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/elit/ - Erotic Literature
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A Sissy Story Dee 13/01/12(Sat)18:49 No. 18110 ID: 9b0c45


James swallowed hard as he walked toward the front door. He rang the doorbell and stood fidgeting on the stoop. James was a popular enough guy. He was a surfer with the classic long blond hair, blue eyed beach bum look, he was also a star swimmer -- the only freshman to make the varsity squad. Despite this he was nervous. This was the first time he’d gone to a girls house when her parents weren’t home. Not only that, but the girl, Julie, was the hottest freshman at school. The door swung open and Tommy, Julie’s brother, stood inside.

“Hey come on in,” said Tommy.

James stepped through the door and looked up at Tommy -- a senior and the captain of the swim team. He was at least 6 inches taller than him. Most guys were taller than James, who was barely 5-foot 7-inches. He walked into the hallway and looked into the living room where Chris -- Tommy’s best friend -- was sitting on the couch playing xbox. Chris was a wrestler and was short and broad chested, although he was still taller than James.

“Who invited the midget?” Chris called out.

“My sister,” said Tommy. “She’s upstairs in her room. Go on up its the first door on the right.”

James thanked Tommy and gave Chris the finger as he ran up the stairs. He took a deep breath and slowly opened the door. Julie was laying on her bed listening to her ipod and flipping through facebook on her laptop. She was laying on her stomach in just a sweater and panties. Her socked feet were crossed in the air behind her.

James felt his cock grow in his pants as he admired her smooth cream colored legs that led to a large round ass and narrow waist. Her straight blond hair was cut into a short bob. She looked back noticing James. Her big blue eyes widened and her pink lips parted leaving a surprised look on her gorgeous face. She pulled a blanket over her legs.

“Jeez, James why didn’t you knock?” She exclaimed.

“Oh, I’m sorry I thought you knew I was coming,” he replied sheepishly.

“Well,” she said with a smile. “you’ve seen me in my undies. It’s only fair I get to see you.”

This made James already hardening dick jump to attention. James blushed, closed the door and stepped into the room. He agreed to the punishment, and began racking his brain to come up with a way to hide his hardon. He turned his back to Julie, who was now sitting up on her bed, and unzipped his jeans letting them fall to his feet. He stepped out of them and kicked them aside.

“There, now you’ve seen me.” James said.

Julie got up and strolled over to him. She looked him up and down, noticing he shaved his legs -- for the swim team no doubt. She turn around and press her ass against his.

“I think your ass is wider than mine!” she teased turning around. “You have very girly hips.”

James’ face turned bright red. He knew he had wide hips that was one of the things that made him so good at the breaststroke, but getting called girly by the hottest girl in school made him want to crawl under her bed and die. Sensing she’d embarrassed him she turned him around and kissed him softly on the lips.

“Don’t worry, all the girls think you have a cute butt,” she said.

She ran her fingers through his long hair. A mischievous smirk spread on her face before she said, “Shaved legs, a girly butt, long hair. I think I have an idea. I’m going to dress you up!”

“No. Absolutely not,” James said.

“Oh come on it’ll be fun,” Julie laughed then reached down and gripped his hard cock through his boxers. “I promise.”

James reluctantly agreed, but thought he could name a few things a guy with a massive boner in the bedroom of a hot girl would consider more fun. While James stripped Julie began pulling out various clothes and underwear. Standing stark naked in the middle of Julie’s room, James thought things were going ok. So he was naked for a different reason than he hoped, but he was still naked. It was only a matter of time until she was too right?

Julie walked over holding a black lace cheekie thong. Getting on her knees in front of James she pulled it up over his smooth legs and up to his waist. His hard cock was poking out the top of the panties. Julie frowned at it.

“Well this won’t do,” she said.

Yanking the panties down to the floor, Julie looked up at James and smiled. She reached up and took his cock firmly in her hand massaging it while looking into his eyes. Moving her face toward his smoothly shaven crotch she licked with one broad stroke from the base of his balls all the way to the head of his cock.

Pausing with the tip against her lips, Julie slowly took it into her mouth while she gently cupped and massaged his balls. He felt her fingers tease further behind his balls, which surprised him but made him even more excited. With a sigh of pleasure James ran his fingers through her soft hair as she started to bob her head on his dick. Faster and deeper she worked his cock into her mouth and down her throat. With his hand on her head James started to hump Julie’s face until her nose was pressed against his pelvis and his balls slapped against her chin.

Julie slid her hand between his legs and wiggled her finger between his cheeks as she continued to take him all the way down her throat. Her middle finger found his tight asshole. James moaned while Julie teased his hole moving it around and increasing the pressure against it. Just as he felt her finger slide into his ass his cock erupted shooting a massive load straight down Julie’s throat. She continued to work his cock until every last drop of cum was sucked out leaving his spent cock flaccid. Legs shaking he looked down at Julie who smiled up at him as she wiped the cum from her chin.

“Ok that thong should fit just right now,” she smiled.

Dee 13/01/12(Sat)20:44 No. 18112 ID: 9b0c45

James stood in the middle of Julie’s room still in bliss from the amazing blow job he just got. In fact with his load blown the idea of being dressed up in girls clothes wasn’t entirely unpleasant. The black lace thong Julie just pull over his hips felt nice and soft against his skin. He started to think that this actually could be fun.

Julie laid out the rest of the outfit on her bed. First she put a black strapless bra around his chest. She stuffed it with wads of tissue since there was no way he was going to fill out her 36c bra the way she could. Over the bra went a form fitting black halter top and thigh length pink frilly skirt went on the bottom. Over his smooth legs -- shaved for the swim team -- he pulled sheer black knee high socks.

Julie led James to the mirror to get a look. It was an odd feeling seeing his surfer guy head on top a sexy girls body. Julie, standing next to him reached down and squeezed his ass.

“You’ve got a hot body,” she said. “Now we have to work on your makeup.”

“No, no this is far enough,” James said. “If any of the guys found out I dressed up like a girl I’d never hear the end of it.”

“What if I show you my tits?” she offered.

James gave it a half seconds thought before agreeing. Stepping back Julie lifted her sweater exposing beautifully round and perky breasts with cute little pink nipples in the center.

“Ok you got a look now I get to play,” she laughed.

She sat James down and went through all the makeup applying foundation, blush, mascara, lipstick, nail polish, the works. She even plucked his eyebrows. She found a pair of silver hooped clip-on earrings and a silver necklaces for James to wear. To complete the transformation Julie pulled James’ hair back into pigtails.

“You are the best doll ever,” Julie said. “Have a look you’re a hotty.”

James got up and went to the mirror again and his jaw dropped at the sight. He didn’t recognize the hot chick in the mirror. His wider than normal hips made the skirt flare out and drape nicely over his round ass. His body appeared more curvy thanks to the stuffed bra and his skinny waist showed just a little between the halter top and the skirt. But the most dramatic change was to his face. Gone was his unkempt beach hair, instead it was cute pigtails, and the make up changed his face. He barely recognized himself; his eyes looked bigger, his chin narrower, his cheeks higher and everything looked more feminine.

“Whoa, I totally look like a chick,” James gawked.

“You sure do, Jamie,” Julie said as she snapped a picture with her phone.

“Hey no pictures!” he exclaimed.

“Oh common we have to document what a sexy little girl you make,” she laughed raising the camera again. “Now show me pouty.”

“Jamie” continued to object briefly, but eventually relented and played along striking sexy poses around her room. They spent so long playing dress up that they lost track of time until there was a knock at the door.

“Julie your brother says you’ll be late for practice if you don’t leave right now,” Chris said as he swung the door open.

“Oh shit,” Julie said as she hurriedly pulled on sweatpants and sneakers.

“Wow, who’s the babe?” Chris said as he walked through the door. A look of revelation came to his face as he said, “Don’t tell me... The midget?”

“Oh yeah, we were playing dress up,” Julie laughed running toward the door. “Sorry I have to run James. You can leave the clothes and stuff on the bed.”

Julie flew out of the room and down the stairs. Tommy was already pulling the car out to take her to practice. Back in her room Chris continued to stare wide mouthed at Jamie, taking in his fully transformed body.

“Holy shit, I can’t believe you’re the same guy,” Chris said. “Fuck, I can’t believe you’re a guy at all!”

“So I suppose you’re going to tell everyone at school about this,” Jamie squeaked.

“Well that depends,” Chris said walking forward toward James. He put his hand on Jamie’s’ ass and asked, “What will you do for me if I don’t?”

“I’m not doing that,” Jamie said his voice quivering.

“That’s too bad,” Chris said.

Chris grabbed Jamie’s wrist and in one fluid motion twisted his arm back and up behind his back, slamming him down over Julie’s desk. Chris looked down and with his other hand lifted the skirt up over Jamie’s ass making a sound of approval. Jamie looked back and watched Chris unbutton and pulled a huge cock from his pants. Jamie’s eyes widened at the sight of it while Chris pulled the black thong down just enough to expose his asshole.

“I know,” Chris smiled. “It’s more than 8 inches.”

Chris spread Jamie’s cheeks apart and spit right onto his hole. He slowly spread it around the hole with his finger making a slow circle before sliding it all the way inside him. Jamie gasped as he felt his ass being penetrated, wiggling away. Chris twisted his arm harder.

“Calm down you’re going to have to take something much bigger than that,” he said slapping his cock against James’ ass. “I have to say though you have a gorgeous asshole.”

“Please don’t do this,” Jamie begged.

Chris just smiled and started to press his cock head against James tight pink butt hole. Squirming Jamie reached back with his free hand to try and push Chris off. Chris batted his hand away and pressed harder with his cock. Suddenly the tip popped in causing Jamie’s mouth to go wide. Chris pushed in slowly making Jamie take more and more length and girth as he did. He felt Jamie’s anus grip down tightly around his hard dick. When his cock slid in half way he pulled out slightly then rammed into Jamie’s ass who cried out with pain. Jamie reached back again, this time Chris grabbed his other wrist and pulled both arms back straight. This lifted Jamie’s chest off the desk causing his “tits” to bounce up and down as Chris started to hump him.

Chris used his hold on Jamie’s arms to help him thrust hard and fast into his virgin bum. The trusts came faster and deeper as Jamie’s tight ass began to loosen and accommodate the huge girthy cock. The mix of pain and pleasure was almost overwhelming for Julie, but as Chris continued the pain lessened while the pleasure grew immensely. Before long he found himself pushing back against the cock and wiggling his hips up and down.

“Oh yeah babe grind on my dick,” Chris moaned. “God you make a hot little slut.”

“Fuck you!” Jamie managed to grunt as Chris pounded his ass.

Jamie looked across the room and found the wall mirror. From that it angle it seemed to show a small blond teen girl bent over a desk, a muscular guy held her by the wrists fucking her from behind. Her mouth was open emitting soft moans. Her panties had slipped down around her knees and if you weren’t looking you wouldn’t notice her small soft dick slapping against the desk with every thrust.

