An Office for Growth (SweetAnnie40 + sissykaitlin)

Watching how easily you move to please and serve makes me smile. The only question I have now is what to do about you and work. I have an idea I've always wanted to do but never had someone to do it. I never was able to play with someone like you so maybe you'll agree to it. For now, I sit back to enjoy the show.

You are hyper-focused on the first cock in your mouth and the second. By the fifth cock in your mouth as another moves into your slick and dripping pussy, you are just experiencing the idea of it, the push of the cock stretching your lips and sliding into your throat again and again until the cum blasts forth, spurting then flowing. You feel the hands holding your hips and thrusting hard into your eager ass, your body jerking with each thrust slamming his body into yours, your breasts moving back and forth in rhythm.

I come sit on the bed as you're starting to get double-fucked by guys who started on you and are ready for a longer, 'second round'. I caress your body and whisper in your ear what a beautiful sissy slut you are, how wonderfully you suck cock and how much cum you've swallowed.

The fifth man entering me has me gasping--drooling as I suck on the cock in front of me as I try to gather myself. My back arches and I can feel my balls smacking back and forth with each thrust. I let out a moan feeling the cum drying on the back of my thighs. As you sit down I pull back on the cock in my mouth and turn towards you--wanting desperately to kiss you but not doing so.

All I can think is about how tomorrow is going to feel after having been used for so long this evening. As the man fills my boi pussy I let out a gasp as I realize just how deep he is as I feel his balls pressing against my ass.

Finally, there is a lull in the line of men wanting your mouth though they continue to fuck your pussy long and hard. You watch me as I strip naked and get back on the bed. I touch your cum-drenched face and kiss you. I let you feel the deep feelings I have for you and the joy I have in helping you find your sissy self.

I reach under to find your cock. It is still hard after these couple hours of sex games, the head slick with precum. I stroke you as we kiss, firm and fast, until you gasp in a girly voice and I feel the cum stream over my fingers.

I let you ride it as you feel a fat cock thrusting in your pussy. We'll have to work on habituating you to cum just from having cock in your pussy.

"The real test is when your pressure has been released... are you still a sissy? Do you still perform with passion? These gentlemen will be observing that."

With that, I arrange myself on the bed in front of you, legs spread and I draw your head down between my thighs. You have work to do...

I react to your touch by turning my head--my lips kissing and sucking on your fingers. I let out a moan as you reach under and touch my cock--my back arching as I realize just how close I am to my own orgasm. As my cum leaks out of my cock I let out a deep moan and press my ass back against the man who is filling me.

As you arrange yourself in front of me I arch my back, like a cat, and lower myself to you so that i can taste you while the man behind me continues to use my boi pussy. My lips wrap gently around your clit as I slip one and then two fingers deep inside of you--moving them slowly, at first. My tongue darts out lapping at your sex as I suck on your clit.

The man begins to drive deep into me--with more ferocity than the other men before him and I can feel my body reacting to him as I become conscious of my cock bouncing about as I try to concentrate on pleasuring you.

I see how quickly your little cock recovers from being sissy fucked and I smile. Then I lean back, caress my breasts and lose myself to your fingers and tongue, letting you take me over the edge again and again...

Eventually, you suck each man one last time and they leave us with many compliments and begging to do this again soon. Your boi pussy is stretched and a little raw even with all the lube they used. You can viscerally still feel fat cocks fucking you and you know you'll have that sensation-memory forever.

I let you lie down and cuddle next to me as you play with your hair and you nuzzle my nipple, sucking it.

"Where do we go from here, sissy? Do you even come back to work or do you start a new life?"

My lips wrapped around your nipple I playfully tease it with my teeth and tongue pleasuring in seeing how hard I can make it. I pull it into my mouth as I suck on it and I can feel your body reacting to my lips and I grin.

"Whatever you think is best, Ms." I blush knowing that not working is going to be strange but not sure what else to do. "Uhm, what about my bills Ms? And my rent and student loans and..." I sigh knowing that my responsibilities are many but not certain what is going to happen.

"Well, like most people it looks like working isn't a choice for you. But I think we can find a winning situation. If you were willing, I think we could move you to be my executive assistant. Linda is planning on leaving soon and I don't have a replacement for her. Of course... you'd have to have a proper appearance, like the rest of the girls..."

