Ch. 01: First Beginnings

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Jaime goes on an adventure and finds more than he wanted.
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Jamie moved carefully as he stepped into his stepsister's room praying he wouldn't be caught. He'd have been lying if he said he wasn't afraid of her. He'd always been a small boy. At 16 he was only 5' 3, had an effeminate petite build and almost no muscle definition. She

On the other hand was indeed taller than he was, 5' 7" at least with a well defined arms and legs from her many years running cross country. Luckily for him however she was currently distracted with her boyfriend down stairs.

AJ Wright was everything Jamie wasn't. Tall, athletic, and well toned, he was popular too. He was captain and ace of their school's state champion men's volleyball team. Jamie hated him. His mother had married Brianna's dad three years ago and ever since he met her, he'd wanted her. He'd fantasized over her, dreamt about her and masturbated to images of her. Then last year she'd started dating AJ. It made Jamie's blood boil to think that the one woman he wanted was with some one else.

Steeling his resolve he crept across the room and to her dresser. Moving as slowly as he could he eased open her top drawer. There he found it, his prize, and light blue thong.

"Find what you're looking for?" asked a voice behind him. Snapping around in shock he hid the evidence behind his back.

"B-Bri!" He said with a start. There she was, his stepsister, wearing a black anime shirt and a pair of tight short shorts. She was standing in the door of her room, her feet spread and fists braced on her hips. The look of dark fury on her face told him he'd be hard pressed to convince her he wasn't doing anything.

"Well?" She demanded not budging "you find anything?" Jamie felt the blood drain from his face.

"I, I, uh..." Jamie trailed off. He had no idea how he was going to get out of this. He watched as Bri walked toward him slowly. As he went to step around her she caught him and shoved him back in front of her. At the same time she reached around a plucked his prize from his hands. When she saw what it was she laughed cruelly.

"Seriously?" She asked twirling the thong around a finger "are you that desperate to get in my panties." Jamie shook his head vehemently.

"It's not like that," he argued "I found them in the bathroom and was just returning them to you." He prayed his bluff would work. Bri appeared thoughtful for a moment.

"Really?" She questioned "that's funny. Since I just folded them and put them in there an hour ago." Dread dropped into the pit of his stomach. He'd been caught. Bri's expression changed again as though a thought struck her.

"Alright if you want them that bad," she mused. She dangled the panties by one finger "strip." Color immediately rushed back into Jamie's face.

"Wh-what?" He stuttered.

"Now," growled Bri, "unless we need to tell my dad you're in here stealing my panties." Seeing he had no other choice, Jamie reluctantly pulled off his shirt before pushing the sweats he'd been wearing to the floor and stepping out of them leaving himself only in his boxers. He saw Bri raise an eyebrow

"Boxers too," she said in a low voice. Jamie's mouth dropped open but no sound came out. He gazed around the room desperately searching for a way out. He found none. Gulping heavily, he hooked his thumbs in his waist band and slowly removed his boxers. He now stood naked in his stepsister's room. He wasn't sure what he had expected, but the laugh certainly wasn't it.

"What is that," she said between laughs "you seriously thought you could get me, with that?" He looked up and saw she was pointing at his crotch. He looked to his dick and saw it was standing fully erect, even now the embarrassment had him hard.

"What?" He asked "what's funny?" Bri snorted.

"Your dick," she said "if you can call it that. What is it? Like 3 inches?" His embarrassment redoubled he moved to cover himself. "Ah, ah, ah." Jamie looked back up and saw Bri holding her hand out to him the panties still dangling from her finger. Jamie stared at them blankly.

"You want in my panties so bad," she clarified "here's your chance. Put them on bitch." Jamie couldn't breath. With no other choice his meekly took them from her and held them open. Gulping once again he bent over and stepped into them one leg at a time. The feeling of the silk on his skin sent shivers through him as he pull them up his legs. He felt the back slip between his cheek and nestle there as the front cupped his smooth balls. He'd never liked mass amounts of body hair so kept his dick, balls and ass shaven. Bri had got silent. He looked up at her to see her staring thoughtfully at him. He was about to open his mouth to ask what was wrong when there was a knock on the door. Terror gripped him.

"Hey babe where'd you go?" asked AJ as he stepped inside the room. He came to a stop as he took in the scene before him. "What the..."

"Hey baby perfect timing," said Brianna, she walked toward her boyfriend. Taking his face in her hands she pulled his head down and gave him a searing kiss. AJ returned the hot kiss with energy. When she pulled away she wrapped her arm around his waist and turned back to face Jamie.

"I came up here to grab something and found this little bitch going through my panty drawer," she explained "I figured if he wanted in my panties that bad, I'd let him." AJ face clouded darkly at the mentions of Jamie's adventure but cleared up with a hearty laugh as he understood what Bri was saying.

"So the little bitch is wearing your panties eh?" He asked only to embarrass Jamie.

"Exactly," affirmed Bri "but I've developed a bit of a problem." AJ looked at her with a raised eyebrow in question. "You see, he's being such a subby little bitch that it's got me all hot and bothered. Do you think you could help me baby?" Jamie saw a smirk cross AJ's face. He glanced at Jamie before looking back at Bri.

"If you want it," he said "then go get it." Bri eagerly dropped to her knees and her hands flew straight to his belt. A couple quick motions and his belt, button and fly were undone. As he watched Bri pulled the front of AJ boxers down. His dick spring out and slapped her right in the face. Jamie's jaw dropped. His dick was at least 9 inches. And it was think, he could guess the diameter but it was almost as thick as his wrist. Without hesitation, Bri gripped the base of her boyfriend's dick and licked it from base to head.

