An Office for Growth (SweetAnnie40 + sissykaitlin)

[sissykaitlin]

I bite my lip as I watch him reach down to his cock and lift it to me. I wink and feeling bold ask him if he wants me to lick his cock clean for him. Before giggling and sitting back--watching as he gently fondled himself.

 

[SweetAnnie40]

"Suck my cock, girlie" he growls and his cock is starting to stiffen a little.

 

[sissykaitlin]

I blush and lower myself to his cock. "Yes, sir." I wrap my lips around the tip and my tongue swirls around the head as I try to stimulate him.

 

[SweetAnnie40]

His cock swells in your mouth and you taste his cummy juices. He isn't so anxious to cum this time and your moments become minutes of mouth pleasure as you practice everything that makes him moan and sigh.

You're not sure how long it has been when his sounds change and you know he is going to cum.

"Suck it and swallow it, you sissy slut," he pants and then moans as it is about to shoot...

 

[sissykaitlin]

I wrap my lips around his cock as he reaches another orgasm--taking his cock deep down my throat and milking his balls as he explodes into my mouth. I swallow--gasping for air. My hands on his ass--holding him deep inside of me--not allowing a drip to escape.

"Did Mistress train a good slut, Sir?" I giggle and look up--wiping my lips clean as I do so. Wondering what Mistress would be thinking if she were to see me now.

 

[SweetAnnie40]

"Damn..." he moans as his orgasm subsides and he looks at you. He leans forward to take a cummy kiss from you and then urges you on to your back. His strong hands gently spread your legs and he settles between them, pushing your skirt up around your waist and pulling your wet panties down enough to release your clit.

His eyes are glazed over with arousal as he slides forward and you feel his mouth envelope your clit: warm, wet, and gentle. He's done this before...

 

[sissykaitlin]

As he kisses me I let out a moan--tasting him and feeling his scruff against my cheek. I am surprised that he so openly welcomes the cummy kiss and giggle playfully--sticking my tongue deep into his mouth. As he urges me back I wonder what he has in mind.

As he pulls my panties down I blush--feeling my clit released. "Mmmm, fuck." is all that I can manage as he wraps his lips around my clit. My back arches and I raise my hips encouraging him to take me deep as I feel the room starting to spin with excitement.

 

[SweetAnnie40]

You hadn't expected this but his talented mouth makes you feel so good. His tongue works your clit all over, sucking it as his fingers stroke your shaft and massage your balls. He is clearly sucking and encouraging your cum to build and you feel your orgasm begin to build, bigger than you've ever felt before as you lick your lips and taste his thick cum.

 

[sissykaitlin]

I let out a groan as I quickly realize how close I am to cumming. My hands run through my hair as I gently caress his face as he takes my cock. I let out a moan letting him know that I am about ready to explode--my legs quivering as i get closer and closer.

 

[SweetAnnie40]

He moans in pleasure and works your flesh more urgently. The pleasure overloads you and you begin to spasm, waves of joy rushing and burning your body as you erupt over and over, filling his mouth with your sissy sperm. He coaxes you on and on until you get too sensitive and gently push him back.

He licks his lips and smiles at you, propping his head up on his arm, elbow on the bed. He makes his way up the bed to kiss you and you taste your cum mixing...



You wake in the morning feeling complete and refreshed. The bed is empty but he left you a rose and $2,500.

 

[sissykaitlin]

I roll over and find that I am caked in cum. I can feel it dry against my skin and face and between my legs. The money on the nightstand surprises me and I pick it up--counting it out. I bite my lip--incredibly embarrassed to find what I have become. I contemplate calling you at the office but know that I shouldn't. Not yet.

I step into the bathroom and fill up the tub--the water hot. I add some bubbles to make it a bubble bath and slide into the water--submerging myself as I was myself clean from the sweat and cum of the previous night.

 

[SweetAnnie40]

You begin to doze and dream in the tub, wakened later only by your phone ringing. Clutching a towel to yourself up under your armpits like a girl, you reach the phone, see that I'm calling and answer it.

"Well, sweetie, how did you like being a girl for me last night?"

 

[sissykaitlin]

I blush and feel my breath catch in my throat. "Oh, Ms. Annie! How do I ever thank you?" I sit on the side of the bed and bite my lip--thinking about the feeling on the man's cock filling my sissy cunt and his emptying his balls down my throat.

I let out a small giggle. "Hehe, I certainly had fun Ms. Annie and I know that I have so much more to learn. I hope that I will be able to continue to please you, Ms."

