When One Thing Leads to Another Ch. 05

"I....um, I....cummed myself during it."

Excited squeals from Paige and Nikki echoed again through the hallway, and I didn't know what to say next. Defending myself seemed useless. What could I possibly say that could save face? Trying to explain 'Well, it wasn't just the spanking that made me cum, it was the butt plug, the outfit, and Brad's thighs, too' only sounded more emasculating.

Nikki could barely contain herself, "Oh my god, I have SO many questions."

Paige's reaction was more subdued as she took in my confession. A sly smile crept onto her pretty face as she joined in on the teasing.

"Just wow, I had no idea you were so kinky. So now I just have to ask... how amazing must Brad's cock be to turn you into such a little slut for him?"

I was speechless as I looked up at the three girls. I had never heard Paige talk like this before. Before I could get anything to come out of my mouth, Mckenzie interjected.

"Oh girls, you don't even know. He's acting all coy and shy now, but you should see how desperate he is for it in private."

I could see that evil glint in Mckenzie's eye as she turned to me and shamelessly continued on.

"Why don't you go show them what Brad's dick is like? Go inside and grab your best friend that you use to practice giving him blowjobs with."

She couldn't be serious. There's no way she actually expected me to bring out the pink dildo molded as Brad's cock they bought for me and ordered me to practice with. There was literally a man in my apartment that she had just fucked. But I also knew that I had no choice.

I tried my best to keep the fabric of my lingerie from popping out when I stood up and slowly trudged my way to the door. I could still feel all three sets of eyes judging me as I fumbled with my keys in the door. After what felt like minutes, the key finally turned and I stepped in.

Even though I was now in my own apartment, I had never felt less comfortable in it. I cringed knowing the dildo was in a bathroom drawer and I'd have walk past my bedroom door where another man lay who had made it his. I could only keep my head down as I entered the bathroom and found what I was looking for.

There, sitting in a matching hot pink satin bag, was my as Mckenzie put it, my 'new best friend'. At this point I had spent countless hours sucking every inch of it, with many of those hours under her supervision. To make matters even worse, my penis involuntarily stiffened again as I picked it up. Per usual.

As I speed-walked out of the bathroom, I couldn't help but glance into my partially opened bedroom door. All I could make out was a large naked leg hanging over the side of my bed. I grimaced and kept moving. Suddenly, his deep voice rung out.

"Cuck, Stop."

I froze as his footsteps make their way towards me. My bedroom door swung open and his naked body now filled up the doorframe. It was impossible not to notice his much-larger-than-mine cock swinging below his well sculpted body. Intrusive thoughts and images of Mckenzie riding it made their way through my mind.

"Eyes up here," the cocky college fuckboy commanded as he smirked at me, "And tell your girl I'm ready for another round."

I simply nodded in shame as he made his way back into my room. I couldn't believe that I was being spoken down to by this douchebag in my own apartment, let alone that I was just caught staring at another man's dick.

As I reached my door to the hallway, I could still hear Mckenzie casually chatting about her new sex life to Paige and Nikki. Mckenzie was explaining the benefits of having me plan out her dates, especially with the story of the missing students in the news.

"You'd never believe it, but he's like my personal secretary, the way he manages my dating apps," I could hear Mckenzie say.

Paige and Nikki sounded thoroughly entertained as she went on describing the demeaning things I would do to help her get laid. I wondered if they could lose any more respect for me. The pink satin bag in my hand told me they could. Suddenly, the voice growled from my room.

"The fuck are you waiting for?"

I scurried through the door and back into the hallway. Somehow I was already submissive to that jerk. But in my rush to get out, I had completely forgotten how ridiculous I looked holding a pink satin bag shaped like a dildo. To make matters worse, my shaking hands fumbled it as I attempted to open the bag, causing the dildo to fall and bounce towards the girl's feet.

Without thinking, I scrambled to pick them up but I immediately knew I screwed up. Mckenzie's lace teddy was unmistakably exposed. I carefully shuffled my way over to the wall, hoping to mitigate the damage. But it was already done. Even with my head down, I could tell Paige and Nikki were whispering to each other. They didn't leave me in suspense for long.

