Caught by My Boss Pt. 03

The few weeks following Derick fucking my brains out against the office window established a new routine in my life. I was now regularly shaving my body of any hair below my shoulders. What had once been an awkward attempt at upkeep was now almost a meditative practice as I would relax in a hot shower or bath and remove any trace of manly hair from my body. To help my skin stay healthy with all the shaving I had begun moisturizing and taking more care of it than ever before and it paid off. My entire body was as smooth, soft, and enticing as any real woman I had ever seen.

One day after work Derick pulled me into his office and directed me to a bag that was sitting on his desk. I peeked into the bag and couldn't suppress a gleeful chuckle as I spilled the contents on the desktop. He had brought me a wide variety of his wife's lingerie and underwear for me to try on. Derick had me try on and model each and every piece and outfit he had brought for him over the next hour and I felt sexier and sexier as I slipped each new piece on. My heart raced looking at the selection I had before me but Derick told me it all had to go back as his wife would definitely notice all of it missing. However, he told me I had an "unofficial" performance bonus coming and that I should use it to get some of my own clothing.

With his help we put together a pretty sizable shopping list for me. All sorts and colors of stockings, garters, panties, bras, skirts, and even some jewelry and accessories. Each new package that arrived as it was all delivered was ripped open and its contents excitedly pulled out so I could try it on. All of a sudden I found myself with every sissy's dream collection; I didn't have a single "regular" girls outfit, if you looked into that section of my closet you would know you were looking at the wardrobe of an absolute slut.

Each day I was expected to show up to work early and meet Derick in his office where I would typically blow him to completion before our coworkers showed up. Sucking his dick had become my new coffee - a surefire way to perk me up for the day. I was also to show Derick which pair of panties and bra I was wearing that day beneath my regular work clothes. In case we had time for some extra play on any given day I was also to pack some extra slutty clothes in my work bag that I could slip into when the office was empty. Even if we didn't manage to do so every day, Derick demanded to see what I had brought in and would punish me with a rough spanking if I got lazy and re-used clothes day to day.

I was in sissy heaven. Having Derick provide me with all these rules and tasks to follow to turn me into his own little whore felt so right to me and everything quickly became second nature to me. Although I had always desired something like this, even me from just a couple months ago would be shocked to see me now. My hole was so used to being plugged, fingered, rimmed, or fucked all the time and being filled up in any way now just made me feel like everything was where it should be in the world.

One morning, as I had finished showing Derick that day's outfit - a stringy blue thong with tiny bows along the hips and matching bra - he pulled a small box out of his desk drawer. I looked at him as he pushed it across to me.

"What's this?" I asked, reaching my hand out for the box.

"You'll see, and I think you'll like it. Not that it matters anyway because you WILL wear this." he answered sternly.

I opened the box and was greeted by a small plastic chastity cage nestled in some white tissue paper. I had never worn one but immediately recognized the device and looked up at Derick.

"Go ahead, try it on."

I pulled it from the box and felt my penis twitching as I considered what wearing it meant. I slipped it on before I got too hard and after a bit of fumbling managed to secure and lock the cage. I looked down at my cock in its new home, wondering how long I would be wearing it. Derick's satisfied laugh caught my attention and as I turned to him I saw him holding what I assumed was the key to the lock on my cage. He noticed where my eyes were looking and started waving the key back and forth gently.

"Ahh, you catch on quick. This is the only key that will let your sissy cock out of that cage. You can't have it but no need to worry, Andi, I'll hold on to it for you and keep it safe." Derick said as he kept the key waving before me as if he wanted to hypnotize me.

"Yes, Sir. When can I get out?"

"Shh, shhh, shhh. Don't worry about getting out. We'll take care of that when the time comes. Besides, it's about time you get started on your day." he motioned for me to leave.

