My Manager The Mistress

He grunted loudly as he came, thrusting deep inside me with each shot, my legs shaking as another orgasm rippled through my body. He drove his long cock deep inside me one last time, before slowly pulling himself out of me leaving his load to dribble out of my hole and onto the bed.

"Good girl," she said from the other side of the room, a grin on her face and her hand in her underwear.

I should probably explain how I ended up in this situation. For that, I need to go back a few weeks, but first a little bit about myself. My name is Blake and I'm in my early 20s. I've always had a slim, almost feminine body with a plump butt, bigger than what you would expect for someone my size. I'd never really thought about how feminine my body was growing up, not until my late teens at least. This was when I decided one day when I was alone in the house to try on a pair of my sister's underwear. To this day, I still have no idea what made me decide to suddenly do this, other than an urge to see what I would look like in a pair of women's underwear. It was a pair of lacy pink boyshorts. I had taken them out of the dryer and snuck them into my room, ready for when I would have the house to myself.

Putting them on and looking in the mirror, I was immediately surprised by how much better they made me look. Pulling them up slightly so that I was almost giving myself a wedgie, they seemed to make my butt look even bigger. What was even more surprising, however, was what was happening on the other side. As soon as I had put the panties on, my dick had started to grow and by the time I had finished admiring my rear end in the mirror, I was fully hard. I stood there in confusion for a few moments, a wealth of new feelings flooding me. Suddenly, an idea popped into my head. I ran back downstairs to the dryer and rifled through it again, eventually finding what I was looking for, a lacy pink balconette bra to go with the underwear which I took up back into my bedroom. I took off my T-shirt and put the bra on. I struggled to do the clasp up, so I had to spin it around so that it was at the front to do it up and put it on properly.

Once I had the bra on, I looked at myself in the mirror again and my dick felt like it got even harder. It also felt like it could erupt at any moment. The panties were bulging so much it felt like that fabric was going to burst. I couldn't understand why my body was reacting to wearing women's underwear like this. I didn't get a chance to think about it much as, just then, I heard the front door open. Shit! They were back early. I couldn't let them see me like this. Quickly, I went to take off my sister's underwear but the second I touched them, the fabric rubbed against my dick and I immediately came, my legs wobbling slightly from the pleasure. I stood there in shock for a moment but the sound of someone coming up the stairs brought me back to reality and I pulled off the cum stained panties and bra, threw them under the bed, and put my clothes back on.

After that, I would put on a bra and a pair of panties whenever I had the house to myself. I eventually bought my own so that I wouldn't have to keep wearing my sister's. Fast forward a few years and I now have my own flat and when I'm at home, I wear some form of lingerie almost constantly. On occasion, I'd even go outside, sometimes to the shops, with a bra on under my normal clothes. This would usually make me extremely aroused and I'd often masturbate when I got back home. I'd often go to bed in some sort of lingerie too, usually just my bra and panties but sometimes a cute pink babydoll with matching pink hipster panties. It was this outfit that I had been wearing when I went to bed one night a few weeks ago. I woke up in the morning and looked at my phone. Shit! My alarm hadn't gone off and I had to be at work in twenty minutes! I shot out of bed, took off my baby doll, and got ready for work in record time, running out of the door and jumping onto my bike. I somehow managed to get there only a few minutes late, but nobody seemed to notice anyway.

Most of my work day passed without anything interesting happening except the brief conversation I had with the girl I had a crush on. Her name was Abby and she was about the same age as me. She had long plaited ginger hair, a face dusted with freckles, and a smile that never failed to make my face redden. I thought she was the prettiest girl I'd ever seen. I guess it also didn't hurt that she had a nice body too; about 5 foot 5, a pair of small but perky breasts. It wasn't long after this conversation and I was bent over cleaning a spillage up that I heard the telltale sounds of my manager, Katerina walking in my direction. She was originally from Greece, but she'd lived over here for so long that her accent was only mild. She was about 5 foot 7, had dyed plum-coloured hair and her breasts were a cup size or two bigger than Abby's, not that I'd noticed on the few occasions that I had been around her when she happened to bend over or anything! She often wore a leather jacket and a short skirt, accentuating her large but firm arse, and thigh-high, high-heeled leather boots which is why you always knew when she was coming.

