Playing to Win: A Contemporary Romance Box Set

by Romi Hart

  I shrugged. “I don’t know. Ryan may have done terrible things in his past, but he hasn’t been that way with me.”

  Helena bit her lip in thought. “You may not know this. God knows everyone else does, but I thought the same thing about a guy on the football team. People warned me about him.” She glanced at Gloria, who nodded in agreement. “But, I was convinced he was different with me. He told me he was a changed man.” She crossed her arms, looking out the window, her dark hair fell into her blue eyes that were brimming with tears.

  Gloria put an arm around her. “Oh, Helena!”

  Helena wiped her eyes. “I was humiliated. I don’t want the same thing to happen to you.”

  Naomi absently pulled on her curly ponytail. “How can we figure out if Ryan is for real or not?”

  Looking down into my Flat White, I admitted sadly, “I don’t know.”

  Naomi twirled a curl in her finger. “I wish there was some way, where you could test guys to figure out if they’re being genuine.”

  Gloria shrugged. “Hook him up to a lie detector test?”

  Naomi blew a raspberry. “We could hire a fortune teller?”

  Helena sat up, her eyes glinting in thought as she scanned the ceiling. She then looked at me with a serious look on her face. “We could test him, in a challenge of sorts. If he fails, then we know what kind of guy he is.”

  "What do you mean? How?" I was curious about what Helena had in mind.

  Gloria’s eyes lit up. “Like a sting operation?”

  Helena nodded her head slowly, smiling at Gloria. “Yes!” She tapped her finger on the table. “Delta Pi is having a frat party tomorrow night. Is Ryan planning on taking you?”

  I shook my head. “No. He hasn’t mentioned it.”

  Helena shook her head with a dramatic eye roll. “He hasn’t even mentioned it to you? It’s Delta Pi’s Toga party. It’s the party of the Fall semester.”

  I shrugged. “We don’t really go out much. We watch movies.”

  Gloria’s eyes opened in surprise. “Sorry, but that sounds like a red flag to me.”

  Helena vehemently agreed, “Total red flag.” She shook her head in disdain, “As soon as we find out the true Ryan Romero, he will be out of your life and you can move on to a nice guy, who will take you out places, like the biggest party of Fall term.”

  Was it really a red flag? I was more of a homebody anyway. I liked that Ryan and I didn’t go out to parties together. And who said he didn’t take me out places? He had just taken me to the pier the night before.

  Helena leaned in. “If Ryan asks you to go, say you’re too sick and stay at home. Leave the rest to me.”

  Gloria persisted, “We don’t want you wasting a single minute on this guy if he’s really a douchebag.”

  I looked to Naomi, whose eyebrows were crinkled with distress. “We don’t want you to get hurt.”

  Helena sighed deeply. “That’s the last thing I want to happen to you. Take it from me, it’s devastating to trust someone that will just turn around and betray you.”

  I thought about Ryan and all the nights where we just cuddled on the couch. Was it too good to be true? Was he really a bad boy underneath all of his perfect gentleman exterior?

  Looking at Helena, I said, “Okay. I’m game.”

  My feelings for Ryan were growing. If he failed Helena’s test, I still had time to salvage what was left of my heart. I hoped she was wrong, but like my teammates said, how do you really know someone?

  12

  Ryan

  Delta Pi’s big Toga party was Friday night. In the past, I loved going just so I could take my pick of all the girls dressed in white sheets. This year, I was more than happy to miss out on all the debauchery.

  Kassie couldn’t hold her liquor and I wasn’t down to go out and party without her. If we were going to go to a frat party together, I much preferred to not go to one of the biggest ones of the year.

  But the guys on the team wouldn’t take no for an answer. After practice, in the locker room, Neil chided, “It’s our last year, man. The last year where it’s socially respectable to wear a sheet in public.”

  I unstrapped the ice bag from my shoulder. “Kassie isn’t a party girl.”

  Trent threw his cleats into his locker. “Natalie’s going.”

  “You and Natalie a thing now?” I asked.

  Trent rubbed his hand together. “Yes… No.” He paused in thought. “I don’t know?”

  I shook my head and laughed. “Good luck with that.”

