Age Progression

Continued from: Two Days a Captive

A post from slave sarah 

As I wrote about in my last post, I just spent the better part of two days in a BDSM jail cell, with my throbbing pussy locked into a chastity belt a majority of the time. I was only removed from my cell to be whipped or sexually used by my Master. It was a very heavy scene that spanned the two days of my captivity. I loved and hated it equally...

Master did some tender aftercare with me and took me to a room that also had a lockable cell door, but appeared much more comfortable than the previous space I was in. 

Everything was pink and ruffled and adorable. Almost immediately I felt comforted in this space. I felt little and vulnerable. Russell sat me down and explained a new plan he had for me. 

I was told that this space was the alternative to being in the stark and dank jail cell for my sessions, that this "little" space would be the first step in my age progression. It was made very clear to me that I would be required to wear crinkly diapers on occasion and I would be required to dress in extremely elaborate sissy attire, almost like a doll, with Mary Janes, ankle socks or even white tights. 

Russell explained that his role would become a Daddy Dom and I would be his "little". I would have rules, boundaries and be protected and cared for while under Daddy's control. Consequences would no longer involve bondage apparatus and whippings, rather, I was told I would be given childish punishments like over-the-knee spanking, mouth soaping and timeouts. The diapers, the outfits and my new lifestyle when at the Facility, would be extremely humiliating, he went on to explain, before showing me little child's calendar on the wall. 

Russell told me that through obedience, acceptance of my new role and good behaviour, I will earn gold stars on my calendar. It sounded like if I kneel and suck Daddy's cock for instance, and accept his cum into my mouth, then all cute-like, thank Daddy for his cum once I have swallowed it, I would earn a gold star on my chart.

If I achieve enough stars, I would be promoted in "age". From what I was told the next stage would involve me dressed as a schoolgirl in short tartan jumpers and skirts. There would be no more diapers used but discipline would now involve a cane, paddle and strap, not just a hand-spanking over Daddy's knee. My room would change and I would be attending the classroom upstairs, for many of my scenes. 

Again, I would be subject to a system of either demerit points or gold stars, based on my submission, behaviour and obedience. Russell explained that after this stage, if I earn a promotion again, I enter an "older" schoolgirl role. Knee socks become thigh-highs or tights, my skirts become sluttier and shorter and my heels get higher. 

The more he explained the more I was really starting to enjoy this concept of age progression. Apparently after the second schoolgirl look, I would become a slutty secretary and one step closer to what Russell was calling an Upper Floor sex slave, which I also liked the sounds of. If it's anything like the Upper Floor porn site where the girls are in those red and black seamed stockings, I'm all in! I'd love to be used like that and be that well trained. 

This entire plan also involves demerit points. Ying and yang I guess. You can't have pleasure without pain, and there can't be gold stars without also having demerits. Russell explained to me that if demerit points were earned, I could be demoted down a rung, like suddenly regressing from schoolgirl, back into diapers and into the pink room for instance. If I was so naughty that I am demoted from the pink room, I end up back in the jail cell, left alone and only released to be flogged and aggressively fucked.

This was definitely the incentive I needed, before agreeing to all of this. I didn't want to end up in shackles, locked in that jail cell and left alone again. I seductively plopped my bare, recently whipped ass onto Russell's lap and he pulled me in for a lovely embrace. 

I did my very best sucky and needy, baby-voice and for the first time, called Russell, "Daddy". 

"What do you say we get you out of that chastity belt and into a comfy diaper little one?" He asked me. 

Of course I purred back to him immediately, "yes Daddy." 

After some time spent at the vanity table and mirror, and with Daddy coaching me on, I surprised even myself when my reflection suddenly involved ringlets a hair bow and heavy make-up. 

It was nice to be rid of the clunky metal chastity belt but I was dreadfully humiliated when I had to adopt a diaper pose for my new Daddy. Like suddenly I was shy and modest?! This gorgeous man just spent two days violating all three of my fuck-holes with his penis. Pussy-to-mouth, ass-to-mouth and back again...yet this was the embarrassing part for me? Having to hold my legs wide and in the air while Daddy powders my pussy and anus, then slides a crinkly diaper under my tailbone. 

I had to put on this hideous, ridiculous satin dress but I was relieved that it hid my diaper. Next came white knee socks and little doll heels in blue gingham. 

This was a horrible and devious predicament I had just agreed to. My outfit and my new role was humiliating beyond belief, but the humiliation was only making my pussy wet and achy. The humiliation wasn't excruciating to the point that I would purposely act out and become demoted, just to be rid of these clothes. If I acted up I would be punished and surely end up naked, shackled and returned to the jail cell. 

