Adventures of Wyn Pt. 01

These stories are my fantasies and how I'd love to live my life. Any person or company presented are fictional.

Title: "It could've gone worse!"

So, I was pretty excited when I moved out of my parents' house to live on my own. I was well-versed with how to cook, clean and all that stuff. Money wasn't too tight too, but I always was afraid to live alone because I'd think what would happen if something happened to me and I couldn't call the ambulance or something.

Anyway, over a year, I passed through this nervousness by just watching porn at night, mostly straight stuff. Then I watched one of those "sissy Hypno" videos. It didn't directly change me but got me curious. So I started to experiment with my fingers. I was really surprised how good it felt to be filled and so I craved more. I started buying enema kits, dildos, and before I knew, I started to hit the gym to have a toned body.

In a year, not only I beat my fear of being alone, but I also got a hand-filling ass to go with. I couldn't get a perfect hourglass figure, due to having a training program without the help of a trainer, but I was looking good. I also visited the local beauty salon to get waxed now and then. I used to be so hairy since I'm European, but after more than a year, I guess it took 20 months to completely become hairless, I was complete.

All that exercise, careful diet, painful waxes, lotions, and skincare products has led me to be a girly looking guy. I looked at my naked body in front of the mirror, and I let a sigh. I mean, not out of frustration, but out of excitement. I wanted to watch myself getting fucked, just like in the videos.

I kept training with plugs and dildos, but nothing can prepare you for the real thing, I believe. Mom and dad visited me every month, but they didn't even notice my change until I dyed my hair to red. They asked why the change and I told them that I like the color. They were not supportive of course, but what's done was done.

So, with a body and mind that begs to get fucked, I decided that I'd hit a gay bar in the city. They would only be open after midnight, and me having work, I needed to go to the bar on Friday. In a week, I bought some thigh-high socks, some cotton pink and white panties, and a few skirts to have some easy access for a quickie. I was eager to have sex with someone.

On Friday night, around 10 pm, I started to get prepared. Cleaned my ass out, slid a plug inside, wearing my white thigh-high socks along with sneakers, slid into my skirt, wore this geeky sweatshirt I had and just left home. In one year, my hair wasn't as long as I wanted, but it barely reached my shoulders, and that seemed enough when I looked at the mirror.

On the bus, there were not many people to judge you when you are traveling around 11 pm. No one to judge you but the bus driver. It took me around 40 minutes to get to the bar, and I saw it that people were already going in. I walked happily to the queue, there were not many people when I got there. When I approached the bouncer, he said that I could not enter, because I was a girl.

Getting a comment like that made me all happy inside. A girl. I didn't think I was that girly since I was somewhat long, but he made my night even before I entered. I just showed him my ID, and when he understood that I was a man, he let me in. That was it. I was going to hook up with a stranger and let them fuck my ass. It was very hot and taboo for me, I was getting tingled in my face just my thinking about it.

The place was not that crowded, so I just sat on the bar, asked for a cocktail and started to wait for it. Then it happened. I felt a hand on my butt. I turned around to see who it was. I was not angry about it, I just wanted to see that man. But the crowd was already pouring in, masses walking left and right. Couldn't even point the man, because there were already five guys behind me, hoping to get a drink.

After the bartender passed my cocktail to me, I just drank it slowly, dancing to the music slightly. I'm an awful dancer. So I just moved on my feet, from one foot to another, slightly swaying around. When I finished my cocktail, I just left the bar to go to the restroom, to freshen up and all. When I did, the place was already full. More than six guys were washing their faces. I think one of them had nausea so the others were his friends. As I entered, they grabbed their friend and left, so I was left alone in the restroom.

I kept looking at myself and sighed. I mean, it didn't work as I intended. No one came to me, and I was too shy to ask for some fuck by myself. I was going to leave the bar. I walked to the door, and at the same time, I saw this tall, well taller than me, dude blocking the door. He said;

"Hey. You seem frustrated, baby. Everything's fine?"

So I thought that would be my chance. I told him why I came to the bar and all. He grinned and his hand traveled over my waist like we were flirting in the restroom. After I was done, he just blurted that he told me that we could do it in my home.

I accepted without thinking about it. I mean, damn, I wanted to get fucked, and I was going to get fucked. So we left the bar, I hopped in his car. He asked me where I lived, I gave him my address. He drove me to my home. By the way, I live in a housing estate, with a few apartments towering in it. The parking lot is outside of the estate area, so he just parked and said;

"So, you live here? I know it's late to ask but if you wanna back down I can just..."

He was probably going to say some stuff like "Hey if you wanna bail, that's okay." or other stuff but I was just busy reaching to his zipper and taking his cock out. Nuh-uh! No way I was giving up! Things came this far, I wasn't going to back down now.

So he laughed when I was fidgeting with the zipper, and he helped. I felt like a dork. Remember what I said about nothing prepares you for the real thing? This is what I meant. I just leaned aside and looked at his cock. He was hard, like a diamond, and his cock was thick. I could stroke with both hands, but I couldn't wrap my hands around it. He was definitely above average. My dick's not that big, and I'm a grower so when I'm flaccid, it's really small. When he teased me about if I was going to suck it or just drool for it, I just latched onto that big fat meat.

I was slurping and kissing all that length, drooling and making the whole thing wet with my saliva, spit-shining the dick I wanted in my ass. When I slid my tongue over his glands, he let that cute moan, made me latch my mouth on his crown. I'm not gonna lie, precum was so tasty. I usually would taste my cum and precum to get used to the taste, but that's when I learned that everyone would have different tastes.

