As I walked into the hotel room hours in advance, my cock was rock hard with anticipation. The last time me, my lover Amy, and her husband Matt were all together, it was my dear love Amy's turn to be in charge. Amy had Matt and I dress like two Fifties sluts. The kind of girls uptight parents used to believe would cause the downfall of society.
It was both Matt and I's first times with other males though not my first time dressed up. He is still fairly new to this as his wife just discovered his secret but he took well to being a little cross dressing slut. Today, it's my turn. I get in the shower and make sure my body is completely absent of hair. Once I'm done, the first phase of the fun begins.
I go to one of the four bags I've prepared in advance for tonight. One is just regular clothes, the other three contain a plethora of clothes designed for maximum fulfillment of one of my darkest fantasies. I open up the bag to reveal a virtual wet dream of feminine apparel. I start with the black satin thong. I've always loved the feel of sating against my freshly shaved cock. Next is the black satin and lace garter belt. I know that stay up stockings exist but I've always loved the look of a garter belt and stocking over my legs. I take the garter belt and wrap it around my waist and make sure to put the suspenders on the inside of my thong just make sure I can take them off and leave my stockings on. Next, of course are the stockings themselves. They are simple black sheer stockings with lace tops that I attach to my garter belt. My cock is rock hard at this and no one is even here.
The real fun begins when I put on my white satin blouse. Before, I was just your regular cross dressing slut, but putting on this blouse starts getting me into character. The ruffles down the center of it are the ultimate height of femininity along with semi-high shoulders, but the leather skirt and the six-inch black patent leather stiletto heels I have on have put me into full on mistress mode. Why mistress instead of master you ask? Because when I'm en femme, I prefer to take on a female persona while still maintaining my masculine identity. I'm not a trans person nor do I wish to be one. I'm a guy with a cock and I love having it wrapped in the most feminine apparel. With that said, I've also always been attracted to cross-dressers, transvestites and shemales. I too find it strange that things penises normally repulse me, but as soon as one puts on a pair of panties, or in any way tries to pass for female, suddenly I can't imagine that cock anywhere but my ass or mouth.
I go back to my bag and grab the bottle of Bushmills to settle my nerves. I know they'll be here soon. Once I've settled my nerves, I hear their car pull into the parking lot. I take off the heels and quickly put on socks and a heavy bath robe. Neither of them has seen me like this and I don't want to spoil the surprise. I hear their idle chat as they approach the door and knock. I open it at greet them both with long, passionate kisses. I can tell they're both just as hot and heavy in the loins as me, but they'll have to wait. Amy kind of knows what's going to happen as part of it was her idea, but she doesn't quite know everything I have in store for the two of them tonight. A girl has to have her secrets.
I take two of the four bags I have and designate which one is for whom. As far as I know, neither of them knows what's in their bag. I tell them to get dressed wearing nothing but what's in the bags and to present themselves to me when done. With that, I retire to the bathroom to relieve my bladder and take another swig of whiskey. I've never been so nervous yet so excited about something at the same time. It takes all of the self-control I have for my cock not to rip through my panties and skirt.
I close the door and immediately hear the sounds of the bags opening and the items being laid out and put on. This gives me time to apply my make-up. I'm no expert in the matter but I've watched enough videos on Youtube and practiced enough to have gotten the basic idea. I remember watching my cousins go through this process as a kid before they went out to the clubs and always felt insanely jealous. Not because they were beautiful girls that I definitely had a few impure thoughts about, but because I wished I could dress up and join them. Oh well. At least I always had their wardrobes to steal from. One benefit to living in a Latin household is that all of the curvy girls had clothes that stretched.
First I apply my mascara and eyeliner. Not too gaudy, just enough to make my eyes stand out. Next is my foundation. I've never been much of a fan of the stuff, but given that even if I shave my face completely smooth, you can see where my beard normally is. That's not at all ladylike and I won't stand for it. Next is my lipstick. It's simple a simple mid-hue red. It's not bright enough to scream whore and not-dark enough to either. It simply says, "I'm in charge tonight."
After what felt like ten minutes of fussing around with my make-up but turned out to be closer to an hour, Amy calls out that she and Matt are ready to present themselves. I tie my long hair into a tight bun and put my heels back on. The last step is my bra with my 36DD breast forms. If I'm going to look the part, I'm going to feel it as well. I peek out and see that they are both being good slaves and are on their knees with their eyes down and hand across their laps. I put on my heels and walk out to inspect them.
