Not long after my eighteenth birthday, a close family friend introduced me to an exclusive club for the rich and powerful. It didn’t have a name. Supposedly it wasn’t even a legal entity. It was just referred to as The Club. Very ‘Eyes Wide Shut’ you may be thinking. Yes and no. It wasn’t free. Dad was footing the bill, of course, because my education has always been paramount to him. I found out later that he could have bought me a Foggy Bottom brownstone for what my membership cost but I would come to appreciate his investment.
Once a year the club held a party at a secret location in the DC area to welcome new members. Becoming a member when most guys my age were still cruising malls to meet chicks was meant to demonstrate to me that limitations were for little people as if that hadn’t already been the lesson of my entire life up til now.
The night of my initiation I met ‘uncle’ Drew at a swank steakhouse in Georgetown knowing nothing about it. It was a month after my birthday and he pitched the dinner as an apology for missing my party if you could call it that. Just me and the fam and the servants pretending to enjoy ourselves until Mom got drunk and lit into Janka for some perceived sign of disrespect. I told him there was no need for an apology.
He had been Dad’s partner since they founded the firm twenty five years ago so convo with him usually trended towards the good ole’ days when he and pop were young guns taking on the legal establishment. Riveting stuff. He insisted I would be glad if I showed.
I couldn’t flat out refuse a close family friend so with the expectation of another evening spent laboriously feigning interest in genius legal maneuvers, I accepted.
When the hostess led me to his table in a private room at the back of the restaurant I was unsurprised to see him sitting next to a stunning freckle skinned redhead in her late thirties. She was pretty if severe and dressed as she had just come from the office. Not really his type based on his history, but still.
I *was* a little surprised to see a second woman sitting across from her next to the only open seat left at the four top.
I know who Kelly Ripa is because whenever I am home I am required to start my days absorbing her vapid nonsense from various TVs throughout the house whether or not Mother is even home. The maids have a regimen. Though the entire format is an insult to humanity I have to admit that I have lingered in front of that odious show to play the *No Means Yes* game I learned at boarding school with Kelly Ripa as the protagonist. What I wouldn’t do to Kelly Ripa.
Either I was crazy or that was Kelly Ripa sitting there with her hair pulled up in twin buns kind of like that chick from the original Star Wars. (Yes, I’ve seen it. And yes, I liked it.) She and Drew stood up as I approached while the redheaded woman remained seated. My confusion must have been obvious because she laughed as I approached and said, “I told you so.” to Drew. The illusion wore off the more I studied her, but at the very least they had to be related. The same square jaw and dazzling smile. The same pixieish prepubescent body in spite of the fact that she was probably forty. I tried to act cool once I realized my mistake but it was way too late for that. I forced myself to stop staring at her and gave Drew a manly hug.
I saw that they had been there long enough to have a round of drinks. Or at least two of them were drinking. Drew introduced me to the double bunned blond, Amanda, but neglected to introduce the attractive redhead still seated next to him. I ignored the oversight and introduced myself to her. She took my offered hand and smiled thinly, but didn’t speak. I had no idea what passed for acceptable behavior in their world so I let it pass and sat down across from Drew feeling young and underdressed.
I was in the middle of answering some small talk questions about my plans for college as if anyone gave a shit when the waitress came in to take our orders. She took Amanda’s order then asked the redhead who’s name I had not yet learned what she would have. The woman gave the waitress an insincere smile then looked expectantly at Drew. Okay, that was weird. Drew smiled a humorless smile right back at her but allowed the silence to continue. As the seconds mounted the air in our little room thickened with awkward.
After about thirty or forty seconds of silence from everybody, our waitress gave a subtle shake of her head as if just remembering that time hadn’t stopped and pivoted smoothly in my direction.
“And for the gentleman?”
Now it was my turn to gawp in silence. Food? My mind was fully highjacked with processing the implications of the woman’s unwillingness or inability to speak, and she wanted to know about food? I must have added another ten or fifteen seconds to the subjective years of silence from our team when Drew, enjoying the shit out of all of this finally ended the embargo by joking that I was too young and naive to know what was good yet. He ordered steaks and scotch for both of us and said that the lady needed nothing. The waitress accepted all this without question and left the room with only her pink cheeks betraying any recognition of the tangible weirdness at our table.
The blond made eye contact with me for just a second before she looked away again but that was all it took to tell me something wasn’t kosher here. Drew saw me getting it and smiled a Cheshire grin. Any expectations of a boring obligatory dinner with a family friend vaporized as the night suddenly became a portal to something wicked and adult. She wasn’t being rude, she wasn’t *allowed* to speak. I looked back at her and saw her cheeks darken with humiliation as I finally joined the party.
Drew grinned at me and gave me the eyebrow waggle as if to say, ‘Watch this!’
“Take off your jacket,” he ordered her. She took a moment to look affronted, but then she did it. Fuck me.
“And your bra.” This time she glared at him with an expression that said, ‘Really?’
I looked at Amanda to see how she was reacting to this, but she just looked at me briefly with a coy smile and returned to watching them impassively. What the fuck?
They stared at each other for a few seconds more until Drew raised his eyebrows in a silent question. She seemed to be calculating something. My mind raced. Why the fuck was this woman being made to abase herself in front of a kid? I was at a fucking, loss. I definitely wasn’t bored, though.
Without looking away from Drew she reached behind her back with one arm and unfastened her bra. Then she did that slip an arm out of one sleeve and pull the empty bra from the other thing that looks like a magic trick to men. She started to stuff her lacy white bra into the pocket of her jacket now hanging on the back of her chair when Drew interrupted her.
