Trust Fund Baby

Even though I had made the decision to dump Madison, to exit the toxic relationship and start living life as a young Trust Fund Baby, she got me off four times that night. I just couldn't get enough of her, as she regaled me with tales of her exploits with the men. Initially, I thought that she was embellishing the lewd details, but as I viewed the security footage between orgasms, I came to the conclusion that she was actually holding back.

Olivia, Jody and my girlfriend had behaved like total fuck-toys for the lucky millionaires, and the two blondes had even serviced a young black man, as he sat in my exotic car. The sheer indignity of it made me come as hard as I ever had, and in the morning I awoke to Madison's soft lips on my cock.

She was so completely irresistible, that I knew in my soul that I would never leave her. At that point, marriage seemed like the most palatable option, and I considered driving her to Tiffany Jewellers that afternoon, and purchasing her a ridiculously expensive token of my intent to do the right thing, if only to stop her incessant fucking around.

Madison apparently had matrimony on her mind too, although predictably she approached it from a more sexual angle. She had her own ideas of how to make me her husband, and as she alternated between giving me a loving blow-job, and edging me with her lubricated hands, she shared her thoughts with me.

"One thing this party reinforced for me is that men come much more quickly with the attentions of two women," she said, stating the fucking obvious. "I would like to introduce other women into our bed, after we are married," she added, trying to force my hand.

My mind went immediately to Jody, although I didn't dare to mention her by name. I was obsessed with the young blonde, and would have loved nothing more than to get balls-deep inside her tight pussy.

"What do you fantasize about, Pete?" Madison asked me, as I approached my orgasm.

Truth be told, at this point in my young life, I loved rim-jobs, and one of my most profound orgasms was when I fucked Samantha in the rest-room of the patio bar, as Olivia ate my ass. As evidenced by the interaction between Olivia and Madison on my security footage, Samantha was still a bone of contention, both because she was barely eighteen and Olivia had purchased her teenage pussy for me. For this reason, I didn't dare mention her, although of late, my new obsession was Jody.

Had I been completely candid I would have told Madison that my fantasy would be a three-way with her and Jody, but not wishing to inflame the situation, I blurted out my second best option.

"I am perfectly happy with our sex-life Madison," I began, somewhat truthfully. "However, I would like to have a young girl eat my ass during our sexual activity."

"Any particular activity?" Madison asked, as she edged me closer to my orgasm. "Or all of them?"

"All of them," I answered unequivocally as I got closer.

"Even hand-jobs?" she taunted me, knowing exactly where this was heading. "Would this be more enjoyable if you had another girl's tongue in your ass?"

As I processed her provocative choice of words, she slipped her moist lips over the tip of my cock, and I spurted between them. I don't know how my body was capable of such semen production, but as Madison parted her lips, so that I could watch her swallow my load, I noticed a prodigious amount in her mouth.

"I can make that happen for you, Pete," she added cheerfully. "Once we are married I will bring in a rim-job girl for you. Maybe she can just live here with us."

It was all I could think about all day. I imagined waking up in the morning and taking a shower, with Madison on her knees blowing me, while the rim-job girl ate my ass. I visualized myself fucking my girlfriend doggy-style, while the rim-job girl lay underneath me, with her tongue in my anal passage. In my fantasy, the rim-job girl was Jody, but I dare not even mention her as a candidate for the position, particularly as it was contingent upon us being married, which was several months away at the very earliest.

A few days went by without any further mention of Madison being prepared to fulfill my fantasy, and I considered it on hold until we got married. Then one afternoon, shortly after Madison got back from work, Olivia showed up at my place. She had two suitcases with her and stood on my doorstep awaiting an invitation to enter.

I had heard a rumor that she had been brutally assaulted by a client, and it had shaken her so badly, that she had decided to get out of the escort business. However, even though she had taken a regular job at Walmart to try and get back on her feet, there was no way that she could afford her rent and she ended up getting evicted. I had always had a great relationship with Olivia, and even though most of it was sexual in nature, I genuinely liked her. However, today she seemed subdued, sad almost, barely making eye-contact with me as she entered my luxurious condominium.