  Jordan stretched out his hamstrings. “Just bring her, Romero! Come on!”

  Neil nudged me. “Don’t you want to see her draped in a sheet?”

  I sighed. Kassie would definitely look sexy in a toga. Thoughts of her blonde hair down on her bare shoulders invaded my mind.

  Pulling out my phone, I put a hand up. “Okay. Let me call her.”

  Trent hit me on the back of my head. “Attaboy!”

  As the phone rang, I held a finger to my lips to shut them up.

  "Hi, Ryan." Kassie's voice sounded muffled.

  I rotated and stretched my shoulder. “Hey. You want to go the toga party tonight? I wasn’t planning on going, but I have a sheet at home with your name on it. We don’t have to drink either.”

  Kassie coughed. “I’d love to, but I’m sick!”

  I turned away from my friends who were staring at me. “Oh. You want to come over then? I can make you some soup. We can watch that new horror series on Netflix. It just came out today.”

  Kassie coughed again. “No. You should go without me. The toga party sounds fun. I don’t want you to miss out.”

  “Miss out? No. I don’t care. Let me pick you up.” The guys crowded around me, shaking their heads vigorously. I pushed them away from me.

  Kassie was persistent. “I’m already in my pajamas and in bed. I just need a good night’s sleep.”

  “Okay. Tomorrow then? Can I pick you up tomorrow morning?” I was disappointed I wouldn’t be seeing her.

  “Sure. Call me in the morning,” Kassie said sleepily.

  “Okay. Good night.” I hung up the phone to the guys cheering.

  “All right, Romero! We get our old Ryan back for one night!” Neil howled.

  We hadn’t had a guys’ night in awhile anyway ever since I’d met Kassie. It was our last year together. As much as I wanted to see Kassie right then to check on her, I’d see her in the morning.

  After running back to my place for a quick shower and dinner, I met the guys at Delta Pi. The festivities were already in full gear. As expected, there were hot girls all over the place, wearing toga gear. Some were dressed in white bikinis. How bikinis were related to togas, I was unsure, but no one was complaining. I was in a sheet lazily slung over my shoulder and held in place with a belt at my waist.

  Trent and Natalie were happily talking together in a corner. It looked like things were going well.

  Jordan handed me a cup of beer. “I’m glad you came.” He held up his cup in a toast.

  “To our last year.” I tapped my red plastic cup with his.

  Sipping the beer, I noticed some of the cheerleaders were at the party. Seeing them made me think about Kassie. I hoped she was okay. Pulling out my phone, I tapped on her name to text her, but hesitated. She said she was going to sleep. I thought better of bothering her. She probably needed her rest.

  I sighed and pushed my phone back into my pocket. When I looked up, Jordan was talking to a girl in a white bikini. Her friend, also only in a skimpy white two-piece, stood nearby eyeing me with bedroom eyes. Not wanting to interact with the girl, I scooted away to an empty corner.

  From across the room, the white bikini girl kept smiling at me. Before, I would have swooped that girl up in a snap. I might have even taken her to a room upstairs for a quickie. That night, I was completely uninterested. Not picking up my indifferent vibes, the bikini girl started to totter her way over to me with determination in her eyes.

  Sh
it. I spun around to find my exit. To my left, I saw Helena gliding towards me.

  Bikini girl or Helena?

  At least I knew Helena so I stepped towards her, stopping the bikini girl in her tracks. Phew.

  Helena had on a gold laurel crown in her black hair. She wasn’t wearing a sheet but had on a white gauzy floor length dress. I always thought Helena was beautiful. It was a shame that running back had treated her so poorly.

  Helena smiled, placing her hands on my chest. “Ryan!”

  This was completely unlike the Helena I'd known since freshman year. She was much too reserved to throw out touchy-feely greetings.

  “Hi, Helena,” I said, taking a step back.

  Helena immediately stepped forward. “Are you having a good night?”

  Shrugging, I looked around. “Honestly? After three years of this, it’s kinda getting old.”

  Helena wrapped her arms around my neck. “I completely agree. You want to get out of here? Somewhere where we can be alone?”

