Best Mistake I Ever Made

©2025 by the author using the pen name Smuttyandfun

All Rights Reserved.

This is for the On The Job Challenge 2025. As always, your votes and comments are much appreciated.

Everyone is over the age of eighteen.

TORI

Oh boy, I really screwed up this time.

I still can't believe I kissed my boss. And I'm not talking about a little peck on the cheek. No, this was hot. Tongue tangling, body clutching, breast heaving, erection humping, pussy melting, five alarm freaking HOT!

Now that we were taking a breather to catch our breath, I was staring at the floor; because I couldn't even look at him after what we'd done. Especially since he was getting married soon. Which meant I had no business even touching him, never mind nearly tearing his clothes off and practically tackling him to the floor.

My lips felt swollen. And down below I felt hot, wet, and so needy. We'd come so close to stepping over the line it was crazy.

I couldn't deny it, part of me would have been okay with it, too. We could have written it off as just a onetime thing, and blamed it on the booze. I mean who hasn't had a drunken fling?

Eason and I have a great relationship and loved to tease each other and joke around in the office. He is so easy to work for, he's more like a friend than a boss. But now that we'd kissed, he seemed like something entirely different, like a mountain I desperately wanted to climb, until we reached the peak - hopefully together.

Earlier tonight, after we'd finally finished and had everything ready for our big presentation on Monday morning, Eason suggested we have a drink to celebrate. We'd been working together as a team trying to land this client for months, so a drink sounded like a great idea, considering all the long hard hours we'd put in together.

Since the rest of the agency had gone home, it was just the two of us, along with a big bottle of Crown Royal and a bucket of ice.

Though the details are a little fuzzy, I'll never forget the heated look in his eyes as he gazed into mine, across the butter soft leather couch in his office, while he kept re-filling my glass. His gaze was so hypnotic, it was nearly enough to melt panties, while my nipples grew hard as diamonds, straining against my bra. Naturally, my mind wandered off, wondering what it would feel like to have the courage to taste his perfect lips.

"You know, I sometimes wonder what I'd ever do without you, Tori," he'd said, smiling into my eyes as he'd topped up my drink.

Truth was, I was so crazy in love with him -- though he didn't know it -- I couldn't imagine what I was going to do without him, once I finally got tired of watching his gorgeous ass strut around the office, knowing he could never be mine.

Even if he wasn't engaged to marry a stunningly beautiful, rake thin creature like Bettina, I knew with my curvy hour-glass figure, I wasn't his type.

Hot guys like him never looked twice at Rubenesque women like me. And why would they, when they could have models or actresses with bodies to die for.

But at least I could take solace in the fact that we managed to pull apart before things went too far, and stopped once we'd shared that steaming hot kiss.

EASON

What the fuck was I thinking, kissing my assistant like that? Though, I couldn't lie, I didn't regret it. I'd often wondered what it would feel like, and now I knew. Just tasting her lips, felt like heaven. And I know I'd never gotten as hard, just from sharing a kiss.

Trying to think of what to say, I raked a hand through my hair, wondering why I didn't feel more guilty. Especially since I'm supposed to be getting married in a couple of months, and I've never cheated in my life. Yet, somehow, I still managed to fuck up, and dive in for a taste of those sexy lips.

Though Bettina and I might be going through a rough patch, hopefully we could work it out. But messin' around with Tori sure as hell wasn't going to do anything to help me fix my shaky relationship with my fiancée.

But illicit or not, I knew that kiss was something that would live with me forever. All it took was one taste of her, and I was ready to tear her clothes off to find out how incredible it would feel to explore that luscious body once I dragged her to the floor.

Somehow, I found the courage to tell her how I felt. "Look, I'm sorry, Tori. I don't know what I was thinking. Maybe we just had too much to drink. But..."

"But what?" She eyed me, looking kind of worried, like I was about to blame her, when the whole thing was my fault, since I was the one pouring the drinks, and also the one who let things get out of control.

Deciding I might as well be honest, I looked into her big brown eyes and told her the truth. "I'm not going to lie, I enjoyed every second of it. I know we crossed a line, but it just felt so good to finally give in and explore that sexy mouth."

