Halloween Hookup

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Not to be read by anyone under 18, unless you’re a hot chick.

In which case my address is:

6669 NE 42nd St.

Utica, NY (not really, but you can still drop by and see who lives there if you want)

The following is completely fictional. Any resemblance to reality is entirely coincidental. Contents of this story are merely creative license, not unlike a TV show or movie that uses real people in fictional settings and situations. However, if you do have video or pictures of events similar to the ones described below, feel free to forward them to me for closer examination. Feedback, comments, praise, criticism, death threats, nude photos, etc. can be sent to voodoojoe2000 at yahoo dot com (come on, you can assemble that into an actual e-mail address).

For personal use only. Feel free to distribute to friends, enemies, lovers, hopeful lovers, whatever, just keep my name and e-mail address on the story or I shall hunt you down and make you write the whole damn thing out by hand.

Celeb of choice in this story is Debby Ryan. The codes are (MF, cons, oral, anal). Go fuck yourself and go read something else if you dislike those codes or want something more. Or better yet, write it yourself.

Halloween Hookup

By voodoojoe

Carrying two garment bags with costumes in them, Debby Ryan pushed open the door of her boyfriend’s house. Closing the door behind her Debby was about to call out when she spotted something that made her pause.

Closing the distance she picked up the high heel that most definitely wasn’t her boyfriend’s. Even if she wanted to believe that he might be into wearing such a thing, it was way too small anyway. So still holding the shoe in her hand she turned and headed straight for his bedroom.

Hearing moans and the squeak of springs as she neared the door, Debby felt like a hand had reached into her chest and taken hold of her heart. Part of her wanted to run so she could still claim the shoe belonged to his mom or sister or something and maybe the moans were because she ate something spicy that gave her heartburn so she was laying on his bed, making the springs squeak, and this or that.

But while denial sounded like a whole lot more fun than whatever she was likely to find on the other side of the door, Debby knew she had to find out for herself. If the bastard was cheating on her, it would hurt, but it would be better to find out sooner than down the road when she was getting really serious about him.

Grabbing the doorknob Debby quietly turned it. Pushing the door open the first thing she noticed was the volume of the noises inside the room getting louder. Second thing she noticed was the sight her boyfriend’s bare ass as he thrust into the waiting pussy of some slut on her hands and knees in front of him.

“What the FUCK!” Debby screamed, causing her boyfriend and his slut to dive for cover.

“Debby?” Wes responded, pulling a pillow in front of his crotch. “It’s not what it looks like.”

“Fuck you,” Debby snarled, throwing the shoe at him and making him duck as it hit and knocked over a lamp from the table next to the bed.

“Debs, I swear,” Wes started before Debby gave a look so cold and icy he instantly shut his mouth.

“We are through,” Debby snapped. “Don’t ever call me, come near me, or even think about me. In fact, I think I’ll keep your key just in case you decide to do any of things. That way I can come back and smash everything I can find. Then for fun I might just go into the garage with a baseball bat and take a few swings at your precious little car.”

“You wouldn’t,” Wes said, his eyes narrowing at her threat to his classic Mustang.

“Try me,” Debby said before fixing her eyes on the perfect little blonde slut trying to hide under the covers. “He’s yours now, but you should remember that once a cheater, always a cheater.”

Before either of them could say anything Debby turned and grabbed the door. Before walking through it though she turned and gave Wes a malevolent grin as pushed over the bookshelves Wes had next to the door. It toppled over and smashed into his flat screen television on its way down.

“Fucking bitch,” Wes cursed as Debby slammed the door behind her.

* * * * *

Sitting in her bedroom staring at the garment bags, Debby wanted to do anything but one of the costumes on and go to a Halloween party. She’d rented the costumes and was supposed to take her boyfriend, but that obviously wasn’t going to happen. In fact, the only thing keeping her from just not going at all was the fact that her friend Robin would want to know why, and then Robin would come drag her to the party anyway.

Sighing, Debby got up. Grabbing the costume that was for her she opened it up and pulled out the tight, very short strapless green dress that made up the main part of her costume. Next came the miniature hat and small velvet basket.

Shrugging her shoulders she quickly disrobed. Picking up the dress she held it against her body and was shocked at just how short it was. She was supposed to be a sexy leprechaun with her boyfriend as her pot of gold, but now she was stuck going alone, in a dress that was likely to make every guy ask her about getting lucky.

Opening her dresser drawer she pulled out a pair of white thigh-high stockings to pair with the dress. As she slid them up her legs she realized that even though they went to mid-thigh they almost reached the bottom of the dress.

“If I’m going to do it, I might as well go all the way,” Debby said, grabbing a pair of black strappy heels to wear with it.

When she had everything on she turned to look at herself in the mirror. The dress had little shamrocks all over the loose-fitting skirt while the tight, curve hugging bodice had a simple white accent around her cleavage. On her head was a little green top hat that was attached to headband she covered with her hair.

“I really hope Robin has alcohol,” Debby said, grabbing the soft velvet basket and tucking some money and phone and a couple other small essentials into a side pocket. She really wasn’t a drinker, like at all, but after everything that had happened she figured the only way she was going to make it more than fifteen minutes was if she had something to numb her up a bit.

Before exiting she stopped in the kitchen and opened the plastic bag sitting on the counter. Earlier she’d stopped by the store and bought some gold coins to put in her basket so it looked like a small pot of gold. She’d planned on passing them out to friends but now was tempted to just sit and peel the gold foil off the chocolates and eat them all.

Pushing that thought out of her mind Debby collected herself once again. Grabbing her keys she headed for the door. She was going to go to the party and have fun and think as little about the cheating asshole as possible.

* * * * *

“Where’s Wes?” Robin asked, the moment she saw that Debby was alone.

“Lets just say he’s not coming,” Debby muttered, frowning as she walked past Robin.

“What? Why not?” Robin asked, not leaving it alone because she was the curious type.

Cute, petite girl with brown hair, Robin had been one of the first people Debby had met when she’d moved to LA from Texas to pursue her career. They’d become immediate friends and had spent more than a few nights talking about boys and sex and each were the first call they’d made after they’d lost their virginities.

“I went to drop off his costume and well, he wasn’t exactly alone,” Debby said, pushing her way through the crowd of party goers.

“Oh my god,” Robin gasped. “Yours looks awesome, by the way.”

