After her ordeal, Sally had unlocked Courtney from her bondage, let her rest and given her something to drink. Then she led her to a bathroom, where Courtney could attend to her bodily functions.
Next, Sally brought Courtney to one of the upstairs bedrooms, where she could more fully tend to her charge.
Sally had removed her latex maid’s uniform before she had bathed Courtney, since latex did not breathe; and being in a hot steamy bathroom would only intensify her discomfort and increase the risk of tearing the costly garment. Which did not have much of a lifespan anyway. Wearing the latex had made her sweat, and what Sally wanted most of all was a hot bath and plenty to drink to replace her fluid loss.
Two nude women in a steamy bathroom, one bathing the other. Sally took a sponge loaded with body wash, and cleaned the sweat off of Courtney’s lush, naked body. She cleaned her back, then her breasts, and between her legs. Then she washed her hair, and made her stand up in the bathtub. She finished by washing her legs and feet.
When Courtney had exited the tub, Sally proceeded to completely dry her naked body, and wrapped her hair in a towel.
Inside the bedroom, Sally dried Courtney’s hair with an electric hair dryer, and seated before a cosmetics mirror, set her hair.
“Wow,” said Courtney, “I look like a million bucks.”
“Thank you,” said Sally. “I took hairdressing and makeup, which comes in handy when you serve a mistress. Now I have a cool drink for you and something to eat, then you can take a little rest while I bathe myself.”
“Not Mistress Vera?”
“She is quite capable of taking care of herself.”
“Yes, ma’am.”
Courtney was served some ice tea, and a turkey and cheese sandwich, and she was immediately tired. She yawned a couple of times.
“Thank you,” said Courtney as she finished her meal.
“You’re welcome. Now sit still on the bed.”
Sally then gathered Courtney’s hair behind her head, and used a scrunchy to hold it in place. Then she locked a D-Ring collar around her neck again, followed by matching bracelets on her wrists and ankles. Her freedom from bondage had only lasted as long as her bath.
Then Sally took a short chain from the night table and locked it to Courtney’s collar, and then locked the other end to a ring bolt set in the wall above her.
“There now. Just so you don’t get any ideas about exploring when I take my own bath and toilette,” said Sally to her bound and naked companion, “so why don’t you just take a nice little nap before tonight’s bedroom activities?”
“Courtney, wake up,” said Sally.
“What…where am I?” Courtney replied, her mind sleepy and confused.
“You’re in one of the upstairs bedrooms. How do you feel?”
Courtney sat up, and rubbed the sand from her eyes. She had been in a deep sleep in the most comfortable bed she had ever been in her life.
“Fine, thank you.”
“You were dead asleep, it’s almost a shame to wake you.”
“Thanks.”
Sally then produced a glass of water from the night table, where a pitcher and a couple of glasses sat on a lace doily.
Courtney took a few careful sips, as her eyes focused on a luxurious bedroom.
“How do you feel?” Sally asked for the second time.
“Better, thank you.”
“Good, after that session that you just had, I was very concerned. But you came through with flying colors.”
“Have you ever been whipped like that?” Courtney asked Sally, who was still dressed in her Maid’s uniform.
“Sure. Mistress Vera uses me for practice sessions.”
“I can’t believe that I’m asking questions like this,” stated Courtney.
“That’s because we have entered a different reality,” Sally answered, “for us, a world of pain and pleasure; bondage and discipline; leather and latex; and enhanced femininity are now our normal existence.”
Courtney sat up in bed, and then lifted the covers off her naked body.
“Careful now,” Sally cautioned.
Courtney gradually got to her feet, and stood naked before the dresser mirror. She gasped seeing the red marks on her skin.
“They will fade,” said Sally, “Mistress Vera never made you bleed or even broke your skin. She’s an expert with the whip. It wouldn’t do, to hurt paying customers.”
“I feel different,” Courtney observed.
“Happy that you’ve been harshly whipped?”
“Yes, in a strange way,” Courtney answered.
“You’ve joined a very special society of women who have deliberately chosen the whip as their method of sexual release, who engage in bondage and discipline, and wear leather and latex as their clothing. Are you up to a sexual session?” asked Sally.
