Oliver's Story

It is horrific growing up as a person you despise, feeling trapped inside a contradicting body. From a very early age, I wanted to rip my penis off and flush it down the toilet. But, much more than that, I hated looking like a man and being considered male to all who saw me. Even my name offended me. Every time I heard my name, Oliver, I wanted to be sick. I knew I was not Oliver and just wanted to be seen as Olivia, just, Olivia.

My school days were endless and oppressive, and I despised every moment of my youth. Being effeminate, the mocking and name-calling, I had to endure was incessant torture. I had no refuge at home either. My father despised me for not being his strapping son. I was a weakling to him, and definitely not a chip off the old block. His torment was even worse than that of the others at school, always emotionally eviscerating and often physical. The only person who understood my suffering was my mother, who not only empathized with me for the brutalities I suffered and often intervened with my horrible father.  

When I was ten years old, my parents got divorced. I was, no doubt, a great catalyst in the demise of their marriage. I had no conflicting emotions about it, and when he left, it turned out to be one of the happiest days of my miserable youth. How I managed to live through the following eight years, however, is still a mystery to me. Being a sissy boy when you are young is brutal. Day in and day out, unspeakable and hateful events punctuated my existence. The only relief from my torture was being ensconced in my mother’s loving arms.

After finishing school, my mother finally took me to a psychologist. I was afraid and sceptical of the professional, whom I feared, would deem me as unworthy as the rest of the outside world, but I quickly found that the shrink was someone with whom I could be comfortable. After endless consultations with the psychologist, fortunately, I was finally on the road to becoming a woman.

Fortuitously, money was not an object and my metamorphosis soon got underway. The road to gender correction is long and arduous, but most of all, it is incomprehensibly expensive. I was grateful that the new gift of life came with no financial burden. By now, I had stopped wanting to rip off and flush my penis, the least of my concerns, and knew that the corrective surgery process would be a challenging ordeal. The operations that I would have to undergo would take place in Thailand, the most well-renown destination for gender transformations. While the surgeries might have seemed daunting to many, to me it was the embodiment of the yellow brick road.

Regrettably, the final stage of my liberation would only take place one year hence. There were necessary precursors en route and I would have to commence a long regime of hormone and antiandrogen treatments, which I got warned could wreak havoc with my mind. According to the doctor in charge of my case, he had never seen a better candidate than me in his life. I was five-foot-six-tall, very slim, with innately feminine features. My hands and feet were petite and my body was practically hairless. A further plus is that I was born without Adam’s apple. Allegedly, my sparse patches of facial hair would easily get taken care of with electrolysis and with the hormone treatment, resulting in a naturally feminine-looking chin and neck. Mercifully, by contrast, I had a thick mop of hair on my head.

I got told that with the hormone treatment I would never grow large breasts, but that after two years I would probably have decent B-cup size tits. Naturally, breast augmentation could be performed later on if I so wished, but this was not an initial concern to me. My emancipation would liberate me from the gender prison I had lived in.

I already had a very feminine voice, always one of the beacons for my tormenters, so I could finally take advantage of what had been a source of shame and agony for me. The inherently feminine tone of my voice would also soften with hormone treatment. According to the doctor, over the following couple of years, subcutaneous fat deposits would naturally appear on my hips, because of the hormone changes, which would temper my angularities, and give me an even more womanly appearance. With the oestrogen and other pills I would take, my skin would also become softer and my nipples would become sensitive as my areolas developed a female look. I could hardly wait!

To see the changes as Olivia materialized and I could begin to live my new life, was mind-blowing. The week after my hormone therapy regimen got underway my mom took me shopping as a treat. Part of this stage of my liberation was to live as a woman in the world rather than just in my head and heart. I had always worn ‘camp’ clothing but had never actually dressed as a woman. With the determination of a general on a war campaign, my mother led me through a gauntlet of power shopping. Trying on the clothes in the stores was a bit unnerving at first, but seeing glimpses of Olivia in the mirror as I put them on, was awesome. The kowtowing of the salespeople desperate for their commissions was an endless source of amusement, but their enthusiasm worked to our mutual benefit. With a plethora of shopping bags, we eventually arrived home, late that afternoon.

