Back To Fucked Up: Teenage Wasteland

Trish’s flashlight briefly flittered over the covers above their heads, before focusing on the open magazine and its glossy pages. There was a handsome college boy and a beautiful girl the same age. Both of them were naked. The girl had the boy’s cock in her mouth.

“Look at her suck that thing,” Trish giggled. “How the fuck did she get that much into her mouth?”

“It is pretty big,” Jessica agreed, almost involuntarily. The girl was kneeling in front of the boy, his cock halfway into her mouth. He was so hung that Jessica thought the tip would be somewhere down her throat, so why did she look so happy? That thing had to be choking her.

Really, Jessica would’ve rather aimed her flashlight at Trish. Trish was taller than her mother now and she’d dyed her long, thick hair a deep red that made her look ravishing. She was still a teenager, but her body was something else entirely, as luscious and sensual as an adult could possibly be—miles away from the malnourished, sun-starved scrawniness Jessica saw in her mirror. 

It was amazing that they were sleeping in the same bed; they didn’t look like they were the same species. And Trish had those nice, full breasts. Jessica had nothing like those. Most guys couldn’t take their eyes off of Trish’s melons. And it seemed like her nipples were always hard.

Trish turned the page. Her flashlight glared over its contents again. “You think that’s big? What about these?”

The guys in the picture were having a literal cock-measuring contest. All of them were so huge that Jessica thought it had to be Photoshop.

“Oh, they’re real,” Trish said, seeming to read Jessica’s mind. “You can tell by the veins—ever had one as big as those?”

“About,” Jessica bluffed.

“Yeah, my boyfriends have all been nothing compared to these guys.” Trish turned the page a little wistfully. “I wish I could meet someone this big.”

“Geez,” Jessica exclaimed, seeing a girl bent down on all fours, facing away from the man and the rigid cock that was buried almost entirely in her asshole. 

“Silly boy. Doesn’t even know which hole it goes in,” Trish quipped.

Jessica bit her lip, wondering how much those two could’ve been paid for a picture like this. What if someone recognized them? Wouldn’t their lives be over? Still, Jessica found herself wishing she knew a guy that big.

“Can you imagine how that must feel?” Trish breathed in her ear. “When it’s all the way in?”

Jessica shook her head. “It’s fake. It must be fake. A guy’s thing just wouldn’t fit in there.”

“Sure it would. Your asshole goes up into your stomach, and that goes up into your mouth, so anything that can fit in your mouth can fit up there.”

“But it would hurt!” Jessica protested.

“Well, isn’t it worth hurting some for a guy that big? Just imagine how it would feel in your pussy. That’d be worth having it in your ass.”

Jessica pushed Trish’s flashlight away from the picture. “A good boyfriend wouldn’t ask you to do something that hurt. I mean, what’s wrong with my pussy? Why can’t he just put it in my puss?”

Trish focused her flashlight back on the picture. “Maybe she likes it. She certainly looks like she likes it.”

“She’s pretending.”

“I don’t think I could pretend with something that big up my ass.”

“Well, it’s Photoshopped too, so…”

“It’s Photoshopped and she’s pretending?” Trish asked. “What’s next, are you going to tell me it’s really a drawing?”

Jessica turned the page for Trish, who proved easily distracted by the next picture. So was Jessica, though she more wondered what was going through the heads of the girls in the pictures. One girl sucking a guy’s balls, another his cockhead, another licking his shaft, and another straddling his face? Were they all paid the same or did they only get a fourth as much as the one girl who’d taken him in her ass? The girl with the ass certainly deserved more—that looked like a lot more work.

The next page had two women. One was flat on her back, her legs spread apart. The other woman had a dildo strapped to a harness on her waist. She was thrusting it inside of the first woman. Jessica couldn’t stop looking at it.

“Well, I suppose that’s one way to get a big cock,” Trish commented. “Just buy one. Big as you like.”

