When One Thing Leads to Another Ch. 04

So I've signed you up for a highly rated three-hour intensive blowjob class. You should be receiving the email confirmation shortly. And before you ask, the answer is 'Yes'. It will be an in-person class."

My stomach felt like I was on a roller-coaster drop. I began to plea.

"Brad, please no. I can't go to a public blowjob class. Anything else. Please. Please?"

His tone got angrier.

"What the fuck did we just talk about?! These are not suggestions!"

Even though he was behind a screen, I began to slink away.

"You will be going to this class. You will sit next to all the other slutty girls who want to learn how to suck cock. I'm sure there will even be a couple guys there, too. And most importantly, you'll be the best little enthusiastic student they've ever had."

A million scenarios of things going horribly wrong flashed in my mind. All I could get my body to do was silently nod.

"Fortunately for you, Mckenzie volunteered to take the class with you. See? This is what I'm talking about. This initiative is what I want from you.

Now your little outburst there doesn't put me at ease. So given that Mckenzie here is so much more advanced, you'll be sending her daily updates on how your blowjob practices are going."

Mckenzie began to giggle, "Aww, I'm like your blowjob coach."

The familiar combination of arousal and shame flew through my body. My cock was now beginning to create a tent in my black panties. Brad's voice soon broke the silence again.

"Mckenzie is already aware but unfortunately my work will be keeping me quite busy in London for the foreseeable future. Therefore it'll be some time before I'm able to fly back here."

Finally, some relief. This was the first piece of good news yet today.

"Because of that, your girlfriend and I had a long talk about your... let's call it... your 'sexual inadequacies', in regards to both your size and your stamina, and it would be just so unfair to her if she was only stuck with your penis while I'm away."

I could barely look at the screen I was so embarrassed, but I couldn't face myself to look down either and see my now completely erect penis.

"It's a good thing I'm not a jealous man so maybe you can think of this as a thank you to Mckenzie for being your new 'blowjob coach,'" Brad laughed, "But it'll now be your personal job to make sure she's getting sexually satisfied by as many men as she wants."

I could see Mckenzie beaming in Brad's arms. I wanted to cry as Brad continued to laugh.

"That means you'll basically be the little secretary for her pussy. You'll manage her dating apps, being a sexy flirt with every hot man who swipes in her direction. You'll get phone numbers from these hot men, you'll plan out cute dates with these hot men, and you'll even gladly accept dick pics from these hot men."

Mckenzie's face continued to shimmer as Brad described the ways I'd be forced to find her great sex. My penis was now straining against my panties, threatening to rip through the fabric.

"And of course you'll be just as enthusiastic with this as you will be at your blowjob class," Brad said as his eyes pierced my screen.

"Now one last thing, let me see the marks from your punishment."

I could barely speak at this point. On top of that, there'd be no hiding that I was still wearing panties and that I was hard as a rock. It wasn't until Brad cleared his throat that I awkwardly positioned my camera behind me, exposing my sore and red pantied-cheeks.

I closed my eyes as their laughs echoed through the phone. Brad spoke one last time.

"Mckenzie is going to send you a couple lotions you need to pick up in order to moisturize and repair that redness. This is important as I'm sure you know that you'll earn more spankings in the future. Send her a pic when you buy them.

And since you like these panties so much, pick up more pairs while you're out shopping. You'll obviously keep those on for the trip.

Now lastly, look at me and tell me the truth. You're so hard right now, aren't you?"

Brad and Mckenzie didn't even need my nod for confirmation given how red my face was.

"Of course you are." Brad said smugly as he hung up the phone.

My room was once again silent as I slowly took in everything from the call. I couldn't see an end in sight. Every day moving forward would require me to debase myself in front of Mckenzie in some new creative way.

Oddly, neither of them had brought up Patrick. But I didn't have time to worry about that yet.

*Bzzzz Bzzzz Bzzzz Bzzzz*

I couldn't believe they were fucking again. All of a sudden, I needed to get out of the apartment and get some fresh air. At least this was an excuse to pick up the lotions and panties Brad demanded me to get. I slipped on a shirt and put pair of sweatpants over my panties. I crossed my fingers and went out the door.

