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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.

71 posts omitted. Last 50 shown.
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

Anonymous 15/07/02(Thu)20:52 No. 23709 ID: e2489c


going to read the rest over the weekend and see if I would be up to it.

am pretty hooked so far

i wrote ex ex why btw

Anonymous 15/07/20(Mon)12:46 No. 23744 ID: ba1f0b


i would suck your sack if you wrote more (and it was any good)

Anonymous 15/07/21(Tue)03:34 No. 23749 ID: 908e6e

Any progress?

Anonymous 16/04/15(Fri)08:14 No. 24199 ID: d95d41

I still jack it to the first chapter of this story every now and then.

Anonymous 17/09/20(Wed)17:58 No. 25149 ID: 8d339d

it seems long dead but bravo

Dee 18/07/31(Tue)01:03 No. 25728 ID: b02fea

Wow surprised this is still on here. I'll try to get around to writing more.

Anonymous 18/08/19(Sun)01:37 No. 25751 ID: cf26e5


Dee 18/08/27(Mon)18:05 No. 25764 ID: b02fea

Part XII

Jets of steaming hot water splashed over James’ face. He ran his hands back over his head spreading water over his long blond hair. His eyes closed, he rubbed a bar of soap over his body from his small shoulders down his sides to his wide girlish hips. He let the bar slide over his ass cheeks and down his thighs, washing away the marker ink from the night before. He paused for a moment at an odd bruise on his right butt cheek that he didn’t remember having before. He poked it gently and it pulsed out a dull pain. Where had it come from? It felt like a bruise you would get after having a shot, but James hadn’t been to the doctor in months.

Shrugging at the mysterious bruise James rinsed his body then turned his attention to his hair, shampooing and conditioning it with care. As he returned the conditioner to the shower shelf he notices a pink razor laying there and looked down at the stubble forming on his crotch and legs. He grabbed the razor and ran it up from his ankles over his calves and thighs. He then went to work on his crotch and balls, gently shaving himself smooth. Finally he spread his ass cheeks and took extra care to remove every hint of hair from his crack.

James returned the razor to its holder and turned the knobs on the shower cutting off the flow of steamy water. He reached out of the shower stall and grabbed a fluffy blue towel from the rack. He began mopping up water from his body as he stepped out of the shower.

“How’re you feeling?” Julie asked smiling as she sat on the toilet.

“Ah, Jesus,” James said jumping at the sound of her voice. “I didn’t know you were in here.”

“Sorry had to use the toilet,” Julie said. “My head is killing me. I had way too many Jello shots.”

“Yeah, mine too,” James said wrapping the towel around his waist. “I don’t think I ever want to drink again.”

“Oh, give it a few hours,” Julie said laughing. “Anyway, turn around.”

James turned his back to her and after a few seconds heard the sound of a flushing toilet. He turned back and Julie had moved toward him holding out a paper shopping bag.

“Here’s a present from me and the girls,” she said. “For putting up with all our torture last night.”

James took the bag and opened it peering inside. What he saw were dozens of pieces of brightly colored fabric. He reached in and drew one out. It was bright blue cotton. As he held it up to his face he could see clearly this was a pair of thong panties and his heart beat a little faster. Julie took another step toward him and took the thong from his hand. She got on one knee and held out the thong beckoning for James to step in it. His cock hardened as he thought about putting on girls underwear again. Every time he’d down so in the past it ended with him bent over, but the feeling of soft cotton between his cheeks was too much to pass up. He stepped in and Julie pulled the panties up over his girlish hips.

“These are all for you,” Julie said nodding toward the shopping bag. “No more boxers. Even when you’re wearing boys clothes you have to have panties on underneath.”

“All the time?” James asked a little panicked.

“All the time.” Julie answered. “I will be checking.”

James’ mind whirled. How was he going to keep him mom from finding his new panties? How would he change for gym class or swim practice?

“Here’s your other present,” Julie said.

