Meeting His Matchbydj2020©
I first saw her on the tube; I'd missed my usual train and had to wait for then next one. She'd boarded just ahead of me and stood facing away from me with her hand on the pole to steady herself as the train pulled away. She was about 5'9, slim with blonde hair and was dressed in a dark business suit with a tight pencil skirt on which finished below her knees, she had high heels on which tautened her calves and raised her up to over 6 foot. She was a vision anyway, but as she bent over to place her bag between her feet it placed her pert ass in a position of prominence I found my breath was taken from me. She got off at the stop before mine and I watched her walk away from me, as she stepped out the carriage she looked round and I saw her face for the first time her green eyes were playful, haughty and full of confidence, she had high cheekbones and looked about 10 years older than me at around 40, fantastic at 40 would be a more accurate description.
I found myself running late about a week after that and instead of rushing for my train I took my time and allowed my mind to wander back to that mysterious blonde lady who had had such an effect on me. I could see her, I could smell her, I could almost taste her and I knew I wanted to be with her. She was on the platform when I arrived, with the same bag by her feet. I followed her on the train, she found a seat and I sat on the opposite side. She was dressed similarly wearing a shorter skirt this time and as she crossed her legs her stocking tops and suspenders showed briefly before she readjusted her skirt. She must have seen me notice as she looked at me, she held my gaze and allowed a small smile to form as she looked me over. She then uncrossed and re-crossed her legs again this time leaving her skirt ridden up and pointedly ignored me for the rest of the trip. I watched her go again now I didn't just want her I needed her.
The next day I wasn't running late, I was on time for my new tube, she smiled as she saw me arrive and invited me onto the tube before her brushing my leg with hers as we boarded and directed me to pole where she stood behind me grasping the pole just under my hand. I turned to introduce myself; she stopped me with a finger over my lips and turned me back around. We rode in silence for the majority of the journey; she interlocked my leg with hers and gently brushed my thigh with it whilst caressing the pole suggestively with her hand. She was in control, at her stop she simply said tomorrow. It was after she'd left that I'd noticed she had left her bag and the doors were closing. It was too late to return it to her now, I held the bag up for her to see, and she bit her lip, smiled mischievously and winked.
That evening I was filled with thoughts about her, I wondered hat her plans were and if that smile, that wink was an invitation to open the bag, as if she'd left something in it for me. I finally decided to open the bag, the first thing I saw was a note in the top compartment, saying naughty boy you'll be punished for this. I guess she had wanted me to open it, so I then opened up the bag and couldn't believe what I found. There was leather, latex, restraints, whips, chains, cuffs, gags, blindfolds, candles, butt plugs, lube dildo's, strap-ons and a note. The note said today was a test, you want this that's why I left you the bag, you're mine now and tomorrow I'm going to take you, I suggest you use the plugs because I am a bitch without mercy I am going to bend you over and fuck your ass hard and long. I am going to punish you for looking at my thighs, for thinking about me without my permission, for looking at my ass when I bent over (I could feel your eyes on me). One more thing make sure you're clean there's a douche in there.
I put the stuff back in the bag and put the bag in the wardrobe, I hadn't signed on for this, I could just return the bag tomorrow and have done with it. I couldn't believe she thought I'd go for this I'd never done anything like this before. Yet I wanted her, I couldn't get the image that she had implanted with that note of hers out of my head. Maybe I deserved to be punished, she was right I'd fantasised about her, I so wanted to bend her over, pull up her skirt, pull down her knickers and feel her warmth and tightness as I entered her. It was clear to me now I'd wanted her completely, I wanted her mouth, I'd wanted her sex and I'd wanted her ass and I wasn't going to get it.
However, I could give her my mouth and my ass in the way that I wanted hers and I could take the punishment I deserved. I hadn't even realised it, but I'd already got her bag out of the wardrobe and had emptied the contents onto my bed. I grabbed the douche and went to the bathroom, I followed the instructions and tried to insert it into my ass, it wouldn't go in and it was far thinner than all her dildo's and plugs. I lubricated it and this time it slipped in, I squeezed and emptied the contents into my ass, before the urge to expel my bowels took over, everything came out and I couldn't have stopped it had I wanted. I did it again and found I enjoyed the sensation.
Prepared I grabbed the smallest dildo which was 7 inches in length, had a circumference of just under 5 inches and had a tapered end, put some lube on my ass and onto the dildo and tried to insert it. It didn't want to go in, my ass just tightened up. This was not going to be easy, I started to panic I might not be able to serve her, my desires which had gone from taking her too been taken by her might go unfulfilled. I searched through her butt plugs and found an inflatable one. I took it in turns trying this and the dildo until I was able to take insert the dildo into my ass. It went the whole way in and thought, but I was still tight and it hurt when I moved it in and out, just when I thought I'd succeeded. I wiggled it around and my anal muscles finally started to relax, as I continued to fuck myself I caught sight of myself in the mirror, thought what am I doing.
I stopped pulled out the dildo, put the stuff I'd used in the sink and went to get a beer, disgusted with myself. An hour later I was back in the bedroom fucking my own ass with a bigger dildo, some strap on porn on the internet showing a guy tied up in a dungeon been taken at both ends by 2 hot mistresses egging each other on, whilst pulling myself off. As I came I could feel my ass gripping and releasing on the dildo, the mysterious blonde was right I did want this and I knew I'd let her do anything to me. I went to sleep exhausted and dreamt of her taking me.
The next day I couldn't get any work done, I spent it in a state of constant arousal hoping and praying she'd take me, nervous that she'd change her mind and decide she didn't want me, nervous that she wouldn't change her mind and would fuck and punish me, because the there really would be no going back. I arrived early at the station; I didn't want to miss her. She wasn't there, I waited for the next train and she still hadn't arrived. I was mad I wanted to go, but I was hers and I waited over an hour before I felt a hand around mine as she took her bag back. She just looked me in the eye and said I told you that you were mine.