"Olivia is staying with us for a while," Madison informed me. "She is down on her luck and has found herself temporarily homeless. I offered her a job as our live-in maid because I know you guys have history."

"You are welcome to stay here until you get back on your feet, Olivia," I said genuinely. "Let me know if you need anything from me."

"Don't be too familiar with the staff, Pete," Madison warned me. "We are not running a charity here. I hired Olivia to do our laundry and keep our place spotless, not to hang out and chit-chat."

"Let me show you to your room at least," I offered, picking up her suitcases, and heading towards our primary guest accommodations.

"She will sleep in the study," Madison informed me, in a tone that left no room for discussion.

As I walked Olivia down the long hallway to the smallest room in my condo, I offered my apologies.

"I will get you your own bathroom," I assured her, as we reached the door to her new sleeping quarters.

The study was kind of a catch-all storage room, with a pocket door that didn't even lock. Madison had cleared most of the boxes from it, and a single mattress was on the floor, reminding me of how college dorm-room accommodation is often depicted.

"Thanks Pete," Olivia said softly, as she gave me a hug. "I won't be here long, hopefully," she added.

That night, as Madison and I played cards on my ocean-front balcony, Olivia worked tirelessly, vacuuming, dusting, cleaning the kitchen and generally busying herself. At one point I asked Madison what their arrangement was, and it became apparent that she had locked Olivia into a poor man's version of golden handcuffs. We were paying her four grand a month, plus accommodation to be our domestic servant. This was about twice what Walmart paid per month, and would help her on the road to financial recovery, burdened as she was with thousands of dollars of medical bills relating to her sexual assault, coupled with her recent eviction.

"I own that bitch," Madison said coldly, their history clearly driving Madison's poor treatment of the younger woman.

I should have stuck up for Olivia more, especially as years after Madison and I broke up, Olivia and I remained close friends. However, I tried to justify my inaction and kept coming up with excuses to not intervene in their initial power struggle. Olivia had after all been one of Madison's competitors in the Newport Beach escort scene, and had set me up with Samantha to fuck with my girlfriend. Olivia had even rubbed Madison's face in it, taunting her about the fact that Samantha was only eighteen years of age, when I fucked her. There was no love lost between the two of them, and it pleased Madison no end to finally have the younger girl under her thumb.

Their initial power struggle was very brief, with Olivia capitulating when she got sued for the costs related to her eviction, and Madison offering to pay for it, in exchange for immediate compliance. From that day forward, Olivia wore a commercial cleaning uniform at all times around my home, in an effort to reduce my sexual attraction to her, and referred to us as Miss Madison and Mr. Pete, to enforce the gulf in our social status.

Occasionally I would speak to Olivia one on one, reverting immediately back to our friendship and free of the formalities of titles. However, when Madison was around, which became increasingly more common as she cut her work back to three days a week, I was required to have minimal contact with "Liv" as we both called her.

That is why it was so surprising to me the first time Olivia joined us in sexual activity. Madison had obviously choreographed the whole thing, because it went according to how she had predicted our love-life would be once we were married, and she procured a rim-job girl for me.

Madison and I were in the shower, and she was on her knees giving me one of her world class, edging blow-jobs. The water wasn't running but the heater was on, and so it was very comfortable in the enclosure. Madison brought me maddeningly close to climax several times, until I could stand it no more.

"Please, Madison," I finally whimpered, "let me come."

"Are you close, baby?" she teased. "Wouldn't it feel nice to have a girl's tongue in your ass while you come in my mouth?"

Before I could even verbalize my answer, I was aware that someone had joined us in the large enclosure. I felt her nails first, raking across my ass, causing me to break out in goosebumps. This was followed closely by her warm breath, as she knelt behind me. Parting my buttocks with her soft hands, she extended her tongue and gently licked my taint.

"Put your foot up on the step, baby," Madison instructed me, as I raised my right leg and rested it upon the shower ledge, that was about eighteen inches above the enclosure floor. "Give the rim-job girl room to do her job."

Elevating my foot had the effect of spreading my ass-cheeks, and I felt the mystery tongue graze across the entrance to my asshole. Madison had already brought me to the edge several times, so as soon as the moist tongue entered my anal-cavity, and began to wiggle around in its depths, I exploded in Madison's mouth. It was a tremendous orgasm, greatly enhanced by the protracted edging session that preceded it, and by the time I had regained my composure, the mystery girl was gone.

