Trust Fund Baby Pt. 02

Even though I had enjoyed more sex in the last three days, than I had in the last six months, I knew I wasn't going to last long. Madison was just too beautiful, too perfectly scented, dressed in her alluring lingerie, as I took her from behind. Her La Perla panties, which she had pulled to one side, rubbed against the side of my shaft as I slid in and out of her tight pussy, the silky material adding another level of stimulation to my experience.

"Blow your load inside me, baby," Madison squealed excitedly, as she appeared to approach orgasm.

She looked back over her shoulder, locked eyes with me, and came all over my cock, an orgasm that I now recognized as having been faked. A few seconds later, as she begged me to unload my nuts, I erupted with a loud roar, and ejaculated deep inside her.

My head was still spinning when she asked me to excuse her, and she stepped into an adjoining room. Moments later, I heard the sounds of a shower running, and Madison began to clean herself up.

As I waited patiently in her makeshift bedroom, I noticed that her handbag was still on the side table, partially opened. I couldn't resist taking a peek inside, curious as I was about her birth-control. As I looked inside, keeping one ear open in case the shower stopped running, I noticed a wad of cash lying on the top of her purse. I reached in to grab it, fanning the crisp hundred dollar bills open to assess the amount. I estimated there was about three grand in cash, an amount that was quickly confirmed when I saw the deposit slip wrapped around the outside of the wad.

The deposit slip, which Madison had torn from her check-book, gave me some additional information on the mystery woman. I learned her full name was Madison DuPont, she lived in an apartment in a seedy part of town, and she was about to deposit thirty-two hundred dollars in cash, into her personal checking account, the account and routing numbers of which were emblazoned on the pre-printed deposit slip. I took a quick picture of the deposit slip and moved away from her bag.

My interest turned to the LaPerla shopping bag that rested on top of a pile of boxes. As I peeked inside it I noticed several items of expensive lingerie. There were a few pairs of panties, some garter-belts and a beautiful silk babydoll in an exquisite shade of yellow. I couldn't help noticing that all of the price tags were still attached, and I wasn't sure if this was to enable Madison to return the items if she needed the cash, or if it was Clarkson's way of putting a price on her services.

There was an unsealed card inside the bag too, and my curiosity got the better of me and I ended up opening it. Inside the card was one thousand dollars in cash, in crisp hundred dollar bills and a small handwritten inscription.

"Thanks for Christening my new car babydoll. See you next month."

I felt my cock throb at the notion that Clarkson had paid Madison a grand to suck his cock, in addition to the gift of several pieces of very expensive lingerie. I wanted to total up the retail cost of the LaPerla items, but only got about halfway through when the shower stopped running. There must have been at least two thousand dollars worth of intimates in that bag, for fuck's sake.

Madison emerged from the bathroom a few moments later, in a completely different, but equally alluring set of lingerie. She sat at the beautifully lit make-up mirror by her closet, and started to apply her makeup. We chatted as she got herself pretty for our evening out, and once her make-up was done, she approached me, looking absolutely stunning.

She kissed me on the lips, and we began to make out, enjoying an extended, open-mouthed kiss. My cock stiffened involuntarily, and it was not lost on Madison.

"Would you like a little release before we head out?" she teased, lowering herself to her knees without waiting for an answer.

You have to remember that I was only eighteen years old, in a constant state of arousal, and capable, under the right provocation, of multiple orgasms per day. As Madison knelt before me, ten years my senior, and a seasoned manipulator of men, my cock throbbed in my jeans, leaking profusely into my briefs.

I know my erection was visible, straining as it was against the confines of my undies. Madison stroked me through my jeans, and looked up at me from her knees.

"Are you always erect?" she asked innocently, her blue eyes sparkling as she teased me.

"Around you," I stammered.

"Oh, I am sure Olivia got you hard too," she said cruelly, "I hear some good things about that girl."

I clammed up, but as Madison untucked my shirt from my jeans, it was apparent that she wasn't holding any grudges. Madison removed my shirt and my Apple Watch, my questioning look evoking a response from her.

"I hate blowing guys when they are wearing a watch," she said, giving me an uncharacteristically detailed insight to her life. "I always feel like I am on the clock. Take your time, baby. There is no rush."

