Trippin with Tiffany
- 2 years ago
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Chapter 1 - Becoming Tiffany free porn video
I guess it's fair to say I'm a creature of personal desire. And while that may be true, I also recognize that without the unique circumstances associated with my upbringing, there is little chance I'd be who I've become.
My parents both worked for a large hedge fund and were killed during the World Trade Center collapse in 2001. I was only one year old at the time and too young to understand what had happened. I still have some fuzzy memories of my parents, but nothing I can really recall in detail.
I was adopted by my Aunt Jessie who lived North of Tampa and worked as a marketing director for the Bucs. She was my Mom's only sibling and was the free spirit of the family, living with her life partner, who I came to know as Aunt Deb. Both of them were amazingly loving, and nurturing. All their friends were part of the LGBT community and I had no idea that my "family" was unique until I started school and discovered that most kids had what some would refer to as more traditional families.
To me though, I never would have wanted things any other way. They were always taking me on some new adventure, and I got to see life through their eyes all the beauty it had to offer.
I also grew up totally comfortable with the human body and didn't see it as anything to be covered or embarrassed about. We had a large backyard and pool and both my Aunts shunned the need for swimwear and were active naturists. I can honestly say I've spent more time naked than clothed.
I think I was probably fourteen before I realized my body wasn't developing the way other boy's bodies were. I had always been skinny, with narrow shoulders and finer features than my friends, but my voice still hadn't broken, nor had I developed any hair on my body. I talked to Aunt Jessie about this and she took me to a close friend of hers who was a doctor to run some tests.
The initial physical exam didn't turn up anything out of the ordinary. I was actually very well "developed" in the manhood area, although he noted my balls and scrotum were smaller than normal. The lab tests though revealed a very low testosterone level in my system.
The doctor said he could prescribe testosterone treatments that should bring on a normal puberty phase for me. I told him I'd like to think about it and talk with my Aunts some before making a decision.
Over dinner that night, I told my Aunts I liked who I was and how I looked and didn't think I wanted to go through the treatment. They said it was totally my choice and the only thing that mattered was me being who I wanted to be. I explained that if I was totally honest, I actually preferred being more female.
I told them I had much more in common with women than men and the idea of having a muscular body with lots of body hair totally turned me off. They suggested that it might be a good idea to go through some counseling to fully understand my feeling and desires, which I agreed to do.
Over the course of the next six months, I was able to confirm my preference for living as a female, although my sexual orientation was very much up in the air. That said, the idea of going through a full sex change operation didn't appeal to me either. I decided on my own unique path, with my Aunts fully embraced.
With my exceedingly low testosterone level, my voice never really dropped and my body retained it's slighter frame. I let my hair grow out and my Aunts helped me learn to do my hair and makeup and helped me choose a female wardrobe. They also began home schooling me so I could make the transition without dealing with all the social challenges of doing it publicly while in school.
By the time I was sixteen, I had been living as a girl for over a year and a half. I could go out with my Aunts and their friends and be totally confident of being accepted as their niece, and a very attractive one at that. I was completely flat chested, but wore a bra with inserts that gave me modest, but acceptable looking breasts.
Everyone fully accepted me being trans and I think my Aunts assumed that eventually, I would make a decision to fully transition once I was ready. Other ideas were developing in my head though.
Although I never went through many of the physical changes associated with puberty, I definitely made up for it in terms of horniness. My cock worked just fine and I spent hours masturbating in my room. I got hard with the least provocation and would stay that way for hours it seemed.
I found special underwear online that helped me hide my male endowment, but still had to be careful with what I wore out. More and more, I felt totally comfortable as a woman, but loved having a nice hard cock between my legs. The truth was I loved being both sexes and neither sex. I didn't want to fit into any one category and loved the idea of being just me.
I was totally turned on by the shemale porn I found on line. I knew I was attracted to both men and women and the whole concept kept growing more and more appealing. I finally sat my Aunts down and told them I had decided to live my life as a shemale and I wanted to get breast implants.
Even with their incredibly liberal and accepting attitudes, this took a while for them to fully accept. They ultimately said it was my own life choice and they fully supported it. However, I would need to wait until I was eighteen before getting the surgery and I'd have to pay for it myself.
I asked them how I was going to afford the surgery and that’s when they told me about the trust fund that had been set up for me following the death of my parents. Between their accumulated savings, life insurance, and an additional benefit from the hedge fund, I was actually worth well over $15M, which I would gain access to once I turned 18.
I planned my surgery for my eighteenth birthday and my Aunts helped me find the very best plastic surgeon in the state. The recovery period took several weeks, but the results were nothing short of spectacular. I now had very perky 34B breasts and it was nearly impossible to tell they weren't totally natural.
I continued living with my Aunts for the next six months, continuing to refine my appearance and my own self-image. I'll always remember the day I stood naked in front of a full-length mirror and finally judged myself to be exactly the person I had been working to become.
I was 5'8" and 125lbs, with straight blonde hair that fell below my shoulders. My face was oval shaped and very feminine, with green eyes and full pouty lips. My carefully developed exercise routine had given me a tight firm figure that looked amazing in a pencil dress. I had been naturally gifted with a sexy round ass, which was the perfect compliment to my new, firm breasts. While it had taken a full six months of electrolysis, my body was now totally and permanently hair free.
Of course, there was that one single feature that highlighted the fact that I was no ordinary female, a totally smooth, bare, and perfectly formed seven inch penis. I was totally turned on and it was no surprise it was currently rock hard. It stood straight out in front of me, with pronounced veins and a big, purple, circumcised head. My scrotum was small and held my balls up and tight. I was now the perfect shemale.
I realize I have totally neglected to describe any sexual experiences to this point beyond masturbation. But make no mistake, I had enough experience to know that my body loved to please and be pleased.
Men and women both loved my soft feminine body and the pleasure I could offer with my mouth and tongue. They also both loved how I could fuck for as long as it took to fully satisfy their desires.
But more than anything, I loved the feeling of a big cock sliding deep into my ass. It was like it had been made expressly for the purpose. And for me, there was no better orgasm, feeling it build deep inside me and rocking my body with waves of pleasure, while my cock released a steady stream of cum for more than a minute.
I suppose that's where I will turn next in my story, to my sexual awakening and how I discovered that the body I had created was adored by men and women, and could offer pleasures both unique and secretly desired. And through that awakening, I discovered my own desires and how boundless they could be.
Elissa
- 22.06.2020
- 24
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- Category:
- Trans
