School Fling Anthology: Class Is in Session

by Jessica Wood

She leaned down and kissed my lips tenderly. I moved my arms around her and pulled her closer to me. The warmth of her body seemed to shield me from all the unhappy memories from my past. I eagerly kissed her back, wanting to taste all the sweetness her lips had to offer.

  As our kiss deepened, my hunger for her grew. My hands moved frantically up her back and grabbed her hair at the nape of her neck. Suddenly, she pulled away, and I thought I had hurt her.

  “What’s wrong?” I looked at her, searching her face for any signs that she was in pain.

  “Why do you sleep around with so many girls?” I could sense a hint of concern in her voice.

  “Because I can.” I had been completely caught off guard by her question and responded without thinking. But as soon as I saw the hurt on her face and felt the stiffening of her body, I knew I had said the wrong thing. “But with you…” I jumped in immediately, trying to salvage things. “With you, it feels different.”

  “What do you mean by that?” I could tell she was surprised by what I’d said—and probably happy that I’d said it.

  “I’m not sure I can explain it,” I admitted. “I’m not sure I know myself. But somehow I think I knew you were someone I would really like and actually care about from that very first day I saw you on the stairs with that old stain on your shirt.”

  There was an amused look on her face. “Are you sure you weren’t staring at my breasts?”

  I laughed. “Yes, I really wasn’t! Scout’s honor,” I said with my fingers up, giving the Boy Scouts’ sign.

  “You weren’t in Boy Scouts, were you?” She gave me a doubtful gaze.

  I laughed again. “Okay, fine. You got me, I wasn’t. But girls seem to love men who used to be a Boy Scout.”

  She rolled her eyes and got up from my lap.

  “Hey, where are you going? My lap misses you.” I tried to sound like I was just joking, but I wasn’t.

  “I’m getting a glass of water.” She looked back at me as she headed toward the kitchen. “But I’m thinking of going to bed.”

  I gazed after her, waiting for her to say something else, something that would be remotely close to inviting me to stay the night.

  But as she filled her cup with water in silence, my heart sank. She wasn’t going to ask me to stay. I got up and walked toward the door. I knew the gentlemanly thing to do was to go and hug her goodnight and thank her for a nice night, but I wasn’t sure I could bear the rejection.

  “Where are you going?” She took a sip of her water before putting it down on the counter.

  “You said you were heading to bed, so I figure that was my cue to leave.” I avoided her gaze, unwilling to let her see how angry I was.

  “Oh?” She paused for a few agonizing seconds. “I thought you could stay the night.” I could hear a glee in her voice.

  I looked up at her, saw the smirk on her face, and knew instantly that she had been playing me this whole time. She saw the understanding in my eyes and began to giggle. “Why you!” I headed toward her, and when she saw me coming, she shrieked and darted for the living room. I chased after her and grabbed her by the waist, pulling her down with me on the bed in the corner of the living room. “You were totally making me think that you wanted me to leave!”

  She started laughing uncontrollably as I began to tickle her. “You deserve it!” she screamed between her fits of laughter.

  “You’re such a tease!” I finally let go of her and lay next to her on the bed to catch my breath.

  “True story,” she agreed breathlessly. “Wow, now I’m really tired.” She looked over at me apologetically. “Sorry about teasing you, but I just couldn’t resist, especially with you.”

  I chuckled. “And why do I get special treatment?”

  “Because I like you.” I was taken aback by her unexpected honesty. From the expression on her face, I knew that she, too, was surprised by her own bluntness.

  “I’m glad you feel that way.” My voice was soft and low as I looked into her warm hazel eyes.

  She inched up toward me and kissed my lips softly. “Let’s get ready for bed.”

  I nodded.

  A few minutes later, I found myself shirtless again with my briefs on and my arms around her as I spooned her. “You’re so beautiful, Alex,” I murmured into her ear. She stirred gently in my arms.

  I reveled in the softness of her skin as I ran my hand along the side of her body. I heard her inhale sharply and felt her quiver as I moved my calloused fingers across her stomach, pulling her closer towards me. I felt her back arch slightly against my cock, and I fought back a groan of pleasure as the curve of her ass rubbed against the ever-growing erection in my briefs.

