Femdom Chronicles Ch. 08

"I'm feeling ill at ease about this Jie. Should I be guilty, after all I'm with subby?"

"Didn't you tell me the other night you informed him that you were meeting a guy?"

"Yeah, but..."

"But what?"

I was pretty terse about it, and didn't really give him a chance to respond."

"I agree with that- you've got him wrapped up in his girly boy persona, wearing sissy wear and so forth. You're entitled to play occasionally with a more manly guy. He needs to accept it."

"Thanks, but I'm not ready to have sex with this guy, at least not tonight. Maybe we can find a dark out of the way spot and get pretty naughty, that will be within the rules."

"Well, whatever you do, just don't be wracked with guilt. You deserve this!"

"Okay, thanks as always for the encouragement."

I wore a short, navy blue, pleated skirt which flared out from the hips, much like a tennis skirt, with my black G-string underneath. I added a partially transparent off white blouse with my a black demi-bra, along with tasteful makeup. I looked and felt sexy. Once I stepped into the hip dance club frequented mostly by a younger clientele, I was buzzing with excitement. I was a tad late, and quickly located my group. Sean was there, sipping a beer and smiling, looking relaxed. He approached me and we kissed a few feet from the bar, tongues playing. It occurred to me he had to be at least twenty years younger than me, he was likely about thirty.

"Nice to see you Wang! You look... great. Love your skirt." I greeted the others, and we chatted as a group, Sean with his arm around my waist, fiddling with my skirt's waistband.

Jie gave me a thumbs up, and mouthed, "you go girl". My date and I were soon mixing it up on the dance floor, dirty dancing, with him rubbing up against me from behind, our pelvic areas in sync. I did nothing to discourage this, instead my hand found his backside, before I inserted it under his jeans and briefs, exploring his taut glutes. More sexy dancing, hands on each other hips, thighs swaying, before he glided his hand up my skirt while behind me. This was too much, too public, and I found the gumption to move his hand away. At the end of the song, he led us to a quiet, dark hallway in the rear of the club near the restrooms.

More passionate kissing and this time, while he used his body to shield me, I let his hands roam under my dress and up to my G-string. I groaned as he rubbed my moist labia under the thin fabric of my panties while my hands lightly grazed his engorged sex over his jeans. We were both turned on, and taking me firmly by the hand, he led us to a handicapped stall in the women's restroom, getting surprised looks before we closed the door. I promptly had his hard cock out, and began stroking it, though was uncertain how far I wanted this to go. Sean had his back against the wall, moaning at my attentions; meanwhile he reached under my dress, moved my panties aside and fingered my pussy before leaning into me and whispering we should go to his place.

This was a bridge too far. Stepping back, I shook my head. "I'm sorry Sean, I'm not ready for that, umm, not tonight."

He uttered a few obscenities, uncomfortably zipping up his fly. "At your age and a tease? I'm past high school stuff, getting all hot and bothered, then what? We're adults!" he practically shouted. Clearly unhappy, he bolted out of the bathroom, and I did not see him again that evening.

The rest of my evening was uneventful, and feeling like a third wheel with Jie, her date and the other couples, I took an Uber home at an early hour.

*****

It was the next day, and wearing only his black G-string, my subby sat next to me as I relaxed on the couch after our greetings. I had briefly spanked him over a dining chair to get him in his subby zone, and decided to tease him briefly with a few details about my prior evening's hot fun with my date.

I kissed him, running my hands over his chest and pinching his nipples. "Mmm, nice my sub. I did meet that cute guy Sean last night at the club, and again, there was no sex and no phone numbers were exchanged- but we got, umm, I guess we got a little naughty. He's so masculine, and had a lovely scent of cologne. I hope you appreciate that I respected your concerns. I'm not sure if you want to hear the salacious details, but..." I paused deliberately, teasing. I was testing his reaction.

"The salacious details, with your date? Umm, I'm glad you didn't have sex with him, but..." There was a long pause, I wanted to see if he would ask. He looked downward, and timidly spoke in a soft voice. "Yes, I guess I want to know, not every detail, but..."

"That's fair," I chortled, while I fondled his unit over his panties.