“On the table.”
She paused for only a second this time, then held out her hand at shoulder level and let the bra fall to the table in front of her with a defiant glare at Drew as if to say, ‘Is that all you got?’ and leaned back against her chair. I couldn’t help but notice that her decidedly puffy areolae were now plainly visible through her clingy blouse. I shifted a little in my seat.
Now it was Drew’s turn to flash an insincere smile at her before turning his attention back to meaningless conversation with me while we all silently agreed to pretend not to notice that he was openly humiliating this woman.
When the waitress returned with our drinks she joined us in pretending not to notice that the woman’s bra was sitting on the table and quickly hustled from the room with assurances that our dinners would be out soon.
It got weirder. Halfway through the longest meal of my life Drew stood up from the table mid diatribe about all the potential avenues forward a man my age has open to them if only they had the wisdom thing I have heard variations on from various elders over the years, and stepped behind the redhead. Without a break in his ‘keys to the universe’ monologue, he grabbed the back of her head by her ponytail. She didn’t seem surprised by this strange intimacy and just stared ahead at Amanda. Drew was saying something about the semantical differences of the word ’takers’ while he reached around with his free hand and roughly smeared her face.
I had questions.
I glanced at Amanda and caught her giving the other woman a subtle nod.
Okay, lots of questions.
The redhead didn’t resist as he guided her forward and down to the table until her cheek was pressed into the bra with her reddening face bent towards me. She was breathing quickly through her nose as her angry green eyes met mine again. In spite of the fact that she was the one being abused, I was intimidated by her electric gaze.
From his pocket Drew produced a pair of handcuffs. Motherfucking handcuffs! She didn’t even resist as he proceeded to lock her hands together behind her back.
He leaned her back in her chair again and grabbed the front of her shirt with both hands. He looked at me with a wicked grin and said, “In this life, you either take what you want, or you take what you are given.” And with that, he ripped her shirt apart sending little white buttons skittering across the table and floor. He sat back down in his chair with a casual air like he was just returning from the bathroom or something.
“So, Daniel… your dad tells me you are thinking about a career in law.”
I didn’t even try to answer. One of her small teardrop-shaped tits was completely uncovered by the open shirt. The sight of one conical pale and puffy areola jutting from the freckled globe of her breast made me gasp inwardly. (I hoped.) Her artfully applied makeup was smudged and streaked, and her hair was a drunken nest of wavy strays pulled loose from her careful ponytail. She was shaking and breathing heavily through her nose but she maintained a defiant expression as she glared off into the distance.
Guiltily, I realized I had been staring at her heaving chest when I noticed that both Amanda and Drew were looking at me with mirthful expressions. I felt my cheeks get hot.
I don’t remember much more about our conversation after that because I was probably dissociating a little. (Yes, I’ve had a little therapy.) And because my focus was 100% on not looking at the tit. At some point, it occurred to me that Amanda was touching me a lot when we spoke. Not that I minded, but I was only certain of the fact that I was out of my depth so I was assuming nothing.
I remember asking myself over and over if I should do something to help the nameless woman because she was clearly unhappy, but it was Drew doing it. Plus, she was going along with it. Not only that, but Amanda was somehow in cahoots with her. Clearly I did not have all the data yet. I ate a few more bites of steak confused and embarrassed at my complicity.
The waitress returned to our room only once more to deliver a check and to her credit showed no signs that anything was out of the ordinary. I guess she’s seen some things.
When thank fucking God that dinner ended we were met by a limo out front. The woman’s coat, bra, and purse were abandoned at our table as Drew led her out of the restaurant through the dinner crowd still cuffed like he was perp walking an especially sexy criminal he had just taken down by violent means. Only her form-fitting grey skirt showed no signs of damage. Not sure how people read what was going on but nobody did a fucking thing about it as he frog-marched her tits out to the limo. I did see a couple of phones pop up to record our parade as Amanda trailed them and I followed behind her in a daze trying to recalibrate my expectations on the fly.
We were met by a fit and somehow menacing Japanese man in a driver’s uniform holding open a small aluminum case while a second even more menacing Japanese man in a similar uniform stood by the open door of the car. Two dudes for one limo seemed excessive but Drew seemed okay with it. He parked the blond facing the guy with the case. He made it clear with his hands that she was not to move once he released her then took out his cell, wallet, and keys and placed them in the open case. The chauffeur closed it and pressed some buttons on a numeric panel on the front of the case which made a small blue window light up. Drew pressed his right thumb to the glowing window and the case made a little mechanical whirring noise before audibly locking. The man turned and placed the case in the cab of the limo reemerging with a second case which he then held open for Amanda. She placed her compact handbag in the case and repeated what Drew had done. The man in livery held open a case for me and I looked at Drew. He nodded to me that I should do the same.
It was fucking weird to give up my shit but if that was the price for entering this rabbit hole, then I was in.
Drew bent the cuffed woman forward by what remained of her ponytail and guided her to the front of the spacious stretch with his other hand on her tight ass. Amanda gave me a saucy wink and bent over to follow them in before turning left to sit in the back. I hoped real hard that I was right about what that meant.
Once inside Drew arranged the redhead next to him with their backs to the opaqued window between us and the chauffeur and the other chauffeur while I stood dumbly in the doorway not knowing where to go.
Amanda patted the bench next to her in the back. I lurched in her direction grateful to have one and sat down with a couple of feet of empty couch between us. The door slid closed behind me and a moment later we felt the car accelerate into the night.
Source: reddit.com/r/eroticliterature/comments/f92qfy/the_initiate_bdsm_non_cons_mff