Trust Fund Baby Pt. 03

I took Olivia and Samantha home with me that night, although my mind kept drifting to what Madison was up to. As a seasoned courtesan she was an expert in men's pleasure, and I am sure Baldwin got his money's worth, if any actually exchanged hands. Maybe she fucked him just to get back at me. I will never know. However, it damaged our relationship irreparably, and forced me to grow up far quicker than I wanted to.

Someone else was forced to grow up much quicker than they wanted to that night also. Samantha Jane Thompson, as her Missouri Driver License identified her, made the transition from innocent Mid-West teenager to sex-worker, in the opulent surroundings of my ocean-front condominium that evening. I trusted Olivia enough not to set me up with an underage girl, but my curiosity got the better of me, and under the pretense of serving Samantha alcohol, I demanded age verification. Her hand was trembling as she held out her ID for my inspection. I took a photo of her License, and the girls excused themselves to go and freshen up.

Samantha's Driver License not only provided me with her birthdate, but also gave me additional insights into her situation. The fact that she had not yet surrendered her Missouri License for a California one, was a clear indicator that she had recently relocated to the area, as California requires new residents to do so within ten days of arrival. A quick google search on her address, informed me that she lived in the wealthy St. Louis suburb of Compton Heights, and as I perused her social media, I learned she had attended a private parochial school. If Facebook was to be believed, she also had a loving family, which begged the question what had she been doing bent over the counter of a public restroom with her panties around her ankles.

I heard the girls laughing as they entered my oversized shower enclosure, and I instinctively decided to join them. I was determined to have Samantha give me a rim-job before the night was over, and having seen that her objection seemed to be hygiene based, figured the shower would be the perfect environment for her first foray into ass-eating.

When I entered the shower the girls were very receptive to my presence and the three of us started to make out. Even though it was a paid encounter, there was a connection between us, and it didn't feel mechanical or forced. I wanted to assuage any concerns that Samantha had about hygiene, so we spent several minutes playfully soaping each other up. Once I was covered in suds, I put my foot up on the shower step, and shaved my asshole, taint and nut-sack. I made sure that my cock, balls, taint and asshole were squeaky clean and hair-free, before I used the shower extension to hose myself off. Once I was prepped for my upcoming rim-job, I hosed the girls off.

After I turned the water off, we kissed for a few more minutes and then Olivia sank slowly to her knees before me. The heater was on in my bathroom so it was nice and warm in there, and Samantha and I continued our tender make-out session, as Olivia started to suck my cock. I had already promised her five hundred dollars to come home with me, and she was prepared to earn it. Olivia is a very talented cocksucker but I wanted more so I rested my hands on Samantha's shoulders and applied some light downward pressure.

Even though she was only eighteen years old, and not a seasoned pro like Olivia, Samantha did understand the universal signal to kneel, and did so upon my request. The two girls began to take turns blowing me, Olivia giving Samantha guidance on how I liked to be pampered. At some point, Olivia began to nibble my nutsack, with Samantha following suit shortly after. I looked down occasionally, enjoying the sight of two young girls kneeling before me, working in tandem to pleasure me.

When I spread my legs further apart, Olivia understood my subtle hint, lowered her face beneath my scrotum and began to lick my taint. Samantha resumed her tender blowjob, as Olivia worked on my under-carriage. Even though I had already fucked Samantha, I definitely wanted her to give me a rim-job before this night was over, and the shower seemed like the most likely location for this to occur. So, I decided to take the bull by the horns and make it happen.

"Get behind me Olivia," I instructed the young girl. "You know what I like."

This limited set of instructions was enough for Olivia, and having already some knowledge of my sexual proclivities, she scooted around the back of me, and parted my butt-cheeks with her dainty hands. I gasped with pleasure as I felt the tip of her tongue graze my asshole, and as she began to eat my ass, Samantha continued to blow me. If I hadn't been so resolute in my quest to have every single one of my sexual partners eat my ass, I would have just enjoyed the combined efforts of the two young hotties, and blown my load down Samantha's throat.

However, I wanted Samantha's cute, upturned nose between my buttocks so I told her so.