  Then, before I registered what was happening, her hand grabbed mine and she guided me up to her breast. I didn’t need any additional encouragement. I eagerly cupped her full breast and drew in a ragged breath as I felt her nipple harden against my palm.

  “God, I want to fuck you so bad right now,” I whispered into her ear.

  She shook her head gently but didn’t say a thing. Instead, I could hear her uneven breathing and noticed her closed eyes as she focused on my thumb that was encircling her hard nipple. I knew she was turned on and that made me happy. My hand moved down from her breast and toward the warmth that radiated from between her inner thighs. I wanted to see how wet I had gotten her. As my fingers moved beneath her lace panties, her hand stopped me.

  “I’m not sure,” came her raspy voice.

  “No, let me do this,” I begged. “Let me make you feel amazing. I don’t want anything else in return.” My voice was raw and hoarse as I tried not to lose control of myself with her. I wanted nothing more than to be deep inside her, but I knew she probably wasn’t going to let me do that tonight. But even if my cock couldn’t be inside her, I wanted—no, I needed—to feel her wet, velvety center.

  She did not resist when my fingers moved over her panties. I could feel her wetness through the thin layer of lace and I felt my hard cock rub against my briefs as my pelvis involuntarily thrust forward against her back. I knew she felt it, and by her moan that was in time with my thrust, I knew she’d enjoyed it. I moved my fingers underneath her panties again—this time, she didn’t stop me. I let out a primal groan as my fingers entered her silky core.

  She heaved and I felt her clench against my index and middle fingers. “God, you’re so wet,” I groaned. My cock wanted to fuck her hard, but I controlled myself. My focus was on her and her pleasure.

  She moaned and whimpered as my fingers moved in and out of her, slowly at first, but faster and deeper with each thrust. She rocked her ass rhythmically against my now rock-hard cock.

  “Fuck, you drive me crazy!” I wanted more than anything to replace my fingers with my cock, but I reminded myself that this was all about her.

  I turned her around to face me and stood over her so I could use both hands. I saw the undeniable desire swimming in her eyes and heard her pant. I smiled at how much pleasure I was giving her and how much that made me happy. I drove my fingers inside her again, and without much effort, she gasped as I curled my fingers inside her and found her G-spot. I circled the thumb of my other hand rapidly around her clit and within seconds, she began to spasm and convulse as she reached the brink of ecstasy.

  “Oh God. That was amazing,” she moaned. She grabbed my face with her hands and kissed me forcefully. “You’re amazing. Thank you.” She gave me a sleepy grin as she slid back down onto her pillow, shifted a few times, and closed her eyes, leaving me staring at her in shock with a painful erection pushing out against my briefs.

  That’s it? I wasn’t expecting sex, but as I watched her sleeping in front of me, I knew I had expected at least something. Anything.

  As I lay in the bed, wide awake and staring blankly at the ceiling, I could not believe this had just happened to me. I had just fingered a girl to the point of orgasm and got absolutely nothing in return from her. And yet, as sexually frustrated as I was, I wasn’t pissed off a
t her. I was confused because I was actually happy that I had pleased her.

  Who the fuck am I?

  A few minutes had passed and I’d finally begun to accept the fact that nothing else was going to happen tonight. I looked down at my still erect cock and knew I needed to take care of it. As I got up to head to the bathroom, I felt her shift her weight beside me as she turned toward me.

  “Just kidding,” she whispered and I saw a devious smile curl her lips. “We’re not done yet.”

  The shock I felt must have shown on my face because she began to laugh uncontrollably.

  “We’re not done?” I repeated.

  She bit her bottom lip and eyed my cock. “Nope, we’re nowhere near done,” she purred. I saw the hunger in her eyes and all the blood in my body instantly rushed down to my erection in response.

  “You fucking tease. You left me hanging and pretended to sleep that entire time.” I couldn’t believe she had pulled a fast one on me like that.

  She laughed as she pulled me down into the bed with her. “I enjoyed watching you squirm.”

