Caught by My Boss Pt. 02

The blaring sound of my alarm stirred me from an unusually deep sleep; it was one of those mornings that truly made me regret the obnoxious tone I used for my alarm but without it I'd never get out of bed. I began my normal zombielike morning routine to prepare for the day and it wasn't until I sat down to eat a quick breakfast that I felt the tenderness of my ass and all the events of the previous day came flooding into my mind.

Somehow I had messed up and left my incriminating online accounts logged in on a company computer and my boss Derick had found them. My fantasy of being a sissy girl and serving a dominant manly man had suddenly become all too real and remembering Derick's messages he had sent the night before made me think it was only going to get more and more real for me. A strangely exhilarating sinking feeling overtook my stomach, accompanied by a tingling in my cock as I ran through what might happen that day at Derick's hands. He had instructed me to bring a razor and there weren't any doubts in my mind as to why. As much as I'd fantasized and played around at being a sissy, I knew Derick was about to take me the rest of the way.

Snapping out of my reverie I glanced at the time and realized I had to hurry in order to get to work early as Derick had ordered. The short drive in to work felt like it took forever and when I arrived I noticed only Derick's car in the lot out front. I wondered how long he had been there and what he was preparing for me inside while I sat in the car until my phone buzzed in my pocket.

"I see you out there. Better not be having second thoughts, get inside." the text from Derick read.

I entered the building and deposited my proper work things at my station and made my way to Derick's office with my shaving supplies and his wife's lingerie that I had cleaned of all evidence of the previous day's activities. He was standing in front of his desk, leaning against and looking at the door waiting on my arrival. He threw me a bullish smirk as I came through the door and looked at me while I stood there meekly, almost as if to say 'I knew it'. He didn't say a word until I approached him and handed him the seductive set of lingerie I had worn, almost reluctant to let it go.

"Good. You can listen to orders." Derick said. "We have just enough time to get you ready for your overtime duties today after work, let's get to it."

"Yes, sir." I said with a crack in my voice.

I had never called Derick 'Sir' before and certainly hadn't planned on doing so but once again he had this subconscious effect on me that just told my brain he was superior and that I needed to acknowledge that fact.

He pointed towards the private bathroom in his office and followed behind me as I made my way over. I opened the door to see the lights were already on and there was hot water running from the sink faucet, making the small room feel warm and steamy. Derick ordered me to strip and promptly kicked my clothing out into his office. I was left naked and clutching the small bag containing the razor and shaving cream that I'd brought along.

"We both know what you'll be doing here so you may as well get started. I'll be right here watching so try and make it sexy while you're at it." he said as he urged me towards the sink with a nod of his head.

Of course I knew what he wanted. Despite my slender and relatively hairless physique I had never committed to shaving my body hair completely and I knew that was about to change. With trembling hands I set out my supplies and got to work lathering myself with the shaving cream beginning at my chest and arms. There wasn't much hair to remove so I made quick work of my upper body with an occasional glance to the door where Derick stood overseeing the process. As I started applying the cream to my groin and legs, Derick stepped in and grabbed my leg by the thigh, lifting it to rest my foot on the edge of the sink.

"I like my girls completely smooth and hairless, much prettier that way." he said as he took some of the cream himself and started rubbing it over my ass cheeks and inside my crack.

I lost myself under even this light touch of his once again, my eyes closing and my head drifting back as I felt his strong hands and fingers roam across my ass. He covered my tender hole and played with it using a fingertip until I let a small moan escape my lips and then he stopped, backing away.

"That hole especially has to be nice and smooth for me. I don't like getting hair in my mouth when I eat pussy."

I nearly whimpered as his hands left my ass but got right back to work. Covering my groin, balls, and thighs with shaving cream. As I passed the razor over my skin, I was shocked at how quickly I was beginning to look truly feminine. With a lack of hair, my slender legs and small but perky butt could easily have passed for a real girl's. I was getting excited at the sight, thought, and feel of the whole process and my dick began to jump and harden. I was embarrassed that even this was turning me on so I attempted to hide it by holding my dick in my hand and shaving around the base but to no avail.

