Dominated By My Boss

When I was a young lady in my twenties, I had an affair with a senior director at my company. He was assigned as my mentor and business coach. Tom was in his forties and extremely handsome; it’s fair to say I had a crush from day one. I was no virgin, but he made me feel like I was; he made me feel things I’d never felt before. However, I’m getting ahead of myself.

The affair started clique, a company Christmas party, and staying at a hotel, and I ended up in Tom’s bed. We were both pissed, and it was a flurry of stripping and a quick but satisfying fuck. That started an almost two-year affair with Tom; it was an affair as he was married.

Some of the things we got up to brought out a nature a didn’t know I had. For example, we would often meet in a hotel after work; Tom would always come into our regional office during the day and in private, ask me how much I was looking forward to the evening. When at the hotel, he would always ask the question again. He would then make me lift my skirt up, pull my panties and tights down and inspect the crotch of my underwear to see how stained and wet they were. If they were, he was pleased; if they were not, he would then tell me he was going to do a ‘film check’ With me holding my skirt up and my panties around my knees, he would put two fingers in me and out and then part them to see how moist I was; thankfully, I always passed the ‘film test’ We would then have a very refined dinner before heading back to his suite. He always bought me a g*ft of some nature: underwear, j*wellery and once a luxury SPA weekend away for my mother and me.

Unlike with other lovers, I was totally submissive to Tom, and I loved being dominated; I never knew what to expect. However, I sometimes could feel my pussy creaming as I went to his room in the hotel life. Other memorable events: this was the 1990s, and I like most women, still had a full bush. He once shaved me; he took great care, and the vibrations from his razer caused me to orgasm. I had never allowed any ‘bottom play’, but Tom took my anal cherry, which became a regular feature of our love life. During a business meeting, he would ask me to take my panties off in the office and hand them to him; although we were alone, there was a window that overlooked a large office with banks of desks. I was then told not to wear underwear for the rest of the day, and he would make regular checks to ensure I was compliant. I loved the feel of his fingers running through my pussy in the lift to the company restaurant. Later in the evening, we would be sat in the bar at the hotel, and he would hand me my panties back, and I would have to put them back on in the bar; although I became good at secretly putting them on under the table, I was spotted a couple of times as I hitched them up into place.

I joined him on a business trip to New York for a few days. One evening he shaved me and gave me a very short white skirt to wear. I used to have long, slender legs, but the skirt only covered my modesty, and my lacy panties could be seen when I sat down. He asked me how it felt to know that most of the men in the restaurant had probably seen what I had under my skirt. I said that as I was in America and thousands of miles from home, it didn’t bother me as I wouldn’t see any of these men again. He smiled and told me to go to the loo and take my knickers off when I returned to give them to him. Even though I’ had a few drinks, I was horrified but complied. My pussy didn’t even have hair to hide behind!! I knew from the almost whip-lash action from some men passing that they had seen my most private feminine place, and a few even saw Tom’s fingers dancing through the lips of that place. Later he fucked me in his hotel room in a Manhattan hotel; he first made me stand naked in the window; we were about ten floors up, but I’m sure I was seen nude by passersby on the street below. He fucked me with all the lights in the room on, too, had anybody been in the adjacent buildings; they would have gotten free porn show that night.

Before Tom, I’d never seen a butt plug, nipple clamps or a love egg. After work one evening, he fitted the butt plug nipple clamps, inserted the love egg and took me out for dinner! I didn’t make it through the main course before I came. Tom was a great dancer who had some serious moves; On another occasion, he stripped me nude in the hotel room and attached a three-way chain that clipped to my nipples and clit. As we danced, he pull on the chain, which stimulated three of my sensitive erogenous zones. He was fully dressed, and I was nude, and of course, the hotel room lights were on, and the curtains were open.

On another business trip to London, there was a knock at the hotel room door, and a gorgeous blonde girl was admitted into our room. She was a high-class escort as Tom wanted a menage trois!! I was terrified; however, I again enjoyed myself. She was very beautiful and sexy. I tasted another women’s pussy for the first time and had a woman lick me out. I sucked Tom’s cock after it had been inside her pussy (yes, he had a condom on). At one point, I had Imogen (no idea if that was her real name) licking me out as I sucked Tom off. I also knelt in front of Tom naked with Imogen beside me as Tom came over our faces.

I’d never been spanked, not even by my parents. I recall being naked over his knee as he paddled my ass and occasionally stuck a finger up my pussy. I had an orgasm whilst being spanked! He once made me lay in the doggy position over his desk in the boardroom and, with a marker, put a big T on one of my buttocks and an M on the other. He thought it was extremely funny that including my arse hole spelt TOM! I then spent the rest of the workday with his name on my bum. It took ages to wash it off.

After two years, he left the company for a better position, and I was dumped; in fairness, I was ready for the relationship to end as I’d just met the man I would marry. It was a hell of a ride whilst it lasted.