Not The First Time He Imaginedbysuper_chicken©
He was a 22-year old virgin. He hated it. He didn't know why girls didn't like him. But he had ideas. He couldn't understand why guys he knew who were even shier than him could get chicks. He could meet girls. He had friends who were girls. But he could never take it to the next step. He could never show his interest properly. Part of this was because he had never been big on the physical contact: hugging and that kind of stuff. He also couldn't ask the right questions or give the right answers or something. Well, whatever it was there was nothing he could do about it. So he fantasized. And he tried to get the best orgasm possible.
He couldn't remember when he first heard about prostate stimulation. Probably somewhere on the net. He had seen it in "Road Trip," on the Sopranos and some kinky Showcase show. So he had decided to try it. And that's what he was doing now. He had told his parents he had rediscovered bananas as a food source. If they had looked in the compost they would have seen lots of mashed bananas and lots of peels.
So he separated one from the bunch. He went upstairs to his parents' bedroom and grabbed the Vaseline. Just the thought of the pleasure made him a little hard. He went back to his room and lay down on the bed. He never closed the blinds because no one could see him from the street. He pulled off his pants and his underwear and pulled up his shirt. He put two layers of Kleenex on his stomach to keep the cum off him.
The first part was always the hardest. Getting the banana in. The end pierced his asshole and he winced a little in pain. He dug in to the wall of his ass and grimaced. Finally, he nursed the banana through his sphincter and he felt the end hit the prostate. His cock always got as hard and as long as ever when he did it. He began to pump the banana in slowly. Then harder. And faster. It slipped out. He forced it back in. He hoped this time he could keep his other hand off his cock and get a real prostate orgasm. Every other time the pleasure was too much. He would give in a whack off.
* * * * *
She was 18. She had just moved into the neighbourhood. She didn't know anyone on the street but it didn't matter since she'd be leaving for university in a month or two. Her shift at work was over and she didn't really know what to do with herself. She looked at herself in the mirror, stroking her dirty blonde hair and examining her perky breasts. She thought about it for a second and then changed her mind. She'd play video games. It was in her brother's room. Her brother was a bit of an astronomy buff.
She walked into her brother's room at the front of the house and headed for his bed next to the window. She turned on the Playstation. She glanced out the window. Holy shit, she thought. It looked like there was a naked person in the house across the street. Without thinking, she grabbed the telescope and looked through it. She saw a guy. Near her age but a little older. His legs were bent and his ass in the air. She laughed. He was pushing a banana into his ass. What a fag. His face was grimacing. Then he grabbed his cock and whacked it a couple of times. Come spurted out onto some strategically placed Kleenex on his stomach. He was still writhing. He kept writhing and writhing. Stroking his cock and trying to force the banana back in. She couldn't believe the orgasm was still going. That's weird, for a guy, she thought. He stopped moving. He looked disappointed for some reason. Then he started grinning. He got up and moved out of sight. When he reappeared he had more Kleenex and he was dressed. He walked out of the room and into the hall.
Holy shit, she thought. She had just watched a gay guy masturbate. That's hilarious. She was gonna have fun telling her friends about it. Once they got back from up north, that is.
The next day she couldn't stop thinking about what she had seen the day before. None of the guys she had been with were like that, she thought. But she didn't know why. She had always like guys. But when it came to sex girls were just better. She had had her first lesbian experience at 16. She had been delivering flyers two summers ago, and a thirty-ish lady, Ms McGuire, had invited her in for some lemonade. From there, she was introduced to the world of girls. She soon introduced a couple of her friends to it over some booze. She wasn't a lesbian, but girls were just more sensitive to each other's needs. She still liked guys. She was going to marry one. But she had to find one who didn't just want a blowjob and a fuck and then went to sleep.
She went into her brother's room. It was almost time. He wasn't there. She waited. And waited. Then she gave up and played video games. An hour or so passed and she saw him come in fully dressed. She grabbed the telescope. He had a banana. But he also had a magazine. She looked closer as he took off his clothes and opened up the magazine. He put it against his legs while he slowly stuck the banana into his asshole. She was shocked. The picture she could barely make out was of two girls fucking. They had a double-tipped dildo thrusting into their pussies. If he's gay, why is he looking at girls?
