Riley's Diary: Clubbing

Dear Diary,

Last night was amazing! I woke up in the morning and before I headed to work, I saw a package sitting outside my door for me with a note on it;

"Thought you might like these. Hope to see you tonight at the Hefty Schlong. -- Daddy ♥"

I was giddy as I quickly rushed back in and opened it up. Inside was a very cute undersized little shirt with a blue sweater, a purple mini skirt, purple semi see-through stockings, green long socks, blue boots and a thick large bracelet with condoms inside. It took a few moments for me to set up everything up on my bed and I couldn't stop smiling after I left for work. I was excited all day, fantasizing about seeing Daddy at the club and spending some well-deserved time with him. As soon as I got done with work, I rushed home and changed into the special clothes. I kept checking myself out in the mirror, spinning and twirling. I had to wear panties since the skirt was so short my tiny little cock would have been visible to anyone. I left and got a cab to the club. Even as I got closer, I could hear the music booming.

As I got out the bouncer took one look at me and pointed me to the back entrance. I headed back where the music wasn't as loud and the door was had two guards outside. I approached them and they grinned as I got closer, checking out my legs and body. One of them got closer. I was scared of his much larger frame and blushed as he leaned down and grabbed my crotch, feeling my tiny little cock and balls. He smiled and signaled the other one to open the door who was laughing.

"This is the boss's special guest" He laughed as he stood straight up. "Just go straight through the hall, boss isn't here yet."

He spanked my ass as he pushed me a long. I went through a dimly lit corridor passing door after door. As I crossed each one, I could hear moans and groans coming from each one. My tiny little cock was hard as I kept walking, trying to ignore the sounds. One door was slightly ajar and I could see a rather fat old man grinning as girl was on top of him, rubbing her breasts on his face as she rode his deceptively impressive cock and a sissy like me licked his balls. I quickly passed by, hoping they hadn't seen me, but I just could not get the image out of my head.

I quickly rushed to the door at the end as the music got louder and louder. I burst through the door and I was suddenly overwhelmed by the loud music, colorful neon lights and crowd of people dancing and drinking. There was a stage in the middle where a femboy was pole dancing. His tiny little cock was rubbing against the pole as some men and futas surrounded the stage laughing and throwing money at him. Behind the little sissy stripper was a rather gifted futa who showed of her cock by flailing it around and dancing and smiling at everyone. It was all a lot for me and I walked to the other end, where the bar was. I grabbed a drink and went to another corner to watch from a far and wait for Daddy. By now the futa and femboy had gone from being playful and silly to raunchy hardcore fucking on stage. I bit my lip as I felt my tiny little cock leaking precum just from watching. It took every muscle and nerve in my body to stop myself from touching myself.

As I was busy watching, I didn't even notice two men standing close to me and checking me out. As I slowly sipped my drink one of the handsome buff men got closer to me and grabbed my ass making me jump and drop my drink. He looked to his other friend who had his eyes keenly locked on the bulge.

"Looks like this little sissy is lost" he said as he pulled up my skirt to get a better view.

"Nah! I don't think so. Look at this!" The other one grinned as he lifted up my skirt to see my little bulge.

I could see his pants bulging as he saw my little wet panties. I felt powerless as one grabbed my hand and pulled me along to the bathroom. It was another dimly lit room with a dirty floor. One got into a separate stall and the other one pulled me into the one next to it. I got a glance of the glory hole and the other guy pulling his pants down as the other one grabbed me and pulled me close to his chest as he spanked my ass and squeezed it before pushing me down to my knees. My face dragged along his body until my knees were on the dirty floor. By this point I didn't even care about it as I saw his massive musky cock come out of his pants.

"Now be a good little slut!" He leaned down and whispered to me as he stuffed his cock into my eager mouth.

"Me next!" The guy in the next stall said as he shoved his cock through the glory hole.

I licked the cock in my mouth. The musk was so overwhelming I was leaking precum all over my legs. I grabbed his legs as I moved further, letting his whole cock go down my throat until my chin rubbed his balls. He pet my head before grabbing my hair and pushing me back. I started bobbing my head back and forth as I reached to the side and grabbed the other guy's cock and began rubbing it. My hand was already a bit wet from my own precum, lubricating it. My head was grabbed again and pulled as high up as my throat could possibly take it. I began choking and drooling over it until he pulled me off and threw me towards the other cock. I eagerly began sucking it as my hands rested on the stall walls. I felt the pressure of a knee being put against the back of my head as I choked and drooled on the other cock and could hear them both laughing. He didn't let go until I could feel his warm cum flowing down my throat. As he pulled out, I took a deep breathe before I was suddenly pulled back to the big, black, wet cock which my tongue was more than willing to lick and clean as his precum was oozing out on top of it. I held his legs like before as I sucked his balls one by one, my nose rubbing onto the cock as the precum slowly dripped over me. He grabbed my head as he began to groan. He pulled me up and pushed me down onto his cock letting it go deep down my throat before he began slowly humping my mouth and pumped my mouth full of cum. He finally let go as he stopped panting and his cock got limp. I fell to the floor as he walked out and threw a tissue roll at me from off the counter.

"Thanks! You've been a good little slut!"

I panted heavily as I slowly got up and sat on the closed toilet seat, cleaning myself up. I licked my lips and grinned as I tasted his cum. After seeing the futa and femboy get it on in the middle of the room had gotten me hot and horny, I really needed that. I stood up and fixed up my skirt and shirt and went out of the room. The strippers were off the pole and walking around as a girl was now dancing on the pole. I grabbed a drink and then another from the bar and sat their as I waited and finished them. As I was on my third and a bit drunk a futa came over to me. Her massive breasts were just barely covered by some large heart shaped pasties and her cock was covered by what looked like a very long sock with hearts all over it. It seemed like she was looking for me for a while as she suddenly jumped up and did a little clap as she saw me.

