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."
"Thanks."
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.