I blush and smiled. "I would love to be your assistant, Ms. What would you have me do?" I had come to expect that this would change everything about my work-life balance but I hadn't realized just how quickly it would come to be. Despite myself I couldn't help but be excited--happy that I had managed to keep to myself for the most part throughout my time at the company.

My tongue flicked over your nipple as I continued to pinch and massage your breasts.

"I've got some work travel coming up. I'll need to leave you in the hands of Margaret and Elisa, two of the executive admins. They'll take care of you over the next week and then the following Monday you should be all ready for your new position."

With that, we fall asleep together, waking just before dawn for some more sissy games before checking out of the hotel. You return to your home and it seems surreal with all your guy clothes and other distractions. You want to think of nothing but becoming more sissy and pleasing me. You're thrilled when you get a text from Elisa.

"Hey girlfriend, heard the news. Congratulations! Since it is Saturday, we have the whole day. You ready for this?"

I know that the thrill that runs up my spine is in anticipation for what is to come. I go through my closet and touch the male clothes and then I slip my hand below my waistline and my fingers touch the satin panties that I wore the night before and I smile--knowing that it is all real.

I read the text and nod. I reply. "I'm ready for whatever you have in mind, Elisa!" I sit on the couch for a moment before realizing that I'm going to have to get ready for what is planned for the day!

(Please share your preparations for their arrival in one hour. Describe everything you are or are not wearing when they arrive.)

SweetAnnie40 said:

(Please share your preparations for their arrival in one hour. Describe everything you are or are not wearing when they arrive.)

Click to expand...

Come on, honey, don't be shy...

I stand up and move towards the mirror. I quickly shower and wipe myself off. I slip into a pair of panties and spin checking myself out in the mirror. I apply the breast forms you gave me and slip into the bra. I smile playfully in the mirror and practice winking before ensuring that my face is clean shaven. As I am pulling on my stockings I hear someone at the door. I jump--only half dressed and run to the bathroom where my wig and dress are waiting.

I yell out as I get to the bathroom, "One minute, please!" I'm nearly out of breath wondering who could be at the door.

You wrap the short silk kimono I gave you around yourself before you get to the door. Glancing at the hallway mirror you pause, amazed at how femme you look, the swell of your 'breasts' in the kimono, the drape of your wig hair over your shoulder, your done-well-enough makeup.

The doorbell rings again and you rush to open it, your heart racing as you realize this might not be Margaret and Elisa! The door swings open, revealing you dressed as a woman and you breathe out heavily in relief.



"Hey girl!" calls out Elisa displaying a bottle of wine in her hand. She flips her short blonde hair and sweeps in, kissing you on both cheeks. You feel her breasts rubbing yours and already start to get hard in your panties. "We're going to have so! much! Fun!!!"

Behind her, Margaret with her long brunette hair comes in more sedately, more amazed, mouth open seeing you like this. "Kelley?" she asks quietly while Elisa is already moving into your kitchen and finding wine glasses. "Or do you use a different name?"

I feel relief wash over me as I open the door to discover Elisa and Margaret standing in the hallway. "You two made me so nervous!!" I take the bottle of wine and smile. "I knew I filled that ice bucket earlier for a reason! Come in and we can open it up. I've got to finish getting ready." I blush as I pull back the kimono exposing my undressed state.

I smile at Margaret, nervously. "Hii, Margaret. I wasn't expecting to see you..." I blush a little bit and laugh--knowing that I'll always be surprised by what will happen as more people get exposed to my new identity. "I hadn't really thought about the name, honestly. What do you think?"

I pull on a skirt and a top that covers my chest.

Elisa and Margaret bring the wine and follow you upstairs to your room as you look for the skirt and blouse. They look around as they walk and look around your room. You pause and follow their eyes, looking at the nicely furnished but very neutral or even male decor. You watch them as they walk around, inspecting things.

You're amazed that these two women that you know as powerful executive administrators at work are here in your room seeing you dressed girly. The power they have over you is palpable, their strong womanhood makes your attempts so far quite inadequate.

