The Making of Jesi : Part 1

Disclaimer: While this story is based upon true events that occurred over many years there are several aspects of the story that that are fictional. Primarily, the dates in which the events occurred have been changed for a variety of reasons as have the frequency of sexual encounters but not by much.

Hi … my name is Jess. So many years have passed and as I sit here contemplating the events in my life it is very easy to be comfortable with and, at the very same time, aroused by the path I traveled. To be totally honest I would not go back and change any one aspect of it although I would probably add more experimentation. My thoughts go back to a time several months after my eighteenth birthday.

I was an only child who was pampered by his parents to the extent that my early development lay completely in their hands and, of course, an adult nanny – the hands of three adults. My parents’ employment required our constant relocation throughout the world. In addition, I was not allowed to travel to a majority of the locations where they conducted their work; however, I was housed in a safe place as close to them as could be arranged. Obviously, I spent the early years in the hands of a variety of nannies whose skills addressed the current needs necessary to my home schooling.

This, obviously, created some pros and cons with regard to my evolution as a person. Being taught and controlled constantly by an adult provided me with a great learning experience but, at the same time, provided a one-sided view of the world – an adult view. Over the years it was instilled in me that knowledge given by an adult was not to be questioned but was to be embraced as the truth. I can’t express to you how important this concept is as it relates to this and the following chapters. In short, I was a naïve and trusting young man. “Impressionable” would be a one word description.

A short time after my eighteenth birthday, and having been home schooled throughout my life, my parents applied for a high school diploma on my behalf. They were in a hurry to obtain the document as we were to be relocated for a two to three year assignment overseas. A week after the application was processed we received notice that a diploma would not be forthcoming due to an oversight on my parents’ part. It seemed I would be required to complete two electives, of my choice, before I could graduate. I will never forget the frustration of my parents as we sat in my uncle’s condo in southern California.

Uncle Jim was not actually my blood uncle but was a longtime friend of my father who I had been told to consider as a relative. Since my parents were scheduled to leave in two days they were frantic to come up with a remedy. By late afternoon the consensus seemed to be that we would just have to wait until we returned home from the assignment; however, I could tell they were not totally at ease with that plan. Primarily, the concern was that I would not be able to go to college as planned, at least not until much later in life. That evening, after my Uncle Jim had returned home from his part-time job, we sat down to dinner and began to discuss the issue once more.

During that discussion my uncle proposed that it would solve the problem if I just stayed with him and attend school at a nearby all boys academy. At first my parents were not in agreement but, as my uncle pointed out, it would be better for me to get the required electives done while I was close to the age of a high school senior. In addition, he noted that I would benefit from the opportunity of meeting young men close to my age – something I was sorely missing in my life. He continued by saying that I would be living in a senior citizen community and with only two classes I would not be overcome by the experience. In the end, it was decided that this option would be best for me.

As I went upstairs to bed I was, not only, convinced that the problem had been resolved but was also becoming excited about this new adventure. A short time later I awoke needing to use the restroom and as I walked down the hall I became aware that my parents and uncle were still awake and talking downstairs in the living room. As I stood at the top of the stairs I clearly heard my mother express her concern over the plan we had agreed to.

“Jim, I know this is probably the best solution to the situation we are facing, but I worry that the plan could affect Jess negatively! I am concerned as to how he will be treated due to his small stature and effeminate mannerisms. To him he is quite normal acting but we can all agree that if it were not for his clothes and name he would most likely be taken as a young girl. He even speaks with a tone one would associate with a female!”

I was shocked! A girl! I thought maybe I had heard her wrong. I instantly scrutinized how I spoke, looked and acted but I could not associate my demeanor as being girlish.

“Look,” Jim replied, “I will keep a close eye on him and I will speak with him on a daily basis to make sure he is comfortable and happy. If there is any hint that he is being bullied, insulted, or treated in any negative way I will pull him out of the school and get a home school professional to take over here at the house. But I still have to think that giving him this opportunity to develop is essential.”

My mother did not respond for several seconds as she was most likely mulling over Jim’s argument. Finally I heard her say, “Okay, that makes me feel much better. Please, assure me you will be vigilant!”

“I promise, I will take care of everything,” Jim stated.

I returned to my room no longer having a need to urinate. Laying there for hours I again reviewed and analyzed my demeanor but, as hard as I tried, I could not identify the mannerisms that would lead someone to identify me as a female. I admitted to myself that I was indeed short and somewhat slim. I also could accept that my voice was a little high pitched and that my skin was very soft but that was probably due to the skin lotion I used regularly.

