Trust Fund Baby Pt. 13

She had been used as a sex-toy for the last several months, by multiple different men, so I knew that Billy hadn't offended her sensibilities. Before I could ask her what was wrong, she blurted it out.

"You had a vasectomy before we even met?" she cried. "You knew we could never have babies?"

That conversation would be our last. Unbeknownst to me, Madison had been saving up her money from her odd jobs in the neighborhood, and that night she drifted out of my life, whereupon I never heard from her again.

She disappeared from Instagram and Facebook, and no-one in Newport Beach could shed any light on her whereabouts, so I gave up wondering where she had landed, although I am certain it was not a lateral move, given the abysmal physical condition she was in. I did ask George if she had gone to him for shelter, but he hadn't heard from her. I just hoped that she hadn't sought refuge in the hood with Maxwell, as he was probably one of the few people who would have actually helped her, based on their sexual history.

After Madison disappeared, Olivia and I settled into our friends with occasional benefits relationship, and I paid her four grand a month to procure young pussy for me. She was phenomenal at finding desperate women for me to assert myself over. As a former runaway herself, she knew exactly where to find disenfranchised teenagers, and because she was of a similar age, and was non-threatening with her Goth persona and casual drug use, they trusted her immediately. In fact, if I felt like some strange, Olivia could often procure me a desperate and hungry twenty-something year old girl within a couple of hours.

You could see the wheels turning in their young minds, as they processed what they had to do, to stay in the opulence of my five bedroom ocean-front house. I would give them space initially, allow them the luxury of a hot shower or a relaxing soak in the tub, which for many of them was long overdue. Once they were clean, and feeling better about themselves, I would feed them.

As I got to learn more about the young runaways, one of the defining characteristics was hunger. A lot of these girls had subsisted on handouts, fast food, and occasionally even dumpster-diving, so when they were presented with the opportunity to eat excellent quality food, in unlimited quantities, they were eternally grateful.

Gratitude was the perfect catalyst to sex, and even though there was never any inference of a quid pro quo situation, most of the young girls understood that there would be some expectation of payback. They often turned to Olivia for guidance, and she would advise them of my proclivity for analingus, and then report back to me as to their reactions.

Rimming is quite a mainstream sexual activity among my generation, so most of these young women had eaten a man's ass in the past. However, occasionally Olivia would encounter an innocent, previously sheltered runaway, who was blissfully unaware that these kinds of perversions existed, and I would take it upon myself to educate the young girl. Most young women are fairly malleable, particularly if they are feeling a sense of obligation, which the vast majority of them did, having been saved from the mean streets of Southern California.

Occasionally I would find someone who was so grateful for my intervention, that their feelings would be far stronger, and in an attempt to remain within the sanctity of my home, they would not only be willing to do whatever I wanted sexually, but would also actively encourage other young women to submit to me.

These young women, as they emerged from the crowd due to their enthusiasm for meeting my every need, were designated as "Team Leaders" by Olivia. I could only have one Team Leader in the house at one time, due to the "too many Chiefs, too few Indians" conundrum, and so this led to some healthy competition within the household for the much sort-after bestowal of honor.

Upon earning this title, the lucky teenager would be expected to demonstrate an exceptionally enthusiastic approach to my needs, to advise and inform others of my favorite proclivities, and to assist Olivia in the procurement of new young women, who were referred to as house-pets. My home could comfortably accommodate eight house-pets at a time, two to a room, in the unlikely event that I wasn't in the mood to take any of them to my master suite.

More often than not, I would enjoy the company of three or four of them, and the remainder of the young women could enjoy a restful night's sleep in their own beds. This was how it worked in theory, although in practice, the limited space and the rotating door meant that someone was always on the verge of being kicked to the curb. This created a healthy competition within the house, and I was constantly being offered sex as I went about my day, particularly from women who felt as if they were no longer in the inner-circle.

In fact, the evening selection process was a great method of control, as just by ignoring a beautiful women, I could elevate her level of anxiety at the prospect of being back on the streets, thus ensuring that sometime during the following day she would pull me aside, and negotiate the terms of her inclusion in tonight's sexual activity.