Hearing Trish say that, still looking at the picture, Jessica felt a ticklish feeling in her clit. She moved to adjust her nightie, pulling it so the hem would be between her legs, help hide her—status.

Trish saw her flushed face, the slight trembling in Jessica’s hand as she tried to aim her flashlight not particularly at the picture while not taking the beam of light off it either. “I have one, you know.”

“One what?” Jessica asked.

“A dildo. It even has straps. You wanna try it? It’s better than touching yourself.”

“No… no, I couldn’t…” Jessica said, but Trish was already out of bed, going to her closet. “You can’t possibly have one.”

“You think my mom cares what I do or don’t have so long as I have the right dress size?” Trish opened up one of the fan mail packages she usually left unopened, but let pile up in her room in a combination of defiance and self-recrimination. She took what looked like a garter belt out of it. “She checks for chocolate, not cock.”

And then Trish attached the dildo to it… Jessica put one hand on the arm that held her flashlight, just to be sure she wouldn’t shine it on Trish. “What’s that thing?” Jessica asked, playing as dumb as possible. 

“You know what it is,” Trish laughed. “What do you wanna do with it? Suck it? Ride it?” Trish shook it around. “Maybe take it up the ass.”

Now Jessica turned her flashlight off. “Cut it out, Trish. You’re being weird.”

“There’s no such thing as weird in show business. I’m particular.” Trish came over to stand by the side of the bed, dangling the dildo in Jessica’s face, and Jessica couldn’t believe the size of it. “It’s Patsy, Patsy… I’m here to entertain you, numbnuts… make you feel good… help you relax…”

“I’m tired. I’m going to sleep.” Jessica rolled over, facing away from the strap-on, but didn’t close her eyes.

“Bullshit. You’re not tired. Look at you. You’re all turned on. I thought you were frigid, but real cocks aren’t what you’re into, huh? At least, not as much as this.”

Jessica squeezed her thighs together. “Stop acting like everyone wants to fuck you just because you have tits now.”

Trish picked up some hand lotion from the nightstand. She poured it across the dildo and nonchalantly rubbed it around the dildo’s length. “Don’t be angry, Jess. I know you’ve wanted to fuck me for a while now. Back then, you wanted to hug me, then you wanted to kiss me… now this is what you want.”

“You’re deluded. You show me a bunch of sex pictures, then when I get turned on, you say I’m hot for you.”

“Okay then. Look at me. Look at me like I’m just some girl wearing a hunk of plastic and you don’t give a shit.”

Jessica thrust herself the other way, saw Trish pulling up her nightgown, exposing the fine hairs of her crotch—even that looked perfect—and the dildo strapped to her groin, hanging between her legs like a man’s. 

With Jessica watching, Trish knelt on the bed. The dildo was so close, closer than Jessica had ever been to a guy, but not as close as she’d been to Trish. She’d been in Trish’s arms, but not like this.

“Go on. Feel it,” Trish urged. “Just like the real thing, right? Maybe a little smoother. Not as warm. Does it matter, though? I don’t think anyone would really notice while it’s going in and out of you. There’s probably just this motion.”

As Trish spoke, soft and soothing, she reached down to lift Jessica’s nightgown. She gently caressed everything she revealed, running her other hand through Jessica’s pubic hair, up her belly, along the pert contours of her breasts. The nipples got stiffer and stiffer. Jessica couldn’t hide how she felt anymore. 

“Squeeze my tits? It feels different when you do it—it feels right. Is the door locked?” Jessica whimpered. “What if your mom comes in? She has a key.”

“She’s also had a handful of pills and a fifth of gin,” Trish said. “She wouldn’t notice an earthquake right now. Relax, Jess. I know what it’s like. You’re tense. You need relief. I can give it to myself, but you, you’re just… fucked. You need someone to do it for you.”

Jessica pinched her lips together. “You could have anyone. Anybody you wanted.”

“You could’ve let my mom keep… being my mom. You didn’t.”

“So this is how you thank me?”

