Cumdump Sheila – The Beginning

Jake didn’t sleep much last night. He kicked the sheets and climbed out of bed with a curse. “That fucking bitch shattered my life, and now she won’t even let me sleep in peace,” he muttered to himself. It’s been more than a month, but he still couldn’t get her out of his head.

He wandered around his one BHK apartment, lifelessly brushing his teeth. Then he heard the doorbell ring. He opened the door to find his uncle and his cousin smiling pleasantly at him. Shit!

Jake had totally forgotten about this arrangement. His cousin Shawn was trying out the MBA entrance examinations, and he wanted his help in preparing for it. He hated that kid. Always looking up to him like he was some role model. “My life is shit now, and the fucker wants my help.”

His uncle embraced him. “Jakey, how long has it been?” He hated that name. “Oh, you look so haggard. Not getting enough sleep, eh?”

“I’m alright, uncle. You can come in if you want.”

“No, not me, Jakey. I have to leave now. I just wanted to make sure that this fellow reached here safely,” he said, pointing to Shawn.

His cousin had his eyes fixed on his shoes most of the time, with one hand across his chest. Sometimes he looked up to his face. When Jake did the same, he turned away. The last time Jake saw Shawn was at a marriage ceremony. Shawn was fifteen then.

After six years, he still looked much the same. He was taller now, but his face lacked manliness. His body was petite with his t-shirt sleeves hanging loosely over his biceps, and his belly was curved inwards.

His head looked like it was shaved recently, tiny hair standing upright like freshly cut grass. An overall lack of confidence oozed from him.

His father left not long after. Jake led him inside and didn’t waste a second to let the boy know his displeasure. “Look, this is not something that I wanted. I had no choice in this. Our mothers cooked up this idea.”

The boy looked at him sadly, holding his bag with both hands. “I was told that you were okay with this.”

“I already said that I wasn’t, didn’t I?” he scoffed. Shawn blanched. “Anyway, we’re in this now. I told your mother that I would help you so…”

Shawn waited in silence, with a distant look in his eye. “Let’s make some things clear,” Jake continued. “You’re living with me for free. So you have to do all the household chores. You okay with that?” The boy nodded. “Good. Next, don’t invite anyone here without my permission. In fact, don’t invite anyone period.”

“I won’t,” said Shawn.

“Next, if I’m gonna coach you, then I’m gonna be rough on you. Be prepared.” The boy nodded timidly. “Good. You’re sleeping in my room. On the floor, not on the bed. I can lend you a straw mat. You’ll sleep on that.”

Jake began coaching Shawn late in the evening. There was a study table in his room with a computer chair. They began with Logical Reasoning. Shawn was given two hours to work on four pages of previous year questions. The boy began his work fervently.

After watching his progress for a while, Jake went to the living room to watch some TV. Mohanlal’s superhit movie Spadikam was on, so he decided to watch that. He stopped the movie midway, too aroused by the actress’s figure. “Now, I gotta jack off.”

Opening his laptop, he browsed some porn sites. “Don’t they have any new stuff here?” He settled for some teacher-student porn that he had already seen a thousand times and started stroking his cock. It was so dull that he couldn’t even keep his erection on for long.

“You have to be kidding me.” Jake looked for other options. “There’s gotta be something that I haven’t watched.” He scrolled and scrolled and then stopped at the shemale tag. He gulped. Jake had watched shemale porn once and promised that day that he will never watch it again.

But desperate times called for desperate measures. He played a video from the taboo section. A shemale was riding a man hard, her cock dangling wildly as she bounced. “God, a cock on a girl is the greatest thing ever!” Jake started stroking his cock again, which was now rock hard.

He moaned and shifted in his seat. He was near the precipice of a huge ejaculation when Shawn walked in.

“Brother, the two hours are up, and I completed…” Shawn stopped and stared at him in shock. The laptop screen wasn’t facing him, so he didn’t see what Jake was watching. He only saw him petting his cock.

