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

by Plendl, Taryn

  “You smell like sugar cookies,” Rico says between our lips.

  My eyes shift to the all-seeing camera on his nightstand and then back to him. When he smirks, I know anything that happens or is said is all for show.

  My hand skims the front of his red, silk boxers. The material feels like pure ecstasy under my touch. We roll until I’m above him, his body trapped under mine.

  I tuck my hand into his boxers where I find something I don’t expect. My fingers wrap around him. Maybe he needs a small boost. Every time we’ve been together, I haven’t had to work too hard. He’s a sure thing. The guy can be hard at the drop of a dime.

  So, what the hell is this?

  “Everything okay in there?” I ask. I don’t mean to stare, but I look between us and peek between the small gap my hand makes in the material. Still soft. Hmm . . . That’s going to be hard to work with.

  “I don’t know what’s happening,” he admits, embarrassed by his lack of firmness.

  “Well, we can’t do this whole shebang without working equipment, Rico.” My chest hurts when I try to hold back the small laugh begging to come forward.

  “Why don’t you put your mouth on it?” He skims his tongue along the inside of his cheek. His amusement is both infuriating and amusing.

  With a challenging wink from Rico, I surrender and dip my head as I pull the material of his shorts down. My lips cover him, and he jolts. After a mental pat on the back to congratulate myself for a job well done, I lower my mouth over his length several times. The hard ridges turn soft. Again. I pop up, leaving my hand wrapped around him, not willing to fully give up.

  “Are you shitting me?” I bark, stroking him in hopes of keeping what little erection we have going strong. “You sure know how to make Mrs. Claus feel like a champion.”

  “I can’t believe this is happening.” Rico covers his eyes, giving me the perfect opportunity to laugh unnoticed. “This has never happened.”

  “You don’t need to tell me. I know.” I sit back, still with him in my hand. “Okay, maybe you’re camera shy. I have an idea.” Rico’s embarrassment has my guilt flying into overdrive. “Keep your eyes shut and clear your mind.” He does as I say and thankfully, doesn’t look at me because I don’t know if I can make eye contact with him without losing my shit.

  My hand tightens, my pace switching from slow to fast. There’s no movement. No change. Rico takes a deep breath and frowns, his head thrashing against the comforter. His frustration with himself is evident.

  “Why don’t you tell me why this is what you wanted for your Secret Santa gift?” The question is meant to distract him. I stroke him several times, absently looking around the room at all the effort he put into the night.

  “For starters, what guy doesn’t dream of recording himself? And I stupidly assumed it would be hot, but it never occurred to me that not-so-little Rico wouldn’t deliver in the moment.” He sits up and glances down at his unresponsiveness. His breath labors and I can practically hear him pray for this all to come to an end.

  “Relax.” I push his back down onto the mattress. Never in a million years did I ever picture myself talking Rico through getting himself up.

  “Are you fucking kidding me right now?” he shouts. His hand claps down on the mattress proving his frustration.

  I stay silent, offering him my old school handjob skills. As I quicken my pace, he grows hard for a split second and then falls limp. The burn in my forearm warns me to stop, but the last thing I want is for Rico to feel defeated. I continue for . . . Well, I don’t even know how long it takes, but it feels like an eternity.

  No. No. Now is not the time to cramp up.

  Once again, he thickens, but it couldn’t be at the worst time. My hand aches and burns as I spring from the bed, releasing him from my hold. I dance on my tiptoes and attempt to shake the horrid sensation from my fingers.

  “Are you okay?” Rico sits up in the bed. “Why’d you stop? I was getting there.”

  I glare daggers at him and his now-hard cock as he lays on his back, all his glory on display. My arms flail to the side. My annoyance grows.

  “Why’d I stop?” I repeat his question. “Well, let’s see here. You couldn’t get it up, and then to help you along, I gave you what could go down as the longest handjob ever on record, and because the universe hates me, my hand cramps up.”

  Rico covers his mouth, hiding his enjoyment. We fall into a fit of laughter about how absurd the whole situation is. This isn’t our first time, and we are bumbling through it like virgins.

