Losing My Anal Virginity Was Hotter Than I Expected

The night I gave myself to my affair partner — completely

A do not enter sign symbolizing my attitude before my first anal sex experience with my adulterous affair partner.
Photo by Tim Mossholder on Unsplash

He greeted me coolly at the door, then sat, staring blankly into the next room. He’d booked a small suite for the evening, but that was before our fight. I’d relocated to his city not long before, and now that we could be together more often, everything was falling apart.

I thought I was losing him.

That we’d even fought scared me. I knew I was in trouble then and hadn’t even seen it coming. Not until it exploded in my face.

I was in love with him.

I stood, with my coat on, wondering if I should leave. He hadn’t given me much more than a one-word response to anything I’d said since he opened the door. He was quiet but didn’t seem angry as much as he was sad, so I waited for him to open up.

When we’d lived apart, he’d seen other people, but I hadn’t seen many. The risk of an affair where I’d been living was too high. Of the few I’d chatted with, none were strangers. I either knew them through work, the community, or mutuals. What was interesting was finding out who was on the prowl.

Although I was desperate, I wasn’t desperate enough to be the talk of the town, so never went through with it.

My business trips were a different story. As I’d traveled across the country, I’d had a few dates, but none left an impression. I was still feeling things out when we’d met, and I was excited by the attention so kept looking.

The only reason we were together as often as we were was that I went to his city more often than anywhere else. I’d discovered early on that dates were very hard to arrange from a long distance.

My travel windows were so small the people I was chatting with often couldn’t fit my schedule.

It was easier with him because I knew in advance when I’d be there so he had plenty of time to make the arrangements.

Coordinating availability is often the most challenging part of arranging an adulterous date.

And our problem that night wasn’t my lack of success in making a date, but a date I’d managed to make.

I don’t even know why I told him. My wingman asked me why I did because most men can’t handle sharing a woman no matter what they say.

Of course, me sharing him with other women didn’t seem to be a problem for him. Bastard.

Finally, after five awkward minutes, he invited me onto the bed and asked me to lay down. Still dressed, he hung on to me as he never had before.

We lay there for about half-an-hour, and when he finally began to relax, I fished his cock out and started stroking him.

He didn’t resist, so I took him in my mouth and began sucking him. It didn’t take much to change his mood after that.

When he took out his phone, I knew things were back on track. He knew how horny being filmed made me. From there, we quickly undressed and got down to business.

“Turn over,” he directed, in a way I couldn’t refuse.

He could be intense when he wanted to be, and I loved it when he took charge. Being ordered around lights me on fire.

“I want your ass,” it wasn’t a question.

“Ok,” I responded, closing my eyes.

His directness was how he asked. It wasn’t a demand. I had a choice, and I knew he’d respect my decision. He’s never done anything without verbalizing.

He was a gentle and considerate lover who’d never forced himself on me. But when he was like this, I would do anything for him.

It was a pretty tall ask.

I’d never been fucked there. The idea had never appealed to me. Others had asked, but until that moment, I’d always said no.

I felt cold gel dripping on to my perineum and anus. Then he began rubbing his cockhead along my crack. He’d always loved my ass but had never talked about taking me there.

Entering slowly, I felt his head slide past my sphincter and press on the inner one. It was uncomfortable in a way, but not painful. I relaxed and let him work himself inside me.

Once seated, he lowered down on me, covering my back with his chest, but still holding himself up. I felt protected by his body, covering mine. We stayed like that for a moment before he slowly began fucking me.

I felt his cock in a way I never had before. Holding him tightly, I felt the definition of his shaft. It wasn’t exactly painful or uncomfortable, but it wasn’t familiar either.

I grunted with each thrust as he drove himself into me at a slow and steady pace as he took me.

He didn’t ask if I was ok but fucked me in silence. Using me, using my ass, satisfying himself with my body.

I was growing wetter with each thrust. God, it was so fucking intense, me laying there, giving myself to him, and him taking me as he pleased.

His breathing changed. He was close. I love the sound he makes when he cums. An animalistic low, forceful grunting as he tries to hold his orgasm back.

Aroused beyond belief, I begged him to cum in me.

Burying himself, I felt his cock jerk and throb inside me as his sperm jetted deep into my ass. His arms tensed around me and held me tightly. I felt the heavenly weight of his body pressing me into the mattress as his passion entered my body.

He exhaled in a long, satisfying breath that told me he’d finished.

“Thank you,” he whispered as he nuzzled and kissed my neck, and withdrew himself. Releasing me.

It was so intense.

His forcefulness, power, and passion were beyond anything I’d experienced with him. He knew no one had been there before and that’s why he wanted it. And it was why I wanted him to have it.

He wanted me for himself. All of me.

Despite the fire inside him, he entered me gently and without force. He gave me time to adjust. I felt safe with him. I trusted him and knew he’d never hurt me.

In letting him have me, I let him mark his territory. I showed him that night I was completely his and no one else’s.

And I let him because I love him, and never want to lose him.


Here’s another one of my firsts —I Smoked a Joint For the First Time in 30 Years With My Affair Partner
And I didn’t even turn into a junkie.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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