Rich had endured yet another bad date. Twenty years old and he couldn't close the deal or even secure a second outing. He didn't understand why. He was handsome, in good shape, and a nice, sensitive young man. Frustrated and feeling less than a man, Rich stormed upstairs to his room, locked the door, and obeyed his sulking, sensitive heart, submerging deeply into his feminine persona. I'm not much of a man anyway, he berated himself as he stripped out of his clothes and pulled on a pair of peach satin panties from the secret chest under his bed. I might as well be a pretty girl.

Warm tears welled in his big, blue eyes as he dolled himself up, feeling a strange mix of misery and excitement. He donned white thigh-high stockings and an unpadded peach-colored bralette of satin, matching his panties. His penis reacted to the silky-smooth feeling of submerging headlong into his feminine persona. His eyelids still hot, he slipped on his small, multicolored robe. Beginning to enjoy the femininity blossoming within, he reached for his secret makeup pouch and applied lip gloss, mascara, and blush. Watching himself transform into a cutie made him nervous, but pulled him out of his misery and into a delicious, vulnerable kind of sweetness.

He felt tiny, pretty, dainty, and safe. Snug in his pretty persona, Rich got into bed and sank slowly toward sleep, the night's failure still playing in his mind. He wished he could talk to his sister about it but couldn't risk being seen en femme by his parents. Patricia had already known about his proclivity, having walked in on him once by mistake, and then several times on purpose. She took to making fun of him, talking to him like a little girl. Though it was very humiliating, for some odd reason he didn't understand, Rich liked it when she teased him. He liked it even more when she touched his lingerie in various places on his body and facetiously complimented him.

I wish Patricia would come into my room and just hold me. Make me the little spoon and caress me all over. It would feel so good to have her stroke hair and say, 'Everything's gonna be okay sweetheart.' Oh if she would just put her hands on my butt and pat me. Mmm, that would be perfect. Rich fell into a serene slumber dreaming of his sister's touch.

The next morning, Rich was awoken by the familiar sound of someone trying to get into his room bypassing the lock. Patricia, his little sister, was probably using a card to sneak into his room again. Lying on his tummy, he turned his head to look past the foot of the bed at the door just as Patricia entered. Just then he remembered what he had been wearing, and his nerves immediately began to buzz.

"Trish, what the hell? Get out!" He knew she wouldn't leave and he didn't want her to. He secretly wished she would do what she'd done last time she caught him in bed wearing feminine lingerie.

"No, I don't think I will," she sang jovially coming toward the bed. She stopped short and gasped. "Is-is that mascara!? And blush!? Lemme see!" Rich growled and covered his face with his blanket only forcing his annoying little sister to peel it away, down past his shoulders. She gasped giddily when she saw thin, peach shoulder straps. "And a bra! Does that mean you're wearing panties? I wanna see, I wanna see!" She pulled the covers down her brother's body as he tried to keep a one-haded grip on his bedding. "Don't be shy, Cassie Cutie!"

"Don't call me that," Rich said weakly as he eyed his little sister. She was wearing a T-shirt and probably panties. He couldn't see due to the length of the shirt that just barely passed her middle. He took in the enticing sight of her pudgy little body, perfectly plump thighs, and bounteous breasts. She never walked around the house like this unless their parents were away. Rich wondered why.

"If you don't want people calling you a cutie, you should dress so cute," she shrugged, tentatively touching his panties I'm back. The first time Patricia had touched Rich's ass in panties, he tried with all his might to hate it, reacting as if he did. But he instantly fell in love with that feeling - of a girl seeing his sensitive side and being inexplicably drawn to it. And the physical feel was exquisite.

"Urgh," Rich growled, "You're such a little weirdo."

"Says the boy in makeup, bra, and panties." She quickly grew reacquainted with her brother's booty, rubbing it through the soft fabric. "You have the best little bubble butt, Cassie. A perfect handful. I bet it makes all the girls jealous and turns all the boys on."

It felt extraordinarily good to be treated in this way. His sister's words were like honey in his ears and her hands were like the wings of an angel. His skin prickled, absorbing the heavenly sensations. But he couldn't let her know that. He had to protest. If only a little.

"Touching your own brother like this is like really strange behavior, you know? Especially since you say you're a lesbian." She stopped her rubbing but kept her hands on her brother's ass.

"I am a lesbian, Cassie, sweetie," she said giggling and trying with the waistband of Rich's panties. "That's why I like this pretty, girly butt in these sweet-looking little panties. You're so adorable." She slowly began to pull Rich's panties down.

