Caught by My Boss

I knocked twice on the door to my boss' office, paused for a moment while turning the doorknob, and pushed through into the smaller room not at all expecting to see what I did. My boss, Derick, had sent me a text asking me to stop by his office and see him on my way out of work that day. Innocuous sounding but when I opened the door I found him sitting in his chair, with a very familiar looking picture of a sissy in pink lingerie full screen on a laptop. My heart was racing before my mind even truly registered what was happening. That was the laptop I had used for a project a few weeks before, and apparently had logged in, and stayed logged in, with my throw away porn and sex email account.

"Not what I expected to see on here when I opened it up." Derick said, with a sort of a chuckle. "That's you, right?"

"Heh, umm... yeah it is.. I guess. Ah -" I stammered pointlessly.

"You guess? Well, I guess so too and we can't both be wrong. Now, there's another thing that I seem to recognize about this picture, what do you think?"

My heart jumped to an even higher pace as I realized what he meant. The previous summer Derick and his wife had gone on a two week vacation and asked me to house sit their plants and cats. They offered to let me stay at the house which was much nicer than mine so I readily agreed. Of course I spent much of my free time during those two weeks digging through dressers and closets looking for sexy things to wear courtesy of my boss' wife. I found no shortage, and took many pictures in various outfits along the way. The picture my boss was currently looking at was taken in one of the sexiest hot pink sets his wife owned, no doubt he recognized it.

"You can't even speak," Derick snorted as he looked me in the face. "Of course you know what I'm talking about. It's one thing for me to find pictures of one of my "trusted" employees dressed up like a slut on my computer but to see that slut dressed up in my own wife's lingerie?!"

"Derick, look, I'm sorry. I don't even know what to say right now." I managed to say, my voice shaky as it passed my lips.

"Ha. Well lucky enough I know how to remedy the situation. I'll run it by you even though you really don't seem to have much choice."

�� My mind was reeling as I still stood in the doorway to his office as Derick motioned for me to sit. I approached the chair across from his but when I got close he reached his leg out and slid the chair away from me. I looked up at him and he just nodded to the floor at his feet, where I took my place. He looked down at me and addressed me with a dark grin.

"So, I'm going to go ahead and assume that you didn't want me to see those pictures. Or those messages and everything else that you have saved in that email." Derick spoke slowly and calmly, while I could merely nod along desperately to his words, hardly believing them but knowing I had no choice.

"In order for nobody else to see those pictures, you're going to do some extra... overtime work... for me. You see, Andrew, for a while now I've been so busy with work here that things between Rachel and I have gone a little cold. I still love her and all that but I never get to fuck my wife any more... it's been two months since we last made time! Honestly as much as I miss making love to her, I just need a hole to use and fuck more often than not."

�� I could see the desperation in his face and hear the plea in his voice. I now knew exactly what was coming and found a part of myself accepting, if not anticipating, what was about to happen to me. My boss and some of his friends, all men around 10 years older than me at 26, were the braggadocios type and I heard many times before favourable references to the size of Derick's penis - which I never wanted but secretly cherished.

"You look pretty fucking hot in Rachel's lingerie there, I can't even lie." Derick said slowly, fighting the words coming out of his mouth. "It doesn't even feel gay, you look like such a girly little bitch there. I never imagined.."

"Has she worn these for you any time lately?" I asked, forgetting to act apprehensive of the tension in the air.

"No, you wearing these when you watched the house were the last person in them. I think you'll be the next person in them too, bitch."

Derick stood from his seat and stepped forwards into me. His crotch of course at face level to me sitting on the floor, and I could see a large outline of his cock under his pants. I was taken aback until he grabbed my head and shoved it into himself and I could smell the musk of his manliness and breathed it in intoxicatingly. I reached for his belt and he let me undo it but as soon as I started opening his pants and freeing his cock he grabbed both my wrists. Derick was a much stronger and thicker man than I was so easily held my hands in place as he rubbed his cock against my face through his underwear.

