Trust Fund Baby Pt. 07

I have no clue what they did to the poor girl, but when the two of them returned after nine days, Olivia was a completely different person. She was much more compliant, broken even, although her injuries seemed to be psychological rather than physical. She showed Madison far more deference than before, any glimmer of resentment in her eyes having been crushed.

Madison gave me no notice of their imminent return, she just showed up at my front door in an Uber, with several suitcases full of her new purchases, with Olivia in tow. When I say "in tow" I mean it in the most literal sense, as the younger woman followed directly behind Madison on the end of a dog leash. She was collared too, wearing a black leather collar similar to the one she wore when I first dominated her. Olivia had her head bowed down in defeat, the resistance that she had exhibited at every stage of her forced submission to Madison, completely ground out of her.

"Kneel," Madison instructed, as Olivia obediently lowered herself to her knees. "Stay."

As the young Uber driver began to bring the suitcases into my entryway, Madison instructed me to run her a bath. I had gone well over a week without sex, and in an attempt to get into her good books and maybe earn some release, I obeyed her immediately.

"Liv, make sure you tip the driver," Madison ordered, as I followed her down the hallway.

After I ran Madison's bath, she dismissed me with instructions to pour her a glass of wine. As I made my way into my kitchen, I noticed Olivia was kneeling by my front door, apparently obeying Madison's directive by sucking the Uber driver's cock, presumably for his tip. I was tempted to save her from this indignity, and give the young man a hundred dollar gratuity. However, as I tentatively approached them, she stopped blowing him momentarily, and imploring me with her eyes to leave them alone, she waved me away.

Years later, after Madison was long gone, and Olivia and I were still friends, I apologized for my lack of intervention. However, at the time, I didn't want to do anything to jeopardize my prospects of sex, so I kept walking towards the bathroom.

"Is Liv taking care of the Uber driver?" she asked with a cruel smile, as I placed her wine glass on the shelf adjacent to my Japanese soaking tub.

Madison didn't even wait for my answer, taking a large sip of her wine, before turning her attentions to me.

"Evidently, you behaved yourself, in my absence?" she asked rhetorically, the tent in the front of my shorts giving her the evidence that she needed to assure her that I had not pleasured myself, and was in desperate need of relief.

Madison had added plenty of bubble-bath to her soaking tub, and her body was obscured by the prodigious amount of suds gathered on top of the water. However, as she assessed my level of arousal, and determined that I was craving her touch, she raised one of her perfectly manicured hands from the water, and raked her hot pink nails across my bulge. I let out a whimper at her caress, and we both knew that the status quo had been restored, and she had me exactly where she wanted me.

As she fondled my nuts through my shorts, any thoughts of terminating the relationship evaporated, replaced by a steely determination to do whatever she wanted, thereby increasing my chances of getting some release. I heard the front door close, and Madison sat upright in the deep soaking-tub, exposing her breasts and upper-torso. As my eyes were drawn reflexively to her perfect, surgically-enhanced boobs, I noticed the first evidence that she had also been subjected to some physical abuse.

She had love-bites all over her tits, bruises across her shoulders, and some kind of ligature marks around her neck. I went to verbalize my concerns, but she silenced me with a stern look, and an assurance that she was okay.

"You should see Liv," she said with a giggle, "that bitch took the brunt of it. It took us four days to break her. In fact, it sounds like the Uber driver left. Get her in here."

My heart sank as I processed her words, wondering what the hell Steve had put Olivia through, to have earned the characterization of having been broken. I went to leave the bathroom, but Madison stopped me at the door.

"You don't need to chase her down," she said dismissively. "Call her. She responds to Liv or rim-job girl, although I am going to get a whistle to summon her when we are home."

"Liv," I said quietly, not wanting to be too forceful with my young friend, the first time I beckoned her.

Seconds later, Olivia appeared outside the door, disrobing silently before entering the bathroom and kneeling by the tub in which Madison was luxuriating. Ever conscious of the dynamic between Madison and Olivia, and the consequences of evoking any jealousy from my girlfriend, I lowered my eyes and averted my gaze from Olivia's naked body.

