We were colleagues and it always felt dangerous between us. She was in her early thirties and I had just turned fifty. At first we actively disliked each other, perhaps reacting to the arrogance that we are both prone to, but that slowly changed. We found that we worked well together and started to flirt, particularly after a drink or two on overnight business trips.
She was tall, blond, beautiful, posh, and very fond of wearing designer high heels that made her almost as tall as my 6’ 1”. It was her shoes and my fascination with them that led to drunken conversations that revealed her dominant and my subservient side. In time we discovered that we both had dominant and submissive tendencies, and actually, the first time we crossed a line I spanked her. It was tentative, not yet intended to inflict pain, her bottom in tight blue jeans across my lap, and her long legs and red stilettos stretched down to the floor.
When we weren’t away on business, we tested each other’s subservience by text message. We demanded acts and photographic proof of submission, digging deep into a cruel imagination that we shared. During the working day, if she was the one in charge, I would be expected to respond immediately to a text. A typical task would involve going to a stall in the executive bathroom, removing all my clothes, masturbating until I was on the verge of orgasm, and then spanking my erect cock multiple times with a long plastic ruler. I was not allowed to cum. It wasn’t unusual for her to make me do this half a dozen times in a day. My cock and balls would be raw, red, and aching.
On a day like this, she enjoyed visiting my office at the end of the day to tease and gloat, enjoying my discomfort and frustration. I was actually senior to her at work, but it didn’t feel like that as she sat behind my desk and watched me stand in the corner of my own office with my hands on my head. Sometimes she chose to add to my humiliation and frustration by making me wear her lace panties and a butt plug in the office.
I would take the dominant role too, although I ultimately concluded that her dominant character was stronger than mine. On one memorable occasion, I summoned her to my office. I had her shut the door and sit across the desk from me. She knew what was coming because I had teased her about it by text. Her customary swagger was missing and she looked nervous, her face a little flushed. I had her lift up her skirt, slip a hand inside her panties, and bring herself to the edge of orgasm. With fingers still wet with her own juices, I told her to unbutton her blouse and bare her breasts. Her tits were nicely rounded with large areoles. I watched and smiled as she, at my instruction, clamped a wooden clothes peg (clothespin) on each nipple. I made her sit there for several minutes. I could see the pain in her eyes, but she determinedly said nothing.
All this is to give you a sense of our relationship. It wasn’t straightforward and it wasn’t casual, we were deeply connected by our darker sexual instincts. Our relationship did ebb and flow over time, partly because that level of emotional and sexual energy isn’t sustainable. We had been going through one of our quieter periods when we realised we both had business trips to a city in Germany at the same time.
I had been fantasising and craving her dominance, and of course, she made me beg for it. A one-sided negotiation via text and a picture sent of me naked and on my knees on a hard, tiled bathroom floor.
“Please Mistress, please, I beg you.” Yes, I called her Mistress. When I felt this level of need it came easily. If you haven’t felt that need, it’s hard to explain. For me, I think it comes from the deep sexual thrill I get from being humiliated rather than any desire for pain.
Ahead of the trip, we texted a lot and our excitement and my trepidation grew. In begging for her dominance, I had given her license to take me deeper into my submissiveness. She instructed me to buy a large butt plug and to bring it with me. I spent more time naked on my hands and knees, trying to get used to inserting the plug and to the feel of it filling and stretching me. The thought of doing this in front of her scared me. She also instructed me to bring six wooden clothes pegs with me, clearly intending to take her revenge for that time in my office.
The night before we departed I made a stupid mistake. She sent me a text telling me which suit to wear for the trip and to wear mismatched socks. I take pride in my appearance at work and she knew I would struggle with this. I did struggle massively, unreasonably, and my response can only be described as a tantrum. Briefly, the dominant me asserted itself, I didn’t dress as I’d been told and I knew I would pay for it.
After a working day that I thought would never end, we arrived at our hotel. She gave me instructions to shower, dress again in my suit and tie, and to bring two large gin and tonics to her room at exactly 7.30. I dared not be late and was outside her room several minutes early, feeling like a waiter with the drinks balanced on a tray. I knocked nervously on her door at exactly 7.30 and she opened it with a stern look on her face but a mischievous glint in her eye.
