Trust Fund Baby Pt. 03

If you are reading this with a hint of skepticism, remember that as a single, reasonably good looking, trust-fund baby, I had far more opportunities than the typical twenty something male. Most women viewed me as marriage-material, and did whatever I asked sexually, without much pushback.

As I matured, my game improved exponentially, my self-confidence increased, and each year I gained a significant amount of net worth. This encouraged me to prioritize my sexual fulfillment in relationships. I wasn't completely selfish in bed, but my primary focus was my pleasure, and I enjoyed rim-jobs. In fact, the only thing I liked more than having a young girl willingly eat my ass, was coercing someone that found the act demeaning or repulsive, into sticking her tongue up my ass.

The second thing I learned from that night was the importance of documenting my partners' ages, particularly if they looked younger than twenty-five. I always required photo ID prior to engaging in any sexual activity, and was constantly reminded how many beautiful woman under the age of twenty-one, were trolling in bars.

In the morning, after Olivia and I had eaten breakfast, I settled up with her. I never minded paying her, in fact she was the one exception to my rule of spending as little as possible to get laid. I gave her one thousand dollars for her company, knowing full well that she had no intention of forwarding Samantha's cash to her. She also gave me the receipt for Samantha's suit, purchased from the sale rack at Nordstrom, the lingerie and shoes that the young blonde had worn to replicate Madison's look, and the bottle of Madison's favorite perfume, that Samantha had been heavily spritzed with as she waited for me, bent over the bathroom countertop. Money well spent, I thought, as I handed it over, rounded up to the nearest hundred.

After Olivia left my place, I felt a pervading sadness as I realized that I had possibly blown it with Madison. She still hadn't given me her phone number, but I didn't want too much time to elapse before I tried to patch things up. For this reason, I decided to stop by her work unexpectedly, which didn't go well.

Bronson was there, flirting shamelessly with my girl, as she rang up his latest purchase.

I don't know if Madison and Bronson were fucking with me, but he rested his hand on her ass for the entire time that she processed his order. Madison hardly acknowledged me, and I stood there like a third wheel as they flirted incessantly. She drove me crazy with desire for her, and made me insanely jealous at the same time.

Madison seemed to really enjoy Bronson's attention, and was laughing playfully at his banter and constantly toying with her hair. I know men respond to girlish behavior and Madison's was downright coquettish. As he left he kissed her on the lips and they said their goodbyes.

"See you tonight, gorgeous," he said in his deep, masculine voice, as he strode confidently out of the showroom.

"Phil," he said, acknowledging me as he passed.

I wanted to respond, "Benson," giving him the same disrespect by getting his name wrong too. I wasn't sure if his mistake was inadvertent or intentional, but either way, being called the wrong name is a kick in the nuts.

After Bronson left, Madison turned on me.

"What the fuck are you doing here, Pete?" she asked angrily. "I am working."

Standing up for myself was a skill that I would acquire later on in life, but at the tender age of eighteen, I wasn't going to engage with Madison.

"I wanted to apologize for last night, and I don't have your phone number," I responded, recognizing how lame I sounded, as soon as the words left my lips.

Madison didn't acknowledge that she had never given me her phone number, and changed the subject.

"Did you get my panties from the dry-cleaners yet?" she asked, "the La Perla ones I left at your place."

"Yes," I lied.

I hadn't even taken them yet, as I was using them to jerk off in Madison's absence, multiple times. I guess my plan was to replace them with a brand new pair, but I hadn't given it much thought, and I shuffled around nervously in front of her under this line of questioning.

Madison made eye-contact with me, and I could tell that she knew I was lying. I was an eighteen year old sexually inexperienced boy. She had fucked my brains out and left me her panties as a souvenir. Of course, I would jerk off on them.

"I will get them the next time I see you," she said, raising the possibility that we could reconcile. "Keep Olivia's thieving hands away from them."

"I won't be seeing..." I began, before she cut me off.

"I don't care how often you and Olivia fuck," she said without expression. "You and I are both single, free to fuck whoever we want. I just don't want that skank stealing my expensive underwear."

This seemed like the right time to ask her about Steve Baldwin, but the second I mentioned the events of the previous evening, she cut me off.