“Yes, ma’am,” Courtney proudly replied, still admiring her marks in the mirror.
“Enter,” said Mistress Vera, when she heard the knock on her bedroom door.
Vera had a bedroom larger than some city apartments. In addition to a large double four poster bed (often used to secure her submissive females); there was a large dresser; desk and two chairs; cosmetics table complete with chair and mirror; big LCD TV mounted on the wall; and a large black leather footstool; lastly an exquisite complete bathroom.
The doorknob turned, and the door swung inwards admitting Sally and Courtney. Sally was dressed in a kimono robe with Japanese characters printed on the fabric. Around her neck was a smaller collar than the usual once she regularly wore; but it still denoted that she was owned by Mistress Vera.
In her right hand was the leather loop of a dog leash, the other end of which was attached to a D-ring collar that circled and was locked around Courtney's neck. Courtney was naked, with the familiar wrist and ankle bracelets locked onto her limbs. Her wrists were locked behind her back, and her feet were locked into a pair of four inch black high heels. A short chain hobbled her ankles together, restricting her movement. Lastly, a red rubber ball-gag was locked around her neck for easy access.
Sally gently pulled on the dog leash, and Courtney had no alternative but to follow meekly behind.
She then closed the door behind them, and walked Courtney behind her and presented her charge to Mistress Vera who was seated on a chair in front of her cosmetic table.
“Excellent, Sally. Did she give you any trouble or resistance?” Vera inquired.
“No, Mistress. In fact, she’s eager for more punishment and to sexually please you,” Sally answered.
“It appears that we have found a true female masochist,” Vera observed.
“Yes, Mistress,” Sally answered.
“Lay her on the leather footstool and bind her arms and legs to it. That way we can use her both at the same time.”
“Yes, Mistress.”
First Sally led Courtney to the bedroom closet, and placed the loop of her leash around the doorknob, limiting her movement. Then Sally placed the black leather footstool in an empty part of the bedroom floor, and moved chairs at both its head and foot.
Sally then unhooked Courtney’s leash from the doorknob, and led her to the footstool. She removed her ankle chain, and then released her wrists.
“You may lay down on the footstool,” Sally ordered.
“Yes, ma’am,” Courtney answered.
“She’s ready, Mistress.”
“Very good, Sally.”
“Thank you, Mistress.”
Mistress Vera then sat in the black leather chair directly in front of Courtney, removed her robe, and sat down naked. She was a truly beautiful woman. Then she opened her legs to reveal her sex to her naked submissive on the footstool.
“Courtney, you’re now going to satisfy me sexually. But not too quickly. I don’t want a fast orgasm, or you’ll get punished again. Meanwhile, Sally will be fucking you from behind with a dildo harness. So we’ll be using two of your bodily orifices at the same time. Just like in a porn film, darling. But before we start, I have a question to ask you.”
“Yes, Mistress,” Courtney replied.
“Have you ever had anal sex? Did a man ever use your bottom hole?”
“No, Mistress.”
“Ever had an enema or a colonoscopy?”
“No, Mistress,” Courtney answered, her face blushing in shame at the idea.
“Really, we have an anal virgin, Sally,” observed Mistress Vera.
“Yes, Mistress,” Sally replied.
“Now as your Mistress, that means I am going to use your bottom hole first. Nothing serious, just two of my gloved fingers. Tomorrow Sally is going to first give you an enema to clean you out; then make you wear a small training butt plug for a few hours so you get used to how one feels up your bottom. Since you’re so enthusiastic about home bondage I suggest you get a butt plug to attach to your dildo harness and chastity belt. I don’t often punish a girl anally, but I do expect that they understand that I have complete freedom to use their naked bodies as I see fit, and that includes their bottom hole. Do you understand?”
“Yes, Mistress,” Courtney answered.
“Nothing humiliates a high class woman like having a butt plug up her bottom, and when you get one at home, I’m sure you’ll appreciate it using Zoom to conduct business meetings with a butt plug up your ass.”
“Yes, Mistress,” Courtney replied.