"What are you doing!?" he asked, half panicked.

"I wanna see it," Patricia said, continuing to pull her brother's panties just below the bow of his supple ass. She giggled. "It's so cute, Cassie. Don't be shy about it. You know what they say, 'If you got it, flaunt it.'"

"You're insane," Rich said but did not move. Patricia started to softly caress his ass again, the skin-to-skin contact unbelievably precious to Rich. After about a minute of absolute bliss, causing his cock to go fully erect underneath him, Patricia stopped. When Rich looked back toward his little sister, she was removing her t-shirt, a huge smile spread across her pretty, round face as she carefully pulled the top through her long, ink-black hair. She was wearing a royal blue bra and green panties.

"What the hell are you doing?" Rich asked incredulously, eating his little sister's delicious body with his famished eyes.

"Well, I can't let you be the only comfortable one, Cassie girl. That wouldn't be fair. Don't you want us both comfy for our sleepover?"

"Whatever," Rich grumbled, looking away from his sexy sister to the mirror, covertly eying her plump ass and portly thighs. She was wearing a pair of green gingham cheeky panties, making her rump look extra enticing. He watched as Trish climbed onto his bed and straddled his thighs, returning her sweaty palms to his rounded derriere. He allowed a comfortable sigh.

"There you go, baby girl. Just enjoy it. Let mommy take care of you, sweetheart."

Rich had never felt more like a sexy girl. He treasured the moment, knowing he'd never feel such bliss for the rest of his life. If his sister only knew how much all this teasing and humiliation was turning him on, she'd probably think he was a total freak. Even as he thought this, he felt Trish spread his ass cheeks apart. Just a little bit before letting his two, supple buns come back together.

Patricia bit her lip as she glimpsed the sight of her brother's tiny, hairless anus, sealing the memory in her skull. "Your booty is so smooth baby girl. You go out to get it waxed, Cassie?"

"Mhm," Rich answered in his feminine persona for the first time. It felt... nice. So so nice.

"Can I see?" Patricia's voice was extremely soft. How could Rich say no? How could he say yes? He said nothing.

Taking it as an invitation, Patricia spread her brother open and gasped. "It's so cute and smooth. It's perfect!" Rich couldn't help but smile, though his heart hammered and his nerves buzzed with nervous energy.

"Thank you," he whispered, resting in his feminine energy.

"Cassie, you're such a special little girl, you know that?" Trish caressed her way up her brother's ass, to his back and down again.

"Mmm, yes," he sighed, surrendering.

He watched in the mirror as his sister leaned down over his body until her lips were just above his right ear, her warm, soft body caressing his entire backside, her soft hands caressing his back underneath his silk robe. She met his eyes in the mirror and gave a smile, then whispered into his ear. "I love you, Cassie." When her brother only moaned she admonished him. "Tell Mommy you love her, baby."

"I-I love you, Mommy." He said, flushing with humiliation as his cock twitched against his sheets.

"Such a good girl." His sister unhooked his bra and separated the straps, then sat up again to massage his ass. But then, Rich felt his sister tugging his panties down. In a panic, he snapped his legs closed.

"Hey! W-what the hell are you doing?" The objection was soft but the fear was real. He didn't know how he would explain his hard cock and why the front of his panties was soaked in precum.

"I just wanna see how smooth the rest of your body is, Cassie. I didn't mean to startle you, honey."

"I think I should keep these on. What we're doing is weird enough as it is. We don't have to be naked."

"Are you scared for Mommy to see your clitty, baby? Did I accidentally turn you on?" Rich froze, breathing heavily, looking over his shoulder at his sexy, dirty-talking sister. "Would it make you more comfortable if I was naked too, sweetheart?" She pulled her panties down and showed him the slimy gusset. "See, sweetie, mommy gets wet too. It's just us girls so it's okay." She pulled her panties completely off and handed them to her brother. "You want my panties don't you?"

After the briefest pause, he reached out and took the damp garment. Patricia smiled big. "I knew you wanted mommy's panties."

Rich marveled at the ball of warm secrets he held in his hands as his sister pulled his panties down, and then up one nylon-coated leg. She gently pushed one knee aside, revealing her brother's hard cock lying flat between his legs, his tip glistening with precum. She simply hummed in appreciation of his intimate places, then returned her hands to his ass, massaging upward and outward, distorting and opening his pretty hole. "Oh, Cassie, you have such a precious pussy. Mmm, Mommy loves your sweet cunt."

