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F*cking Awkward
Author: Taryn Plendl






Dear 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.




Tara Sivec



With This Ring…



Taryn Plendl



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.

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