Trust Fund Baby Pt. 12

The transformation in Madison's appearance was unbelievable when she returned from her shower. As an avid user of Instagram, I was well aware of the prevalence of filters in photos of young women. However, I had only ever seen Madison dolled up, and in the harsh light of day, her natural beauty left a lot to be desired.

Her hair was still wet, and hung limply from her head, lacking any of the body or weight that the hairdryer and accompanying products provided. She was without her fake eyelashes which always made her eyes look stunning, and had removed her piercing blue eye-contacts. She still possessed some nice blue eyes, but they paled in comparison to her colored contact lenses. She wasn't wearing any makeup either, the skillful application of which made her look several years younger, and accentuated her best features, her plump lips and her sculpted cheek-bones.

As Madison entered the room she looked smaller too, and when I noticed that she was barefoot, it occurred to me that the five inches of height-loss made her look much less like a runway model than normal. The Walmart sweatsuit looked ridiculous on her, unflattering and two sizes too big, the exposed price tags announcing to the world that each piece had cost seven dollars and ninety nine cents. As I got closer to her, I reflexively inhaled her scent, and instead of the usual intoxicating aroma, I was greeted by the smell of Dove Soap.

"Would you still fuck her?" Olivia asked me, once it was evident that I had absorbed every detail.

"Excuse me, Olivia?" I asked, bewildered by this strange question.

"As it stands, would you still want to have sex with Madison?" she intoned slowly. "Pete, please be honest with me."

"Yes," I said hesitantly. "I think so."

While it wasn't a glowing admission of desire for my ex-girlfriend, it was enough to spur a threatening response from Olivia, after seeing a smile appear on Madison's face.

"Well, we will work on that," Olivia said ominously. "After lunch. Tuna sandwiches on sourdough bread, Madison," Olivia said, as if she was at a deli-counter. "You may eat too."

Any resistance had been ground out of Madison by her disturbing encounter with the shock collar, and as I looked on in amazement, my ex-girlfriend began to prepare lunch for the three of us. Olivia opened a bottle of wine, grabbed two glasses and ushered me out onto one of my ocean-front balconies.

It was a beautiful day on the Newport Beach coast, and as we sat and sipped our wine, I began to anticipate harmony within my home. It appeared that Madison was prepared to submit to Olivia's whims, at least as long as she had nowhere else to go. I knew that she wouldn't be with us for very long, but would find another older man to take care of her. Of course, as the stories of her subjugation at Baldwin's house circulated the tight-knit community, there were less and less interested parties, but if Madison lowered her sights slightly, and increased the frequency and intensity of the sex-acts that she exchanged for a safe place to live, it wouldn't take her long to find another benefactor.

What I couldn't have known at that time, was that Olivia was well aware of Madison's plans, and had decided to derail them. Madison ate in the kitchen as Olivia and I enjoyed the view from the balcony, and after lunch the dishes and wine glasses magically got cleaned and put away.

Olivia took control of Madison immediately after lunch, with virtually no pushback from the older girl. After forcing Madison to kneel before her, Olivia reattached the shock collar, although she did make a point of leaving the remote in the kitchen.

"I really don't want to have to use this," she threatened, as she placed the remote on the countertop.

It was very evident from Madison's compliant nature that she wanted no part of the shock collar and the two of them disappeared into the guest bathroom. Ten minutes later, Olivia called me to come and join them.

"Would you still fuck her?" Olivia asked, as I looked over at the latest modifications that she had made to Madison.

Madison's ever-present nail extensions were now gone, a small pile of bright pink nail clippings evident on the vanity, where Olivia had instructed her to cut them off. Her hair was a couple of inches shorter too, the matching platinum blonde hair extensions having been removed and tossed on the bed.

"Pete, please," Madison begged. "Those extensions cost me six hundred dollars. Don't let her throw them away."

"They actually cost me six hundred dollars," I corrected her. "I paid for them. You are free to leave at any time, I will even drop you off if you need a ride. However, as long as you are in my house, you will obey Olivia's instructions. Understand?"

Madison tried to lower her head in submission, but the shock collar prevented her from doing so. She seemed to recognize that the minor changes Olivia had made to her appearance were temporary, and easy to fix. While they had diminished her looks significantly, it would only take a few minutes to restore her to her former glory.

