My first kiss and my first time on our last night together [MF]

“Jess? Are you awake?”

I opened my eyes as I tried to recall where I was, and who would be waking me up in the middle of the night. A faint smell of smoke was in the air, and I was curled up in the back of my best friend’s SUV.

“God you look so beautiful like this.”

Slowly I started to come to my senses— it was the last weekend before Labor Day, and we were all headed to different universities by the end of the week. To celebrate our last summer together, we had built a bonfire and bribed our older siblings to bring us beer in a field outside of town. I hadn’t had much to drink, but the evening was dragging me down and I told everyone that I was calling it a night. Jake had encouraged me to sleep it off in his car before morning came. Morning, and a new life without Jake. Morning and a fresh start without the guy who I’d had an unrequited crush on for as long as I could remember. I could’ve sworn it was Jake’s voice, but he’d never said anything like that to me before.

“Jess, it’s me. Scoot over, I’m joining you.”

I sat up and looked at him, finally fully awake.

“Hey you. You calling it a night, too? I‘ll go sleep in my own car so you can crash here.”

“No please don’t leave,” he said, grabbing my hand. We both stared down at our joined fingers, and I felt a jolt of lightening at the contact. In the 18 years that we’d been best friends, he’d never held my hand. “Please don’t leave, I have to tell you something.”

“Sure,” I said, trying to stay calm and not shift in my seat. How embarrassing that just sitting there next to him in the dark was enough to make my pussy wet.

“Look, Jess, I don’t know how to say this, but I just can’t let you go without telling you…”

“Telling me what?” I said, after a pause.

“Telling you that… that I like you, Jess. I like you a lot. I’ve liked you for years but I never got up the courage to say anything. You don’t have to say anything back just, please… let me kiss you? Just once?”

Holy shit holy shit holy shit holy shit. Could this be real life? The guy I’d been crushing on for ages had been crushing on me, too? Fuck. Could I tell him that I’d never been kissed? I was 18 years old, a high school graduate, able to vote and sign on a student loan and shit, but never able to let anyone close enough to kiss me?

“What about Lauren?” I said, biting my lip and feeling guilty about lusting after someone with a girlfriend.

“We broke up this afternoon. She didn’t want to do long distance. I can’t believe I forgot to tell you. I was just so glad to be free to show you how I feel. But I… if you don’t want to I understand.”

I bit my lip a little harder, trying to find the word and the courage to ask for what I’ve wanted for so long. I looked up and locked eyes with him. Slowly, I closed my eyes and leaned forward, like they do in the movies.

Jake’s lips brushed against mine gently, not demanding but inquiring. My first kiss, and I had no idea what the fuck I was doing. So I opened my lips just a bit, and kissed him back.

It was like a switch was flipped. Now Jake was kissing me urgently, needily, his tongue slipping into my mouth. I pressed myself against him and shyly tangled my tongue with his. He let go of my fingers and rested his hands on my hips instead. When his tongue began thrusting into my mouth, I sucked on it and welcomed it deeper. He pulled away with groan and I realized that I’d been making embarrassing little moaning noises.

“Holy shit, Jess” he said, squinting at me in the dark.

“I’m sorry, did I do it wrong? Shit, I’m sorry… I—”

“Hell no you didn’t do it wrong, that was fucking unbelievable and you know it.”

I looked away, trying not to let him see the blush on my face.

“You know that was good, don’t you?” He said, touching my cheek and turning my face toward his.

“I… honestly I don’t have anything else to compare it to.” I mumbled, wishing I could just crawl into a hole and die of embarrassment.

“That was your first kiss? You gave me your first kiss.” He said, surprised but kind of… proud?

I took a deep breath, and decided to be brave. “Yes. You got my first kiss, Jake… and I’d like to give you a few other firsts, too.” With that, I moved his hands off my hips and put them on my breasts.

Now, I know I’m not exactly a model, but 4 years of varsity volleyball meant that I was passably fit with a tight and round, if not overly large, ass. But my tits are by far my best asset. That night I was wearing a strapless push-up bra and a skimpy tank top. My breasts were overflowing and just begging to be released.

Slowly he cupped and squeezed my boobs, staring at his hands on my chest with disbelief in his eyes. When he finally looked up, his breathing and his voice was rough. “Let me see them.”

I could not believe this is happening. I couldn’t believe I was stripping for my best friend, the guy I’d been masturbating to since I discovered masturbation. Feeling a little bit bold, I decided to put on a little show. I grabbed the bottom of my tank top and eased it up, ever-so-slowly, revealing skin inch by inch. Finally I tossed my shirt into the front seat and looked him in the eye. Holding the strapless cups with one hand, I reached around with the other and unclasped my bra.