  “Come here.” He reaches out. I place my hand in his, and he starts to rub the almost non-existent pain away. The gesture is sweet, and I find myself melting into his lap. “Maybe we should start over. This isn’t how I saw this all going.”

  “No?” I raise an eyebrow. “Most pornos don’t start off with an awkward handjob and a hand cramp?”

  “Not the ones I’ve seen, at least.” Rico kisses the tip of my nose. The gesture is sweet and somehow fitting for the situation. Unlike his soft kiss, he flips me harshly on my back and drops down to his knees beside the bed. His talented hands shimmy my panties over my hips and thighs until I’m only wearing my thigh high stockings and skirt.

  “Just lay there and enjoy, Mrs. Claus. Maybe I can redeem myself.” Rico dips his head between my legs, and I gladly open up for him. The evidence in my lack of ability to say no to someone like Rico is clear. For fuck’s sake, I’m spending my night dressed up as Santa’s slutty wife as he buries his face between my thighs.

  “Holy shit,” I whisper when his tongue skates over my opening. My eyes clamp shut to focus on every move his tongue makes. The sensation is wet and rough, then light and airy. If he keeps this up, I’ll be spent in seconds.

  Through my gasps, I hear a humming. Confused, I sit up and rest on my elbows. What’s that sound? I almost forget about him between my legs until I feel a vibration on my clit. That’s something that should rocket me into bliss but only confuses me. I focus on the noise and immediately kick out my leg. My heel hits the laptop, and it falls to the floor, causing the loudest crash.

  “What the hell?” Rico shouts, startled. “What are you doing?” He springs up from the floor.

  “What am I doing? What are you doing?” I turn the attention back to him. “Were you just humming along with the song?”

  “Umm . . .” Rico blushes.

  “Talking to Violet about oral sex, huh?” I grin, flabbergasted by the whole situation. A while back, I’d suggested Violet hum a song to make giving head easier. Loosen her throat, if you will. “That’s not for you. It only works when a girl does it on a guy.”

  “Seemed to be working on you just fine.” He beams with pride.

  “I can’t do this. My head’s all over the place, and your rendition totally threw me off.” I point to my white boy shorts with peppermint candies all over them.

  “So, we aren’t going to finish this?” He sets the laptop back on the nightstand and pulls me to my feet as he stands to his full height. “That means you owe me another present. You can’t leave him like this, now that you’ve got him all riled up.”

  I ignore his request.

  “Just so you know, next year, if I pull your name, I’m throwing it back in. Sexual favors are not allowed on your Christmas list anymore, Rico.”

  “Seeing you dressed in this has been enough of a gift for me.” He brushes his thumb over the velvet fabric before adjusting himself inside his tented boxers.

  “Ugh.” I groan. “How is it even possible I still find you adorably charming? And why did I agree to this?”

  “Mrs. Claus is notoriously obedient,” Rico answers, pulling a white t-shirt on. His grin beams in my direction.

  I shake my head at how idiotic I was to think this of all things would stop Rico and me from being what we so naturally are. A hot mess.

  * * *

  We barrel into the kitchen in a fit of laughter, recalling Rico’s lack of blood flow, but stop sh
ort at the sight of all of our friends sitting around the kitchen table in an almost painful silence.

  “Hey,” Rico offers, stepping around me. He clearly doesn’t see the way they’re gawking at us as he steps to the fridge to pull out the carton of eggs. I watch as he starts to crack several into a bowl.

  Violet and Kennedy’s comically stoic faces are a dead giveaway. Something is going on, and no one wants to say anything. But why?

  My attempt to read Graham and Dan is a fail because neither will look me in the eyes. When they start to giggle like school girls, Violet kicks Dan to shut him up.

  “Seriously, guys, what’s going on?” I beg. “You guys are acting weird, and it’s freaking me out.”

  “Rico, will you make me a soft boiled egg?” Dan calls out, over exaggerating the word soft. His laughter thunders through the kitchen.

