Mistress — you asked me for my biggest fantasy. Here it is.
I check into a nice hotel and get bumped to a suite after the hotel messes up my reservation. I open my suitcase and put away all of my clothing. I take a shower, shave my face (I’ve already had a Brazilian, which was a humiliation in of itself, the girl snickering as she yanked my tender bits smooth). I paint my toenails pink. Mommy won’t let me paint them red. “Red is a a color for women. Pink is a color for girls. You won’t be a woman until a man has fucked you”. I pull the black lace garter around my waist and pull up seamed stockings, making sure they’re straight. This makes me so hard, just doing that. My little penis jutting out. I’m nearly shaking I’m so excited. Just as I’m fastening the last stocking holder a knock comes from the door.
"Room service," says the voice. I look through the peephole and see a young black man in a uniform.
"I didn’t order anything," I say.
"Champagne, sir. Complements of the management. To apologize for the earlier mixup."
"Just a moment," I say. I fetch the plush white terri cloth robe. I answer the door and he wheels the cart, a bottle on ice and a few glasses. He puts them on the side table, and turns to me.
That’s when I realize on the bed is laid out my dress, my heels, my bra, and this young fellow has noticed them. He’s handsome, tall, a nice face. Why is it that I am repulsed by men until I make myself feminine, and then suddenly I’m boy crazy?
Oh well. He’ll probably think I have my wife here, I figure, and those are her clothes. I realize I should tip him. I grab my wallet, and as I’m fishing for a dollar or two I follow his gaze to my feet. There they are, obviously stocking clad and with my painted toes. He has a smile on his face. A snicker, maybe.
I go past the dollars aside and pull out a $20. “Thank you for bringing this up, and for your discretion.”
"I’m sure I don’t know what you’re referring to, sir," he says. "And thank you."
When he’s gone, I’m flushed with the horror of what just happened. I can’t believe it. Almost caught. Part of me wants to back out, check out, go home. But I don’t. I open the bottle and slam a glass of champagne. I open the robe and look down at myself, and wriggle my toes in the stockings. The silky fabric hugging my legs. My little cock swells again.
I do my makeup next, then pull on my bra and my dress and step into my heels. I look at myself in the mirror. Put on a little music and dance. I take a few pictures on my phone, drink some more champagne.
When the whole bottle is nearly done another knock comes at the door, and then to my shock the door just opens. The young man from before comes in, accompanied by another black man about his age, this fellow huskier than the first.
"Don’t be scared," the first one said, closing the door behind him. "We’re not going to do anything here, I just wanted to show my friend. We both have a thing for little white sissies. I just wanted to show him what a little sissy looks like."
"Y-y-you should leave," I say, now scared.
"It’s okay, girly," says the second one. "We’re nice guys. We won’t do anything you don’t want. How about you give us a glass of that champagne, and we can just talk. Just a couple nice men with a nice girl, that’s all." Something about his tone soothed me. Made me believe they didn’t have my worst health in mind.
"Okay," I say. I pour them measures, and we toast each other, but I keep my distance. We chat about the weather. About the hotel and the city. They are nice, smiling and friendly. I loosen up, and maybe it’s the drink, but I feel pretty good.
"I want to dance," says the second one, and he walks right up to me, and puts his arms around me. He pulls me close, and I just decide to go with it. We sway. I lay my head on his shoulder. He’s strong. I feel weak next to him, insignificant. "Mmmm, you’re sexy," he says, and I feel sexy. I feel desirable. Feminine.
He smells good, a little cologne, a little sweat. He presses his whole body against me. And then, he spins me, and pulls me back against him, reaching down and pulls my dress up over my hips to reveal my stiff little penis. “Check this shit out,” he says.
The first guy, still in his uniform, comes right up to me. He takes my face into his hands, and kisses me. It’s a deep, wet kiss, warm and makes me weak in the knees. I take in a stuttering breath, I’m quivering with fear, desire, humiliation. I moan into his mouth.
"Yeah, that’s it," he says. "Told you we could turn this bitch out," he says. He kisses me again, pressing into me from the front, while the second one is pressuring my back, grinding his big hard cock against my ass, pressing me forward, both into the other. He’s got his lips on my neck, my ear, he’s whispering "You’re so sexy. We want you fuck you so bad. Feel how hard you made us?" I do, and it’s transporting me to another place. I feel high on them. I feel like a woman who has coaxed an erection out of a man.
The first presses my shoulder and I go down onto my knees, my dress being held up by my iron erection, leaking precum. They gather in front of me and they unzip their pants. I reach inside and pull out two of the most beautiful cocks I’ve ever seen in my life. “You know what to do, sissy,” the second one says.
They are both so hard, so big. I’ve never looked at a cock up close before, and never seen one besides mine. It’s skinny, the one in my pants, and kind of small. One of these is fat and stubby, but still longer than mine. The other an elegant shaft, dark chocolate brown, with a rounded head shiny from the skin stretching taut.
With an encouraging shove on the back of my head I lick the tip of one, then the other. I open my mouth and, for the first time, allow another man to enter my body. I take the first inch of the first man’s beautiful cock, and I let out another moan. “Shit,” he says, “that feels so fucking good.” I feel him shift, his dick moves deeper into my mouth. But he doesn’t push it oo deep, not yet.
I come clear and go to the other, having to stretch my mouth open so wide to take him. They both smell human, male, sweaty. “Feel my balls,” he says. I do with my other hand, they’re pendulous, soft. I stroke them as he moans. He takes my hair into his hand and pumps my mouth. “She’s got me on the edge.”
"Feed her," the other man says, and the first one does — my mouth flooding with warm ejaculate. It’s mushroomy, male, salty — so thick and warm. I whimper, close my mouth and swallow.
"Damn," he says. "This bitch has it down."
"Back on me," the first man says. I take him into my mouth, and he fucks it like he wants, shoving deeper into my mouth. I block him with my fist so he can’t go too deep and with my hand jerking him and my hot lips on his cock, he pulls back and puts it right on my lips. "Open up," he says, and shoots into my mouth, streams hitting the roof of my mouth, my throat, dripping all over the open cavity, dripping with saliva and semen. I glance up to see the second man snapping pictures with his phone.
Panic must fill my eye, but he smiles. “Don’t worry doll. Nobody will see these but us.”
I stand up, wobbly, and drink some champagne. I go to sit, but the first one grabs my arm. “Oh no, that was just the first act, sweetheart. Get your ass on the bed now.”
Later, I’m laying in bed ravished, scared, alone, unsure of what just happened. They’re dressed now, joking around. The first one pulls something from his coat pocket. A bottle of red nail polish. “Compliments of your wife, you faggot.” They laugh together as they open the door. “Should we put a ‘free blowjobs’ sign on the door? Maybe ‘Takes it up the pussy like a pro?” And then they’re gone, except for the taste of them.
I hope you like my story, Mistress. I’d do anything for you if you’d make it real for me.