  “You have no idea how pissed off I was that you left me hanging like that.”

  “I can imagine,” she giggled. “Are you pissed off now?” She pulled me in and kissed me.

  “Not at all,” I said in a low, husky voice. I saw a spark in her eyes and knew she wanted me as much as I wanted her.

  I slowly moved my hands down under her shirt and felt the warmth of her soft skin against my calloused hands. I removed her shirt and inhaled sharply when I saw her full, perfect breasts. “Fuck. You’re so hot.” I felt her shiver against me, and she pulled me in for another kiss. Her lips were sweet and supple as they gently planted kisses on my face and across my neck. Her breasts drove me crazy as they crushed against my naked chest. When I felt her hot breath against my ear, I felt my cock grow harder in response, needing to be deep inside her.

  My lips and tongue, working in unison with one another, began to roam the hot spots around her neck and her ears. There were five defined freckles that dotted the edge of her collarbone. I traced them with my lips, sending shivers down her body. I saw goose bumps appear on her soft skin, waking up from their slumber, cheering me on as I explored more of her skin.

  I moved down toward her breasts, wasting no time as I took one of them into my mouth. My tongue eagerly circled and licked her hard nipple. I heard her whimper as she arched her hips up toward me and my pelvis instinctively thrust downward to meet her. I let out a primal groan as she brushed against my cock that was desperately pushing out against my briefs.

  “God, I want you inside me,” she begged as I pressed my cock against her panties. She grabbed my face and kissed me hard, her soft, wet tongue sending electric, hot shockwaves through my body, intensifying the growing throb of my erection.

  “You have no idea how much I’ve wanted you to say that.” My voice was hoarse and low. “Let me take off your panties.” I gave her a sinful smile and I saw the growing need glisten in her eyes. I moved down her body with my lips. As I explored the soft curves of her body, I could feel her chest heave up and down as her breathing became more ragged and heavy. As my lips reached her inner thighs, I gently removed her panties and my breath caught as I saw her wet pussy, ready and waiting for me to be inside it. When my nose registered her intoxicating scent, I felt my rock-hard cock throb in pain. She smelled sweet and inviting, like fresh dew on a spring morning. An overwhelming urge to taste her came over me as I inhaled deeply. But I pulled away, reminding myself that I didn’t go down on girls.

  It wasn’t until I pulled away from her that I noticed the thin strip of hair above her pussy. That’s my girl. A landing strip. “Do you know how fucking hot you are?” I groaned. I pulled down my briefs, allowing my cock to spring out, and watched her eyes widen when she saw it. She sucked in a breath and bit her bottom lip, hard, and she reached for it. I threw my head back as her soft hand moved up my shaft. “Fuck, you’re driving me crazy. We need a condom now before I explode.”

  Her hand stopped moving suddenly and I looked at her.

  “What?” Then her expression changed, like she just remembered something. “Oh, I do have condoms…but they’re the Trojan Magnum Ecstasy condoms I got as a gag gift.”

  I laughed and motioned down to my long, stiff cock. “I don’t think I’ll have a problem with that.”

  Her eyes darted to my large erection and I saw the want in her eyes.

  “Where is it? I’ll go get it.”

  “In the top drawer.”

  I got up and opened the drawer. Not only did I see the packet of condoms, I also saw something else I recognized. I pulled it out and showed it to her with a smirk on my face. “This looks familiar.”

  She looked up at me and saw the pink fuzzy handcuffs in my hand. “Oh, that was a part of a gag gift my friend gave me with the condoms.” She blushed a hue of cherry plum.

  I licked my lips and gazed at her lustfully. “Well the condoms aren’t a gag gift anymore, are they? Let’s convert the handcuffs too.”

  I watched her reaction, wanting to see how kinky she was willing to get. She blushed a deeper red and giggled. But to my surprise, she put her wrists together in front of her and said, “Why not?”

  “You never cease to amaze me, Alex.” I secured the handcuffs on one of her wrists. “Are you sure? Because you’re playing with fire when you let someone like me have free reign over your body.”

