Jack sat in Madam Mapleton's office, squirming in the comfortable chair in front of her desk. The reason for his unease was directly related to the Madam's recent streak of cruel and sometimes unusual punishments. She had yet to relax from her efforts to make his life miserable, so a trip to her office could never bode well.

In time Mrs. Mapleton arrived, smiling at him as she sat down behind her large mahogany desk. Jack licked his lips, "Madam… always a pleasure. Whatever can I help you with?"

Mapleton smiled again, seeming to enjoy his unease, "You just sit tight; we'll be having company in a moment here."

Jack's mind raced; who would need to see him and Mrs. Mapleton? His gut sank as he thought it might be Captain Vain; if the vengeful man came by to gloat he may learn of all the… things that the Madam had seen done to him…

But Vain wasn't who entered the office then; instead, the figure of Lady Eleanor Guthrie stood in the doorway looking Jack over before she entered to be seated across from Madam Mapleton. Jack felt confused but remained quiet, curious about the unexpected visit.

Miss Guthrie opened conversation, looking to Mrs. Mapleton, "I assume you got my message concerning my interest in your… property."

The Madam smiled, nodding, "Indeed, Miss Guthrie, but if you have heard much about him, then I'm sure you know that Jack is of sentimental value to me, besides being a great earner."

Eleanor gave a tight smile, "Just tell me how much; I'm sure you know I can afford it."

As the two women haggled a sale price for Jack, he stood in slack-jawed awe of the sudden twist of events, his heart soaring with the prospect of release from his hellish imprisonment. Miss Guthrie, for whatever reason, had come to save him!

Perhaps Max had changed her mind and decided to help him after all. Bonnie may have convinced her to put in for a favor from her ex-lover, since Bonnie and Max seemed to be getting ever closer these days. But however it happened; it was a day of joy!

Jack did his best not to smile, lest he give Mrs. Mapleton cause to keep him, since the spiteful old bitch would be ruffled to see him less miserable. Price decided, they stood, Mapleton shaking Guthrie's hand and nodding toward Jack, "He can be a handful at times, I'll warn you…"

She walked across the room to a cabinet that Jack had come to know as the storage-place for items of unnecessary violence. From here she removed one of the straps she had punished him with early in his tenure.

She handed the leather strip to Eleanor, "…But if you are firm with him, he'll straighten out just fine; see how compliant I have made him."

Eleanor raised an eyebrow at this and took the implement. "Come along, Jack."

Jack wasted no time, and now that the deal had been struck, he didn't bother hiding his smile of relief anymore. He expected his optimism to annoy Mrs. Mapleton, but instead of a frown, she only gave him a sly smile back, which in turn caused him to frown again. What did the old cunt know that he didn't?

Despite the cloud that the Madam had placed over his rescue, Jack managed to find his elation again quickly enough as he was escorted from the Brothel to Eleanor's own offices. As they walked, he took in a deep breath, smiling, "Ah, freedom. I owe you a debt of gratitude, Miss Guthrie, but for now, I think I need to go get a drink…"

Eleanor turned to face him, "That would be a mistake, Jack. Once Vain learns that I've… acquired you, you won't be safe anywhere but my compound." On seeing his face fall, she went on, "And like you said; you owe me now, and I intend to see how you can be of use to me."

She turned, heading up the steps to the second floor, and Jack frowned as he contemplated how he had traded one gilded cage for another. Well, he thought, this cage seemed a hell of a lot better than the last one.

Jack spent the next several days standing around Miss Guthrie's office, feeling mostly like an unneeded paperweight. A few times he was able to help her concerning business plans, but Eleanor was a shrewd person in this field, and rarely needed help.

So he spent most of his time with the ultimately mundane tasks of sweeping the second floor office and filing paperwork, along with an assortment of other flavorless activities when he wasn't simply doing nothing at all.

