F*cking Awkward

C
opyright © 2016

The copyrights of With This Ring…Taryn Plendl; Wicked Weekend by A.D. Justice; Sex, Blue Balls, and a little Vatooing gone horribly wrong…by Ahren Sanders; Side Tracked by Aly Martinez; A Night to Remember by Amanda Maxlyn; It Started With a Drink by B.A. Wolfe; Ballcuzzi by Brooke Blaine and Ella Frank; Too Many of Us by Brooke Page; One Night Oh God No by Carey Heywood; #MyBigFatStupidHookUp by Christine Zolendz; Definitely a J Name by CM Foss; After the Treehouse by Dina Littner; Drew and Kiera Film Love Scene by Heather C. Leigh; Happy Birthday, Jesus by HJ Bellus; Hot Hands by K. Langston; Cockblocked by Laura Ward; My Kind of Girl by Lex Martin; Toytastrophe by Liv Morris; Blowjobs, baked beans, and cabbage…Oh, my! by Mel Ballew; Love Interrupted by R.E. Hunter; Sunburned by Stacy Kestwick; Knotted Up by Tiffany Aleman; and Is There a Baby in This Cup? by Trudy Stiles are held by the respective authors.

All rights reserved. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the publisher, except in the case of brief quotations embodied in critical reviews and certain other noncommercial uses permitted by copyright law.

This is a work of fiction.  Names, characters, places, and incidents are the products of the author's imagination or are used fictitiously.  Any resemblance to actual events, locales, or persons, living or dead, is entirely coincidental.

D
ear reader
:

Congratulations on purchasing the Awkward Sex Anthology! A bunch of amazing authors in a group called FTN (We could tell you what this means, but then we'd have to kill you) got together to write the most awkward sex scenes you could imagine, all for charity. You might be thinking to yourself, "I can't believe I just bought a book called F*cking Awkward" and I'm here to tell you, it's much better than the titles that were rejected:

F*cking Toasters

F*cking Goats

F*cking a Box of Captain Crunch

F*cking a T-Rex While Playing the Trumpet

F*cking My Best Friend's Neighbor's Stepsister's Starbucks Manager While Wearing a Toga

F*cking a Toga

I'm just kidding! Nobody wrote a story about f*cking a goat! It was a wombat, actually, and no one pressed charges, so it's fine. The author is fine, the wombat is fine, EVERYONE IS FINE AND I DIDN'T NEED THERAPY SO STOP LOOKING AT ME LIKE THAT.

Did you know that six out of every seven people in the entire world have experienced an awkward sexual encounter? It's true. I've done extensive research. And by extensive, I mean I did a poll of all the adults in my house - 2 dogs, 3 cats, and my husband and I. I'm pretty sure my dog Fat Ralph was lying when he told me he'd never experienced anything awkward during sex, but he had his nuts cut off when he was six weeks old and is still quite bitter about the whole thing and threatens me with a dog bone shank whenever we chat about sex, so I think it's best if I stop questioning him about the time I found him in the backyard with a jar of peanut butter, two frogs and the neighbor's cat wearing pasties. 

The cat was the one wearing pasties, FYI, not Fat Ralph. That would just be weird. 

So, grab some booze, sit back, and enjoy these hilariously awkward sex scenes. Give yourself a pat on the back for purchasing a book for charity and another one for never experiencing something as crazy as what you're about to read. Unless you have. In that case, it's okay to cry and rock back and forth in the corner screaming, "IT WAS ONLY THAT ONE TIME AND I HAD NO IDEA I WASN'T SUPPOSED TO PUT THAT CUCUMBER THERE!" Six out of seven of us totally understand. Except for Fat Ralph. He's totally judging you right now.

XO

Tara Sivec

I
took
one last glance around the room, just to be sure that everything was in place. My girl would be home soon, and I intended to surprise her with a night she’d never forget.

