Awkward Flirting Novels & Stories

I was once the beloved daughter of the powerful Alpha and Luna of The Midnight Ridge Pack. I thought I had everything—a loving family, a protective brother, and a perfect fated mate—Steve Dolton, the strongest Beta of The Midnight Ridge Pack and the man I had loved for eighteen years. But when I turned eighteen, my world shattered. I discovered that I had been switched at birth and that Penny was the true heir of the pack. In an instant, I became the most awkward existence within The Midnight Ridge Pack. Though my parents promised I would always be their daughter, when Penny offended The Rogue King, they didn’t hesitate to make me take the blame and threw me into the infamous rogue den. I endured torture from silver chains and wolfsbane, my body covered in scars, becoming the lowest slave in the rogue den. It wasn’t until the fifth year that my brother-Alpha Joe and my former fiancé- Steve, came to the rogue den to take me back to The Midnight Ridge Pack. I overheard the casual chatter of the servants. "Does she seriously think she can come back?" "She made Miss Penny suffer outside for over a decade, stole ten years of happiness from her, and now she has the audacity to return and keep taking what belongs to Miss Penny. Shameless." "I heard that bringing her back this time is to help Miss Penny..." My throat tightened, and my palms grew cold. "Julia, come back home with us. We were wrong about you!" "Steve and I will treat you twice as well. You're still our precious little princess!" Amid their urging and apologies, I loosened my hand grip on the tattered hem of my dress. I had already promised to marry the son of The Rogue King. Our wedding was just around the corner.

~You were there when my heart fell for you, but you were never there when my heart yearned for you, still, you never got out of my heart~ I thought it was good to leave because it seemed like they were on their date. I turned around suddenly Newt called. 'Prisha, is that you? Wow! what a pleasant surprise..." I slowly turned towards him, forcing a smile, and replied, "Hey! Newt, nice to see you..." "What are you doing here? Where is your friend Kriste? It is a little awkward to see you without her. I have noticed you two going everywhere together be it washroom as well," he mocked chuckling. Even though I didn't found it even a little funny, I forced a smile and replied, "I am just wandering around the town alone. As I was bored staying home. And about Kristen, she might be busy somewhere." "Oh! anyway come and join us. I want to introduce you to my..." "Girlfriend," before his words were completed my mind had already said it loud. so, I hastily interrupted him, "I am so sorry. I need to rush back home. My mom called me twice. Bye..." Before he could react, I was already out of the restaurant at great speed. The sky was covered with heavy black clouds and soon one after another drops of rain drip down along with my tears. I walked few steps but was not able to go any further. I fell on my knees getting weak to stand and slowly eyes got blur. Soon, I collapsed on the ground and before my eyes were forced to shut, I saw someone walking towards me.

Kael was raised on one unshakable belief: fated mates were a weakness. Stories of alphas losing their minds, their control, and eventually their lives over mates had been passed down like cautionary tales. His great-grandfather had been one of them, brought to ruin by the unbearable loss of his mate. Kael’s grandfather had made sure that never happened again, enforcing strict laws which prioritized strength over sentiment. The pack thrived under that discipline. No one bonded. No one lost themselves. Kael believed in those laws. He wanted to believe. But wanting and doing weren’t exactly the same thing. Now, standing face to face with his fated mate, he was at a crossroads. Accepting them could fracture everything he was taught to protect. Rejecting them might break something in him that he would never be able to fix. Either way, the consequences were inevitable and permanent. Max never asked for much out of life. Just to finish her endless list of chores quickly so she could go to school, where the world felt wide and full of things to learn. Existing quietly had always been her way, keeping her head down, staying out of trouble, and doing her best to be invisible. But nothing about her life was simple.The most popular boy in school suddenly seemed interested in her for reasons she couldn’t understand. He was good looking, admired by all and magnetic, while she was awkward, quiet and unimportant. Soon, Max would find out that she wasn’t so small after all, and her life, every strange, shadowed part of it, was just one piece in a much bigger puzzle. And Kael? He wasn’t just the school’s golden boy. He was the beginning of everything.

Shane Floyd and I have been dating for seven years, and my parents keep pressuring us to get married. However, Shane keeps saying the same two words. "Let's wait." My parents think we aren't financially ready, so they prepare a generous wedding gift for us. They even buy us a car and a house. However, Shane still says the same two words. "Let's wait." I have no idea what Shane is waiting for, but I decide to wait with him. At our class reunion, I bring out a cake I have prepared for Shane. "Today's Shane's 30th birthday." My classmates start gossiping at once. "I just remembered something. Shane Floyd and Amelia Wood made a pact that if they were both still unmarried at 30 years old, they'd get together!" Amelia Wood smiles shyly. "His wife is right here. Let's not bring that up." Shane simply glances at me. "We're not married, so she's not my wife. I promised I'd wait for you until you turned 30 years old. I didn't break my promise." My heart lurches as I hold the cake. Now I finally know what Shane has been waiting for. As the crowd teases him, Shane leans in to blow out the candles and make a wish. "Here goes my first wish. I wish Amelia is still single." That's enough. I gently set the cake down without making a scene. As the crowd exchanges awkward glances, I turn and leave with my dignity intact. Downstairs, a cab driver is calling out to passersby. "Miss, do you need a ride? Are you waiting for anyone else?" I open the door and get in the cab. "Let's go. I'm not waiting for anyone."

