The Enchantress: Debt Guild

Frustration, humiliation, exhaustion. The stink and itch of trickling and accumulated sweat, the discomfort at the knees and neck which gnaws away at the mind.

Delegate.

Everyone moaned about the conference….but you always found a way to amuse yourself. There was usually a lady in the hotel bar, maybe looking for some funattached fun. Alpha corporate males with an expense account bigger than their cocks proved to be popular with some of these ladies.

Tonight was no different, you had the final workshop session in the morning and you took your usual place at the bar. Looking around the lounge, the lady that was catching your eye wasn’t your type. Older, certainly. Maybe 50? But a firm, slim figure. She had a sleek, short haircut…..black with a hint of grey mixed in. Her expression was stern, dark eyes intently looking around the scene in the bar. She was wearing a pair of leather thigh boots, matching short skirt and silk blouse. Her make up was quite discreet, pale skin with mascara accentuating her already deep eyes and scarlet lips…..she was quite intimidating in an understated way.

You found yourself staring too much and she matched your gaze…..the look was unwavering and she carried on until you looked away, embarrassed. So much for the alpha corporate male as you sipped your rum in shrunken silence. A whiff of perfume and the creak of leather soon invaded your senses as you turned to see her standing next to you. She was a few inches taller and her demeanour reminded you of a lioness. Casually watching a baby zebra meander around a watering hole before deciding to take it down.

“A drink would be appropriate now, seeing as you’ve spent the last half hour watching me.” Her voice was clipped with an accent, possibly British, possibly Irish. You fumbled to get the bartender’s attention and she ordered a large red wine. You talked….or rather you rambled nervously. Her cool countenance was extremely off putting and you really didn’t know how to act. She was gracious and smiled at the right moments, but her eyes never smiled….not once. She asked if you wanted to fuck her this evening….you sat, struck dumb by the direct question.

“This is why you’re here, isn’t it? To find some easy pussy and to fulfill whatever thrills you?”

You nodded, a little unsure if this would offend her. Instead she smiled again….a genuine one this time and ordered a bottle of champagne. Of course, it was charged to you and she placed her hand on your crotch….your cock springing into life. She tutted, and told you to follow her up to the room. You watched her ass sway in the soft, fitted leather. Her walk was regal, the long boots oozing dominance and you felt like a filthy peasant.

The elevator ride was tense as she stood close to you, but not once acknowledging you…..the short walk to her room and the door was opened. She pushed you on the bed, ordering you to undress. You quickly removed everything as she popped the champagne open. You sat, butt naked watching as she slowly stalked around the room…..her short skirt clinging against her hips and ass.

“Go into the bathroom and shower. I don’t approve of dirty cocks….if I’m going to take something in my mouth, I want it clean.”

You got up and headed into the shower and took care to wash throughly. You even brushed your teeth as you heard music start to play from within the room. You reappeared and she was sitting there, the two glasses of champagne sitting on the dressing table. She handed you one and she guzzled her glass in a single go. You did the same as she poured another….the heat in the room seemed be getting more intense as you felt like your muscles were made of stone. She drank her glass quickly again and you tried to reach for yours….but the strength had evaporated from you. Your fingers were moving in slow motion, your face felt numb and you were dimly aware of your slurred voice. The lady patted you on the head and gently laid you down……

Your eyes opened. The room was dim and the music was still playing. The champagne bottle was next to the bed and you tried to move. You looked down and your heart leapt. Despite the sluggishness, you were fully awake now. The shiny dress you seemed to be wearing was tight. The red ropes coiled around you were also very tight. You tried to call out, but the ball jammed in your mouth stopped any intelligent conversation. The reflection in the mirror filled in the blanks. The sissy slut opposite was indeed you. A short brown wig, leather collar with steel ring attached and a pair of red high heels were forced onto your feet. The makeup was painted on like a true whore and you struggled furiously.

The bathroom door opened and the lady walked out. Her boots were now swapped for a shiny patent pair, fully adorned with buckles running the whole length of the boot….right up to her crotch. She was wearing a latex body suit and long latex gloves. Her hair was slicked back and her demonic eyes almost glowed in the dimness of the room. But the one thing that drew your attention was the massive, jet black cock strapped to her groin. A veined, glistening monster….maybe 8-10 inches long. You shook your head as she strutted over to the bedside table and grabbed a few implements you couldn’t quite make out.

“You really can’t hold your drink, can you, boy? I was afraid I’d have to amuse myself tonight….luckily you made a recovery.”

She moved toward you and quickly grabbed your limp dick. A yelp from you was rewarded with a stinging slap across the face. The black plastic chastity cage was skilfully placed on you and she held the key in front of your disbelieving eyes. She smirked and sat down in the chair opposite you….her boot raised and lifting the dress up to expose your caged cock. A sigh and a chuckle came from her cruel red lips as she started to stroke her huge phallus. Quickly and rhythmically jerking it up and down.

