Consumerism Ch. 11-15

Story Info
I crossdress and share a room with my boss during a NYC trip.
5.3k words
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Part 2 of the 7 part series

Updated 12/16/2023
Created 07/14/2023
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11. Outbound Flight

I enter the cramped first-class bathroom, shut the door, and lock it. There is pink noise all around as the jet streams through the sky slightly muted inside the closed off bathroom stall. Normally when I pee on planes I always sit down. Flying makes me a little anxious. Generally, I am fine in my seat. I'm not worried the plane is going to crash or something; I realize that's extremely rare. But standing makes me wary due to turbulence. I look at the toilet. Not dressed like this. I refuse to sit and pee wearing a dress. I'll take my chances, thank you very much. I open the lid, lift my dress, pull my cock from my panties, pee standing like a man, and flush.

I can hear Mr. Bentley laughing. Before I departed to the bathroom, he had struck up a conversation with the gentleman sitting across the aisle from us. Mr. Bentley was trying to put his new Hermès black leather Apple watch in airplane mode. He should just give it to me. I can figure it out for him.

I soap my hands.

"Yeah, it was a birthday gift." I hear Mr. Bentley's voice speak through the thin bathroom door.

I wash my hands.

There's muted chuckling outside. "No actually, that would be the one my secretary gave me. When we were alone in my bedroom. The one she gave me on her knees." More laughter.

I roll my eyes

The door opens. I walk to him and wait patiently.

Mr. Bentley smirks at me, cocks his head, and gets up from his seat. "Hey, before we left the office did you remember to pack my day planner and that new copy ofThe New York Times?" he asks. "We can do the crossword tomorrow morning when we wake up together at the hotel."

"I got it covered, Chief," I respond as I sit down in my leather seat. I notice the man across the aisle stares at us wide eyed. I blush and sink into my chair.

12. Amuse Hotel -- New York City

My eyes peer into the dark void of the blindfold he wrapped around my head. I wear the new Myla lingerie he purchased for me, black and lacy stockings, strapped to a black and frilly garter belt above a thin strapped G-string pair of panties that has black lace over a thin white triangle covering my hard erect penis. The brassier is black and gauzy over white cups. It hangs over the breast forms he bought. It felt so weird looking at me in the mirror when I put them on. Suddenly I had boobs. I didn't like it until I saw the seams on my shoulders. These are fake; just another fashion accessory for him to dress me in. It helps me look cute for him and make him come.

I'm lying on my stomach on the bed with my white high heels strapped to my feet. He's heavy on top of me, pulling at my arms. My hands grab the brass bars of the headboard. I feel his rough, masculine hands pry my fingers off, one by one. He drags me. There's a clicking noise. I pull on my arms and metal clacks against brass. It seemed we had just barely checked in at our hotel. I expected he'd take me out to dinner. We'd drink fine wine together. I'd give him a nice wet blowjob before bedtime and cuddling. Instead, here I was, just recently arrived in our New York hotel room, already dressed in lingerie, blindfolded, and handcuffed to the brass headboard of our rented bed.

The last time I saw him he wore a wool, gray and blue plaid two-button Canali jacket, matching suit trousers held up by a black leather Versace belt with a shiny brass circular logo bearing buckle, over a silk dress shirt, blue tie, and white pocket square. I don't know how he is dressed now. He is off me, and I hear hands fiddling with something. Most likely he searches through our suitcase for something. The hotel door opens before slamming shut. I'm alone. I pull on my arms and the handcuffs scrape up against the brass bars of the bed. I'm stuck here. My body squirms forward. If I get my head close enough, maybe I can remove the blindfold. No, I shouldn't do that. He told me to keep it on. I can't just disobey him like that. I wonder where he went. He could have relaxed here. Sent me on an errand for him. I always love to go and get him coffees and sandwiches. He likes me to bring him the little milk cups. "I know how much you like to slurp white stuff," he always says before he snickers, creams in my coffee, and carefully raises the cup to my lips for me to slurp. I like to lick my lips before going back to my desk and fantasizing about how he tricked me into letting him come in my mouth.

I pull at my left cuff with my right hand. He double locked them. I'm stuck. Why did he lock me up like this? He wouldn't do all of this for a blowjob. He must want to have sex with me in the way gay men do. I guess he expects to put his hard cock up my ass. I rattle the cuffs. His penis is so big though. I've never stuck anything up my ass before. Him fitting that big prick of his inside me; it's awfully ambitious of him.