“Thanks, I needed that,” Debby said, forcing a small laugh. She’d never been able to tell whether Robin always knew the right thing to say, or if it just happened to be that whatever came out of Robin’s mouth was the thing she needed to hear. Either way, the small brunette always managed to cheer her up.

“I’m betting you also need a beer,” Robin said, pointing toward the large metal tub full of ice and various bottles of beer. When Debby blanched, Robin shrugged and reached the other way to grab a bottle of liquor. “I’m not even going to look at the label to see what I’m pouring you.”

“It’s brown,” Debby said as Robin poured a measure of alcohol into a glass.

Picking up the glass, Debby lifted it to her lips. She didn’t even bother to sniff it or swirl it in the glass or any of those techniques. Instead she tilted her head back and let the fire water slide down her throat, warming her mouth and throat along the way.

“Huh, I guess it was scotch,” Robin said, finally looking at the label. “Considering you’re a sexy leprechaun, I should be giving you Irish whiskey, shouldn’t I?”

“Doesn’t matter, just keep ‘em coming,” Debby said, her already husky voice getting a bit hoarser thanks to the scotch.

“Here, try this,” Robin said, pouring out of a different bottle.

With the first drink still emitting warm sensations in her stomach, Debby took the second one a little slower. She took two sips from it, savoring the smoky flavor profile before she pushed the glass back in front of Robin.

“Take it easy there,” Robin said, remembering the last time Debby had been like this. She’d downed a few shots of tequila and wound up passed out in a bedroom while Robin made sure no guy got anywhere near her. “One more and then you’re done for a while.”

“You’re no fun,” Debby said, even though she knew her friend was right. She was already beginning to feel the very early effects as the alcohol started to enter her blood stream.

“Just being protective of my bestie,” Robin said, giving Debby a hug. “Wouldn’t want some strange guy taking advantage of you when you’re drunk and vulnerable.”

“Maybe that’s what I need,” Debby grunted, taking a sip of whatever Robin had poured into her glass. “Just find some random guy to hook up with.”

“If that’s really what you want, I can think of a couple guys that think you’re hot but aren’t really relationship material,” Robin offered. “That way you wouldn’t have to worry about them sticking around if you don’t want them to.”

“Are they any good?” Debby asked, knowing that while Robin wasn’t a slut, she wasn’t exactly fresh off the showroom floor or anything either.

“I wouldn’t recommend them to you if they weren’t,” Robin said, grinning. “But you’re not the one night stand type and we both know it.”

“Maybe that’s my problem,” Debby sighed, taking a sip of her drink. “I’m not wild enough so guys start looking elsewhere.”

“Find some guy, flirt with him, and then give him your number,” Robin said, putting an arm around her best friend’s shoulders. “And if you really have to have sex with him tonight, be smart about it.”

“Yes, mom,” Debby said, laughing because it was usually the other way around. Normally Robin was the one contemplating something crazy and she was the conscience trying to talk her down.

* * * * *

“Wow, sexy leprechaun? Nice,” said a guy dressed as Where’s Waldo? as Debby walked by.

“Thanks, have some gold,” Debby said, handing Waldo a chocolate coin. “But Waldo? Really?”

“Hey, I was a big fan as a kid,” he said. “Actually, I forgot so I just threw something together. I saw the red and white striped sweater and bought the hat this afternoon, and bam, I’m Waldo.”

“What about the glasses?” Debby asked, grinning.

“Oh, they’re actually mine,” Waldo said, lifting the glasses away from his eyes. “Wear them every day. Blind as a bat without them. Right now you look a bit like a green cupcake with red frosting.”

“I sound delicious,” Debby said.

“You look delicious, too,” Waldo said, making Debby blush.

“Who’s your friend?” a guy dressed as The Lone Ranger asked Waldo as he looked Debby up and down.

“Uh,” Waldo said, having not gotten Debby’s name yet.

“Veronica,” Debby said, giving them a fake name for the fun of it. “But everyone calls me Roni.”

“Nice to meet you, Roni, I’m Eric,” Lone Ranger said, extending his arm to offer her a beer.

“Nice to meet you too, Eric,” Debby said, trying to be as casual as she could as she looked up them up and down.

Eric was tall and broad shouldered. And while she couldn’t quite tell under his loose cowboy shirt, he sure looked like he was solidly built. Waldo, meanwhile, was shorter and thinner, but had a warmth and openness to his features that was largely missing from Eric.

“So, how do you two know Robin?” Debby asked, opening the beer.

“We came with a friend that goes to school with her,” Waldo said.

“So you don’t really know her?” Debby asked, trying to decide between them.

Just from immediate impressions, Waldo seemed like the nicer, more considerate of the pair. But Eric was hotter and had a confidence about him that made her think he’d be better in bed if she went through with it while Waldo was more the type she’d want to date.

“So, Roni, why don’t we find a quieter place to chat?” Eric asked, as if reading her thoughts.

“Well, I was kind of talking to Waldo here,” Debby said, feeling a rush of nerves as she was confronted with the reality of what she’d been looking for.

“I meant all three of us should find some place to sit and talk,” Eric said, trying to suppress his disappointment. He’d seen the way she’d looked at him and had been hoping to get her alone and see just how far she was willing to go.

“I know just the place,” Debby said, quickly draining the rest of the bottle of beer before leading them away.

“Might need reinforcements,” Eric said, grabbing a few extra beers before following after her.

* * * * *

Leading them up the stairs, Debby pushed open the door that led into the attic. Robin’s parents had finished it into a game room of sorts when Robin’s older brothers had been teenagers and when they moved out Robin had taken it over as a hangout spot for her and her friends.

As Debby sat down on one of the couches with a guy on either side of her she tried to turn her mind towards the task of deciding which one she wanted, or if she even wanted to go through with it. Complicating matters though was the thin layer of alcohol keeping the neurons in her brain from firing properly.

“Mmm,” Debby moaned as Eric took a chance and snapped her out of her thoughts by turning her head and kissing her.

As if sensing that Debby was trying to choose between them, Waldo put his hand on her cheek and broke her kiss with Eric by turning her towards him. Before Debby even realized what was happening Waldo leaned in a kissed her.