"You know this naughty talk isn't helping, right?" She said with a little smirk, giving me a show of her dimples.

I couldn't stop myself from chuckling, as I admitted she was right. "I know. But I just find you so enticing, all it took was a couple of drinks and I kind of lost my mind there for a minute."

I watched her get up, and start stacking the folders on my desk, mumbling, "Well, it's probably best if we just put this behind us and pretend it never happened."

Though she was right, the way her lush, firm ass was swaying, sure as hell wasn't helping things to settle down.

I got to my feet and tried to step behind her. "Let me help you, Tori," I said as she stepped to the side, brushing her ass against my swollen cock.

She looked back at the obvious bulge in my pants, and bit into her lip, fighting back a smile. "Is that what you want to help me with?" she asked, making me laugh.

"I'm sorry. I know we should try and behave ourselves, and shouldn't let this go any further." I could see the amusement in her eyes, because obviously we were failing, badly. Which made me want to break out laughing, but somehow, I held back, because this whole thing was just so crazy, because even though she was off limits, I still wanted her more than my next breath.

I was feeling so entranced, just from gazing into the warmth of her eyes, I actually jumped when my phone chimed. Considering it was after eleven, I had a feeling it would be Bettina, since she always called me late at night.

"Hey, you," I said, trying to act cool, like I hadn't just been dry-humping my gorgeous assistant while nearly kissing her senseless.

"So... I thought I'd let you know that I found us an amazing flat in walking distance of my office," Bettina said, as though I had already agreed to move there. "It's tiny, but super cute, so I think we can make it work."

I hated that she'd already taken for granted that I planned to change my life for her. But I didn't want to argue, especially once I noticed Tori pointing at the door, wondering if she should leave.

When I shook my head, Tori nodded and took the seat beside me on the couch, where I'd patted.

I could tell from the way she was giggling, that Bettina had probably been drinking. I noticed every time she called, she seemed to be out partying with her co-workers, which had me wondering what else she might be doing now that she was on her own.

Suddenly, I froze, shocked to hear a man's voice, murmuring into the phone, "Baby, you can talk to him later, but this can't wait."

"Who the hell is that?" I asked, wondering what the heck she was doing with someone at four o'clock in the morning.

Bettina giggled. "Oh, don't worry. It's just Nigel. I had a few gummies and I got so high last night, he offered to take me home, so I'd be safe."

"So, the two of you are sharing a fucking bed?" I said, feeling stunned.

"If you think I'm going to behave like a nun, just because we're engaged, you've got another think coming. I've got needs that aren't being met, now that we're living half-way across the world from each other."

Looking embarrassed on my behalf, Tori winced, since she'd heard every word.

"Well, I don't remember agreeing to an open relationship, Bettina," I said, struggling to keep my temper in check and my voice down.

"Don't worry, baby. All I did was give him a little head. It's not like we fucked or anything."

My blood boiled as I heard the guy laughing into the phone, whispering, "As soon you as you hang up, I'm gonna plow that little fanny."

I was so enraged, I couldn't sit still, and I got up and started pacing. Though I knew I'd stepped over the line with Tori, at least we never let it go too far, and stopped at a kiss - and we'd kept our damn clothes on. But hearing that my fiancée was in bed with another man, was the last straw.

Bettina kept giggling, and I noticed her breathing was getting choppy, probably because good old Nigel was running his hands over her body, getting ready to plow her.

"I think I'd better go, babes," she said, with a smile in her voice, undoubtedly directed at her bedmate.

I was so angry and confused, I hung up without bothering to say goodbye.

"I'm sorry, Eason," Tori said, as I dropped onto the couch beside her, running a hand over my face, wondering if I was crazy for ever agreeing to marry someone so flighty.

"I can't believe she'd do something like that. Though, I've been having doubts about us for a while," I admitted. "Lately I'd been wondering if we should even be getting married. Last few weeks, every time she calls, we end up doing more arguing than talking. She got so angry last night she hung up on me when I wouldn't agree to move there. I think I mentioned that she landed a new job in London. And she told me, if I really love her, that I should be willing to give up my job here and start over in England, so we can be together. So, maybe she's trying to get back at me by fooling around with someone else."

"But why would you leave, when you've just been promoted to VP of marketing?" Tori said, sounding shocked.

