When One Thing Leads to Another Ch. 05

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The humiliating grand finale, and an alternative perspective.
18.2k words
4.91
14.7k
15

Part 5 of the 5 part series

Updated 06/15/2023
Created 01/27/2023
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Thanks for reading! See the previous chapters 1, 2, 3, & 4 for the completed picture on everything!

-----

My eyes stared at the ceiling for what felt like hours. I knew it actually wasn't that long, though. My internal clock guessed that I had been sitting in my hallway for about twenty-five minutes now.

Every now and then I'd begin to get nervous, but thankfully this moment was one of the calmer ones. I didn't have my phone to keep me occupied, or even a watch to keep track of time. It was just me, sitting alone outside my front door in my building's hallway, dressed in a t-shirt and mesh shorts.

And a powder blue colored lace teddy.

As I readjusted myself against the wall, I could feel the tight fabric that was hugging my body pull with every move under my clothes. The dainty blue lingerie wiggled its way even further up my butt, while the straps over my shoulders twisted and tugged against my smooth skin.

My penis stirred as the sliding lace lingerie served as a humiliating reminder of my predicament. As usual.

From the other end of the hallway, a noise. My pulse quickened. As I heard the elevator moving past my floor, I let out a sigh of relief. At least for another few moments, I was in the clear.

It wasn't just the teddy I was wearing that was causing me to want to be left alone. At least my shirt and shorts were, if just barely, covering the sexy blue fabric from being out in the open. It was so much more than that.

It was the shadowed outline of my lingerie underneath my shirt, noticeable over my shoulders and down my back. It was my perfectly shaved arms and legs sticking out of my clothes. It was the matching shiny clear gloss on both my fingernails and toenails, all exposed to the world.

And it was also the unmistakable sounds of my girlfriend getting fucked by another man radiating through the wall.

Even though I had gotten too use to hearing Mckenzie's rhythmic moans and whimpers as other lovers pleasured her, I still winced with every one of her squeals. The worst of it was that after listening in after so many dates, I was now familiar with the spectrum of sounds Mckenzie would make during sex.

I knew both the slower, longer moans when she was passionately getting fucked as well as the quicker, higher yelps when she was getting close to cumming. And obviously the final explosive screams as she would get brought to orgasm. I was even familiar with the noises she made when she was faking it. Embarrassingly, I had quickly recognized those sounds.

My eyes darted back down the empty hallway as the elevator made another sound... Just passing by again on it's way down to the lobby.

Another sigh of relief. Probably around thirty minutes now.

Every single time I had to plan Mckenzie's date nights with other lovers it was humiliating, but this time I was particularly on edge. It wasn't even because she had chosen my bed this time to fuck another man on. She had already done that before.

This time, though, I had nowhere to go.

Ever since Brad ordered me to manage to Mckenzie's dating apps with him in London, much of my free time now revolved around making sure her sex life flourished. Each morning, I'd log in and reluctantly begin teasing and flirting with a whole host of men under her profiles. Given Mckenzie's looks, there were always matches.

I'd then go through the painful process of making comparisons based on their looks, their muscles, their compatibility with Mckenzie, and, ugh, their bulges. As I should've guessed, the size of their bulges had been the dominating factor on whether she'd considered the date to be successful or not so far.

And poor dates led to punishments. So that's why I was here. Sitting alone in my hallway. Forced to listen in as she got loudly fucked in my bed.

To add extra insult to injury, Mckenzie wanted me to switch it up and told me to find her someone 'younger' this time. I remember by face burning red as I lowered the age on her profile's preferences and began swiping through images of the new set of men, many of them students from the local university. I immediately got bombarded with messages from a host of horny college guys all trying to have sex with my girlfriend. And I had to pick one to do it.

I nervously looked down the empty hallway as Mckenzie's squeals began to pick up. Ever since that first humiliating night I met Brad at Mckenzie's friend's wedding, my whole life felt like a blur. I was still in disbelief at how this had become my new normal. Even just a night like tonight felt like a dream. Less than an hour ago, I was fast asleep.

My mind flashed back to that moment I was awoken...

----

*Bang! Bang! Bang!*

It took a moment for my disoriented brain to comprehend that the loud knocking sounds weren't a dream, and that they were actually coming from my door.