While Waldo was trying to turn Debby towards his side, Eric had moved on to other things. He’d been staring at her tits and couldn’t help but test the waters by reaching out and cupping one of them through her dress. And as great as they looked, they felt even better as he softly squeezed it.

Between the kissing and the fondling Debby could feel her body starting to respond. When she broke the kiss with Waldo Eric swooped in to reclaim her lips. With Waldo left unattended, he quickly followed Eric’s lead by squeezing and kneading her other breast. He then raised the game by slipping a hand behind her back to unzip her dress.

With things moving just a little too fast, Debby broke the kiss with Eric and gently pushed their hands away. The room felt like it was a hundred degrees and she was panting slightly from the kissing. Wanting to take a moment and calm herself down, Debby reached out and picked up one of the beers that Eric had brought with him and set on the table in front of the couch.

“Whew, it’s hot in here,” Debby said, taking a sip of her beer.

“It must be the heat from the people downstairs making its way up here,” Waldo said, following Debby’s lead and opening a beer.

“That must be it,” Eric agreed, trying to come up with his next move. He knew there was pussy in the offing, but he could also tell that she was the type that needed convincing so he didn’t want to push too hard and have her clam up instead.

“I like your mask,” Debby said to Eric, cringing inside at her attempt to make small talk.

“Here,” Eric said, pulling the mask off and putting it on Debby. “Now you’re a masked lawman hunting down those that try to steal your gold.”

“How do I look?” Debby asked, modeling the mask for the guys.

“Hottest leprechaun the old west ever saw,” Waldo said, taking a sip of his beer.

“Here, you can have it back,” Debby said, starting to take the mask off.

“Keep it, it looks better on you,” Eric said, leaning in to kiss her again.

Catching her by surprise a bit, Eric pushed his advantage. He pressed her back into the couch as his hands explored her upper body. When she moaned and pressed back into him, he slipped his hand behind her and took hold of her zipper.

This time when she felt her zipper being pulled down Debby didn’t stop it. In fact she even leaned forward to give Eric better access and make it easier for him to pull down her dress far enough for her bra-encased tits to come into view.

Almost as soon as Eric had pulled down Debby’s dress, he’d reached for the hook on her bra. After minimal fumbling the clasp popped open and Debby’s tits were fully exposed. Her nipples had already been semi-hard from everything that had been going on, but the feel of the air hitting them took them most of the rest of the way.

His breath catching in his throat at the sight of Debby’s amazing tits, Waldo couldn’t help himself as he leaned down to take one of her nipples into his mouth. Groaning at the feel of a warm, moist mouth latching onto her nipple, Debby instinctively brought a hand to the back of Waldo’s head to hold it tighter to her chest.

Taking Debby’s lack of objection, and even participation, as permission, Eric slid a hand down her stomach. Reaching her leg he slid it underneath her dress, slowly moving it up her smooth thigh until his fingers found the fabric of her panties.

Feeling Eric’s fingers rubbing her through her panties while Waldo sucked on her nipple, Debby suddenly realized that choosing between them might not be an option. She’d gone too far to suddenly send one of them out of the room while she fucked his friend. It was pretty much all or nothing at this point and Debby was having as much trouble deciding which as she was over which one of the guys to choose.

At first she’d been leaning towards Eric but then she’d started to swing towards Waldo since he seemed to be the better kisser. But Eric was definitely the more aggressive of the pair and would be more likely to give her that little extra push she was likely to need to go through with it all.

Part of Debby’s brain was screaming for her to stop everything and go home before things got out of hand. But she spent way too much time being careful and listening to that part of her brain. Right now she wanted to ignore that voice and give herself over to the pleasure.

When Debby still didn’t stop him Eric pulled the material of Debby’s panties to the side and dragged his middle finger along the length of her slit. She was absolutely soaked and when he pushed his finger into her pussy it slid inside with ease.

“Ohhhh,” Debby moaned, spreading her legs wider as she firmly decided that she was going to get fucked. Even if that meant fucking both of them, she wasn’t about to stop and she wasn’t going to send one of them away.

Finger slowly pumping into Debby’s pussy, Eric took hold of one of her hands, the one nearest to him. Placing it in his lap he moaned when Debby pressed her palm against his cock and rubbed it through his pants.

Feeling Eric’s manhood in her hand, Debby’s arousal took another leap. It wasn’t huge, but it wasn’t small either. She couldn’t tell the exact measurements without seeing it or even getting a good grip on it, but she figured it was at least six or seven inches with solid girth. It did make her curious about Waldo though.

So Debby found herself slipping a hand up Waldo’s leg until her hand came into contact with the lump in pants. She yanked her hand away like she’d been burned at what she found though. His cock had felt like it was at least a couple inches longer than Eric’s but also quite a bit thicker. It was easily the biggest cock she’d ever felt and suddenly all she could think about was getting a better look.

Finding the zipper to Waldo’s pants, Debby tugged it down. It had barely stopped before Debby was slipping her hand through the fly and worming its way into his boxers in search of his rod. When she found it she wrapped her hand around the shaft and marveled at how thick it was.

Wanting to see it she pulled it out of his pants and couldn’t believe her eyes. If anything, her estimates had been on the conservative side. While she wouldn’t say it was a foot long and looked like a baby’s arm holding an apple or anything, it was probably actually closer to that than it was to what she was used to.

“Suck his cock,” Eric whispered into her ear, noticing the way she was transfixed by the sight of it.

Taking a deep breath Debby slowly leaned over. She scooted around on the couch until she could get her head into Waldo’s lap, feeling Eric shift around as well to make room for her to stretch out a bit.

After a moment of closer inspection with her face so close Debby finally opened her mouth and took the head between her lips. Waldo moaned and sank further into the couch as she felt her mouth stretch around his cock.

As Debby started to work more of Waldo’s cock into her mouth Eric set about getting her naked. Slipping his finger from her pussy he grabbed hold of her dress and started working it down the rest of her body. When Debby planted a foot on the ground and an elbow on the couch to lift up he finally got it far enough that he could pull it the rest of the way.

Down to just her panties, Debby wasn’t surprised when she felt Eric’s hands take hold of the waistband and start to pull them down. She felt an extra thrill as Eric dropped her panties on the ground knowing that she was naked, save for her stockings, in front of two guys, even on top of the fact that she had a few inches of cock in her mouth.