"Bettina knows full well what I'd be giving up if I left here. And to be honest, I'm not really big on the idea of having to start over in another country. Plus, things were starting to cool off between us even before she left."

"I guess us fooling around isn't really helping." Tori said, looking guilty.

With my eyes on hers, I stroked her cheek, and dragged my thumb across her full bottom lip, while she stared up at me, looking conflicted. "Actually, that kiss kind of opened my eyes. Because what we just shared made me realize that I've never in my life experienced that kind of passion, which I think I should be feeling with the woman I'd planned to marry."

I pulled her into my lap, and groaned when Tori began rubbing herself against what was straining in my boxers while she grinned and told me, "I know, I'm bad. But a girl can dream, right?"

She had my chest heaving, while I struggled to contain myself. I reminded myself, after what we'd just done, I should not even be thinking about sliding my hands over her lush round ass. Nor should I be copping a feel of her luscious breasts. Pressing a kiss against her ear, I whispered, "I know it's wrong, but I just want you so badly right now, I can barely hold back."

Tori eyed me, looking confused. I could imagine the guilt weighing on her, now that she'd messed around with a man who she assumed was about to be married. Even though I had been more than happy to mess around with her.

Teasing my cock with her hot little puss, Tori whispered in a throaty purr, "Then don't hold back. Just take me, Eason."

That was all I had to hear. I grabbed her ass, pulled her close, and kissed her, while she wrapped her arms around my neck, eagerly sliding her tongue between my lips.

Tori moaned as I hiked her dress up and slid my hands into her panties, getting off on the feeling of finally getting a chance to squeeze her warm, soft ass as she plaintively whimpered against my lips.

She had me so stoked, my heart felt like it was pounding out of my chest. The way she had her legs wrapped around my waist, grinding her pussy against my throbbing cock, she had me rock hard in a heartbeat.

"I need to see you naked," I told her, while we feverishly kissed.

I got us to our feet and I unzipped, and let my pants fall to floor. While she watched, I unbuttoned my shirt and tossed it aside. Then it was my turn to stare when my gorgeous young assistant stepped back and did a playful little strip tease for me, a fun little bump and grind, casting aside her dress, and kicking off her heels while playfully eyeing what was straining against my boxers. Till she was standing before me in nothing but an uber sexy black lace push-up bra and tiny thong that barely covered her pussy.

"You really are beautiful," I whispered, as I reached out to pull her into my arms.

Though I was tempted to drag her down to the floor, so we could mate like bunnies, resisting the urge, I lifted her off her feet and carried her back to the couch.

I think Tori was surprised at my restraint, as I enjoyed running my hands through her long, shimmering auburn hair, while dusting kisses over her stunningly pretty face.

"You know I've always had a thing for you," I confessed. "But you're so beautiful, I just assumed you were attached."

I thought it was adorable the way she blushed. "Well, I guess I should tell you that I was thinking about quitting, because I just couldn't stand the idea of you getting married, and living your life with someone else. When I'd been hoping..."

"Hoping for what?"

"I'd always hoped that one day you'd notice me." She looked hurt when I threw back my head and laughed, as she wrinkled her nose and asked, "What's so funny?"

"I'm laughing because I knew from the first moment I set eyes on you, that I was in trouble. But you're just so damn good at your job, I didn't want to risk screwing things up between us, which is why I started dating my neighbor Bettina. If I had even an inkling that you were interested, I think we would have gotten together long before this, because if you've even crooked a finger at me, I wouldn't have been able to resist you."

Flashing a teasing smile, she unclipped her bra, freeing her luscious breasts. I think my heart almost stalled in my chest, sure I'd never seen anything as enticing as my gorgeous assistant, smiling into my eyes, while I got off on the feeling of finally being able to cup her warm, soft breasts in my hands.

"You're absolutely perfect," I whispered as I claimed her lips in a smoking hot kiss.

"Eason, please. I need to feel you inside me," she pleaded as I teased her nipples with my thumbs, while she shivered, grinding herself against my throbbing cock.

"Damn it, I don't have a condom," I said, wondering where the hell I could get one at this time of night.

Tori grinned. "Well, I'm clean and I'm on the pill. So..."

