When One Thing Leads to Another Ch. 05

Day #17: All I could think about was being penetrated. For nearly forty frustrating minutes, I played with myself using the fourth dildo to no release.

Day #19: For as horny as I was, it felt like my penis had officially given up. My body's new sexual pleasure center had officially become my ass.

Day #20: With embarrassed pride, I was finally able to fully take the largest training dildo. Once again, it ended in frustration and I became desperate for Brad's cock in me.

Day #21: I knew I needed to give myself a day off to prepare for Brad the next day but that didn't make it go by any easier. My new phone background provided a regular reminder of Brad's dick and what I could expect the next day.

The cock cage had won. And it wasn't even close.

In only a few weeks the cage had made me obsess an unhealthy amount over another man's penis. I'd catch myself worrying over whether Brad would even want to fuck me. What had happened to me?

And the worst of it was that I was fully aware of what was happening every step of the way but there was nothing I could do to stop it. The effects of the cage started off slow but the pressure eventually wore down my defenses. I painfully had to watch as my body gradually betrayed me. Part of me hated it, but another part of me was so aroused and excited by it. It was only inevitable that the latter would win out...

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The night had finally come.

It was now six o'clock, two hours before I was supposed to meet Brad at his hotel room. I had no idea what to expect and he still hadn't even acknowledged the picture I had first sent him of my penis in the cage. In fact, neither him nor Mckenzie had said anything to me since then. But even still, I knew I needed to be at the hotel by 8:00 pm.

My completely shaved naked body stood over the expensive lingerie that Brad had purchased. I both dreaded and desired putting them on. On top was a delicately sewn white bustier with thin lines of pink etched into the design. Unlike the training corsets I'd been ordered to wear in the past, this fabric was much more elastic, allowing me to breathe while also fitting snug around my midsection. The stretchy material made its way pass my belly button and wrapped itself across my lower back. Dangling from the bottom of it were four garter straps.

As I lifted the dainty white panties from the box next, another note in Brad's handwriting tumbled out. Instructions were listed that contained more writing than the first note, but still went straight to the point.

"Wear the panties over the straps."

"Let the front desk know when you've arrived. They'll give you my room number."

The first rule would be easy. The second rule made me a little nervous but there was nothing I could do right now. So I focused on the first by putting on the stockings next. The matching white pair glided perfectly up my smooth legs, settling just below my two cheeks. I had reluctantly become more efficient in attaching garters and soon all four had connected the stockings to my bustier.

Lastly, I slid up the delicate white panties, which fit perfectly over my caged penis. It didn't take me long to realize that wearing the panties over the straps meant that they were easily removable. I did have some difficulty choosing what to wear over the lingerie but I ultimately went with a simple dark shirt and a pair of jeans.

What I also decided was to bring Patrick's green jacket with me to give to Mckenzie. Since Patrick was hooking up with her roommate, Corrie, maybe I could get the jacket back to him that way. Initially I hoped to avoid including Mckenzie in it at all given the whole 'I gave Patrick a blowjob' part of it, but I had been holding onto the jacket for too long now. Maybe she wouldn't ask questions to why I had it? Also, once I discovered that I had accidentally grabbed that ID card from the floor of Patrick's car, it made it more important that I get that back to him. I threw the ID in Patrick's green jacket pocket and began making my way towards the hotel.

It was beginning to hit me what I was doing as my ride pulled up to the hotel. The constant state of arousal of my body had been disguising how crazy this all would've seemed to me just months before. Here I was, shaved smooth and in white lingerie, about to enter my male lover's hotel room for him to take my anal virginity. Also, Mckenzie, my girlfriend, would be there to watch.

I immediately became very self conscious as I walked inside the extravagant hotel. Every step brought another tug on my garter straps. The feeling would vibrate down my stockinged leg. Even under my shirt and Patrick's jacket, I was convinced everyone could see the straps from the bustier sticking out.

After wandering the massive lobby for a few moments, I took a deep breath and made my way towards the front desk where an attractive blonde woman in a business suit stood. Trying to sound as confident as possible, I firmly gave Brad's name. She smiled back at me before reaching into a drawer and handing me a small box.