Chris pulled Jamie off the desk humped him to the ground. Jamie was on his knees, ass in the air while Chris pushed his head into the carpet. He pulled out and spit into Jamies hole giving himself extra lube the pushed it in balls deep with one thrust. Despite himself Jamie was enjoying the feeling of his ass being plowed. With every thrust Chris pushed the walls of Jamie’s ass furth open.

“Spread your ass cheeks,” Chris commanded. Jamie reached back and spread his cheeks wide, allowing Christ to push even deeper inside him.

Chris thrusted even harder making Jamie feel everyone in the pit of his stomach. The two sets of balls slapped together while Chris reach down and cupped one of Jamie’s tits. Jamie was feeling overwhelmed with pleasure. He began to collapse forward until he was laying flat on the floor shaking uncontrollably.

Suddenly Chris stopped thrusting and Jamie felt the cock shoved up his ass beginning to bulge and spurt warm cum into his body. Still cumming Chris began to withdraw his dick, saving one last blast of cum for Jamie’s crack. Jamie could feel warm goo leaking from his used hole. Chris laid on top of him catching his breath for a moment. When he finally stood up he saw Tommy standing in the doorway.

Anonymous 13/01/19(Sat)21:25 No. 18160 ID: e73a2f

really good!

tSade!O9S.2cqv5k 13/01/20(Sun)16:31 No. 18165 ID: e1353d

Mmm, that was deliciously yummy. I like how you don't really explain *why* he's stripping in her room, but frankly it doesn't matter. I would like a bit more details on the penetration but... I think it was hot even as it was.

If you decide to continue this, I'm looking forward to more abuse of his poor little ass. And probably his face. :)

Anonymous 13/01/21(Mon)07:04 No. 18167 ID: 8de8f1

more please that was good

Dee 13/01/22(Tue)00:35 No. 18172 ID: 9b0c45

Thanks guys i've been busy lately but i'll get around to parts 3 and 4 soon :)

Anonymous 13/02/17(Sun)00:03 No. 18335 ID: 7218bc


Dee 13/02/21(Thu)02:07 No. 18362 ID: 9b0c45


Chris froze standing over Jamie, his big cock wet with cum and ass juice, still hard after raping the little sissy. He looked over at Tommy standing in the doorway who was staring at Jamie with a mixture of shock and mischief on his face.

“Who’s the chick?” Tommy asked. “And what the hell happened? I left for like five minutes!”

“That’s no chick,” Chris smirked. “It’s fucking James. Your sister and he were playing dress up. I figured I’d let him know what it’s really like to be a girl.”

Tommy walked over to Jamie who was still face down on the floor, collapsed from the hard ass pounding he’d just endured. He could feel his hole tighten up and his muscles relax a little in the few minutes since Chris had cum inside him. Tommy bent down and rolled Jamie over.

“Come on babe sit up,” Tommy cooed lifting Jamie into a sitting position. “Wow, Julie did a great job. I wouldn’t be able to tell your were a guy except for this.”

As he spoke he reached under Jamie’s skirt and softly tugged on his flaccid penis, which immediately began to harden. Tommy smiled and withdrew his hand. He looked over at Chris. The two of them had been in situations like this before. Often they’d fuck their girlfriends in the same room and had talked about how much they wanted to double team a girl. He knew this was wrong, but just couldn’t pass up such a golden opportunity.

“Well Chris you certainly gave this little slut a good warm up, how about we see just how slutty she really is?” Tommy smiled. “It looks like there is some cum left on Chris’s dick. You know a good slut doesn’t let any go to waste. Open your mouth babe.”

Jamie’s eyes widened in shock. He’d been hoping Tommy would be his savior and rescue him from this ordeal. Instead he was watching Chris walk forward with his big tool bouncing in front of him. Tommy stood behind Jamie and lifted him up to his knees and Chris stopped in front of them. His hard wet cock swung in Jamie’s face. Chris put his hand on Jamie’s head and quickly rotated his hips slapping his 8-inch dick across the sissy’s face.

“Stop this please,”Jamie whimpered. “There is no way I’m sucking your fucking dick.”

“Oh you’ll suck it,” Chris said and quickly snapped a picture with his phone of Jamie next to his cock. “Because if you don’t we’ll make everyone think you did anyway. Do it and this will just be between us.”

Jamie gulped. He knew there was nothing he could do. Looking up with fear in his eyes, he reluctantly let his mouth hang open. He reached forward and grasped Chris’s cock firmly in his hand and moved his head in between Chris’s legs. Staring up at a pair of big hairy balls, he closed his eyes and moved in, licked them with a broad flat tongue. He took them in his mouth, rolling them around while starting to massage Chris’s dick.

While Jamie licked and sucked Chris’s balls Tommy looked down at Jamie’s cute round ass. He reached under Jamie’s skirt and grasped his cheeks. He firmly held them -- massaging and pulling them apart. Letting go he ran his middle finger all the way from the base of Jamie’s balls up his crack and lingered over his tight pink asshole.

Jamie moaned and quivered at Tommy’s touch, but continued to work on Chris’s cock. Chris stepped back and sat down on the bed. He grabbed Jamie’s cute blond pigtails and pulled him forward and up onto all fours. Chris lifted his cock up with one hand and pulled Jamie to it by his hair. Jamie looked at Chris with pure hatred as he let the tip of his cock slip between his lips.

Tommy knelt behind Jamie and admired his cute little hole. He spit on his fingers and with one fluid motion pushed them into Jamie’s boy cunt. Jamie gasped opening his mouth, which let Chris push more cock in. Tommy was amazed at how tight his hole was even after being fucked by Chris. He worked his fingered in and out getting him ready.

Chris’s cock felt even bigger in Jamie’s mouth than it had in his ass. He bobbed his head up and down sucking it in while Chris pushed his head down on it. Suddenly Jamie felt something hard and heavy flopped onto his ass. He looked back with the cock still in his mouth to see Tommy’s massive member swinging behind him. It was thicker than Chris’s and at least an inch longer, he let out a small whimper muffled by the dick in his mouth.

Jamie looked over at the mirror again, amazed at the sight. A skinny blond teen on all fours with a face full of cock about to have her ass plowed. It was something he would have gotten off to -- if it wasn’t for the fact that he was the cute blond.

Tommy moved forward pulling his fingers out of Jamie. He spit on Jamie’s ass and rubbed it over his hole. He placed the head of his huge cock against Jamie’s puckered hole. Tommy could feel his cock pounding in anticipation as he pushed forward. Jamie’s ass resisted at first, which caused Tommy’s cock head to mash up against it. Jamie moaned on Chris’s cock, he was beginning to really love the sensation of having a dick pressing against his hole. He rocked back a bit pushing out with his hole.

Tommy’s cock head slipped into the hot tight anus and he felt it grip down around it. Tommy put his hands on Jamie’s hips and slowly pushed further as Jamie’s ass was forced open. The feeling of the massive dick sliding into his ass made Jamie suck more voraciously on Chris’s cock. Whereas before he was sucking out of fear, the cock in his ass made him crave even more cock.

Jamie reached forward and grabbed Chris’s thighs opening his mouth trying to take more and more down his throat. While he did, Tommy spit down on his shaft as it disappeared deeper and deeper in the sissy slut’s ass. Jamie could feel the cocks on either end of him, one pushing out the walls of his throat the other the walls in his rectum.

Tommy, with about two-thirds of his cock in Jamie, pulled out a bit and pushed in again feeling the tight walls of Jamie’s ass and his clenching sphincter move over the shaft of his cock. He began humping his ass faster and pushing deeper.

Chris looked back at Tommy fucking Jamie’s slutty ass as he felt his warm wet mouth sucking on his cock. He couldn’t believe he had more cum after the massive load he dumped into the boy-whore’s ass, but he felt another climax growing. Just as Jamie finally managed to push the cock all the way down his throat, burying his nose in Chris’s pubes, he felt it pull out quickly. Jamie gasped for air, mouth wide open, as Chris’s monstrous dick shot rope after rope of sticky white jizz all over his face and mouth.

“Oh yeah slut you give some good head,” Chris sighed. “Tell me how good my cock tastes you fucking skank.”

“You’re such a bastard,” Jamie managed while still gasping for air, but let a small smile spread on his face.

“See I knew you were a whore on the inside,” Chris said.

“Maybe you’d like the taste of your own ass too,” Tommy added.

Tommy quickly withdrew his dick and sat down on the bed next to Chris. He pulled Jamie over and pushed his head down. Jamie had a look of surprise as Tommy’s huge dick was forced balls deep into his face. He gagged, his eyes watered, but he could taste the distinctly earthy bitter taste of his ass juices on Tommy’s pole. Tommy released and Jamie again came gasping up for air.

“Come sit on my dick like a good little girl,” Tommy commanded.

Jamie was starting to get into it. He stood, curtsied, and turned around. Daintily lifting his skirt he sat back as Tommy guided his fleshy missile at Jamie’s target hole. With Tommy’s hands on his cheeks Jamie felt a big dick once again force its way into his ass. Tommy began thrusting up and Jamie winced slightly as he felt the dick pounding in him, like someone was punching him in the gut from the inside.

After a moment the unpleasant sensation subsided and he willingly bounced up and down on Tommy’s lap, feeling his boobs bounce with him. It was a strange but exciting feeling. Jamie pulled his feet off the floor and curled them behind him on the bed. He leaned forward and put his hands on Tommy’s knees and began rocking his hips against the massive pole penetrating him. His skirt flared and lifted up as he moved his hips faster and worked them up and down and in circles. Tommy reached forward and cupped his fake tits as Jamie gyrated on his meat. Tommy could feel his orgasm building.

“Hold your cheeks apart,” Tommy said. “I want to see how much I damaged your ass.”

Jamie reached back and pulled his ass open. He leaned forward and savored the feeling as inch by inch Tommy’s dick slid out. It finally came flopping back leaving a wide open gaping hole. Tommy took his stick in his hand and with a couple quick jerks fountains of cum came shooting out. The cum shot all over Jamie’s ass and a few shots went straight into his gaping hole.

Tommy pulled Jamie toward him and with a long stroke licked from Jamie’s hairless balls up to his still gaping hole. Tommy snaked his tongue inside tasting his own cum in Jamie’s used up ass. Jamie moan out Tommy’s name as he licked and suck on sissy-pussy. He collapsed backward curling up between Chris and Tommy, still moaning and shaking.

“Well, gee, Chris I think we might have a new fuck-toy on our hands,” Tommy smiled.

“Yeah we’re going to have to make this a regular appointment,” Chris agreed.

Dee 13/02/21(Thu)05:57 No. 18365 ID: 9b0c45

Sorry it took so long but i promise I'll keep them coming

Anonymous 13/02/21(Thu)22:24 No. 18367 ID: 29900d

Well, if you keep them coming, you'll keep us cumming!

tSade!O9S.2cqv5k 13/02/24(Sun)16:23 No. 18381 ID: e1353d

I love you so much. I absolutely adore stories about submissive boys and cross-dressing. Yummy! Wonderfully yummy.