I did see a pattern emerge among the young women who expressed a reticence to eat my ass, and it was related to their reservations about cleanliness. I could understand their reluctance, as I wouldn't want to stick my nose between a pair of dirty ass-cheeks. However, this dilemma was easily solved once Olivia or the Team Leader got involved. Depending on the girl, I would either shower with them, and after demonstrating that I was squeaky clean, would force them to eat my ass in the undoubtably hygienic environment. Or, I would have them blow me while Olivia rimmed me, and then at some point order them to switch places. This worked wonders, as the new girl would recognize that the act wasn't as repugnant as they had previously considered, and encouraged by Olivia's enthusiasm, would often stick their tongue deep into my asshole.

Of course, in these days of fluid gender-identity, some of the runways that ended up in my ocean-front mansion were lesbians, although they would often try and hide it. Olivia made it abundantly clear that I still expected to use them, orally, anally and vaginally, but she would often pair them up with a like-minded girl, so that they could also get their needs met. As time passed, some of my favorite encounters were with lesbians, and I thoroughly enjoyed watching their internal struggle, as they traded what must have felt like unnatural-feeling sex, for a warm, safe place to stay.

Occasionally, Olivia would discover a jewel when the house was already full, and I would have to discard one of my girls, to make room for a new one. Initially, I dreaded these impromptu purges, but as it became apparent that the girls would stoop to new personal lows in order to remain in the sanctuary of my home, they became my favorite event. The girls named the dreaded cull, Judgment Day, and as word spread around the house that we needed to make room for some new girls today, I prepared myself for a sexually active morning.

Judgment Day, which slowly evolved into my favorite day of the month, began early this one particular morning. It was right before Christmas, and while the weather in Southern California is such that it is not that uncomfortable being homeless in December, any feelings of being homesick, or of general malaise, would have been amplified by the Christmas spirit, prevalent amongst the majority of residents.

I felt a pair of soft, young lips on my cock early in the morning, and slowly awoke from my slumber. As I looked down between my legs, Jessica withdrew her lips slowly from my cock, looked up at me with a seductive smile, and made the first of many pitches that I would hear that day.

"How would you like to wake up to this every morning?" she asked enthusiastically.

While I appreciated her efforts, I was also astounded at her naivety. I knew that she was new in the house, but surely she had been here enough days to realize that this was exactly how I was roused from my slumber, each and every morning. As I looked at my alarm clock, and saw that it was 4.45am, I wanted to give her extra credit for being the first girl up and ready to pleasure me this morning, and also for presenting herself to me fully made-up and with her hair styled perfectly. However, she needed to know the truth, so as she lowered her lips back onto my cock-head, I responded.

"I wake up to a blowjob every morning," I said condescendingly, enjoying the complete control I had over this nineteen year old red-head. "What can you offer to differentiate yourself from the other seven warm, eager mouths in the house?"

"Get rid of those two bitches, and I will show you," she responded confidently, as she momentarily removed her lips from my cock.

I am sure that the two young women who had shared my bed that night were not expecting to be booted out before 5am, but as I admired their tight, teenage asses as they scurried out of my bedroom, Jessica got back to work.

As she resumed her enthusiastic blowjob, I kicked the bed covers from my legs, and began to critique the young woman. I was laying on my back and she had maneuvered herself into position between my legs, as she blew me. She had a nice enough body, her tight little ass peeking out from beneath the copper chemise that she was wearing, which contrasted beautifully with her red hair. As she looked up at me with her green eyes, I realized that she was pretty too, and judging by the smile on her face, was amenable to doing whatever it took to secure her place in my home.

If I was being overly critical, her skin was milky-white, which was probably due to her natural, Irish-looking complexion rather than her avoiding the sun, particularly as we had found this lone stray on the sand in Venice Beach. Also her nails were way too short for my liking, although that was easily corrected. With eight girls in the house, there was always someone who knew their way around the nail-bar that I had set up in my utility room, and as Jessica ran her perfectly-filed nails under my nuts and began to tease my taint, I decided that I would modify her after she had sucked me off, treating her to some fire-engine red, nail extensions.