"Like I said, Pete, we are both free to fuck whoever we want."

Suppressing my jealousy, I changed tact.

"Can I see you tonight, Madison?" I asked, the desperation evident in my voice.

"I have plans tonight," she began coldly, "with Bronson."

"Cancel them, Madison," I began assertively, "let me take you out tonight."

"Cancel?" she responded incredulously. "I can't afford to. Bronson is paying me seven hundred and fifty dollars for tonight. I have bills to pay, Pete."

"Please," I added lamely.

"I would love to see you tonight, baby," Madison said, softening her tone towards me, as she moved into my personal space. "Believe me, I love spending time with you, but tonight is work, and I need the money."

It took me a second to digest that Bronson was going to enjoy my girl tonight for the measly sum of seven hundred and fifty dollars. At the same time, my uncle's words rattled around in my brain.

"The good ones don't have to ask you for money."

I knew I was making a big mistake the second I asked her, setting a precedent by altering the nature of our relationship from casual sex, to that of a paid encounter.

"Will you cancel Bronson and go out with me, if I pay the seven hundred and fifty dollars?" I asked.

"You don't have to do that, baby," she said sweetly. "I am free Monday night, we can go do something then."

It was Friday afternoon, and Monday was four nights away, which meant Madison had plans the next three nights. As I struggled to come to terms with the fact that three guys were going to jerk off on her this weekend, my jealousy surfaced and I reiterated my desire.

"Cancel Bronson, Madison," I said, trying not to sound too desperate. "I will give you his fee."

In that fateful moment, our future was cemented, as a pay per play relationship, and Madison immediately softened towards me.

"I would love that, sweetheart," she said enthusiastically. "I love spending time with you. Let me call Bronson."

Before I had a chance to realize that I had fucked up, or to change my mind, Madison called Bronson. She engaged in a very flirty, several minute long conversation with him, during which she made apologies and excuses for not being able to join him tonight.

"I will make it up to you, baby," she cooed, stoking my jealousy.

Right before she hung up, she even had the audacity to say, "No, baby, it has nothing to do with Phil," not bothering to correct his misuse of my name.

After she hung up, Madison told me to pick her up from work at seven that evening.

"I get off work at four," she informed me, "but it will take me a while to get ready for my hot date!" she teased.

It did seem odd that she asked me to pick her up from work, rather than her place. However, I knew from her paycheck stub that she lived in a shitty part of town, so I assumed that she was embarrassed for me to see her place. I was excited at the prospect of upgrading Madison's living arrangement, if I could just persuade her to move in with me.

As luck would have it, my uncle called me right as I was leaving the Tom Ford store. I started to bring him up to speed on the events since we last spoke and after a few minutes, he cut me off.

"Something is not right," he said. "I smell a rat. Let me call you back."

Less than an hour later, my uncle called me back. He did warn me that I was not going to like the news he had for me, before revealing incontrovertible evidence that Madison was trying to scam me. Apparently, on a hunch, my uncle called the Tom Ford flagship store in Beverly Hills and asked to speak to Bronson. A few seconds later, a masculine voice answered, identifying himself as Bronson, head buyer for Tom Ford.

"Bronson is a co-worker of Madison's," he revealed, much to my surprise.

Emboldened by his initial success, my uncle called back and asked for the Store Manager of Tom Ford, Newport Beach. Posing as a vendor for custom store lighting, my uncle first tried to see if he could arrange a meeting to discuss the potential of upgrading the lights in the Fashion Island Store. As soon as the Store Manager explained that those decisions were made at the corporate level, my uncle offered to bribe the Store Manager to "grease the wheel" as it were.

"I told him I would treat him and his wife to lunch at Fleming's Steakhouse, if he could facilitate a meeting," my uncle began. "He told me that he was a Vegan, and that his boyfriend would kill him if he stepped foot in a steakhouse."

"Madison's boss is gay?" I responded.

"Like most men in the custom clothier industry, yes. Would appear so," my uncle said quietly. "But, wait, there is more. I had a buddy of mine call the Store Manager back, claiming to be from a courier company trying to deliver Madison's replacement passport. My friend asked if it would be okay to deliver the important document to Madison's work, because she needed to sign for it. The Manager let it slip that Madison was living at the store, and as long as it was delivered during the opening hours, someone could sign for it."