"Damn, even this is turning you on? You keep proving yourself to be even more of a slut than I thought, Andi." he chortled from behind me. This time I couldn't bring myself to meet his gaze.

With a bit of clumsiness I managed to get my entire genital area shaved bare. I ran a hand over myself and felt the tingly freshness of just shaved skin, sending a small shiver of pleasure through my body. I finished off my legs and soon stood before Derick feeling more naked than I ever have before, now unable to even think about hiding my arousal. He looked me over from head to toe. Bending me forward over the sink and spreading my ass to inspect the job I had done. With a satisfied grunt, he smacked me lightly on the butt and walked out of the bathroom to his office. I wordlessly followed.

"Alright Andi, good work. You'll get better at that soon enough because I want you doing it everyday before you leave home. My little slut is to be smooth and clean at all times, understood?" he said.

"Yes, sir. Of course I understand." I dropped my eyes to the floor as I again called him sir without thinking.

"Good girl, I like that. 'Sir' works well for me I think." he replied with a smirk. "Now back in the chair like you were yesterday."

I made my way over to the chair Derick had taken me on the day before and climbed up on it on my knees, my ass jutting out backwards. Derick approached and ran his fingers all across my smooth body; the pleasurable tingle I felt from my own hands was eclipsed by the downright ecstasy of feeling his hands explore my smooth skin. He placed a hand on either ass cheek and spread me open to take in his property. I could practically feel his eyes devouring me and my hole was puckering with anticipation. I was expecting a repeat of the day before, maybe a finger or even his dick if he thought I was still loosened up for him. It was a shock when I felt his soft wet tongue on my hole and I gasped in pleasure. Though it wasn't overly intense of a feeling it was so delicately pleasurable that I knew I had to keep myself smooth if this was what getting eaten out felt like.

Derick's tongue slowly flicked across and around my hole, teasing me mercilessly. He would flatten his tongue out and spread the entire thing across my ass before pulling back and licking me with short quick strokes of the sharper tip of his tongue. It felt incredible and before long I was moaning as loud as I had been when he'd been balls deep inside me the day before. After a few minutes of this he must have decided I was ready for more because I felt his tongue starting to breach my hole. He slowly pushed it in and out, going further each time until I felt the scratchiness of his stubble on my ass. He basically fucked me with his tongue while I clasped onto the back of the chair for dear life.

Just when I couldn't take it anymore and was about to start begging for his cock inside me, Derick pulled back and stood up. I frantically swiveled around in the chair, looking at him with my best attempt at 'please fuck me' eyes. He snorted a brief laugh and turned away, walking to the other side of his desk and pulling open a drawer.

"You have a tasty pussy Andi, I could get used to that." he said, rummaging around in the desk for a moment before pulling out a metallic butt plug with a shiny purple jewel at the base.

He walked back around to me and pushed the plug to my face and into my mouth.

"Unfortunately I have some important calls to make, not to mention everyone else will start showing up any minute now, so that's all the prepwork you get. I'm going to put this plug in you and you're going to go back out there and have a regular day at work. Then come see me at quitting time - and the plug better still be there."

"Yes sir, it will be."  was all I could reply as he pulled the plug from my mouth.

He nodded and gave me a firm spank before he plunged the toy into my ass, giving it a couple jiggles and turns to make me squirm. Placing his hands under my armpits he lifted me from the chair and jerked a thumb to the office door. I gathered my clothes and ran out to get dressed before anybody showed up for work.

It was a long day full of anticipation and tension. I was amongst my coworkers who were all having a regular day at work while I was there, shaved bare beneath my clothes and with my ass plugged by a toy that our boss had put in me after licking my asshole like a pussy. I could hardly focus on work let alone office small talk between coworkers with the ever present feeling of my ass being filled and my constant looking to Derick or his office for some sign of approval. Derick played his part much better than me, hardly even glancing my way let alone saying anything to me. While the rational side of my brain told me he was just being covert, the submissive sissy in me was yearning for attention. He knew what he was doing and it was working well, maybe better than he even expected.