"A gift from our guest for you."

I took a closer look at. It was a small container of bright red lipstick. My fake confidence instantly deflated and I knew my cheeks were now blushing in full view of the attendant. All I could do was lower my head and mutter a soft 'thank you' to her as she handed me the lipstick. I guess Brad needed to humiliate me one last time.

With a more amused smile on her face now, she gave me his suite number and pointed me to the elevators. I had assumed from the room number that it would be pretty high up, but based on the floors in the elevator bank, which his was already lit up for, Brad was literally on the top floor. I guess the new work he was doing was paying him well.

As the elevator went up, my phone began to vibrate. For the first time since I put on the cage, there was a message from Brad. As usual, it was directly to the point.

"Only be wearing your lingerie when you knock. Hurry up."

On one hand, I was almost relieved to see a message from him after so much silence. On the other hand, reality was setting in and I was now coming to terms with being completely exposed in a few moments. Also, my updated phone background of his naked body reminded me of what I should expect on the other side of the door.

Possibilities flooded my mind as the elevator continued up. One thing I hoped for was that it would only be Brad and Mckenzie in the suite. I was losing track of everyone who had seen this version of me. There was obviously Mckenzie's roommates, Corrie and Lydia, who got a front row view of me serving them in lingerie. Paige and Nikki were on the list now, too. So were Mandy and her friend Hailey, who got to enjoy watching Brad insert a butt plug in me. Lastly, I had almost forgotten, there was the man I ran into after the wedding in the stairwell when I was only in lingerie. Thankfully, I didn't have to see him the next day at brunch.

And ugh, Kristina. My ex. I couldn't even think of her without my face turning red. Surprisingly, Kristina had been relatively quiet since that night Mckenzie video-called her while I was in my compromised state. What she had done, though, was sign me up for messages from a panties company her friend owned. The regular alerts I received about lingerie sales served as daily reminders of what my jilted ex now had over me.

By the time I made it to his room, I still didn't have much of a plan. All I could find was a small unlocked room down the hallway with an ice machine in it. The door had a large window in it but this would have to do. Once I slipped in, the first thing I began to do was apply the lipstick. By now, I knew better. Also by now, I had reluctantly become an expert with applying it, even with speed. All I needed was the reflection in the glass.

Things were about to get trickier. After taking a final glimpse down the hallway, I quickly slipped out of my jacket and shoes. Goosebumps already covered my arms even before I lifted up my shirt, putting my lingerie on full display. Off went the pants and I immediately felt completely hyper-exposed. The cool hotel air conditioning was now making me shiver. After removing my valuables and stacking the clothes next to the ice machine, the moment had come. I didn't love leaving Patrick's jacket and ID out in the open, but I didn't really have a choice.

I peaked my head down the hall once more and scampered over to Brad's door.

Closing my eyes, I knocked...

...and nothing.

I awkwardly stood there in the hallway while the seconds passed by like hours. As nervous as I was, I knew my chances of getting caught were lower than they were the night I had first met Brad and was ordered to be outside that hotel room wearing Mckenzie's panties. But even though there were only a couple suites on the floor and therefore less people, all it would take was one person to walk by. I swore I could hear increasing noises in the nearby stairwell.

Finally, what sounded like footsteps from inside the room made their way to the other side of the door. It swung open and there stood Mckenzie, looking as sexy as ever, only wearing a shower robe.

"I always knew you'd come! And you look soooo fucking hot right now."

My body flinched as her loud voice echoed down the hall. And she was right, I never stood a chance once that cage was on and locked.

As Mckenzie led me inside the massive suite, I looked around in awe. Floor to ceiling windows lined the walls and overlooked the city's skyline while avant-garde artwork decorated the interior. There was a closed set of ornate double doors on the far side of the room that Mckenzie brought me towards. I quickly determined that was Brad's bedroom and my stomach started doing somersaults.

That's where Brad was. And he was waiting to fuck me.

"We just had sex a little while ago," Mckenzie whispered while giggling in my ear, "I wanted him to last longer in you."

