Trust Fund Baby Pt. 13

After several months of living with me free of charge, Olivia suggested that Madison should get a job, and contribute to the cost of running the household. It was comical really, given the fact that my trust fund paid me one hundred and sixty thousand dollars per month, and was due to increase to two hundred and twenty five thousand dollars per month, on my twenty-first birthday.

However, Olivia was adamant that Madison not be given a free ride, and so I arranged for her to get a paper-route, delivering the Orange County Register seven days a week. Madison was understandably humiliated by the prospect of delivering newspapers in our immediate neighborhood, particularly as she didn't own a car. Her new job required her to get up at five in the morning, and took her almost three hours per day to complete. At the end of the first pay-period, she received a check for just over three hundred dollars, and at Olivia's insistence signed it over to me, as payment for her food and lodging.

"You don't need money, Madison," Olivia taunted. "I cut your hair, and we let you buy whatever clothes you need at the Goodwill store. You don't have any other expenses to worry about."

There were a couple of incidental benefits of Madison's paper-route that didn't become obvious until she had been doing it for a few weeks. Firstly, being outside for long periods of time, caused some physical improvements in her appearance, as she lost some of her flab, and her milky-white skin began to turn brown. Secondly, as she met some of the neighbors for the first time, and word got around the complex that she was available to walk dogs, or water house-plants, she picked up some extra work, the payment for which Olivia generously allowed her to keep.

For the most part Madison and Olivia co-existed in my house, although Olivia started to expect oral-sex from her house-pet more and more frequently. She also dominated Madison more often, particularly when I was out of the house, although I didn't become aware of this until I came home early one day from a meeting that was canceled at the last minute.

As the months passed I turned twenty-one, and with the substantial increase in my monthly stipend, I upgraded my home, moving to a five thousand square foot house on the sand in Newport Beach. Located as it was in a small community of custom homes behind a secure guarded gate, my new place had a five-car garage, a huge circular driveway and, more importantly to Olivia, enough rooms that we could designate one as a punishment room.

Olivia had spent many hours in Baldwin's specially designed, sound-proofed, quasi-torture chamber, and knew exactly how to equip ours. She hired a contractor to sound-proof it and to install black-out shades, so that she could add light-deprivation to Madison's ordeal. Once the ominous-looking room was finished, we installed a heavy-duty metal door, that could be remotely unlocked by my phone, in case of emergency. The finishing touches were applied by a local dominatrix, who walked Olivia through the purchase of bondage equipment and furniture.

Olivia had one wall mirrored from floor to ceiling, which enabled her to view Madison's anguished looks as she put her through her paces. Occasionally, she would make Madison strip naked, and Olivia would critique her hirsute, unattractive form, comparing her to a large, poster-sized print that we had mounted next to the mirror. Taken on Madison's best day, in very flattering light, with the perfect clarity and detail of a 4K camera, it was my iPhone home-screen for several months. Essentially a portfolio quality head-shot, taken moments after Madison had been treated to a full make-over, it was sufficiently alluring to have prevented me from hooking up with a high-class escort, when I was in New York staying at the Peninsula Hotel.

Koko had been flirting with me in the bar of the upscale hotel, we had agreed on price and I had outlined my sexual proclivities. One look at my phone to check the time, and that photo, depicting a perfect, flawless image of Madison, was enough for me, despite my raging erection, to walk away from that adorable young Asian escort.

That phenomenal image, blown up to larger than life size, cut Madison to the core. I am sure it contributed to her emotional fragility, as she stood there stripped of all her superficial, but highly desirable cosmetic touches, and was assaulted by a reminder of her former glory. In fact, if Olivia was feeling particularly cruel, she would put a naked Madison in the punishment room with the bright lights on, and just let her digest the picture, which highlighted the decline in her physical attraction.

There was a small glory-hole right under the poster, a four foot high box in which Madison could kneel, and anonymously service whoever Olivia felt was deserving of a treat. While they were getting sucked off, the guys could stare at the oversized photo depicting Madison in her glory days, while Olivia would constantly assure them that the girl in the box, was indeed the girl in the photo.

