Sissy Stories

Taking inspiration from all the wonderfully sexy posts on tumblr and adding my own little story. I hope you enjoy. 👙🧚‍♀️🫦👯‍♀️🎊

[jadorefitness]

[sknyssy1980]

I like that he still looks. Even after everything I’ve done to him, when I’m wiggling and showing off my body, flaunting what he is now denied, I like that he will still timidly sneaks a peak. With his slender, smooth, feminine body also on display in his own sexy, little, gym outfit, there isn’t much for him to do with this rush of arousal other than to blush, squirm from the feeling of his little locked peen throbbing away in his tight little panties, and reapply himself to his girly workout routine. Watching him get all worked up, but be too soft and effeminate to do anything with his urges except throwing himself into keeping his legs shapely, his tummy taught, and his little booty nice and pert is such a wonderfully tantalizing training program for my little sissy’s body and mind.

As far as moving my little bestie’s feminization along, nothing can compare with bringing my favorite little femboy to the gym. Where else can he go where he gets to feel so inadequate along side all the real men with their big alpha muscles, wear such provocative girly outfits, feel like such a sissy around the sexy women that treat him like a girlfriend, AND get to actively work on making his body even more feminine? Nothing could’ve helped him more with the transition from being my boyfriend to becoming my pussy free sissy bestie more than our time together getting all tight and right at the gym. He’s just so delightfully demure and defeated after a good workout that it’s the best time to take him out for a quick bite, gossip about all the guys I’m seeing, have him help me get ready for a date, and then send him to bed while I saunter off in the manly arms of one of my lovers.

It’s why I like that he still looks. Even though he has surrendered to daily panties, weekly waxings, monthly manicures, and constant chastity, nothing gives me the thrill of those early days quite like seeing the longing in his eyes when he dares to forget himself and experience lust for his bestie. Even though the consequence of this is always me overpowering the wimpy little sissy, pulling his booty shorts down, pulling his thong panty up, and spanking his cute, exposed, little tushy, I can’t even pretend that I don’t enjoy it. I’ll smile, giggle, give him a little extra wiggle, all so he can really feel the ever widening chasm between his masculine desires for me and his pussy free pansy existence.

Every time we go through this little routine, I know it breaks his will to the point where he won’t be able to muster the energy to even try to reassert his pathetic manhood. He’ll spend AT LEAST the rest of day in his girly clothes, prancing around, fussing over his makeup, wallowing in the erotic draw of his complete emasculation. It’s part of the reason why I insist we hit the gym a minimum of five days a week. His body is becoming taut and feminine, his little clitty is becoming accustomed to being soft and small when aroused, and his mind is losing the ability to even imagine anything different. I don’t know if it will be the crunches, lunges, or the twerk aerobics, but eventually, something will break his puny masculinity to the point that all that will be left is my very in shape sissy bestie. I can’t wait.

[sissy-space]

Lets work on you sissy!

[sknyssy1980]

Is that FINALLY a little smile I see? Getting to feel all vulnerable and sexy isn’t all bad now is it?

I know, I know, you’re A LOT more exposed than you’re used to, but you really only have yourself to blame. If you’re hadn’t been sneakily wearing those beta boy boxers and jerking your little clitty like a disgusting little brute, you wouldn’t be in this predicament now would you?

Maybe when your girly tan lines really set in you’ll finally learn your lesson. I’m hoping that when you’re naked and deciding what to wear and you see the unrelentingly feminine lines of a bikini emblazoned into your smooth skin, you’ll have the peace of mind to leave your boxers in the drawer and instead select and wiggle your way into some of your pretty little panties. And when all this submission and femininity inevitably turns you on, you’ll see your girly tan lines and leave the masculine tugging to real men, and instead you’ll daintily rub your little clitty through your panties like a good little sissy. Of course, if this doesn’t work, I’ll have no choice but to lock your dinky winky up in a tiny pink chastity cage and let your small soft pee pee, hammered by the constant denial of all your sexual energy, reprogram your brain about how you should comport yourself.

I do truly hope that it doesn’t come to that. I just adore how every time you choose to wear pretty little panties and rub your peen like a well behaved girly boy, you’re reinforcing your own emasculation. It’s just SO sweet that every time you pick panties and rubbing over boxers and jerking, you are irreversibly molding yourself into a more perfect, pussy free, sissy bestie for me. I would just hate for us both to lose the thrill of you actively choosing to be an effeminate, twinky, femboy. Hopefully, the permanence of the bikini tan lines will be all the irrefutable proof you need to accept that you are at your most honest and happy when you’re a dutiful little panty boy.

Now, I said I tan lines, not burn lines, so come come, I’ve got to put this suntan lotion all over your body.

Yes, that does feel nice, doesn’t it sissy?

You like getting to feel my fingers work their way into all of your nooks and crannies, getting to wiggle and moan like a girly boy because you know your femininity keeps you safe. Even with your adorable little bikini bulge throbbing, we both know this is just some girly fun. We both know this will go no further than an innocent little flirtation because you’re a pussy free pansy, and we both find THAT terribly exhilarating. Hopefully you’ve been paying attention to how us girls touch each other because I’m expecting you to behave yourself like the sweet little sissy that you are when you’re lotioning me and all of my girlfriends up.

Well of course they’re coming. We can’t have a pool party with just two people, don’t be silly. The whole point of your girly tan lines is that they will make it impossible for you to hide your true nature in any intimate moments. Any time after today that you find yourself in a situation where you’re taking your clothes off with someone else, they will automatically know that you’re a sissy. You’re going to need to learn how to behave when it’s intimate and there is nowhere to hide, and I promise you that with how cute and defenseless you look right now, all the girls are going to want to have at least one intimate moment with you so you’ll get lots of practice.

That’s right my sweetie. You’re about to experience the world of sexy sissy privilege at your first girly pool party. As long as you behave like the demure, bashful, sweet, little, sissy that you are, you can expect to get the pretty princess treatment. You’ll be tickled, cuddled, kissed, and caressed right up unto the point where it’s your bedtime we send you off and continue the party with some real men.

Now, no one will know if you do or if you don’t, but how exquisite would it be to be tucked into your bed, wearing a flirty little nightie, rubbing your panties like a good girl, while all your lady crushes are in the arms of real men? And to make it even better, now that you have girly tan lines, you know full well that even if you squirt, you’ll stay in your nightie until you wake up the next day and wiggle your way into a fresh pair of girly panties. Who knows, maybe you’ll be so inspired that you’ll decide to not cummy cums at all and instead you’ll let your little weeny peeny throb away in your panties so you can reach new levels of euphoria in your sissy sub space from your self inflicted denial. So what do you say, doesn’t that sound just divine?

Of course it’s your decision, it’s ALWAYS your decision. Your tan lines have set in well enough that if you’re REALLY not ready to publicly proclaim yourself as a pansy you can go home and be a lonely little panty boy. But if you want to stay and make your cute little cheekies twerk while you dance, delicately rub lotion into our soft voluptuous bodies, and play along with whatever other flirty girly games we decide on, I promise you’ll have one of the most delightfully titillating experiences of your whole life. However, you should know that this much pleasure isn’t without danger. If you decide to stay, you can’t just get swept away in the feminine glee of the party, you’ll have to remain somewhat vigilant. A lot of my girlfriends just adore a sissy, are naturally aggressive, and might just become so enamored with your feminine charms that they’ll try to take control of you by locking your little dickie up in one of THEIR chastity cages.

If that happens, I would have no choice but to share you with them, and you would have to do whatever they said if you ever wanted to feel your little dickie get stiff again. After all the work I’ve put into you, I do not want to share my sissy bestie. Hopefully you can resist the urge to completely lose control and actually live out your sexy sissy fantasies by letting another woman tempt and tantalize you into chastity. Can you even imagine having two beautiful women all jealous and competing over who can inspire you to be the most effeminate and pretty? I just don’t know how I’d behave if you emasculated yourself in some special way for any one of my girlfriends.

I’d probably have to spank you until you did something even girlier for me. Maybe I should just send you home right now…what’s that?

Oh, you’d like to stay for the pool party?

Even with how embarrassing it’ll be for you?

Even with the potential danger that you’ll be seduced into a chastity cage?

Okay, if that’s what you want, I’ll allow it. You can stay. Now run along and go touch up your makeup so you can properly greet the girls, they’ll be arriving any second now!

[saturne21]

[sknyssy1980]

Now that we’re both properly dressed, we can have the intimate, flirty, girly fun I promised you. Oh sweetie, are you still feeling shy? That is SO cute!

Since you’re feeling so bashful, I’ll get us started by showing you MY panties. So what do you think sweetie? Do you like my panties? Do you think they’re pretty? Sexy? Now, will you be a good sissy bestie and show me yours?

Oh my. Those are some VERY flirty little panties you have on princess. You did such a good job picking them out. They look so sexy on you.

Why don’t you give me one of your soft sissy kisses? Mmmm, that’s nice. Give me one more. Isn’t this more fun than when you were my boyfriend?

You never got to get all pretty with me before. I can tell by how much your quivering little bulge is making your panties all gooey that you’re enjoying playing these sexy girly games with me. Showing off our sexy panties, wiggling around, and sharing soft little kissies is so much more intimate, so much more honest, than anything we did before. Which is why I want you to commit to only wearing panties from now on sweetie.

I know, I know it’s scary, but with your slender little body, your submissive temperament, your effeminate affect, and your tiny weeny peeny, being a sexy little sissy that wears pretty panties everyday really is the best option for you. In your tight girly panties you’ll have no worries, you’ll just get to be a sweet, soft, small, pussy free, pansy. All of those burdensome masculine responsibilities that you’ve always fallen so short of, you’ll just get to leave them to all the real men out there. Doesn’t that sound nice?

Oh yay! I’m SO glad you ready for this. Now come on, if we hurry we won’t be late to our appointment at the beauty salon. Don’t be silly, now that you’re a panty wearing sissy you have to get your body waxed, your nails manicured, and your hair styled into a sexy little pixie cut.

Well, if you’re REALLY that nervous about it, I suppose you can change out of your skirt and get into some leggings. Of course you have to wear girly clothes, after the salon we’re going to this great little lingerie boutique I know to get you all the panties, bralettes, and nighties you’re going to need to feel something soft, silky, and feminine on your body all the time. Without your girly clothes announcing you as a prissy femboy in pursuit of some pretty panties, we both know you’ll be too self conscious and shy to put in the proper time and care that’s necessary into picking out your intimates.

