How I Became A Crossdressing Sissy

  • 1 year ago
  • 17 min read

When I turned 18 and went away to college, I was a chubby virgin boy with a healthy obsession with panties. Lace and Satin were alway my favorite, but I enjoyed cotton too. The way they felt when I wrapped them around my 5 inch cock and jerked off felt amazing. I never came in them, because I didn't want to face the embarrassment of getting caught washing them.

Once I moved and was on my own, with the exception of my roommate Nee, I spent a lot of the extra funds I had building my panty collection. Not thinking about sizes, just how they felt and looked (I used to tell the cashiers they were for my girlfriend if they gave me some strange looks). Then one day, I found a pair of these string bikini cut panties that were pink with yellow ducks on them (silly i know, but I thought they were ADORABLE), but they only had two sizes and the smallest was a size 8. So I grabbed that pair and went back to the apartment.

They felt incredible, but they were so big it was awkward to jerk off. So I decided to see if they would fit me, and I could just jerk off with the front part of the panties. They fit perfectly! It was the best masturbation experience I had to that day!

So I began buying every pair of panties in my size from that day forward! I had satin panties, string bikini panties, but my favorite had to be thongs! The way they hugged my little balls, and when I'd stroke it with the thong on... You could feel the back side rubbing between your cheeks. It felt so wonderful!

About a month went by and Nee and myself had become pretty good friends, and he was none the wiser of my panty fetish. Until one day I was in my bedroom taking care of myself in this bright blue lace g-string, Nee knocked on my door. Before I could even ask him to give me a second he opened it and said "Hey, I'm getting some..."

His stare is still imprinted in my brain, I'm still not sure what he was thinking. But he closed the door and we never spoke of it again... until after Christmas break.

We were casually chatting about school, and if we had met any girls. Of course, I was too busy masturbating to look for a girlfriend, but he hadn't had much luck either. He said he was feeling a little lonely, and kind of embarrassed because most of his friends had already been through a few girlfriends and had lost their virginity.

I assured him that I was a virgin too, and it wasn't a big deal. It will happen when it should... Then I told him: "Until then, practice your moves"

He asked me what I meant, and I said: When I was a young teenage I had a body pillow that I would fold in half and fuck. The conversation got a bit uncomfortable as he said he thought that was weird and he didn't want to do that. We sat in silence for a bit... I felt really bad for him, and I wanted to help.

I came up with an idea: "Man this is going to sound weird, but what if you practiced on me?"

He got up from the couch: "What the fuck?! I'm not gay, bro.."

I reassured him: "No, you don't have to fuck me! I'll just lay here on my stomach and you can dry hump my ass until you cum."

"Nah... Fuck that" he said as he walked to the kitchen. "That's gay, bro"

"I know it SOUNDS gay, but I know you also don't want to be embarrassed if you don't perform well with the girl." I said. "You've already caught me wearing panties, so you know I have some.... I'll just put a pair on, we can put a blanket over my head and you can imagine it's some chick."

"I'm good man... I'm just gonna get some sleep." He said.

We left the conversation at that. Things had become slightly awkward between us. He didn't look me in the eye, and we didn't speak much. Valentine's Day came around, and by this point, I had began wearing panties quite often around the house. I wasn't comfortable wearing them in public, but at home I could be myself. And I was now a guy who loved wearing panties. Nee, either didn't know or ignored it. He was supposed to go on a date with some girl named Julie... or Jackie... I can't remember. When all of a sudden...

"Fuck!" Nee said from the kitchen.

"What's going on?" I asked

"Nothing." He said, clearly not wanting to have a conversation with me.

"Ok... Sorry I asked"

"I got stood up. She said her dad didn't want her dating a black guy.. Fucking racist people." He was upset, and rightfully so. "This was going to be my night, and now i've got nothing.."

"I'm sorry man... I was gonna order pizza, and I know a guy who will hook us up with some beers if you want?" I asked.

"Yeah, fine... Whatever.. Fuck it, I've obviously got nothing else to do." He said.

As the night went on, we ate and split of a twelve pack of some cheap light beer. We were pretty drunk, because we didn't drink very often. I stood up to go to the restroom when Nee said his first words in about an hour:

"Your panties are showing" He said..

"Oh shit, I'm sorry man." I pulled my basketball shorts up to hide them. I went and peed, and as I came back he pantsed me (Which to be fair is pretty easy to do in basketball shorts). I stumbled, and he laughed. I bent over to pull my shorts up and he said:

"Not a bad ass... too bad you're a guy"

"So you were looking, huh?" I asked with a smirk.

"I glanced." He said "That satin is pretty shiny, kind of hard not too."

"Do you want to feel them?" I asked

"I'm not grabbing your dick, bro." He said.

"No!" I said laughing... "Touch my ass, you said it didn't look bad, so just touch it!"

He sat his beer on the table, and started rubbing and grabbing my ass cheeks.

"How does it feel?" I asked.

"Maybe it's just the panties, but you've got a pretty soft ass." He said.

I turned my head and looked at his crotch, and could already see the bulge in his pants. So I turned back around, and bent over until my fingers touched the floor.

"Now... how does it look?" I asked.

"Fuck. It looks nice" He said.

My heart was pounding through my chest. I had never been in su

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Written by sarahthesissy
Uploaded November 25, 2020
Notes The story of a chubby white boy finding his sissy self at college, with his black roommate.

"He was holding on to my panties for leverage as they were shoved up between my ass cheeks. Every few thrusts he'd slap my ass, and I was sure it was beet red... But I loved it. After about ten minutes of feeling his big black cock rubbing up against me he said:

"Fuck, I'm gonna cum""
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