Harland was trapped. Wearing his sister's clothes, even if in secret, had been no big deal to him, but she'd caught him, and it had been a big deal to her; or, so he'd thought. He almost cried when she laughed at him, but he'd held himself in check and waited to see what she would do. Harland had not been well schooled in the way of the teen female mind; he was about to be. She had indeed laughed herself silly and had been on the verge of going downstairs to tell the whole family about it; he'd barely been able to stop her; he'd had to beg on his knees. How long she'd keep it to herself he couldn't tell. Caria, his eighteen year-old twin, had a big mouth even for a teenage girl. It was going to cost him to keep her from telling on himâ€”a lot.
It was a three day weekend. It was raining and the two of them were at home alone until the following Monday. Parents and twenty-two year old brother Nathaniel were away at their aunt's house for a barbecue that had certainly been rained out, he thought; but they'd stay there anyway; it was a hundred miles to the north; they'd stay and visit. This was his chance to make it right with Caria. He wandered into the den where she was sucking on a popsicle and watching some mindless soap opera.
He sat down on the sofa opposite the big recliner where she had found a perch. She eyed him with the smartaleck smile that was her trademark. She'd always seemed so mature to him.
"Your clothes don't match," she said. "Wanna wear something of mine?"
His stomach churned. "Very funny," he said weakly.
"I thought so," she said. "It was a genuine offer. Do you want to wear something of mine: a house dress or something? I could probably find a pair of panties that would fit you if you'd like. Yes, panties, for that tight little twat of yours." She began to laugh hysterically.
"Cariaâ€”please!" He sounded like a whining little boy, he knew, but he couldn't risk upsetting her by demanding that she stop. She had him and she knew it.
"Please what?" she asked too pleasantly. "You wear my clothes secretly. Why don't you just wear them openly? I mean no one is around but us, and I know your secret. So, just accept my offer and get out of those awful no-match rags you always wear in public and get into something nice."
She sounded serious. She sounded odd. Terror seized him and shut down any thoughts that he might otherwise have had. He must have looked terrified too. Her tone changed. Her next words sounded almost sympathetic.
"Look Harland, I know you want to talk to me. You are afraid that I might tell on you. Well, I might. I might not, but I might. If I do, you are ruined; you'll never live it down. Dad will probably strap the hide off of you unless he is too embarrassed about having a sissy boy for a son to even get near you. Mom will probably put you into therapy or something. But no matter what happens, life as you know it would be over for sure."
She paused. He couldn't bring himself to look her in the eyes. He stared at the floor riven with fear and desperation. "What can I do?" he whispered in a husky voice.
"Do? Well, change your clothes like I said," she said. "I know you want to. Who knows, maybe I won't tell if you do. So, what do you say?"
He looked at her with puppy-dog eyes. "You mean if I get dressedâ€”inâ€”your stuffâ€”you won't tell?"
He looked so forlorn to her. "I said maybe. If you do what I say, if you don't give me a hard time, if I think you'll be the obedient little brother from now on; Well, I might think it would be to my advantage to keep your little secret."
"I don't understand?"
"Yes you do. I want you to be at my beck and call. You're going to be my little sissy boy, my slave really. Have any problem with that?"
"Then you have until mom and dad get back to find out what the alternative is going to be like. My offer is good for the next five minutes. After that, no deal." She went back to watching her show.
He sat stock still. He had to think. He couldn't think. He was trapped, utterly trapped. The choices were both horrible. Maybe if he took her offer she'd grow bored with the game and let him off. Sooner or later she'd let him off; he had to hope she would; it was his only chance. "Okay." He didn't look up; the carpet still held it's fascination for him.
"I'll do what you want."
"And what's that?" She was enjoying the game now. The longer he stalled the better she liked it.
His face was Confederate gray with despair. "I'll do as you say. I will be your slave."
She eased back in the recliner. She eyed him. The popsicle had long since disappeared down her esophagus; she chewed on the stick now. She was wearing a tight pair of black hip-huggers and a white half shirt that would have revealed the bottoms of her braless A-cup boobs if anyone had stooped over and looked up. "Good. I am going to like having
a sissy boy slave. I think we'll have some fun together. Just remember, I'm the boss. Your job is to obey. Am I clear?"
"Okay, strip yourself naked and don't waste any time."
