Riley's Diary: Maid's Day In

Dear Diary,

Today was a weird day. I was at work, waiting tables and I got a message I was not expecting. It was a daddy I had met at a club, and he wanted to meet me. This was enough to get me excited, but his other request just got me so turned on.

"Hey honey! It was so fun meeting you at that party. I actually needed your help with something. Why don't you come to my place tonight? And wear a maid's uniform, I have some plans for us 😘."

I spent the rest of my time at work just imagining what he had in mind. I had to go to the work bathroom several times to jerk off. I could still remember his massive cock in my mouth from the party and couldn't wait to get some more. I kept checking my watch and as soon as it was 5, I was out the door and went directly to Sissy R Us. Luckily, they had a skimpy pink one in stock. It was a pink top that was tight and low to show off my chest and sleeveless with lots of frills. The skirt it came with frilly and very short, so short that it just barely covered my hips. I quickly changed into it and pulled over a coat and got a cab to his place.

I was dropped outside a large mansion and slowly made my way to the door. I was smiling the whole time, and erect as I thought of what fun he had planned. I knocked on the door, holding my coat tightly as I waited outside. I could hear footsteps coming closer to the door and this is where the day started getting weirder.

The door was opened by a voluptuous older woman. She greeted me with a smile, like she was expecting me.

"Oh, hello there! You must be the help my friend sent."

"Y-yes I am the help!" I quickly entered, thinking this was a bad prank. "Your friend said you needed some help?"

"Yes, I did! Although, I was expecting a maid." She asked a bit confused as I was hugging my coat, not wanting to show her my outfit. I really thought that daddy wanted me to work as an actual maid. I felt miserable as I looked around at the magnificent place, covered in beautiful art and sculptures. As I was looking around, I didn't even notice her walk up behind me and begin to remove my coat. I quickly jumped back blushing bright red as I turned to her.

"No no no, its okay, I think I'll keep it on. What did you need my help with?"

She looked a bit dejected as she walked deeper into the house. "I just needed someone to help clean up some messes here and there."

As she walked, I began to notice something odd. Some of the art was of futanaris, and more importantly, it even kind of resembled her. I followed her into what seemed to be her living room. There was already a glass of wine on the coffee table as she sat down on the couch and put her legs up on it. She pointed down, close to the edge of the couch at a puddle of... something.

"Could you start here?" She grinned.

"Of course, ma'am!"

She threw me a rag and I quickly got on my knees to begin cleaning. It was then that I saw something I really should have expected. Between her very expensive looking red dress, was a bulge, and a very big one at that. I felt so stupid and was to awkward to apologize so I just kept cleaning, slowly working my way between the couch and table, under her. She was sipping wine as I was rubbing and cleaning and I suddenly felt something on my coat.

"Oops!" She jolted up as she had spilt some of her wine on my coat. "I didn't mean to!"

I quickly got up, pulling and trying to examine my coat, until she grabbed it.

"It's fine! I'll get it cleaned up, just give it to me." She smiled as she stuck out her hands.

I figured this was the best way to break the ice. I slowly took it off. She smiled as she saw my skimpy uniform and probably also saw my tiny little bulge. She grinned as she grabbed it.

"So, you are a maid!" She smiled as she began walking away. "Just clean up here and I'll have some more work for you."

I smiled back, glad I wasn't being a complete idiot and began cleaning away happily, smiling as I scrubbed the floor. Before I was done, she came back. This time she had changed her clothes. A loose fitting shirt, and a pair of lace panties that were just barely holding her flaccid cock. She smiled as she sat down in the same position as before, but this time, I could see her cock more easily. As soon as I was done, I sat up, on my knees and smiled.

"All done!"

"Are you sure?"

"Yes ma'am! I'm ready for my next task." I grinned as I tried to keep my eyes off her cock.

She noticed my stare and grinned as she slowly slid of her panties, letting her cock breathe. She leaned back, "well, I did need some other help." She grabbed her shaft and began playing with her cock. I quickly crawled under her and popped my head between her legs. Her balls were kind of saggy and I began by licking them. I kissed them, stuck my tongue out felt each wrinkle and vein I could, as she was rubbing her shaft. It got visibly harder as I slowly worked my way up to the base of the shaft with my tongue. She grabbed my hand and placed it on her cock and we both rubbed her cock together. She spread her legs more, letting her cock rest on my face as I continued to lick the shaft. She pushed me down onto the floor as she stood above me and used her cock to play with my lips. I stuck my tongue out and licked the tip, feeling her precum seeping down into my mouth. She painted my face with her precum while giggling and rubbing her cock.

"Having fun as a maid?" She said as she began moaning softly.

"Yes ma'am." I responded, loving the taste of her precum and her cock over me like a pendulum.

"Good! I'm glad he sent me such a good little slut." She smiled as she began dunking her cock into my mouth.

The next half hour felt like a blur as she just played with me like a toy. She didn't fuck me at all, making me edge and precum the whole time. I could see she was enjoying herself and having fun making me edge. I thought she was finally going to fuck me, but suddenly someone rung the door bell and she stopped.