"So... nice panties," Nikki choked out through a muffled laugh.

Before I could open my mouth, Mckenzie nearly shouted, "Wait! You're wearing panties right now?! I have to see!"

I was horny, embarrassed, and now, a little perplexed. Of course she knew I was wearing panties, she told me to wear them! But then it dawned on me, she was faking acting surprised to humiliate me even more.

And it was working. Both Paige and Nikki were looking incredulously at me. I desperately mouthed the word 'no' to Mckenzie and shook my head but her stern look in response told me I had no choice. I had resigned myself to the fact I'd be exposing my lingerie, but I couldn't let them see my shame boner.

With my eyes closed, I turned away from the three of them and slowly lowered my shorts and lifted the back of my shirt. All I could do was wince as their catcalls filled the hallway. At least Mckenzie didn't make me turn around, but she was continuing her surprised act.

"Ohmygod, that's mine! I literally got fucked in it tonight! Is that what took you so long when you went in there? You needed to slip on my used lingerie?"

I wanted to yell at the top of my lungs and defend myself but there was no point. I could only look up at them and meekly nod. They already knew I was Mckenzie and Brad's little sissy cuckold anyway. Why would it matter much?

Mckenzie's voice softened but still contained that mocking undertone, "Oh baby, if you really want to wear my panties, you can just ask me. I can even take you shopping for more of your own."

The worst of it was that her teasing had reminded me of what her man in my bedroom had told me to tell her. And I knew I'd end up in much more trouble if I didn't relay that to Mckenzie. I took a deep breath and repeated the info, but my words came out more as a barely audible mumble.

"Yourloverintherewantstoseeyou."

Mckenzie's lips curled into a smile as spoke, "What was that? Speak up."

Through gritted teeth, I forced the words out again, "Your lover in my room, he wants to see you.. wants to have sex with you again."

Both Paige and Nikki both squealed at this, making it even more painful. Nikki even called out to Mckenzie, "You lucky girl!"

Mckenzie played it off, "Oh, you girls are the lucky ones. These younger guys have so much stamina."

She then turned to me, "Well, I better not keep him waiting long."

Her voice then lowered to a whisper as she pulled her lips to my ear, "You're actually the lucky one that I didn't make you show off your tiny boner in your cute little lingerie to the girls. I just know you're hard as a rock right now, right?"

It wouldn't have even mattered if she could see the outline of my erection poking into my lingerie since my blushing face had already given it away.

"And by the way, you left your phone next to the bed. Let's just say we recorded you some videos on it that I expect you to be watching tonight. And I want you to think about what Brad fucking you will be like while you do."

There was no pride left in me as I obediently agreed. For a moment, her voice got softer.

"Tonight was so hot, and my date was perfect.. I love how wet this makes both of us."

Mckenzie's attention now diverted towards Nikki and Paige, "Well goodnight girls, I obviously have to go now."

The three shared a laugh as Mckenzie went on, "By the way, she makes an excellent maid if you need your apartment cleaned."

Paige giggled back, "Really?"

Did Mckenzie really need to expose absolutely everything? And ugh, 'she'.

"Oh, such an amazing maid. Just ask my roommates. Besides, she still owes you from that night you let her sleep on your couch. And she'll wear whatever outfit you'd want her to wear."

Flashes of being forced to clean Mckenzie's apartment while she was on a date in front of her two roommates, Corrie and Lydia, flew through my mind. They'd never look at me the same. Just like Paige and Nikki wouldn't either now.

The two girls' half jokingly weighed Mckenzie's proposal.

Nikki responded with a smirk, "We'll, we are having a bunch with the girls from our sorority over in a few weeks for a reunion. Maybe we'll have to take 'her' up on it."

I outwardly cringed as she placed a special emphasis on 'her', but underneath my lingerie, my penis was straining at the thought of being Paige's maid.

It was then that finally, just finally, Mckenzie waved goodbye and turned back towards my door.

She gave me a sly look over her shoulder and lifted up her shirt, showing off her perfect butt. That was the last image of her I saw before the door slammed shut behind her.