"Switch places girls," I said, in a tone that did not invite discussion.

Olivia cheerfully emerged from between my ass-cheeks, scooting around to the front of me, and taking the tip of my cock between her moist lips. Samantha, for her part, obeyed my directive, and scooted behind me, but she was much less enthusiastic about her new role. In fact, as Olivia threw her heart and soul into my blowjob, Samantha began to half-heartedly nibble my buttocks. While it felt divine to have a girl that had recently graduated Catholic High School, giving any kind of attention to my rear end, I wanted more, and asked Olivia to intercede.

"Show Samantha what I like," I said firmly, trying to maintain control of the two of them.

Once the two of them were behind me, I could sense Samantha's reluctance to fully engage in ass-play. To her credit, Olivia was offering words of encouragement to the young blonde, and I hoped that she was softening her up to the idea.

"He's clean, Sam," Olivia said sweetly. "Freshly-shaven too. Honestly, there is no odor or taste back there."

Samantha clearly still had some reservations, and I wondered if it was due to her strict religious upbringing. She did start to lick my ass-cheeks which was a step in the right direction, but her overall demeanor was tentative, to say the least. Olivia continued to encourage Samantha and finally I felt her tongue graze my taint, which felt fucking fantastic.

"Good girl, Sam," I said appreciatively, "right there, that feels great, baby."

Surprisingly enough, that seemed to lower some of her inhibitions, and as I continued to shower her with positive affirmations, she extended her tongue and caressed my taint gently with it.

"Yeah, baby, you got this," I said sweetly, "that feels awesome."

"Raise your head up slightly, Samantha," Olivia instructed her young protégé, "extend your tongue until you feel the entrance to his asshole."

In Samantha's defense, she was on her knees behind a guy that she had just met, being asked to stick her tongue inside his butthole, so I didn't begrudge her tentative approach. However, my financial situation, and the myriad of sexual opportunities that it afforded me, had made me quite demanding when it came to the actions of young women. I was done with her "good Catholic girl" act, and reached around behind my butt and grabbed the back of her head. Once I had her skull cradled within my large hand, I applied some forward pressure, and slowly forced her face towards my asshole.

Samantha put up some token resistance, but as Olivia held my ass-cheeks apart, she allowed me to place her exactly where I wanted her. Once her nose was touching my asshole, she raised her head slightly, extended her tongue, and began to lick my ass.

"Good girl, Samantha," I said as she began to lick me more enthusiastically.

This was the first time I had ever forced a woman to do something sexually for me, and I was emboldened by the positive outcome, more than I was regretting my actions. Later on in life, I would learn that a small percentage of women need to be forced into certain sexual acts, in order to assuage their guilt. Samantha was one such woman, her repressed Catholic School upbringing causing her to look at every intimate act as something to be ashamed of.

As it turned out, Olivia had coerced her into having sex with me in the gender-neutral restroom, by offering her a roof over her head if she got with the program. Samantha had arrived in Los Angeles as a teenage runaway, with no money, no contacts and no place to stay. She had encountered Olivia at a local coffee shop, and Olivia had sensed her desperation and channeled that into a free sexual encounter for me. She had even taken Samantha shopping for an outfit to closely resemble Madison. Olivia had promised Samantha five hundred dollars and a place to stay if she let me fuck her, and Samantha had folded like a pack of cards, rather than call her parents for help.

Now as Samantha was being forced to eat my ass, Olivia stepped up once again to help me out.

"Pete will pay you extra if you act like you are enjoying yourself," she said firmly, trying to convince Samantha to put a smile on her face.

"How much?" she countered, clearly interested, as she removed her face from between my ass-cheeks.

"Samantha, I will pay you one thousand dollars if you act like you are having fun rimming me," I offered.

Truth is, I was sick of watching the look of disdain on her face every time I looked over my shoulder and made eye-contact with her, and it would have been well worth a grand to see her smiling. Seasoned hookers know the importance of keeping smiling, no matter the assignment. In fact, as I would later learn, most won't engage in sex-acts that they find truly repulsive, for fear that they won't be able to keep smiling throughout. However, this decision is made prior to such engagement, and most hookers only facilitate a man's fetish if they know they can keep smiling throughout its duration.