Trish shook her head. “I just want to make you feel good, Jess. Quit hating yourself for five minutes. Let me like you.”

Jessica gasped, thrilled, as Trish’s delicate fingers played over her swelling clitoris. She wanted more, but Trish didn’t give it to her. Not yet. Instead she bent down and kissed her. There was a softness, a tenderness, that Jessica could barely take without breaking. The reason why she didn’t hug, didn’t hold hands, shoved Trish away but now she couldn’t. Her body was gravitating to the feelings Trish was giving it while her mind was lost. 

Trish kissed her deeper, tongue slipping inside her mouth, and Jessica’s hips churned as if she were touching herself. She wanted Trish, wanted to be Trish’s, take her no matter how many layers of defense she’d put up between them.

Trish swung her leg over Jessica, now straddling her, the strap-on dragging across Jessica’s navel. “Do you want it inside you?” Trish breathed. “I want you to have it. I want to fuck you with it.”

Jessica couldn’t speak anymore. Her body was talking for her. All she had to do was give in and being close to Trish, it already felt so good…

She moaned, put her arms around Trish, crushing Trish’s luscious breasts to her own until they could’ve been hers. She pulled her gown off, throwing it onto the floor—Trish was already embracing her again, flesh against flesh, almost as if she were trying to get to the obscene desire Jessica felt deep inside herself. Jessica was past the point of no return, willing to let Trish do anything to her. Defenseless, unarmored, trusting Trish to love her the way she didn’t know how to love herself…

Trish’s fingers went back down to her cunt, her clit—it already seemed like a small eternity since she had touched her there. Jessica groaned as they gave her the ecstasy she’d nearly forgotten she’d wanted so much; it didn’t seem as important as how Trish had kissed her. The rosy lips of her sex parted under Trish’s touch, letting in sharp thrills that seemed to spill everywhere, resonate in Jessica’s swollen clit…

“I’m not supposed to come this fast,” Jessica moaned, all she could think with her cunt roiling, her hips working up and down like a musical instrument Trish’s fingers were playing.

“Maybe I want you to come,” Trish teased her. “Feel my cock. Do it.” She took Jessica’s right hand and pulled it down to the slippery dildo. The other went to her own pussy. “Play with my pussy, Jess. Jack off my cock.”

“Oh fuck,” Jessica breathed, pumping one hand on the dildo, the other hand stroking Trish’s labia. Her own pussy was wet, the center of the trembling that went through all her body.

“Fuck is right, baby,” Trish grinned. “All this fucking black hoodie, Nirvana shit—you just needed to get laid. I’m gonna help you out with that, Jessica. I’m gonna make you come like you fucking dream about when you touch herself.” Her voice dipped to a low whisper. “I’ll fuck you in the ass, Jess.”

Just hearing her, Jessica knew she wasn’t kidding. Trish really was going to feed that big dildo into her butt. Jessica sucked in her cheeks, trying to think what that might feel like. Despite her earlier misgivings, now she wanted it as bad as a drug. She wanted to give Trish anything she asked, so long as she kept being hers.

Jessica started to roll over, but Trish didn’t want to be given, she wanted to take. She put the flat of her hand on the small of Jessica’s back and shoved her down, pressing her breasts into the mattress while keeping her ass in the air.

Taking up position behind her, Trish opened Jessica’s legs wider with her knees, then dropped her face to Jessica’s ass. Despite Jessica’s slenderness, her ass had some sizable curves, and Trish enjoyed the warm pressure on either side of her face while she ran her tongue between Jessica’s cheeks, lapping at her tiny anus to prepare it.

“I want your ass higher,” Trish said, and to her delight, Jessica obeyed, lifting up her ass in an open invitation of a gesture. 

Trish didn’t know if Jessica was a virgin—the boundaries of their friendship had many jagged edges—but she could tell from how tight Jessica was that there was no way she wasn’t an anal virgin. Trish was going to claim that hole.