With Debby’s mouth occupied Eric was left with the conundrum of whether he should be a nice guy and give her a little oral of her own or if he should just grab hold of his cock and ram it home. Ultimately he chose option A though and slid off the couch onto his knees. Pushing her knees apart he leaned in let his tongue have some fun.

“Uhhhh,” Debby moaned around Waldo’s cock as Eric lapped up some of her juices.

Having very little experience giving and receiving head at the same time, even in a sixty-nine, Debby had trouble concentrating on the large cock in her mouth while Eric licked her pussy. Each time his tongue flicked her clit Debby moaned and paused momentarily in her own oral ministrations before resuming bobbing up and down on Waldo’s cock.

“How’s her pussy?” Waldo asked Eric, his eyes traveling from the red hair in his lap over her impressive tits and flat stomach to where his friend was experimenting with different tongue techniques in search of what Debby liked most.

“Pretty fucking sweet,” Eric said, using his fingers to spread her labia to give Waldo a better look. “Want to switch?”

“Okay,” Waldo said.  While Debby was solid in her cock sucking, she wasn’t so spectacular that he’d refuse to share.

Pulling Debby off his cock Waldo started to slide off the couch. Almost without thought he leaned in and gave her a soft kiss before standing up.

Sitting up on the couch she watched as Eric hurriedly removed his pants. When he hooked his fingers in his boxers and pushed them down she was pleased to note that while he wasn’t as big as Waldo, he was still a bit bigger than her now ex.

As Eric settled on the couch next to her reached her hand out and gripped his cock. It was about the same length as her ex boyfriend’s, but a bit thicker and it felt really good in her hand. And as she stroked it she figured it was maybe even a little thicker than Waldo’s, even if it wasn’t as long.

Licking her lips she leaned down and dragged her tongue along the length of the shaft. Reaching the head she licked along the sensitive ridge of the mushroom head, drawing a groan of approval from Eric. As she finally took the head into her mouth she used her free hand to fondle his balls.

Dropping to his knees in front of Debby Waldo put his hands on her knees. Sliding them along her thighs until he reached her hips. Continuing along he let his hands caress her stomach, his fingers fanning out to softly rub and stroke her smooth skin as he made his way towards her chest.

“Mmm,” Debby moaned around Eric’s cock as Waldo’s hands found her tits.

Squeezing her tits in his hands Waldo gently kneaded them, pushing them together and pulling them apart. While still playing with her tits he leaned forward and placed a kiss just below her belly button, then another a little lower.

When Debby spread her legs wider Waldo finally let go of her tits and dove in. Where Eric had gone easy and slow Waldo went hard and fast and had Debby squirming almost immediately. Grabbing her hips to hold her somewhat in place Waldo attacked her clit with zeal.

Bucking her hips against Waldo’s face Debby felt days, and even weeks, of sexual frustration coming to the surface. Her ex had never been a big fan of cunnilingus and had practically needed to beg him to get him to do it. So to have not only one, but two guys do it without her even having to ask was a surprise to say the least.

Combined with the excitement of doing something so drastically different from anything she’d ever even contemplated, Waldo’s tongue rapidly had her on the verge of coming. Normally it took a while for her to get there, if she even got there at all, so it was shocking when she felt the first spasms hit her so quickly.

“Ohhh muhhh gahhh,” Debby groaned around Eric’s cock as she came.

Clamping her thighs against Waldo’s head she arched her back and lifted her butt off the couch. Her eyes rolled up in the back of her head and her body shook as it was wracked with waves of pleasure.

When she started to come Debby lost all ability to focus on anything but the ecstasy coursing through her. So to be safe Eric pulled her mouth off his cock and watched as she writhed in pleasure .

“Come here,” Eric said, hooking his hands under Debby’s arms and pulling her into his lap when she’d finally settled down.

Still a bit lost in the glow of her orgasm Debby put up no resistance as he moved her so she was straddling his lap facing him. When she started to come around she felt him lifting her up and positioning his cock at the entrance to her pussy.

“Ohhhh,” Debby moaned as she started to sink down on Eric’s cock.

As she lowered herself onto his cock Debby closed her eyes and reveled in the way her pussy stretched so deliciously around the hard organ. With the penetration coming right on the heels of her orgasm her body was still all tingly and just made everything feel that much better as she settled in Eric’s lap with his cock buried to the hilt inside her.

Gripping Debby’s ass Eric lifted her up until half of his cock was out of her pussy. Reversing course he pulled her down, stuffing his cock back inside. When Debby moaned he started lifting her up again, this time a little further.

“Fuck she’s tight,” Eric grunted as Debby started moving on her own.

“I bet,” Waldo said, his eyes roaming over Debby’s body as he waited for his turn.

After making her come Waldo had stood up and quickly ditched his clothes. And since Debby was currently occupied he figured he had a couple options. He could either wait patiently for Eric to finish and hope she was still in the mood, or he could find other ways to occupy himself.

Seeing as how he’d never been a particularly patient person, Waldo moved onto the couch next to them on his knees. Reaching out his hands he cupped the closest boob to him with one and put the other one on the back of her neck.

When Waldo started turning her head and steering it towards his crotch Debby got the message. Taking hold of Waldo’s cock she let Eric take back control of the fucking as she took Waldo into her mouth.

As Eric used his grip on her ass to bounce her up and down on his cock while she bobbed her head up and down on Waldo’s rod, it dawned on Debby that she was playing with two cocks at the same time. It was something she never would’ve thought she’d do, even when she was telling Robin that she wanted to shake things up and cut loose. And it only got hotter when Waldo started to slowly thrust his hips, fucking her mouth as Eric fucked her pussy.

“Wait wait wait,” Debby said, pulling her mouth off Waldo’s cock. “I want to switch.”

“Fine,” Eric said, pulling her down onto his cock and holding her there for a moment before letting her lift all the way off.

“Got any lube?” Waldo asked.

“Huh?” Debby asked as she stood up.

“Some girls can have a little trouble taking the whole thing without a little help,” Waldo answered. It was a bit of an annoyance at times, but having a large cock had been a godsend in high school when word had gotten out and girls started lining up to see if it was true.

“Uh, yeah, top drawer,” Debby said, pointing at the end table next to the couch. Robin liked to keep a few things in there just in case she was spending time up there with a guy and got a little too busy to go back to her room.

