Sydney Sweetwater 01

Sydney Sweetwater 01

Hey, I'm Sid and I live a pretty successful life as Sydney Sweetwater on the weekends. My secret to becoming a successful cross dresser and fem role player comes mostly from my roommate's friends whenever they stop by to watch a game or play some video games. And mind you that I said Kenny's friends. I don't push anything on the roomie because we have to live in harmony and stuff, so I don't practice on him, but his friends are open targets as far as I'm concerned.

His friends are my blackboard and I rarely miss a chance to give a lesson or absorb a lesson or two. And you know what? They have learned to deal with my queerness since last summer. And sure, they all give me the business about my queer lifestyle from time to time, but one of my lessons learned is how to level up on my flirting whenever they crank up the snide comments. And you know what else? Hah, I think I'm winning! Well, you know, right? Even a slender boy in makeup and a cute skirt is going to win most of the time.

Not that I wear just a skirt too much anymore. I mean, even the straightest guys who drink enough beer while watching hanging out can only take so much. I mean, last August I wore a sea shell luau type bikini top and a short skirt and all that ended up doing as was to confirmed to them that I was truly a boy. Now, why Jake had to mention how far I was from being a man is beyond me, but as I smoothed out my skirt and sat on his lap to call him out as a naughty boy, well, let's just say that Jake takes a lot less jabs at me these days. Like I said, I think I'm winning.

And last August is where my story starts. Not only did Jake play his little exposure game with my skirt at my expense, Nick seemed to be staring a lot more than laughing and I mean he was staring me down. Thankfully for Nick, I was the only who noticed his eye target, which tells you something about where everyone else was looking. That was a turning point of sorts, a point of no return if you will, I think.

It was later that evening when I was cleaning up the plates and cups when Nick found his way into the kitchen, which he carefully planned out to make sure he had a few moments alone with me. I mean, damn, for the previous three months, I was the occasional joke and then there I was, not the joke. I don't know what came over Nick, but he made the most of his few moments of alone time.

And don't get me wrong. I didn't squeal, I didn't push him away and I may have returned his hugging efforts as we talked in private. By the way, I absolutely participated in the secret embrace, but he started it. I knew who had his arms around me and he knew who he had his arms around, but SOB, it felt so natural. I'm not saying it was the beginning of the end, but it was the beginning of regular stolen moments, for sure.

And thanks to last year's football season, OMG, there were so many stolen moments! There were so many moments in the kitchen, a few on the rear deck, a few in the back hallway, and OMG, the laundry room, so many times in the laundry room!

I even snuck him into my bedroom once so we could expand our flirting properly, if that was something that he wanted, and OMG, that was sex without being sex! I was the aggressor that time, but I was just following the rules of engagement per the old saying that goes "one thing always leads to another" as I nervously unbuckled his cargo shorts and released his hard manhood. I broke free from our embrace and spun around to offer up my soft backside and that turned out to be quite the next step for us. LOL, it also turned out to be something that he really liked and he took full advantage of the situation. I even leveled up and quietly pushed my cotton capri pants down for him. LOL, yup, another thing that he really liked, but our time was short because the roomie and Jake were still in the living room watching a game and I knew they would be getting suspicious soon.

"Do you have any condoms in your bedroom, Sydney?"

"No Nick, maybe another time, but listen, sometimes the T-Girls on Chang let their boyfriends stroke off on their asses, if that's something that interests you. I mean, that's sexy, right?"

"Oh, do those T-Girls on Chang also sometimes suck off their boyfriends?"

"Hah, all the damn time, but we're not there yet. Just keep doing what you're doing and finish before one of the guys comes looking for you."

Well, I still wasn't sure what was going on behind me, but it felt nice and his moans told me that he was enjoying it, so I gyrated my buns up and down for him figuring that he would say something if that wasn't working for him.

And then before I knew it, I was face down on the bed and he was thrusting between my cheeks like halftime was almost over. And oh, yeah, he was trying to get inside of me, which also felt alright, but certainly wasn't working due to the dryness. And then before I knew it, he rolled me over and climbed up my body.

"Get it wet, Sydney. Just put it in your mouth for a minute."

"Nick, this is a big step."

And then, LOL, he was just waiting for me to open my mouth to speak, right? Why the hell I had a grip on him as he towered over me was beyond me, but he seized the moment and he pushed forward and again, before I knew it, well, we took a big step! It was such a surprise to have a mouthful of hard cock that I barely moved, which he didn't care about as he began to thrust in and out of my mouth while I laid there looking up at him.

"Suck me, Sydney. Suck me dry."

I tried to create a suction around his fat manhood, which was a maybe or a maybe not because I never had a hard dick in the mouth before. However, it must have been good enough because he began to grunt and unload his load directly down my throat. And let me tell you, I must really be a fem boy sissy because I had never released that many streams at once ever in my life. The ropes of his seed just kept squirting and he kept moaning and OMG, he kept thrusting deeper and deeper into my throat. I mean, like I could feel his head blocking my throat.

"Ahh, that was good Sydney. Now, get some condoms in here for the next time."

"Kiss me, Nick or shove it back in my mouth for a moment. I want some lip action."

Hah, there no asking him twice, right? I mean, he was a little limp, but he jabbed his rod back into my open mouth and allowed me to actually perform the proper duties. By the way, LOL, a spent dick is so much easier to handle than a hard one. He even reached down and rubbed me, you know, sort of. Now, that didn't last too long because he was sensitive, but it was valuable practice for me.

"You better go back to the living room, Nick."

"Yup, are you coming?"

"Ah, no, I need a little recovery time. You can say good bye to me in here before you leave if you want to. I don't think you need to sneak in, by the way."

I cleaned myself up a bit, changed into my jammies, crawled under the covers and called up the football season for the rest of season. The way I figured it, he would get what he wanted by the end of the season and who knew what the playoff weekends might bring.

Just as I was dozing off, I heard a soft knock on my bedroom. Of course, it was Nick and he slipped inside very quietly and closed the door behind him. I mean, it's always polite to say goodbye to the host, right?

End Sydney Sweetwater 01