*Bang! Bang! Bang!*

Barely awake, I grabbed a shirt and a pair of shorts off the ground and basically sleepwalked over to the door. Even in my hazy state, I had a pretty good idea who it was. I could already feel my stomach tightening up in knots.

*Bang! Bang! Bang!*

I finally reached the door and peered through the peephole. My fears were confirmed. There stood Mckenzie, looking as stunning as ever. And just behind her was the silhouette of a large man. A man I obviously recognized as it had been me that he had been flirting with.

My heart skipped a beat. At least the past two times Mckenzie had brought someone back to my apartment after one of her dates, I was given ample warning.

*Bang! Bang! Bang!*

I took a deep breath and sheepishly cracked open the door.

Without any hesitation the man shoved the door into my face, pushing me backwards. The cocky college jock gave me a demeaning look, smirked, and casually walked over to my kitchen where he served himself a beer from my fridge. He turned to me as he walked towards my bedroom.

"Don't worry, cuck, I'll take good care of her."

teased, "I bet you're already getting hard just thinking about what he's going to do to me."

There was no denying it. As much as I didn't want to admit it, my penis was betraying me once again. I still wasn't even fully awake yet, but my cock was already straining against my mesh shorts. Mckenzie lightly tapped them, confirming her suspicions. Through a knowing smile, she went on.

"Or just think about what he already did to me. The bathrooms at the club were private stalls."

Her soft hand made its way under my shorts. In one motion, she gripped my now erect cock and used it to pull me close to her. She squeezed the head as she whispered into my ear.

"I'm so fucking wet right now."

In one motion, she guided my cock out of my shorts and towards to the bottom of her mini skirt, pressing upwards against the fabric. I gasped as it made contact with her smooth thighs. Still gripping my penis with her hand, she slowly led it to her pussy, the material from her skirt bunching up on my shaft.

My legs quivered as the tip of my cock pressed up against her slit. I was now so turned on I could barely stand up straight. Mckenzie hadn't fucked me since before this whole ordeal with Brad began and I would do anything for it right now. Somehow my brain had even forgotten that there was another man in my bedroom that she had brought back.

And Mckenzie wasn't lying. She was so fucking wet.

She pressed herself further against me until a feeling of warmth made its way over the head of my penis. A soft moan escaped me as I finally felt the familiar sensation of her pussy wrapped around me. I instinctively began to press myself forward, but her hand firmly held me back, leaving only the head inside her. I could only whimper in response as a devilish grin formed on Mckenzie's face.

"It's frustrating, isn't it? Not being able to cum?"

I could feel my face turning even redder as she spoke.

"That's why I need men like Brad to fuck me. Men like the one you set me up with tonight to fuck me in your bed."

I knew she could see that her humiliating words were only turning me on more. Her smirk widened even further as she continued on.

"But don't be jealous, baby, maybe you'll get to cum when Brad finally fucks you. I can't even tell you how hot it gets me thinking about you bouncing on his cock like the little desperate slut you are."

My penis involuntarily thrusted forward at the thought. Even though I was barely in her, I was so embarrassingly close to cumming. I somehow blushed even more as I glanced into Mckenzie's knowing eyes.

"Don't even think about getting off or I'll have to tell Brad," she scolded me with a grin, "I'm sure he'll spank you so hard you won't be able to sit down for a week."

It took every ounce of energy I had left to pull away from Mckenzie without cumming myself, especially since each word coming from her mouth was pushing me closer and closer to the edge. I lowered my head as she laughed.

"In all your horniness you didn't even notice that I wasn't wearing anything under my skirt anymore."

Mckenzie was right. I hadn't notice. And the main reason why I should've noticed was because I was the one that had picked out and purchased her lingerie. Just another shameful job I was required to do alongside setting up her dates. She then reached into her purse and pulled out a rolled up piece of clothing that I immediately recognized.

A powder blue lace teddy.

I stood there in silence as she tossed it to me.

"Put it on."

Somehow, once again, Mckenzie has destroyed any fight I had left in me. I quickly and obediently removed my remaining clothes and began struggling to slip on the much too small for me lingerie. Even after loosening the straps around my shoulders as far as they could go (which I had reluctantly become an expert in), the lace fabric was still shoved so far up my butt cheeks.