In what looks like well-choreographed unison, they both lean forward and kiss my shoes, then say, "Good Evening, Mistress." It sends a shiver up my spine and more blood rushes to my loins. With that, I order them both to their feet. Like good slaves, they avert their eyes and stand slowly enough as to not fall, but also remain graceful. They've only seen my stocking feet and shoes at this point. From here, I begin to inspect the two specimens in front of me.
First is Matt, or should I say, Sissy Matt. He stands before me in the frilliest pink dress I could find that would fit his six foot frame. I would have gone with white, but he's no virgin. Keeping his eyes to the floor, I do a full walkaround to make sure he did as he was told. His body is hair free, just the way I like my girls. His platinum blonde, bob cut wig with bangs is as in place and as it should be, His ears are pierced with simple pearl earrings to accentuate the sheer lining of the neck on the dress. On his hands are simple white lace gloves that go just past his wrist. His petticoat is nice and wide as it should be under his dress to give it that layers effect along with giving me easy access later. I lift up the back of his petticoat to reveal his pick, frilly rumba panties. His ass looks so delicious in them and, like a good girl, he remember to put his garters on the inside of his panties. I give a quick poke of his asshole to make sure his butt plug is in place. It is. I then reach around the front to make sure his chastity device is as well and that his balls are appropriately swollen from having not cum since the last time we were together. The seams on his pink stockings are straight and even like they should be. I have him in simple pink four inch Mary Jane shoes with blocky heels and ankle straps. They're not as slutty as I'd like, but he had trouble with the six inch heels similar to mine last time we were together so I figured I'd take some mercy on him in this respect seeing as later, he will be shown none. Once I've given him a good once over, I order him to look at me so I may inspect his face.
This is his first glance at my white satin blouse with my made up face and jutting breasts. His face is a look of both excitement and apprehension. I'm sure he's always wanted this, but never knew it would happen. I look into his modestly made up face with a combination of pure sadistic glee and unabashed lust. He couldn't pass to save his life just by virtue of the way nature constructed his body, but neither could I. That's part of the thrill of all of this for me at least.
Having inspected him, I tell Amy, "Good girl. Had he not passed muster, you would have suffered for it." She responds with a meek, "Thank you, Mistress." While keeping her head down. I look back into Matt's eyes before I take him into a long, passionate, wet kiss. Our tongues dance in each other's mouths like Russian acrobats and you'd never know we weren't long time lovers by how hot it gets. This is partially because of how beautiful he looks and partially because I know his cock is straining against its plastic cage. Like I said earlier, it's sadistic glee and unabashed lust. Again, it takes all of my restraint not to take him right now and my cock is certainly ready. With him passing muster, I send him to the corner with his head to the wall as I still have one more slave to inspect; only she kind of knows what's going to happen and is just as wet as me.
Next is my slave and lover Amy. In contrast to her husband, I have her dressed as slutty as possible. Her long dark curly hair cascades behind her neck like a waterfall of feminine beauty. The black dress I have on her is simple enough in its construction, but the see-through fabric and tight figure hugging material leave little to the imagination. The tight, leather corset top barely contains her ample breasts and the shiny rivets on it do little to stifle my lust. The corset is pulled so tight as to give her some semblance of an hourglass figure, but given how plump her body is, it makes her delicious ass look even better. I move down and inspect her black satin, high cut bikini panties with her garters on the inside as well. They make her ass look even yummier than her husband standing the corner awaiting his turn. I follow the natural contours of her plump body down a little more to where the suspenders of her corset meet the black lace stockings I've assigned her to wear. I've seen her in regular nylons before, but the way the black lace mixes with the sheer fabric of her dress play exactly as they did in my head. On her feet are simple black two inch chunky heels. This is partially because she's a bit clumsy in regular heels but more so that I may tower over her to assert my authority. Ever present is the scent of her obviously excited pussy. Had my body been able to secrete such a smell, I would have long suffocated both of my slaves. Having gotten my seal of approval, I lift her head up so she can finally see me in all of my glory.
The look on her face says it all. Had I not been the one in charge, she would have thrown me to the bed and ridden me like mechanical bull until she had an orgasmic coma. Being a good slave, she restrains herself. We lock eyes and enjoy a nice kiss as well. It's not as dirty as the one I had with Matt, but this one says "I love you. Thank you for this" more than it does me trying to assert my authority. She knows who's in charge and is more than happy about it.
