Journey Of A Repressed Young Shemale To A Vibrant Confident Transgender

Most shemales have similar beginnings with early feelings of being different and confused and uncomfortable in our skin.  Being male at birth , I always felt at ease with other boys but different from being a buddy and more like a boyfriend .  Growing up in a very rural , very conservative area was a further impediment to being able to express my true feelings.  Farming and timber were the primary sources of employment in my area and my nearest neighbors were African Americans so they were my playmates and confidantes. We played together and when we were old enough , we worked the fields together.  We developed very close relationships , they being typically masculine and me being somewhat of an effeminate sissy.  At first they chided me with  remarks about me being girly, but later as we matured our relationships took on a more protective nature. I would fiercely intervene on their behalf when racial slurs were aimed at them and they stood up for me when outsiders would attempt to demean me for my feminine proclivity.  It was normal for us to do all manner of things together as we worked our chores including attending to the call of nature. Hidden in the cornfields , we were free to do as we pleased as long as the work was done. Naturally, I was very curious about their bodies including their genital area which dwarfed mine . There came a day when I was alone with one of my companions when , he noticed me staring at his cock as he relieved himself . When he asked why , I explained that it was so big . He asked if I would like to feel it to which I readily replied in the affirmative. As I grasped it in my small hand, it began to grow until it was long, thick and hard . He then clasped his much larger hand around mine and told me to stroke it. I complied with his request and felt myself getting excited and aroused as I felt his cock pulsate and quiver as I continued to stroke it. To my surprise , after a few moments, he stiffened , and held my hand even tighter inside his and pulled me to him as a thick white emission erupted from inside our clasped hands . I was beside myself with a thrill which I could not explain but instinctively knew that I like what we had done and that it was normal for me to feel this way.   He cautioned me not to tell anyone what we had done and I promised him that I wouldn't divulge it to anyone , but I asked him to promise we could do it again soon.  This became a regular thing between us and as we became more intimate with our feelings, and our activity took on more advanced touching , feeling  and verbal expressions mostly by me , of course, but he allowed me to continue and even encouraged me to take things to the next level . It began with him inviting me to kiss his cock which graduated to me sucking it while I stroked him . At first I allowed his sperm to shoot onto the ground , but eventually, after I tasted it , I began to enjoy it and even to the point where I would not allow even a drop to escape my lips . Despite all of our enhanced sexual activity , I felt like I was missing something and often felt somewhat frustrated afterward . Little did I know that was all going to change when one day he suggested we try something different. When he explained that since I enjoyed being girly, I should let him treat me like a girl and insert his cock into my male pussy. The thought of it was at the same time exhilarating but terrifying as he had a tremendous cock and I was quite small . My excitement soon overtook my fear and he promised to be gentle and take it slow .  The pain was so severe, the first attempt was futile but after he lubricated me , we tried again . It was still painful  but I was determined to be what he wanted me to be . Although , we were both clumsy in our actions , he achieved an orgasm which made me very happy and convinced me to continue until I could totally accommodate his size and learn to enjoy it myself.   From those humble first beginnings , I learned to be not only an efficient cocksucker but a shemale who loved and relished being ravaged by my big strong boyfriend  . Of course, all things must come to an end and our relationship did when he started dating a real girl . I was distraught for quite a while and had no other close friend to whom I could reveal myself , but a gurl does what a gurl has to do and even though I continued to be repressed and frustrated, I was confident that things would get better and WOW, did they and in a big way.  So this is the first installment in my blog series with more to come in my metamorphosis from a youthful shemale to a fully confident  and brave transgender.  

• Add Comment
• View Blog