If anyone knew what I was doing they’d think I was crazy — but I didn’t care. I needed to get this done and Kyle was the perfect guy to do the job.
Kyle and I had grown up on the same street where we played for hours on end. We’d play hide and seek, ride our bikes, have water gun fights and campouts in the backyard. I remember changing my T-shirt in front of him after we jumped in the lake and he didn’t even bat an eye. Granted, I had nothing to show at the age of 7, but still. We were uninhibited in each other’s presence — completely and utterly comfortable and vulnerable without even realizing it.
But those seemed like such distant memories now. That was when we were young and carefree. Now we were both seniors in high school and we had an image to uphold. Well, Kyle did. He was lucky enough to be in the “popular” crowd. He was always naturally athletic, focused, and determined. I’d never known him to give up on anything in life. His deep dimples, whispie blond hair, and blue-ish gray eyes secured him a position as one of the school’s biggest heartthrobs.
And then there was me. Awkward, a little chubby, with pencil straight hair and zero clue about applying make-up or pouting my lips. I had a small group of friends. I wasn’t a total loser but I wasn’t getting invites to the Homecoming after-parties, that’s for sure.
Kyle and I didn’t really talk at school. No one knew we’d grown up as best friends. He wasn’t cruel or nasty — not like some of the other assholes in his circle of friends. He was kind and humble. He’d wave to me in the hallway or make small talk in the lunchline. He never bullied me and never seemed embarrassed by our friendship.
Perhaps it was because he remembered our pact. The pact we had made when we were 13 years old and shit started getting weird. Our bodies were changing. Our friends were telling stories about first kisses and rounding the bases. Kyle had a girlfriend in middle school who let him feel her up. I never had any boyfriends and worried I never would. It was at that moment that Kyle and I made a deal — if either of us was still a virgin by graduation, we’d be each other’s first.
I don’t know if either of us thought we’d actually collect on our agreement, but as graduation and prom night grew near, I needed a plan. I had just started dating a new boy named Bobby and we were renting a hotel room after prom. I wasn’t sure what was going to happen but I did know that I wasn’t about to embarrass myself. I wanted to be prepared. I had no idea what sex felt like. Sure, a few guys had awkwardly fingered me in the movie theater and on the ferris wheel at the county fair but sex was different. Wasn’t it?
I sat impatiently on my bed, tapping my foot and trying to control my breathing. Just when I began to doubt Klye was coming, I heard the familiar sound of the ladder hitting my windowsill. It was how he had always come to my room. I rushed over and pulled open the window just as Kyle’s hands wrapped around the edge, pulling himself inside.
I stepped back, giving him room to enter and stand up. He was wearing his red basketball jersey, jeans and a backwards hat. I anxiously played with the bottom of my T-shirt, suddenly very aware that I wasn’t wearing a bra.
“Hi”, I said nervously.
“Hi,” he said, sounding much more confident and relaxed than I expected.
When I told Kyle I wanted him to come over and take my virginity, he didn’t even flinch. Was it because he was such a sex God that this was just another notch on his belt? Or was it because he was a good friend, who made a pact, and was keeping his word?
We stood there for a moment just staring at each other. Then, without thinking, I blurted out, “Did you bring a condom?”
He reached into his pocket and pulled out a shiny blue package, looking up at me with a grin and a wink. Wow, okay, so we were really going to do this.
I nodded at him. “Good.”
He walked past me and plopped himself down on my bed. Kyle had been in my room more times than I could count but somehow this time was different. Something was actually going to happen. He was going to see me naked. I instantly felt a wave of nausea come over me.
“Maybe this was a bad idea,” I said as the anxiety rose in my stomach and up into my throat.
Kyle reached up and grabbed my hand, pulling me down to sit beside him.
“Carly, relax. It’s me.” His voice was calm and kind.
I instantly felt a sense of relief. He’s right. He had been my best friend forever and if anyone was going to see me naked for the first time, it might as well be him
Without thinking and before I could change my mind, I swiftly lifted my T-shirt up over my head, exposing my perky tits. I kept my eyes closed, afraid to see Kyle’s reaction. When a few moments of silence passed and I couldn’t take the suspense any longer, I slowly opened one eye at a time. Kyle was sitting in the same position, just staring at me — a mix of surprise and, was that excitement in his eyes?