I listen outside. Our hotel room is on the third floor. I can hear New York City traffic as it passes up and down the street by the hotel. Occasionally, I hear the subway rumble underneath the ground below. My cock is hard. I wish he was here with me right now.

The hotel room door opens, and I hear him enter the room again. A plastic bag rustles in his hand. I remain quiet. After several moments of silence, I apprehend a pop noise. Cold wet fluid drips down on my ass. His course hands begin to rub and massage my bottom cheeks. Shit, he's going to try to fuck my ass. I feel more cold liquid. His fingers knead my curvy butt. Oh no, his fingers are getting closer. Cold liquid drips directly on to my asshole. I feel some of it seep inside me. It's so cold. I shiver. A wet finger rubs at my virgin trench. Adrenaline spikes in my veins. "Chief, I'm sorry I'm not ready for this," I blurt, breathe quickly, sweat, and gasp.

I hear rustling followed by a sliding noise. I continue to breathe quickly. A thwacking noise sounds loudly and suddenly. My left ass cheek sears in pain, my eyes moisten and glass, I wince, and I clench my teeth. More cold liquid pours on to my asshole. I feel fingers rub inside of me. I pull back my hands and the metal handcuffs clank and rattle against the brass bars of the bed. My insides are cold, wet, and increasingly well lubricated. I twist my wrists. The tip of a finger wiggles its way inside me. "Chief, I can't do this," I beg, shed a tear, and tremor.

Another thwack and he strikes my right side this time. My ass writhes in pain, my hands grab on to a horizontal brass bar from the other side of the headboard, my breaths saw irregularly, and my glassy eyes leak inside the blindfold. Suddenly my breath seems to leave my body, my pulse quickens, mind buzzes, eyes sparkle, hips gyrate and mouth grins masochistically. "Oh God Chief, fuck me in the ass please!" I squeal.

I feel one greased up finger penetrate inside me. It hurts but no more than the belt he strikes me with. Soon there is another finger inside of me followed by a third. Fuck, his hand might as well be having a party up in there. It hurts and I wince. He's opening me up, lubing it up in there. Preparing me for his fat penis. "Please fuck me Chief," I whimper.

After several moments manipulating the inside of my asshole, I feel one of the three fingers withdraw. The remaining two probe deeply inside of me. As I feel two of them press forcefully against the wall of my anal cavity. I gasp, part my lips, and grow pleasurable goosebumps on my arms and legs. His fingers rub, squeeze, and make love to my lumpy little gland. My cheeks burn, arms hang to my side, mouth silent, and posture sags. Inside my body, shivers radiate, tingles all over, and pleasure conquers all. He plays me like a lifeless human piano.

I gasp, moan, vibrate, hold the brass bar tightly, and pucker my asshole around his penetrating fingers. The subway passes underground. He fucks me roughly with his two fingers. "Chief, oh my gosh, the way that feels..." I babble, pause, coo for him, and pant.

He strikes my left ass cheek again with the loudest, cruelest thwack so far. My ass burns, stings, and quakes. The blindfold feels wet on my face. I hiss, grind my teeth, shake, and rock back and forth on the bed. I lie lifelessly for a moment before my body rockets back to life. "Fuck me Chief!" I shout, flush, squirm and release pained, perverted laughter. "Fuck my ass." My body is full of energy and alert. The desire to please him overwhelms me. Every time his rough fingers grope at my helpless pleasure gland, I feel my body quake in it. All the way to very tip of my toes tightly crammed into my white stilettos.

His fingers puppet me as I feel him climb up the bed. It creaks under his additional weight. I shiver all over, sometimes warm and sometimes frigid. He withdraws his wet fingers from my sore, greased up ass, and leaves me writhing on the bed. The skin on my ass stings, my hole feels sore, my body alert, my mouth gasps between pants and my cock is rock hard against the Myla. I feel cold liquid pour directly into my asshole, and I clatter my teeth, feel my neck hairs straighten, and vibrate my shoulders. I can't see what he's doing. I hear a zipper being pulled down. Holy fuck. My heart pounds. I rattle the cuffs against the brass. The subtle sound of skin sliding against skin fills the room. The subway passes underneath. My mind floods with images of the one we took from the airport. The long tube-like train with a bread loaf shaped front with a little window in its center pushing through those tight narrow tunnels to transport tourists and commuters. A moan escapes my parted lips.