That evening, a fashion show of epic proportions took place in our home, and my mother and I just loved it. It was not vanity, but it felt wonderful as I took my first steps of transforming into a woman. During that evening mom also gave me many of her jewellery pieces, to amplify my transformation. Her taste was impeccable and her stash of jewels enhanced every outfit. I soaked it all up and had never had a more exciting night in my life. My metamorphosis had truly begun and in bed that night, exhausted and exhilarated, tears of joy spilled from my eyes.

The following day, we visited my hairdresser where my long brown hair got enhanced with highlights and cut to perfection. I wore a suitable outfit for the daytime and looked fetching. I think we were both intoxicated with the emergence of Olivia, and my mom and I were equally thrilled to see me transform. When I emerged from the hairdresser, I had the most stylish shoulder-length cut with perfect colour. I looked stunning. That evening, a beautician arrived at our home and I got my first masterclass in the art of makeup. Observing myself in the mirror and seeing myself in full bloom for the first time, both mom and I were amazed and overcome. I cried myself to sleep again that night, happier than I had ever been in my life.

Over the next year, I lived as, Olivia, and with every passing day, the dread of being Oliver kept diminishing. I would often shop with mom and have lunch with her friends, ‘the girls’ as she referred to them. Becoming one of them was totally fulfilling. I did very little other socialising during this period and never having made friends at school, this was not a problem for me. As time passed, so did my self-confidence. All I could think about as I still lived a secluded existence that year, was my final destination.

One who is not transgender would naturally suppose that I would’ve had gay friends, but I did not. I never saw myself as gay, nor was I ever interested in a gay relationship. Please understand I was not homophobic, but for me being a transvestite and living on the fringes of gay society was simply not an option. Given the psychological regimen that I underwent during the year, in tandem with the hormone therapy, I also knew that challenges would always present themselves throughout my life. There would be many challenges ahead for me, but I was confident that I would be able to deal with them, as and when they arose.

A new thought had become part of my reality. I felt, that given my positive attitude, I would eventually meet a man who would deal with my situation before I would be able to lead a fulfilled existence as a woman in a loving relationship with a husband.

Eventually, a week before I was about to depart for Thailand I impulsively decided to visit a local cocktail bar one evening. My confidence had been building steadily, and the vision of myself and my life had been clarifying itself in my mind. I suppose the outing was a ‘finale’ celebration of some sort, in an attempt to bid my former existence farewell.

When I returned from Thailand, Oliver would be gone, and Olivia would have been reborn. My mother was going out that evening and I decided not to tell her about my rash decision, knowing she would worry that I was not ready.

A few weeks earlier, on one of the girls’ shopping extravaganzas, I had purchased the most beautiful cocktail dress in an unusual shade that the salesperson referred to as, ‘chartreuse.’ It is an unusual shade of green, but according to the salesperson, I was one of the few women who could pull it off. By now, my makeup skills had been well refined and my breasts were developing rather nicely. I took great care with my appearance that evening and when I was finally about to leave home, I looked sensational.

Everything was perfect; my hair, makeup, dress, shoes, accessories, including the diamond studs my mom had given me. Observing myself in the mirror before I departed tears came to my eyes, resulting in the necessity for a makeup reconstruction. This, in itself, overcame me, because to experience such an everyday occurrence any woman would consider a burden, to me was a privilege.

Finally, I made my way to the sophisticated cocktail lounge that I had earmarked for this occasion. After arriving at the lounge, I ordered a glass of white wine and sat demurely savouring the atmosphere and bristling with delight at the thought of being so close to my final destination. It even thrilled me to see the hint of my perfect shade of lipstick on the napkin.

My reverie suddenly got interrupted. My heart almost stopped when Royce, a senior when I was in my first year of high school, walked into the bar and sat down at the counter not far from me. Royce was the school stud and from what I could remember, was the son of a man who owned a successful construction company. He was tall, dark, and handsome, along with any other clichés you could possibly wish to add. Not only was he a very bright student, but good at all the sports in which he participated. In short, he was the guy that all the males at the school wanted to be, and all the women wanted to bed.  

I almost felt myself wilt as I observed him and hoped like hell that he would notice me. I had got warned, coached, and had theorized about the moment when my former and future lives would collide, but to have it happen on my first solo outing, was terrifying.

