A Proper Fitting for a Sissy

[Baby Bobby]

A Proper Fitting for a Sissy


My name is Tiffany Johnson.
I'm 29 years old and I work at Chastity Services, along with my best friend. Primarily what we do, is to fit males for chastity devices, sometimes willingly, other times...not so much. But either way, any male coming into my shop will leave with his little pen-is imprisoned and secured under lock and key.

I deal with a lot of sissies in my profession. I find that they tend to have a fascination with panties, or dressing up like women, or some other such perverted fetish. We get geeky guys coming in on their own and they're curious about the concept of chastity and I'm only too happy to help them out. They're often shy and easily intimidated so that's just what I do. Its fun to watch them blush and squirm in my office, especially since I've always had a thing for dressing provocatively, wearing low cut tops that display my big breasts and snug skirts to show off plenty of leg.
I like to question them bluntly about their masturbating habits, how often they do it, as well as what they masturbate to. They always blush furiously when I question them but they're too weak-willed to actually get up and leave.
 
The fact is, I can spot a sissy from a mile away and I love nothing more than to humiliate them in any way I can. I've been that way for as long as I can remember, all through out my junior and high schools, but truth be told, I started even before that, in grade school.

Of course, a proper fitting for a chastity device means having them drop their drawers so I can measure their pathetic little pen-ises. They probably come in thinking I'll be very clinical and dry like a professional nurse but in fact, I'm just the opposite. It's inevitably a mortifying experience for the guy, and I take every opportunity to embarrass him, making disparaging comments about his size and telling him just what a pansy he is. I also make sure to tell all of them that I assume they're virgins and that they've never been with a girl before.
 
With regards to the devices themselves, its surprising, but what a lot of women don't realize is just how small of one you can stuff a guy's pen-is into. I don't want these sissies to have so much as a millimeter to be able to grow in, so I always make a point of fitting them in the smallest chastity device I can get them into. Fortunately, we have lots of the smaller, harder to find sizes than you can't get online, so the sissy boy is usually both shocked and ashamed at what we can fit him for.

We also talk to a lot of our manufacturers, giving them constant feedback and as a consequence, almost all of them now offer pink versions of their devices. And we make a point of pushing that color as a choice for most of our males, browbeating the wimps until they finally cave in. Believe me--nothing looks more pathetic than a male wearing a pink chastity cage around his tiny package and shaved crotch. No woman will ever take him seriously after they see that.
 
One of my favorite tricks is to fit them for a device, lock them into it, and at the end of the sale, I appear to hand over the keys.
Little do they realize that the keys I gave them aren't the real ones, since I always keep those in a safe, secret location, but they don't find that out until they get home, and sometimes, not even for several days. After that, I screen my calls, just to ensure the little sissies will squirm with panic and fear. I want them to experience at least a full week of real chastity, outside of their control--not knowing if they'll ever be able to touch their pathetic wee-wees again.

It never ceases to amaze me what you can make a locked, desperate sissy do, just to get access to the real keys. And I make sure that whatever I demand of them will be extremely humiliating for him to endure.
 
In high school, I was something of a bully to the weaker guys and I've only become more determined to put these wimps in their place in my professional life. At 5' 10", I am on the tall side, and in my 5" heels, I tower over most guys, especially sissies. My haughty, imperious nature is more than enough to make them tremble but being tall also helps.

Growing up, I was an early bloomer and I was already sporting a generous C cup by my 14th birthday. By 18, I was outgrowing my DD bras from Victoria's Secret. Nowadays, I have to order my bras online from specialty stores to get ones that will fit. A 34EE size cup just isn't to be found at Nordstrom's.

All too often, these pervs coming into our shop try to steal glances down my low cut tops when they think I'm not looking, but I always catch them and scold them mercilessly, making the little creep blush bright red with shame.

The other day, I had an interesting visit from a couple that I think is worth relating.

A husband and wife came into our office last week and right away, I could tell the guy was a sissy. He seemed really nervous, and had difficulty making eye contact with me. Instead, his gaze would dart anxiously around the room, as if he were trying to find some way of an escape.
By contrast, the woman was cool and collected, confident and self assured--everything her husband wasn't. She looked to be in her mid-thirties, with jet black hair and a slim, yet curvy figure. She dressed smartly, with a close-fitted blouse and a skirt that showcased her long legs.