"Hmm, pink suits you Blake," she said as she walked past me. It took me a moment to register what she'd said, and then I shot up, my hand instinctively moving to pull my trousers up. I looked over at Katerina, who winked at me before turning her head and going around the corner. I looked down, slowly lifting the waistband of my trousers so I could see inside. My heart dropped. In my rush to get ready for work, I'd forgotten to take off the panties I'd been wearing. I could feel my face going bright red. Luckily nobody else had seen or I would have never heard the end of it. Hopefully, Katerina would show some discretion as a manager. The rest of my shift went by in a blur, I was constantly conscious of keeping my trousers up and not letting them slip down even a tiny bit. When my shift was finally over, I rushed to the exit so I could hurry home and get away from the embarrassment of earlier but then I heard the clip-clopping of high heels on the floor.

"Blake, can I see you in my office before you leave?" I heard Katerina ask. I turned around slowly and nodded, dreading what was about to come next. I followed her to her office where she shut the door behind me and went over to her desk and sat in her chair.

"I'm going to need you to stay a couple of hours late tomorrow to help me with a few things," she said, her face not giving anything away as to what those things might be. Relief flooded through my body. Sure, I had to stay a couple of hours extra tomorrow, but at least it wasn't anything to do with what she saw earlier.

"Sure, Katerina," I replied with a relieved smile.

"Thank you, Blake," she said, gesturing that I could leave. I turned around and was about to open the door when she spoke up again. "Oh and Blake? Make sure you're wearing something pink again."

She grinned at me as she said this and my face went bright red again. I quickly opened the door and walked as fast as I could out of the exit. As soon as I got home, I just sat on my bed for a while thinking about what had just happened. Slowly, my embarrassment started to turn into something else. It built and it built until I couldn't deny it anymore. I was turned on. So much so, that I pulled my trousers down and started to stroke my dick. Does the idea of being caught wearing women's underwear by my boss really turn me on that much? I guess so. I started to think about the look Katerina gave me as I stroked myself, very quickly bringing myself to an orgasm. I cupped my hand in front of my dick to catch my load as it shot out, before bringing my hand to my mouth, pouring it in, and swallowing it. I'd only done this a couple of times before but now definitely seemed like a good time to do it.

Waking up the next morning, I remembered what Katerina had said about wearing something pink. I didn't want to wear pink underwear again. It might have turned me on for Katerina to see me wearing them but I'm not sure I would feel the same if my co-workers saw. I decided to wear my pink lacey (of course) bralette. Having no underwire, it shouldn't show through my work shirt but, just to be sure, I put a jumper on over it as well. My shift went by without incident, Katerina was in her office most of the day so I didn't see her but I did work with Abby for a while which I very much enjoyed. Eventually, the end of the day came and everyone left leaving just me and Katerina. I walked over to her office and knocked on the door.

"Come in Blake." I heard from behind the door. I turned the handle, opened the door, and entered the office, shutting the door behind me. Katerina was sitting at her desk, doing something on her computer. She motioned for me to sit on the chair on the other side of the desk. I sat there for a few minutes waiting for her to finish. When she had finished, she looked up at me.

"Thanks for staying late, Blake," she said with a smile. "What I want you to help me with isn't work-related, I hope that's okay?". I shrugged and nodded. "Good," she added, before fiddling with something under her desk. Then she spun around on her chair and stood up, facing away from me as she shuffled her way from behind her desk and around to where I was sitting. Once she was stood in front of me I could see what she had been fiddling with under her desk as my eyes slowly moved down from her face to where usually the short skirt she wore would be but instead, just a few inches from my face, was a small realistic strap on dildo attached around her waist. My jaw dropped slightly and I swallowed nervously as I couldn't take my eyes off what my boss was wearing.

"What's the matter, Blake?" she asked, a huge grin plastered across her face. "Don't pretend you

don't want this. Wearing those cute little panties, I know you want it. Did you wear something pink as I asked?" I nodded. "Let me see." I took off my jumper and unbuttoned my work shirt, revealing my bra. "Mmm...very pretty." she moaned as she started to stroke the shaft of her strap-on.