She took a larger bundle of fabric from the bathroom counter and presented it to James. On top he recognized the shape of a bra, taking the strap in his hand. Then he unfolded the bundle, which unfurled into the shape of a yellow sun dress. His cheeks burned red.

“Can’t I just be a boy?” James said looking over at Julie.

She looked back at him sympathetically and moved toward him. Her soft full lips pursed as she leaned in to kiss him. Their lips met and James instantly forgot his embarrassment as he tasted her sweat saliva. She wrapped her arms around his shoulders then moved her mouth next to his ear.

“No,” she whispered then withdrew. “Put on the dress and do your makeup. I’ll be upstairs.”

Julie was in the kitchen eating breakfast with Sarah and Mandy when James emerged from the basement. The dress flowed around his toned thighs and flared out over his wide hips. He’d returned as Jamie, in full makeup with his hair braided loosely behind him.

“Well don’t you look cute this morning,” Mandy said giggling.

Jamie ignored her and pulled out a chair as Julie set a bowl of cereal in front of him. He ate in silence as the girls chatted back and forth. They all had homework to get down and decided to get on their way after breakfast.

“Do you want me to drop you at home?” Sarah asked Jamie.

“What, like this?” He said motioning down. “I can’t go home in a dress.”

“Well then where do you want to go?” Sarah replied.

James thought for a few moments. He didn’t have any clothes at Julie’s house. The girls had gotten rid of what he’d originally worn to the mall. Where could he get something to change into?

“Take me to Sam Fischer’s house,” He said.

Sam was his best friend. Jamie really didn’t want him to know he was cross dressing, but it was better than his mom or step-dad finding out. Jamie hoped Sam would understand once he’d told him what had happened.

Sarah agreed and they all left in her Jeep waving goodbye to Julie. They weaved their way through the tree lined streets, Jamie directing Sarah to Sam’s house until they pulled up in front of a small bungalow. Jamie stepped out of the car and walked to the door as Sarah sped off. He prayed Sam would be home alone as he rung the doorbell.

“Hey,” Sam said a little confused as he swung the door open. “Can I help you?”

All of a sudden Jamie felt his stomach tighten and panic began to rise in his chest. He hadn’t thought about what he was going to say or how he could explain himself. Would Sam tell him to get out? Would this ruin their friendship?

“I, uh, I’m… Jamie,” James stammered. “Can I come in for a minute?”

“Yeah, I guess, sure,” Sam said a bit wary at the hot young girl who’d suddenly appeared at his doorstep.

They walked inside and Jamie was relieved to see that Sam was home alone. This was normal for Sam, whose Mom was often out working one of her many jobs. Sam walked to the couch and sat down. Jamie sat next to him.

“So, not to be rude, but what are you doing here?” Sam asked after a few moments of awkward silence.

Sam swallowed hard and looked into his friends eyes. He had big green eyes framed by shaggy dark brown hair. His face was tanned, as was the rest of his athletic body. They grew up surfing and swimming together, but this was the first time Jamie had really looked into his eyes.

“This is going to sound weird,” Jamie said. “But, you know me and I need your help.”

“Okay, what do you need?” Sam asked.

“I need to borrow some of your clothes,” Jamie said.

“What?” Sam said laughing. “What do you need me clothes for.”

“I’m… It’s me… James,” Jamie said his face burning red.

“No fucking way,” Sam said laughing harder now.

“No, really it is,” Jamie said getting a little annoyed. “Julie has been making me crossdress for some weird contest.”

“James put you up to this,” Sam said. “If he thinks I’m dumb enough to fall for this…”

“It really is me!” Jamie said more forcefully.

“Prove it,” Sam said.

Jamie frowned at him then stood up. He walked in front of him and stood there for Sam to inspect. Sam looked from his hairless legs up to the cute dress and finally to the soft feminine face and long blond hair. Jamie blinked his long eyelashes then reached down to the hem of his dress. He lifted it up to his stomach revealing his blue panties to Sam, which showed the bulge of his cock.

