How I Became A Crossdressing Sissy
- 9 months ago
- 17 min read
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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 ch a vulnerable position before. I stood up and walked to my bedroom, and he followed me.
"I'm not going to fuck you, bro. I'm straight." Nee said.
"I know, and I don't want you to. But your cock is hard as a rock, so I'm just offering you a little release. I can keep these panties on, and you can rub your dick on my ass until you cum... If you want?"
I felt like I was begging for it at this point... I never thought about if I was into guys. I've just always thought about women, I just never thought I'd be able to get with one so I never tried. This, however, was fun for me! I felt vulnerable and in control at the same time. It was such a weird and ecstatic feeling that I already had pre-cum in panties.
"Can we put the comforter over your head?" He asked.
"Absolutely!" I exclaimed.
I climbed up on the edge of the bed, threw the blanked over my head, and got into position. I tried to spread my knees as far apart as I could, but I wasn't very flexible. Luckily my mattress and boxspring sat on the floor and Nee was about six foot two, so it was ok.
I heard his belt buckle shift, then a zipper... I could hear him stroking his cock almost trying to work up the nerve.
"It's ok, Nee..." I reassured him.
He placed his huge dick right in the center of my ass cheeks, and he grabbed my ass with his hand as he began to move back and forth slowly. I couldn't believe this was happening. I had never used a dildo, and I never thought I would feel another mans dick on my ass. But it felt so fucking good.
"Do you like that?" I asked
"Yeah, Feels good" he said, as he kept humping my ass. The smoothness of the satin panties felt like a delight as his dick moved up and down. I noticed he began to move faster. As he moved faster, he spanked my left cheek. I winced.
"Oh!" I said. I wasn't expecting a swat, but it honestly felt fitting.
"You like that, bitch?" He said as he was humping my ass at a much faster pace. "You like my fat black cock on your ass cheeks?"
"Fuck yeah I do" I didn't know what to say, and that was all that came to mind... I never thought I'd be in the position to be the girl, so I never planned a dialogue for dirty talk.
"I bet you wish I'd fuck that ass, don't you bitch?!" he asked as he was humping harder, and faster.
(Wait.. what? Where is this going? Is he going to fuck me? Am I ready for that? Do I even want that) I asked myself, but needed to respond so I just said in a much higher voice than before...
"Fuck yes! I want you to fuck me!"
"No, Anal is only for good bitches." He smacked my ass. "And you're a bad bitch" He smacked my ass again.
He grabbed me by my hips and kept thrusting away for the next few minutes. He then stopped, grabbed the back of my panties and gave me the biggest wedgie I had ever received. My testicles were in pain, but I couldn't tell him. He put his dick in the middle of my ass cheeks, and now I can feel his flesh touching my ass. Now he wasn't just rubbing up against my panties, he was rubbing up against my ass cheeks too.
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"
He backed up, and I pulled my panties out from my ass and I said the first thing I could think of:
"Cum for me, Nee. Cum on my pantied ass"
Seconds later, he let out a grunt and I felt it. It was warm, thick, and all over the back of my ass. At this point the panties felt like they were being glued to my ass, as the cum soaked through the fibers. I stayed in position, and he put his dick back on my ass and started rubbing again.
I could feel his cock getting softer, going back to a flaccid state. He backed up, and I could hear him putting his clothes back on. He said:
"Thanks man. I needed that."
"No way, bro. Thank you!" I'm not sure why I said that, he got way more pleasure than I did. But for some strange reason, I loved it.
We both went to sleep in our respective beds, but the next morning there was something different about Nee. He was back to his old self. We were laughing, and cutting up with each other. We started watching tv, and playing video games together again. I had my friend back!
The weekend rolled around, and I asked Nee what he had planned.
"Nothing" He said. "You?"
"Nothing at all" I said. We sat in silence for a moment, but I was missing his dick rubbing up against me. I was wearing a pink thong with a black lace trim, and I decided to go for it.
I stood up, turned around, and faced the couch. I pulled my shorts down to my ankles and exposed my thong to him.
He smiled and said: "Another round?" I simply smiled and nodded.
This time we didn't need a blanket, and with me only wearing a thong I could really feel him up against my ass! My chest and face were up against the wall, as my knees were in the couch cushions. He wasn't even inside of me and we were pounding so loud I thought the neighbors would hear.
The next thing I know, he's grabbing the back of my thong. I initially thought it was for leverage again, but instead he wrapped it around his cock. This was as close to getting fucked by a man as I had ever been. I was sure he was going to stick it in me, as I felt his throbbing cock between my ass cheeks.
(This is it) I thought to myself. (I'm going to lose my virginity to a guy)
But he didn't fuck me. Instead he came so hard it got all over my back, and missed most of my ass. He sat down, and asked me:
"Do you mind showering real quick, so we don't get cum on the couch?"
"Oh yeah, of course." I said. He smacked my ass as I walked away.
