Taking my chubby friend’s virginity to thank him for helping me pass the statistics exam.
I went to a small high school with a minimal sports program, so there thankfully weren’t too many big egos floating through the hallways the way there are in stereotypical American high school movies. But, being bored teenagers in a small town, we did have the occasional romantic drama as people started hooking up with each other. And, as one of the students who had an easy enough puberty and a lot of interest in getting validation about her new body, I was occasionally at the centre of that drama. It isn’t super relevant to this story, but I wanted to share that background to show I wasn’t some blushing virgin at the start of these events.
My friend James, on the other hand, was a blushing virgin, and he was extremely self-conscious about it. Although I’m sure the national average is higher, most people in our grade had started having sex by age 15 or 16, leaving James upset about his still intact virginity on the eve of his 18th birthday. I called him at midnight, sang him “Happy Birthday,” and then heard silence. “James? Jimmy? Jimbo?”
A sigh came from the other end of the line. “Another year. And I’m still a virgin.”
“Oh, my god. This again? It isn’t a big deal! You’re going to get to college and fuck girls all the time.”
“And lose my v-card to a classmate who will then tell everyone how much I suck at it? No, thank you.”
“I don’t know what to tell you, bud. We keep having this conversation. You complain about being a virgin, and I tell you it isn’t a big deal, and then we talk about it again a week later. I’m not trying to be an asshole, but complaining about it isn’t going to make any girls want to fuck you.”
A pause on the other side of the line. “Harsh, but fair.”
“It’s what I’m here for, baby boy.”
“I’m a legal adult and older than you, ass.”
Over the next couple of months, James slowly shifted his attitude. He was way more pleasant to be around because we knew he wouldn’t start whining about his virginity if any of us talked about our sex lives, and none of my other female friends felt like he was subtly trying to pressure them into pity fucking him. I helped him work on his confidence in other ways as well, teaching him how to style his hair and dress for his body type, instead of just rolling out of bed and wearing whatever oversized hand-me-downs he got from his brother.
My birthday came and went, and we were finally almost at the end of our final semester of high school. And I was going to fail statistics. James was our resident math genius, and he felt like he owed me for helping him gain enough confidence to talk to girls. He still hadn’t slept with one, but he once got a handjob from a sweet, student government nerd from our grade while sitting under the bleachers. I know this because he texted me as soon as he finished.
James came over after school every day for two weeks to help me cram a semester’s worth of statistics into my Swiss cheese brain. His patience and his kindness while helping me study without any expectation of a reward made me look at him in a way I hadn’t before. He wasn’t the same whiny kid with terrible hair, ill-fitting clothes, and no confidence that he had been six or seven months ago. Instead, he was a sweet, chubby guy with some semblance of self-assuredness who just needed someone to give him a chance.
The change had been so gradual over the last several months that I hadn’t realized that I was becoming attracted to him. He cared more about his attitude and appearance, and that made him not just less of a drag – it made him hot.
The statistics exam came and went, and James was with me when my parents got the email from my teacher letting them know I passed and could walk at graduation. I threw my arms around him, and he spun me around, my whole family jumping and screaming excitedly. Pulling away, I noticed the way his eyes stayed glued to my lips, and his hands lingered on my waist a little too long to be unintentional. But we were in my parents’ computer room, with my entire immediate family celebrating around us, and there was nothing that could be done about it.
Our friend group rented a house together for a beach week about an hour away, and James drove us over together. He parked on the side of the street and looked over at me, tension filling the air. I glanced down at his soft lips and thought about closing the distance, but the sound of knuckles rapping on the car window made us jump. “Are you guys hot-boxing?” our friend Jillian shouted, her boyfriend Tom peering into the backseat windows to see if anyone else was in the car with us.
I didn’t risk looking over at James, not wanting to see the disappointment on his face. “I’m dry, but I think that Naomi has some!” I called out as I opened the door and slid out.
Beach week was exactly as expected: days spent getting tan and high and nights spent getting drunk. On around the third day of our vacation, I was slightly sunburned and very cumulatively hungover. I plopped down in the sand next to James under a large beach umbrella, my head pounding and my body dehydrated from the combination of alcohol and daily sun exposure. “How are you holding up?” I asked him, glancing over and squinting in the punishing sunlight.
“I love the beach,” he said happily, sipping on a cold beer in a paper bag, “the sun, the waves, the beautiful girls in bikinis. What’s not to like?”
I laughed lightly, his good mood infectious, and stole a sip of his drink. “Why don’t you get out there and enjoy the water, then?”
James looked down, his cheeks getting pink. “I, uh, I don’t want to take off my shirt.”
“Why, do you have a sunburn?”
“No, stretch marks.”
“Everybody has stretch marks, James.”