Madison touched her perfectly glossed lips against my stomach, and I almost jumped out of my skin. I was so infatuated with this woman, that every time she touched me it felt out of this world. Her lips were just above the tip of my cock, fighting as it was with the waistband of my briefs to escape. She licked my stomach just below my belly button, heading steadily south. She had me right where she wanted me, and we both knew it.

Occasionally I would look down, just to make sure I wasn't dreaming. A lean, toned, tanned goddess came into view as I did so, her blonde hair spilling down the length of her back, as she knelt before me in her lingerie, her glossed lips glued to my stomach, just above my pelvic region. When she rubbed the palm of her hand across my erection, I expelled a large glob of pre-cum, my briefs dampening immediately.

Madison knelt before me, lips and tongue teasing my stomach, perfectly manicured fingernails raking across my leaking cock, for several minutes. My breathing was ragged now, my eyes closed in anticipation of another of her world-class blowjobs. I imagined coming on her face, my semen splattered all over her lips and nose, as she looked up at me, smiling through her baby blues.

"Have you ever given a woman a facial?" Madison asked, seemingly able to read my mind.

As she applied more pressure to my cock, through my jeans, I felt my nuts tighten and I knew I was approaching orgasm.

"I would love it if you came on my face," she teased, looking up at me and licking her lips.

The continuous pressure of my over the jeans handjob, combined with Madison's expert verbal stimulation, conspired to push me over the edge, and my face reddened with embarrassment, as I convulsed and blew my load in my pants. It was a tremendously satisfying orgasm too, which was surprising, as I would have expected it to be tinged with disappointment at the lost opportunity of getting some real action from Madison.

Madison was unflustered by my premature ejaculation, and remained kneeling before me, in no hurry to get up. She unzipped my jeans, pulled them down around my ankles, and admired her handiwork, contained as it was within my soaked briefs. I think if she had jumped to her feet and left me standing there alone, I would have felt extremely self-conscious, but as she remained kneeling before me, in just her lingerie, my cock stirred as I considered the possibilities.

Madison removed my jeans and then pulled my underwear down, before removing them, and tossing them on top of the pile of my clothes.

"Take a shower," she instructed me, "then we will head out."

I am not embarrassed to admit that I got another erection in the shower. I thought about jerking off, but it seemed like Madison was going to take care of my needs, so I tried to hide it with my towel, after I got out of the shower. Madison noticed right away, grabbing the towel from me, and teasing me as I stood naked before her.

"Fuck, don't you ever stay soft?" she teased. "Get dressed, I am hungry."

I knew this was payback time. We were going to end up in some very expensive restaurant, Madison ordering truffles by the gram, and bottles of Dom Perignon. To be honest, that didn't even bother me. I could afford to spoil her, especially after how she had treated me. I reached for my jeans and my underwear, when she spoke.

"I want my boy-toy commando tonight," she ordered, as I left my underwear on the floor, and shoehorned my erection into my jeans.

We left shortly after, Madison grabbing me a long Tom Ford leather coat for modesty.

"Leave the price tags in," she told me, "I will return it tomorrow."

As I tucked the price tags inside the collar, I saw that the coat cost a little over four grand. Again, within my comfort zone, although I tried to stick to my uncle's advice of only spending money on things that would feel good. To my surprise, when we got in my Lambo, Madison wanted to go to the place where we first met, and eat on the patio. This was a very modest restaurant, and it made me question whether Madison was into me, solely for my money.

Madison and I enjoyed a great dinner, and I noticed more female eyes on me, with each passing hour. I don't know if word had got around the bar that I was an eighteen year old trust-fund baby, or if it was pulling up in an outrageously loud Lamborghini, but it was clear I had no shortage of options in that bar. Madison ended up ordering a chicken Caesar salad, and two glasses of wine and when the bill came it was less than sixty dollars. She was very appreciative when I paid, and as we sat enjoying our cocktails, she was absentmindedly stroking my cock, through my jeans.

"Madison," I whispered hoarsely, "I don't have any underwear on. My wet spot will show in my jeans."

"Then don't come in your pants this time," she said with a giggle, "save some for me."