Before I could get another word in he ushered me out into the main room and closed the door behind me. I made sure I was presentable for regular work and sat at my own desk, gently tracing my fingers over the hard plastic of the cage through my pants. I had taken another step into my submission to Derick. He essentially owned my penis, my very masculinity, after this moment and I hadn't even thought about resisting. What kind of man lets another man control his access to his own cock? The stab of shame I felt was quickly drowned out by the erotic feeling of this willful humiliation I was subjecting myself to. The sensation of my dick attempting to harden in vain against the cage was distracting at first but through the course of the day became just another layer of my sissy life. Each throb I felt in the cage was at first an annoyance but quickly became a reminder of the fact that I was merely a man on the outside, inside I was a slutty little sissy girl.

Eventually I managed to collect myself and properly focus on my work. Too much apparently as I hadn't even noticed everybody else leave until Derick shouted at me from his office.

"Where's my slut? She knows better than to keep me waiting?" the bark of his voice startled me from my desk.

I burst out of my chair and nearly ran to his office to find him sitting at his desk and facing the door, waiting for me.

"So, how does your new little cage feel?" he asked, his fingers tented in front of his chin to partially obscure the smirk on his face.

"I think I like it, Sir. I do, actually, I do like it, it feels... natural." my sheepish response made his smirk widen.

"Good. It does make you look like that much more of a natural girl, which I think we both enjoy."

"Yes, sir, I agree."

"Well why don't you come over here and thank me then?" he said with a carnal growl in his voice.

I quickly shed my clothes and rushed to my spot on the floor between Derick's legs. I could see the familiar profile of his cock getting hard in his pants and began running my hands along his thighs and over his crotch. I leaned my face forward and my mouth started to water as I sniffed in the manly scent of Derick's cock and balls through the fabric of his pants. Hurriedly, I undid his belt and zipper and he lifted his ass to allow me to slide his pants and briefs down to his knees. His hard cock sprung free and stood before me, staring me in the face. I licked my lips as it twitched and once again just had to take in the sight of his beautiful penis. The thick veiny shaft stood so hard and fully engorged over his large hairy ball sack and the huge head that I loved so much was already glistening with pre cum. I licked at the slit and tasted the sweet taste of his juice, running it over my lips as I looked up at him.

Derick was looking down at me and watching me with a slight twist at the corners of his mouth. It was around this point in a blowjob that he got tired of my fangirling over his cock and shoved it down my throat but this time he seemed to be enjoying my performance and so I was determined to show him my gratitude for letting me savor his manhood. I lapped at the slippery pre cum that was increasingly leaking from him and used it to lubricate the fat tip of his cock. I took a moment to revel in the beauty of the shiny glans before taking it in my mouth and attacking it from all angles with my tongue.

The groan I heard from above encouraged me to start sucking and licking his cock with a fervor. After making out with the tip for a minute or two I started kissing my way down his shaft with small pecks. Once I arrived at his balls the kisses turned into soft flicks of my tongue as I teased his scrotum. I knew he liked his balls played with but only delicately so with my softest touch I licked and sucked each one into my mouth and looked up past his hard cock to see his eyes rolled back in pleasure. I felt like such a proud slut as I knelt before him and worked my tongue and lips across his balls - my thank you for him locking my dick away.

I started to lick my way back up the shaft of his cock, it was so thick that I needed to make sure he was wet all over before I even thought of taking it in my throat. Up and down my tongue went along the hard smooth shaft and I would trace the bulging veins with the tip of my tongue whenever I found one. It wasn't long before his cock was coated and I was ready to start giving him what I knew he truly wanted.

Starting slowly, I engulfed his head in my mouth and relaxed my jaw as I began to lower my face towards the base of his cock. Not that I was an overly experienced cocksucker at this point but I had been giving Derick nearly daily blowjobs for almost a month now and still felt as though I was drowning when I tried deepthroating him. Yet I found myself addicted to the challenge, not to mention the vicarious pleasure I got through his own pleasure.

"Aghhh, fuck yes, Andi. Suck that thick cock deep into your throat." a breathless Derick moaned at me. His hand finally found the back of my head as I felt his fingers in my hair.

Even though I always wanted to take my time blowing him, it did always turn me on when he would take control and push me further onto him and this was no exception. The firm touch of his hand on my head excited me and it wasn't long before I was easily taking more than half his length in and out with each motion.