My wife and I had agreed to spend the holiday at my parents' house. Right before we walked out the door, she said, "I forgot to change my address again. The package was delivered to Grant's place!" I went still. Three years of marriage, and yet she had never once updated her default shipping address. A microwave she ordered online was delivered to her ex-boyfriend. She said it worked out, since his microwave was broken anyway. The anniversary gift she had picked out for me was signed for by her ex-boyfriend. She said it would be too awkward to ask for it back. The Valentine's Day gift she ordered for me online ended up in her ex-boyfriend's hands. She said she could not give me something secondhand, so she let him keep it. This time, she was ordering a holiday gift basket, and I had reminded her two weeks in advance. It still went to her ex-boyfriend. I kept my voice as steady as I could. "Go get it back. Drive over there right now." Her expression darkened. "He already signed for it. How am I supposed to get it back? We'll just pick something up on the way." "Get it back," I said. "Do you have to be so petty?" she snapped. "You're a grown man. You always have to make such a big deal out of everything." Every time something ended up at her ex-boyfriend's place and I asked her to get it back, that was the answer I got. My hands clenched until the knuckles went white as I watched her slam the door on her way out. I ignored the dull ache in my chest and sent a message to my lawyer. "Happy holidays. Could you please draft a divorce agreement for me? Thank you."

I'm a mafia princess with crippling social anxiety. My fiancé, Rocco Falcone, is our family's consigliere. He’s the exact opposite of me—extroverted, effortlessly charming, a master at reading and bending people. He's supposed to be my protector. My only link to the outside world. Tonight was the charity gala for my late mother. I was hiding in the darkest corner, a mask covering my face. Rocco was supposed to give the speech. My speech. He never showed. [Emergency. Sorry. Skip the speech, I know you hate the attention. Driver will take you home after the auction. Don't wait up.] Then I saw Livia’s new post. It was a picture of Rocco, draping his suit jacket over her shoulders. He was looking down at her, his eyes full of a tenderness he never showed me. The caption was a gut punch: [No prom date, so my big bro saved the day! Couldn't have done it without him! ] The cold hit me. Bone deep. He ditched a memorial for my dead mother... to take his stepsister to a university dance? The guests began whispering and sneering that I, the famously awkward, socially crippled princess, couldn’t even force a word out. I stared at the whiskey I’d ordered for him. The ice in my glass was melting. Just like the hope in my heart. When I got back to our empty penthouse, my screen was lit up with missed calls and texts from Rocco. The last one came in thirty minutes ago: [Aurelia, trouble at Livia's prom. You know how she gets. Couldn't leave her. Your mother's gala means everything. I'll make it up to you, I promise. Next time will be perfect. Trust me.] I didn't reply. An engagement held together by "next time." Was a promise like that even worth keeping?

On the eve of our engagement ceremony, I noticed that Angelina Manning, my rich girlfriend, wasn't paying attention at all when we were shopping together. I bought a hotdog from a nearby food truck and passed it to Angelina's lips. To my surprise, she tossed it to the ground furiously. "Devon Fuller, my family wants a son-in-law who can carry himself with confidence and poise! Stop buying these cheap things! You'll just end up embarrassing me even more! How can my parents ever accept you if you keep doing things like this?" Feeling rather awkward, I picked up the hotdog and threw it into a nearby trash can. Then, I nodded in response so that I could maintain our four-year relationship. "Okay." I thought that was the end of the outburst, but Angelina decided to get engaged to Jeffrey Terell the next day. "Devon, Jeffrey committed suicide and got admitted into the hospital just so he could be with me. Once he's back to normal, I'll definitely return to you." I still nodded and broke up with Angelina. "Okay." After that, I left. Four years later, Angelina shows up at my residence with the diamond ring she had used to propose to me back then. "Devon, Jeffrey has agreed to file for a divorce from me. We can finally be together again! I told you before that I can return to your side as soon as Jeffrey lets go of his obsession over me and stops hurting himself." I frown at Angelina, who looks all loving and affectionate. At the same time, I mentally curse myself for picking this particular time to come home. After all, I've decided to come back to my cottage just to grab something on a whim, only to bump into my delusional ex-girlfriend. I just push her toward the door. "Excuse me. I don't want to be late picking up my kid from school."

