Made a Maid Ch. 02

(Chapter Two of an on going serial of the adventures of Josie May. Enjoy!)

Last I left you, I was bound, gagged, blindfolded, and completely in drag in my roommate Madeline's room. Her boyfriend Ivan's cum was still dripping out of my freshly fucked ass, and the door is opening behind me. My heart is beating in my throat, I'm positive that it's another man come to take part in my humiliation and ravaging. The door creaks open, and I tremble, absolutely sure that I'm about to be raped, when I feel something soft and furry rub against my ankle. It's only the cat. Thank God.

Ivan and Madeline step out of the shower, and take off my blindfold. "We hope you had fun, Josie," Madeline coos in my ear as she removes my ball gag at the same time Ivan removes my handcuffs. Ivan looks like a god with only a towel around his waist, he must be at least six foot five and built, I didn't get to get a good look at him while he was fucking me. It still hasn't really sunken in that I just got fucked by a big gorgeous guy.

"I did," I say standing up, rubbing my wrists where the handcuffs were digging in. "But maybe next time you don't have to lock me up, I'll let you fuck me anytime." I wink at Ivan while I pull up my panties.

"Oh believe me baby, I'll be doing just that, and soon," Ivan says and slaps my ass playfully.

"Oh you bitch!" Mad shouts at me as she slaps my ass, giggling "Go clean yourself up! We have a big day tomorrow!"

I take a long shower that night. What did she mean we have a big day? For fucks sakes, I'd say today was a big day! I'd never even really thought about being with a guy before and now my ass ached, and cum still seemed to be oozing from it even hours after Ivan had fucked me. I smoke a joint and drink a glass of wine reveling in the feeling that I just had my first cock pounded into me. My eyelids heavy from sedation, I pass out and sleep deeply.

I wake up the next day on my own, I smell coffee and breakfast coming from the kitchen. I feel a sense of panic, "Oh no!" I cry out. I get my hair ready in record time, and throw on long silk robe that Madeline had bought me. I tip toe out into the hallway, and peek around into the kitchen, Madeline's sitting at the counter with two cups of coffee and a big breakfast spread. She notices me and calls me over,

"Hey don't be shy, I made us breakfast this morning. Have some coffee!" She pulls a bar stool out for me, and I slink up to the counter with her.

"Thanks Mad, I'm sorry I didn't get up earlier," I sip my coffee and pick some fruit off the plate,

"It's okay Josie, you must've been tired. I understand. Look, Ivan and I have been giving it some thought, and I'm going to be moving in with him. We're going to get married, and we want to start a family. I know you don't really have anywhere to go, and you're not coming with us, so I'd like to give you this condo." She grips my hand on the counter, I practically drop the coffee on my lap.

"You can't give me this place! It's way too nice. How am I going to pay for this? What about our arrangement?" Again a sense of panic, I had just resigned myself to being this girl's maid and toy, and now I'm being dumped?

"Look, you're still my bitch," she grins evilly, "I'm just not going to live here any more. That means I'm also not going to be paying your bills any more. I'm giving you a condo, that should be plenty."

"What am I going to do for money?"

"That's what I wanted to talk to you about. One of Ivan's clients is a doctor. A plastic surgeon, actually," that panic starts coming back right about now, I know where this is going, "and he was watching you last night on the web cam, and he thinks you're gorgeous. He thinks he could make you even more gorgeous. He would like you to stay with him for a few months, he will give you ten thousand dollars a month, and subsidize any surgeries you might be wanting." My heart is racing, this is huge, a once in a life time opportunity, what will my parents think if I do this? My family? My friends?

"Mad, you know, I never really thought about becoming.." I'm lying when I say that to her, "I mean.. That's a big step.. I mean.. Just the reality of it, it all sounds so difficult." She stops me by holding my hand,

"Josie, just meet him. Just talk with him. His name is James, he's a very nice guy. I'll help you get ready to go out." We get me ready to go out for the first time as Josie, Madeline helps me do my makeup and hair in a less slutty way. I put on a sensible outfit of a pair of nice designer jeans that Madeline is letting me borrow, they make my ass look great and my legs look like they go forever. I put on some flats so I'm not towering over everyone, and a sensible top. "You look great Josie, lets go."

