The Sleepover

Literotic asexstories – The Sleepover by MHanna8800,MHanna8800
“Aren’t we a little old to be having a sleepover?” Andrew asked Tobin. Tobin shrugged.

“We’re all adults here, and my older sister still has them. Having fun is all that matters.”

Andrew and Tobin concluded their long walk up to Tobin’s house.

“My mom is so strict. No shoes, no socks on the carpet. So, take them off now.”

Andrew, wearing a t shirt, jeans, and sneakers and socks, doubled over to remove his footwear. Tobin kicked off his sandals and opened the door.

Tobin’s house was huge and tidy. Andrew stepped slowly, his hot feet cooling on the icy hardwood floor. He noticed a beautiful girl laying on the couch looking back at him. She stood up and approached.

“I didn’t know you were having a boyfriend over, Tobin,” she said mockingly.

“I see you’ve met Chelsea,” Tobin said to Andrew. Chelsea was wearing a near transparent lace blouse with no bra. Andrew could see her nipples almost perfectly. Below that, she wore leather leggings that stopped at the ankle. Her toenails were painted purple.

“Nice to meet you,” Andrew stammered. An erection quickly formed in his small penis. Chelsea took notice, unimpressed.

“See you around the house,” she said breathily. Andrew wildly fantasized about sneaking off to a bathroom in the house and showing her she had judged him wrong.

“Let’s go check out the pool,” Tobin suggested.

The duo’s bare feet slapped through the house to the back door, where a gorgeous older woman lay naked next to a large swimming pool. Andrew’s little boner shot back up.

“This must be your friend. Does he know the rules of the house?” she asked, sitting up slightly, her big tits shifting and shaking on her chest.

“I’m teaching them as we go,” Tobin said.

The mother rolled her eyes. “Shower before and after swimming. Swim nude, sleep nude.”

Andrew looked to Tobin like it was a joke, but Tobin wasn’t laughing. Seeing Tobin’s mother naked in front of him told Andrew everything he had to know.

“There’s a shower in the pool house,” Tobin said, leading Andrew to the building next to the pool. Immediately upon entering, Tobin took his shirt off and reached for his waistband.

“Whoa! I don’t want to see you naked!” Andrew protested.

“It’s the rules. I don’t care what you see. I want to swim, and if you do too, we’re going to see everything.” Tobin tugged his pants and underwear off at the same time, revealing a huge penis that bounced against his balls when he stood back up. Then, he stepped into the shower and waited for Andrew to join him.

Andrew was mesmerized. Tobin’s dick was soft, and his was hard, yet at that moment, Tobin’s member was four times the size of Andrew’s. He would be very humiliated if the truth was revealed, especially if Chelsea saw him compared to her brother.

“I don’t want to shower with you!” Andrew said.

“Come on! I showed you mine, so show me yours.”

Andrew reached for his shirt but hesitated. Tobin, taller and stronger, stepped out of the shower to pants his friend, revealing his little secret.

“Ha ha ha! It’s so small. I didn’t know they could be this small!” Tobin laughed. He dragged Andrew into the shower and handed him the soap. Andrew covered his genitals with his hands, trying not to stare at Tobin’s superior penis.

Unable to dry off, Tobin ran straight from the shower to the pool and jumped in. Andrew stepped out awkwardly, saw Chelsea peering through an upstairs window, and ran back inside the pool house.

“I don’t want to swim anymore!” Andrew yelled at his friend.

“Why, because you don’t want my family to see your little dick? They’ll see it eventually, so why not rip the bandage off?”

Andrew, without a towel, put his clothes back on while he was wet. While attempting to do so, he discovered Tobin had ripped his underwear, rendering the pair unusable. Now he just had his wet t shirt and jeans. He laid in the sun to dry off while Tobin played in the water, big dick taunting Andrew.

Dinner was relatively more normal. The mother wore a pantsuit and served everyone their plates. She had determined that Andrew’s wet clothes were not fit to be worn at her dinner table, so she handed him some of Chelsea’s old clothes (Tobin’s were too big for Andrew, especially the underwear). Andrew ate dinner wearing a crop top, panties, and close fitting sweatpants. Chelsea, already in her nighttime attire of near lingerie, snickered at Andrew’s dick outline.

Soon after, the friends went to the basement to play video games. Tobin sat across the couch, his feet nearly touching Andrew. Andrew began to realize how sexually he viewed his friend.

Bedtime came, and the mother enforced her rules of nude sleeping by collecting everyone’s clothing, starting with Tobin. Andrew sheepishly removed his panties and handed them to her. The mother looked at the penis and smirked, then continued down the hall, where Chelsea would undress just out of view of Andrew. Now he was alone with his naked best friend.