"Check her out, Pete," Madison instructed me. "This is what it takes to achieve total compliance."

I lifted my eyes slowly, and was greeted with a shocking sight. Olivia had been badly beaten, and judging by the red marks around her wrists, neck and ankles, had been restrained for long periods of time. There was no other possible explanation for her ligature wounds, and she also had bruises and bite marks across her chest, although she still bore the teeth imprints, suggesting that she was subjected to more than mere love-bites.

There were numerous red welts across her back and buttocks, suggesting that she had been severely whipped. I swallowed involuntarily as I processed her wounds.

"Rattan cane," Madison said cheerfully. "This was the instrument that finally got through to her."

"Madison, does she need medical attention?" I asked fearfully, recognizing that my girlfriend was blinded by hate for her younger rival.

"I sent a few photos of her to my Doctor friend at the clinic, and he assured me that her wounds are both temporary and non-threatening," she responded dispassionately. "Up on all fours," she added, as Olivia got into the doggy-style position.

"Her ass is a little torn up," Madison said with a giggle, "Baldwin sodomized her regularly to soften up her resistance."

As my eyes wandered across Olivia's shapely buttocks I noticed the traces of blood first, both on the inside of her ass-cheeks and on her inner-thighs. They had obviously decided not to allow her to clean herself up, probably to induce shock in me, but the specks of blood were the least of my concerns for her physical well-being. Her asshole was gaping, wide-open from the ongoing ass-fucking that she had been subjected to at the hands of Baldwin.

"Steve did this?" I asked shakily, not knowing how to react.

"Most of it," Madison said proudly, as she admired the physical evidence of the sustained abuse. "I butt-fucked her this morning to reinforce the hierarchy between us."

"Are you okay, Olivia," I whispered quietly. "Do you need to see a Doctor?"

"I am fine, Mr. Pete," she said resolutely, "I am happy to be home to serve you guys."

Even though I wasn't convinced that Olivia wouldn't have benefited from a medical check-up, Madison was moving on.

"Pete has been a very good boy, Liv," she said condescendingly. "He has earned some release. Be a pet and take his clothes off."

In the past when Madison had used such disparaging language to direct her, Olivia had glared at her, but as she began to unzip my shorts, any resistance that she may have once had, was gone. It had been nine days since I had been touched by a woman, and as Olivia's dainty fingers brushed against my skin as she relieved me of my clothing, I felt my cock stiffen. By the time I was naked, I had an erection, and Madison instructed me to kneel by the side of the deep Japanese soaking-tub, and scoot forward.

As I did so, the tip of my cock rested on the side of the tub, and Madison moved her lips towards it, resting her chin on the ledge, inches from my cock-head. I could feel her warm breath on my glans, as she locked her baby blue eyes onto mine, and with a glint in her eye, began to tease me.

"Tell Liv where you want her," Madison taunted me, as she extended her tongue and licked the pre-cum from my cock-head.

I was in an impossible position, torn between being in desperate need of release, and wanting to be respectful of my young friend Olivia.

"Olivia," I began with an unsteady voice.

"Liv," Madison corrected me. "You may refer to our maid as Liv, or rim-job girl," she added, as she took the end of my cock between her moist lips.

"Liv," I whispered hoarsely, as I felt my nuts constrict, under the intense pressure of my nine day load.

"Spread your knees slightly further apart, Mr. Pete," Olivia said sweetly. "Let me help Miss Madison get you off."

I was grateful for Olivia's interpretation of my desires, as it saved me from having to use demeaning language to direct her. I wanted to ejaculate more than anything, even if it was at the expense of her dignity. As I spread my knees slightly, Olivia placed her hands on my buttocks, and parted them to facilitate her access. As soon as I felt her tongue graze my taint, I knew that I wasn't going to last very long.

I had been used to coming four or five times a day, as Madison offered me twenty-four hour unrestricted access to all three of her holes. Basically, whenever I felt the urge to blow my load, I would tell her and she would offer me immediate release, with no concerns for her pleasure. In addition to my constant solicitation of sex, she would often awaken me with a blow-job, ensuring that I started my day with an empty nut-sack.