“This could have been you. But I got the idea that you might prefer taking cock, rather than giving it. A shame really, I just reapplied my lipstick for nothing. But don’t worry, baby. I’ll make sure that I’ll reapply yours….i plan on having it smeared all around my big, black dick. You like my big, black dick, sweetie?”

You shook your head and she ground her boot heel into your cage. She would educate you for the whole night to come. A vibe constantly forcing your little girly cock to swell in its prison while a real piece of equipment took your virgin ass.

Perhaps you won’t be returning to the conference next year…..or maybe you will. I guess your lady will decide that.

Gender Gap. Part 2

I laid the latex maid outfits out for my new toy to look at. I had taken the liberty to include contrasting cages too. He gurgled a protest around the ball gag and I slapped him hard across the face. He whimpered a little bit and I grabbed his shrunken balls roughly….

“Now, you little streak of rat’s piss. This is what will be happening. I’m going to give you a choice. It will be the only one you’ll get while you’re in my company. Pick a dress and a cage. We’re going to film a little video and it will be uploaded to every account you have…..LinkedIn, Facebook, tinder…..Grindr. I say that, because you might get a lot of new followers who like sissy cunts.”

He cried in pain as I then spitefully twisted his nipples. When he stopped snivelling he grunted and nodded his head toward the black dress. It was predictable, but at least the cage would be nice and pink for my little whore. In truth, he would be wearing both at various points, but we had to start somewhere. I locked the cage on his disgusting cock and tugged it once in place. Another gagged yelp escaped his mouth and another slap followed.

I stood him up and forced the dress on his body. The glossy latex clung to him, with the skirt flitting out nicely at the bottom. I spun him around and inserted a matching pink anal plug up his ass. His eyes widened as the toy invaded his rectum and he slumped in resignation. I was disappointed, I was expecting this ‘alpha’ prick to put up a fight…..but he was cowed and humiliated already.

I produced the black stockings and put them on his legs….one of them was laddered….enhancing his look of a used slut. The high heels were too small, but I wedged his trotters in them and dragged him to his feet. He tottered unsteadily, more groans of pain emanating from his drooling lips.

“There. We’re almost done. But you look far too ugly and I want a pretty maid, don’t I? So, I think we need to see if I can perform a miracle and turn you into something even I might want to fuck.”

I grabbed the make up bag and started to apply the rouge and the lipstick. His lips were perfectly wrapped around the ball gag, making it easier to paint him into a tart. Next, the garish blue eye shadow, mascara and false lashes.

I stood back and checked my work so far. “My goodness, you really are a wanton sissy aren’t you? If I check your cage I wonder if you like it so far.”

Of course he had a mirror in his office and I shunted him over to look. He struggled and tried to curse at me….so I stuck my hand up his ass and started to manoeuvre the plug around. He shrieked like a bitch and guess what? The dreary little cock was straining in its prison. I chuckled and brought him back to the chair to continue his makeover. The auburn wig wasn’t quite his colour, but he looked presentable from behind at least. The setting up of the camera took time, but at last we were ready as I got him on all fours….crawling around his office and shaking his plugged ass for me. I lifted the skirt and the base of the squat plug was firmly on show, along with the cock cage dangling uselessly in front.

The leather slave collar was buckled on and I led him around the office a few times. When I bent him over his desk, i made sure his cuffs were tight. He saw me take the strapon and step into it….i did it slowly and deliberately just to give him time to beg….but it wasn’t going to change my mind.

The camera was set and so was I……the plug would be removed and there would be no doubt, the little slag’s mascara would be running down his face….

TBC

The problem with not giving a fuck about what people think of you and not firing within the gender binary is it just makes humiliation and shame so much less effective. Or rather changes how it affects me.

I'm a slut, a whore? Yes, yes I am. And damn proud.

Being feminized? I worship a goddess. I'm being elevated closer to what I worship? Hell yeah!

Kiss your boots? Bowing before you and showing my submission to you so directly is amazing.

I'm a cuckold? Oh you mean, I'm not claiming ownership of my partner's sexuality!

But the changes meaning becomes centered so much in the context of your dominant. It can be:

Pride: I'm your slut, your whore? Oh yes I am. I crave you so much I'll do whatever it takes to please you.

Surrender: you want to feminize me? Of course! I'm yours and happy to serve as your doll.

Acceptance: Kiss your boots? I'm your submissive and will happily show my devotion however you want it to be seen.

Trust: I'm a cuckold? I can't satisfy you sexually but I want you to be satisfied regardless. You may be getting fucked properly now, but no one can replace me in your heart.

Don't get me wrong, as a lover of being in chastity, there's something so hot and humiliating about knowing that you can't satisfy your partner. But it's not because that's what the world expects, it's between the two of us.