In fact, after I told Olivia that the Doctor at the sexual health clinic had assured Madison that the risk of STIs from oral sex was infinitesimal, Olivia increased the frequency of the sexual favors, handing them out for the slightest reason. My new security guards enjoyed regular trips to the punishment room, although they renamed it the pleasure palace. I felt secure knowing that they had increased the vigilance of their patrols, in exchange for the occasional trip into what they must have considered nirvana.

Of course, because Madison no longer drove, she wasn't required to present any identification to the security team in order to get a parking pass for her vehicle. So, they were never able to make the connection between the mousy, flat-chested, androgynous looking individual who slipped out of the gates at five thirty in the morning on a bicycle, and the goddess who adorned the poster on the wall above the glory-hole box, in which she knelt.

Painted black, and filled with predominantly black or stainless steel instruments of torture, it gave me the creeps to even go in there, and after a few weeks, we constructed a fake bookshelf to completely hide the entrance to the room. I didn't really have any sadistic tendencies, although I did enjoy subjugating women through anal-sex, particularly if I was their first time. Olivia however, got her jollies from putting Madison through the ringer, and on several occasions would emerge from behind the metal door in a very high state of arousal, and wanting to fuck.

The shock collar was on display on the wall of the punishment room, although Madison's compliance, achieved more through fear than actual pain, ensured that it never needed to be used. Olivia denied Madison any sexual release too, and as she got into her mid-thirties, and approached her sexual peak, she was on edge for much of the time. Olivia would restrain Madison and tease her mercilessly with a variety of sex-toys, driving her maddeningly close to orgasm, but not allowing her to achieve release.

After several days of tease and denial, Olivia would offer Madison a chance to enjoy an orgasm, extracting increasingly humiliating favors from her in exchange. At first, I found their interaction arousing, particularly as I usually ended up benefiting from Olivia's desires, once she got excited. However, as time went on, I withdrew from their sordid power games, and turned a blind eye.

I only interceded twice, and both times I was unfortunately too late to do anything other than voice my disapproval, after the fact. The first time was when I went out of town for a few days, to see a friend on the East Coast. On my return, a visibly defeated Madison was hobbling around my kitchen, making little effort to hide the pain she was in. I rarely asked Madison how she was feeling, content to see her world condensed to being a live-in house-pet, as payback for all the shit she had put me through.

However, seeking to ensure that she wasn't in need of medical attention, I asked her if she was okay, which resulted in her bursting into tears. As she pulled up the back of her Walmart sweatshirt, I was assaulted by the visual of a huge tattoo just above her ass.

The location was classic tramp-stamp, even though I felt the size of the marking was too large for her frame. Similar in size and design to the "Property of Maxwell" Henna tattoo, that Madison had forced Olivia to wear for her first interracial encounter, this permanent display of submission was a large inscription that announced that Madison DuPont was now, "Olivia's Bitch."

"What the fuck?" I blurted out involuntarily. "Did you consent to this, Madison?"

Olivia had joined us now, a look of pride on her face as she entered the kitchen waving a piece of paper at me.

"Here is her signed consent form," Olivia announced cheerfully. "Complete with the disclaimers about being over eighteen, not being under the influence of drugs or alcohol, and not being under threat of coercion. Signed and dated by Madison, and witnessed by the receptionist at the tattoo parlor."

As I perused the document, it was clear that while it indemnified Olivia or I from any legal action, there had to have been some underlying threat, for her to have signed it. It had shaken Madison to the core, as she adjusted to the reality that even when she eventually moved on, she would have a permanent reminder of her subjugation by Olivia.

"I like it," Olivia said proudly. "In fact I am taking Madison to the beach tomorrow, to show it off."

The second time I interceded, was when one of Madison's saline implants broke. She had undergone breast augmentation almost twelve years prior to the accident, and when I called the Doctor he was not overly concerned. He told me that the older implants only had a life-expectancy of fifteen years, and it was not uncommon for one or both to fail. Fortunately, the saline solution that filled the bag was not harmful to the body, and other than the unflattering look of misshapen, unsymmetrical tits, surgery was not a medical necessity.

