This tale features trans lesbian extreme femdom. If that isn't your jam you might want to skip it.
Taylor knew that Andrea had wicked plans for her after work that would attain a new plateau in their growing relationship. She was used to serving her employer's wicked desires at the end of the evening, but Andrea had warned her that she planned to take complete control of her and that there would be a ceremony commemorating that escalation tonight. She knew that this was a watershed event. It was full of excitement and dread for her. There would be pain, of that she was certain, but the deep arousal that she felt when Andrea held her and the need she had for the control she exercised over her outweighed the fear of how she would be made to suffer.
Her huge cock had been battling against the tape holding it down all night. Whenever Andrea was near her excitement grew, particularly because her beautiful boss touched her whenever possibly, sometimes slipping her hand under her short skirt to fondle her bound meat or stroke her ass.
During her break she'd been obliged to kneel at Andrea's feet behind her desk and suck her to an impressive orgasm that filled her mouth with scalding cum. The flavor had remained on her tastebuds as she served her tables for nearly half an hour. She felt self-conscious that her customers might smell her cock breath.
The thought of Andrea's cock always filled her with lustful thoughts of being impaled to receive powerful thrusts that excited her beyond words. Taylor had to admit that she liked getting fucked even more than she enjoyed sucking cock, particularly when it was Andrea fucking her because she took her pleasure so ruthlessly. Her anus had ached ever since the first time. Her Mistress never got enough, and she seemed to have no concern for how her brutal treatment affected Taylor, unlike Brad who was sometimes too gentle with her.
That casual treatment of her slave applied to every aspect of their relationship. She enjoyed playing with her genitals immeasurably and utilized her vast collection of toys to experiment with various levels of agony when they played. The thought that tonight would exceed previous excursions into Andrea's sadistic experiments on her body terrified her, but despite that her cock throbbed in anticipation.
"You have no idea how hard I'm going to use you tonight, my little slut."
Taylor hadn't noticed Andrea slipping up to whisper into her ear from behind. The soft warning made her shudder.
"There's a gentleman at table five who expressed an interest in a special service."
"Yes, Mistress."
The worst part of Taylor's job was moments like this. Andrea pimped her out infrequently, but when she did it was expected that she would serve the guest who requested her in any way that was demanded. She knew who was seated at the table in question and dreaded what was to come. The man was fat, ugly and had a nasty manner. He'd tried to grope her when she brought his last drink and made a lewd comment.
"You got such a pretty mouth why don't you wrap it around my cock?"
So, Andrea made it official. Now she had to suck the pig's dick. She decided to get it over with and marched to table five, took his beastly hand and led him back to the office where she guided him to a chair, helped him lower his pants and fished his little Peyronie curved cock out and went to work. She fondled his balls and sucked him as efficiently as possible.
As soon as he shot his load she rose and left for the bathroom to spit his foul ejaculate into the toilet.
Andrea intercepted her as she emerged and grabbed her face.
"He said you were rude and did a shitty job."
"Sorry Mistress."
"I expect better from my slave, bitch. Next time I send you to service a good customer I expect rave reviews on what an excellent slut you are. We will revisit this tonight, trust me."
When Andrea released Taylor's face, she swatted her hard between her legs. The blow doubled her over and she cried out in agony. As Andrea stalked away Taylor cried in a mixture of pain from her balls and terror at what Andrea now planned for later.
Closing time only served to double her dread. Andrea led her to their apartment by hooking a finger under her collar as she marched her roughly down the street, Surely, anyone who witnessed her humiliation knew that she was a slave who was on her way to severe punishment for some infraction. In case the visual clues were not sufficient humiliation, Andrea lectured her sternly and in a loud voice as she dragged her along.
When she pulled Taylor up the front steps of their brownstone the collar choked her harshly. Once inside Andrea marched to the display of implements of torture hanging on a rack against the wall by the bed.
"You've got ten seconds to be naked, slut."
Taylor had already begun removing her work uniform but increased her pace, fairly ripping her stockings and panties off. Even so she was not quick enough to suit Andrea who stormed up to her and tore the tape securing her cock off rudely and clutched her balls in a fierce grip eliciting a howl of agony.
"If you think that hurts, consider it a caress, slut."
"Yes, M-mistress."
"On your knees."
"When I direct you to pleasure a client and he or she is not satisfied you will suffer terribly. My reputation is always to be forefront in your mind as you serve anyone I loan you to. IS THAT FUCKING CLEAR, SLUT!"
She slashed the crop she had selected from the rack across Taylor's tits. She raked back and forth repeatedly making them bounce wildly under the rain of brutal blows.
Taylor cried out at each lash as bright red welts popped out on her tender tits.
"Shut up, bitch."
She brought the crop down on Taylor's traitorous cock that was standing up belying the pain and terror she was feeling. Taylor shrieked at the agony of that blow. Andrea grabbed her by the throat and hissed.
"I told you to shut it. Go fetch the big cock gag, that'll keep you quiet."
Taylor rose awkwardly and staggered to the rack of torture devices. She took a gag that was shaped like a thick cock, about 5" equipped with two straps.
"Get the largest butt plug too.".
"And lube?"
"No lube."
Taylor scowled at this, but Andrea caught her reaction and glared pointedly at her.
"Have you got something to say, slut?"
No response was forthcoming.
"No? Then get your ass over here."
Taylor stumbled over to Andrea and handed her the required equipment, then fell to her knees at her Mistress' feet.
"All fours, ass high."
Tayor dropped her hands to the floor and arched her back to lift her butt provocatively.
"Mouth open."
Taylor opened her mouth wide, and Andre leaned over to slip the phallic gag in. Taylor worked her jaw to settle the intruder in. Then Adnrea attached the straps to fix the device securely in place.
She signaled her to spin around and present her ass for the next step. Taylor's reluctance was obvious knowing the agony that taking the plug with no lube would entail.
Taylor was resigned to Andrea's intention to insert the plug without benefit of lubrication. She struggled with her fear and desire warring in her emotions. She was besotted with Andrea, but terrified at the same time. She knew that Andrea could be incredibly cruel, yet she inspired the most overwhelming passion that Taylor had ever felt. Even the way she felt about Brad was pale by comparison.
When Taylor felt the tip of the plug touch her ring instinctively began to clench but by an act of will she began to relax and pushed out to accept the monstrous plug and save herself the pain she knew would come with any resistance.
"Open wide, you don't want to fight this."
Taylor knew that Andrea was being kind in her way, warning her that resistance was futile and that she would have her way with her regardless. The pressure was gentle and slowly built as the plug forced her anus open.
The pain grew in intensity as the girth of the plug widened the deeper it went. Taylor whimpered at first and then cried out. Andrea stared intently at the effect her toy was having, distending Taylor's. hole grotesquely. She considered how easily she would be able to fist her after this, which made her cock harder and prompted pre cum to drip down her shaft.
