Chapter 5

Eddie was insistent that my aunt wouldn’t get any “lube,” and from the grins on the other girls’ faces, that didn’t sound good for her. Either she didn’t care, or she didn’t think he was serious.

“No one’s going to sit here and let you milk yourself like the cow you are to get wet! You should’ve shown up greased up like the other reindeer. Now, if there are no questions, get into two lines—single file. Men on this side, reindeer on the other. As a reindeer gets pinned or works through all eight men, she moves to the winner’s circle—or the loser’s pit.”

Eddie made it clear that “winning” meant getting pinned, while “losing” meant squatting off to the side with no attention at all.

“It’s Candy Cane time! Let the games begin!”

Evan raised his hand, looking genuinely confused. “So ... do we all go for the same girl, or is it one guy, one girl, and they’re done?”

Eddie smirked and cocked his head. “What do you think, Evan? Do these look like the kind of wanton trollops that would let an entire line of men have a go at them before they’re satisfied?”

The guys lined up, and I slipped to the back of the line, unsure how to play. I figured I’d watch and figure it out by the time it was my turn. “Uptown Funk” was blasting through the speakers, and the beat had everyone moving. The reindeer swayed and laughed in their line, their energy electric. Blitzen had taken a spot at the back, too, probably for the same reason I did—trying to stay low-key while figuring things out.

Evan’s awkward silence answered that question, and Eddie clapped his hands. “if the reindeer makes it past eight tries, she heads to the loser’s circle and can’t play in the next game. That’s the rule. I don’t make ‘em up! Oh wait, I did make that one up!” Eddie laughed. “Alright! Reindeer games – eight guys have a chance to pin the tail on the reindeer. If she gets tailed, she’s done – and waits in the winner’s circle, shaking what’s got. She’ll wait off to the side, fat reindeer ass sticking out, holding her knees like the good little reindeer slut she is -proud of what hole she got pinned.”

I started to get a hard-on just thinking about how eager these women were to be pinned in a “hole.”

Dancer, who was next, made a sour face and stuck out her tongue at us when Eddie called out, “Fat reindeer ass.”

“If they don’t get pinned, shame on the party guests! They’ll be on consolation prize duty during the ring toss game that follows! Dancer, you’re up first!” Eddie announced, grinning. He applied a blindfold to her – but didn’t explain why. He faced her to the wall and made her touch her nose and tits to it.

It seemed like everyone except for Evan and me knew what was happening and why, and neither of us asked.

Dancer took her spot: initially, palms flat against the wall, nose to it, legs apart, and presenting her thick ass with an exaggerated wiggle. “Okay, Dancer reporting in to get my tail!”

Eddie, ever the showman, cranked up Kung Fu Fighting on the stereo, giving the whole scene a ridiculous, playful vibe. Everyone started singing along to the goofy lyrics, and I couldn’t help but laugh. It was silly, over the top, and somehow worked.

Jerry stepped up first, candy cane in hand, looking like he actually wanted to win. He was blindfolded and spun around several times before being let loose with his candy cane.

She had rope around her ass and tied to her wrist, but Jerry lifted it up – clearly and placed the candy cane on her butt – clearly indicating that’s where it was going to end up. Dancer didn’t seem to mind at all. If anything, I’d say she was downright flattered.

Evan and Harley weren’t the only couple here. I guessed that Dancer and Jerry were both married, probably to other people at this party. No one seemed jealous or uneasy about it. Instead, everyone was buzzing with excitement, cheering, and clapping to get the game underway!

Dancer glanced back over her shoulder, giving another exaggerated wiggle. “Come on, Jerry! I can’t present a bigger target than this!” she teased. She removed her hands from the wall and held her ass cheeks apart for him – showing us both holes spread wide.

The girls kept chanting directions to help him- or mislead him. “Colder ... colder ... warmer ... nope!” to help him find his way forward.

Jerry’s candy cane missed completely, clattering to the floor. He threw his hands up, groaning, as the room exploded with laughter.

Dancer let out a loud, fake sigh of relief. “Phew! You missed! Guess I don’t have to make an example of you!” she teased, grinning.

Next up was Gary. He stepped forward, his brows furrowed like he was about to solve a math problem. “Come on, Gary, you got this!” Daisy called out, her voice dripping with fake encouragement.