We take Madeline's car, and she drives. Her car's nicer and she knows where we're going anyway. On the drive over, we get stopped at a red light next to a pick up with a young man driving. He's on my side of the car and I can't help but notice him looking at me, I roll down my window and decide to flirt a little. "Like what you see, honey?" Pulling down my sunglasses, I wink at him.

"Baby, you two pretty little girls should be in here with me," I can tell he's undressing me with his eyes, good thing when the light turns green, we take a left and he takes a right. I have to say, I am starting to like the attention.

"You're getting a kick out of this aren't you?" Madeline says giddily, noticing my smile.

"I think I could get used to it, that's for sure." I coo back at her.

We aren't on the road much longer until we get to what must be Dr. James' office. It's a big building, and we park in their garage. We take the elevator up, it stops the next floor up and a couple of business suit wearing men step in. They're good looking guys, and I can tell that they're trying not to stare at the two young ladies in the elevator with them. I revel in the attention, I also make sure to brush up against the younger man accidentally, and he takes a long smell of my perfume. Walking out I sway my hips sexily, and glance back at them as we exit the elevator.

"You're loving this." Madeline says squeezing my hand as we get up to the receptionist's desk, "I believe Dr. James has an appointment with a Ms. Josie May today." The receptionist clicks a few times and taps a few keys on her computer as she looks me over a bit.

"Ah yes, there you are. The doctor will be with you ladies in a couple of minutes. Have a seat." The receptionist is cute, if a little bit older. I still have my sunglasses on, and I don't think she can tell that I'm watching her watch me. I can't tell if she can tell I'm a boy, of if she's jealous of my legs. I shrug it off, cross my legs and flip through a magazine while I wait for the doctor. After a few minutes, the door to the office opens, and a tall well dressed man in a white coat steps out.

"Ladies, please come in," he motions to us and holds the door open for us to enter, he doesn't move much out of the way to let me in, and I have to brush against him. I can definitely feel the bulge in his pants. "I've been pretty excited to meet you Ms. May. You are much more beautiful in person. My name is James, I'm sure Madeline already told you about me. Please, sit."

I nod, smiling, "She did," I can feel myself starting to blush knowing full well that this man has already seen what I have to offer, and he is definitely looking at me as if I were already naked. Madeline and I sit down on the couch in his office, I cross my legs nervously.

"I'm sure Madeline didn't tell you that my work is stressful, and the next few months are going to be no different," he's standing right in front of me and he puts his foot up on the coffee table in front of the sofa. "I've got a lot of surgeries and conferences coming up in, and I won't be able to tend to my home the way I usually like to. I'm looking for a live-in maid," he licks his lips, and continues, "I'm also looking for someone to take care of my special needs." He puts a finger under my chin and lifts my face up to get a better look at me, taking off my sunglasses, he caresses my cheek. "Do you know what I mean?"

I nod again, blushing, "I think so," my cock is starting to stir, straining against of lace of my panties, it doesn't help that Madeline is stroking my thigh. The bulge in his pants has grown during the course of his monologue, and it's continuing to grow. He doesn't hesitate to start unzipping his pants, I stop him by taking over. I pull him closer to me and start removing his belt, undoing the top button his pants fall to the floor as Madeline is busy working on taking off mine. As James reaches down to kiss me hard on the mouth his tongue wrestling mine down, my hands move to his thighs, rubbing them all around. Madeline rubs my growing bulge through my panties as I start to trace my hands around James' cock through his boxers.

"Josie, I need you to suck my cock," I don't hesitate pulling his boxers down letting his large thick cock spring forward nearly smacking me in the face. "Come on baby, put those sweet big lips on my meat." I start by licking it all over, letting my tongue trace circles up and down his shaft, running the tip of my tongue under his head and down to his balls. "Don't tease me, slut, I know you want my whole seven inches. I've seen you get fucked, I know you love cock." With this, I crack open my lips, letting his cock invade my hot mouth, pushing my tongue against the bottom of his cock. He moans loudly as his balls rest on my chin, he ignores my gagging and holds my head down against his pelvis.

"Just relax baby," Madeline coos pulling my little dick out of my panties, "Just let him in," she starts stroking my rock hard cock.

