For several years now, I have been tempted to go out dressed as a sexy girl on Halloween night. There have been several problems with that scenario.
First, I'm a guy, and I don't even remotely pass as a crossdresser, especially with the beard and moustache.
I had also been dabbling with chastity recently, going so far as doing Locktober online. I figured that going to a party would be extra painful and I wouldn't enjoy it too much.
But I was determined to enjoy myself – Locktober may have played a part, as I was getting very horny three weeks into October – so I started making an actual plan.
I asked the organizers about my facial hair, and they said "sure, if you go the extra mile on the costume and make-up".
But Halloween is October 31 after all, so I talked about my plan to my keyholder/online mistress, and she agreed I could get my key back at 5pm, go to the party, send her some proof pic right before midnight, and then I would be free to unlock.
To make sure I wouldn't cheat, she made me tie one of those plastic zippers with a unique number and send her a photo, before she would give me access to the key.
If the zipper was not attached to the cage in the proof pic shot at midnight, I would be in big trouble.
(Of course chastity cages can be broken out of, it was mostly a question of trust between us, and I knew full well that if I betrayed that trust, I could say bye bye to kinky fun online with her)
So, on Saturday morning, I set out on my plan.
First I shaved my face as best I could. I set out on a clean goatee, very much John Willie-like.
I had found some hair removal cream that was safe for my face, so I made sure my goatee was very clean.
Then I applied stronger hair removal cream to my legs, and made sure they were clean as well.
Morning preparations done, I went about enjoying my day, buying some food and cooking, and enjoying the feeling of silken smooth legs.
At around five, it was time to start getting ready.
I put on some fishnet bodysuit, for the goth look, over which I put a form-fitting gown.
Next part was a shiny waist cincher. I would not pass as a girl, but I would at least try to look shapely!
I also had a long black wig to try on, and a black choker that hid my Adam apple.
If you can picture this out, I looked a bit like Elvira, but very flat-busted, and without any make-up.
Oops, time to put on some flesh-colored padded bra. I didn't want to overdo it, but now I had at least some hint of a curve.
As for make-up, I had watched a lot of internet tutorials, and dabbled a bit. This was Halloween after all, so I went all the way: very pale foundation, dark lipstick and mascara to make my eyes look bigger.
I didn't quite recognize myself in the mirror. Even with the goatee, I looked pretty damn sexy.
To calm my nerves, I downed two shots of whiskey. I decided to skip dinner: my stomach was all flutters and butterflies anyway.
I had ordered an uber at 8:30, sharp. I looked online if my keyholder was around, but nope. So I kept fidgeting until it was time to go. I had prepared a small backpack, with my drop-dead black heels in there, the wig and a few other trinkets, including my chastity keys.
I put on a long trenchcoat and went to the rendez-vous point. I figured, I might get a bad mark from uber from showing up half-crossdressed, but with the trenchcoat, the only really unusual thing was my make-up, and since it was Halloween I hoped it would be alright.
One thing kinky people always overestimate is the interest other people will pay to their games. The uber driver didn't even bat an eye. Obviously, as long as he was getting paid, he was happy. The ride was not very long, and I actually knew my destination, having been there once or twice already.
There was some faint music. The party was just starting. As usual in those venues, there was a location where I could change, leave my trenchcoat, remove my sneakers, put on the heels and the wig.
I had a small chain necklace, from which I suspended my chastity keys. The locker's ticket, along with my phone, went into a hidden pouch on the dress's waist. One last make-up touch-up and I was ready to paint the town red!
Getting there early was good. I'm not too fond of busy crowds, so I had a chance to practice my dance moves before the floor was overcrowded. After all, I wasn't really used to dancing in heels. "Dancing queen" I am not!
The floor slowly filled up. There were some awesome costumes, lots of sexy nurses, vampires, and a few more exotic creatures. One woman had rubber tentacles over her arms and was sexily wrapping them around her boyfriend.
I tried to make eye contact a few times, even had a few dance moves with some sexy women, but it didn't seem to go anywhere. What can I say? I'm shy!
Just then, the DJ was getting into things. His current theme seemed to be oldies, which suited me. And "the monster mash" is perfect for Halloween.
Suddenly, a voice behind me called:
"Oh my, what are we going to call you, Elvis or Elvira?"
I turned around and had to lower my gaze to this elfin girl dressed up like Tinkerbell, but in red and green latex.
This young, sexy petite thing was hitting on me!
Of course, I didn't know what to say, but this didn't seem to phase her at all.
The next song was "Dead Man's Party".
