Sissifying a hard body was more than fun. It made me happy. I loved turning my fit fantasy men into sissies on the down-low. On the hotel room desk, I placed a selection of new cosmetics. Cherry pink lipstick, matte eyeshadows, a simple mascara, and blush. The essentials for the transformation.
He stood between the toilet and the tub in the dress and stockings. Baby had put himself in a corner. Mark looked at his chiseled features under the curly blond wig and smiled. It wasn’t a smile of joy. It’s what relief looks like. “Thank you, Mistress,” shot out of his mouth when he saw me in the door. He was quick to comply and anxious to please. While I enjoyed the compliance, a little resistance would be nice. The multi layered skirt was short, just to the edge of his ass. He had picked it out and had it delivered to my house. The only condition on the play was I keep his things with me.
“Bend over and show me your ass.” I fought the urge to use the common courtesy of please and thank you. Mark hesitated. He placed his hands on the back of the toile and straddled the basin. I dipped the anal plug in the tub of lubricant. I amplified his sense of vulnerability with silence, I tickled and careless his ass and asshole under the satin panties, the satin of the skirt rustled as I used my nails on the fine hairs at the edges and pressed my thumb to his asshole. Only when a moan and body shutter indicated the intensity of his arousal did I proceed. I order him to masturbate as I lift his skirt, his arousal makes insertion easier. I knew the large plug would stretch his asshole and make him all to aware of it with a playful smack on the ass and a “good boy.” He stands upright and faces me. His 6′ 1″ frame contained in satin ribbons and bows pleased me. He is very beautiful, yet venerable. My nipples ached they were so erect.
“Come with me.” In the bedroom, I had pushed the table aside. There was ample space on the floor. “If you are going to be my dolly, you have to know how to play the sissy games girls play. I grab a small container, sit on the floor, and motion for Mark to join me. Matter-of-factly I say, “We will start with something simple.” Mark fusses with adjusting himself to sit cross-legged in front of me. I smirk with amusement as he struggles to be graceful. Good girls learn early on to be seen and not heard. I pass him a ball and six jacks. I show him how to bounce a ball and pick up the jacks.
He fumbles the ball and scrambles after it too many times to count. He is visibly flustered. I simply tell him to start again. Once he can bounce the ball and pick up a jack, I reward him with a “good girl” and a sweet kiss on the forehead. He blushes and waits.
I continue to push his expectations to the side and offer another juvenile pass time. “Good sissies know how to play nicely and know how to play girlie games.” I teach him a clapping game, Miss Mary Mac. He is agitated. I smack his fingers when he makes a mistake and remind him that 6-year-old girls can do this. His face is flushed and the wig is sticking to him. He stumbles, but masters the rhythm and the words, I’m satisfied.
“Are you having fun? If you are going to be a true sissy, we need to get you ready, that rough face is just not going to do at all. Crawl to the chair and wait. Don’t touch anything.”
I sit in the chair between the desk and the window with a cold glass of water. “Go ahead, make yourself pretty for me.”
I watch as he examines the items laid before him. He touches each item gingerly, not quite sure where to start.
“Start with the eye shadow. “
“Yes, Mistress.” It’s odd. I suddenly realize I don’t need to be called Mistress, his desire to please and actions demonstrate his obedience.
He is tentative in opening and applying the color. I lean against the desk and move a curl to the side. His fingers are too large for the small sponge tip applicator. He reaches to adjust the desk lamp and pause, “May I, Mistress?” I nod in approval and approach him. I slide the cosmetic to the side and sit on the desk facing him. The dildo makes a somewhat awkward bulge in my jeans. Adjusting my crotch, I settle in front of him. Placing a finger under Mark’s chin, I apply an excessive amount of eyeshadow, mascara, and blush to my little slut. I pluck a few stray eyebrows, just to enhance the experience. “The price of beauty sweet-heart,” I quip. The final touch is a deep red lipstick. I lean to the side so he can see his reflection. He is my doll, my dress-up barbie. The makeup is over the top, but there a change in his features. With the blond waves and the makeup s/he is my little slut.
“Undo my pants,” I order. S/he does as she’s told. “You know what to do,” I motion to the dildo in my strap on. I lean back on the desk, freeing up my pelvis to move. I raise my ass so s/he can pull my jeans down and free to cock. S/he is hesitant.
“Be a good slut and put that cherry mouth to good use.” My tone is flat and indifferent. S/he bends forward and takes the tip into her mouth. I place my hand on the top of her head, not pushing, but encouraging a rhythm. Words of praise and pleasure for Mark’s efforts are rewarded. S/he is on task taking the silicon cock deeper into his throat, gagging and drooling saliva. I’m wet from his attention but show no sign of pleasure. He licks and sucks the cock while I rock my hips, I slowly edge forward, pushing his chair back until I can stand. Marks mascara is running a little from watery eyes. His lipstick is smeared.
“Look at yourself, a slutty mess, and we’re just getting started,” I say as I use his skirt to draw him close. “Present yourself for inspection.” Mark interlaces his fingers behind his neck and stands with his legs apart.
Moving the panties to the side reminds my sissy that she is still a man. “You really can’t control yourself, can you?” I stroke his cock slowly as I speak. I intensify the stroking until he can no longer be silent. I am close, my words are stern, but softly spoken. I remind him of his flaws, and I how disappointed I am with him. “Where is all the enthusiasm I saw when we met and talked about you wanting to serve me?” I query. My stroking has him driven to distraction. He doesn’t answer. I stop mid-stroke.
“I’m bored; you bore me.” I walk to the window abandoning him and the intimate moment. He is exposed.
“I’m sorry, Mistress,” he mumbles. And he goes to cover himself.
I watch his reflection, waiting until he squirms, one shoulder drops, he thinks it’s done. I turn, “are you ok? Are we still green?”