“You better hope he doesn’t!” Dancer shot back, smirking over her shoulder. “My ass isn’t taking another round tonight.”

Gary lined up his shot, taking it way too seriously. The candy cane smacked the wall just above Dancer’s head, and the whole room lost it. Dancer spun around dramatically, clutching her chest like she’d just dodged a bullet. “Warm, but still fail! Thank God. I owe you one, Gary!” She gave him a playful wink as he slinked back to the line.

I stayed at the back of the lineup—not because anyone told me to, but because it felt easier to let everyone else go first. From there, I found myself watching Mrs. Sanderson - casually. Smiling, grooving to the music, unaware that I was watching. Almost shy. Her big, doe-like eyes flicked toward me, just for a second, before darting away. She made no attempt to cover her nudity – somehow, I felt like a jerk for daring to look at her huge nipples. They weren’t FOR me – and yet I indulged myself and admired the slope, and wait, they stuck straight out – more so, I admired how bold she was for just standing there with everything hanging out.

I doubted that I wouldn’t have been self-conscious if the tables were turned, and I was naked in a room full of fully dressed women.

I had no idea what I was going to do when it was finally my turn. Watching the others wasn’t helping—they all laughed and teased, but no one was explaining a damn thing. And still, every time I glanced at Mrs. Sanderson, I felt the knot in my stomach twist a little tighter. Was she nervous? Flirty? The way her gaze lingered, even for a heartbeat, felt like a question I didn’t know how to answer.

Maybe it was the tequila I’d had earlier, but with each turn that passed, my confidence started creeping up.

Three people had already taken their turns, and now it was Evan’s turn to pin the candy cane on the reindeer—or whatever we were calling this outrageous game. It was basically a super kinky version of Pin the Tail on the Donkey, except both the pinner and the pinnee were blindfolded, and tequila was involved. I still wasn’t entirely sure if we were supposed to try and stick the candy cane in their butts or something. I was hoping someone else would figure it out before I got to the front of the line.

I couldn’t imagine pitching this idea to some girls for the first time. “You’ll stand naked, and we’ll try to shove a candy cane up your butt while you are blindfolded ... sound good? Why are you leaving.”

a reindeer got pinned, they were out, and nobody else got a try—but they ‘won.’ I wasn’t sure how having a candy cane in the butt made them a winner, but everyone further back in line lost their chance. That alone added pressure. I was the last guy, so if they got past me, they ‘lost,’ and I was sure somehow that would be my fault, too.

The guys in front of me kept whispering and trying to throw Evan off, their voices just loud enough to carry over the noise. “Left ... left ... warmer ... warmer!” they called out, their laughter obvious.

Meanwhile, the girls weren’t helping either, shouting just as loudly but giving conflicting instructions. “Right! No, higher—no, no, lower!” The chaotic mix of voices only added to the tension.

Dancer, blindfolded and grinning like this was her personal stage, wiggled her ass and teased over her shoulder, “C’mon, Evan, don’t listen to them. Trust your instincts! Or do you need me to make it easier for you?”

Evan, candy cane in hand, stepped forward, his movements cautious but determined. The room was practically buzzing with anticipation, the playful chaos making it impossible to tell if anyone actually wanted him to succeed—or fail miserably. The combination of conflicting advice and playful teasing was enough to make Evan hesitate, his grip tightening on the candy cane. He took a deep breath, adjusted his stance, and carefully leaned forward. The room held its collective breath as he made his attempt.

The Candy Cane – went straight into this woman’s pussy – she bucked her hips and slid back on it while it was still in her hands.

“Bullseye!” Dancer cried, spinning around with a grin. “Evan, you’re officially my favorite tonight. Harley’s gonna have to fight me for you.”

My sister was one of the ones laughing and applauding the hardest – like a good sport, genuinely happy that her friend was pinned, and her boyfriend had done the deed.

The room exploded with cheers and laughter as Evan’s face turned beet red. He stepped back, clutching the candy cane like it was some kind of trophy, looking half proud and half mortified.

Evan’s aim wasn’t perfect, but it didn’t need to be. The candy cane stuck just well enough for the group to declare it a solid “hit.” Dancer let out a delighted laugh, spun around, and planted a quick kiss on his cheek. “Not bad for your first try!” she teased before sauntering over to the “pinned” lineup. She bent forward slightly, hands on her knees, her stance making it clear she was ready for whatever came next.