With all of the excess time, it was easy for him to notice that Eleanor spent quite a bit of time staring out of her window at the balcony across the way, where Max often retreated from the brothel for fresh air. Finally one day he approached her while she was glancing so, and spoke on the matter, "You should go see her."

Eleanor whipped around, glaring at him so fiercely that he took a step backwards, "She won't have me; I've tried. I can never have her, and it is at least partly your fault! "

Jack stammered, finding himself caught unawares at the sudden anger he found himself under, "I-I swear I never meant to come between the two of you, and I apologize profusely for any involvement of mine that might have led to this!"

Eleanor stalked over to him, glaring at him still as she growled, "Is it true that you and Bonnie are together?"

Jack raised an eyebrow, confused and not entirely sure how much of his… complicated relationship with Bonnie he would want to reveal, "Well… we have fucked… why does she have anything to do with this?"

"She is as guilty as you are for everything that led to me losing her, and I intend to make you both realize that you don't cross me. I can see by your face that you care for her, so I think I know exactly what to do; I'm going to let you go be with her."

Jack's brow furrowed, "I'm afraid I don't understand…"

Guthrie moved to her desk and opened a drawer, pulling something heavy and metal out to set it on down with a thud. "You're going to be wearing this. Be sure to let your lover know that I have the key."

Jack had to look it over a moment before he realized it for what it was; a chastity belt, complete with an intricate lock to prevent anyone opening it that didn't have the key. "Oh. Are you sure you can't just let us make it up to you some other way?"

Eleanor shook her head, still glaring, "You two will be denied from being lovers, just as you denied me. Now put it on, and go see her."

Jack let out a long sigh as he picked up the device, looking it over and wondering how he was going to get out of this one. "I understand you are upset, Miss Guthrie, but you can honestly expect…"

His sentence trailed off when he looked up and saw that Eleanor had retrieved the strap that Mapleton had given her. "I paid far too much gold for you to simply tell me no. I know what the Madam did to keep you in check, too; don't think I won't."

Jack gulped, frozen in place by the unexpected threat, "But…"

"Now!" she yelled.

Jack began putting the girdle on quickly. As embarrassing as wearing it could be, he could tell by the look in Eleanor's eyes that things could get far more humiliating if he didn't comply…

"Take off your pants."

Jack hesitated, and Bonnie shot him a suspicious look, "What, you with Guthrie now, you won't do what your told anymore?"

She strode across the room and yanked his pants down, despite Jack's feeble protest, "Wait…!"

Bonnie's eyes went wide, "What the fuck?! What is this?"

Jack explained what Guthrie had told him, and Bonnie laughed into his face. "If that cunt wants to play this game, she sure as hell shouldn't have picked you." She grabbed him by the collar, yanking him down so that he was on his knees, "I can find other ways for you to get me off…"

Jack licked his lips, unable to hide his arousal at the way she pushed him around. He had always relished how Bonnie took charge, loved her for it in fact, though he doubted his love was reciprocated. "Yes, she seems to have forgotten that favors extend beyond the hips…"

Bonnie smiled, closing her eyes, "Now shut up and put your mouth to better use."

Jack returned a bit ruffled, and Guthrie surprised him by drawing close, sniffing him, "You smell of sex; did that bitch pick the lock or something?"

Jack shook his head, a little surprised that she had been able to smell what they had done. He made a mental note to bathe before returning in the future, assuming Guthrie let him go back at all. "No, ma'am, you can inspect it if you like; it hasn't been tampered with."

Guthrie glared, realization dawning on her features, "You fucked her with your mouth."

Jack jumped with guilt, "W-well, you never said specifically that I couldn't please her orally…"

She slapped him, and Jack stared down at the floor as she screamed her anger, and then all of a sudden she grew calm again, walking over to sit at her desk, "Get out."

Jack looked over her way, and noting that she wouldn't even look at him as she busied herself with her work, he quietly left the room to retreat to the servant's quarters where he slept.

The next morning Jack went to Guthrie's office early, planning to apologize for his failing and ask forgiveness; after all, Eleanor had still saved him from a fate perhaps worse than death, and he thought he might get out of putting the chafing chastity belt back on if he could curry a bit of favor.

