Told Him What I’ve Never Told Anyone

My friend Jeremy finally found my secret dress-up obsession

The night before, my friend Jeremy and myself was wandering around the city, just chatting and talking. we ended up getting an iced coffee, he only had enough for one. we shared the the drink. Only after I had drank out of the cup did he mention that he was feeling sick.

I told him I didn’t really care that he was sick and proceeded to continue drinking anyway. we walked around some more before we walked him home to his place and said our goodbye’s for the night.

On my way home, I realized that I had lost my phone and that I wouldn’t be finding it again. The next day, during the school day, I had to access a laptop to check my messages. I messaged everybody that I regularly chatted with and told them what happened and that I wouldn’t be able to meet up any time soon.

During all of that, I had started to feel the sickness growing within me, my nose became runny and I started feeling colder. After a while of it getting worse, I decided to skip the rest of the day and hang out with Jeremy since he had already had the sickness.

I had gotten home and started up a bath to keep myself hot and clean. I stayed in the bath until Jeremy came into the house and asked if I was already to go. I quickly dried myself and put on the clothes i brought with me. just socks, track pants, and a sweater.

we started waking toward his place on the other side of town and we decided to take the train tracks to get there. we had been walking and talking for about 2 hours as the sun began to set and it was getting darker and colder.

Jeremy didn’t understand why I was getting so cold, so I had to explain to him that I had gotten his cold and that I also shave my body. he asked if I had any extra cloths in my backpack, I said yes but was trying to deflect the question since the cloths that I had were women’s cloths.

He kept pushing and pointing out spots on the tracks where I could change. I told him that I was fine for now and that the tracks isn’t a very good place to change. he said that we could go to a school where I could find someplace dark along the back to change and where he could connect to the internet.

We got to the school and jumped a fence and found a place were it was dark enough and away from anyone else. it was lit up by the moon light so it was easier to find the cloths in my backpack. Jeremy sat around the corner of the wall I was changing from and I took the cloths out of the bag and began to take my own cloths off. when I was naked and putting on a pair of black lace panties, he turned the corner and sat down in front of me,

He asked why I was changing into those and I told him that wearing women’s cloths under my own would keep me warm and comfortable, also the fact that I didn’t have any underwear on before I left the house.

As I continued changing, he kept snickering at me for wearing women’s cloths and how that if any other guy could see me, they would get instantly hard. He watched as I slipped on my leggings and shirt. He noticed actually how thin my legs were and that I was looking very feminine. I slipped on my jean short shorts over the leggings and buttoned it all up

I quickly redressed the cloths I had been wearing over top of everything when he asked me to show him the cloths I had brought since he would have never guessed I would like wearing women’s cloths. I took the cloths back off and showed him what I looked like, he asked me to take down my hair, so I did.

He told me that I looked hot as a girl as I put the clothes back on, and we continued our walk. everything went back to normal, until we decided to wander into an almost pitch black park in a small forest area. he grabbed my hand and we began walking. since I didn’t my glasses, I couldn’t see in front of me. he tried turning on his phone light, but his phone died.

We continued walking further into the park and at this point, there was no light to be seen. As we continued walking, he began slowly rubbing his hand against my ass. I enjoyed it and wrapped my arms around his.

he put his hand down into my track pants started pulling down my shorts. I asked if he wanted to sit down, he agreed. we walked us towards a tree and he sat down. As he was sitting, I quickly pulled off the pants and sweater. I sat beside him and he was pulling on my shorts. I lifted my myself to allow him to pull them off, which he pulled off the leggings at the same time.

I was now down to my shirt and panties. He pulled off his own pants and pulled me towards his dick. i grabbed it and started sucking on the tip. he was messaging my dick through my panties and I took his whole dick into my mouth. We did this for a few minutes when he lifted my up and placed me on his lap. I moved my panties to the side as he began poking my ass with his dick. he shoved me down quickly and began bouncing me. I was trying my best to just hold myself up and he continued his thing.

After about 5 minutes, he came inside me and we just sat there. It felt like an hour before he pulled out and we got dressed. we continued walking together and chatting as if nothing had changed.

we walked him home and I walked back to my own home. of course I stayed in my women’s cloths all the way home.

its been about 3 days since this has happened and I have yet to experience it again.

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