Harley stepped up next, full of her usual sass. “Alright, boys, time to try your luck,” she called over her shoulder, throwing in a playful wiggle. “Let’s see if anyone here can handle this!”

“Crap,” I muttered under my breath as the line moved forward. “Someone pin her before it’s my turn...”

One by one, the guys ahead of me missed, and each failed attempt was met with louder taunts from the girls and groans from the guys. Eddie couldn’t resist chiming in when it was his turn, dramatically yelling, “A swing and a miss, Uncle!” as his candy cane went wide.

Harley seemed almost too into the game, playful and open to being pinned. I couldn’t believe what I was seeing. My big sister—usually the one with a steady boyfriend all through high school—was acting like this was the most fun she’d had in ages. Watching her now, I couldn’t help but wonder how often she acted this way and whether Evan would even care—or get jealous.

She wasted no time spreading her legs wide, presenting a target without a shred of shame. Both holes were glistening with lube, and she wore a bemused, devil-may-care expression. My parents didn’t seem to disapprove—though I noticed my father wasn’t exactly staring in awe either. I tried to act like this wasn’t blowing my mind, but it was a losing battle.

My parents had clearly been part of this lifestyle for a long time, but Evan and Harley were still new to their relationship. I couldn’t even imagine how she’d convinced him to come to a party like this, let alone be okay with it. The whole situation felt impossible to wrap my head around.

I was eighth in line, and the way the rotation worked, every guy got one try against each reindeer unless someone pinned her first. If no one managed to pin the reindeer after all eight of us—Jerry, Gary, Marty, Evan, Harold, my dad, Eddie, and me—then she was out and lost. Win or lose, the next reindeer stepped up, but the rotation didn’t reset to the beginning. If someone pinned her before all eight attempts were used, the next girl came up, and the turn continued with the guy after the one who made the Pin. For example, if Evan pinned Harley, Harold would start on the next reindeer. Every guy got one shot per reindeer, keeping it “fair”—if you could call getting a candy cane shoved up your ass fair.

Dad stepped up next; Eddie spun him around several times, sheepish look on his face, candy cane in hand, his usual laid-back confidence masking what I could tell was a bit of nervousness.

My sister was already in position, blindfolded and waiting hands holding her ass cheeks apart nice and wide – I could see EVERYTHING.

“Last year, you were afraid to be pinned. Still afraid, pumpkin?” Dad teased; his tone playful but with a definite edge.

Harley shot back immediately with sass and confidence. “The name is Donder, and I’m going to be disappointed if you don’t pin me!” She wiggled her hips for emphasis, earning a round of laughter from everyone watching.

From the sidelines, Daisy chimed in with her own brand of encouragement. “Come on, Steven! That girl’s asshole is tight, teach her a lesson, she’s playing big-girl Reindeer games now!” It was both crass and degrading, but somehow, it still felt like she was being supportive of both of them.

I was shocked that my Mom was supportive, but all of the reindeer seemed to root for each other – even though most of them could also be catty and vindictive at times. “Don’t hold back, Steven! She’s been fully trained this year. She can take anything you can dish out! Any hole, any time!! She’s DSL material!”

All the women, including my sister and Mrs. Sanderson, pumped their fists or clapped and shouted, “DSL!”

Mom noticed me standing off to the side and shot me a quick, exasperated glance—like she’d just remembered I was there and realized what she’d said.

Dad lined up, spun once for effect, and took his shot. The candy cane missed entirely, smacking the wall with a hollow thud. The room erupted into laughter, and Dad gave a shrug like he didn’t care, though I could tell it stung a little.

Harley, ever the show woman, lifted her blindfold slightly and turned her head toward him with a grin. “Nice try,” she said, her voice warm despite the teasing. Then, leaning in, she planted a quick kiss on his lips before dropping the blindfold back into place. “Better luck next year, old man.”

“You better be full DSL by next year!” Dad patted her bottom and handed his blindfold to Eddie because my uncle was next before me in the rotation.

She leaned in closer, her voice low and teasing but excited “I never thought about being a real member!” She turned in my mother’s direction, still in her blindfold, and asked, “Would you train me? To be a full member?”