Nikki began to head towards her door as well, but not before giving me one quick amused look. Surprisingly though, Paige stayed behind in the hallway. Her eyes looked me up and down one final time before giving me a naughty glance. In one motion, Paige hiked up her pencil skirt, revealing both her tan upper thighs and a light blue thong that split her fit cheeks, before she chuckled.

"Our panties match."

My poor cock gave one last cry for attention at the sight and just like that, her door was shut and I was once again alone in the hallway. Well, just me and this godawful bright pink dildo.

-----

The next morning couldn't have come soon enough. It had been a horny and restless night in the hotel room and I just needed to get back to my own bed, even if another man had been in it the night before. After leaving my apartment, I was luckily able to book a last minute room at a decent rate not far from my apartment. At least something had gone my way. It didn't make me feel any less embarrassed when I showed up at the front desk only carrying a pink satin bag, though.

And I was still wearing Mckenzie's powder blue teddy underneath my shorts and t-shirt. There was chafing all over my body at this point from it, especially on my shoulders and my butt where the fabric pulled the tightest. When Mckenzie said she recorded 'some videos' on my phone, she might as well just told me the entire night was on it. At least that's what it felt like. Some of the highlights (or lowlights) included:

- Mckenzie's POV view of her unbuckling his jeans and pulling out his cock while laying on top of my bed.

- A close up of Mckenzie opening and putting a large condom on his cock while simultaneously stroking it.

- The naked upper body of Mckenzie as she bounced up and down on top of him (This was by far the least difficult to watch).

- Several photos of the two of them the following morning fooling around in my shower.

- My new phone background was a zoomed in crystal clear image of Brad's large cock. I knew better than to change it.

Not only that, but Mckenzie had also sent me a video from the club bathroom stall taken on her phone. It contained Mckenzie getting fucked from behind over the sink by that douchebag college kid in front of a mirror. I had watched while he pulled off the condom and began cumming all over the back of her powder blue teddy.

The same teddy I was still wearing.

And the same teddy that I had exposed my butt and back to the night before to Paige and Nikki.

I shook my head as a new wave of humiliation flooded over me at the thought. All I needed was to make it home and I was finally coming up to my building. As I passed through the lobby, I noticed a half opened package leaning up near the mailboxes. I groaned when I noticed my apartment number written on the side. The London return address already confirmed it was from Brad.

Ugh, someone had definitely sorted through the box already, too. Unlike the past packages for me that Mckenzie and Brad would 'accidentally' send to Paige and Nikki's room, though, this one actually had my correct apartment number on it. I guess that wouldn't stop the girls from sneaking a peak anymore.

I did my best to avoid looking at it as I carried it into the elevator and towards my door. I could already see a note written in Brad's handwriting. Oddly, for as much control as he currently had over my life, I hadn't seen Brad in quite some time. He said his job was keeping him busy and he was right. In fact, the last time I was with him in person was after the Halloween party, and I obviously remembered how that ended. Although him being busy sure didn't stop him from setting rules around Mckenzie and my sex lives.

Even though Mckenzie and her lover were gone when I opened my door, the unmistakable smell of sex still permeated the air. All I could do was grimace at the condom wrappers littered near my bed and the damp towels lying out in front of my shower. Although I was dreading it, I knew it be in my best interest to open the package sooner than later. Putting these things off had always led to worse consequences and punishments.

Within the package were three smaller boxes, along with the note. The first I immediately recognized as being from a high end lingerie company and opening it up confirmed it. Inside was an exquisite stark white set, with stockings included. It wasn't lost on me what that color typically symbolized. Suddenly, my stomach tensed up when I saw the contents of the second box.

It was an anal training kit.

Inside were multiple dildos, each getting progressively wider and deeper. And of course they all had to be hot pink, matching the dildo I already owned.

What was I expecting, though? There'd be no way I could just take Brad's cock (and maybe even, I'd reluctantly admit, enjoy it) without practicing with something smaller. Even the butt plug I had worn before couldn't capture having a real man's dick inside of me. Just the thought of it made me both shiver and horny.

The third box, however, just brought disappointment. It was a cock cage. And like everything else they bought for me, it was extremely well made. Through every ordeal I had been through so far, Brad and Mckenzie had never taken away my ability to cum. In fact, I knew they both enjoyed it when I would cum and immediately regret it.