Anonymous 13/02/27(Wed)20:32 No. 18396 ID: 6cad57

fantastic so far, thankyou

Anonymous 13/03/12(Tue)22:39 No. 18494 ID: ba1009

Very hot! Pls continue

Dee 13/03/30(Sat)20:34 No. 18610 ID: 9b0c45


James spent the next week at school doing his best to avoid Tommy, Chris and Julie. It was fairly easy to stay away from Tommy and Chris. They were in a different year so they had no classes together and both drove in so he didn’t have to see them on the bus.

Julie was another matter. They had a bunch of classes together and usually sat near each other on the bus. He got a ride into school the first few days of the week, pretending to miss the bus, and would turn and walk the opposite direction whenever he saw her.

James thought he just might make it through the week without having to be reminded of the embarrassment he went through last weekend. It was bad enough that he couldn’t help picturing Tommy’s cock sliding into his ass every time he tried to jerk off.

He had just about made it through to the end of the day Friday. He was putting his books in his locker about to head out to the bus. He closed the door and was face to face with Julie. He jumped back, startled to see her. She must have snuck up while he was busy storing his books.

“Why are you avoiding me?” she asked with a crossed look on her face.

“I’m not avoiding you,” James lied. He turned and started to walk away, but Julie followed at his side.

“I’m sorry if I embarrassed you last weekend,” she said. “It was just a bit of fun.”

“No it’s not that,” James said. “I mean I would like to spend more time with you, ya know, dressed like a guy. Maybe we could hang out Saturday? You do kinda owe me.”

“I’m going to the mall with a couple friends Saturday, but you’re welcome to come with us,” Julie said. “Why don’t you meet us there around noon? They’re coming back to my house to sleep over that night, but we can drop you off at home on the way back.”

James agreed and went home that night feeling pretty good about himself. He was going to hang out all day with three hot girls and Julie seemed to really want to do stuff with him. On top of that she didn’t know what he did after she went to practice, so his chances of making her his girlfriend were still good.

When Saturday came he had his Mom drop him at the mall and he went to meet the girls at the food court. Julie and her two friends were finishing up lunch and sitting near the windows in the large crowded food court. James knew the two other girls, but not well. They were both Juniors and pretty popular. To Julie’s right was Mandya short creamy skinned redhead with the nicest ass James had ever seen and one of the bigger racks in school. To Julie’s left was Sarah, a mocha skinned beauty with curly black hair and almond shaped eyes. She was a thin, toned runner and had a reputation as little bit of a man-eater.

James walked up to the table nervously. Julie looked up and saw him; she smiled and waved him over. He introduced himself to the girls and asked what stores they were planning to hit up. Julie said she wanted to buy a new spring dress and the other girls were just seeing if anything caught their eye.

For the next few hours James got the pleasure of playing judge as the girls tried on new clothes and asked his opinion. As it was getting closer to when they had agreed to leave the mall Julie flashed a devilish smile and quickly pulled James into a dressing room.

At first James thought he was going to get lucky, but it quickly became clear the girls had another idea. Mandy and Sarah popped their heads over the walls of the changing room stall and looked in at James and Julie laughing.

James’ face turned bright red as he looked up at the two older girls laughing at him.

“You told them,” he guessed becoming more embarrassed by the second.

“Yeah I showed them those pictures of you all dressed up,” Julie explained. “They thought you were a hotty and wanted to dress you up too... we picked out an outfit for you to try on!”

Mandy and Sarah handed over some clothes picked out from the store and James was already shaking his head “no” vigorously. There was no way he could wear what they wanted him to -- a pink bra and panty set, a thin plain white t-shirt that wouldn’t even cover his belly button, a black miniskirt that would probably show the bottom of his butt cheeks, thigh high white stockings and black sandals with a chunky high heel.

“Oh come on,” Julie pouted looking at James’ shaking head. “What if me and Mandy make out for 30 seconds, would you play along then?”

James thought back to what happened the last time he made a similar bargain, he ended up having his ass pounded by two big cocks. This time though they were in the middle of a mall in a locked stall, what could happen? So he agreed.

Julie smiled and watched intently as the two beautiful girls kissed over the changing room stall wall. Their lips and tongues pressed together, eyes closed clearly enjoying the moment. James felt his dick grow in his pants watching the hot lesbian lip locking. After they finished James stripped naked and pulled the panties up over his ass. They were cut in a bikini style and only covered about a third of his ass cheek letting the rest of his big round ass hang out. Julie helped him get the bra on and stuffed the 36c cups with some socks. He pulled the short belly shirt on and noticed the bright pink bra was clearly visible through it just as Julie pulled the miniskirt over his hips. The bottoms of his butt cheeks peeked out below the extremely short skirt. The stocking and shoes completed the outfit. James looked at himself in the full length mirror admiring his slutty girl look and Julie pulled a makeup kit out of her purse.

“No way, we’re in the middle of the mall I’m not putting makeup on!” James protested.

“It’s fine I have wipes we can get it off before we leave,” Julie said. “Please, they really wanted to see how sexy you look all done up right.”

James reluctantly agreed, but he just couldn’t seem to say no to Julie. Julie’s make up job this time was a little less subtle, using darker eye shadow and more eyeliner. A black ribbon choker necklace and a quick braided ponytail finished his transformation.

“Girls,” Julie smiled. “Meet my new friend Jamie!”

“Wow you look so hot babe,” Sarah smiled.

“Yeah I can’t believe it you look totally different,” Mandy said. “I couldn’t tell if I didn’t know.”

James stared at himself in the mirror and butterflies immediately started churning in his stomach. He had been trying to tell himself he had hated what happened last weekend, but becoming Jamie again felt amazing and exciting. While he admired himself in the mirror Julie gathered his boy clothes and threw them up to Mandy who dropped them in her stall out of James’ reach.

“Sooo, I was thinking,” Julie giggled. “How would you like to come to our sleepover tonight?”

“Hell yeah I would!” James exclaimed still unaware his clothes had been pilfered.

“Well the thing is my parents would never let a boy sleepover, but I bet they’d let my new girl-friend Jamie,” Julie said.

Jamie looked around the stall noticing his clothes were missing and his jaw dropped as he realized what the girls had planned.

“Please don’t do this,” Jamie pleaded.

“Oh it’ll be fun!” Julie smiled. “Wait here for a few minutes then come out. We’ll text you with a few things you need to do before meeting us at the car. Here’s your cell and a purse to keep it in.”

“You want me to steal these clothes?” Jamie asked aghast.

“It’s fine we took the tags off no one will notice,” Sarah said.

The three girls left laughing about the situation they’d left Jamie in. Jamie started to mull over his options. He could go out and take some guys clothes and change into those and leave the mall as a guy. Then of course he probably would completely blow whatever chance he had with Julie. He could just run through the mall to the car, but that would probably just draw more attention. He would just have to do what they told him and hope that he got a good reward when they got to Julie’s house.

Jamie took a deep breath, opened the changing room door and slowly stepped out into the crowded store.

tSade!O9S.2cqv5k 13/03/30(Sat)23:50 No. 18611 ID: e1353d

I'm loving this story. Thank you so very much for posting it. I like that it wasn't completely submission on his part, but you know that he's going to both regret and enjoy what is coming next. :)

Anonymous 13/04/09(Tue)23:07 No. 18677 ID: ba1009

Damn good stuff!!! Can't wait for the next chapter

Anonymous 13/04/16(Tue)22:57 No. 18713 ID: 62e7c5

not so patiently awaiting the next installment

Anonymous 13/04/28(Sun)09:23 No. 18785 ID: 62e7c5

this is my favorite story on this board, last desperate bump for OP

Anonymous 13/04/28(Sun)19:40 No. 18793 ID: b51dbf

want more chapters!

Dee 13/04/30(Tue)01:26 No. 18805 ID: 9b0c45


Jamie stepped slowly out of the store, wobbling as he got used to walking in heels for the first time. His face bright red and his stomach going wild with butterflies he walked to the exit and out into the crowded mall. Thankfully no alarms went off and none of the clerks stopped him to asked where he got the clothes.

He started to walk in the direction of Sarah’s car -- she was the girls ride -- which was all the way on the other side of the mall. He tried not to catch anyones eye and kept pulling the skirt down, which was constantly riding up exposing his ass.

As he walked he started to notice guys glancing over at him or checking out his butt. He even heard a couple whistle in his direction. Jamie started to smile and feel more comfortable. Not only could they not tell he had a dick stuffed inside his miniskirt, but they thought he was hot! Just as Jamie’s confidence was growing he heard his cellphone beep telling him he had a new text.

“Go buy a cute jacket it’s chilly out,” the text from Julie read.

Jamie turned and headed to the nearest store that sold girls clothing. He quickly grabbed a long black peacoat and walked to the checkout line. Still unsure on his heels, Jamie stumbled and fell to his hands and knees right in front of a group of college age guys. His skirt pulled up and exposed his whole ass to the group.

“Hey are you ok sweetie?” One of the guys said as he bent down and helped Jamie up. Jamie thanked him for his help and couldn’t help noticing his hand firmly placed on his ass. Jamie’s heart began to race and his cock jumped to attention. Why was he getting excited by a guy, he wondered?

“Thanks I’m fine,” Jamie squeaked. Surprisingly he didn’t find putting on a higher pitched voice that difficult. He readjusted his skirt trying to hide his huge boner without giving his secret away.

“Ok well be careful,” The guy smiled and patted Jamie’s ass. “I’m Mark.”

“I’m Jamie, nice to meet you,” Jamie smiled flirtatiously.

“Let me get that for you,” Mark said reaching out and taking the jacket from Jamie. He put his arm around Jamie’s waist and guided him toward the register.

Being a girl isn’t so bad, Jamie thought, guys help you up and buy you stuff what’re all those girls always complaining about?

They started to walk toward the counter to pay, but Julie felt Mark’s hand steer her away toward the dressing room.

“What are you doing?” Jamie asked.

“Well you’ve got to try it on first to make sure it fits,” Mark smiled.

No one was in the dressing room and Mark’s friends hung around by the entrance to “keep guard” whatever that meant. Jamie slipped to jacket on letting it hang open and flare around his wide hips. Mark looked him up and down making approving sounds as he did.

Jamie looked up into his deep green eyes framed handsomely by his shiny black hair. He was taller than Jamie and well built with a little chest hair peeking out from his collar. Mark leaned in and firmly pressed his lips against Jamie’s.

Jamie’s eyes went wide then closed slowly feeling Mark’s strong lips against his and his tongue probing Jamie’s mouth. It was a different sensation than kissing a girl. Jamie wasn’t in control, Mark was and this made Jamie’s heart pound with excitement. His right leg bent at the knee slowly raising his foot into the air.

Mark pulled Jamie in close letting his hands glide down to Jamie’s round bottom, squeezing it hard. Jamie squeaked as he did and began kissing him even more voraciously, twirling his and tongue around Mark’s mouth, tasting every last bit of his saliva.