“Harley, DSL training isn’t just a fun little game—it’s a full commitment to prepare for the initiation. We all had to do it. I can’t just let you waltz in the club without that. It’s physically intense, mentally challenging, and, yes, sexually demanding. You’d be expected to go far beyond playful service at a party like this. Before you even think about starting, you’d need to have a long conversation with Evan. This is a commitment and it’s definitely not just one night of fun. If you’re serious about earning your DSL wings, you’ll have to prove you’re ready for everything that comes with it.”

“Wings? I thought we got DSL horns,” my aunt crowed. Instead of angel wings, she wanted devil horns. I still didn’t know what DSL stood for, but I was starting to get the idea it was some kind of sex club. I noticed Blitzen blushing – I wondered if she was considering joining it – or even a member.

The other girls were supportive, whooping, shaking their fists, and trying to welcome my sister into their club and encourage my Mom to consider supporting her for membership.

My Mom folded her arms, her tone softening as she spoke to Harley. “DSL isn’t something you jump into lightly,” she said as she glanced at me and back at Harley – perhaps signaling her discomfort with the conversation while I was present. “DSL is more than a club—it’s a sorority of sisters who count on each other, hold each other to high standards, and expect full commitment. And let’s not forget, your brother is here. Maybe we can enjoy the party now and talk about it later and get someone to stick a candy cane up your ass and another in your mouth, so you do less talking and more smiling?”

The guests laughed about that. Harley frowned but nodded. “Mom, we have to be totally honest at the party—that’s the rules. I think Nick has an idea of what DSL is about, and it’s not a charity anyway ... but fine, we’ll talk later; someone shut me up,” she opened her mouth wide as if offering to let someone put a candy cane down her throat.

From the sidelines, Dancer snorted and added with a laugh, “We kind of ARE a charity; we do give it away.”

Prancer didn’t miss a beat, smirking as she chimed in. “Speak for yourself. I charge when I can. Get away with it!! Sell a little skin on the weekend,” the two girls high fived. I got the impression that she meant prostitution – my mind boggled.

Harley returned to her position, confident and ready for another attempt to pin a tail into her pussy and asshole. She presented herself to her uncle.

Eddie went up before me, and of course, he had to make a spectacle of it. Blindfolded and spun like a drunk at last call, he stumbled forward, gripping the candy cane like it was a weapon. The room erupted with shouted directions, most of them nonsense meant to throw him off. When he finally lunged, the candy cane smacked the wall a foot too high, bouncing off and landing with a hollow clatter. Eddie yanked off the blindfold and turned to the crowd with a smug grin. “Guess I overshot and missed the hole! We should paint a bullseye on your fat asses to make it easier!”

He slapped my sister’s ass. She remained in position and reminded him that he was blindfolded, so he couldn’t see it anyway.

“Doesn’t matter, sexy as hell to see a woman with a bullseye on her ass! For what it’s worth, and my opinion ain’t worth piss in the DSL; I think you would make a fine Dick Sucking Lady!”

There it was – what DSL really stood for. I had heard my aunt say that casually in the kitchen, but it was so outrageous that I wrote it off as something of a joke. No one corrected him, and the girls backed him up and applauded.

My Mom shot me a maternal glance, her eyes soft with a mix of concern and apology. It was the kind of look that said she knew I’d pieced together more than she ever intended me to and maybe more than she was ready for. For a moment, her confident facade slipped, replaced by something almost vulnerable, before she straightened her posture and turned her attention back to the game.

“You are up, Nick!! This is what you came here for, right?” She applauded as they encouraged me to step forward.

The candy cane wasn’t made of real candy at all. It was a latex dildo shaped like a candy cane – slathered with a jelly-like Vaseline that made it feel sticky – but also easier to slide in. There was a 32-ounce container labeled “Sex-Grease” to re-apply as needed by my sister’s feet.

My dad, Eddie, guys I’d never met before, the DSL ladies, even Blitzen—everyone seemed to pile on with words of encouragement. I could feel the weight of their eyes and the weight of every missed attempt, pressing down on me like a lead balloon. My confidence, already shaky, was starting to slip. Eddie tied the blindfold snugly around my head, the grin on his face practically radiating through the fabric. Then, with dramatic flair, he spun me around like I was the main event of the night.