For a short while, he simply sat enjoying his drink, but just as my tension began to abate, he glanced in my direction. I felt my throat constricting when he got off his barstool and moved in my direction.

“Hi, my name’s, Royce,” he said, introducing himself.

“I am Olivia,” I replied nervously.

“This isn’t some corny pickup line, Olivia, but I feel like I have met you before,” he continued.

“I’m sorry,” I lied, “But I don’t recall meeting you before.” How I got the sentence out without stuttering or even passing out from terror, I still do not know.

Frowning he asked, “Where did you go to school?”

Before my brain engaged properly, I uttered the name of the school that we had both attended, to my inner horror.

“Ah,” he answered, “When did you graduate?”

With my mind partially functioning again, I replied with another lie, “Actually, I’ve just graduated,” I said, having actually graduated a year earlier.

“Oh,” he replied, then with a faux stern look he continued, “Then you really shouldn’t be in this bar.”

“Please don’t expose me,” I answered, feigning angst.

“Well, if you allow me to join you, I won’t say a thing,” he playfully continued the charade.

I gestured for him to take a seat with an air of resignation. For the next while, we continued chatting and as we did so, my nervousness subsided. The conversation was not easy but I did my best to deflect the conversation away from me and focus it on his life. Regrettably, however, I ran out of ideas and the spotlight eventually returned to me.

“So, what are your future plans?” he asked.

“Well, I am going abroad in a few days and will be away for the next month,” I replied. “After that, I hope to do quite a bit of travelling in my gap year,” I concluded, considering the last comment to be a masterstroke.

“But, you are planning to go to college after that?” he asked.

“Yes, maybe, but I am not focussed on that at the moment,” I answered.

“Would you at least allow me to take you out to dinner upon your return?” he inquired.

Trying to extricate myself from this sticky situation, I parried. Then, seeing Royce’s serious face I quickly asked, “Aren’t you married yet?”

With a laugh he retorted, “No. Incidentally, I am not even engaged or dating anyone at present. By the way, it’s a dinner invitation, not a marriage proposal,” he added with a wink.

“A month is a long time,” I countered.

“Not if someone is as beautiful as you,” he said teasingly, and with a very sexy smile.

“Thank you, you’re very kind,” I answered with a frisson of excitement running through me, which unnerved me even further, “But I’m not really interested in dating at the moment.”

“I’m excited that you are assuming it’s a date when I earlier qualified that it wasn’t. I no such assumption or declaration of intent,” he taunted me. Then, gently, he added, “It won’t be a date, just a dinner, hopefully, the first of many,” he jested.

“I’ll think about it,” I replied, smiling demurely.

“Cool, but then you’ll have to give me your phone number. I promise, I won’t harass you,” he responded.

I thought of giving Royce a fictitious number, but afraid that he would immediately check to see if he had programmed the correct number, I decided against that course of action. He did not check after I recited my number. I then hurriedly made a lame excuse about my mom who fictitiously wasn’t feeling too great that evening, and apologised for needing to depart early. After Royce saw me to my car I left with my heart palpitating.

The following day, I relayed my misadventure to my mom. After it was apparent that she wasn’t upset with me for my unannounced solo venture, I supplied her with all the details. “Did you have fun, my baby,” she asked with a conspiratorial laugh. Not only was she not upset, but she also delighted in the details of my adventure with me.

“God mom, it was nerve-wracking,” I answered, as we giggled like two little girls.

Two nights later, at around eight, the front door buzzed. Mom and I were perplexed because we had not received notification from the security gate of the complex. Presuming it was a neighbour who had popped by, we opened the door.

“Good evening Olivia,” Royce uttered as my heart began to thump in my chest. I was so gobsmacked that my mother had to step in and introduce herself.

“I’m Suzie, Olivia’s mom, please, come in,” mom responded, as I stood horrified.

After moving through to the lounge, mom and I exchanged glances, and when she was satisfied that I was not freaking out she left us to arrange our coffee. I had so many conflicting emotions while Royce and I were alone. Knowing that Royce had tracked me down because he wanted to see me sent my mind into a total spin.