"Understood," she whispered.

"Would you still fuck her, Pete?" Olivia repeated, her obsession with my attraction to Madison becoming more and more apparent.

"Olivia," I said, choosing my words carefully. "Madison was my first love and after all we have been through, I still find her attractive."

After I left the room I heard the two of them talking animatedly, and some of Madison's fire had returned, presumably emboldened by my statement of attraction to her. A few moments later, the two of them entered the living room, and I noticed Madison's hands were bound behind her back. Olivia dragged the frightened girl into the garage and I followed out of concern that she was going to shock her again.

As I stood in the doorway, Olivia forced Madison to her knees on the cement floor, before storming out of the garage. Returning a few seconds later with my hair clippers in her hand, she made a chilling proclamation.

"You won't want to fuck this bitch when I am done with her," she said coldly. "Neither will half the men in Newport Beach."

As I watched on in disbelief, Olivia straddled Madison's upper back to prevent her from standing up, grabbed a fistful of Madison's still damp hair, and began to shear her like a lamb. Madison was powerless to stop Olivia with her hands bound tightly behind her back, but she was crying and screaming for me to intercede.

I watched impassively as Olivia ran the hair clippers over Madison's head, systematically removing her beautiful blonde hair, which fell in clumps to the garage floor.

"Pete, please, for fuck's sake," Madison begged me. "Stop her."

Her impassioned pleas fell on deaf ears, and even though she was in a considerable amount of distress, it wasn't pain that she was feeling, but rather the coming to terms with the fact that her femininity and allure was in large part due to her phenomenal, long platinum hair. Once Olivia had chopped most of it off, rendering Madison quite physically unappealing, she switched clipper guards, selecting a size one, which delivers a uniform cut of exactly one eighth of an inch in length.

Madison continued to beg me for intervention, although by this time the damage was done, and Olivia was merely tidying up the crew-cut. Madison was sobbing uncontrollably now, but Olivia showed no mercy and dragged her into the house, positioned her in front of a large mirrored wall, and told her to kneel.

"Would you fuck her now, Pete?" Olivia asked with a giggle, realizing that she had completely altered Madison's outward appearance.

When I declined to answer, Madison sobbed quietly, as she absorbed her reflection in the mirror. With most of the superficial elements removed, she looked very plain, matronly almost, as she knelt in her baggy Walmart sweatsuit. Short hair did not suit Madison, and as Olivia taunted her, she closed her eyes to block out the visual of herself, and wept.

"You can leave the house if you want," Olivia offered. "We will drive you wherever you wish. An upscale bar, South Coast Plaza mall, the Lamborghini dealership, your usual hangouts to meet wealthy men. Of course, they won't notice you now," she added cruelly. "Get used to being a three instead of a ten."

Everything Olivia said, whilst unnecessarily cruel, was true. Southern California was a magnet for hot chicks from all over the United States. Every aspiring model or actress in the country gravitated towards the Greater Los Angeles area, and once they arrived they quickly learned the go-to places to meet a Sugar Daddy. Settled predominantly in Newport Beach, Beverly Hills and Malibu, exceptionally beautiful women could write their own ticket, using men as a stepping stool until they found a sufficiently wealthy one to marry.

The Sugar Daddies played their own version of the game, their wealth giving them access to unbelievably hot chicks, with the richest guys having the pick of the litter. Madison had played that game for close to a decade, but time runs out for everyone, and stripped of all her cosmetic enhancements, at thirty years old she was no longer able to compete.

"Well?" Olivia said, pressing Madison for an answer. "Are we taking you somewhere or are you going to get with the program?"

"What do you want from me, Olivia," Madison sobbed. "Just tell me. I will do it."

You could feel the tension in the room dissipate as Madison capitulated to the younger woman. In much the same way that a horse-breaker tames a wild mustang, Olivia had broken Madison. She had given up the fight, decided that, for the time being at least, she needed a roof over her head more than she needed her dignity. As she knelt before the younger girl, her head forced skyward by the considerable height of the shock collar, there was a look of resignation on her face. Olivia in contrast, wore a triumphant look on her face, and was visibly aroused. She had finally subdued her nemesis, and the control was making her wet.