“Yes, Mistress.” He is short on words, but his body language is relaxed and comfortable.
I retrieve a small leather-covered paddle and a silicone cock ring without prompting Mark turns and lifts his skirt. Never wanting to miss an opportunity, I smack his ass with my bare hand until the skin is pinked up.
“Thank you, Mistress.”
“Good, Sissy, that was enjoyable, but I wanted your cock.” I spit in my hand and wet him so I can slide the ring on. “Are we green?” He nods but doesn’t speak. “I think it’s time you demonstrate your maid skills. I would like a cup of tea, one milk, one sugar. And while I am enjoying my tea, you will be my footstool.”
I picked up my phone and gave it a passing glance while watching my sissy-maid attempt to be elegant. S/he presented me with my tea and positioned himself on all fours. As my footstool, he would learn patience. I place my feet on his back and sip the tea. I trace along his back, down over his ass, and along his stomach with my foot. “Well, you have a little think about. What you could have done wrong while I finish this lovely tea, even if it is too hot.” Ensuring he is still erect. I read blurbs on my phone and turned on my music. I rise and leave my footstool.
“Do you know how many mistakes you just made?”
I return to the window. The glass is icy. The cold on my back is refreshing.
“Ok, Slut! Let’s put that manly strength to use. The table needs to be moved. I want space in front of the window.”
“Yes, Mistress” he says indifferently.
Sternly I spit at him, “do show some enthusiasm, you waste of air. Get my strap, hands on the dresser, and drop those panties.”
His humiliation and embarrassment were evident with the hesitation of bringing his panties to his knees and lifting his skirt. I checked that the color of his cock was still right. I slide my icy fingers along his balls and around his engorged member. He moans in pleasure at the attention. Jizz seeps as I pump. I use the lubrication to remove the cock ring. I have been edging him for hours. I check that the cup I took from the bathroom earlier is on the table.
His body is quivering from the intense attention. I stop. Move around, to look into his face. “Now your punishment for not using please and thank you, making my tea too hot and not cleaning the bathroom up after you used it. There will be 15 straps on your ass, 15 on your thighs, I want a nice red behind to play with. Count for me. If you cum while I am punishing, you. I will stop and you will have to put on your street clothes and go home. Tell me, you understand.”
“I understand.” I smack him across the face. “You worm, who are speaking to?”
“I’m sorry Mistress, I forgot myself. I am unworthy.” He drops to the floor, placing his face on the ground, arms forward, and ass in the air. He moves so quickly his skirt leaves his ass exposed, he wiggles his ass, trying to get it to fall into place. His panties had dropped to his ankles when he prostrated himself. I step on his fingers, watching his face carefully. I press until his face winces.
Without prompting, Mark’s words are measured and careful, “thank you, Mistress, thank you for teaching me. I am not worthy.”
I go to the bathroom and get his underwear. He is still on the floor with his ass in the air, I grab his hair and bring him to the kneeling position.
The underwear is balled up in my hand. I intentionally don’t speak. I hold them in his face until he opens his mouth. I wait until his mouth is wide, and I stuff them it.
“Stop wasting my time, Assume the position. You panty waste.” I retrieve my strap from the table. Without warning, I deliver the first strike across his thighs. He counts one loud and clear. I flick his skirt up, caressing his ass and plug. I tap his legs to open wider, so his balls hang free, and I can see the ass plug. I deliver the strap at changing speed and intensity of each impact. At the halfway point, I take his penis in hand and stroke his engorged cock. The marks cover his thighs and ass thoroughly.
“Do you want to cum?”
“Yes, Mistress, please, Mistress.”
I step away. “Let’s try that response again.”
He is confused.
“When do you get to cum?” I ask from behind him.
A light bulb goes off. “When you say so,” he says brightly.
“Good. Take off the dress and stand in front of the window.” He did as I asked, carefully hanging the dress back in the closet. I opt not to rush him at this point. As I begin to lube my strap-on, I speak, “now you see that cup on the table, I am going to fuck you in the ass, and when you cum, you cum into that cup.”
I give him the lube to stroke my dildo, I tweak and pinch his nipples. His eyes closed, and his breathing becomes ragged. At the window, I arrange him as though he was on a St. Andrew’s cross, remove the ass plug and toss it onto a towel I had placed on the floor earlier in the day. I remind him, that he is on display for the whole city as I grease his asshole and load the tip of the cock with lube before I slowly fuck his ass. I have him hold his ass cheeks apart and guide the cock slowly, feeling his ass release and take it all. I keep it buried, pressing my body towards his back. His chest presses into the window have the desired effect of shaking his senses. The thrill of being on display tangled with the icy window against his chest amuses me. I increase the rhythm as he settles back on my cock. The control is invigorating, his inhibition is intoxicating. Words and sound of surrender tumble from his mouth His pleasure is palpable. I barely need to move; he’s writhing and doing all the work. It’s like a standing reverse cowboy. When I am satisfied, and he hasn’t lost his erection, I pull out and leave him there. I pass him the cup.
“You can cum in the cup.” Without hesitation, he masturbates and comes almost immediately. He squeezes every drop into the cup.
“Drink it” is all I say without inflection. He throws it back like a tequila shot. Mark is spent, his makeup has run, and his wig is disheveled, he is naked, and his cock is becoming flaccid.
I sit in the chair; my shirt is damp and clings to my erect nipples. I rub and caress them as I watch him try and figure out if he should stay or come to me. He kneels in front of me and says nothing.
“What does my little slut want? I ask.
He motions to my chest. He leans against my chest, and I pull off the wig. He settles in as my nails gently scratch his head. We make small talk. He strokes the curve of my breast. I close my eyes. My mind is quiet. The session is done.