Halloween Filled with Surprises

It was 7 PM when I hopped on my bike and made my way over. "630 Collins St. Wear the big plug." was all she texted me just 15 minutes prior. It was the first time Miss Daphne had messaged me all week, and I'd been anxiously awaiting word the entire time.

She was the only thing on my mind since the previous Sunday, when she had absolutely rocked my world and left me in a puddle of subspace that took me hours to crawl out from. That day, she tied me flat on the floor, blindfolded and gagged me, unlocked my chastity cage, and teased me relentlessly with her feet. She left me horny and unsatisfied that day, icing me down and locking the cage back in place. She put headphones over my ears and did something for about 10 minutes before removing one headphone, whispering in my ear "good luck Vivienne. See you soon", then untying a single hand and making her exit. She had taken to calling me Vivienne whenever we were alone, insisting i view myself in a more feminine light so ling as I was under her clutches. By the time I had untied myself, I could see what she meant by "good luck"; she took my entire bag of sex toys (an extensive array of toys at this point) and hid each toy somewhere else in my apartment. I had to scramble to find everything before my roommate came home. I was annoyed but I knew she enjoyed inconveniencing me like this. If it pleased Miss Daphne, then I was willing to tolerate anything.

I recognized the address: it was a mutual friend of ours, Tessa. She was the one who had introduced us, although these days Tessa was closer with Daphne than myself, as was I.

It was Halloween night, and I wasn't sure what the plan was. I wasnt big on costumes, and hadn't worn one tonight. As I arrived at the house, knocked on the door, and Tessa answered.

"Hey dude, come on in. I was just putting on makeup. Daphne's out back"

I made my way to the backyard, and took in a sight to behold; Miss Daphne was sitting on the patio, wearing a skimpy black dress and 6 inch black stiletto heels. On her head, a pair of devil's horns completed the look. Around her neck, the key to my chastity cage was clear and visible for anyone to see. My cock throbbed inside the cage and in that moment, I felt every inch of the plug

"Like what you see, Viv? Im a succubus!"

I gathered myself and replied to my Mistress. "You look amazing Miss--"

"Lets just stick to Daphne tonight. Dont wanna tip anything off to our friend. She is still in the bathroom, though. You can greet me properly, if you do it fast."

I collapsed to my knees and gave her heeled toe a gentle kiss, once on each foot, just like she expected. Then I sat on the patio steps as she sat above me.

"You bring a costume?" She asked me.

"No. Didnt have time."

"Figured you might say that. You're in luck. I got you something. It's in my bag, just inside here. Wait till Tessa is done in the bathroom, then go to the bathroom to change. You can put it on under your regular clothes."

Once Tessa was back outside, I excused myself to the bathroom and fetched the bag in Daphne's purse on the way. In the bathroom, I saw what she'd gifted me: it was a chiffon French maids outfit, complete with lace and covering almost nothing. Also in the bag was a note which read: "deposit your boy underwear here. Vivienne no longer gets to wear underwear." Changing into the slutty outfit, I felt myself sinking into subspace, but knowing I'd have to keep my composure for whatever the rest of the night had in store. As I was wrapping up in the bathroom, I got a text from Miss Daphne: "send me a picture in the outfit. I want to see you Vivienne. I want one from the front and another with you spreading those cheeks and showing off that plug." With that I stripped down again, and sent some of the most revealing pictures of myself that I'd ever taken. I was humiliated beyond belief, but still so deeply submissive that I didn't hesitate to send the pictures over. My caged cock, brushed gently by the chiffon, was now pressing against my jeans causing a bulge that felt noticeable, if only to me.

I came back outside into the backyard, to find Daphne and Tessa giggling to each other in conversation. Maybe I was paranoid, but the way Tessa looked at me when I came outside made me feel like she could see right through my normal clothes onto the chiffon, lace, and hard plastic underneath. Something about her stare, like she was reassessing me after receiving some new information. I glanced at the key on Miss Daphnes neck, and wondered if Tessa had asked what the key was for. I wondered if Miss Daphne answered truthfully. Tessa was the one who broke the momentary silence:

"We were thinking about heading to the Halloween party at Bis Bar tonight. You joining?"

"Hell yea, I'm down."

"Great! We were gonna order a car, but you've got your bike here. You wanna bike there and meet us or leave the bike here tonight and come back for it tomorrow? "

I thought about the choice. The house we were at was far from my home, and I had class early the next day. I needed the bike, regardless of how badly I wanted to ride in the car with them. I opted to bike to the party, and apologized to the ladies for the inconvenience. Miss Daphne grinned at my decision.

