My boss was a right bitch. I’d never liked her and I wasn’t the only one. Her rages, her outbursts, her bullying ways were relentless. It was common for me and some of the other guys to talk about fucking her, it was a way of letting off steam and making light of the situation. But the fact of the matter was, she was terrifying - 6 foot tall, a strong build and a steely gaze. She was far from ugly too let me tell you which is always enough to strike fear into any man’s heart. She had long, luscious black hair and full, pouty lips that were mostly painted red.
She lived nearby to me and occasionally she would give me a lift home if she saw me walking. The conversation was always stilted and uneasy so it was something I preferred to avoid if possible.
Today was not going to be one of those days. In fact today had been an awful day and she’d made it that way. She’d shot the usual put downs my way, criticised my work in the most sarcastic manner possible and generally made me feel like a piece of shit - there‘d just been more of it than was usual and she‘d seemed to have thrived on it. I’d felt humiliation well up inside me and I knew it wasn’t going to go away just by leaving the office. Of all days, she chose this one to pick me up on the way home.
What I wasn’t expecting was her to invite me in to hers for a quick drink. She had seemed quite sincere, almost sweet as she’d asked me so I didn’t like to refuse. I was also of course scared of what she’d be like tomorrow if I rejected her. So, with trepidation, I went into her home. It was exquisite. The furnishings were modern but with a classic feel, everything was immaculate and VERY expensive. This was a woman of control and taste - she knew exactly what she wanted.
I sat down in the living room as she walked to the kitchen and I realised I hasn’t told her what I wanted. She hadn’t asked me. She shouted something through about how she rarely got to know her colleagues out of work beyond general small talk way. I thought to myself that it was hardly surprising, this hardcore bitch was never going to get any invites out. Somehow the coldness of her, admittedly, fine home only made me dislike her more, brought out more of the resentment I felt towards her.
She walked back into the living room with 2 cocktails. I tried to suppress the look of surprise but inside I was thinking, “A cocktail? Hardly a man’s drink is it?” She paused slightly as she walked towards me, clocking the expression on my face. Raising one eyebrow, she said with a husky voice and a slightly wicked smile, “You never know, you might just like it.”
She sat close to me on the sofa and ploughed on with her talk about the office. “I had singled you out from the start,” she said looking directly at me. I felt a rush of shock and discomfort. Where the hell was she going with all of this? Sure, I had joked about fucking her but I didn’t think I’d actually have the nerve to do it in reality. “You have a certain quality that I like,” she continued, “very sweet, very giving.” I smiled but she could see it wasn’t genuine. What the hell did she mean by that? She knew nothing about me.
“You probably think I’m hardly fit to judge, seeing as I hardly know you.” My eyes suddenly widened at this insight. “But you’re wrong”, she said leaning over to me, “I know exactly what you are.” She was almost purring in her glee, the glint in her eyes told me she was getting aroused by her little game. She lifted her hand and gently stroked my hair. “So timid,” she whispered, “hardly a man at all.” My heart was pounding. I should be angry but I couldn’t get past the fear. I’d known all my life that I didn’t feel up to being a man. I fought and buried the sense of failure, tried to fit in with the guys and hoped and prayed no-one would ever notice.
“I bet you’ve barely enough dick for a proper hard on right now.” She reached straight between my legs and grabbed my cock. She was right in that I was getting an erection - but now I feared her laughing at the size of my penis. Surely this was going to make it go down. She pressed hard on my crotch, caressing my cock, scrutinising my manhood. I let out a whimper. I hadn’t meant to. Our eyes met immediately - mine pleading with her not to mock me, hers merely amused. She cupped my face, pulling me closer to her, “looks like you’re ready to show yourself to me,” she said in a low voice, “it’s time to stop hiding.”
She stood up and it was clear I was to follow her upstairs. I tried to find the courage and the words to tell her no, but the coward in me won. I followed her. In my mind I was still convincing myself that I would just fuck and her and get the hell out. Hopefully she wouldn’t play too many games with me in the process.
Her bedroom was as perfectly well judged as the rest of the house, with an enormous bed being the centre piece. I couldn’t help but notice that it had ornate iron bars as part of its design. I shuddered. My boss stood in front of me, her 2 inch height advantage suddenly becoming more apparent. “Strip.” I slowly took my clothes off as she watched me. I felt exposed and inside I was screaming to run, to save myself the pain of this humiliation. So why was my cock twitching with the excitement as she ran her cool, emotionless gaze all over me. She clearly had ideas, I just wished she would throw me a scrap of comfort and tell me what they were. “There, a clean slate to work with, “ she said, “that feels better doesn’t it?” It didn’t but I nodded.