He looked down at my body with desire. I felt a rush of excitement come over me and my nipples began to harden. I bit my lip and squirmed slightly in my seat, feeling suddenly vulnerable.
Kyle’s hand slowly rose up and extended toward my breast.
“Can… I.. touch them?” His voice was shaky and unsteady.
I nodded, appreciative of his respect and manners.
His hand felt foreign on my skin. His left palm slowly caressed my right breast in small circles. He squeezed it tenderly and I flinched.
“Did I hurt you?” He moved backward, sounding remorseful.
I quickly reached down and grabbed his hands in mine.
“No!” I reassured him. “Not at all. Actually…”, I continued, “It feels nice.”
Kyle moved his body in front of mine, as I laid back onto the bed. Both his hands slid slowly up my torso, cupping my small breasts. He kneaded them firmly. My nipples perked as his fingers grazed them affectionately. I was actually surprised by just how good it felt. Other boys had touched my tits through a bra but not like this. They were eager and rough and impatient. Kyle’s touch was gentle and soft.
I felt the heat begin to collect in my belly, as it moved down between my legs. Kyle crawled farther onto the bed, forcing me backward onto the pillows. He was between my legs now, his mouth on my body. He kissed my stomach and the round edges of my breasts. My hips instinctively pressed upward into his crotch. I could feel his growing erection through his jeans. I pushed harder, pressing my clit against the hard shaft in his pants. His kisses became more eager and deeper — he sucked my left nipple into his mouth while twirling the other one between his fingertips. I let out a small moan. His hips grinded back toward me, our bodies moving in rhythm together. My clit rubbed against my jeans, spreading my pussy lips open.
Kyle sat up and removed his hat and shirt. His chest and stomach were toned and hairless. I reached up and traced the lines of his pecs and abs. He straddled me, unbuttoning my shorts and sliding them down onto the bedroom floor. I reached up to unbutton his jeans, lowering the zipper and pulling his cock free. I’d never seen a dick up close. I’d felt a few but they were never this hard and it was always dark. It looked as I expected and I was shocked by my sudden urge to put it in my mouth. I’d never given head before but practiced on my hairbrush a few times.
I sat up slightly, leaning downward to get within reach of the tip. I licked the drops of precum that were pouring from his tiny hole. He let out a deep-throated grunt. I was overcome by excitement at the thought of pleasuring Kyle. There were at least a dozen girls from school who would die to be in my position right now — but they weren’t. I was. Kyle had chosen me.
With that thought, I drove his dick into my mouth, grabbing the base of the shaft. I engulfed his entire shaft in my mouth, licking and sucking the soft, tight skin. He held my hair back, watching and moaning. I continued to suck and lick him as he drove his hips upward, wanting to go deeper. I gagged slightly and felt him pull out of my mouth.
“Shit, I’m sorry.” There was that same apologetic tone.
I smiled, pulling him back toward me. I shoved his cock back in my mouth without hesitation, this time grabbing his balls simultaneously. Kyle’s body relaxed as he let me ravish his cock and balls. I was better at this than I thought. Apparently, too good. Kyle pulled out again but this time to stop himself from cumming.
I laid back down, and traced the lines of my tits and stomach with my fingertips.
“Where’d that condom go?” I asked teasingly.
Kyle fumbled for his jeans and removed the package, tearing it open eagerly. I watched as he slid the clear rubber over his erection which stood straight up toward the ceiling. I was ready. My nerves were now nonexistent. I wanted Kyle to fuck me. I wanted him to be my first.
I spread my legs wide, making room for him. Kyle leaned down and kissed my pussy gently before pulling himself upward, supporting his body over mine.
“Are you ready?” he asked, grinning down at me.
I grabbed the sides of his body and nodded my head.
I braced myself as I felt Kyle guide the tip of his cock into my hole. I was shocked by how wet I was and how easily it broke the barrier of my virgin pussy. I gripped his body tightly. It was a strange combination of pleasure and a burning sensation.
“Are you okay?” he asked before going any further.
“Yeah, yeah, I’m good”, I reassured him — and myself.
Kyle thrusted inside me a little deeper and I felt a sudden rush of pain. I squeezed his arms tightly and let out a tiny cry. His body tightened and he froze completely.
“Carly!” Concern filled his voice. “Do you want me to stop?”
I shook my head vigorously.