She moved closer to me so that the dildo was almost touching my lips. Up close like this, I could see that it wasn't made out of the usual dildo material, it almost looked like skin. Katerina started to gently touch my lips with the tip of the dildo.

"I want you to suck my dick Blake," she said, staring intently at me. I thought for a few moments. Something about Katerina telling me to do something like this gave me a weird feeling inside. It was like a mixture of being turned on and wanting to be ordered about. Tentatively, I moved forward slightly and licked the tip of the dildo. It really did feel like skin. I licked the tip a little more before putting my lips over the head. Slowly, I started to move up and down slightly taking a little bit more in each time. It was about 5 inches long and very quickly I was getting close to deepthroating it but, before I had worked myself up to that point, Katerina suddenly thrust into my mouth, forcing me to deepthroat. She held it there for a few seconds as I gagged and tears began to run down my face. Just as I thought I was going to pass out through lack of air, she pulled out, leaving the soaking wet dildo just in front of my mouth, allowing me to catch my breath. But as soon as I got my breath back, she pushed the strap-on back into my mouth, put her hand on the top of my head, and began to fuck my face. It took me a little while to overcome the urge to gag and start to breathe through my nose but, once I did, I just let Katerina take over and relaxed, enjoying the feeling of my boss using my mouth like this. I could feel my dick getting harder and harder and the bulging in my boxers must have been noticeable.

"Mmm...I knew sucking my dick would make you hard, but this is just a start," Katerina said as she sped up the fucking of my face. My eyes began to water again and spit was dribbling out of my mouth and down my chin. I could hear myself making small gagging noises each time she thrust into my throat. She continued this for a few more minutes before pulling the strap-on out of my mouth again.

"Up," she said, gesturing for me to stand, which I did. She moved the chair I had been sitting on to the other side of the room. "Take your clothes off and bend over my desk," she commanded. I stood there, dumbfounded at what she said. "Don't make me repeat myself," she added, her voice rising slightly in volume. I did as she asked, taking off my trousers, and fumbling with the button for a while as I did so, before slipping out of my boxers and bending over her desk. Katerina moved to her side of the desk, went into one of the drawers, and pulled something out of it before coming back around behind me. My heart started to race; was she about to put something up my arse? I'd never had anything up there before and I wasn't sure how I would feel about it. Behind me, I heard the noise of something being opened and then being squirted. I buried my face in the desk, dreading what was about to happen. Katerina moved close behind me, and then I felt a cold, wet finger start to probe around my hole. I immediately tensed up and the finger withdrew.

"Relax," Katerina said. "This won't hurt."

It took me a few moments, but eventually, I managed to get my body to relax. The finger returned to my hole and slowly pushed its way inside. I thought I would tense up again once it went inside but I found myself relaxing even more. I liked it. Katerina moved her finger around inside, occasionally brushing up against something that gave me a strange feeling and made my legs tremble slightly. After a while, she pulled her finger back out, leaving me feeling disappointed. But then I felt something else cold and wet push against my hole. It was bigger than a finger this time. It kept pushing against my hole and, slowly, it pushed inside until I could feel Katerina's pelvis pressed against me. She left the strap-on there, not moving for a while, probably to let me get used to it. After a couple of minutes, she slowly started to pull back and I found myself unconsciously moving back, trying to keep her inside me.

"Someone wants it bad..." purred Katerina. "Well, who am I to deny such a good girl?"

And then she thrust hard, immediately making me forget the fact that I was just called a girl. She pulled back, then thrust hard again and again, quickly getting into a rhythm of fucking me hard. I tried to bury my face in my arms to stop the sounds about to come out of my mouth but it didn't work and I was soon letting out high-pitched moans of pleasure. My moans must have been pleasing to Katerina because she started to fuck me faster, making me moan even more. When I woke up this morning, I would never have imagined myself being fucked in the arse by my boss over her desk. I certainly wouldn't have imagined enjoying it. The speed with which she was fucking me now had made my dick rock hard and I could feel an orgasm slowly building up. I wasn't even touching my dick yet somehow I was getting close to cumming, I didn't understand how that could happen. A couple more minutes passed and I was on the verge of an orgasm. I don't know how, maybe she noticed something in my body language, but Katerina must have been able to tell how close I was. Suddenly, she pulled out of me.