His cock was now deep enough that my lips were coated in thick saliva and dripping all over Derick too. I could see the slickness running down his cock and into his pubic hair, enticing me to go further and further down. The more his hardness filled my throat the sluttier I began to feel and the more I wanted it all the way inside me. I wanted my nose nestled in his shiny wet pubes while he emptied his big masculine balls down my abused throat.

It was then that I felt something wet against my thigh and took a moment to glance down at myself. Unable to get hard in its cage, my penis had been absolutely gushing pre cum and my panties and legs were basically soaked. It turned me on to think of myself as a sissy girl on her knees, getting wet and ready to be fucked while sucking her man's cock.

Turning my attention fully back to Derick's cock, I was now determined to take it all and in only a couple spirited head bobs I met my goal. Derick groaned loudly and clamped his hand down to hold me in place with his entire cock in my throat, his pubes brushing my nose and face, and his balls resting against my chin. I did the best I could to slide and suction cup my tongue along the bottom of his shaft while he held me there, not capable of much else.

Derick's strong grasp pulled my head back and up off his cock to allow himself to stand up from the chair. He kicked off his pants and slowly brought my lips to the tip of his dick while he looked down on me.

"Ready for it, slut?" he teased me.

"Ye-"

I hadn't even gotten one word out before he shoved my head down and docked his hardness back in my throat. He gave me a quick second to prepare myself and pulled my head back before slamming me down again, his hardness violently filling my mouth and throat. As the pace of his assault picked up, the thick lubricating saliva was dangling from my lips and chin, sticking to his balls in gooey strands whenever they slammed against my chin.

Derick had facefucked me before - often - but this was proving to be the most intense time yet and the sheer amount that I was leaking from within my cage left me no room to deny my own enjoyment. At the end of the day, Derick's commandeering use of my body for his own pleasure was the major turn on for me in all of this and getting my throat fucked like this was that feeling in it's purest form.

He was pounding his cock so hard and so deep into me that with each thrust I would gag heavily, my whole body retching at the invasion while my mind was ablaze with hedonistic satisfaction. I could hardly see through the tears filling my eyes, I could hardly breathe through the mucous and spit that was forcibly redirected through my nose, and yet I could have described that moment as pure bliss as I dug my fingertips into Derick's muscular thighs and held on for dear life.

With two slow final strokes, Derick pulled me off of him and let me slump back on the floor in a daze. It took more effort than it should have to bring my eyes up to his and see that he was nowhere near done with me yet. I collected my breath as we both looked at each other wordlessly, knowing what we wanted next.

I took it upon myself to rise to my feet between Derick and his desk, standing face to face for a moment before turning around and perking my smooth butt out towards him. I leaned forward and rested my hands on the desk to brace myself while I spread feet apart and arched my back like a good slut.

I coyly half turned my face to peer at him over my shoulder and saw Derick standing behind me, eying my ass like a predator sizes up its prey. The tiny blue thong I had on barely covered my asshole and he wasted no time in yanking it down my hips and letting it fall as far down as my spread legs would allow. It always turned me on so much when he didn't even have time to fully remove my panties and just pulled them down or to the side to get access to my hole.

"Mmm, I know that tight pussy is all ready for me. I can see it twitching for this cock." Derick uttered as I felt his fingers begin prodding at my hole.

He reached around me to grab a condom and a bottle of lube we kept at the ready in his desk and squirted a quick glob onto my hole. He rushed to work it into me and smeared a layer over his now wrapped up dick before he got to work.

"Tell me that pussy is ready for me, Andi. I want to hear you say it."

"You know it is, Sir. My pussy is so ready for your big thick cock inside it, please!" I whimpered as I wiggled my butt for him.

Derick didn't need any more encouragement and slowly but surely slid the tip into my waiting hole. My tight ring gave way quickly to his hardness and I had barely felt the ridge of the head pop in before he slammed the rest of it into me with such a force that my hands gave way and I collapsed onto my chest on the desk.