Press up tightly with him, Jamie could feel Mark’s hard cock through his jeans. He looked up wide-eyed at the older man who placed a hand on his shoulder and pressed down letting Jamie know what he wanted.

“You don’t have to buy me the coat,” Jamie pleaded. “Please I don’t want to do this.”

“Aww honey is this your first time?” Mark asked.

Jamie’s faced burned and he shook his head “no.” Just last weekend he’s sucked off two massive dicks, but he didn’t want to make it a third.

“Then what’s the problem?” Mark asked rhetorically. “You’re just so hot you’ve got me wild I promise it’ll be quick.”

Mark unbuttoned his pants and lifted his cock and balls out. They bounced in front of Jamie’s innocent sissy face. He wasn’t quite as long as Tommy, but he was thick and had the biggest balls Jamie had ever seen.

Mark ran his fingers through Jamie’s hair and pulled the young slut’s face into his crotch. Jamie lifted his chin watching as Mark’s member bobbed in the air in front of him. Mark’s big balls loomed over Jamie. Mark lowered them dragging the soft heavy sack down Jamie’s innocent looking face.

Jamie stuck his tongue out letting the salty, hairy sack slide slowly down it followed by the thick shaft of Mark’s cock. He tasted the length of it pausing momentarily to enjoy the taste of precum at the tip. Jamie glanced quickly at the mirror to his side and felt his own cock grow at the sight of his girly appearance and the meaty cock he was licking.

Mark noticed Jamie’s eyes move to the mirror and smiled, saying “Yeah you look good licking my cock sweety, now take it all in your mouth.”

Jamie opened up obediently and Mark started to slide his wide cock head into the sissy sluts mouth. Jamie’s lips gripped down on the shaft and he wagged his tongue back and forth around the shaft as Mark pushed it in and pulled it out slowly.

The smell of Marks pubes and the feeling of sucking a dick made thoughts of last weekend’s fun with Chris and Tommy come rushing back, which cause blood to go rushing to his cock. A large bulge began to poke from beneath Jamies miniskirt as Mark reached down and placed his hands on the back of Jamie’s head.

This cock sucking thing wasn’t so bad Jamie thought as he worked his lips up and down along Mark’s penis. It was really just like sucking a big nailless thumb and the cum had a sort of pleasant brininess. He reached up and began to craddle Mark’s balls causing the older man to moan out his name.

As Mark began to get more pleasure from Jamie’s cock sucking he started forcing his stick further and further into Jamie’s mouth. He began humping and pushing Jamie’s head down. He thrusted forward and Jamie felt the door of the dressing room against the back of his head. Trapped against the door he was helpless as Mark pounded his hips against his face. The thick cock was forced repeatedly all the way down his throat and Jamie struggled not to tear up and make his make-up run. For a moment Jamie forgot the massive dick abusing his mouth and thought how absurd it was that a week ago he had his dick in Julie’s mouth and now he was worried that he’d ruin his mascara if he deep-throats a cock for too long.

“Ooo yeah baby I’m gunna fill your belly with my cum,” Mark moaned humping harder, banging Jamie’s head against the door.

Jamie placed his hands on Mark’s hips and guided him in when suddenly Mark thrusted all the way in and held there. Jamie could feel the cockpulsing cum inside him, he kept sucking taking every jet of sticky juice he could. When Mark was finally drained dry he slumped back onto a bench in the dressing room.

“Wow you’re amazing sweety,” Mark said. “How old are you?”

“Thanks,” Jamie blushed. “I’m 15, how old are you.”

“Oh wow I’m 21,” Mark answered. “Don’t tell anyone about this and I’ll keep buying you stuff, ok?”

Jamie nodded and the two left the dressing room and walked to the counter to pay for the jacket. Mark plunked down the cash and kept his word to buy it for Jamie. As he handed it to Jamie he slipped his number into the shopping bag and told “her” to call him so he could take “her” shopping again.

They parted ways at the front of the shop and jamie watched as Mark walked away with his friend high-fiving him. He smiled and looked down at his phone.

“Get a guys number,” Julie’s text read.

“Already done, what’s next,” He wrote back.

Dee 13/04/30(Tue)01:36 No. 18806 ID: 9b0c45

Thanks for the nice words about this story. I'm glad you like it!

Anonymous 13/04/30(Tue)03:03 No. 18809 ID: ba1009

Great stuff!!! Don't keep us waiting so long next time. This story is awesome!!

tSade!O9S.2cqv5k 13/04/30(Tue)15:41 No. 18814 ID: e1353d

Yummy! I love his descent, it is so sexy. Thank you very much for posting.

Anonymous 13/05/07(Tue)18:08 No. 18887 ID: 62e7c5

don't want to rush op, but also don't want the story to die

Dee 13/05/07(Tue)23:58 No. 18889 ID: 9b0c45

Don't worry I'm working on it :) and I appreciate the interest!

Anonymous 13/05/09(Thu)05:33 No. 18897 ID: 5c8304

Loving this story, want more!

Anonymous 13/05/13(Mon)06:50 No. 18925 ID: ba1009

Thanks for taking time to write such a good story! Keep up the good work

Anonymous 13/05/18(Sat)15:27 No. 18964 ID: 62e7c5

bumping for the almighty glorious OP

Anonymous 13/05/19(Sun)07:46 No. 18967 ID: f6293f

a bump for the greatest story on /elit/
can't wait for more!

Anonymous 13/05/21(Tue)19:11 No. 18984 ID: 82a74f

this needs update!!

Dee 13/05/22(Wed)15:16 No. 18989 ID: 9b0c45


Jamie strolled down the corridors of the mall, a mischievous smirk on his face, popping his hips left and right like a runway model. He’d been resisting all this up until now. He’d been embarrassed, humiliated, abused and ashamed. All he’d been thinking about was the depraved acts he’d been forced into.

But not right now. Something occurred to him while watching Mark walk away with his friends. Up until this point his love life was rejection on top of rejection. Girls at school barely acknowledged he existed, but when he was dressed up as Jamie all he got was attention.
Guys couldn’t stop staring at him as he strutted through the mall. They whistled, swung their heads around. All he had to do was smile in a guys direction and he could make him do whatever he wanted.

Sure he had to put out, but even that was bothering him less. There was something that got him very excited thinking about a hard cock throbbing and pulsing inside him. He hadn’t wanted to admit it before, but he couldn’t stop thinking about Tommy’s huge cock sliding powerfully into his sissy ass.

Just as he noticed another guy checking out his round bottom, accentuated by the short black skirt Julie, Mandy and Sarah had dressed him in, another text popped up on his phone.

“Get supplies for tonight: Jello packet, bandanas, rope, markers, ky, bananas, condoms,” it read.

Jamie had an idea what some of those might be for and his heart began to beat faster, his cheeks began to turn red and his cock grew in his panties. Were they really thinking of doing what he thought they were?

he turned around and began to walk back toward a convenience store he’d passed a minute ago, wobbling a little on his heels as he did. His long quick strides caused the skirt to lift up exposing his butt. He laughed as he noticed a mother quickly slap her hand over her young sons eyes, her mouth wide in shock.

He spent a few minutes in the store finding all the items, but eventually was able to gather them all -- even the bananas. As he was grabbing the last thing on the list -- the ky -- Julie popped out from around the shelves and yelled “BOO!”

Jamie jumped back in shock and yelped. The heels tripped him up and he fell back on his butt. His legs spread wide showing Julie the large lump in his panties that contained his sissy cock. She giggled as she helped him get to his feet.

“Nice package,” Julie laughed. “Did you find everything?”

“Yeah I got it all,” Jamie replied.

“Perfect!” she answered. “Now turn around and bend over a little.”

“What?!” Jamie exclaimed. “Why?”

“Just do it and I’ll take you to the car,” she promised.

Jamie agreed. He quickly looked around and saw that the store was pretty much empty. He bent slightly at the waist and put his hands up on the shelf in front of him. Julie smiled and flipped the skirt up over his ass. She reached forward and gently tugged the front of the thong down just a little and slapped a flesh colored sticker just inside his hip. She pulled the panties back up and the skirt down and told his he could turn around.

Jamie reached down and ran his fingers over the sticker, which felt like a large square band-aid.

“What the hell was that?” he asked.

“Oh nothing,” Julie smirked. “Come on now the girls are waiting!”

The two teens went to the counter, paid for the items and re-entered the mall corridors. Julie guided Jamie through the mall, the two of them turning head the whole way. They made their way to the center of the mall and stopped at the glass elevator that bordered the food court.

Julie pushed the up button and the doors opened. They stepped into the elevator and looked out through the clear back wall. On the other side a group of guys around their age sat laughing and eating. One of the guys looked up and saw them walk into the elevator. He signaled his friends who proceeded to whoop, wave and blow kisses at Jamie and Julie.

Jamie, who was feeling more and more comfortable playing the role of “hot chick,” waved coyly and even blew a few kissed back. Julie laughed at the dirty little flirt she’d created just as an idea popped into her head.

“Oh you have to moon them!” Julie exclaimed.

“No way I’ll get caught,” Jamie replied.

“Oh come on you’ve got such a cute butt,” Julie said. “You should show it off.”

Jamie grinned turned, bent over and quickly lifted the skirt wiggling his bare bottom at the group of guys. This sent them into a frenzy hollering and high-fiving each other. Jamie turned around to blow them one last kiss as the elevator began to rise. Just as his did Julie, in one quick motion pulled the skirt and thong down down around his knees.

A look of shock popped onto Jamies face as he looked down at the semi-hard dick swinging between his legs. He looked up and saw the guys shocked faces staring at him. They shrank slowly as the elevator rose and Jamie yanked the skirt and panties back up over him.

“WHAT THE FUCK!” he yelled at Julie who was laughing uncontrollably. “That wasn’t funny!”

“Yes... it... was,” Julie managed to answer between bouts of riotous laughter.

Jamie left the elevator in a huff, strolling quickly ahead. He left Julie in his wake, but only got a few yards from the elevator when he felt a strong hand grab his arm. Jamie turned to see a tall slightly overweight security guard towering over him. His stomach knotted up as he looked at the guards stern face.

“Miss,” he growled. “you’re going to have to come with me.”

Anonymous 13/05/22(Wed)18:55 No. 18990 ID: 82a74f

oh i can tell where this is going =]

Anonymous 13/05/22(Wed)21:30 No. 18992 ID: 7e2b62

It both amuses me and turns me on that you allow Main character his dreams (delusions) and then beat him down with the hard throbbing 'reality'

Anonymous 13/05/22(Wed)23:14 No. 18993 ID: ba1009

Another great chapter. Thanks

Anonymous 13/05/28(Tue)17:53 No. 19035 ID: 62e7c5

just bamping to let OP know we're still reading

tSade!O9S.2cqv5k 13/05/28(Tue)22:30 No. 19036 ID: e1353d

Yep, evil cliffhanger filled with potential. :)

Anonymous 13/06/03(Mon)04:03 No. 19077 ID: f6293f

Anxiously awaiting the next chapter OP, keep it up :)

Anonymous 13/06/09(Sun)07:07 No. 19119 ID: 62e7c5

so I guess OP died, all good things must come to an end I suppose

Dee 13/06/12(Wed)01:56 No. 19156 ID: 9b0c45


The guard held Jamie by the upper arm and began to drag him through the mall toward the guard station. Jamie looked around desperately searching the crowd for Julie, but couldn’t find her among the dozens of people streaming through the mall.