While I wasn't fully aware of their history, I knew that they had known each other for a few years, and harbored a healthy disdain for each other. They had both worked the nice hotels and cocktail bars of Newport Beach as escorts, although the demographic of their respective clientele was markedly different.

Madison trolled for wealthy men, an exclusive consort available for hire for the night or often on a long-term basis. Wildly expensive, she catered to the man who wanted exclusivity, and was willing to pay for the privilege. Olivia, on the other hand, while harboring aspirations of being a high-class escort, was available for pretty much everything, by the hour, occasionally even offering a "quick visit" on the now-defunct Craigslist website, for about sixty dollars.

The "quick visit," which was a staple in the escort section of Craigslist, was a fifteen minute session, enabling the lucky punter a covered release, through penetrative or oral sex. This was the main difference between the two women, as any form of sexual release with Madison was likely going to cost you at least ten times that amount.

I had leveled the playing field between the two of them, by inviting Olivia to live in my home as an equal, whereas Madison had to constantly earn her right to stay. As Olivia approached Madison, it became apparent that the time for her to earn her lodging was upon us.

Olivia removed the shock collar from Madison's neck, and supporting her weight by her shoulders, gently lowered her to the floor. Madison's hands were still bound tightly behind her back, but once she signaled that she was comfortable, Olivia began to disrobe.

"Do you need some privacy?" I asked, fully prepared to leave the room.

"No, Pete," she said softly. "You should witness this."

Olivia took her sweet time to undress, driving home the fact that Madison was hers to play with, as she saw fit. Once she was naked, she placed her feet either side of Madison's shoulders, and lowered herself slowly to her knees, so that her pussy was right above Madison's mouth.

"Eat me out," Olivia ordered.

I watched on intently as Madison extended her tongue and began to lap at Olivia's clitoris. Madison wasn't a lesbian by any means, but she had participated in some paid encounters with wealthy Newport Beach women, and she had certainly engaged in her fair share of lesbian sex-shows for older established men. For these reasons, she knew her way around the female anatomy, and it wasn't long before she started to evoke a physical reaction from Olivia.

Olivia had a rocking little body, and while our relationship had morphed into a very close friendship, we still made love occasionally. As I watched her nipples harden under Madison's tender ministrations, I felt my cock stir in my pants. The events of the day, while highly distressing for Madison, had got Olivia's juices flowing, and her vaginal secretions were transferring to Madison's face, as she ate the younger girl out.

Even with her hands tied behind her back, Madison was doing a phenomenal job of bringing Olivia to the boil, although I imagine it would have felt even better, if Madison's hands were free to roam. As Olivia approached her climax, I knelt next to her, and began to kiss her tenderly. She let out a moan of appreciation as we French-kissed, and stiffened up when I began to caress her erect nipples.

I looked down at Madison a couple of times as she dutifully attended to Olivia's needs, and was surprised to find that our sexual chemistry was gone. In fact I felt nothing towards her as we both tried to bring Olivia to climax. Our situation reminded me a little of our recent threesome with Maxwell, when Madison cuckolded me with the young black man, riding his cock as I sucked his nuts, just before he forced me to rim him.

Now that the shoe was on the other foot, I wanted to rub Madison's nose in it, and I lowered my lips to Olivia's nipples and began to suck them. I maintained eye-contact with Madison as I pleasured her nemesis, but without her piercing blue contact lenses, and her platinum blonde hair, I didn't find her that attractive.

"Oh, Pete, right there," Olivia whispered, as I took one of her nipples between my teeth, and gently bit it.

Olivia reached her climax a few seconds later, crying out as she came all over Madison's face. I think the protracted power struggle between the two of them had taken its toll on both parties, and for now they were content to co-exist, even though it was obviously Olivia's world in which they lived. After she composed herself, Olivia signaled for Madison to keep licking, reaching her second orgasm with far more alacrity. Between my ex-fiancée and I, we coaxed four orgasms out of Olivia, and when she was done, she sat on Madison's face, breathing heavily, wearing a contented look.

Any relief that Madison may have felt was short-lived, as Olivia got a second wind.

"Untie her hands, and get the bitch up on all fours," Olivia instructed me.