The promise of an extra payday spurred Samantha into action, and for a few moments she was grinning broadly as she rimmed me.

"Look at me girl," I ordered her, as I looked down over my shoulder.

To her credit, Samantha was a quick learner, and as she looked up at me adoringly, with a huge smile on her face, my experience was transformed and I felt myself on the path to my release.

"Fuck yeah, Sam," I said, in awe of her improved attitude. "That is perfect."

Samantha let out a little giggle, winked at me, and stuck her tongue deep into my asshole. I turned back to look down at Olivia, made eye-contact with her as she blew me and mouthed the words, "thank you."

A few moments later as the two of them focused solely on my pleasure, I felt my nuts constrict and told Olivia I was close. I ended up blowing my load down her throat, as Samantha wiggled her tongue around just inside my anus.

I could sense some shame on Samantha's part after I ejaculated, and she struggled to look me in the eye. The three of us climbed into bed shortly after I came, and I drifted off quickly as the girls lay there whispering to each other.

In the morning as soon as I woke up, like most people I grabbed my phone to check my messages. I had a text from Madison which I opened with baited breath. I was hoping that she was going to apologize for her bitchiness last night, and to assure me that she hadn't hooked up with Steve. My heart sank as I looked at the two pictures she had attached to the text. The first one, taken from the passenger seat of his Ferrari, showed Samantha walking away awkwardly in her high-heeled Louboutins, unaccustomed as she was to wearing such footwear. The photo was purposefully unflattering, highlighting Samantha's ill-fitting suit, replete with numerous creases in the skirt and the dried "ice-cream stain" on the back of it, just above the hem.

The second photo, artfully posed, and presumably taken by Steve, showed Madison draped over the rear lip spoiler of his multi-million dollar Ferrari. She was bent at the waist, her hands resting on the transparent engine cover for support. Her skirt was hiked up several inches, revealing her garter-belt, and the fact that she still wasn't wearing any panties. Her long blonde hair cascaded flawlessly down her back, and as she looked back over her shoulder, her body language seemed to invite the lucky bastard that took this picture, to get balls-deep inside her.

Her perfectly glossed lips were slightly parted, as open an invitation for a blowjob as you are ever likely to see. Her blue eyes twinkled as she smiled back at the camera, seemingly encouraging him to take her over the back of his car, while simultaneously evoking envy in everyone else who viewed the picture, including her primary target, me. The photo was captioned "the real deal."

I hated everything about this fucking photo, but to my horror, my cock stiffened involuntarily as I gazed at it. Realizing that Olivia was still naked in my bed, I rolled her over onto her stomach and entered her from behind. Less than five minutes later, exercising my right as a paying customer to focus solely on my needs, and with the image of Madison etched into my brain, I ejaculated deep inside Olivia's young pussy. I took a quick shower and then went to join the girls for breakfast.

As often is the case when young men have overnight guests, I wanted to get rid of them sooner than later, so I was relieved when I learned that Samantha had already gone. That is until I saw Olivia holding a note that she had left on the breakfast table. Apparently her Catholic upbringing had made her question her actions of the previous evening. In fact, as she described her feelings of disgust at some of the sex acts she had performed "under the influence of alcohol," and detailed her dismay at having accepted cash in exchange for such acts, it was evident that she was not cut out for the big city. She had crumpled the hundred dollar bills up and left them with the note, and I watched with amusement as Olivia swooped up the cash with a promise to send it to her friend.

I spoke to Samantha briefly just before she boarded her flight to St. Louis. She harbored no ill-will towards me, but had decided that her teenage rebel runaway episode was over, and she was returning home to her parents, and enrolling in the local community college, until she figured out her long-term plan. I felt like I had done my bit for society, by setting her back on the straight and narrow, much the same way the "scared straight" program realigns the priorities of young offenders. I wished her luck and told her to let me know if she ever needed anything, although I extended this offer solely to reduce any potential malice she might feel towards me in the future. I had, after all, pretty much forced her to eat my ass.

