Trust Fund Baby Pt. 07

After Madison caught Olivia goofing off, she made some changes around the house, with immediate effect. Firstly, she purchased Olivia a pedometer, and required her to wear it whenever Madison was out of the house. Olivia was tasked with a goal of twenty thousand steps per day, which ensured she never had a moments rest, and had to be constantly on the move. She was denied her clothing privileges once again, and forbidden to shave her pubic area, the unruly growth of her bush becoming very off-putting to me within just a couple of weeks.

While her unkempt pubis was designed to reduce my interest in the younger woman, it was evident that Madison planned to tidy her up for her dates with Maxwell and Clarkson.

After all, "make sure the bitch shaves her pussy," was one of the last things the black guy had said upon hearing that he was going to enjoy Olivia. I felt sorry for the young girl as she scurried naked around my home, constantly moving in an attempt to register twenty thousand steps on her pedometer. Olivia had been working as an escort for a few years, and as such, prided herself on her personal grooming and appearance. Within just a couple of weeks, denied the privilege of shaving, her pussy, legs and underarms were showing signs of neglect, and it was affecting her self-esteem.

Being kept naked twenty-four hours a day probably didn't help her self-confidence either, especially as Madison never permitted Olivia any modesty, even when the personal trainer came in, three times a week. He ogled her initially, barely able to contain his astonishment at the revelation that I had a naked house servant.

However, despite repeated offers from Madison for him to enjoy a blow-job from Olivia, the personal trainer left her alone, wary I think that any move on my house-maid would jeopardize his employment status. This rejection further cemented Olivia's lack of self-worth, and Madison frequently taunted the younger girl about it.

"You ugly unkempt slut," she mocked her one day as Olivia was scrubbing our kitchen floor. "Even the personal trainer, a man with elevated levels of testosterone, doesn't have any interest in you."

I know I should have intervened, but I was much more concerned about the prospect of losing Madison, than I was with protecting Olivia. Once a month, Olivia's make-over would begin, signaling the approach of her visit with Clarkson. The beauticians would arrive, and over the course of several hours would feminize the young girl, completely transforming her from a hirsute house maid, to a beautiful object of desire. I avoided Olivia on these make-over days, as the sight and scent of her once she was prepared for Clarkson's enjoyment, made me erect.

Olivia would be waxed from head to toe, before having her eyebrows plucked and shaped. After she was hairless from the eyes down, her entire body would be moisturized, using a scented lotion that smelled divine. Her anal passage would be lubricated, and an oversized, black butt-plug would be wedged inside her, in the event that Clarkson wanted to ass-fuck her.

Next would be the application of her press-on, fake nail extensions, chosen for the simplicity with which they could be added and removed, and then she would have her make-up professionally done. Her lipgloss and eye shadow would be chosen to carefully match whatever color lingerie Clarkson had selected for today's encounter. At his request, the intimate ensembles of both women would be hanging on the back of my bedroom door overnight, just to rub my nose in it.

Madison would get dressed immediately after the cosmetology team left, while requiring Olivia to remain naked. It was at this point that I tried wholeheartedly to avoid Olivia, as knowing that I was on restriction for the day, while Clarkson was about to enjoy the two women in my life, elevated my level of arousal. The sight of her naked, hairless body, artfully feminized and intoxicatingly scented, made my cock harden every time, and I knew that this would put me in a compromising position if Madison noticed.

Olivia's skin glistened with the moisturizer, and the hairdresser knew exactly how to extract the maximum amount of femininity and youthfulness from her. On top of that, her rosebud was sufficiently well lubricated that it was noticeable from a distance. The Anal-Ease petroleum jelly coated her inner-thighs and the inside of her buttocks as she moved gingerly around my condominium, with the black plug protruding from her.

It truly was a startling transformation of the young girl, and my only regret was that it occurred just once a month, on the very day that I was on sexual restriction. Madison also underwent a professional hair and make-up session on Clarkson's special day, although she was always so beautifully presented, that it was nowhere near as noticeable.

Madison would make no attempt to hide her jealousy when Olivia was all dolled up, and often made extremely hurtful comments.

