Trust Fund Baby Pt. 16

It was with a healthy degree of terror that I waited, bent over the desk for Georgie to show up and introduce himself. Whatever I had done to warrant being kidnapped and feminized for his enjoyment was beyond me, and I had a million questions spinning around inside my head, as I waited for him. That bastard kept me hanging too, and Joelle came back into the room twice more to spritz me with additional perfume, before Georgie finally entered the room.

As soon as I heard her voice, I recognized her from my days at Saddleback College. It was Gina, the Women's Studies Major that I had taken as my sugar baby in her Freshman year. The last time I saw her she was lying on the tiled floor of the gender-neutral shower block, unconscious from a drug overdose, in a puddle of urine with semen flowing freely from all three of her orifices. I stopped hanging around the College Campus at that point due to the increased police presence, and I never bothered to enquire after the young woman.

"Gina," I asked hesitantly. "Is that really you?"

"Georgina Thompson in the flesh," she said confidently, as she rounded the desk and came into my direct sight line. "How are you Pete?" she added as an afterthought, although it didn't seem like she was going to wait for an answer.

I was tightly restrained over the large wooden desk, and I had to strain to lift my head up, in order to communicate with her.

"I have waited a long time for this moment," she said quietly. "Ever since you urinated on me in that shower block, I have dreamed of retribution."

"Gina," I pleaded, recognizing the gravity of my situation. "I was just a kid."

"And I wasn't?" she responded angrily. "Choose your words carefully, Pete," she threatened. "I hold your future in my hands."

I swallowed hard as I processed her words. With the recent passing of my uncle, I had no family left on earth. If Gina did snuff me out, no-one would even know. I quickly decided to remain passive, in order not to inflame her. As I lay bent over the desk in silence, Gina continued.

"You, Joe and Nick were on my list," she began ominously. "As you can see I have already dealt with Joelle and Nikki. Those bitches are eternally grateful for my mercy and will do whatever I tell them to."

"Gina, please," I begged.

"Silence," she barked, as I stopped talking and lay there whimpering.

"After you stopped hanging around at Saddleback, I got my shit together," she began. "I graduated college, and immediately got a job under the protective auspices of the alma mater. Revenge was the one thing that kept me sane until I achieved very high wealth and status. I have already extracted it on those two other bimbos, and it is now your turn to pay."

My fear was all-consuming now, as I realized that Gina had me exactly where she wanted me. I was shaking uncontrollably, as she laid a large strap-on cock on the table, right under my nose.

"Here's what happens next," she said quietly, enjoying the complete control she had over me. "First of all, I am going to fuck you in the ass. Will I be your first such experience?" she added with a giggle. "I love taking anal-cherries."

"Gina, please," I begged, as I struggled in vain against my bonds. "Can we talk about this?"

"I go by Georgie now," she stated, deflecting my question. "After I sodomize you, we can talk about your future. I can't decide whether to put you on a plane to Brazil for full gender-reassignment surgery, the way I did with most of the other guys who abused me back in College, or whether to just feminize you a little bit, the way I did with Joelle and Nikki."

I was scared shitless now, as this crazy fucking bitch began to secure the imposing looking latex phallus into her leather harness. As she locked it into place with an ominous click, and began to grease it with what appeared to be Vaseline, I begged for mercy. My pleas fell on deaf ears, but she did clarify what she considered to be the half-measures of forced feminization that she had applied to Joelle and Nikki.

"They are pre-op transsexuals," she informed me. "They still have their male organs although they are both unable to have or sustain an erection. I chemically castrated them, which is my plan for you in order to mitigate the harm you do to the young females of Newport Beach. I thought maybe you had learned your lesson, but once I heard about your "Make Daddy Proud" event, I decided that you needed to have your nuts clipped, too. An eighteen year old High Society Debutante working in your strip-club, for fuck's sake."

"That was a huge misunderstanding, Georgie," I cried. "I was doing a young woman a favor because her dad was being an asshole. Call Jessie Baldwin and ask her. I will give you her number. Please."

"If you fucking lie to me, Pete, it will make things much worse for you," she threatened.

