Caught by My Boss Pt. 03

I was walking out of the building and once again ran into the overnight security guard, a man I had seen more and more of lately as my escapades with Derick lasted longer after work hours. I gave him a brief nod which he returned with what I thought was a wink. Did I see that right? Either way, I was rushing through my walk of shame from work to my car as usual and had no interest in stopping so I kept my pace up and my head down.

Once home I shed all my work and sissy clothes to be completely nude as I drew a warm bath. I was in total need of a relaxing soak to ease my abused body - and likely prepare it for more of the same the next day. I had been soaking for a few minutes and let my mind drift off to relive the pleasures of the afternoon which caused my cock to begin getting hard. Or attempting to at least through the cage. I was in such a focused rush to get out of work that I had forgotten that Derick left the damn thing on me!

I sat in the hot steamy bath and played around with the plastic device that held my penis prisoner. Running my fingers along the edges and the small lock that held it all in place made me contemplate the situation I was in. While I had already been submitting to Derick since he found my pictures on his computer, he now essentially controlled access to my own body. To my cock, my very manhood. It would be hard to argue that I belonged to him now, his little sissy slut to use as he pleased.

Despite a moment of panic when it sunk in that I was locked up like this as long as Derick wanted, my cock kept trying to get hard and I in no way could tell myself it was against my will. Somehow after all the stimulation I had already, I was getting horny again and needed more.

I got out of the tub and dried off, my dick leaking pre cum from the cage already. I didn't even think about how I could get the cage off and jerk off, I went straight for my toy box and fished out my favorite dildo and some lube. It was a nicely realistic white cock about 9" in length with veins running down the length of the shaft to the balls with a big suction cup base that let me stick it basically anywhere I wanted. I brought it back into the bathroom which was still humid from the hot bath and stuck the dildo to the wall above the tub.

I placed one foot in the tub and the other out on the dry floor to give myself some stability. I lubed up a finger which I stuck into my tender hole and then spread another squirt of the slimy jelly all over the dildo which was protruding from the wall at waist height. I bent over and backed myself up until I could feel the tip poking at my butt cheek. I reached a hand behind me and lined the toy up with my ass and pushed back onto the head of the rubber cock.

Comparing it to Derick, the dildo had next to nothing for a head and it slid unopposed into my well used hole. I took a couple inches in and then backed off an inch or so and using this pattern quickly slid myself all the way down onto the cock. My cheeks touched the tile of the bathroom wall and I felt the balls of the toy touching my own while it felt like the head of the dildo was scratching at my stomach. While it didn't have too much in the way of girth, I had always loved how deep this toy could get and taking it all the way in always made me feel like a proud slut.

I sat for a moment with the full length of the dildo inside me before I steadied myself and began rocking back and forth. I quickly picked up my pace and the length I was taking in so that I promptly went from fucking myself with half of the toy's length to taking the entire 9" fully in and out of my ass. Feeling the veiny length of the fake cock penetrate me sent waves of pleasure through my entire body and caused my legs to shake after only a couple of minutes.

Without Derick controlling the cock that was fucking my ass I was a bit more lucid and aware than I would have otherwise been and felt that I had better slow down before slipping and breaking my neck in the tub. What a scene that would have left for people to discover, I thought.

I plucked the dildo from the wall and set it lower down, just above and parallel to the rim of the tub. This, along with a folded up towel I placed on the rim, allowed me to sort of half squat half lie down on the bathtub in a sort of one person doggie style. It was one of my favorite ways to play with a suction dildo as it allowed me to go crazy either moving my ass back and forth on the toy or using my arms to slide my whole body in a more gentle manner.

I took the position and found to my surprise that having the cage on my cock actually made this way easier. Before my cock would inevitably flop around off the towel cause me to stop and reset but as I slid myself on and off the toy a few times I found that the cage kept everything neatly out of the way.

Excited with this new upgrade to my solo play, I fucked myself silly with the toy and lost track of how many radiating orgasms my prostate gave me. Judging by the soaking wet towel that was underneath me it was more than a few by the time I was done.

