Made a Maid Ch. 01

Big Tits

(This is my first story. I love feedback! Enjoy!)

So there I was, handcuffed, gagged, blindfolded, in full drag, with my panties around my ankles, bent forward, and unable to move. My mind was racing, when is she coming back? What if someone see’s me like this? Oh God, what have I gotten myself into? While I stood there, my heart jumping out of my throat, I could hear footsteps and the door unlocking behind me. All of the blood drained out of my face and I started to panic, I knew I was in trouble, but I think it’s important to go over what got me here.

My name’s Joel, I’m 21 and I’ve already kind of fucked up my life. I won’t go into great detail, but why any credit card company would give an 18 year old kid an available credit of $25,000 is far beyond me, they know he’s just going to max it out on drugs! Well, maybe not you, but that’s what I did. Anyway, soon enough I ran out of money to pay for my habits and I had to move out of my decently nice apartment. Lucky for me I’ve got lots of friends, and one of them, Madeline, invited me to stay with her, she has a spare room with a bathroom and doesn’t want much in rent. Her place is really nice, so I agree and move in.

She’s the perfect roommate, she doesn’t bother me, cleans up after herself, and watches the same TV that I do. She’s also not bad to look at, she’s only 23, about five foot seven inches, thin, but with a nice ass. Her straight black hair falls just above her shoulders, and she loves to wear mini skirts, showing off her great legs. Like I said, she’s the perfect roommate. We’ve always flirted, and I don’t blame her, I mean, I’m not that bad to look at either. I’m about five foot nine inches, thin, but with a nice ass. I’ve never been a big guy, and I keep my face clean and groomed for my job. Anyway, we’ve always flirted, but nothing’s ever happened, I always thought it would be like kissing my sister.

We had been living together for a few months at this point, and February was coming up. She was nuts for Valentine’s Day, and she had just started dating this new boy. She had just gotten back from the mall with a bunch of bags,

“Hey Joel, do you think Ivan will like any of these?” She starts to pull things out of the bags, showing me a matching skirt, bra, thong, lingerie set with a babydoll. They were all black with hod red trim.

“Sure he will Mad, I still just think it’s hillarious that you’re dating someone named Ivan. Who name’s their kid Ivan anyway?” I try not to let my eyes linger on the lingerie that she’s holding over herself in front of the mirror, she shoots me a glare and shoots back.

“Well what the fuck kind of name is Joel huh? They couldn’t just stop at Joe? Had to throw in another consonant?” She winks at me, and throws the lingerie and a pair of shoes in my lap, “But really, what do you think?” I try to feign disinterest, but I can’t help but thumb the soft fabric, and the soft leather of the black pumps, “Ew, alright, don’t get a boner or anything thinking about me in those Joel.” She snatches the items from me, and throws them back in the bag, and tosses them in her room.

“They look great Mad, I’m sure he’ll love ’em,” I get back up and start idly doing the dishes,

“Thanks,” she says heading out the door again, “I’ll be back soon, I’ve got to run some errands.” That girl is always going in and out, she can never just make one trip. I finish up the dishes, and try to not think about the lingerie that she threw at me.

I think I should explain, I love dressing in girl’s clothes, I’ve been doing it since I was a little kid, and I’ve continued until now. I’m not, however, a pervert, I have my own clothes! I try to push the idea of trying on my roommate’s lingerie out of my head, but after an hour being on my own in the condo, I can’t resist any more.

I sneak into her room, even though the house is empty I’m tip-toeing. I find the bag, and pull the items out and inspect them closer. First are the shoes, they’re cute, black leather pumps, with a cute red trim. They must be about five inches high, I check her size, and there’s no way I could fit in those, and I’m not about to stretch out her brand new pumps- no matter how cute they’d look on me. Next the thong and bra set, really cute. Black lace with red trim all the way around the top of the cups, and the top of the thong. I disrobe quickly, and look at my smooth shaved naked body in front of her full length mirror, I’ve always had a slight frame, and I’ve worked on it by running and working out. I pull the panties on slowly, letting the lace caress my long smooth legs, until finally nestling between the cheeks of my cute tanned butt. I know a lot of Asian guys say their cocks aren’t small, but I’m only half Asian, and mine is pretty small, I say this because all of the cocks I’ve seen are at least four inches longer than mine. In any case, I tuck my little cock between my legs, I love the feeling of it pushing against the soft lace of the thong. I pull up the short black and red lace mini skirt, it barely covers up my ass. I put the Bostancı Sınırsız Escort bra on, and I note that my roommate and I wear the same size. I slip on the babydoll, and admire myself again in the mirror, the look isn’t quite complete, so I prance over to my room, and pull out some black stay up thigh highs, my falsies, my wig, and my four inch black patent pumps. I put on some music and smoke part of a joint while I do my make up in my bathroom, shaking my hips idly while I paint my face and fix my wig.