Chelsea and I had been a couple for almost nine months, and the woman completely changed my life. I was lucky to have her, I knew this. When we met, I was pretty much a self-indulgent asshole. Fortunately, she saw more in me than that and gave me a chance that I surely didn’t deserve.

Chelsea worked with my best friend, Trevor and his wife, Ava, so Trevor had texted me when Chelsea left work so I would be ready when she got here. He knew I was planning something, and he had my back, just like he always did.

Candles flickered from the dresser and champagne chilled next to the bed. The small black velvet bag sat at the foot of the bed where I could get to it easily. I groaned and adjusted my hard cock. The anticipation of the evening to come had been too much for me. I was pretty sure I’d been hard for hours.

“Hello?” Chelsea’s voice rang through the apartment. The sound of her heels on the hard wood floor echoed as she walked toward the bedroom. My heart sped up, suddenly nervous for her reaction. What if she thought I was crazy for trying something new?

“Nick?” She questioned, opening the bedroom door and coming to a complete stop, jaw hanging open in surprise.

“Hey,” I managed to speak, watching her reaction closely as her eyes roamed over my bare torso, down to the obvious bulge in my jeans and back up. When she smiled, I let myself exhale for the first time since she walked into the room.

“Hey, yourself,” she said, shutting the door behind her and walking toward me. “What do we have here?” I pulled her into my arms when she was close enough, holding her against me and breathing in her sweet scent. Her hair hung over her shoulder in cascading red curls and my fingers danced through them, loving how they felt.

“We’ve both been so busy; I just thought we could spend a night in.” I kissed her soft lips gently.

“I think that sounds like a wonderful idea.” She grinned, kissing me back.

I walked to the bottle of champagne, carefully opening it so the contents didn’t spill. With only a few drops on the floor, I proudly poured us each a glass, handing Chelsea hers before taking an undignified gulp of my own. She sipped from her glass, trying to school her features. I could see the corners of her mouth turn up slightly. She had to know that I was completely out of my element here. Chelsea was the first and only girl I’d ever put any effort into, so romancing someone was almost a foreign concept for me.

After several sips, I took her glass from her, setting it on the dresser before pulling her to me again. Gathering her long hair to the side, I exposed her neck, placing gentle kisses to her soft skin. I felt her shiver in my arms, making me grin. God, I loved that I affected her.

Leading her to the bed, I slowly lifted her shirt over her head, groaning when her lace bra came into view. “Fucking gorgeous” I groaned, cupping her breasts in my hands. Chelsea had a runner’s body, tight and lean. She was the opposite of every woman I dated before her, yet she was exactly what I wanted, now and forever.

Slowly, I unclasped her bra, dropping it to the floor before moving onto her skirt. As the skirt fell, I moaned at the sight of her matching lace panties and garter belt with thigh-high stockings. “Fuck woman, you’re like a wet dream.” My fingers slipped below the waist of her panties, sliding them down her legs, keeping the garter belt and stockings in place.

Once I had her just where I wanted, I backed her to the bed, easing her down so she was laying back. I knelt on the floor, spreading her legs wide, cursing at the pinch of my rock-hard cock, stilled confined. Without a word, I moved in, running my tongue through her cleft, groaning at the sweet taste of my girl.

“Yes!” Chelsea moaned, urging me on.

I ran my tongue over her clit in quick succession, just how she liked it. I could feel her beginning to tremble, her breathing faster and moans louder. Slipping a finger inside, moving with the same tempo of my tongue, I heard her gasp as her body went tense, her walls gripping my finger from the inside.

“Fuck me, Chelsea, that was the hottest thing I’ve ever seen.” I slipped my finger out of her, standing up and helping her scoot further onto the bed. “Roll over.” I instructed.

“What are you up to, Nick?” She asked, eyeing me curiously.

“Trust me.”

As she rolled over, I reached for the velvet bag, reaching into it until I found what I was feeling for. The small flogger had little leather hearts hanging from the eight inch leather straps. I had never used something like this before, but I’d watched my fair share of porn, and I figured this wouldn’t be too hard.