She steered me onto the next train, no words were exchanged until we reached her stop. She said we got off here, I'll lead the way. I guess this was my last chance to change my mind, but I didn't even question her commands. She lived close to the station and let me into a plush apartment block. I had the pleasure of watching her walk up 5 flights of stairs; she knew exactly what effect she was having on me as I got harder each step she took. As she stopped outside her door and took her keys out she leaned up close and said once we're through that door you do everything I say, immediately and without question, do you understand all I could do was nod.
She opened the door to reveal a hall and let me inside, closing the door behind us. Before I had taken 2 paces she commanded to stop and stand still, she rounded me, slapped me, loosened my belt and unbuttoned my trousers letting them fall around my ankles, she grabbed my throbbing cock and ordered me to pull my pants down to my knees. Mmmn I like a hard cock, you will keep it that way or be punished, she slapped me again and I understood. She took my manhood in her hand and led me over to the kitchen table, and then she bent down and put her mouth close up to my cock so I could feel her hot breath on me. She looked up at me licked her lips and said would you like some Tea.
Slightly taken aback I said sure fine, so she went over and flicked the kettle on, returning with a whip. She told me the kettle will boil in about 5 minutes, time for pain. You can beg for mercy but won't get any, the whipping will continue until the kettle has boiled. Scream if you like the place is sound proofed, but you will count out loud each stroke and say Thank you Mistress, lose count, fail to thank Mistress and I'll have to boil another kettle. With that she smiled, drew the whip up and brought it down hard on my cock. I screamed out loud, not only had I not been expecting to be whipped there, but it had hurt, fortunately I had the wherewithal to start counting and say thank you. She let out a cruel laugh and whipped my cock again before moving on to my ass, though she also found time to whip my thighs and hands.
By the time the kettle had boiled my ass was red and hot, she basked in its glow and congratulated me on completing the warm up and winning the use of lube. It was a privilege she said, that could be taken away. She asked me if I'd taken her advice and used the plugs and toys, I said yes, she inspected them and saw they were clean, did you properly disinfect these toys, yes Mistress I said, did you use a condom with them, yes Mistress I said. She slapped me and asked me again did you use a condom with them, yes Mistress I said. Good for you she said you get lube and she slapped me again.
With that she pulled up her skirt, when she had it lifted just above her knees I could see the tip of a strap-on close to her thighs and wondered how I'd not noticed it before as it was bigger than those in her bag, then it became clear she was wearing it like a holster on the inside of her thighs, using garter belts to hold it in place. She continued to drawer her skirt up and freed the enormous toy from her garter belts. She saw my expression as I was looking at her strap-on, pointed and said this isn't that big, we'll expand you over time if you're a good slave and worthy of my continued attention.
Now suck me off and make sure you make it nice and wet, it'll benefit you later. I went to work on her cock, I sucked it like I wanted mine sucking, making sure to coat it all in my saliva; she seemed to appreciate the effort and fucked my mouth a little making me gag. She stopped drew my gaze to hers and said you need to take it, is your mouth dry. I nodded, she took it out of my mouth, bent down and spat in my mouth, I thanked her and she spat again in my mouth before placing her cock deep in my mouth and fucking me. I fought the gag reflex and instead of trying to take fit her cock down my throat I just opened up as wide as could and tried to relax. I felt it push through and slide down my throat and she face fucked me like that for 30 seconds before withdrawing and then using long slow deep strokes on me.
She then withdrew her cock, put a condom on it and provided me with the lube to put on her cock and my ass. She then said I don't need to hear you again and shoved a ball gag in my mouth and blindfolded me. She wandered around me using some of her cuffs to strap me firmly against the table. I couldn't move and couldn't speak, she teased my cock with her caress to check it was still hard for her fortunately for me I'd never been so hard in my life.
I like my men bent over she said, now it's time to fuck you as you had wanted to do to me. She pressed the toy against my ass and waggled it around letting me feel the size and weight of the weapon she wielded before pushing it into me in one motion, it hurt and she knew as she held it there, spanked me, leaned in and told me it would be al-right as when she had finished with me I'd have no more trouble with this toy, that she was going to gape me with this ever-hard toy.
She was true to her word and fucked me hard and deep, towards the end of the fucking she would draw it all the way out and slip it straight back into my now accommodating ass. After she had finished with me, she remembered she'd never had that cup of tea so she put the kettle on again and returned to mercilessly whip my ass whilst it was boiling. This time she used a cane, my screams were muffled through the gag, but I was glad it was in as I couldn't see how I could possibly have thanked her and counted each stroke. My cock had lost it's erection with the power of those strokes. She slapped me and left me as she went to have her tea.
I didn't know how long she left me there, I know I could here her walking around and I couldn't help but picture her wonderful ass, to my amazement my erection had returned. It was then that she came back, she untied me, removed my gag and blindfold. She had changed from her business suit and was clad head to foot in leather. Her black thigh high boots were Italian leather and moulded for her legs, above that was a strap on bigger than the one she had taken me with before; she called it the czar, which was sitting below her tight corset. Her face was covered by a black cat girl mask.
You're free to go and never return she said, however if you want to see me again, you'll have to beg me to cane you and take my new cock. I thought it was humiliating been tied up and fucked, but now I could leave or I could beg for a caning and cock I couldn't take. Oh one more thing she said as she pointed to a video camera in the corner of the room I'll be filming you begging for it if you choose to stay. I had no choice I assumed the position and begged for her to cane me and to fuck me, to do anything and be allowed to come back. She smiled; I may even let you have a copy of the tape she said.