 

[SweetAnnie40]

"I'm so glad. In your new position at the office, you'll be expected to 'entertain' customers that way frequently so I'm glad you enjoyed it. They give us a lot of very lucrative business in exchange for these 'dates'."

"Now, get yourself pulled together. I have a car waiting for you downstairs. We need to get you ready for the office."

 

[sissykaitlin]

I blush. "Yes, Ms. Annie. I will be down for the car momentarily." I hadn't even thought about making it into the office today but with the sudden realization that I am still expected in I quickly go about pulling on some panties and making myself presentable.

 

[SweetAnnie40]

You emerge from the building in full femme and see a black Suburban waiting for you. A muscular man in a slick chauffeur's suit opens the door for you and helps you climb into the car. Within moments, the car pulls away from the curb and heads into traffic.

You're a little surprised when the car takes you to the doors of an up-scale mall, a mall that shouldn't be open yet but I'm standing out front in one of my finely tailored dresses and heels.

"Hi honey," I greet you warmly with a hug and pat on your bottom. "You did so well. I'm most pleased that you enjoyed it so completely."

I lead you into the mall and to several stores where they have opened early and pretty sales girls help me get you outfitted with a dozen mix/match separates that can all work for your time in the office as a professional woman. You carry the load of clothing back out of the mall with me as the doors open and a crowd of people start coming in.

We get back into the black Suburban and move smoothly away from the mall.

"I think you are aware of what the girls do in my office during office hours. We have a business to run and you'll be expected to perform at a high level there. You also now have an idea of what our 'evening' work is like. It won't always be an overnight but you'll be expected to entertain our client, man or woman, in any way they desire. We've set you up in a new apartment where you will always have been a woman. All your possessions have been moved over, except your male clothes, of course. We destroyed those or donated them to good will. I supervised giving you a basic wardrobe of women's clothing, underwear, exercise outfits like tights and yoga pants, sneakers, heels, and much more. I'm sure you'll take advantage of your substantial raise to add to that wardrobe with your own style and taste or with items clients ask you to wear. Lyle, here," indicating the driver on the other side of the glass partition, "is your driver. You have a new cell phone with him on speed dial. He is available 24x7 to don't hesitate to call him for whatever use you might make of him." With that last bit, I give you a leering look.

"I'd expected to have to give you a long regimen of training with dildos, strap-on play, and more to get you ready for male clients but you've surpassed all my expectations. So, my dear, do you have any questions? Any concerns?"

 

[sissykaitlin]

I am shocked to find the black suv waiting for me. I had always thought that only the rich and famous got such service! And, yet, here was a luxury sedan with blacked out windows waiting for me. When we reach the mall I catch my breath--knowing that it hasn't opened yet and surprised to see you outside. As you pat me on the bottom I smile at the chauffeur who is eyeing the two of us.

As we get ready to leave I can see everyone eyeing us as we leave. A couple of people I overhear asking who we are that we got access before everyone else. I feel so special and elated to be by your side. As we slide back into the suburban I smile and wistfully wonder what I was doing with my life, before now.

"Oh, Ms. Annie. You are much to kind to me. I will do whatever is necessary to please and work for you, Ms. I cannot believe you bought me a new apartment!!" Knowing that I will be getting away from my roommates and moving into a space that I can make my own thrills me. I smile innocently and giggle as you leer at me as you mention that Lyle is for my own personal use. I roll down the window that separates us from him and lean forward. "We're going to get along just fine, aren't we, Lyle?" My hands massage his shoulders and I trace my fingers over his chest.

I blush and bite my lip as you compliment how I have exceeded your expectations. "But, Ms..." I smile hestantly and gulp--not wanting to appear too bold. "I'd still love to be used and trained by you, if that is acceptable. I'm sure I still have so much to learn!" I bat my eyelashes and sit back, not having any further questions and wait patiently for us to arrive at our destination.

 

[SweetAnnie40]

The SUV pulls up in front of a posh apartment building and I get out.

"Lyle will take you to your apartment, make sure you get your keys and everything is in order. Come to my apartment this evening around 7pm and I'll put you through your paces. We have to make sure you're prepared to please our female clients as well. You may choose what to wear for me, but impress me on how sensual you can be. Until this evening."

With that, you are alone with Lyle as he drives you to your apartment. Your touching of him earlier got a nice smile from him and you saw a bulge grow in his pants, a remarkable bulge.

