A Short Sissy Story My First Time

Hi, my name is Jim and I'm 19 and at this very moment, I'm holding a beautiful, six-inch cock in my hands. It belongs to my best friend Bernie. He's a year older than I am. And this is a short story about the transformation of our relationship.

We've been best friends forever and I've always looked up to him. He's taller, older, stronger and way smarter than I am. He's kinda has always ordered me around. Like, "Hey Jim, get me a coke, or put a DVD in the player, fill the bong." And now, "Suck my dick." I don't really mind him bossing me around. In fact I kinda like it. Makes me fell all tingly inside.

His parents are Antiquers', so they are usually gone on weekends. So, Bernie and I have the house pretty much to ourselves. Well, a few months ago we were watching porn and getting high. This girl was giving a guy a blow job and Bernie said, "Man, I bet that feels good." Maybe because I was stoned, maybe because I always am looking for ways to please him, probably both, I blurted out, "Want me to do that to you?"

He laughed and said, "I didn't know you were a faggot and I'm definitely am not, so NO, I don't want you to do that to me."

I was embarrassed and added, "But if we pretend, I'm a girl and keep my hair down over my face, it would be okay, wouldn't it?"

I have long hair and so I put it done over my face and said, "See, I mean we'd only be pretending right and you want to know what it feels like. I won't tell anyone, I promise. You can watch the video and pretend I'm the girl. That would be okay, wouldn't it?"

He looked at me and there was a long pause. Then he looked at the TV screen watching the girl still sucking the guy's cock and, maybe he was high too, or curious or really wanted to know what it felt like to have his cock sucked, he said, "Okay, I guess it would be okay, but you can't tell anyone."

"I won't."

We both took another hit from the bong and he stood up. He unbuckled his belt, pulled down his jeans and his underwear. His cock sprang out already hard from watching the video. He slid off his jeans and underwear. He kept his shirt and socks on. I had never seen his cock before. It was thicker than mine and longer. He was circumcised and the head of his cock was swollen. He sat back on the sofa and spread his legs apart. I slid off the sofa and between his legs. I looked up at him and brushed my hair in front of my face. He glanced down at me and then at the TV saying, "Ok, I'm going to watch the movie and pretend you're the girl."

My breathing became heavy as I looked at his engorged cock. I reached up and slid my fingers around it. He gasped and whispered, "Oh God." His dick felt warm, soft and hard all at the same time. I tightened my grip slightly. My heart was pounding in my chest. I moved my head closer and licked the underside of his shaft working my way up to the tip, tasting his salty, pure pre-cum. I inhaled his musky scent. I couldn't believe I was really doing this! I had never really thought about it before, but there I was, holding, and licking my best friend's cock.

I imitated what I saw the girl doing in the video. I licked around his circumcised helmet and then sucked it past my lips, into my mouth, running my tongue up and down his pee-hole.

Bernie moaned outload, "OH GOD JIMMY!"

He hadn't called me Jimmy in such a long time. It made me feel like a girl. His girl.

I wrapped the fingers of both hands around his cock. I wanted it. I needed it. I loved the way it felt in my mouth.

Again, he moaned, "OH GOD, JIMMY! OH MY GOD!"

His moaning made me want to please him more. I sucked more of his cock into my mouth. I kept massaging it with my fingers.

"YES JIMMY, JUST LIKE THAT! DON'T STOP! OH, FUCKING CHRIST! THAT FEELS INCREDIBLE!"

His cock stiffened and grew even more in my hands. The head of his cock expanded in my mouth.

"OH GOD, OH DEAR GOD! I'M GOING TO CUM! JESUS, JIMMY, YOU'RE GOING TO MAKE ME CUM!"

He lifted the hair from my face and watched as his cock spasmed in my mouth, filling it with his warm, smooth textured cum. I gulped it down feeling his cock pulsating in my fingers as he pumped his cum into my mouth.

I lifted my head off his dick as I swallowed his last spurt.

I thought, "Oh God, what have I done? Am I a faggot?" I felt ashamed, humiliated. Did Bernie hate me now? Did he despise me? Did he think of me now as a pathetic little sissy cock sucking boy. The kind we had joked about before.

I still held his softening cock in my fingers when he said, "Man, I've never cum so hard in my life! Can you do it some more?"

I looked up at him. He was staring down at me. He rubbed the side of my head with one hand. Yes, he didn't hate me! He didn't loath me! He hadn't lost respect for me. He liked what I had done and he wanted MORE! I licked the head of his cock.

I clamped my lips back onto the soft head of his now semi-hard cock and sucked the remaining cum out of the shaft. He let out a loud sigh, moved the hair from my face and this time he watched me.

So, that is how it all got started. Of course, now, I wear make-up, a dash of perfume. my hair in ponytails, I shave off all my body hair and I wear girly clothes for him. I do it all just to please him. It's our little secret.

He hasn't sucked and probably never will suck my dick. But that's okay.

We've been watching a lot of anal sex porn lately and I've notice he's been checking out my ass. I think he's going to be taking my anal virginity soon. Which will really make me his 'gurl'.

Well, he just asked me to suck his cock and I never refuse him. I hope you enjoyed my little tale as much as I liked telling you about it. Remember, it's our secret, okay?