F*CKING AWKWARD HOLIDAYS: 25 Short Stories of Awkward Holiday Encounters

by Plendl, Taryn

  “Fuck, come up here,” he murmured, “You’re too good at that, holy shit.”

  I crawled up his body, without taking my hands off his cock. Then, I spun around, lifting the back of my dress up over my hips. Slowly, I bent over and slid my panties down my legs. “Slide that big fucking cock in here,” I purred. Fuck, I hope I sounded sexy and not like a complete loser.

  “Damn, this is the hottest thing that’s ever happened to me,” he breathed, slapping his hand across my ass.

  I squealed with delight, and slid my hands up my thighs, over my ass and spread myself open for him, “Yeah, well, it’s about to get a fuck of a lot hotter.”

  He shifted closer, grazing his hardness over my wet lips, teasing me, driving me crazy with a wild aching need to be filled. I couldn’t wait any longer; I pushed my ass back against him, gliding over his big thick cock. I cried out; pain mixed with pleasure, as he stretched me out and filled me completely.

  With a deep low moan, he reached up and grabbed the hair at the nape of my neck and twisted it tightly in his fist. “You’re fucking perfect, you know that?” He tugged his hand until my neck was stretched back. Then, he leaned over and kissed right below my ear, thrusting hard and deep inside me.

  A warm tingling feeling coiled in my clit and ballooned up between my legs, “Oh God, I’m going to come. Don’t stop. Please,” I begged, loving the way the sensation slowly throbbed and spread like warmth inside me until it shattered into a hard explosive orgasm that shook my legs and stole my breath away.

  “Oh shit, that’s hot. That’s so fucking hot,” he breathed heavily, as I pulsed around him. “Fuck, you come so hard. It feels so fucking good.”

  He moved quicker, more urgently. Then, he slipped out and pressed against the opening of my ass.

  “Can I come in your ass?” he asked, low. “I’m so close.”

  Hell no. Hell fucking no. Not with that nuclear weapon of ass destruction. “Not my ass. I’m going to shit on your dick…” Holy crap, I’d never been so crude.

  “I don’t care. Shit on me.”

  What? Ew. That’s so fucking gross. How the fuck do I get outta this? “Next time. We’ll use lube, and I won’t eat burritos for lunch.”

  He chuckled and sunk back inside me with a low moan.

  “I want you to come on my cock again,” he whispered, leaning over me and fanning hot breath into my ear. “That felt incredible.” His hand slipped around the front of me and reached between my legs. Warm wet fingertips pinched tightly over my clit, and I was there again, crying out for him to fuck me harder. He did too. He gripped me tighter, and pounded into me mercilessly until his cock was bucking and twitching deep inside me, grunting, “I’m coming. Fuck, I’m coming.”

  He stilled, holding me tight against his chest for a moment, panting heavily. After a few moments, he slowly eased himself out of me and pressed his forehead into the back of my shoulder. The heat of his breath tickled through the material of my dress. “That was insane,” he whispered. “I’ve never come that hard before.”

  The loss of him inside me was somehow devastating—I felt hollow and exhausted.

  Still breathing heavily, he zipped up and kicked at the full condom he dropped on the floor, until it was jammed into the corner of the booth. I stepped back, my body still trembling, but sated like I’d never felt before.

  “That was honestly the hottest fuck I’ve ever had,” he said, his half hidden eyes darting back and forth between mine.

  We fixed ourselves quickly, giggling, and stepped outside the small booth to a strange sudden silence. Everyone sat frozen, all eyes and heads turned toward us. Behind them in the front of the room, which I hadn’t seen before, were two large screens, each one somehow playing loops of explicit photos.

  The devil and his gothic clad mistress.

  Immediately, a sharp, painful fire stabbed across my chest and nausea rolled like a churning sea in my abdomen. How could no one have told us what happened in the booths would be projected up onto the screens? A raw naked feeling of filth and utter shame crawled like slime through my body. Right before I ran and curled myself up into a fetal position on a heavily-trafficked street, Heath reached out and grasped my hand.