"Look Andy, you can be gay or whatever you want to be but I'm not. I'm not going to let a guy suck my cock. You only get that privilege if you're a girl, get it?" He shoved me back lightly and zipped up his pants. His eyes looked down on me expectantly.

"Yes, I get it..."

"Meet me in my office same time tomorrow and we'll follow up on this. If I bring you that outfit again I expect you to act like the slut you look like while wearing it, ok?"

"Yes Derick, of course.." I couldn't look him in the eye, staring at the floor until I felt him look away. I took the chance to stand up and rush from his office.

I sat in my car for at least 20 minutes processing what had just taken place. Something that felt so surreal and yet was going to have major implications in my day to day life for the foreseeable future. I nervously drove home and having no appetite, merely turned on a hot shower and soaked until the water ran cold. The entire time thinking about how stupid or careless I could have been to leave that info in the laptop. So reckless! Yet a part of me kept flashing with excitement at the idea of Derick using me as his secret slut. Being a married man's physical outlet instead of his wife had always been a fantasy of mine. I had a hard time sleeping that night, but when I finally drifted off I must have slept well for all of a sudden it was morning and my alarm was ringing to go to work.

I got in for the day and didn't actually see Derick at first which only heightened my anticipation for when I would. I had a somewhat mobile job so I would be in and out of the main building semi- frequently and it wasn't until that afternoon that I finally made contact with Derick. The tension had been building in my stomach so when I finally saw his office door open and heard him inside, I took the chance and slipped in. He was just finishing up a phone call so I quickly closed the door behind me and sat at his feet on the floor. I didn't even think about sitting anywhere else after what had happened the day before, and by the time it did occur to me it seemed right to stay where I was. Derick certainly agreed as he looked down at me with a smile on his bearded face.

"Good girl. I knew you would remember your place. Have any good dreams last night?" He asked me, rather deviously and that only turned me on more. He knew what he was doing.

"I couldn't get you off my mind... I'm not new to feeling like a sissy but I've never felt like somebody's personal sissy and I think I like it."

Derick laughed and said, "Of course you did, you little bitch. You think I didn't know that? I'm going to make you my little sissy save but only because I know you truly want it too. We both want it, and that's exactly why you have no choice left but to accept it."

"At any rate," he continued. "I told you to come back here at the same time as yesterday and you are way too early. We need this place empty before you set foot in here again. Now, get out."

He spoke so sternly I once again felt myself on autopilot following his orders. I got up and left his office and robotically went through the rest of my day. Feeling the time crawl by and yet at the same speed past as I found myself once again unsure of what I wanted to happen. When finally the time came that everyone in the office had gone home, I approached his door again. Finding it ajar I pushed it open and was greeted by an empty room. However, laid out on his desk was the pink set of his wife's lingerie that I had worn. A lacy bralette that clung tight and had a small frilly shawl along the top that swished around when moved. Tight fitting panties that consisted mostly of tiny straps and more lace than any true solid material but they hugged my plump ass in just the right way. Finally he had brought some black thigh high stockings with tiny pink rose-shaped bows along the top.

I approached the desk and was studying the lingerie, running my fingers over the soft fabrics and remembering how it felt on my body when I first wore it. I felt my own cock hardening at the memory and quickly started grabbing at the lingerie. I had most of it in my hands and held up to my face, inhaling deeply whatever scents I could from the clothing when I heard a noise behind me. I turned to see Derick had returned to his office and was at the door, standing in the door frame and completely blocking the only exit. He was staring at me with what could only be described as hunger on his face.

"Put it on. All of it." he said to me.

I didn't hesitate but I did fumble in my nervousness and so after taking a few minutes to dress properly I attempted a little curtsy for him to tell him I was ready.

"On your knees. This time you get what you wanted, girl."

I dropped to my knees and began to gather myself for what was about to happen to me in this office. I was running all sorts of scenarios and outcomes through my mind while I knelt in front of Derick, eyeing the visible bulge in his pants. While he seemed pleased he clearly didn't appreciate my hesitating as he grabbed the back of my head with a strong hand and firmly pushed me forward towards his covered cock. He began rubbing my face against it, making me feel the cock that I had just been envisioning myself servicing to completion. A small moan escaped my lips which caused Derick to snort in laughter.