No more fussing missy. If you don’t get that sweet little tushy of yours moving right now, I will give you a spanking AND lock that little clitty of yours in a chastity cage for AT LEAST one month.

That’s what I thought. Stop looking so worried and give me a smile. You’re SO much prettier when you smile that if I don’t see you smiling all day I’m going to have to punish you. There we go. Oh my God, we’re going to have so much fun!

[feminizedcuckolds]

You hadn’t seen your wife for almost a year, a long time of step-by-step complete feminization under your mother-in-law’s supervision. You felt an intense shiver of fear going down your spine when you saw her at the door of your room, but she smiled and said, “Don’t worry, sweetie, you are now exactly the hubby I have always wanted. Come with me; I am going to introduce you to my lover. No, sweetie, you don’t need to put any more clothes on; you look perfect dressed as you are now.”

[sknyssy1980]

H..h..hello Sir. It’s a pleasure to meet you. T…thank you for stepping in and taking care of my wife while Mommy was taking care of me.

Yes Sir, both my wife and I really needed A LOT of taking care of. We both needed someone to help us feel pretty, dainty, and feminine.

Well Sir, for my wife that meant a big strong man like you was needed to fill her tight wet pussy up, and for me, it meant that my Mommy had to exude the necessary sensual dominance so that I could accept that I’m a pussy free sissy.

Oh yes Sir, after a year of chastity, feminization, and getting punished for not being pretty enough, I have fully accepted and embraced my role as a sweet, soft, sissy princess. I can’t even imagine spending a single second where my locked little softy isn’t resting in the tight embrace of some pretty panties. Mommy trained me so well Sir that I honestly can’t even remember what it feels like to be a man. Having to act with confidence and command, wear rough and tough clothing, and having a free pee pee that is expected to get and stay hard when it needs too?

No thank you Sir. I’d rather stay safe, soft, and locked, protected from the tough world of men by all my pretty girly things, and only have to worry about doing a good job on my daily chores. Mommy taught me that even do I was a terrible failure as a man, I can still be valuable as a sissy if….if you’ll let me Sir.

Of course it’s your decision Sir, you’re the man of the house. Mommy said I could only move back into your home with your blessing. She says that if you say yes, you’ll have to take on the responsibility of holding my chastity keys and in return for that favor I will be the home’s dutiful, dainty, sissy maid. Everything will be neat, clean, and tidy. There will be a place for everyone and everyone will be in their proper place.

Oh yes Sir, I do have a sissy maid dress, lots of them in fact. I’m not usually prancing about like this, all exposed and vulnerable in just my little panties. But everything I do put on my smooth and slender body is meant to reinforce my status as a…a pussy free, beta, sissy, cuckold. Mommy always made sure that I looked and felt like a soft, wimpy, effeminate, princess every hour of every day. I’ve spent so much time truly enjoying being pretty that now when I wiggle my way into my pretty panties and clasp myself into my matching bralette it feels like the most natural thing in the world.

But I do have to say Sir, being in your strong, intimidating, masculine presence, it somehow, unimaginably makes it make EVEN more sense why my wife left me with Mommy for a year to be feminized. Compared to you, I so clearly never had any business even trying to be a man. My body is too puny and slender, my temperament too submissive, my affect too effeminate, and my…my…peen is too small. To have any value, I HAD to learn to be pretty, to get comfortable in panties, and be ready and willing to serve.

I love my wife Sir. I want to be near her. But to have her love me back and actually want me around, I need to be the soft, pretty, sissy hubby she always desired. I understand, that as a sissy, that my wife has needs that I can’t possibly fulfill.

That’s why I’m so…so grateful to you Sir. Having a real alpha like you to take all the manly responsibilities in my marriage is the only way it could work. If…if you let come home and take control of my chastity keys, I promise I will do everything a little sissy like me can to support and nurture your relationship with my wife.

Well for starters Sir, she will live in domestic bliss, every household chore will be taken care of. She’ll have all that stress free time to spend in your big powerful arms. I’ll make sure all of your date nights are extra special by filling the preparation for them with as much girly fun as I can. Beauty treatments, shopping for sexy lingerie, giggling and gossiping about all the naughty things she wants to do with you, I’ll lovingly do whatever it takes so that you and my wife can enjoy each other. And once you’re together, you won’t even see me as I have a very early beta boy bedtime and will be spending every weekend with Mommy. So please Sir, will you please take charge of keeping my little weeny peeny small and soft as you’ve taken charge of keeping my wife stretched and satisfied?

[saturne21]

[sknyssy1980]

A sissy trilogy, I hope you enjoy reading them as much as I enjoyed writing them.

Part 1

Part 2

————————————————————————————————

When I first met Becky’s little beta husband, I didn’t understand the relationship. How could a complete knock out like Becky find anything attractive about such a small, soft, slender, simp? But then Becky started to let little hints about their marriage slip and I couldn’t help but watch as my contempt turned into curiosity. Panty play, cuckolding, chastity? Each little salacious tidbit made me want to not only hear more but actually covet the sensual dominance that Becky has with her little sissy.

I wanted in. So when Becks explained the concept of cucksitting, I pounced. I found that moving from my little fantasies of dominance to actually having the pliant little pansy, aching from months of nonstop chastity, in my clutches to be such an overwhelming aphrodisiac that I could hardly contain myself. The power I had over such a pretty, delicate, little, sissy was intoxicating. I just had to push the envelope.

The first time I cucksat him, I had us both strip down to our lingerie so I could try to teach the quivering little sissy how to hump and rub his adorable little panty bump on a pillow. I knew this alone was crossing a line, but that didn’t stop me from pushing the little sissy’s face down into the bed and grinding my kitty into his plump little tushy until both of our panties got moist. Emasculating the little femboy until he trembled with desire, only to send the pretty petal to bed unrelieved, still aching and yearning, filled me with such a feeling of erotic power that when the little princess shyly presented himself to me for his pre-beddy-bye inspection, and I saw how pretty and delicate he looked in his flirty little nightie, I knew I needed to keep this sissy in my life. I made sure I imprinted into his subconscious by cuddling up to him in his bed, letting my hands wander along the straps of his lingerie, and teasingly whispering into his ear how much his wife was enjoying getting plowed by real man as my little princess drifted off to sleep.

Fortunately, I wasn’t exaggerating. Becky’s appetite for getting her kitty stretched and filled by a real man’s alpha cock was insatiable. In almost no time I was back to cucksitting my favorite little sissy. After I’d stripped him down to his darling sheer pink panty and bralette set, I was impressed by all the progress my princess has made on his hump and rubbing. He’d clearly been practicing. He needed only a little coaching to finally completely let go of whatever fragments of his silly male ego he had left and allow his head to be filled with the sexy, flirty, girly thoughts he needed to be able to hump out a caged squirt.

It would’ve only been fair to let the sissy experience the overwhelming pleasure of a release after so long pent up in that tiny cage. He had earned it and it wouldn’t have done that much damage to his emasculation since his little softy was still safely locked up and he had completely surrendered his mind to his soft and effeminate thoughts and desires. No matter what happened, he’d still only want to a be a pretty princess that loved wiggling around in girly panties until all his goo leaked out of his soft, caged, clitty.

I could’ve let all that happen, but I didn’t. Instead I pressed his pretty face down and let him grind his cute little panty bump on my kitty until he got right to the edge of a squirt and then I pulled back. It was so delightful to hear him whimper and to watch him bounce his booty like a slutty little sissy yearning for the release that was just beyond his grasp. Before I put my little darling to bed, I let him know that even though he now has the power to hump and rub his way to a squirt, he will instead be doing his little sissy thrusts into a pillow everyday like a slutty girl and then stop, let his soft, caged, unsatisfied, little pee pee quiver, and then squirm like a weak beta all under my supervision. I made the sweet little sissy surrender whatever privacy Becky had let him keep to me by having him place a nanny cam in the corner of his room and then I marked him as mine by riding his caged dinky winky until I’ve coated all of his nether regions in my juices.

Everyday after that, I made him strip down to his bralette and panties and hump and rub himself right to edge of a squirt and every night I invaded his dreams by playing sissy hypnosis while he slept. Through both he came to relish his own denial because it keeps his head filled with soft, sweet, sexy, girly thoughts. He knows that squirting will only silence those precious voices that keep him in his blissful sissy sub space. As he accepts that edging is better than squirting, his old self fades to the back and his new femboy persona takes the spotlight at center stage.

I get to hear an insiders perspective about the process from gossiping with Becky. At first it’s just that he’s stopped pleading for panty breaks or to be released from chastity. Then it’s how, all on his own, he’s only wearing his girly clothes when he’s at home, which quickly evolves to him begging and pleading to be allowed to quit his job and work at a beauty salon so he can be a swishy, prissy, sissy all the time. Ironically, I find myself wiggling in my seat, crossing and recrossing my legs, as Becky recounts these enticing little episodes of her husband’s descent into submissive femininity. For her part, Becky just adores having the constant presence of all of this pent up effeminate sexual energy mincing about her house, fawning all over her, and looking SO pretty and delicate all the time. It is such a relief to FINALLY be rid of the wimpy beta husband and begin this new sexy sissy wife era.

I’m happy for them both. It was never my intent to break up their marriage. However, I also will not be missing out on all the sweet fruits of my labor, so, through a few subtle hints dropped here and there and the gentle coaxing of her sissy wife, Becky starte to develop deeper feelings for one of her bulls. Having a boyfriend takes time, and when you have a pretty little princess of a husband using all of his feminine charms to beg you to spend more time with your big strong alpha boyfriend, how could anyone resist?

Dates turn to weekends, weekends turn to weeks, until finally Becky decided to take a two month pleasure cruise with her bull and leave her darling little sissy hubby in my care as his extended cucksitter. Now we get to spend so much time in our sexy little outfits, sharing sweet little kissies while humping and rubbing until I finish and my darling little sissy is left as a leaky, quivering, horny, mess. This is when I discovered the most exquisitely delightful development. Apparently, my pretty prissy princess had internalized his programming and training to such a degree that when he starts getting close to edge, he begs to be allowed to slow down or stop his sexy sissy thrusties all together.

Hearing my little sissy’s voice desperately pleading to keep all of his girly goo in his tiny testes so that his mind can remain overrun by his sexy sissy thoughts tickles me so endlessly that I need more. I have to keep pushing the envelope, so I do the unthinkable. I unlock my little sissy’s chastity cage, letting his adorable little dickie out for the first time in probably years. Once his peen is free, I see both needy hunger and outright terror play across my little pansy’s pretty face. To help soothe the poor dear, I help him put on a very pretty, very tight, compression thong panty before his little guy can stiffen up.