  Then, I smiled to myself and stood straighter. Nobody knew who either of us was! The only one who knew our costumes was the person who’d purchased them all.

  “Jane?” Someone dressed like a sexy robot whispered. “I’m so happy you took my advice!”

  Oh shit.

  “J-Jane?” the man I just met biblically stammered, peeling off his mask. Zeke’s face stared back at me, “I thought you were Julia!”

  Oh my God, I was going to have to boil my vagina! “I thought you were Heath!” I choked, swallowing back vomit.

  “Someone needs to stop the live feed of pictures to our website!” someone in the back of the room called as everyone else pushed back their chairs, stood up and started to applaud.

  Nope, not fucking awkward at all.

  The End

  * * *

  About the Author

  Christine Zolendz resides in New York City with her favorite NYPD detective and their two beautiful daughters. She loves reading, writing, wine, and caramel lattes. Get to know her better by visiting her Website, Facebook Page, or signing up for her Newsletter.

  The Miracle of Lights

  Dina Littner

  Rosie dips two fingers under the band of my boxers. She runs them from one hip to the other and back again. Absent minded touching is one of Rosie’s thinking “tells.” Her fingers wander when she has something to say but can’t find the right words.

  Mike nods toward her other hand which is drawing circles on his thigh. She elongates and shrinks the radius of each swirl varying the pattern from his knee to his boxer briefs.

  He once told me that it’s a rare form of ambidexterity for someone to “use both hands for different purposes with equal facility.” In other words, Rosie is talented as fuck and Mike’s a genius-geek who knows too much useless shit.

  Rosie readjusts between us on the hotel bed. She grabs another pillow and props herself higher. The fabric of her thin tank top slides up to show the soft curves of her stomach and the creases at the bottoms of her breasts. She’s exquisite. And she’s ours.

  Mike nods at me again and we make a silent agreement. We’ll let Rosie think this one out uninterrupted. Too many times we’ve disrupted her trailing fingers and concentration with hard dicks and sexy times only to never find out what was on her mind.

  Not that I’m not getting aroused. I mean, my dick’s already hard from the sweet dance of her fingertips right there. It takes a sustained force of will not to make a move on her. Maybe she’ll make a move on me. On us.

  I’m sure Rosie is thinking about what she wants to say to her parents tonight when we come out to them about our threesome relationship. We’ve been together nearly a year and we all agreed it’s time to be as open with our families as we are in our college town.

  We came up to Portland a day early to tour the city and spend our first night away together. Tonight we’ll celebrate Chanukah with Rosie’s family and sleep at her family’s house. She told us her mom made a sleeping diagram because there are so many overnight guests. Mike and I get the couches in the den. I’d rather we were sleeping in her room.

  There’s nothing sexual between Mike and me—except Rosie, of course. And, while his knee might touch my arm or my elbow might touch his hip while we’re in bed, the two of us are only interested in making Rosie scream in pleasure. Not that she’s a screamer. She’s actually quiet in bed, so her loud loss of control is more of a goal.

  When Rosie suggested that the three of us get together, I balked. I was not remotely interested in having sex with, around or near another guy’s dick. Mike was reluctant, too, but he had his own reasons. Rosie and I just didn’t know what they were at the time.

  Rosie put our anti-naked-man views in perspective with one question. “Have you ever watched g
uy-on-girl porn?”

  Of course we had. And our simultaneous, “Yeah,” answers were embarrassing enough, but admitting it to our super-hot and apparently super-kinky, best girl-as-a-friend? Major, major shame-faces.

  “Well, then you’ve seen erect penises. And”—Rosie gave us an all-knowing wink—“I’ll bet you got off to them, too. It’ll be just like that. You don’t have to touch each other. Just focus on me.”

  We worked through the hesitations and concerns. Now we are here today, ready to confess our love to the people Rosie loves most.

  “Guys,” Rosie says, interrupting my thoughts in her I-mean-business voice. The voice that’s in direct contrast to the way she’s now gripping my dick, and Mike’s, over our underwear. “I’ve decided I’m not going to say anything to Mom and Dad.”

  Wait, what? Did Rosie just renege on our agreement?