"Good game" he said. I laughed.
The next week went by and it was starting to become a nightly ritual for us. By the end of the week, I stopped wearing shorts. I was walking around in panties and a t-shirt. As Friday night came around, I wanted to do something fun... So I went to the lingerie store and picked up some stockings and a wig... Then went to the women's department store in the next town (So I wouldn't be seen by someone I know) and picked up a dress that fit and some cute heels. A fun little black dress, and some red heels. I had never worn heels, and it was challenging.
I came back to the apartment, and Nee was sitting on the couch. He saw my bags, and smiled. He said:
"It's a surprise!" I said.
I went into my bathroom, and I shaved everything completely off. Until today, I never thought I needed to. But today felt special. After I shaved, I showered, and walked into the bedroom to change. I put my stockings on, then a cute little red thong, then the dress, the wig, and finally the heels. I looked at myself in my floor mirror, and tried to walk. These things were so difficult but if I walk slow enough I can manage.
After about 10 minutes I built up the nerve to go see what he thought.
I opened the door, he saw me. He Smiled, then laughed endearingly.
"What are you doing?" He said.
"I just thought, i'd look more like the part. If we're pretending I'm a girl, I should look more girly." I explained.
"Well, you definitely look like a sissy girl to me."
I smiled and walked over to him. Grabbed the bottom of my dress and asked:
"What do you think?"
"Looks good" he said.
The next part has me confused to this day. In the biggest impulse moment of my life, I dropped to my knees in front of him. I spread his legs and started to unbuckle his shorts.
"Whoa. What's this?" He said.
"Just relax, daddy. I'll be your girl today." I said as I unzipped his pants, and pulled out his dick. His cock, even flaccid, is twice the size of mine hard. I was so shocked seeing it up close, as I had never really looked at it before today.
I started to jerk slowly, and I couldn't believe I was about to do what I was preparing to do. As his cock was getting slightly harder, I looked him in the eyes and said:
"I want to taste it"
"Go ahead then." He said.
I put his cock in my mouth and I could feel it getting harder and bigger in between my lips. It's a feeling I'll never forget. He was full on now, and I was sucking like I actually knew what I was doing. I tried to go deep, but my gag reflex wouldn't allow it. I was maybe only two inches down the shaft. That was as far as I could go, so I backed my head up and started licking down the sides. Up and down, each and every side until every inch of his cock was soaked with my saliva.
"Do you like that?" I asked.
"Fuck yeah" He said softly, just taking it in.
I put his cock back in my mouth, and was jerking his shaft with my right hand.
"Oh, fuck that feels good babe"
Babe? He's never called me babe! I liked it.
He grabbed my head, and used it like a fleshlight. Up and down, Up and down. I was gagging, but trying not to cough from it.
Finally he pulled my head back, and said:
"Get that ass on the couch."
"Yes, daddy." I said.
He lifted my dress up, and started humping my ass. But his wet cock and my panties were making things difficult. So I pulled them off, and he said:
This was the first time I gave him a bare ass job. He had his dick completely between my ass cheeks, but he wasn't penetrating me.
"I'm gonna cum" He said.
I stopped him, turned around and dropped to my knees. I wanted to taste it! I put his dick in my mouth as he let out a grunt, and I felt it hit the back of my throat. I felt like it was a shot glass worth of cum.
"Let me see." He said, but I had already swallowed it. I showed him my tongue and he laughed.
"Now we don't have to clean up." I said and we both chuckled.
We sat on the couch. Nee in his boxers, and me in my dress with my panties on the ground. He looked me in the eyes and smiled, I smiled back.
"You know... I'm not gay." He said. "I mean it's totally ok if you are, and I'll be honest, that blowjob felt great. But I can't fuck you. I'm into women. I appreciate everything you've done for me, but eventually I'll get a girlfriend, and I don't want you to be upset by that."
"Oh no, That's totally cool. I promise, I was just helping out a friend. I'm not gay, either. It's just what good friends do." I said, trying to save some dignity. I wasn't sure if I was gay. I had never thought about it. But I was at least bisexual, considering these last few months. "But I'm still here for you, if you need some... you know. Release." I said.
He laughed. "I appreciate that."
For the rest of the semester it was the same. I wore cute outfits, sucked his cock, and he came all over me. Almost daily. I had the fuck buddy I never thought I'd have. I was his naughty little girl, until I wasn't. At the end of the semester, I came home to a note that simply said:
Going back home to go to work with my dad. Catch You Later, bro.
Catch you later, bro? What the fuck was that? I figured the ending would be a bit more meaningful than that. But I said to hell with it. I was staying in the apartment for the summer, and needed money to cover his half of the rent... I clearly do better as a girl, than I do as a guy. Now the ad on Craigslist reads:
Sissy ready to please. Blowjobs and assjobs $50, willing to do more for the right price.
We all have to pay the bills. :)