Trust Fund Baby Pt. 04

By contrast, the Trashy Lingerie website was anything but artful. Much more graphic in nature, offering an eroticized, almost fetishized display, it showcased breathtakingly beautiful women as sexual objects of desire. The models on its highly sexually charged homepage were famous in their own right, but were tattooed, pin-up girls like Dita Von Teese. Whereas the Victoria's Secret Angels were photographed engaging in pleasurable pursuits such as playing tennis, having picnics or visiting the local art gallery, the Trashy Lingerie girls were depicted as being completely available for sex.

They were posed in highly erotic positions, often kneeling while looking up submissively at the camera, or in the doggy-style position with their head looking back over one shoulder, as if anticipating which hole was about to get violated. In fact, in one of the provocatively arranged photos that were featured on the homepage, a tattooed woman dressed in a skin-tight latex catsuit, was on all fours with her face emerging from a stainless steel bowl that rested on the floor. The bowl, stenciled as it was with some cute cat paw-prints, was filled with whipped cream, and as the woman lifted her face from the creamy contents, the photographer managed to capture the exact moment that she licked her lips. She had a large dollop of whipped cream on the end of her nose too, the implication being too overt to ignore.

"You like?" Madison asked with a giggle, as she felt my cock rise against the rear of her thigh, depositing traces of my pre-cum on her plaid stockings.

"Amazing," I said quietly, "that is so fucking hot."

"Wait until you see the Schoolgirl Uniforms," she said seductively, "they are incredible."

As we stood against the edge of my desk, me spooning her as we perused the website, I knew I was going to get hard again. The combination of the suggestively posed models, and Madison promising me the world if I bought her the Schoolgirl Uniform, was too much for me at my tender age, and my cock slowly stiffened. Madison leaned forward slightly, in a barely perceptible motion, and reached one of her soft hands behind her back. She began to rub her thumb across the tip of my cock, smearing my pre-cum all over my glans, as I watched in awe as she scrolled through the website until we reached the Trashy Schoolgirl page.

This page was right up my alley, photographed as it was using an angelic-looking platinum blonde, with no tattoos or piercings, seemingly chosen for this photo shoot for her youthful innocence. There were dozens of different options and accessories, so much so that it was overwhelming.

"They offer a Reform Schoolgirl option and a Prep Schoolgirl option," Madison informed me cheerfully, her familiarity with the website leading me to believe she had spent a lot of time here.

We did check out both options, but the Reform Schoolgirl was more hardcore, incorporating leather into the "bad girl" uniform, while the Prep School option wasn't as detailed, a bit more of a Halloween costume than a fantasy outfit. The cherubic innocence of the Trashy Schoolgirl uniform was more my style, so we quickly returned to that page.

As I scrolled through the predominantly red-plaid items, I noticed that there were tennis skirts, garter skirts, pleated skirts, short sleeve front-tie spandex tops, and too many accessories to contemplate. Madison sensed that I was overwhelmed by the choices, and closed her laptop momentarily so that we could regroup.

"I want you inside me," she whispered, as she grabbed the tip of my cock and positioned it on her taint, the inference being that either hole was available.

"Pussy," I said weakly, my desire interfering with my ability to communicate.

Madison slid her tiny thong panties to one side, and I slipped right inside that tight, warm orifice. As we stood against the desk, I began to rock slowly inside of her. Madison opened her laptop, signed in, and navigated to the Trashy Lingerie check-out page.

"I saved a Schoolgirl Uniform in my basket," she said helpfully. "I think you will like it, Pete."

With that proclamation issued, she bent further over my desk, positioning herself in such a way that I could look at the computer screen as I fucked her. As I checked out the items that she had saved for future purchase, the first thing I noticed was the total price, five hundred and sixty dollars.

"That includes the shoes, baby," Madison offered, as if she read my mind.

As she scrolled slowly through the pictures, the attention to detail and inclusion of every conceivable accessory rendered the price immaterial. I wanted to see her in that fantasy costume, whatever the cost. Fantasy costume it was too, the way she had optioned it out. The red-plaid skirt that she had selected was the shortest one available, and barely covered the buttocks of the gorgeous young woman who was modeling it on the website. Pleated, like a tennis skirt, but affording much less modesty, it was paired with a white spandex crop-top, the plaid collar and under-boob ties, contrasting beautifully with the white stretchy material of the tiny garment.