The next day, she had decided. She was going to introduce herself. After all, it was the neighbourly thing to do.
He had just got home from work. He was fixing himself a snack. The doorbell rang. Fuck, he thought. Just when I'm trying to eat. Who could that possibly be? He opened the door and saw a high school chick. She was a lot shorter than his 6'4". She had dirty blonde hair. She was wearing jeans and one of those blue and white striped shirts that exposed her midriff a little. Her shirt was open to the last button. He hated those shirts but he could never look away. He told himself he hated girls exposing themselves to anyone like that. She had a petite backpack over one shoulder. Typical stupid high school girl, he thought.
"Hi, I'm Mandy." She said. "I just moved in across the street. Saw you come in a second ago and I thought I'd say hi."
"Well, uh, that's uh, very neighbourly of you." He stammered. Wow, he lucked out. This chick was hot. But she'd not want him once she knew him. They never did. "Uh, come on in."
As the door closed she turned to him and grabbed his cock through his jeans.
"Holy shit..." he barely got out.
She leaned towards him and said, "We're going up stairs, you first."
He obediently headed up the stairs. As he walked ahead of her she took her right index finger and lightly brushed him on his rear from his taint along his crack to his waist. He turned and she smiled.
"What?" she asked.
They got to his bedroom.
"Sit down." She commanded.
He did, and so did she. She put her backpack on the floor.
"So tell me about yourself."
"What do you want to know?" he responded.
"Sex stuff." She said.
He felt his cock get slightly hard in his pants. Every time he talked to girls about sex he got hard. Fuck, he was gonna blow it.
"Uh, there isn't much to tell. I'm a virgin."
"A virgin!" She started to laugh. Then she stopped.
"Sorry, I guess that's cool. So you just can't get any cock or what?"
He looked shocked.
"You're gay, aren't you?"
He was pissed. Fucking teenagers. They always decide you're gay if you're a virgin. The last time he had been trying to start something with this girl she had thought the same thing. And she had told all her friends.
"Just because I'm a virgin doesn't mean I'm gay. Grow up. Ever heard of abstinence?"
"I know you're gay. I saw you fucking yourself with a banana the other day."
His face flushed. "Fuck, really?"
She nodded. "You loved it!" She laughed at him.
He felt really embarrassed. But no use in denying it.
"Well, I like the feeling. Ever heard of prostate stimulation? It's true."
"Real men don't shove shit in their asses."
Fuck, this girl is mean, he thought. But she's so hot. He wanted to throw her out but he couldn't.
"It works, seriously. I've been trying harder and harder to get the best orgasm ever. I just can't take it and I always whack off instead of waiting for the banana to make me cum."
"Hahahah," she laughed, "you're such a loser! If you're not gay why don't you fuck some girls?"
"I can't get any girls to..." he stopped because her hand was on his leg. His cock was getting harder. She felt the familiar wetness between her legs.
"I think you need to be fucked by a girl so you don't stay a fag."
"I'm not a fag!"
"I know you are!" She laughed again.
She began to undue his jeans.
"What are you doing?" he asked in disbelief.
"What does it look like? Shut up! No wonder you don't get girls!"
She pulled down his pants and saw the shape of his cock through his underwear. She got off the bed on got down on her knees. She pulled off his underwear and revealed 6 inches of male organ. She had seen bigger. She had blown bigger. No problem though. This would be easy. She took it in his mouth and she felt him convulse. He came immediately and she almost choked.
"Asshole!" she yelled. She kept the cum in her mouth and stood up. She said in a garbled manner, "That wasn't cool."
"I told you I'd never been with anyone."
"We're gonna have to fix that. But first, you gotta be punished. Kiss me, " she commanded.
He looked up at her. She leant down. Their lips met in an open mouther kiss. She grabbed him by the shoulders and forced her cum-covered tongue into his mouth. He recognized the familiar taster of his own cum that he licked off his fingers after he masturbated.
"Ummm, you liked that didn't you?" she asked.
"Ok, here we go again."
She spit the rest of the cum into some Kleenex and she got down on her knees again. She took his cock, which was still hard, and put it back in her mouth. She moved up and down the shaft. She alternated between licking the shaft and deep throating. He moaned even though it hurt. He hated how his dick felt when he whacked twice in a row. It felt the same now. But it felt so good at the same time. She took off her shirt and bra and slapped his dick on her tits. She laughed when he stared at her, kind of shocked.