After we left the bar, I walked Madison to my car, using the full-length leather coat to conceal my hard-on. We pulled out of there, a crowd having assembled around the bright orange exotic car.

"Where to?" I asked innocently, hoping to prolong the evening.

To my surprise, Madison asked me to take her to a drive-thru Bank of America ATM.

"I need to deposit some cash," she informed me nonchalantly.

When we got to the ATM, she handed me her card and the wad of cash. I grabbed a deposit envelope, sealed the cash inside it, and slid her card into the machine. After she shared her PIN with me, I started to process the deposit.

"How much?" I asked.

"Thirty-two hundred," she said, without any hint of emotion.

After the deposit was accepted, I handed her the receipt, which she balled up and tossed in my coin tray.

"Let's go to your place," she directed me, "I want to fuck."

Even though I was only eighteen, I knew enough about women to know that they didn't need to have sex multiple times a day. Madison had a hidden agenda and now that I had picked my uncle's brains, I knew that she was trying to get me to impregnate her. Sure, she would toss in a few handjobs and the occasional blowjob to placate me, but the vast majority of our sexual interludes would involve me blowing my load inside her.

I decided to play along, knowing that my vasectomy indemnified me from any risk. When we got to my place, I hung up my Tom Ford leather coat, and went to use the restroom. Madison, feeling ever more at home, poured herself a glass of wine, turned on some music, and stripped down to her lingerie, which was an exceptionally pretty shade of dusty rose.

When I returned to my living room, I gave her the quick once over. Taking in the details of her La Perla lingerie and Christian Louboutin shoes, I calculated that she was wearing about two thousand dollars worth of clothing, in her scantily clad state. About half of her monthly pay from Tom Ford. Something didn't add up and even though I knew Clarkson was sponsoring her, I needed to find out what other sources of income she had. Maybe she had millions in the bank?

I excused myself, telling Madison that I had left my phone in my car. As I lifted the scissor door to my Lambo, I went straight for the crumpled up Bank of America ATM receipt, from earlier. The receipt indicated a pending deposit of thirty-two hundred dollars, and a current available balance of about sixteen hundred dollars. I am no financial forensic scientist, but knowing that her paycheck was deposited two days ago, and being the second to last day of the month, her rent was probably due in two days, this woman was living paycheck to paycheck, and someone was helping her out.

I knew it was none of my business, but if Madison was playing me for some kind of long term gain, I needed to know. I really liked her, and I needed to know how much it was going to cost me to keep her in my life. I could afford her, whatever the price, but I needed to know the amount. When I returned to my living room, Madison was laying on her back on my white sheepskin rug.

She had removed her panties, tossed them on top of mine, and was masturbating.

"Kneel there and watch me," she instructed, as she approached her orgasm.

It was incredibly sexy to watch Madison bring herself off using just her fingers. She was still wearing the La Perla lingerie set, a half-cup bra that raised her perky tits up, and a silk garter-belt with exquisite detail around the straps, which supported the silk stockings. Her Louboutins adorned her feet, the heels digging into the sheepskin rug as she arched her back and approached climax.

My cock swelled in my pants as Madison pleasured herself. After four or five vocal orgasms, she told me to unzip my pants. As I followed her instructions, I removed my cock and knelt next to her transfixed by the show she was giving me.

"You may jerk off on me," she offered, "but here are the rules. Don't touch my head or face while you are masturbating. When you are ready to come, shoot your load below my tits."

With that very specific set of instructions issued, Madison resumed her showtime for me. I started to jerk off following her instructions to the letter. I was permitted to fondle her breasts, as I understood it, and so I did so.

"Tell me when you are close, baby," she implored me.

I knew it wouldn't take long, and a few moments after Madison enjoyed another powerful climax, I told her I was close.

"Come on me, baby," she whispered seductively. "Soak me with your jism. Blow your load on my shaved pussy to mark it as yours."

I threw my head back, cried out her name, and erupted all over her stomach and pelvic region, as she looked at me with her innocent blue eyes, and talked dirty to me. It was a fantastic release on my part, and once I was done coming, she patted the sheepskin rug, and I collapsed next to her.

"Holy fuck," I said, through ragged breaths, "that was hot, Madison!"