After coffee had got served my mother stayed a short while longer, before politely excusing herself again. I was itching to find out how he knew where I lived and finally asked. Royce told me that he had made it his business to find out, but would not divulge the details. We continued chatting for a while and my mind continued to churn over how he’d found me before he finally ‘got down to business.’

Royce told me that he had googled our school website the day after our meeting and simply could not find any record of me. He went on to say, that he had found a photo of a guy named Oliver who looked remarkably like me, and who had graduated the year before.

“Is he your brother by any chance?” Royce innocently questioned.

I sat quietly observing him. I had been caught out, cornered, and simply had nowhere to go.

All the warnings I had received over the past two years hit me with a bang.  Resignedly, I decided to ‘take the bull by the horns.’

With a very shaky voice, I replied, “I am Oliver.”

A look of total bewilderment crossed Royce’s face. It was not angry, but a look of bewilderment.

Gingerly, I began to relate my story to him. I surprised myself with the amount I divulged about my feelings and my journey from hell toward paradise, as I continued I found myself needing to tell Royce more and more. As I did so, he frowned with extreme concentration and when I concluded my story, I finished off by saying, “I‘m really sorry about this, but in fairness, I did tell you that I wasn’t interested in dating. I really had no intention of misleading you.”

“But… Jesus, you’re fucking beautiful,” he stated with a look of puzzlement.

“I am really, really, very sorry Royce,” I again uttered with absolute sincerity.

As his facial expression began to relax, he surprised me by asking comprehensive details about my transformation. Naturally, my earlier speech had only dealt with the basics, but when I got to what was happening I commenced telling him everything about the therapy and the surgeries. He did not have much to say after his first few questions, but he hung on to every word. I knew how overwhelming it must be for him and I understood the consternation he must have felt.

When Royce was about to leave later, I was exhausted by the trauma of my disclosure. As we walked to his vehicle before his departure, Royce stared at me intently. “I will be calling you when you get back,” he said, before reiterating, “I will definitely be calling you.”

The intensity of his declaration stunned me.

That night, I lay in my bed with a million thoughts flooding through my mind. I had just been through the most challenging ordeal of my life and wondered how many more times I would have to endure this same trauma. I knew I was up to the challenge, but knowing it did not lessen the impact of the evening. I was also convinced that I would never see Royce again, reasoning that in the light of day he would come to his senses. Heartbroken, I finally drifted off to sleep.  

The next few days were a blur for me and filled with arduous travel and pre-op consultations. All I can recall from that period was getting wheeled into the theatre prior to my operation.

Several hours later, I awoke and had to endure the discomfort of post-operation headaches and nausea as the anaesthetics worked through my system.

It was early the following morning before I was compos mentis. Through my grogginess, I got lifted when my elated doctor and beaming mother told me that the operation had gone brilliantly. After a few days, according to him, there would only be one final procedure before my new life would truly commence. The pain and discomfort were bearable and I looked forward to clearing that final hurdle and ending my long and difficult journey.

On the second morning after my final operation, my mother popped her head into my room and announced that I had a special visitor. My doctor had not been in to see me thus far that morning and I simply assumed that my mother was being slightly theatrical. Upon opening the door completely, Royce entered the room. Seeing him, as he approached my bed flummoxed me, as I wondered what the hell, he was doing here. Make no mistake I was delighted to see him, which in itself threw me a bit. His smile of genuine concern and relief warmed me in ways that were new to me.

Royce had decided to take a brief holiday in Thailand and was staying at a resort a short way off. Baffled by his timing, and choice of destination, the warmth of his concern negated all my misgivings.

He visited me three times a day for the following four days. Each visit lasted a blissful hour, and mom respectfully made herself rather scarce. Royce also began kissing me on his visits and the exhilaration of that was awesome. I had never kissed anybody intimately before and this newfound closeness was strange and very exciting for me.

I had no way of knowing that what I was doing was acceptable to him, or indeed if it was considered good or bad. Royce, fortunately, appeared very pleased with the positive results of my surgery.

On the last evening of his stay, Royce became rather serious. “Would you allow me to be your first lover?” he inquired.

Observing the startled and questioning look on my face he continued, “According to your mom, after you leave here and you get back, a further two weeks of recuperation will be needed, before… Well, you will be ready to test your new equipment,” he said in a cumbersome manner while flashing an impish grin. We both laughed like two delighted school kids after the comment.

