Chastity with Ex as Keyholder Ch. 06bychastity_sissy©
My Ex knew me. She knew me better than I knew myself. She knew it had been a deep, disregarded fantasy of mine to be a helpless maid amongst a variety of men and women, all dressed up in pretty outfits demanding drinks and snacks from the maids passing by.
She had, without a doubt, put "the guy" in his place. My cock was completely locked away in full metal, and it would require an ER visit to physically remove the device without a key. I didn't really trust myself with a pair of bolt cutters, especially since the cage was so small and the angle completely awkward.
All of her friends thought it was completely hilarious, of course. They thought I was just an off-the-wall sort of character who liked attention. And it really wouldn't have been that weird, if it hadn't been me and I hadn't been wearing the metal chastity device. I would have thought it completely entertaining for my hot Ex and her hot friends to have some random guy all dressed up as a maid serving drinks to everyone at a Halloween party.
I still hadn't completely adjusted to the new cage, either. In fact, I had never really adjusted to the other plastic cage! Any device that keeps the male organ from attaining its natural state of arousal cannot be gotten used to in my book. I wish I could get adjusted to these devices because then it might not be such a slow, constant, torturous experience.
As it was, I had never dressed in public before. All my dressing had been done in private, maybe amongst a select girl or two who were kinky enough to handle it. This was a completely different environment for me, and I had a feeling certain girls could sense it, especially when I could swear they were whispering to each other after I had walked by.
In reality, I was creating a lot of this in my own head. My Ex had gone shopping and bought me a relatively modest maid outfit for this party. The hem length was long enough and the petticoat offered enough volume to completely hide any trace of a chastity device. Now, if one of the girls got sloppy drunk and started grabbing at my crotch, there was obviously nothing I could do about it.
The top part of the costume covered my chest and shoulders, but my Ex also bought me a nice push-up bra to give the illusion of breasts. Then there was the wig and makeup. I never really was huge on the wig and makeup piece of dressing, but my Ex decided it would all be a fun part of the show to have me completely done up, head to toe.
Hours before the party I was shaving my legs and considering my options. Here I was, a moderately successful IT professional with a nice apartment, car, and income. How easy would it really be for my Ex to bring it all crashing down? She apparently had added my boss as a friend on Facebook. He'd add any girl with a cute ass. Could I find another job, delete my Facebook account, desert my apartment, and run away from all of this?
As I soaked there in the tub, I realized it was a yes and no question -- the same as it had been since this whole thing started. Maybe it was an addiction, an addiction to being denied the pleasure of orgasms while simultaneously being humiliated with wearing the quintessential pieces of what I considered female attire. Would I really want this to end, if I could really make it happen without causing several life altering decision to be made?
The decision was apparently made as I slid the black nylon stockings up my now smooth, soft legs. The metal chastity device glistened in the bathroom light. It was shorter and smaller than the plastic device, allowing no hardness whatsoever. It occurred to me that my Ex had probably spent a generous amount of cash on a device like this, a bill which she hadn't sent my way. My cock bulged against the confines of the cage, wishing against hope for any type of relief, but the metal held firm. The teasing was constant, even more so than the plastic device.
Normally, if I had been going to work or doing something mundane, my cock my get naturally flaccid, but tonight was different. I was shaking by the time I had gotten out of the bathtub. Tonight I would be displayed in front of my Ex, her hot Hooters friends, and all of their male guests. I had no idea what to expect. I couldn't even remember the last time I had had an orgasm at this point, but it felt like it had been over a month. I couldn't remember anything but being insanely horny and both loving and hating my Ex for understanding me more after our relationship had ended.
"I'm going to make you the best looking maid tonight," my Ex said after I had slid the nylons up my now hairless legs. She had her complete make-up kit with her and she was serious. "You do have some nice features, you know, had you been a girl. Might have been a better thing since you won't ever get to use that dick again," she said giggling. "All locked up in chastity, can't even get a boner anymore. Sucks to be you!"
I could only sit there in front of my mirror while she applied the multitude of layers that condone a proper make-up job. The foundation, the blush, the eye liner, the lipstick...and she was an expert. By the time she was done, I could hardly believe the version of me I saw in the mirror.
I dare to say...I looked almost...hot!
However, you could still tell something was off. If you looked hard enough, you could definitely tell something was amiss, but it wasn't obvious by any means. My Ex had done a marvelous job.
