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Interrogation Chronicles: One-Night Shrink (Chapter 1)
🕑 Added 2025-06-12 13:00:03 +0000 UTCThe three-day conference was over, but I still had another night to make the most of the trip before flying home to my wife, and frankly, the nights were the only real reason I signed up for these kinds of corporate time-wasters anyway. I was two-for-two the past couple evenings, scoring with a couple of girls fresh out of college who were impressed by my business cards, not to mention the heat I came packing in my jockstrap. Not that I had both of them at once, obviously. I’m not THAT much of a player. One was a solid 8, and to be honest, the other was just barely a 7 with makeup on, but God she made up the difference with the sexiest kind of low self-esteem, so I can’t complain.
Tonight, though, I was ready to go out with a bang, pun fully intended. I’d have my best wingman Doug by my side again, despite all his hemming-and-hawing about whether he was doing the “right” thing by helping me do this. He’s certainly lost his edge since getting married. The agreement we landed on is he looks the other way after helping me clinch a deal with a new piece, and I take to my grave that time last year he got stupid drunk and ate ass on somebody we’re both, in hindsight, 70% sure was a dude.
Anyhow, we freshened up, hit the ATM, and checked out a watering hole a little more upper crust than the semi-respectable dives we’d visited the first two nights. At first I had my eye on some of the girls I guessed were in marketing or finance: serious, sexy, definitely under thirty, and ripe for one-night stands. However, as we wandered up to the top floor of the glitzy place to get the lay of the land, pretty much every plan I had for how this night would proceed was rewritten the moment I laid eyes on her. I know, it sounds corny, but this wasn’t so much a “love at first sight” situation as a “holy fucking Christ-and-a-half just look at those tits” situation.
Just so I don’t sound too single-minded, though, while the rack on this woman seated at the end of the top-floor bar was unquestionably the most mesmerizing pair I’d ever had the pleasure to ogle, rigidly perky and cream-white and epically humongous, she had plenty of other qualities which drew my attention and forced me to adjust my stance so my pants didn’t tent too much. The legs on this woman seemed to go on for days, but with the kind of little-extra thickness in the thigh and hindquarter region that I always value in a hookup, mostly for grabbing and clapping purposes later in the heat of a good fuck, but which can be tragically hard to find in some of the pencil-thin co-eds I usually chase.
She had some roomy hips, but a waist with an hourglass inward-slope that forced me to wonder for a moment if she was even real. Those marvelously spacious knockers were still the main course though, and undoubtedly augmented, but I didn’t care about that – the fake ones, when done correctly like these appeared to be, only meant you had more license to go H.A.M. during the buildup. Not a hair was out of place, silky and straight as it draped over her shoulder, and strangely luminous despite its obsidian-black hue. Her face was utterly bewitching; she wasn’t a conventional knockout-10, but lovely and beguiling nonetheless, supremely elegant in ways that my normal game also couldn’t hope to claim. The fluttering eyelashes framing her shadowed lids, the high cheekbones, the natural-pursing of her crimson-glossed lips, and even her eyes that seemed to pierce into me before she’d even met my gaze all gave me a difficult choice of staring transfixed at her face or her monstrously bulbous boobs, though obviously I settled on the latter.
What puzzled me the most was the determination of her age. From certain angles, I guessed she was fifteen years older than me – though I don’t say that with any disgust – and from others, barely five. Her complexion was, especially under the glamorous bar lights, pale as the moon, and that went double for her mammoth cleavage, showing “character” in a few places, but by no means saggy or wrinkly, even with the seasoned volume of age freckles she had on display. I don’t usually go for women older than me, let alone my same age, but sometimes I’m just in the mood for someone who knows exactly what she’s doing every step of the way, and I felt surer about this one than I did any other figure in the building. Hot as those grad school girls can be, a lot of them suffer when it comes to more complicated sexual finales, and some of the really dopey ones can’t even handle the basics. Plus, in spite of any extra “experience” this dark-haired beauty may have had, she lacked all the usual no-gos that forty-something chicks sometimes have. Those funbags boldly defied gravity, even for all their incredible lightly-jiggly mass, that ass absolutely wouldn’t quit, and even the way her long fingers curled around that martini glass stem, so strong and still delicate, intrigued me.
“So what’re you thinking?” Doug asked, sighing wistfully as he gazed at a blonde woman downstairs he was too ethical to try getting with, but I was already marching toward the bar. He hustled after me, taking up some empty space close but not too close to my chosen target, who as far as I could tell was here alone.