I must have been quite a sight to see me like that! I mean, if you knew me, I’m kind of a guy’s guy, but there I am, standing tall and proud and dressed like a hot girl. I just finished putting on my mascara, when I remember that my roommate will be coming home any minute now. Frantically, I kick off my pumps, and take off all her lingerie while running to her room. I put all her delicates back in their bags, and pick all my clothes up off her floor, and run back to my room. I lock the door, and dress back up in some of my things. She comes home a few hours later, and that gives me time to take off all my make up and return to my boy look, so I can go and hang out with her in the kitchen. I love the idea that she has no idea what I do when she’s away.

I cook us some dinner, and we chat idly over wine. We talk about her boyfriend, and her boyfriend’s funny name. We kill more than a bottle of wine, which is pretty normal for us, and retire to our rooms.

I sink into my bed and let the wine take over. My heavy eyelids making it difficult to pay attention to what’s on my TV, I’m just about to fall asleep when my door swings open.

“What the fuck Joel?!” My roommate bursts into the room, hitting me, “I knew you were a fucking freak, but you’re a pervert too?”

“Wha- what are you..” I’m confused, rubbing the blur out of my eyes. Confusion gives way to shock when she says, “I know you tried on my lingerie, Joel.” Time seems to stop as all of the blood drains out of my face, all I can stammer out is, “H- how.. How did you find out?”

“My laptop was open, and the web cam was on. Ivan was watching, and when he saw you start taking off his clothes, he started recording. He sent me the video, and I have to say,” as she derided me I felt myself shrinking away, “you are one pretty little sissy.” I was surprised by that last part.

“Pr- pretty?” Was all I could say.

“Yeah, pretty.” She sat down on my bed, “I’ve known for a while that you’re a crossdresser. Come on, the ladies razors in your bathroom? And I can tell when make up has been spilled on the counter.. And there are scuff marks on the hard wood floor, and I never wear my pumps in the house, so they must be coming from yours.” My face was sheet white as she laid out the evidence, I cursed myself for being so careless. “Now, I’m pretty mad that you wore my gift to my boyfriend, and showed him that hot little body of yours in MY lingerie..”

I eked out an “I’m sorry,” before she stopped me with a finger gently on my lips.

“Look, I’ve known for a long time, I’ve just been trying to figure out how to let you know that I know. This is perfect.”


“Yes, perfect. Here’s what we’re going to do. Starting tomorrow, you’re going to be in drag around the house twenty four seven. You’re going to be my maid and personal assistant. Don’t worry, it’s not going to be that bad for you. You won’t have to pay me rent any more,” she caressed my face gently, “Doesn’t that sound like fun for you?”


“Don’t worry, if you say no, which I’m pretty sure you won’t, I’ll be releasing that video of you to all of your friends, coworkers, and family. I won’t think twice about outing you, I mean you really should do it yourself, come on, you’re gorgeous, but don’t think that I won’t do it for you.”


“Yeah, there will be time for that too,” she winked at me as she turned to go out the door, “Good night Josie. Sleep well, you have a big day ahead of you tomorrow.”

I toss and turn all night, and I need to smoke quite a bit of pot to calm my nerves enough to sleep. I wake up to my alarm, and look around. There’s a note taped to the inside of my door. Groggily, I open it up:

“Hey Josie, (I hope you don’t mind me calling you that) don’t forget about our chat last night! I’d love breakfast in bed.


“Well fuck, she was serious.” I look through my drawers and try to find something at least decent for me to wear. Too bad none of my girl clothes are meant to be worn out, I don’t really have anything that covers me up, not that I really have a reason to be shy at this point. I pull out the most conservative outfit I can, which still consists of a skirt that’s way too short, and a top that pushes my fake tits way up. I start by tucking in my little cock, which seems to be displaying my embarrassment by being even smaller today, into a pair of tight white cotton panties. I follow up by stuffing my 34C cup bra with my silicone falsies, throwing on a Bostancı Suriyeli Escort tight red top over that. Finally, I pull up my short black skirt, and put on my four inch stiletto pumps. I do my makeup, fix my hair, and hesitantly open my door to the hallway, and head into the kitchen, my pumps clicking down the hardwood hallway.