By the time people began packing up and filtering out of the office I was a mess. I could hardly talk without clenching my teeth first to make sure my voice didn't come out as a whimper and my underwear was completely soaked in precum from the stimulation my ass was getting. My hole twitched almost endlessly around the plug and I had caught myself a few times throughout the day dreaming that it was Derick inside me, although I knew that if that were the case I'd be feeling much fuller. Finally, after the last of my coworkers had left, I sensed my opportunity and made my way over to Derick's office. Knocking lightly on the door, I pushed it open a crack and waited for his voice. After not hearing anything for a moment or two I peered inside to find it empty, Derick was nowhere to be seen!

"How could he be doing this to me?" I thought, frantically looking around to see if I had simply missed him elsewhere in the main office.

There was no sign of him and I was worried that he had left early for some reason without me noticing. I practically sprinted over to the window above our parking lot and sighed in relief when I saw his car there. I relaxed for a moment looking out the window until I heard a noise behind me and felt two unmistakably firm hands grip my shoulders. Derick spun me around and pushed me to the floor, grabbing my arms and pinning them above my head. He looked down on me and licked his lips, clearly satisfied with his little "prank" he had pulled. I wasn't as happy about it but wasn't in any position to argue, he had me on my knees with my back and arms held up against the window, in full view of anybody who might walk by.

"Did I scare you, Andi?" he asked. "Sorry about that, just had to run downstairs to maintenance for a second, I thought you had made it all day without breaking so maybe another five minutes without my cock wouldn't hurt but looks like I was wrong."

"Please, Derick, I've been needing it all day. This plug is driving me wild, I need your co-" I begged him until I was interrupted by a firm slap on the cheek from his free hand.

"I thought I told you I liked being called 'sir', don't forget it!" he said gruffly.

"Of course, sir, I'm sorry. I can't focus on anything right now.." my eyes dropped to the floor as I spoke quietly to him.

"I'll allow it without any real punishment - for now - but soon you had better learn to be a good slut and ALWAYS do as I say, understood?"

All it took was a quick nod on my part for him to reach down and unzip his pants. He didn't remove them completely but fished his cock from within and left it hanging in the air before me. I was finally back face to face with my newest, greatest desire and it must have showed in my eyes.

"Ahhh, all of a sudden you seem like you can focus, huh?" Derick asked, massaging his quickly hardening member with one hand.

I opened my mouth to speak and he pushed his prominent ridged head past my lips. Giving up on saying anything, my mouth was relegated to its new primary duty and I started sucking him off as he pushed in further and further. I had practiced sucking my dildos before but a situation like this - my hands pinned above me and my back pressed against the wall, trapping me between a rock and a hard dick if you will - was never something I could have recreated. The helplessness I felt only served to turn me on even more, I couldn't have escaped even if I wanted to.

It was an expectedly sloppy blowjob. My lips and Derick's stiff cock were dripping with saliva and I was losing myself in the service of this man. Feeling him gliding across my tongue and lips, hearing his grunts and moans telling me I was doing a good job, and looking up with my eyes to see him staring down at me in lust all combined to fully switch my brain into slut mode. I didn't care that anybody who happened to be walking by outside would have a full view of what was going on, in fact I probably didn't even register the thought.

Derick began taking over more and picked up the pace until he was fucking my face with no mercy. My head was now pressed against the window as he thrust his dick in and out of my mouth while all I could do was keep my teeth out of the way. His head drifted back and he was staring at the ceiling while he took my mouth. Knowing he was feeling so good and that it was because of me sent chills of pleasure through my body that built up until I felt a spasm at my groin and began moaning myself, as best as I could with a hard penis shoved down my throat.

"Did you just cum?" Derick was suddenly looking down at me with a surprised look on his face. "What a good little slut, you came just from sucking me off?!"

There was no shame in my system any more so in response I merely looked up at Derick and returned his incredulous stare. Even he seemed surprised by what he had created, though the groundwork was already there and he had just been the catalyst. I had spent many nights alone fantasizing about situations like this one while playing with myself and any combination of toys that I had at my disposal.