Without even realizing it I had spent nearly two hours in the bathroom fucking myself with the dildo. Derick was right about the cage, I was definitely feeling like more of a sissy slut with my cock locked up. Any time I felt doubt seeping into my mind about whether or not I actually wanted the cage on I heard Derick's voice in my head reassuring me that it was what any girl would truly want.

Feeling satisfied and proud of myself, I slipped into one of the new lacy nighties I had ordered at Derick's behest. I was still not used to the electric feeling of slipping into something soft and silky with freshly shaved skin and got almost as excited to put on my girly sleepwear as I would get putting on the sexy lingerie I now owned as well.

I slept like a log and rose feeling energized when I began my new morning routine. I was showered, shaved, and sporting some tight-hugging boyshort style panties trimmed in lace under my work clothes as I made my way to work. Everything was seeming as usual, or as usual as things were lately, until I got to my cubicle to drop off my things before my check in with Derick. Only when I turned to head to his office I saw that the door was open but he wasn't there. I knew Derick was in the building - I had seen his car when I pulled in, but there was no sign of him.

I entered Derick's office, thinking maybe he was in the bathroom but found nothing there either. I walked over to his desk and found a small pink sticky note with a message addressed to me. The hastily scribbled writing read:

"Andi, we have a problem that I'm going to need you to help me with. Can't explain now but when you see this you need to come find me downstairs ASAP. Main floor, near maintenance."

Derick was normally careful about calling me Andi in writing so something felt off right away but it's not as if I had much choice. I wasn't sure what to expect and endless possibilities flooded my head while I took the stairs down to buy me some time and collect myself.

None of the outcomes I imagined in my head made any sense and I became even more confused as I wandered the empty main floor of the building looking for Derick. I had no idea where 'maintenance' even was, that was the least of my concerns when I was a regular employee. After a few minutes of feeling lost, I finally heard Derick's agitated voice coming from behind a door down the hall I was in. I hurried my pace up and had my hand on the doorknob about to turn it when I realized it wasn't Derick's voice I heard in there. I only realized it when Derick himself spoke up and I heard the difference, not only in the voice but also the tone. The first voice seemed more aggressive and demanding so I had just assumed it was Derick but when I actually heard him speak he sounded more desperate and pleading than I had ever heard before.

My heart pounded in my chest and I hesitated with my hand on the doorknob as I suddenly got a sinking feeling about what was going to happen when I opened that door. I felt paralyzed as I held my hand on the knob and must have gotten caught up contemplating running away when I came to with a start and rattled the door in the frame. The conversation on the other side of the door stopped abruptly and the door whipped open from inside. In the supply room I saw Derick leaning back against a shelf, both hands held atop his head as he looked at me with a furrowed brow. I could tell he wasn't happy but at the same time he didn't look angry to me, or at the very least not angry at me, but he made no motion to speak or address me at all.

The other voice I heard belonged to the second man in the room. A man whose name I didn't know despite the familiar face. Slowly realization set in and I found myself eye to eye with the overnight security guard who was looking at me with a lecherous visage as I stood in the doorway, his lips twisted in a dark smirk which contorted as he spoke to me.

"Well there we go. We're all here! Glad you could join us... Andi, right? Derick here has been telling me all about you." he spoke slowly, drawing his words out and clearly enjoying the discomfort they caused me. "Come on in, no time to waste."

I darted my eyes to Derick seeking guidance but he merely nodded at me to listen to the man and hung his head. My feet moved reluctantly and carried me into the small room until I was standing in between Derick and the security guard.

This was nowhere close to anything I had imagined on my way down from Derick's office and while it still wasn't clear what exactly was happening, I knew it was far from my control and I would just have to play along and find out. I stood meekly between the two men and pondered my fate nervously but as I stole glances to the new stranger and noted how he looked down on me possessively, my cock began to betray my inner desires and I felt it twitching with increased regularity in its cage.

I knew I was right to be nervous based on Derick's body language but whether or not I was right to be getting turned on, even if it was almost subconscious, I would have to wait to find out...