In Adultery, Never Regret The Sex

Make the sex worth it.

Photo by MARK ADRIANE on Unsplash

I didn’t fall into my affair by accident. I didn’t get drunk at an office party or take an interest in my neighbor.

I chose to have an affair without a potential affair partner on the horizon. I didn’t even know how to get there. An affair had been the last thing on my mind.

Because it was a deliberate choice, I was able to think about the things I wanted out of it before I started. Admittedly, my mind was sex addled at the time, but I told myself,

“You might regret the affair one day, but never regret the sex.”

I promised myself I’d never regret the sex, and I kept that promise.

This motto has seen me through to some good times and helped me avoid dead ends. And it’s what led me back to my long-term affair partner after I stretched my legs a bit.

Dr. No

Because while he was the first, he wasn’t the only one. One guy promised me the moon and the stars. He said he could help me deal with my hub because he was a psychologist. He promised to work with me to overcome my depression, as well.

At the time, I thought, sure, why not? He sent me a nice message. We met in a hotel a few times and had a good time. Then out of the blue, he sent me this pissy email about how he was tired of putting all the effort in and said I wasn’t.

I was like, what? All the effort?

He and some others fail to realize there was no shortage of eligible cock to choose from on my end. I’d figured out quickly that it was a seller’s market when pussy was on offer. Cock was never my problem. Shitty sex and people were.

When I opened my second Ashley Madison account, this asshole sent me the exact same messages he did the first time. Cut and paste. Pathetic. Even now, well over two years later, he’s still sniffing around for a piece. Times must be tough out there.

Next, please.

Running Man

The next guy I met was ok, if not a little needy. He bought me this massive dildo and tried fucking me with it, but it wouldn’t fit. As he pressed it into me, I tried crawling away from the monster. I still have it, but there’s no way it’ll work. That was our second date, and after sex, he started talking about leaving his wife and running away with me!

Um, no.

Ricky Bobby

There was a man with a Porsche SUV. We fucked in the back seat. It was ok, but I’d sort of thought, if you can afford the car I’m sucking you off in, you could probably get a hotel. We couldn’t go back to mine because too many work colleagues were staying there. We met again on another trip and went through the same car situation. My lover asked for some pictures.

Ricky Bobby was nice enough, but I do my best work on a bed, thank you.

All the while, I was getting to know my lover better, and every time I was with someone, I couldn’t help comparing them to him.

Mr. Big

After Christmas, there was a last-minute hotel meeting with a man twenty years younger than me. He was a big boy. After the first round, he started a bath for me, and I wasn’t sure if he would drown me or not, but he didn’t. Before the second round, I’d been using my little bullet vibrator. When he held my legs up on the side of the bed and began to fuck me, he told me to put the vibrator between us.

I did, and bingo! That was nice, but I did have to remind him my older lady’s legs don’t always go the way he wanted them to. I never saw him again. My lover didn’t like this date because it was a last-minute thing. He was probably jealous of his age and cock.

I’d also thought he was too young and too big, and while not disappointing, he wasn’t for me.

Flaccido Domingo

Then there was a man who spent a great deal of time between my legs, but when it came time to put the condom on, he went flaccid. I sucked him and tried again, but it didn’t work. So I ended up sucking him off, which was fine. He’d done an excellent job on me.

But I was looking for a cock that could go a little farther.

Titsy Mallone

I met a guy at his office. He was friendly but only wanted to suck my boobs, which was fine, but he wouldn’t touch my pussy, which needed it. Boy, did I need it. He also wouldn’t let me feel his cock because that was too much like cheating to him. Seriously, you have my tits in your mouth, and you don’t think that’s cheating?

I’m pretty sure wifey wouldn’t have seen the line the same way he did. To me, I’d think,

I’ve already bought the ticket, so why not go the rest of the way? It’s the same price, right?

I had a tension headache when I left because teasing does that to me after a while. I was cheating because I needed more vitamin D, not saliva covered tits.

I didn’t see him again.

49 Shades of Gray

Then I was tied up BDSM style and had a Magic Wand © strapped to my pussy. He told me most women have an orgasm after 15 minutes. At the thirty-minute mark, he had to get in there with his fingers, and after another ten, he gave up, exhausted. I sucked and fucked him after he untied me. I still hear from this guy now and again. Unfortunately, there was this little gag-me-with-his-cock-awkwardness that was a touch offside for me.

My lover encouraged me to go on this date, but he didn’t like the gagging thing either. He also bought me a Magic Wand © for my birthday not long after. Maybe he thought that would keep me away from this guy. He was also the guy my lover poked my bum over. He’s emailed the odd time, but usually only when he was looking for a plus one, to some sex thing.

My lover was jealous of him, so I guess it all worked out in the end.

My Guy

These guys were on my side trips and never in my lover’s city. When I was there, he’d pick me up at the airport, take me to my hotel, and fuck me. Then come back two or three more times during the week for more.

And of these men, my lover was the best. He was the kindest, most gentle, and gentlemanly of them all. He still thanks me after we have sex. He also snuggles up without me asking and stays put when I fall asleep and fart.

That’s true love.

He’s never in a rush to leave, and he talks to me in a way my husband never has.

It took me a while to figure it out, but I had the one I was looking for from the start, and not one of them measured up to him.

The others were good at certain things, but none of them delivered the whole package. My lover instinctively knew what I needed and always worked hard to give it to me. He encouraged me to see other men to relieve my stress when I couldn’t be with him, and I loved him for that even though a couple of them bothered him.

I was a kid in a candy store, and I couldn’t see him right in front of me. It took me a while to see him for the man he was and had been all along, and I’m grateful he was patient with me.

Never regret the sex

I never went back to anyone where the sex and aftercare were terrible. I promised myself I would never regret the sex and I haven’t yet. I’ve had some disappointing experiences, but I didn’t go back for more. And that’s really the point of my motto.

Life’s too short for shitty sex or shitty people.


This was my introduction to adultery —Adultery & Losing My Second Virginity
My first naked playdate.medium.com

He doesn’t mind me being with other men —A 48-Year-Old Married Mom’s First Sex Club Visit With Her Secret Lover
They treated me like a queen.medium.com


© Teresa J. Conway, 2020

By Teresa J Conway on .

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Exported from Medium on April 8, 2021.

Author of How to Cheat: Field Notes from an Adulteress, several short stories, I'm active on Medium @teresajconway where I sometimes share my blog posts, and I'm a fair-weather tweeter @tjconway69.

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