“Like what you see?” Tobin joked. Andrew couldn’t hide his growing erection.

“When do I get my clothes back?” Andrew asked Tobin.

“After breakfast. We all eat naked.”

Andrew was horrified. “I don’t want Chelsea to see me like this again!”

“You have a little thing for my sister, huh? Well, there’s no way she’d go for a guy your size. She’s had boyfriends over before, and they were all bigger than me.”

“I don’t want to talk about this. I just want to go to bed,” Andrew huffed. Tobin had a kind sized bed, and a couch on the other side of the room with one afghan on it. Andrew covered as much as he could with the afghan and drifted off to sleep.

He awoke to a pinching feeling on his genitals. It was dark in the room, but he could see something shiny covering his penis. Andrew reached for it, and felt metal separating his hand from his dick, which was trying to get hard but didn’t have room. A metal ring around his dick and balls kept his member short.

He shook Tobin awake.

“What is this thing on my penis?”

“I was waiting for you to notice,” Tobin said happily, “I did that to you while you were asleep a few hours ago. It’s called a chastity cage. You’re locked in it until I decide to use the key.”

“Use the key now! This thing hurts!”

“Yeah, you can’t get a boner with it on. That’s the idea.”

“Take it off!” Andrew said. He noticed Tobin’s dick get harder.

“I’m not going to take it off until you do something for me,” Tobin said, throwing his sheets off him.

Andrew was hit with a wave of arousal, his body shuddering from his aching penis. They both knew Andrew was attracted to Tobin.

“Give me a blowjob.” Tobin grabbed his dick by the base and pointed it at Andrew. Andrew licked the head of Tobin’s dick, then put as much of it as he could into his mouth.

“Ah… oh! Oh!” Tobin said, Andrew’s mouth giving him extreme pleasure. Orgasm was fast approaching. Andrew’s tiny compressed penis leaked seminal fluid uncontrollably.

Tobin got close to coming and grabbed Andrew’s head, forcing his dick into his throat. Andrew gasped for air. Tobin’s hot load trickled down his neck and kept coming with each powerful thrust of his hips. Tears formed in Andrew’s eyes. Finally, Tobin released him.

“That was… so… good,” Tobin said, flicking Andrew’s little cage. Andrew’s penis tingled with so much excitement. He badly wanted to jerk off and come his own smaller load.

“Please unlock me, Tobin. I want to come so bad.”

“The key’s not in this room. It’s in Chelsea’s. You can sneak in there and look for it now, she must be asleep,” Tobin said, soon to go back to sleep.

Andrew couldn’t sleep throbbing against his cage. He crept down the hallway and carefully opened the door to Chelsea’s room.

Chelsea naked was the most beautiful woman Andrew had ever seen. Her tits, her tanned thighs, her shaved pussy. She lay on top of her bedspread, perfectly asleep.

Andrew had to be careful while searching the room. He started with what was already open to see, then tried desk drawers, then dresser drawers. Before he got to the closet, the bedside lamp clicked on.

Andrew dropped to the floor and covered his cage with his hands. Chelsea laughed.

“Looking for the key?”

Andrew, humiliated, nodded.

“Show me.”

Andrew stood and showed her his predicament. She cackled at his tiny penis, made smaller by cold metal.

“I wondered what Tobin wanted with one of my toys for boys. I had a pretty good idea. That’s why the key is around my neck.” Chelsea shook her chest at Andrew, the key bouncing off of her tits.

“I really want to get out. He locked me in while I was asleep,” Andrew said.

“What did he make you do? Suck his big, long dick?” Chelsea said, caressing her pussy. “If you’re willing to do that, why should anyone with the key let you go?”

Chelsea ran into the bathroom and held the key over the toilet. Andrew chased her, then stopped when he realized what she was threatening.

“Beg for me not to do it.”

“I’ll do anything you want! Please, anything! Just don’t flush the key!”

Chelsea nodded. She sprinted past him and threw the key in her safe, then slammed it shut.

“Looks like you’re my bitch now,” she taunted cruelly, “How long can you go before you come in your little cage? One week? One month? Six months? How long before you agree to take me brother’s big cock up your ass?”

Chelsea grabbed him by the cage.

“You’re going to move in here. You will give my foot massages, shower with me, dress like a girl. When my boyfriends come over, you will watch them fuck me. Then, they might fuck you. After that becomes your life for, say, three weeks, I’m going to try to make you cum in your little cage. If you don’t, I’ll let you go. If you can come in the cage, then why should I ever let you out?”

Andrew whimpered. He felt close to an orgasm just from her touching him. He thought his life had just become much harder–ironically, he might never get hard again.