Lenny was a nineteen-year-old virgin. He was also firmly in the closet. No one knew he was gay and he planned to keep it that way until he'd saved up enough money for college.
Mom was the town whore. Not literally, but in his hometown any hint of promiscuity was close enough. Mom didn't care about labels. Lenny knew she'd be fine with his sexuality once he left town. In the mean time, he wasn't going to encourage the town gossips.
Lenny was a virgin but he was still a boy. He spent most of his time thinking about the one thing he couldn't have. That was the one and only reason Lenny dated. Not boys mind you. Lenny dated girls. To keep him busy and distracted from his wanton desires.
He was currently juggling three pretties and that didn't include his best friend Shannon. He might as well count Shannon as the fourth girl but it was another instance of keeping up appearance. Everyone in school knew Shannon was head over heels for Lenny, including Lenny himself.
Friendship with Shannon was a guilty pleasure. He used her worst of all because Shannon was the key to Tim. There were evenings spent cuddling with Shannon on the couch so that he could watch Tim laugh at something on TV. And the afternoons spent cuddling on a lawn chair so he could watch Tim blot his damp skin with a fresh towel. Or the mornings waking up in Shannon's bed, after a purposeful late night, so he could bump into Tim in the bathroom.
All that time spent deceiving his (supposed) best friend for a lurid glance of her brother. The guilt didn't stop him. Images of Tim's cut calves, tight thighs, ripped abs, and sculpted arms always won over the guilt.
Lenny jerked off in private and fantasized in public and generally lived within inches of being found out. And that's what lead him to the most embarrassing moment of his entire life. Living on the edge took him to a place he could have never imagined.
A week after his 19th birthday Shannon came over with a "gag" gift. She kept calling it a gag but in a way that made him think there was more to it. She called it a gag in the same way she joked about jumping his bones.
Shannon, in her super tight pink tube top and micro-mini skirt, curled up on the bed next to Lenny and took out a long box. She said, in her best fuck-me voice, "I wanted to wait until we had a moment of privacy."
Lenny teased, "Privacy?"
"Until your mom left." Shannon admitted grudgingly. "Just open it."
Lenny tore off the pink bow and the loud pink wrapping. He ripped the tape and shook out the contents of the box. Onto the bed fell the biggest pink dildo he'd ever seen.
She smiled and he felt his heart skip a beat. His eyes widened blankly, like a deer in headlights, as he stared at her. She knew. This was her way of telling him that she knew.
"Don't be scared of it." Shannon picked up the dildo and waggled it at him. "It's just a dildo."
Lenny swallowed and tried to think of something to say. He wanted to run. Or maybe lay back and heave a sigh of relief. He couldn't decide, so he just stared at the thing.
She smiled wickedly and thwaped him on the arm with it. Lenny cringed. Her smile disappeared. She fell back on the bed and let out a disappointed sigh.
"God. It's just a joke. I didn't mean anything by it."
He squeaked, "You didn't?"
She looked over at him angrily. "I wasn't suggesting you should use it on me, or anything."
Lenny blinked.
Fueled by her anger, she sat up and snarled at him, "Or maybe I was."
A feeling of relief washed over him. This wasn't her way of telling him she knew. This was her way of telling him what he already knew. This was her not- so-subtle way of saying that she wanted to be more than friends.
"What's wrong about me?" Shannon demanded and then laid into him, "Why wouldn't you consider a little kink with your best friend? You go out with all the other girls. And I've heard the stories-"
"Hey!" Lenny interrupted rudely. "I told you. Those girls lie. We signed a contract. And I don't-"
"You're still on about that fucking contract?"
All serious like Lenny said, "That priest came to our school-"
"Oh. My. God." Shannon groaned and rolled off the bed. "Please don't tell me AGAIN about that sanctimonious fucking priest and how you bought into his stupid contract."
Shannon threw the dildo down on the bed next to him. "Happy fucking birthday."
Lenny heard her stomp from his room. He heard her slam the front door. He stared at the pink latex dildo and wondered what the hell just happened. Lenny picked up the anatomically correct device. He stood the dildo up on his chest and pointed it at the ceiling.
It was pretty in it's own way. Lenny loved the look of a hard dick. Mom's boyfriends used to tease Lenny mercilessly. One particular boyfriend liked to drink beer and watch porn. He's asked if Lenny liked "those big titties" on the screen. Lenny'd agree, just to keep the peace, but he wasn't looking at the titties.
Lenny stared at the porn star and his eyes went naturally to the guys cock. It was while starting at that long, hard porn dick that Lenny first realized he wasn't like the other boys. He didn't want to see the titties. He yearned for those stolen moments where he got to stare at that beautiful cock.
Lenny wasn't a dumb kid. He picked up pretty quickly that liking boys just wasn't gonna fly in this town. And, as the kid of the town whore, he knew better than to sneak around. There was no defensive way to hide his predilection. He had to go on the offense.
The dildo was making him hard. Lenny knew well enough the shape of his own penis. He spent enough time stroking the damn thing. Lenny touched the dildo with a finger. He ran a finger around the head of the dildo.