Once as everything is safe and secure, I tickle his throbbing little panty bump as I explain that it will be his responsibility to make sure that his little dickie stays soft and girly. I “threaten” my tender little tulip that if he slips up and lets his cute little clitty get hard, I will make him hump and rub to completion. No more sexy girly thoughts, no more getting to feel dainty, delicate, and pretty, just a sad little sissy with a spent little peen. While literally quivering under my steady panty caresses, my pretty princess promises to keep his dinky winky small, soft, and unsatisfied.

After this, the most extraordinarily sexy game of cat and mouse ensues. There is absolutely nothing more delightfully arousing than an unlocked sissy who is truly terrified of his little pee pee getting hard and having to squirt. I am no longer confined to taking him to the edge when we hump and rub together but can now make my sissy wiggle his hips and let out his little, sexy, girly, moans whenever I have the whim to catch the little dear and make him mine. The game resets only after we’ve gone past kisses and caresses, my hands start finding their way into his panties, and my pretty princess’s only defense of his sissy virtue is to flirtatiously giggle, wiggle, and work his way down so that he can give me kitty kisses until I’m satiated.

All good things eventually must come to an end. However, before I return Becky’s sissy hubby to her, there is one last thing I have to do to make sure that my imprint on his psyche is so deeply penetrating that it can never be removed. Right before she arrives to pick him up, I get out his favorite pillows, strip us both down to our snatched little bodysuits, and have him start rubbing and humping his little pee pee mound right into the pillow. It doesn’t take long for him to reach the edge, but instead of allowing him to stop like I normally do, I push his face down and grind my kitty into his adorably plump little tushy. At first he tries to resist, but it just feels SO good that he can’t help himself from twerking like a little sissy slut in heat.

It doesn’t take him long to cross the threshold of orgasmic inevitability and then squirt until his whole bottom half is one big sticky mess. As he lies there quivering in the afterglow, I gently start cleaning him up and tenderly coax out the revelation than even after his squirt his head is still filled with girly voices that are still commanding him to be delicate, dainty, and pretty. I explain that, at this point, a soft pee pee squirt every now and then, and with proper supervision, won’t be able to bend the bars of his sissy mind prison. As I tenderly lock up his spent little peen back into its tiny chastity cage, I tell him that so long as he keeps it a secret, keep this feeling just between us, I will start to allow him to leak out a cummy cums when he’s been an extra good, sugar and spice and everything nice, little, sissy.

With a final little slap on his booty, I send my precious little pansy scampering away to make himself extra pretty for his wife’s imminent arrival. I will miss having my personal panty boy mincing about my home, but we now share something special, something that is just ours. He will be an attentive, submissive, effeminate, sissy wife to Becky, but he will only be a slutty squirt slut for me, and for all my work, that is more than enough. So when I give him his kiss goodbye, I do it without reservations, knowing at least one little soft piece of him will always be mine.

[sissyforhose]

You can get what you really want if you ask for it in the right way.

[sknyssy1980]

You want to ask. You’ve wanted to ask for your whole adult life. You’re just too timid and shy to articulate your desires into words. That’s okay sweetie, I know small soft boys like you have a hard time asserting their shameful sissy sensuality. That’s why we’re here to practice.

Now, before we get started, why don’t you strip out of that ridiculous beta boy costume you have on and shimmy your way into a nice, tight, pretty, pair of panties.

Oh yes sweetie, this is “entirely necessary.” While you’re still training for real life situations, you’re going to find it SO much easier to learn to express what you are really craving if you’ve already surrendered to those needs. Besides, it just us “girls” here anyways, no need to be so bashful. However, for that little act of rebellious deceit, why don’t you also wrap and clasp yourself into the matching bralette as well. We need to begin our lessons from a place of honesty sissy.

There we go. Don’t you look pretty. It feels really good to have your small soft penis be so firmly held in such tight girly panties, doesn’t it’s sissy?

You know that’s all you have to do. You just have to admit how much you like having your small, soft, little pee pee all wrapped up in pretty, pink, lacy, panties. I know you feel the most safe and sexy when it’s obvious that you’re pussy free because you’re so clearly an effeminate pansy. That’s what you truly want isn’t it?

Why don’t we start practicing expressing those desires.

Yes sweetie, you can rub your cute little panty bump while we practice. Now say it, say “my little pee pee is too soft and small for pussy, can I please wear some pretty panties instead?”

That was SO good princess! Try again.

And again.

And again.

And again.

It feels SO good to let go and freely say what you really want. Now say it one more time.

I know, I know princess. Saying your shameful secret desires out loud makes your little dinky winky want to pop. But sissies like you don’t get to squirt just because they want to. Little sissies like you are denied their pee pee pleasures unless they can prove that they’re well behaved, obedient, pretty, little, girly boys.

I’m so glad you asked. Of course I know exactly what you need to do to be considered a good little sissy worthy of a squirt. If you want to have a cummy cums, you’ll go to wherever you hide your girly clothes and put them on over that absolutely delightful bralette and panty set you currently have on. You’ll spend your day doing household chores, stopping every hour to rub your little panty bump and practice your panties over pussy mantra, until your 8:30 bedtime where you’ll be expected to be under your covers, lights out, and wearing one of your frilly little nighties.

The next morning, you’ll immediately put on another flirty little bralette and panty set, wiggle your way into some new girly clothes, and repeat the routine. It’s only on that second morning that you can reach down and rub your adorable little panty bump until you make a squirty squirt. This, by the way, is your new protocol anytime you want to pleasure yourself to completion. Any unauthorized squirts will mean forfeiture of all your beta boy boxers, 24/7 panties, and months and months of chastity.

Yes princess, you are correct. So long as you want to remain a secret sissy, these new rules mean you’ll only be able to cummy cum on Monday morning after having spent the entire weekend as a fabulous, little, twinkie, femboy. But don’t worry your pretty little head about it. I’m sure that with all the practice you’ll be getting expressing what you really crave, a cute little sissy like you will be to able to negotiate new ways to spend more time in your girly clothes and lingerie so you can squirt a few more times a week, which frankly, is more than enough for a sissy with a small, soft, weeny peeny.

[jadorefitness]

[sknyssy1980]

C’mon out sissy! It’s okay. There’s no need to be shy. We’re all in our nighties too.

Oh my God, you are just too cute!

Of course you’re the only one in pink silly. We had to do something special to commemorate you. It’s not every day, after all, that a little girly boy like you gathers all the most important women in his life for a sleepover so he can publicly commit the rest of his life to being a pussy free, panty wearing, pretty princess now is it?

For everyone single one of us, taking you in and sharing you as our friendzoned, beta, bestie was an absolute delight, but it doesn’t even come close to the amount of fun we’re all going to have now that you’re our soft, twinky, femboy. And don’t worry, we’re going to make sure you’re safe and protected for every little mincing step of your girly journey.

Well for starters, we’re going to make sure there is no hiding your feminine side, not even from yourself. You’ll have a monthly waxing appointment to keep your skin soft and smooth, and a weekly tanning one so your bikini tan lines are always there to proudly proclaim you as a sissy to anyone who sees them. Keeping your body’s naturally feminine features so accentuated will make it so much easier for you to accept that you’ll be wearing pretty panties every day.

That’s right sissy, you’ll be getting rid of all your boring beta boy boxers, undershirts, and pajamas and replacing them with flirty, delicate panties, camisoles, and nighties. You’re also going to buy enough girly lounge clothes to wear every minute you’re in your home. To support you, we’re going to be checking in on you a couple of times a day to make sure you’re behaving yourself like a good little sissy. If you are, we’ll reward you by letting you two finger tug your little clitty while we tease you about how much of a pansy you are until you squirt and empty your tiny testes.

If you’re a good femboy, your little pee pee is going to be so drained that it’ll always be soft, small, and limp as it snuggly sits in your pretty panties. Of course, you could misbehave, in which case, will give you the tough love you need by spanking your little booty and locking your dinky winky up in a tiny pink chastity cage

Awwwww, that makes you feel all tingly and hot in your panties doesn’t it sissy?

No need to by shy about it, we can all see you adorable weeny peeny throbbing away. You’ve been SO good today, why don’t you pull the little guy out?

Oh my God, your little clitty is just TOO cute! Look it how it’s just barely big enough to peak out over the top of your panties! Now get down on your knees and then spread them open so we can all get a good view. Yes sweetie, just like that.

Look at how excited your little dickie is! You can go ahead and daintily hold it with two of your manicured fingers and start giving it your adorable little tuggy tugs. There we go! Feel SO good doesn’t it?

We’re going to do this until your tiny testes are completely drained. We want our sissy to be a perfectly pussy free, functionally impotent, pretty, little pansy, with a soft squishy little mound in his panties and a mind free from the distractions of sexual arousal. When you’re feeling all hot in the panties, we all know how easy it is for you to get into your sissy sub space and prance around, which is fine, but we want you feeling like an effeminate panty princess in your quiet calm moments as well. We’re going to spend this whole slumber party monitoring you so we can determine what is the exact amount of pee pee playtime you need to keep you as a docile, demure, soft, sexless, sissy.

Oh that going to do it! Yes sweetie, rub it all out until you’re completely drained.

I know, I know my precious little pansy. I know after good satisfying squirty squirt you want to take your panties off and try to pretend to be a “normal” guy, but unless you want that little dicklet of yours locked into a tiny pink chastity cage for an indefinite period of time, you’ll not only stay in your panties, but you’ll also behave like the effeminate, prissy, little, sissy we all love and adore.

You’ll have plenty of opportunities to show us what an obedient little sissy you with all the fun, flirty, girly, games we have planned before your bedtime.

Like what? Well, the girls and I were thinking of truth or dare, getting all cuddled up and watching a rom com, twerking at a dance party, and of course gossiping about all the real men in our lives. We might even make you write some naughty DM’s to some of the guys on our dating apps. Doesn’t that sound like fun?

Don’t you worry your pretty little head about that sweetie. If any of our activities causes a stirring in your panties, you just let one of us know and we’ll get you right back on your knees and have you rub yourself like the pretty, pussy free, prissy, princess that you are. We’re all here to take care of you sweetie. Even after the slumber party, we’ll be checking in on you, giving you the teasing you like so you can drain your testes and keep your little clitty limp and cute in your pretty panties. But enough dawdling princess, we have the cutest little kissing game to play with you, you’re just going to love it.