Sam stared at the bulge then up at Jamie then back at the bulge. He reached out and gently rubbed his hand over the front of his friends panties feeling the contours of his friend’s cock through the thin cotton. His palm pressed against Jamie’s balls cupping them firmly as his fingers closed around the shaft holding it through the panties.

“It’s really you?” Sam asked quietly.

Jamie nodded.

“Fuck that’s hot,” Sam said rushing to his feet.

Jamie’s eyes went wide in surprise as Sam came face to face with him. Sam pressed his lips against Jamie’s and slid his tongue between “her” lips. Their tongues swirled and played together as Sam cupped Jamie’s balls under her dress. As Sam kissed her, Jamie suddenly felt an overwhelming wave of pleasure. She kissed him back voraciously, nibbling his lip, forgetting that this was her former best friend. She’d never felt more like a girl.

Sam swung Jamie around and pushed her onto the couch flat on her back. He flipped her dress up and looked down at the small lump in her panties. He rubbed it lovingly, biting his lower lip, then pulled the thong down exposing Jamie’s hard cock. He held the shaft in his hand and began to rub it up and down slowly. At the same time he unbuttoned his own pants and wiggled them off his waist. His own cock bounced out from his underwear. Jamie had seen it before, but not hard. It was long and thick. Bigger than Jamie expected it would be, but not as big as Tommy or even Chris. Jamie pulled his knees in toward his chest exposing his smooth pink asshole to Sam.

“I’m not going to be your first am I?” Sam said smirking as Jamie shook his head no. “Good. You should be getting with every guy in our school. Fuck you make a hot girl.”

Sam grabbed his own cock while continuing to massage Jamie’s. He rubbed the head up and down between Jamie’s butt crack. Jamie felt his stomach flutter as the hard smooth mushroom tip slid between his cheeks. Sam stopped at Jamie’s hole and began to press in. The pressure on his asshole made waves of pleasure shoot through his body causing him to cum in Sam’s hand. Sam took some on his fingertips then reached up and slid them into Jamie’s mouth. She sucked his fingers greedily, the taste of salt warm cum making her relive her past sessions.

As Jamie sucked his fingers Sam push his hips in hard and Jamie felt his cock head pop inside her. She moaned like a whore as Sam pushed his cock inch by inch deeper inside her. He pulled his fingers out of her mouth and grabbed both her ankles as he started to hump her. His hips slapped against her ass causing it to bounce and jiggle as he fucked her. Jamie’s mouth opened wide as she moaned louder and louder, turning into screams of pleasure as he worked the full length of his cock into her ass.

Humping as fast and hard as he could Sam released Jamie’s ankles and fell forward onto her. He pulled her hips back against him as he leaned into a long kiss with her. Jamie felt the cock in her ass tense and engorge inside her then Sam’s body shook and quivered. He jerked his hips over and over shooting more and more cum inside her. His orgasim felt like it lasted forever. When he finally pulled out a stream of thick milky white cum ran out of Jamie’s used asshole.

Sam collapsed on top of Jamie breathing heavily.

“Sorry, I have a pretty big thing for sissies,” he panted.

Anonymous 18/09/04(Tue)11:45 No. 25774 ID: e52cc8

holy shit thank you
please keep posting more

Hope ther is more to come Anonymous 18/09/19(Wed)02:55 No. 25789 ID: 557069

Happy to see another chapter

Anonymous 18/10/09(Tue)17:25 No. 25808 ID: b02fea


Jamie’s butt cheeks slapped against Sam’s thighs as she bounced up and down in his lap. He arched his hips as she sat down sliding the full length of his cock deep into her ass. Her mouth hung open letting out gentle moans even as the corners of her lips turned up in a small smile.

She didn’t know what it was about Sam, but having him inside her gave her more pleasure than any guy before. He wasn’t as thick or long as some of the others, not that he was small, but the way he moved inside her and the way he looked at her made her feel like a real girl. Of course, she wasn’t a real girl as the semi-hard cock and balls flipping and flopping between her thighs proved.