"Madison lives upstairs at the Tom Ford store?" I asked incredulously.

"That is what her Manager said," my uncle assured me. "I don't know why," he continued, "but Madison is playing you."

As soon as I had confirmation that at least two of Madison's supposed pay for play encounters were fabricated, I thanked my uncle, and headed for the bar, where we had met. George was there, cleaning glasses and preparing for the evening rush.

After a brief hello, I got straight to business, holding out a crisp one hundred dollar bill for him to salivate over.

"No judgment, no drama, George," I began in a friendly manner. "Have you ever had a sexual encounter with Madison?"

I knew he was telling the truth, the moment he responded, without hesitation, and making eye-contact with me the entire time.

"Not unless you count me rubbing one out thinking about her," he began candidly. "Madison is a sexy bitch, and I would fuck her in a heartbeat, but she is way out of my league, bro. Unfortunately, we both know it," he added wistfully.

"Thanks George," I said, handing the hundred dollar bill to him.

"The two Asian guys in the limo," I continued, handing him another hundred in good faith. "What's their story?"

"High stakes poker players," he said without missing a beat. "They take Madison gambling with them quite regularly. They say she is a lucky charm, but in truth, she counts cards, for a cut of the winnings. She asked me to pretend she was escorting them, said she would make it worth my while, but she never came through."

After I left the bar, I had some decisions to make. I had an explanation for all four of Madison's supposed jerk-off sessions, the wad of cash she had deposited, and her attempted manipulation of George. I needed confirmation of one more thing before I confronted her.

I ended up driving to the address on her paycheck, which was a ramshackle apartment building in a seedy part of town. When I located her unit, there was an eviction notice on the door, dated about a week ago.

I called my uncle again with the latest news, and he ran me through my options. I thought he would advise me to never see her again, but instead he told me to meet her tonight, as planned.

"Pay her the seven-fifty," he advised, "and do everything you have ever wanted to do to her, before you cut the bitch loose."

It was with a heavy heart that I hung up the phone. I knew my uncle was right. Madison had tried to hustle me from the second she met me, pretending to be into me, when she was really just trying to get into my wallet. Once I knew definitively that she was playing me, it evoked a response in me to want to dump her. However, it weighed heavily on me that despite our torrid love affair, she hadn't given me a rim-job yet. I knew I would regret it forever, if I let that opportunity slip through my fingers. So, with this in mind, I called her shortly after I spoke to my uncle, to modify our plans.

"Something came up, Madison," I lied. "Can you grab a bite to eat before I pick you up? Then we can go straight to my place for a drink."

Madison was agreeable, and now that I knew the gravity of her financial situation, it made sense. She was no doubt focusing on the seven hundred and fifty dollars, more than the events of the evening. After I hung up with her, I drove to the La Perla store and replaced her soiled panties. I removed the tags, gasping at the one hundred and forty dollar price. Then I went home and poured myself a stiff vodka. This led to two more drinks, and once I realized that I couldn't drive, I booked a Lincoln Town Car to pick Madison up at work, and bring her to my place.

Madison looked phenomenal when she arrived at my ocean-front apartment. The sun was just setting and it was the first time she had seen the view from my place in daylight. Although my apartment was, in itself, a panty-dropper, the view was absolutely incredible. Madison seemed completely unimpressed, no doubt her enthusiasm jaded by having been in so many rich guys' houses.

The sun was reflecting on the blue Pacific Ocean as it set, highlighting the beauty of Madison's eyes, as she kissed me on the lips and smiled at me. My cock throbbed the second I inhaled her scent, such was my sexual attraction to her.

"I have something for you," I said handing her the La Perla panties that I had purchased that day. "Freshly laundered."

After I handed her the panties, I spoke again.

"I have your fee, too," I added, handing her seven hundred and fifty dollars in cash.

"You don't have to pay me up front, silly," she scoffed. "I trust you!"

"Working girls always get paid up front," I said coldly, setting the tone for our evening.