Although my extreme paranoia made it seem much worse, the shopping trip was fairly uneventful. There was nothing suspicious about a guy picking up lotions and a set of black panties. But even still, I could've sworn the attractive middle-aged woman scanning 'the panty purchase for my girlfriend' gave me a knowing look. I just knew the young saleswoman was hiding a grin as she pointed out lotions around the store. It wasn't until after I sent Mckenzie the required pictures that it all made more sense. I quickly received texts back.

-----

MCKENZIE

good work on the creams! your butt cheeks will thank you!!

panties = borrrrring, but at least you got them

now make sure to keep an eye out for the dildo in the mail..

ps - it looks like someone forgot to take off their pink collar from last night ;)

-----

It only took three days for the Brad's dildo to arrive. My constant checking for the package was pointless as Mckenzie had 'accidently' shipped it directly to Paige's apartment once again. This time the girls just left the opened package in front of my door for anyone to see. They didn't even bother to hide that they read the damning note Mckenzie had left inside.

The dildo was somehow worse than I imagined. It actually was a nearly identical replica of Brad's impressive cock. Not only that, his larger than average balls were included as well. Behind the balls was a suction cup that seemed to grip everything. The worst part, though, was the color.

It was hot pink.

Also, the packaging made it very clear exactly what it was, it was a custom made dildo. They even included a matching hot pink stick of lipstick and the color images of the pictures Mckenzie submitted of Brad's erect cock which Paige, Nikki, and Erin had all now likely seen. And if that wasn't clear enough, Mckenzie's note left no question of whose cock it was and why I needed to practice sucking it.

I waited until almost midnight to send Mckenzie the confirmation text that I had received the dildo in hopes that she'd already be asleep. My heart sank as my phone immediately received a video call from her.

The next hour was one of the longest hours of my life. Mckenzie constantly spoke down to me as if I was just a horny eighteen year old trying to impress her prom date. She repremanded me when I forgot to put on lipstick (Brad's rule!) and teased me when the penis got inevitably hard. She loved to remind me of all the things she had coerced me to do. She even made me take handwritten notes on blowjob techniques.

By the time Mckenzie's 'class' was over, I had not a shred of pride left. And we hadn't even moved past sucking on the head of the penis. A full hour of just kneeling and swirling my tongue. My entire body was screaming 'no' as I profusely thanked her for the lesson. I just knew I'd be punished if I didn't.

And that's just how my days began to go.

Usually once a day, typically right after work, Mckenzie would call and my blowjob 'lessons' would begin. I soon became an expert in positioning my phone's camera so Mckenzie could watch from the best angles. As much as I hated to admit it, several of the tongue motions had become muscle memory. My hot pink lipstick was soon getting put on perfectly every time. It was only deep throating that there was no improvement in.

As mortifying as my blowjob 'lessons' were, I still couldn't bring myself to search for guys to fuck Mckenzie. I tried to avoid it but she quickly began to bring it up regularly. By our third lesson she had already sent me her favorite photos of herself to use on the dating apps. The longer I dragged my feet, the more humiliating Mckenzie's lessons would become.

She'd make me place the suction cup of the dildo on a mirror so I'd have to stare at myself as I practiced. I'd be forced to lay in uncomfortable positions, my entire mouth just wrapped around the balls. She'd give me homework. I'd spend entire lessons only in panties. Sometimes she wouldn't do anything at all, and for the entire hour I'd just simply have to suck. And like clockwork, she'd mercilessly tease when my penis started getting hard. Every time.

It wasn't long before I gave in. I sheepishly downloaded an app and began setting up her profile. Just looking at the sexy photos Mckenzie has chosen would bring feelings of jealousy. Eventually, Mckenzie's profile was completed. I could barely look at it. If I wasn't already, I was now officially her cuck. And now I had find her men to satisfy her.

After hovering over for what seemed like an eternity, I finally pressed the button to have the profile go live. It was so emasculating swiping through all these men's profiles being forced to think who Mckenzie's type would be. It wasn't long before a man returned the swipe and a conversation box opened up.