Mistress Vera rose to her feet from the leather chair and walked a few steps to her dresser. On it was a black leather riding crop, nipple clamps, a butt plug, a box of rubber gloves, and lastly a jar of lubricant.
She placed the gloves on her hands, and opening the jar, removed a dollop of lubricant which she spread on the gloved fingers of her right hand. The she seated herself in the leather chair facing Courtney’s exposed bottom.
“Hands on your cheeks and open yourself, and relax, Courtney. I’m not going to hurt you,” said Mistress Vera.
“Yes, Mistress Vera,” replied a nervous Courtney.
Quivering with shame and embarrassment, since she had never exposed her nether regions to any type of either medical examination or sexual use; Courtney opened her bottom to Mistress Vera’s probing index and middle fingers.
“Relax, darling,” Vera intoned.
Courtney felt the hand of Mistress Vera gradually slide between her buttocks, and nearly jumped in surprise when she could feel two digits probing her bottom hole.
“Relax, relax, just open yourself to a new feeling of pleasure.”
Mistress Vera probed Courtney’s anus, pushing first one finger inside then two. She had taken a liberal amount of lubricant to smooth the passage of her fingers inside Courtney’s virgin bottom.
Courtney resisted at first, but gradually she opened her anal sphincter to allow Vera’s fingers inside her bottom, moaning with obvious pleasure after the recent whipping.
“That’s good,” Mistress Vera complimented her charge.
“Thank you, Mistress,” Courtney was barely able to speak out the words, as she was so shocked at having her bottom invaded for the first time.
Courtney opened herself, and Vera was able to insert both of her fingers inside her bottom hole. Ever so gradually, she removed her fingers, and then thrust them back inside Courtney’s anus, making her sigh at the new feeling that she was experiencing.
“Very good, Courtney, you’re doing excellent for an anal virgin.”
“Thank you, Mistress.”
Still holding her bottom cheeks apart, Courtney stole a look at the bedroom mirror. There she saw herself laying naked on the black leather footstool holding her ass cheeks apart, while a naked Mistress Vera sat behind her with one her hands up her ass.
Courtney blushed with shame and a humiliation that she had never felt before. Somehow this was even more disgraceful than being chained from the ceiling, naked and in the shape of an “X” while being whipped.
Somehow, all of the self bondage that she had practiced at home, and seeing a professional mistress, had all been preparation for this moment. This was the moment of truth when she finally felt like a true submissive who had surrendered her naked body to her Mistress.
She opened her bottom hole, and Mistress Vera was able to insert both fingers easily.
“Excellent, Courtney. I see that you have learned anal control.”
“Yes, Mistress,” tearfully answered Courtney.
“You’re still tight, which is predictable, which is why you’re going to have to wear a butt plug occasionally from now on. Would you like to try a small one?”
“Yes, Mistress,” Courtney answered, surprising herself by agreeing to yet another violation of her person.
“Thank you, dear. It will be another new feeling to experience. You can stop holding your buttocks apart,” ordered Mistress Vera as she removed her fingers from Courtney’s no longer virgin asshole.
Mistress Vera again got to her feet, and strode again to her dresser. She picked up a small trainer butt plug, opened a foil condom packet and then placed the lubricated condom on the rubber plug. She then added even more lubricant, and it shone in the bedroom lights.
Vera then walked to the head of the footstool, and displayed the butt plug to her charge.
“Courtney, see how it’s shaped. It gradually widens, then when past your anal sphincter it tapers, so that you can’t expel it no matter how hard you try. Think you can take it inside?”
“Yes, Mistress.”
“Good girl,” complimented Mistress Vera.
Vera then walked back behind Courtney, and again seated herself behind her naked submissive. Without even being told, Courtney opened her buttocks to receive the butt plug in her bottom.
“Very good, Courtney.”
“Thank you, Mistress.”
Very gently, Mistress Vera slid the butt plug between Courtney’s ass cheeks. Since she was already open, Vera easily pushed the plug inside Courtney, and her action elicited a moan from the naked girl. Vera continued to push the plug slowly, and when she found resistance reassured Courtney that she was doing fine.
