Femdom Chronicles Ch. 08

Story Info
She locks subby in chastity, and expands his boy-boy play.
11k words
4.36
9.2k
6

Part 8 of the 8 part series

Updated 06/10/2023
Created 08/26/2021
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Domme's POV

I texted my sub from work on Wednesday suggesting a time for our evening at my condo. My workweek had been unusually busy, and I looked forward to spanking and more with my subetta. And as he had agreed to propose a new showing of loyalty to me (I had wrangled this agreement out of him the prior weekend), I especially wanted to hear his new offer.

I arrived just prior to six P.M., with subby boy arriving a bit later- just enough time to get into my favorite spanking attire of leggings, a loose fitting soft cotton tee, and no bra. I sipped mint tea on the couch as he entered my living room, greeting me in his lacy black panties and thigh high tights after disrobing in my kitchen area.

"Hello, you look sexy in your girly outfit! Anyone notice your sexy underthings at work?"

Displaying a small grin at the corners of his mouth, he retorted quietly. "Thankfully, no. They were a bit scratchy but one gets used to it I guess."

"Hmm, please retrieve the silver ball toy from my drawer in my bedroom, you know the one, before we begin our play for this evening." As he handed me the toy, I nodded and pointed to his knees in the direction of the yoga pad. "Please first pull down your cute panties to your thighs." He obeyed quietly and knelt and kissed the top of each of my feet. "Okay, get in the upright position now, and spread your legs with your torso vertical."

"That's my femboy. You know your place, and such a lovely view of your man parts, with your balls hanging down all nice for me." I tweaked his cock with the silver ball toy, and then landed three firm strikes on his scrotum.

Subby flinched at his mid-section, groaning. "Well, that reminds you of my dominant role, doesn't it?"

"Mmph, yes," he nodded.

"I know you have family responsibilities tonight and time is short, so let's get right to it. Why don't you sit below me there on the floor pad, just lean against my legs."

"On the floor, my domme?"

"Yes please, that's the way I want it. Seems fitting, don't you think, you below me on the floor?" I asked rhetorically. He quietly obeyed and adjusted his position as requested, while I remained sitting on the couch, very much in control. "That's my good pet. So let's have it, your new showing of loyalty, speak up!"

"Yes, well I have given it some thought. First, I wanted to suggest that we expand my spankings to public places, like the parking lot at the bar-restaurant. Does that count?"

"Sorry, it's too risky to regularly conduct bare bottomed spankings in public, especially for you. A good reminder about that parking lot option though, I bet Jie would enjoy it. You have other ideas, yes?" I questioned tersely, in a demanding tone.

"Yes. Would it please you to add more girly wear and feminization to my attire? Any new items and so forth would be at your discretion."

I flashed a quick smile. "My, that is a proper response indeed, I'm happy with your suggestion my sub. And soon to be my pussy boy in your new femboy attire! Be ready this Friday evening, I'm sure I'll have some new items and more in accordance with your proposal. Mmm, my girly parts are tingling as I think about it. I'll need you to attend to that tonight, but first, let's get you over my knee. Please pull down those lacy things and get naked for me. Let's use the wood slat tonight to celebrate your idea- we will soon have you dolled up like such a girly boy! Just imagine the possibilities. Please retrieve the slat for your spanking from my room. Run along now," I chortled, slapping him on the behind as he stood to procure the tool for his own whacking.

I relished the feeling of power as he lay over my lap, with me seated on a dining chair. Pausing before commencing his bare bottom smacking, I proceeded to deliver a series of thwacks to his milky white nether cheeks, which were cherry red after his paddling! My girly parts were wet and aroused as I stripped off my leggings and panties, and promptly stepped to the couch. "Okay my sub, place the yoga pad before me and get between my legs, on your knees of course. It's time to worship your domme's petals and clit, with some much needed oral attention. Mmm."

*****

My subby boy left shortly after completing his oral tasks- it was a weeknight. I was pleased with his lack of pushback to my expanded control, yet I knew the weekend may yield a different attitude from him, and possible efforts to negotiate a different arrangement. I resolved to be unwavering and adhere to my new protocols on Friday.

I was quickly on the phone to my good friend Jie after ordering dinner, and relayed to her my sub's obeisance to my rules, and his latest agreement to add more femboy wear to his wardrobe. "OMG Jie, this really gives me latitude to engage in edgier pussy boy themes, as you have put it."