I started to push myself up but one of Derick's strong hands landed on my back in between my shoulder blades and held me down while I felt him pulling out of my ass. He pulled completely out and repeated the same maneuver a few times - slowly easing the head in and then giving me the rest of it in one hard fast thrust.

I was already moaning like a total whore and he had probably given me under ten strokes. He knew just how to work his cock inside me to get my body accepting it as fast as possible. I heard my chastity cage clicking against the wood of the desk as his balls-deep thrusts began to get quicker and harder until he was full on jack-hammering me while pushing me down onto his desk and all the paperwork he had been dealing with that day. There seemed to be a fair amount of it, maybe that's why he seemed so tensed up and in need of release.

Derick maintained his manic pounding for an impressively long time. I knew I never would have been able to fuck like he does and was just glad to be able to receive something like it at the very least. When my brain wasn't being totally scrambled by what his cock was doing to me I sometimes just found myself being in awe of his sexual prowess.

My legs were shaking when Derick eased up and slid out of me. Whereas I used to feel relief when he pulled out, I was so accustomed to his cock inside me that now when he pulled out I had an insatiable need for it to fill me up again as soon as possible. I blindly reached a hand behind me to try to locate his cock and stick in my hole again but instead felt Derick catch my wrist with a firm grip. He spun me around and with a face devoid of any emotion but sexual hunger he lifted me and sat me on the desk. Derick lifted my legs to place them on his shoulders and gently pushed me to lie back on the desk and lined himself up with my ass.

"Fuck, Andi, I sometimes forget that you've never taken a real cock before this. You are a born slut, girl, I tell you." Derick said without taking his eyes off his cock as it slid into me.

"Mhmm, thank you Sir. Hearing that turns me on so fucking much I can't believe it." my head rolled to the side and I gasped as his stiff dick entered me and slid along my prostate.

The pleasure radiated through my entire body as he fucked me now with slow and easy strokes, getting used to the depth this position allowed him to hit. Every dozen strokes or so he would pull out and tap his cock on my smooth ball sack and look down at me in such an emasculating way that I thought I would cum right then and there.

"This cage works for you. You seem like such a girly slut with it on, you know that?"

The only response he got from me was a whimpering moan as he bottomed out inside me. He moved his hands to grip the backs of my thighs and held my legs up on his shoulders as he started fucking me harder again. I got more and more vocal as he picked up and my hands were frantically gripping at the desk top as the pleasure built up within me again.

I felt a rush of tingling warmth followed by an explosion of ecstasy and looked down to see my soft little dick spurting an obscene amount of cum from its cage. Derick maintained the pace of his thrusts and it felt like each one added another few seconds to my orgasm. It felt like the pleasure would never end and each stroke of Derick's cock made my own squirt more cum from the confines of the cage.

By the time the pleasure subsided I was absolutely drenched in my own fluids. Derick was mopping it off my stomach with his hand and scooping it into my mouth. I would hold his hand in both of mine and suckle the cum from his finger as he fed me my own load mouthful by mouthful. I had never produced that much cum before in any of our previous encounters and I think we were both amazed at how much there was.

Derick wasn't far behind me as his breathing picked up and he fucked me faster and faster. His groans got more desperate and I felt his hands gripping me tighter as he slammed a final few thrusts into me before unleashing a mighty roar of pleasure. I could feel him twitching in my ass and knew he was cumming which filled my own body with the submissive joy of knowing I had filled my role as expected.

He left his cock in me for a few moments and slid out. I lifted myself to lean on my elbows and watched him slip the condom from his dick. I was admiring the weapon he had just obliterated me with when he walked forwards and turned the condom inside out before my face. I eagerly opened my mouth as he emptied his load onto my tongue and lips.

"Good girl, drink up. I've never seen such a cum guzzler like you before. You even lapped up all of your own..." Derick said as he wiped the last bits of cum from his fingers onto my lips.

"Mmm, thank you sir. I really can't lie, I love it so much." I said as I licked at the cum that was glazing my lips.

We set about getting ourselves cleaned up and dressed when Derick noticed that we must have lost track of time and he was already late to get home. He took off and left me to straighten up his desk for him, we had made a mess of basically everything on it.