Sissy Mi Meets Mr. Master

This is the first in a series about a man with a serious fetish for crossdressing, cock-pleasing and cum, finally committing to a worthy master. This story is 100% imaginary, it is over the top, it is intentionally unrealistic, etc. I have no actual experience in this field, it's just fun to fantasize and write about. Not intended to impress anyone on a literary level, just hoping to make people want to feel themselves up a bit ;)

This is amongst the gayest things I have ever written (consider that your warning). If transvestism and gay sex don't make you want to rub one out, this story is not for you.

*note: I like to use the word "zazzy" instead of "daddy". If you say it out loud to yourself, it is intended to be said in the gayest voice/accent/inflection/whatever you can possibly make.

.....................

I had a slow week where I wasn't that horny but ooh I'm back girl! And I'm so fucking horny, I can feel it in my asshole. I can hardly keep my hands off of (or out of) myself! I need to get fucked in my asshole right now. I MUST find the right MAN to OWN MY ASS! So I stop in a public restroom and switch into my girl clothes- my Sissy Mi clothes.

Sissy Mi is the alter ego I slip into when I want to be treated like a slut. On this occasion, I put on a skintight, hot pink tube skirt with a matching hot pink tube top with a black cropped zip hoodie over it, a blue wig, blue heart sunglasses and pink thigh-high hooker boots. I wasn't wearing underwear and was packing a dildo up my asshole which was clearly visible, as my skirt rode above the dildo.

The skirt was also doing fuck-all to hide my dick, especially since the way I was dressed had me feeling attracted to myself and I was walking around with a half-chub. I wasn't trying to hide shit. I did not look like a woman who just happened to be over 6 feet tall, I looked like a man wearing women's clothing and if you had seen me, you would have pulled your fucking dick out right then and there. The pink and blue looked fucking hot juxtaposed against my waxed smooth, dark brown, toned stomach, which I oiled up just a little so it would be shiny and catch the right man's attention. I wore strawberry lip gloss and sucked on a little lolly pop while I walked around looking for cock, looking as slutty and as desperate as possible. And for my final touch, I wore a collar around my neck that said SLUT, which has a leash I can attach to it. I kept the leash in my purse until I was ready to reward the right gentleman with my body and my skills.

There was no way I wasn't going to get some cock tonight. Now it was time to fuck strangers until I found the right one! I sucked a guy's cock, balls and ass at a bus stop. I gave another guy a rimjob in the bathroom at a gas station. I hung around at a local bar until Mr. Brazilian Perfection himself walked in, all sweaty from some sports activity or some shit like that. I had finally found him - my master.

He was gorgeous, with his little dimples and his muscles. He looked like the Latino guy from Saved by the Bell, but a little taller. He sat next to me at the bar so i immediately and very forwardly started flirting with him. I kept talking about his cock, his balls and his ass. How hot he was, how hot his muscles were.

"Ooh, look at you!" I said, all flirtatiously, getting way too close to him, totally popping his bubble. "You're hot!" I put my hand on his chest and rubbed him down his sexy, hard six-pack stomach. He was shy but didn't back off at all. His smile told me all I needed to know.

Bashfully he said, "Thank you" He had a deep voice and a thick accent. I couldn't believe he was real.

"Can I feel your muscles, hot boy?"

He hunched his shoulders and said, "Sure, I guess."

I ran my hands up and down his arm, squeezing his bicep as I maintained eye contact, with a gratuitous and highly exaggerated, "Ooohh baby, you're SO strong!"

He giggled in disbelief.

"Can I feel your other muscles, hot boy?"

"What, my legs?"

I glanced down at his little gym shorts. He had beautiful, muscular legs, which were clearly waxed but we all know I wasn't interested in his legs. I made eye contact with him as I put a fingertip on his leg and slowly ran it upward.

"You have very nice legs, sir, but the muscle I'm talking about is up HERE": I stopped just above the edge of his shorts. He was hard and it was showing, but for some reason, he was still trying to play straight. I don't know who he thought he was fooling with those little ass shorts on but ok.

"I want your cock, Hot Boy!" I said, totally deadpan, putting him on the spot in front of whoever he thought he was impressing by pretending to be straight. "I WANT YOUR BIG BEAUTIFUL COCK RIGHT UP MY FUCKING ASSHOLE, HOT SEXY PERFECT MAN!!!" I said even louder. "AND I KNOW YOU WANT MY HOLE TOO BECAUSE I CAN FEEL HOW HARD YOU ARE! (I squeezed his big, hard dick) Come on, Mr. Perfect, fucking give it to me already!!!"

I was laughing as I tugged at the lump in his shorts and though he was laughing too, I could see he was starting to get embarrassed and I didn't want to spoil my chance to stuff him inside me, so I calmed down briefly. I asked if he'd ever fucked something with a dick before. He lied and said no. I told him to buy me a drink and text any friends who might be interested in some hot warm anus and some bomb ass head, and then take me to his place.