  Okay. This was crazy. Helena never ever came on to guys so boldly. Plus, I knew that she had an anti-athlete dating mantra. Something wasn’t right.

  I pushed her away. “Thanks, Helena, but I’m good. I think I’m just going to head out.”

  Her face looked genuinely surprised. The bikini girl’s face lit up, watching me hurry away from Helena. I needed to get out of there fast.

  As I walked to my car, Helena’s behavior unsettled me. It was so unlike her usual character. Whatever the reason, I needed to tell Kassie right away. Lots of people were at that party. I couldn’t risk anyone getting the wrong idea and telling her something that was untrue.

  I drove to Boyd Hall and parked outside. Still, I couldn’t shake Helena’s weird behavior. She’d never shown any interest in me before after all the years of knowing each other. Suddenly, a horrible thought came to me.

  Was I being set up? Kassie was so sweet natured. She’d never do something so dishonest, would she?

  With my heart racing, I called Kassie.

  She answered after a few rings. “Hello? Ryan?”

  “Kassie, I’m outside. I need to talk to you.”

  I could hear her getting up. “Okay. Is everything ok?”

  I got out of my car and started to pace. “I just need to talk to you, please.”

  She took in a sharp breath. “I’ll be right out.”

  In minutes, Kassie walked up to my car in her pink pajamas and a robe. She hugged me. “You okay? Is everything okay?”

  I pulled away from her, holding onto her hands. “Something really weird happened tonight.”

  Kassie shook her head. “What happened?”

  Still in disbelief, I said, “Helena Baker came onto me.”

  Kassie pulled away. “Then what happened?”

  “What do you mean? Nothing. I left and came straight here.”

  Her face brightened. “Really?” She threw her arms around me. “I knew you would pass the test!”

  I pushed her away. “Test?” Turning away from her, I mulled over the night’s events. I knew there was no way Helena was suddenly interested in me.

  I turned back to Kassie. “How could you set me up like that?”

  Kassie hugged herself. “They were telling me how much of a player you were. How you were going to hurt me. It was a stupid thing to do. I’m sorry.”

  Seeing her face full of regret, I put my arms around her, pulling her in close. “No. I get it. I get why you did it, but it still hurts that you don’t trust me.”

  Kassie began to cry, burying her face in my chest. “I’m so sorry.”

  With my finger, I raised her face to look at me. “I’ve never felt this way about anyone in my life. I know I have a reputation, but I would never hurt you.” Looking into her face, I realized she didn’t look sick at all. “Are you even sick?”

  She shook her head slowly. “No. All of it was a lie.”

  That stung me. Worried, I asked, “What about this? Us? Is that a lie?”

  Kassie shook her head, tears falling from her face. “No. I care about you so much, Ryan. That’s why I was so scared. That’s why I wanted to see if you’d pass that stupid test.” She threw her head into her hands. “I was so stupid. I’m sorry I lied. I never meant to hurt you.” She looked up at me sadly. “I just didn’t know how you felt about me.”

  I held Kassie against my chest, feeling her body rise and fall in heaving sobs. "I care about you so much," I spoke softly into her ear. "Please don’t cry. Will you stay the night with me? Do you think you’re ready?”

  She looked up at me with a tear streaked face and without hesitation whispered, “Yes. I’d love to. I’ve never been more ready.”

  13

  Kassie

  Was there a doubt in my mind that Ryan would fail Helena’s test? No. But, I’d gotten swept up in my teammate’s plans. A small part of me wanted to prove to everyone that Ryan was as genuine as I knew him to be.

  When he asked me to go back to his place, I was more than ready. The test was stupid and dishonest, but it solidified in my mind and my heart that Ryan Romero only had eyes for me.

  I looked down at my pajamas and robe. “Should I go in and change?” I giggled.

  Ryan pulled me close to him. “No. You look beautiful just like this.” He kissed me on my lips, brushing my face with his fingertips. “Are you sure you’re ready?”

  I hugged him, breathing in his sandalwood and ginger scent. “Yes. I’m ready.”

  He looked into my eyes and kissed me again. “Let’s go or I’m not going to be able to control myself. I might take you right here.”