“What the fuck you staring at? You wanna watch me jack off?” The boy stood frozen. “Go back in there, idiot. And don’t call me brother. I’m your master.”

Shawn walked back in with haste. “Bloody idiot, he ruined my mood.” Pulling up his shorts, Jake got up and walked to the room. Shawn was in his chair, his hands on his lap, and his eyes fixed on the book in front of him.

“I… I worked out 26 questions,” said Shawn, his face red.

Jake looked at him with a scowl on his face. “Twenty-six? That’s all you did? I told you to work out all the questions, and all you did is 26?” He was still pissed off that he ruined his mood.

“I didn’t have the time, there… there were a lot of questions and… and some of them were really confusing.”

“It is meant to be confusing, you fucking idiot.”

Shawn almost teared up at that. “Why are you so mean to me, brother?”

“Don’t call me that. Call me, master. I’m your master. And I’m mean to you for your own fucking good.”

“Okay, master,” said Shawn, his voice breaking.

“What the fuck? Are you crying? What are you, a girl?” Jake laughed.

“No, I’m not,” Shawn said, wiping his tears.

“Yes, you are. You’re a girl,” Jake said, laughing louder. When Shawn protested, Jake pulled him up by his shirt. “I’m your master. If I say you’re a girl, then you’re a girl.” Just then, an idea hit him. “You know what… I’m gonna do something now.”

He picked a marker from the desk and wrote ‘I AM A GIRL’ on Shawn’s forehead and then wrote ‘KISS’ and ‘ME’ on his cheeks. “There we go,” he said, letting Shawn go.

Shawn looked in the mirror and gasped. “What have you done?”

“MASTER!” Jake bellowed. “Address me as master, or I’ll knock your teeth out.”

“Yes, master,” said Shawn obediently.

Jake slept soundly that night. Shawn slept on the floor on a straw mat that Jake gave him. He woke up the next day to rest his eyes on a pleasant view. Shawn had prepared tea for him. After placing it on the table, he was about to leave when Jake yawned.

“Good morning, master,” he said cordially. He was surprised to see that Shawn still had the ink from last night on his face. “Such a submissive guy.”

“Good morning. You can leave now.”

Shawn bowed slightly and left. As he was leaving, Jake’s eyes lingered on his ass. ‘Not a badass for a guy.’

Jake had work that day from nine in the morning to six-thirty in the evening. He told Shawn that he would be back by seven and asked him to clean the place while he was gone. The rest of the day was a blur. The office hours were dull, as usual. Nothing interesting ever happened.

He couldn’t wait to go back to his cozy apartment and bully his cousin some more. Bullying him gave him more pleasure than masturbating. Jake got off from work way earlier than expected. He reached his apartment at about five o’clock. The floor looked spotless, clean as a whistle.

There weren’t any dirty clothes anywhere, and the books were assorted neatly on the bookshelf. Visibly impressed, he looked around for Shawn. A soft giggle came from Jake’s room. The door to the room was ajar.

He opened it to find a hot girl in her panties, lying on the bed. She had her headphones on, and she was watching something. But wait, that’s not a girl.

“Shawn… you?”

Alarmed, Shawn sprang up from the bed, losing the headphones and all. The black satin bra he wore fitted him loosely, but the thong looked perfect on him.

“Brother… I mean, master, I….” He stood up, fumbling for words, covering his crotch with his hands.

“What the fuck are you doing with my girlfriend’s lingerie?”

“This is your girlfriend’s?”

“My ex-girlfriend. But that doesn’t… what the fuck are you doing?” He asked exasperated.

“I, I don’t know. I found these in the cupboard and I… I remembered you calling me a girl, and… one thing led to another.” Shawn said, stammering a little.

“I don’t even… how long have you been wearing that?”

“It felt so good, and you were supposed to return at seven, so… I’ll take it off now.”

