My mistress has a date tonight. First I am to dress as her “personal” maid. She took great care to emphasize the word “personal.” Then I am to help her get ready for her date.
Mistress laces me into a tight corset. This is always a constant reminder of my sissy and subserviant status, since I can feel the corset with every breath. She gently tweaks my tiny nipples and then gives me the bra I am to wear tonight. A training bra, with no falsies. I arrange it on myself as I realize how inadequate I am as an impersonator of a woman.
She gives me some lacy panties to step into, commenting that she has no use for my cock this evening — she has a date with a real man. I roll the thigh high black seamed stockings up my legs and attach them to the garters of the corset. Mistress examines me to make sure the seams are straight. Then I put the short, black maid’s dress over my head. It does not provide much covering for my ass and thighs, and the garters will show if I bend even a little. I step into my black high heels, which changes my balance and is another constant, subtle reminder of my sissy status. A maid’s cap is pinned in my own hair, and I realize I am not even to have the benefit of a wig tonight. The final touch is a lacy apron that I tie in a bow behind my back.
Mistress tells me to hurry up and sit down on the toilet seat, for her date will be coming soon and there is still much to be done. Her date! It is not enough that Mistress likes to embarrass me in front of her female friends, but now her male friends too! And with no wig and no falsies, I am not going to make a very convincing female, am I?
Fortunately Mistress enjoys putting makeup on me, so perhaps I will have an adrogenous look today. Mistress must be in a playful mood, because she puts far too much mascara, eyeliner and blush on me, and apparently she wants me to look very cheap. She outlines my lips very precisely in a dark lip pencil, and then fills them with a brush in a nice red. I’ve never liked that dark pencil — there’s something too obvious, too whory about it. Then she takes a vaseline like jelly with her fingertip and rubs it thickly over my red lips. This gives them an unnatural, almost metallic sheen, but apparently that is the look she wants me to have tonight.
Mistress hands me a bottle of nail polish in a matching shade to my lipstick, and tells me to do my nails while she takes a shower. “Oh, and change the sheets and make my bed first, Sissy,” she tells me. Another humiliation — I have to make the bed ready for her and her date from when they come back home at the end of the evening!
I make her bed and then do my nails while I wait for Mistress to emerge from the shower. As I wait and as I blow on my nails for them to dry, I glance at the lingerie she has left out that she will be wearing tonight. I see her push-up Wonderbra. Mistress has a gorgeous figure including perfectly round, white 34B breasts, and she needs no extra cleavage to show herself off. One of my pet peeves about Mistress is that she really has no idea how drop-dead gorgeous she is. Of course, she doesn’t believe me when I tell her that. But if she is wearing the Wonderbra, then this must be an important date for her tonight. I will have to do whatever I can to help her.
Mistress emerges from the shower and I am there for her with a large towel to cover her and pat her dry. She allows me to pat her all over with the towel, which gives me a little pleasure. I then powder her gently with a big powder puff full of a sweet smelling talc. She tells me to spend extra time on her breasts, which of course I do very lovingly. She has me hold her tiny panties out for her to step into, and I see her tiny pubic hair triangle disappear into them. Then she has me hold her Wonderbra for her to insert her breasts into. I hold the bra cups and struggle not to reach out and fondle her lovely breasts. I clasp the bra behind her. This bra does wonders for her cleavage and I look at Mistress with awe. She slips on her high heeled slippers. She is SO sexy.
Mistress has me blow dry her hair, and then she has me brush it for her. I lovingly stand behind her and brush her beautiful hair. This is an act that only a true submissive can understand. It is truly my pleasure to do this — I don’t think Mistress really comprehends that. Then Mistress allows me the privilege of handing her cosmetics as she does her own makeup. She lets me hold the mascara bottle as she makes up her long lashes. She lets me hold her eye shadow case as she gently strokes the color on her eyelids. She lets me hold her blusher compact as she strokes a little color on her cheeks. On other occasions she has made me masturbate while watching her do her makeup, and my cock remembers that, but this is not the plan tonight. Finally she tells me to unscrew her Estee Lauder lipstick in rose, and then she carefully colors her lips. I could watch Mistress apply her lipstick for hours, it is just so sexy. I am completely turned on by the sight of it. Mistress tells me she is done with her makeup. And she is gorgeous.
Suddenly the doorbell rings, and Mistress tells me to answer it. “Shall I tell him you’re not finished dressing yet?” I ask her. “Oh no,” she tells me, “I am finished.”
Mistress is beautifully made up, but she is only wearing a bra and panties and slippers. How can she go out like that? Then it dawns on me — they’re not going out. It’s an evening at home, with her dressed only in her lingerie. What does that mean for me?
I open the door and let him in. He introduces himself as Brad. I suppose he’s good looking — if Mistress likes that type. He stares at me, not knowing what to think, since Mistress has not quite made me into my feminine best. He gives me a sly smile, since he undoubtedly knows my secret, that I may be Mistress’s maid, but I am certainly not a female one. However, he is too much a gentleman to say this.