Finally, the widest point of the plug was inside past Courtney’s anal sphincter and it popped into place. It was seated inside her body, and would be held in place by Courtney’s own body. She would not be able to remove it by clenching her muscles; it would have to be pulled out, same as it had been pushed in.
“Courtney, why don’t you get to your feet and walk around? This was you’ll get used to having a plug up your bottom,” Mistress Vera suggested.
“Yes, Mistress,” Courtney quickly agreed.
Courtney stood up, and felt the invader inside her. Having worn a dildo harness, she was used to the feeling of an alien object inside her sex. But this was somehow different.
She took a few cautious steps, and discovered that she waddled like a duck. The butt plug had changed her balance ever so slightly.
“I feel like a duck, Mistress,” observed Courtney.
“Everyone says that,” Vera replied, “remember, this is the smallest butt plug. There are larger ones.”
“I’ve seen some ridiculous ones online and in porn,” Courtney admitted.
“Yes, and those will damage the anus, which unlike your female sex, only has a certain amount of stretch before you actually tear the rectum. Those big ones are only for show, just like the women who get massive boob jobs for adolescent male fantasies,” stated Mistress Vera.
“Thank you, Mistress Vera,” Courtney answered.
Courtney took the advice given her, and walked around the bedroom, getting used to the plug inside her. She felt like her bowels were full.
“Tomorrow I have to leave for a business appointment that I cannot cancel, so Sally will be taking care of you. You will be wearing an apron that will make you look like a tart, dressed entirely in white, and be wearing a harness to keep a butt plug inside you at all times. Do you understand?”
“Yes, Mistress Vera.”
“Very good. How does the plug feel?”
“I think that I can get used to it, Mistress.”
“Good. Since you’ve taken so enthusiastically to bondage and discipline, you will be a good submissive. Now we can continue,” ordered Mistress Vera.
“Mistress?” asked Courtney.
“Yes, Courtney.”
“Can I keep the plug inside me for the rest of our bedroom session?”
“Why Courtney, you’re such a natural,” Vera complimented her.
“Thank you, Mistress Vera.”
“What do you use to clean yourself when you visit the bathroom?” Vera inquired.
“Flushable wipes, Mistress.”
“You are to stop using those immediately. They may be flushable, but unlike toilet paper, they do not disintegrate in the sewer system. They eventually combine with fats, and create a fatberg that clogs the sewers. From now on, you will use toilet paper, and for your anus, place some Vaseline on the paper to properly clean yourself out. Just as you would clean a baby’s bottom,” chuckled Mistress Vera.
“Yes, Mistress.”
“You also should not use Vaseline to lubricate your butt plug, since the petroleum will disintegrate the condom that will cover your plug. You will use KY Lubricant for that purpose,” Vera instructed her charge.
“Yes, Mistress.”
“Now that you have learned how I want you to take care of your bottom, I expect you will do as I order from now on.”
“Yes, Mistress Vera.”
“Excellent, Courtney I want you to lay on the footstool once again. I don’t think that you need to be bound to it, given your enthusiasm for bondage.”
“Yes, Mistress Vera.”
Courtney again lay on the footstool, except this time with her head between Vera’s shapely legs.
“Very good Courtney. Sally, could you take my gloves and hand me the riding crop on the dresser? Also, you may put on your dildo harness. We’re now going to entertain our guest,” said Mistress Vera.
Courtney’s face was now between Mistress Vera’s legs, and she was sucking and licking her exposed outer lips. From time to time, she would stick her tongue inside, past her inner lips, and lick the hard nub of her clitoris within. That would make Vera moan with pleasure, and throw her head back in the throes of ecstasy. Meanwhile, to spur Courtney on, Vera would tap the coiled leather tip at the end of the riding crop in order to spur her on.
At Courtney’s other end, Sally was holding onto her waist and was fucking her from behind with a male shaped rubber cock that was covered by a latex condom. She rhythmically thrust the cock inside Courtney, then withdrew it, only to repeat her earlier push once again.
“Ooooooooh,” Courtney would moan whenever the rubber cock was pushed deep inside her, while at the same time she was servicing Mistress Vera.