Jake looked at the slight bulge in his cousin’s panties, and the image of the shemale bouncing on a man’s dick crossed his mind. “No,” he said sternly. “You’re not going to take it off. That’s your punishment for touching my stuff while I was gone.”

“You want me to wear this all night?” Shawn asked with a stupid look on his face.

“Not all night. I want you to wear it all day, every day. Not just the panties and the bra, my dear,” he said, walking closer to the scared boy. “I want you to dress like a girl. I want to see you in a saree, in a nightdress, in a skirt,” he was an inch away from Shawn’s face. “That’s your punishment.”

Shawn’s smooth dusky face twisted into a smile, just a little, before resuming its horrified guise. Shawn wore a knee-length night-dress to bed. He had an embarrassed look on his face as he entered the room. “It was nice that someone was wearing it,” thought Jake.

His girlfriend returned everything that he bought her after their breakup. He could see now that it was a blessing in disguise. Jake watched his cousin curl up on the floor, his dress riding up to expose his fleshy buttocks. His cock stirred in his pants.

Weeks went by. Shawn was transforming before his eyes, looking more and more like a girl every day. He now wore sarees and churidars and skirts when he was at home — sometimes, he even went outside in that getup. With his allowance money, he bought nail polish, lipstick, mascara, even a wig.

In addition to all this, he regularly shaved his face and chest, not allowing any unwanted hair to take away his femininity. Shawn was now Sheila.

They were living like husband and wife. When Jake came home after work, chai was ready, followed by a leg massage. After that, he would coach Sheila a bit. He was now used to calling him Sheila, and Sheila would respond in an effeminate voice.

Whenever he heard that voice, his cock would harden, and he would think of all the things that he wanted Shawn to scream in that voice. But no. He was not gay. He was not going to fuck another guy. At least that’s what he told himself.

This perfect paradise that he lived in was almost spoiled one day. The day Shawn’s dad dropped in unexpectedly. Jake’s eyes went wide when he opened the door. “Hey, Jakey,” he said warmly and hugged him. “Where’s my son?”

Opening the door wide, he barged into the room, anxious to see his child. Beads of sweat formed on Jake’s brow. His uncle can be quick to anger, and his wrath was a terrible one. Luckily, the door to his bedroom was closed. Sheila must have heard him coming. “Why is the door closed, Jakey?”

“Sheil… I mean… Shawn must be studying, uncle,” he gulped. “I just got home from work.”

It took a while for Shawn to come out. Understandably so. He was in a saree and had tons of makeup on. After a couple of minutes, he finally came out wearing normal boy clothes and seemingly out of breath.

His father embraced him when he saw him and inquired about his progress. Shawn put in a good word for Jake. His father thanked him, patting him on the back.

“Good job, Jakey. The purpose of education is to educate others.”

Jake nodded in agreement.

“Working hard is good, son,” he told Shawn. “But I fear that you’re overdoing it. Why don’t we all go for a movie today?”

Shawn glanced at Jake for a second. “But, don’t you have to go back, father?”

“No, no. I’m going by the night train. We have plenty of time.”

The movie theater was an old one. The seats were torn, and some had their sponges hanging out. They sat in the second row on the left side. Shawn sat in the center, his father and Jake on either side.

The movie wasn’t any good. Before long, Jake was yawning. He would have dozed off to sleep if it wasn’t for the hot item-song. That was the only part of the movie that he was interested in. The actress was scantily clothed, and she was dancing in the rain. Her bulging tits gave him a hard-on.

That’s when he felt a hand on his crotch. It was Shawn’s. His cousin must have noticed how turned on he was. He rubbed Jake’s crotch and slowly unzipped the jeans. Jake was in heaven. A nice handjob in a rundown theatre. That was like a scene from his fantasies. Jake squirmed in his seat, his eyes closed in pleasure.

With a tight grip on his cock, his cousin’s strokes got faster, jerking him off like an expert. It’s a miracle that his uncle didn’t see any of this. He didn’t even hear all the squeaking noises that both of their chairs made.