Mistress emerges and they kiss deeply, oblivious to my presence, although why should they care. Brad’s eyes bulge at the sight of Mistress’s sexy breasts, almost spilling out form her Wonderbra. I help him remove his jacket, and I offer them a drink. As I leave to get their drinks, they start making out on the couch, and Mistress starts to unbutton Brad’s shirt.
By the time I return with the drinks they are making out passionately. Mistress tells me to bring the drinks into the bedroom. I do, and they both come in too. Mistress then tells me to make myself useful. “Useful?” I repeat. I am not sure what she means.
“Sissy!” Now Mistress is mad at me. “You’re supposed to be my personal maid. Do I have to spell it out for you? Make yourself useful and help Brad remove his pants.” I cringe at the thought of this, and I try not to look at him as I kneel down, loosen his belt and help him step out of his pants.
“Well, Sissy?” Mistress says next. I know what she expects, but I can’t react. At this point Brad knows too. “Sissy!” Now she is really pissed at me. “Remove his undershorts this instant! But for your insolence to my guest, I want you to put your hands behind your back, and lower his undershorts with your teeth!”
Mistress did not apply enough blush to my cheeks to hide the embarrassment as I slowly comply with her command. I need to put my face right up to him as I gently grab the waistband with my teeth and carefully lower his shorts down his legs. Mistress has surely done it again. She has no end of ways to humiliate me.
But she is still mad at me for having to tell me each little detail. She asks Brad if he thinks I need a spanking. Brad is not sure what to make of this, but he is turned on by the sight of Mistress, he is turned on from their making out on the couch, and he is turned on by this sissy maid being made to remove his shorts with her teeth. I am still kneeling and Brad’s erection is right at my face. I am actually relieved that Mistress is apparently not going to make me get more intimately involved with Brad.
Mistress grabs her hairbrush — the hairbrush that I lovingly used to brush her beautiful hair not long ago — sits down in a chair and motions for me to lay down in her lap. She flips up my skirt, and I wonder if she is going to pull down my panties. She pauses for the longest moment, and I know all three of us are thinking about this. Fortunately, she decides to leave them on — for now.
Mistress starts spanking me on my panty covered ass with her hairbrush. She has one of my arms bent behind me, as she wails away with her other hand. She is hitting me hard, and I start to scream. Mistress decides she doesn’t want to hear my sissy screaming, and she tells Brad to take his undershorts and stuff them in my mouth. I am SO humiliated. Brad spreads my glossy red lips and inserts his shorts in my mouth. Mistress keeps wailing away. My screams are muffled, but I am crying. Brad watches the scene, and his erection grows.
Finally Mistress has had enough of spanking me. She asks me if I have learned my lesson, and if I will be a useful personal maid. I nod tearfully. She tells Brad, “Don’t worry, while you and I are busy Sissy will wash and iron your shorts for you.” How’s that for a humiliation? I have to wash his shorts in the next room while they make love?
Mistress wipes my tears and tells me that she know how I can be useful to her. She tells me to take Brad’s shorts out of my mouth. She removes her panties and lays down on the bed. She spreads her beautiful legs and motions to me to come to her. “Get me nice and wet for Brad, Sissy.”
I am always eager to get Mistress nice and wet, although not for someone else. It is especially embarrassing to go down on Mistress while someone else is watching. But when Mistress speaks, I must obey. I kneel between her legs on the bed, gently spread her lips, and go to work. Mistress must have been mistaken — she is already quite wet. Kissing Brad and spanking me probably helped get her wet. But I lick her for awhile until she tells me to stop.
Brad is standing there with his big erection waiting for his turn. He is certainly ready. But Mistress says that she wants him to wear a condom. I know there is always one ready in her nightstand drawer. “Uh, Sissy?”
I am red-faced as I know what Mistress expects me to do. I go to her nightstand drawer and get a condom. I remove the wrapper and gaze at it. How I wish it were going on me, and then … But that will never happen. I resign myself to the unpleasant task of taking Brad’s cock in my hands and rolling the condom on his erection. Mistress spreads her legs invitingly once more. Her pussy hair glistens — due to me, I wish I could remind them both. Brad leans forward toward Mistress. Mistress then speaks up again.
“Uh Sissy? I want you to insert Brad into me.”
Will there be no end to Mistress’s indignities? So as Brad gets into position, I take his condom covered erection with one hand, gently spread Mistress’s lips again with my other hand, and ease him into her.
What next, I wonder to myself. Will I have to push it in and out too?
Mistress thankfully tells me, “Thank you Sissy. That will be all for now. Go into the bathroom and fix your makeup — it’s a mess. Make sure your lipstick is the way it was when Brad first arrived. Nice and red and glossy. Then when your lipstick is right, I want you to jerk off into your pretty panties. Leave them on, because we’re going to check. And then don’t forget to wash and iron Brad’s shorts.”
And with that Mistress dismissed me with a wave of her hand, Brad started pumping away, and I retired to the bathroom to follow Mistress’s commands.