Seeing me like that must have had an effect on him as the facefucking abruptly stopped and he withdrew. My jaw was left hanging open and thick, slippery drool was trailing from my lips down my chin and soaking my throat and the collar of my shirt. Derick's cock was glistening with the same coating and it looked downright delicious. I craned my neck forward to get it back in my mouth but Derick held me still against the wall. Once I gave up trying he let go of me and I nearly collapsed on the floor, I had been so used to him holding me in position.

"Stand up, slut, and turn around. Get those men's clothes off you too, it doesn't look right." Derick commanded.

I was grateful for the tight quarters between him and the window as I rose on shaky legs, feeling that I may fall at any second but knew I wouldn't get far with him there. It wasn't until I had stripped and turned my back to him that it really sunk in how exposed I was in this position. He shoved me forward between my shoulders and I threw my arms out against the window to catch myself. I was bent forward in front of this man as he was readying to plow my ass in full view of a floor to ceiling window. There was hardly any chance of somebody seeing but if they did there would be zero doubt as to what was happening. Somehow, I felt even more on display when Derick turned and headed for his office. I knew better than to move since he hadn't instructed me to do anything and so sat there waiting until he returned with the set of lingerie we had 'borrowed' from his wife.

He tossed it at my feet and knew he didn't need to instruct me on what to do. I slipped into the skimpy pink bra, panties, and stockings with familiarity. However, what was unfamiliar was the feeling of the sleek soft fabric running along my now shaved legs and body. It was electric and I nearly moaned just putting it all on. My own dick, not nearly as impressive as Derick's, was rock hard and straining against the thin panties by the time I was dressed and ready for him.

"That's a good little sissy, Andi. Rachel would notice if this stuff went missing but you look so fucking hot dressed up like a slut that we're going to have to get you outfitted with your own things. Your new sissy uniform." Derick spoke as his eyes devoured the sight of me.

"Oh, please sir, I would love to have more of my own clothes to wear for you whenever you want." I had nicked a few pairs of panties throughout my life but never made the step towards purchasing anything, let alone matching sets like the one I was wearing, and the thought of having a stocked closet excited me.

Derick gave me little time to dwell on that as he shoved me back into position against the window and took hold of my ass in both hands. He pulled the narrow back of the panties to the side and clicked his tongue in approval as he pushed on the plug that was still in my ass. Slowly turning it and pulling it in and out he teased me for a minute before sliding the plug fully out of me. It had only been lubricated with spit so by this point in the day it was a bit dry and I jolted a little when he extracted it. Derick obviously enjoyed my discomfort as he chuckled and reached the plug around to my face and into my mouth. I sucked the metal of the plug and could taste myself on it, pleasantly surprised that it wasn't as bad as I expected. After coating the plug with a fresh supply of saliva, Derick returned it to my ass to push it in and out a few more times before dropping the plug to the floor.

He once again took my ass cheeks in his hands and spread them wide open. I turned my head over my shoulder to see him looking at my hole which was no doubt showing signs of his handiwork over the past couple days - I certainly felt it. Any discomfort was put away when he leaned forward and once again stuck his tongue out and into my hole, the muscle incapable of resisting allowing him to slide right into me. Moving his tongue around and in and out soon drove me wild and had me moaning in pleasure once again.

This go around we weren't constricted by time and expecting anybody to show up in the office so he spent what felt like a blissful eternity pleasuring my hole. He added a thick finger to the mix, reaching inside me and teasing my prostate as his tongue circled around what he labeled my 'sissy pussy'. His finger rubbing on my prostate combined with the feeling of his tongue working me sent waves of pleasure through my body. I could feel myself leaking precum and soaking my panties once again while I leaned on the window with all my weight. My face was pressed against the glass and every moan or wail that left my lips fogged up the window, mixing with the drool that was getting smeared from my face onto the glass to obscure my view outside, not that I was taking in the sights by any means.