he took forever to really touch me but he used ice on my nipples finger fucked me to orgasm and then had to leave for a meeting. The End.

What, not enough? Continue reading

A fantastic two-date day | Mr. Fox & #14

Mr Fox and I had a great first coffee date and we both wanted more. Our text conversation continued and the next thing I knew he was booking lunch for the two of us the following day. He picked a restaurant near my office and made the reservation and just made it happen.

I liked that.

I wore a short black puffy skirt and a light blue leather jacket, with three inch heels. Given he’s 6’4″ I can wear those heels and still look up to him. It’s nice, actually. There are days when I feel great and know I can strut my stuff and that day was one of those days.

We met at a sky high restaurant in a fancy hotel. Ever the gentleman, he held doors open, waited until I was seated, and made sure I was comfortable. I had meetings in the afternoon otherwise would have loved a glass of wine.  Continue reading

A fantastic two-date day | Mr. Fox & #14

Mr Fox and I had a great first coffee date and we both wanted more. Our text conversation continued and the next thing I knew he was booking lunch for the two of us the following day. He picked a restaurant near my office and made the reservation and just made it happen.

I liked that.

I wore a short black puffy skirt and a light blue leather jacket, with three inch heels. Given he’s 6’4″ I can wear those heels and still look up to him. It’s nice, actually. There are days when I feel great and know I can strut my stuff and that day was one of those days.

We met at a sky high restaurant in a fancy hotel. Ever the gentleman, he held doors open, waited until I was seated, and made sure I was comfortable. I had meetings in the afternoon otherwise would have loved a glass of wine.  Continue reading

Meet Mister Fox

Mr. Fox reached out to me on Plenty of Fish. He made a clever reference to my job in relation to his, and it was easy for me to respond.

His profile showed a very handsome, very tall (6’4″) 49 year old long-divorced professional. He has a teenage child, a love of craft beer, and enjoys exploring restaurants. In a notable departure from my latest boyfriends, he has a full head of hair.

You know the next part: witty and interesting messaging back and forth on the dating site, he asked to move to text, and it continued at a reasonable pace and was red flag free (Madeline, it is possible). I was quite excited about meeting this one. Continue reading

Fu*king the oldest guy ever

The Agent and I leave together. I’m obsessing about being able to take my contacts out so we go to my place. We get to my place by taxi. I’m a horrible host…don’t offer him anything to drink. We just start kissing and go upstairs and then we are naked except he’s still wearing his boxers. I recall thinking he has a very good body for an old guy. He has his hand between my legs and it feels very good. The last thing he said to me before I pass out was “I can’t wait to be inside you”.

I wake up at 6am and my head is throbbing; I feel horrible. My mouth feels like something died in it and my contacts are permanently adhered to my eyeballs. I’m tucked in beside the Agent, head on his arm. That at least feels nice. I don’t panic when I look at him…he still looks good in the light of day. He gets up to go pee then I do the same and then realize I need to puke. My bathroom is an ensuite so I run the water and the fan and hope to god he doesn’t hear me – because there’s nothing classier than a woman who fucks on the first date and gets so drunk she pukes.

We go back to sleep. Wake up at 9am. The medicine and puking helped and although quite hung over, I don’t feel like death anymore. He starts kissing me. Hand between my legs. I find myself wishing for NIM and how he touches me. The Agent’s skin looks old…not his body. I’m thinking this as he’s kissing me, mouth on my breast, hand between my legs, and I’ve got my hand on his cock. My inner dialogue is something like this:

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 10pm, 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.

Continue reading

The myth of pleasure from a cabana boy

One pervasive comment or joke I heard a lot after I became single – from married girlfriends, mostly – is that what I should do is get me some young stud for sex. I mean, they call it lots of different things, but that’s the bottom line. I think this is a fascinating topic and certainly one that has no lack of popular culture references.

One part of the attraction – for sure – is that when a young guy pursues you, it feels really darn good.  I’m 40, and this 25-year-old, who could have all the toned, smooth, energetic young ladies he wants, wants me?  Wow.  It’s a great thing and anyone who says it’s not an ego boost is lying.  I’m not sure what the attraction really is about, however – so I’ve asked many of them. Continue reading