"What can I say?" she said sweetly. "Now, get finished dressing up and we'll head over to my place!"
Without messing up the make-up, I finished dressing in the maid uniform my Ex had provided. I slid my apartment key off my usual key ring and put it in the waistband of my pantyhose, hoping I would be dropped off at some point.
"You really want me to go out like this?" I asked, feeling extremely nervous about venturing into the real world with nothing but a maid uniform.
"Um, yes. How else are you going to get to my party?" my Ex said, opening the front door. "You look super hot and no one will know you're not a girl unless they get up very close."
As instructed, I vacated the safe haven of my apartment and ventured into the real world. The wind grazed my legs and I felt it all the way up to my ass, sending tingles down my thighs and to my toes. The feeling was amplified by the pantyhose I was wearing, the shimmery, tight fabric constantly hugging my legs.
Of course, my metal cage was holding firm against the numerous attempts by my cock to get hard. Everything felt a little new to me. Sitting in my Ex's car, feeling the wind around me. At a stop light, a couple of dudes tried to flirt with us. I didn't know what to do. I never considered myself gay, but dressed up like this with my cock all locked away, and not having an orgasm in month, I could actually see myself pleasuring a cock. Shake your head in disgust, if you will, but become horny enough and denied orgasms long enough, and you'd be surprised what leaps your brain will make.
The thought both scared and excited me, but I kept my mind to myself. My Ex did most of the talking.
"Wait until you see my costume! It's so cute. It's a throw back, but it's always a hit and I haven't worn it in years. Now, when we get there, you need to start loading shots onto trays for when the guests arrive. My boyfriend is working late at the gym so he won't be at the party until later. Does it make you nervous to know you'll meet the man with The Cock?" she asked giggling.
And yes, it did!
Like a good little maid, I started filling small paper cups with shots of liquor, allowing me to take my mind off the entire situation. Here I was, dressed up as a French maid, locked up in chastity, and about to serve at my Ex's Halloween party. What could possibly go wrong?
Someone knocked on the door. I froze, a deer in the headlights, unsure what to do. The person knocked again.
"Um, get that maid!" my Ex called from the bedroom.
I steadied myself and carefully walked to the door in my heels. Taking a breath I opened the door.
I couldn't believe who I saw. It was Kara, the girl from the gym! The hot brunette had decided to be a sexy little Dorothy with black heeled shoes, white tights, and a frilly little dress complete with a small basket.
"Well, well," she said. "Aren't you going to offer to take my purse?"
My cock was raging inside the metal cage, battling the limits of the chastity tube. I wouldn't even call it a tube, it wasn't long enough to be a tube. My cock had barely enough room to just exist flaccid, let alone constantly attempting to get hard.
I tried to hide my discomfort as an inability to walk deftly in heels.
"I didn't know you were friends," Kara said as we walked into the kitchen. "She mentioned someone was going to be our guest maid for the evening. I have to admit, you do pull off the whole maid look pretty well."
"Thanks?" I said, unsure how to respond.
"Oh, it's a compliment!" Kara said, eyeing me up and down. "How did she convince you to do this?"
Not wanting to admit my Ex had my dick locked up in chastity, I said, "It sounded kind of fun, I suppose."
"Oh, it will be!" my Ex said coming around the corner.
Now, uniforms are sort of my thing. Hooters uniforms, school girl uniforms, the whole array. My Ex had apparently resurrected her high school cheerleader uniform, complete with the bodysuit and pantyhose.
"You look so cute!" Kara said, hugging my Ex.
"I figured it'd be fun to be a cheerleader for the night. Plus, Jack here loves the pantyhose, don't you Jack?"
Blushing, I said, "Oh, you know it!"
The girls giggled, exchanging a slight glance that I almost didn't catch.
"Then that means he must love my white tights, too!" Kara said.
"Yeah, Jack's pretty much a hosiery slut, aren't you?"
Had I not been extremely aroused, dressed up, and locked in chastity, I would have been horrified by my Ex's comments.
"It's a good thing you can't get hard, though, since it would be bad for a maid to be walking around with a huge boner," my Ex said.
What the hell was she doing?
And just at that moment, more people started to arrive. Apparently, they didn't care about knocking. Within the next several minutes, my Ex's apartment was flooded with people. I tried to keep up with the influx of bodies, but my drink tray was always empty.