[a-lesbian-sissy-2]

[sknyssy1980]

Everything has just fallen into place since I told my little sissy hubby that he’s only allowed to wear his girly clothes when he’s at home. It’s ended all the pretense and misunderstandings that this is some sort of sexy little game that we’re playing. There is no more confusion now that every time my pretty little hubby gets home, he immediately strips off all of his clothes, showers, shaves, rubs on his moisturizer, spritzes his perfume, and then goes and wiggles his way into his girly clothes. While he minces about with his pert booty, exposed midriff, and adorable little pee pee bump on display, he knows that his only real role is as my pretty, pussy free, homemaker. It is now everything that happens outside of our home that is the fantasy, the illusion, the game.

My little princess does all his chores, demurely follows all my instructions, keeps his little clitty aching and denied, and helps me find and date real men because it is his truest forms of self expression. Having to tuck his little clitty into a tight pretty thong panty, clasp on its matching bralette, shimmy his way into leggings, and wiggle into a matching, snatched, girly top every day has freed my precious little pansy from all the pressures and anxiety of manhood. He knows he can stay and frolic in the erotic wonder of his sissy sub space so long as he can keep his tiny testes brimming full with his girly goo. To help him keep his hands out of panties, we’ve installed nanny cams all over our home and made any unauthorized diddling punishable by spankings, embarrassingly early bedtimes, and, when he’s been particularly naughty, there’s nothing quite like his tiny chastity cage to make sure his weeny peeny stays small, soft, and needy.

As much fun as chastity play is, my preferred method for keeping my hubby’s peen cute and limp is a tight thong panty and the compression of his snatched leggings. I just love being able to make my little sissy squirm and moan with tender pinches to his little pee pee bump whenever I want to. Also, having such easy access to his clitty, living with that constant temptation, but being too wimpy and timid to do anything about it is the best imaginable reminder of his complete emasculation. All that pressure in his panties keeps his gait mincing, his wrists limp, his voice soft, his gestures small and effeminate, and his temperament submissive.

Even when I come home late and smelling of sex, having my pretty princess be constantly encapsulated in his soft feminine clothes makes it so he stays my demure, doting, sissy wife. He’ll meet me at the door, holding a glass of wine for me, offering innocent little sissy kisses as he ushers me in. He’ll strip me down, not so he can enjoy my naked body like a real man would, he knows he’s not built for that, instead his touch is light, soft, and feminine as he washes and massages my tender, post coital, body. After I’ve been properly pampered, I’ll have my pretty sissy peel his leggings down to his knees, pull the front of his panties down so his little dickie can stand at attention, kneel down in between my legs, and then do a slow two finger tug of his wimpy shrimpy as I tell him all the lurid details of my sexual escapades. When things get hot, I’ll have him soothe me with tender little kissies on my kitty, sometimes I’ll let him squirt, usually I’ll make him tuck his quivering, leaky, unspent, clitty back into the tight hold of his panties and leggings.

Making everyday mandatory girly day was the best decision of our whole marriage. Through endless repetition we have built a lifestyle where our roles are clear, our expectations can go unspoken, and we’re both free to live as our truest selves. Eventually I might put my sissy in dresses and skirts, I could use a nice firm girdle to compress his dicklet so it stays small and soft, but I do love getting to see every curve of his girly bod on display as a proper femboy. Maybe the next thing I’ll make him wiggle into are some tight, micro, booty shorts that’ll leave his precious little tushy cheeks hanging out the bottom while also being in line with girly boy aesthetic that I adore.

Whatever I decide, there will be no breaks for my sissy. He will be in girly clothes everyday. He will feel the soft, tantalizing, tightness of femininity encapsulate his whole body, fill him with desire, and then have to surrender to the reality that he is too much of an effeminate pansy to find any release without my express permission. While I openly and brazenly enjoy getting filled by real men, my pussy free, sissy, cuck’s only outlet will be making himself even prettier and girlier for me. This how it will be today, tomorrow, and always.

[sissymissyxo]

[sknyssy1980]

It doesn’t matter that I have plans. They’re cancelled now. Instead of going out for a drink with a woman I think might actually be romantically interested in meek little me, I’ve been sent to my room to thoroughly emasculate myself like the puny little sissy that I am. With a sigh, I slowly march to my room and start stripping out of my date outfit. I feel all the exuberance from being a “normal” guy, who wears cotton boxers, and goes out on dates with pretty women, shift into the seductive draw of having my masculinity revoked.

When I catch my naked reflection in my bedroom mirror, I have to confess that the only actual fantasy was thinking I could somehow hide the fact that I’m SO obviously a sissy. There is no explaining away the inherent femininity of my soft, smooth, little, girly bod. I can’t hide how slender, small, and squishy I am. No matter what I try, my little dickie will inevitably reveal that it’s at its most excited when it’s ridiculed, feminized, and denied.

This time is no exception as my dinky winky stands at full attention, quivering in anticipation of the coming activities. Given the mood that my bestie is in, I know that the very last thing that she’s going to have patience for is my little pee pee tenting my panties, so with hands that are trembling from a mountain of erotic dread, I set myself to the task of locking my weeny peeny up in my tiny pink chastity cage. Feeling my little clitty contained is one of the authentically erotic experiences I know, the only problem I have with being locked is that my bestie has the only keys and I never know how long she is going to keep me small, soft, and denied. Feeling SO powerless makes my peen impotently throb in its tiny cage and I can’t stop myself from letting out a little girly moan.

Now that it’s time to get dressed, I open the special little drawer in my nightstand revealing the extensive lingerie collection within. Everything is lovingly folded and organized, incredibly damning evidence of my eager and adoring participation in my own sissification. I select and shimmy my way into a pink, super sheer, thong panty and matching bralette because when bestie is fed up with guys nothing soothes her better than easily being able to see my locked little softy. With that in mind, I put on my pink, pleated, micro miniskirt and its matching, cropped, cami top with dainty little bows on its spaghetti straps.

The only way out is now through, so I dutifully sit at my vanity and with a very practiced hand start putting on my makeup. With so much of my own time, skill, and attention working to make me even prettier, it is not just my appearance that gets transformed, my whole internal life becomes daintier, softer, and girlier as well. By the time I am finished, my looks, thoughts, and feelings, all belong to the twinky femboy that I see reflected back at me. I am now ready to giggle, gossip, and cuddle with the woman of dreams, the deepest and most profound crush of my whole life, as a harmless, pussy free, sissy princess. I blow myself a little kiss, saucily snap my fingers, and head out to play some girly games with my bestie.

[sissy-space]

[sknyssy1980]

Oh sweetie, I’m SO proud of you! Deciding to embrace your femininity and express your true self, your sissy self, is so brave. I promise I’m going to be there supporting you through every dainty step of your girly journey. Whether I’m giving you encouraging little kissies and caresses, or, if you need my tough love teste taps and chastity sentences, I’m ready to do whatever it takes to make sure you meet your full sissy potential.

Your worried little face is SO CUTE! There’s no reason to be scared princess. We will take things nice and slow. After all, a pretty flower like you takes time to fully open up.

We’ll start with a simple monthly waxing appointment so your slender little girly bod can be soft and smooth all the time. You’ll feel SO feminine and pretty whenever you see or feel yourself. And when that makes you excited, and you want to pursue that pleasure, the only other rule you’ll have to follow is that you’ll have to wiggle your way into your flirty feminine lingerie to do it.

Yes silly, every single time. Whenever you’re seeking sexual gratification, you’re going to have to put on either one of your pretty bralette and panty sets or one your wispy nightie combos. I know that because you’re SO submissive being obedient is such an aphrodisiac that you won’t be able to help yourself from following my rules. You’ll get to feel like such a sissy when you’re all alone and getting all pretty for a quick dickie diddle that you’ll do it every single time.

Well, I suppose, hypothetically speaking, if you were to EVER actually go on a date, then yes, you would have to be wearing your pretty delicates just in case things go that far. To make sure you’re totally safe, I’m going to have to insist that anytime that you’re around a woman and things could conceivably take a romantic turn, you’ll have to be wearing some flirty girly panties and a matching bralette. We can leave no doubt or confusion that your little weeny peeny just isn’t made for pussy. Every woman will have to know that you’re more of a sweet, soft, squishy, cuddle buddy bestie than any sort of lover or boyfriend.

Haha, that’s so funny. I don’t actually see that happening, but fine, if a woman ever just “whisks you off your feet” and you’re unprepared, you’ll have to ask her if you can borrow some of her lingerie because you can only feel sexy when you’re in touch with your feminine side. Can you imagine her reaction when you’re pleading for something silky and pretty to wear? Oh my god, it’s going to be SO hilarious.

No no no sweetie. There’s no backing out of this.

Hmmmm, I think someone needs to go put on his panties and stand in the corner.

Yes sissy, just like that. You can stay there until you settle down and accept the fact that you are and always will be a pussy free panty princess. Eventually you will wear only girly clothes, your little pee pee will be locked in chastity, and your head will be entirely focused on how to make yourself even prettier. But there’s plenty of time for that. I don’t want the titillating excitement of the destination to ruin the transformative joy of the journey. One step at time sissy, one dainty step at a time.

[saturne21]

[sknyssy1980]

Oh my God, how did I end up here? How did I let this happen? My little pee pee answers my questions by impotently pulsing in its tiny chastity cage. I squirm in shameful delight as I feel my locked softy pull my wispy thong panty even deeper into my booty. The reason I’m wearing polka dot, denim, booty shorts with a matching, cropped, corset top for a girly shopping trip with my ex girlfriend/current bestie Becky is because I’m a sissy.

It was my deepest darkest secret. The shameful truth that all of my sexual desires and fantasies were totally wrapped into feeling like a dainty, girly, denied, panty princess was completely obvious if you knew what you looking for. My puny muscles, slender frame, effeminate mannerisms, shy demeanor, and submissive temperament were all the evidence any one would need to know that I have slipped into a pair of pretty panties to pleasure myself on more than a few occasions. No matter how hard I tried to hide these facts, if you were looking for a sissy to dominate, you would easily pick me out, and from the moment she first saw me, Becky wanted a sissy.

There I was, a meek little wall flower shyly sipping my drink at a hot party that I had somehow gotten invited to when Becky sauntered over to me and started flirting. Right away, Becky took control as her hands wandered and squeezed my soft squishy body, she whispered in my ear how pretty and cute she thought I was, she pressed into me until I was pinned against the wall, and then she took tender little kisses on my lips. I was so flustered by having this absolute knockout waltz over and dominate me so aggressively that my only response was to babble, stammer, and blush. Becky reached into my pockets, seductively tickling me as she went down, pulled out my phone, and then scheduled herself into my calendar for a date the very next evening.