As her smooth fingertips approached my asshole, she removed her lips from me, and spoke.

"Turn on your side, Papa," she whispered softly, using the nickname that all of the girls adopted within moments of entering my home. "I know what you like."

As Jessica rose to her knees to allow me to roll over onto my side, she sucked her middle finger lewdly, as if she was craving something in her mouth. I nodded my approval, and after I was in position, she put her head in my crotch and continued to blow me. Jessica briefly rested one of her hands on my buttocks, before maneuvering it between my ass-cheeks. As she parted my butt-cheeks, she slipped the tip of her middle finger, which was well lubricated from her attempts to simulate fellatio, between them. Then, to my astonishment, she stuck this wet digit right through my sphincter, and applying just the right amount of pressure, forced the finger deep inside of me.

A few seconds later, when she expertly located my prostate, and began to massage the walnut-size gland with a perfect technique, I began to appreciate her lack of nail extensions. Two things became evident very quickly as she caressed my prostate. Firstly, she had undoubtedly done this before, and secondly, the short nails, and the way that they had been so smoothly filed, was intentional. I had fairly limited experience with prostate massage, having previously always had a young girl's tongue inside my anal-passage, instead of their finger.

However, as Jessica expertly stroked my inner gland, I felt an otherworldly sensation within, and a strong desire to piss. A few moments later, as my nuts constricted and I ejaculated in her mouth, I realized that the pressure created by her finger being deep inside of my ass, had contributed to the feeling of needing to pee. My orgasm was very intense, quite possibly one of the strongest ever induced by a single girl, in a one on one encounter. It also lasted much longer than usual, and as Jessica continued to caress my prostate while simultaneously blowing me, I felt my nuts throb as they continued to unload their contents.

A steady stream of semen flowed from the tip of my cock as Jessica milked me, and several minutes elapsed before I could tell that I was done ejaculating.

"Holy fuck, Jessica," I said with a laugh, as she looked up at me admiringly. "I think you completely drained my nuts. I can't believe I came so much, especially as at first it felt like I needed to piss."

"That's quite normal, Papa," she said sweetly. "The act of prostate massage puts pressure on the bladder, and creates the sensation of needing to pee. However, it is the first thing in the morning, so if you need to go, just go."

While I certainly didn't need her permission to go and use the restroom, once she put her lips back on me, I realized that I had misunderstood her. Jessica closed her lips firmly around the very tip of my cock, and keeping her middle finger embedded deep inside my asshole, held me firmly in place. I needed to be one hundred percent sure of her intentions, as she waited patiently on her side for me, with my cock-head just inside her mouth.

"Here?" I asked tentatively, as she nodded her head enthusiastically to confirm her consent.

I did need to go quite badly, and even though my restroom was less than twenty feet from me, I was quite comfortable in my bed, and it was only 5am I told myself, as I justified my actions. Jessica remained passively on her side, lips clamped around my cock, occasionally looking up at me and smiling.

"I want you to keep your nails exactly the way they are," I instructed her, as the first trickle of piss exited my cock.

Jessica greedily swallowed it, as if it were some kind of life-sustaining fluid, and over the ensuing minutes, I slowly emptied my bladder into her willing mouth. The combination of trying to urinate through a semi-erect cock, and her continued stimulation of my prostate gland, caused the flow to stop and start sporadically, and by the time I had finished, nearly three minutes had elapsed, and I was hard again.

Recognizing that I was ready to go again, but not necessarily in the mood to be in close proximity to someone with piss breath, Jessica removed her middle finger from my asshole, climbed out of my bed, and headed for my bedroom door.

"Who shall I send in to take care of that, Papa?" she asked, motioning towards my visible erection, and without the slightest trace of jealousy.