I knew that it had to be Olivia, but when I dried and dressed myself and returned to my living area, there was no sign of our live-in maid. I caught sight of her scurrying down the hallway wearing some rubber gloves, and turned to ask Madison what she was doing.

"Who, the rim-job girl?" Madison said with a giggle. "She is scrubbing our toilets. Do you need her for something?"

I knew that Madison's insistence on referring to Olivia as the "rim-job girl" was an attempt to humiliate her, but it didn't sit well with me, particularly as they both were now living in my condominium. Now wasn't the time to correct Madison's rudeness, although I recognized that her behavior needed to be addressed.

The next day, when Madison was at work, I tried to have a conversation with Olivia, but she was very distant and continued to call me Mr. Pete. Finally, after my repeated efforts to get through to her, she begged me to leave her alone.

"Mr. Pete, please," she implored. "I desperately need this job and a roof over my head. Miss Madison has made it very clear to me that she will kick me out if I show any interest in you. Please let me do my job and follow her instructions."

I felt sorry for Olivia, as I knew that she was between a rock and a hard place. Her brutal sexual assault had rendered her petrified to work as an escort, and yet her precarious financial situation forced her to have a job. Madison had extended her a lifeline, but that came with a heavy price, and it involved complete submission to my girlfriend.

As soon as Madison realized that rim-jobs were my thing, and it became obvious that this sexual act clashed directly with her agenda of wanting me to impregnate her, she had decided to invite other young women to join us in the bedroom. As luck would have it, Olivia fell upon hard times right around the time that we needed a "rim-job girl," and got the position by default.

There were some obvious advantages to using Olivia. First of all I trusted her implicitly, and we had some sexual history. I never had to worry about an ulterior motive with Olivia, and the more time she spent with her nose between my ass-cheeks, the better the rim-job was.

Because there was no love lost between them, Madison enjoyed stepping into the dominant role, although she was unnecessarily disrespectful to the younger woman. Olivia tolerated it as long as she was being paid, but I could see the hatred in her eyes as Madison continued to push her to her breaking point, and I figured that one day it would all come to a head. For the time being, at least, as long as Olivia was broke and homeless, she seemed determined to obey all of Madison's increasingly depraved requests.

I should have intervened more on Olivia's behalf, as Madison's treatment of her became more and more demeaning, and occasionally even brutal. To a casual observer, Madison's frequent sexual assaults of Olivia didn't seem any different than the attack that caused Olivia to quit sex work. They had about the same level of sustained violence and the resultant injuries were very similar. I imagine the main difference was that Madison's attacks were in a controlled environment, with no fear of escalation to the point that loss of life was a consideration.

After the encounters, Olivia was free to go to her room, clean up, lick her wounds and recuperate without fear of further violation. Madison, highly aroused after her violent domination of her house-maid, would pleasure herself and then enjoy a long hot bath. It was during one of these long soaks in the tub that Olivia finally approached me for help, an impassioned plea from an old friend that was in desperate need of intervention.

She was pretty beat-up, having been hog-tied and subjected to a lengthy ass-fucking session with a intimidating looking black strap-on. As she catalogued her injuries, which in most situations would have resulted in the intervention of a medical professional, I made the decision to get her out of my place for the night. As Madison luxuriated in her bath, I urged Olivia to pack some essentials, and I booked her into the local Marriott Hotel for two nights, so that she could recuperate.

I called a cab for her, and knowing that Madison had added Olivia's iPhone to our "Find my phone" app, gave the young girl some additional advice.

"Turn your phone off as soon as you get into the cab," I instructed her. "Once you are checked in, leave a message for me at the front desk. If you need to get hold of me, use the computer in the hotel lobby. E-mail only," I advised.

As I hustled the frightened young girl out of my front door, I made two decisions. Firstly, I was going to remove Olivia from any dangers posed to her by Madison, keeping her in the hotel for a lengthy stay, if I needed to. Secondly, I was going to confront Madison about her unacceptable treatment of Olivia, and give her a much needed ultimatum.