"Wow, you are certainly leading him into more advanced territory, well done!" We eagerly went online, perusing various sites for girly wear and the like for men, finding a bra and panty set. She then led me to an item that was described as "baby pink sissy panties" and a layered ultra frilly "sissy skirt" that fit above the hips and only partially covered the butt cheeks! I added a black garter/lacy panty item to our purchases before we finished.

We both agreed that I would need to be stern and unyielding if he balked at wearing our purchases. Jie pointed out that he was a reluctant sub. "You may want to gradually introduce them over time."

"Yes, I'm thinking the sissy skirt especially will go in the closet at least for this weekend. This will really ratchet up his feminization. Going to have him model the items for me Friday after work, and you're welcome to join the fun. Can you make it?"

"Yes, for an hour or so! Maybe have him model the items and wait on us in his sissy- wear while we relax with our wine and crackers."

"And we should tease him, wearing them will clearly mark him as our sissy!"

"Indeed, let the teasing begin! Looking forward to it."

*****

I arranged to leave work early Friday evening, and found several items on my porch from UPS that I had ordered. As I unwrapped them, my pussy was already getting worked up. Subby was in for a surprise!

I set out on my bed a girly bra and panty set, a black lacy G-string-garter belt combo that came as one piece, and bright pink, sissy pouch panties, replete with pink ribbon bows on the front and back waistline. I expected these would take some effort (and maybe the threat of a thrashing!) to get on him. Still to yet arrive was his sissy skirt.

Slipping into my comfy attire, I arranged a few spanking implements on the coffee table, before finishing work emails. He arrived promptly around six PM, and quickly shed his work pants and shirt, displaying his lacy magenta panties and black midthigh tights. "Greetings my girly boy, I see you wore your thigh highs like my obedient pet!" I kissed him on the cheek before directing him to fetch us two waters. "Mine should be in a midsized glass please, and be sure that it's chilled."

He set about his tasks, and we quickly reconvened in the living room. I planned to promptly exert my control in order to set the tone for the evening. Please strip and lean over the end of the couch, time to get your sexy nether cheeks warmed up. I grabbed the wooden slat, stepped behind him and began vigorously whacking him with quick, repetitive swats. "Always good to reinforce our roles after our work day, would you agree?" I quizzed.

"Yes my dominant, but not much doubt you're in charge!"

"That's correct, my subby." That's enough for now. Jie will be arriving shortly, so let's step to the bedroom. I have some cute lingerie for you to model while we relax with our wine. Isn't that exciting? Well, perhaps not for you, but there are advantages to being the domme!"

As he gazed in amazement at the lacy feminine items displayed on my bed, I knew I needed to get things started before he began having second thoughts. "Okay, let's begin with this bra and panties set. (They were partially transparent, black,

adorned with tiny red flowers. The top was more like a bralette, with very limited cups, and the panties included a frilly one inch skirt attached at the waistline and were a G-string in back.) He promptly stepped into the panties but hesitated when I picked up the matching bra.

"Umm, isn't this a bit much, a bra? It's not like..."

I was ready for pushback, and abruptly interjected. "You agreed the enhanced girly wear was to be at my discretion; it was your suggestion. And this is what I have selected. Is there going to be a problem? If so, we can revisit the wooden slat!" I tersely snapped. "I expect you to model all the items on the bed tonight for us, understood?"

Verbally chastised, he looked downward, and meekly replied. "Yes my domme, my apologies, I need to be a good subby for you."

"Yes you do. Bend over the bed." I smacked him several times with my hand, the sound ringing out. "No more backtalk! Now let me help you get into your cute bralette." And I proceeded to clip it together in the back before stepping back to gaze at him, suppressing a laugh. The bra was a first! "Very feminine, my sub. Please step into your three inch heeled sandals and your thigh highs and matching panties, and get me a glass of wine. Bring it to the living room."

Jie entered my condo as he handed me a glass of Merlot. "In here, you're just in time for subetta to model his new feminine wear." We greeted each other and she quickly seated herself. "Please get her a glass of wine, and begin!"

He brought out the wine, and strode in front of the coffee table, offering different views of the bra-panty lingerie set. Jie joined in on the teasing. "So girly, like the tiny waist skirt on the panties, and partly transparent-we can see glimpses of his man parts. And he looks darling in his little bralette. It's his weekend sissy wear!"