One date would lead to another. In each one, Becky would nonchalantly exert dominance by picking me up, bringing me little gifts like flowers, perfumes, and jewelry, and then paying for everything. She was always the one who would be advancing our intimacy from tickles, to kisses, to rubbing. While I was in her arms there was a nonstop monologue about how pretty I looked, how soft I felt, and how I moaned just like a girl. Any effort by me to assert myself was immediately shut down as Becky would easily overpower and pin me until I promised to behave like her demure and dainty little beta boy. She would end every date by sensually massaging between my legs until I was trembling gooey mess and then she would send me to bed after I promised that wouldn’t diddle myself without her permission.

I was in heaven and things only got better as Becky started extending our dates into our homes and stripping us both out of our clothes. Once as I was in my boxers and Becky was just wearing the absolute sexiest bra and panty sets that I had ever seen, she would push me down, get on top of me, and then sensually rub and gyrate into me. While she did this she made me confess how much I loved feeling dainty and powerless and, in excruciating detail, how much I adored her lingerie. Right when Becky had me worked to the absolute edge, she would stop and tell me that I was just too pretty for pussy, but maybe I’d prefer panties instead.

I tried to resist. I’d laugh the comment off or pretend like I didn’t know what she was talking about. But with the fantasy that had been haunting my erotic imagination since puberty suddenly coming to fruition right before my very eyes, there was literally no chance that eventually I wouldn’t be seduced into becoming Becky’s little sissy princess. It was the very first time that she actually peeled me out of my boxers, took my little weeny peeny in her hands, and with a little kiss asked me if my tiny clitty was finally ready for panties that I inevitably surrendered.

There were, of course, additional terms. I had to pledge to be pussy free while Becky would continue dating and being ravished by real men so I would also be a cuckold. I would wear pretty panty and bralette sets every day, and soft flirty nighties every night. so I would always feel the delicate embrace of lovely lingerie. Finally, my little weeny peeny would be locked up in a tiny pink chastity cage and I would only be allowed to squirt if I was an obedient, effeminate, pretty, sissy.

Earning a squirt has meant a lot of different things. I had to commit to a daily beauty routine to keep my skin smooth and soft. Every night I needed to make sure I was in bed with the lights out by my 9pm beta boy bedtime. My body had to stay tight and right so I spent an hour every morning learning different flirty girly dances. And to make sure that my vocabulary, mannerisms, and thoughts were all appropriately effeminate. I only consumed feminine media and spent the hour before bed deep in the sway of sissy hypnosis videos.

However, today the thing that I had to do to prove that I am an obedient, effeminate, pretty, sissy that deserves a squirt was to publicly humiliate myself by letting Becky dress me up whichever way she wanted for a girls’ trip to the mall to replace my entire wardrobe with flirty feminine clothing and help Becky pick something sexy out for her date with a real man tonight. I feel so vulnerable and emasculated as my scantily clad super bestie pulls me from one boutique to another. The only thing keeping the spotlight off of me and allowing me to somewhat fade to the background is the way I mince about, how I’m now naturally limp at the wrist, and how I only speak with a soft lilting lisp. My innate femininity is my camouflage, my protection, my only real defense, and so I allow it to consume me.

It’s in this state that Becky and I go from perusing the feminine clothing on the racks to stripping each other down to our intimates in the dressing rooms so we can try on the sexy looks and make flirty girly poses as we giggle, wiggle, and model for one another. As Becky and I intimately fawn and fuss over one another, my tiny cage becomes impossibly tight, my panties get undeniably gooey, and I am completely enthralled by Becky’s power and beauty. Being SO close to her while staying small and soft, wrapped and trapped in femininity, denied her body and my manhood, is SO perfect that I feel all of my desires for a “normal” life melt and fade away.

Every purchase is now a promise that I’ll get to extend my sentence as a pussy free, panty loving, sissy princess. It’s only after I’ve bought more than enough girly clothes that it’s all I’ll ever have to wear that I get entangled in Becky’s embrace and feel the heat from her luscious body pressing into mine. We coyly giggle and share innocent little sissy kisses over my accomplishment today. My girly destiny is sealed and I couldn’t be happier.

[girlie-points]

[sknyssy1980]

From VERY early on in our relationship, Ana had been incredibly forward in letting me know I wasn’t what she considered boyfriend material. She explained, in excruciating detail, how she liked tall, strong, ruggedly handsome, alpha guys that were brimming over with confidence and swagger. She would go as far as showing me pictures of her dates and then bully and cajole me into admitting that compared to them, I was way too small, soft, and shy for Ana to ever consider romantically. After these confessions, Ana would wrap me in a tight embrace, give me little kissies on the lips, and tell me how even though I’m way too effeminate for her as a boyfriend, I do make for the sweetest little bestie a girl could ask for.

I should’ve run away. I should’ve have picked my shattered dignity up off the ground and done my best to find a real connection somewhere else. It’s just that I loved Ana SO much and her dismissive emasculating comments hit the central nerve of my erotic imagination harder and deeper than anything I had ever experienced before. She was so completely wired into my pleasure centers that the humiliation and embarrassment was never too much for me. If anything, as she went from ordering me to run errands for her, to doing all her household chores, to paying for beauty treatments and lingerie for her dates, to accepting that I was no longer allowed to date, to having to commit to being pussy free, to promising that I would only diddle myself with her expressed permission, and to accepting that I had to be home for my 8pm beta boy bedtime, I just kept on wanting more and more.

So when she came to me with the idea of us taking a six week girls’ trip I was terrified mostly because regardless of what this newest disgrace would entail, we both already knew I would inevitably say yes to it. She explained how we would be the best travel companions if I could make myself into her sweet, soft, sissy bestie. All I’d have to do is just let her accentuate how effeminate, sexlessly soft, and submissive I am by wearing pretty panties, locking my little pee pee up in tiny chastity cage, and letting her press a large butt plug into my tight booty hole every day of our six week vacation. As I started to recoil, Ana pursued, hands on my thighs, whispering in my ear that she knows all shy, soft, small boys like me have tried on panties before. Wouldn’t it be wonderful to drop all the pretense and have special intimate girly time with my bestie doing all the things that make me tremble and leak?

I melted. I didn’t know how Ana knew about my shameful secret desires but she did. My eroticized fears about being an inferior man and an effeminate pansy were formed over a lifetime of rejection, getting picked last, bullied, friendzoned, and humiliated. They were now being brought out into the open for the very first time, and instead of running from them like I had done before, I surrendered. Ana clapped her hands and giggled and suddenly my life became filled with things like a full body waxing, eye brow sculpting, facials, manicures, pedicures, and getting my hair styled into a pixie cut all to get ready for our trip.

After each appointment, Ana would take me to a local lingerie boutique to purchase a few panties and a couple of nighties that I would be wearing on our trip. It’s always such a humiliating affair. Every time Ana would force me to take my time with each piece of lingerie while she loudly interrogated me about why I always seemed to prefer very wispy delicates that were awash in bows and ruffles. I stuttered through my responses with a blush that could be interpreted as proclaiming to the world that I was a sissy who craved being as girly as possible.

Once as I had made my selections, and the whole boutique knew I was an effeminate panty boy, we would turn our attention to picking out a lingerie set that Ana could wear for date that night. The whole shameful production would repeat, this time with me bashfully holding my girly panties and nighties while commenting on what kind of lingerie I thought would turn a real man on. The final death swipe to whatever fragile grasp I still had on my masculinity would happen as I was paying for everything. I would stand there, blushing beyond belief and wishing I could just sink into the floor as Ana would always explain to the cashier that she would be taking all of our purchases home since she wanted my life in lingerie to start with our trip and little sissies can’t be trusted to not play with their panties.

The day of the trip, I arrived at Ana’s house as my first stop on the way to the airport. Just the thought that today is the day that I will finally be stepping into, pulling up, and then tucking myself into one of the girly panties that I have purchased would me more than enough to send me into a tizzy, but it is SO beyond that since Ana has forbidden me from diddling myself for the past two weeks. I’m absolutely trembling when Ana opens the door wearing only a black sheer peignoir and a matching bra and panty set. She explains, as she pulls into her home, that she figured that the best thing she could do to make me as comfortable as possible when I’m putting on my panties in front of her for the first time is to make it a fun girly panty party for the both of us. Before I can even really catch my breadth, I’m in Ana’s bedroom, with my small, soft, squishy body completely exposed, holding a lacy pink thong panty as Ana expectantly looks on.

Nothing looks that out of place as I slowly run the panty up my smooth slender legs and then create an adorable panty panty bump by tucking my small quivering pee pee into the girly thong. The tight embrace of the tiny panty is so uniquely feminine. The delicate material constrains my little clitty in the front while the thong divides my booty cheeks in the back. I’m overwhelmed by a swirling emotional hurricane of arousal and shame.

It’s in this moment of deep internal turmoil that Ana wheels out a pink suitcase and hands me a lacy pink bandeau bralette that perfectly matches my panties. She lets me know that I have a choice to make. I can take the suitcase that I packed and spend the next six weeks as a lonely secret sissy, wearing panties with a locked little softy and a plugged booty without any release OR, I could take the suitcase that she packed and spend the next six weeks as her very special twinky femboy. We could then play ALL the flirty girly games she knows I’ve fantasized about AND she’d let me work out a caged squirty squirt by humping a pillow and a vibe once a week.

With a predatory smile on her face, Ana lets me know that if I want to be her pretty panty princess, I’m going to have to put on my matching bralette just like I will be doing everyday for the next six weeks. Feeling the desperate throbbing of my little peen pull my thong even deeper into my booty cheeks, I don’t have the bandwidth to even pretend that I have to think this over as I clasp myself into the bralette. Ana is so overjoyed at how cute I look that she pulls me in for a deep hug that presses our bodies together and then lets it linger so we can feel the warm caress of each others’ soft skin. It’s during this sensual embrace, where hands gently explore and little kissies are shared that Ana has me tell her how happy I am to finally be pretty and pussy free.