Elisa finds your drawer where you have a couple cock-shaped dildos and a vibrator. She laughs and pulls them out to look at them. Margaret is blushing and seems much more surprised by all this than her friend.

"What name?" responds Elisa. "That's a pretty personal decision. You might want to think about that since you're going to live with it."

"Live with it?"

"Didn't she explain it to you? Okay, sit down, sweetie. Here is what is going to happen. Margaret and I are going to supervise your transformation for now. If you do well enough, you'll be hired on as a female executive administrator working for Annie at the company. Do you know what we do?"

"You keep everything organized, manage their calendars, and..." you trail off, not knowing what else.

"There are a lot of 'duties' we perform to make our bosses and the company look good. Many of these duties are performed outside of the office, at night, in hotel rooms or at private parties. We are very talented and good at what we do. You'll need a lot of training and be thoroughly tested before you're offered the job."

"What... what if that isn't what I want?" you ask nervously even though your cock is rock hard in your panties. You hide it by holding the skirt in front of you.

"Sure it is and anyway, it isn't your choice any more. We're doing this whether we do it the hard way or the easy way. The only question is will you enjoy the hard way or easy way more, ha ha."

I blush as Elisa & Margaret walk around the room. I scramble to clean-up even though I know it is already too late. I blush and quickly finish dressing before I scramble trying to throw my dirty clothes into the hamper and cover up the dirty underwear and socks. My knees shake when I think about everything that has changed in such a short period of time. As Elisa opens the drawer filled with my toys I want to say please stop! But I don't.

I sit down and listen to the offer. I nod getting increasingly excited at the prospect. I attempt to cover myself up but know that I am not doing a great job of concealing my growing excitement. I blush and cross my legs. A part of me remains hesitant and wants to stop but I know at this point I cannot and that I will have to recommit myself. I sigh softly and gather myself.

The more talk of a name the more I think about it. "Well, Ms. Elisa and Margaret, what do you think of Katy?" I blush and pull at the bottom of my skirt knowing that it keeps riding further and further up and not being able to keep it down.

"Katy... Katy..." muses Elisa as her hand wanders up under your skirt to grab and hold your erect cock in your panties. "I like it. And obviously..." (slight squeeze to your cock) "You like it too. All of this. That's good. We transformed one poor fellow who resisted the whole way."

"Anyway, Katy is good. Oh, Margaret, remember that night in Vegas when we were assigned to 'entertain' Katy Perry? Damn that girl loves to... well, client privacy, you know. Maybe you'll get to service your namesake someday, Katy."

"Well, we have a lot to do, I think this room is the first step. Who can feel girly here?" mused Elisa walking around the room again.

"Finish getting dressed, honey. We're going out."

"Wait, with me dressed as a woman?"

"Of course, Katy, how else would you be dressed? Margaret can tease your hair and do your makeup. You're already one of the most femme guys I've met so you should pass pretty well."

I let out a moan as Elisa squeezes my cock. "Mm, fuck." I gasp and catch my breath. I blush as she mentions a wild night in Las Vegas. "I just want to keep you happy, Ms. Whatever it takes." As Elisa walks around the room I blush knowing that I have much to learn from these women.

I quickly finish getting dressed--pulling up my pantyhose and pulling the dress down that I have chosen for the day. I run around my room tidying up and finishing my preparations.

"Well, I think I'm ready for make-up, Margaret." I blush and come out of my room into the family room where they are sitting on the couch, waiting for me.

"You know, Maggie," muses Elisa as you walk over to the couch. She reaches under your dress and grasps your cock through your panties. She begins to slowly stroke your rock hard member. "I think it is easier without this crazy clit sticking out, tenting her panties and dress. Totally ruins the illusion. Should I make her cum?"

The stroking gets harder and firmer and you know you're already close. You let out a moan.

Margaret pulls Elisa's hand away, leaving you to slowly ease back from the edge of a major explosion. You know you've leaved more cum in your panties.

"No silly, sissies lose focus if you let them cum. She'll be properly motivated and attentive if she's waiting to see if we'll let her cum. But you're right about her figure. If she can't control that thing, we'll have to."

Margaret digs around in one of the bags they brought and pulls out a pink plastic mechanism.



