Adultery & Losing My Second Virginity
By: Teresa J Conway
Tags: Romance, Relationships, Sexuality, Sex, Erotica

How to Cheat

Adultery & Losing My Second Virginity

My first naked playdate.

Photo by Sharon McCutcheon on Unsplash

My affair partner sensed my fear. I was worried about meeting and having sex on our first date. We’d been sexting madly for weeks, but that was different. Meeting then getting naked? I wasn’t so sure.

He suggested we meet at a fast-food restaurant parking lot in town the night before our date. It was a nice ice breaker, and the busy location made me feel secure. He joined me in my rental and was a perfect gentleman, even as I let him slide his hand under my blouse. I’m glad he didn’t have much time because I would have done him in the car. I was so horny I wanted to scream. I molested myself fiercely when I got back to the hotel.

I’ve had other first dates since and have slept with a few on meeting. I try not to and never tell them I would. It’s awkward enough when I’m not into the guy so can only imagine how much harder it would be if he thought he was getting laid.

Meeting for coffee is better. You get to know each other, and it’s easier to let them down if you have to (or they have to…bastards).

Before our date the next night, I stopped by a local grocery to pick up a few things: fruit and cheese trays, shrimp ring, wine, bottles of water, and condoms. I’d never purchased condoms before, and I was overwhelmed at the variety. I chose the box colour I liked and headed to the cash. I had no idea what I was doing but knew enough to bring protection myself.

The lady at the counter was ten years older than me, and I was so embarrassed I couldn’t make eye contact. I was a goofy kid and couldn’t wait to get out of there. Cringeworthy doesn’t describe it.

Was this happening? Autopilot got me back to my room. I set everything out but still couldn’t believe what I was doing. Me! The good mommy volunteer with clubs and the PTA.

I hadn’t had sex in a decade and not been with anyone other than hub in 25 years. Yet here I was laying out snacks for a man I was going to fuck in twenty minutes! I’d been wet all day and couldn’t concentrate; I still couldn’t. Thank god, no one at work noticed.

Meeting him in the lobby reminded me how sexy he was, and I tried not to check him out too much as we rode the elevator back to the suite. Although feeling awkward, once inside, I began to relax. I poured the wine, and we settled on the couch. I don’t remember what we talked about, other than his shellfish allergy. For god sakes, this was a playdate; I scolded myself. I was a soccer mom! Why didn’t I ask about allergies?

He was fingering me two minutes after the shrimp was in the fridge. I was naked not long after that. He laid me back on the couch; still fully dressed, he knelt down and devoured me. His passion was unlike any man I’d known. He didn’t let up for an hour; it was ecstasy.

From the couch, we moved to the bedroom, where he continued to work me over with his lips and tongue, licking, kissing and sucking as he went. He couldn’t get enough of me.

We had the fruit and wine during a pause, as we snuggled; he drank the water he no doubt needed. Laying together, he ran his hand over my curves and told me how sexy I was. He tugged and bit my nipples as I used my toy. I couldn’t have asked for better. He took care of me in a way I’d never known. I was on centre stage and he kept me there all night.

I melted in his gaze. He’d known how long I’d gone and worked hard to give me a little back. His sexts and promises weren’t hollow. I can’t recall everything we did, but remember longing for more. He was the first man to go down on me without asking for a blow job.

The hours vanished as he worshipped me. I was in a trance as I sucked him in the shower, the warm water cascading over us. I wanted him and would have sold my soul to keep him there, in my mouth a little longer.

Early the next morning, an overwhelming joy filled me. My pussy well used, my reflection glowing back at me from the mirror. I sent him a quick thank you and floated into the office, him filling my thoughts.

I was reborn. No longer one of the names my husband called me, but a woman again, a sexy full-figured woman that men wanted. Well, one man anyway. He was enough to pull me back from where the loneliness had taken me. I’d only ever wanted one man, but that dream had faded long ago.

As I grew in my adulterous double-life, I let my curiosity guide me. It was liberating, but I’ll never have better than that night. The night I lost my second virginity.

An excerpt from my book, How to Cheat: Field Notes from an Adulteress.