Taking the head first, I sucked it, swirled my tongue around and kissed the tip like a wanton slut. I needed this badly, so I reached for it. I slowly moved further on his dick, it was thick, my lips were not able to fit that monster in. I was not gagging, I beat that reflex in a few weeks by poking my throat with my toothbrush whenever I was washing my mouth, and I was just leaking saliva all over his length. I was moaning when I was sucking his cock, just because it turned me on too much.

He laughed and said;

"Damn, you wanna get fucked that badly?"

while I was sucking him, and I looked up after he said so. I mean, if it was me sucking cock, I thought it was very obvious that I did want to get filled in my ass. So I looked up asked;

"Yeah... what gave it away?"

jokingly while stroking his wet dick with a smile. He laughed even more and slapped my ass, then said;

"You've been wiggling your ass since you started to suck me."

I did not even realize it, but he was right. I was moving my hips left and right, even my toes curled in anticipation. I bit my lower lip, then nodded to him before dipping my mouth in, licking his balls and kissing his taint while slapping the big white meat on my face.

He then grabbed my hair, pulled me up to his face, and kissed me. I normally would find this very romantic and lovely, even get on his lap to enjoy that kiss, but I was too horny to acknowledge any kind of affection, so I kept stroking his dick, even when he was kissing me.

He broke the kiss afterward, and just lowered my head on his cock. He moved his hips, filling my mouth with his fat cock, making me suck it deep by keeping my head down and pushing his cock up to fill my mouth. I was really happy by my mouth being used, made me feel like a slut. He kept going harder and faster, slapping my ass, slapping my face, pulling my hair.

Then he pulled my hair and spat on my face, then slapped it and called me a faggot. At that moment, I just went off the edge, I let the sluttiest of moans I could, even without thinking about it, and I licked my lips and smiled to him warmly while stroking his cock real fast, making my hands and his cock all covered in precum and saliva. He opened the door of his car, and said;

"Let's go to your home and get a bed. I wanna pound you for the whole night."

I obliged, chin dripping saliva, face full of lust, hair messed up. We walked to the entrance, I opened the door with my keycard thingy -don't really know its name- and we got in the elevator. There, he kept groping me and kissing me until we left the elevator, then we got out of the elevator and got in my home. I didn't even try to take off my shoes or anything because as we entered, he just lifted me on his lap and kissed me.

He walked around the home, with me on his lap, kissing, trying to find the bedroom. When he walked past by it, I tapped on his shoulder and moved my head to the bedroom's direction. We entered in, he threw me on the bed, then laid next to me. He laid back, pulled me on top and ground his hips against mine while squeezing my butt. I kept kissing him and fidgeting with the zipper again. When his hard pecker was out, I spent no time and started to poke my asshole with that cock. I was horny enough to ride his dick until tomorrow morning.

I couldn't push it in, because my hands were slightly shaking in excitement, so he did it for me. That was it. I felt a small stinging pain at first, but then it was bliss. The feeling was superb, nothing like I've ever felt before. His alpha dick was slowly entering me, his hands spreading my ass cheeks, my eyes slowly rolling back. I hugged his neck with both arms, my hips swaying left to right in wanton need.

"That's right... fill my ass with that fat cock. Fuck my tight little butt!"

I couldn't even think straight while he was plowing me, even slowly. My toes were curled inside my sneakers, my thighs were shaking, my butt creating those ripples as I got filled again and again. Soon, he would just start going faster, slapping my ass and making me ride that cock fast enough to make me moan loudly. The bed started to creak as he kept going faster, and I started to moan louder.

"Yes! Yes! Fuck me! Fuck my fucking ass! Breed my little boy pussy! Open my ass wide with your cock!"

From that point forward, we did many different things. Me getting drilled by his huge cock while my legs were spread, hugging him and begging to get fucked. Him putting me on my knees and just fucking me like a bitch dog in heat, balls slapping into each other. My face on the edge of the bed while he fucked it like a pocket pussy, begging to be filled. With a few more positions that do not come to mind right off the bat, we finished with me on the prone, and him pounding me into the bed with all the grunts and moans.

My arms were behind my back, spreading my ass for him and his hands were resting next to my head, curled in fists and providing support when he was piledriving my ass to next week. I felt nothing but utmost lust to be his sex toy, getting fucked by him for hours, days, weeks, years to come.

Then it happened. I felt a twitch in me. And another. And another. Before I realized, he was completely still, hilted in my ass, hugging me from behind, pulling my hair aside to kiss my neck and bite my ear. He was cumming inside me, and I was leaking my cum onto the sheets. My legs twitched in pleasure, my moans were high-pitched, my hands were hugging his arms that completely restricted me from escaping the warm cumming session.

Out of breath, he slowly pulled his cock out, then flopped away and let a relaxed sigh. Being intoxicated by his roughness, I just rolled over on his chest, resting my head on it while my hands were slowly treading his body.

"Mmh... that was all I could've asked for..."

He wrapped an arm around my body, hugged me tight and put a kiss on my forehead, like the romantic dork he is, then he smiled to me and asked;

"So... I'm Craig. What's your name?"

"I'm Wyn."

"Wyn, do you wanna date with me? You know, we could hang out, go to films, do-"

Before he could go further, I just latched my lips onto his, kissing him deeply, one hand cupping his cheek.

"I would love to have a date."

With that, clock almost hitting 6 am, the last thing I remember was Craig hugging me and going to sleep along with me.

-To be continued...