He shifted on the bed, moving to better accommodate the half-wood in his pants. He circled thumb and finger under the head of the dildo and slid the ring down to the base. Then he repeated the motion back up the shaft.
Lenny licked his hand. He smoothed it over the smooth synthetic penis and petted around the width of it. Impatiently Lenny jerked at his belt buckle. The jingle of his pants was immediately followed by the sight of his own member.
He brought the fake phallice up to his lips and licked at the plastic tip. He slid the pink dildo between his lips and licked around the tip with his tongue. Lenny put the head in his mouth and gently sucked.
His eyes closed, dildo in mouth, Lenny grabbed at his penis. He repeated the process of circling finger and thumb around the head and then using his hand to pet down to the base. He began to slowly jerk off while sucking on the dildo. Lenny pushed the plastic penis deep into his mouth, imitating what he'd seen on porn. He gagged a little as the dildo hit the back of his mouth.
Lenny popped the plastic penis from his mouth. He jumped up, kicking off his shoes, and let his pants shimmy down to his ankles. Hopping around in white sweat socks, Lenny shed his underwear and pants. He dug through the bedside table until he found the single sample of cherry flavored lube he saved from Halloween.
He tore off the top and squirted the cold liquid onto the plastic penis. Lenny spread the lube around, fully bathing the dildo in it. He held up the dildo and smiled at it. For a moment he stared and then the smile faded.
A confounded look spread over Lenny's face. He sighed and turned around in a circle. He ended up back where he started, in front of the bed. With a shrug Lenny knelt down. He leaned forward, one elbow braced against the bed, and reached around with the dildo. Spreading his legs, Lenny sloppily slid the dildo around his buttcrack, seeking entry.
Lenny spread his legs wider and leaned forward more. The tip of the dildo found the right hole but there was more resistance than he expected. He held onto the bed with his free hand and pushed firmly with the other. The head of the dildo slipped up into his anus and Lenny let out a surprised grunt.
It felt different than he imagined. A little uncomfortable. But a good kind of discomfort. For a moment he thought about abandoning the whole thing but his dick was hard and he was already half way there. Lenny pressed the dildo deeper. His eyes scrunched shut and his mouth opened wide as the dildo slid firmly up into his anus.
He shifted his free arm around and took hold of his dick. Lenny braced his face against the bed. The feeling of jerking off with the dildo in his anus was incredible. Lenny wasn't sure how long he'd last. He slid his hand up and down, faster and faster, over his throbbing dick. Spurred on by sensation, Lenny began to slowly fuck his ass with the dildo.
Lenny groaned and missed the sound of someone opening the front door. He was so absorbed in jerking off and fucking his ass, that he didn't notice until it was too late. Shannon pushed open the door, said something about being a "real ass", and he jumped up.
Shannon stopped, stunned, and stood still in the open doorway. His hard dick was full mast and it pointed straight at her. The dildo slid out of his ass with a slick "pop" and the sound echoed through the room.
"Was there..." Shannon stalled and then started again, "Was that in your ass?"
Her accusing finger pointed at the dildo on the floor between his feet. Lenny stepped forward and Shannon stepped back. Lenny held up a hand, signaling for her to stop. The confused look on her face only matched the determined look on his. This time she stayed in place.
He walked forward and grabbed her hair. Lenny put his mouth over hers in an aggressive, open-mouthed kiss. She grabbed him, holding on tightly as he tore at her clothes. In his head he played every scene from every porn he'd ever seen.
Lenny threw her on the bed and mounted her ferociously. He closed his eyes and rammed into her. She cried out, a sound of pleasure and triumph. He leaned down on top of her and pounded his cock into her. Lenny turned his face away as he fucked her. With deft strokes Lenny finished was he'd started minutes before.
He rolled off and stared at the ceiling. That certainly wasn't the way he expected it to go. She wasn't even the right sex. He couldn't believe he just popped his cherry with a girl. Shannon curled up around him. If she were a cat, she would've purred.
Lenny waved towards the floor and the discarded dildo, "About that-"
She interrupted, "I always knew you were a freak."
"Yeah." He responded dully.
"You could have told me. If all you needed was a little kink, well then, I'm you're girl."
"A little kink." He repeated.
She swirled a finger around his chest. "I'll do anything you want. Whenever you want." Shannon levered up over him and leered down at him. "I'm your sex kitten. Your fuck goddess. You weren't raised to be a nice boy. You need a woman that can satisfy you're every need. And I'm that woman."
Lenny smiled weakly. She curled up on top of him and made a sound of content.
"You're that woman." Lenny repeated.
He put resigned arms around her and knew that this moment was a speedy end to his treacherous ways.
Two months later Lenny stepped onto a bus. He waved down at Shannon. She was crying and it wasn't the first of her tears. He didn't have enough money for college but he had enough to leave town. And he couldn't keep making excuses. There was nothing she wanted more than a repeat performance and it just wasn't in him to give her one.
So Lenny stepped onto the bus. He left behind him a town, a mother, a closet, and the girl that took his virginity. And a pink dildo, that gave him a first taste of what he was missing and lead him to his last taste of what he didn't want.
The End.
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