"Well, there was some passionate kissing while we were dirty dancing, and I'm so bad, I ran my hands under his pants and silky briefs to his tight glutes. At the end of the song, he clutched my hand and led me to a quiet spot at the back near the restrooms. He was so confident, forceful and manly. We kissed, and there was some touching of each other's naughty parts over briefs and panties." I paused. (Sub was looking down, but tellingly, his member was tumescent.) "After a few minutes, Sean grabbed my wrist and we ended up in the women's restroom. Once inside an empty stall, our hands were roaming to bared pussy and cock, and it was, well, you know, really sexy, both of us were aroused. But when he suggested we go to his place, I declined, and then he was rude, mumbled a few obscenities, zipped up his pants and just left."

Subby wore his sad puppy dog look, yet surprisingly, seemed to be quietly accepting. "Don't be jealous my subby, I'm here with YOU today. I hope you are you proud that your domme enjoyed a sexy scene with a handsome young guy, and I followed our rules- no sex or phone numbers."

"Well, it's a little unsettling," he finally blurted out, "but the submissive part of me, uhh, I guess as my domme... umm, I'm, umm, you're entitled, and it sounds like you had a sexy good time."

"Thank you for admitting that my subby! Hmm, I'm curious, did hearing about my hot sexy fun, did you find it all titillating?"

"I guess the subby part of me, umm, yes, but uhh..."

"Thanks again but enough about that, I need to retrieve the slat from the bedroom. Please wait for me on your knees like my good pet." I whacked him a several times with the wooden tool and after bringing some color to his nether cheeks, announced "I'm going to organize a few things, a girly item for you I've yet to introduce, that we're going to have you model today. When I call, you will join me in the bedroom."

"Yes my domme," he muttered.

Once in my bedroom, I got out his frilly, ulta feminine pink skirt- that even the site described as a sissy skirt. It was twelve inches in length and designed to be worn high over the hips with the bottom hem not fully covering the butt, replete with several layers of lace and frills and white borders at the top and bottom. Subby had yet to see, or wear this, but it was time.

Summoning him to my room, he immediately noticed the skirt. "Isn't that pretty," I teased, "and it matches your pink G-string, don't you think? It's your new sissy skirt! Let's have you try it on." I was openly smirking as I observed him.

He looked taken aback, stepped back away from it, displaying a grimace-like expression. "Umm, you're saying you want me to wear that? Umm..."

"Let's not do something rash, that will require punishment, and yes, I want you to step into that. I'm sure you'll look like my good sissy boy," I chided. "Remember, you agreed to more feminization that would be at my discretion. This is one of the items I selected."

He looked upset, almost like he was ready to cry, very submissive yet digging in. "Please, don't make me wear that," he implored in a rather high pitched, plaintive wail. "I don't know if I can. Isn't there another way?"

A light bulb went on in my head- I sensed an opportunity. "Well, we talked about this as your showing of loyalty that you agreed to in lieu of chastity. Since you picked the option of expanded girly wear, and are seemingly unable to comply, it's up to me to select another way to demonstrate your submission. I will allow you a choice. Either wear the frilly pink sissy skirt for me, and maybe my guests, or let's get you in the chastity device Jie has so generously provided."

"Your guests? That's too much. Umm, may I ask for a different, umm, method?" he stammered. "I want to please you, but.."

I cut him off, stood with hands on hips and spoke sternly. "No, those are the only choices. You are to choose the skirt or chastity. Which will it be?"

"May I have time to consider this, and may I try on the cage thing?" This was what I had hoped for, though I attempted to keep poker faced. And despite his protestations, he was not defiant. He did not challenge the options offered, instead seemingly resigned to picking one of them.

"Of course my sub. I quickly pulled out the plastic cage from my dresser, removed it from a small box, and showed the parts to him; his cock was suddenly at least partially tumescent! "I will allow a trial run, but only one. I'm going to apply a frozen fruit bag to get your man parts calmed down, then we'll put this on for the rest of the day until you leave. You can have until tomorrow morning to decide, first thing. Understood?"

He nodded. "Yes, if those are the only choices, then..."

"They are indeed!" First I applied some ice to his unit. It was not long before I had maneuvered the plastic ring around the base of his shrunken cock and balls. Next I carefully settled his now smallish cock into the little cage, and fitted the bolts attached to it into the holes on the ring. I placed the small lock that came with the kit through the eyebolt connecting the two pieces, needing only to push down to lock it! I paused. "Okay my pet, do I have permission to lock you up?"