“No, no, I’m okay. Keep going.” I’d come this far, I wasn’t about to turn back now.
I braced myself again as Kyle’s dick made the final plunge into my tender cunt. I laid still, becoming accustomed to the feeling of a cock inside my body. It felt like an uncomfortable, awkward pressure. Kyle didn’t move — just stayed in one position, letting my body acclimate.
I nodded and let out a heavy sigh.
“Okay, keep going.”
Kyle nodded in agreement and moved with slow, short motions. His shaft slid in and out of my tight hole. The burning subsided slightly as my pussy welcomed the unfamiliar object. I could tell he was holding back grunts and moans. It felt good for him and that thought alone heightened my pleasure.
Despite my discomfort, I pushed my hips upward an inch further until I felt his balls graze the lines of my ass.
“Oh God,” Kyle was trying so hard not to climax. I held him tighter and widened my legs. The sounds of his pleasure were getting me increasingly excited.
I pulled his body closer, matching his movements with my own.
“Fuck, Carly…” he breathed evenly, trying to control himself, “You’re so fucking tight. It feels too good.”
I let out a sigh of satisfaction and pleasure. Kyle was fucking me and it felt amazing. My desire overcame the pain and burning and I wanted him to cum. I wanted to make Kyle cum inside me.
“It’s okay,” I reassured him, “Keep going. Fuck me until you cum.”
And with that, he did. Kyle let out the loudest grunt yet and began fucking me hard and fast. I held his body tightly as he shook and trembled after just a few more strokes. I reached up and muffled his moans beneath my hand. I didn’t want to wake my parents.
Kyle’s body slowly relaxed and he lowered himself on top of me. I rested my chin on his shoulder, enjoying the sensation of his dick still inside me.
“I’m sorry,” I heard him say into the pillow beside my head.
“Sorry?” I asked, confused. “For what?”
“You didn’t finish,” he said, sounding mournful.
I couldn’t help but laugh.
“Girls never finish the first time,” I reassured him. “It hurts too much.”
Kyle pulled his body upward, looking down at me with a look of utter horror.
“I hurt you?” He sounded crushed.
I reached up and grabbed his face.
“No, you didn’t hurt me. I mean, well, it’s just uncomfortable and burned a little bit. But it was great! Perfect, in fact. Thank you.” I smiled affectionately at him, then continued. “I hear it gets better for girls every time they do it.”
A look of determination came over Kyle’s face.
“Okay then,” he said, sounding determined. “Then I guess we’ll just have to keep trying until it feels good.”
I was shocked and pleasantly surprised by his statement. I smiled up at him with admiration but before I could speak, a huge grin spread across his face.
“But, in the meantime…” he slid back down onto his stomach, propping his face directly in front of my pussy. “I don’t accept unsatisfied customers.” And to my delight and surprise, Kyle buried his face in my cunt.
I couldn’t let her down. I was standing in my bedroom, giving myself a pep talk. I looked in the mirror, running my hair through my hair before pulling my hat snuggly in place. I’d had sex before. It wasn’t like this was my first time but this was the first time it mattered. Carly was counting on me. She was sweet and vulnerable and I didn’t want to fuck this up. Every girl remembers their first time. Don’t they?
I guess you could say my relationship with Carly was complicated. We’d grown up together. We were the best of friends. But that was 10 years ago, back when status and looks didn’t matter. Back before there were jocks and nerds and stupid fucking reputations to uphold. I really didn’t have much to complain about since I came out on top. I was one of the popular guys at school and could pretty much have any girl I wanted.
Too bad I didn’t want any of them. Random hook-ups were fine but none of them knew how to hold a conversation. All they did was giggle, twirl their hair, and pretend to know about football. Carly was different. She was never worried about what other people thought about her and that’s what I liked most. She was confident without being stuck up.
Even though we didn’t talk much after entering high school, I always kept an eye on her. Always made sure she was okay and that no one bothered her. She didn’t deserve that. She was a sweet girl. Which is why when she called on me that night to uphold the pact we’d made a few years prior, I couldn’t say no. She needed me and I didn’t want to go back on my promise.
I looked at myself in the mirror one more time. You can do this, Kyle, I thought. I straightened my hair, checked my breath, and touched my pocket to make sure the condom I’d bought earlier was still there. Check. I had everything I needed.
