This story is about female domination. If that bothers you please feel free not to read.
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I met her at the St Regis. It was a black tie gala for a foundation headed by Brenda, the wife of my law firm's managing partner. I was named partner a few weeks prior and part of the cost of punching the golden ticket was to donate mid five figures for a seat on the foundation's board. No matter, I'd busted my ass for ten years and I felt on top of the world as I took my seat at the dais.
Janey approached me on my second trip to the bar. She introduced herself with a firm handshake and a bone dry Hendrick's martini with three olives.
Janey winked at me as she handed me the drink, "I do my homework."
"I see that."
She was beautiful. Tall and slender -- she looked athletic but not at all out of place in the expensive dress she was wearing. I was on guard though. I did quite well with women but Janey was a NYC ten and I felt skeptical that she was pure in her intentions. I guessed mid to late 20's and having just cracked 40 that meant dateable but nothing serious.
We chatted for 30 minutes or so. She was charming; I felt smitten by her attention and had to be dragged away by Brenda to give my speech. It turned out she was an associate at a small but prestigious boutique law firm that my firm worked with a bit in the M&A space. As a litigator I wasn't terribly familiar with that area but we had several mutual acquaintances. I found out later that a woman who worked at Janey's firm had recommended me to her after we had worked together on a pro bono matter. Janey had arranged for her firm to buy a table in order to introduce herself.
I looked for Janey after the festivities but couldn't find her. Disappointed, I eventually headed home with a distant second choice. Over the next few days I thought of Janey to the point of distraction. I could have tracked down her number but felt that a slow play would be better suited given the age disparity. I remained skeptical she had romantic inclinations towards me but couldn't help but remain hopeful.
Exactly a week after the gala I received a text from Janey telling me to meet her for dinner at D' Amico's at 9:00 that evening. I was flattered with her pursuit and felt butterflies at the thought of meeting her again. At the same time, I was annoyed that she expected me to drop everything and meet her in less than an hour. On top of that, D' Amico's was the toughest table to get in town. I replied a bit condescendingly that it might be tough for me to get a table with such short notice. She replied that she was having a drink at the bar with a friend and her table would be ready soon.
Her reply humbled me and I excused myself from the friends I was sharing a drink with. I hustled to meet Janey. She looked gorgeous again. She greeted me warmly and we were seated as soon as I arrived. Janey spoke to the waiter in fluent Italian and soon the wine and food courses were coming with no input from myself. The waiter made a point of having Janey taste the wine and never said a word to me. Nevertheless, the dinner was amazing and Janey even more charming than before. Whipsmart and funny. Also more forward than I was accustomed to -- she grabbed my knee several times during the dinner and even lightly traced my cock with her foot as the waiter brought the lamb shank. At the end of the meal I tried to grab the check but Janey had taken care of it. A car was waiting for us outside and I tried to remain nonchalant as Janey told me she was coming back to my place for a nightcap.
My doorman winked at me when he saw the beauty on my arm. My conceit and excitement covered up the discomfort with Janey having called all the shots up to now. I assured myself that things would certainly be different in my apartment. I imagined having her in my bed with her ankles up by her ears.
Janey never gave ground. She poured us both a Scotch neat by the time I hung her jacket. We talked for hours and there was never quite the right moment to make a move. I noted it was past 2:00 AM when she excused herself to use the facilities and I was determined to close the deal upon her return.
Janey threw me off balance by walking past me and sitting across from me in a leather accent chair. She stared into my eyes and spread her legs slightly as she beckoned me to her with a finger. I approached without thinking and felt awkward as I stood in front of her. She reclined back in the chair as she told me to get down. I sat on the coffee table behind me. She lifted her hips in that magical way women do when they are taking off their panties and I couldn't help but stare between her legs as she told me to kneel. I hesitated and in a sterner voice Janey said, "kneel baby... I want to see if your pretty mouth can do more than talk."