When he couldn’t hold it in anymore, he groaned softly and ejaculated all over the seat in front of him. His cousin withdrew his hand, and Jake saw him lick his fingers.

After the movie, they went back to Jake’s apartment. His uncle rested there for a while. Shawn fixed up some dinner for both of them. At the dinner table, Jake stole a glance at his cousin when he could.

Shawn smiled whenever he caught his gaze. He was dressed like a guy now — in a shirt and some jeans — but that didn’t stop Jake from fantasizing about him.

“WOW! That was a good meal, son. You really can cook,” his uncle said, shouldering a bag and preparing to leave. “Jakey, my boy! Always nice to see you,” he said, giving him a hug.

“God, I’m so full. Jakey, walk me to the bus stand.”

Jake closed the door with a bang. He was waiting for his uncle to leave this time, and now he wanted him to walk him to the bus stand? Jake couldn’t wait to get his hands on Shawn.

After half an hour, his uncle’s bus came. He waved his hand as the bus left, and when it was finally out of sight, he ran. He ran as he had never run before, almost crashing into an old man when he turned a corner.

He climbed up the steps of his building and reaching his apartment, he opened the door. A clattering of pans could be heard, so he dashed into the kitchen. Shawn was startled when he saw him. He was washing the dishes. “Brother, you scared me!”

Jake smiled and lifted his cousin with his strong arms. His cousin gave a sharp yelp when he swept him off the floor. So small, he seemed in his muscular arms. So helpless. He threw Shawn on the bed, who sat up and looked at him in surprise. Jake took off his shirt and unbuckled his belt.

His cousin stared at the bulge in his underwear, his eyes gleaming with desire. For a moment, he seemed to be hypnotized as his dreams had finally come to pass. He snapped out of his reverie and said, “Brother, at least wait for me to put on some makeup.”

“We don’t have the time,” said Jake, climbing on the bed, crawling over his cousin. “I want you now.” His face was inches away from his cousin’s now, and his eyes shone with lust.

Jake stuck his tongue inside Shawn’s mouth, and he accepted it gladly. Their warm lips smushed together, and their saliva mixed around their intertwined tongues. His large body was crushing his cousin’s petite one, and he had to gasp for breath every now and then.

Shawn’s hands explored his body, passing under his boxers to get a feel of his cock, rubbing his back, pressing his buttocks. They twisted and rolled on the bed, each with their arms wrapped around the other. Little by little, Jake was letting loose. His inhibitions about fucking a guy was slowly fading.

Tearing his cousin’s shirt with the buttons still on, Jake feasted on his nipples. He chewed and bit them, making his cousin moan, holding onto the hairs on his back.

“Brother, please be gentle,” his cousin said, moaning in his slutty girl voice. That made him hornier, and he chewed his nipple even more roughly. His other nipple, he squeezed between his fingers, and that made him moan even louder.

Jake sat up and took his cock out. Shawn hurried to remove his pants. Jake helped him. And that’s when he saw it. His cousin was wearing panties.

“You’re still wearing them?” he asked.

“Of course, I am. I am a girl, brother,” he said, biting his lips.

“What a slut you are!”

Jake bend down and kissed him again. Carefully positioning his large body, he placed his cock on top of his cousin’s. He then pulled the panty down, halfway to his cousin’s knees. Shawn’s tiny cock was crushed by his enormous mass. Then, slowly, he started rubbing his large cock on his cousin’s tiny one.

Jake kissed the neck and the earlobes, tasting the sweat and the sex. Already, precum was leaking. The sticky goo stuck to both their bellies as their bodies writhed in pleasure. Jake never felt as dominant as he felt now. His cousin was more submissive and petite than any girl he knew – the perfect lay.

What a graphic scene it was! His sweat pouring down on Shawn. Oily cock rubbing against oily cock. There they were, a small thin guy, crushed under his hairy, hunk cousin, their lips sloppily interlocked.