With one last little squeeze, Ana lets me go and says it’s time for us to get dressed for the flight. Ana goes first and had selected a midi denim dress with a v deep neck that featured a double tie front and semi pleated skirt. And has me pull the dress up and over her voluptuous hips, and then because the v neck was so deep that it left the middle of her chest bare she asked me to remove her bra. When I faltered, she told me not too worry, a large part of my training to be a proper femboy will involve learning how to behave like a girlie bestie in intimate situations. All I have to remember for right now is that I’m not a real man and not act like one. My hands tremble, my breadth is short, and my panties feel especially tight as I unhook Ana’s bra, positioned her perfect breasts within her dress, and then tie her in. In response, she giggles, gives my panties a playful tug, and tells me how being a bashful little sissy seems to come so naturally for me.

Now it’s my turn. I literally gasp as Ana shows me the matching denim romper she expects me to wear. It has a halter top, a micro mini booty short bottom, and for the tiny amount that it does cover, its snatched fit will leave nothing to the imagination. As I beg and plead how I don’t want to be a panty boy anymore, Ana calmly folds her arms, cocks her head, and lets me know that even though she didn’t plan on spanking me before our trip even begins, she will if she has to. With tears in my eyes and heat in my panties, I step into the tiny romper and feel it encapsulate me in humiliating femininity.

The halter top shows off how effeminate my puny shoulders and arms really are. The micro mini bottom has my booty cheeks leaking out and leaves my entire legs completely exposed. However, it is the little peen bump in the front of my romper that makes me feel the most like an emasculated sissy. When Ana tenderly pinches my bump, I squirm and moan in delight as she tells me to enjoy this while it lasts because the moment we get to our hotel room my dinky winky will be starting its six week chastity sentence.

She wasn’t joking. The airports and flights were a blur. The whole time I kept my eyes down, listened to my heels click clacking on the linoleum, smelled my flowery perfume, felt the soft and tight embrace of my girly clothes, and held onto Ana’s hand like the shy, scared, shame filled, sissy that I am. The minute we get into our hotel room, Ana strips me down to my bralette and now VERY moist panties, has me ice my little peen until the swelling goes down and I feel numb, and then she very deftly puts the tiny pink chastity cage on me and locks it shut. As my weeny peeny warms back up, I’m mesmerized by the feeling of it impotently trying to grow, the sensation of being excited and electrically sensitive while staying small and soft is just beyond.

Ana now has me strip her down and we go take a shower together. With my little softy all locked up we can safely wash each other’s bodies, flirtatiously share kissies, and sensually press and rub our wet slippery bodies against one another. After we dry each other off, gently lotion each other up, and help one another into our delicates, Ana lets me know that it’s time for me to get plugged. I’m scared but I obediently get on the bed, bend over so my face is pressed into the mattress and my booty is up in the air, and feel Ana slowly peel my wispy little panties down my legs.

I feel one well lubed finger probe and then penetrate my tight little hole as I gasp and then moan. The combination of the second finger sliding in and rhythmically loosening me up while my little caged clitty stays small and soft has me surrendering all control to my inner sissy. There is nothing left but my girly desires to be filled when I reach back and spread my cheeks for the plug. There’s a touch, a push to the middle, a sucking in, and then a thud as the plug pushes out any lingering masculinity I have left. While I’m still trying to catch my breath, Ana daintily pulls my tight little thong panty snugly back into place.

Once I’ve recovered, Ana has me unpack our bags as she explains her vision for my behavior. As I’m hanging and putting away flirty feminine outfits, pretty lingerie, and scandalous little string bikinis, Ana tells me that she expects a girly girlfriend that always offers up obedience with a smile, a fun femboy wing sissy that helps her pick up real men, and an effeminate little twink that will stay pantied and plugged even when he gets sent to the room alone because she’s busy hooking up. Throbbing in erotic euphoria I surrender to all of Ana’s terms. She has me kiss her panties until she finishes to seal the deal.

After we dress each other in flirty little shorts and cami tops, we go out to take our first stroll through our exotic beach town. This is when Ana has me confess that I’m having fun. When she points out that this is just the first day out of six weeks where I’ll be locked in chastity, plugged, and wearing panties, I feel my little cage get tight with the implications. I already can’t even imagine returning back to my old life. When this is all over, who will I even be when it’s time to go back home? With a knowing little squeeze of my hand, Ana says she ready for us to go change into our tiny bikinis and hit the beach.

[planetthicknessmain-deactivated]

Top 5 PAWGS in the game rn!!

[sknyssy1980]

A sissy trilogy, I hope you enjoy reading them as much as I enjoyed writing them.

Part 1

Part 2

——————————————————————————————————-

Now that my sweet little sissy’s self image and erotic world are completely molded around his overwhelming desire for my voluptuous powerful body, we both spend A LOT more time in our delicates together. When we’re both disrobed in this manner, he gets to feel especially small, soft, and submissive in contrast to my size, strength, and dominance. During this morning’s feminization training, he sits and girlishly squirms in complete adoration of my thick body as I demonstrate how to move with flirtatious ladylike allure. After all the training and correction he’s received, when it’s his turn to put on a little show for me, he is now SO dainty and demure with his movements that I can’t help myself from rewarding him by manhandling his soft little body and pressing him deeply into mine.

There is nothing that makes my little princess’s weeny peeny throb quite like when our interplay creates a contrast between my feminine power and his effeminate passivity. Through the wonderful process of training my little pansy, his sense of self worth, affirmation, and delight now only come when he behaves like a cute, ditzy, little, priss. While he is in my arms, my little sissy shows the extent of his rewiring as he daintily wraps his legs around my torso and gently drapes his arms on my neck. My strong hands cup and squeeze his plump little booty cheeks as he cutely giggles and squirms in girlish euphoria. He has the sweetest little smile on his face and alluringly feminine arch to his back as he starts softly giving me his sweet little sissy kisses.

With a last little squeeze that makes him let out a little girly moan, I set my sweet soft sissy down so he can mince his way back to his room and get dressed. From his very first day with me, when he would whimper and cry from having to dress himself in girly clothes, I always insisted that he self selects what he is going to wear every single day. I believe it’s an integral part of a sissy’s training to have to decide for himself what type of soft, submissive, sexy, femininity he’s in the mood to express. My sissy has mostly gravitated towards ensembles that are flirty and feminine and showcase his slender girly body by being totally snatched and revealing lots of skin.

Today is no exception, my little princess shyly reappears in tiny pink booty shorts, a matching cropped cami, white knee high stockings, and cute pink heels. His smooth and slender legs, his plump little booty, his taught midriff, and his tiny chastity bump all look absolutely dainty and delicious in his wonderfully girly clothes. Next comes the fun part, with the cutest little growl imaginable my little sissy throws himself into me in an absolutely darling effort to knock me back. Since he’s SO cute in his wimpy futility, I always give him a few moments before I easily manhandle him across my lap with his puny arms pinned behind his back. Now I gently pull his little booty shorts down, and although his tiny thong panty doesn’t really need it, I still pull it so it is wedged even deeper into his booty cheeks, leaving his plump little backside completely exposed before I start his morning spanking.

In order to set the proper tone for the day, my big strong hand spanks his little booty until his gasps go to whimpers and then to out and out sobbing. Now that I’ve thoroughly established dominance and completely broken any lingering dignity or self respect that might’ve been trying to reemerge, I give his red tushy a few gentle rubs, tickle his tiny testes, and then pull his little booty shorts snugly back into place and send him on his way to clean himself up and do his makeup. From the very first time that my former lover Claire brought her wimpy beta husband around, I could see his potential to become the perfect, pussy free, panty loving, soft, sweet, sissy princess. Right away, I knew I had to have him.

This came with pleasurable task of having to bring Claire back into my sexual orbit. Given how much she enjoyed cucking her little hubby and submitting to feminine dominance, rewrapping Claire in my seductive spider web and making her wiggle until she confessed that, at her deepest levels, she needed the steady presence of a cock of a real man was actually quite simple. When it came with a promise that I’d keep her little beta husband and apply enough pressure to break his feeble masculinity and then rebuild him as a lovingly locked, permanently soft, flirtatiously ditzy, panty boy sissy toy, Claire couldn’t resist. During this time, it took awhile to draw out and nurture his latent and hidden girly desires, flirty femininity, and the pleasure of being a pretty panty boy, but when I added that to the natural shame and humiliation that all weak betas feel when they are emasculated, I had achieved the perfect blend. He not only lived up to, but actually exceeded, all of the sissy potential I first saw in him.

As if on queue, my darling peaks his head out. His makeup is perfect, luscious red wet lips, flirty eyes, a hint of glitter, and his pixie cut styled into cute little pig tails. With big fluttering doe eyes and a precious little giggle, he crawls into my lap and gives me the sweetest little sissy kiss before he starts his daily chores and feminization trainings. Although I haven’t even dropped a hint that Claire is on her way, I can tell that he suspects something special is happening since I haven’t allowed him to hold his little vibe against chastity cage and coax out a soft pee pee cummy cums for longer than usual. He is of course responding to his extra pent up sexual energy exactly as he was trained, by being an even flirtier, girlier, daintier, little sissy.

The way Claire waltzes in, looking absolutely ravishing in a red, sheer lace, micro mini dress, and then commanding my little pansy drop to his knees, grabbing the back of his head, and then pressing his face right into her silky black panties, you’d think she was trying to steal him back again. However, the truth is that since she started more seriously dating her current boyfriend Michael, we haven’t seen as much of her lately. There are no hurt feelings about Claire’s visits becoming more and more infrequent. We all understand that as much as she craves my feminine dominance and adores my sissy’s effeminate submission, Claire is just wired to always prioritize real men and their big alpha cocks.

None of that is of any particular importance at the moment since Claire and her somewhat estranged sissy hubby are all giggles and wiggles as they strip each other down, help one another get into their matching, itsy bitsy, pink, bikinis, and then make sure that they every inch of each other’s body is glistening with baby oil. Now they can start my full body massage and truly worship all my sensual curves and muscles as they press their slippery bodies into me and each other. While this is happening, Claire and I chit chat about our sexual exploits and all the naughty things we’ve been doing lately. We intersperse our steamy gossip with a steady interrogation of my little panty princess about all the reasons why he loves having his little pee pee locked up in a tight tiny chastity cage.

Hearing my sissy gush about how being kept small, soft, and contained makes him feel safe from the pressures of masculinity and free to be pretty and girly does something to Claire and I. When he gets to how his long denials from squirting allow him to focus and surrender into living entirely in the sissy dreamworld of his fantasies, both Claire and I are SO overcome by the sexual tension that we have no choice but to put my little pansy in between us and take turns of having having him kiss our panties or grind his plump little tushy on our kitties. It’s only after we both gloriously finish and my sissy is so wound up that his puny body is trembling, he’s short of breadth, and his locked little clitty is visibly quivering in its tiny cage that I give Claire the go ahead to break the news to him that she will be divorcing him so she can take the next step with her boyfriend Michael. My little darling proves again how thorough his training has been by showing genuine excitement about his soon to be former wife moving on with such a virile alpha like Michael.