No one really cared that I was really a guy dressed up like a maid. Half the people were drunk on arrival and probably thought I really was a girl. Several guys grabbed my ass as I walked by with the empty drink tray. I can't deny it made me a little aroused to know other men were considering me attractive.
I was surrounded by scantily clad women, some of whom wore pantyhose or tights, causing my poor cock to try and get hard. I had hoped my cock would learn that the metal cage was even more secure than the plastic one, but it didn't. Time and time again I felt my cock push against the boundaries of the metal cage.
My Ex knew exactly what she had done. Here I was, with no way to get an erection, dressed up as a sissy maid, surrounded by hot girls and guys.
The next two hours passed by me in a blur of serving drinks to drunken people, avoid groping hands, and trying to find my Ex, who had become somewhat hard to find in her own apartment.
I was refilling the shot tray when Kara came over, who was a little tipsy at this point.
"So what did she mean that you can't get hard?" Kara asked.
"Oh, uh, the pantyhose...they kind of keep a guy in his place, you know what I mean?" I said trying to play it off.
Kara definitely had an adventurous look in her eye.
"So you get hard wearing pantyhose?" she said, giggling. "No wonder being a maid sounded fun to you! Since you're a maid, would you clean my red shoes if I told you to?" Kara asked, sipping her drink.
If anyone could be more hot than my Ex, it would have to be Kara. She had these large, doe-like eyes that combined forces with her prominent cheek bones that created this adorable, yet exquisitely beautiful face. I couldn't believe such words were coming from her sweet mouth.
"I uh, yes, I suppose, since I am a maid and all," I said, kneeling down before her.
Would my Ex be angry I was worshipping another girl's feet? Without knowing what to do, I knelt down with a paper towel I had grabbed last minute, and began polishing Kara's left high heeled shoe.
Apparently, several of the drunk people around us thought it was incredibly funny and created a small circle around us.
"You call that cleaning?" I heard one drunken male voice shout.
Others began to join in. "Yeah! Use your mouth! Lick it! Lick it!"
Before I knew it, half the part was standing around this display, apparently entertained by the sight of a maid cleaning the heels of a sexy Dorothy, and shouting commands.
"Yeah, Jack, lick'em!" Kara said giggling.
Without a second thought, I was licking her shoes. The crowd loved it. And when I say crowd, it felt like a hundred people to me, but there weren't more than twenty people in my Ex's place. I had unwittingly become a central part of the Halloween entertainment.
"Suck on the heels, maid!" I heard some female voice yell out. And then, everyone was yelling for it.
I looked up at Kara and she only smiled, pushing her high heeled foot in my face, obviously having fun with the whole situation.
"How often do you see Dorothy getting to boss a maid around?" she asked the crowd, who was obviously enjoying watching a hot Dorothy give orders to a French Maid.
And there I was, dressed up as a maid, locked in chastity, licking the high heels of my Ex's hot friend in front of an entire crowd of people. My cock desperately launched an attack against the confines of the metal cage, but it only resulted in precum dribble. I could feel the warm liquid slowly dripping into my panties, but there was nothing I could do about it.
I loved the taste of her plastic heels. My tongue couldn't get enough. And somehow, I sensed that Kara also enjoyed it. There was something in her smile that was more than just a casual amusement, but I couldn't tell if it was the extreme arousal, alcohol, or intense humiliation that was making me see something that really wasn't there.
I suppose it's ironic that I was so incredibly horny, yet completely unable to even get a boner in this situation. Here I was, surrounded by hot girls in skimpy outfits, most of them including pantyhose, while sucking on the heels of another very hot girl who was wearing pantyhose while locked up in chastity, dressed as a maid.
It was completely ridiculous, but the people seemed to be on board with what was happening. Apparently, public humiliation is perfect for intoxicated people. All the while, Kara simply sipped her drink, playing the part of a semi-interested sexy lady.
My Ex finally came out of nowhere. She said, "Oh good, you found a good use for the maid. Okay everyone, my boyfriend is finally about to come home! So this party can really get started!"
And with that, I had to face the realization that I would finally meet the man with the cock who was currently fucking my Ex...while I was locked up in chastity...unable to get hard or have an orgasm...at least until my Ex said it was allowed. And did I mention I was the one who dumped her? Note to self; be aware of dumping kinky girlfriends for future retribution.
Just then, my Ex's current boyfriend walked into the room.