The moans of his cousin rose to a feverish pitch, and Jake himself felt that he was on edge. They both hugged each other tightly and orgasmed. Their cocks pumped cum in unison, and their bodies were glued in an embrace.

Shawn got up after a while. He rolled Jake over, and standing, he pulled his panty up. His brown buttocks bounced, making a soft sound. “I’m going for a shower, brother,” he said, getting a towel.

Jake didn’t respond. He was exhausted. The bathroom door closed, and the sounds of the shower running were heard. Jake lay there for a while, his eyes closed. When his cock was hard again, he got up and walked to the bathroom.

Shawn was standing under the shower, his panty still on. Water ran over his smooth body, which was sparkling under the candescent light. His panty looked like it was almost coming off as if the water was pushing it down. Jake admired the views for a while, standing by the door.

After a minute, he came forward and stood behind him, his erect penis already poking Shawn’s crack. Jake hugged him from behind and kissed the nape of his neck. Shawn held on to his arms and, turning around, kissed his lips. Jake had now had enough foreplay.

His strong hands then tore off the panty and pushed down his cousin. The boy fell and was now on all fours. Jake stood tall over him, stroking his penis as he looked at his cousin’s puckered butthole. The doggy position. Jake’s favorite.

A finger went inside the boy’s hole, and he cried. But even in his cries, he sounded like a girl. Kneeling properly, Jake inserted another finger inside his cousin. The boy screamed and craned his neck around, his hair sticking to his face as the water from the shower was constantly beating down on them.

“It hurts, master,” cried Shawn.

“Not master. Call me, brother. I like that better,” said Jake, shoving both fingers deep inside.

“Brother, please!” the boy screamed.

“Yes. Like that. Whenever we fuck, I want you to call me brother,” he took his fingers out.

He opened the boy’s hole wide and thrust his cock in. Shawn screamed. This time it was all pain. But his cock was only halfway in. The floors were slippery. Without taking it out, Jake thrust it in deeper, to tear open his hole some more. The boy was almost crying now and begging him to stop.

Jake took his cock out, and Shawn sighed in relief. He gave a second thrust, and the boy yelped. This time it hit deeper, and Shawn’s body was pushed forward. The boy held onto the toilet for support. Jake took his cock out for the second and final time.

Pushing it in again, he began his ruthless fucking. He could feel his cousin’s tight hole closing around him, but Jake just pushed harder. The first few minutes were agony for Shawn. He was hugging the toilet, crying, pleading. Jake was relentless. Hitting deeper and deeper and even deeper.

Then, the scene began to change for Shawn. His cousin’s cock was beginning to feel good inside him. Pain became a pleasure. The cold water was raining down on him, but he was hot. He began to sing sweet moans. Uh… ahhh… oh god. He was still hugging the toilet, and his knees scraped forward with every thrust.

“Oh, yes, brother. Harder, ahhh, harder, please,” he said.

“I will, you whore.” With that promise, Jake rammed so hard that the sound of his crotch hitting his ass was like a thunderclap. Being thankful, the boy moaned loudly, praising his brother’s cock.

“Oh… oh… oh, what a big cock you have… brother.”

And there he lay, his face pressed against the toilet rim, dominated by the will and strength of his cousin. Every time Jake’s cock tore through him, he sang praises of it. A symphony of moans and grunts were heard, and the neighbors believed that Jake was fucking some nasty whore in there.

“Call me Sheila, the whore,” he begged. And his master obliged. “Cumdump Sheila,” he called him, spanking his bubble butt. That’s when he felt it. Jake’s cock spasmed, and he felt a warmth inside him. Loads after loads of his semen were dumped inside. At the same time, the boy also finished and ejaculated all over the floor, without even once touching his cock.

That was the best night of his life. That was the night he became Cumdump Sheila.

Thanks for reading! Send your feedback at [email protected].