"Georgie," I began to beg, "if you let me go I will sell my strip-club and donate all of the proceeds to the cause of your choosing. The National Organization of Women, The Women's League, whatever you decide."

"That is a start," she conceded, as she rounded the desk, and opened the drawer. "Tell me more."

I started to babble incoherently, my mind scrambled by the threat of complete gender reassignment, in South America, for fuck's sake. I was offering compromises and firing questions at the same time, fixating on how I could return to the United States with a male passport and a pair of 38D breasts. Georgie listened for a couple of moments and then pressed the remote control to my electrically-charged, cock-ring to shut me up.

Georgie must have held the button down for way longer than Nikki did, because I thrashed around on the table trying to escape my bonds, as the searing pain surged through my testicles. I almost passed out, such was the intensity of the agony, and I heard Georgie let out a satisfied giggle.

"Let's fuck first, Pete," she said quietly. "Then you can beg me to keep your male identity intact."

Georgie withdrew a pair of scissors from the desk drawer, and roughly tore a crude opening in the back of my silk boy-shorts, nicking my bare flesh in the process, which drew blood. I was trembling now, aware that my life was in her hands. After she laid the scissors down in front of my face, the blood visible on the stainless steel blade, she lined up her phallus with the opening of my well-lubricated anus, and waited at the entrance of it.

"We are at the freight terminal of John Wayne International Airport," she informed me, which answered one of my questions, leaving approximately one thousand unanswered. "My private jet is here, and we have already been granted approval for take-off. One of my options is to incapacitate you and then load you as freight. We can get to Brazil in less than a day, stopping in Canada first, which has less invasive policies regarding transportation of livestock, and then again in Mexico City to refuel."

"Transportation of livestock?" I repeated with a shaky voice.

"Yes," Georgie answered cheerfully. "If I declare you as a household pet there are various mandatory inspections. However, as livestock I just need to produce the appropriate vaccination certificates and we are good to go. You will be asleep anyway, and there is minimal likelihood of a secondary inspection."

"Georgie," I begged, as she pushed slightly against my sphincter. "I will spend the rest of my life championing women's rights, if you let me go back home today."

"I am trying to decide if I can trust you," she said. "Although you must know that my extraction agents can pick you up anytime I desire."

"Please," I begged. "Show me some mercy."

"Decisions, decisions," she sang in a playful voice, as she eased forward inside of my ass. "Whether to allow you to remain as Pete, or to transform you into Petra."

I cried out in anguish as she forced her way through my sphincter, and this emboldened Georgie to continue to belittle me.

"Do you remember your sage words of advice when you pissed on me in the shower?" she asked, that singular event seemingly driving her hatred of me.

"Something about making sacrifices?" I said, through my heavy breathing. "I was just trying to motivate you, Gina."

"Georgie," she said angrily. "I go by Georgie now. That is the last time I will remind you."

"Georgie," I repeated, the stress and pain beginning to overwhelm me. "Georgie."

"I remember it verbatim," she whispered. "In fact, those words have haunted me for over twenty years."

"I am sorry, Georgie," I wailed, as she adjusted her position slightly in order to penetrate me more deeply.

"One day, when you are running your own little fiefdom," she began, in a detached, monotone voice, "remember the sacrifices you made for your education."

My heart sank as I remembered the dehumanizing encounter in vivid detail. I had urinated on the young girl, before paying her with a Traveler's Check with the words "Golden Shower," inscribed on the memo line.

"Payback is a bitch," Georgie said coldly.

I had sodomized literally hundreds of young women by this time in my life, getting my jollies from their plaintive cries as they tried to deal with the emotional and physical pain of losing their anal-cherry. I had never once given any thought to the discomfort associated with first-time anal sex, but as Georgie forced her way inside my anal cavity, it brought tears to my eyes.

Georgie rained insults and threats down on me as she slowly impaled me with her strap-on phallus. My mind kept focusing on what the hell faced me if I was put on a plane to Rio de Janeiro for complete gender-reassignment, until the pain of being sodomized forced me to deal with my current crisis, instead of my future one. Georgie made me cry out for mercy as she butt-fucked me, and after a protracted session, she finally withdrew the strap-on from my tender asshole.

