Me (18M) becoming my best friend’s (20M) crossdressing sissy girlfriend. CH 01 – First Encounter

Jackson and I grew up just down the road from each other. I always called him Jax for short. Even though he was 2 years older than me, he never acted too cool to hang out with me and during our teenage years we spent a lot of time together.

As we got older I began to notice him a little more. Maybe I looked a little too long when he took his shirt off at the pool and caught a look at his butt when we had to change clothes or something. I never thought I was gay, but Jax just seemed stronger and more masculine then me. I never developed the strong chin and jawline he did and I could never grow any facial hair. I was just thinner and smaller than him and never gained any muscle. I was just “softer.”

I remember how it started… I was going through a goth emo phase. I grew my hair out and let it fall over one side of my face. My dad hated it, but my mom encouraged it. I even wore a little eyeliner from time to time. I guess I was just trying to find myself.

One day Jax was driving us to the mall. At a red light, the people in the car next to us stared at us. “What’s their problem” I asked. “They probably just think I’m driving my girlfriend around” Jax laughed. When he said that, I got an odd feeling. I never thought of it like that, but I guess in a way I was kind of a feminine partner to Jax. He drove, I rode. I made us lunch a lot. I just followed him wherever he went. “You think I look like your girlfriend?” I asked. “Well, sort of” Jax replied. “I mean you have long hair and wear eyeliner. You’re smaller and kind of thin. It’s an easy mistake for someone to make.” “Oh” I thought. I didn’t really know what to say after that.

When I got home that night, after everyone went to bed, I went to the bathroom that my sister and I shared. I found her makeup bag and pulled out a few things. Foundation, blush, a dark red lipstick, mascara to compliment my eye liner. ‘Wow” I said softly to myself. “I really do look like a girl.” I had this tingly feeling in my lower stomach. Wearing makeup, feeling so feminine…it felt really good. I wanted to explore this more.

That weekend, my sister had a cheerleader tournament out of town and my parents went with her. They never made me go to those things. They figured Jax would come over and he and I would just hang out. They were right. Jax came over around lunch and we started watching TV together.

I got up and went to the bathroom. I put on the makeup like before and nervously walked back down the hall to the living room where Jax was sitting on the couch.

“Dude..what did you do?” Jax exclaimed. I was embarrassed. I dropped my head a little. “Well, I was thinking about the other day…when you said I kind of looked like a girl. I thought I might see what I looked like if I tried a little more.” “Well, you really do” Jax said. “I didn’t mean to startle or embarrass you, I was just surprised” he added.

I turned to leave, but Jax grabbed my hand and pulled me to sit on the couch. “No, you don’t have to leave” he said. “You can just chill here for a bit.” I sat down. Nervous and excited at the same time. I tried to just remain calm and not do anything weird. “You know, I didn’t just say you looked like a girl” Jax said. “I said you looked like my girlfriend.” “Oh, yeah” I said. I was so nervous, I couldn’t even put a whole sentence together. “Maybe we could pretend you were my girlfriend for a little bit” he said. “Just to see how it feels.” “Umm, yeah, I guess so” again, so nervous I couldn’t speak fully.

A few moments passed and I hadn’t realized Jax was still holding my hand from before. But now his fingers were beginning to play with mine and my heart began beating a little faster. I looked over at him and he reached up to tuck my hair behind my ear. He let his hand drift down the side of my face and rest on my shoulder.

He lifted my hand and let it rest on his lap. It was then that I noticed the buldge in his pants. It wasn’t huge or anything, but I definitely noticed it. It felt firm and I was unsure what to do next. He slid his hand from my shoulder and onto my thigh. I just kind of looked at him and I guess I bit my lower lip a little. He seemed to tug me a little closer to him and then my hand felt his buldge move. It was more noticeable now and there wasn’t really any mistaking what we were both thinking.