More than that, Jessica trusted her to fuck it, to give her pleasure no matter how much it might hurt. Trish felt a heady sense of power, and even more of warmth, having Jessica trust her that much. 

Jessica wouldn’t have believed she trusted Trish that much either—had so many feelings for her that they swirled around until she couldn’t tell quite what they were, except for warm and fuzzy like those Disney movies they were both supposed to hate. 

But she was waving her ass around, now knowing that Trish enjoyed the sight of it, wanted it. Her asshole, moist from Trish’s tongue, throbbed eagerly. She couldn’t imagine how it would feel when Trish’s cock was inside it.

“Now open up for me,” Trish said. 

Jessica knew what she wanted—they weren’t sisters, but sometimes it was like they had the same mind, the same soul. She reached behind herself and opened up her buttocks with both hands, then tried to relax her muscles. 

She didn’t know how Trish’s dildo would fit up her ass. It seemed like it would split her in half first. But if it did, she wouldn’t care. Her heart pounded down into the bedsprings of the mattress. Jessica felt alive.

She winced as the tip of the dildo went into her. She shivered from head to toe, now knowing that it was really happening, it was all going into her. It hurt! It was tight, too tight to possibly give into how big she knew the dildo to be. But Jessica felt exhilaration too. Trish was doing it. She was fucking her in the ass. Whatever else happened, this would always be theirs.

“Shit, Trish,” Jessica moaned, wiggling her ass around the impalement going further and further into it. “You always have been a pain in my ass…” She lifted her hips up, giving Trish more access to her asshole. She wanted more.

Trish laughed. She wanted to give Jessica more. “And you’ve always been a needy little bitch,” she said warmly. “Guess this is what you’ve been needing, huh?” 

Trish took hold of Jessica’s narrow hips—so slim, so tomboyish—and pumped into her, watching in wonder as Jessica’s anus stretched to fit in her thick dildo. It took another few minutes and a careful dance of her hips, but finally she was all the way into Jessica.

Jessica panted for breath as Trish filled her to the brim over and over again. No matter how many times Trish hilted the dildo inside her, it always felt bigger, deeper. Thank God for the lubricant, sounding off wetly every time Trish entered her, letting the dildo slip almost effortlessly through the conquered territory Trish had made of her ass.

“Harder!” Jessica groaned, choking on her plea. “Oh, oh… harder!”

Trish fucked Jessica’s asshole as hard as she could, knowing that Jessica could take it, that Jessica was far stronger than her slender body would suggest. 

Jessica’s body was on fire. She pulled a pillow underneath her head and buried her screaming mouth in it, acutely aware of everything around her. The sheets beneath her stained with sweat. The grunts Trish let out as she drove into Jessica’s body. Finally, her own impossible pleasure as it blossomed into something Jessica had never felt before, her body wanting nothing more than to serve Trish and knowing that Trish wanted her to come. She’d never orgasmed so hard before. Never.

“Hnnnn!” Trish groaned out, pulled along with Jessica’s orgasm, her cunt rubbing against the base of the strap-on. Maybe that was how attuned they were to each other. Jessica couldn’t imagine that she was getting off without Trish enjoying it.

Trish laid on top of her, face down on her back. Jessica inhaled and Trish exhaled, both of them glistening with what felt like the same sweat. Finally, Trish pulled out of her and laid down on the bed, her strap-on still erect in the air, which seemed horribly ironic for some reason. Jessica nestled against her and stroked the dildo a few times, which made Trish laugh.

“You’re mine,” Trish purred.

“Uh-huh,” Jessica agreed. “Just keep making me come like that.”

“You keep coming for me like that,” Trish told her. “Fuck, you came like you loved me.”

“You fucked me like you loved me.”

“I love your ass.”

“I love your strap-on. Maybe I should date it.”

“Go ahead. We’re not dating,” Trish grinned. “We’re fucking.”

“I don’t care what you call it. Just don’t stop.”