"Wow, you haven't even actually touched or seen my cock yet and you're already moaning like a whore." he chuckled as he pulled my head back a slight bit from his crotch. "Might as well pull it out and get your hands on it."

He unzipped his pants and pulled the flaps aside as I watched in awe. Only when he paused for a moment and gently but firmly slapped my cheek did I realize he wanted me to do the rest, carrying on from where we left off the day before. I pulled his belt loose and slid his pants down his legs until they bunched up at his knees. His cock was visibly straining against his tight briefs so I reached a trembling finger up to the elastic band of his underwear and started pulling them down his hips. The band slid over the base of his shaft and I felt my heart skipping a beat as I was about to be eye� to eye with my long time boss' hard cock. While I was dressed up as a slut in his own wife's lingerie... not where I had imagined my career would be taking me.

After what felt like forever his dick, now pretty well fully hard, flopped out from its restraints and bobbed in the air in front of my face in all its glory. My jaw dropped when I saw it; what a specimen of manliness. He had slightly above average length, probably six or six and half inches, but it was the girth and form of it that really took control of my mind. It had to be nearly as thick as a beer can with a head so perfectly sculpted for one purpose... to invade. The large, hard as rock mushroom head of his dick aimed at my face like a weapon, threatening to conquer me as though it would push past my defences with ease. The thing we both knew, however, was that no real fight was going to be put up on my part, I had long succumbed to the reality of what was going to happen to me and was instead drawn in by sheer lust.

"Ha, I knew you were going to like what you saw. But quit staring, time to get to work slut!" Derick spoke gruffly as he slowly thrust himself towards me.

My mouth was already open, whether from shock of what was happening or merely in preparation of what was to come, and so the invading head of his cock slid past my lips and onto my tongue, sending shivers through my body. A man's penis was now in my mouth for the first time in my life and it was none other than my boss who was on the giving end. My lips closed around him and my tongue started to explore the underside of his cock as his girth filled my mouth. It was difficult to even get started as I felt overwhelmed by his hardness but he didn't seem to care as simply shoving it forward further into my mouth, and eventually my throat, was pleasing him enough. He groaned as he forced his cock onto me while I sputtered drool down my lips and chin.

He made me make eye contact with him as he pushed further and further, his thick cock absolutely taking over me as it filled my throat and became the barrier to me breathing. I was so overstimulated that he pulled back a bit while leaving his cock on my tongue again but allowing me to breathe. My chest was heaving, my eyes watering, my nose and mouth were leaking like crazy and yet all I could do was close my lips back around his dick and start sucking it again. He left me to my own pace now and I greedily slurped on the wet head of his cock, becoming addicted to the taste of his sweet pre-cum. I clearly had room to improve skill-wise but nobody could argue my passion as I licked, kissed, and sucked his cock from balls to tip in a downright frenzy.

"Fuck, you clearly had your inner slut pent up too long Andi. She needed this maybe even more than I did!" Derick exclaimed.

Even though he used my "normal" name there was something in the way he said it that just told me he wasn't talking to Andy, his employee, he was talking to Andi, his little slutty side piece. The girl on her knees before him whose entire focus was pleasing his cock. He pulled all the way out of my lips and gently slapped his cock head on my mouth and face, looking me over with pursed lips. I stuck my tongue out and opened my mouth, unsure what he wanted but doing my best to be a good slut for him. He put his hands on his hips and very slowly thrust back and forth, sliding half of his cock gently into my mouth as he looked down over me.

I tried reaching up to grab him and take him deeper but he slapped my hand away any time I did causing me to get antsy and keep trying harder and harder until he merely grabbed both my wrists in his much bigger hands and held them in place while he gently slid his cock in and out of my mouth. The teasing carried on for what must have been another ten minutes or so until finally I was practically begging to take all of his cock in my mouth. He asked me once if I truly wanted it and before I had even fully answered "yes" he shoved forward until I was gagging and choking on his full cock. His balls touching my chin were comforting me while I "suffered" from his cock stretching my throat and jaw open but I knew I had to make it feel good for him, not only out of fear of what he would do but I realized that was my purpose.