I lead her over to the bed tell her to lie on her back and take off the dress. She won't need it now. I just wanted to see her in it. I tie her hand to the bed post and I blindfold her. I reach into my goodie bag and pull out my, paddle, flogger and feathers, along with a few other electronic devices I'm surprised I found in a Walgreens. I tell her that she's my big, beautiful, precious girl and that I love her. She swoons with passion as I give her another deep kiss. It's strange that I don't want to hurt her, but that she wants to be hurt. One could make the argument that she's really in charge as I'm the one doing what she likes, but she's the one tied to the bed.
The first thing I do is lick her neck. The response is immediate. She rapidly inhales and strains against the ropes. I know my girl and what sends her over the edge. I continue working my way down to her ample breasts. She's stacked like a wall at Costco. I reach into her corset and start toying with her nipples while I rub my stocking covered legs over her dripping cunt. I remove one hand and move it down there. I slide my finger into her then quickly remove it. I inhale deeply then I bring it to her mouth. I order to suck my finger clean before I give her another deep kiss so we can share in her juices. Next is the feather. I run it all up and down her body further teasing her lovely shape and further causing her to quiver. It's enough to send her into an uncontrollable orgasm, one of many more to come. I put the feather away and release her from her bonds and tell her to get on all fours. I'm not done with her just yet.
I reach into my bag and pull out a set of industrial earmuffs. I saunter over to Matt and tell her to turn around. She catches a quick glimpse of her wife before I turn her head towards me and give her another long passionate kiss with lots of tongue while reaching into her panties and playing with her still restrained and aching cock. I reassure her that she'll have her turn soon enough but for now; she must put on the earmuffs and face the wall again. This so I can go to town on her wife without her hearing it further adding to my control over her.
Amy is still on all fours and blindfolded with her ass facing me. The front of her panties is soaked beyond measure. From back here, I can fully appreciate how the combination of her panties, garters, stockings and shoes truly make her this paragon of submissive femininity. It's strange to think that this is a woman I've cuddled with on numerous occasions while watching a movie and have looked longingly into her eyes on numerous occasions knowing that she felt the same about me as I did for her. She truly is the love of my life. With that said, I grab the flogger and start gently running it over her exposed skin before I start playfully spanking her with it. It doesn't hurt her too much, but she certainly feels it and her blindfold makes the feeling so much more intense. Unknown to her, I've grabbed the paddle and without warning, I rear back and give her a good solid whack on her round ass. She recoils in pain for a split second before exhaling pure submissive lust. I ask her if my little slut wants more.
Suppressing another impending orgasm, she simply says "Yes, Mistress Derek." I proceed to give her swat after swat until she buckles under the weight of her orgasm. Once she composes herself, I have her sit down and pour herself a drink because now it's Matt's turn and I want her to have a front row seat of her initiation into my stable.
I walk back over to Matt and tell her that she has been a good slave and that now it's her turn to serve me. I take her by the hand and lead her to the bed that still reeks of her wife's cum. I ask her if she is ready to become my proper slave. She seems hesitant at first but looks over at her wife who reassures her that it's okay. She looks me in the eye and says "Yes, Mistress Derek, I am ready and willing to be your sissy boy slave." I look her in the eye, remove the pink collar from my bag that says "Derek's" on it in shiny diamonds and give her yet another deep kiss. This time, her wife gets to sit there and enjoy it.
I grab one of the chairs in the room and bring it behind her. I order her to bend over so I can remove her butt plug. With a sharp wet sound, the plug is out. She breathes a slight sigh of relief but this is short lived as I replace it with one I brought that has a built in vibrator and a radio control unit. I replace her plug with this one and order her to sit down. I grab the rope and tie her to the chair immobilizing her hands and feet. I tell Amy to get back on the bed and sit down.
Once I'm confident she's secure, I stand in front of her to inspect my handiwork. I reach into my bag of goodies and pull out the "back massager" I found at Walgreens. I bend down to lift up Matt's dress and petticoat and pull her panties to the floor revealing her aching clit stick still in its plastic cage. I retrieve the key from Amy and tease Matt with it making her beg for release. "Sorry, darling" I say, "It's not quite time for that. I said it was your turn and it is, but as my slave, you're also my toy and I'll play with you as I see fit."
He replies with another "Yes Mistress Derek" like a good slave. Matt's torment begins with me toying with her nipples through the satin dress she's had on for the last two hours. I alternate between nipples while continuing to kiss her deeply and massage her cock with my stockings. I then get down on my knees and take her chastity covered maleness into my mouth. The cage is soaked with her girl juices and is quite sweet in my mouth.