I had only a vague idea if the man was attractive or not but he was shirtless a lot in his pictures with very defined muscles. I pathetically thought Mckenzie would like that. I couldn't stop blushing. I was going through a man's photos, checking him out. This was soon interupted by the conversation window coming back up.

He was now aggressively flirting with me. I felt like throwing up. I couldn't believe I was now preparing Mckenzie to get fucked. Fortunately, the man wanted to grab a drink that evening. I picked a place and time and I began working up the nerve to tell Mckenzie.

She was ecstatic. I reluctantly showed her his photes which, to my dismay, she thoroughly enjoyed. That night I stayed in. and I did my best to distract myself. Soon after, though, my phone began to ring. It was a video chat from Mckenzie.

That's when I knew I was fucked. The date had gone terrible and she was livid. She began absolutely furious when she found out he was the first and only person I matched her with so far. But it wasn't until she brought up telling Brad that I got really concerned.

I was soon filled with anxiety over what Brad's punishment for me would be. As I nervously waited, I bit my tongue and tried my best to find Mckenzie proper matches. I looked for common interests. I googled how to flirt like a girl. I even embarrassingly spent time staring at her prospective men's bulges to make sure they would measure up. I finally put my ego aside and set her up with a man I genuinely thought would fuck her right that weekend.

It wasn't until I told Mckenzie about her new date that she finally broke the news of what my punishment would be. First, though, I had to sell her on the new man. I blushed as I described his muscular back and shoulders and his lucrative profession. I winced inside as I zoomed in on a tight bathing suit photo that showed off an impressive bulge. I could tell she was excited. It was soon after that she explained how I'd be punished.

While Mckenzie would be on her date, I'd be required to go to her apartment and get it ready in case she brought the man home. That would include a full cleaning and any other favors she requested while out on her date. All things considered, I was somewhat relieved. My hands reflexively covered my ass as memories of Brad's last painful punishment coursed through my head and bottom. I'd take this over that.

Like always, though, just as I was getting a tiny bit comfortable, the kick in the gut came. It was 6:27 pm when the email came in innocuously enough. In fact, I almost deleted it.

The Blowjob Class. It was a confirmation receipt.

My stomach dropped. This was actually real. I would be going to an intensive in-person class on how to give a man a blowjob. And it was this Saturday.

Not only that, Brad scheduled the class on the same day as Mckenzie's date. That meant that she'd have to go straight from the class to her date and I'd have go straight from the class to her apartment to clean. I needed to prepare for another long night..

The next day a package covered in overnight stickers from London was delivered to my apartment. Inside was another box and a short note from Brad.

"Don't open until Saturday morning."

All of a sudden I began to dread this weekend. It wasn't like I had been looking forward to it beforehand, but I had done a good job of blocking it. Out of sight. Out of mind. But now it was in sight, and very much in my mind.

I barely slept that night before. Scenario after scenario rolled by in my head, each one ending worse than the other. In some weird sense, that pink bunny costume provided me a disguise to hide behind. There was a peculiar confidence that came with being in a bold outfit like that, a confidence I did not have dressed like a boy anymore.

Still groggy, I was woken up to a simple winky face text from Mckenzie. I guess that was my cue to open the box Brad had sent. Inside the box was what I was privately expecting.

Lingerie.

The familiar combination of humiliation and arousal trickled in as my hand grazed the high end fabric. Also included within the box was another note from Brad, this one slightly longer.

"Wear the corset all day. You'll wear this before you leave. Including tonight. Make sure everything is shaved."

Embarrassing memories flashed in my mind of the last time I was told to shave myself like this. I still had quite some time before the class but I remembered that shaving took forever last time. I gave a small groan as I looked at my body. My hair had been finally growing back from last time.

Thankfully this time was much easier than last. I still had less hair and I already knew the awkward positions I'd need to get in. The only thing worse this time was that my penis had already gotten hard even before I made it into the shower. I also still had the moisturizer products Mckenzie gave me last time for afterwards.

Ugh, the corset, though. I was just thankful I hadn't thrown it away. I had no idea how to put it on. Last time Mckenzie had done it. Only after watching several tutorials online was I was able to tighten it enough to Brad's liking. I did my best to distract myself throughout the day but the corset provided a constant reminder of what I had to look forward to. Eventually the afternoon came and I made my way over to the box of lingerie.

