Now that’s quite an admission for an otherwise fairly alpha male. I mean, I’ve never been the bar-brawling type, especially with the careful psychological training we got in aikido about ethical use of force. But I didn’t get to where I’ve gotten in the, shall we say, rather intense legal world, by not striving to win, I’m sure you’ll appreciate. I never did figure out any language to even hint to a woman about what I so desperately hoped she’d do (because she really wanted to, I mean, not just to please me, which I suspect at least some women would genuinely try if it had a chance of pleasing me). And finally, after my move to San Francisco, I kind of gave up on that pipe dream. I reconnected with a couple of old fucking-buddies from my clerking days, and contented myself with a robust internet habit of reading about men submitting their bare asses to the dommes of their dreams.
And then, everything changed, at first without my even realizing it. A new paralegal was assigned to assist my clerks. I glanced twice when I first saw her, as she perfectly fit the profile: petite, slender, brunette (piled on her head in a charming chignon), generous Italian mouth under huge brown eyes, small breasted for a Mediterranean-bred woman, and, of course, a delectable firm round overtly female ass above long slender legs. She would be in charge of my correspondence as well, and had an air of bemused competence about her that I found charmingly spirited. It was as though she were saying, “Yes, I’m well aware you are very accomplished and handsome and totally admirable in my eyes, but that doesn’t make me your inferior or incapable of finding amusement in noting and subtly teasing you about your foibles…”
Coming from a woman who already rang my chimes in so many other ways, this saucy attitude absolutely sucked me in, in a way that I hadn’t felt since…well, actually, ever. She stayed on my mind, her friendly, sardonic gaze lingering in my thoughts, until finally I gave in to my overpowering impulse to investigate this very unprecedented state of being she induced in me. I called her into my office at the end of work one day, after everyone had left but me (it was a matter of honor to her to arrive before I did and leave after – how she knew those times, I’ll never know). I felt shaky, a bit trembling, like I never had since in my entire dating career. I never once asked a woman out without an iron-clad indication that my move would meet with unambivalent approval. A little bit arrogant, I’m sure you’ll agree…but have no fear, as you will soon see I have been…humbled…in the most thorough way imaginable.
I finally just sighed, aware of my deepening flush that so gave me away only around my Mother, and now, apparently her. By the way, she had (and still has, of course, aside from Mommy) a name: It is Hattie, short for Harriett, and she looked at me inquisitively with those alert brown eyes, waiting to find out what I wanted. I stammered out, “Hattie…I don’t know if you’ve…sensed my interest, but I find myself quite…strongly…attracted to you…I wonder if you’d…go out with me?”
For about the only time since, she took pity on me in my miserable suspense and smiled her megawatt grin and dropped a dead wink as she retorted, “Jesus Christ, Judge, I thought you’d never ask!”
The wash of relief that overtook my body was unprecedented, as I seemed to intuitively relax into the powerful way in which she has held me in relationship, literally ever since that very moment. I smiled and said, “You’d best call me Jacob, Hattie, and do you see any reason why we couldn’t have a drink?”
And then she again showed mercy and took the next step for me, “Oh, Jacob, don’t you be so silly. We shouldn’t be seen together socially, so how about you drive me to your place and we can have a drink there, if you’d like?”
Well, I absolutely would like, and since I wasn’t wearing robes and my suit jacket was on its hanger behind my door, the solid evidence of how much I liked that idea was quite evident to my sharp-eyed paralegal. She gave another wink and murmured, “Well, I guess you would, wouldn’t you? I’ll get my coat and meet you in the parking garage, Jacob, and we’ll take it from there!” Soon, we were out on the warm late autumn evening, and then in the elevator on the way up to my condo on the 17th floor. I’ll admit to a bit of vanity, as I paid a premium for the ultimate killer post card view from Berkeley to the Golden Gate. And when we entered the foyer and there was the late-sunset skyscape, she was suitably (though still a bit wryly) impressed.