My husband was working over the holidays, again. He’d been sent out of town to oversee one of the Family’s dock operations and a string of gambling houses.. I decided to buy a ticket and surprise him. Only business class was left. Staring at the five-figure price, I gritted my teeth and spent a year’s worth of savings. Then I couldn’t even figure out how to pull down the damn tray table. The socialite seated next to me let out a cold laugh. “Never flown business class before?” I forced an awkward smile. “My apologies. You must be… important. You have that aura.” “Oh, me? No. The man who keeps me is important. He’d charter a private jet if I asked. Business class is practically slumming it.” I blinked. “A… keeper? That’s rare.” “Not really. I’m his secretary. I mess up a lot. Cost him a fortune. He yells at me until I cry. And then, well… crying leads to other things.” She winked. “You know how it is.” “Funny,” I said, my voice tight. “My husband has an assistant who helps him manage accounts for the docks. She’s always messing things up too.” “You’re married?” She looked me over, head to toe. “My man has a wife about your age. Says he’s sick of her. That touching her is boring. Says I’m more exciting just brushing my hair out of my face.” She leaned closer. “I told him I wanted to see him for New Year’s. So he told the wife he had to work.” The diamond on her finger caught the light. It was identical to the wedding band I’d lost. My body went cold. No. Matteo was just a low-level enforcer. A foot soldier the Family occasionally trusted with small operations—dock shipments, backroom gambling, nothing more. When did he become a Don?

After being reborn, I secretly switch the man I want to marry the most to the useless scion who loves flirting with me that lives next door. My dad, who's a high-ranking military colonel, is quite surprised by my choice, but he respects my wishes. In my past life, when Dad asked who I liked the most in the entire neighborhood, I had written down Damian Conrad's name. He nodded and told me, "This man has contributed greatly to the country despite only joining the army for three years. His future will definitely be a bright one. "A man as just and fair as him will undoubtedly be a good man who takes good care of his family and stays devoted to them." Dad immediately arranged for the two families to meet. Everyone thought that it was a rare and fated union. Our wedding was very grand and high-profile. Most of the people living in the military base came over to celebrate our wedding. But Damian set off for the frontier half a year after our marriage, with the excuse of wanting to contribute to the country. Not only did he leave me behind to take care of my in-laws on my own, but he also cut off all contact with me when Dad was severely ill. When I was finally done dealing with Dad's funeral matters, all I received was the bad news of Damian's death at the frontier. Crushed by the devastation and despair of the news, I fell into severe depression. Soon, I took my own life by jumping off the building. After my death, my soul refused to fade away at all. 40 years later, an elderly man and woman with graying hair showed up before my grave. With an arm around Heidi Myers' waist, Damian paid his respects to me at my grave. "It's my fault for lying to you back then, Carla. But Heidi doesn't have much time to live, so I can resort to desperate measures. Please let everything go and stop pestering her, Carla. If you really are resentful, feel free to come at me instead." It turns out that Damian loved Heidi this much that he was willing to fake his death just to trick me. But at the same time, they were so superstitious that they thought I was the one pestering Heidi, causing her to be afflicted with a terminal cancer. Now that I found out about the truth, I finally let my obsession go. When I open my eyes again, I realize I've returned to the day Dad asks me who I want to marry the most.

“Shh, little girl,” he growled, teeth catching my bottom lip. I fought the moan, but he circled my clit, my hips jerked helplessly against his hand. Then he pushed my panties aside and sank two thick fingers inside me. I soaked his palm, knees buckling as tremors wracked me. “That’s it, cum for me,” he whispered against my ear. I did. Waves crashed through me while he held me up, stroking gently, murmuring filthy praise that made it sweeter, deeper, more shattering than anything I’d ever felt with a woman. I’m a lesbian. I’ve always known it, claimed it shamelessly. I’ve mapped women’s bodies with my mouth, hands, loving every touch and gasp. My best friend’s tongue between my legs has made me come countless times. The only man I tried, my ex, was awkward, unsatisfying. I swore off them forever. I love women. I love my best friend. So why does this man, her father, the one I should never want make me wetter with one stroke than she ever has? Why am I aching for his cock, pushed inside me, thrusting relentlessly, filling me, ruining me in ways no woman could? Why does bending over his desk for him feel like the right thing to do? One forbidden touch. One devastating truth: I might never want another woman again. When I rejected the vice chancellor's advances, my best friend's obsessive aunt, she threatened expulsion. My friend took me to her father, the college owner. One look at his body and I was lost. That night in their home, hiding in the kitchen while watching him cook, I touched myself, craving what is forbidden. Will my best friend discover my sudden addiction to her father? Will her aunt ever stop wanting me?