She snakes her hand under your dress and into your panties, grasping your cock around the base. She squeezes firmly, slowly cutting off the blood flow. Amazingly you feel yourself softening. Once you're soft, she quickly slips the cage over your cock and behind your balls, locking it with a click. You immediately try to get erect again but wince as you realize that it totally prevents that. Glancing in the mirror, you see your dress is undisturbed by any hint of masculinity.

"Good, now I think we should go have a professional do the make-up the first time. Teach her some things. Come, Katy, we're going to the salon!"

I blush as I feel my cock softening in Margaret's grasp and I let out a soft gasp as she pinches my cock into the cage. When I look down I blush seeing the pink cage that has enclosed my cock and how my skirt has ridden up my thighs leaving me so exposed. I stand up and my hands move over my skirt as I look in the mirror.

A soft moan escapes from me as I hear mention of going out to a salon. I look up catching Margaret's eye. "Yes, Ms. Are you... sure?" I blush knowing that I am thrilled and yet I do not want to embarrass the ladies that stand in front of me.

"You look gorge, Katy," enthuses Elisa who takes your hand and leads you firmly out of the house to the car. Stepping out in public en femme is like jumping into a pool of water. You are literally gasping and your cock is straining in its cage as you see people walking nearby looking over at you. Your outfit is quite daring compares to your companions so you get in the car as quick as you can.

You calm down some on the drive, at least until they pull up at the largest mall in town. Hundreds if not thousands of people are moving to and fro. Your heart is racing. You'll be exposed, looked at, humiliated if they see you're a guy... but if you pull it off... those looks will be envy from the women and lust from the men. The thought of being so femme and pretty that you could get a guy's cock hard is so powerful in your mind that you almost feel like you could cum even caged.

I lock the car and lead you and the others toward the mall. Margaret whispers advice to you as you walk about swinging your hips, how to walk in the heels (one foot in front of the other in a line), keeping good posture, and more. Before you know it you've got a killer walk and are getting all the envious and lustful stares you could dream about.

Once inside the mall, we make a line toward the PINK! Salon. The place is quite busy and full of exclusively women. If there were husbands or boyfriends around they found somewhere else in the mall to be this afternoon. There is a line for the stylists so I put our name in and lead you back to the rear of the salon which is a lingerie department.

I hand you a pink buzzer like they use for people waiting at restaurants. "They'll buzz us when the stylist is free. Too bad you can't keep that in your panties!" I tease with a "wow" face.

I blush at Elisa's compliment. "Thank you, Ms." Feeling everyone's eyes on me I slip into the car quickly without realizing that the skirt that I am wearing is sliding further and further up my thighs. I look down once you both are in the car and blush--pulling my skirt down and covering up my cage. I relax on the drive but know that I can't relax too much as I know that something fun is planned.

When we park at the mall I let a soft groan. "Are you sure??" I slide out of the car making sure that my dress keeps everything covered. I smile at Margaret as she encourages me and offers advice on my walk. Leaning over I whisper in her ear. "I'm going to owe you later--so please let me know, Ms." I blush and continue walking feeling the eyes of all of the other guests and blushing as I catch a few men blatantly staring.

As we make our way through the PINK! Salon I bite my lower lip. "Are you sure that I'm welcome here, Ms?" I blush and giggle as you tell me "They'll buzz us when the stylist is free. Too bad you can't keep that in your panties!" As we enter the lingerie section I smile as I watch the other patrons and smile immediately knowing which ones have a similar taste to my own.

The lingerie section is laid out in little rooms with different themes... daily wear for women... sheer and lacey for date nights... satiny confections for sex and slumber... strappy and corset styles... leather/latex/bondage styles... costumes like maid's uniforms and over-the-top sissy dresses. We walk through them and I watch for your reactions to see what makes your eyes light up.

My eyes widen as we enter the salon and browse over the display tables. I bite my lower lip. My eyes linger on the sexy items knowing how much I would love to seen and displayed for you. I reach out my fingers tracing over their materials. And, yet, I also look at the more daily items--conscious that I will need to be able to dress for daily activities as they are assigned.

"Ms..." I blush and look over my shoulder towards the saleswoman. "I love it all!" I blush and cover my mouth as a smile starts to spread across my face.