"Worth three grand?" she asked me, in response.

I didn't really understand the question, so Madison expanded on it.

"I don't want to hide anything from you," she began ominously. "I deposited my three grand in cash in front of you, hoping that it would invite questions from you, but you don't seem that concerned, which is a good sign, I guess."

"Concerned?" I repeated, a little confused. "Madison, should I be concerned?"

"Not from a standpoint of contracting an STI, or from me having penetrative sex with other men," she added candidly. "However, I don't make enough money to pay my bills, so I supplement my income with the occasional sex show. What you experienced tonight is typical. Nothing risky, nothing intimate, just mutual masturbation."

"That's how you got the three grand?" I asked. "From a bunch of guys jerking off on you?"

"Two guys," she corrected me. "Two Asian guys took me for drinks at our patio a few nights ago. They were in Newport Beach on business and wanted to blow off some steam. They had a limousine and I left with them. One thing led to another and I ended up dancing and masturbating for them on the floor of the limousine."

"And they jerked off on you, Madison?" I asked, trying to process what I was hearing.

"I invited them to," she clarified. "Gave them the same set of rules that you just followed."

As it sank in, and my initial shock dissipated, I quickly came to terms with it. The risk of pregnancy or STIs was very low. They were on vacation, so I wouldn't have to ever meet them. I was okay with this. Then it dawned on me, there must have been others.

"How many men have paid to jerk off on you, Madison?" I asked, dreading the answer.

"A few," she said, being intentionally evasive.

"Anybody I know?" I asked reflexively, before I could stop myself.

Madison smiled at me before she answered, and I knew right then that she was deriving some pleasure from my discomfort.

She hesitated for dramatic effect and then whispered, "Are you sure you want to know?"

I was a kid. A jealous eighteen year old who had just been treated to the sexual highlights of my life, by this alluring older woman. Even though it would change absolutely nothing, I wanted to know.

"How many?" I repeated, hating myself for getting an erection during this conversation.

Madison observed my stiffening cock, reached the palm of her hand over to it, and rubbed my cock-head as we lay together. My pre-cum was evident to her touch, spread as it was all around the tip of my cock.

"Does it turn you on to hear about me with other men, baby?" she taunted me, knowing that she was getting into my head.

I let out a whimper, too embarrassed to admit that I found this arousing.

"I will take that as a yes," she teased.

Madison toyed with me for a few seconds and then asked me to mount her.

I just couldn't stop myself. As if in some trance, I rolled over on top of her, and she opened her legs and invited me inside her. I slid right in, and let out a whimper of pleasure as her tight pussy enveloped me. Madison put one hand on my ass, pulled me into her, and we started to fuck.

"My boss, of course," she began, as if every cute woman in Southern California let their boss jerk off on them.

"At work?" I asked, needing to know every detail, as I increased the speed and depth of my strokes.

"Yes, baby," she cooed, "every day at work."

What the fuck? Every day? I struggled to process that idea, and then she spoke again.

"That is why I have a daybed and a closet full of lingerie at my work," she added, as I pounded into her. "My boss enjoys jerking off on me almost every single day," she taunted. "Although we have never fucked, baby," she assured me, as if this made everything cool.

I had closed my eyes by now, trying to visualize Madison's Store Manager stood over her with his dick in his hand, as she reclined on the daybed in her expensive lingerie. If I hadn't already come so many times in the last forty-eight hours, I would have busted a nut by now. This was new to me, being inside a beautiful woman as she taunted me with her exploits with other men. Somewhat humiliating but definitely titillating and helping me towards my release.

"Who else?" I whimpered, knowing that any additional revelations would probably put me over the edge. "Who else, Madison?"

"Bronson," she said, enjoying watching me squirm and writhe with pleasure inside her. "Bronson is one of my regulars. He enjoyed me right after you left, although I had to give him a little extra play today, because I kept him waiting five minutes."

"Extra play?" I asked shakily, as I knew I was almost there.

"Don't worry, baby," she assured me, "you are the only one of my lovers that actually gets to fuck me."

"Madison," I exclaimed, "I am close."

"I know baby," Madison said condescendingly, "I know. Men always start whimpering and shaking when they are close. Bronson loves to..."