Sally had an excellent view of her rubber cock penetrating Courtney’s sex from behind, as well as the base of the rubber butt plug peeking out from between her ass cheeks. Courtney’s back was marked by her recent whipping, and she watched as Mistress Vera would tap her back to urge her on. However, from the way Courtney was licking and sucking Vera’s pussy, she didn’t need much encouragement at all.
Mistress Vera was quite correct in her judgment that Courtney was indeed a female masochist, unlike the majority of her clients that merely wanted to experience a little bondage and discipline in order to spice up their boring sex lives with their husbands, boyfriends, or girlfriends.
Sally’s job was to fuck Courtney from behind, which was something that she enjoyed and was very good at. After all, Vera’s clients were all wealthy women, although bitches would have been a more correct term. She was sure that these rich women treated others like dirt; especially the corporate executives who thought they were goddesses just because they had an office and a title. But they were really just insecure cunts who needed discipline to show themselves that they were no different than any other woman.
Soon, Mistress Vera’s bedroom had the unmistakable odor of sex. With three hot and horny women engaged in sex, the air was filled with female hormones, one reinforcing the other.
“Make me come,” ordered Mistress Vera.
Courtney’s face was deep into Vera’s sex, her lips smeared with her female secretions. Her tongue, after teasing all around Vera’s inner lips, had found the way to her clitoris. She gave her total attention to pleasing Vera and giving the woman a great orgasm, who had just a few hours earlier had given her a severe session with the whip.
After first being used in the library by Maid Sally; and then harshly whipped by Mistress Vera afterwards, Courtney had thought that she might be used up for the night. Instead, all the punishments had done was to fuel her sexual desires for more bondage and discipline, followed by Sapphic lovemaking.
She was indeed a tart.
While her attention was mainly on pleasing Mistress Vera, Courtney could feel the occasional tap of the riding on her back, urging her on to continue servicing her Mistress. At the same time, Courtney could feel her hips held by Sally, who was fucking her from behind with a dildo harness.
“Ooooooooh.” Mistress Vera moaned, as Courtney’s efforts bore fruit to bring her Mistress to orgasm.
It was a strange tableaux indeed as Courtney pleased one woman while getting used from behind.
Finally, after much moaning on her part, Mistress Vera was finally ready to come. She had held back the rising tide of orgasms for as long as she could, for a Mistress had to demonstrate self-control. But she was still a woman, after all, and eventually she surrendered to the inevitable.
“Oooooooooh,” cried Mistress Vera, as she came and her female ejaculations squirted all over Courtney’s face.
At the same time, Courtney came herself as the constant pounding of the rubber dildo from behind had finally succeeded in bringing herself to orgasm as well.
“Ooooooooh,” moaned Courtney as much as she was able with her face buried in Vera’s wet sex.
It was an enormous coincidence that both Mistress Vera and Courtney came both at the same time. Their moans and cries filled the bedroom as they climaxed together, both in the throes of pleasure.
Wave after wave of orgasms coursed through their naked bodies, and sweat formed on Vera’s breasts and ran down her exposed body. Courtney bounced exposed against the black leather footstool, her bare body rubbing against the leather, which only further sexually excited her. Leather was a superb aphrodisiac indeed, whether one was using it to punish a submissive or being inhaled by her as well.
Finally, Vera slumped back in her chair, and pulled her moist pussy away from Courtney’s mouth. There were no other sounds in the room except for the breathing of the two women who had climaxed.
“Excellent, Courtney,” commented Mistress Vera.
“Thank you, Mistress,” Courtney replied quickly, even though she was short of breath herself.
Mistress Vera rose from her leather chair, glad that she placed a towel under her sex so there would be no problem with cleaning the expensive leather. She picked up the towel, and looked at Courtney and Sally.
“While usual, I have a business meeting early on Sunday morning. So that means I have to get some sleep, and get ready for tomorrow. Sally, you may have Courtney for tonight, and use her in any way you wish. Do you consent, Courtney?” Vera questioned.
“Yes, Mistress,” Courtney answered.
“Before I leave at nine am I want to see Courtney in her apron with a harness around her sex and a butt plug up her bottom,” Vera ordered.