"Then I think we'd better get naked before I embarrass myself by coming in my boxers."

I peeled off her thong and groaned as I got her on her back and spread her legs, eager to dive in and have a taste of her pretty pink pussy. "Every inch of you is beautiful," I whispered as I flattened my tongue and had my first taste of her sweet tight puss.

"Ooh, that feels incredible," she cooed, digging her hands into my sandy blonde hair. As I licked a path from her tight back pucker to her swollen clit, suckling it between my lips, and flicking it with my tongue, driving her closer and closer to the edge.

I couldn't believe how tight she felt as I eased a finger inside her and gave her a little finger fucking that had her shivering right to her toes.

As much as I was enjoying feasting on her tight little puss, I was so desperate to get my boxers off and get inside her, I had to roll off her and get to my feet.

I loved the way her eyes flared when I stood, tugged off my boxers and tossed them aside, freeing my throbbing cock. "Oh my gosh, is that going to fit?" she asked looking a little worried as she watched me slide my erection through my fist as I eyed her luscious body.

"Don't worry, I'll take my time. And I promise, it'll fit." I was kind of thick and pretty long, and definitely didn't want to hurt her, so I knew I had to go slow.

"If you say so," she said sounding a little nervous, as I got between her legs, and pressed a kiss to her lips as clutched her thighs and spread her open. Looking down between us, seeing my cock poised at her opening, I had such an urge to thrust so I could feel the heat of her wrapping around me. But I took my time and carefully eased my way in, till I'd managed to pop my cockhead just inside her tight little channel. "You're so tight," I murmured as I bent and kissed each breast in turn, while carefully flexing my hips so I could get in a little deeper.

I loved the way she was smiling into my eyes, as I dusted kisses over her face as I slowly began to thrust, till I'd worked us into a nice steady rhythm. Till she finally murmured the words I was dying to hear, "Ooh, that feels good, Eason. Tight, but really good."

"You feel like heaven," I told her as I picked up my pace and began to ride her, while she wrapped herself around me, quivering in my arms.

Part of me could hardly believe that we were naked on my couch having sex, because I'd always been careful to hide my feelings. But there was no getting around it anymore, I was in love with her, and I was glad I was finally able to show her how I felt, as we made love.

It was such an incredible feeling, to be pumping into her body, while she clenched her inner muscles around me, drawing me in even deeper, almost begging me to come.

Gradually, I began to feel the pressure mounting, building up from my balls, as we got closer and closer to reaching the peak. I loved the way she went into a full-body shudder as she came, while I let out a deep satisfied growl as I let go. And with one hard thrust, I came like a volcano erupting, while I held her tight and kissed her with everything I had.

Even after I came, I kept thrusting. It just felt so good to finally be buried deep inside her, that I hated to pull out.

She looked elated as I felt, as I kissed her and said, "Wow!"

Careful not to crush her, I rolled us onto our sides so I could her stroke my hand along her back as I slowly I came down from the high of coming harder than I'd ever come.

I loved the feeling of having Tori's warm soft body curled around me as we slept together, curled up on the couch. I could feel the heat of her lips pressed against my neck, like she was still kissing me in her sleep.

She blinked her eyes, looking a little confused when my phone started chiming. Though I grabbed it off the floor as quickly as I could, it still had the effect of an alarm clock, jarring us awake.

I groaned when I looked at the call display and saw it was Bettina, because I had nothing left to say to her. "So...," she said, "I hope that little performance did the trick and made you jealous enough to want to quit your job and get your ass over here to be with me."

I knew I had to tell her the truth. "Bettina, I'm sorry, but I think we're done. I don't know if that guy was really in bed with you last night or not. But it doesn't matter. We never really discussed how things were going to change for us once you took that job without even discussing it with me. I'm happy here, and I don't want to leave. I'm sorry but... it's over."

"You've got to be kidding. Can't you take a joke? I only did it to you make you realize that if you don't quit your job and join me, you could lose me to someone else."

"I really hope you do meet someone else. Because I'm not willing to give up the life I have here."

"Okay fine. Then I'll tell you the truth. I was with Nigel last night, and it was incredible. The guy's a beast in bed, and I loved it."