Sorry for the long wait, have had this story saved in drafts for 2 years now but I stopped using Literotica and kinda forgot it existed until I hopped back on...whoopsie. Hope you enjoy!
I woke up excited for the first time all summer. Today was the last day I would have to serve these vile creatures; I had actually managed to make it through the whole summer cleaning and being humiliated and treated like I was less than human, all while holding back pure hatred for my mistresses. Of course they had to know how much I despised them, they weren't stupid. But the fact that I hated them so much just turned them on more, I could see it in their eyes. I got out of bed and put my uniform on, as humiliating as wearing my diaper was I couldn't help feel snug and comfortable in it. A layer of protection while also reminding me of what a stinky baby I was for making messes. My pussy was a throbbing and sensitive mess, just aching to be touched. I took a deep breath and avoided the temptation, heading downstairs to get breakfast ready.
I walked into the kitchen to find waffles sitting on the counter, "good morning piggy." Lisa greeted me cheerfully as I entered. "Since today's your last day with us, we decided to give you a special treat. Eat up!"
I couldn't believe the words that I was hearing. 'Is this some kind of trick?' I wondered. Why would they be nice to me on my last day, I thought they would torture me for sure. I decided to just count my blessings and not question it, the waffles tasted delicious and for the first time in three months I was in a good mood. I ate every last bite and cleaned up after myself before getting the vacuum to start cleaning. "Oh there's no need for that today." Anna said watching me head towards the closet. "We're not going to have you clean on your last day, today's a day for celebration, not more work."
Was I dreaming? This didn't even seem real. "Thank you Mistress!" I responded happily. "If I don't need to clean today, what would like me to do?"
"Oh that's simple," she replied. "Just enjoy yourself, watch a little TV. If we need you, we'll call for you."
That last line had a different tone. It didn't sound like she truly wanted me to enjoy myself but like there was a surprise she was hiding. I started to feel nervous as I sat down, what would they make me do to suffer on my last day? I tried not to think about it as I turned the TV on and let myself relax. Whatever it was I'm sure I can manage, especially considering everything else I've endured so far. A few hours passed before I heard the little bell that told me to come upstairs to service my masters. I walked up slowly, anxious to know what was in store for me. I entered Lisa's room and found all of my mistresses standing together completely naked. My clit instinctively began to itch, I had not orgasmed all summer long, despite being teased consistency and their naked bodies had my undivided attention. "Mia, my dear." Lisa began, "you have been a constant help all summer long and I think you may be our favorite slave so far. You deserve a real reward for all your dedication. Today you're finally going to be allowed to have an orgasm, cum as much as your little heart desires. Then after today, you will be free, we will wire-transfer every last dollar you will need for school."
"I...I don't know what to say. Thank you!"
"No need to thank us, we'll be having just as much fun. Trust me." Stacey said.
They all looked like they were holding back laughter, it made me nervous. They all moved away from the bed and behind them I saw four very large dildos lined up. "Uhhhh..." I said uneasily, "what do you plan on doing with those?"
"Well that's simple," Karen responded.
All the older women were now putting harnesses on. "We're gonna fuck that tight teen ass of yours." She finished in a matter-of-fact tone.
I gulped. Sweat starting beading around my brow as I stared in fear at the big black dildos that lay in front me. They had to be at least 10 inches and were quite big in girth as well. I never had anything bigger in my butt than the enema before, which may have been practice for this, the more I thought about it. "Well don't be shy, we're doing this for you after all." Lisa said motioning me towards the king-sized bed.
I found myself walking over, almost in a trance; my eyes were fixated on the massive cocks that were about to penetrate my smallest hole. I got on to the bed and the ladies all joined me, surrounding me as they took my uniform and diaper off before admiring my naked body. Anna picked my diaper up and held it to her face as she inhaled deeply. "Mmmmm..." She let out a soft moan.
Stacey sighed. "I truly am jealous of your young perky tits, Mia." She said as she reached over and began to fondle them them.