"Well that makeover was a complete waste of time," she said in a bitchy tone right after the beauticians had left. "Your nose is going to be between Clarkson's fat butt-cheeks all morning. He won't even see your face."

I was still vacillating between proposing to Madison, in order to gain the monogamy that I so desired, or trying to pluck up the courage to leave her. The fact that my cock responded favorably to Olivia gave me some encouragement that maybe I could have a sexually fulfilling life, without Madison around. However, now that Madison had wormed her way deep inside my psyche, knew all my hot buttons, and currently provided me with the additional stimulation of a rim-job during each and every orgasm, it made the likelihood of me ever leaving her diminish with every passing day.

Between the two women, they got me off five or six times a day, and even though I would occasionally wake up in the morning with virtually no desire to orgasm, the second Madison decided she wanted me erect, I was absolutely powerless to prevent it from happening.

That is why I detested restriction day so much. Madison had stopped marking the calendar on our fridge with an imprint of her glossed lips, which served to designate the upcoming Clarkson encounter. My new signal would be the appearance of two identical lingerie ensembles, gathered in their entirety, and hung on the back of my bedroom door.

This provocative visual invariably triggered my libido, and while Madison was amenable to my every sexual desire, the fact that restriction day loomed made me extremely horny. Madison knew this of course, and in a move that made me question why I was still with her, required all sexual activity just before restriction day, to take place in my master bedroom, in full view of the intimates that they were planning to wear to service Clarkson.

This was a double-edged sword for me, as the sight of their exquisitely beautiful lingerie, brought me to climax much more quickly, but was also tough to look at immediately after I blew my load. Olivia spent the majority of these sessions behind me, with her tongue in my ass, as the sight of her having gone thirty days without seeing a razor blade, was difficult for me to watch. Had I been allowed to enjoy her the following day, with her hairless, scented body and her flawless hair and make-up, I would have certainly wanted to witness her sucking my cock, or even have engaged in a sixty-nine session with her.

The first time Clarkson enjoyed both of the girls, was the Thursday morning of his wardrobe makeover. Madison made me drive them to the Tom Ford store in my truck, and while I tried my hardest not to stare at the two flawlessly presented girls, I couldn't escape the scent of them. Long after I parked up to allow Madison to be Clarkson's personal shopper, and even with the windows of my truck open, the intoxicating scent still permeated the air.

I couldn't help stealing the occasional glance through the windows of the showroom, and each time I had to turn away in disgust. The two girls were flirting incessantly with the older man, and Madison spent much of the session kneeling in front of him, under the pretense of adjusting the hem of his pants. The personal shopper experience took about an hour, during which time Clarkson dropped over forty grand on suits, shoes and accessories.

I never saw Madison after she got up from her knees and rang up his purchases. Olivia came out to my truck with an arm full of dress shirts, and tossed them onto the back seat, through the open window.

"These need to go to the dry-cleaners on El Camino Real," she informed me, "heavy starch. Miss Madison is ready for you to watch the store while we entertain Mr. Clarkson."

I exited the truck on autopilot, dreading the next part of my day and wondering how the fuck I had got roped into taking Clarkson's brand new dress shirts to be ironed and starched. Olivia asked me for my keys so that she could close the windows of my truck.

"Pete, for fuck's sake, there are nine grand worth of shirts on your back seat," she admonished me.

I dragged my ass reluctantly into the Tom Ford showroom, just as Clarkson disappeared from the top of the stairway into Madison's make-shift living accommodation. Olivia scurried up the stairs, without looking back, focused on the task at hand, emptying the nuts of my girlfriend's lover.

Luckily for me, during the two hours that I paced the empty Tom Ford showroom, no customers entered the building. This wasn't that unusual for a weekday morning, the exorbitant prices of the upscale clothier reducing the volume of customers, and the customer service component which featured the personal shopper services, making much of the store's business by appointment.

I say lucky for me, because for much of the two hour customer appreciation session bestowed upon Clarkson by Olivia and Madison, there were lewd sounds emanating from upstairs. Who knows what the hell was happening up there, but at some point somebody was getting spanked, hard. A few moments later, I heard an anguished wail from the top of the stairs, followed by the unmistakable sounds of someone getting butt-fucked. I prayed to God that it was Olivia, as I heard the slapping sounds accompanied by the grunting of someone that was either giving birth, or getting impaled by something that didn't fit comfortably inside the orifice it was violating.