Furthermore, I concluded, even though my blonde hair was longer than currently worn by most young men it did not mean that it was girlish … or did it. Yes, I did not participate in sports but when had I ever had that opportunity. Then it occurred to me that I actually had no interest in sports. Just as I fell off to sleep, a fitful sleep, I knew I probably needed to try and change the way I acted, looked and spoke.

I awoke in the next morning still considering what I had overheard the night before on the landing. Going straight to the shower I explored my genitals because surely if I had a penis and balls nobody could think I was a female. Yes, they were there in all their glory but it did not take me long to realize that having them and seeing them were two different issues. I elected not use lotion before getting dressed.

After dressing I went downstairs for breakfast and to prepare for a trip to the high school with my mother to register for the necessary classes I would need to obtain my diploma. My mother was at the table and had set out cereal and milk.

“Good morning mom,” I said with as low a voice as I could muster.

“What’s wrong with your voice,” she asked. “Are you feeling okay – you sound sick.”

“No, I am fine,” I replied. “Maybe my voice is changing as I am getting older.”

My mother looked at me with that look that always told me she thought I was full of it. “Are you kidding around or do I need to take you to a clinic for a checkup?”

Realizing immediately that I was not going to pull off a change in my voice overnight and deciding that taking the chance of getting a shot should I opt for the clinic convinced me to rethink my plan. “Yes, I am just kidding – I am fine,” I said with a light giggle. So much for change I said to myself as I went back upstairs to apply some lotion.

The registration process went smoothly. Much to my mother’s protests I chose to take two electives that I was pretty sure would not take much effort to pass and courses that had some interest on my part. I had received a very nice digital camera and several lenses for my eighteenth birthday so I signed up for Introduction to Photography as my first choice. Other options for my second choice were limited but a drama class seemed to be my best bet. How hard could that be I wondered?

My parents, after much hugging and kissing, finally departed the next morning to catch their flight out of the country. It had not dawned on me until that very moment that I would not see them for a very long time. Tears flowed down my cheeks, much like a girl I thought and much to my chagrin, as we said our goodbyes.

My uncle and I retired to the living room right after we watched the taxi fade away. As I sat across from him I realized how little I actually knew about my surrogate uncle. I contemplated that realization in earnest while I struggled with what to say. He was a very nice man in his mid to late 50’s and while he was older he obviously worked out. There was no mid-line bulge, he had all his hair, his shirt did not hide his muscular physic and the magazine he was thumbing through was, judging from the photograph on the cover, a muscle man issue.

As if he had read my mine Uncle Jim looked up from his magazine and said, “I suppose we don’t know each other that well but I am sure time will take care of that Jess. But in the meantime, is there anything you want to ask me or is there anything you want or need while you are here?”

“I have not had time to think about things I might need but I will give it some thought. I suppose, judging from the magazine, you are way into working out?”

“Yeah,” he replied, “I work out most every day when I get home and sometimes on the weekends. You think you might be interested in working out with me?”

“Well, no I don’t believe I would be interested in that,” I said before giving his inquiry some thought. Damn, I could have said yes to illustrate that I am actually a somewhat macho young guy I thought. So I followed that missed opportunity by saying “I would not mind watching you work out though.”

Stupid – even in my mind that sounded so girly! But even as stupid as that sounded Uncle Jim just smiled and said, “Great, you can spot for me.”

“Spot – what does that mean?” Hoping beyond hope that it meant something manly.

“Oh, sorry ... it means that you are there to help should the weight be too much for me. Don’t worry, I will show you how that works later.”

“Okay,” I replied.

“Anything else?”

“Well, I think I would like to get a computer. I have only a beginner understanding of how computers work but it would help with school. I need to be honest here … when I have asked for one, my parents have always said no. Something about all the inappropriate stuff on the internet.”

“Hmm,” he said as he gave my request some thought. “Tell you what, I will agree as long as you keep it between you and me. You are 18 so what you research and look at on the internet is your business. Just be aware that the first rule of the internet, especially chat rooms, is that you never give out your real name and/or address to anyone. Do you understand me?” He said all this with a somewhat coy grin on his face.

“Okay. I promise you I will never do that.”

“Great. I have an older computer upstairs that I am not using. It will be prefect for you. I am off tomorrow so we can set it up in your room. I would let you use mine but I think you should have all the privacy you want. How does that sound? One thing though, when you email your parents you will need to use my computer. That way we won’t be giving away the fact that you have your own computer … agreed?

“That would be perfect. Thank you! While on the subject I would like to get a driver’s license. I have done a lot of driving with my father but just never had the opportunity or need to get a license.”