Something about losing this freedom felt like a step too far. I knew I couldn't dwell on it, though. Mckenzie could've seen the package when she left this morning. Also, if Nikki and Paige really did sift through it, they could've told Mckenzie, especially now that they were 'such best friends'. In any case, Brad would know that it was delivered and the clock would be ticking.

I knew I could always say no if I really wanted to. Having Brad inside me both scared and thrilled me at the same time. I couldn't believe how far away and how close the night I first met Brad as Mckenzie's wedding date felt. I'd never believe then that I'd be truly considering getting fucked by a man while wearing sexy lingerie in front of Mckenzie right now.

All I knew was that I had to make a decision quick. I even debated if I should jerk off one last time first. Eventually I felt that I could always back out if I wanted. Intentionally trying to give it as little thought as possible, I washed everything, including myself, and clicked the cage into place.

A moment went by.

I immediately regretted it.

The weight of what I just did was dawning on me. In a last ditch effort, I searched the package for the key but I knew better. Brad wouldn't have sent it with one. All I could find were instructions on how to clean the cage while it was being worn. I bowed my head in defeat.

Last but not least, I pulled out the note from Brad from the package. It was simply a location (a very high-end hotel downtown), a time (8:00 pm), and a date (three weeks from now).

21 days.

21 days, I'd have to wait, at the very minimum, for me to be able to cum. I couldn't think of a period I had even gone even half that amount of time since I had first begun jerking off. I knew I wasn't done yet. I grabbed my phone, took a close up photo of my poor locked away cock, and forwarded to my group chat with Mckenzie and Brad.

All I got in response was a laughing emoji from Mckenzie. No acknowledgement whatsoever from Brad.

Day #1: My anger with the entire situation had given me a sense of confidence. Even just for myself, I wanted to prove I could say no to Brad's cock if I wanted to.

Day #2: It wasn't until I went to sleep that night the first issues began creeping up. I was woken up by my semi-hard penis pressed up against the cage. I squirmed a bit but was finally about to fall back asleep.

Day #5: Things were really beginning to get more difficult. At least two to three times a day my cock would strain up against its prison. All the box it came in contained was instructions on how to wash it properly.

Day #7: I was getting worried. I could notice my brain getting subconsciously more horny, it wasn't used to going this long without release. Women I passed, both on the street and on advertisements, were suddenly more attractive. The smallest triggers would remind me of my locked up penis. I'd wake up at least once a night.

Day #10: Today was an important decision day. I had pushed it off as long as I could but I knew I needed to begin training my ass with the kit Brad had sent me. Given my current state, part of me was now even looking forward to it.

I took out the smallest of the five dildos. Like the other four, it had a base like a butt plug, but it went deeper and maintained its thickness longer than a butt plug did. Compared to the previous toys that had unfortunately been up me, it contained more similarities to the toy Mckenzie had used on me rather than the vibrating plug Brad had ordered me to put in.

These humiliating memories inevitably caused my penis to press up against its cage. The straining had only gotten worse as I lubed up the dildo and slowly began to insert it into my butt.

Even though my ass hadn't been played with since that night with Mckenzie, my hole easily swallowed the toy. The unique, but familiar anal sensations flooded my senses. Maybe it was due to not cumming in so long, but everything felt completely amplified. I ultimately needed to stop because my penis pressing against the cage became too painful.

Day #11: I needed to take a day off after getting self-conscious from enjoying myself too much the day before.

Day #12: I practiced with dildo number two. Like the first one, I could take it without much issue. And also like the first one, I began to become so unbelievably turned on as I played with it. This time my cock finally went soft at one point with the toy still in me.

Day #14: The days felt like they were getting longer and longer. At this point, I was always just a little horny and I kept catching myself actually looking forward to my anal training sessions.

Day #15: I was able to take the third dildo. Even though my body was so aroused, my penis didn't even bother getting hard as I slowly inserted and removed the toy.

Day #16: My body slept through the night without my straining penis waking me up. It felt like my brain was slowly getting reprogrammed to anticipate these new sensations. Somehow, thoughts of Brad fucking me were actually beginning to feel desirable.