I took a new lover. 

My AFF profile was open for a few months last Summer and early Fall. It’s where I met Leo, as some of you may remember. I have zero recollection whether I met anyone else in person from that site – it’s funny how time erases some people and not others – but there was another man who tried and we simply couldn’t connect.

I never wrote about him, because I never met him. The last interaction was him asking me to meet one weekend morning for coffee, then when I agreed to the time and place he went silent. It was the second or third time it didn’t work due to his flakiness so when he reached out again, I scolded him and said no thank you.

That was enough for him to not try again. Until recently. Continue reading

A small-town hookup.

I was away for work for one night. A town I couldn’t get to on a direct flight, so I suffered annoying airport layovers and airplanes so tiny the smallest of carry on bags won’t fit.

Two days of travel for a few hour event; just for me to shake hands and congratulate team members and say thank you. Drink some wine and eat appetizers. I didn’t have Liam and was happy to do it. It’s a seaside town which I love.

I arrived without incident.

As I pulled the rental car into the valet parking for the hotel, I noticed a very cute, very young valet. He came over to retrieve my cars keys, and recited his script of “where are you joining us from today?” Continue reading

The beating of my cervix. Then a slow fade.

So the last we heard of Lewis, he was on my couch showing me his massive cock. Well, massive for me. I’m sure it’s all relative.

That was Wednesday night. We planned to see each other the following Tuesday. Even if he turned out to not be relationship potential, I was really excited to experience someone of his size. Shallow, perhaps, but I wanted it to happen. If needed, I was even going to break one of my texting guidelines (generally let them set the pace of communications) in order for that to happen.

Thursday morning I sent him a “good morning handsome” text. No response. At 1pm I told him he was responsible for my inability to focus on my work. He said:

“Good Afternoon! Me? Innocent little me? Well…I’m sorry but it was worth it! I pictured you on your hands and knees and I was eating your pussy and ass out from behind…then I slept like a baby…”

It’s funny how the gut works.  Continue reading

Boy-Toy applications are now being accepted

In the now 7 months since I started dating again, I’ve become more comfortable with the notion that some guys – especially those looking for sex – are like boomerangs. They come back. Many guys I saw in the early fall ended up being one-night stands, whether I wanted them to be or not. What has astounded me is the number of these men who boomerang.

One notable example is The Chef – not to be confused with The Cook.  This young guy (29) is actually a professional chef. He was the second young guy I agreed to meet off an online dating site (the first was the messed-up 26 year-old), and it was partially because his profession was interesting. He had a full sleeve tattoo on one arm – of his favorite fruits and vegetables.  I no longer remember our online dating interactions, but I do remember our first date.
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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.

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I shat where I ate

I refer of course to the expression relating to affairs and sex with co-workers, don’t shit where you eat.  Although when preparing to write this, I realize I’ve been involved with four men who work for the same company.  But since this company is so large, I’ve only broken the rule once with someone in really close proximity (the fooling around with a co-worker while still married dude).

My second dalliance I should definitely write more about – he lived a several-hour-plane-ride-away and we fell in love. after falling in lust.  It was heady and exciting and I think about him as being responsible for my sexual awakening.  We are both now split from our exes but it’s just not meant to be.

I’ll skip the third – not because he’s not worth writing about but because I want to get to the recent.

About a month ago, we had a huge party at a hotel to celebrate a milestone at work.  People came from cities within a couple of hour radius.  About 700 people in total.

A female colleague and I were milling about the party, drinking our wine and enjoying the food.  In walks this guy who we both notice at once.  Tall, extraordinarily handsome, shaved head, built, well dressed, exuding confidence.  She says “where the fuck has he been all this time” since neither of us have ever seen him before.  Now, she’s married and I’m not, so I have dibs.  I do a subtle (well, an attempt to be subtle) walk around to try to see his name tag.  Nope, we’ve never heard of him.
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