There’s an apron on the counter, with another note:

“French toast and coffee, by 10am”

It was already 9:35am, I didn’t have much time. I’m not used to getting dressed quickly. The bread was just about the hit the skillet as Madeline bursts out of her room, still in her pajamas.

“It’s 10:01. Where’s my breakfast?”

“I’m sorry, I-” she stopped me again by placing a finger over my painted red lips, she then gestured to me to turn around, I just stood there looking confused.

“Turn around,”

“But.. Why?”

“Turn around.” She glared at me hard, and I sheepishly turn around, with out warning, I feel a hard slap across my ass, “Next time, I’ll take you over my knee and pull your panties off first.” I could feel my face turn bright red, I was speechless! “Now finish up my breakfast, and bring it to me in bed.” Madeline poured herself a cup of coffee, and took a long sip while she looked me up and down. I had never ever felt so violated, I had also never ever been dressed up in front of someone before. I had also never been so turned on before, my cock was straining against the soft cotton of my panties, drops of pre cum undoubtedly being squeezed out.

In a daze, I finish making her breakfast, I arrange a plate, and arrange the plate on a tray. I walk it over to her room, lucky for me I waited tables for years, I have great balance with a tray. I knock on her door, and I hear a muffled “come in.”

“I’m sorry I had to spank you like that Josie, but you weren’t following directions. If you just follow my directions properly, I won’t have to do that to you any more! Now come, let’s talk about your new arrangements while I eat my beautiful looking breakfast, good job by the way.” I sat obediently, feeling an odd sense of fulfillment at her small complement. “You look great today too, who taught you to do your make up?”

“I taught myself,” I squeaked,

“Now that just won’t do, can’t you talk like a girl? A little bit higher? A bit more sultry? Try it again.”

“I taught myself,” I tried hard to go up an octave, this seemed to please her.

“That’s much better. Well, that’s impressive, Josie. So, here’s what’s going to happen, you’re going to cook and clean for me, I promise it won’t be more than a few hours of work a day. You’re going to be my best girlfriend too, you’re going to gossip with me, and do my nails and toenails, and so on. You can go out as a boy, but the rest of the time, you’re to be dressed as a girl the whole time you’re under my roof. If I decide to bring my boyfriend over, and have my maid cook us a wonderful dinner, you won’t have any problems with that. He’s already seen the best of you anyway. Does this sound agreeable?”

“But what about my job..?” I almost let myself talk like Joel again, but I slipped effortlessly into my new voice,

“Don’t worry about your job. I’ll pay the rent, I’ll pay your bills, I’ll pay for the food. I’m hiring you now, and don’t worry, I love buying my best girlfriends gifts!” She sounds giddy when she says ‘best girlfriends,’ the shock is still setting in for me for this entire situation. I’m being blackmailed into being a sexy maid for my girl roommate, if I didn’t feel so exposed, and if it weren’t happening to me, it would be funny, but as it’s my new reality, I can’t help but feel a little violated. She finishes her breakfast, and gestures at me to take the dishes away.

“Now Josie, don’t feel down on yourself. It seems to me that you like your new role,” she gestures at my now impossible to hide bulge in my skirt. My face turns an even brighter shade of red than it already was. “Isn’t that going to be a little distracting to your duties my dear?” Her voice has a wicked tone to it. She pulls me closer to her bed, and she gets out from under the covers. Her face is inches from my crotch, she sniffs at me. “You still smell like a boy, not a bad thing, but I like my girlfriends to smell like girls,” she looks around in her nightstand for a second, and pulls out a bottle of perfume and hands it to me. I don’t miss a beat as I spray myself with it, and hand it back to her. She lifts up my skirt and gives the crotch of my panties a spritz as well.

“Now you smell good..” I can feel her hot breath through the cotton of my panties, I’m nearly breathless. She teases a finger around the modest outline of my throbbing cock. “You’ve got a mighty big clitty here Josie, not big enough to be a cock, but a perfect size for a big throbbing clit.” In one motion, my panties are around my ankles, and her mouth is on my cock. With no effort, her nose is grinding into my pelvis as my little cock fills her mouth, she massages the underside with her tongue, Bostancı İranlı Escort and it doesn’t take long before I feel myself getting ready to cum.