My only reprieve would be through promotion. Promotion away from these silly clothes and this dreadful role. For this I had to be a good girl for Daddy, and earn those gold stars on my chart! When his penis was produced a short time later, I wasted no time in going for gold! I'll be the best LG this DD has ever experienced! 

"Ohhh Daddddddy!! It's so big." I purred to him as his cock began to swell in my little hand. 

"Daddy, I love it when it grows in my mouth!" I continued on with my vulnerable, baby-voice. 

Daddy was so gentle and caring with me. Not only did I earn a gold star that day, but also a pussy full of Daddy's cum! 

Thank you Daddy!
 

slave sarah

xoxo

Continued in: Working from Home

And the winner is...

Continued from: Sissy School

It was the final day, the grand finale, of sissy Lexi's weekend under the care of this dominant couple. Lexi is the name provided to this hetero male, every Friday when he checks himself in for a weekend of crippling humiliation, cuckolding and "forced" bi-sexuality. 

On Sunday's, after Sunday school had finished for Lexi, he brought a note home to his "parents" indicating his bare bottom was caned at school for misbehaviour. He now has to feel the wrath of either Mommy or Daddy. 

Like a wheel of chance, Lexi nervously stood in front of his simulated parents, and tore open the envelope he was holding. After a quick glance at the card inside, he held back tears, focused his eyes toward Erin and squeaked out: 

"Mommy, may I please be given a spanking, Ma'am?" 

"Yes young lady, you may," Erin spoke sternly. "Now get that bum bare and get in the corner." Erin barked. 

"Yes Ma'am," Lexi replied. 

"Mommy will come get you when it's time Alexis," Erin added. She clicked out of the room to go change into more of an old-fashioned, Mommy look. 

For the next 45 minutes, Lexi stood in the living room corner with his caned bum on display. Brad watched TV in the same room and puttered around within earshot and in the kitchen, carrying on with his vanilla life, as the sissy nervously waited. 

He had plenty of quiet thought while he was in timeout, to process the fact that he was about to spanked by Mommy. His stomach sickened with humiliation, as he reflected on the times he has been spanked over Brad's lap, sometimes fully naked in only his chastity cage and having to call him "Daddy". 

He had a genuine fear of Daddy's belt, that Brad would snap through the loops of his jeans before doubling it over, causing the buckle to jingle. 

Today however, Lexi now knew he was in for a little less humiliating spanking, at the hands of "Mommy", but equally, if not more of a severe blistering of his bare bum. Erin was always more strict with maternal discipline of this kind and she used more implements than Daddy spankings. 

Lexi shivered with nerves, as he thought about Mommy's slipper, her wooden spoon and tears began to form when his mind fixated on her long-handled bath brush and how brutally severe it can be. 

But...this was all something he asked this couple for, it was his fantasy...as a sissy spanko cuckold. 

Lexi's quiet reflection in the corner ended quickly and shockingly, as Erin grabbed him by the earlobe and marched him out of the room. 

"Let's go young lady, you're totally in for it." Erin threatened. 

Sunday spankings for Lexi are sometimes witnessed, Mommy spanking the naughty little Lexi in front of Daddy and so on, but not today. Erin wanted the wails of sobbing and cracks of wood against buttocks to echo down the stairs where Brad would remain. 

She lobe-marched the poor sissy all the way to Mommy and Daddy's bedroom where Lexi was stripped nude to just her school socks and Mary Janes. The OTK chair was waiting, and Lexi was stood directly in front of Mommy. Once Erin sat, her vantage point would be directly on the tiny pink chastity cage that was locked onto Lexi's penis. 

Mommy cupped the cage and balls into her hand. 

"Are you becoming aroused young lady?" She asked. 

Lexi groaned in utter humiliation, mewing out a, "Mommy, nooooo!"

"Is your little pee pee trying to get hard in that cage Alexa?" Erin continued as she reached for the dreaded bath brush. 

Sissy Lexi, overwhelmed by the relentless humiliation and fear of the spanking to come, began to cry big wet tears. 

"There we go young lady, right where Mommy needs you to be, its ok to cry", Erin cooed to him. "Now, lets get this unsightly thing covered up before you go over Mommy's knee. I don't want any white stains on my stockings." Erin stated. 

With that, she produced a pink satin pouch, trimmed with delicate lace and an elasticized opening. She slipped this humiliating item over Lexi's chastity cage and his balls. He continued to softly cry as his face reddened even further. 

Erin took up a more comfortable seat on the couch and draped Lexi across her strict lap. With Lexi's torso supported by the couch, Erin began the long and thorough warm-up with her hand. 