"Riley! I have been looking all over for you!" She smiled as she checked me out. "Come with me, your friend wants to see you!"

I got up and stumbled a bit as she grabbed my hand to help me up. I followed behind her as her ass jiggled and my eyes were glued to it. I was back in the corridor of rooms but this time instead of going straight we took a couple of turns left and right until we were outside a large room.

"This is his office. He is expecting you!" She got close to my face as she whispered and spanked my ass as she turned around and left.

I opened the door slowly as I entered. Inside was a large desk with two chairs in front of it and Daddy sat across. He smiled as he saw me enter and waved me over while he was on a call. I sat on one of the chairs as he finished up the call.

"Oh wow! You look exactly as I imagined you would!" He put his phone down as he checked me out.

"Thank you, Daddy." I grinned as I stood up and spun around and showed off the gift, he got me.

"Have you been a good little slut?" He grinned as I could see him rubbing his cock under the table.

"Yes Daddy! I love being your good little slut." I grinned as I pulled up my skirt showing him my plump ass.

"Good, I have another little gift for you." He grinned as he handed me a wrapped-up box.

I leaned forward and grabbed it. I neatly undid the bow and ripped the wrapping from one side. As I pulled off the wrapping I almost laughed out loud as I saw a Drilldo®. I pulled the top off and shook it upside down, my mouth watering as I had wanted to get this for a while. The rather interesting looking dildo dropped out along with some accessories.

"I take you like it then?" Daddy said as he smiled watching me get excited.

"I love it Daddy!" I was grinning from ear to ear as I examined it and the other accessories.

"I thought you might. Since our last visit to Sissys R Us you couldn't get your eyes off of it. Let's see you try it out then?" He smiled as he leaned back on his chair.

I looked at him with a naughty smile. I eagerly took off my skirt and panties, showing him my tiny little hard cock. He smiled as he watched me lube up the tip and slowly put it on the floor and carefully got on top of it. Before I could sit on it, he stopped me.

"Let's do this completely naked!" He smiled as he got up and locked the door.

He sat on one of the larger chairs after taking off his own clothes. He sat down, his big rock-hard cock in his hands. He slowly rubbed it watching me take off my own clothes. I stood in front of him and smiled as I slowly got down and grabbed my cheeks, pulling them apart as I let it slowly enter. I let out a little moan as it penetrated my tight little hole. I smiled like a little slut as Daddy watched me, grinning and rubbing his cock. As it got fully inside me, I felt a shiver go through my body as it turned on. The room was suddenly filled with the sound of the whirring inside the dildo and soon after overpowered by the sound of my moans. Daddy was enjoying himself as he saw my face. He got up and I suddenly became quiet thinking he wanted me to suck his cock. I closed my eyes and had my mouth open until I heard a click and opened my eyes to Daddy sitting back down. I looked down to see that the Drilldo® had been strapped onto me. I carefully got off my knees as it was now stuck inside me.

"Now crawl to Daddy. His cock needs a tongue bath." Daddy smiled as he beckoned me with his finger, his other hand still on his lovely big cock.

I gave him a slutty smile as I crawled forward. My mouth wide open as he pointed his cock towards me. I crawled until it was in my mouth. I looked up at him as I grinned and licked his tip, playing with it and swirling my tongue around it. He grabbed me by the side of my head, pulling my hair up. As I was still on my knees he let go as I eagerly kissed his cock, letting my soft lips touch his throbbing veins and then slowly sucking in the tip into my mouth. I felt him petting my head as he whispered good sissy. I started bobbing my head up and down onto his cock. It was already throbbing inside my mouth as I looked up at him and he looked down at me. He was breathing heavily as the Drilldo® ramped up to max speed. I wanted to moan but I just couldn't let go of Daddy's cock. It just fit so perfectly in my mouth and throat, the smell was intoxicating and the taste was like nothing else. I could not stop even as my tiny little cock was gushing out precum. I sucked Daddy's cock as deep as I could until Daddy stood up and pushed me down. He gently pulled out the Drilldo® and got on his knees, examining my now gaping hole. He slid two fingers in easily and laughed.

"Don't worry, my cocks much larger!"

Before I could say anything, I felt his strong hands grabbing my waist as he stuffed his cock into my hole. I let out a loud moan as my finger nails dug into the floor carpeting. He slowly moved deeper and deeper, pushing as much as he could until I felt his balls rubbing mine. I gripped the floor as tight as I could as he began pulling out and thrusting in and out. The room was now filled with the sound of his hips hitting my soft plump cheeks. I could no longer moan as I was completely powerless. I bit my lip as I began drooling like a mindless slut. His cock was throbbing inside me as he groaned before tightening his grip and going fully inside me. He unloaded all his baby batter inside me. My cock began leaking again as I felt his hot sticky goo fill me up. He stayed inside me as I felt his cock slowly get softer. As soon as he pulled out, I turned around and quickly licked his cock clean. He pet my head as he caught his breathe. As soon as I was done, he got up and put on his clothes, he threw some money at me as he was leaving the room.

"Thanks, I'll see you soon. That should be enough to get you home. You should consider working for me some time."

With that he left the room. I got up and collected the toy and its accessories, put on my clothes and cleaned up. Daddy had really filled me up as even in the cab I could feel my hole still leaking cum. As soon as I got home, I put the new toy in the special toys cupboard and took off my clothes. I fell onto bed naked and still leaking Daddy's cum.