“Mad, I’m going to cum..” I moan as girly sounding as I can, she doesn’t move her mouth from my cock and I cum, nearly doubling over onto the bed as she drains my balls of their seed. She doesn’t swallow, instead she looks me in the eye, and pulls me down to her level and kisses me hard, depositing my entire hot load into my own my mouth. I can’t control the grimace on my face, she notices that and instructs me to swallow.

“Now Josie, all the good girls swallow. Me, I’m not a good girl, and there is no way I am drinking your sissy cum. Now swallow that cum and go do the dishes.” I obediently swallow, and pull up my panties before I gather the dishes up and return to the kitchen.

Days pass with the same routine, I get up and get dressed, and there’s a note taped to the inside of my door with a breakfast request. I make her breakfast, and serve it to her in bed. She rewards me with a blowjob, and sends me back out to do chores. I hang out and clean while she’s at work, and I usually have to relieve myself a few times because being dressed up all day turns me on. Every once in a while, she returns with a new outfit for me to wear, which I am to promptly model for her. I cook her dinner every night, and draw her bath, before I’m dismissed to my room.

Every once in a while, I know her boyfriend is home. Madeline hasn’t made me meet Ivan as Josie yet, but I’m pretty sure it’s going to happen. He’s usually only here late, after dinner, and usually leaves after fucking her.

One day I have a note that reads:

“Breakfast for two today.”

“Fuck.” I know what’s coming. I fix breakfast, and knock on her door. She tells me to come in, and I can hear a man laughing in the room. I take a deep breath and walk in. Ivan’s lying in bed with Madeline, and he’s laughing, we’ve met before, but not like this.

“God damn honey, you weren’t kidding. You’ve turned him into a real slut maid!”

“Baby, be nice, she’s my sultry assistant,” she winks at me, feigning defending me, I can feel his eyes on me, and I’m at the same time turned on and feeling violated.

They dismiss me, and he smacks my ass on my way out, which makes Madeline giggle to no end. They come out of their room eventually, practically dumping their dishes on my lap.

“We’re going out for most of the say Josie, you can have the day off today.” Madeline says to me, as Ivan eyes me hungrily on his way out.

Even having the day off, I still just lounged around in some of the more casual clothes that Madeline has bought for me. At this point, I’m pretty much entirely comfortable crossdressed at home, and I stay dressed even on my days off. Madeline likes it. The day goes by uneventfully and I eventually retire to my room. Madeline and Ivan get back late, and they go straight to their room.

I’m almost sleeping, smoking a joint in my room. I’m still dressed up from the day. I hear the door creak open,

“Oh hey Mad, you want so-” I’m stopped with a hard slap across my face.

“Madeline kept you from me for too long, she kept saying you weren’t ready. Well, I saw the way you were looking at me earlier today. Your eyes might be saying no, but your whole body screams yes.” Ivan stood there, seeming like he towered over me. He quickly stuffs a ball gag into my mouth before I can make a sound. I can’t make much of a struggle, as I’m still stunned from the slap across my face, he clicks some handcuffs onto my wrists with my arms in front of me, and he pulls me up to my feet. He walks me back to their room, where Madeline is laying naked in the bed, disheveled, obviously just fucked.

“I tried to stop him Josie, but he’s soo convincing. You’ll see what I mean soon.”Madeline says as she idly watches Ivan push me over the sofa in the sitting area of her bedroom, she takes the handcuffs off only long enough to attach the restraints to the sofa. He pulls me skirt up, and yanks my panties down, my rock hard cock springing forward.

“Mad, get over here and take care of that. You know how much I love my sissies soft and limp,” and without hesitation Madeline is under me jacking me off, it doesn’t take long before I blow my load into her cupped hand. She immediately smears it across my face, which makes Ivan laugh. “Look at her, helpless, I love you baby, thanks for finding me another fresh sissy.” He slaps my ass hard, leaving red welts where his fingers met my bare ass. He then starts massaging my virgin asshole, smearing spit onto my puckered hole. Before long, he has a finger in me, I moan through the gag, the pain soon subsiding to pleasure. He fingers my ass for a few minutes before he starts smearing lube over my hole as well. “I want you nice and ready for me to fuck you, slut. I am going to make you beg for my cock.”

His fingers massage the inside of my asshole for what felts like hours before my flaccid cock started oozing cum, Madeline takes off my gag, and starts hand feeding my my own cum, which I greedily lap up off her fingers. Ivan takes the cock out of his boxers, it springs to life growing to its full and thick nine inches, it throbs as Madeline takes it into her mouth, lapping it and getting it wet and ready while her boyfriend fingered my ass.

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