Tinkerbell smiled at me "oh girl, I love this song."
"So do I," I managed to reply.
And so she started dancing. If you recall, that song is pretty energetic! Danny Elfman can swing a tune! I was doing my best to follow the nimble girl, gyrating my hips and trying my best not to break an ankle, mesmerized by the way she moved in her latex. She had platinum blond hair and hazel eyes, a gaze that felt much older and piercing than she looked.
Obviously, the cage was reminding me of its presence. Just a few more minutes and I would be able to go to the bathroom, take my proof picture, and finally remove the cage.
But we danced through two more songs. I could see some sweat pearling on her bare arms, which means she was positively cooking in her costume.
Suddenly, she threw her arms around me and kissed me.
You know how most women are passive and let you kiss them? She was not one of those women! I felt her tongue explore my mouth, and she even bit my lips a little. At the same time, my senses got assaulted by her full-on musk, a mix of sweat, latex and excitation.
I know it's a full-on cliché, but for a few minutes, time stopped. Then she came up for air and said "How about we grab a drink?"
"Sure, I'm paying."
So we went to the bar for cocktails, and sat down on stools. In this area the music was subdued. We chit-chatted for a bit. Turns out Ruby was working as an independent graphics designer, living only a few subway stations from my place. Apparently, she had a whole workshop to herself. She certainly was successful.
After the cocktail, as I was getting ready to go back to dance, she grabbed my ass and said "no, you don't go there gurl, I have other plans for those cheeks."
Mesmerized, I let her lead me to another area of a party, some kind of semi-public play area.
"Elvira has been a pretty naughty witch. We can't really burn you at the stake, but I want to see those bad buns red hot, baby," she said as she directed me to some kind of X cross, and started locking my hands in manacles attached high on both arms.
By this point, the cage check and unlocking was pretty much forgotten, though my dick was trying its best to escape its prison on its own.
She grabbed a paddle and gently swatted my bottom, then slowly started to lean into it.
After about 40 swats, my bottom felt pretty hot and red. I was in submissive heaven.
That was when she noticed my necklace.
"What the heck are those for?"
"Those are the keys to my heart". (corny I know)
"Oh yeah baby, sure. I know what THOSE are," she replied and gave my crotch a squeeze, copping a feel for the cage, and my blue balls.
"My, what have we here?" she acted surprised.
It was painful, but my caged cock felt otherwise and tried to grow even further. If I wasn't restrained, I would have already taken the cage off, as it was after midnight. But as I stood half-hanging from the cross, I was still trapped, even though willingly.
I groaned, between the pain on my ass and the stifled erection, this was going a bit far. Much to my dismay, she took the keys from the necklace, and just told me "I'll be back."
Suddenly I felt very cold, and tried my best to escape. But those play manacles were sturdy, and it's pretty hard to escape when your hands are tied separately. She came back a few minutes later. She wasn't holding the keys. I had no idea where they could be!
"Well, you'll be surprised to know that Miss D. is a good friend of mine on FetLife. When you told her about your plan, she also told me. She figured it would be the best gift ever, to end online Locktober with a real life experience. I don't think you're going to mind too much. Your locked cock seems to approve anyhow. I've always wanted a sexy sissy as a girlfriend.
“Don't even think about asking for the keys back. Not yet. And anyhow..." She snapped some photos. "There, even with the make-up, your face is very recognizable. I doubt you want these all over Facebook."
Almost as an afterthought “oh, and I just sent some backup copies to Miss D., just in case you think you can overpower me and delete them from my phone.”
“Besides, you were supposed to send a proof pic around midnight, and it’s now nearly 3 in the morning. Oh, one last detail.” She snipped out the numbered plastic tag. “Now even if you send a picture, your online keyholder will know you tempered with the cage.”
So here we are, at next year's Halloween party. Gone is the vamp-themed Elvira outfit. This year I'm going as a french maid, complete with the feather duster.
My mistress over the last year has been very strict. I spent a full month unlocked while my new PA piercing was healing, with stern warnings over letting it heal properly and not fooling around. Not that I have fooled around a lot over the rest of the year, at least not with my chastised cock!
Ruby told me that if I'm a good little maid who does everything she says, she might give me a treat after the night ends!
So here I am, locked in a pillory. She already used the crop to make sure my ass is an attractive cherry-red, glowing as much as the princess plug up my bum.
Then she shows me a sign that says:
"blowjobs 5€
pegging 10€
fucking 20€"
"I expect to get at least 500€ from you tonight. Otherwise, you can forget about getting unlocked before Valentine's day."