Jamie’s throat dried and his lip quivered. He choked back a sob, but felt very close to breaking out into full blown tears. He looked up at the guard; he had close cut hair and milk chocolate colored skin. He looked like he had been quite strong a decade or so ago, but advancing age had robbed him of his physique.

They passed through a door into the outer chamber of the guard station. A secretary sat at the front desk flipping through a magazine with long fake nails. Her big hair swayed as she looked up at Jamie being escorted in. Looking him up and down she flashed a dirty look. Her face said it all, “What a slut.”

The guard and Jamie strolled down a hallway and entered the second door on the left, which led into a small room containing one old wooden desk and two chairs. A nameplate on the desk read “Guard James Wade.”

Guard Wade spun Jamie down into one of the chairs and then casually sat on a corner of the desk.

“Do you know why I brought you here?” Wade asked.

“No,” Jamie lied.

“I saw you mooning on the elevator,” Wade said. “That sort of behavior is strictly prohibited here. Now I need to know your name and phone number, so I can have your parents pick you up.”

Jamie’s heart began pounding in his ears. He yelped and at a near panic began to beg for forgiveness. “Oh please sir no I promise I will never do that again,” He pleaded. “I know it was wrong, I’ll do anything! Just please don’t call my parents.”

It had never occurred to him that his parents might catch him dressed as a girl. He had no idea what they’d do, but he was sure his father -- a man’s man if there ever was one -- would at the very least give him the beating of a lifetime.

Guard Wade thought for a minute, scowling down at Jamie, then a small smirk crept onto his face. He told Jamie to stand up and put “her” hands on the desk.

“I’m going to have to frisk you to check for contraband, miss,” Wade explained as he placed his hands on Jamie’s waist. He slowly ran his large hands up Jamie’s sides, following the contours of his body. He stopped at Jamie’s armpits, sliding his hands forward he ran them under Jamie’s “tits” and gently fondled them. Jamie felt a large cylindrical object press against his thigh. He bit his lip nervously.

Wade began to work his way down to Jamie’s hips then continued to his ass. He slid his hands under the skirt, lifting and parting the cheeks, squeezing them in both hands. He flipped the skirt up exposing Jamie’s bottom covered by pink panties.

“Well, well, well,” Wade said. “So this is what you felt the whole mall needed to see. I must say it is a pleasant sight, but miss it’s dangerous to show off like that in public. A man might get the wrong idea.”

“I know sir,” Jamie said with his hands on the desk arching his back, raising his butt in the air. “It was stupid and promise I won’t do it again.”

“I’m sure you won’t,” Wade said, “But I at least have to punish you for breaking the rules.”

He sat on the chair, grabbing Jamie’s wrist and pulling him down across his lap. With his skirt still flipped up Wade pulled the panties down just enough to expose two smooth milky white ass cheeks. The guard reached down and slowly unhooked something from his belt.

He raised it showing Jamie the hard, cold, black nightstick he carried with him, letting it fall gently across Jamie’s ass. Jamie bit his lip harder and looked up pathetically at the large man. Wade looked right into Jamie’s eye as he raised the stick. He brought it down swooshing through the air and connected squarely across both Jamie’s cheeks, holding the the club against his ass again. Jamie cried out with a high pitched wail. He felt the strike from the nightstick like a bolt of electricity that shot through his body.

Wade raised it again, bringing it down just as hard hitting Jamie’s sissy ass again. Jamie groaned and whimpered as the jolt from the hit travel from his ass to his stomach and up to his jaw, which clenched tight.

Wade was relentless bringing the stick up and slamming it down again and again and again. Jamie began to squirm, cry and beg for him to stop, but at the same time for some reason he couldn’t explain his cock began to harden in his pink girly panties. As Wade brought the big black pole whipping down for a twelfth time Jamie shifted and pressed his cock against Wade’s thigh.

Wade looked confused for a moment then angry. He lifted Jamie sobbing to his feet. He stood legs shaking, knees apart with his ass end to Wade. The guard reached forward and ran his hands quickly up Jamie’s thighs over the front of his panties. In one big hard he squeezed down on Jamie’s balls and small hard shaft.

“What the fuck is this?” Wade growled.

Jamie looked back into the large man’s furious eyes. He gasped, stammering and stuttering, but failing to get any words out. Wade pulled the panties to the ground violently, and watched as the sissy’s balls and little hard cock flopped down between his legs.

Wade looked at the cock then at Jamie. He began to bellow incomprehensibly at Jamie, who could only make out “fucking pervert” and “crossdressing faggot” amid a flurry of swears and slurs. Jamie looked back terrified at the enraged security guard, totally exposed.

Wade flew to his feet, grabbed Jamie’s long blond hair and slammed her head down onto the desk with his left hand. His right hand raised high in the air began raining blow after blow against Jamie’s already bright red ass. He wasn’t in control as he had been before. The strikes were coming faster and much less accurately. Some connected to the meat of his ass, but others hit his tail bone or upper thighs. Jamie was barely able to make any noise as the blows came so fast he was running out of breath. All that he could get out were small squeaks, “eek, eek, eek”s of protest. Tears ran down his cheeks.

Wade, huffing and puffing, looked down disgusted at the pathetic little he/she he’d mistaken for a sexy teen girl. He switched his grip on the night-stick and sneering meanly pressed the tip against Jamie’s boy-pussy. Without lube or waiting for Jamie’s still tight teen anus to adjust to the hard object Wade pushed as hard and quickly as he could.

Jamie cried out, feeling the plastic tip of the stick push his pink hole several inches in before it popped open accepting the object. He felt his stomach jump and a shot of pain and pleasure shoot from his feet upward as the shaft moved quickly inside him, sliding fast past his quivering hole. The stick wasn’t as thick as the cocks he’d taken, but it was several inches longer and he felt an uncomfortable pressure in his stomach.

Wade began to mercilessly pump the nightstick in and out of Jamie’s ass. He looked down watching as the unlubed stick would pull the young boys asshole out several inches as he withdrew it then would push it in several more as he slammed it back in. He shoved the long shaft as far up as he could, leaving it there.

Wade lifted Jamie by the hair, twisting him around and plopping him down on the ground next to the desk. Jamie’s was on his knees, feet tucked under him, with the few inches of black night-stick poking out of his bottom touching the ground. Wade held his hair, forcing his head back on the desk with his neck pressed uncomfortable against the edge, body curled under him. He reached back and grabbed Wade’s arm, but didn’t have the strength to free himself.

Wade moved in front of Jamie with his back to him, still holding Jamie’s hair behind himself. He unbuckled his belt and let his trousers fall to the floor then pulled his boxers down exposing a large black ass. A huge half stiff cock huge between his legs and two big hairy balls.

“Now lets see that faggot tongue you little freak,” Wade snarled over his shoulder.

Jamie pursed his lips and shook his head, fear in his eyes. Wade pulled his hair back digging the edge of the desk into his neck. Jamie squirmed and struggled, but as he did he moved the nightstick buried in his ass causing pleasure and pain to emanate from his hole. He closed his eyes, crinkled his nose and stuck his tongue out just a bit.

Wade shuffled back moving his two large, round, black cheeks on either side of Jamie’s girly, innocent, teen face. As the black fleshy mounds began to come close Jamie opened one eye a crack peeking into the dark crevasse. Dark tangled brambles of hair poked from between a chocolate colored valley that centered around a near black puckered hole. The smell was earthy and pungent. A mix of sweat and body smell, with just a hint of musty shit.

Jamie’s face disappeared between the black man’s cheeks as Wade sat back on the young “girl’s” face. Jamie felt his tongue make contact with skin and was surprised to find that it didn’t taste terrible. The hair felt rough on his tongue, but as Wade began to rub his ass up and down against Jamie’s face, Jamie felt his tongue touch asshole. He gasped a little letting his tongue slip out further.

Wade lifted up dragging his ass then his big heavy balls across Jamie’s made-up face. His chest covered in a stuffed bra heaved under him, his skirt had fallen back down, but stuck up in the front raised by his hard dick. Wade grabbed one of Jamie’s hands and pushed it through his legs. He put Jamie’s hand around his cock -- it didn’t make it all the way around the thick shaft -- then closed his over big hand over it. He began to slowly rub Jamie’s hand over his cock, sitting back more, pressing down on Jamie’s face.

Jamie could barely breath, as his tongue was pinned outside his mouth pressed flat against the back man’s asshole. Wade rocked his hips, grinding his asshole over the warm wet tongue. As the two of their hands moved faster and faster up and down Wade’s cock Jamie’s body moved as well causing the long shaft he was sitting on the move circularly inside him. The sensation of his insides being stirred by a foreign object cause his cock to harden further, even as his saliva was coating another man’s asshole.

“Oh yeah you little slut eat that ass,” Wade moaned his fury subsiding as his pleasure grew.

Jamie felt the large man’s cock begin to bulge and throb harder in his hand. He gasped for air, but all he could suck in was black skin, causing his tongue to slide quickly into Wade’s dark hole. Wade moaned loudly and suddenly Jamie felt a rush of fresh air followed by a large, round, black cock head stuffed into his mouth. Jamie collapsed downward as Wade let go of his hair causing the nightstick to push another couple inches inside him. At the same time Wade unloaded jet after jet of thick cum into Jamie’s sissy mouth.

Jamie sat on the long, black pole with a mouth full of cum, but before he could swallow Wade pulled his cock back then brought his heavy wide hand down slapping Jamie hard in the face. Jamie was knocked sideways, his mouth opened spraying the huge load of cum across the floor, falling to his hands and knees. As he did Wade grabbed the handle of the night stick and ripped it out of Jamie’s ass. He swung it back in a circular motion then followed through bringing it up between Jamie’s legs squashing his little pink balls against his pelvis with a sickening thwack.

Jamie yelped like a puppy being stepped on underfoot. He jolted forward, knees clenched together, onto the floor in the fetal position. He mouth hung open. With one wet sounding cough he brought up a thick glob of cum that hit the floor in one sticky mass.

“Gunna flash your faggot ass around here again?” Wade taunted at the silent shaking sissy-boy. “Didn’t think so.”

Dee 13/06/12(Wed)02:01 No. 19157 ID: 9b0c45


Nope I'm not dead, it just takes me some time to get out another chapter. Have to find the time and be in the right mood. If you know what I mean ;)

Anonymous 13/06/12(Wed)02:23 No. 19158 ID: ef29e2

Yes! The story continues! Don't ever stop Dee

tSade!O9S.2cqv5k 13/06/13(Thu)15:43 No. 19173 ID: e1353d

Oh, I liked it a lot. Thank you.