She walked over to her underwear drawer and pulled out a bra and panties set. They were a soft, light pink, covered in frills and lace. The panties were see through. She had to be kidding. She tossed them over to me, “Put them on.” I stood still but my eyes darted over to the door. She caught my look and walked directly to the door, there was an angry air about her. I looked away as I heard her turn the key. “I shouldn’t have to tell you again, you fucking half wit, put them on.” Her voice was commanding and stern, but there was real rage building up in her too. I fumbled for the lingerie, my hands shaking. She rolled her eyes and tutted loudly, striding back over to me. She picked up the bra, placed the straps around my arms and then clasped it in place behind my back. That single act was like she was tying me up, binding me in some way. I wanted to be free but was not strong enough to fight back. She pulled on the panties, tucking my erection into it. She lightly brushed her hand against me, the soft fabric moving over my cock and sending waves of pleasure through me. I closed my eyes, trying to block the reality of me standing before her dressed as a woman. But how the soft material and the tightness of her bra around my chest felt betrayed my true thoughts. My mind was as trapped as my body was.
Next she produced a suspender belt, stockings and the highest pair of heels I’d ever seen. Placing the belt around my waist, she pulled it tight. A further piece of my maleness was being subjugated as she secured it behind me. She had me raise my legs one at a time as she pulled on the silk stockings and snapped them in place. She placed the black, 10 inch heels before me and her eyes ordered me to step into them. My height was raised but my balance was precarious. I felt even more vulnerable.
She saw my unsteady bearing and looked scornful, “A failure as a man and now a pathetic example of a woman.” She snapped her fingers and gestured to the large bed, “Lie down and spread your legs.” Fear prevented me from moving, but she took advantage of my weakened state, pushing me from behind. It wasn’t a forceful push but it was enough to make me topple onto the bed as she had wanted. I nervously shuffled myself into the middle and slowly parted my legs. The wicked smile slowly crossed her face again. “Good girl,” she sniggered. Reaching into the cabinet, she pulled out some silk ties. “No…” My protestations were merely above a high pitched squeak. Normally I’d have maybe just about been strong enough to fight her off but I was shaking and weakened by the prolonged angst. She sat astride me and pinned down one of my arms with her knee, laughing as she did so. She grabbed my free arm and tied it to the bars on the bed. Having done the same with my other wrist, she then moved to my ankles. I was spread out before her on her bed - her toy, her disposable plaything.
She crawled her way up the bed, arms placed either side of me, her groin pressed against mine, she looked down at me and grinned as she rubbed up and down. “Does your sweet, little pussy like that?” she asked, “Is your cunt getting wet and hungry for dick?” My eyes closed, body restrained I hardly knew what I wanted or what I was any more. The lines between my mind and hers, my body and hers, were blurred. She had taken me over completely and her will was my own. I then heard a buzzing noise. Looking up at her I saw that she had a large, life-like dildo in her hand. There was no fear left in me, my reflex reaction now was to want her to put it between my legs, I could almost sense what it would feel like to have her thrust a cock into my moist pussy.
She trailed her dildo down my stomach, “I know you want to feel my cock against your clit.” I stretched my body at the thought of the ecstasy this would bring, my hands and feet pulling against the ties. She took the tip of the vibrator and brushed it gently against my glans. I could hardly bear the wonderful sensation. I strained against the ties again, this time to try to part my legs wider, urging her to slide it into the pussy I was imagining I had. She pulled the dildo away and, lifting her skirt, pushed it into her own cunt, covering it with her glistening juices. Slowly withdrawing it, she leant over my face, her lips close to mine. “I want you to taste your wetness,” she said as she brought the shaft to my mouth, the overwhelming scent of an aroused female close to me. She put the tip in my mouth and I licked the wet cock, then running my tongue along the length. My mind was full of the image of this large, engorged cock having been inside me, wanting me. I was trembling and desperate to climax but my submission to her, to womanhood, rendered me helpless.
I felt her pulling down my panties. “And now, my pretty and obedient whore, I’m going to fuck you until I’m done with you.” She was above me, her arms supporting her weight, her legs in-between mine. I felt her slide onto me, every sensation in my mind told me it was her cock entering me. I was being taken at last. Her movements were forceful and commanding, every thrust feeding her lust. She moaned with a low sound from the back of her throat and when she tossed her hair back I could see how her eyes burned with passion. As she used me harder and harder, I knew she was nearing her climax.
Suddenly, she pressed her lips against mine, a kiss so fierce and deep I felt a sting of pain. As she kissed me she cried out and I felt the pleasure pulsing through her body as the weight of her crushed me. As if by unspoken agreement, her coming gave me permission to feel the pleasure of my own climax. An explosion of sensation took me whole - I was helpless and at her mercy as every ounce of strength drained from me. As my orgasm subsided and I lay on her bed spread eagled and satisfied, she planted a single, soft kiss on my lips.
Standing at her front door, dressed in my own clothes once again, I mumbled a good bye to her. Even after her using me for her own gratification, she still had an intensity in her stare, a permanent lust. She stroked the side of my face and planted a kiss on my cheek, before smiling and closing the door. I started my walk home, trying to comprehend how I felt about what had happened, of what she had made me. And as I walked I felt the soft rub of her panties on my skin, her last order to me being that I was to wear them home. I knew she would be buying me more to wear for her at work and my stomach lurched with anticipation.