Subby was blushing, though in his decidedly femboy outfit, I could understand why. "Yes and wait until you see his pink pouch panties. Come with me to the bedroom my pussy boy so we can get those on you! These were bright pink with a pouch that had barely enough room for his cock and balls, though the site claimed the small pouch was elasticized and expandable. The waistline was made of frilly lace replete with pink bows. Subby raised his eyebrows but compliantly stepped into the dainty panties. He had to gingerly open the pouch before carefully settling his man parts into it. There was no spare room there!

I stepped back and gazed, smirking. "You look very much like a sissy boy in those. Give me a minute to join my friend then please come in." He just nodded, already with a deep red blush spread across his cheeks.

We gawked at him as he stepped into the living room in his pink panties with bows, heeled sandals, and thigh highs. Jie was again quick to chide. "My, those are so girly, with his little cock and balls inside the lacy pink compartment. And the dainty bows; please turn around, sissy boy." As he did so, she continued with her running commentary. "And two more pink bows in the backside, just totally..."

"Yes, he's our sissy waiter," I chortled, "with the dainty pink pouch for his dicklet and then his heels. Please go get us some cheese and crackers, and refill my wine!" (This was the first time I had referenced the size of his member; it seemed appropriate as it was time to ramp up the teasing.)

As he returned using a tray to hold our items, there was more chatter. "Thank you, it's nice having our own sissy maid tonight!" Jie giggled. Subby cast his eyes down. This had to be humiliating for him, yet I detected his pouch had filled out and expanded. Could he be turned on?

"You can wait for us next to the dining table while we chat, girly boy." I took Jie to the bedroom to show her the other items.

"Hmm, I have to leave soon. Can I see him in the black G-string-garter belt piece with his bra top? More sissy wear for subetta, though not quite as girly as the pink pouch thing!" I supervised my sissy's wardrobe change, making sure he used a hanger for the pouch panties, before directing him into the dark bra and a black panty with attached faux garters.

He was clearly uncomfortable, especially with the bra, and once again hesitated. "Please, do I really need to wear the bra?" he pleaded annoyingly.

"We already went over this, you are being a disobedient sissy" and I clasped his wrist firmly and led him to the living room. "Lean over the straight back chair while I get you restrained. Sorry Jie, but he whined about his femme attire one time too many. Time to set him straight."

"I agree, best to nip it in the bud!"

"Subby, I will remind you that you agreed just two nights ago to enhanced girly wear and so forth, AND that these were to be at my discretion. Correct?"

"Yes my domme, I'm sorry, it's just..."

I abruptly interrupted. "Enough! This will be brief but very firm!"

I once again clasped the firm wooden slat. Whack!...Whack!...Whack!

"Owww, Jesus fuck, please!"

I was undeterred by his cries, pausing between each strike, allowing each one to settle in. I furiously paddled him before stopping, his nether cheeks now crimson red. "I expect better behavior from you, especially when I invite guests, understood?"

Still restrained over the straight back chair, he nodded and quietly apologized. Jie and I exchanged glances, and I led him back to the bedroom where he dutifully put on the black bra and panties with the faux garters without complaint. "That's better my subetta. That looks very girly on you, especially the faux garter thing. And there are a few more feminine items coming soon!"

Standing in front of me in his black lacy G-string and bralette, he nodded quietly, blushing, seemingly resigned to his plight. "You're blushing but your cock is showing tumescence, just like I thought. You're a natural submissive, don't fight it. Are you enjoying this?"

"Umm, don't know. I guess part of me does. But..."

"There are no buts. Please follow me into the living room, and model that for us before Jie has to leave."

***

It was Submission Sunday and I sat lazily on the couch with my laptop, perusing an online femdom site. Subetta was on his way.

I had decided to go easier on the girly and sissy boy themes for the day. Jie and I had really put him through a humiliation wringer with his introduction to sissy wear, and I wanted the day to be kinky, but also allow my sub to enjoy our sex at some point. (I would enjoy it too of course, especially with me on top directing things!) Too much submission without a release for him, could lead to problems. I needed to keep him hooked.

And we were planning another girls' night for the upcoming Friday. This time it was more like a couples' night (Sean, the hot guy I met previously,, was likely coming). Though subby had stated more than once that he "was not comfortable" with my girls' nights, his submission was deepening, and I expected him to accept my decisions. I would notify him of the upcoming event at the club during the week.