Madison had pre-selected a plaid garter-belt, not unlike the one she was currently wearing, but with much more attention to detail. Tiny red bows adorned the top of all four straps, and there were two matching bows on the front of the stretch-silk lingerie. There were matching stockings, and a garter, plaid hair bows, plaid gauntlets and some very sexy high-heeled black ankle boots. These shoes had red plaid accents around the top, and a clip-on plaid bow attached to the toes of each one. A red choker completed the ensemble, which was the icing on the cake.

"What do you think baby?" she asked innocently, "can we afford it?"

I picked up my pace a touch, and began to thrust more deeply inside Madison's pussy as she continued to build value in the ludicrously expensive outfit.

"Please, baby," she said, changing her tactics from teasing me to begging. "You won't regret buying it. I will let you bend me over your desk and fuck my ass, while I wear it," she promised.

I let out a whimper at the thought of that, and stared intently at the pictorial of the Schoolgirl uniform, depicted on the website.

"Only thing is," she added dejectedly, "you won't be able to come inside my tight little pussy. I am home from college for the summer break, and my parents would freak out if I ever got birth-control pills, so I only let guys ass-fuck me, or I give them blowjobs."

"Oh, Madison, I am getting close," I whispered, her words doing an effective job of breaking me.

"Don't come inside me, Pete," she said in a girlish voice. "My parents will kill me if I get pregnant. Pull out before you orgasm. You can blow your load on my ass."

With her final words ringing in my ears, I waited until the very last second, stepped back abruptly, and grabbing the tip of my cock, began to jerk myself furiously. Madison threw her head back, her long platinum hair almost reaching the garter-belt that she was wearing. She had a pronounced arch in her toned back, and my first rope of ejaculate splatted almost halfway up it, landing mainly in her hair.

"Come all over me, baby," she said cheerfully, as I continued to blow my load in her platinum locks, and all over her tight butt-cheeks.

I was panting when I finished my orgasm, in a state of elevated arousal, almost euphoria, and it took me several moments to compose myself. I slumped across Madison's back, struggling to catch my breath, as she continued to tease me verbally.

"Something tells me you are going to love having a naughty schoolgirl around your place," she said with a giggle. "Can I order it, Pete?"

In typical Madison style, over the course of the next two hours, as she coaxed two more loads from me, we spent my brief recovery time between orgasms, perusing the Trashy Lingerie website. As Madison alternated between flattering and pleasuring me, she changed my position on the value of such high-priced custom made costumes, and I ended up spending nineteen hundred dollars on five additional fantasy ensembles. In a scene that would be repeated numerous times over the course of our tumultuous relationship, she got exactly what she wanted, in exchange for completely draining my nuts.

The costumes arrived about a month later, during which time Madison made two trips to the Trashy Lingerie store on La Cienega Blvd, in Los Angeles, for adjustments and custom fittings. The store was just south of Melrose Avenue, a famous shopping street in LA, and Madison ended up buying some more fantasy clothing and accessories during her time there.

I was losing track of her spending but it just didn't matter. I had already paid last month's credit card bill, and the nineteen hundred dollars she had spent on fantasy costumes had been long forgotten. My bank account received a healthy infusion of cash on the first of the month, as the next trust-fund disbursement of one hundred and sixty thousand dollars was released to me.

In fact, it took the intervention of my uncle before we finally calculated that she had spent in excess of ten grand of my money in the last thirty day period. That revelation didn't bother me, and my uncle had to agree that it wasn't much in the grand scheme of things. However, when I shared the fact that Madison was also an authorized user on two of Clarkson's credit cards, he became much more concerned.

"Why on earth would she still have access to his credit cards?" my uncle asked with incredulity. "And what is the monthly limit?"

Truth was, I had no clue how much Madison was allowed to spend per month on Clarkson's credit card, and I answered that question honestly. I did know that the other card was a LaPerla charge card, and that he settled it each month without any discussion of what she had spent. When I told my uncle that, he reacted predictably.