"Oh baby," said Bri "I love the taste of your dick." She licked the phallus several more times before wrapping her mouth around the head. AJ groaned in pleasure. As he watched Jamie couldn't help but feel his dick stiffen. As he looked down in astonishment he saw a dark patch forming in the material of the thong at the tip of his dick.

Loud slurping sounds reach's his ears. He looked up and saw Bri, her head bobbing up and down as she sucked his dick. He watched for long moments as she serviced her boyfriend. He couldn't help his gaze falling back to his own dick, the dark spot growing more and more as the sounds for Bri sucking dick. A harsh laugh reached his ears.

"What the hell is that?" Asked AJ "is that supposed to be a dick?" Bri pulled her mouth off him with a pop.

"Cute isn't it," she asked "but with a tool like that, can he even call himself a man? He might as well be a girl." Bri feel silent again gazing thoughtfully at Jamie as she idly stroked AJ's dick.

"In fact, get over here Jamie," she demands standing up. Panic crosses Jamie's face, he stares at his stepsister for a long moment. "Now!" The shout galvanizes Jamie into action. He stumbled forward until his stood in front of them. Before he truly understood what was happened he felt Bri's hand on head pressing down. A tap against the back of his knee had him falling to his knees. He looked up and saw AJ's pale thick wet dick staring him in the face.

"Wait, wait," he protested but felt a hand grip the bottom of his jaw.

"Open up bitch," he heard Bri order. "You're going to suck his dick." Jamie tried to clamp his mouth shut. Whimpers left his throat as he tried to resist. He felt Bri squeeze his cheeks puckering his lips and causing a small gap. His eyes sprang open as he felt the tip of AJ's dick brush against his lips.

"There you go," closed Brianna "open that pretty mouth of yours." Jamie felt her squeeze his nose closed. He tried to hold his breath, he did but it all became too much and the second he open his mouth to take in air, AJ slipped his dick into his mouth.

"Fuck he's got a warm mouth," groaned AJ. Jamie continued to whimper as he struggled to cope with AJ's massive dick in his mouth. Jamie couldn't explain what he was feeling, he hated this. So why was his dick so hard? Painfully hard in fact. Bri's hands began moving his head back and forth, up and down her boyfriend's dick.

"I'm glad you like it baby," she said "though I'm not sure 'he' is the proper term for this little sissy." As the word reached his ears Jamie felt his dick twitch the hardest it ever had. Then he felt a drop of AJ's precum hit his tongue. It was all took much, with Bri's words in her ears, the taste of AJ's precum on his tongue combined with the musk of AJ's groin and the feel of his lips around AJ's thick dick, his sense overloaded. He hallowed his cheeks in a reflective long suck as his orgasm exploded through him.

AJ groaned as he sucked, but Bri was observant, she'd been curious how far she could push her effeminate step brother. Now she had at least part of the answer.

"This sissy is cumming baby," she marveled "he's cumming from sucking your dick." She pulled him off AJ's dick and pushed him back. She he lean back on his elbows the light colored panties were completely soaked with his orgasm.

"What a slut," said AJ "get back up here bitch." Riding his post orgasmic bliss Jamie sat back up and, not realizing he was doing it, took AJ back in his mouth again. He hadn't realized that Bri was no longer forcing him. In fact her hands hadn't touched him. He simply sucked, because his brain wasn't allowing anything thing else. He inexperiencedly bobbed his head up and down, sucking as he went.

For long minutes he sucked until his jaw hurt. AJ seemed to notice he was tiring because he suddenly gripped Jamie's hair and pulled him off his dick. Jamie's

Mouth came off AJ with a loud pop, he was panting, his tongue slightly out as drool ran down his chin. He was briefly aware of AJ talking to Bri and Bri stroking him.

The first splash of cum on his face woke snapped him out of it. He became aware of AJ's dick shooting rope after rope of hot sticky cum all over his face. He closed his eyes and mouth a simply endured. Finally AJ wiped the tip of his dick clean on Jamie's lips and stepped away. Jamie heard a drawer open and close. Then he felt hands, Bri's he thought, lifting him to his feet and guiding him by the hand. When they finally stopped Bri spoke.

"Take a shower and get cleaned up," she said "when you get done up these on, they're on the vanity, and then get dressed. Believe me little brother, I will be checking later." Jamie finally stripped off his sister's panties and fumbled for the shower. He cleaned quickly, washing his hair, face and body thankful the events of the even were over. He cut the water for the shower and grabbed his towel off the rack. But it was as he step out of the shower and caught a glimpse of what his sister had left on the vanity that his stomach dropped.

There, waiting for him, was a pair of pink panties.

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Bi_fun_guy10Bi_fun_guy103 months ago

Hot story, I can't wait to read the next chapter...

tslover1963tslover19633 months ago

Brings back memories of my first time forced feminization and forced to suck a big cock, as it’s Jaime, I came in my panties from just sucking it, and he did cum in my mouth, swallowed my first humongous load

BiCowboyDFWBiCowboyDFW3 months ago

Oooo. More please!!

AnonymousAnonymous3 months ago

I loved the story. Jamie's initiation was very erotic and I can't wait for chapter 2!

dreamer31adreamer31a3 months ago

good start cant wait for more just like lucky Jamie

xx

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