The smile on her face widened as she felt Sam’s cock engorge, pushing out the walls of her asshole. This was the fourth time he’d fucked her today and her bum was feeling nice and loose, accommodating his cock easily. Sam grabbed her hips and thrust up hard. She could feel the head of his cock poking up toward her stomach.

He held her down, pressing his hips up as his stomach began to spasm. He groaned and his body jerked back. Jamie smiled widely feeling yet another big load of cum fill her bum. His hips twitched up and down over and over. They thrust into Jamie so quickly it felt like his cock was almost vibrating in her ass. He stiffened one last time then collapsed back onto the couch.

Jamie slid forward and felt his cock slide out of her asshole. The head popped out giving Jamie one last jolt of pleasure, making her let out a giggle.

“Turn around, babe,” Sam said. “I want to see what I did to you.”

Jamie smirked and spun around in front of Sam. Her dress was crumpled on the floor and her thong was hanging from one ankle, but she still wore her bra. She bent over and spread her butt cheeks with her hands. She pushed out and felt a river of cum run down her leg. Her butthole was red from being repeatedly penetrated and it gaped open about and inch.

“Beautiful,” Sam said reached out.

He grasped one of Jamie’s checks then slowly circled her open asshole with two fingers. She shuddered as goosebumps appeared on her legs. He slid two fingers in feeling little resistance then withdrew them. They were covered in cum. He sat up and presented them to Jamie. She looked into his eyes as she took his fingers in her mouth.

The salty taste of cum mixed wonderfully with the earthy flavor of her ass. Her eyes rolled and she licked and sucked his fingers. He withdrew them and kissed her deeply, tasting his own cum on Jamies tongue.

The two friends collapsed onto the couch, kissing and caressing each other. Finally they just lay next two one another, Jamie wrapping herself around Sam.

“That was fucking amazing,” Sam said out of breath. “I still can’t believe that’s you.”

“I can’t believe how good your cock felt inside me,” Jamie said. “Like it always kind of felt good, but you’re like on another level!”

“You can take it anytime you want,” Sam laughed.

“Shit,” Jamie said noticing the time. “I have to get home, but this was great. Can I borrow some clothes?”

“I dunno,” Sam said sitting up. “You make such a good girl why would you want to change into guy clothes?”

“Because my parents would murder me if they saw me like this,” Jamie said.

“Are you kidding me?” Sam said. “Your mom would love having another girl.”

“Seriously I need to borrow your clothes,” Jamie said more forcefully. “Come on, you got to fuck me four times. I deserve the clothes.”

“Yeah, alright,” Sam said. “But you have to keep the panties on.”

Jamie stood up and pulled her bright blue thong up from her ankles and over her thighs. She wiggled her wide girly hips pulling them up to her waist. As she did she felt the thin strip of cotton slide in between her butt cheeks. She smiled at Sam.

Sam took her into his room and gave her a pair of jeans and a hoodie. Jamie pulled the jeans up and found them a bit tight around the butt, but they fit. Then the hoodie went on, which made the bra Jamie was wearing harder to notice. Her face was still made up like a girl though, so she went to the bathroom sink and wasted it off then redid her hair in a more boyish style. When she left the bathroom she was back to being James.

“What a shame,” Sam said frowning.

Usually James felt relieved to be back in boy clothes, but this time he felt just a little bit sad about it. Still he needed to get home.

He made the short walk from Sam’s house to his and found it empty. He didn’t have to go through all that with Sam after all, he thought. He didn’t regret it though. In fact he was certain he’d be Jamie again soon with Sam.

He hid all his new panties and bras deep in his bottom drawer where his mom wouldn’t find them. He wasn’t sure what she’d do if she did, but he didn’t want to find out. It wasn’t long after he finished hiding them that his mom and stepdad walked into the house with his brother and sister in tow.

“Oh, hi honey, did you have a nice sleep over?” James’ mom asked.

“Uh, yeah, it was pretty fun,” James said. “I’m kind of tired though, so I’ll probably just go to my room.”