"Listen to her, Josie." James starts thrusting his meat into my wet mouth, I start to relax. In twenty strokes or so I stop gagging, and spit starts to drip out of the corners of my mouth. Every time he pulls his cock out, I have enough time to let the tip of my tongue circle his head before he thrusts his cock deep against the back of my throat again. By this time, Madeline has my whole cock in her mouth and she's just sucking, moaning into my crotch. I start moaning onto James' cock, and this seems to push him over the edge as I can feel his body start to tense up, his seed exploding into my mouth, "God that's good, I'm going to cum, don't stop Josie," he groans as he holds his cock in my mouth and I can't help but swallow his load. Even after I suck down every drop of his cum, I still frantically suck his cock until it shrinks down to a flaccid state. I can't handle it anymore either, and I cum into Madeline's mouth, she of course holds it in her mouth and makes me drink it.

"You just love drinking cum don't you Josie?" Madeline says pinches my arm giggling, as I lick my lips cleaning the dripping cum from the corners of my mouth.

"Mm hmm," I finish wiping up the cum from my face and what was left on my cock and lick my fingers clean, "I think I love it."

James and I pull our pants back on, and he composes himself and takes a seat behind his desk, "I think it's time we can talk about the details now." He tells me what surgeries he plans on giving to me, I tell him I don't want to lose my cock or the ability to cum, so he rules out full sexual reassignment surgery and hormones. We make plans on refining my feminine features, including breast augmentation, a few facial surgeries, electrolysis to remove my hair, and hip and butt implants. We also make arrangements for me to live at his place five nights out of the week, and to travel with him on the few conferences he has to go on. We part ways, and I get a dirty look from his receptionist on the way out.

Over the next few days, I get my things in order, and make arrangements to have my name legally changed. I tell my mom about my plans for transformation, and she cries. She tells me that she kind of always knew I wasn't quite supposed to be a boy, and that she'll always love me. My dad, however, just hangs up on me. I tell a few friends, and the new me is met with mixed reception. When the time came, I packed up a few sets of clothes and got ready to move into James' place. My hair still wasn't long enough to wear on it's own, but it was long enough to hold a weave, that gives me straight black hair that falls half way down my back.

I drive my car over to James' house, which is more like a mansion, and park in his driveway. I check myself in the window of my car, fixing my eyeshadow and reapplying my lipstick before I head down the driveway, my four inch heels clicking on the concrete, my knee length red and black dress is flowing in the slight breeze, and my suitcase rolling behind me. I get to the door, and before I can knock James opens it, he greets me with a soft kiss on the lips, and pulls me inside closing and locking the door behind him.

"This place is amazing," I notice that he's not wearing shoes, and I kick my heels off into the corner.

"I'll give you the grand tour later, cutie, but first thing's first," he licks his lips, grinning at me hungrily, I can't help but feel a little violated but still turned on, "Dinner. Madeline tells me you're a great chef." I smile, and he laughs, "I know what you were thinking, that can wait. I'm hungry now." I put on an apron, and get to work. I search his fridge and pantry,

"James, why don't you go find a bottle of red for me. I can't cook with out a glass of wine." I wink at him as coyly as I can muster, and start getting pots and pans on the stove. He promptly returns with a couple of glasses and bottle of good Italian red. We chat while I cook, and three glasses of red wine later I serve him Pasta Puttanesca. Over dinner, I can not help but feel extremely attracted to him. Turns out, he's only thirty, he's already made his first million, he is cultured, likes food and wine, and he is very handsome in candle light. I am giddy over the attention he is paying me, soon enough my stocking clad foot is rubbing the inside of his thigh, and his hands caress up and down the inside of mine. Shivers run up and down my spine as we eat, my inebriation compounding my excitement and arousal, my cock strains against my panties and drops of precum begin to wet the lace of my black low cut thong, I rub my foot against the growing bulge in the crotch his pants. This makes him moan, and that just encourages me to continue.

A bottle and a half later, we are done with dinner. James stands up, takes my hand, and leads me to the couch in the adjacent living room. I have him sit down, and he turns on some music. The lights are dim and the music is soft, I start to dance for him. Moving my body with the rhythm, trying to look as sexy and as feminine as I can. I've danced as Josie before when I was living with Madeline, but never in front of anyone. He smiles, and puts his hands on my calves, caressing my legs, the fabric of the stockings increasing the sensations. I continue dancing for him and lean over kissing him on the lips softly, before I turn around, bending over, dropping to the floor showing off my ass to him. He pulls my dress up and massages my butt for a second, his fingers just barely touching the head of my cock tucked between my legs. James' pants are open, and he's stroking his cock slowly.