"This is a trial run, yes?"

"Yes my sub, you can still choose your frilly pink sissy skirt tomorrow morning if you like."

"Go ahead my domme."

Click! "That's my good pet, now with your man parts all locked up for me. I like it!"

*****

It was late the next morning and my sub was driving to my condo. After having caged him the day prior, he was surprisingly accommodating about his new predicament. There was little complaining and he learned a few things about functioning while wearing his "man cover". There was taking a pee sitting down, and also adjusting to wearing it in public- we went out for dinner while it was on him. Fortunately, he had worn loose fitting khakis, and his cage was not really noticeable. I unlocked him when he left, and I found myself with a bit of anticipation over his decision. It was no secret to both of us I had been wanting to lock him up for a few months as part of my growing control.

As I sat absentmindedly looking at work emails the next day in my computer room, he entered my living room wearing only a pair of lacy panties. I greeted him with a peck on the cheek and took him by the hand to my bedroom where I had laid out his two choices: the pink sissy skirt and, next to it, the plastic chastity cage. I knew I needed to be stern lest he try to wriggle out of our agreement. "Okay my sub, please step out of your panties, It is time for you to choose. I assume you have given the matter some thought."

He looked anxious, and stared uncomfortably at the sissy skirt, then frowned. "Uh, yes. May I ask a few questions about the cage option?"

I paused for effect and tried to downplay exactly how much wearing it would change things and my control over him. "Of course, go ahead."

"Umm, if I go with chastity, how often will I wear this? And will I have a key during the work week when our schedules get busy or at my house?"

"I had expected this and tersely replied. I will be the only keyholder, and will take into consideration your concerns but am not going to negotiate with you. It is past time that you wear this as a demonstration of your loyalty. I will expect you to wear this today, but will unlock it before you head home. There will be occasion to wear it during the work week of course, but it will be introduced gradually at my discretion. On the weekends, you will be locked except on special occasions.

"So is it your choice to be placed in a cage?"

"Umm, I just can't wear that skirt, so I am inclined toward chastity. So just to be clear. If I wear the cage for you, then that skirt and others, and I also request all bra's and the pink pouch panty thing are part of my one hard limit, and I will not be expected to wear them."

"Hmm, always trying to negotiate. I will agree that skirts and one other piece are considered shelved, provided you are on good behavior. What is your other item?"

"No bras or bralettes please."

'

"Done, everything else my girly boy is at my discretion, provided you are on good behavior. Time to get on your cage! Hands at your sides, now sir, and keep them there." I carefully got the plastic ring around his unit and ball sack and slowly settled his member inside the rather smallish tube. All that remained was to lock the two pieces together and place the lock through the eyebolt connecting them. I did so but waited to click the lock.

I paused, allowing the moment to settle in. "Okay, do I have your permission to lock up your cock?"

He sighed but responded. "Yes my domme."

CLICK! "That's my good chastity boy!" I exclaimed.

"Mmm, lovely, lie on the bed on your back while I get the restraints. Let's celebrate shall we! I need my chastity femboy to worship and lick me all nice! Jie will be joining us in a while, so we best not dither!"

And I promptly restrained my naked and caged subby to the front corner bedposts, stripped and joined him. "Seems appropriate for you to be restrained like this my chastity sub. I do so like the sound of that!" I delicately handled his plastic encased cock, lifting it up and lightly fondling it. "Can you feel that at all?"

"Not really, the plastic cover, umm, you know."

"How about when I fondle your balls underneath, like this?" I teased.

"Uhhh, yes, that's a turn on, but...."

"Oh, look at your poor little dicklet, can't grow much in that thing! And how about when I pinch your nipples and kiss you like this! I played with his nipples and we locked lips, with him groaning. Pulling away. I looked down at his unit. My your dicklet is straining against his cage. Poor boy! Going to be very easy to tease you with that on."

"Enough. With your cock locked and unavailable, it's time for you to worship my girl parts and focus on my pleasure!" Turned on by my newfound control, I straddled his torso with my hips, and shifted forward on my knees until my moist folds and clitty were over his nose and mouth. "Mmm, time for that lovely tongue of yours to get busy my sub. Make me cum!"