“Not like I have them.”
“So what? Are you going to just sit by the ocean and let life pass you by because you’re too nervous?”
“You know,” he said angrily, grabbing his towel and shaking it roughly to get the sand off, “not every conversation with you has to end in a truth bomb.”
He stormed back to the beach house. “James, wait!” I called out, but he didn’t turn around.
I gathered my things and jogged after him, the hot sand burning the soles of my feet. I didn’t catch up with him until we were in the beach house’s shell-themed living room, staring angrily at each other across the length of the couch. “Are you just going to storm away from difficult conversations?” I spat at him rhetorically.
“Are you just going to keep nagging at me until I become who you think I should be?”
“Name one FUCKING time I suggested you do something that didn’t turn out well for you.”
“That’s not the point!”
“Then what is? Why are you mad at me?”
“I don’t know! I don’t even know if I’m mad at you or if I’m just mad in general!”
“Well, that’s fucking helpful.”
James sat on the couch and put his face in his hands, groaning loudly. “I know you have just been trying to help me. And I know that everything you’ve done has been necessary and good for me. But I just don’t know why you’ve been doing it.”
“Because I want you to be happy and stop holding yourself back.”
“You know what’s stopping me from being happy.”
“Are you serious? You’re blaming this on your virginity again?”
“You don’t get it! It’s a cloud hanging over my head! It’s something I think about every morning when I wake up and every night before I go to sleep. I haven’t gone a day without thinking about it in years and feeling like everybody is laughing at me. And I’ve stopped bringing it up because I could see it was pushing people away, but I never stopped thinking about it.”
“That — that sounds awful.”
He looked over at me, surprised that I wasn’t fighting with him. I continued. “I’m not agreeing that you should feel that way, but I know what it’s like to obsess over something and feel like you can’t do anything to change it.”
“Yeah. I do, so come on.”
I took James’s hand and pulled him off the couch and towards the stairs leading to the second floor. “What are you doing?” he asked cautiously.
He was silent, and a look over my shoulder showed me that his face was flushed and his mouth open slightly, his wide eyes staring at me as I led him up the stairs. I brought him into my bedroom and sat him on the bed, going back to the door to close and lock it. I got a condom out of my backpack and tossed it on the bed. “Are you serious?” he asked breathlessly, his tongue peeking out to wet his lips.
I stood in front of him and bent down to kiss him softly, my hands cupping his face. He responded immediately, his hands gripping my waist and his lips moving urgently against mine. I kissed down his neck and lightly took his shirt hem in my hands. “Can I take this off?”
“Why are you doing this? Is this a pity fuck?”
“I’m doing this because I want to,” I said truthfully.
He lifted his arms, and I slid the shirt up and over his head, tossing it on the ground behind me. I didn’t give him time to be self-conscious, capturing his mouth again before he could think too much about being shirtless in front of me. His hands mimicked mine, pulling my pool cover over my head to reveal my skimpy bikini. His eyes darkened as he stared. “You’ve been wearing this all week, but I haven’t had the chance to see you in it up close.”
“I’m happy to keep it on if you’d like.”
I laughed and kissed him again, reaching behind myself and untying my bikini along my bra line. I detached from his lips long enough to pull the bikini top over my head, exposing my tits to him for the first time – probably the first time he had ever seen tits in person. He pounced, his hands coming up to grip them and pull them against his face as he kissed all over my chest. I took advantage of his distraction to slip my bikini bottoms down my legs. “Do you want to try fingering me?”
He nodded enthusiastically, his lips parted as he stared at my naked form. “Give me your hand,” I whispered.
He looked up at me and did as I asked, placing his right hand in my palm. I gently brought it down my body until it reached my freshly-shaven pussy, locking eyes with him as I guided his fingers to touch me the way I wanted to be touched. Directing his hand, I lightly circled my clit with his pointer and middle fingers. “That’s my clit,” I moaned, my head tipping backwards as he started to do the movements on his own, “It’s really sensitive, so don’t press too hard.”
He nodded, leaning forward to kiss my chest again and bringing his left hand up to cup my tits. “You can play with my nipples at the same time,” I suggested, “Just be gentle at least at first.”
“Can I use my mouth?”
He took my left nipple in his mouth, flicking his tongue against it as he gently played with my right nipple with his fingers. The fingers on my pussy kept up their soft circling, but he started to drift away from my clit. I gently moved his hand back to my clit, biting my lip as I looked down at him. “That’s good, James.”
He flushed with pride. “Let’s get on the bed,” I suggested, “but first you need to take off your swimsuit.”
He stood up and kissed me again, one hand tangling into my hair and the other pressing against the small of my back. I wrapped my arms around the back of his neck and deepened the kiss, sucking gently on his bottom lip. He groaned against me, his hands starting to wander over my skin.
