As I went home that day from the office, I kept asking myself:
Who is Naughty?
Why is this person doing this to me? What did I do to deserve this? It could not just be because of the screen sharing that they recorded. No, it could not just be a chance thing. I was sure they had to know me. Those thoughts and images of me masturbating in my lingerie haunted me all night long.
The rest of the week followed the same pattern. I would get in before 9:00 am. Log into a video chat with Naughty, one way video as he/she never revealed themselves. I would put my white garter belt and white stockings on and then wear my white panties with lace trim overtop. I would then drain the cum filled water glass from the day before into my mouth. Swish it around and swallow. I was not to drink anything for one hour. I was told to savour the flavour. I would then put my work clothes back on overtop and go about working.
At 4:30 pm, we would reconvene and I would once again masturbate into a cup with only a 1/4 inch of water now, in my lingerie, yes my lingerie as I was reminded daily, for Naughty. I would drink half of my own semen and then change and leave for home at 5:00 pm.
I had hoped that the humiliation would end and that Naughty would get tired of this afterwards, but I was wrong, sorely wrong. Things were just beginning. My life would never be the same again.
The following Monday it felt weird to be in the office again. Two whole days without stockings, without a garter belt, without panties. Part of me dreaded going to work. I would have to dress up again. I would drink spunk again. My spunk. The taste would linger on my tongue and in my mouth.
Part of me was oddly enough, excited. I was "on" all the time. The feel of the stockings on my legs was surprisingly nice. No it was more than nice, but I did not want to admit that to myself. I couldn't. I was a man. Nor could I admit that the panties felt better than my briefs. Yes they did. And every time I saw my legs, my own legs, part of me was turned on. No this could not be happening to me. I am a man.
I was early and so was Denise. We exchanged pleasantries and shared the semi-mundane happenings of our weekends, then set about getting to work. I entered my office and closed the door.
8:45. No emails from Naughty. Maybe I was in the clear?
8:50. Nothing.
8:55. Nothing.
8:59, an email arrived. Shit.
Last week seemed like it was all a dream, no not a dream, a nightmare, but one that was long ago. Now I realized it wasn't.
I opened the email. Again it had a link to our own private chat room, complete with video, for me to show at least. Naughty never turned his/hers on. I did all the sharing. I was told to wait for the next package, it should be arriving soon, then to log back in and not open it.
Another package? What I did not have enough lingerie already? Now I got nervous. More nervous than before. I knew this had not ended, I knew it had escalated. Where was this going? How far till I was done?
At 9:30, I heard someone talking to Denise through my partially opened door. After he left I stepped out. She was just rising up to bring me the parcel. Today this hot brunette had on a pink blouse, red pleated skirt with pink stockings and heals. Red loop earrings, thick red bracelets, bright pink lipstick, pink blush and of course pointy red nails on her perfect, dainty fingers.
"Oh, you must have heard? There is another package for you. A bit larger than last time as you can see, brought over by the same company." She paused and looked down at it.
"Here you go. What was in the last one?" She finished with as she handed it to me.
All the time I was watching her. I watched as she swung her chair towards me, which partially spread her legs, and focused on her skirt as it ruffled a bit, then straightened as she got up and stood on her super hot legs. Then as the package was being offered to me I saw her fingers and nails. Man were they a turn on. Hell, she was a turn on.
I would call this blue-eyed brunette a 10, as would most men.
As I took the package from her I heard her question. "Personal stuff from a former client is all." I lied. I had to. I wondered how many more packages would come. How many more times I would have to lie to Denise.
I felt bad as I looked away and returned to my office. I again reminded her that I was not to be disturbed for the next 30 minutes. As she acknowledged this she crooked her head a little, a hint of inquisitiveness on her face.
I was in the chat room again. Naughty was there, waiting for me.
"Take off your clothes. All of them. Do it now."
Once again I was removing my tie and unbuttoning my shirt. Pants were carefully laid on top and my briefs I stuck in one of my desk drawers. I stood in front of the computer and its camera. My manhood fully exposed. I was getting semi-erect again.
Once again my penis was betraying me. I should not be getting excited at this. For all I knew there was some sick 80 year old man at the other end of the video chat, or maybe some bored housewife, or... I had spent a lot of time already wondering. Everyone in my office, and those from the video chat were now suspect, even Denise. Who was it?
I looked down at the screen and read what I expected to see.
"Open the package and put your fresh lingerie on".
It was what I half dreaded and was half excited about. More lingerie. My lingerie. That thought settled upon me again. I was a man. I was not gay. Why was I putting lingerie on again? Yes, or my life would be ruined. Got it.
I pulled out a lacy pink garter belt, pink stockings, pink panties and I almost gasped, a lacy pink bra. At the bottom of the box there also was a lacy white bra to match my first lingerie set and a pair of white high heels.
No this was not happening.
But it was.
I fastened the garter belt around my waist, just above my hips. I had become better at this over the past week and it only took 3 tries to get the clasp in. Then I rolled the stockings up both legs. They felt silky smooth on my legs, like the ones did last week. I did the clasps from the garter belt and then pulled up the lace trimmed pink panties overtop.
This felt strange but also strangely familiar. This was not happening. I was getting accustomed to lingerie. Accustomed to wearing my lingerie.
Then I hesitantly picked up and sized up the bra. Yes, I had a little bit of man-boobs, but not much. I was not slim but not overweight either. I looked at the screen.
As I hesitated Naughty added "Put your bra on. Put your bra on now."
My bra, yes my bra. I looked down and meekly began to put it on. I was turned on and humiliated at the same time.
I put both arms through the straps, adjusted the cups over my "breasts" and then tried to get the clasps together. Again and again I tried. Finally I hooked the bra and adjusted it to make it fit as best as it could. It actually sort of did. Weird. My cock was gaining strength.
I looked at the screen. "Good, you look good." A compliment that was not landing really as such with me. I felt more exposed now than ever.
"And telling from your penis, you like it too." My head hung down a bit.
"You can put your clothes on overtop."
Luckily I had chosen a wine coloured shirt today so it easily hid the pink of the bra underneath. I was still very self conscious of it so I put my suit jacket on as well.
"You will be visited by a client of mine. Yours now actually."
Mine? Naughty had been in the video chat session, under a different name 10 days before. He/she obviously knew my clients on that day or was one of them. This was escalating.
"What is going on? That was not part of the agreement," I typed.
I feared what would happen next. Up to now it was only me. But another person, in the same room as me, with likely nothing but my lingerie on? That would not end well. For me at least.
Naughty hesitated, then replied "Our agreement was that you would do as you were told. Period. Or I would release videos to your wife and boss. Are we terminating the agreement? If so I will send last weeks videos and this morning's in fact. Let me know. Now."
Reluctantly and defeatedly I replied "I will do as you ask. Do not send the videos."
"Good. I would really hate to see you divorced and in the poorhouse. Emma deserves better than that."
Shit, Naughty knows my wife's name.
"Now your client is coming at 12 noon. He will be meeting with you during your lunch hour. You should thank me for that. Denise will be away at lunch."