  Graham reaches into the fruit bowl on the middle of the table. “These bananas are soft. Amanda, do these feel soft to you?”

  “Stop it.” Kennedy elbows him in the side.

  As an epiphany strikes, I scurry over to the stove where Rico is in his own world, unaware of the events unfolding behind his back. I whisper my fear to him, and he twists, spatula in hand, to address our friends. His mouth widens with shock.

  “How?” he asks. “We would’ve heard all of you in the stairway, so how do you know?”

  Graham stands and grabs the remote from the center island. The TV mounted in the corner is powered on, and my heart drops to my stomach. This can’t be happening. This can’t be real. Rico’s bedroom is on the screen. I’d think it was a picture, but the candles flicker in the darkness.

  “So, remember when we wanted to surprise Ben with the signed baseball jersey?” Graham asks.

  “I don’t understand what that has to do with this,” I interrupt, pointing to the television, then looking back at Rico.

  “Well, we’d set up a live feed from Rico’s laptop to our television, so when Ben walked into his room, he’d see the jersey on his bed. We thought it would be more exciting to see his initial surprise without us actually being in the room.” Kennedy stands.

  “So, what you are telling me is that we just . . . You guys just s-s-saw . . .” I stutter. “Everything?”

  “Holy shit,” Rico barks. “I must’ve pushed the wrong button. Instead of record, I pushed . . .”

  “Live stream.” Dan finishes his thought for him. He turns his back to hide his elation.

  “If it’s any consolation, you really pulled off the Mrs. Claus getup.” Violet wraps an arm around my shoulder and pulls me in close.

  “And if it that doesn’t help, Rico’s head blocked the money shot. Your poinsettia was perfectly covered,” Kennedy adds as she sits down on Graham’s lap.

  “I want to die. Literally die.” My cheeks burn with full-blown embarrassment. “This is your fault.” I point at Rico. “And your fault.” I turn to Kennedy. “If you hadn’t suggested this stupid Secret Santa, I wouldn’t have found myself in this position.”

  “Something tells me,” Kennedy points between Rico and me, “you would still somehow find yourself in this position.”

  “The “Twinkle, Twinkle” trick really does work, though,” Dan says. “And it takes a real man, in bright red, silk boxers to even attempt it. You have to at least give the guy some credit.”

  “Yeah, give me some credit.” Rico points the spatula back at me. As if he’s recuperated from the whole embarrassing situation, he turns to stir the eggs.

  “I hate all of you. This is why I was opposed to the Secret Santa to begin with.” I stomp my feet and storm out.

  “There’s nothing secret about Santa this year,” Graham shouts. Even though he can’t see me, I raise my middle finger.

  “Christmas can go fuck itself,” I yell back. Their laughter rings throughout the bottom level of the house.

  This wretched holiday will be filled with snow, tinsel, and mistletoe. All the things I hate.

  Add in the live-streamed porn, and you’ve got an All-American Awkward Christmas.

  The End

  You can find more of these characters in the Our Worlds Series!

  When Our Worlds Collide

  When Our Worlds Fall Apart

  When Our Worlds Stand Still

  * * *

  About the Author

  Lindsey Iler lives in Michigan with her husband and children. When she isn’t writing, she loves to read and spend time with family and friends. To get to know her better, check out her website (http://www.lindseyiler.com) and Facebook Page (http://www.facebook.com/lindseyilerbooks).

  An Oral Exam

  Liv Morris

  After ending my last conference call, I could finally head home. Even today, on New Year’s Eve, I found myself as the last person in the building. But it’s the end of the month, not to mention year-end, so numbers needed to be tallied. I was the Mid-West’s head of sales for a major pharmaceutical. Yes, I was one of those big bad people who worked for the evil drug companies. However, it paid my bills even if it did tug at my conscience on occasion.

  I stood up and pushed my chair under my desk, then pushed my arms into the sleeves of my suit’s jacket. But before I could make an escape, my office door opened up. Expecting the janitor, my eyes went wide when a woman dressed in a tight red suit walked in. I only made it to her boobs before she spoke.