I hooked my fingers under the waistband of his swimsuit, lightly tickling the skin on his soft belly as I ran my fingertips under the fabric. He pulled down the swim shorts and crushed my naked body against his, his erection pressing against my hip as he kissed me desperately. I slid my hands up his sides and around his back, loving how soft his skin was and the way he shivered at my touch. “What do you want to try first?” I asked him breathlessly.
“Can we sixty-nine?”
I nodded, smiling excitedly at him. “Lay on the bed. And focus on my clit with your lips and tongue. And don’t use your teeth!”
He laid down in the centre of the bed and scooted down when I waved him over. I swung my leg over him and backed up until my dripping pussy was over his mouth. His hands gripped my ass and brought me down slowly until I made contact with his face. He tentatively snaked out his tongue and brushed it against my clit, enjoying the moan I made in response. Once I was confident that he didn’t need further direction, I took his cock in my mouth and started bobbing my head up and down. He groaned against my pussy, sending delicious vibrations against my clit. I moaned against his cock in response, taking the full length of him into my mouth until he bottomed out.
We lay there for a while, teasing with our mouths and moaning against each other. I knew I wouldn’t be able to cum with the gentle pressure he was providing, but I also didn’t want to tell him to press harder and risk having him hurt my clit accidentally. I drew back from his dick and spoke softly. “Do you want to have sex now?”
His mouth froze. I lifted my pussy off his face so he could speak more easily. “Are you sure?” he whispered reverently, clearly terrified I would change my mind or he would wake up and find this was all a dream.
“Fuck yeah, I’m sure.”
I slid off of him and ripped open the condom wrapper with my teeth. He watched intently, propping himself up on his elbows. I tossed the wrapper over my shoulder and pinched the tip, rolling the condom down the length of his erection. He instantly went soft in my hand. I looked up at him, surprised. “Oh my fucking god, that is mortifying,” he moaned, covering his face with his hands.
I pulled off the condom and tossed it to the side, smoothing out my face to a neutral expression. “It happens all the time and is nothing to be embarrassed about.”
I circled his cock with my lips and began sucking it, enjoying the feeling of it growing and filling my mouth. One of his hands pushed my hair away from my face as he watched my head bob on his cock. I locked eyes with him and suctioned my cheeks, loving the look of reverence and pleasure on his face. Swirling my tongue around the tip, I used my hand to stroke the length of his cock until he was fully hard again. I pulled my face back for a moment. “Keep yourself hard for a sec.”
He reached a hand down and took over for me, jerking his cock roughly as he watched me get up and walk across the room. I took out a couple of condoms and tossed them on the bed. His eyes widened when he saw how many there were. “Just in case it happens again,” I explained, “because, again, it happens all the time.”
He smiled gratefully, almost all embarrassment gone. “Can you put it on like I just showed you?” I asked.
He nodded, grabbing one of the condoms and tearing it away from the others. I lay down on the bed next to him and spread my legs, motioning for him to kneel between them. He put on the condom and leaned down to kiss me, his still-hard, condom-covered cock brushing against my pussy. I broke the kiss to grab his cock, guiding it down to my pussy. “It’s farther down than you’d expect,” I told him, pulling him towards me until the tip was teasing my entrance, “Now push in.”
He leaned forward on his elbows, covering my body with his, and then pushed his cock in.
“Holy shit,” he whispered against my neck.
“Fuck, you feel good,” I moaned softly.
I felt him smile against my skin and I wrapped my arms around his back, holding him tightly. “Do I just…?” he asked, trailing off.
“Do what feels natural,” I whispered breathily, “You won’t break me.”
He pushed up onto his hands and started thrusting into me slowly. “Oh my fucking god,” he moaned, looking between us to watch his cock disappearing into my pussy with every thrust as if he couldn’t believe it was happening.
I scratched his back softly with my fingernails. “You can go harder if you’d like,” I murmured.
He locked eyes with me, a look of wonder on his face. “I don’t want to hurt you.”
“Vaginas are designed to push out whole-ass babies. I can handle it.”
He leaned down on his elbows and kissed me roughly before burying his head in my neck and starting to fuck me. My moans filled the air, and I wrapped my legs around his hips so that he could push into me deeper and deeper with every thrust. I wrapped my arms around his shoulders, whispering his name with a moan into his ear. “You feel so fucking good, James,” I murmured, tickling his ear with my lips.
He groaned and bucked wildly against me, panting. “I’m getting close,” he strained.
“Cum for me, James,” I begged in his ear, “Please cum for me.”