He didn't text anyone. He sipped his drink with a smirk. He kept trying to talk to me like he wanted to get to know me better. That's not how I do things. If I get to know you, I might not wanna fuck you, so I would rather get to the fucking part first since that's the priority. I tried to be good and control myself but my hands kept trailing back to him. I kept feeling up his chest, his arms, his six pack...his cock. I couldn't contain myself, I tried to pull the cock and balls out of his little short-shorts and tried to suck him off right there, but he politely declined, a few times. I kept BEGGING for it "give it to me give it to me please i need it!"

People were starting to look at us, which excited me because I was eager to show this sexy stranger how bad I wanted him. Each time my skin touched his, I felt like I was just about to cum. My cock was very hard and because I was wearing a dress that was intentionally too short and too tight, it was very visible.

Eventually, a bartender asked us to leave. I acted like I was mad about it, but I was actually quite happy because this was my opportunity to give myself to Mr. Brazilian Perfection. We ran around to the alley behind the bar and i ate his ass and let him cum in my mouth. Sure, we kissed for a bit, but I quickly began jerking his cock. I didn't even suck it before I told him to turn around. The true key to a man's heart is to tongue him up the ass as soon as you know you are HIS.

"Please take me home with you Mr. Brazilian Perfection, so you can make me yours?" I handed him the leash attached to the choker i was wearing that said SLUT as I continued to suck-fuck his sweet asshole. He was DELICIOUS! He tasted like salty apple sauce someone had farted into.

Now free from his short-shorts and only wearing a shirt and sneakers, he walked me like a dog to his car where I sucked him all the way back to his place as he fucked my ass with the dildo I had stored inside it. He pulled it out and sucked on it himself a couple times. He said I taste like strawberry shortcake that someone spilled cumin into. He couldn't get enough.

When we got out of the car, he swept me off my feet and walked me upstairs like a lady. We gazed into each other's eyes and kissed.

"Mr. Brazilian Perfection, baby..."

"Yes, my love," he said yearningly.

"I need you to make me your little bitch, baby, PLEASE."

I grabbed him by the neck, he grabbed me by the throat and we kissed as he slid a finger up my ass with the hand he was cradling me with while he walked me up to his place. We kept gazing into earth other's eyes with his finger inside me, as he carried me away like a princess to his castle. I had never experienced anything like this in my few previous crossdressing adventures. Normally, I just fuck hot guys in bar bathrooms and behind buildings and stuff like that.

We got inside, he laid me down on his bed and we continued kissing, passionately and gently while jerking each other's dicks off. Finally, he holds me down by my throat and holds eye contact with me as he mounts me. My hole gaped eagerly for him. I was wide open. He knew how bad I wanted it, so he teased me and made me beg.

"You say you want to be my bitch?" He said, with the tip of his cock just barely touching my wide open anus.

"Yes I do!" I cried aloud. "I DO! I DO!!!"

"Then say it baby," he whispered

"I WANT TO BE YOUR BITCH, ZAZZY!" I screamed.

He gave me the tip and then yanked it out again, holding it upright as he demanded, "SAY IT AGAIN!"

"I WANT TO BE YOUR BITCH, ZAZZY!" I screamed even louder, tears now streaming down my face. I couldn't fucking handle how horny I was, I felt like my body was literally going to explode.

Again, he gives me the tip and YANKS it back out, HARD!

"AGAIN!"

I screamed it again. This time he rammed the whole fucking thing right up my ass one time and then YANKED it again! Right when I was learning to love this sensation, he started fucking me for real, very fast.

"Keep saying it," he said. I did as i was told. I just repeated the sentence over and over and over again as he fucked me into anal submission with his hand around my throat. I started slamming my ass down on his cock, causing my own big ass dick to bounce off of my abs.

He YANKED his big fucking dick out of my asshole again, stood up on the bed and placed his ass above my face.

"Keep saying it," he demanded. I did as I was told. I kept repeating the phrase "I want to be your bitch, zazzy" with my cries being muffled by his hot, musky, hard ass cheeks are his sweet little hole. This goes on for at least 30 minutes, with me hugging his ass and giving him the deepest rimjob I could.

Eventually he got up off me, still standing on the bed, and told me to let him lay down so I could get on top of him. I do as told, of course. Now I'm riding my Brazilian zazzy. My giant cock bounces off his stomach as I'm bouncing up and down, taking his big cock inside me, moaning loudly, if not screaming in ecstasy. I'm running my fingernails up and down his muscular chest and torso, passionately kissing him intermittently. I am his bitch. I belong to HIM. He calls me his lady. He holds me by the neck right now, but he will spank me repeatedly later when he has me bent over. And he will squeeze my neck tight as he unloads his cum-filled balls into my subservient asshole. And I will love every second of it and beg for more.

I'll do anything for him.