And I proceeded to fuck his face with my vulva, grinding on him while I I gradually found a noisy release, uttering my sex noises before I rested, the folds of my pussy sitting on his his nose, lips and chin, his lower face a mess. "Mmph, I needed that. What a rush! I suspect we'll be doing much more of that, now that you're all locked up for me."

"I'm glad you enjoyed my domme." We snuggled and kissed for a bit with me rubbing his chest but leaving his unit alone, not wanting to incessantly tease his now gloved up cock. I eventually unclipped him. "Let's get up, Jie will be here soon. Please get out the orange juice and sparkling wine and make us each a mimosa, my pet. Time to celebrate with my kinky friend."

I cleaned up and got comfortably attired in my tight black leggings, tee and hoodie before assisting him with the kitchen duties. Heading for the bedroom, I picked out his outfit. "I want you to look nice for Jie, so let's have you wear the thigh high lacy black tights, the transparent black panties- not the G-string, that won't cover your cage, and your three inch heeled sandals. Get those on, and meet us out in the living room. Jie is coming upstairs now!"

My best friend and kink partner and I chatted and sipped our mimosas as subby joined us in his sexy outfit, cage and all. "Please get us each a water my sub and one for yourself, pronto sir." He stood before me after setting down the water bottles. "Why don't you greet Jie today as you would normally me-on your knees from the pad- we have already laid it out for you."

"Of course my domme," and he obediently knelt, removed Jie's left shoe that she raised for him, and lavished her toe with a lovely tongue bath. "Greetings Jie!"

"Thank you, nice to see you and I understand you have accepted your proper role- wearing the cage for your domme. Now please if I may ask him to stand and remove his panties so that I may inspect his new plastic adornment. So exciting."

"Of course Jie, and I nodded for him to bare his newly encased member. She moved to the edge of the couch and lifted his tubed cock, then examined and rubbed his balls and the plastic over his unit. It's more like a mushroom in his little cage, not much room in there, so cute. You can't feel much but I see it's trying to grow as I rub below, on your balls! Do you like?"

"It's different, Miss Jie, a little frustrating, but I know it pleases my domme for me to wear it."

"Mmm, indeed it does, good boy. Okay my sub, let's get you restrained, we're both going to take a turn with the slat! Chastity boy's like you need your Sunday maintenance spankings. You know the drill."

Jie decided to use the smaller paddle and got his backside warmed up, before I unleashed on his tender nether cheeks. He eventually began yelping and crying out for mercy. "Hmm, you carrying on like that turns me on, and lets me know I'm doing a good job!"

"Agreed my friend, his cheeks are cherry red- and I'm sure stinging a bit. Another lovely thrashing! And that got me going too- I'll have to tend to it later at home."

"Okay chastity boy, let me unclip you and then please head to your favorite part of the room for some corner time!"

Jie and I chatted a bit in the kitchen about possible options for play, before catching up on our jobs and the new guy she was dating. She had found him on a kink site, he was her sub in training- but also boyfriend material with a career and a homeowner. She had to leave and I had work meetings to prepare for. First, I needed a brief chat with my newly chastised sub before I unlocked him. I brought him to the bedroom, he was still in his lacy tights- and cage!

"Okay subby, let's sit on the bed shall we. Just wanted to go over the weekly plan with you. You'll still be wearing your lacy panties, and why don't you wear your sexy black tights twice this week- you decide which days. Please come over after work on Thursday to attend to my needs and we'll see about your chastity cage then."

"Umm, what do you mean, see about my chastity cage? May I ask?"

"You just did. We're going to need a rule: No pestering me about when you'll be wearing your man cover for me, and when I will unlock you. Those decisions are completely at my discretion. Now lean over the bed so I may provide some attention to your rosebud. You'll be getting more of that as my chastity boy. But first, get in the bathroom and clean up down there."

After a pause, he knelt on the bed, with head down and butt up. "That's it, a very submissive pose, your little pink bud is front and center! I'm going to lube it a bit before using my fingers as a warm up. I put a thin plastic glove on and began lightly fingering his rosebud while rubbing his balls. Mmm, my pussy boy, you like that don't you?"

"Uhh, I guess my domme. Though it's frustrating with that thing on."

"Oh, is subby's cock trying to get hard? Never mind, let me get the thin pink dildo. Time for some more rigorous treatment!" I began manually fucking him with the dildo, slowly at first, then more deeply, to the hilt of the tool. "How's that feel? Is your butthole properly lubricated?"