  I don’t understand. It was her idea to tell our families—we’d talk to her parents during Chanukah and my parents at Christmas. Mike will tell his mom over the summer when he goes home again. Money’s an issue for him—a flight back to New Jersey to talk about his love-life is not in the budget right now.

  “No, Rosie.” Mike rolls the “R” in her name with his slight Spanish accent. “We all agreed. They need to know... about us.”

  It’s not fair for her to unilaterally change our plan. We need to talk this out and decide together. “What are you worried about, love? I know that they might not be happy at first, but…”

  “There’s no way they can handle this. Us. C’mon, guys. What sane parents can accept that their college-age daughter is living and sleeping with two men at the same time?”

  Rosie squeezes my dick and in doing so quite effectively derails my response. I cover her hand with mine to stop her and get this conversation back on track, but when I see our dual grasp on my cock straining against the fabric, I’m done talking. It’s time to fuck.

  No one can argue that I’m a weak, weak man.

  Mike grunts on the other side of her. “Don’t distract us, baby.” His head is thrown back on the pillow, and his hips press up and up.

  She’s got him by the balls. Literally.

  Rosie flips over and pulls Mike’s underwear off. She takes his dick deep down her throat and stops when her lips reach the bottom of his shaft. She doesn’t move, except to blink and flare her nostrils for air.

  Mike moans and tries to thrust up, but she waits.

  And Mike waits.

  And I wait. Eager to see what Rosie will do next.

  One Mississippi. Two Mississippi. Three…Ten…Fourteen...

  Mike whispers to Rosie in Spanish. I don’t know much of the language but it’s clear he’s begging her to move. “Muevete, por favor. Please.”

  And damn if I’m not rooting for her to put my best friend out of the best kind of misery there is on this Earth.

  She doesn’t relent though. She holds him deep and breathes.

  When I reach thirty in my head, that’s when Rosie drags her mouth up his dick at an excruciatingly slow pace. Her lips tease the tip of his cock before she shifts her ass in the air and shakes her hips. With one look through lowered eyelashes, my invitation to join in the fun is extended.

  Discussion over.

  * * *

  Four hours later, we approach Rosie’s childhood home dressed for the party. Mike and I wear khaki pants and button-down shirts. Rosie is gorgeous in a flouncy skirt and tight sweater.

  I stop them both by the garage door. “We have to tell your parents, Rosie.”

  Other than when my dick was buried inside of her earlier, I’ve been stuck on the fact that she doesn’t want to share our status with her family. Fuck. I’m ready for the world to know how much we mean to each other. Why isn’t she?

  She huffs, her breath visible in the cool night air. “My family is going to freak out. You don’t know what they’re like.”

  Mike pulls Rosie to him from behind and then leans back against the garage door. The position creates a perfect arch that pushes her breasts high and tilts her hips out at the right angle for me to—

  “The point is for everyone to know,” Mike says into her hair. “You don’t hide who we are at school and we can’t hide who we are here.”

  Ahh. Good strategy, Mike.

  I crowd Rosie until she’s sandwiched between us and whisper, “At home, you like it when people notice us.”

  Rosie’s comfortable with our lifestyle whether we’re on campus or out and about in the small town built around our liberal university. She doesn’t hesitate to be affectionate with both of us in public and no matter the audience, the fact that she has two boyfriends is a non-issue for her.

  Rosie studies her hair ends. “Look, if the time is right, we’ll tell them. But I make that call. Okay?”

  It’s a better deal than her refusal two minutes ago.

  My consent is a hard and fast kiss. I press my body into Rosie’s, which pushes her tight between Mike and me. This is where she belongs. Always and in every situation.

  There’s a whirr sound and the door rises, jostling our position. Rosie darts to the sidewalk leaving Mike and me chest-to-chest in an off-balance hug. We struggle to get ourselves upright, but the awkward attempt to separate doesn’t work and I end up pulling Mike closer.

  The fucker smiles up at me and says, “Hey, chica.”

  A man in his late twenties stands inside the garage, watching us with interest. “Sorry, I interrupted whatever you guys were, umm, doing.” Then he steps toward our girl and grabs her in a big bear hug. “Rosie!”

