Upstairs, Paul walks down the hallway; the carpets appear worn with a garish rose pattern on it typical of the eighties. He stops in front of Room 605 and sets down his suitcase on the floor. Paul’s palms sweat, so the man wipes them on his trousers and then knocks on the door. He knocks so weakly the first time the occupant of the room doesn’t hear. Paul summons his courage and knocks harder.
“Just a minute,” came a woman’s voice from inside the room.
Paul’s face feels hot and burning, his stomach is a knotted ball of tension. The man sweats heavily as he waits for the door to open. Then it does but only a crack, the chain is still on. A beautiful redhead white woman peers through the crack at Paul who only sees a sliver of her face.
“I thought it was you, honey, but a lassie living alone can’t be too canny,” the woman said in a lilting Scottish accent.
She closes the door so she can remove the chain. The door opens. Paul carries his suitcase into Room 605. The woman shuts the door, locks and chains it. She’s a damned good-looking woman, a voluptuous, full-bodied Scottish beauty. The woman is tall, about five foot eight in her bare feet. The high-heels she wears make her even taller than Paul. She’s thirty years old, has long, fiery red hair parted in the middle. It falls in shimmering waves to the center of her back.
It’s the middle of the afternoon, but the woman wears a black satin gown. It fits tightly on her seductive, lush body. Her skin is very white. Her eyes were deep and dark, and her wide-lipped mouth painted with glossy red lipstick. Her face is skillfully made-up. The woman goes back into the center of the room. The satin gown pulled taut across her buttocks, and they roll from side to side under the fabric.
“So you managed to get away this afternoon,” she said and laughed lightly.
“Yes, Mistress Susan, I-I don’t have to be home until dinner,” Paul said his head low.
“That’s good, honey because we got a lot to do this afternoon, you and I.”
Several bottles stand on top of a cabinet. Susan’s room at the hotel has a living room, a bedroom, and a bathroom. There are many fresh flowers in vases, filling the room with sweet perfume. The redhead splashes some whiskey over ice in a glass, and then ads a bit of water then returns to Paul.
“Before we can start having fun, darling, there’s one important little detail to take care of.”
“Yes, yes, of course,” Paul said and fumbles out his wallet and pulls ten hundred pound notes out of it.
“Thanks, darling,” Susan said, taking the money, “Business before pleasure and all that.” She goes into the bedroom, hides the money in a secret place, and returns to the living room holding a leather strap and a length of rope. “Did ya bring your things, honey?”
Paul’s eyes are hot and shiny. “Yes, Mistress Susan.”
The leather strap is fifteen inches long, two inches wide and makes of thick black leather. Susan let it dangle across her thighs. “Have you been a good sissy boi this week, or a bad sissy boi?”
“Bad,” Paul said. His voice seems to have changed. It’s now a breathless, husky whisper, rasping with excitement. “I’ve been very naughty, Mistress.”
“I’m sure of that,” Susan said, rolling her eyes. “And you know what I do to naughty little sissies, don’t you, darling? I punish them. I make them behave.”
Susan stands near Paul. Her gown has a plunging V-neckline. Paul stares at the white tops of her smooth, soft, swelling breasts. Her breasts rise and fall with slow, deep breathing. Her pink nipples, which are sharp and pointed, are only inches away from Paul’s chest. Without warning, Susan slaps his face. The man’s head rocks from the impact of the blow. There’s the meaty smack of flesh against flesh. There’s a bright red mark on his cheek, the imprint of her open hand. His eyes mist with tears. Susan raises her hand again as if to strike him. Paul cries out and cringes, making her laugh. She uses her hand to caress his other cheek, the one she hasn’t hit.
“Poor baby,” Susan croons. “You love it, don’t you?”
“Yes, Mistress, I love it,” Paul said softly.
Paul’s voice still has that soft, quivering quality it had ever since he entered the room. It’s very different from his natural voice, which is deep and rich. The sissy man closes his eyes as Susan strokes his cheek. She toys with his hair, twisting the strands into tiny ringlets. Susan hauls off and slaps his other cheek. Paul, taken by surprise, cries out.
“Ahhhhhhh!”
“You’re looking a bit peaked and pale, so I thought I’d put some color in those cheeks. Wasn’t that a nice thing of me to do?” Choking back a sob, he nods. “Like they say, actions speak louder than words,” Susan said coldly. “If you really want to thank me, you can get down on your knees and kiss my pretty little feet.”
Paul awkwardly kneels. Susan spreads her legs shoulder-width apart and rests her hands on her hips. Paul lowers his face to the top of her right foot. Her shoes have open toes. Paul presses his puckered lips to her toes. The sissy man sticks out his tongue to lick them, but Susan scolds him for taking that liberty.
“I told you to kiss them, not to slobber all over them. What an ill-mannered and ill-trained little boi you are. I can see that I’m going to have to give you what-for and tan your hide before you’re of any use to me.”
“Yes, Mistress.”
The woman makes him kiss her other foot and then commands him to rise and stand.
“The first and most important thing for you to do is to take off those ugly, horrible men’s clothes. They look ridiculous on you. I ought to whip your butt twice as hard for daring to wear such ugly, unbecoming garments. Now get those clothes off, and I mean right now. Move…”
“Yes, Mistress.”