The slipper came next for this sissy slave, followed by the wooden spoon and finally the vicious bath brush. Erin didn't let up until she was sure Lexi's wails could be heard by the neighbours, amidst the deep, wooden smacks. Lexi was crying out, "I'll be a good girl Mommy, please no more," when Erin finally finished with him. 

Again, it was Sunday, now late in the afternoon. Erin or Brad deliver the same manner of spanking to Lexi every Sunday, to mark the end of his weekend of sissy slavery. They each ensure that Lexi feels the spanking all throughout the week, right up until the following Friday, when he's ready to return to them once again. 

Lexi spends about an hour in the corner when his spanking finishes, with his bare bum on display. He usually continues to cry for part of his timeout, all while listening to Erin and Brad fuck on the bed, or fuck right beside him. 

Lexi's penis is never brought up in a sexual context, there is never mention of a key to unlock it. If he ever asks permission to be unlocked he gets punished immediately. 

This poor sissy gets to listen only and sometimes taste. 

Once Brad has unloaded into Erin's gorgeous pussy, Lexi once again has a chance to taste his sweet Mistress but yes, it will involve taking Brad's cock into his mouth. 

Lexi is then on the clean-up detail of Brad's cock first, sucking and licking it fully clean, before tending to Erin's pussy, to clean and consume all of the cum. 

The sissy is then sent to the bathroom with nail polish remover and makeup remover, his male clothes are returned to him and he is sent on his way. 

Brad makes himself scarce and Erin sees Lexi to the door, kissing him on the cheek and cheerfully saying, "see you next Friday Huni!" 

What a lifestyle! 

**Special thanks to the fan and reader who submissively suggested this entire storyline**

It started here, with a post called Sissy slave to a couple

Mistress Andrea

xoxo 

 

Sissy School

Continued from: Wait for him by the door

Based on the progression of these latest stories, you can now see how this poor sissy's weekend of kink-captivity is organized and structured. 

Arrival and check-in was the initial transformation on Friday, the application of pretty nail polish and make-up, then a slutty sissy outfit. Saturday was a full day spent in a lockable maid dress with all the trimmings and now, on Sunday, Lexi was dressed and ready for "Sunday School", having just performed her morning ritual. 

Under the watchful eye of Erin, Lexi would be writing punishment lines on the chalkboard, sitting quietly at her desk and reading sissy erotica and basically spend the entire morning in a form of detention. Under his little plaid skirt were delicate, silk panties in stark white. Under his panties, his tiny pink chastity cage housed his denied penis. 

The schoolgirl look was deeply humiliating for Lexi. He was even made to wear a bra that matched his panties, with little fake, A-cup titties inside. What was most dreadful and butterfly-inducing about Sunday's however, was that Sunday was the real spanking day. 

Lexi was given an entry spanking on Friday night, over Erin's knee but that was nothing compared to what was to come. Lexi knew that around noon, his fantasy Sunday School day would end. He would be held behind after class to be caned by the teacher for poor behaviour. 

Then, with a note from the teacher in-hand, his fantasy takes him "home", to a domestic setting, where he has to hand the teacher's note to his strict parents. Apparently this was a thing back in the days of school-endorsed corporal punishment. If you were caned or paddled at school, you'd absolutely be getting the belt or hairbrush back home by Mom or Dad. 

This particular sissy, wanted the type of spanking that didn't really begin, until he is wishing it was over, with plenty of kicking and crying like a little girl. 

The school bell snapped Lexi from a trance-like state at his desk. Erin, playing the role of the strict teacher, stood and beckoned the naughty schoolgirl over near the pommel horse. 

"You know the drill young lady," Erin spoke and patted the top of the horse. 

Lexi lowered his head and began to remove his skirt completely, followed by his panties. Both were neatly folded and placed on the teachers desk. Then, Lexi draped himself over the pommel horse, standing on his highest tiptoes with legs spread. 

Erin gave the humiliated sissy 18 strokes of the school-cane and made him count them aloud, thanking her after each stroke. The caning left Lexi with a lovely pattern of raised welts, from his upper buttocks to the backs of his thighs. 

He was then placed in timeout while Erin prepared a note for his "parents". 

As the fantasy day continued for Lexi, he now found himself standing before Mom and Dad, handing them the teachers note and explaining that he got in trouble at school and was caned. 

"Go select an envelope young lady", Erin ordered, now playing the role of Lexi's Mom. 

"Yes Mommy," he replied. 

Lexi shamefully clicked out of the room in her Mary Jane heels and crisp knee socks, and down the hallway to the home office. She performs this same ritual every Sunday, while under the care of Erin and Brad, all while wearing different styles and versions of schoolgirl uniforms. 