"My plane for Rio leaves in ninety minutes," she said, clearly enjoying my anguish. "Convince me why you shouldn't be on it, asleep in your crate."

As I began to articulate my thoughts on how I could help her cause, I was grateful that the cessation of pain allowed me to speak clearly and concisely. I made an impassioned plea for my life, and after a few moments Georgie cut me off.

"You know what Pete," she said cheerfully, as she unlocked the phallus from its harness. "I modified Nikki and Joelle because they didn't demonstrate the abject contrition that you just did. They spent two years in Brazil, between the extensive physical modifications, and the transgendered brothels that they worked in, to pay for their medical bills. I am inclined to believe you, but I need a little more from you."

As she wiped her soiled strap-on in my hair to clean it, I offered her additional concessions, and by the time I was done, I had committed twenty five percent of my monthly allowance to the charity of her choosing, the immediate cessation of my involvement in the strip-club business, and a promise that I would no longer use and abuse the young vulnerable women of Newport Beach.

Seemingly content with my concessions and the palpable remorse I had demonstrated, Georgie released me from my bonds, and told me to kneel by her side. I obeyed her reflexively, one brief torture session having been sufficient to make me toe the line. Also, she hadn't yet released me from the confines of the cock-ring, and she still had the remote in her hand to fully ensure my compliance.

"I will be right back," she said cheerfully. "Stay on your knees."

It would be a huge understatement to say that I was quivering with fear, as I waited on my knees for her to return. After what seemed like an eternity, Georgie breezed back into the room, waving her phone in my face.

"Well," she began slowly, enjoying my torment. "I spoke to Jessie Baldwin, and luckily for you, she confirmed your rendition of the Make Daddy Proud event. Jessie claims you treated her very well throughout your brief relationship, which is in sharp contrast to the way you abused every other young woman who was sucked into your sordid web. I am going to let you go, but I want you to see what awaits you if you don't follow through," she said firmly. "Joelle, Nikki, come."

Despite being beckoned as if they were puppies, the girls showed no sign of resentment or resistance as they sashayed into the room, their exaggerated femininity belying the fact that they were both still male, at least in the eyes of the law.

They were identically attired in silky lingerie, not dissimilar to the intimates that I had been forced to wear for my reunion with Georgie. They also wore garter-belts and stockings, which along with their sky-high heels, only added to their feminine allure.

"Dance," Georgie instructed the two bimbo-looking girls.

As excruciatingly painful as it was for me to have to witness their debasement, it must have been ten times worse for them, as they began to gyrate their hips, ensuring that their motions were perfectly synchronized. They were both very sensual dancers and I found myself wondering if they moved so lightly under the bed sheets.

Georgie made them perform for her amusement for several moments, the lack of music making the humiliation even more pronounced, as the only sound was their high heels clacking on the marble floor.

"Strip," Georgie ordered, as the two of them stopped dancing, and began to disrobe in a seductive and alluring manner.

They had obviously been forced to do this before, because they worked in almost perfect synchronicity, shedding their silky lingerie in a clearly choreographed manner, until they ended up butt-naked, in just their high-heels, facing away from me. As I admired their beautifully sculpted, completely hairless bodies, Georgie gave me a detailed rundown of their collective efforts and sacrifices, in order to have achieved such desirable physiques.

"This transformation took a significant toll," she assured me proudly. "Both physical and financial. Although I made the girls work in a transgendered brothel in Rio, until they had earned back every cent that I had fronted them," she added softly. "That took two years."

"Two years," I repeated, to no-one in particular, as I knelt uncomfortably on the marble floor.

"Their platinum-blonde, waist-length wigs were two thousand dollars," Georgie said in disgust. "It costs a fortune to feminize an Alpha male. Although now that the girls' natural hair has grown out to my desired length, I have kept the wig for my next victim," she added ominously, as we made eye-contact.

Georgie had a devious smirk on her face which caused me to look away immediately, before she issued her next command.

"Arch your backs," Georgie told Joelle and Nikki.