Madison was distraught with her new body image, having always flaunted her considerable assets. She begged me to allow her to have a fresh set of "C" cups, but I informed her that it was Olivia's call. Of course, Olivia extracted all kinds of concessions from my ex-fiancée, before finally agreeing to a consultation with a breast augmentation specialist. Olivia dropped the bombshell at the medical appointment, agreeing to fund the cosmetic enhancements, only if Madison agreed to the insertion of "A" cups.

Faced with the choice between grotesquely unsymmetrical tits, with one a full "C" and the other basically a chest indentation, Madison succumbed to pressure and chose the lesser of the two evils. In her unisex, oversized clothes, with a completely flat chest, she looked like a young boy, as she hustled around my neighborhood, delivering newspapers on her bicycle.

Inexplicably, after all of the physical and mental abuse that Olivia subjected my former fiancée to, it was an innocuous remark on my behalf, that ended up being the straw that broke the camel's back. Olivia had gone out of town to a punk-rock concert, and in a moment of weakness I decided to enjoy Madison's oral attention. Of course, as unattractive as she now was, I didn't want to have to look at the bitch, so I told her to kneel in her glory-hole box and wait for me.

As I readied myself for my blow-job by watching some pornography on my big screen, my friend Billy called me to see if he could stop by for a beer. It wasn't the best timing, seeing as how I already had an erection, but I hadn't seen him for a few months, and I invited him over. I figured we would have a couple of brews, then he would leave and I could go and face-fuck Madison through the glory-hole.

One thing led to another, and we ended up having several drinks together. After we were both buzzed, the conversation turned to Madison. He barely knew her, having only met her briefly on two occasions. In typical Madison style, upon learning that he was a forty something year old mail carrier, she didn't give him the time of day.

"Are you still living with Madison?" Billy asked me, barely trying to conceal his interest in her.

"She's still here," I said quietly, "although we aren't really a couple anymore."

"Jesus, why not?" he asked. "I thought you were going to marry her eventually. That chick is so hot."

Billy wasn't immersed in the Newport Beach scene, and wouldn't have been aware of Madison's downfall, or her diminished sexual appeal. To this day, I have no idea why this seemed like a good idea at the time, but with my judgment impaired by the alcohol, I offered her up to him. She was already on her knees in the glory-hole box, and Billy obviously had the hots for her, so I just blurted it out.

"I will make the bitch suck you off, if you want," I said, as he looked at me in astonishment.

After I assured him that I wasn't kidding, I expanded on the offer.

"I have a glory-hole set up in my pleasure room, Billy," I began. "To save Madison the embarrassment of knowing that she just blew one of my friends, I will shield you from her. Give me five minutes to prepare her."

Of course, Madison was already on her knees in the four foot high box, but I didn't want Billy to think that I was a total sicko, so I pretended to fetch Madison. A few minutes later, I stuck my head around the door, and caught sight of him pacing nervously around the room, his erection visible in his pants.

"The bitch is ready," I announced. "Are you?"

Billy didn't need to be asked twice, and as we entered the sound-proofed room, I was happy that I had already opened the imposing metal door earlier that evening, in anticipation of using Madison for my own pleasure. I allowed him to go first, the excitement written all over his face as he unzipped his pants, and fished his erect cock from his underwear.

I stepped back a couple of paces to give him some privacy, and as he sidled up to the hole in the front of the box, I turned on the spotlights, positioned in such a way that they illuminated the phenomenal head-shot taken of Madison, on her very best day.

"Jesus Christ," Billy said quietly, as he looked at the huge poster, seemingly absorbing every detail. "She is a fucking incredibly beautiful woman. Is it really her inside the box?"

"The woman on that poster is about to blow you," I assured him. "How would you like it?"

As Billy contemplated the fact that this was a custom-ordered experience, he inserted his cock through the hole, and with his eyes firmly locked on the poster, let out a whimper as Madison's lips closed around his cock-head.

"I like having my frenulum teased," he said quietly, seemingly not wanting to push his luck.

Before I even had a chance to confirm that Madison had understood his preference, Billy let out another moan.

"Fuck yeah, right there, Madison," he muttered. "That is perfect."

I knew he wasn't going to last long as soon as I saw his legs start to tremble, and as he stood against the hole, the only audible sounds were his heavy breathing, and the lewd slurping sounds emanating from the box, as Madison worshipped Billy's frenulum.