Once Madison was in the desired position, Olivia retrieved a bejeweled, pink dog-collar, made of leather with a few rhinestones on it, and the name "Scamp" embossed onto the front of it, in a contrasting shade of pink.

Madison, or "Scamp," as we would refer to her that afternoon, knelt silently on all fours as the collar was affixed around her neck. You could tell by the dejected look on her face, that Madison hated this humiliation, but I was onboard the second I saw it, and gleefully adopted my role.

"Does your puppy need a drink?" I asked with a chuckle. "That bitch looks thirsty."

"She probably is," Olivia said, as I moved towards her and kissed her gently on the lips. "Can you get her something to drink while I get ready? Her bowl is in the utility room."

Even though the days of them being engaged in a power struggle were now behind them, I still thoroughly enjoyed watching Olivia assert herself over my ex-fiancée. As Olivia readied herself, I retrieved the bowl from the utility room, and filled it with clean water.

The stainless steel doggy-bowl was adorned with stenciled paw-prints and the name "Scamp" written in large letters across the front. As I placed the bowl on the ground in front of her, Madison extended her tongue, and lapped the water up like the bitch she was, thereby assuming ownership of it.

When Olivia returned, she was wearing a large black strap-on cock, and brandishing a long doggy tail that was attached to a butt-plug.

While I couldn't wait to see that snooty cunt Madison crawling around my living room floor with a doggy tail rising proudly from her ass, I also didn't want to injure her permanently. For this reason, I felt obligated to inform Olivia that Madison had sustained some minor injuries during her stay in Newport Coast. Before I could get into any of the details, Olivia cut me off.

"Pete, I am well aware of Madison's injuries," she began dispassionately, "as is half of Newport Beach. In fact, if you must know, I attended a few of those parties where Jamie invited all and sundry to ass-fuck her. It was quite brutal, as you can probably imagine. Don't worry, Pete," Olivia assured me, as she started to lube up the butt-plug end of the doggy tail. "My specialty is the infliction of pain, without causing any long-term damage."

To her credit, the younger girl did manage to wedge that doggy-tail into Madison's anus without much drama, even though Madison fought her all the way, the clenching visible as she tightened her sphincter against the threat of a new invasion.

Once the tail was inserted, Olivia knelt behind Madison and fucked her vaginally. I am sure the last thing Madison wanted was to achieve orgasm under such humiliating circumstances, but Olivia ordered Madison to stimulate her own clitoris, and under their combined efforts she climaxed. Olivia withdrew the phallus from Madison's wet pussy and wiped the secretions onto her buttocks.

"I need a nap," Olivia announced, as I helped her to her feet.

We made no effort to assist Madison as we left for my master bedroom. To her credit, Madison never asked us to, seemingly at ease with her role as our sub. We ended up keeping her there for the rest of the afternoon, with the tail protruding from her asshole, as Olivia and I snuggled in my King Size bed.

"That went well," I whispered, as I spooned her and kissed the back of her neck.

"It's a start," Olivia responded ominously. "I will get her where I need her to be."

I never gave Madison much thought as I drifted off to sleep, the wine easing me into my mid-afternoon nap. However, when I woke up less than thirty minutes later, Olivia was fast asleep and I had an erection. I was still a young man, fast approaching twenty years old, but with the capacity to ejaculate eight or nine times a day, under the right provocation.

I went into the bathroom to jerk off, but as soon as I remembered that we had taken Madison as our house-maid, I decide to use her instead. When she saw me coming down the hallway, naked with an obvious erection, she smiled and batted her eyes at me. Whilst this might have elevated my arousal a few hours ago, this was not the same woman who I had lusted over for all these months. Madison seemed to forget that she had been stripped of her allure by the forced removal of her cosmetic enhancements, and with her head shaved tight, she just wasn't that attractive.

That said, I am a man, and I had an erection, and Madison possessed three very available holes that I could use, if I were so inclined.

I didn't even ask her, I am embarrassed to admit. Bowing to my carnal desires, I pulled the tail out of her ass, rolled her onto her back, spread her legs roughly apart, lifted her knees so that her feet rested flat on the floor, and eased my way into her tight pussy. Unsurprisingly, she was still wet, having self-lubricated from the fucking that Olivia had given her.