Periodically, the sounds of a young woman in the throes of an orgasm filled the air, although I knew Madison well enough to know that she was faking hers. Either way, it would have been emasculating to have those sounds of delight witnessed by a customer, so I was grateful for the lack of traffic in the store.

As much as I detested the idea that Clarkson was getting sucked off by my girlfriend as a token of appreciation for his custom, I couldn't help notice that I had an erection the entire time. Finally, after what seemed like an eternity, Clarkson appeared at the top of the staircase, a smug, satisfied smile on his face, as the girls continued to fawn over him.

As they began to descend the stairs, the first thing I noticed was that neither of them were holding a new-born baby, which confirmed my suspicion that the pained grunting sounds were from anal-sex, not childbirth. It still didn't satisfy my curiosity about which one of them he had sodomized, although as I saw them both limping gingerly down the stairs, it was evident that both of them had been ass-fucked.

They were both still wearing the peach chemises that they had entertained him in, although Madison had added a Tom Ford trench coat for modesty, as she was technically still at work. Olivia was afforded no such protection, and looked like a total fuck-toy as she took her place by the front door.

He barely acknowledged me when he passed me on his way out, although he had his hand on Madison's ass as she escorted him to the door, where Olivia was waiting with the shoes and accessories he had ordered.

"Your suits will be tailored in about a week," Madison said cheerfully. "Pete will pick your shirts up from the dry-cleaners as soon as they are ready."

Clarkson gave me a condescending nod, and then he and Madison shared a tender embrace at the front door. She seemed reluctant to part from his extended hug, and raised her eyes to his, before they engaged in an open-mouthed kiss. Clarkson extended his leg towards her, parted her trench coat to reveal her scantily clad frame, and she moved closer into his personal space.

As he lovingly kissed her, she began to gently gyrate her crotch against his leg, which was now positioned between her thighs. Whether it was done to infuriate me, or was an involuntary reaction to the new stimulation, I will never know, but she began to dry-hump his leg like a bitch in heat. Clarkson, never one to shy away from confrontation, looked over in my direction to make sure that I was watching, and then slipped his hand inside her trench coat and began to openly grope my girlfriend's breasts.

I was powerless to say anything as Madison had been very forthright about exercising her rights to fuck and suck whoever she wanted, until I proposed to her. In addition, Clarkson had just dropped forty grand on his new wardrobe, and probably felt entitled to feel up my woman.

"See you soon, sugar lips," he said as he patted her ass, and they enjoyed one more passionate kiss.

When he finally exited the showroom, Madison stayed by the window, waving like a doting wife, until he got into his car and left the parking lot. She couldn't contain her excitement as she moved towards Olivia.

"Thirteen hundred dollars commission," Madison exclaimed, as she high-fived Olivia, in an uncharacteristic moment of solidarity between the two of them. "Not bad for getting a tired old man off three times," she added, giving me an unwanted insight into Clarkson's pleasure session.

By this point in our relationship, Madison knew that her extra-curricular activities aroused me intensely, and as she approached me her gaze was focused on my crotch. Under normal circumstances I would have tried to hide it, but the sights and sounds of their hook-up had made my cock rock-hard, and I was hoping that Madison would cut me some slack, and consider my restriction day done.

"Watch the store, Liv," Madison instructed the younger girl. "My manager should be here in about twenty minutes. Should be more than enough time for Pete," she added with a giggle.

Once she set the expectations for my time-frame, we headed upstairs, into the small living accommodation where Madison still kept some clothes and personal effects. Evidence of Clarkson's two-girl session was everywhere, and while I would have preferred to clear it away, I knew we didn't have much time.

The day-bed had obviously been used, as the covers were folded back and one of the pillows was propped up against the end wall. The other pillow was lying on the floor next to the bed, the inference being that one of the girls had been kneeling on it. There were two pairs of identical panties discarded on the floor, next to a large strap-on that was coated with vaginal secretions. Also lying on the floor was the black butt-plug that Olivia had been wearing earlier that morning.