Mckenzie giggled as I stood there in the moonlight of my apartment in her teddy. I knew I must've looked ridiculous. And the worst part was that my erection was so obvious, pushing out against the light blue material. Every second I stood there felt like an hour. I was now painfully self-aware again that there was another man in my bedroom who could come out at any moment.

After a few more stressful moments of her just taking the view in, Mckenzie grasped my hard penis through the lingerie and began walking me towards the door. Without any hesitation, she swung the door open, exposing me to the empty hallway.

Silently, she pointed to the ground in front of the door. I didn't need any clarification on what she meant. She then tossed my t-shirt and mesh shorts into the hallway and slammed the door shut.

---

So here I was, still sitting in front of my door, and still listening to Mckenzie having sex behind it.

My internal clock guessed I had now crossed the forty minute mark in sitting there. Usually by this point Mckenzie would've already had cum, typically more than once, and they'd be winding down, but tonight they were still going strong. In fact, her satisfied moans were only getting louder. My fingers were crossed as I looked back down the empty hallway, hoping my luck would last just a few more minutes.

Noises from the elevator grabbed my attention. It was coming up from the lobby. I closed my eyes and held my breath once more. I only needed ten more minutes.

*Ding*

My stomach dropped. I could hear the elevator doors begin to open.

Two perky voices echoed down the hallway. I wanted to scream. Anyone but Paige and Nikki again.

I bowed my head in resignation as the two sets of heels of my next door neighbors made their way closer and closer just as Mckenzie's cries were coming to an apex. Any second now and the girls would turn the corner and see me pathetically sitting there. I braced myself for the worst.

Suddenly, the clicking of their heels stopped.

"Oh my god, Nikki! Do you hear that? Is he getting laid in there?!"

I cringed as Paige's voice rung out. Nikki's voice teased her in response.

"Ah! Are you jealous? I seem to remember someone having a little crush at one point!"

I began to blush. I couldn't believe Paige used to have a crush on me given I was sure she now knew me as just a cucked little sissy. Flashbacks of being locked out of my room only wearing a bunny costume zoomed through my mind. I closed my eyes in dread.

Two loud squeals confirmed the inevitable and I eventually forced my eyes back open. There, standing above me, were Paige and Nikki, both whispering and laughing to each other. I could read Nikki's lips say to Paige something along the lines of 'That makes a lot more sense.'

And of course they were absolutely stunning. Both of the girls looked as if they were coming from work functions. Paige glowed in an emerald green silk blouse that was tucked into a short and tight pencil skirt. Her tan legs and fit body popped out of the outfit. Nikki wore a cream colored pair of pants that accentuated her shapely butt with a matching cream blazer.

Even though neither girl was particularly tall, I felt incredibly tiny as they stood over in their heels. That familiar combination of shame and arousal began to fill my cheeks and my penis as Mckenzie's moans became impossible to ignore. To make it even worse, the man's grunts were also now audible through the wall. There went any chance I could pretend Mckenzie was alone.

Paige and Nikki silently looked down at me with amused smiles on their faces as we listened to Mckenzie and her lover quite obviously cum. By the time their voices had finally died down, my face was bright pink and my penis was back to being rock hard.

The awkward silence was finally broken by Paige who now had her hand covering her mouth to stifle a laugh.

"So...um... are you just, like, listening to them have sex?"

Nikki joined in, "...in your own apartment?"

A thousand responses flashed through my mind and none of them seemed any good. Maybe I could make it sound like we were swingers or something? I knew it was desperate, but it was a last ditch effort to save some pride. I tried my best to speak with confidence.

"Hey! I know this seems a little weird, but the two of us have an arrangement where we can both, um, have sex with others and, um.."

My voice was nearly quivering as I began to drift off. I knew I wasn't sounding very believable and judging by the girls' expressions, they didn't look very convinced.

"Really? Both of you?"

There was definitely some underlying sarcasm in Nikki's voice and Paige was still eyeing me suspiciously. All I could do was double down and meekly nod in response.

The girls smiled to each other and thankfully made their way to their apartment door. But just as they were about to step in, my door swung open.

And out stepped Mckenzie, wearing only the t-shirt belonging to the guy she just fucked.

She took another step into the hallway. The shirt barely made it's way past the bottom of her fit butt. I felt a pang in my stomach knowing she wasn't wearing any panties underneath.

Mckenzie looked towards Paige and Nikki for a moment and then nonchalantly tossed my phone and wallet in my direction. Before the girls could say anything, Mckenzie spoke up.