“Sure. I will stop and pick you up a book so you can start studying for the test and I will take you out somewhere to practice. I have an old VW van you can use when you get your license. It is not much but it is better than walking.” Yes, Uncle Jim had been a hippy I learned and had actually lived in the van for a while back in the day.

I went to bed that night finding it hard to sleep as I, not only, thought of how much I would miss my parents but with a tingling in my stomach about my newfound access to the internet and a car. With the start of school more than 4 months away I would have ample opportunity to explore the vast reaches of the net and become an accomplished driver. Little did I know what lay out there for me to consider and explore could change my entire outlook on life.

Early the next morning Uncle Jim and I spent the morning in the attic retrieving and setting up my computer. My uncle spent over an hour configuring the computer hard drive, as he called it, to allow internet access. Finally, he announced that it was done and that he would afford me the opportunity, under his guidance, to install start up user and password identities. As I sat at the computer he directed me through the process. I came up with a user name and a password that did not identify me. He had told me when I entered these identifiers that he was turning his head so he would not know what they were; however, years later I would come to realize that he had lied … I now believe he did not turn his head away as I entered them.

For over three weeks I “surfed” the web as I learned it was called. Everything from photography to acting was devoured to the point that I cringed at the thought of reading another article. When not on the computer I was learning everything there was to learn about weightlifting except, of course, how to actually work out. While at first I did not get much out it I slowly began to look forward to the sessions. Watching my uncle press the weights and do his squats while wearing only tennis shoes and shorts was for some reason quite exhilarating. I did wonder why my stomach got kind of queasy when I watched him go through his workout, but dismissed the feeling.

It was not until the third week that something happened that would slowly lead me into a transition that I had never contemplated. My uncle was laying on his back on the bench and was using dumb bells that were intended to work his chest muscles. As I watched I noticed that there was a significant bulge in his shorts that I had never noticed before. While wondering why I had never noticed it before I realized that these new shorts appeared to be new and seemed to fit him a little tighter. It was so mesmerizing that even though I tried not to stare I repeatedly kept looking back at the bulge and wondering what it looked like without the shorts.

As I thought about that I became aware of a funny sensation in the pit of my stomach and, for some reason, the room seemed to get awfully hot. As soon as he finished his reps I ran up to my room feeling like a total pervert. I was filled with dread as I kept wondering if my uncle had noticed anything. How would I look him in the eye if he did? Would he notify my parents that I was a deviate? Would he demand I leave his house? So many questions. I didn’t know at this point what was happening but I knew I had the resource to find out – my computer beckoned. It would be a week before I had the nerve to get on the computer mostly because I feared that once I looked into the subject everyone would know how much of a pervert I am. But the day finally came.

My uncle had left for work so I had the house and my computer to myself. The nervousness that I felt as I showered seemed to permeate my entire body to the point that I thought my heart would burst out of my chest. My thoughts kept reeling around my brain – what do I look for and under what terms do I search? My excitement was causing my hands … no, my entire body, to tremble as I sat down before the tool I would use to find answers. I brought up my search engine then typed in the word “penis.” The computer whirled and spat and after what seemed an eternity flashed a wide variety of websites available to answer my questions.

But where to start … it was so daunting. Nervously I selected a site that linked penis to masturbation. Since I had never masturbated before I was thinking I should give that some consideration. Within seconds of selecting the site the screen was saturated with digital images of “cocks” as they were called. Each image depicted cocks in various stages of arousal including sperm shooting out over the naked chest of the person stroking the cock. My own cock immediately became hard - so hard it hurt … it felt like my hard cock was trying to push out through the end of itself. So hot … I hurriedly exited the internet as quickly as I could. Laying back on the bed I started visualizing the images I had seen on the site while grabbing and then stroking my very hard cock. My passion seemed to have no limits … with each stroke my excitement mounted.

I was in a frenzy as I pounded my cock until I began squirting sperm all over my stomach and chest … some actually hitting me under my chin. How good did that feel I keep asking as I slowly began to relax? Although I just had an orgasm, and you would think I would be satisfied, I found myself wanting more … do it again … but my cock did not seem to want to respond. Maybe later.

Maybe later did not happen over the next few weeks as I began to experience a lot of guilt with what I had done and, especially, that I had done it while thinking of cocks! What a pervert I had become I thought – maybe I should have been a girl I wondered. I also believed, and I was so sure it was just because I felt guilty, that my computer often looked different than I had left it. How could that be I wondered since I was the only one who had the sign-on information? Obviously I was over-thinking things … or was I.