The Night I Lost My Mistress

Today Mistress picked me up from the airport and said "I have something special planned for tonight and it's a surprise." We chatted about mundane things on the drive to her place, but my mind raced with what she might have in mind. I know I hadn't had my "A" game going the last couple of visits so this was my chance to really buckle down and show her how much she means to me. We went into the house and I immediately took off my clothes and locked them in the box by the door then proceeded to the basement, assumed the inspection position and waited for Mistress. It didn't take long before Mistress entered and began inspecting me. She always started out with tweezers looking for even the smallest hair I may have missed so she could slowly pull it out in punishment for having missed it in the first place. She pulled 6 and told me "good boy". Next she locked on my chastity device and pushed her finger into the middle of my back to signal me to bend over. Once I did I felt her rubbing lube on my ass before quickly popping a finger inside, then another and then a third. She spun them around in me forcing my hole to open more. When she was done she pulled her fingers out and smacked me on the ass. "Good job, but I want you to go douche again then meet me upstairs in my bedroom." I hurried off to do as I was told wondering if this might finally be the time she lets me fuck her. The more I thought about it the stranger that sounded since she had locked me in chastity first.When I was done I proceeded upstairs and knocked on the door. My knock was greeted with an "Enter" command and when I did she was sitting on the bed with clothes laying out around her. She said "Tonight we're taking you to a bar dressed as a woman. We're going to let you practice your walking in heels in a real world situation and see how you do. I've bought you a wig and am going to help you with your makeup. Bend over and spread your cheeks." She quickly popped something in my ass and pulled it out, well that's not entirely true because I still felt something inside me. She showed me the tampon tube she had just inserted in me and gave a quick tug on the string to make sure it was in properly and the string was dangling appropriately. This made her smiles and she said "Just wanted you to feel like a real woman. We will start with the foundations and put on your bra and panties first." They were red lace gstring and bra with a rear closure but the bra had an extra strap on the back. She noticed me trying to figure it out and said "Just put it on and I'll help you with those." The string from the panties almost immediately disappeared in my crack. I added the bra and when I had it closed she smiled and ordered me to turn around. When I did I heard 2 clicks and felt something cold on my back. "I wanted to make sure this stayed on so I added a lock to the closure and just to make sure I locked those 2 extra staps closed so you can't slip the straps over your shoulders to get out of it." She spun me around and adjusted my panties to cover my cage until she was satisfied with how it looked before making sure my tampon string was still dangling between my cheeks. Now she tosses me a very short white miniskirt. Without a word I put it on, but it barely covers the end of my chastity cage and only half my ass. She tells me to turn around and when I'm done I see her smile gleefully again. Now she tosses me a hot pink cutoff shirt that has "I love cum". I look longingly at her, but she nods her head and points at the shirt. I put it on and she openly laughs. "This is going to be fun." Next she puts a set of 6" heels on me and locks them on. I'm already over 6' so I am now toweringly tall. She orders me to sit down at the makeup table. She adds foundation, lipstick, eyeliner, eyeshadow, plucks my eyebrows until she is happy with them, adds fake lashes, a new collar and the wig before painting my finger and toenails. She closes the bathroom door and tells me to come over and look at myself in the full-length mirror on the door. No doubt I make an ugly girl, but Mistress seems pleased. She hands me a black clutch and tells me "You will want this later, but don't open it just yet." She attaches a metal leash to my chastity cage and leads me out to the car in the garage before we take off for the club. It's a quiet ride as I struggle with being out in public like this. Every so often she runs her hand up my inner thigh and pulls my legs apart so she can flick her finger at my balls and watch me squirm. When we finally arrive at the club it's still daylight. Mistress gets out and crosses over and opens my door. She reaches in, grabs the leash and gives it a quick, sharp jerk. OK, guess I need to get out as I groan from the pain. I'm not good at this and manage to give the entire parking lot a free show as I turn to get out, stand up and straighten out my clothes. Mistress reminds me to take my clutch with me and when I bend over to get it out of the car she tells me to "Stand still". I hear her rummaging through her purse then I feel her writing something on my upper thighs with a marker. I wonder what that is all about. I hear her phone take a picture and she tells me "I'm done, you can stand up now." Mistress puts a sharpie back in her purse and leads me in by the leash. Once inside she walks me around the bar twice and finally says "I think we will have a drink at the bar." We go over to the bar and she orders us two glasses of red wine. Mistress pushes on my back gently and I lean forward over the bar a bit before she removes her hand. We stand there for a bit chatting and sipping our wine when she slides her hand up my skirt, grabs a hand full of ass and gives it a good squeeze as she smiles at me slides her hand down my butt cheeks and gives my tampon string a couple of gentle tugs. Mistress hands me my drink, picks hers up and leads me around the bar by the leash a few more times sipping her glass and chatting with me before we go back to the bar and she orders us another round. Once the new drinks show up a second set of glasses quickly follow. Mistress enquires about them and learns they were sent by a gentleman at a booth in the corner. Mistress picks up her glass and tells me to get the others as she leads me over to the booth. She slides in an orders me to squat next to the end of the booth. The two of them whisper back and forth for a few minutes, giggling and drinking. Mistress tells me to quickly drink down a glass of wine. She reaches over, lifts up the front of my skirt and disconnects her leash. Next she removes the new collar she gave me before we left and replaces it with a wider leather collar and locks it in place. Next, she locks a heavy metal chain to it and laughs. Mistress slides out of the booth, hands me the clutch she gave me and tells me to open it. When I look inside I can see it is filled with rubbers and lube syringes. She winks at me and says "Be good now because you sucked for me the last few sessions.", shows me a picture on her phone of what she wrote on my thighs and walks out the door. I am horrified to see that she wrote "Need Cock" on my thighs! I stand up to follow her but am quickly pulled to the ground by a forceful jerk on my collar. I look up at the man on the end of the chain and he flashes me the keys to my locks. He smiles and says "You're my bitch now." I think to myself, this is all a game right?! She is just fucking with my mind and didn't actually give me to this guy, right? He hands me another glass of wine and tells me "Drink it." I put the glass to my lips to take a sip and he grabs the glass, holding it to my mouth so I have to drink it all. When the glass is empty he pulls on my chain and says "Let's go". I have no choice but to follow him out of the bar or end up on my face being dragged out. I can't put up any resistance in these damn heels and I struggle to keep up with his pace. We get over to his motorcycle and he locks the other end of my chain to back of it. He slides his hands under my skirt exposing my ass to anyone who happens. He spreads grabs one cheek and lifts it up to spread my ass open before he wraps my tampon string around his finger on his other hand and slowly pulls it out. He smiles while he watches my face as the tampon, now swollen by the lube Mistress put in me earlier forces my ass open. "I hope you have more of these in that purse because you're going to need them by morning." He pulls my chin to him with one hand and slides his tongue down my throat as he slides two of his massive fingers fully deep up my ass. He uses my ass to lift me even higher onto my toes forcing my heels to come off the ground. He pulls his hand from my chin, reaches under my skirt and gives my balls a quick squeeze and a tug while he slides his fingers in and out of my ass. When he finally lets go of me he says "We're going to the club house next so I can show you off and pass you around. Your Mistress said you always wanted a gang bang so tonight is your lucky night bitch." He unzips his pants, pulls out his cock and tells me "Get on your knees and start sucking bitch! I get the first blowjob tonight." I slink to my knees and open my mouth to accept both his cock and my destiny for the night as I hope that this is all a game for Mistress and that she will return for me.

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