At the first touch of leather to skin, Chelsea moaned. I began slowly, just dragging the leather up and down her back and ass. When I felt like I’d gotten the hang of it and she seemed to be enjoying the feel of it, I flicked my wrist, snapping it against her skin.

“Ooh!” Chelsea yelped.

“Too much?” I asked, worried that I hurt her.

“No, just surprised me. It felt good.”

I continued the same motions, snapping her sporadically then dragging it up and down, each time producing a pleasurable moan from her. “Let me try you,” She suggested, rolling over and looking at me. I hadn’t thought about changing roles, but her moans had intrigued me, so I shrugged and lay down, handing the flogger to her.

Chelsea straddled me, sitting on my ass as she began dragging the leather straps over my skin. The softness of it felt surprisingly good.

Snap.

The slight sting got my attention, but it didn’t hurt.

“Did that sting?” She asked.

“Not really.” I shrugged, relaxing into the bed as the leather trailed again.

Snap.

“How about that?” She asked. The sting had been a bit more than before, but it still wasn’t painful.

“Fine.” I shrugged, barely laying my head on my arms before she started again.

Snap! Snap! Snap! Snap!

Warning bells began to go off in my head as I reached back and grabbed a hold of her small wrist, halting her flogging in mid air. Her face morphed from determination to regret quickly.

“I’m sorry. I guess I got carried away.” Her voice was soft.

“I think so, you little dominatrix,” I said, prying the flogger out of her hand and tossing it across the room, well out of her reach. “I think we are done with that.” The sting in my back was still apparent even after she stopped.

“Sorry, babe.” Her sheepish grin made me smile.

Chelsea reached for me. “My turn, Nick.” I went willingly, my throbbing cock needing some relief.

She slipped her fingers into the waist of my pants, pulling me closer and taking my mouth in a soft kiss, tongues tasting and warring. My entire groin was throbbing now—almost painfully. “Please, Chelsea,” I begged.

After much unnecessary seduction, she finally pulled my pants down, following with my underwear. “Holy shit, Nick!” Chelsea exclaimed.

“I know, baby.” I smiled, her reaction inflating my ego.

“What did you do?” The change in her voice had me opening my eyes to see what was wrong. Chelsea was looking at my dick with a strange look on her face. Her hands reached for me, but stopped just short of touching.

“Chelsea? What’s wrong?” My eyes followed to where she was staring.

“What the fuck?” I exclaimed, finally seeing exactly what had Chelsea worried.

I was aroused, that was for sure, but that wasn’t the reason for my throbbing groin after all.

My fucking junk was purple! Swollen and fucking circulation-cut off-purple!

“Oh my god, Chelsea! Help me get it off!”

“Get what off?” Chelsea looked at me, completely confused.

“The cock ring.” In my attempt to make this night memorable, I’d purchased a metal cock ring and placed it around my balls and penis. The guy at the adult book store asked if I had experience with the rings, and I assured him that I did, not wanting to look stupid. Maybe I should’ve listened to him.

“Why do you have a cock ring, Nick?” Chelsea looked up at me, her eyes wide.

“I thought it would be exciting.” I shrugged, the panic welling up.

“Okay, lay down. I’ll try to put some lube on it.” I lay back as she instructed, watching as she went to work on my hard cock, just not in the way I’d planned. Each touch was almost painful. My skin was so sensitive. When she tugged on the metal, I shot off the bed.

“That’s not going to work. It fucking hurts!” I didn’t want to panic, but I couldn’t help it.

“I’m going to call Talia,” Chelsea said, climbing off the bed.

“No!” Talia was the last person I wanted to know about this. She was Chelsea and Ava’s best friend and my other best friend, Tom’s girlfriend. She also happened to be an ER nurse, and I would never hear the end of this if she got involved.