"Here we are, Miss. Rockford Square." It is a new, up-and-coming part of town and Rockford Square is a new, high end apartment complex reaching up twelve stories. Lyle escorts you inside, introduces you to the hotel manager (Gus Williams) and the lobby staff (two college girls: Suella and Lydia). You get your electronic passkey, tell them how you would like your mail handled, and if you want any regular special services like laundry, any meals, grocery shopping for you, etc. If you wish, they will arrange for a girl to become your assistant and take care of as many mundane chores as a woman in your position might require.

'A woman in your position'. The phrase rings in your head as you realize they all took you completely for a woman. Your voice had always been a little soft and higher pitches than you'd wanted in the past but it works perfectly for you now.

Your apartment is one of four large suites on the penthouse floor. It is quite spacious with a huge walk-in closet that is maybe 10% full of a woman's wardrobe. I've thought of everything, providing you with bathroom products, the clothes, good food in the refrigerator and an exercise program to attain and keep your most feminine figure posted to the door of the refrigerator. You see that many of your personal effects survived from your old place: your favorite books and such.

"I suspect you'll want to recover from a 'working night'," says Lyle slowly, but if you need anything from me, let me know. "Otherwise I'll be downstairs at 6:45pm to take you to Miss Annie's."

 

[sissykaitlin]

I nod as you instruct me to go with Lyle and to my new apartment. I blush--feeling that I am being handled to an extent but knowing that this is to be expected in my own situation and that this is something that I have always desired--to be under the guidance and instruction of someone else.

I gasp when Lyle pulls up to Rockford Square. "Are..." I lean forward from the backseat and place a hand on Lyle's shoulder--slowly allowing my fingers to trace lower over his chest. "Are you sure this is for me, Lyle. This is so overwhelming and so much more than anything I would have ever expected." Once I enter the apartment I realize just how much has been considered and planned for. I gulp as I see the pink in the closet but there is also a lot of black and grey and shiny outfits. Almost as if there is every color imaginable in the closet.

As Lyle mentions that he'll be back around 6:45pm I realize that he is still there. "Lyle, will you fill the tub for me before you go?" I smile at him as he moves towards the bathroom. As his back is turned and he is out of the room I slip out of my clothing and down to my panties. The water is still running, filling the tub. "Lyle add some bubble bath okay? I'll be there in a moment."

I enter the bathroom unashamed of who I have become. I walk over to the sink and look in the mirror. "I've got to take this make-up off before I take my bath, Lyle. How's the water feeling?" I catch his eye in the mirror and wink. "You've been such a huge help to me today. How can I repay you for your assistance? I know that Ms. Annie would want be a good girl and show my appreciation..." I blush and know that this could take a while and that I should rest before meeting up with Ms. Annie later but I know my manners.

 

[SweetAnnie40]

Lyle smiles wide and starts to strip off his clothes. Within a minute he is naked with a huge thick cock erect and jutting out from between his legs. He looks at you to see what you'll do.

 

[sissykaitlin]

I smile at Lyle and drop to my knees. My right hand wraps around his shaft and my left hand teases his balls. "You've got to be quick now, Lyle. I've got to be sure that I'm ready for Ms. Annie when she comes back." With that said I spit on Lyle's cock and start to stroked his shaft quickly lowering myself so that I can wrap my lips around his balls.

 

[SweetAnnie40]

Lyle grunts and you feel his cock swell in your grip. Your expert attention has him shuddering within a few minutes. He moans when your mouth wraps around the thick cock head, stretching your lips and his hips can't help but thrust just a little, filling your mouth with his meat. He puts his hand on your head, gently for now.

 

[sissykaitlin]

I gag slightly on his thick cock. While the man from the night before was long, Lyle is thick and I can feel his cock stretching my mouth. As Lyle places his hand on the back of my head I push forward--trying to take as much of his thick meat as I can. My hands wrapping around the back of his thighs pulling him forward.

 

[SweetAnnie40]

"Oh fuck bitch take it in your throat," he growls, consumed by the pleasure you're giving him and pushing.

 

[sissykaitlin]

I can feel his hands on the back of my head, holding me in place as his cock fills my mouth. I moan around his cock and gasp at how he has filled me. My tongue traces over his foreskin as he holds me in place and I feel his knees buckle slightly as his orgasm overcomes him. His warm cum explodes into my mouth and I can feel some of it dripping down my chin but my hands, on the back of his thighs, hold him in place so that he does not leave my mouth as I try to milk the cum out of him.

As he pulls away from me I smile and open my mouth showing him the cum that has filled my mouth. I swallow it and stand up. "Mmm, thank you honey." I step forward and kiss him gently before pulling away. "I've got to get ready for my Ms Annie-- so I'd better hurry and get cleaned up so that I am presentable."