Humilated in silk and satin
Ever since Caroline started work in my firm 7 years ago I always found her to be a bit special. Not just that she was intelligent, efficient and good at her job, but also in the way she carried herself, her demeanour, the way she dressed and the way she spoke. Class just seemed to ooze out of her.
She joined the firm from university as a financial analyst. Before university she had been to a girls boarding school and she clearly had that ‘polish’ that a good private education can give you.
Seven years on she has lost the awkwardness of youth and had become a very confident young woman. She was going places in my firm, of which I was the Chief Executive. I would be lying if I said that I noticed her only for her work. I noticed the way she walked, the way her hips swayed when she wore her high heels; I noticed the classiness of her clothes, so well cut and clearly bought at designer shops.
As time went by I started to notice her more and more, to the point where I was captivated by her. I found myself daydreaming and fantasising about her .. usually in the middle of a boring meeting. I remember clearly the day that I first masturbated while thinking of her. I was in a board meeting and had to call for some financial figures, so Caroline brought them to me …. she leaned over me as she put the papers on the table and then proceeded to explain what were the figures I needed to concentrate on. I caught the smell of her perfume and her silk blouse brushed gently against my arm. Omg! I was instantly in a state of arousal.
When the meeting broke up I immediately rushed to the toilet and locked myself into a stall and I had the most fantastic orgasm as I fantasised about Caroline. After that there was no stopping me. Time and time again I masturbated while at work; sometimes two or three times a day. I masturbated so much that I stopped having sex with my wife. Caroline became my obsession.
I had noticed that Caroline would bring in spare clothes on a hanger or in a holdall, into which she would change if she was going out on the town after work. One evening, after everyone had gone home and the cleaners had finished their work I went to Caroline’s work station. The office was dark, but I could see reasonably clearly by the light from the street that was coming through the window. She had a dress hanging on the coat stand, and I noticed a sports bag under her desk. I pulled the bag out and opened the zip.
Inside the bag was a lovely selection of bras, knickers, tights, holdups, stockings and suspenders. Just like her clothes, her underwear was extremely classy.
My breathing became very short, my hands trembled, I could feel blood rushing to my face … and the blood was gushing into my cock too. Omg, I was so excited. I took hold of a lovely pair of pink silk knickers and held them to my face. Oh they smelled so good!
I was afraid someone may have come into the office and would have found it difficult to explain why I was in a darkened office in an area I would not normally be. So, I quickly put the knickers back in the bag and took the bag with me to my office. When there I took out everything; several matching sets of bras and knickers as well as the many pairs of nylons, some worn and some clearly brand new.
With the gorgeous underwear spread across my desk I quickly dropped my trousers and pants and started to wank. It took no time at all for me to ejaculate massively across my desk, thankfully missing all of Caroline’s undies. I quickly cleaned up and got the lingerie back in the bag, then quickly back to her desk.
I knew that I had crossed a line. No longer content with masturbating in the toilets, I was now looking out for opportunities to fantasise about her underwear, and also to use her underwear. Omg, I knew I was addicted.
Over the next 6 months my behaviour became obsessive, and the frequency of such events increased to at least twice a week. The more frequent I did it, the more careless I became. First, I was not so careful about the way I put the lingerie back in the bag and secondly I was beginning to get cum on the lingerie. I got cum on the lingerie because I was not just wanking over it on the desk; I was actually wearing it while I was wanking.
Yes, I was imagining myself as Caroline’s sissy. I dressed up and strutted around in her stockings, suspenders, knickers and bra. There in my darkened office, late at night, sometimes in the early hours of the morning I would walk around in Caroline’s lingerie, and then adding one of her dresses and also a pair of her shoes. I became a total sissy, but the ejaculations, when I allowed myself to cum, were absolutely fantastic; the best I have ever had. But I really could not control them by now, so from time to time I would get cum all over the underwear and nylons. I did my best to clean it up and hoped it would dry so she would not noticed.
It seems obvious looking back that I was bound to be caught, but I was blinded by my excitement. So it transpired, late on a dark winter evening, I was dressed in black stockings, black suspenders, French knickers and bra, with my feet squeezed into a pair of Caroline’s black patent heels I was on the point of ejaculation when the light of my office was flicked on and standing in the door was Caroline, flanked by two of her junior colleagues. I had been ambushed. The cameras started to click immediately. I was done.
There has been a big price to pay. Firstly, in order to keep the photos off of social media the three women had immediate promotions and massive pay rises. But it did not stop there. On a very regular basis I have to attend a ritual humiliation; I take it in turn to go to the house or flat of each of the three women, where I have to dress up as a sissy and clean their house or flat. I am subjected to all sorts of verbal humiliation, but it doesn’t stop there. Invariably I will have to accept a spanking and often times a fucking, courtesy of a strap on. More recently, they have got really bold and now I am often spit-roasted by two of them while the third looks on and films the event.
At times like this it is often to look at the positives. At least I now get to wear the underwear of three gorgeous ladies, not just Caroline, and they still allow me to masturbate. Happy days!!