He had not expected her to say anything like this. "Butâ€”butâ€”Caria! I'd be exposed in front of you! You're my sister. I'd be naked in front of you! Please gawd! Don't make me be naked in front of you. I'll wear the clothes. Anything. But not..."
"Yes. You're going to be naked in front of me. Frankly I'm curious as to just what your dick is going to look like.
"You're a slave Harland. I own you. You have no rights that I do not approve of. Get your stinky clothes off and get naked, and do it immediately."
He hadn't really had any idea what to expect. He stood up from his couch slowly and began to unbutton his shirt. He let it drop to the floor. His eyes pleaded with her to let him off, but he knew her. Caria was a hard hearted sister; she always had been. His shoes and jeans were next. He hesitated at pushing down his under pants, but a raised eyebrow from her made him put his thumbs into the waistband and begin pushing them down toward his knees, slowly.
He was stark naked. His stiff and pulsating penis pointed six and half inches into the air almost straight up from his ball sac. Caria smiled critically at her brother's tool and his balls; she noted with interest that his balls had sparse hairs growing out from them. She had seen a number of naked boys and played with them, and they with her; Harland stacked up well with all of them. She'd be investigating her property minutely very shortly. "Hmm. You're not as much of a pipsqueak as I thought you'd be, little sissy boy. We have a nice fat thingy there don't we. And it's kinda long too. I'm gonna enjoy this. Oh yes, I am going to enjoy this," she said almost too quietly, almost to herself.
She stood and walked toward the stairs. Turning, she looked at her little brother and smiled sympathetically. "Go stand with your face in the corner until I come back."
"Harland, You don't get it. You are being punished. Sneaking into my room. Taking my things. Playing your little games. The thing is, if you had asked me. Had you been straight with me, I wouldn't have mindedâ€”wellâ€”after I got over the initial shock. But, the sneaking around pissed me off; your bad luck. You will do as I say until I feel you have paid for what you did."
She hadn't known about his little games until she had seen him preening himself after school one day when the house should have been deserted except for himself. She'd come home early, watched for a little while and then confronted him. She had seen the possibilities from the first moment. He was such a wimp; she'd be able to manipulate him at will.
"Yes, Harland, Oh. And Harland, if you displease me, I will spank you with a switch; just like dad does."
Harland paled. He knew Caria would find a pretext to use the switch. She was already thinking about it. He was had. He knew it. The only good thing was that she could not possibly make it hurt as much as his father could. She was a girl and she did not even top one hundred pounds.
She disappeared up the stairs. He took his place in the corner with his hands at his sides. He was naked, he was alone with his thoughts, and he had raging erection he sincerely wished he could control. He thought about masturbating, but he was certain that that would earn him the switch.
His sister? What did she want from him? She was going to play with him; he was sure of that. She did turn him on, he was ashamed to admit, but he felt strange about it. What if she used himâ€”sexually? He feared her, but she aroused him. He heard her return, but he did not turn around immediately; he waited for her to tell him to.
"Turn around Harland."
What met his vision "was" a vision. She was in a light yellow sheath dress, high heels, her hair was in a ponytail, and she was clearly wearing no bra! And there was something else; she smelled wonderful.
She didn't have to bully him; the way she was right at that moment; he would have volunteered to be her slave. On an impulse he dropped to his knees in front of her. It evidently pleased her because she smiled a truly radiant smile.
"Very good, Harland. So, you like the way I look. Well you're going to be just as pretty after I'm through with you; I have some ideas."
"Ideas?" he said as he gazed up at her.
"Uh-huh. First things first. We're going to shave off all of your male hair except for the hair on your head and your eyebrows. Can't have a little sissy boy with too much body hair now can we."
Leading him up stairs she pushed him into the bathroom where a scented bath had already been drawn for him. She coaxed him into it and handed him a pink razor. "Shave," she commanded him. After she had depilated the rest of his body hair, she dried him, took him from the tub, and sat him down at her vanity. She began to put his longish hair up in curlers.
Having finished with his hair, she turned her attention next to his face: eye liner, mascara, lipstick, a touch of pink to his cheeks and she was ready to dress him.