I have an eye for detail, and looking at her fidgeting husband, I felt certain that he was wearing diapers underneath his trousers. He seemed very self conscious, and he shifted in his seat, as if desperately trying to hide his childish underwear.
Definitely a sissy.

After sitting them down in my office, I offered her coffee (purposely ignoring him) and took a seat before them, crossing my legs in a deliberate manner to test her sissy husband's reaction. Sure enough, although he tried to hide it, his eyes couldn't avoid staring as my short skirt rode up my thighs.

"Tell me how I can be of assistance," I said, smiling pleasantly as I looked the wife in the eyes.

"My name is Leanne and this is my husband, Conrad," she said, referring to her spouse with a dismissive thrust of her extended thumb.
"He has a chronic masturbating habit and I want to put a stop to it."

"That's disgusting," I said firmly as I looked him up and down with disdain.

His face went bright red and he looked away, tugging at his collar anxiously.

"How often do you play with yourself, Conrad?" I asked him point blank.

His mouth opened, but it seemed there was no dignified way to answer the question, especially with his domineering wife right next to him.

"Every chance he gets," she replied without hesitation, "I make him wear diapers because of his nightly bedwetting, and Cassie simply can't resist the soft cotton Birdseye I pin him into."

I shook my head and stared hard at her wilting husband.

"I thought as much...am I right that he's wearing his diapers now?"

"Yes he is--he made a fuss about coming down here today so after a trip over my knee, he got to wear his nighttime diapers instead of his regular underwear.
"Cassie--why don't you show Ms. Johnson here your pampers?"

Her hubby shot a panicked look back at her and he shook his head pleadingly, silently beseeching her for mercy.

"Cassie? Do you need another dose of the hairbrush? Because I'll do it right here and now if you want to push me."

The color drained out of her hubby's face and with a sob of shame, he slowly stood up. Fumbling with his zipper and clasp, he clumsily managed to undo them and his trousers slid down his slim, hairless thighs, revealing his prissy, embarrassing diapers. Obviously designed to ensure maximum humiliation for the wearer, Leanne had chosen a pair of pink nursery print plastic panties with babyish white ruffles around the legs and waistband.

"Well--I see who wears the pants in this relationship," I snickered, "Are you wet, sissy boy?"

Conrad shook his head miserably but didn't look up at me.

"Answer her when you are spoken to," his wife barked.

"N-no Ma'am," he whispered meekly.

"Good, let's try to keep it that way," I told him, "You might as well take those pants all the way off, you won't be needing them for a while anyway."

Conrad bit his lip and slowly removed his pants, folding them neatly and putting them on my desk. He looked absolutely ridiculous in his polo and bulky pink diapers and I noticed he took his seat gingerly, presumably because his bottom was still smarting from his earlier spanking.

Returning my attention to Leanne, I gave her my usual sales pitch.
"Now--I have a number of chastity devices for you to choose from for your little sissy here," I explained to her, "Depending on his size and your preferences, we have steel, plastic, and a number of colors, although I think pink would suit Cassie here the best."

"I agree," she replied, "More than anything, I want it to be super secure so that's there's no chance he can escape from it or have access to his little pen-is."

"Oh--absolutely. Trust me when I tell you that after today, your sissy's masturbating days are over for good," I assured her.

Out of the corner of my eye, I could see her hubby cringe with fear.

"Now--we have two kinds of devices--those with spikes and those without."

"Spikes?" she asked in confusion.

"Oh yes, some of our devices have spikes inside, to discourage any sort of arousal from the wearer. They're very good at making him focus on other things--like his chores around the house, for instance," I explained.
"They're usually not a problem for everyday wear, until he starts getting turned on, that is. At that point, the head of his pen-is will begin pushing against the spikes, quickly discouraging any further thoughts of naughty behavior," I said, eyeing her fidgeting sissy with a knowing grin.

"Oh--that would be perfect," Leanne agreed, "That way, when my boyfriend is over, Cassie will be less interested in what's happening to me and more focused on his mopping duties."

"Oh--you have a boyfriend?" I asked intrigued.