Anonymous 13/06/24(Mon)04:44 No. 19259 ID: ef29e2


Dee 13/07/03(Wed)15:13 No. 19301 ID: 9b0c45


Jamie dressed in silence then slowly walked out into the hall. His legs were pressed close together, pain still radiating out from where the security guard smashed his nightstick into his balls. When he got to the entrance he found Julie waiting there for him.

“Oh my god are you ok,” Julie asked as she shot to her feet and gave Jamie a hug.

“I’m fine,” Jamie replied angrily as he kept moving toward the door.

He stepped out into the mall, Julie following close behind. He didn’t care how he looked. He didn’t care that his hair was a mess, that his mascara was streaked from tears or that his skirt was hiked up too high. He and Julie rushed through the crowd and out to Sarah’s Jeep. Along the way he told Julie what Wade had done to him and demanded she take him home. He never wanted to see her again, he thought.

When they got to the car Sarah was at the wheel with Mandy next to her in the front seat. Julie and Jamie got into the back as the two older girls asked about what had happened. Julie explained and suggested they bring Jamie straight to his house.

“Fuck that,” Sarah replied.

“Sarah he was basically tortured,” Julie pleaded.

“Look, I thought you wanted to make him your sissy slave,” Sarah said.

“I did,” Julie nodded.

“Then you need to toughen up and quit taking all his shit,” Sarah said sternly. She turned to Jamie, reaching back and clamped her hand down on his balls. He cried out and put his hands around Sarah’s arm, but he couldn’t get her off. He gasped in intense pain as his balls were already sore from earlier.

“Ok bitch,” Sarah said to Jamie, “now I don’t want to hear anymore ‘Oh, I don’t want to do this’ or ‘I’m not doing what you say.’ Shut-the-fuck-up.”

Jamie bit his lip and nodded.

“You belong to Julie now and you’ll do what she says,” Sarah commanded. “You are a girl now, and a slutty one at that. Do you understand?”

Jamie nodded again, but tried to pull her hand off his balls again.

“No! Hands at your sides,” Sarah barked. “Those aren’t your balls anymore those are Julie’s and only she can get me off them. Now are you ready to do everything your mistress tells you?”

“Yes, yes please I am!” Jamie cried.

“Good, first things first, fix your makeup,” Sarah said as she released her grip on his nuts.

Jamie, with Julie’s assistance, wiped away the tears and smeared makeup and re-did “her” face. Jamie looked in the mirror and recognized the young girl looking back. He’d become familiar with “her” and she’d been through a lot in the last week. He took a deep breath and resigned himself to just a little more abuse. However, he thought to himself that this was it -- he’d never allow them to make him Jamie ever again.

As the girls drove through the city streets toward Julie’s house Julie whispered in Jamie’s ear trying to reassure him that he’d have fun. She promised she wouldn’t hurt him, that he’d get to have fun too as long as he did what she and her friends said. Jamie was silent still angry over what happened at the guard station, but at least the pain had mostly subsided. He closed his eyes and felt the wind through his hair as the four of them sped on with the top of the Wrangler down.

The Jeep came to a stop at a red light and a convertible full of guys pulled up next to them. They began hooting out catcalls and asking for the girls numbers. Mandy, the more playfull of the bunch, pulled her shirt up and bounced in her seat. Her large milk white breasts heaved up and down, the pink nipples pursed up and pointy in the cool evening air. Jamie smiled and reached around the seat and cupped her tits in his hands squeezing and lifting them then letting them drop. If he had to be here he’d at least make it worth his while. The guys in the car went wild over the perceived lesbianism.

Mandy laughed and turned in her seat, her boobs still bare. She reached back and pulled Jamie up. Jamie moved in and felt her warm breath on his cheek. Her full lips came to his. They were soft but planted firmly against his mouth. She tasted of strawberry lip gloss and smelled of perfume. Her tongue slipped between his lips exploring his mouth. Finally, he thought, maybe this whole dress-up thing would pay off.

From the other car the guys were going wild watching the two “girls” make-out. They looked young and hot, their tongues darting into each others mouths, eyes closed. One even had her tits out. The cars were quite close, maybe three feet apart as the boys leaned over the get an even better look. One of the guys in the back seat stood and pulled his gym shorts down just enough for his hardon to pop out. He readjusted his shorts so the elastic waistband was tucked behind his balls. He threw his legs over the side of the car and sat on top of the door stroking himself.

Mandy pulled back from the kiss with Jamie as the light turned green. The two cars accelerated next to each other with the one boy still sitting partially outside exposing himself to the girls. They came to a stop at a light a block down the road. Jamie looked forward at the straight expanse in front of them. There were another half-dozen lights before their turn.

The girls were giggling at the sight of the boys cock flopping in the breeze.

“Go touch it!” Julie exclaimed to Jamie, who was the closest to the boy.

Jamie began to object, but remembered the vice like grip Sarah had on his balls, which caused him to choke back his complaint. He leaned out the window and flashed the boys a girly smile then reached out and gently laid his hand on the boys dick. As he did the light turned green and the cars lurched forward. Jamie fell forward slightly and tightened his grip around the cock for balance, making the boy moan aloud with pleasure.

At the next light Julie pushed Jamie a bit further out of the car. His hips were balanced on the side of the Jeep and one hand was firmly holding the car as the other was still around the strange man’s penis. The boy reached out and grabbed Jamie’s hair lifting “her” up toward his crotch. He pulled Jamie’s hand away and pointed his meat at Jamie’s mouth.

Jamie closed his eyes and felt the warm round flesh touch his lips. They parted as they had for the other cocks before -- he had now had four other dicks in his mouth -- allowing the swollen head to slip inside his mouth. He pushed his tongue out sliding it down the shaft flattening it out and curling it lengthwise around the boys dick. He swirled it around coating the cock in saliva as he began to push more of it into his sissy face.

The light turned green and the two cars sped off again, the drivers attempting to keep them perfectly even. The boys car hit a pothole causing the car to bounce down then sharply up. The boys cock thrusted out then quickly in because of the bump plunging it deep down Jamie’s throat. He was getting better at accommodating dicks down his throat, but the quick move caught him by surprise. He eyes went wide and his mouth gaped open, the boys balls pressed against his chin. On the streets no one could see what was going on between the vehicles and behind them a loan sedan with two middle-aged women in it looked on aghast.

Julie had her hands on Jamie’s hips holding him, ready in case “she” need help back into the Jeep. Mandy turned back and flipped Jamie’s skirt up and pulled his panties back exposing the sissy’s cock and ass to Julie. She looked down at the hairless crack with the wrinkled pink hole at the center -- still slightly open from it’s encounter with the nightstick.

Julie leaned in and slurped the balls into her mouth rolling them around with her tongue, her nose pressed against her sissy slaves asshole. Jamie moaned with pleasure, his mouth and throat full of thick hard cock. His moaning causing a slight vibration that transferred to the boy who was building toward orgasm.

Julie reached down and took Jamie’s girl-meat in her hand and stroked it downward as though she were milking a cow. She moved her hand expertly putting just the right amount of pressure on the shaft while she sloppily slobbered on his balls. Each time the cars came to a stop at a light Jamie would bob his head on the dick then hold on for dear life as they took off again.

As the cars came to the last light Jamie worked the boys cock as voraciously as he could. He rocked his head back and forth and swirled his tongue around the base. He pulled back pressing his lips tightly around the thick meat licking hungrily at the tip then pushing back down taking it deep down his throat. All the while Julie stroked his sissy-dick coming closer and closer to causing an eruption.

Just as the light turned green and the Jeep began its turn Jamie felt the boys cock swell in his mouth and begin to shoot jets of warm cum. In the middle of the boys orgasm the cars slipped apart and Jamie looked on as the boy moved away spouting cum onto the street. Jamie collapsed forward losing the other car around the corner and relaxed allowing his own cock to spurt his own “milk” onto the Jeep’s back seat.

When he had shot the last of his load Julie let his balls slip for her mouth and pulled him back inside. He looked down at the puddle of cum he’d left and blushed.

“Well done slut,” Sarah called back to him. “Now, clean up your mess!”

Jamie frowned and bent down. He knew how the girls would want him to clean up. He put his face next to the milky pool and began to lick and slurp up his own jiz. Julie held her toy’s hair back as “she” licked the seat clean. When Jamie had finally eaten all the cum he could get off the seat, the car pulled into the driveway at Julie’s house.

“Ok,” Julie smiled. “Ready for the real fun to begin?”

Anonymous 13/07/03(Wed)17:01 No. 19304 ID: ef29e2

Good stuff! Can't wait to see what happens next

:((( 13/07/03(Wed)17:48 No. 19305 ID: 41b2e3

This is great so far, but am I the only one who wants Jamie to be cut some slack? I know it revolves around him being a complete sissy, but maybe give him some glory by having at least one thing go his way, maybe Julie finally hooks up with him or Sarah gives him a reward for what he's been through. Feel free to ignore this, but it'd free up the plot for new twists and I for one feel a little bad for Jamie as he's been dicked around with so much (pardon the pun)

Anonymous 13/07/03(Wed)23:20 No. 19308 ID: e38a5d

I don't see your point. It sounds like Jamie's getting all cock he wants deep-down, isn't he?

Dee 13/07/03(Wed)23:57 No. 19309 ID: 9b0c45


I see where you are coming from (he has had it kind of rough), but his story is about a transformation (with a lot of sex along the way) so having him get some "glory" (at least in the way I think you mean) would actually be a step backward for him. I'm not saying it won't happen though (I don't want to spoil the story). I hope that this makes sense :) and thanks for the input!

tSade!O9S.2cqv5k 13/07/04(Thu)18:27 No. 19316 ID: e1353d

I found the Sarah's response to be a bit sudden, but otherwise I loved it.

Anonymous 13/07/04(Thu)20:20 No. 19318 ID: e38a5d

This is a great story. I don't know why I find the idea of turned into a cute slutty girl such a turn-on but I do -_-;;. I loved all the chapters except for the rape chapter since I find interracial disgusting, my favorite chapter is the last one where he makes out with Mandy like he's one of the girls but it was all so he could turn on the boys. He's really like a slutty teenage girl now. I wish I was him.

Anonymous 13/07/15(Mon)10:29 No. 19371 ID: f6293f

Anticipation bump

Anonymous 13/07/15(Mon)15:33 No. 19372 ID: 270179

Sucks to be him. Or it's awesome. Guess it depends on perspective.

Anonymous 13/07/23(Tue)10:33 No. 19433 ID: 51236a

I *NEED* the next chapter!