Before she put him in his feminine clothes, she crooked a finger at him and beckoned him with it to come to her. She produced an unusual looking thing, device. It looked like a bikini bathing suit, but it had a hallow tube in the front. "This is your chastity belt, Harland. You put it on like underpants, but your penis goes into the sheath there and must always point down. It will allow you to go peepeeâ€”sitting, like a girlâ€”but you cannot get an erection while you are wearing it. I bought it, and not without some embarrassment, when I first figured out how I was going to discipline you. You like?" she said impishly.
"Yes. I like it, Caria. I like it if you like it." He was totally pussywhipped now and they both knew it. "Do I have to wear it all of the time?"
"I'll tell you when you can take it off. I just don't want you playing with yourself. I might want to use you and you won't be able to perform if you play with yourself.
Yes, if you're good, I might let you fuck me or something. And if you please me, it might get to be regular. If not, I will punish you, and then you will learn how to please me." She strode away from him toward the coffee table in front of the couch. Oh, I do like being the boss!" she said with obvious relish.
He started to protest. She raised her hand to silence him. "Oh, I might not be very experienced about this stuff, but I know about boys and their ways; I've seen lots of boys' thingies."
Harland's face betrayed his shock "You've done stuff with boys!"
"Yes, silly. Of course. probably not much of what you're thinking though. Still, I've seen plenty of cocks and I have wants that I want to have satisfied, and maybe you can be useful that way; we'll see. Anyway, you won't be jacking off any time soon, not wearing this you won't." She helped him slip on the thing that would imprison his cock. He felt her snap or lock something behind him. He knew it had to be the locking device that would keep him chaste until she thought best.
It bothered him quite a lot that she would not let him relieve himself by masturbating. He was bound to be half crazy with desire by the time she released him.
From the coffee table she gathered the skirt and panties he would have to wear while she was in control. He didn't mind wearing the female clothes she had selected; he'd always liked that. He did mind not having any say in the matter; it was a little scary. He was, he realized, determined to be obedient. What worried him; however, was the fact that he seemed to be falling in love with his sister. She could do anything she wanted to him and he would kiss her feet for it. Nevertheless, it was still a little scary.
"My! don't you look sexy in your panties. Now, the skirt sissy boy. That's right, it zips up the side. Doesn't it feel nice and airy underneath. We girls really like that. It makes us feel so vulnerable, and yet so powerful; we know every boy who sees us in a skirt wants to
get their stinky hands under it. You do too don't you little girly-boy. You do, don't you." She was laughing at him and he felt strangely freeâ€”excited.
"Yes," he said softly, almost humbly. "I have always wanted to feel under a girl's skirt, butâ€” but..."
"But you've never had the nerve." She laughed uncontrollably, almost choking in the process. Harland was so humiliated his penis shrank back into his body like a snail back into its shell. "Well, little brother, today's your lucky day. I'm gonna take your cherry." She began to release his hair from the restrictive curlers. His hair fell free, tousled and beautiful. "Looks good," she commented.
Harland didn't comprehend what she had said immediately. Then it dawned on him. She was going to let him screw her! "You mean..."
"Yes, Harland, you're getting your first piece of ass today, and it's going to be your very own sisterâ€”me. Come here. Get down on your knees," she commanded him. "Yes, that's right. Now, you can put your hand under my dressâ€”slowly. That's right, Harland. Feel up your sister."
His hands caressed her thighs inching their way up to the cleft in her pubis. She spread her legs slightly so his fingertips could touch her slit through her panties. Harland was sweating profusely. He was shaking. He felt giddy. She pulled back from him; he had never felt so deprived. He needed to feel her some more, but she was denying him.
"But, Harland, I'm doing it for me not for you. So, you will be treated to your first serious spanking beforehand. That oughta keep you from cumming too soon."
Harland was shell-shocked. He didn't care if she beat him within an inch of his life. He was going to get to push his cock into her hole, her outrageously beautiful hole, and that was all he could focus on. Caria smiled benignly at him.
"I'm going to give you a serious dose of the switch," she said calmly.
"Yes. And thank you, Caria. I will always serve you if you let me do you no matter how hard my spankings are. But couldn't I feel you some more first?"
"No." The sincerity of his avowal delighted her. He had a nice cock. Harland was only five foot two. He had an almost frail looking body, but his cock was thick and fairly long, maybe six inches. How many nights had she had to do herself because there were no cocks around to do her. She wasn't a slut after all. She couldn't just spread her legs for every boy in town. She had let a dozen boys feel her up. And one or two even got to suck her titties; she'd given each of them a yeoman-like blow job. But that had been it, except for one guy.