“We got pizza,” James’ stepdad said. “At least have a slice first.”

James agreed and they all sat around the table munching on pizza. He couldn’t help but think about the thin piece of cotton between his cheeks as his family talked around him. He cheeks burned red at the thought.

“Are you okay?” His stepdad asked. “You look kind of flushed.”

“Yeah, I don’t feel great,” James said picking his plate up. “I’m going to go to my room.”

As he turned the remainder of his pizza slid off the plate and hit the floor. He bent over quickly and snagged the pizza then stood up again. When he turned toward the garbage he saw a strange look had crossed his stepdad’s face.

“Well, um, goodnight,” James said as he tossed his pizza in the trash and retreated from the room.

He locked the door and threw himself onto the bed. What was that look about? James hoped it was just because he’d been acting strange, but had a sinking feeling. Had he revealed his thong to his stepdad when he bent over? He went to the mirror in his room and bent over in front of it. His thong did ride up enough to see it if someone was looking. Was his stepdad looking at his ass?

Jame changed into his pajama pants and a tshirt, but kept the thong on. He crawled under the covers and tried to think about something, other than his stepdad seeing him in panties.

Anonymous 18/10/18(Thu)13:27 No. 25837 ID: 557069


tSade!O9S.2cqv5k 18/10/19(Fri)03:45 No. 25839 ID: 4c5c71

Well, those are some awesome new chapters. Thank you!

Anonymous 18/11/07(Wed)15:43 No. 25858 ID: c054a2

Fantastic story what will happen with Jamie next

Anonymous 19/01/13(Sun)11:48 No. 25923 ID: 9827a1


Anticipation 19/02/04(Mon)06:51 No. 25951 ID: f818f4


Please I want more 19/02/22(Fri)16:08 No. 25981 ID: 5844ca


Dee 19/03/27(Wed)16:23 No. 26025 ID: 194c8f

Part XIV

James stood in front of his dresser looking down into the top drawer as morning light filled his room. In the center, folded haphazardly, were his boxer briefs -- all grays and blues. Tucked in the back left of the drawer was a colorful ball of pink and green and yellow panties.

James took a pair of boxers in his hand, looked at it and sighed. He laid them back in the drawer and grasped a lacy turquoise thong. He dropped the towel he had around his waist to the floor and stepped into the panties.

They felt soft and thin against his skin. As he pulled them up over his wide hips the thong slid between his round butt cheeks causing his cock to go instantly hard. He looked up into the mirror, his long blond hair fell down over his shoulders.

Maybe it was his imagination, but even without makeup his face was looking more feminine. His lips were fuller, his cheeks softer and his eyes seemed bigger. His thin body led down to his wide hips, which were accented by the thong underwear. He legs were cream colored and freshly shaved.

For half a second James considered just putting on a dress and going to school as Jamie, which made his stomach flip with excitement, but he let the thought pass. All Julie wanted was for him to wear panties and that’s all he would do.

James quickly found his jeans and a t-shirt then brushed his hair back out of his face. He checked to make sure his thong wasn’t peeking out from over his jeans. They were tucked down safely, but James noticed how much tighter his pants were against his butt. As he walked downstairs his shirt brushed against his nipples which tingled with pleasure. He pecs and nipples were much more sensitive this morning.

He wolfed down his breakfast and was out the door before his stepfather made it downstairs. James was still worried he’d seen his thong yesterday and was eager to avoid that conversation.

After the quick bus ride James entered his high school for the first time in girls underwear. His face burned red thinking about them as he walked through the crowded halls, but not one seemed to notice anything different about him. He heart began to beat slower as he opened his locker.

“Hey Jamie,” a voice sang from a few lockers away.

It was Julie walking toward him with a grin on her face.

“Oh, hey,” James said. “How’s it going.”

“Fine,” Julie said. “I’m just ready to check to see if your wearing the panties I gave you.”

Her voice was entirely too loud for James’ comfort and he thought he saw a few heads turn their way.