His hands touch my battered cheeks and I shudder. A wet tear escapes underneath the blindfold and runs down my face. His hands hold the raw and tender cheeks, spreads them open, the skin of my asshole which is normally closed opens, and I feel cool air waft into my cold lubricated ass. Something taps against my hole and produces a subtle clunking sound. My lower body shivers. I feel something push into my butt. Fatter than a finger. It had to be my boss's veiny penis. He's devirginizing me. I take shallow breaths, swallow hard, wet my lips, and pull my elbows to my side. My ass hurts both inside and out.

It pokes, pushes, prods, pummels, and pries open my insides. Better off not to fight him. Just let him do whatever else he wants to accomplish in there. He could have it. My ass virginity. It's ok. There was nothing I was doing with it anyways. I don't mind it at all. Being his little bitch like this. I spread my legs for him, relax my puckered asshole, and allow my body to go limp. He conquers my asshole, puts his penis fully inside of me, and plunders my virginity. My mouth opens, gasps, and I gaze inwardly. I shiver, wince in pain, and delight in my own impalement. It's warmer and tighter inside of me than I would have ever expected. I moan. My cock is so hard and throbbing. I wish I could stroke it.

Like he did with his fingers, he manipulates his ruling penis inside of my servile ass so that as he thrusts back and forth inside of me, he squeezes my prostate, and it squishes like a tiny lemon. My whole body feels all juicy whenever he does it, everything trembles, I moan, grant him full access to my body and my stomach flutters. Aside from my sore overwhelmed hole and my raw and battered ass cheeks, I feel stimulated, full of energy, and eagerly secretarial for him. I never thought being fucked by a man would be like this. My guess was the first time would be painful, slow, and awkward. But I felt like I could stay up all night with him scheduling appointments for business meetings to take place inside of my accommodating butthole, or maybe my wet thirsty mouth. My heart races in excitement at the prospect of squeezing the brass bar, having his cock up my ass, getting fingerfucked again and again, sucking his penis with glossed lips, letting him beat me with his belt, and having him come inside me before he comes inside me. "Fuck me Chief!" I beg and I gasp. "Stroke my penis. Make me come. Please."

He pulls his penis out of my ass, strikes me a fourth time, thwacks me louder than all the other times, and causes me to shriek in pain, shudder all over, and sweat cold all over my body. I don't know if I passed out briefly or not. It's so hard to tell blindfolded like this with all senses so dulled by the pleasure and the torment. The pain sears and the soggy blindfold feels soaked at this point. The cuffs rattle violently against the brass bars. His wet hand spreads more cold lubricant inside my ass before giving my helpless gland a few squeezes. A moan escapes my lips. He pulls out his fingers and mounts me again using his fat penis. I don't dare do anything that he might interpret as resistance. He fucks my ass steady, makes sure his thick shaft manipulates my prostate in the process, and allows his penis to puppet my body as if it were a character in a children's show. "I will not touch it," he snarls at me. "But I will make you come. Only as a woman does. Sweetheart, you gave it all to me tonight. I dressed you in lingerie, beat you like a man disciplines his insubordinate wife, blindfolded you and handcuffed you to my bed post, and fucked you up your cunt while you begged for it. It's not just your virginity I took tonight. I took any right you had to ever refer to yourself again as a man." He chuckles.

I sweat, swallow, cave my chest, and pretend to smile to get him to shut up. I appreciate that the blindfold hides my eyes. He's right. No man would ever behave so disgracefully like this. It wouldn't be so easy anymore after tonight. Looking at myself in the mirror as a man. Being with another woman while remembering the way I let him treat me like this. He could be right. Maybe I am deep down a transwoman. Somehow it got hidden from me for reasons I just can't explain. I feel him grunt and gasp behind me. He wants to come. Somehow, I can sense it. Maybe I'll just see how it feels. Give myself a little taste of what it's like. Letting him cream my hole for me like a man does inside a woman's vagina. He moans and holds my tender asscheeks tight with his rough hands. "I want your come Chief," I beg him. "Cream my pussy, please."

His cock spasms and I feel him shoot warm come deep into my ass. It was a strange sensation. My anal cavity is so tightly wrapped around his cock that I feel ever throb, spasm, ejection of semen, the big globs, the precision jets, and the frothy squirts. I smile, lower my head, relax my arms, keep my legs spread wide and body open to him, and warmly welcome his manly come into my submissive body. I don't mind it one bit. Now I try to do what he wants. Come for him like a woman. Without any stimulation to my penis. I concentrate on all his warm cum inside of me. God, I'm such a nasty little slut. My cock throbs. I want to come so bad. My mind imagines him pumping his cock inside my hole, blowing thick loads inside me, and him pulling out only to watch hot semen ooze out of my freshly creamed hole. It's not enough. I can't do it. Come without being touched. I hear him getting up. "Wait, stop!" I yell, sweat, whimper, and tremble. "Chief, you have to make me come. Please." The door to the hotel room slams shut. I'm alone.