Opening the drawer Waldo quickly spotted the small bottle of lube nestled between a sleeve of condoms and a pair of handcuffs that he spent a moment thinking about before grabbing the lube and closing the drawer. Popping the cap on the bottle he squirted some along the shaft of his cock before using his free hand to smear it around and coat his shaft.

Turning his attention back to the business at hand Waldo noticed that Debby had spun around onto her hands and knees with her ass facing him. Eric was still sitting on the couch but this time with Debby taking hold of his cock and getting ready to suck on it.

Stroking Eric’s cock with her hand Debby bent down and wrapped her lips around the head of his cock. She could taste herself on him as she let her tongue swirl around the head before slowly working more of his cock into her mouth.

It wasn’t the first time Debby had tasted herself. She’d sucked her ex’s cock after he’d fucked her as well as licking her fingers occasionally after masturbating, but in her current frame of mind it made her wonder for a moment what another woman might taste like. But the possible taste of pussy didn’t last long in her brain with two cocks begging for her attention.

Getting onto the couch behind Debby Waldo grabbed hold of her hips. He let his hands wander over the globes of her ass before grasping his cock and aiming it at her entrance. Easing forward he watched as the head split Debby’s labia and stretched to accommodate him.

As Waldo pushed deeper into her Debby couldn’t believe it. It already felt like she had a couple feet of cock stuffed inside her and yet Waldo still somehow kept finding a little more to thrust into her. He was touching parts of her that had never been touched by a man’s cock before and he wasn’t even done.

Finally reaching bottom, Waldo felt the tip of his cock press against her cervix just as his pelvis pressed against hers. Moving both hands to her hips Waldo slowly pulled a couple inches out of her before pushing forward again, letting her get used to the length before really giving it to her.

“Oh shit,” Debby grunted as Waldo started fucking her with short strokes.

“You like that?” Waldo asked, making sure not to thrust all the way into her for fear of battering her cervix.

“Oh god, yesss,” Debby moaned, unable to focus on anything but the massive cock rubbing against newly discovered sections of her pussy.

As Waldo fucked her from behind Debby turned her attention back to the cock in front of her. Engulfing it she slowly worked more of it into her mouth until she was about halfway down it. With her hand stroking the shaft she applied to suction to the half that was in her mouth as she pulled her head back until she was sucking on just the head.

Feeling Debby’s tongue swirling around his cock Eric put a hand on the back of her head. Pushing gently to get her to sink her mouth further down his cock, Eric reached his other hand underneath her to fondle one of her tits. They were swinging underneath her with each thrust Waldo made into her from behind and he couldn’t resist giving one of them a feel.

With Waldo fucking her from behind and Eric’s cock sliding in and out of her mouth Debby felt a bit like a piece of meat being used as a human fuck doll. But rather than be disgusted and turned off, it was having the opposite effect on her. She was totally getting off on having the two men fuck her like that.

But the problem seemed to be that Waldo was entirely too aware of the size of his cock. Normally that wasn’t a bad thing, but it kept him from really opening it up and fucking her with reckless abandon. He wasn’t moving at a snail’s pace or anything, but it was measured enough that her climax was building incrementally inside her instead of rapidly like she craved.

“Mmmm,” Debby moaned around Eric’s cock as his hand moved to her other breast.

“Ready to switch yet?” Eric asked, wanting more of Debby’s cunt.

“I guess,” Waldo said, regretfully. He obviously would’ve liked to keep fucking her, but a break would definitely let him last longer, and by extension let him fuck her some more later, so he wasn’t going to fight it.

When Waldo had pulled out of Debby’s snatch Eric moved quickly. Picking her up he dropped her on her back and moved over her. Reaching between them he grabbed his cock and aimed it at her pussy before lunging forward and burying his entire cock into her in one thrust.

“Ohhhh,” Debby groaned as Eric immediately pulled back until just the head was still inside.

Draping one of Debby’s legs over his shoulder and hooking the other around his waist he plunged his cock back into her. She was dripping wet, along with the lube Waldo had added to the mix, and his cock moved easily as he sought to give her the orgasm she so clearly wanted and needed.

“Fuck, uhh, meee,” Debby hissed, holding on for dear life as Eric drilled into her.

“Want to keep her quiet?” Eric asked Waldo, remembering that there might or might not still be a bunch of people downstairs. Even if it was unlikely any of them might hear Debby over the sound of the music and conversations and such, it was a risk none of them really wanted to take.

“I think I can handle that,” Waldo said, grinning as he moved so he was standing next to the couch with cock near her head.

“Uhh, yeah,” Debby grunted as she shifted on the couch so her head was hanging off the edge.

Unable to move much as Eric pounded into her pussy Debby just opened her mouth and reached for Waldo. When his cock found her mouth he pushed forward slowly. He pushed until he bumped against the back of her throat and when he started to pull back Debby wrapped her hand around the shaft just above the spot where he’d bottom out in her mouth.

With her hand in place Waldo started to fuck her mouth, pushing in until her hand pressed against her lips and stopped him. Each time Eric pushed into Debby’s pussy Waldo pulled out of her mouth and then reversed course when Eric pulled out.

In synch the two of them spit roasted Debby, her tits shaking with each thrust Eric made into her. She could feel the pressure starting to build up in her midsection as her orgasm swell inside her. It was probably a good thing her mouth was stuffed full of cock because her moans were getting louder and closer together until finally her climax burst forth.

“Ohhhh fuhhhh,” Debby gasped as she came all over Eric’s cock.

After trading off and on to cool off a bit in Debby’s mouth, Eric wasn’t too worried as her pussy clamping down tightly. So he kept right on thrusting, barely slowing down to account for the extra pressure. But he miscalculated and the rhythmic squeezing of her pussy milking him started taking more of a toll on him than he would’ve thought.

“Don’t come inside her,” Waldo said, recognizing the look on Eric’s face and not wanting to slog through his friend’s jizz.

Feeling himself approach the point of no return, Eric slammed into Debby one more time. With a grunt Eric grabbed hold of his cock and ripped it out of Debby’s cunt and squeezed the base while thinking unsexy thoughts to keep from blowing his load.

Pulling his cock out of Debby’s mouth Waldo started to move around to take Eric’s place in her pussy when he remembered the bottle of lube. Picking it up from where he’d left it earlier, he started to wonder just how far she’d be willing to go.