He arrived and entered naked, jolting me out of my mental meanderings. We greeted each other and I quickly directed him to put on a pair of black lacy panties, "though I like you nude as you are too!"

I had brought out my own coffee and he grabbed a chilled water, and I directed him to sit before me on the floor over the yoga pad, while I seated myself on the couch. Okay, my sub, if you are good today, we will each get rewarded with our sex, with me on top, though the nipple clamps will be coming out for a spin."

He smiled and thanked me. "First, though, let's get you over my lap for some spankings- our favorite kink! We will use the wooden slat today again, so please stand next to the straight back chair while I grab our favorite spanking tool from the coffee table."

After administering his whacking, I directed him to the corner of the living room. Please plant your nose in the corner and contemplate how you can be a better submissive for me. I viewed him for a second as he settled in the corner and stood immediately behind him. "Your butt cheeks are pretty red and mottled with marks. Poor subby!" I chortled. "I'm heading to the bedroom to get things organized and then I will call you in.

I laid out the yoga pad, grabbed the Japanese nipple clamps and placed them at the head of the bed, before stripping off my clothing, and settling on the bed with my legs spread, vulva displayed near the bed's edge.

"Okay, please join me in here."

He entered the room and knew what to do, settling in front of me. "Time for some pussy worship, let's put that talented tongue of yours to good use!" Kneeling before me, he took his time and licked, nibbled and sucked me to another scrumptious orgasm. I grinned as I came down from my high. "Crawl up on the bed and let's see what we can do for you!"

Having been without a release for a week, he responded quickly to my stimulations to his sex. "Mmm, that's my sub, such a nice hard cock! Lie back and I'll attach the nipple clamps before I ride you!" And in short order, I straddled him and plunged my core down on his unit, our thighs moving in unison as we enjoyed our sex.

"Mmm, feels so good, thank you."

"Ummph, yes, I want you to come for me, my pet. Shoot your load inside me!" It was not long before he closed his eyes and groaned, making his sex sounds. He came and I joined in, reaching a smaller release myself! As we lay next to each other, I unclipped his clamps and we enjoyed our post-coital glow.

Before he left, I reminded him that our Wednesday night after work special was on again that week, "and every week my girly boy. See you at 6 P.M. We'll talk about the upcoming weekend then."

*****

I had to work late Wednesday and texted him that we would talk on the phone later that evening. After getting home and ordering food in, I called.

We exchanged greetings and light chatter before I got to the point. "Sorry I missed you tonight, I was looking forward to seeing you in the cute G-string panty and bra. And of course, my midweek pussy worship session! But I also need to go over with you the plan for Friday night. Just letting you know Friday is another night out with the girls for me. Though my friends are bringing dates to the same dance club, and I may be, well, there may be a young guy for me too..." I paused for effect.

"What does that mean? Are you umm...?" he stammered.

"Am I meeting him there? Yes, that is likely, and it's the same guy I got frisky with last time. He's really masculine with a nicely trimmed dark beard and looks pretty ripped in his form fitting dress shirt and jeans. I can't imagine him wearing femboy and sissy clothes like my subetta. You don't want to deny me my sexy fun with my young manly play toy, do you?"

"Uh, not sure what to think, I do want to be your good subby, but umm, he is your play toy?"

"Oh, is my little girly boy jealous? Don't be. Just accept and be my good submissive, like you said. And not too worry, I'll keep to our protocol: no sex and keep it at the clubs. I'll be sure to share any sexy details with you on Saturday, while you cuddle up on the yoga pad in your lace and frills. You're still my special subby! Maybe we can break in the new dildo I ordered on your cute rosebud, I know you'd enjoy that! And there's one more special item for you to wear too, its ultra girly!"

I was pleased with the lack of argument to my rather candid announcement. I pretty much informed him I was meeting a hot date at the club- and quickly moved the

topic.

*****

I called Jie as I drove home from work on Friday before we met at the club. She confirmed through a mutual friend that my unofficial date (Sean), was indeed going to meet me. I felt an inexplicable pang in my stomach, one I usually associated with anxiety. What was this- was I having second thoughts, or was it excitement? It could be guilt. I knew he would have expectations, this would be our second meeting.