"He's staying the night. You'll need to get a hotel or something."

I couldn't believe she was being so direct in front of Paige and Nikki. Mckenzie then turned to them and smirked.

"Oh, hi girls. Is he bothering you?"

I couldn't do anything but just sit there and take the embarrassment. They both giggled to each other and shook their heads. I breathed a sigh of relief as Mckenzie began to step back towards the door.

Oddly Paige and Nikki hadn't moved yet. I glanced over towards them and caught eyes with Nikki. She gave me a small mischievous smile, turned towards Mckenzie, and pointed at her shirt. Fighting through a laugh, she spoke out.

"Did you, did you graduate school there, too? Paige and I are recent alums."

I looked up at Mckenzie's shirt and groaned. It was the logo of the local university. Without missing a beat, She responded right back.

"Oh, this? This belongs to the man I'm with in there. He's a student."

I felt myself shrink even further into the floor. Paige covered her mouth with her hand and Nikki flashed me a knowing smile. This was the opening she was looking for.

"So.. if you don't mind me asking, but both of you are just fine with each other having sex with other people?"

Mckenzie let out a laugh, "What makes you think we both do?"

Nikki pointed at me. I felt my stomach drop.

"He did. He said that the two of you had an 'arrangement'."

Mckenzie's devilish smirk returned. I knew I was in trouble.

"If by 'arrangement', you mean that he finds me dick to ride and then I tell him all about it afterwards, then you'd be right. I'm sure he was bragging to you girls how he meticulously planned my successful and, let's say, satisfying date tonight, right?"

All I could do was shudder as Mckenzie turned in my direction.

"I'm going to have to tell Brad about this."

My hands instinctively went to cover my poor butt cheeks.

I was too ashamed to look up at Paige and Nikki at this point but I could hear them whispering back and forth to each other. Paige, holding in a smile, finally chirped up.

"Is Brad..is Brad going to spank him again?"

I wanted to curl up into an even smaller ball on the floor as Mckenzie's smirk turned into a look of surprise.

"Again?"

Paige didn't hesitate, "Well...on Halloween, Nikki and I came back home from the club and he's sleeping outside his apartment because he was locked out. Actually not all that different than today. Except he's not dressed as an adorable pink bunny tonight."

I couldn't believe how casual their conversation about me sounded as Paige continued on.

"And since we're so nice, we offered him our couch to sleep on. Anyways, Nikki luckily noticed that, um, someone's bare ass happened to be just a little red..."

But right now my face felt even redder then my butt was that night. I couldn't bring myself to look up at the three girls cackling above me as memories from that evening flickered by...that god forsaken pink costume... Brad's intense spanking... waking up on the hallway floor...and that humiliating blowjob I gave Patrick after finally getting back into my apartment. Somehow that last part with Patrick seemed to be my only remaining secret.

Nikki piped up next, "So.. I just have to ask, what did he do that earned him a spanking?"

Mckenzie leaned over until she was face to face with me. Her icy, condescending smile gave me chills.

"Why don't you lift your head and answer her question? Let's pretend Brad was here. He'd want you to tell them the truth and be proud doing it."

I groaned to myself. That was such a lie. Brad literally got off on my humiliation, the less proud I was, the harder he got off. I reluctantly looked towards Paige and Nikki's amused faces and began to speak softly, tripping over my words.

"Umm, yeah, I guess, uh, you kind of know Brad now. Well, sometimes he, uh, wants Mckenzie... or me... to blow him."

My voice trembled as I watched Paige and Nikki react. Yet somehow the worst part was my own penis, rock hard and straining against my lingerie.

"And when Brad was away, I was supposed to practice giving blowjobs, and I didn't do what he said..."

Mckenzie gleefully nodded along as I struggled through each word.

"...so Brad spanked me as a punishment."

I couldn't believe that I was exposing myself to my neighbors like this. I also couldn't believe that they somehow even seemed a little into it. I could feel my penis stiffen again as they both gave me mock sympathy.

"Oh, don't feel too sorry for him," Mckenzie laughed as she turned to face me, "Why don't you tell them what happened during your punishment?"

I looked back at her in shock and began to stumble over my words. I desperately tried to catch eyes with her and shake my head, but Mckenzie's now firm expression told me I didn't have a choice but to answer.