If I had known then what I know now, I would never have given Madison the ultimatum. For one reason they rarely work, particularly when the person with the least amount of leverage, issues it. All I had to offer was a free ride, something that several hundred eligible Newport Beach bachelors could also provide Madison, if they were so inclined. For her part, Madison offered me unrestricted access to otherworldly sex, which for me at the tender age of eighteen, was an unparalleled experience.

As soon as I told Madison to leave Olivia alone or face the consequences, she laughed in my face and left the room. About twenty minutes later, as she emerged from the master bedroom with a small travel bag, I heard the unmistakable sound of a twelve cylinder Ferrari revving outside my front door.

"I will be back later to pick up some more of my shit," she said dispassionately, "Steve's car has a tiny trunk. All I can fit in are the bare essentials."

Even though I knew it was Baldwin's Ferrari in my driveway, it was a kick in the nuts when she mentioned his name.

"How long are you going for, Madison?" I asked, hearing the shakiness in my own voice.

"Until you get your head out of your ass and stop giving me fucking ultimatums," she said angrily.

Baldwin honked his horn twice, seemingly disinterested in entering my home.

"Oh," Madison said cheerfully, "I nearly forgot my birth-control pills."

With that taunt hanging in the air, I heard her Louboutins click down the tiled hallway, and she breezed into our bathroom. As soon as she left me alone with her travel bag, I knew exactly what she was doing. Unable to suppress my curiosity, I approached the bag and peeked inside.

I probably shouldn't have been surprised, but Madison's definition of "bare essentials" was a little different from mine. Whereas I would have viewed my electric shaver, my iPhone charger and my toiletries as essential items, Madison's travel bag was full of lingerie, high-heeled shoes and bathing suits. I felt my jealousy surge through me as I saw my Valentine's Day gift in her travel bag, the exquisite blue chemise having been dry-cleaned for enjoyment by Baldwin.

I stepped back from the bag when I heard her coming down my hallway, her birth-control pills evident in her hand.

"Can't forget these," she said cheerfully, as she waved them in my face. "Wouldn't want to get knocked up! I won't be needing these either," she added, as she slid her LaPerla panties down her slender legs, and kicked them off in my hallway.

"Don't go, Madison," I said weakly. "Please, can't we figure this out?"

"Too late for that, Pete," she exclaimed. "You will have plenty of time to ruminate on your ultimatum. Everything okay in my travel bag? Did you see your Valentine's gift in there, recently dry-cleaned for Baldwin's enjoyment?" she added, reveling in my discomfort.

I am not sure if it was my red face or my visible erection that tipped her off to my snooping, but she was all over me, and we both knew it.

"It looks like you approve," she added coldly, as she stared at my crotch.

I was so embarrassed by my body's response and obvious betrayal, that I looked down dejectedly at the floor, unable to answer her.

"Be a sweetheart, baby, and carry my bag to the car," Madison said with a giggle, enjoying my turmoil as she walked excitedly towards the bright red Ferrari.

It was emasculating enough to be forced to carry my girlfriend's travel bag to her lover's car, but when that prick opened the trunk remotely without exiting his hyper-car, it was another kick in the nuts.

"We've got to stop meeting like this, Pete," he said with a deep laugh. "I am gonna keep her for a few days," he added, as if he was borrowing my lawn mower.

After her bag was loaded into the Ferrari, they sped down the driveway and I returned inside, where her panties lay discarded in my hallway.

Baldwin ended up keeping Madison for nine days, and despite my repeated attempts to call and text her, she never responded. She never came back for any more of her stuff either, choosing instead to purchase almost eighteen thousand dollars worth of clothes, using my credit card. A few hours after Madison left, I stopped by the Marriott to see if Olivia needed anything, but she had also checked out.

I knew Baldwin had both of the girls at his place, although I wasn't sure how they had found Olivia so quickly. He posted regularly on Facebook, and it was apparent that Olivia had resumed her role as live-in maid, at her new residence. One picture showed Baldwin and Madison chilling by his swimming pool, as Olivia served them lunch. In another post, Olivia was washing Baldwin's Ferrari, while dressed in a bathing suit and a pair of ridiculous "fuck-me" pumps.