On the corner of the desk in the office are a stack of manila envelopes. There is nothing written on them and they are in no logical order of any kind. Within the envelops is a single 5x8 card. Lexi is required to select an envelope, at random, and bring it back to Erin and Brad, unopened. 

On the little 5x8 card within the envelope, it will have one of two words written on it: 

Mommy

or

Daddy

As I'm sure you've already guessed, each week when Lexi performs this vulnerable ritual, the title on the card selected is the person who will punish Lexi. 

The embarrassed sissy will stand before Erin and Brad, unseal the envelope and look at the title on the card. Then he is required to say: 

"Daddy, may I please be given a spanking, Sir?" or;

"Mommy, may I please be given a spanking, Ma'am?" 

This is performed, all while he is dressed like a naughty schoolgirl, with his penis locked in a chastity cage, his wig in pigtails and heavy make-up on. My gawd I'd want to crawl right under the floor, this would be so humiliating! 

Is there a huge difference between a spanking from Mommy versus a spanking from Daddy, in Lexi's world? Apparently not a huge difference, both are serious spankings and always end in tears, both are predominately administered over-the-knee. With a Mommy-card selection, Lexi would likely receive her hairbrush. With a Daddy selection, he'll most definitely be getting Daddy's belt. 

Who's lap will Lexi's bare bum be draped across very shortly? What's your guess?

Doesn't she just look like she should have a wooden spoon in her hand? Maybe it'll be Mommy's strict lap this week.

Or, over one of Daddy's knees? So he can pin Lexi's flailing feet down with his other leg? 

Lexi stood before Erin and Brad and tore open the envelope...

Mistress Andrea

xoxo

Continued in: And the winner is...

 

Wait for him by the door

Continued from: Sissy's morning ritual

Brad actually works on Saturdays. So after fucking his hot wife, having his dick cleaned off by his wife's sissy slave, he hit the showers, changed and left for work. 

Meanwhile, Lexi was being dressed into his frilly maid attire with stockings and heels, and layers upon layers of ruffles and bows. 

Saturday is the first full day of his sissy captivity and all he has to look forward to are lists upon lists of chores. 

All domestic duties that Erin would be doing while her hubby is at work, are done by Lexi. Chores like handwashing Erin's panties, the soiled ones that sissy so diligently held against the wall with his nose, is an example of one of these chores. 

And Lexi does all of this, with an anal plug up his ass. 

Toward the end of the day, as Erin is finished up with her tanning, her shopping and a professional massage, she returns home to find Lexi still working away in the kitchen, scrubbing the sink.  

"Go wait for him by the door Sweetie," Erin would say to Lexi, usually about 15 minutes before Brad would arrive home. 

When he comes through the door, he is pleasantly greeted by the sight of a submissive and kneeling sissy maid.

"May I please suck your cock Sir?" Lexi has been trained to say, upon Brad's arrival. Sometimes he says no, but it's usually a yes, and he gets a full blowjob to completion, as soon as he gets in the door. 

What a lifestyle!

Brad will grunt and shiver through an orgasm, as bursts of cum ricochet off Lexi's uvula and get swallowed down into his tummy. An appetizer before dinner I guess. 

Brad and Erin retire to the parlour and are served drinks by their sissy maid, while he also prepares a romantic dinner setting for the pair of them.  

Saturday evenings, Lexi gets a little more involved in the sexual activity of this couple, as Brad fucks Erin's pussy, directly over his face. The sissy remains in his chastity cage and still in maid lingerie with heels. It must be dreadfully humiliating, to have Brad's balls bouncing off his nose and tea-bagging his face, as he fucks Erin.

This is one of the few times that Erin allows her sissy to lick her pussy. She just loves the sensation so much, having her clit licked while her pussy is getting railed. The odd time, Brad will dip his cock into Lexi's mouth, to give him more of a taste of Erin. 

Once Brad cums into Erin's pussy, Lexi's mouth is in the perfect position to accept the cascading goo, as it bubbles and oozes from her, directly down Lexi's open hatch. Lexi verbally thanks Brad for his cum, then it's early bedtime. 

Again, just like Friday night, Lexi is dressed in something skimpy, frilly and pink, and is put to bed by Erin and locked into the princess bedroom. 

By 8AM the next morning, he'll be back in the parlour, holding the giant, black cock in his mouth while he waits for Erin to get up. The morning ritual has begun yet again and Lexi will soon be back in their room, holding Erin's panty gusset to the wall and listening to this hot couple have morning sex. 

Sunday morning to be exact. One final day of sissy captivity, before Lexi has to bust out the nail polish remover and return to vanilla life, vanilla, notwithstanding his chastity cage and panty girdles.