"Go on now sissy. Someone's at the door, go and open it, like a good maid." She smiled as she sat back down on the couch. "And leave these here!" She smiled as she pulled off my panties as I was getting up to check the door.

I blushed as I got up and ran to the door. I composed myself as I reached it and wiped the precum from my face. I opened the door, my tiny cock hard and clearly visible in my uniform. I was so shocked when I saw who it was. I did my best to control screaming with joy as I saw the daddy that had sent me here. He was smiling as he saw me.

"Good evening miss!" He winked at me.

"Good evening Dadd- I mean sir" I corrected myself, holding back my slutty smile.

"I hope I'm not too late." He walked in and gave me a spank and smiled. "Glad you had the right clothes!"

"Thank you, sir!" I yelped from his spank.

He put his hand around me, cupping my cheeks as he walked in and greeted the futa. They talked for a few minutes, the whole time he played and squeezed my ass and she continued to rub her cock in front of both of us.

"She is such a good slut! Thank you for getting her!" She smiled

"I know, her mouth feels great! And she's always so eager to please." He pushed me forward between both of them.

"Now be a good maid and help master undress." She smiled as she rubbed her cock on me.

I could not hold it anymore and quickly unbuttoned his pants and pulled down his pants, letting his cock rub against mine. I took of his shirt and my chest rubbed against his manly chest making me audibly whimper. They both laughed as they saw how eager I was. I stood between both of them as blushing and smiling not knowing where to start. Daddy got on his knees as he bent me over and the futa grabbed my head, shoving her cock into my mouth. My eyes widened as I felt daddy's tongue playing with my tight little bussy. His hands firmly grabbed my cheeks as he dug deeper and deeper into me, penetrating my hole. I was standing on my toes as the futas cock was in my throat and I was choking and drooling on it as she was thrusting inside me.

After about 5 minutes of continually widening my holes, they finally decided to switch. As the futa slid her cock out, I fell on the floor, panting for air, but instead Daddy shoved his cock into my mouth. I began moving my head back and forth, feeling it throbbing inside my mouth. The futa spanked my ass several times until I could feel her cock being aligned against my hole. I tried to look back but Daddy grabbed my head and began skull fucking me. I held the floor to remain stood up but the futa shoved her cock into me, making my knees weak and my whole body shiver as I felt it crawling into me. Both cocks were so huge, it almost felt like they were both meeting inside my body. I was drooling and cumming, feeling both cocks throbbing inside me. I could hear them both laugh as they high fived and grabbed each other hands. They were now working back and forth in the same motion, crushing my insides. My mind felt numb as I felt the warm cum leak and then burst inside me. They didn't stop until both of them were flaccid and even then, kept their cocks inside for a few minutes. When they finally pulled out, I lay on my back with a big grin, a cum covered maid's uniform and a gaping hole. The both of them panted as they looked down at me.

"Wow, so how did you like it?" Daddy asked as he wiped his sweat from his forehead.

"It was fun!" She laughed as she spanked my ass, making some cum spurt out.

"Good! Let's rest up and go for another round?" Daddy asked as he began putting his clothes on.

"Definitely! I have a couple more in me!" She laughed again as she dressed herself up again. "Now be a good sissy and get us some drinks!" She spanked me as both of them sat on the couch.

I got up and went to the kitchen, I got them both two tall glasses of Orange juice and came back carrying it in a tray. They both grinned as they saw me enter and made room for me to sit between both of them. I sat in the middle, as I placed the tray on the table. They both quickly finished their drinks and became more relaxed and slouched down on the couch. That was until they saw my tiny little cock was already hard.

"Wow! He's already hard and ready for more" She asked Daddy a bit shocked

"Yes, he's a good little slut" Daddy smiled as he pet my head.

She leaned forward and grabbed my tiny cock with just her thumb and index finger. "The operative word being 'little'" She giggled.

"Or 'slut'" He retorted as he stuck his thumb into my mouth, and me being a good slut began sucking on it like a cock. It all became too much for me as she began playing with my cock and I came onto her hand.

They both laughed as she wiped her hand into my mouth to clean it. I could see both of them were ready for more as I gently placed my hand on both of their cocks and they were hard and throbbing. She smiled as she fed me a pill, which I eagerly swallowed and then began kissing both of them one by one. Soon we were all getting up and heading out back to the pool.

That is pretty much all that I remember clearly, the rest of the night was a blur. I do remember the large pool but not getting in it. I remember a sex swing, a bunch of dildos, vibrators, a big statue, and even a car ride and looking out the window at several people. I woke up the next day, somehow in my own bed. My costume was crumpled up on the floor and there were some cum stains on my sheets. My ass was still sore, and as I rubbed it, my hand caught a note, it read:

"We had so much fun with you! You are the best! Sorry for drugging you, but you were so much looser and more fun after it. Visit me any time you want. -- Victoria"

So that is pretty much it. I think I might just visit her again sometime. I should also definitely thank Daddy in some way.