He tugged again and I kind of slowly went to my knees on the floor in front of him. He reached down and ran his finger through my hair and tucked it behind my ear again. I was so nervous, I didn’t move. Then he reached up and unbuttoned his pants and started to slide them down. Once they were passed his knees his buldge was pressing against his boxers so tight, I thought they might rip. I hadn’t noticed, but now I could feel my own buldge in my tight pants. Jax slid down his boxers and there was his cock. I was in disbelief at first. But here it was, inches from my face and standing straight up. I couldn’t think of what to say or do so I just slowly reached up and grabbed it.

It was warm and his pubic hair felt course in my soft hand. He started breathing heavily when I grabbed his dick and I looked up at his face. His eyes closed slowly and he laid his head back on the couch. I leaned in further and opened my mouth slightly. I let the head of his cock enter my mouth and just kind of held it there. It began to pulse in my mouth and I felt him thrust a little. I opened my mouth a little further and it slide in a little deeper.

I stroked it a little and as I did, I began to salivate more. This let his thrusts move a little smoother in my mouth and then my tongue pressed on the underside of his dick. “Whoa” I thought silently to myself. “I’m giving Jax a blowjob right now.” It had just dawned on me what we were doing. I was so caught up in the moment, that it hadn’t set in that I was sucking my best friend’s dick. We had gone from just chilling on a Saturday afternoon to me sucking him off in a matter of minutes.

It was such an odd sensation at first. Warm firm flesh in my mouth. I had imagined it would feel hard and cold, like a bone. But it was soft, yet firm. And it was hot almost. Every time he thrust into my throat or I bobbed my head down it brought me close to him and I could smell his crotch. It was unique, not bad, but something I had never experienced.

It was then that his thrusts got quicker and a little deeper. I hadn’t taken him out of my mouth since I started, I was afraid that might upset him. He pulled my head down onto him more and I braced myself against his thighs. He held my head down again and he grunted, just then I felt a blast of hot liquid in the back of my mouth and throat. Jax was cumming in my mouth. I closed my eyes and tried to breathe through my nose. He thrust some more and the cum filled whatever space was left in my mouth.

I felt his grip relax and his thrust receded. I could breathe normally again, but I kept his cock in my mouth. I swallowed his cum and then slowly slid his dick out of my mouth. There were lipstick smears on his shaft and I felt a tear run down my face. I just stayed there for a second and couldn’t move. Jax breathed deeply “oh God, that felt good” he said. I wiped the tear from my cheek and then wiped the saliva that was around my mouth. Jax reached down and pulled up his pants and I sat back on the couch again.

We sat there silently for a bit, only the sound of the TV in the room. I don’t remember what was on, I was just replaying the whole event in my mind. I kept remembering the feel of it, the smell, the pressure of my buldge against my pants. Jax stood up and I looked up at him from the couch. He said he was going to head back to his house, but that he would text me later. He left and I was still just sitting on the couch. Never had I imagined that I would have done that. But I know I liked it. And I wanted to do it again.

I went to my room and took off my own pants. I barely touched my own penis and I came almost instantly. A wave of relief and release washed over me. I felt so relaxed. After I cleaned up, I knew I wanted to have Jax again. I would need to go further than just a little make up though. I wanted Jax to see me as his girlfriend, not just his whimpy little guy friend. I went rummaging through my sister’s stuff. She had so many clothes, she wouldn’t notice a few missing.

I found some of her old underwear in the back of a drawer and some spaghetti strap shirts she didn’t wear anymore. It wasn’t the prettiest or most feminine thing, but it would have to do.

I spent about an hour modeling for myself in the panties in front of the mirror and trying to figure out how to put on a bra. After I got the hang of it I put the top on. If not for the small buldge in the panties and the relatively flat chest under the bra, I might have been considered passable. Still, wearing such girly things made me feel so good. I kept thinking of Jax’s cock. I closed my eyes and could almost feel it in my mouth again. The buldge in my panties began to grow again and the desire for him grew so strong I felt crazy.

I couldn’t wait for him to text me later. I didn’t know what he would say or how I would even respond. All I knew was that I wanted more if this and I hope he did and well.

Source: reddit.com/r/Erotica/comments/u182wi/me_18m_becoming_my_best_friends_20m_crossdressing