I never spoke to Samantha again, although I followed her on social media for several years after our one-night stand. She really was a beautiful woman, although she was never going to reap the benefits of her genetic blessing, living in Missouri. Truly gorgeous girls have the world at their feet, and had Samantha remained in Southern California, she could have snagged herself a wealthy husband, and enjoyed a life of privileged luxury.

However, in the suburbs of St.Louis, with its lowered expectations and diminished opportunities, she ended up marrying a young man who was in the military, and working at the local Walmart. Shortly after she returned to the Mid-West, Samantha posted some pictures of herself wearing the suit that I had fucked her in. My dried semen-stain was clearly visible on the back of the skirt, once again highlighting the difference between her and Madison, who never left the house without being impeccably dressed. Years later, as I checked in on her Facebook page, Samantha had lost a lot of her allure. She was still good-looking, but her crappy Ford Escort and charity-shop clothing did little to showcase her beauty.

I made the mistake of liking one of her pictures once, and was surprised that she sent me a PM. Even though the tone was friendly, there was an undertone of blackmail contained with the pleasantries. She did accept that our sex was consensual but her assertion that she "was a very young girl" seemed to imply some kind of veiled threat.

I was in my mid-twenties by this time, and had been the subject of more than one blackmail attempt, which comes with the territory of being a promiscuous, wealthy young man. Experience had taught me to address the problem head-on, and I immediately sent Samantha a photo of me holding her Missouri Driver License that provided incontrovertible evidence that she was of legal age, at the time of our hookup.

Even though I had refuted her suggestion that she was underage at the time of our encounter, I still felt the need to quash any suggestion that she was coerced into anything, even though I had clearly forced her into analingus. My condominium was equipped with a state of the art security system, that included multiple CCTV cameras throughout the space. I had designated the master bedroom and bathroom as areas of surveillance, which meant I had a 4K camera concealed in the ceiling of each room. I reviewed the security footage from my night in the shower with Samantha and Olivia, and selected one screen-shot from the video I had surreptitiously shot.

Much of this video depicted her resistance to the demeaning sex-act that I was requiring her to perform, and was actually quite hard to watch. Samantha was a breathtakingly beautiful young girl, with an angelic face. Not only did she not deserve to be on her knees with her tongue between a man's butt-cheeks, but she did not look old enough to be engaging in any intimate acts. The entire time she was back there, her face bore a look of disgust or shame, her youth and lack of experience contributing to her reticence to object. She could barely make eye-contact with me, even as I looked over my shoulder frequently and continued to offer her words of encouragement. This clearly was not a consensual sex-act.

If the authorities had viewed the film in its entirety, especially the part where I had manhandled the young blonde's face between my buttocks, they would have recognized that I had coerced Samantha into eating my ass. However, separated from the rest of the footage, and taken completely out of context, this screen-shot was very damning to Samantha, and completely refuted her claims of being forced.

In the picture I am standing naked in the shower looking admiringly over my shoulder at Samantha, as she knelt behind me with her tongue in my ass. The look of despair that she had been wearing for much of the rim-job had dissipated momentarily, and as she looked up at me, her blue eyes peeking through her blonde bangs, she actually had a huge smile on her face. I knew that she was smiling because I had just offered her a thousand dollars to pretend that she was enjoying herself, but again, taken out of context there was no way that she could claim that she wasn't willingly engaged in analingus.

Once I had refuted the suggestion that she was either underaged or acting under duress, I threatened to post the photo on an open Facebook group for St. Louis military wives, that I knew she contributed to. Her tone changed immediately after my warning, becoming much more conciliatory, and after a few more pleasant exchanges, I never heard from her again.

I learned a couple of valuable lessons the night of my threesome with Samantha and Olivia, and they shaped the way I viewed random hookups moving forward. Firstly, from that day forward, I regarded each encounter as the last time I would ever see the woman. Viewed from that perspective, with my primary sexual goal being to receive a rim-job from every woman that I was intimate with, I made sure that it happened on the first date.