"I think that's enough for today. You can go," she said, leaving me in a state of aroused confusion for a few seconds. Eventually, I stood up and started to put my clothes back on. "Oh and I have meetings in Manchester next Monday, you're coming with me. I think you can learn a few things." I nodded at her, still confused at what had just happened. I finished getting dressed then we both left after locking up. I made my way home in a bit of a daze but as soon as I got back, I couldn't stop myself from immediately masturbating while thinking about being plowed by Katerina. Since she had already gotten me so close before, it wasn't long at all before I was shooting my load all over my stomach and chest. I lay there breathing heavily for a few minutes before I scooped it up with my fingers and then licked them clean.

Skipping ahead a little bit to the following Monday, Katerina had told me to meet her at the train station. I was sitting waiting on the platform, just scrolling through my phone to pass the time. She hadn't told me to wear anything this time. I'm not sure I would have been able to wear anything out in public for so long anyway, so this was probably a good thing. A few minutes later I heard the sound of high-heeled boots walking along the platform behind me. I knew straight away who it was and stood up, turning around to see Katerina walking towards me pulling a large suitcase behind her. It seemed a bit big for just one night but I just assumed it was full of work stuff. Our train started to pull into the station just as she reached where I was so there wasn't much time for pleasantries but I did help her with getting the suitcase onto the train and into the luggage rack. The train journey took about two hours; Katerina spent the time doing work on her laptop, and I just watched videos on my phone.

Once we arrived, we took a taxi to the hotel where the meetings were taking place and checked into our room. For some reason, we didn't have separate rooms but at least we had separate beds so I supposed we'd manage somehow. Once we'd dropped all our things in our room, Katerina went off to a meeting saying she'd be back in a couple of hours. I wasn't sure what I was supposed to learn if I wasn't even in any of the meetings but I assumed she wouldn't bring me here for no reason so I went about finding something to do while I waited for her to come back, watching TV for a little bit, then going down to the hotel bar to get something to eat. When I was done killing time, I went back to the room thinking that Katerina shouldn't be too long before she was back but, when I opened the door to the room, she was already there. She was stood next to her bed laying various dresses across it.

"Sorry," I said, thinking she was about to get changed. "I'll come back in a bit once you're done."

"Don't be silly," she replied, smiling brightly. "These aren't for me, they're for you." I stood there in the doorway for a bit, not sure what to say. Anyone else would have probably turned around and left immediately but the slowly growing bulge in my boxers gave away what I was thinking. I stepped into the room, shutting the door behind me, and went over to sit down on my bed, facing the other bed. Once Katerina had finished laying the dresses out, she went into her suitcase and pulled out different bras and panties, a few pairs of shoes, and some wigs, laying them out with the dresses. She then stood up and moved to the side so I could see everything.

"I want you to pick an outfit. Dress, shoes, underwear, wig, everything." Katerina said, folding her arms as she stared at me. I stood up and walked over to the collection of clothes. I looked at the dresses first. They were all cami dresses but of various lengths, colours, and cleavage. There was a red one, a black one and a pink one. Of course, I picked the pink one as I always do. The pink dress also just happened to be the one shortest in length and that would show the most cleavage if I had breasts. Next, the shoes. There were multiple types of shoes each in a few different colours. My eyes were drawn to a pair of pink lace-up open-toe stiletto heels. The heels were a few inches high and very thin so I wasn't sure how I'd be able to walk in them, but I just couldn't resist them. Besides, it's not like I was going anywhere, presumably Katerina wanted to dress me up before getting the strap-on out again. My heart leaped at the thought. I picked a pair of pink Brazilian underwear and matched them with a pink push-up bra. Not that I had anything to push up, obviously, I just thought it looked really cute. Finally, there were three wigs; a long blonde one, a short brunette one, and a medium-length black one. I thought about it for a minute before choosing the blonde one. I thought it would go better with all the pink I'd chosen.