“Roll over,” Waldo told Debby.

Still in the aftermath of her orgasm Debby didn’t even think twice as she moved to comply. She rolled over onto her stomach and, figuring he wanted to fuck her from behind again, lifted up onto her hands and knees.

Moving in behind her Waldo put a hand on one of Debby’s butt cheeks, softly caressing it. Opening the bottle of lube he turned it upside down and let a small stream of it squirt into the crack of her ass, trailing down over her asshole and pussy.

“I want to fuck your ass,” Waldo said, deciding it wasn’t the time for subtlety as he ran a finger over Debby’s asshole, spreading some of the lube around.

“I don’t, ohhhh,” Debby said, her body going rigid in shock as Waldo pushed the tip of his finger against her rosebud and penetrating it to the first knuckle.

“Have you ever had anything up your ass?” Waldo asked even though it was pretty obvious from the way her anus gripped his finger that she hadn’t, at least nothing bigger than a finger.

“Nooo,” Debby said, unsure whether the finger in her ass felt good or not. It really hadn’t hurt and it had felt kinda weird as he’d worked it in, but as he started wiggling it and fucked her with a couple inches of his finger it started feeling really hot.

“If you don’t want to, I’ll fuck your pussy some more, but I think you want it,” Waldo said, noticing the way she was almost imperceptibly pushing back against his invading finger.

“I never,” Debby grunted, biting her lower lip.

According to Robin, anal sex depended a lot on whether the guy was gentle and took it slow or not. The first time Robin had let a boyfriend talk her into it he’d taken his time and really made sure she enjoyed herself. And while she hadn’t come because her boyfriend had been sixteen and fucking a tight ass for the first time and had barely lasted a couple minutes, Robin knew immediately it wouldn’t be the last time.

Of course, Debby had also heard Robin’s stories about guys just jamming it in there and going to town without any real thought about how she was doing. Those guys not only got their access to her ass revoked, they often didn’t even access to anything else of Robin’s again.

“How about you be on top so you’re in control?” Waldo asked, pulling his finger out of her ass. Wrapping his arms around her midsection he pulled her on top of him as he moved to sit down on the couch. “You can be in charge of everything.”

“Everything?” Debby asked, really intrigued as she felt his cock pressed into the crack of her ass as she say in his lap.

“Everything,” Waldo answered, reaching around to cup her tits. “You can be in charge of how fast, how far, even how long.”

“I guess,” Debby said nervously as she decided if she’d come this far, a little further wouldn’t hurt too much. Especially since they hadn’t recognized her and she’d given them a fake name, and Robin wouldn’t say anything, so there really wasn’t a risk of them saying anything. As far as they were concerned she was just some random girl they met at a party and who cares if a random girl gets totally slutty, right?

Bringing her legs up onto the couch, Debby planted them on either side of Waldo’s thighs. Reaching behind her she put a hand on the back of the couch to steady her as she lifted up. She could feel Waldo’s cock moving against her as he sought her asshole.

After raising up for what seemed like forever, Debby finally felt the head of Waldo’s cock pressing against her back door. She paused for a moment, feeling a wave of nerves hit her as she thought about what she was about to do, but she pushed those thoughts out of her head and pushed ever so softly down against his cock.

“Relax,” Waldo said, feeling her tense up and block his entry.

Closing her eyes Debby took a deep breath. His hands were still cupping her tits and they tweaked her nipples to take her mind off she was doing. It must have worked because she started to relax and suddenly her asshole caved and she plunged down a couple inches before managing to catch herself.

“Holy fuck,” Debby gasped, barely able to breathe as she felt her asshole stretched around the head of Waldo’s cock.

“Holy fuck is right,” Waldo grunted, feeling her asshole gripping him tighter than anything he’d ever felt.

Forcing herself to breathe Debby pushed down again, taking another inch or so into her ass before stopping. It hurt a lot, but oddly not quite as much as she would have thought. Rather than the intense shooting pain she’d been expecting, it was more of a dull ache, especially the further removed from the initial penetration she got.

Lifting up again Debby felt the cock sliding through the tight ring of her anus and actually felt a few sparks of pleasure shoot through her. Pushing back down Debby started to slowly bounce on Waldo’s cock, soon working roughly half of his cock in and out of her tight asshole.

“That is fucking hot,” Eric said, grinning as he watched Debby tentatively work her ass up and down his buddy’s cock.

“I think she likes it too,” Waldo said as Debby’s bounces started getting bigger and her grunts of exertion were slowly replaced by low moans.

“Do you? Do you like taking it in the ass?” Eric asked Debby even though he could see the answer written all over her face as she finally reached the end and found herself sitting in Waldo’s lap with his entire cock buried deep in her asshole.

“Kinda,” Debby admitted, rotating her hips and feeling Waldo’s cock press against different parts of her rectum as she moved.

“Looks like more than kinda,” Eric said as Debby lifted up until about half of Waldo’s cock was outside of her ass.

“Leave her alone,” Waldo said, moving his hands down to her hips to help her bounce on his cock.

Shrugging his shoulders Eric moved closed to the couch. As Debby moved up and down he made eye contact with her and then looked down at where his still-hard cock was waving in the air in front of him.

Catching his hint Debby leaned forward and opened her mouth. Taking Eric’s cock back into her mouth she tasted her juices on his shaft as she worked her way down. She had trouble focusing on both of them at the same time, so she deferred a bit. She left Waldo use his grip on her hips to lift her up and down while she concentrated a bit more on sucking Eric’s cock. Then when she felt Waldo start to tire a bit she resumed bouncing while Eric put a hand on the  back of her head and fucked her mouth.

“Shit, stop, stop,” Waldo grunted, the tightness of Debby’s ass beginning to be too much for him on the heels of the blow jobs and fucking her pussy.

Stopping, Debby gingerly lifted off his cock. When it slipped from her ass she tried to move to the side but Eric slipped his arms underneath her thighs and lifted her effortlessly. Picking her up he moved to the other end of the couch and set her down on her feet.

“My turn,” Eric said, grinning as he spun her around and pushed her forward until she was bent at the waist.