During the day, she would constantly tease me, either through her gentle caresses, her sexy outfits, or my favorite, her verbal taunts. Her sole aim was to keep me erect for the major part of each day, which wasn't difficult considering our chemistry, my short refractory period, and my youth.

Imagine then, my elevated state of arousal after having gone nine days without release, and you can see how quickly I approached my orgasm, as the two girls sucked and rimmed me, in unison. As we got into a rhythm, Madison rested her head on the ledge of the soaking tub, and I fucked her mouth. Olivia put her hands on my hips, to stabilize herself, which also enabled her to keep her tongue between my butt-cheeks as I rocked back and forward.

I let out another whimper as I felt my nuts tighten, which was Olivia's cue to stick her tongue inside my anal-passage. Moments later she began to wiggle it around inside me, and shortly after this new stimulation, I unloaded my nuts into Madison's warm mouth. After nine days it was a stupendous orgasm, and I had to support myself against the side of the tub to prevent my collapse. Madison kept my cock between her lips until it softened, and when she finally released it, she issued her next directive.

"Leave us, rim-job girl," she said dismissively, as Olivia removed her tongue from my asshole.

I felt Olivia stand up behind me, and she departed the bathroom in silence. At the last second I turned to see her pass through the doorway, her obedience a remarkable testament to the power of corporal punishment, and the red welts all over her ass and lower back, a fitting reminder of Madison's dominance over our new house-maid.

At Madison's insistence, we kept Liv naked for the first month after her thrashing with the rattan cane, both to cement her place as the low man on the totem-pole in our house, and to let her be reminded of what awaited her if she failed to be sufficiently compliant. Madison brought that particular instrument of torture home from Baldwin's place a few days after Liv got home, mounting it prominently on our fireplace as if to provide a constant reminder to the young girl to toe the line.

By this point in time, Madison had cut her work back to three days a week. I ran this development by my uncle, out of concern that her change in work status could potentially create a scenario under which I appeared to be supporting her. Madison got along really well with her boss, due to her prodigious sales volume, and at my suggestion, he agreed to continue to designate her as a full-time employee. This preserved her health benefits and also created a paper trail to suggest that she was still working full-time, thus reducing her legal claim against me for support, in the event that we ever broke up.

Even though Madison was only gone three days a week, I allowed Olivia the privilege of being clothed whenever my girlfriend wasn't home. I also insisted that she take it easy on these days, and when there were chores that needed to be done, I actually helped her. We quickly rekindled our friendship, and while she was scared to death of Madison, we had some great times when we were alone, and I felt a strong connection with her.

Our relationship was complicated by the fact that Madison started to utilize Olivia's rim-job talents more frequently. While I thoroughly enjoyed her tongue in my ass, it was strange to spend the afternoon as equals, conversing or playing chess, only to have her on her knees behind me as I fucked Madison doggy-style just before bed. Madison soon realized that I came more quickly when I was receiving analingus, and incorporated Olivia into nearly all of our sexual encounters.

Madison did an effective job of diminishing Olivia's worth, and I rarely saw or spoke to her when Madison was home. She still got me off five or six times a day, and Olivia would join us once we were coupled, her eager tongue lapping away at my asshole, serving to speed up my orgasms. Immediately after I came, she would retreat to her room, and Madison and I would snuggle in our post-coital bliss, even though I was the only one that had orgasmed. I am not sure if Olivia ever had an orgasm, but she seemed content to focus on my pleasure, in exchange for room, board and four grand a month.

About two months after Olivia moved in with us, Madison unexpectedly came home early from work. Olivia and I were on one of my ocean-front balconies, listening to music and playing cards, and we never even heard Madison come through the front door. Judging by Madison's reaction, you would think she had caught us fucking on the living room floor, and my girlfriend laid into me verbally after banishing Olivia to her make-shift bedroom. After her barrage of threats, she sent me to my room to reflect on my mistakes.