Sunday's come with a routine and ritual also, you may even call it...Sunday school.  

Mistress Andrea

xoxo

Continued in: Sissy School

Sissy's morning Ritual

Continued from: Sissy slave to a couple

On Saturday mornings, Lexi's cell door electronically unlocks at 7AM, the exact time his alarm clock sounds. I can picture him waking up in a daze, cloaked by Disney princess sheets and looking down at his sheer lingerie. He would feel his morning erection competing with the rigid bars of his chastity cage and would be feeling the thin band of his thong panties, riding into his ass crack. 

Brad and Erin are undisturbed by their sissy and get to sleep in on Saturday mornings, while Lexi heads for the shower. He is then responsible for doing his own make-up and wig and is required to re-dress in the same lingerie he slept in. 

Any deviation of this morning ritual, would result in severe punishment and likely a month or two added to his next chastity unlock date. 

To compliment Lexi's sissy attire, some strappy heels are provided in his room. Strappy so his toenail polish can pop, a perfect match to his pink outfit. 

Next comes the first of many, major humiliations of the day for poor Lexi. Just outside of his sissy bedroom, in the gentlemen's palour and adjacent to Erin and Brad's bedroom, this awaits: 

The picture doesn't do it a ton of justice as there's nothing to compare the size to, but it's a giant, realistic, black cock. 

Lexi knows what is required of him but is always apprehensive at first. 

Fearful of additional punishment, Lexi continues with his morning ritual. He gets down on his knees and takes the vascular, giant black cock into his mouth and just holds the pose. It's now around 8AM and by the rules that Erin has establish for her sissy, this is the way she wants to find him, when she wakes up. Feminized, denied, humiliated and holding a great big cock between his painted lips.

"Good girl!" Erin will coo to him, when she finds Lexi exactly how she wanted him positioned. 

Yes, in case you are wondering, Erin wears bedroom heels in the mornings, because she's a hottie. 

Erin then releases Lexi and they both click into the bedroom and over to the unwashed laundry hamper. Lexi has to kneel and find the panties that Erin wore yesterday, under her business attire, as Brad watches on. 

Cornertime is far more embarrassing and shameful when you have to hold an object against the wall with your nose. I've seen this done with a coin or with a piece of paper, the shamed individual is under strict orders that they will be harshly punished if the item drops. Additionally, with their nose pressed to the wall, it causes the bum to jut-out nicely and is a good way to present a spanked bottom. 

Erin uses a similar tactic, only her method is a little more devious. She makes poor Lexi open the inner gusset of her panties, the one's she was in all day yesterday, and hold the delicate material against the wall with his nose. 

How dreadfully humiliating for him, and the worst part is yet to come. 

Haunted and enchanted by the lingering scent of his Mistress, Lexi now has to listen to her have sex with her husband Brad. Lexi is under very harsh threats to not let the panties fall to the floor and sometimes his wrists are even cuffed behind his back. 

Painfully, Lexi now hears the unmistakable sounds of a cock being sucked, a pussy being licked and that first audible gasp from Erin, as she takes Brad's entire length into her pussy. 

Poor sissy can do nothing but listen and focus on that panty gusset with all the wonderful scents it captured a day earlier. 

The over stimulus that Lexi was now experiencing, combined with his crushing humiliation and having to listen to Erin and Brad both orgasm, had his little cock straining in its cage. 

Then came the gut-sinking order from Erin, one that Lexi knows well, from having performed this Saturday morning ritual many times before...

"Alexis huni, clean him up," escaped Erin's lips. 

Lexi slowly reached for the panties he was holding against the wall with his nose, still not letting them drop. He folded them carefully and neatly, trying to prolong the inevitable for as long as possible. Eventually, he hung his head in shame and wobbled in his heels toward Brad. 

"May I please clean you off Sir?" Lexi managed to squeak out, before dropping to his knees. 

"Of course," Brad cheerfully replied. 

Erin watched on as her husband guided Lexi's head onto his cock. Lexi cleaned down the shaft of the erect penis with his mouth, sucked a few times and polished each of Brad's balls with his tongue. 

"Thank you Sir." Lexi peeped out, after removing Brad's dick from his mouth. 

Brad began to head for the shower and in leaving, heard Lexi ask Erin, "may I please clean you up Ma'am?"

Once Brad's cum was suckled from Erin's hot pussy and swallowed by Lexi, this officially represented the end of sissy's morning ritual. 

Gawd damn this sounds so humiliating for him!

Could it get any worse? Silly question likely...of course it will. 

Mistress Andrea

xoxo

Continued in: Wait for him by the door