  I giggled at the thought, wanting Ryan just as badly. A dirty thought jumped into my mind imagining Ryan propping me up on the hood of his car and ravaging me.

  On the ride to his place, I ran my fingers through his thick hair, something I loved to do because it made Ryan squirm. I could see his crotch rising and getting bigger, exciting me.

  I was finally going to turn in my V card, and it was going to be with someone I really cared about it. My best friend in high school, Monica, also a cheerleader, lost her virginity our junior year. She urged me to just get it over with like she did with Mario, a basketball player on the varsity team.

  Losing my virginity was not something I wanted to get over with. Frankie, my only boyfriend in high school, and I never got to the point of me considering losing my virginity to him. Plus, I was too busy in high school with my gymnastic lessons, AP classes, cheerleading, and ECO Club. We barely even made out.

  I was glad I hadn’t listened to Monica and waited for the right person to come along. My first time was going to be special with someone I cared about and who cared about me. Monica and the basketball player hadn’t even really dated. She was determined to lose her V card, and Mario was just the lucky guy she picked. My first time was going to be different.

  When we got back to Ryan’s place, I was a bowl of jellied nerves. I wanted him, but I didn’t know what to expect. Plus, I was afraid of the pain. Ryan led me to his bedroom and sat me on the bed.

  He threw off his toga sheet, revealing his muscular chest and torso. All he had on was dark grey boxer briefs. OMG. Ryan was smoking hot.

  I fidgeted with the comforter and looked down at my feet. “I’m scared,” I whispered.

  Ryan knelt down in front of me, brushing my hair out of my face. “We can take it really slow, okay?”

  I smiled at him, nodding. “Okay.”

  He slipped off my pink robe, kissing me. He carefully unbuttoned my pajama top. His fingertips lightly brushed my chest sending tingles throughout my body. He pushed the pajama top down off my shoulders. I always wore bralettes when I slept and that night I had on a lacy baby pink bralette on.

  Ryan kissed down my neck to my clavicle. His fingertips stroked my back gently, once again making my spine tingle from his gentle touch. Slowly, he kissed me further down from my chest to my bellybutton.

  With his teeth, he pulled the drawstrin
g of my pants. He looked up at me with a boyish grin. I giggled as he slipped my pants off down to my ankles. He then grabbed the pant legs and tugged like a magician. “Abracadabra! Now! You have no pants!”

  I laughed again. My anxiety began to melt away. Not expecting to see Ryan at all that night, I somehow luckily put on a matching bra and panties set. Ryan looked me over. “You look amazing in pink.”

  I blushed. “It’s my favorite color.”

  Ryan laughed and furrowed his brow in thought. “No. Is it?”

  I giggled again. He was being adorable.

  He sat up on his knees, moving closer to me. “As much as I love this bra, I’d like to take it off.”

  I nodded. “Okay.”

  Ryan reached around my back, looking for a clasp. I shook my head. "It's a bralette. Here." I pulled the bralette up and over my head. My breasts spilled out.

  Ryan grabbed my right breast, thumbing the nipple. He whispered, “I learn new things every day.” He licked my lips with his tongue before slipping it into my mouth. His other hand cupped my left breast. My nipples began to harden at his touch.

  I thought of the night we were in the kitchen and wanted his tongue lapping at my sensitive fat nipples. As if reading my mind, Ryan’s head lowered. His tongue reached out and licked my right nipple, swirling around it in a circle while his other hand tweaked and pinched my left one. I moaned, enjoying Ryan’s tongue on my breast.

  Ryan looked up with desire in his eyes. “I need to take these panties off you.”

  I nodded. “Please do.”

  Ryan gently tugged my panties down, revealing my pussy that was already wet and throbbing just from kissing and my nipples being licked and tweaked. I’d picked up the habit of shaving the hair off my pussy from the girls on the cheerleading team.

  Ryan looked at my bald pussy with sex in his eyes. “Your pussy is so pretty. God. Everything about you is so pretty.” With an index finger and thumb, he opened my lips and touched his tongue to my swollen clit. Throwing my head back, I gasped from the delicious sensation.

  With his other hand, he slowly slipped in his index finger. I moaned again, watching Ryan eat me and fuck me with his finger.