"Pete, something is wrong with this picture," he said as I squirmed on the other end of the line. "A man doesn't purchase lingerie for another man's woman, without good reason."

I wasn't about to tell him that Madison sucked Clarkson off once a month in the front seat of his car. Or that during this particular regularly scheduled event, I was on sexual restriction. I couldn't let him know how pussy-whipped I was, so I played dumb, which only stoked his curiosity. He ended up driving over to my place the following day, when Madison was at work.

"First of all, son," he said, addressing me the way he often did since my Dad's premature death, "I am proud of you for making Madison continue to work full-time. That is a very smart decision on your part."

Niceties dispensed with, we began what would end up being a detailed inventory of Madison's possessions, and an in-depth forensic financial analysis of her spending habits. We went through her closet first, which in itself yielded some surprises. I was already aware that Madison had numerous duplicates of LaPerla lingerie piled high in her closet drawers, the majority of which still had the tags on. What I didn't know was that this duplicity extended to her regular wardrobe too.

She had numerous Tom Ford suits that still had the tags affixed, duplicate silk blouses, and other high-end designer clothes and handbags that she hadn't cut the tags from. Even her beloved Christian Louboutins were separated into "indoor" and "outdoor" shoes, the assumption being that she could return any of the pairs that showed no evidence of wear on the soles.

"Did you buy her all of this shit, Pete?" my uncle asked me, holding up a mint green thong, with the one hundred and forty dollar price tag still attached.

Under this line of questioning, I had to come clean. I told my uncle that to my knowledge, Clarkson and possibly Steve Baldwin were still helping Madison out financially, although I disavowed any knowledge of either bring a pay for play relationship.

"Well," he continued patiently, "which of these garments did you buy her?"

I was getting flustered now, as I realized I wasn't able to differentiate between the lingerie I had purchased for Madison, and the silky intimates her other lovers had treated her to.

"This is fucked up Pete," my uncle continued, anxiety palpable in his voice. "It is one thing to buy your girl the latest iPhone and allow her to call who she pleases. However, this is different, this is lingerie. It should be personal."

Years later, my uncle's words would make sense to me. As I developed healthy, monogamous relationships, lingerie came to represent a very personal and intimate connection between my partner and I. On more than one Valentine's Day, I went shopping for a particularly enticing piece of women's underwear, and ensured that it was beautifully wrapped and presented, before giving it to my girlfriend. The intimacy stemmed from the fact that I had taken the time to shop personally for the gift, and that she would later reveal it to me, and wear it for my pleasure as much as hers.

Madison on the other hand had two individual LaPerla charge accounts, both of which appeared to have no actual pre-set spending limit. In contrast to the way that my future partners and I shared the intimacy of a beautifully constructed silk gift, Madison merely acquired them en masse, and viewed them as interchangeable. She put zero effort into separating our respective purchases, and if the truth was known, I probably couldn't have separated our gifts, even if I had wanted to. There were so many duplicates, in addition to the fact that there were multiple pieces that still had the price tags affixed to them.

My uncle was spurred on by what he perceived to be the gravity of the situation, and with renewed vigor, we began to search her closet. The first unexpected discovery was a shoebox full of cash, that in my uncle's estimation contained thirty to forty thousand dollars, in mostly used hundred dollar bills. Shortly after this discovery, we came across almost two years of credit card statements, issued in Clarkson's name, but clearly identifying Madison as an authorized user.

"This will help establish which clothes he bought her," my uncle said, without enthusiasm, "although it will be a lot of work."

Using the SKU numbers on the tags still affixed to the clothes, and the sticky labels on the soles of her shoes, we were able to find most of the charges on the credit card. Clarkson had indeed paid for most of her designer handbags, suits and Louboutins. Judging by the amount he allowed her to charge over the last two years, they must have had a very fulfilling sex life. Shortly after this discovery, we found the LaPerla charge card statements. Using the same methodology, we came to the conclusion that Clarkson had purchased much of her lingerie, and that Madison had lumped our gifts in together, with no effort made to distinguish them.