Shivers ran up and down my body and I felt my nipples become erect in response to the touching and my pussy felt tingly and wet as they all started touching me up and down; massaging my boobs, squeezing and tugging my aroused nipples, rubbing my ass in a circular motion. Lisa tugged on my engorged nipples a bit harder and Anna moved her hand down to my sticky pelvic area and touched my swollen clit. Lightning bolts shot around the inside of my slit as she rubbed my clit in a circular motion. Karen sat behind me giving my cute bubble butt a good squeeze. "Oh yeah, this ass was made for fucking. I can't believe we've waited three long months to do this." She said in an excited tone, before giving it a light slap.
At this point I was sufficiently turned on; their breasts were right in my face and all I wanted to do in that moment was suckle on their engorged and rock-hard nipples. I found it amazing that even after all this time I was still turned on by them, despite everything they put me through. They all reached for their preferred cock and strapped the dildo onto their harness. "Who wants to go first ladies?" Lisa asked.
My horniness turned to fear in a blink of an eye. They were all sitting in a circle around me, looking me up and down with a hungry look in their eyes. "I think I'll take first crack at that ass." Anna finally answered.
I got on all fours over instinctively; I could feel my anus tense up in fear before a finger pushed its way inside. "OH." I said in surprise.
Anna kept fingering my ass while rubbing my pussy with her free hand. She leaned over me and whispered in my ear: "Are you ready to have your sweet ass fucked piggy?"
I didn't even get a chance to respond before I felt the finger disappear and an immense pressure building on my bottom immediately followed. "Oof, even with all that training this teen asshole is still as tight as her first fingering." Anna commented. "Guess we'll have to change that."
Anna pulled back for a second and rubbed some lube on her large cock and proceeded to lick her lips. She reached over and pulled my face so I was looking at her and the large cock attached to her, I was too much in shock to do much other than gulp loudly and stare at the member in fear. "Spit on it." Anna instructed. "I want you to add your own lube to the cock that's gonna turn you inside out."
I hesitated for a second before leaning over the cock and letting some spit dribble from my mouth. Anna rubbed the spit and lube up and down the shaft and head before pushing my face away again and setting herself up behind me. She rubbed the massive toy up and down my crack, building anticipation. I then felt two hands part both my butt cheeks and again I felt an intense pressure on my backside but this time I felt my anal walls open a bit. I let out a guttural groan as Anna slipped the big cockhead past my small brown ring. "That's better!" She said with glee. "Now the real fun begins."
"Mmmmmm...Oh Mia, your ass is built for a good fucking." Anna said sadistically as she slowly pushed her way past my entrance, forcing the cock deeper and deeper into my ass.
I gripped the bed sheets and let out more whimpers of pain as my sphincter began receiving the punishment of a lifetime. "Just a few more inches..." she said softly as she began focusing intensely on my teen bottom taking the cock of a mature women.
It felt like it was all the way inside my stomach before her thighs made contact with my ass and all the women looked at me with sick pleasure in their eyes as their friend was now balls-deep inside my butthole. "Can't believe she took it all!" Stacey said in wonder. "I was sure that nubile body of hers was going to snap in half."
"We trained her well." Lisa responded as she picked up a small vibrator and reached under her friend's harness to give her pleasure.
"We sure did!" Anna exclaimed. "Feeling these juicy cheeks bounce against my thighs is doing wonders for me."
She pulled all the way out before shoving it back in, faster this time and with more force. I was groaning, tears leaking from my eyes as I endured the immense pain and Miss Anna began to pick her speed up very gradually, finding her rhythm. "Mm...mm...mm...mm..." I moaned repeatedly.
The others were waiting their turn patiently. Touching each other and rubbing vibrators over their clits as they all watched my teen ass get pounded from behind, like it was a live-action porno they were directing and watching in real-time.
I never felt more in pain, it felt like a was taking a massive shit in reverse. My sensitive butt was beginning to be pounded roughly but at the same time I started to feel good. The friction rubbing my inner walls and the feeling of being full made my pussy feel amazing and I started moving back forth in time with the thrusts without even realizing it. "This little buttslut is really enjoying herself!" Karen said in surprise. "I suppose we really were successful in turning her into our little buttslut-bitch."
Anna took that as words of encouragement and starting moving her hips faster and faster. "Fuck that little whore!" Stacey growled aggressively while Stacey was moving her hand under her cock to rub her hot pussy.