As I watched her standing in my doorway, with an agreeable smile on her face, I realized that she was exactly the kind of girl that I needed in the house. Clearly very resourceful, she possessed a unique sexual skill that I found highly arousing, but was also not burdened with a jealous streak, the way many young women are.

"Send Casey in," I instructed the young red-head. "Brush your teeth and then join us," I added, as her face lit up into a broad smile.

"Yes, Papa," she said excitedly. "Thank you, Papa."

The wheels were already turning in my head, as her tight little ass shimmied out of my master suite. With Jessica's place in the house cemented, I needed to make sure that none of the other girls cut off their fingernails, in an attempt to emulate her talents at prostate massage. There was only a need in the house for one such specialist, and until such time that I tired of her, she was my go-to prostate girl. It would be tough to improve on her technique anyway, so unless some girl showed up who was an expert at milking in her own right, which was reasonably unlikely, Jessica could remain at my place.

A quiet tap on my door signaled the presence of Casey, and as I commanded her to enter, she came in shyly. Casey was a recent arrival, a twenty-two year old petite Asian spinner, who had fled an abusive relationship, ending up homeless in the process. Olivia found this one panhandling at the Greyhound bus station, trying to rustle up enough cash to catch a bus out of California.

Olivia talked Casey off the ledge, and upon learning that the young girl didn't even know which state she was bound for, convinced her that she needed a safe place to gather her thoughts. I could tell that she was broken the second she came into my home, before I even learned about her abusive ex-boyfriend. However, even as she stood before me shuffling uncomfortably, as Olivia made the introductions, I could also tell that she had the potential to clean up really nice.

As she entered my bedroom, head bowed slightly in submission, Casey looked phenomenal, far exceeding my expectations. She was wearing a white silk babydoll, with matching stockings and a garter-belt, that contrasted beautifully with her jet-black hair, and dark skin. I knew that she was nervous around men, understandably given the abusive nature of her previous relationship. However, any feelings of inadequacy that she harbored as a result weren't my problem, and I wasn't going to make any concessions because of her piss-poor choice of boyfriend.

"Twirl for me," I instructed her, setting the tone for our first encounter. "Nice and slow. Good girl."

My condescending tone struck a chord with her, and she flashed me a look of resistance. If my time with Madison had taught me anything about women, it was that if you give them an inch, they will take a mile. Cognizant of the fact that Casey's options were limited, I decided to assert myself over her. I had plucked her out of the bus station, allowed her the luxury of an extended soak in my Japanese tub, and fed her. Now, as she rotated slowly before me, dressed up in about a thousand dollars worth of LaPerla lingerie, it was payback time, and we both knew it.

"Come," I beckoned, as she nervously approached my bedside.

Experience with the endless stream of young runaways that came through the revolving door of my ocean-front mansion, had taught me that the direct approach was always best. With this in mind, I clarified the situation for the beautiful Asian.

"You don't have to be here, if you don't want to, Casey," I said in a gentle tone. "You can spend a couple of nights here, relax and recuperate, then I will give you whatever bus fare you need to start your life over again. Which state are you friends and family in?"

It was a purely rhetorical question, as I had already been briefed by Olivia that the young Asian girl didn't even know what bus to catch out of California, such was the non-existence of her friends and family. Casey flinched at the notion of being back on the streets, even if I was offering to put out with a full stomach and a pocket full of cash. I could see the wheels turning in her pretty little head, and having seemingly weighed her options, she stepped forward.

'Kneel," I said, as she reached the bedside.

I wasn't trying to be an asshole, but I had a house full of young girls, and Judgment Day was upon us. I had some decisions to make, and while Casey certainly met the physical requirements, I needed to assess her demeanor, of which obedience played a huge part. She reacted much more decisively this time, sinking quickly to her knees. Once she was kneeling by the side of my bed, I moved over to her, and positioned myself in such a way that she was between my thighs.

It didn't take a rocket scientist to figure out what I wanted from her, but verbal instruction is a big part of control, so I gave her directions in an authoritative manner.

"Suck my cock, Casey," I ordered her. "Nice and slow, as if you are honored to do so."