I Was His First Cheat

Photo by Andrey Zvyagintsev on Unsplash

As I entered the hotel lobby, I saw him sitting in a chair, patiently waiting for me. We were both a little early, him more so. We had the room from 9:30–4, but it was a little before nine. I figured they’d let us in as soon as I checked in, so I wasn’t worried.

Was I nervous? A little. It was exciting to have this day finally come. When the hours of waiting turned into minutes, though, I felt a surge of anxiety, fear, and excitement, like when I first started meeting strangers for sex.

I think it’s normal to feel that meeting for sex for the first time. Sure, I’d sucked him off the week before, but that was different. We were in the heat of the moment (I created), and it was easy to give in.

Check in

He started to get up when I came in and met me at the desk. I said hi and gave him a little kiss as I took my wallet out and passed my ID and credit card to the desk clerk.

He seemed a little nervous as well but was hiding it. It’s funny how life’s mundane activities, such as checking into a hotel, can take the heat out of a situation.

As I collected my key card and confirmed we could go to the room, I started to relax. He picked up my bags, as I’d stopped for goodies, and brought my toys and some wine I’d picked up on the weekend.

The room

The room was the generic sort found in those non-descript hotels along the highway that caters to travelers and degenerates like us. Queen bed, double couch, small table with a couple of chairs, bar fridge, etc. Nothing crazy, but it would suit us.

I drew the curtains and put some music on — I have a portable blue tooth speaker that helps set the mood.

He was dressed for work in business casual khakis and a golf shirt — he had his building pass on his neck, for show, he texted. I was in a plain light floral summer dress and matching tan underthings. I don’t usually wear hose in the summer because I love the feeling of the breeze on my legs.

We’d been chatting for about a month, so making small talk easy as I poured us wine and set up our snacks. Then, finally, I put our lunch in the fridge. I’d brought fruit and cheese trays and cold cuts and buns for later.

He sat on the couch as I worked and told me how nice my bum looked, which I always appreciate. My lover likes my bum too.


Refilling my wine, I turned down the bed, and I finally sat down beside him to relax. What I love most about a hotel meet with this much time is there’s no rush. After more small talk that wasn’t going anywhere, I finally asked,

“Are you ready?”

“As ready as I’ll ever be. Just tell me what you want me to do.”

“You can kiss me,” I put my wine down on the coffee table and turned to him as he leaned in. His mouth tasted fresh and clean, which I liked. It was nice but a little awkward, which was cute.

“You can touch me too, you know,” I whispered in his ear as he nibbled at my neck. God, I wanted him on me, but he seemed to need encouragement. I felt the wine I’d knocked back setting up and was getting a little horny from the kiss and the hotness of the whole thing.

He put his hand on my knee, and I slid it up my leg to my crotch. I needed him to start working me over. My pussy was aching.

He figured it out with the right encouragement but didn’t try too hard to slip his fingers inside my leg band to get at me. But, of course, when he fingered me the week before lunch, I took my panties off for him, so maybe I didn’t notice his hesitation.

I took over

Slowly drawing away, I reached for my wine, stood up, and took a long pull staring into his eyes as I swayed to Pitbull’s I Know You Want Me.

One, two, three, four, uno, dos, tres, cuatro…

Setting the empty cup down, I kicked off my sling backs, pushed the straps off my shoulders, unzipped, and dropped my dress to the floor.

Stepping out of it as I swayed my hips, I unhooked my bra and dropped it behind me.

Standing before him, I held out my hands and took his. Then, I put them on my hips and hooked my thumbs in my panties to push them down while holding his hands. He soon got the hint and pulled them down until they fell past my knees.

Now my pussy was at his eye level. Retaking his hands, I pulled him up, put them on my ass, wrapped my arms around him, and kissed him deeply as I pressed into him, still swaying to the music.

Pulling back, I undid the button on his shirt, tugged it from his pants, drew it up over his head, and helped him take it off. Then, dropping my hands to his belt, I opened his pants. I could feel his cock pressing against me, so I knew he was into me but couldn’t seem to take the lead.

I gave him a squeeze as he slipped out of his shoes. Then, I helped him out of his pants as I lowered myself in front of him. He smelled sweet like he had the first time I sucked him.

I couldn’t help but compare him to my lover. My lover often has me stripped, and something in his mouth before the door shuts. The first time we met for sex, I was naked, and he went down on me within ten minutes. Of course, he doesn’t always do that, but damn, when he does, it makes me feel so wanted…

Getting down to business

Now, in his socks and boxers and kneeling in front of him, I teased his cock out of his undies. Then, stroking him, I looked into his eyes and smiled.

“Is this what you wanted?” I asked coyly. He didn’t answer, but let out a deep sigh, closed his eyes, and reached out to caress my hair.

It was.

He didn’t pull me to his cock but stroked my hair. He was so gentle I wasn’t sure how long we’d stay like that if I didn’t move.

I took him into my mouth and ran my tongue around his head, and he let out a quiet moan. I took him a little slower than when I got him off in the car. I needed him to last but wanted him to get a taste of what was coming.

Holding his hips, I took him as deep as possible by pulling myself onto him. I get a little gaggy, but it was deep enough to give his cock a good mouth fuck to a remix of the Eurythmics’s Sweet Dreams.

When he started to pulse back, pushing a little deeper and holding my head with both hands, I was happy he was finally doing something on his own. I tried not to think about gagging as he pumped my mouth but let him enjoy himself. He was still very gentle and acted like I was fine china.

I let him take the lead for a minute or so before backing off. My pussy was feeling sorely neglected, and I needed something.