When I arrived at Carly’s house I saw her bedroom light was on. The ladder was resting against the siding, like always. I placed it by her window and climbed up, tapping quietly on the glass. It was late and I was sure her parents and sister were sleeping. Carly opened the window just as I made my ascent.
She was wearing a loose T-shirt and no bra. I could almost make her areolas out and was surprised that my dick reacted with a twitch. She moved backward, giving me room to stand up. I smiled slightly as she played with the bottom of her T-shirt nervously.
“Hi,” she said, not making eye contact.
“Hi,” I said, hoping to sound more confident than I felt.
I needed to be confident and in control. I had a job to do and Carly needed me. I’d been in her room more times than I could count but tonight was different. Something in the air felt different. Was it anticipation or sexual tension? I think it was a little of both.
Carly was anxious too, which is why she nervously blurted out, “Did you bring a condom?”
I reached into my pocket, pulling out the shiny blue package. I gave her a playful wink and she nodded.
I moved past her, oddly aware of the fact that she wasn’t wearing a bra, and plopped down onto her bed. Carly didn’t look at me as she continued to fiddle with the bottom of her T-shirt.
“Maybe this was a bad idea,” she said quickly.
I grabbed her hands and pulled her to sit beside me. Her skin was warm and soft. I smiled up at her.
“Carly, relax. It’s me.”
I couldn’t judge her reaction. Her face seemed to soften a bit. I think she was finally starting to relax. Any doubts I had were erased when she swiftly removed her shirt, revealing two perfectly round breasts. My breath caught in my throat. I swallowed hard. My mouth was instantly dry. Carly’s body was more beautiful than I’d imagined. Actually, I’d never really imagined her naked but now that she was sitting topless in front of me, I wondered why I hadn’t ever looked at her that way before?
I wanted to feel her.
“Can I touch them?” I asked hesitantly, my hand instinctively raising up toward her perky tits.
She smiled and nodded as my hands made contact with her skin. Like tiny teardrops, her breasts fit perfectly in my palm. I squeezed them firmly and she flinched. I jumped back, worried I’d done something wrong.
“Did I hurt you?” I asked, slightly concerned.
“No,” she said, reaching down and placing my hands back on her chest. “Not at all. Actually, it feels nice.”
She seemed surprised by how good it felt. Blood rushed to my cock as I positioned myself at the end of the bed, between her knees. I explored her soft tits, kneading them firmly and playing with her nipples. I switched from pinching to twisting them, reading her body language.
I gently pushed her back onto the bed, crawling onto the edge to join her. She moved her body back until she was resting on the pillows. As she reclined comfortably, I worked my hands and mouth down her neck and chest. She tasted sweet and smelled like crisp clean linens. My cock was throbbing now. I knew I should’ve jerked off before coming over. Too late now. Now it was all a game of control and willpower.
I felt a rush of excitement as Carly began pressing her crotch into my leg. Her pussy easily found my erection as she ground against it, gently gyrating her body against mine. I sat up momentarily, removing my hat and shirt. I couldn’t believe how badly I wanted her hands on my body. As if reading my mind, she reached up, tracing my pecs and stomach with her fingertips. Her touch was gentle but confident. My nipples hardened in unison with my cock.
I undid her jeans, sliding them down off her body. She returned the favor by unbuttoning my jeans and releasing my cock. She held it firmly in her hand, her eyes fixated on its length and girth. Her soft touch felt amazing on my raw flesh. I wondered if she knew what to do with it but before I could speak, she leaned down, taking me in her mouth.
I gasped at the sudden sense of warmth and wetness around my shaft. I held her hair back, watching her head move up and down on my tool. She licked and sucked it as if she’d done this before. I briefly wondered if she had but then realized it didn’t matter. I was here now and it was my cock in her mouth. And fuck it felt good. I moaned slightly as she continued to work the entire length of my cock. I couldn’t help but thrust forward, shoving myself deeper down her throat. She gagged, pulling me free.
“Shit,” I apologized. “I’m sorry.” I hadn’t meant to make her gag.
To my surprise and delight, she smiled back up at me, pulling my dick back into her mouth and down her throat. She sucked harder now, creating a firm seal between her gorgeous mouth and my tool. She grabbed my balls, squeezing them with just the right amount of pressure. The sensation of her hands and mouth were intoxicating and I thought I might come at that very moment. I pulled her head away, breaking contact and letting out a heavy, calming breath. I couldn’t come yet. It was too soon.