Again, in perfect unison they raised their heads skyward, which arched their slender toned backs, and made the tips of their almost white hair, brush against the top of their tight asses. Their long, natural tresses were phenomenal, both in appearance and condition, and I wondered how much time each week they devoted to their hair treatments. The resultant look had a healthy shine, appearing almost silk-like and certainly soft to the touch.

"Hair up," Georgie instructed.

Upon hearing her latest command, the girls placed the palm of their right hand directly against the back of their neck and lifted their hair over their right shoulder. As both of their necks came into view, there was a large raised tattoo visible at the base of their respective skulls.

The wording, particularly provocative as it would remain there for life, caused me to swallow hard once again. I hadn't ever seen a tattoo quite like these before, as the words "Georgie's Toy" seemed to be raised above their skin, instead of underneath it.

"Where did they get those tattoos done?" I asked. "They are very unique."

"Brazil," Georgie answered cheerfully. "Although they are not tattoos. I branded them."

"Branded?" I asked incredulously, on the verge of pissing myself, but trying to remain respectful of her at all times.

"Like I said, Pete," she whispered softly. "I consider these pieces of shit livestock. I want them to wear a brand of ownership."

I didn't know what to say. I was completely lost for words, unable to verbalize what was going through my head, which was a combination of revulsion, shock and sheer terror.

"In retrospect, I shouldn't have used a hot brand," Georgie said quietly, as if she was discussing the incorrect choice of paint color for her living room. "They were out of action for a month as the wounds healed, which cost me a small fortune in lost revenue at the brothel. There just weren't any other options in Brazil," she added. "What do think of their asses?" she asked, changing the subject completely.

"Just about fucking perfect," I mused, trying to be complimentary of her work, as I admired their pert, upturned buttocks.

"Countless hours on a StairMaster," Georgie informed me, aware of my fascination with anal sex. "Combined with a strict weight-loss regimen, liposuction of the upper thighs, and periodic hyaluronic acid injections. These bitches are high-maintenance."

I shuddered as I realized how close I had been to a similar fate. Nikki and Joelle offered zero resistance as Georgie referred to them as bitches, and put them on display as if they were her house-pets. After I had taken in every square inch, she addressed them again.

"Turn and face me."

Once again, rotating in the same direction, and in perfect unison, Joelle and Nikki turned one hundred and eighty degrees in order to face Georgie. As I knelt silently by her side, I was grateful to have dodged this humiliating fate.

Joelle and Nikki, despite their demeaning circumstances, both wore huge smiles on their faces, as if they were honored to be in the presence of their mistress. Of course, with my extensive history of enslaving desperate women, I knew first-hand that most humans are relatively happy as long as their current life experience is better than their most recent. Nikki and Joelle would happily put up with Georgie's dehumanizing treatment of them, as long as they didn't have to return to the transgendered brothel, in the slums of Rio.

Standing before us, with their matching manicured nails on display as they hid their genital areas with their crossed hands, they looked like two coquettish young girls. Even as my body was hairless, I felt very masculine in the company of these two highly feminized she-males.

Now that they were no longer in the humid environment of the shower block, Joelle and Nikki had taken the time to do their make-up. They had made an obvious effort to appear similar, and were both wearing hot-pink lip gloss to match their brightly colored nails.

I was used to a more subtle application of make-up, in which the goal was to highlight youth and innocence, in a muted way. By contrast, Joelle and Nikki looked like a couple of street walkers with their garish lip color, and I wondered whether this is how they had presented themselves when they had been forced to suck their way through Rio, to repay Georgie for their surgeries.

Once again, Georgie allowed me to take in every detail, and I marveled at their perfect tits. I had dated numerous women who had undergone breast-enhancement surgery, but I had never seen such perfectly sized, identically symmetrical, breasts. Their proportions were ideal, skinny yet toned legs, flat taut abdomens, incredible upper bodies, topped off with the most amazing set of fake tits I had ever seen. Even their nipples, each of which were surrounded by a perfectly sized areola, stood erect, inviting male attention. These were two of the most physically desirable women I had ever encountered, and for a split second I forgot that they were men.

"Hands-up," Georgie ordered, completely shattering the illusion.