It’s during their tender embrace where my pretty panty boy is apologizing for being such a failure of a man in their marriage that I let him know that he’ll be the perfect sissy wife to me in our marriage. When his confusion transforms to the realization that I have I just proposed to him, my little princess squeals in delight and leaps into my arms and purrs little I do’s in between his soft girly kissies. I explain that marriage to me means our dynamic will only deepen. He will have to retire from his career and his more androgynous womenswear and live exclusively in dresses and skirts as my little sissy homemaker. Going forward he will only ever be sexy but never sexual as his little softy will be locked in an even smaller cage with no key. His response to my conditions is just even more wiggling in ecstasy.

The formal process of signing the divorce papers is completely overshadowed by the joy of slipping a diamond ring onto my blushing fiancée’s very manicured hand. Claire pops a bottle of champagne and as we all sip and celebrate it suddenly became so evidently clear that Claire’s boyfriend Michael also deserves to partake in the festivities. Michael being SUCH an alpha that he can actually handle both Claire and myself at the same time makes the planning easy. We will start with a fancy dinner, get things going by dancing and grinding at a club, and then let all that energy go by finishing the evening with an all out threesome back at my place.

There is no room for an effeminate little sissy in these kinds of activities, and our dinner reservation is way past his bedtime anyways, but we do figure out that my little princess can participate by helping Claire and I get all sexy for Michael and then deciding to forfeit the squirty squirt I was going to allow him to have today. We’ll turn on all the Bluetooth cameras in his room so that throughout the evening, whenever we want to add a pinch of amusing dominance, we can sneak a peak at my little darling in his pretty nightie squirming around in his bed and impotently leaking into his tight little panties. Whenever I let my sissy “decide” to keep his dinky winky locked and denied, the combination of heartbreak and arousal always make him look extra pretty. He’s just too cute as he meekly squeaks out that as much as needs to squirt, the thrill and shame of keeping himself small, soft, and overwhelmed by desire are just too tempting to pass on. His precious trembling little voice continues by saying that if having him squirm and yearn in unyielding denial is the only he can make the day extra special for Claire, Michael, and myself, then he will submit to role and do his part.

I know that the emasculation of the moment only makes his cage feel tighter, the vulnerable femininity of his little thong bikini more pronounced, and deepens his understanding that only his only value comes from being a pretty, pussy free, panty boy. Because his behavior has just been exemplary, I decide he’s earned one of his favorites treats, so I hoist him into air by his bikini bottoms and hold him there dangling while I walk him to his bedroom to change his clothes. Both Claire and I fuss over and baby him as we get him into a fresh little silky pink panty and bralette set, then a sheer, sleeveless, pink, bodysuit with white polka dots, and finally a tiny, white, pleated, mini skirt. He looks absolutely darling when we finish by putting a pink hairband with a cute bow on his head and strappy white heels featuring little flowers on his feet.

Now it’s his turn to help Claire and I get ready. He starts by washing our bodies, shaving our legs, and trimming our coochies. Next it’s getting us into our outfits, first it’s our lingerie, where he has to spends lots of time on all the buckles and clasps, then it’s getting us into and zipping up our devastatingly short cocktail dresses. As Claire and I do our makeup, my little sissy spends his time on his hands and knees, going between our legs, giving us sweet little kisses on our panties to help get our kitties nice a ready for Michael.

Normally, this is the point in the evening where I would send my sissy away to get ready for bed on his own, but given how obedient he has been, and the momentous nature of the day, something a little more special is called for. So I pick my little princess up, holding him so his face is pressed into my ample cleavage, and carry him to his room where Claire and I once again strip him down to just his tiny pink chastity cage. We let a beautiful peach babydoll nightie that is all pretty ruffles and girly pleats cascade down his body and then pull the matching panties and some sheer control top pantyhose almost all the way up. Then in one deft maneuver, I unlock and remove his chastity cage, and before his weeny peeny has a chance to grow, I snugly tuck him into his tight little panties and the control top pantyhose.

The sudden freedom has my sissy so surprised that he is speechless. He’s completely mesmerized by the almost forgotten sensation of being out of his cage. I start lovingly rubbing his constrained little panty bump as I explain that on the same day that he got divorced, engaged, cucked by both his ex wife and current fiancée, that the only thing keeping him from the full pleasure of a hard pee pee squirt will be his own submissive effeminate nature. While we are out worshipping and getting filled by Michael’s alpha cock, his own little pee pee will be right there for him to take, but under the watchful eye of all these cameras, he’ll just squirm and moan like a good little sissy. We let him know that when we check in on him and giggle about how deprived, inferior, and weak he is, it will only make Michael stronger, harder, and more powerful for us. To make sure the temptation of a free clitty is ramped all the way up, we give my little sissy his final sensual pee pee squeezes and lingering kisses. As we shut the door and turn off the light, both Claire and I thank him for giving us all such a delightful present on such a special day.

[crochasteslave]

Yes Goddess! Thank you Goddess!

[sknyssy1980]

So, did you do it?

You did?!?

Oh my God you have to show me!

Oh sweetie, you don’t have to be shy. Now that your little clitty is safely kept small and soft in its tiny chastity cage, it’s more like we’re just a couple of girlfriends hanging out. Look, I’ll take my leggings off just to show you that it’s no big deal now that your little wormy worm is all locked up.

I’m glad you like my panties sweetie. Us girls get to wear darling little panties like these to showcase our small feminine bodies and make us feel dainty and pretty. Alright, let’s see what you have on. Shimmy your way out of those hilarious big gruff man jeans that you have on.

Hmmmm, I don’t know how to nicely tell you this, but you look absolutely ridiculous in those boxers. Everything looks out place, nothing fits. It’s just WAY too much fabric for your tiny waist, slender legs, and dainty bulge. If this is what you were giving, there’s no wonder why no girls EVER took you seriously. You look completely ridiculous, take them off love. Take. Them. Off.

There we go. That’s SO much better. Your locked little softy is just BEYOND precious. Now give me the keys sweetie so I can keep you safe.

I know it’s scary darling, but I promise you’ll feel SO much better if you just relinquish control of your erotic life to me. Even though your little guy is SO small and puny, look at how he’s bullied you into a lifetime of humiliation, ridicule, and heartbreak. He has you running around, embarrassing yourself with this pathetic “regular guy” cosplay you got going on, while the real you, the authentic you, is just yearning to be free. Can you imagine the wonderful, fulfilling, sexy life waiting for you if you allow yourself to be the soft, dainty, little sissy I know you fantasize about.

Of course I know, I’ve always known. You have such an obviously girlish build to your body and you’re so naturally effeminate and submissive that it was always the worst kept secret in the whole world. All you have to do is give me the key sweetie and you can let go of all the pressure from trying to be something you’re VERY clearly not cut out for. You’ll no longer have to pretend that you’re interested in girls, sex, and relationships. You’ll just get to completely devote yourself to being my very special, pretty, panty wearing, pussy free, sissy bestie. Doesn’t that sound great?

There we go. Now just let me put these keys in a safe space and then we can get started on turning you into a perfect pretty princess. We’re going to have SO much girly fun together. I’m SO excited!

[tayla-babygirl-x00]

[sknyssy1980]

At first I was totally mad at Claire for bringing her puny loser husband along to our girls’ day shopping trip. Our special trips to the mall are supposed to be a time to celebrate how pretty and delicate our femininity makes us feel together. I just thought that we weren’t going to be able to enjoy the delicate touch and flirty fun that has always been SO delightfully provocative with any man, even one as wimpy and soft as her husband, in tow. So imagine my surprise when I discovered that what I took as a weak, ineffectual, beta male was actually a sweet, dainty, effeminate, sissy.

They showed up to my home together. Claire in front looking beautiful as always, her husband a step behind, bashfully looking down to avoid eye contact, trying his best to take up as little space as possible, tethered to his spot by Claire firmly folding his outstretched hand. It was when I first took in what the little pansy was wearing that I started to realize that I was in for a naughty little treat of a day. The little darling looked SO cute in his navy blue, short sleeved, knitted, jumpsuit. The snatched fit hugged every curve of his slender girly body and was particularly adorable in the way it revealed each cheek of his plump little booty and his tiny peen.

It was with a squeeze of his very well manicured hand that Claire ushered him forward and told him to tell me what they had practiced. In a soft stuttering voice, the darling little sissy told me how the only thing that truly turned him on and made him feel alive was when he got to be such an effeminate little sissy that there was no doubt that he had to be kept pussy free. He told me how Claire made sure he always felt like that by making him replace all of his boxers and undershirts with bralette and panty sets, spend all of his time at home in womenswear, commit to a daily beauty routine, get a very thorough spanking and corner time if he stopped acting like a little priss, and making her perfect little kitty the exclusive territory of her very manly boyfriend. He got even quieter as he told me that even though it was unbelievably humiliating for him, he was SO excited to go shopping with Claire and I so he could add dresses and skirts to his girly ensemble of feminine short sets, rompers, pant sets, and jumpsuits.

Learning that Claire’s husband, whom I have always taken for a typical wimpy simp, was actually a VERY cute little sissy was a revelation that left me speechless. In a move that showed how deeply Claire’s feminization training had transformed him, he delicately took my hand and told me that to insure that there was no way he’d ruin this girls’ day with any of pathetic attempts at masculinity, he had agreed to lock up his clitty in a tiny chastity cage for a full month to both physically and mentally prepare himself for today. I don’t know what came over me, but having this sweet girly boy open up to me like a delicate flower, I just had to have him. I stepped towards him, and as he deliciously squirmed in front of me, I unzipped his jumpsuit, first revealing his smooth soft skin, then his very pretty, pink, flower embroidered, sheer, bralette, and finally, with a little tugging, his locked little softy sitting nice and snug in his tight matching panties. Seeing the little sissy so exposed and vulnerable before me, I became so convinced that this was a great idea that I kissed the little darling on the lips and then whisked him and Claire into my car and then off to our day of shopping.