She lowered herself back down onto the bed. Her body was beautiful. Different from the stick figure girls I’d been with. She had curves and they felt amazing. She had the body of a woman. She played with her nipples, tracing her ribs and stomach with her fingertips.
“Where’d that condom go?” she asked, playfully biting her lip.
I fumbled for my jeans, finding the condom and eagerly ripping open the wrapper. It was easy to slide on since my cock was harder than ever, sticking straight up toward the ceiling. Carly watched intently, biting her lip and tickling her belly.
She spread her legs wide, showcasing her gorgeous virgin pussy. I dipped down, kissing it gently before moving between her legs. I held my weight up, not wanting to place too much pressure on her.
“Are you ready?” I asked cautiously.
She reached up, grabbed my sides, and nodded slowly. I grabbed my shaft, gently pressing the tip of my erection into her hole. She was wetter than I expected. The first inch slid in easily, without resistance. Her fingers dug into my flesh as I continued to penetrate her virgin pussy.
“Are you okay?” I wanted to make sure I wasn’t hurting her but it felt so good.
“Yeah, yeah, I’m good,” she said, her eyes closed. Her body was tense. I didn’t know how this felt for her. Was it painful?
I waited a minute before pushing into her a little deeper. Her grip tightened on my arms and her body stiffened as she let out a quiet whimper. I froze, afraid to move.
“Carly, do you want me to stop?” I asked, holding myself still.
She shook her head. “No, no, I’m ok”, she said breathily. “Keep going.”
I obeyed, giving in to my desire to fully enter her. I plunged my dick into her wetness. I paused momentarily, letting her tight vagina strangle my throbbing dick. It felt amazing. She held her breath before urging me to continue.
I pulled myself in and out of her slowly, careful not to move too fast. Her thick cream acted like the perfect lubricant. I was surprised by how wet she was and struggled not to erupt inside her. I squinted hard, gripping the pillow below her head and trying to focus on anything other than the amazing sensation between my legs. She pushed her hips upward, meeting mine and plunging my cock even deeper into her forbidden zone. My balls were touching her ass now, tickling her sensitive tight skin.
“Oh God,” the words escaped my mouth as I struggled to maintain control. Carly spread her legs even further, continuing to thrust upward, matching my movements.
“Fuck, Carly…”, I said between heavy breaths. “You’re so fucking tight. It feels too good.” I wasn’t sure how much longer I could wait. I wanted her to come but didn’t know if she would.
A strange smile was spread across Carly’s face. It wasn’t one of sexual satisfaction but more contentment.
“It’s okay,” she whispered through her pursed lips. “Keep going. Fuck me until you come.”
Her words rushed over me and I knew I couldn’t wait. I fucked her hard and fast. It only took a few seconds for my cock to explode inside her. I grunted under my breath, trying desperately not to make too much noise. Carly helped my clasping her hand over my mouth. She was smiling in delight over my body shaking orgasms.
I collapsed on top of her, my head nestled into her neck. She held me, our bodies still connected.
“I’m sorry,” I said, feeling slightly inadequate.
“Sorry?” she asked, sounding confused. “For what?”
“You didn’t finish.”
She laughed. “Girls never finish the first time. It hurts too much.”
I loved her honesty but instantly felt terrible that I’d just enjoyed one of the best fucks of my life and she was in pain.
“I hurt you?” I asked, feeling wounded.
She reached up and cradled my face in her soft hands.
“No, you didn’t hurt me,” she smiled sweetly. “I mean, well, it’s just uncomfortable and burned a little bit. But it was great!” She was really struggling to make me feel better. “Perfect, in fact. Thank you,” she said and really sounded grateful. “I hear it gets better for girls every time they do it.
I’d heard that too and suddenly, had an idea.
“Okay then,” I said. “Then I guess we’ll just have to keep trying until it feels good.”
Carly looked taken aback. I smiled wide at her. I wanted to make her feel as good as she made me feel. I wasn’t nervous or self-conscious around Carly. I could be myself and that made the sex even better.
Then, another thought came over me.
“In the meantime…”, I moved down her body, my face positioned perfectly in front of her pussy. I looked up at her with a devilish smile. “I don’t accept unsatisfied customers”. And with that, I dove my face greedily into her pussy, making quick work of getting Carly off.