Paul’s trembling hands quickly strip off his clothes. He’s in good condition. His torso is lean, and his belly is flat. The man’s hips are slender, and his buttocks are white, rounded, and boyish. His pubic bush is dark brown and thickly curled. His soft cock is thin and very short, barely a nub on top of his small hairy balls. Paul’s body is lightly hairy.
“So, you don’t wear lingerie under your street clothes, do you? That’s very careful of you, very discreet. I like that.”
“Yes, Mistress,” Paul said meekly.
Susan lifts the suitcase, places it down on a tabletop, and opens it. Frilly feminine garments fill the case. A sweet scent of perfume comes out. The redhead then pulls out a garter belt. It is made of pink lace and has four fat, frilly garters.
“Now, this is more like it,” she said wide-eyed. “A sissy boi like you is so unsuited to regular men’s clothing.”
“Yes, Mistress.”
Susan closes fingers around his small soft dick and squeezes it lightly. It twitches against her fingers. It stiffens and grows, thickening into a full-blooded erection. The sexy woman stares at his four-inch boner and smirks.
“You’ve got it bad, baby. Just talking about it gets your clit all stiff.”
“Yes, Mistress.”
She releases his dick. It’s now fully erect and juts from his hips like a horizontal handle of red flesh that jerks and bobs. Susan pins the garter belt around his waist. As she adjusts the tiny hooks, which hold the belt close, she fondles his soft, smooth buttocks. She squeezes his right buttock, kneading it.
“I feel sorry for your poor ass today, sissy. I’m really going to tear it up, for your own good, of course.”
“Yes, Mistress.”
Paul shivers when he feels the lacy garment against his flesh. Goosebumps rise on his skin. His dicklette jerks in response to her fondling of his ass.
“Let’s see what else you all brought in that traveling bag. Ooh, you’ve gets lots of pretties, don’t you? Here, put these stockings on.”
“Yes, Mistress.”
Paul sits. His bare buttocks rest against the velvet covering of an armchair. Susan hands him a pair of white, rolled nylons. Paul extends his leg, arching his toes with lady-like delicacy. He pulls the stocking on his foot, arranging the toes and the heel in their proper place. Then, slowly and carefully to avoid putting runs in the stocking, he pulls it up his long leg, rolling it over his knee and up his thigh. His trembling fingers slip the metal garter tab over the stocking top, pinning it into place. Susan sips her drink and watches him.
Paul utterly absorbed now, pulls on the second stocking. He stands making a bizarre image, with his small erect dick and his tiny balls framed by the frilly garter belt, the fat garters, and the white stocking tops. Susan approves of the transformation with a nod. She takes a pair of panties from the suitcase, spreads them in her hands and dangles them in front of Paul’s hot, sweating face. The panties are pink satin, cut full, with lots of ribbons and lace.
“Here, put these on,” Susan said. “Although it’s really a waste of time since they’re only going to come down again soon enough.”
Paul shivers as he steps into the panties and pulls them up his legs. Like the stockings and garter belt, the panties are in Paul’s exact size. The panties would’ve fit him perfectly, except for the way that his hard dicklette tents them in the crotch, stretching them out of shape. Susan fondles his clit through the panties.
“That nasty clit of yours spoils the look of your pretty panties, Paula. I’ll have to do something about that, but I believe I’ll dress you before anything else.”
Susan put a bra on him. The bra is white, with lacy cups. The cups have foam rubber inserts, which give the illusion of small but firm breasts. A slight covering of hair is on Paul’s chest. Susan frowns and pulls on the tiny hairs until he cries out in pain.
“You’d look a hell of a lot more convincing if your body was shaved as smooth as a billiard ball, darling,” Susan said coldly.
“You know that I can’t do that, Mistress,” Paul whines. “My wife would notice something like that instantly and ask questions.”
“Just tell her you get a skin rash and your doctor ordered you to shave clean,” Susan suggests.
“It won’t work. Caroline’s a very bright woman, and she’ll surely check with the doctor.” Paul frowns. “Sometimes I think she suspects me now.”
“You know, I feel sorry for you, Paula, leading a double life like this,” Susan said warmly. “Listen, why don’t you just go to your wife and confess you’re a small dick sissy cross-dresser? She might surprise you.”
“I couldn’t…” Paul said blushing, “I just couldn’t. I wouldn’t know how to start.”
“Just sit down with her and explain you have certain desires. Tell her nothing turns you on like being dressed and used like a woman,” Susan said. “Hell, you never know. It might even turn her on.”
“Caroline would never understand…” Paul said, shaking. “She used to be a wild girl when she was younger, running around all night. Now she’s married and the mother of two kids. She just couldn’t relate to this.”
“Suit yourself,” Susan said with a shrug. “It’s just a suggestion. Nevertheless, you ought to think about it. After all, what are you going to do? Spend the rest of your life sneaking around, searching for dommes who’ll dress and punish you, and treat you like a baby dick sissy girl in every way?”
“I might have to do just that,” Paul said and grimaces. “Please, can we talk about something else, Mistress?”
“Surely, we can talk about the ass-whipping I’m going to give you. I just wanted to give you some good advice. But you’re too silly to follow it, which is just one more reason why you should have that bottom of yours whipped raw.” Susan holds a length of rope, the thin kind often uses for clotheslines. “I’m through talking, Paula. It’s time for your punishment. Since I know what a little baby dick sissy wimp you are I’m gonna tie you after you put your pretty shoes on.”
*****
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