While she had a pretty good idea what he meant, Debby was still taken a bit by surprised when she felt the head of Eric’s cock press against her sill gaping asshole. Having already taken one cock up her ass, and her asshole hadn’t closed much, the head of Eric’s cock penetrated her asshole with ease. There was a modicum of pain as she was stretched out again, and even a little further due to Eric’s added girth, but not even nearly as much as the first time.

“Now you get to know what it’s really like to have your ass fucked,” Eric promised, gripping her hips with both hands.

Debby was a little worried at that, but she needn’t have been. While Eric was a bit more forceful as he pushed his cock deep into Debby’s welcoming ass, he was still mindful enough to the fact that she’d just lost her anal virginity and might not be ready for the advanced course.

When Eric was balls deep in her ass he pulled back until the tight ring of her anus was positioned just behind the crown of his cock. Tugging on her hips he pulled her back firmly until his pelvis bounced off the cheeks of her ass.

“Oh god,” Debby grunted, her head sagging as a mix of pain and pleasure exploded in her brain.

Starting off at a moderate pace Eric fucked Debby’s ass with a power that hadn’t been there when she’d been riding Waldo. On each stroke into her, he slammed his cock into her ass with authority and after a handful of thrusts the pain started to recede and the pleasure shone through.

“Ohhh, fuck, uhhh, my ass,” Debby grunted, pushing back to meet his thrusts.

“Looks like our friend wants some more attention,” Eric said, causing Debby to lift her head and notice Waldo’s cock pointed right at her, mere inches from her face.

Debby started to protest as she remembered where exactly his cock had been but just as she opened her mouth Eric drove into her ass and her complaint turned into a loud moan. With her mouth open, Waldo took it as acquiescence and started to feed his cock to her.

As Waldo’s dirty cock entered her mouth Debby’s eyes opened wide. She tried to pull away, but that just impaled her even more on Eric’s cock. She tried to say something, but with a large piece of man meat stuffed into her mouth it just came out as muffled gobbledygook. But as Waldo pushed more of his cock into her mouth she came to the realization that even though it had just come out of her ass, it didn’t taste that bad. In fact, once she accounted for the naughtiness of it, it was actually pretty good.

“So fucking tight,” Eric grunted as he pounded Debby’s ass, trying to ignore the ache in his balls telling him he was getting close.

“Don’t come yet,” Waldo said, grinning.

“I’m not sure I have a choice,” Eric hissed, not wanting to pull out of the super snug confines of Debby’s asshole.

“Pull out and think about your grandma in a bikini or something,” Waldo said. “Because I think our friend here might want to try a DP.”

“Shit,” Eric said, his cock throbbing and damn near blowing at the mere thought.

Somewhere in the midst of Debby’s pleasure soaked brain the couple brain cells that hadn’t been overloaded started buzzing. A moment later a few more cells woke up and joined in, until finally enough of them got the message through and Debby realized what they were talking about.

While surfing porn tubes with Robin when they were fifteen and curious about sex, they’d stumbled onto a video where a girl had found herself sandwiched between two men. Debby had initially been disgusted as she’d watched the two large men use the poor woman but as the video went on she’d realized that the woman had been moaning and even begged for more. The image of the woman in the throes ecstasy as two cocks pummeled her holes at the same time had stuck with her, even as she’d written off the whole thing as being something that didn’t actually happen in real life.

Yet there Debby was, being spit roasted by two guys while they talked about both fucking her at the same time. As with pretty much everything over the last couple hours she wanted to grab her clothes and run, but a bigger part of herself wanted to go with the flow and see if it wound up being as fun as everything else she’d tried tonight.

“You want to try it, don’t you, Roni?” Waldo asked, using the fake name Debby had given them.

“Yeah,” Debby admitted as Eric pulled his cock out of her ass.

“Say it,” Waldo said, moving in behind Debby.

“I want you both to fuck me,” Debby hissed as she felt Waldo pull her cheeks apart. “I want to feel both of you fucking me at the same time.”

“Then you should probably clean up Eric,” Waldo said as he aimed his cock at her slowly closing asshole.

“Ohhhh,” Debby moaned as she felt Waldo’s cock push inside her ass. There was still a little pain as she was stretched once more, but it was getting less and less each time. She wasn’t sure whether it was because she was getting used to it or if she was just numbed up a bit, or some other factor her brain wasn’t able to process at the moment. The end result was the same no matter what though, she found herself enjoying getting her ass fucked more and more each time.

Opening her eyes she found Eric’s cock in front of her face and didn’t even hesitate opening her mouth. With one hand on the arm of the couch to steady her she used her other hand to grab hold of Eric’s cock and aim it at her open mouth. Diving onto Eric’s cock Debby closed her mouth around the head and sucked on it, tasting her ass all over it.

“Oh god,” Debby gasped when Waldo gave her a sharp thrust to bury the last couple inches up her ass. He was so deep inside her it felt like his cock was going to poke out her throat or something.

Not having been as strenuous in his fucking of Debby as Eric had, Waldo wasn’t in nearly as much danger of blowing his load. So he was able to set a solid pace, giving Debby hard, powerful thrusts into her tight ass while she noisily slurped away at Eric’s cock.

“You ready, or do you want to suck cock some more?” Waldo asked Debby.

“Weddy,” Debby responded, her answer muffled around Eric’s cock though both of them understood without too much effort.

When Eric pulled back and slid his cock out Debby’s mouth, Waldo slipped an arm around her waist. Pulling her up into a standing position Waldo pressed his chest against her back and lifted her enough for her feet to leave the ground. She gave a little squeak, both at the unexpected move, but also at how gravity seemed to force his cock even deeper into her ass.

Holding Debby up Waldo moved until he was in the middle of the couch. Carefully he sat down and moved his butt towards the edge. Moving his hands he grabbed Debby’s legs and positioned them so that her feet on the couch on either side of his thighs, leaving her nice and open for Eric.

As Eric moved in front of her Debby suddenly felt a wave of nerves hit her. The cock in her ass already felt huge, she couldn’t even begin to imagine what it might feel like to have both her holes filled at the same time. But she was committed to at least trying, no matter how nervous it was making her as she felt Eric drag the head of his cock along the length of her slit before locating the opening and easing forward.

“Holy gahhh,” Debby groaned, her head lolling backward as the head of Eric’s cock entered her pussy.

There was an not insignificant amount of pain as her holes were stretched wider than ever before, but there was also quite a bit of pleasure as her pussy hugged Eric’s invading cock even tighter. It was all so intense that it was all Debby could do to keep from being overwhelmed by it.