  “Hello, Mr. Jordan. I was hoping to catch you before you left for the day. Do you have a few minutes?”

  As I took in the woman’s beauty, I saw a familiar face, though she was dressed differently than normal. Her clothes spoke of seduction and appealed to my dick; and my fingers, not to mention my lips, because this woman’s curves should be explored, and worshipped. Mentally slapping myself, I remembered where I was standing, in my office. Dammit.

  “Well, this is a pleasant surprise. What can I do for you today?” I raised one eyebrow in anticipation, then perched myself on the corner of my desk.

  Without an immediate answer, she turned to close the door behind her. Interesting, since I didn’t officially invite her in, though she knows me good enough to enter without a thought.

  “I heard there was a position open in your department. I wanted to talk to you about it,” she said while sashaying toward me while her curvy hips worked my dick into a semi-hard trance.

  I shifted myself on the desk and swallowed. A warm smile met me, one that knew exactly how she was turning me on. Minx.

  “You might be in luck. I have a position open working under me,” I said while dishing up a side smirk.

  “Working under you?” she questioned while moving in front of me. I nodded in response. “What are the requirements for this job?”

  “Willing to follow my instructions. Come when I call. Attention to details in all things.” She sat her designer bag beside me on my desk, and placed her free hands on my thighs. But I wished she would move them higher to where my erection pressed against the zipper of my suit pants. The pressure bordered on painful.

  “I have proven talents in all those areas. Would you like me to show you?” She ran the tip of her tongue across her lips and bit down.

  “We could consider it a part of your informal interview,” I teased back at her, taking her bait.

  I picked her hands up in mine, and walked around to the chair behind my desk. Grasping her hips, I lifted her up on my desk. An intake of breath from the surprising touch left her lungs.

  She slipped off her killer red heels as I sat down in my chair. I watched her delicate feet slide up my thighs to the full-on bulge in my pants. With one foot, she pressed against me and I hissed. Her soft touch burned my skin, but I wanted to be consumed with more, like her mouth.

  “What tests do I need to take for this position?” she asked coyly as she peeked down at me through her lashes.

  “I think an oral test would be smart. Are you game?” I asked with a seductive smile. Her eyes twinkled with mischief in an unguarded and sexy as hell way. God, I missed th
is look from her.

  “I need this position, and I am willing to do anything for it. Anything.” She stressed and added a wink. She slipped from the edge of the desk to fall in front of me on her knees. I closed my eyes for a brief moment as I imagined what came next, and hopefully that was me.

  “I love your dedication to getting the job done,” I said. She brought her hands to my belt buckle and hesitated.

  “May I?” she asked.

  “By all means. Let’s say your oral test has begun.” One of her brows rose as she met my challenge and started to unbuckle my pants.

  With skilled expertise, she had me open to my boxers in seconds. “Raise your hips.”

  I gave her an admonishing stare. “Is that how you plan to speak to me as your boss? I need to know before I hire you.”

  Looking away, and then returning to face me, I watched her try to conceal the laughter in her eyes. “Please, sir. Would you raise your hips?” she asked, playing along with my demands.

  “That’s better. I hope you remember this for all our future interactions. That is if I hire you.” She glanced back up at me, and I swore she was holding back an epic eye roll.

  I raised my hips as she moved my boxer briefs over my hips. One of her hands freed my dick from its prison.

  She moved her mouth closer to me, and I held my breath in anticipation of what she might do next.

  “Do you like to be in control?” she asked. Her mouth only inches away from where I needed her most.

  I ran my fingers through the strands of long hair. I took a fist full and pulled until she was looking straight me. “I do.”

  A shiver ran through her at my declaration. “Now suck me in your mouth.”

  She parted her red lips and tongued my dick from base to tip. I closed my eyes as the welcomed sensations washed over me.

  “Just like that, you dirty girl.” A smile crossed her lips as she slid my entire dick into her mouth. “You’re fucking hired,” I hissed.

  She ran her hands up my thighs, her fingernails pressed into my skin, most likely leaving marks.