Standing up, I gave him a big sloppy kiss making sure he got a taste of his pre-cum as I pushed my tongue into his mouth. Some guys don’t like that, but he didn’t seem to my mind, and if he did, he didn’t show it.

My lover would have laughed and turned his head away before our lips made contact. Sorry, that’s not for me, he’d always say with a smile.

Turning to the bed, I sat down on the edge with my legs spread wide, giving him a great view of my now glistening pussy and thin red hairs fringing my nether yayeh. Then, pulling him towards me, he was squarely between my legs.

I gave his cock one last suck before looking up.

My turn

“My turn,” I ordered with gentle authority.

Laying back before him, he was slow to descend to my pussy but got there. He was taking me in with his eyes and told me how sexy I was, and while I was flattered, he thought so. But I needed him to get going.

After a few tentative licks, he got a little more comfortable. It mostly felt good, but I don’t think he was listening to me. Just as he hit the spot and my breath ragged, he’d move his mouth and tongue elsewhere. Again and again, he did that.

Fuck, it was annoying, but I tried to make the best of it and not let him know how bad he was. My legs were draped over his shoulders, and his arms were wrapped around my hips.

I left him there for five minutes and moaned through the shitty parts. I figured he was no good because he didn’t like it, so I tried to get off by torturing him a little. When he got a little tentative, I’d moan, say yes, press his back with my heels and force his face into me.

My man will stay on the spot and only come up for air if he’s gone too deep. He’s vigorous, dedicated, and most importantly, he listens to my body. I don’t think this guy could do what I wanted if I pointed at it and talked him through it.

He was afraid of pussy, but like most men, had no problem cumming in my mouth.

I never have an orgasm from oral, but I know how good it was based on how long it takes to get there with a toy. Usually, my lover will lift his head, stand up, bring me my wand, and finger me as I finish. Or suck my boobs as I stroke him with my free hand.

Toy time

When I finally let him go, I asked him to pass me my toy bag and dug out my Magic Wand. I was wet enough from his saliva, but his approach was so disjointed I almost had to start from scratch.

As I toyed, I told him to lie down and hold me. I wasn’t upset with him, but I needed some fucking attention at that point, or my head would explode. He felt good as he scootched in, and I enjoyed his fingers tugging on my nipples and the way he kissed my neck and chest, but my wand was doing the heavy lifting.

I think he was getting a little bored watching me orgasm for half an hour, but god, I needed some sexual healing after what his mouth had done to me. Noticing him withdraw his attention was all the encouragement I needed to let it roll for another five minutes.

I dropped his cock and rode my toy with abandon, knowing he hadn’t had his cock in a pussy for five years.

There’s something about a bit of schadenfreude* that just fucking turns me on. I’m not a sociopath because I experience empathy, but I’m probably whatever is on the spectrum right next to it.

When I was done, I moved over, pulled him into the middle of the bed, and rolled him onto his back. Then, I sucked him hard again, mounted him, and, holding the headboard, fucked him bareback with my tits swaying in his face until he came deep inside me.

I was going to insist on a condom, but I needed some cock right then, and taking him like that and letting him cream-pie me was so fucking dirty-hot I almost came again.

Sleepy time

I lay on his chest after he came and let his cock shrink and slowly slip out of me. I love that feeling. Knowing I made him cum, and let our mixed fluids run out of me onto him.

I dozed off for a few minutes and was awoken when he moved to get out from under me. I pulled the blanket over me and continued to doze. I usually don’t do this much work during sex, which tired me. I wondered if this is why my lover always falls asleep after I make him cum.

He got up and went to the bathroom and then joined me. I usually wipe myself, but it was so comfy I didn’t want to move. So I held up the blanket as he returned, and we cuddled again.

Cuddling after sex is what I missed the most after all those years without. We never cuddled any other time, and now hub and I didn’t cuddle at all. So this is the only time I got a nice snuggle, and my friend didn’t disappoint, thank god, because he was getting all Ds so far.

As I lay there, it occurred to me that maybe his wife stopped fucking him because it was too much work.


We got up and had a nice lunch and snacks, a bit more wine and water, and chatted. He’s a super-nice and thoughtful guy but couldn’t take the lead. I’d thought about making him eat his cream pie but fought the urge. We each had a quick shower after lunch to splash off the morning’s fun.

The wrap up

Once again, on the couch, I sucked him hard, and this time made him fuck me doggie until he came again. I was happy he could get it up again, and it lasted a good while, but there was no longer any thought he’d take the lead, so I just told him what I wanted and kept it simple.

He seemed happy with that, and as we were lying in bed, I asked him what he thought. He said he was happy and was turned on by how I took charge.

Someone had to, I thought, smiling to myself.

He asked me what I thought about him, and I lied. I’m sure there’s a lady out there for him, but it wasn’t me. Part of what gets me fired up during sex is a man who uses my body to satisfy himself. The sort of man, like my lover, who knows what he wants and takes it.

That’s not particularly feminist of me, but I like what I like, and being fucked by a man who isn’t afraid to take what he wants is what I like.

This guy was sweet but timid, and I don’t think any amount of sex with him would change his nature. It wasn’t even a sub/dom thing. He didn’t know what he wanted or what I needed, and I’m not sure he’d figure it out.

Don’t get me wrong, I enjoyed popping his adultery cherry, but I’m glad we’d agreed it was a one-and-done thing, so I wouldn’t have to ghost him.

After that performance, no matter what we’d agreed on, he was a one-and-done. I do enough work at home.

When I’m cheating, I want to be worshiped.

Schadenfreude — pleasure on observing misfortune and in particular, the fact that the other somehow deserved the misfortune.

© Teresa J. Conway, 2022

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.

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