With her ass already filled, Debby’s pussy was so tight that Eric couldn’t just slam his cock into her like normal. Instead he had to treat it a bit like he would an asshole, pushing a little into her before pulling back and slowly working it in a bit at a time. It was slow, excruciating progress, but when he finally pushed the last couple inches into her he knew it was going to be worth it.

“So big,” Debby grunted, her brain threatening to shut down from the sensations down below.

She couldn’t really describe what it felt like, other than maybe that it felt like she had two baseball bats shoved inside her. Then when Eric started to pull out such strong signals rushed along her nerve endings up to her brain that her eyes rolled back in her head and she for a moment she was afraid she really was going to pass out.

“Go slooooowww,” Debby hissed, her body shaking under the intensity.

Doing as instructed Eric pulled almost all the way out of Debby’s pussy. With his hands on her thighs he pushed slowly but firmly into her, gritting his teeth at the extreme tightness of her pussy. When his entire cock was buried inside her he once again started to withdraw.

“Ohhhh,” Debby moaned as Eric started fucking her.

After taking a little bit to let Debby get used to having one cock moving inside her Waldo decided to spring into action as well. Putting his hands on her rib cage he started to slowly move his hips, sliding not quite half of his cock in and out of Debby’s asshole.

“Fuck,” Debby grunted as she felt both of them moving and rubbing against each other inside her.

As she started to get used to being stretched out, at least enough that it no longer felt like she was going to be torn in half, she started to loosen up. And as she started to loosen up the guys were able to move a little freer and quicker inside her.

Each time Eric slid out of her pussy Waldo lifted his hips and pushed into Debby’s ass. Then as he started to withdraw Eric lunged forward and stuffed her pussy full of cock. She was constantly being filled and the feeling of them rubbing against each other through the thin membrane that separated her holes was one of the hottest things she’d ever felt.

“Fuck me,” Debby gasped, her eyes glassing over as waves of pleasure hit her over and over.

Hearing the need in her voice Eric picked up speed. Waldo really wasn’t in position to match it and they quickly fell out of sync, but it didn’t matter too much. Debby was too far gone to really notice and the added speed actually helped her hit her first climax.

“Ohhhh gaaaawwwwdddddd,” Debby wailed as she came harder than she would’ve thought possible.

Feeling her holes clamp down on their cocks, Eric and Waldo knew the end was near but that just made them keep going as they searched for their own orgasms. They’d been switching back and forth and holding out for what seemed like days in hopes of stretching it out but they were finally facing the home stretch. Neither of them were going to be able to hold out much longer so there wasn’t much point in trying.

“I’m gonna come,” Waldo warned Debby, his hands up sliding up to cup her tits from underneath.

“Me too,” Eric said, feeling the tingle in his balls that told him it was close.

“Where do you want us to come?” Waldo asked Debby. “Inside you? Want us to fill you up with cum?”

“No, uhh, come on me,” Debby hissed as Eric continued to thrust into her. “I want you come on my, oooh, tits.”

One of Debby’s few predilections was that she liked feeling cum splattering her skin. It had started when her ex had wanted her to let him come in her mouth even though she didn’t like the taste, so she’d pulled him out of her mouth at the last minute and let him come on her tits.

He’d thought it was hot, but the feel of his hot cum hitting her chest had been a revelation. After that she’d taken to doing it as much as possible. A few days later she’d cut it a little closer and pulled her mouth off his cock just as he was exploding and had caught the first couple shots on her nose and chin, which she’d actually liked even more.

“If we’re going to do this…” Eric said, trailing off as he pulled his cock out of her pussy.

Groaning at the sudden emptiness, Debby sat up and let herself be lifted off his cock. As Debby pulled off the mask and slid off of him onto the couch, Waldo stood up. While she dropped to her knees in front of the couch the two guys moved to stand in front of her.

Taking hold of a cock in each hand Debby stroked the shaft of Eric’s cock. Parting her lips she tugged on Waldo’s cock and aimed it towards her open mouth. Wrapping her lips around the head she moaned as she tasted her ass on it and sought to work more of his cock into her mouth in hopes of tasting more of it.

“Really close,” Waldo grunted, feeling his cock start to throb.

Pulling her mouth off his cock she gave it a couple strokes before the first shots erupted out of the tip. The first one hit her on the chin and neck before dripping down onto her tits. The second one hit up and further to the right and streaked across her cheek, even getting a little in her hair. After that she aimed it towards her chest, letting him douse her tits with his goo.

While that was happening Debby had been giving Eric a worthy handjob. Between that and watching her get covered in jizz, he was quickly ready to burst as well. But while he liked seeing her tits coated in white, he liked seeing the white streaks on her face even more.

So with a loud growl of release Eric’s first spurt belched out of his cock and hit her on the forehead, dripping down the bridge of her nose. The second one hit just above her eyebrow and she had to close to eye to keep from getting his cum in it. For the third on he took aim at her closed mouth and watched as it struck right above her lips, some even splattering up into her nostrils. After that they started to peter out and he let it dribble out onto her chest.

“Wow,” Waldo said, staring down at where Debby was absolutely covered in cum. “Is there a tissue or napkin or something around here?”

“Drawer,” Debby said, pointing at the drawer where the lube had come from.

Opening the drawer Eric found a small packet of tissues. Handing them to Debby he and Waldo watched as she used a bunch of them to gradually wipe herself off and clean up. Eric kinda wished he had a picture of it, but figured if he started digging through his pants for his phone she’d notice and get pissed.

The three of them stood there for a bit longer unsure of what exactly to say to each other. With each passing minute the awkwardness grew until Eric gave up. Shrugging his shoulders he started  picking up his clothes. As he got dressed Waldo and Debby quickly followed suit.

“Should we call?” Waldo finally asked when he’d put his costume back on.

“I don’t think so,” Debby said, shaking her head. While she was far from ashamed of what they’d done, having to think about it too much right away might not be the best thing.

“Okay, well I guess we’ll be going then,” Eric said, unsure of what to do.

They settled for a modest hug and a kiss on the cheek before they slipped down the stairs. A few minutes later Robin appeared as if by magic with a shocked look on her face. Debby just grinned and started giving her every last detail.

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