“Yes, Mistress,” Sally replied.
“Good,” commented Vera as she walked into her bathroom, “be sure and clean up on your way out.”
“Now Courtney, I want you to lay on my bed, with your legs open. I’m going to use the riding crop on the sensitive skin between your legs. Not much, just a dozen strokes before you get inside my legs and satisfy me the same way you did Mistress Vera. Then I’ll don my dildo harness again, and fuck you face to face, since I’ve already done it from behind. Do you consent?”
“Yes, ma’am.”
“Good, what is your safe-word?”
“Bitcoin, ma’am.”
Naked Courtney did as she was ordered, and was soon laying on the bed as instructed. Sally sat on a chair in front of her, and held the crop in her tight hand. With her left hand she lightly grasped the woven leather of the crop’s exterior and ran it down the length of the terrible instrument. Then she gently flexed the crop between her two hands.
“What was the first time you felt the riding crop?” Sally asked her naked charge.
“On my first visit to Mistress Vera, several weeks ago, ma’am,” Courtney answered.
“So you only used the flogger on yourself at home?”
“Yes, ma’am. I didn’t think that I could generate enough force with either the crop or the whip by myself.”
“True,” Sally agreed.
“Now then, get ready and count each stroke,” Sally ordered.
“Yes, ma’am,” Courtney answered.
“One.” Swish
“Two.” Swish
“Three.” Swish
“Four.” Swish
“Five, owwwwww,” tearfully cried Courtney.
“Six, owwwwww,”
Sally had carefully delivered the first six strokes on the inside of Courtney’s right thigh.
“Seven, owwww.”
“Eight, owwww.”
“Nine, owwwww.”
“Ten, owwwww,”
“Eleven, owwww.”
“Twelve,” tearfully cried Courtney, since she had just discovered just how sensitive the skin between her legs truly was.
“Very good, Courtney. Now you may rise and kiss the crop, and begin to service me between my legs as instructed.”
“Yes, ma’am,” Courtney tearfully replied.
Sally then seated herself on a black leather chair and opened her legs to accommodate Courtney’s ministrations of her hot, wet, sex. Courtney then knelt between her legs, and began to service her, as instructed. Sally retained the riding crop in her hands, and would occasionally tap Courtney on the back to urge her on.
“What a slut you are,” Sally observed.
“Yes, ma’am,” Courtney answered, between tonguing Sally’s pussy.
“What makes you such a submissive, Courtney? I’ve been in the scene for years now, and have seen many women go under the lash for all sorts of reasons. Some are true masochists who enjoy pain. Others feel guilty about something they did earlier in their lives. I once knew a woman who sought out a Dominatrix because she hadn’t bought the new tires her husband had asked her to, only to have him die in a car accident during an ice storm. What is your reason, Courtney?”
“As you observed, I’m a female masochist, I enjoy pain, ma’am.”
“Tomorrow you’ll experience humiliation as well when I introduce you to an enema, a larger butt plug, and I’ll use the flogger on you as well.”
“Yes, ma’am,” Courtney dutifully answered, as she continued to suck on Sally’s pussy.
Later that night, after Courtney had finished servicing Sally and they had both washed up and gone to bed (Sally let her sleep in her bed, not on the floor); she had awakened.
After she had received her MBA from Columbia University she had gone to work briefly at her family’s investment bank in Connecticut before setting off for Wall Street since her older brothers would eventually head the firm.
One day, down in the vaults she had gone exploring, looking through the old ledgers.
There, in dusty leather-bound volumes, she had found the truth. Her ancestors had financed the slave and cotton trade. In black and white she had read about voyages to Africa, and factors in the Deep South to grow cotton.
Courtney had photographed a few pages with her cell phone, and at home she had printed them out.
That night, she had beaten herself unusually hard with her flogger, ashamed of how her family had made their fortune, which had provided her the money for her upbringing, her social class, and her education.
Certainly she liked bondage and discipline. Being confined and punished gave her the orgasms she wanted.
But that wasn’t the only reason.
THE END of “The Penultimate Truth PT2”