I glance over at Amy on the bed and she is definitely enjoying the show. I can see her rubbing herself like a mad man through her panties. To further had to his torment, I grab the "back massager" and start rubbing it over her cock and balls while periodically jolting her with the remote butt plug. This causes her cock cage to flood with even more of her tasty girl juice and makes my cock ache even more. Satisfied with my work, I give Matt another kiss this time with his girl juice dancing between our tongues.
I signal Amy for the key and I release Matt from his erotica prison. Her clitty springs to life almost instantaneously. Taking in the sight, I stand in front of her and lift up my leather skirt revealing my satin thong. The front is soaked in precum and my cock is still rock hard. I turn slightly and look at Amy. This is so she can see me pull my cock out and shove it into Matt's mouth. He starts working me like a pro. Even though this is only the second time we've done this that either me or her wife knows about, I'm guessing there's a few Harleys in the parking lot she could suck start.
Satisfied that my cock is wet enough, I order him to stop. I take off my wet satin thong and shove it in his mouth so that the crotch is right on top of his tongue. There's no way for him to not taste my womanly essence. I order Amy to lie on her back again and I remove her panties. I take them and place them over his head so that the gusset is right in his nose. He smells his wife's musk and tasting her male lesbian lover's girly juices all while his clitty is dancing free and being teased by the satin dress and receiving the occasional jolt from the plug.
With Amy and me seeing him like this, we're both so horny that we start going at each other like a pair of horny sluts. I slam my cock into her pussy finally satisfying her long held desire. My cock slides into her with no problems as she's just been a torrent of wetness for the last two hours. My cock is made harder by the fact that this sexual creature before me is finally seeing me as I've always wanted her to see me in all of my dominant feminine glory while her sissy husband watches, unable to do anything but sit there unsatisfied. I pound away at her staring deeply and lovingly into her closed eyes knowing that I am absolutely owning her right now and she's loving all of it. After about ten orgasms for her, I finally blow my hot load into her aching pussy causing her to scream in a way that I know half the hotel must have heard.
As she lies there in a semi-comatose state, I turn my attention back to Matt. Still unsure of what to make of the situation and still in sexual torment from his rope and panty restraints, I lift the mask up and order him to clean my cock up. He does so eagerly. I ask him if he's ready to consummate our relationship and I'm not sure anyone could have said yes to such a question any faster than he did. This isn't the first time I've taken him, but it's the first time as his Mistress. I release his bonds and have him stand up. He's still awkward in the heels, but that will change in time.
I order him to bend over and clean up my lover's cunt. He hungrily sucks the mess out of his wife's pussy and swallows it all down. While he's doing this, I grab the lube out of my bag and slather my already erect clit stick and in one swift motion, shove it up his aching boy cunt. I can't see his face but his breath says it all. I start pumping his ass and he pushes back like a bitch in heat. I tell Amy to slide one of the cock rings in my bag onto him and start sucking his clit. I pound away at him until I'm on the brink of orgasm when I stop and have him and Amy lie on the floor.
Like a couple of seals waiting for a fish, I stroke myself to another massive orgasm and shoot jets of cum onto Amy and Matt's faces which I tell them to lick off of each other, the make out for my amusement.
Because I'm not a selfish lover, I look at Matt and tell her that I didn't forget that she has yet to have release. I order her to stand up as I take her place. I signal Amy to get under Matt's dress with me and we start making out around Matt's clit.
After a while, I tell her to stand up. It's now my turn to return the favor. I hungrily take his cock into my mouth and start sensuously licking his shaft and balls. I nibble a little bit and he reacts like a good girl should. I finally take his cock into my mouth and start sucking on it like the last time only then; he was a lot more nervous. It doesn't take much time for my cock to be hard yet again and I start stroking it while sucking his. I find myself rubbing up against his stockings while taking him all the way down my throat. This sends him over the edge and he blasts his load down my throat while I blow mine on his stockings and shoes.
Like a good slut, I swallow every drop in my mouth and I lick my cum off of her shoes. We then make out swapping each other's juices for the first time as lovers. Satisfied, we all lie down on the bed, none of us bothering to change. Why would we? This is one of the best nights of my life and I was able to share it with my girls. The best part is we all know this is only the beginning.
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with this note attached, it has been posted without my permission.
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