Trust Fund Baby Pt. 12

Once I mounted her, we began to fuck. Well, in her passive state, Madison lay there, as I fucked. To my surprise, without the visual stimulation of her piercing blue eyes, and her platinum blonde hair, I could barely stay hard, let alone approach my orgasm. She looked so plain with no make-up, a butch crew-cut and that god awful Walmart sweatshirt that was still damp from Olivia's vaginal secretions. Madison was desperate for me to come inside her, as this would have provided her with some much needed validation that she was still attractive to me.

When she realized that it wasn't going to happen she seemed distraught. Olivia had taken her superficial looks from her, and it would take months to grow her hair long enough to support the addition of hair extensions. A wig wasn't really an option in her line of work, as the caliber of men she was trying to attract wouldn't tolerate her complete lack of femininity. While much of Olivia's handiwork could be reversed in one afternoon at the beauty parlor, her lack of hair was a major problem when it came to finding a new Sugar Daddy.

Her quiet sobs weren't helping me achieve my release either, and at some point I told her to shut the fuck up. To my surprise, she went silent and as I processed the fact that the power dynamic between us was irreversibly changed, I decided to fuck her ass. I didn't ask her either, I just withdrew from her tight, wet pussy, rolled her over onto her front, and lined the tip of my cock up with her rosebud.

Clarkson and Baldwin both used her anally when they were in the mood, so I figured that her ass was mine, as long as she lived under my roof, depending on me for food and shelter.

Madison is the only female that I have ever encountered whose asshole is looser than her pussy, which I think is from the combination of having had vaginal rejuvenation surgery, and a tremendous amount of anal sex. For this reason, it didn't take me long to get balls-deep inside her anal-cavity, and once in, I began to butt-fuck her.

Normally when I get behind Madison, I am treated to the visual of her long, straight platinum blonde hair spilling down her toned back, but as I looked at the back of her recently clipped head, it felt like I was fucking a newly-inducted military recruit, which just wasn't my thing. Finally, after pounding her asshole for about ten minutes, I realized that I wasn't going to be able to get off under the current circumstances, and so I withdrew and went in search of my laptop.

The new dynamic between us was intoxicating, and I found myself taking liberties with Madison that would have been inconceivable just two weeks ago. Figuring I had nothing to lose, I opened my files and found a headshot of Jody. After propping my MacBook up against the back of Madison's head, I knelt between her legs and began to masturbate furiously.

A few moments later, as I stared into Jody's angelic blue eyes, I blew my load all over Madison's tight ass, and then left her there covered in my ejaculate, as I went to take a shower. It felt so good to have escaped my obsession with Madison, and from that day forward, I used her for my own personal needs, never giving hers a second thought.

The following day I allowed Olivia to root through Madison's wardrobe and help herself to whatever she desired. Madison looked forlorn as Olivia tried things on, appropriating anything that she liked the look of. We donated all of Madison's Louboutins to a local charity that collected donations for women entering the workforce, as she and Olivia wore a different shoe size. As we handed the trash bag full of designer shoes to the young charity worker, we both knew that this coveted footwear would never reach the shelves of the store. The obscenely high Louboutins wouldn't have been of any use to the prospective worker anyway, unless the chosen vocation of the indigent woman was stripper or runway model.

At Olivia's suggestion, I allowed Madison to keep one pair of hot-pink Louboutins.

"You never know, Pete. You might want to fuck her one day, or gift her to someone else," Olivia suggested thoughtfully. "She needs one cute outfit."

Other than the one pair of hot-pink designer shoes, we kept Madison barefoot around the house, to diminish both her stature and her status, as she appeared smaller and less confident, without shoes. She was permitted to wear crocs outside of the house, in an unflattering shade of dark brown, or Uggs when it was cold.

We kept Madison in cheap, unisex clothes for the first two months, as Olivia slowly completed the transformation. First up, brown contact lenses to reduce the effect that her eyes used to have on men, and to more closely match her mousy, brown hair which we kept extremely short. Madison was not permitted to wear makeup or perfume, had her nails clipped at all times, and left unpolished. I terminated her regular Brazilian Wax treatments, her eyebrow waxing, her tanning salon sessions, and also forbade her to shave any part of her body. Within just a few months of being confined to my condominium, her hirsute body was milky-white, and she began to cover it up from embarrassment.

The transformation took place quite slowly, over several months, and in many respects this was more emotionally damaging to Madison than if she had been subjected to some life-altering trauma, like going through the windshield in a car crash. A lot of times victims of trauma have an extended support group, and are slowly nursed back to be the best version of themselves.

By contrast, we were trying to make Madison the worst version of herself, by slowly stripping her of her defining quality, which was her beauty and allure to men, through which she had always got her own way.

Now, as a very ordinary, mousy young woman, men barely paid any attention to her, and because she had never been required to develop a personality, she became a very forgettable person. It was interesting to watch Madison's transformation, although for her it was a living nightmare. As her looks and desirability to men diminished, so too did her self-confidence, and by the time Olivia was done with my ex-fiancée, she was a shell of a woman. Men virtually ignored her, and once a week, when we took her out of the house to go to the local charity shop to buy used clothes, it was Olivia who garnered all of the attention.

Inexplicably, Madison began to lose her shape too, developing cellulite and a flabby mid-section. At first I didn't understand why, as the three of us ate the same food most days. Then one day I caught Olivia adding butter to Madison's portion and I flashed her a knowing look. In less than six months, Madison went from a Newport Beach ten, to a four or five on her best day. At least she began to accept her station in life, becoming a docile, yet agreeable house pet in the process.

Over time Madison became increasingly compliant, but once in a while she would express a desire to leave my house, and we would end up dropping her off somewhere in Newport Beach in some Walmart clothes. It happened four or five times, and each time she would show up at the guard shack of my gated condominium complex, practically begging to be let back in.

As she became increasingly less attractive, her options diminished, and once she realized that it was next to impossible for her to survive without her good looks, she gave up trying to further herself. By this time, even regular employment would have been a challenge for Madison. She had no cellphone, no car, no fixed address and had been terminated from her last long-term, stable job for misappropriation of company property. She could have gone back to sex work, but would have been relegated to twenty dollar blow-jobs on the back streets around John Wayne Airport in Santa Ana.

I had her exactly where I wanted her, and we both knew it. That is why the last time she showed up at the entrance to my complex, after exactly fourteen hours on her own, I made her blow the two security guys on duty, before they escorted her to my front door. One guy was a fat, sweaty Mexican named Juan, who had worked there for quite a while. He had known Madison in her glory days, and had probably jerked off thinking about her in the past, as she always flirted with the security detail, back in the day. He was ecstatic when I offered him a freebie, and Olivia was more than happy to run down to the guard shack with a long brown wig and Madison's hot-pink Louboutins, after Juan told us that he missed access to the cheap whores who frequented the Zona Norte in Tijuana, Mexico. As Madison knelt before the fat Mexican, he played with her long brown hair, and called her a puta.

After that humiliating experience, she never asked to leave again, and was a compliant and respectful house-girl for the remainder of the time she lived with me.