She had let Harry Rathstone have her cherry, but she had been younger then, and she didn't know very much. Not like now. She knew the game now. And, now she had the outlet she needed. If she handled it right, her brother would be all she would need to assuage her lust. And he liked to play dress up. Maybe down the line she could find a boy to fuck Harland. Gawd! how she'd love to watch that; especially if she was getting it at the same time. It was something to think about. Yes, she determined: Harland was going to get a royal screwing. Sooner or later Harland would feel a boy's dick pushing its way up his nether hole. She giggled.
He was naked again; she'd stripped him. She wanted him that way for his punishment. She had changed her mind and had substituted a hair brush for the switch she had intended to use; she wanted him over her knee with his penis rubbing her leg through her dress. He stood beside her now. She was beautiful in her yellow sheath, her tawny hair pulled back in a girlish ponytail. She smelled like a girl smells, and it intoxicated him. He was actually looking forward to his spanking. She was explaining now how he was going to get it.
"Do you understand, Harland?"
"Yes, Caria, I understand. If I struggle too much or try to escape from your lap, I will not be allowed to have you afterward. I understand."
She reached out and touched his penis for the first time. It jerked spasmodically at the feel of her cool fingers. She stroked it and she felt it harden. It would soften in a few minutes she was sure, but for the moment it was steel-stiff. She would have to decide what position
she would assume when he took her. It was a delicious decision. Maybe missionary the first timeâ€”maybe doggie style. Yes, doggie style. She wanted him to master her; that was a girl's most precious moment. When she was most submissive to the male of the species. At all other times she would be in control, but for those moments when he was ramming his
cock into her, she was the submissive female being taken by the strong, masterful male. She almost licked her chops; she did lick her lips; Harland noticed and wanted to kiss those lipsâ€”badly.
"Lower yourself over my knees Harland; it is time for your punishment." He followed her directive. His cock began shrinking again; a fear took hold of him. Not a fear of his spanking; he wanted it; it was fear of not being able to take the sting of the hairbrush and losing his opportunity to have his sister under him. He gnashed his teeth.
Caria lightly traced the dark crack between his buttocks with her finger. He jerked at the tickling sensation. She spread his buns apart and gazed at his rear door; it was pink, she was surprised to see. She wondered if it would be painful for him to have another boy ram his dick inside of him. He liked playing the girl. Would he also like being treated like a girlâ€” by a boy? The two were not by any means the same thing; this she knew. But, brought along slowly, she was sure that she could convert her pantywaist brother into a screaming nympho.
Caria raised the hardwood hairbrush high over him and brought it down on the virgin flesh of her male slave. He sucked in air feverishly and jerked like he'd gotten an electric shock. His toes danced madly on the floor and his body stretched into wild, outrageous positions as it tried to compensate for the frightful agony being visited upon his bottom. He shook and mooed and cried and hissed trying everything short of screaming to ease his distress. Caria continued to paddle him relentlessly though at a measured pace. She wasn't trying to kill him, but she was setting the tone for future punishments; he would remember this one and do his best to obey her without question. That was what she was really afterâ€”unquestioning obedience. Harland's buttocks were on fire; he was sure she had drawn blood, but it was only the heat of the blood rushing to the surface of his tortured flesh. His cock had disappeared. Could someone have seen it, the front of his pubis, he would have seemed a female.
She comforted him after she had punished him. He had been good she said. He had taken his medicine and had not struggled unduly. He would get his reward.
For his part Harland was torn by desire for the beautiful Caria on one side, and the searing heat consuming is buns on the other. Caria was seated beside him massaging his upturned flaming flesh with cold cream. After a little while the fire seemed to grow less acute. His penis was regaining some of its majesty. Caria rose and stood a few feet away from him. She began disrobing. When she bent to push her panties down, he lost sight of her charms for a brief moment. When she straightened up, what he saw stunned him. She was the most incredible creature he had ever imagined and more. The nipples of her small titties were pointing straight out. Her pussy lips were involved in a mass of dark brown hair that was unutterably sensual. Her hair, her face, her makeup, her smell; she "was" woman.