"You realize what this means, son, don't you," my uncle began, trying to respect the fact that I loved Madison.

I shook my head in acknowledgment, not wishing to verbalize what we were both thinking. Thankfully, my uncle never forced the issue, and left shortly after, leaving with me with my thoughts. After he left, I tidied up her closet, poured myself a cocktail and sat quietly digesting these new revelations.

What it meant in simple terms was that on more than one occasion I had fucked Madison while she was wearing lingerie that another man had purchased for her. However, this was a double-edged sword, because it also meant that with a great degree of certainty, Clarkson had enjoyed my girlfriend while she wore something sexy that I had paid for. I wondered if she had ever worn one of my intimate gifts when she gave him his monthly, edging blowjob, and if so did they share a laugh about it?

I had a fleeting memory of fucking Madison over a pile of Tom Ford boxes in the storeroom above her work. She had taunted me that Clarkson had paid for the sexy underwear that she was wearing, claiming that he had gifted it to her the last time she sucked him off. At the time, it had contributed to my otherworldly orgasm but in the light of day, it was disrespectful, to say the least.

I called my uncle later that day to thank him for taking it easy on me.

"I know I have made a lot of mistakes when it comes to Madison," I said quietly. "I am just so in love with her, that I am willing to put up with a little crap. Sex is amazing with her, too," I added, my youthful exuberance shining through.

I never confronted Madison about my discoveries when she got home that night, my unwillingness to rock the boat, forcing me to deal with it later on down the road. I did try and pay more attention to the items of lingerie that I bought for her, often asking for a fashion show when she got home from LaPerla. One afternoon, when she returned from the upscale lingerie store, she showed me a beautiful mint-green chemise that she had just purchased. It looked fantastic on her, the thin silk straps highlighting her beautifully sculptured shoulders, and the underwired front lifting and thrusting her boobs together. I wanted to titty-fuck while she wore it, and the thought of blowing my load all over the four hundred dollar garment, kept me hard all evening.

However, when we turned in for the night she was wearing a light peach garter-belt and matching half-bra, and as if she had read my mind, had brought a bottle of KY lubricant to bed.

I didn't give the green chemise a second thought, as Madison unhooked the front clasp of her bra, propped her head up on a silk pillow, and began to seductively lubricate her breasts. She applied a generous helping of the silky liquid to her tits, keeping me fully engaged the entire time with her playful and flirtatious mannerisms. Once her "C" cups were slick with the KY liquid, she squeezed them together and invited me to mount them. As I straddled her, the tip of my cock emerged from between her pert tits, just two inches from her soft lips. At this point, I understood the purpose of the pillow beneath her head, as it positioned her mouth perfectly for me to fuck, should I so desire.

In typical Madison style, she had glossed her lips with a matching light-peach shade of lipstick, and her makeup was flawless, which I took as an invitation to give her a facial.

"Hold my tits together, baby," she told me. "Let me lube you up too."

I placed my hands either side of her surgically enhanced breasts, and as I held them in place, Madison poured most of the rest of the bottle of lube onto the shaft of my cock, which seemed a little excessive.

"I got it, babe," she said cheerfully, as she squeezed her tits tightly around my erect cock. "You can fuck them now."

As soon as I began to rock slowly back and forth between her oily mounds, she extended her tongue and began to lick the tip of my cock. I no longer deemed the amount of lubricant that she had poured all over my cock to be excessive, but rather the perfect amount to create a well-oiled cavity for me to fuck. Madison looked up at me with her beautiful blue eyes, flashed me a broad smile, and slowly parted her glossed lips.

"Fuck my mouth, Pete," she offered. "I want to swallow your load."

At eighteen years of age, this kind of sexual provocation got me off every time, and I felt the familiar churning in my nuts, as she verbally teased me. I began to thrust deeper between her oily mounds, the tip of my cock disappearing between her peach-glossed lips with each forward stroke. Traces of her lipgloss appeared all over the head of my cock, my glans slowly changing color from its natural pink fleshy tone, to light peach.

"I am close, Madison," I warned her, the gentleman in me wanting to give her some notice before I blew my wad.

"I know baby," she cooed. "Men never last very long this way."