Her arm snaked around my waist as we watched the steadily muting colors and she murmured, “This would be a good time to kiss me, Jacob.” What was a properly raised gentleman to do but comply with such a refreshingly forward request? I leaned in for what once again turned out to be the kiss of my life. She was at least six inches shorter than me, probably closer to eight, and weighed about half of my 220 pounds (I was proud to have held the same weight and belt size since college). And yet, from the instant of that kiss, the tender but insistent demand that I show up, be entirely present in what was happening between us, Hattie had me quite firmly in her hands, eventually quite literally. She delighted in demanding my focus absolutely to the intersection between her and me, in a vast number of different ways, as I have come to discover.
Soon her nimble fingers were shucking my coat to the floor and caressing my upper body through my shirt with the same wonderful combination of affection and urgency that she showers me with every single day. We continued our kiss as my hands found her firm back, delighted to cup two perfect taut boyish moons. I moaned into her mouth, and she disengaged a bit to smile and murmur, “Oh, I see our Jacob likes tidy little bottoms, doesn’t he?” She then gave that same part of me an equally brazen fondling to the one I was conducting on her own delightful little ass. And then her hands seemed to migrate to my belt and then my zipper and soon she knelt ever so gracefully to take my dick head in the sweetest most compliant mouth (so different from its usual ironic acerbity) as her hands expertly fondled my balls.
Well, I can tell you, it didn’t take long before I was digging my fingers into her rapidly-disarraying chignon and bellowing my delights as I pumped my spend into her mouth with the most pleasure I could ever recall (to that point…). She cheerfully drank it down, even though she later explained to me she really dislikes the taste and consistency of male ejaculate. But as she also informed me, much later and in the midst of some rather outré torment she was inflicting on me, doing something a bit unpleasant in order to achieve something highly desirable, like drinking in my masculine power through my cock like some sort of succubus, often seems a good bargain to her.
Once I was spent inside her generous mouth, Hattie smiled up at me looking very contented as she drew her mouth off of my cock and rose to kiss me on the lips, making me taste my come along with her own heady aroma. Then she said, “Now it’s Hattie’s turn, Jacob, so where would you like to lay me down so you can eat my pussy until you make me scream?”
I suggested the nearby couch would do just fine, and she led me there with a surprisingly firm grip, still keeping up her intense physical engagement with me via her hands. She seemed to want to be touching me almost, well, fiercely the whole time she was around me, always sending me a message through her caressing hands that she hungered to stroke me, to make me feel…I guess one would have to say…both possessed and loved.
This small dynamo of a woman was not in the least coy, slipping out of her panties quite matter of factly before she lay on the couch and spread her legs, offering herself to me. I knelt and flipped up her skirt, and there it was: her almost completely depilated crotch, its central flower topped with a tiny triangle of short dark brown pubes, the rest left totally hairless. And its lips were swollen and bright pink with her arousal, glistening with her body’s unequivocal message about how welcome my cock was going to be.
I took my time, tantalizing her a bit by nuzzling and licking the delicate creases defining her torso from her hips, lightly grazing the outer edges of her nether lips as she writhed prettily and grasped by head as possessively as I had hers. She whispered fiercely, “Now, Jacob, you don’t want to make me angry, do you? Get that tongue to work right where it belongs, or else!” This threat immediately made my cock surge back to full erection, as I began in earnest to sense the direction, the wonderful, amazing, unhoped for pathway, that this relationship seemed poised to take.
But in the meantime, I had a demanding pussy to eat, and twenty years of training and practice in that art, and I put all of that to work trying my earnest utmost to please this unsettling woman. Not that it was hard to accomplish, as she seemed pretty turned on. I was able to perform just a few lazy, probing encirclements of her clitoris with my tongue before she surged into orgasm. Her paroxysms of pleasure were frankly a little bit daunting to the shy part of me, who was unused to women so frankly shouting out their enjoyment. Thank God the building was fancy enough that its soundproofing ensured I had never heard a peep out of any of my neighbors, so I suppose they haven’t heard us either.