I lay there on the hotel bed. My cock is so hard. There's the bed. I can fuck it. It doesn't feel right though. Not dressed like this. I can't make love to the bed like a man. Not would when I'm in heels, makeup, and lingerie. I want him to make me come anyways, not this borrowed bed.

As I lay there blindfolded alone, I can't help but focus on the pain radiating from my ass. The hole itself was sore but it compared little in degree to the pain I felt on my outside where he had struck me so violently. The pain reminds me of him and makes me wonder where he is or what he's doing right now. Maybe he is buying us wine. You have to buy that specifically from a liquor store here, right? Or maybe I'm confusing New York City with somewhere else. I hope that's where he is. I'd love to drink wine with him. Especially cuddled up on the bed here.

I hope they don't split us up at the training tomorrow with stupid assigned seats. They should let me sit next to him. We can spend all day together. Like at the office but even closer together. I always hate the networking. Small talk, it's not for me. I'd rather just sit there and listen to the presentations, or just talk to him one on one. Ask him about the people at the training. He always knows the good stuff. The sick and twisted gossip. He's good at telling the stories too. Not as good as when I reimagine it in my own head of course. Nobody's better than my sick imagination. But he paints a nice first layer for me to work off in my head. A rough draft for me to mold into a hearty and elaborate manuscript.

The subway rumbles underneath the ground again. That ride with him was nice, even if the train in New Jersey took forever. Him in his expensive Canali suit and me in my dress, heels, and stockings. Sitting next to each other on the seat. His arm wrapped around my shoulder while I glossed my lips. Just your typical corporate executive and his assistant taking the train in NYC together. Nothing weird or perverted at all about us two sitting, well dressed, and looking hot together. All normal, as it should.

I feel so horny still. That was a bit rude of him. Not letting me come before he left. It's ok though. I forgive and forget. Hopefully he'll still want to fool around when he returns. Maybe that's why he left. Nothing like hitting the streets and taking in some of that crisp New York air. He could be clearing his head and getting in the mood to fuck me again. I certainly hope so.

I think about his penis. With the blindfold, I didn't even get to see it today. I'd like to hold it with my hand again. My mind tries reconstructing what it looks like from my memories. Long, veiny, fat, and lovely. Hopefully he lets me play with it when he returns. I hum softly to myself as I recall the birthday present I gave him inside his bedroom. My lips part and I smile while I imagine my hand rubbing up and down his thick pole. I miss him so much right now.

An hour and a half goes by. The whole time I lay there, thinking of him, fantasizing, missing him, hoping he will barge in any minute. Finally, the door opens before slamming shut. My face beams, smiles wide and my body comfortably warms. I hear footsteps. He climbs up on the bed. I smell his smoky cologne as he climbs on top of me. My ears hear a zipper being pulled down. I squeal, giggle, and burst with energy.

He pours cold liquid into my asshole before he penetrates me again with his cock. I wince. It still hurts. The inside is sore. The outside stings. My cock immediately goes rock hard. I shiver, part my lips and relax my body as I feel him pound against my squishy little walnut gland. "Yes Chief, I'm going to come for you." I promise. "Just like you want it. Like a woman." I hold my body tight, let out a moan, set my jaw, and concentrate on the vibrations of his fat cock against my vulnerable submissive secretor. I gasp and I pant. "Oh gawd..." It feels like he's about to burst the poor thing open. I close my eyes before opening them as my lips part slightly and then more fully until my mouth hangs open and I drool. A long moan escapes my lips and I shiver intensely.

I finally begin to come. Just as he said, like a woman. Nothing touching my little cock. Just from his penis inside my ass. It's a lot too. Thick spurts full of volume. My penis might be kind of small and I may have come like a woman but that was clearly a man's thick semen which sprayed out of me. I can sense my asshole pucker and tingle. He has grown still and grabbed my tender cheeks causing me to wince. He slams his large cock hard back and forth into my ass, making no effort to be gentle now that I had came. It hurts as he thrusts into me. He creams my ass again for the second time that night. My ass feels sticky and sweaty, my mouth releases a deep and happy sigh, and I smile distantly and unfocused. It's so great to be his secretary. I pass out.

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