“Keep your voice down,” James whispered. “I’m wearing them I promise.”

“I want to see,” she said. “Come on show me.”

“What? Right here?” James heart was racing again.

Julie moved in so their stomachs were touching then hooked her finger in his waistband. She lowered her head and pulled his jeans down ever so slightly at the hip. She smiled at him and pulled them back in place quickly.

“Good girl,” she whispered.

The rest of the day went fairly normally for James, other than the constant anxiety he got thinking about his thong riding up and being seen. It wasn’t until the final bell rang that James remembered he had swim practice today.

“Shit,” he muttered as he pulled his swim bag from his locker.

All the guys changed into their speedos together. How could he hide the fact that he was wearing a thong when he was changing in front of the entire team?

He walked slowly to the locker room, hoping if he was a few minutes late he’d have it to himself, but as he entered he could hear voices echoing off the tile walls. More than half the team was still in the locker room in various stages of undress. He decided he only had one option.

James looked up and saw Tommy leaning up against a locker in nothing but his black speedo. James eyes flickered down to the large bulge Tommy had stuffed into the small suit. He couldn’t help but picture Tommy’s cock sliding in and out of his asshole.

“How’s it going James?” Tommy said casually.

“Fine,” James squeaked as he lowered his bag onto a bench. “I forgot my suit though, so I can’t swim today. I’ll just go to the weight room.”

“Who forgot their suit this time?” Coach Burrell said sticking his head out of his office and into the locker room.

“Oh that’s me coach,” James said. “Sorry.”

“I am so sick of you guys showing up unprepared,” Burrell said ducking back into his office.

He re emerged holding a black suit balled in his hands and threw it to James.

“Since this has been a continuous problem with this team I came up with a solution,” Burrell said to all the boys in the locker room. “Anyone who forgets their suit will be given that one.”

James unfurled the suit in front of him. He was holding a girls’ one-piece.

“Coach, please,” James said looking at him.

“Too bad,” Burrell said. “Maybe next time you’ll remember your suit.”

Coach Burrell walked back in and shut the door of his office. There was no arguing with him. The guys all burst into fits of hysterical laughter.

“All right knock it off,” Tommy said. “This is all our faults and James is paying for it, so be nice.”

James was glad Tommy was playing it cool, unlike his sister who got a kick out of embarrassing him. He looked around and all the other guys still laughing but they’d returned to getting dressed, mostly ignoring his presence again. He still was wearing the thong though. There was only one way to get it off without anyone noticing -- just going for it.

In a quick motion he yanked his jeans and panties down all at once, balled them up and stuffed them into his bag. He pulled his shirt off and pushed it on top of the pants for extra protection from view. He looked around and no one seemed to have taken any notice. James smiled and exhaled.

He looked down and realized he now had a new problem, his cock was rock hard. He spun quickly to face the lockers, hoping no one noticed. His stomach fluttered as he looked down at the girls’ bathing suit he was about to step into. He considered just quitting the team at that moment, but he knew that would just bring more attention and trouble to him. Plus the idea of the team seeing him in a girls suit got him really excited.

A couple weeks ago he wouldn’t have had the courage, but now he found himself stepping through the leg holes and pulling the suit up over his body. It was a little small and as he put the arm straps over his shoulders the back of the suit rode up. He looked behind him and saw that the suit only covered about half his butt cheeks. The rest hung out in their round creamy glory.

A boy behind him let out a loud wolf whistle. James stared at the lockers as he felt all the eyes in the locker room turn his way. There were a few short bursts of laughter, but those gave way to softer murmuring between the boys. Then he her the clicks of cellphone cameras going off.

He turned quickly and saw every member of his team staring at him. Some of their mouths hung open. Others were pointing cameras where his butt had just been.

“What are you doing?” James said angrily.

“Dude,” a junior named Ben said, “I’m not gay or anything, but you’ve got a hot ass.”