That night, as Olivia and I knelt naked in silence on the stone hearth of the fireplace, Madison enjoyed several glasses of wine. As uncomfortable as the rough finish of the rock was to kneel upon, I knew that she had positioned us there so that we were in plain sight of the rattan cane, mounted as it was just above the mantle. Madison had punished me before, although in the past it was always through sexual denial. This was the first time that the threat of corporal punishment was dangled over my head, and even though I had no idea of how painful it was to be whipped with the cane, Olivia's abject fear and constant shaking filled me with dread.

In my rational mind, I knew that I was free to leave at any time. I was a much bigger physical specimen than Madison, and could have easily overpowered her in a confrontation. I also had the option of calling my uncle to intervene, and as a last resort could have summoned my security detail to escort Madison from my property. However, my fear of my upcoming punishment, was less than my fear of losing Madison, such was the sexual hold she exerted over me. For this reason, I remained on my knees on the cold stone hearth, as she sipped her wine.

Finally, after nearly two hours she approached us, dragging her high-heels across the marble floor of my living area, which signaled her level of intoxication.

"You both really fucked up," she began, slurring her words. "Your poor judgment will not go unpunished."

Madison addressed me first, issuing me a very clear ultimatum, and threatening to move out unless she got some immediate concessions. I caved instantly, without even needing to hear what she wanted, begging her to forgive my temporary lapse of judgment, and promising never to screw up again. Her ultimatum carried much more weight than mine ever could, because I truly feared losing her, or at least losing the unrestricted access to the phenomenal sex she provided. The nine days she had spent at Baldwin's had been torture for me, both in the physical sense of being denied any sexual release, and in the psychological sense of constantly imagining what delights she was providing Baldwin. I never wanted to go through that again, and Madison knew it.

"You know I need to punish you both," she said ominously, as she reached for the rattan cane above the fireplace. "Otherwise our household falls apart."

My heart sank as I processed her threat. I knew that my behavior had been unacceptable, and probably warranted corrective action, however, I was scared stiff of being physically punished.

"Assume the position," she said, as she ran the cane across the palm of her hand.

I had no clue what Madison's desired position was, but as I looked nervously over at Olivia, she had got onto all fours, and lowered her forehead until it touched the ground. This left her in an extremely vulnerable state, with her ass elevated and her eyes facing directly to the floor, with no way to tell when the first blow was coming.

"Madison, please," I begged, involuntarily blurting out my fears, "surely you can extract your pound of flesh without resorting to violence."

"Assume the position, baby," she said more firmly.

I was trembling as I lowered my head to the ground, both from the anticipation of the pain, and from the indignity of being punished for a minor, non-sexual infraction within my own home.

"Madison, please," I begged. "Spare us the cane."

"I am open to suggestions," she said, enjoying the control she exerted over me. "What are the two of you prepared to give up, that will hurt you as much as a good thrashing?"

Put that way, I had absolutely no clue what I could offer her to prevent her from caning my ass. However, as I racked my brain, the only thing I really hated was Madison's monthly oral-worship of Clarkson. It seemed like as good a place as any to start.

"Until we get married, I won't ever give you grief about your monthly blow-job session with Clarkson," I offered.

"I need more than that from you," she said coldly. "Tacit agreement is insufficient. I need your approval, encouragement, even better your participation."

"Until we get married, I will participate then," I agreed, without having a clue what that involved.

"Not specific enough," she countered. "I am going to give you each one stroke of the cane to see if the pain maybe clears your head, and sharpens your negotiation skills. Who wants to go first?"

This wasn't the first test of my manhood but it certainly was the most current, and I was about to fail it. I knew that I should have stepped up and taken the first blow. Olivia was at her place of employment and I was her immediate supervisor. I had allowed her, no encouraged her, to stop working and join me on my balcony in a game of cards. If we had been in an office somewhere, as the manager, I would have been given the harshest punishment. However, because I was an eighteen year old pussy, I allowed my fear to affect my sense of duty, and remained silent.

"No takers?" Madison intoned. "How about alphabetical, baby?" she offered.

Madison had referred to me as baby twice in the last few moments, which seemed incongruous considering she was about to thrash me. However, as with all things she does, it was clearly premeditated, and she moved behind me and rested the cane on my trembling ass.

"I am first?" I questioned, the fear palpable in my voice.

"Well," Madison responded with a smile, "B is before O, baby."