Rich moaned and buried his face in his sister's panties, unable to resist the urge any longer. She smelled of clean sweat, faint soap from Friday morning's shower, and the magnificent ambrosia of feminine arousal. "Mommy's pussy smell good, Cassie girl?" Rich hummed emphatically, smothering himself with the dirty panties. "May I smell your pussy too, baby?" Another affirmative hum, all femme and cutesy. Trish took a tentative whiff of her brother's anus and hummed in youthful delight.

"Oh, yum, Cassie! It smells like candy. Sweet little candy girl." Patricia took several deep, indulgent inhalations of her brother's nether region, humming in deviant delight. Rich only shuddered in response, devouring his sister's saturated panties as she buried her face in his taint. His eyes rolled in his head when he felt his seventeen-year-old sister's warm, wet tongue slide up from near his balls to his hole.

"Oh, God, Trisha!" Rich moaned, clenching his fists in the sheets. She giggled through a moan and sighed a relaxed sigh, lapping wet at her brother's tight anal rim. "Fuck, don't stop, but why are you doing this?"

"Mmm, you like having your sister's tongue all in your asshole, Cassie? It turn you on?" She spit, used his ass cheeks to massage the globule of saliva into his ring, then licked up the sputum.

"This is so fucked," he whispered.

"You like it."

"Yes!" Rich whined girlishly. "Please keep eating my wet pussy!"

Patricia gave a satisfying hum. "Say, 'thank you, Mommy,'" she commanded, kissing a smooth buttock and then spitting between once again.

"Thank you, mommy!" Rich squealed as spittle dripped down through his valley, streaming down his balls. "You're so good to me."

"Such a good girl," Trish praised. "Would you like a treat, sweetie?" she asked, sliding a finger against his tight little ring. "Want me to touch your princess parts and give you cummies?" Rich simply groaned like a girl and quivered. "Say it."

"Mommy please touch my princess parts and give me -mmh- cummies." He could barely get the words out due to utter humiliation and a level of eroticism reserved for angels. He felt wicked for having the fortune to experience such perverse pleasure.

"Sweet baby," Patricia sang tranquily as she slipped the tip of her finger inside her brother's tiny anus. His pliable anus swallowed his sister's delicate middle finger as she sank as deeply into him as she could, then held it. "Such a snug princess," she said, seeing her digit protruding from her brother's perfect, hairless asshole. Then she started to pump her slick finger in and out, oscillating slightly and slowly.

"Touch my clitty?" Rich pleaded with a tone as soft as cool mist. "Please?"

"You don't have to beg mommy to touch your pretty clitty, sweetheart," she cooed melodiously as she reached for his tip, slipping her index finger underneath his cock, curling it and sliding backward to ever so gently stroke his sensitive tip. "You deserve it, Cassie. And it's such a treat to make you my sweet little minx. To make you feel so good. To make you squirm and hiss and hum until you get so excited and squirt your precious cream."

"Ooh, make me squirt," Rich panted desperately, humping his cock against his sister's small fingers as she fingered his asshole. "Oh, I'm gonna squirt so much for you Mommy. You make cum so good." Trish's finger slid light and slick against Rich's cockhead, her finger softly stroking his boy hole. And after a few more strokes, his orgasm sprouted out. "Ooh! Thank you, Mommy! Thank you so much for making your little girl cum!"

"Mm, aren't you just a sweetheart when you have your cummies," Patrica said, watching spurt after spurt of white cream coat her fingers and the sheets between her brother's legs. "That's right love, give me all that sweet, princess cream."

Rich shuddered put the rest of his orgasm, clutching at his bedsheets and smelling his sister's panties. After, he turned over and sat Indian style before Patricia, accepting her two, cummy fingers into his mouth. He licked his seed off his sister's fingers, bobbing and pulling on her hand as if sucking cock. "My God, you're so submissive," she said. "I would love to be with a girl like you."

The two stared at one another for a long moment, a silent conversation taking place between their passionate eyes. "Okay," Rich breathed full of meaning.

"O-okay," Patricia said and gave a faint smile that grew. "Okay," she said more surely and then leaned forward to kiss her brother's sweet, soft, feminine lips. After the kiss, she looked at him as if she was either puzzled as to why it felt so good to kiss her girly brother or perplexed as to why she'd waited so long to seduce him. She leaned in for another kiss, pushing him backward onto the bed.