There was some nodding and mumbling of agreement. James noticed more than a few of the guys were holding their hands over their crotches to hide their excitement. James flipped his hair over his shoulder and smiled at the boys then walked out of the locker room, popping his hips as he did.

Dee 19/03/27(Wed)18:07 No. 26026 ID: 194c8f

Part XV

James walked confidently out onto the pool deck in his one-piece swimsuit. His teammates who had not been in the locker room for Coach Burrell’s punishment looked up in astonishment. The rest of the team streamed out of the locker room behind him.

There was excited chattering all around as everyone explained what had happened in the locker room. There was some light teasing, but mostly amazement at how well he wore the suit.

Ben even grabbed James by the shoulders and forcibly turned him around so his backside faced the team.

“I mean look at that ass,” Ben said. “That’s as nice an ass as any girl in school!”

Every compliment was of course followed with an obligatory, “but I’m not gay,” statement.

“Okay, okay settle down,” Coach Burrell said as he walked from his office across the pool deck. “As you can see from now on there will be consequences for forgetting your suits.”

“And we’re all very grateful it was James who forget his,” Ben said and the team burst into laughter.

James face turned beat red then he jumped as he felt someone pinch his butt. He turned around, but it could’ve been any of a dozen guys.

Burrell ordered the team into the pool, four guys to a lane. Ben jumped in with James, along with two other juniors. They stood in the shallow end waiting for coach to give them direction and James felt a hand gently cup his butt. He looked to Ben, but it wasn’t him and by the time he turned the hand had moved.

All through practice, any time they stopped, James felt hands touch his bottom our crotches brush against him. He couldn’t be imagining it he thought. He’d practiced with this team for weeks and no one had ever even bumped into him.

All the touching and rubbing was driving him wild. He never caught the perpetrator, but with how many times it happened half the guys there must have felt him up.

After ninety minutes of swimming Coach Burrell ordered the team out of the pool. They’d finish up with some sprints. James felt several hands press his lower back, moving him to the front of the group.

“Okay, James and Rob you’re up first,” Burrell said.

James slowly stepped up onto the blocks as a hush grew over the rest of the team. His butt was squarely at eye level now and they were all mesmerized. James stood there feeling so exposed and scared about what came next. When the coach said “Ready” he’d have to bend at the waist in front of everyone in that tiny suit. He knew what would happen.

“Ready,” Coach said.

James bent over and the suit fabric pulled back exposing his entire round butt to the team.

“Hold on,” Coach said. “Stand up.”

When James stood up again the suit had ridden all the way up his bum making it look like he was wearing a thong. He reached back and adjusted the suit over his butt cheeks in an effortlessly girly fashion. A few of the guys groaned softly at the sight.

“Okay, let’s try again,” Coach said and winked at James. “Ready. Set. Go!”

They shot off the blocks and sliced into the water. The hundred yards they swam went by in a flash and James felt hands pulling him up out of the pool. He’d won the sprint, but instead of the usual high fives it was all butt pats for James.

He stood back as the rest of the sprints went by, but unlike pst practices he was never left alone. A few guys were always hanging out with him and again he kept feeling them touching his body stealthily. His mind wandered back to being Jamie and feeling all that attention from guys. He loved it.

The final sprints ended and everyone started toward the locker room. As James got near to the door Coach Burrell called him into his office.

Burrell was half sitting half standing in front of his desk. James walked in, but the coach didn’t offer him a chair so he stood directly in front of him.

“I’m sorry you had to be the example today,” Coach said. “I hope you understand it was to help the team remember their equipment.”

“I… yes I understand,” James said.

“I hope it wasn’t too embarrassing,” Coach said. “If the guys give you a hard time about it let me know.”

“Okay, but they were pretty nice about it,” James said.

“That’s one word for it,” Coach said.

“What do you mean?” James asked.

“It looked to me like more than a few of them would’ve fucked you right there on the pool deck,” Coach said.

“I… I don’t… I mean that’s weird,” James stammered.

“Is it?” Coach said standing up and moving closer to James. “I can’t blame them.”