Without hesitation, she swung the two doors open. The dimmed light inside the bedroom required my eyes a moment to adjust, but I knew exactly who I was looking at. There, in his tight boxer briefs, laying on his bed, was Brad. His sculpted body was leaned up against the headboard, his body on top of the covers. Behind me, Mckenzie followed and closed the doors again.

It was silent for a moment as I took everything in. All I could bring myself to do was awkwardly wave my hand at him.

"Hi....Brad," I softly stammered out. I knew I sounded like a nervous girl in a bar meeting her crush. Brad's look remained indifferent as he lifted his hand and gave me the 'come here' signal.

My mind was on cruise control as I headed towards him, with my eyes sweeping across the room. Brad's bedroom was just as luxurious as the rest of the suite. He continued to beckon me towards him as I reached the front of the bed. Climbing on, I couldn't help but notice an enormous mirror on the wall facing the bed. For a moment I needed to stop and stare at myself. I still couldn't believe what Mckenzie and Brad had turned me in to.

As I crawled on the bed between his spread out legs, his hand signaled me to stop. For a moment, he simply looked me up and down. I could feel his eyes inspecting every inch of my body. He then reached his hand towards my panties and pushed the material to the side, exposing my small cock cage. I could see a slight grin cross his lips.

My heart began to race as I watched him reach towards the dresser and grab a key. Wait, was he actually going to unlock me? I had always hoped so but since no one had spoken to me after I put the cage on, I really had no idea. Without saying a word, Brad simply unlocked the cage, and just like that, I was free.

And nothing happened. Given how unbelievably horny I was, I was reluctantly expecting my penis to immediately get hard, like it always did when Brad and Mckenzie toyed with me. The tight cage had somehow made me look even smaller than usual. Brad pushed my panties back into place and finally spoke.

"So Mckenzie and I made a little bet with each other on if your little cock would spring up when I took it's cage off. She thought it would, but I knew better."

Mckenzie made her way over to the bed and slipped her dainty hand under my panties, squeezing everything underneath. Her cool fingers felt so good on my neglected penis and I was so incredibly turned on, but nothing was happening. I shuddered thinking that the cage maybe rewired my brain somehow. She chuckled as her hand slipped back out of the panties. Then all of a sudden, she pulled me close and gave me a deep passionate kiss. As she pulled away, she smiled at me and whispered 'thank you' in my ear.

I was eventually back in reality, though, and Brad was now pointing to his groin. I knew I needed to impress him, especially after what happened last time. All my blowjob lessons were for this moment. The worst part was is that I knew I would, Mckenzie had unwillingly made me a cock-sucking expert.

With closed eyes, I kicked off the foreplay by crawling between his legs and pressing my mouth against his boxer briefs. It wasn't difficult to make out the outline of Brad's thick, but currently soft, cock in them. After a few moments of teasing him through the fabric, I was able to pull his penis out of the flap using only my lips and tongue. I could faintly make out the taste and smell of Mckenzie's pussy as I sucked away.

Embarrassed pride returned as I began to feel his penis thickening in my mouth. Soon Brad's briefs were completely off and he was hard as a rock. After practicing on the hot pink replica version, it was weirdly refreshing to be sucking on the real thing. I tried to utilize as many of the techniques I had learned as possible. Even outside of impressing him, the closer I could get him to cumming, the quicker he'd fuck me.

I also knew that the real grading wouldn't come until I was deep throating him, something I failed miserably at last time. I proactively began pushing Brad's cock further and further back. My now nearly non-existent gag reflex easily let it pass each time. Soon his sixpack was pushed up against my face. Moaning noises were now coming from Brad above me.

My lips had now left a bright red ring around the base of his cock. My head bounced up and down while he gradually became more aggressive. Eventually, he was holding my head with his hands as he slowly face-fucked me. I didn't want to admit it, but this was now easy for me. I guess I really was a natural.

Brad finally pulled his dick out of my mouth for the last time and began putting lubricant on his fingers. I don't know why I thought I might get actual approval from Brad for my blowjob skills, but I got nothing. Maybe him not punishing me was approval enough.