She told me to put the drinks on a small table and waved me to one of two comfortable chairs next to the table. I sat and she passed me one of the drinks. Being treated as an equal, although I knew it wouldn’t last, was unnerving. My hand shook a little as I took the drink. She smiled, enjoying my discomfort, and we chatted almost casually about the situation in which I found myself, about the transition I was now making from colleague, friend, and equal to Slave. We really had become very intimate friends, sharing so much, particularly each other’s desires, fantasies, and fears. It went much deeper than a sexual liaison in a hotel room because she really knew what I was thinking and feeling at that moment.
Then, still, very casually, she told me to stand up and remove my jacket. I did as instructed before she invited me to sit back down and we continued to sip our drinks and talk. Five minutes passed before she told me to remove another item of clothing of my choice. I took off my shoes and socks and realised as I did that we were enacting a fantasy I had once shared with her by text. I knew now that I was soon going to be sitting naked in front of her. My trousers went next and then my shirt, my fingers trembling as I undid the buttons. She told me to leave my tie on, so it hung loosely around my bare neck.
I sat again, wearing only my underpants and the tie, which was red and matched my embarrassed face and sipped at my drink - now just melting ice. Eventually, she nodded and I stood to complete my slow striptease. I eased my underpants over my hips and down to my ankles. I knew from our previous encounters that I wasn’t allowed to cover myself, so I quickly stepped out of my pants and sat back down. Bizarrely, our conversation continued with me naked but for the tie and her fully clothed. I tried hard to hold my stomach in as I sat in this unflattering position.
I was also embarrassed that my cock was not hard. I had reached the stage where I needed physical attention or Viagra to stay hard. In a moment of submissive honesty, I had told her this and she had taken my Viagra away at the airport that morning. My erection and any satisfaction I may ultimately enjoy really did belong to her.
“What a pathetic little girly cock you have,” she taunted.
“Yes, Mistress.”
She had this way of sneering, lofty and patronising, that really irritated me in the office, but now seemed very appropriate.
She informed me that my tantrum the previous evening meant there would be no gentle easing me in. She was going to start with a hard punishment for that disobedience.
“Yes Mistress,” I said as she told me to pass her the black leather belt from my discarded trousers. She then told me to get down on my knees, spread my legs wide, and lower my head to the floor with my arms out in front of me. I waited my nose against the hotel room carpet and my bottom up in the air. My buttocks were spread and I knew this position left nothing to her imagination. When it came to opportunities to humiliate me, she missed nothing.
I heard the belt swish through the air before cutting across my bottom. Multiple rapid strokes followed and I repeatedly felt the harsh sting of the belt across my buttocks and thighs. I gritted my teeth, knowing that I deserved this. Eventually, she stopped and told me that the last six strokes would be delivered vertically, between my stretched buttocks. To do this she stood over me, her black patent stilettos on either side of my head. Again I heard the swish of the belt before it landed between my buttocks, the tip flicking hard against my anus. The second and third strokes followed the same painful path, but she aimed the fourth lower so that the tip of the belt viciously caught my exposed balls. I cried out in shock and pain.
“Don’t be a baby,” she said, “you have two more like that coming.”
The pain was horrible as the belt flicked twice more hard against my balls, but I was also starting to revel in my submissiveness.
She left me on my knees while she sat back in her chair, about a metre in front of me.
“Have you brought the butt plug and the clothes pegs?" she asked.
“Yes Mistress,” I said.
“Get them,” she said, “but stay on your knees.”
She watched as I crawled back to my jacket and retrieved the items. I started to crawl back but she stopped me.
“Put the plug in your mouth,” she ordered.
It was clean, but further evidence of her attention to detail when it came to humiliating me. I crawled back to her like a dog retrieving a ball, and she took the plug and pegs, putting them on the table next to her.
I continued to kneel before her as she stretched out her leg and one black stiletto.
“Grovel, Slave,” she said, “beg to be allowed to kiss my shoes.” I bowed my head to the floor and begged repeatedly to be given this privilege, which I wanted and needed.
“Please Mistress, please, your Slave begs you.”
She let me grovel and watched. Finally, she said, “You may kiss my shoes but only if you beg first to wear the pegs on your nipples as you do it.”
I begged again and she gave me two of the pegs. Knowing I would at some point have to wear the pegs, I had practiced at home to see if there was a less painful way of doing it. I discovered there was, just about, but it was still very painful - particularly putting them on and taking them off. They were wooden, heavier than the plastic ones you can get, with a vicious steel spring that made them bite hard into sensitive flesh.