"Absolutely. This sissy here is completely incapable of satisfying me so I did what any sane woman would do--I went out and got myself a real man to take care of my needs."

I smiled broadly at her.

"Good for you! Although I'm hardly surprised. I'm finding that most women in your place are doing the exact same thing. Why be stuck with a bedwetting sissy in diapers who can't perform--when you can have a real man in your bed every night who knows just how to satisfy you?"

"Exactly. I leave Cassie to enjoy the wet diapers and crib sheets while I get to enjoy a nice big coc-k every night, reaching places that he never could. I can't tell you the kind of mind-blowing orgasms I enjoy nowadays. Its so night and day from when I used to let Cassie into my bed," she explained with another thumb pointed at her blushing, diapered hubby.

Cassie was fidgeting uncomfortably with all this humiliating talk about his shortcomings and it was clear he wished he could be anywhere but in this room.

"Well, I think its time now that we introduced your sissy to a life without orgasms of any kind, don't you? Should we take some measurements?" I offered.

"Absolutely. Cassie--Pull your diapers down. I know its not much, but it's time to show Ms. Johnson just how pathetic you are."

With a sob of shame, her husband reluctantly began lowering his shameful diapers down his thighs.
And even though I've seen a hundred little peckers like his, I swear--every time its still a bit shocking.
Cassie's pen-is looked like a little nub, no more than an inch, protruding from a small set of balls the size of marbles.

I couldn't help it.
I burst out laughing, covering my mouth as I looked from his ridiculous "manhood", up to his beet red face and then back down at his crotch.

"Oh-my-god," I said astounded, "You weren't kidding--that thing is absolutely pathetic. And you've definitely made the right decision in locking it up--such a tiny little thing like that has no business being free. It needs to be locked up tight, where he can't get at it or play with it."

"I'm glad you agree with me," Leanne concurred, nodding her head.

"Oh yes, believe me--I'll make sure this little bedwetter can never play with himself again," I said, filled with determination.

"You hear that, Cassie?" Leanne said, "I hope your last orgasm in your sissy diapers was a good one because it'll be your last."

Cassie winced and bit his lip, squirming in place while I began taking measurements of his tiny nub. It still had a slight coating of baby powder and in fact, if I hadn't known better, I could have easily believed I was measuring a three year-old, diaper-dependant toddler, instead of a grown man.

"Its good you came here," I told his wife, "Getting devices that will fit for a pen-is of his size are really hard to find. Fortunately, we deal with a lot of sissies so I know I'll have something that will work."

"That's a relief," Leanne confessed.

Going over to the wall behind my desk, I opened several drawers until I found what I was looking for. It was a small pink device, much like a CB6000S, but smaller and with short spikes on the inside of the tube near its tip.
I held it up for her inspection.

Leanne took it in her hands and a big smile crossed her attractive face.

"Yes...yes, this is just what my little sissy needs," she said nodding her head in agreement, "This should keep you focused on your work instead of rubbing your diapers all the time."

After handing it back to me, I disassembled it, and then knelt before her nervous hubby to begin fitting him for his permanent chastity. Quickly, I removed all the spacers and taking the cuff ring, I slipped it behind his little sack.

"This is the part I like," I said winking over at Leanne.

"Say hello to your new best friend, Cassie," I smirked as I held the short pink tube positioned before his pen-is and spat on his pathetic nub. With a quick, non-sexual stroke, I covered his shaft with the saliva and pushed it forcefully into the pink tube, quickly mating the holes in the base with the pins on the cuff ring. Taking the small brass lock, I deftly slipped it through the central pin and snapped it shut with a crisp flourish.

"There you are--another helpless sissy boy made chaste," I said brushing my hands in a gesture of finality.

"Perfect!" Leanne exclaimed, clapping her hands with glee, "That looks wonderful. And the pink is so appropriate for him."

"I couldn't agree more. And its good you keep him shaved down there--he doesn't have any need of pubic hair anyway," I told her.

"Yes, I had it laser removed years ago when I first started putting him in diapers. It makes it so much more hygienic."

Reaching over, Leanne grasped the device and gave it a solid shake, causing Cassie to whimper with anguish. It was obvious the device was on for good, until such time as she decided to unlock it.