Coach Burrell put a hand on James shoulder and slowly pulled the bathing suit strap to the side. He looked down into James eyes. James looked back into his. They were brown. Coach Burrell was handsomer than James remembered noticing before. He had a shaved head and maintained his swimmers build.

“I’ll take that suit back now,” Coach said.

James trembled slightly, but never broke his gaze away from his coach. He slid the other strap off his shoulder then withdrew his arms. He wiggled his body as he slid the suit down to his waist. Coach Burrell leaned in and kissed him deeply on the lips. The coach brushed his hands down James sides and hooked his fingers into the bathing suit.

He pulled the suit slowly over James big round bum then let it fall to the ground. He lifted James with his hands supporting his butt up and then let him down on the desk. James hooked his legs around his coach’s waist, the bathing suit still hanging off one ankle. They kissed passionately, their tongues swirling together.

James had completely lost himself in the moment. The excitement and embarrassment of the swim practice, all the touching had driven him to the point where all he wanted was someone to fuck him hard and long.

Jame lay back on the desk and scooted his butt forward, lifting his legs into the air. He reached back and spread his cheeks apart exposing his tight pink asshole.

“Wow you really want this huh?” Coach Burrell said grabbing his crotch.

Burrell unzipped his pants and reached down for his cock. He pulled it out and let it hang between his legs. It was already half hard, but it continued to grow in front of James ready asshole until it was nearly as large as Tommy’s had been.

The coach held his shaft and pressed the big mushroom tip against James’ tight hole. He rubbed it around in a circle then pressed hard against it. James hole resisted, giving him a wonderful sensation of pressure.

Burrell reached across the desk and opened the top drawer to retrieve a small bottle of lube. He spread it over his cock then wiped some up James butt crack. He smeared a glob on his fingers and slowly pushed them inside James butt hole.

James moaned and arched his back allowing Coach Burrell to explore deeper inside him.

“Did you like dressing as a girl James?” Coach Burrell said with his fingers up James ass.

“Yes and call me Jamie,” Jamie said.

“Of course,” Coach smiled. “Are you ready to get fucked Jamie?”

“Please fuck me,” Jamie breathed.

Coach Burrell withdrew his fingers quickly giving Jamie a small jolt of pleasure. He took his thick cock and pressed against her asshole again. This time the tip slipped in easily and Jamie gasped loudly.

Sounds of slapping flesh filled the coach’s office as he pounded into Jamie. His cock pushed and pulled against her butthole as he filled the young sissy’s ass. Jamie breathed and moaned and Coach Burrell grunted with each thrust. Neither remembered to keep things quiet with the locker room sharing a wall. Jamie didn’t know if there was anyone left in the locker room, but if there was they would certainly hear.

The coach pulled out and lifted Jamie’s butt into the air. He pulled her cheeks apart and watched as her asshole gaped open for a few moments, still craving cock. He let her down then pulled her forward onto the floor.

Jamie looked forward at the hard cock, dripping with lube. He took it in his right hand and push the head into his mouth. It tasted salty and slick from the lube and pre-cum. His own earth taste came through and he bobbed his head up and down on his coaches cock. As he finally took Burrell’s long shaft all the way down his throat he felt it engorge and pulse as he shot cum.

Jamie gulped it all down, but a bit of cum mixed drool ran down his chin as Coach Burrell pulled his cock back.

“You’re amazing,” Coach Burrell whispered down at Jamie. “Why don’t you hang on to that bathing suit.”

Anonymous 19/04/04(Thu)21:21 No. 26033 ID: 190308

Awesome to see an update.

Anonymous 19/04/11(Thu)03:32 No. 26044 ID: c686cf

greatly enjoying what you’ve written so far, and was especially touched/moved/turned on by the sections with jamie and sam. like...i really hope something comes of that and that there’s a good ending someday. also hoping jamie goes full-time. please don’t hint at anything though! thank you for your work!

Anonymous 19/06/17(Mon)08:18 No. 26092 ID: 2a5e9d



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