Jack wandered from the office to her private chambers when he saw that she wasn't waiting for him as she usually was, and knocked lightly on her door, "Milady, are you up?"

The door opened and Jack gazed upon Eleanor in her nightgown, looking disheveled with a glow about her that he couldn't place. The way she looked at him made him uneasy and he looked away, "I apologize, Miss Guthrie, I…"

She surprised him, grabbing hold of his collar and yanking him into her bedroom. Jack yelped as she reached down and took hold of his member, squeezing as she told him huskily, "I thought of a way you could repay me. After all, I do own you…"

Jack was almost eagerly compliant as she ripped his pants off of him and pushed him back to her bed. She wasted no time for foreplay, having apparently already been warmed up; she threw her leg over him, taking only a moment to line his cock up with her hand before shoving herself down on him.

Jack gasped as she began thrusting and gyrating upon him, and he reached up to take her breast in hand, thinking to give her a kiss, but she put both hands on his chest and shoved him back down onto the bed. "No. You are here to please me."

This only made Jack harder. She couldn't know that such treatment aroused him, could she? As she pulsed up and down on his dick he tensed, feeling close to release. She seemed to sense this and stopped, glaring at him, "You had best not cum until I say so; I'm not there yet."

Jack gulped, nodding even as he spoke negatively, "I want to, but I don't know if I can hold it… I've been in a chastity belt during sex recently and…"

Guthrie gave him a humorless smile, "If you don't do as you're told, I'm going to go get the strap."

This was the encouragement he needed, and Jack nodded again his assent. Guthrie took a long moment to just look at him, and Jack had the distinct impression that she was reading him like an open book. Never in his life had he felt so exposed.

Then she drove down on him again, thrusting herself hard on him until sweat beaded on her tensing thighs and across her breasts as they bounced to the rhythm of her fucking. Jack bit his lip, using all of his will to suppress the desire for release.

Finally, she tensed up, her legs squeezing him hard as her body shuddered in the throes of orgasm. She squinted her eyes closed and undulated a long cry as the waves of pleasure cascaded over her. She collapsed on his chest, and Jack could feel her heart hammering as she took fast, deep breaths.

After a while, Eleanor lifted her head, giving him a small smile as she pulled free of his cock, "Maybe I should have invested in a personal toy before now; that was fun." She glanced down and then returned her gaze to his eyes, studying him. "You didn't get off, poor thing."

She reached down, taking his member in her hand and rubbing it gently, causing Jack to stir involuntarily. "Don't worry; I'll take care of you." She jerked him slowly at first, increasing tempo as his breathing quickened until she was beating him off hard.

Jack screamed out loudly as he ejaculated, Eleanor still pumping his penis in her palm as he shuddered in ecstasy. Eleanor leaned in to whisper almost conspiratorially, "I bet Bonnie isn't going to enjoy the fact that you've been fucking around, Jack."

Jack shot her a look, "Wait… this wasn't all contrived just to make my… partner jealous…?"

Guthrie simply gave him a look and rose from the bed, "You can go, now. Put your belt back on and go see your lover again."

Jack was stunned. He was caught between two women's quarrels and it had just gotten him laid. He wasn't sure how to feel about that. He moved numbly back into the office and retrieved the chastity belt, and Eleanor followed soon after to make sure it was locked tightly.

She smiled and gave him a light smack on the ass as she went back to her quarters, "Be sure to tell me exactly how it went."

When Jack returned a few hours later Guthrie took him back to her office alone, unlocking his girdle and taking a deep breath over him, frowning, "You still smell like sex."

Jack recoiled; this time he had bathed… how did she manage to pick up on that? Eleanor frowned, "I can smell her tang on your breath. She doesn't care at all that she can't have your cock does she? So… did you tell her that I fucked you?"