At this point, though, I wasn’t even certain I needed a wingman, especially after I made introductions over the first drinks, learned her name was “Angie” (and fed her mine as “John” just to be safe), and received back a smile that told me she at least tentatively liked what she saw. It was my game to lose now. Still, I appreciated the backup from Doug, who boosted me with a little meaningless back-and-forth between the three of us, just enough to help convince Angie that I most likely didn’t have mason jars of piss lining my shelves at home. Sooner even than usual, however, I gave him the signal to that I’d take it from here. Frankly I think he was grateful, so he could get back to pretending I wasn’t “cheating” on my wife (though can you really call it cheating when the marriage is past the decade mark, getting stale, and she refuses to wear lingerie anymore?) by pining after that twenty-three-year-old blonde downstairs from afar.
“I admire your technique here,” Angie said to me, once Doug had visibly exited the conversation. She angled herself just far enough away from the bar to face me now that I was blessed with a fuller view to her tits, which were windowed by a more revealing neckline than I’d estimated even from seeing that sleek navy-blue dress from the side. It was all I could do to maintain eye contact without venturing lower to explore the seemingly-expanded landscape of paunchy veiny chest flesh. Christ, I hoped I’d get the chance to touch them, and then bury myself in them. “Let’s say you get an eight out of ten this time. I dock you one point for pretending you and your friend didn’t start up that conversation about stock options just to impress me, and another for that fake laugh of yours. Believe me, if I thought that was your real laugh, we wouldn’t even still be talking. And as for finance, trust me, that’s not the way you’re going to hold my interest. Don’t worry, though. That’s a higher score than most receive. You can’t imagine how many times I’m asked whether I come here often. The answer is yes, but not for little boys who want to waste my time.”
Though I didn’t let it show, I was instantly taken aback. Normally an immediate dressing-down like this would’ve been an alarm bell which told me the girl was too smart and too ahead of me in the game already, which was a sure sign she’d depart stage left right when she had me breathing heavier, maybe with a splashed drink decorating my face. A big fat red flag.
Except she’d spoken with such sultry sincerity, held me in her thrall with that exacting gaze which told me she was still invested in whatever-was-happening here, and most likely made that posture adjustment purely to give me a bit more busty eye candy to munch on, that I quieted said alarms and red flags. Like I said, I wanted someone who knew exactly what they were doing, and right now, I was getting the vibe that Angie was clinical perfection when it came to unorthodox sexual maneuvers. If I was going to have a chance at seeing that mastery in action, I’d also have to take the chance that she was too brainy for a one-night stand. One more glimpse of those heavenly hooters told me the risk was worth it, and then some.
“Funny, I think that’s a higher score than I’ve ever gotten,” I said. “The only problem is, you’re really cutting my options short here. The money talk and the laugh are off-limits. That means no business or pleasure.”
“Maybe you’ve just got to re-examine what you count as pleasurable,” Angie smoothly responded, taking a long sip from her drink without breaking eye contact. When she set the glass back down, she gave her shoulders a gentle shimmy, which in turn briefly animated her chest to magnificently wobble again. “Or business too, for that matter, but I think that’s less important. Don’t you?”
“Always.”
I started in on my second drink, and Angie let me buy her another, despite her disinterest in any shows of affluence. I’ve been known to down at least five drinks before really feeling a buzz, which then threw me off when I started feeling a fuzzy headiness by the bottom of that second glass. Still, I didn’t mind, as Angie’s unbelievable assets were likely to blame for my drunken preoccupation, rather than even the stiffest liquor I could’ve ordered. As we talked, both of us skillfully sidestepping many specifics about our lives (another confirmation that she was amenable to the one-night-stand program), I found it truly difficult to keep my gaze from sinking deep into a stare-down with that freckly fault line of her boob flesh like a warm bubble bath. Hell, the dumber the girl is, the more I can usually get away with openly drinking in her goods, even as a way to tell her it’s about time we sealed the deal. In the case of Angie, though, I knew I had to play it cool as long as my willpower allowed me, because her interest and unflinching honesty aside, something told me she wouldn’t take kindly to being looked upon like a living set of beach ball-sized tits on legs.
And yet still an intuitive voice told me that she was inviting me to look at those knockers she was obviously so proud of, daring and desiring my gaze to be drawn there, but was too classy to outright suggest such a thing. Not yet, anyway. So I indulged that instinct.
The neckline on Angie’s blue dress seemed to magically sink lower and vaster each time she made an adjustment in her seated posture, but also, after we’d been sitting together at the upstairs bar for nearing an entire hour now (sorry, Doug), each of us had naturally shifted closer, almost elbow-to-elbow, and we were facing each other more than the wall of glistening libations. When she sighed, I could feel the warmth of her breath on my neck. She was beginning to pitch forward, too, occasionally putting her hand on my shoulder mid-speech and stroking my sleeve with manicured apple-red nails and long fingers that I couldn’t help but imagine would feel fantastic wrapped authoritatively around certain parts of my anatomy. Best of all, this narrowed proximity gave me the best view yet at those bulging prizewinners strapped tightly into her garments like a pair of smuggled watermelons, and while I wasn’t naïve enough to think she hadn’t noticed some or all of my peek-sneaking, my apparent attraction to her biggest roundest features did nothing to dent her enthusiasm. In fact, Angie was smiling and laughing more as my charms melted her haughty somewhat-icy exterior.