  “Bruce!”

  It’s Rosie’s brother.

  He lets her go to shake hands with Mike and me. Rosie makes introductions and does not correct what her brother may have thought he saw between us.

  Hmm. I don’t like this.

  “Take the guys in through the front door, Rosie. Mom has a big welcome planned. I’ll meet you inside after I get the garbage to the curb.” Bruce points toward the front of the house. “Go.”

  * * *

  “...ve-tzi-va-nu le-had-lik ner shel Cha-nu-kah.”

  Rosie finishes the candle prayer and, suddenly the entire family belts out a gospel-worthy, “Ahh-amen.” Then they launch into some happy Hebrew song complete with clapping and joyful “Hey hey heys.” Rosie’s uncle Lenny plays the violin, or maybe it’s a viola. Who knows?

  Mike sings along with the family, the Chanukah card tucked in his back pocket. How the hell does he know the words in this unfamiliar language? Damn. I’ll bet he’s been listening to Chanukah music on his headphones since we made plans to visit Portland a month ago. Smart fucker. I can’t blame the guy for wanting to make a good impression.

  “He’s a good boy, no?” Rosie’s grandmother, Bubbie Beverly remarks in her slight European accent while beaming at Mike.

  Another great strategy, man.

  What’s mine?

  * * *

  Rosie works her way to us through the crowd of relatives as the candles burn and the songs continue. She presses her back into my chest and rests her cheek against Mike’s arm.

  If anyone in her family was paying attention, they’d “see” we’re more than friends. Only, no one is watching. So I do what comes naturally—slide my hand into the back of her jeans and rub a finger through the groove at the top of her ass. Rosie leans into me until she realizes what I’m doing and where I’m doing it. Then she hops away faster than I’ve ever seen her move and claps her hands kindergarten-style.

  Clap clap clapclapclap.

  “Let’s show Mike and Rand how to rock Chanukah Steinberg style!” Rosie’s too-loud and too-perky voice interrupts the current song mid-stream.

  The sudden silence is made worse by everyone staring at us like we’re the obnoxious tourists in the middle of a solemn ritual.

  Rosie ignores the less than enthusiastic response from her family. “I told the guys all about the songs, now it’s time for the food and then presents.” Rosie bounces on her t
oes and makes little butterfly claps that end in a pouty frown over her family’s lack of action. “Okay, people. It’s time to eat dinner. Let’s go,” she commands and points down the hallway.

  On our way to the dining room Rosie stage-whispers, “Hands. Off.” Then she glares and points at poor Mike, who as far as I can tell, didn’t do anything wrong. “You, too.” She storms ahead muttering, “Oh, sweet baby Moses, keep the freaking horndogs at bay.” God, she’s hot when she’s mad.

  Rosie’s Gram Linda must have misheard the remark because she says, “We’re not eating corndogs and gravy, Rosie. It’s the usual Chanukah menu.” The small woman links her arm in mine and winks. Uh, no, she didn’t mishear anything.

  We eat a traditional dinner of steak and fried potatoes—I mean, brisket and latkes, as articulated on the instructional card. It’s delicious, and I’m entertained by her family’s argument about whether the potatoes are better with sour cream or applesauce. Only I didn’t realize the choice was one or the other, and when Mrs. Steinberg sees me eating both toppings together, she looks like she might puke.

  Definitely a demerit on my make-a-good-impression quest.

  * * *

  After dinner, Mike offered his services for trash and clean-up duty. I asked Rosie’s mom what I could do to help and she pointed toward the men.

  “Talk with them.”

  She definitely hates me for my poor Chanukah-food etiquette. I’m sure that’s why I was banished to sit with the menfolk.

  It turns out that Mr. Steinberg and Bruce both work in my field of study and we’ve spent the past thirty minutes going over potential thesis topics to complete my marketing degree.

  Bruce recently opened the Seattle branch of his father’s PR and marketing firm when he returned to the West Coast from New York City. Bruce asked if I would be interested in potential summer internship, but I’m not sure the offer will still be on the table after he learns about my role in his sister’s life.