You can say everything started at a young age when I started having this new but strange desire to look through my sister’s clothes and underwear drawer. A little while after when everyone was out of the house and I made sure nobody was coming back I tried them on. It was at sixteen when I put on my first pair of panties and it changed my world forever. I still remember that magical feeling when the skirt fit me just right and curved my body into this beautiful feminine form.
As a growing teenager, I had a lot of insecurities about my body mostly because of my wider hips and larger girl like ass, while my waist and legs were pretty slim, I kept getting bullied for my big butt and hated it. But there was one moment when I absolutely loved it, when I was crossdressing. As a teenager searching for CD pictures on the internet I stumbled across a large selection of very manly looking CD’s with girl outfits, but when I put on those panties, bras, skirts, dresses or anything I could out my hands on (Apologies to my sister and cousins for all those items that “disappeared”). I looked like a real girl, to a point where even men couldn’t tell the difference… but we’ll get to that later.
Under my bed, I had my secret bag with all the items I “borrowed” from family members, I would even have a nighttime outfit to sleep with and change really quickly early in the morning while everyone’s still sleeping.
Just when I thought that crossdressing was enough, another demon revealed itself to me in the form of an extra friendly classmate. It was in history class, our last period of the day. I was sitting next to a friend that we’ll call John, this person was not one of my good friends but we were definitely on friendly terms. And then it happened, at one point during the class John leaned closer to whisper something in my ear while the old teacher’s back was turned. However, as he was leaning and whispering whatever it was to my ear (still to this day have no idea what he said) his hand shifted and was now placed right on my pants exactly where you think.
I immediately felt a rush of blood through my whole body, my heart started beating hard and my little friend got harder and harder. When friendly John finished his whispering he shifted back to his seat without removing his hand from under the table, a little while after that class was over and I remained there until all my organs went back to their normal state, John quickly left and went home without saying a word, my mind was rushing.
Later that night he sent a text saying he’s bored and if I’d like to come hang out, John’s parents home was about a ten-minute walk from me. We nave really hung prior to that day but it’s safe to say that those ten minutes of a walk took me about five. John had this cool basement that you could go to without passing through the main entrance to the house. It was every child’s dream, a room with a large TV, a bunch of gaming consoles, a couch and a large bed.
When I got there John turned on the TV and we watched MTV for a while. And once again, at one point his hand found its way onto my pants. I loved it, I wanted that hand to stay there forever so I can have this sensation all the time. But I just kept sneaking looks towards the same part of his body which through the basketball shorts was very clearly erect. I took a deep breath and sent the command from my brain to my hand to go on this adventure. I went straight for it and grabbed his big shaft in my palm, it felt so good, it felt better than him touching mine.
My hand started moving as I was feeling his cock, no words were said and after a few minutes of rubbing he simply stood up in front of me, taking off his pants and underwear. It was the first time in my life where I saw a real cock that wasn’t mine, it’s hard to even begin to describe that rush of adrenaline I had at that moment, I just sat there and stared at it right in my face, until he said, “Put it in your mouth.”
All those videos I saw in secret of porn stars sucking flashed through my eyes, I was nervous but something felt right. I really wanted it and although time seemed to have stopped I made the decision in about twenty seconds.
I tilted my head forward slowly opening my mouth. Mind you, I had no idea what I was doing. I kept trying to remember how they did in porn. Luckily, my friend made my first time very easy. He placed his hands on my head and in one swoosh he just inserted his cock straight to my throat, the gag reflex was not late to come and it’s safe to say that John was also watching enough porn without any real life experience. In spite of my resisting throat, I didn’t give up. Slowly, I tilted my head back so his cock would remain in the area of my mouth.
From there on it was smoother sailing. John closed his eyes and started rocking back and forth, humping my face like only a sixteen-year-old knows how. But then it occurred to me! He’s about to cum and my head went back to those porn videos where the girl gets her mouth filled with it. I was kind of nervous but excited and before I could even think he burst in my mouth with the intensity of a grown man. Based on my current experience I can definitely say he was saving that load for at least two days.
I wanted to do this right so I fought the urge to spit it all out due to this new and kind salty and unfamiliar taste that was taking over my mouth but I told myself that I should be like those girls so I released my throat and swallowed the whole thing. Just like in class John quickly vanished saying he’s tired and maybe I should leave.
On the walk home, my body was still in a rush. So many thoughts were flying through my head but the two were most important ones were that I wish I could be all dressed up though this experience and that I want it again and as soon as possible.
Back home, I couldn’t stop thinking about everything as I was wearing a cute shirt and a crop top, touching myself. I began to think if John and I will ever do this again and if we do how do I bring up to topic of me being dressed like a girl. He would for sure make fun of me and I had to quickly think of an alternative. Waking up the next morning I was still wearing my thong and skirt when I got up and looked at my school clothes on the chair, and then it came to me, I can simply wear my regular boy clothes over my girl clothes!
It was a bit scary I must admit, but I wanted it so bad so I decided to just wear the thong underneath my pants. John wasn’t at school that day but I was in the sky, I felt so go and so feminine walking around with this secret under my pants.
More on John and my first encounter with an older daddy in part 2. See you next time!