Anonymous 13/07/23(Tue)16:03 No. 19435 ID: 2b3979


Anonymous 13/07/27(Sat)10:45 No. 19452 ID: f6293f

The next chapter can't come sooner

Anonymous 13/08/03(Sat)21:50 No. 19496 ID: db79ea

I need the next chapter

Anonymous 13/08/04(Sun)03:31 No. 19500 ID: 366e5d

I NEED the next chapter

Anonymous 13/08/06(Tue)07:36 No. 19514 ID: 53f2a1

your need won't make the next chapter come out any sooner

Anonymous 13/08/06(Tue)07:36 No. 19515 ID: 53f2a1

your need won't make the next chapter come out any sooner

Anonymous 13/08/11(Sun)16:08 No. 19550 ID: 1d4f84

begging for an update...please!!!

Anonymous 13/08/18(Sun)05:16 No. 19572 ID: 7b8d0a

i'm sincerely looking forward to any scenes with Julie and Jamie, especially when there's a banana and a bandana involved

Anonymous 13/08/20(Tue)05:27 No. 19579 ID: 7da388

Enjoying this story, hope you keep writing OP.

Anonymous 13/08/21(Wed)02:00 No. 19583 ID: ba9ff7

I hope there's more cum in the next chapter!

Anonymous 13/08/24(Sat)20:13 No. 19592 ID: 270179

Dangit, man (or woman, I dunno, dude),I don't want to wait for the next one! But the more time you take, the better it will be in all likelihood. Good work.

Anonymous 13/09/15(Sun)19:27 No. 19720 ID: a289d7

please don't let this die :(

Anonymous 13/09/19(Thu)23:35 No. 19738 ID: f6293f


Anonymous 13/09/22(Sun)19:52 No. 19754 ID: 8f305c

BUMP in hopes this continues

Anonymous 13/09/22(Sun)22:11 No. 19756 ID: 6a2949

tfw you will never make out with cute girls and suck hot guy dick

Anonymous 13/10/12(Sat)22:25 No. 19906 ID: f6293f


Anonymous 13/10/13(Sun)00:17 No. 19909 ID: 0976da


Anonymous 13/11/02(Sat)15:06 No. 20055 ID: 09b4bb

is dee kill

Anonymous 13/11/03(Sun)16:59 No. 20069 ID: b61645

so mourn is ded

Anonymous 13/11/11(Mon)23:52 No. 20167 ID: f6293f

Such wasted potential

Dee 13/11/12(Tue)00:31 No. 20169 ID: 7c9baf

Wow I didn't realize it'd been so long since I updated this! So sorry for the delay, but I am back to writing and will post some updates soon!

Dee 13/11/15(Fri)01:40 No. 20200 ID: 7c9baf


Jamie looked up at Julie's house from the backseat, his mind flashing back to the events of the previous weekend. Since Julie had first dressed him up and he was discovered and de-virginized by her brother and his best friend, Jamie had come a long way, and the last few hours at the mall had been a rollercoaster for him.

His head was buzzing with thoughts and he wasn't sure what to make of himself. He caught a glimpse of himself in the car mirror and it made his cheeks burn. There staring back at him was the face of a blond nubile, one he'd grown familiar with very quickly, but he still didn't recognizer her as himself.

He pulled his coat on and his mind flashed back to the dressing room with a cock being pushed down his throat as payment for the coat. His stomach did a flip at the thought. Swinging his feet out the door he landed shakily on the high heels he'd been wearing all night. They were quite high and the heel chunky. Black straps closed around his ankles.

He strode toward the door in the wake of Julie and her two friends. The long peacoat extended below his skirt, making it hard for anyone two tell if this young “ladie” was wearing anything under it at all. Jamie crossed the threshold of the front door and looked around toward the living room where he encountered Tommy and Chris last weekend, then watched the girls disappear around a corner.

Following their lead he rounded to the back side of the home entering a large brightly lit modern kitchen. Mandy grabbed the jello packet and began boiling some water.

“For jello shots,” she smiled mischievously back at the others.

“Come here and sit down,” Julie cooed at Jamie and pulled out a chair.

Jamie sat and Julie pulled a chair up in front of him. She pulled one of his feet, still wrapped in the black high heel, and placed in in her lap. Looking into his eyes Julie ran her fingers along his calf and down to the strap, undoing it. She smirked at the stubble in his leg, it had been a day since he shaved them, which he had always done for the swim team.

“Well babe we sure put you through a lot,” Julie smiled. “I think it's time for a little pampering and girl talk.”

Sarah dropped her ipod into a dock on the counter and pulled up her best “party” playlist to which the other girls “woo-ed” and “ow-ed.” Julie pulled out a kit to give Jamie a full mani-pedi and got to work on his toes. Mandy meanwhile was pouring what looked like half a handle of vodka into the jello mix before parking it in the freezer to firm up.

“So um, Jamie,” Julie giggled, “Mandy has been hanging out with Josh, uh Josh Douglas and they fooled around, but well you've seen him in gym class – is he... equipped?”

Jamie turned beat red and stammered a bit, which caused the girls to burst out laughing.

“Oh come on, this is great” Julie said still working on his toe nails. “We've got a new girlfriend with inside knowledge about the dick size of practically every guy in school! Please we need this information!”

“I... I can't that's like against guy code,” Jamie replied.

“You don't look much like a guy to me,” Sarah shot back.

“Come on Jamie, we might be able to share some inside info with you too ya know,” Julie promised.

Jamie smiled and bit his lip. Who would find out he'd talked about this stuff? Plus getting the inside scoop on the other girls could be a major help to his sex life – his straight sex life at least. The lure of such juicy gossip was too much for him.

“Alright,” Jamie smirked in a hushed voice. “Josh is pretty big, a good seven inches I'd say and it's well groomed. Who else do you want to know about?”

The four gossipy girls went back and forth for more than an hour talking about the size of their classmates dicks, which girls were the easiest, what guy has a good six pack and which girls shaved their bush. Julie completed Jamie's mani-pedi and even gave his legs a pass with the razor. By the end of it the jello shots were done and they each took one contained in small dixie cups.

“Well here's to a fun night,” Mandy toasted and they all slurped the shots down. Jamie scrunched his face at the strong taste of booze in the small shot.

“Let's move this party to the basement,” Julie suggested. “My parents are going to be home any minute.”

Anonymous 13/11/15(Fri)23:32 No. 20216 ID: cf7dc5

he's back!

Anonymous 13/11/16(Sat)11:13 No. 20221 ID: 123a5f

Still don't know what that "sticker" was.

Anonymous 13/11/22(Fri)08:11 No. 20319 ID: ad13d4

please hurry

Anonymous 13/11/22(Fri)19:53 No. 20324 ID: 9d2239

I think it means she put Jamie on harmones...

Anonymous 13/11/25(Mon)03:37 No. 20336 ID: 99b796

fuck that's hot

Dee 13/11/27(Wed)00:36 No. 20346 ID: 7c9baf


Jamie slurped another jello shot as the three girls filed down the stairs to Julie's basement. Jamie turned and followed down the narrow staircase and blinked his eyes as they adjusted to the dimmer light. He smirked at the basement decor.

Julie's parents must have held onto every piece of 70s furniture they owned and recreated their first apartment in their basement. The lime green sofa and rust color arm chairs clashed completely. The walls featured trippy art work of various sized circles and the floor was complete with a white shag rug. The only modern things in the room were a new bench press and weigh rack and a flat screen tv.

“Julie, 'Happy Days' called and it wants it's sets back,” Jamie teased.

“Yeah my dad hasn't moved on style-wise since 1977,” Julie laughed. “Thankfully my mom banished this stuff down here.”

Mandy and Sarah took over the couch and Julie had staked out a chair, leaving Jamie to sit as “lady”-like as possible on an old red bean-bag chair. The girls passed around another shot, but Jamie was already starting to feel a buzz. They sucked them down then Sarah turned to Jamie.

“So you got a guys number right?” Sarah asked.

“Yep, his name's Mark,” Jamie replied smiling.

The girls giggled and exchanged devious glances.

“So, um, how'd you get a number before we even told you to?” Mandy asked.

“Oh, I, uhh, I...” Jamie stammered looking for the words. He looked down realizing that it was time to come clean. The girls knew about the guard station and they saw him suck off the boy in the car. His stomach twisted in knots. Telling them everything would guarantee he'd never get with Julie. But who else could he talk to about what he'd been going through?

“He started hitting on me in the store,” Jamie answered. “So I got him to buy me the coat, and I got his number, and I... and I blew him in the dressing room,” Jamie confessed.

“Ow, ow, ow!” the girls responded in unison.

“So is that all you've been up to?” Julie asked. “Because I was wondering, those panties you borrowed last weekend, where'd the cum stains come from?”

Jamie blushed and hung his head. He took a deep breathe then looked up at Julie and said, “Chris... and your brother.”

“Oh shit!” Sarah exclaimed. “You dirty skank!”

“I'm so sorry,” Jamie pleaded. “I was just going to change back and get out of there when Chris found me...” Jamie explained telling all three exactly what happened. He told them about how he'd felt the week after – scared, ashamed, but unable to get it out of his mind – he told them about how he felt in the mall with the guys checking him out and buying him stuff. Maybe it was the shots, maybe the stress of what he'd been through, but he finally snapped and poured out his guts to them. Finally he told them what he'd been feeling all night – that he felt better as Jamie than James.

Julie looked down fondly at him. She got up and slid down next to him in the bean bag chair and kissed him softly on the cheek.

“I'm so happy for you,” she whispered.

“Yes, we're all very happy for the little slut,” Sarah scoffed. “But, if you remember we do have a time frame here.”

“Oh would you lighten up,” Mandy replied. “You clearly have this one in the bag. We can take some time and have a bit of fun too.”

Mandy got up and flipped some music on then downed another shot. She started dancing around the basement and pulled Julie to her feet. They laughed and twisted to the music, then extended a hand each to Jamie pulling “her” up with them. All three jumped and danced together, while Sarah moved off and began digging through her bag.

The girls grinded and danced around the dated furniture, taking shots every few minutes as the music slowed. Jamie let himself fall into the moment, swaying and moving to the music. He closed his eyes and shimmied his hips, bouncing his full ass up and down to the beat. He kept moving losing himself further into the beat of the music, rocking his hips faster up and down. He put his hands on his thighs letting him shake his bum up and down even harder.

Looking up he found himself next to one of the basement's metal support posts. Grabbing it in his hand he danced and spun around it. He hung off the pole then humped against it, moving like the go-go dancers he'd seen pole dancing in movies. He danced faster, harder, faster. His eyes closed moving with the beat. The song stopped.

He opened his eyes and blinked, looking around. Julie and Mandy had stopped dancing. They were standing on either side of Sarah who was holding a large camera. Jamie went beat red. He was so buzzed he hadn't noticed Sarah taking photos at all. Well this wasn't the first time he'd be photographed like this, he thought. What would he have to do this time?

“So what's Mark's number?” Sarah smiled. Jamie gave her the number and the girls started up loading the photos. They laughed and oooed at the photos of Jamie shaking “her” ass to the music. The girls agreed to a few that would definitely keep Mark interested in a further relationship. Jamie looked at himself on the screen totally surprised at how free and relaxed he looked moving to the music as Jamie.