George Thorogood’s gritty riff from Bad to the Bone blasted through the speakers, adding to the electric atmosphere. The crowd clapped and stomped along, shouting things like “Take your time, Nick!” and “You’ve got this!” The energy was infectious, but the pressure was suffocating.

Notably absent was Evan’s voice, and I couldn’t help but wonder what he thought about his girlfriend’s little brother stepping up to pin her. He probably thought we were one deeply perverted family.

Harley, never one to let a moment go by without adding her signature sass, called out with a teasing edge in her voice. “Come on, Nick, aim like a man! You had your first kiss with Mom; this counts as losing your virginity to your sister!”

“Hey!” Comet shot back, barely able to contain her hysterical laughter. I could picture her covering her mouth, trying (and failing) to stifle the chuckles. The crowd erupted, their laughter echoing through the room, and it was painfully obvious they were laughing at me, not with me.

Bad to the Bone

Bad to the Bone

B-b-b-b-b-b-b-bad

B-b-b-b-b-b-b-bad

The group laughed and sang along. I borrowed some of George’s swagger and approached this like the man that my sister said I should be.

I squared my shoulders, refusing to back down. “At least if I pin you, Harley, I won’t have to make up some story about who broke you in for the DSL.”

“Oh, snap!!!” I heard one of the reindeer say, and a wave of excitement fell over the crowd. I must have said something right because my sister had no come back. “Nothing to say, Harley? I mean Donder. I guess I don’t have to stick this dildo in your mouth to shut you up!!”

“It’s a candy cane,” one of the girls corrected. “We love candy in the DSL!!”

I tried to get my bearings. The blindfold wasn’t helping, and the spinning had me completely disoriented.

“Do you even know where a pussy is?” my sister chimed in, shaking her rump triumphantly as if to remind me. “You better not try to stick it in my asshole! I don’t know you well enough for that,” she goofed on me.

The crowd (sans Evan) chanted, “Pin Donder’s Asshole! Pin Donder’s Asshole!”

“Either way, he’s never going to do it,” my sister predicted, and sadly, she was right. My first attempt slid through her legs and hit the wall with a thud.

“Damn, were you trying to rip me in half?” Harley playfully removed her blindfold and gave me a quick kiss on my lips – never in the 18 years I had known this girl had she done that to me before. It was always on the cheeks. I removed my blindfold and hugged her awkwardly. Her boobs pressed against my shirt.

“No hard feelings, little bro! It was your first time; good effort, maybe next year?” she looked in my Mom’s direction, but my Mom said nothing – flat expression.

I realized the implication of what Harley meant. In ONE year, if I were able to come to the party, I’d be able to do these again with my sister. I wasn’t sexually attracted to my sister, but I have to admit – I kind of wanted to shove the dildo in her pussy or ass just to get one over on her. She had goaded me in a way that made me want to do it.

That seemed to be the goal of the teasing and trash-talking – not to hurt the men’s feelings, but to make us feel less guilty about “pinning the tail” and enjoy it.

As the next guy stepped up, Harley’s smugness didn’t last long. Jerry, a burly guy in a red sweater, took his spot, visibly confident. Eddie tied the blindfold snugly over Jerry’s eyes and gave him a few dizzying spins for good measure, the room erupting in laughter as Jerry staggered into position. George Thorogood’s gritty riff blared in the background, setting the scene perfectly.

When Jerry finally steadied himself, he lunged forward with determination. The candy cane hit its mark perfectly, sticking just where it was supposed to. The room erupted into cheers, the men clapping Jerry on the back like he’d just won the championship. Harley, still blindfolded and stiffened at first, then let out a dramatic sigh, her smirk quickly returning.

Jerry stuck the same dildo I had been using right up my sister’s tight little asshole – and it hung out like it was a long tail!!!

“Bullseye!” Jerry called out, pulling off his blindfold to see his handiwork. Harley patted the candy cane tail sticking out from her lower back and gave it a playful tug. “Mmm, peppermint,” she teased with a cheeky grin “Damn, feels good to have a tail!!! Evan, look!!! I got my tail!”

The lube didn’t taste like peppermint at all. It tasted like gross sex jelly. I tasted it when I went back to the end of the line.

My sister pranced over to where Dancer was bending over, bent over, and swayed her ass to the music like a stripper dancing on stage, trying to encourage someone to come up with a dollar bill -proud of the tail in her ass.