The same discomfort arose but I brooked no protest as she wrapped her feet behind my head and brought me into the prettiest pink petals I had ever seen. She gasped as my tongue swept lightly over her clit and moaned appreciatively as I continued to lick her gently. She would direct me occasionally but mostly allowed me to learn how to please her by following her breathing and moans as I licked her.
She fed my uneasiness by telling me that I had teased her all night and it was about time I thanked her on my knees for the dinner. She was further emboldened by my erection that she would occasionally trace with her foot. As her excitement grew, her language became bolder. She told me to look up at her and I felt like one of the countless women I had done the same to as they fellated me. Nevertheless, I knew once I finished with her I would soon be fucking her and the world would be turned right side up again. I put two fingers in her and sped up my tongue on her clit. She came hard and squeezed her thighs tightly on my head as she did so. I expected her to loosen her grip on my head and began to undo my belt as I planned to fuck her right there on that chair.
Janey had other plans though. She kept her legs wrapped around my head and told me to put my tongue in her and to keep looking up at her. I decided to tolerate a bit more in order to get in her pants. I hated her telling me how much she loved knowing that I swallowed and teased me about drinking her cum. It felt emasculating. As though our roles were reversed. My neck began to ache and I tapped her legs to indicate I was done. She smirked slightly and kept me in place for just long enough more to make a point.
She stood up suddenly and was out my door before I could stand properly on my aching knees. I felt humiliated at how Janey had treated me but found myself constantly checking my phone to see if she texted. With no word from her, I slept fitfully and woke up exhausted. I was completely unproductive at work given my constant replaying of the night before. To my chagrin I had to masturbate three times during the day in order to be able to think at all. Every time I brought myself to I couldn't help but think of myself on my knees following her directions.
I waited for her to reach out to me. After the way Janey treated me I knew I would look pathetic to be the first to reach out. After 24 hours I couldn't wait further and shot her a brief text. I broke down and texted again the next day after not hearing back from her. I felt ridiculous. A few days later she texted me a picture of her beautiful pussy with the message, "beg for it." I felt completely flummoxed and my desire to see her again outweighed my common sense and I replied as she asked. I sent about 5 texts in quick succession begging to fuck and lick her pussy but she didn't reply until the next morning with a, "wrong number... lol."
I felt rage and humiliation and swore I wouldn't respond to her again. However, the next night Janey texted me. She apologized for her prior text explaining I was in her contacts immediately above the intended recipient. I appreciated her words but felt jealous that she appeared to be involved with someone else. As we texted back and forth my anger melted and I told myself I was being quite over-sensitive given that we'd been on a single date.
Janey told me to meet her. She was at a club with friends. I was more excited than I cared to admit to see her, nevertheless I was about to decline to maintain my dignity when she sent me a picture of her wearing a skirt so short that I immediately reversed my decision and said I'd meet her.
I gave the bouncer a couple of Franklins to avoid the velvet rope and a hostess brought me to Janey and her friends in the VIP. I was too old for this scene but had a great time regardless. Janey looked amazing and she showered me with attention. After a few drinks and a couple of shots I was feeling no pain. In spite of the loud music we were able to have a conversation. She plainly told me that she liked me a lot but often found men my age to be less fun -- too inhibited and set in their ways. Janey would occasionally lean in and whisper how sexy my mouth was and how she couldn't wait to use it again. I told her how badly I wanted to fuck her. She smiled. Her words were ambiguous, "then do as you're told."
With those words still hanging in the air, she grabbed my hand and led me up to the back of the club. There was a deserted booth and she pulled me in giggling.
"I've always wanted to do this. Are you game?"
I was sure she wanted to fuck and hurriedly began to undo my belt.
"No baby, not yet... lick my ass."
"What?"
"Oh God, you're not really going to be boring?"
She shifted her weight in a way that made me feel as though she might leave. I felt on the defensive. I grabbed her arm, pulled her in and said, "No... I mean yes... I will..." I felt like an awkward teen as she smirked at me and pressed her advantage.