He reluctantly agreed to sending the photos, but felt relieved he wasn't being outed to someone he knew.

Hardly a moment passed between when the girls sent the photos and Mark's response.

“God you're hot baby,” he texted. “Any chance at seeing more?”

The girls looked around at each other.

“Well, lets get to it then” Mandy said.

Jamie looked around nervous. He could tell the girls again had some plan in their heads.

“What? What are you going to do?” Jamie asked timidly.

The girls converged around him and pushed him down on the rug. Mandy took some of the rope Jamie had bought and bound his feet, while Sarah moved forward and bound his wrists. Jamie started to question what was happening, but Sarah took one of the bananas still in its peel and put it against his lips.

Jamie's vision was blurred and his inhibitions lowered by the alcohol. When he felt the large phallic object against his lips he naturally opened them and began sucking. He took the thick fruit down his throat until there was less than an inch poking out between his lips. Jamie, in his drunken state, had his gag reflex numbed to the point he could have kept the banana down his throat indefinitely. Sarah told him to hold it there.

As the girls were binding his hands and feet Julie stripped his skirt and top off, leaving him in his matching pink bra and panties and the white stockings and heels. She pulled out some of the markers and handed them to the girls. They all began drawing on his body. Sarah drew small angel winds by the shoulders, while Mandy wrote “whore” and “Skank” along his thighs. Julie drew a male and female symbol on each butt cheek and an arrow pointing to his crack. Above it she wrote “Fuck hole.”

The girls spent a few minutes writing various insults over Jamie's body. Then Sarah handed a nervous looking Julie the condoms and banana. Jamie looked back at her as she knelt behind him biting her lip, then pulled the panties down a little exposing his ass. Sarah squirted some KY on Julie's fingers, which Julie slowly began to rub between his cheeks.

He dick engorged in the panties as he felt Julie slowly circle her finger around his tight boy-hole. Sarah pushed his shoulders down so his upper body lay against the shag carpet making his ass stick up in the air. He moaned softly on the banana as he felt Julie's finger slide quickly inside him. She pushed it in and out then worked in another.

He felt his hole loosening up, the walls expanding giving him that glorious full sensation he couldn't get enough of. She briefly slid a third finger in then held them there for a moment. She pulled them out and slid a condom over the banana. Pointing it like a gun aim at his hole she moved it forward. Jamie could barely contain his pleasure as he felt the fruit between his cheeks. His hardon popped out of the panties and he moaned louder with ecstasy.

Julie pressed the tip against his hole, which accepted it easily. She pumped it back and forth through his hole. She pulled it out and pushed it back in over and over. Each time the feeling of his pink hole being pushed in then surrendering to the phallus made bolts of electric pleasure shoot through his body.

Finally Julie pulled it out and stepped back. Jamie looked back at the three girls, covered in drawings and insults written in marker, bound at the ankles and wrists with a banana as a gag. His hole remained open and inch or so gaping up at the girls. Sarah snapped several photos of him, but didn't send them to Mark this time.

Jamie's world spun around him. Completely wasted he collapsed on his side. Julie knelt down next to his head and pulled the banana inch by inch out his mouth. She leaned close to his ear.

“So you like my brother, huh?” She whispered.

Jamie heard foot steps on the basement stairs. He looked up just as Tommy reached the bottom step and with that he blacked out.

Dee 13/11/27(Wed)00:36 No. 20347 ID: 7c9baf


Jamie blinked his eyes in the darkness as he came to. He was laying on his back now with his legs in the air, the backs of his knees resting on a bar of some kind. He arms hung at his sides. He could barely see, but guessed that he'd been tied to the bench press. His pink bra was still around his chest, but the panties had been pulled to the side. They still covered his cock, but he could feel something between his cheeks. The feeling, now familiar, of his asshole stretched open by something long and thick. He couldn't see, but he was sure that there was a condom covered banana inserted in his ass.

The feeling of his ass filled with a foreign object made his dick grow inside the panties again. He could tell there was a dim light on behind him, but he couldn't twist his neck to see it.

“Okay, Mandy truth or dare?” Jamie heard Tommy ask.

“Dare, of course,” Mandy replied.

“Alright, but you have to do it,” Tommy said. “Go sit bare-assed on his face.”

“Oh that's easy,” Mandy replied.

Jamie barely had a moment to realize what was going on when he felt Mandy behind him. His eyes had adjusted to the dim light and he could see as she moved above him. Looking up her perfect milky thighs parted at a smooth round apple shaped ass. The guys at school always said she had the best ass of any girl there.

As she lowered herself down her cheeks parted giving Jamie a view between her crack. It was hairless and pink – her puckered hole twitched when it felt Jamie's breath. She leaned forward holding onto the bar and rested her ass on Jamie's face.

He felt her large smooth ass cheeks slide down either side of his face and he breathed in smelling the earthy scents on her ass. He also detected a hint of her cunt smell – she was clearly wet.

Jamie still felt drunk – there was no way to tell how long he'd passed out for, maybe an hour, maybe 10 minutes. In his inebriated state, he barely gave a thought before extending his tongue, laying it flat deep in her crack. He heard her let out a soft moan and felt her rock her hips forward, pulling her crack along his tongue.

He kept his tongue out tasting every bit of her ass as she moved. His tongue slid from just behind her pussy back up her ass. He felt her hole jump as his tongue made contact and open slightly letting him take in the warm fleshy taste of her sphincter. She dragged her ass further against his tongue until he'd licked to the top of her crack.

She moved her ass back and forth coating her ass with his saliva. When his tongue met her hole again she stopped and pressed out. He felt her hole open again, wider this time, and he slid his tongue inside. Her legs began to quiver as he swirled his tongue in her rectum. She pushed her hand between her legs and rubbed her clit furiously as she felt Jamie's tongue working deeper into her ass. Forgetting about the others in the room for a moment she let out a gasp of air and a loud moan as she worked herself toward a climax.

Jamie pushed his tongue as far in as it would go, feeling her hole grip down around it then loosen again. He put his lips around her asshole making a tight seal then sucked in pushing that much deeper inside. She began to shake hard and put all her weigh on his face. He felt a warm liquid run down his chin and neck as Mandy panted, moaned and shook with an orgasm. As she lifted off Jamie felt his face covered in her ass sweat.

“Very nice,” Tommy grinned. “Ok Sarah, truth or dare?”

“Wait no it's my turn to ask,” Mandy objected.

“No way, I'm the only guy I get to go twice, otherwise it'd be unfair,” Tommy said.

“Oh fine, I'll just have more time to think up something really bad for you to do,” Mandy shot back.

“So, Sarah?” Tommy continued.

“Truth,” she answered.

“Alright, hmm let me see,” Tommy mused. “Well since this whole thing was your idea, tell me the truth. Why are you doing this to him?”

“I can't tell you that,” Sarah said.

“You have to it's the rules,” Tommy complained.

“Oh go on, he already knows what you're doing, you might as well tell him why,” Julie said.

“Fine, alright, I'll tell you, but you have to swear you will tell no one about this,” Sarah said.

“Okay I swear.”

“Every year the varsity cheerleaders have a competition. We make any freshman girls who make the squad recruit a guy. They get one upperclassman as a mentor, but they're responsible for getting their guy ready and then we all get together and have them put on a show of sorts,” Sarah explained.

“A fashion show?” Tommy asked.

“Sort of, but with more sex,” Sarah answered. “It's called the Sissy Trials. You get points for completing different challenges before the final show, like fooling a guy and getting him to take your sissy on a date. Or who can get the dirtiest photo of their sissy.”

“So you guys do this every year?”

“Yes, usually to three, maybe four, guys,” Sarah said.

“Why have I not heard about this before?” Tommy asked.

“Well we tend to get guys from other schools, but even when we use guys here they never talk. I mean would you?” Sarah said.

“Good point, so what do you win?”

“Respect, and instant status among the senior girls.” Sarah said. “You get invited to the cool parties, if you like a guy the other girls back off. Stuff like that.”

“Sarah is Julie's mentor, I'm just along for the ride,” Mandy said. “And this year with Julie, she has a secret weapon.”

“What James?” Tommy said.

“Well yeah for one, he's pretty much the best sissy we've found yet,” Sarah said. “I mean usually we have to put them in wigs and glob on make-up to cover their stubble, but he's perfect already. But, no, our real weapon is your Mom.”

“My Mom?” Tommy said confused. “What's she got to do with this.”

“Sorry that one stays a secret,” Sarah smirked. “Now, are you ready? Truth or Dare?”

“Dare,” Tommy smiled.

Anonymous 13/11/27(Wed)03:59 No. 20348 ID: 94ad9c

the mother aye? interesting veeeerrry interesting

Anonymous 13/11/28(Thu)07:06 No. 20351 ID: 2d82d2

Fuck I really want more of this story

Anonymous 13/12/08(Sun)00:36 No. 20421 ID: 0550d2

Thanks for the new updates
Enjoying the story very much
Looking forward to the next chapter
>first for "Jamie woke up from his dream"

Anonymous 13/12/14(Sat)08:58 No. 20469 ID: 80814b

i need moreeeeeeeee ; 3 ;

Anonymous 13/12/31(Tue)10:08 No. 20555 ID: f6293f

Don't die on me now damn it

Anonymous 14/02/16(Sun)03:35 No. 21149 ID: f6293f

R.I.P. in piece a truly fantastic story

Dee 14/02/18(Tue)00:11 No. 21163 ID: 7c9baf


Oh it's not dead just unconscious for the moment. I'll return and finish at some point.

Anonymous 14/04/08(Tue)10:10 No. 21503 ID: 80814b

ughhhhh please come back i've had blue balls for three months

Anonymous 14/04/28(Mon)07:24 No. 21637 ID: 2ba399

Am I the only one who thinks James should end up dead? The poor bastard

Anonymous 14/04/28(Mon)10:50 No. 21640 ID: 01f217

I'd love to be him. Different strokes for different folks I guess.

Anonymous 14/04/30(Wed)09:29 No. 21652 ID: 80814b

Wish the author would write more. o well

Anonymous 14/06/11(Wed)03:48 No. 21924 ID: 638974

this needs a bump

Anonymous 14/07/12(Sat)02:26 No. 22060 ID: a06bd3

this might be dead but it deserves one more bump

Anonymous 14/07/26(Sat)06:49 No. 22122 ID: a9d5a0


Anonymous 14/12/18(Thu)04:22 No. 22986 ID: 93cbab

Desperate Bump

Anonymous 15/01/21(Wed)08:21 No. 23144 ID: 1f54c4

OP let us down

Anonymous 15/04/04(Sat)04:28 No. 23441 ID: 2c45c6

Really need some closure on this awesome story

Anonymous 15/04/22(Wed)08:49 No. 23491 ID: 1f54c4


its been nearly a year and a half since the last update, im pretty sure op died. i wouldnt be opposed to somebody picking this up, its my favorite elit ive seen here

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