Now that we’re at the mall, both Claire and I take our responsibility of training her little hubby to behave like a perfect pretty princess out on a girls’ day shopping trip VERY seriously. We make sure that he knows how to properly prance around a boutique and pick out pretty items for both himself and us. We teach him how to make sexy girly poses and twirl about in his new dresses and skirts. But the most important lesson he learns is how to be soft, seductive, and effeminate in the dressing rooms. The flirtatious giggles as we strip him down to his delicates, being able to both adore and tempt as his hands sensually tickle as they move along our bodies, and how to softly surrender to the fact that this is as exciting and intimate as it can possibly get for a pussy free panty boy like him.

It is Claire’s wonderful idea for her and I to have a double date tonight with our boyfriends in sexy special date night outfits. We decide that we can use her little sissy hubby as the model to try on a bunch of different looks until we find the right one. So our little princess minces about the different boutiques, picking out fun flirty outfits, and then modeling them for us and whatever giggling onlookers are present. The whole scene is SO humiliating for the little sissy, but all it takes is a quick inspection of his panties to see how moist they are from his locked dinky winky steadily leaking into them.

It is when we see the little dear looking so pretty and delicate in a short, belted, pink, miniskirt, a white, long sleeved, snatched bodysuit, sheer pantyhose, and dainty little white heels that we know we have our winner. Or at least very close, Claire and I will go for a color combination that is less over the top girly, more sophisticated, but still keeping the same sexy silhouette. Because this is for our boyfriends, it would be inappropriate to let a pussy free pansy touch our bodies while dressing us, so Claire and I dress each other while the little ninny watches and squirms. We take our time, soft titillating touches, adoring looks, idle chit chat about how our boyfriends would first be enjoying our flirty outfits and then our sexy bodies. The whole time, Claire’s soft, sweet, sissy wife watches us as our girlier reflection, gently rubbing his pantyhose encased legs together as his little locked softy impotently quivers and leaks in his tiny cage.

As we’re leaving, we make for quite the spectacle, two beautiful women and their twinky femboy strutting through the mall, heels loudly clicking on the linoleum, positively slaying. I have to say, our little sissy looks extra cute holding all his shopping bags from the various boutiques we visited today. To make room for all the pretty dresses, skirts, blouses, baby tees, and bodysuits they contain, our little panty boy will have to get rid of the last little bits of his male wardrobe from his closet and drawers and now live exclusively and publicly as an effeminate little sissy. We decide to make one last stop on our way out to celebrate this milestone and get his ears and bellybutton pierced.

Even though the sun is just beginning to set, Claire decides that since her little princess has had such a big day that she’s going to bump up his beta boy bedtime. Both Claire and I help the girly boy strip out of his skirt, bodysuit, pantyhose, and lingerie, and then help him into a pink, silk, babydoll nightie with a matching g-string panty. It’s during our goodnight kisses, when I have the sweet sissy sitting in my lap that I have to confess that I’ve had a simply marvelous time and would love if this little darling could join us next weekend for our girls’ day at the salon and spa. Claire says that this is her sissy hubby’s decision since it would mean another week of chastity. As the pansy ponders this new dilemma, my hands start roaming over his body, I hold my kisses with him a little longer, I feel his soft squishy body squirm and then surrender as he says how much he’d love to have another girly day with us.

We tuck him into bed. We each give one long lingering goodnight kiss and then we turn off the light and close the door. In a couple of minutes our boyfriends will be here and all of this sweet soft feminine build up will find its release in the strong hard arms of real men. The first of many girls’ days with my new very special sissy bestie has come to a close, but right as the mens’ formidable presence enters the space, Claire whispers in my ear that as long as I can commit to a weekly girls’ day she will dress her pretty petal of a hubby up in his sissy maid uniform and send him over to my house to clean and get properly riled up. Right before we throw ourselves into our boyfriends’ big powerful chests, we both let out a little giggle over an unspoken acknowledgement that this schedule means that her little sissy hubby will stay soft, small, and cute as he will never get out of chastity again, how positively delightful.

[sweetsubmissivegirly3-deactivat]

[sknyssy1980]

He’s so timid every time he arrives. He still blushes when strips out of his androgynous but decidedly feminine outfit and reveals his cutesy girly body. I just love how he’s completely smooth and slender and always wrapped in the one of the pretty bralette and panty sets that I insist he wears every single day. His little peen, clearly visible through the delicate fabric of his panties, stays soft and limp since he knows he must completely empty his tiny testes before he visits me or get punished with a month in a chastity cage if he pops a stiffy in my presence.

I never miss a chance to tease and caress my little sissy bestie when he’s feeling SO vulnerable and exposed in only his dainty delicates. While I squeeze his little panty bump, I have him tell me how much he loves being my soft, pretty, pussy free, girly boy. Once as I’m convinced, it’s time to get my pretty princess into a very girly little dress, heels, and makeup. It’s just so precious that even though my little sissy has more clothes on, the overwhelming femininity of being all made up like a proper girly girl makes him even more bashful and demure.

It’s when he’s in this state that girly fun time can truly start. We’ll giggle our way through rom coms, dance to girly pop, discuss fashion and reality TV, do each other’s nails, and of course, gossip about boys. I tell my little sissy bestie EVERYTHING. Every last little detail about all the naughty things I do with all the alpha guys in my life. I’ll even show him pictures and videos of me with them. I know it’s a little mean, especially with how hard my little pansy princess is crushing on me, but while his little dickie sits limply in tight little panties, I’ll make him comment on how big, strong, and handsome my boyfriends are and even write them flirty DM’s for me.

Once as he has thoroughly emasculated and embarrassed himself, it’s time for him to start his chores. He cleans my whole house while I lounge and tease him about how he makes for a MUCH better sissy bestie than he would a boyfriend. When he’s done, he meets me at the couch where I have to confess that he’s done such a good job and looked SO pretty doing it that I might just have to marry him, lock him into a teeny tiny chastity cage, keep him in just his flirty little dresses, and make him my pretty little sissy wife. This always breaks the last little feeble hold he has on his withering manhood as his true effeminate nature soaks in the praise. He’s now ready to squirm like a little priss as he promises me all the ways he going to make himself even girlier for me.

The last thing he needs to do before he goes home and puts himself to bed by his beta boy bedtime is to help me get ready for my date. As he strips me down it truly takes next to no prompting for him to shyly tell me how relieved he is that I have real men in my life to take care of all my needs that he’s way too soft, small, and girly to handle. He’s SO grateful that he gets to share intimate moments like washing my body, making sure I’m soft and smooth all over, getting me into my sexy lingerie, and all his little weeny peeny needs to do is just stay cute and limp in his tight little panties. As I give him his little goodbye kiss, I let him know that if keeps on being such a well behaved and pretty sissy, I might just finally have to consider taking him out on a date one day.

[husband-in-training-1-deactivat]

[sknyssy1980]

Hello Ms. Jessica, I’m here to clean your home.

Why thank you, looking like a cute little sissy snack is always my goal every time I get locked into my sissy maid uniform.

That is correct Ms Jessica, my uniform isn’t the only thing that is locked right now. My little dinky winky has to stay soft, small, and cute because it is locked up tight in its tiny, pink, chastity cage.

Of course Ms Jessica, just let me lift up my little dress so you can inspect my little locked softy all you want.

Oh! Oh my! Yes Ms Jessica, my tiny testes are quite swollen and tender. My wife has kept my peeny weeny locked up in chastity without any squirting for over three weeks now.

Thank you Ms Jessica, there is of course no need for YOU to spend your time rearranging MY panties, but I do truly appreciate it.

Yes, high and tight, so they go deep into my booty, yes, just like that. Thank you SO much. You are too kind.

Thank you Ms Jessica for inviting me into your home. It is quite lovely and I do still get quite embarrassed when I’m dressed like this in public. All those eyes on me, all knowing that I’m a failed man that’s been dominated into panties, chastity, and the servile submissive life of a sissy maid. It just makes me blush and squirm SO much. Oh look at me rambling on again, where would you like me to start?

Oh yes, you’re of course one hundred percent correct. Starting with a spanking will set the proper tone. I’ll just lie across you like so. Would you like me to count off?

1! Ow…thank you Ms Jessica.

2! For reminding me how soft and powerless I am.

3! Thank you Ms Jessica.

4! For showing me how shameful being a sissy is.

5! Thank you Ms Jessica.

6! For demonstrating all your authority and the proper contempt for panty boys.

7! Oh my gosh..ow..Thank you Ms Jessica.

8! For breaking my composure and self control.

9! T…thank you Ms Jessica.

10! For making my little pee pee impotently strain in its tiny cage at my own humiliating emasculation.

Oh…oh wow. Yes, there will be no mistakes over what my role is here after that.

Yes Ms Jessica, even if you want to play flirty girly kissy kiss games while I’m helping you get dressed, after a spanking like that, I’ll never forget that I’m just a delicate, dainty, panty boy and conduct myself accordingly.

I’d love to start by handwashing your lingerie! Oh my gosh, these are SO sexy and naughty!

I mean all these bold black and red pieces, way too strong and and powerful for a little pink and pastel sissy like me.

No no no, I’m not judging. Beautiful confident women like you should wear lingerie like this. I could never wear something so forward because sissies never act, they get acted on, and their dainty delicate’s should reflect that.

For your night out tonight?

You should definitely wear this leopard print teddy, maybe with a skirt or some sheer leggings. You’d look SO hot in that!

Yes Ms Jessica, I’ll wash the teddy first so it’ll have plenty of time to dry. Once as I have the rest of your lingerie finished I’ll do the dusting, clean the dishes, then do the vacuuming and mopping. That should leave enough time to help you get ready for your girls’ night with my wife and still make it home, put on my nightie, do my evening beauty routine, and be in bed by my beta boy bedtime.

That is correct Ms Jessica, by the time you are out with my wife and all your girlfriends drinking, having fun, and flirting with real men, I will have been in bed, with the lights off, in a flirty babydoll nightie with matching panties for hours. My little softy will have impotently throbbed away in its tiny cage as I imagine all the sexy fun mischief you all get up to until sleep eventually overtakes me.

Well, usually I get woken up somewhere in the middle of the night because my wife brought home a lover and I’ll squirm in erotic frustration to the sounds of their passion or she will wake me up because she wants a long sensual lick session where she cums over and over again and I impotently leak into my tight girly panties.

Oh Ms Jessica… what are you doing? Why are you taking your panties off?

You….you want a lick session too?

B..but that will make me get home late and I’ll miss my bedtime. My wife will spank my tender booty cheeks and..

You’re of course right Ms Jessica. That’s not your problem. You are paying for drinks tonight. You should get your money’s worth.