The entire set was lavender with an occasional white trim. There were multiple pieces to it with intricate sections of both lace and satin. I first pulled out the panties. I could feel my penis stir as I reached for them. I slipped them up my smooth legs, giving me goosebumps along the way. The fabric nestled up between my cheeks and tucked my now mostly erect cock in.

I pulled out the stockings next. The tops of them were the same lavender color as the rest of the lingerie, but the rest was a softer purple. If the panties only gave me goosebumps, the stockings gave me full chills against my newly shaved legs.

Next was the bra, but my corset would need to come off first. Fortunately it was much easier to take off than it was to put on and I could finally take deep breaths again. Hesitation came over my body as I began to put on the bra. I shivered thinking about how badly Mckenzie's bra had chafed my shoulders. I grimaced thinking of the pain. Thankfully the satin fabric on this bra was so much more comfortable. It also actually fit.

The last item I hadn't been required to wear before, but I unfortunately already knew what it was. The matching lavender garter belt had four straps that I knew were supposed to hook on to my stockings. I grew perplexed when a closer look at the clasps seemed to show a tiny amount of glue on the straps but I soon realized that meant Brad wanted the straps to be that exact length.

I held the dainty material up. I didn't think there was any chance this could fit around my waist. After unclipping the hook, I wrapped the top of the fabric around my belly button. The material was surpringly stretchy I was just barely able to clasp it around me after sucking in my stomach a little bit. I hated to admit it but the corset training all day had helped as well. I sighed as my penis formed a tent in the panties below me.

The final piece was hooking the garter straps to the stockings. All four straps had fallen to the perfect height, just above the top of the stockings. Brad had obviously planned this out perfectly. It took a frustrating amount of trial and error, but I was eventually able to clasp the four straps to the stockings. For a moment, relief came over me.

Unlike last time, though, I had absolutely no desire to see myself like this. I immediately threw on a pair a jeans, a t-shirt, and a light jacket. Since I knew I'd end up at Mckenzie's apartment, I debated bringing Patrick's jacket to give to Corrie. I ultimately decided against it. I didn't want to bring any additional attention to what happened between Patrick and me.

I was almost glad that I was cutting it close on time because it gave me little chance to dwell on where I was going. I did a final check to make sure that none of the lingerie was showing and I was soon out the door.

-----

And here I was.

For a kinky blowjob class, it was being held in a pretty unimposing room within a regular looking building right in the heart of the city. I had made eye contact with noone in the building on my way up in fear that they'd know which room I was heading to. I took a deep breath and walked through the door.

My rush to not be late had actually made me a few minutes early so the room was still mostly empty when I arrived, the 'instructor' included. There were about a dozen or so seats arranged in a typical classroom layout facing a large desk with a whiteboard behind it. Unlike a typical classroom layout, though, on top of each desk was a box of tissues, a bottle of water, and a small collection of phallic shaped objects. I looked around the room.

There was Mckenzie. In the front row.

She gave me an enthusiastic wave as I resigned myself to the front row seat next to her. She immediately began pulling my jacket off and soon just a t-shirt and jeans were covering my lingerie.

I glanced around the room. The jury was still out on whether this was better or worse than I expected. On the plus side, the size of the class was somewhat small. On the negative side, the collection of items on my desk staring me down was intense.

So far the other people taking the class were keeping to themselves. As I expected, the class was mostly girls. Even still, not being the only guy gave me some relief. Although the others did look to be in relationships with each other. I glanced at Mckenzie. I had a feeling I'd be the only guy there with a girl he'd had a relationship with.

The ages varied as well. There was a small group of college girls loudly gossiping behind me, but also a couple of attractive middle-aged women who seemed to be on a girls night out. Luckily, I knew no one.

Soon a loud pair of heels entered the room and a stunning figure walked towards the front of the room. My eyes were captivated as the tall and thin woman emptied her bag on the large desk. For someone who taught blowjob classes, our instructor seemed to take it seriously. She was dressed as if she just left the office, wearing a tight black pencil skirt and a stark white sleeveless blouse. Her power outfit was complemented by a pair of pink framed glasses that shaped her attractive face.