  She gave me a sinful smile and nodded. “Very sure. I’ve told you before—I like playing with fire.”

  I didn’t wait for any more encouragement. I moved the handcuffs over the middle bar of her bedframe at the head of her bed and secured the other cuff onto her other wrist. With her hands raised above her head, I moved on top her body and slipped on a condom.

  I looked down and admired her naked body. “Baby, I’ve been waiting for this moment for weeks now.”

  “Me too,” she moaned as she arched her hips up toward me.

  I lowered my body on top of her, purposely rubbing my erection along her inner thigh but never entering her. She struggled with the handcuffs that held her hands above her head as she writhed under me and tried to move her hips up to meet me. I watched her squirm with great pleasure and felt a surge of power from delaying the gratification she desperately desired. I wanted to tease her, to make her feel half the agony she had put me through in the past month.

  It took all of my willpower to resist the urge to thrust into her with all that I had. I leaned down and buried my face into the base of her neck. The uneven rasp of my breathing blew through her hair as I positioned my cock in between her inner thighs, pushing the tip against the entrance of her warm, wet pussy. “How much do you want it, baby?” I growled into her ear.

  “I want you now,” she whimpered. “God, please.”

  I lifted my head and looked into her eyes. I wanted to see her reaction when my cock was inside her for the first time. She looked up at me, her eyes filled with molten hot intensity, begging for me to satiate her. I let out a primal groan as I entered her, pushing the full length of my cock into her sweetness. She screamed and I felt her body expand for me as her muscles tightened around me. I drove in and out of her, deeper and faster with each thrust, in time with her gasps and cries.

  After several minutes, I began to spasm as an onslaught of intense pleasure I’d never experienced crashed through my body. I jerked my head back uncontrollably as my muscles tensed.

  “Fuck, I’m about to come, Alex.”

  I opened my eyes and saw her face twist in pleasure, but I knew she wasn’t close to coming yet. Against all reason, I stopped and pulled out of her. I knew if I’d stayed inside her another second, I would have exploded in her and experienced one of the most intense orgasms I’d ever had.

  Why the fuck did I just pull out?

  I knew the answer.

  She was right in front of me. The beautiful woman that made me want different things, that made me want more. As much as
I’d tried to ignore it and fight it, I knew I wanted her to climax first.

  “Did you come?” she asked.

  I shook my head. I was panting as I crouched over her lower body, trying to focus on anything else but her naked body. I needed to steady my erection and delay my orgasm. I could smell her sweetness emanating from between her inner thighs, and for a split second, I wanted to plunge my tongue into the depths of her silky wetness, to drink her intoxicating essence.

  “But why did you pull out then?”

  “I want to watch you orgasm first.” I looked up at her and there was a spark in her eyes.

  “Can you remove the handcuffs? I wanted to hold on to you when I come.”

  I chuckled. “You just want your way with me.”

  “That too.”

  When the handcuffs came off, she stood up and pulled me up. I groaned in pleasure when she moved her leg over my lap and straddled me as I sat on the edge of the bed. She gasped as my cock disappeared deep inside her. Her nails dug down my back as she violently rocked her hips up and down my erection, slowly at first, but with more force and speed each time I entered her.

  “Oh my God, Damian. I’m about to…” she whimpered as her breasts bounced wildly against my chest. But before she could finish her sentence, her body began to heave and convulse in my arms as she arched her back in pleasure.

  “Come for me, baby,” I commanded as I plunged deeper inside her, pushing her off her precipice of ecstasy.

  As her muscles tightened around my cock, my body convulsed uncontrollably as I reached the edge of my own orgasm. “Fuck! Damian!” she cried as her nails dug deeper into my back. When I heard her scream out my name in the throes of pleasure, my whole body was consumed with a high I’d never experienced before, and within seconds, we crashed together into the abyss.

  We collapsed into each other’s arms on the bed. Alexis looked over at me with a wide grin on her face. “That was—”

  “—fucking amazing,” I finished for her. I pulled her into my arms, and within minutes, we both started to drift off. Just before I slipped into a deep sleep, I whispered, “God, Alex. I can never get tired of making love to you like that.”