It was an odd sight—like they were on display, trophies in a game that blurred the lines between playful and primal. Dancer seemed entirely at ease, even pleased, while Harley’s smug expression only grew as she adjusted her stance. They looked like prey caught by hunters, but instead of resisting, they seemed to bask in the attention.

Meanwhile, Eddie passed over another Christmas-themed Peppermint Dildo from what he called the “Toy Box” – a chest of sex toys. Vixen caught it. She bent over, displaying her pussy and ass to the crowd, and squirted a LOT of the sex lube into her hands, spread some on her pussy and asshole- fingering her butt with it.

Then the big blonde turned around and started jerking off the dildo, rubbing the lube up and down the cock. I almost jizzed in my pants watching her perform on the dildo. Everyone else laughed and encouraged her. Jerry handed out half-tequila shots, calling them “reloads,” and made everyone drink a little. All except for me and my sister.

Daisy smirked, leaning in just enough to make her voice drop into that teasing, knowing tone. “I told you DSL wasn’t a charity, but you didn’t want to believe me.”

I was surprised that my aunt was able to speak at a lower volume, and with everyone’s attention on the performance that Vixen was giving us, I had a chance to ask more questions.

Daisy laughed, the sound sharp and unapologetic. “Heck no! There’s no way. Eddie and I are always open and honest about our lifestyle. We don’t go into details; if they knew I’d be a reindeer, they’d beg me to do it all the time at home. I’d have a candy cane up my tail hole every night if Eddie and the boys had their way!”

I smirked, leaning into the teasing. “But I thought you liked being a reindeer. Wouldn’t you love giving them a Christmas gift too?”

“I’d BE the gift, and like I told you in the kitchen, my boys wouldn’t really understand restraint – they’d wear me out!”

She didn’t say anything about being revolted by kissing or allowing her sons to pin her at all – and since she kissed my Mom in front of me, I assumed incest wasn’t a limit – just the frequency.

“You said when they are 18, you are going to invite them, though; what then?”

Daisy tilted her head, her expression softening just slightly. “We’ll have to give them a proper education before they come to something like this—help them understand the boundaries and what this is really about. Limits are important, and I wouldn’t want them walking in without knowing the rules. You’ve done a good job of rolling with things, but I can tell some of this is blowing your mind – especially seeing your sister get nailed up there.”

She indicated Harley shaking her rump playfully like she had won a huge prize by having a dildo stuck up her ass in front of everyone else.

She paused, then smirked knowingly. “See, that’s the problem with your mom’s ‘absolutely not’ approach. All it did was make you curious enough to sneak around to get a peek, connect the dots all wrong, and decide we’re being forced into this, and we’re poor little abused reindeer!” Her voice dripped with hyperbolic self-pity for her plight. “I am not ashamed of getting a dick up the ass, Nick – I’ve taken them before you were born. I love it. My boys know I love sex; I make no secret that we swing, and they’ve met a lot of the guys who are my regulars. I just don’t tell them the details. If they came to this party – they’d have to be prepared to see the details, but that’s ONCE a year we let it all hang out.”

I didn’t get a chance to follow up – the show was back on. Eddie clapped his hands, drawing everyone’s attention. “Alright, folks, let’s keep the spirit alive! Quick reminder: remember those fancy Sexmass cards waiting for you at the end? If your reindeer get pegged, you’re winning ‘em for your rider. That’s Gary for Dancer, and—wait, who’s Harley riding for again? Someone yell it out.”

From the back, Marty sheepishly raised his hand, earning a round of good-natured jeers from the guys. “That’s right,” Eddie grinned. “Don’t let ‘em down, gents!”

“Okay, who is Blitzen riding for?” Eddie asked. No one said anything, and I looked in my mother’s direction. Her blue eyes burned through my soul, and I didn’t raise my hands. I noticed Blitzen looked dejected.

“No problem, we’ll divide those up!!” Eddie moved along with the game. The line of men shuffled forward as the next round began. My Mom was up next. She stepped to the wall with an exaggerated sigh, pulling her hair back and twisting it into a loose bun. “Alright, harpoon the great white whale, boys,” she declared, pressing her chest to the wall. Her arms framed her face as she leaned forward, her voice full of humor and challenge. “Let’s see what you’ve got.”