After a while, the two ladies got up to leave. As they were walking out, Daphne, who was behind Tessa, discreetly passed something into my hand; it was a pair of bunched up panties. I stood there like a child in trouble, frozen in place as the two ladies began to leave. The text message, alongside a picture, came in as they were filing into the car: "those stay in your mouth the whole bike ride over here. Don't keep us waiting, bike hard. When you get to the bar, buy us a round of drinks and then come find us. Hope the plug isnt too uncomfortable with all that biking :)." I took a look at the picture. It was an upskirt shot of Miss Daphne, with no panties on, clearly wearing the same dress. She was magical, and she had now blessed me with the panties she'd been wearing today. As I put them in my mouth, her fragrance filled my mouth and had an intoxicating effect. I wasn't sure if I'd be able to bike from how dazed I was at what was already happening tonight. How did I get so lucky?

Like my Mistress commanded, I biked hard and fast trying to get to the bar not long after them. It was my second ride of the night while plugged, and while she had gotten me used to the notion of plugged biking, it was certainly not a comfortable endeavor. I was winded breathing only through my nose, but I ultimately made it to Bis Bar. I spit out the panties (discreetly, since there were now people everywhere), folded them and stuffed them into my pocket. With that, I made my way into the bar. It was still early, so the bar wasn't too cramped, but there were plenty of people around. I went straight to the bar, and ordered a round of three gin & tonics. I knew these to be the preferred drink of both ladies, amd while I personally didn't enjoy them, I decided to make the bartenders life easy and order the same as the two ladies. With the drinks in hand, I set about looking for Daphne and Tessa. I made my way outside, to a less busy part of the bar, and found the two ladies sitting next to each other in front of a small round table. They were sitting against the wall, on bench style seating, and opposite them was a small, short ottoman that they'd been holding for me. I made my way over, put the drinks on the table, and sat down on the ottoman. As I sat, I realized I was much lower than the two ladies; they almost towered over me from this angle.

"Sorry I'm late. This round's on me."

"All good! We were just talking about costumes. You dont have one!" Said Tessa.

I glanced over at Miss Daphne, who smirked with the knowledge that I did have a costume on, just not one that was presentable at a bar like this.

"Yea. Ive never been much into costumes, you know that. I know thats a bit of a buzz kill thing to say, I'm sorry. Maybe next year."

Tessa took a sip of her gin and responded.

"There's got to be something we can do for a costume. You live close, no? Maybe you could go scrounge something together."

I thought for a second. "I've got a hockey jersey and a Santa hat. Is that a costume?"

The ladies both giggled, and ultimately agreed that, no, a hockey jersey and a Santa hat did not make a Halloween costume. Eventually, Daphne spoke up.

"Why don't we just put some makeup on his face. Its no costume, but its something, and he wouldnt have to go home." As she said this, she smirked at me mischievously. Her legs were crossed, and one foot dangled the heel seductively close to me. She knew she had me, and I was never going to say no.

Tessa agreed: "I guess that'll do. But he cant have any of my makeup. That shit's too expensive for any face but my own."

"Thats fine, I've got some extra for him" responded Daphne. With that, she started pulling out different makeups. Right there, in the back of the bar, Miss Daphne pulled me close, off the ottoman and onto my knees so she could get a better look. She uncrossed her legs and strategically put a leg between mine, close enough to my crotch that she could feel the throbbing cock restrained by the hard plastic cage. She grabbed my chin gently and started putting makeup on my face. She started with lipstick, which was her own shade that she was wearing; it was a bright red shade that highlighted her black outfit perfectly. On me, it would be undeniable to anyone that I was wearing lipstick; it wasn't in the least bit subtle. She then moved onto mascara, which she applied gently. Then came eye shadow, and finally, foundation and powder. After she was done, I looked over at Tessa, playfully, and she sneered and laughed at how I looked. Miss Daphne provided me a mirror to look at myself, and I, too, couldn't help but laugh. I looked absolutely ridiculous, with the red lipstick to the flared eye shadow that Daphne had so masterfully given me.

Miss Daphne looked accomplished. Without her friend knowing, she had completed my night of humiliation, sissifying me almost fully. I spent the rest of the night with the makeup on my face, French maids outfit, cage on my cock, plug in my ass, with nobody but my Mistress the wiser. Only she and I knew the depths of depravity she had sunken me to tonight. That night, as we danced, she would discreetly grab or rub my caged cock here and there, as much a constant reminder that I was hers as the key around her neck.

When I got home later, I realized there was a fairly large precum stain on my pants. I stripped off the pants when a text came in from, who else, Miss Daphne. It read:

"I had fun tonight, sissy. You can take the plug out, but the outfit stays on over night. From here on out, forget that you own underwear. Wherever you go, its underwear free. If you're a good girl, maybe we'll get you some panties to wear one day."