"Clarkson ass-fucked her for his second pop," Madison said without a hint of shame. "Opened that bitch right up. We need a bigger butt-plug."

She must have noticed me steal a glance at the clock, because she admonished me right away.

"Don't concern yourself with the time, Pete," she said in a forceful tone. "We have at least fifteen minutes before my boss arrives. You never last that long."

Even though it was a clear dig at my sexual prowess, I didn't care. I had an erection and Madison knew a hundred ways to get rid of it. As she began to unzip my jeans, apparently dispensing with the usual foreplay, I realized that she had more than enough time to accommodate me.

Once I was naked, Madison laid down on the day-bed, parted her legs and invited me to climb on top of her. I didn't need a second invitation and as I lowered my body towards hers, she guided the tip of my cock into place, and I slid right inside her.

"You may begin," she whispered, taking the lead as she always did.

As soon as I began to thrust in and out of her, two things became very evident. Firstly, she was very wet, a sure sign that being with Clarkson had aroused her. Also, her pussy wasn't as tight as it normally was, which was confusing because Madison claimed that she rarely had penetrative sex with Clarkson. Maybe she had gone the extra mile to thank him for the huge purchase, that had netted her thirteen hundred dollars in commission.

"Liv fucked me with the strap-on," Madison said, as if she was reading my mind. "That thing was huge. Clarkson was messing with me today. He said it was payback for the pounding I gave her on Super Bowl Sunday. That asshole jerked off on us while she was balls-deep in me."

I grunted as I processed her words, and Madison knew I was already on the road to orgasm.

"Did you hear Liv squealing like a pig when he butt-fucked her?" she whispered, as she rested her lips against my ear. "I wouldn't wish that on my worst enemy."

While the thought of Olivia undergoing a complete beauty make-over just to get sodomized by Clarkson was titillating, it was engaging in talk about Madison's extra-curricular activities that always made me come hard. For this reason, I steered the conversation back to my girlfriend.

"Did you watch when he fucked her ass, baby?" I asked shakily.

"I had a bird's eye view," she said excitedly. "I was underneath the two of them, sucking his nuts. Even though he had already come once, he blew a huge load into the Magnum he was wearing. I left it in your truck for you. You are going to eat its contents later, after I make your special ice-cubes."

As she continued to taunt me I felt my nuts constrict, and seconds later I erupted inside her. It was another tremendous orgasm, fueled by Madison's expert verbal taunts, and as soon as I finished ejaculating, Madison glanced at the clock and laughed.

"Well that took all of three minutes," she said cruelly. "I am going to take a shower. Why don't you clean my room up before you leave?"

Later on in life, it would be me issuing such directives to young women who had shared my bed. However, as Madison was firmly in control of our love-life, I followed her directive and began to tidy up. I made the bed, put the two pairs of panties in her laundry hamper and washed and dried the sex toys. She had discarded the peach-colored chemise by the entrance to her shower, and I went to hang it up in her closet before noticing that it was in dire need of dry-cleaning.

I never asked Madison for the full run-down of Clarkson's three orgasms, but by the look of her lingerie, she was wearing this particular garment when he jerked off all over her back. There were numerous semen stains the entire length of the LaPerla chemise, although they had dried to a flaky residue. I ended up taking it with me, as I was heading to the dry-cleaners with her lover's shirts.

When I got downstairs Olivia handed me my keys and looked around nervously for Madison.

"She is still in the shower," I said, which seemed to assuage her concerns about talking to me.

"I fucked the crap out of that bitch," Olivia said spitefully, obviously taking some solace from the encounter. "Clarkson got so excited that he ended up beating off on her, as she was impaled on my strap-on."

"I have seen the proof," I said sheepishly, as I held up the soiled chemise.

In that moment, I felt a strong connection to Olivia, and I wanted to give her a hug. However, Madison had made it crystal clear that we were not to have unnecessary interaction, so I just smiled at her, and started to walk to the door.

"I am sorry about your truck," she said quietly. "Madison made me do it."