"How does it feel, baby?" she asked her cowering hubby.

He shifted his feet and grasped the device gingerly, twisting it a bit in a futile attempt to remove it.

"Can you feel the spikes?" Leanne asked.

With his lower lip trembling in a pout, he shook his head.

"N-not yet," he quivered fearfully.

"I think you can put his diapers back on," I told her, "If you like, I can give you a quick demonstration of the power of the spikes."

While a look of abject fear crossed Cassie's face, his wife smiled wickedly and nodded her head.

"Oh yes--please do."

After his prissy pink diapers were back in place, I sat him down in the chair and spread his legs slightly, bending over him and smiling warmly into his face. With my left hand, I began casually but sensually stroking the silky skin on the tops of my exposed breasts, right where the plump, curvy mounds pushed against each other.

"Do you like big breasts, Cassie?" I whispered in his ear seductively as my other hand reached down and lightly rubbed the front of his diapers. It was soft and cushiony and I could understand why he might be tempted to rub them so much.
Cassie was obviously feeling overwhelmed and he shifted nervously in his seat. Nevertheless, his gaze unerringly fell upon my cleavage and his breathing became heavy and labored. I stroked the shiny plastic front of his diapers lightly--after all, it only takes a little effort to get the right effect.
Sure enough, in just a few moments, he began shifting uncomfortably and a groan of pain escaped his lips.

"Owww!!" he suddenly cried, hastily shoving his hand down the front his diaper to wrestle with his package.
I stood back and watched him, looking down at him with satisfaction as he struggled to extricate his captured wiener from the device. Of course it was quite hopeless and no matter how he pulled or tugged, his pen-is continued to push urgently against the sharp spikes, making him writhe with pain and discomfort.

Leanne and I laughed and she clapped her hands again, immensely pleased with the results.

"Sold!!" she exclaimed happily.

I nodded and smiled, handing over the keys to her as Cassie bunched his fists in mute frustration.

"Be very careful where you put these," I warned her, "I would recommend taking them to your work, or some other inaccessible location. If you hide them in the house, eventually, he'll turn it upside down in order to find them."

"You know what?--I think I'll give them to my boyfriend. He can decide when or if the little sissy ever gets any satisfaction."

"Excellent choice," I commended her.

"Tell me--what's the best way to relieve the built up pressure in his balls?" she asked, "I assume he needs to be 'milked', or something like that."

"Yes, there are a number of ways you can do it. Some people use a device called an Aneros tool to massage his prostate gland. It can be a tedious process but eventually, you can completely empty his balls of any fluid that has built up over the course of a month.
"Some women use a strap-on and they have a once per month session with their sissy to drain him that way. And that's also a memorable way to re-assert your dominance over him.
"Then again, other women just let their boyfriends bend him over a couch and have their way with him--it's totally up to you."

Leanne nodded in understanding.

"Most sissies are very resistant to getting their asses fuc-ked by another man, but after a while, when they realize its the only kind of sex they're ever going to get, they begin looking forward to having a nice big coc-k filling them up inside.
"In any case, there's usually no need to remove his chastity device, it will all come out anyway."

"Well," Leanne said as she stood up, 'I can't say how happy I am that I found you. Your business is an absolute godsend!"

I smiled proudly, extending my hand to shake hers.
"I'm only too happy to provide a valuable service, locking up the pathetic dic-ks of sissies like Cassie here."

As she took out her credit card for payment, she nodded absently to her hubby.

"Cassie--thank Ms. Johnson here for giving you the chastity device you so obviously needed."

By now, his little pen-is had subsided, and he was no longer feeling the sharp spikes within his device.

Clearing his throat, he blushed and shuffled his feet, staring at the floor.

"Th-thank you, Ms. Johnson," he mumbled, his cheeks burning with humiliation.

"Thank you for what?" Leanne prompted him.

"Th-thank you for fitting me for the ch-chastity device I needed," he stumbled submissively.

'You're quite welcome, sissy boy," I said as condescendingly as I could.

Leanne and I shared another laugh at his expense and after ringing her up, I said my goodbyes.

Just another day's job, well done, here at Chastity Services.



THE END