Jack piped up immediately, "Of course… she, uh, just wasn't concerned, I suppose. After all, I am in the custom of bedding multiple women at a time, and it has never bothered her in the past. She has no reason to hate you, you know…"

Finally Jack felt like he might have found a way out of the situation with the chastity belt. If he played his cards right, he could perhaps be with both women, as well. He allowed himself a smile when he thought she wasn't looking.

That smile withered as Guthrie pulled a familiar item from her desk. She allowed one end of the strap to repeatedly smack her other hand as she approached him again. "I don't like being lied to, Jack."

Jack tensed, "I wouldn't dream of it… I told her just as you asked…"

Eleanor raised an eyebrow at him, "Oh, is that what you were lying about? Well, that is direct disobedience, Jack. We're going to have to address that… go to my room… now."

Jack was going to object again, but her threatening advance drove him to retreat in the described direction, so he moved there, his mind awhirl on how he could avoid this new problem. He had in fact not been able to tell Bonnie about having lain with Eleanor; she would have killed him!

Jack sought fast to assuage Eleanor's suspicions, "Milady, I assure you…"

Guthrie didn't seem to be interested in what he had to say, shoving him as she had previously so that he once more lay upon the bed, except that this time she remained clothed and did not join him. She simply said, "Turn over and pull your trousers down."

Jack stared up at her a moment in disbelief, unable to believe that this was happening at all. Memories of his time under Madam Mapleton's care caused his butt-cheeks to clench in anticipation. "Miss Guthrie, please, let me explain myself."

Eleanor shook her head, "No. No more silvered words, no more diplomacy from your conniving tongue. Just do what I tell you to and remember who you work for. Do you want to go back to Mrs. Mapleton?"

Jack thought on his options a moment and then reluctantly pulled his trousers down, even more reluctantly turning onto his stomach. "Alright, I… Ahh!"

His words were cut short as Eleanor began swatting him immediately and earnestly, all the while scolding him. "You would do well to remember that every dog on these seas has at some point attempted to lie to me. I know you didn't do what I told you to, Jack. You haven't got the balls."

Jack grabbed handfuls of the sheets before him and cried out in pain. Eleanor was merciless, and he wasn't sure how much of this he could tolerate.

She went on, "If you had told her, she would most likely have at least returned you with a black eye, but trying to tell me she would be okay with me taking you from her? I wasn't born yesterday, Jack. I put it together, Jack, and I think I know what you see in her, now."

She set the strap aside on a nearby nightstand and sat down next to him, pulling him up onto her lap. She continued her work with her bare hand, the sound of the slapping resounding through the chamber. "But you are mine, now. I've claimed you, and you are mine. That belt won't keep her from seeing the bruises this punishment is going to leave, and she'll know, Jack."

Jack yelled out, "Why?!" He cried, tears streaming down his face in a sudden torrent, "Neither of you really want me, then, this is between the two of you and has nothing to do with me!"

Eleanor took hold of his hair, turning his face so that they stared into each other's eyes, "Why didn't you do what I told you?"

Jack sobbed as his voice broke, "Because I didn't want to find out how much she cares about me, okay?! I just know, deep down that she would just shrug and tell me to eat her out again. It's not that she doesn't care about what you're doing, it's that I'm without value to her, and I don't want to see that…"

Eleanor stopped swatting him a moment, and then started again harder, causing Jack to squirm in her arms, "Didn't you get it when I said I would take care of you? I know what you need, Jack, and I paid gold to have you away from what Vain did to you. You're mine, dammit!"

Jack opened his eyes, wiping the tears away enough to see the sincere look on Guthrie's face. "Wait… what?"

Eleanor smiled at him and stopped her barrage, leaning in close to whisper, "I take care of what's mine."

Jack only stared at her in baffled confusion for a few moments, before timidly reaching out to her, cringing even as he did so.

Guthrie felt sorry for this poor soul, who was so scared even to offer such a gesture, so she surprised him again by hugging him tightly to her chest. She whispered only one word as they held each other there, "Mine."