I’d have to have been crazy at this point to have walked away, when she was giving me so many signals. I had half a mind to invite her to my hotel already so we could start tearing into each other like animals, but that same intuition (which hadn’t yet steered me wrong) told me that Angie herself would want to initiate the main event. If there was one thing I’d learned for certain about this captivating woman over the course of our vague double-entendre-laden chit-chat, it was that she couldn’t stand a man who wanted to be fully in charge. And tonight, by this point in my increasing thirst for Angie and her blubbery intricately-veined bongos, I was perfectly willing to inhabit whatever kind of man she could possibly want me to be.
“So now that we’ve gotten to know each other a little better, John…” Angie said, her freshest drink still hovering by her lips, causing the alcohol to ripple at her warm whisper. “…I have a very telling philosophical question to ask you.”
“Fire away.”
“Ass man or boob man?”
It was lucky I’d had a while now to get used to this woman’s style, or else I might’ve done a spit-take right onto her tits at this question. Of course, much as spewing into her cleavage would probably taint my carefully-crafted reputation with her, I also couldn’t help but prickle with delight at the thought of seeing liquid beads alighting on Angie’s skin like rain, giving her rack even more of a luminescent shine, then tracing down that rotund flesh in wet zagging lines all the way below the cut of her neckline, regretfully out of my sight.
“You really do get a kick out of trying to stump me, don’t you?”
“Not at all,” she replied, setting her glass back down and then hypnotically devoting all unblinking attention to me. That coy smirk broadened in tandem with her garment’s breast window when she again tilted forward by a few more sensuous degrees, revealing precious additional real estate of those gorgeously flabby cream-taut zonkers. “I just find it can be very revealing.”
“You enjoy having things revealed, do you?”
“Only so far as it helps cut a man down to size,” Angie responded with a seductive wink.
“Am I allowed to choose both?”
“Oh, I suppose. But only one can be your title. Something-man. That’s what I’m after. See, it’s part of a theory I’m working on. I tend to find that married men, more than anyone else, have a definitive choice. And I’d like to know if the same applies to you.”
Again the sirens went off in my head. I was normally so good at remembering to take off my wedding ring before I headed out clubbing during these cruising vacations, that I must’ve let the confidence of the past two nights go to my head. Immediately at her invoking of the M-word, I reached for my finger, only to find it was curiously bare. I had remembered to stash the band.
“How did you-”
“There are other ways to tell besides a ring, you know. I could smell the marriage all over you before you even said a word to me,” Angie declared with a straight face, before cracking a smile. “All right, I’m not that good. But it wasn’t long after we started talking that I noticed.”
“Oh.” I tried to play it cool, knowing that any whiff of assholery on my part might lead to trouble, especially if Angie was about to toss a drink in my face after all, despite spending so long first getting my hopes up before showing off her Sherlockian attention to detail. Had she really put in all this time, just to humiliate me later rather than sooner about my no-good cheating ways? “Is that a… problem, or-”
“Please. Do I really strike you as someone who gives two damns about the sanctity of marriage?” the woman laughed, thankfully interrupting me with a lilting giggle, and a dainty slurp from her drink that ended in placing the empty glass back on the bar, rather than chucking it at my nose. When freed, her hand found its way to the shoulder of her dress, gently burrowing a thumb beneath until she found a strap to tug upon at lazy intervals, thus causing one-half of her bosom to go snug inside the regularly narrowing confines of the silky cloth every few seconds. “If anything, that ring you normally wear makes you into a more… interesting way to spend my evening. I don’t believe I’m crossing a line to suggest that you only go on the prowl while you’re away from home. Far away from home. Which means you’re probably finding tedium inside your sacred bonds. Which makes you a more, well, grateful and shall we say… adorably desperate evening companion for a girl like me. How does all that strike you?”
I was getting used to these sly counterintuitively-lascivious takedowns from Angie by now. Even starting to appreciate them, when a lesser man might’ve walked off in a shameful huff. This time, I didn’t so much as bristle inside or out at her brutal yet fair reading of my whole self, especially because she didn’t sound the least bit less interested in sticking around with me tonight, despite having understood my hungry baser instincts better than she’d let on before. Maybe she not only enjoyed, but had a kink for men like me who were getting sick of our wives, and ready to play the part of a living sex doll with a mondo-boobed stranger, so long as it meant some goddamned variety in bed. How could I complain about such an oddly perfect symbiosis between us?
“It strikes me just fine.”
“Good. Not everyone feels that way. But, you still didn’t answer my question.”
“Boob man,” I answered right away. “No contest.”
“I thought as much.”