I observed him for a short while then shyly uttered, “Yes, yes, I would be honoured to have you as my first lover.”

“Good, then I’ll book the honeymoon suite at one of my favourite islands a fortnight after your arrival back,” he concluded. 

When Royce left Thailand, I began to have doubts. I was still slightly wary about Royce’s motivations when I finally arrived home after my transformation. I also had difficulty assuming that he could ultimately accept my transformation. I was the person I had always wanted to be, but I was astute enough to realise that many obstacles still lay ahead for me. A myriad of trepidations clouded my thoughts during this period.

There are a few details, which I should mention about my transformation:

Firstly, my dick-head got reconstructed to create a clitoris for me. Secondly, a small section of my colon got inserted into my inverted penis to give my vagina a natural lubricating function. Lastly, I would always have to utilize a dildo to keep my vagina open, because the ‘wound’ that had been created, would always have the tendency to ‘heal’ itself and close, if not artificially kept open. This would be the reality, which I would have to deal with throughout my life.

After arriving home, Royce popped around most evenings, only missing out when he had a business dinner or a work commitment. As the weeks passed, Royce seemed very excited about our upcoming holiday and I had to keep reminding myself that it was really going to happen.  

The day of our departure finally arrived and after a pleasant flight, we reached our destination. The island was magnificent and the accommodation was breathtaking.

There was no pressure to jump into bed with Royce. In fact, it was quite the opposite. After a relaxing afternoon soaking up the atmosphere, Royce arranged a spectacular meal that got served on our private terrace. I felt like a nervous bride on honeymoon, an image I had always imagined in my reveries. I took special care with my appearance and put on the same green dress that I had worn the night we met. I could tell by Royce’s excited eyes that he approved of my ensemble.

The setting could not have been better, and dinner on the terrace was magical. I knew that whatever happened in the future, I would never forget this evening. There was no rush as we ate a magnificent meal and soaked up the ambiance. There were long lingering glances and our conversation never waned as we discussed innermost thoughts and hopes for the future. Finally, I excused myself to indulge in my bathroom ritual.

I had to calm myself with some deep breaths and pep talks in my head, as I completed my preparation. I made sure every hair was in place, and that every part of me was clean and appealing. With just the tiniest dabs of my mother’s choice of perfume, which I have to admit complemented my own scent magnificently, I exited the bathroom in a negligée I had picked out for this occasion. Royce was already in bed and his eyes washed over me.

After slipping into bed next to him, he just lay looking at me, propped up on one arm. “This is your night, my baby; if anything is uncomfortable to you then we can delay it. There is no pressure at all. I simply love being with you and seeing you live your dream. Olivia, I have been waiting for someone like you all my life.”

Unhesitatingly I replied, “Royce, I have also waited for this moment for all my life and there is nobody I would rather share it with, than you. I am ready for this.” 

Royce sensually began to remove my negligée before moving his body on top of mine. As we kissed, I could feel his masculine strength against my feminine slightness and his hardness on my pussy. As he began ardently, kissing me the greatest moment in life had arrived and I got overcome with emotion. As tears began to stream from my eyes he asked, “Must I stop?”

“No, please don’t,” I purred, “I have never been happier in my life.”

As Royce’s face warmed to a smile, I knew at that moment that I was in love with him. His response, when he finally spoke, was soft but definitive. “Jesus, I love you, baby girl. I have loved you from the first moment I saw you,” he told me with a loving glow on his face.

I was not sure where this would end, but the pleasure overwhelming me at this point was good enough for me. My final liberation was at hand and in a soft voice I replied, “I’m ready.”

Very slowly, Royce began to enter me. I had learned from all my tutoring that the physical side of sex is secondary and that the primary stimulation is mental. I knew that my genitalia would never be able to replicate the sensations of a natural woman, but in my wildest dreams, I could not have imagined how good this felt. The warmth of his ardency aroused my entire being.

Finally, I was a woman and all the years of suffering had ultimately ended as we began to make love. I had no idea what lay ahead, but here and now, my arduous journey was over, and I looked forward to facing all that lay ahead.

Authors Note:

A dear friend of mine named Billy helped me with this very difficult topic. I cannot thank him enough for his input.