I winced and tried to breathe deeply as I attached the pegs to my nipples.
She then said, “This isn’t an order but it would please me to see the other four pegged to your ball sack. Would you like to please me?”
“Yes Mistress,” I said and began to attach the remaining clothes pegs. This resulted in a dull, persistent ache to go with the sharper pain in my nipples. I knelt up in front of her so she could inspect the end result. The four pegs fanned out from my balls must have added to my ridiculous appearance. She leant forward and twisted the pegs on my nipples, making me cry out again. Then she tightened the tie I was still wearing hard against my neck. This level of pain and submission was new for us. She paused and looked hard into my eyes, I think to check I was still in my submissive place. I was.
“You may suck the heel of my shoe, Slut,” she said. “Take it deep into your mouth.”
I bowed my head and, supporting her outstretched foot with my hands, started to run my tongue along the length of the heel. Then I took it into my mouth, at which point she pushed the sole of her shoe hard against my face. The heel went all the way into my mouth and I gagged a little. She laughed and eased the pressure before instructing me to lick every inch of her shoe, including the sole. I did, my tongue soon aching and dry. I felt her shiver a little as my tongue slipped from her shoe onto the top of her stockinged foot. As I moved to her other shoe, I was distracted, but could not escape the hurt inflicted by the pegs.
“Does your pathetic little girly cock need its little blue pill,” she taunted as I knelt up in front of her.
“Yes please, Mistress.” That wasn’t enough, she wanted me to say it: “Please, Mistress, can I have the blue pill for my pathetic little girly cock?”
“I’ll think about it,” she said, “now lie face down and spread eagle on the floor.”
“With the pegs on, Mistress?” I realised the pegs would be trapped between my body and the floor, adding yet more pain.
She slapped my face hard. “How dare you question me. Get on the floor now, you worthless little Slut.”
I lowered myself as gently as could to the floor but instantly felt the pegs tugging sharply at my nipples and balls. She got up and walked slowly around me before I felt the pointed toe of her shoe rest between my splayed legs and against my balls. She told me to lift my hips up. I did this and it gave her the room to lift her foot up harder against my pegged ball sack. I groaned as the pegs twisted into the tender skin there.
She removed her foot and let me lower my hips. I heard her move again and felt the sharp point of a stiletto heel did into the flesh between my shoulder blades. She slowly increased the pressure, pushing my pegged nipples harder against the floor. The pegs twisted and I wailed in pain.
“This is the price you pay for your pathetic limp cock and your little blue pill,” she sneered.
She lifted her foot, easing the pain a little. She moved around again and her foot was on my head, pushing down so that the right side of my face was squashed against the carpet and the left side squashed under her shoe. She pressed down firmly and told me to stick my tongue out. I obeyed and she dropped the Viagra pill to the floor. It missed my tongue and ended up about twelve inches away. She lifted her foot and said: crawl Slave if you want it badly enough, but don’t lift your body away from the floor - and keep your tongue out. Tears filled my eyes as I slowly crawled to the pill, the pegs twisting my flesh, and licked it from the carpet.
“Roll over onto your back,” she instructed. I did so as I swallowed the pill.
“Your cock still looks pathetic,” she said, prodding it with the toe of her shoe.
“Yes Mistress, I have a pathetic limp girly cock.”
Her foot hovered just above my cock and then she brought it down and squashed my cock beneath her shoe.
“Pathetic, so tiny and soft,” she said, “but you may remove the pegs and get me a drink from the minibar.”
With relief and more pain I did as I was told.
While she sipped her drink, I stood in a corner, nose pressed against the wall and hands on my head. My body ached from holding the position, but it was good to be free of the pegs and no longer on my aching knees - although that feeling wasn’t to last for long.
“Fetch the plug, Slave, I want to watch you insert it,” she said with a wicked smile.
She knew I had been dreading this moment because I’d told her during our text conversations. I crawled across to the plug. “Please, Mistress, may I use some lube?” We had discussed this too and she had agreed because the plug was much larger than anything we had experimented with before. Thick, long, black, and very intimidating.
I crawled to a spot on the floor in front of her, my head towards her, and the plug again in my mouth. It is really surprising to me, as someone who can be dominant, how quickly I get used to being naked, on my knees, and repeatedly abused and humiliated.