"You're a natural cocksucker Andi," he said. "You went from choking halfway to deepthroating my entire dick in no time!"

I murmured a response as best I could with his meat filling my mouth, which he laughed at and slowly withdrew. My jaw was slack and my entire face felt numb as I looked at his drool-covered cock before me. The cock which had just undoubtedly taken ownership of me. Derick stood above me, clearly satisfied with himself and hopefully with my performance. He eyed me at his feet in his wife's lingerie and then looked about the room before setting his eyes on the large leather chair behind his desk. He lifted me by the chin until I was standing before him and looked me in the face, making me suddenly aware of how puffy and wet my lips had become. Derick turned me around and patted my ass to direct me towards the chair, instructing me to get up on it with my knees on the seat and my hands holding the back of the chair. I climbed up as though I was hypnotized, obeying his orders without even thinking about it or as if I had no other choice. I did want to do what he was telling me at this point but it still somehow felt as though he held a power over me that made me do what he said. My ass was left perked out towards him and he walked up behind me with unwavering authority to place his hands on my hips.

"What a fucking sight." Derick whistled as his hands slid down my waist and around my ass cheeks. He gave each one a firm slap. "Damn, girl, you have a natural ass on you too! I'm starting to think you were born to be my slut."

"Oh! Ha.. thanks, Derick! I can't even lie, it feels pretty good when you - ah! - hit me like that.." I said, gasping as he continued to smack my ass with his hands.

"Not just a slut but a naughty slut, aren't you? You like that, Andi?"

"Oummm, yes, please! It burns so good when you spank me!" I shouted back, unintentionally loud.

He spanked me from above until I could practically hear my ass cheeks screaming in pain but the second he stopped and gently brushed his fingers across them the relief was nearly orgasmic itself. While he was passing over my ass he would drop his thumb down my crack and press it against my hole for a second or two before he moved on. Each time he found this target my entire body twitched with anticipation. My mind had barely recovered from the facefucking and spanking that I hadn't even considered his big dick going up my ass but of course it felt only natural at this point. I heard him walk away and turned my head to see him digging through his bag to pull out condoms and lube - clearly at least one of us had thought this far ahead. He saw the look in my eyes and smirked at me, popping open the lube and dribbling some on my asshole which he worked in with a firm finger.

"We didn't have time to get you shaved and cleaned up like a real girl for me yet, so unfortunately I'm not going to eat you out today but that treat will come." Derick as he focused on lubricating my tight asshole.

He must have known from the pictures he saw that I wasn't exactly a virgin, I owned a couple dildos and played with my ass on my own many times so my hole warmed up fairly quickly to his slippery finger. Before long I was moaning loudly again while Derick worked his fingers in and out of my hole. I could feel lube dripping down my thighs as stretched me open and counted my blessings that with that cock of his at least he knew that there was never too much lube. I heard him smearing his cock with lube and felt the head slide up and down my twitching hole which drove me wild.

The man knew how to tease a cockslut, I had to give him that. He also knew the right moment to stop teasing and began to firmly press the head of his dick into me. Like I said, I wasn't new to ass play but I had never had a real cock in my ass and never had anything as thick as he was so the moment his head breached my hole was damn near a spiritual experience for me. I felt nerve endings bursting with feelings that I didn't even know I had as he stretched my hole past anything I had ever felt. All this just to get the head inside, but we did it. He paused and lightly toyed with my still red ass cheeks again.

"Good girl, that went in easier than I thought. Maybe you're just that dedicated to being my cockslut, hmm?" he asked, probably rhetorically.

"Yes, Der-ahhh! FUCK!!" I yelped as he diabolically shoved his dick in another couple inches the moment I spoke.

I turned to see him with a mischievous smile on his face, proud of what he'd done. My look of anger faded quickly.