Even though I was humiliated on so many levels (especially when I'd catch glimpses of myself in the mirror), I couldn't even describe the level of my horniness as Brad's lubricated finger began to push aside my panties and press against my shaved hole. An involuntary moan escaped my lips as the familiar feeling of an intruder made its way into my asshole. Mckenzie was now inches from me, studying my reaction as I rocked back and forth on Brad's finger. It wasn't long before a second finger of his joined in exploring me.

And just like that, they were out and Brad was putting lubricant over his large dick. After wiping and cleaning off his hands, he casually flipped me over on to my back. With one motion, he put a pillow underneath my lower back and swiftly pulled off my virginal white panties. Mckenzie was still watching me intently, but her fingers were now rubbing herself as she stared me down. This was only fueling my arousal even more. All my body wanted and craved right now was for Brad to be in me. As he lowered himself on me, he spoke.

"You have to ask."

My body didn't bother putting up a fight because there was nothing to fight. I needed Brad's cock. My words came out quietly, but firmly.

"Please.. please fuck me."

Mckenzie's gave a small squeal next to me as Brad continued to mount me. His well-built arms made their way around my legs and began to lift them. I was thankfully much more comfortable on my back than I was on all fours. My soft exposed penis was now resting on my belly. I closed my eyes as I awaited the tip to press against my eager ass.

And finally, it did.

With only a little push back, the head of Brad's cock began to expand my hole. Even though my eyes were closed, I could still make out Brad's figure over me, slowly lowering himself closer. My hole's resistance weakened as he pressed harder and soon his head popped itself in. I gave a reflexive squeak as his penis crossed the point of no return.

Compared to the training dildos, Brad's cock still bigger than the largest one I used, but not by much. I hated to admit it, but a real cock felt so much better than the cold, hard material of the dildo. A bit of nervousness made its way over my body as he pushed himself deeper and deeper into me. Could I actually take Brad's entire penis?

The answer came sooner than I thought. With a final push, I felt the base of his cock press itself against me. An involuntary moan forced its way out. Mckenzie's breathing intensified next to me as she continued to play with herself.

I had just lost my anal virginity.

I was now being fucked by another man.

It wasn't uncomfortable, but it wasn't very comfortable either. I was familiar with the feeling of being penetrated from the training dildos but was not ready for what it felt like to get penetrated. I was in control then, I wasn't now. Brad's movements were pressing his dick further inside of me, not my own.

My body needed to get used to it. My eyes were still closed tight as I braced myself for every thrust. Soon, though, I began to anticipate Brad's movements. Whether it was conscience or not, my body rocked itself alongside him. As embarrassed as I was, I no longer cared.

Even though I was acting like I wanted to get this over with, there had been a part of me that hoped I'd enjoy it. All I could fantasize about the last few days was Brad fucking me into oblivion after not having cummed in so long. I was finding something so sexy about being this submissive to another person. When he first entered me, I didn't actually think I would like it. Now I wasn't so sure.

As I bounced alongside Brad's thrusts, I was realizing that I had more control than I thought. My body naturally gravitated towards the pace and motion that gave it the most pleasure and so far Brad seemed content to move along with me. That feeling deep within me was beginning to bubble up again the longer I went.

I was soon in my own haze as I took in the sensations of getting fucked. I barely noticed when Brad held my hands down above my head. Or when my cock suddenly became rock hard. Or when I'd loudly moan with every thrust.

But suddenly it all stopped and Brad's voice grumbled out, "Get on all fours."

Without thinking, I blurted out, "No, just keep going!"

I immediately knew I made a mistake. Never say 'no' to Brad. A pang of nervousness hit me. I was going to be punished for that. Brad's stern voice confirmed it for me.

"What did you just say to me?"

I began to stumble over my apology as Mckenzie giggled next to me. Brad then forcibly grabbed the back of my bustier and flipped it over, bringing me with it. I suddenly felt so pathetic as he manipulated me around by my lingerie. I was now in the face down, ass up position. I was also now a little worried, especially once Brad's voice rung out.

"Was someone beginning to enjoy themselves too much? Did someone forget who they were talking to?"

Brad's cock was back inside me again. The new position I was in had completely taken me out of what was becoming my comfort zone. Now I was completely at the mercy of Brad again, just how he intended. His voice continued to pick up.