"How long ago was that picture taken?" he asked, as he rapidly approached his release.

"About two weeks ago," I lied, knowing exactly what he wanted to hear.

Billy let out a final whimper, and announced that he was close, which prompted Madison to reposition her lips around his cock-head. With a low, guttural moan, he tensed up and blew his load into her mouth, never taking his eyes from the beautiful, oversized poster of Madison in her glory days.

"Stay there," I informed him, matter of factly. "Madison would be honored to clean you up."

Billy rested against the side of the box for several moments, gazing at the poster in admiration, as Madison licked his ejaculate from his softening cock. Finally, with a sheepish look on his face, he backed away from the hole, still looking up at the beautiful head-shot.

"Good as you expected?" I asked, stepping forward for my turn.

"I have wanted that bitch to suck my cock from the moment I first laid eyes on her," he admitted. "I just never in a million years...." he added, as his voice trailed off in astonishment.

I knew that the poster on the wall was no longer an accurate depiction of the girl in the box, but the porn from earlier had got me ready to blow my load, and I eased my way through the glory-hole. As Madison started to perform her oral magic on me, Billy and I chatted amiably. I took great care not to mention him by name, both to protect him from any blowback, and to heap additional embarrassment upon Madison, knowing that she had sucked an anonymous cock.

"Does she blow you regularly?" Billy asked, seemingly in awe of my arrangement.

"She hardly ever blew me when we were a couple," I said dismissively. "Too focused on trying to have my baby."

"You guys would have made beautiful babies," he said cheerfully.

"Probably would have," I admitted, "if I hadn't had a vasectomy right after I turned eighteen. Madison spent months trying to get me to impregnate her," I added, laughing. "Dumb slut."

It took me quite a while to reach my climax, especially as I wasn't under the illusion that Madison still looked like the girl on the poster. Billy watched on intently as I verbally abused her, and after I blew my load, I noticed that he was hard again.

"Go again, if you are up for it," I offered, as a smile appeared on Billy's face.

"Are you sure, Pete?" he asked, apparently just being polite, because he stepped forward before I could even respond.

"Enjoy her," I offered. "Talk dirty if you want. Madison didn't give you the time of day when you guys met. It is only fitting that she should end up on her knees with your cock in her mouth."

Billy was a lot more vocal the second time Madison blew him, although he still stared constantly at the poster, as if he was in disbelief that it was Madison in the box.

"Turn around, bro," I said at one point. "Drop your pants and spread your ass-cheeks apart."

Billy looked a little confused as he rotated one hundred and eighty degrees, and rested his naked ass against the hole. His eyes widened shortly after, and I assumed that Madison was rimming him through the hole.

"Holy Christ," he stammered. "This is a first for me!"

As I watched Billy writhing around in ecstasy while Madison ate his ass, it was a stark reminder to me how rare rim-jobs are for regular guys, particularly those in their forties. Billy was twenty years older than me, had a very average job as a mailman, and was not bombarded with offers of sexual favors, the way I constantly was.

Even though my generation viewed analingus as a fairly mainstream sexual act, I am pretty sure that no-one got their ass eaten as much as I did.

Despite Madison's best efforts to give Billy a world-class rim-job, he was still fixated on the poster, and was craning his neck to view it as she ate his ass.

"Turn around if you are more comfortable," I offered. "I just wanted you to see what a great rim-job artist my bitch is."

Billy did turn around to face Madison once again, and as he looked intently at the poster, and verbally abused my ex, he erupted a few moments later, enjoying an orgasm that appeared to be just as intense as his first. Now that he was aware of the program, Billy slumped against the box and allowed Madison to clean him up. After several minutes, he composed himself and withdrew his cock from the glory-hole.

"Jesus, Pete," he said with a huge smile on his face. "That was amazing. Thanks man."

Billy left shortly after that, the demands of his job as a mail carrier requiring him to get up at 5am the following morning. After he left, I went in to the punishment room to let Madison out of the box. When she arose shakily from her knees, struggling to maintain her balance after several hours of confinement, I noticed that she had been crying.