“Why not? She’s off work tonight, and could tell us what to do.” Chelsea looked at me like I was crazy.

“She’s off tonight?” I asked, already grabbing my clothes and stepping into my pants.

“Yes, why?”

“Take me to the hospital, Chelsea. I need help.”

F
ortunately for us
, the Emergency Room wasn’t too busy. We approached the desk and were greeted by the woman behind it. She smiled before asking us what we were here for. I looked to Chelsea for help, but she was texting someone on her phone.

Leaning in, I whispered, “I, um… I have a problem with my, uh, my penis.” Her eyes widened momentarily before she schooled her features. After relaying my information to her, I was given a hospital bracelet and instructed to sit down.

“Who are you texting?” I asked, cringing as my throbbing cock rubbed against my pants as I sat.

“Ava wants to know if she and Trevor should come.”

“You told them?” My mouth dropped.

Chelsea looked at me like I had two heads. “Of course. They’re like family.”

“This isn’t like I’m having a heart attack, Chelsea. I have a fucking metal ring around my balls and cock!” I realized my voice was a little too loud when several eyes landed on us. Thank God that the nurse in triage took mercy on my at that point and called us back.

After taking my blood pressure, which was slightly elevated, and temperature, I was shown to a small room and given a gown to put on. The gown felt so much better than the pressure of my underwear and jeans, and I sat on the bed, slightly relieved. Chelsea sat in the chair and smiled at me like she didn’t have a care in the world.

“Aren’t you even slightly worried? What if I can’t ever have sex again?” The panic started to well up in me. What if I caused permanent damage?

“Hi, Nick. I’m Dr. Shaft.” The man in the scrubs walked in extending his hand to me. He looked to be younger than me.

“Dr. Shaft? Is that a joke?” I asked, looking at his name badge to make sure.

He chuckled and shook his head. “I’m afraid not, and seeing why you are here,” he flipped through my chart, “I guess it is fitting, huh?” Chelsea giggled and I glared at her.

Dr. Shaft washed his hands and put on some gloves before coming over to the side of the bed. “Let’s see what we have going on here.” He pulled up the gown and grimaced when he saw my cock and balls. “Well, this isn’t good.”

“No shit. That’s why we came here. Can you get it off?” I asked, gripping the rail of the bed as Dr. Shaft poked and prodded at my swollen members.

“We’ve got some tricks up our sleeve here. Don’t worry, I’m just going to get the nurse and we’ll get you taken care of.” He tossed his gloves into the trash can and left through the curtain.

“Nick?” A familiar voice came through the curtain and I groaned as my best friend, Tom came into the small room.

“Are you okay?” He looked from Chelsea to me, concern covering his face.

“You texted, Tom too?” I glared at Chelsea, who held her hands up.

“I did not.” She shook her head adamantly.

“Chelsea didn’t text me. Talia got called in to work, so I was just dropping off some dinner. What happened?” Tom came in and stood by the bed. I relaxed a bit, glad to know that Chelsea hadn’t texted
everyone
.

“I had a mishap with something. I’m fine. We should be out of here in no time. I’ll call you later.” I did my best to get Tom to leave, but he wasn’t having it. Tom and Trevor were my best friends, and Chelsea was right, they were family. I knew that Tom was genuinely concerned, but that was only because he had no idea what was really wrong.

“You’re the ‘Cock Ring Guy’?” I groaned loudly at the sound of Talia’s voice as she pushed a metal tray into the room, a smile spreading across her face when she realized her patient was me.

“Talia!” Chelsea jumped up and hugged her. “I feel so much better knowing you’re here.”

“Me too.” She grinned, looking at me. This night just got a whole lot worse.

“Cock Ring?” Tom asked, glancing down at my crotch before grimacing. “Dude!”

“Shut up,” I ground out between my teeth. “It wasn’t supposed to get stuck.”

“Okay, ready to get started?” Dr. Shaft came back in the room, pulling on another pair of gloves.