A strangled groan bubbled from his throat as he stilled his movements and filled the condom with cum. I let him rest for a moment and then gently pushed him off me, instructing him to tie and dispose of the condom. He climbed back on the bed afterwards, laying next to me and panting as he tried to catch his breath. After a moment, he looked over at me. “Did you finish?”
I briefly entertained the idea of lying to preserve his ego, but I ultimately decided his education was more important. “No, I didn’t, but I enjoyed it,” I told him truthfully, turning on my side and cupping his face so he would look me in the eye.
He kissed me softly and then pulled back, looking nervous. “What is it?” I asked.
“Can I try to make you finish now?”
“Yeah, of course! Fingers or mouth? Fair warning that condom lube doesn’t taste great.”
“Fingers, then,” he laughed.
I laid back on the bed and opened my legs, pulling him closer to me on his side. I took his hand again and repeated my motions from earlier, using his fingers to circle my clit. “Is this all it takes?” he asked, kissing my shoulder.
“Sometimes light clit pressure is enough to get me to cum. But I’m going to ask you to finger me.”
He nodded and sat up a bit more. I continued. “Ok, you remember how the entrance is lower than you expected? Take two fingers and gently, GENTLY, slide down until you feel it.”
He did as he was told, and I felt his fingers at my entrance. “Ok now gently push in—“
I cut myself off with a gasp as his fingers filled me. “Did I hurt you?” he asked, suddenly panicked.
I shook my head. “No, it feels really good, fuck, keep moving your fingers.”
He gently dragged his fingers out from my pussy and pushed them in again. I moaned loudly, one of my hands gripping the arm that was holding him up. He tore his eyes away from my pussy to look at me, flushing with pride as he saw the pleasure evident on my face. “Mmm, don’t stop doing that,” I moaned softly, pressing my forehead against his arm.
He fingered me slowly, building up the tension as he slowly increased his speed. Curses started falling from my lips as he massaged my cunt. “Curl your fingers slightly each time you pull out,” I ordered.
I held onto his arm for dear life and moaned loudly as he followed directions, his fingers pressing against my g-spot on each outward stroke. “Holy shit,” he whispered.
“Keep going. Go faster.”
He picked up the pace, fucking me with his fingers. My hips pushed up to meet his fingers, moving on their own accord. I brought a hand down to press gently against my clit as he worked me from the inside, capturing his lips again for a deep, sloppy kiss as an orgasm grew in my belly. I broke the kiss to press my forehead against his neck, one of my hands digging into his arm while the other frantically rubbed my clit. “Fuck, I’m gonna cum. Fuck, James, please don’t stop, please don’t stop!”
James stared at my naked form, his mouth open, as he made me cum, my cunt tensing around his fingers and my body spasming softly as I called out his name. I brought his face down to kiss me as I moaned through my orgasm into his mouth.
As my orgasm slowly dissolved, I pushed Jame’s arm away and he immediately removed his fingers. I turned on my side and hugged him, our naked bodies flush together, and I peppered kisses all along his cheek and down his neck. He squeezed me back tightly, his face nuzzling into my neck. We rested like that for a minute, just holding each other and enjoying the afterglow of having taken this new step together. I rubbed a hand across his back. “How do you feel?” I asked softly.
“Weird,” he said, his face muffled by my skin, “Like, I feel the same, but I also feel like everything’s changed. Like my whole idea of myself is different.”
I giggled. “That’s what happens when you build up your identity around not doing something and then you finally do it.”
He laughed at my neck and squeezed me tighter. “That was amazing,” he whispered, kissing my jaw, “thank you.”
“For helping me pass statistics!”
We laughed together, our giggles tapering off as we stared at each other. I looked up at him and ran a hand through his hair and down to his cheek. I kissed him softly. He kissed me back gently, his tongue brushing against my lower lip. Our bodies relaxed against each other and the bed as we kissed. No sucking in stomachs, no angling ourselves to look “hot.” No pressure. Just one body holding another body comfortably as their lips gently met. I pulled back and gave him another peck. “This can’t become an actual thing, you know,” I whispered.
“Because we’re going to different colleges.”
“But if you want to keep practising this summer…”
His lips attacked mine as he climbed on top of me, and we laughed together at our eagerness as we started again.
Half an hour later, we rejoined our friends on the beach, our little secret weighing between us as we exchanged knowing smiles whenever our friends weren’t looking. I dropped my stuff in the sand and ripped off my cover-up, plopping my relaxed, exhausted body onto my towel. “I’m going to read and tan for a bit. Want to join?” I asked, pulling out a trashy romance novel I had swiped from my mom.
“I think I’m going to swim for a bit!”
“Swim away, then!”
He whipped off his t-shirt and ran to the waves, his body jiggling softly as he ran and a wide smile on his face. He had never looked so handsome.