My Path (The Beginning) - Sissy Story - Pt.1

Good finally I decided to document the side of my life that no one close to me knows about.
I will write about my path from very early age, key events and happenings during my life, which made me decide to have relationships with another man and later recount my few experiences. Note that previously I had certain interest in feminine clothing and feminine attitudes, but it wasn't until I had my first experiences with another man that I decided to share about my life and tastes.


Everything started in a summer with the arrival of a new neighbor, I was very young, approximately 10 years old and my neighbor is 2 or 3 years older than me (currently I'm 26), as the days went by after his arrival we became very good friends, we were the only young ones on the block, we used to play on the sidewalk until it got dark, life in the village was very quiet and boring at the same time without the existence of internet.
One day, I don't exactly remember how or why the conversation started on the sidewalk in front of my house, I began to explain and tell things that at the moment I didn't understand, things about adults, I'm talking about human reproduction, sex, I innocent and curious listened attentively until his stepmother came out and told him to go home, he said goodbye and left.
From that day on, our afternoon conversations changed becoming more intimate, their end was to make me understand and show me things I didn't understand, we were very young and didn't have much knowledge, so it was a discovery path for both of us.
That summer was very special, we discovered things we didn't know, things that aren't taught in school, things that aren't spoken at home, let's take into account our age and the lack of internet back then, there wasn't much information available to us.
As the days went by, our conversations and games became more intimate, both of us used to go to the bottom of a nearby terrain near my house, where we would play and converse away from the eyes and ears of our parents. We had an implicit rule that both of us respected without knowing very well why, no one should tell anything about what we did or talked about to our parents, it was our secret.
I have very few memories of what was happening there, like flashes of things that passed, but I don't remember details. Our most common game was truth or dare, but both knew it would be about the dare or question, it was an excuse to do things we couldn't do elsewhere. I remember dares like showing each other our penises, by the way I remember the first time I saw his penis, it was bigger than mine, I remember being very impressed, indirectly it excited and attracted me, but I didn't know why (btw: at this moment I remember having a very nice and big penis for my age).
Some of the challenges I remember, because yes, most were just due to excitement, it was about supporting each other by imitating a sexual position, which sometimes escalated into one of us having to take off our pants, usually the one in the feminine position. Another common challenge was to masturbate the other a certain exact number of times and we had many more but I don't remember details.
One afternoon, which left a very marked impression on my memory, was one of our last or the last strong experience, so to speak. We were alone in the patio of my house, my father was sleeping so we were both 'safe' for a while, my pool, a pelopincho which my father had put to drain that same afternoon, was practically empty of water when we found ourselves 'playing' in it, as usual we started playing something else but ended up in a real challenge without knowing what level would escalate that day. I don't remember very well how it happened but at some point the game transformed into something more spicy. Both of us were semi-naked in the pelopincho and the game was about who could get in...
I remember sitting on the pool floor with my boxer shorts down, completely turned on, with my penis very hard, and my friend sitting above mine, jumping while I was trying to 'get it in', the game consisted of whoever got it in won... I don't remember if anyone got it in, but after that it was my turn to sit on top of him. It was a different and very exciting experience for me, my friend was sitting with his penis held very hard straight, when he's ready he gives me the okay and I try to sit down aiming to get him 'in' but it didn't happen, instead, every time I feel like his penis is pressing on my anus and then slides between my buttocks until I'm sitting on top of him. It was a very strange sensation, I didn't know what I was feeling, but I really liked it, I remember moving on top of him and that excited us both a lot, but that didn't end there.
After some attempts, we decided to leave the pool, I would take off my clothes after leaving and hang them up to dry, which I did later outside the pool and ended up completely naked in my backyard. My friend and I decided to move to a shadow that happened to fall on a half-blind corner of the patio where you couldn't see through the windows of the house and we continued playing. If I'm not mistaken, we went back to playing truth or dare, and what I remember is seeing my friend kneeling in front of me put my penis in his mouth some times. After that, I remember trying to replicate sexual positions but this time it was different from the others since I was naked and my friend almost was too. Then I remember standing in that corner, my friend grabbing my waist and lifting me up, obviously with intentions to penetrate me, I remember feeling his strong hands holding me up in the air and when he let me down I felt his super hard penis pressing against my anus and then it was between my buttocks (Now that I'm writing this I realize that's where one of my fetishes was born), at that time it really excited me.
So it happened unexpectedly at that moment, we were in that corner, I was elevated by my friend to the point of feeling that again which excited me so much and it was when we heard the patio door open, it was my old man, quickly what came out of my mouth is that we were trying to roll down a ball, hardly believable my argument since I was completely naked with my erect penis and my friend's even harder, it was a moment from which I still blush so I won't give more details but let's say I managed to wriggle out of it quite well and ended up with nothing.
That summer afternoon I had one of the strongest experiences, didn't know what I was feeling but it really liked me, it was something that marked me and made me discover something I didn't know existed, which until this day leaves me with the desire and fantasies to try something similar again with my friend using the experience we both have so far. Currently, he is still my neighbor but never again spoke of that afternoon, and yet that secret remains between us. I am still looking for a way to try something with him again, but I don't know how, I don't know if he feels the same as me, I don't know if he remembers the same as me, I don't know if he would want it, since both of us are 'heterosexuals', but I can't get the idea out of my head to try something again with him, to feel what I felt that afternoon. After this we had some more experiences but none as strong as that.
As I grew older, my interest in feeling feminine was gradually fading but never disappeared, it was rare for me to stay alone at home but I would use the opportunity to dress up in lingerie and my mother's clothes, wear her shoes, enjoy walking around my house like that dressed, trying to replicate feminine attitudes and obviously attempting to fulfill the female role in a sexual relationship but nothing more than that, I didn't feel attracted to men, I didn't like the idea of having relationships with another man.
This was something I used to enjoy doing during the course of high school, since I went to a technical school with a double shift far from my home, which made me lack time and disperse my mind from what I enjoyed doing, but it didn't disappear, it just calmed down. During this period, I had some experiences with girls, only one girlfriend (I'm irresponsible in relationships), I discovered one of the biggest and most expensive vices that are video games, but as for sex always was very straight.
When I finished high school, it wasn't until a year later that this impulse to feel feminine reappeared, but this time with more force, I think in part due to massive pornography consumption, which made me seek new experiences, start consuming transsexual pornography, used to watch them come to the point of ejaculation and compare them to myself (genetically speaking), indirectly started looking at the male member with more affection, something I didn't do before, it excited me to see those hard and veiny cocks and giant hanging balls. This was the beginning of something that eventually got out of hand.
I would take advantage of every moment of solitude and tranquility at home to become as feminine as possible, and act accordingly, usually I'd watch transgender pornography and try to replicate the movements, it really turned me on a lot, but it wasn't enough, I wanted more, I wanted to feel more feminine, I wanted to feel like a woman and please a man. That's how I discovered this niche branch of pornography that are 'hypnotic' videos and started learning more about it without knowing where it would end up, Hours and hours of watching videos that I still consume to this day, as a consequence of this was when I finally decided to look for a man with whom to have relations for the first time.


Up until now my first account, in the next one I will write how it was my first experience with another man, from how I contacted him to the details of that moment so awaited.

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