Madison took the money reluctantly, and awkwardly tucked it into her purse. I moved forward to kiss her, and for the first time since I laid eyes on her, I saw self-doubt on her face.

In the past, I had always allowed Madison to take the lead. She was older, much more sexually experienced, and a natural leader when it came to sex. Now that I had paid for the privilege of being with Madison, it felt different. I felt entitled to get what I wanted, get my money's worth, treat her more like I treated Olivia. I started to kiss Madison, much more aggressively than normal, telegraphing my intent to be the dominant partner today.

She responded favorably to my advances, and began to rub my cock through my jeans. As always, I was in an elevated state of arousal in Madison's company, her pheromones, her perfume and her general state of desirability, conspiring to make my cock leak. She was applying the perfect combination of pressure and rhythm to make my cock throb, and I was on the road to my first orgasm.

I had blown my load into my jeans before, under Madison's expert touch, but today I wanted more. I say I wanted more, but as I had paid for this encounter, I felt like I actually deserved more. I was really surprised when I heard my voice, unwavering and full of confidence.

"Get on your knees, Madison. I want you to suck me off."

Madison looked at me with some surprise in her eyes, seemingly trying to assess my level of seriousness. I put one hand on her shoulder, and applied a little downward force. She allowed me to push her onto her knees, and once she was in my desired position, she began to fumble with my zipper.

Ordinarily, Madison was very composed but I had unnerved her. I lowered my gaze and watched as she undid my jeans. Her gentle teasing strokes had caused me to leak a considerable amount of pre-cum into my briefs, a visible wet spot having formed at the front of them. Madison hooked her thumbs into the waistband of my underwear, and pulled them forward over my erection.

Once my cock-head was exposed, she looked up at me for direction, her gorgeous blue eyes reflecting the setting sun. Madison always used her stunning looks to manipulate men, but now that I had purchased her for the evening, she was going to do my bidding.

"Suck my cock, Madison," I ordered, "nice and slow as if you are honored to blow me."

To her credit, once we had established exactly who was in control, Madison followed direction very well. She began to gently kiss and lick the tip of my cock, giving my cock-head a loving tongue bath. I maintained control of her, dictating the pace of her ministrations, as she nibbled the shaft from top to bottom, before turning her attention to my nuts.

As she enveloped my scrotum In her warm mouth and gently sucked my nuts, I gave her my approval.

"Good girl, Madison, right there baby," I said condescendingly.

Madison looked up at me for approval a couple of times, her beautiful blue eyes peeking out from my nutsack, as the her nose and mouth lay underneath it. I grabbed the tip of my cock and pulled it skyward, while simultaneously spreading my legs further apart.

"Taint," I said assertively.

Truth be told, I was expecting some pushback. Girls as beautiful as Madison presumably didn't have to perform such degrading acts. However, Madison obeyed immediately, her moist tongue moving deeper under my nuts, until I felt the tip of it brush my taint. I let her lick me there for several moments, enjoying her submission to me. I am not sure how much time Madison had spent licking a man's undercarriage, in the past. She was way too pretty to have to engaged in such demeaning acts, but I think she was spurred on by the promise of an easy life, on my dime.

I did fantasize about the prospect of sharing my life with Madison, but my uncle kept trying to get me to realize that I held all of the cards, when it came to my love life. The truth was, Madison tried to trick me into a committed relationship by pretending to allow other men to jerk off on her, for money. Now that I understood that she was a dirty, conniving whore, I intended to treat her as such.

I looked down occasionally, trying to reconcile her femininity and model-looks, with the demeaning sex-act she was being asked to perform.

I was apprehensive about quite how to broach the subject of Madison giving me a rim-job. By the time I was twenty-two years old, as my confidence grew, and I learned how little pushback most women would give me, I modified my approach to that of a much more assumptive one. Once a young lady was in the position that Madison was, kneeling between my thighs with my nuts in her mouth, I would rest my hand gently on the back of her head, and direct her into position.

Most of the time they would get the hint, although occasionally my date would struggle to repress their revulsion, and I needed to be more forceful and apply greater downward pressure to the top of their head. I never asked any woman to perform analingus on me unless I was squeaky clean, and my preferred location for this act of submission was the shower.