"Lean back," she ordered.
He did as he was told. She opened her backpack and got out handcuffs her ex-boyfriend had left at her house. He used to handcuff her while they fucked. He had liked being in control. Now she was in control. Total control. She handcuffed him to the bed frame.
"That's so you don't whack off. Thin of it as postponement of gratification." She appealed to his nerdiness.
"Ok," he whimpered.
She went back to the floor and got back down on her knees. She forced his ass higher in the air. He took his legs off the floor and bent them on the end of the bed. She rubbed his taint and sucked his balls. She licked his hard cock again. Then she licked his right ass cheek. She moved her tongue slowly around the outside of his asshole. She saw his sphincter pucker in anticipation.
"Only a fagot would crave cock like your sphincter is right now, fag!"
She tongued his asshole vigorously and he moaned deeply.
"Ooh, you like that? Tell me!" she ordered.
"Tongue my ass!" he said. "Tongue my ass!" he yelled.
She kept rimming him and sticking her tongue into the hole as far as it would go. She spread his cheeks and tried harder. Then, suddenly, she stopped. She stood up and took off her pants, socks and her red thong. She showed off her body to him.
"I bet you'd like a piece of this," she said as she ran her finger up his shaft.
She walked over to his head and kissed him deeply again.
"Oh yeah, you like the taste of your own ass, don't you?" she told him.
He nodded and tried to kiss her more. She stood up.
"No, no more. Tell me you want me to fuck you," she commanded.
"Fuck me," he muttered.
She went back to the end of the bed and got down on the floor. He couldn't see what she was getting from her backpack. Her heard her making noises but he couldn't move to see her because of the handcuffs.
Out of his sight she put on the strap-on dildo that Mrs. McGuire had given her as her 17th birthday present. She made sure the straps between her legs fit around her clit. She touched herself. This is going to be awesome, she thought.
She stood up with the dildo in plain view of her prey. He stammered but he couldn't get anything out of his mouth. She forced his legs apart and into the air. She licked the left one from top to bottom. Then, suddenly, without any warning and without any mercy, she plunged the 8-inch pink dildo into his waiting asshole.
"Ah, fuck. That hurt," he protested.
"Shhh," she ordered.
She began to fuck him slowly and then faster and harder. He began to moan in simultaneous pain and pleasure. It had never felt like this with the banana, he thought. It hurt so much. But it was so good.
"Fuck me! Harder! HARDER!" he screamed.
She obliged and, holding on to his legs, fucked him in the shitter as hard as she could. All he could think about was whacking it.
"Whack my cock! Whack my cock!" he yelled.
"No, bitch!" she said, almost laughing at how silly it sounded. "That's what the handcuffs are for."
As she pounded his ass she felt the straps of the harness rubbing her clit and she got wetter and wetter. She tweaked one of her nipples and began to stroke her clit. She forced his legs back towards his head and he grimaced. In the throes of passion their lips met as she fucked his ass and he struggled to reach her approaching face. They sucked each others tongues and he bit her lip. She forced his head back down and he started fucking him harder again. His cock and his ass both hurt so much. But he couldn't stop yelling for her to fuck his ass.
He came so much he almost hit himself in the face. She pounded him a couple times more while he writhed and then took the dildo out of his ass. She stuck her fingers in there and then rubbed them along the stomach so they mixed his ass juices with his cum. She stuck the fingers in his mouth and he sucked them off. Then she kissed him deeply.
"Now it's my turn," she said.
She straddled his chest and fed the dildo to his mouth. He tried to take as much as possible but he kept gagging.
"We'll have to work on that," she said as she got up and turned around, sticking her ass into the air above his head.
"Tongue my ass."
He struggled to reach her sphincter because of the handcuffs but when he got there he willingly dove in to it. He rimmed it and probed his tongue into the hole. She stroked her pussy through the straps and kissed his cock and balls more. He rimmed her as hard as he could and she stroked and stroked. She came on his chest, dripping her juices on him. She got up and gave him her juices to lick off her finger. He hungrily complied.