"Have you ever had your pussy eaten, Josie?" He asks, almost sounding short of breath, without breaking my rhythm I answer nervously,

"Not really, you don't have to, I mean," he stops me by ripping my panties down, and burying his face between the cheeks of my butt, his rough face scratching my smooth ass. His tongue was soon tracing circles around my puckered hole, and I thanked God silently that I had payed special attention cleaning myself down there. He reached around me and took my cock into his smooth strong hand, he began to stroke it slowly. "Oh my God!" I gasp breathlessly as he pushes his tongue into my asshole, the sensations making me weak enough in the knees that I would've fallen over if he wasn't holding me by my cock. I reach down and take over stroking his now rock hard cock while he eats my ass out. I can't take much more and my little cock oozes out some cum into his hand, without hesitation, I drop down to my knees and lick my cum clean from his hand, then take his cock into my mouth.

"Get on the couch, Josie, I still wanna play with your ass," he instructs me and I manage to get up on the couch with out taking his cock out of my mouth. He reaches over with two spit wet fingers as far up my ass as he can. I suck his dick harder when his fingers penetrate my hole, still relaxed from his long wet tongue.

As soon as his cock was wet enough, I stop sucking him, and climb over and sit on his, facing him. He pulls my dress off of me, rubbing my falsies through my bra, and caressing me all over. I position my asshole to line up to the head of his cock, and start to lower myself onto it. He moans as I let the his engorged head into my relaxed warm ass, I kiss him as I continue to lower myself slowly until he is firmly balls deep into my ass. He lifts me by the waist with his strong hands and arms, pulling his throbbing swollen cock out until just the tip was in me, holding me there for just a second before driving himself back into me, my balls slapping against his hard abdominal muscles as he fully impaled me again. Kissing him hard again, I put my hands on his chest so I can buck my hips with his cock inside me. I ride him for a minute trying to match the rhythm of his fucking. "I love feeling your cock in me," I whisper to him, flicking the tip of my tongue in his ear.

"I love fucking you, Josie," he moans as he kisses and bites my neck hard. He holds me close to his body and with out a word, he stands up with his cock still inside. He puts my arms over his shoulders and holds me up while he ramps up his fucking to a violent pace. I cry out in pain and pleasure as his cock rips through me as his fingers sink into my thighs where he's holding me up. I do my best to hold on to him, but I can't do it for much longer as he seems to be fucking the strength out of me.

"Baby, I can't hold on," I barely manage to squeak out. James, still carrying me with his engorged swollen meat still in me, walks over to the kitchen table, and lays me down on it. He spreads my legs out and starts to fuck me even harder as I start to stroke my cock, twitching in pleasure on the table. James kisses my feet and sucks my toes while pounding my ass, his hands exploring and caressing my writhing body. It's not long before my cock explodes onto my stomach and all the way up to my face. I lick off the cum that lands on my lips, and stare into James' eyes, my ass muscles still spasming from the exploding orgasm that just rocked me. His pounding becomes slower, and I can see his face tensing up.

"Josie, you're going to make me cum," he moans as I try to tighten my sphincter getting ready to milk the cum from his cock into my ass. James cries out and his whole body tenses up as he pushes hard into me one more time, the familiar feeling of cum filling my rectum washes over my body. I hold him in me and he leans over to kiss me, his hips bucking and his balls draining the last of his cum into my ass. I return his kiss, our tongues exploring each others' mouth tenderly. "I think I could fall for a girl like you, Josie," I wink at him and just kiss him again. We take a shower, and I fall asleep in his arms, basking in the glow of having been fucked for the second time, and loving it.

Over the next few weeks, James and I have a lot of fun with each other. I hang out at his place when he's at work, and by the end of the first month I'm not even going back home on the weekends. I get to hang out with Madeline every once in a while, but not very often as I'm usually home with James. At the end of the two months, I go in for surgery, and over the next few months after that I am in and out of the hospital.