“I didn’t know you were such a tease,” he said, smirking but starting to look a little strained. Slowly I let my bra drop, and let him get a good look at my perky teen tits. He sucked in a breath, and then reached forward to touch them again.

Jesus Christ I was in heaven. Seeing his hands on my chest, my breasts overflowing between his fingers, feeling him roughly pinch my nipples, had me crazy wet and almost ready to come just like that. When he kissed his way down my neck and began planting little kisses around my hard puckered nipples, I began to whimper and rock against the seat a little bit, rubbing my clit on the seam of my daisy duke jean shorts.

“Can I help you with something?” He said between kisses and licks and— holy fuck was that a bite?— not taking his eyes or his attention off the boobs in his hands.

“It’s up to you, Jake,” I halfway moaned, trying not to feel a little frustrated. Am I being greedy, wanting him to get me off when he probably just wanted a kiss?

Suddenly he took a nipple in his mouth and sucked. I nearly fell into his lap from arching my back toward him so hard. I planted my hands on his shoulders, trying to steady myself as he slowly slid a hand down my stomach and into my panties.

When his fingers found my clit, I let out a little cry. He looked up from sucking on my titties and smiled a devilish smile. He slid his fingers farther down, until he found my wet, pulsing pussy.

“Fuuuuuuuck,” we both sighed together. His middle finger slipped in and out of my slick cunt.

“God you’re wet,” he groaned, circling my clit with his thumb as his middle finger continued to work its magic. “And so fucking tight.” He put his mouth back on my breast as he fingered my pussy, and that was when I came all over his hand.

No amount of exploring my own body could compare to that orgasm. I think I saw fucking stars. I was shaking, and he just kept thrusting and sucking until I had to push him away and catch my breath.

Laughing, Jake pulled me into his lap. “I assume that’s your first time coming with someone else, right? You were incredible.” I nodded, and shifted my hips as pleasurable aftershocks coursed through my body. That’s when I noticed his cock throbbing under my ass.

How did I not even think of his dick before? I’d been so caught up in the things he was doing to me, that I hadn’t even thought of touching him back. I shifted again, and his laughing turned to a stifled groan.

“Can I help you?” I asked, feeling saucy and sexy and not-quite satisfied despite the thorough finger-fucking I’d just come down from. I pulled his shirt over his head, wiggling on his lap as I threw it to the front.

“You don’t have to,” he said, looking pained but determined.

“I want to,” I said, crawling out of his lap and kneeling on the floorboards of his car. “I want to more than anything in the world.”

Jake brushed my hair out of my eyes and smiled apologetically while I unbuttoned his jeans and pulled them down, along with his boxers.

Holy shit.

His cock was huge. Granted, I had no real-life experiences to compare it to, but it easily looked as thick as a pornstar’s. “Sorry,” he said, “It’s kinda big. I understand if you don’t want to try anything, Lauren said it’s painful to—“

But he never finished that sentence, because immediately I put his head between my lips and sucked. My first blowjob, and I was determined to make it a good one. I tried to remember all the techniques I’d seen in porn, but I usually skipped the blowjob parts of the videos I watched. I had never really believed that a blowjob could be enjoyable for the person giving it— especially when the person on the receiving end had a schlong so thick I could barely wrap my lips around it. I licked him from base to tip, gently fondling his balls with one hand and stroking him with the other. I couldn’t take very much in my mouth, but as I was tonguing the tip I realized that I was getting wet again. I pictured his cock thrusting into my pussy the way he was thrusting into my throat, and started to moan on it. Jake wrapped my hair around his fist and pulled my head up to kiss me.

“Where the hell did that come from?” he said, between rough, shallow breaths.

“Was it not very good? I would love to practice some more…” I said, leaning over to go back to work.

“Wait!” Jake said, grabbing my face in his hands too look at me. “Where do you want my cum?” He asked, his eyes burning into mine.

“Where do I want it?” I said, never having thought about the question before.

“Do you want me to cum down your throat?” He said, sounding like he wouldn’t mind the idea. The he glanced down at my chest, and I felt his cock twitch in my hand. “Or do you want me to coat your gorgeous tits?”

I bit my lip and considered the question. To be honest, even having enjoyed blowing him I didn’t think I wanted the night to end with a swallow. And while the thought of sleeping with his cum rubbed into my tits made my pussy throb, that didn’t feel quite right either. Fuck it, I thought, why not go for broke… I leaned in and kissed him, biting his lower lip and sucking it toward me for a moment.

“I want you to cum in my pussy. I want you to claim me tonight.”

“Jesus Christ… are you sure? You’re not on birth control, are you?” I shook my head.

“But I’ll buy a Plan B first thing in the morning. I need you tonight. I gave you my first kiss, and I want you to take my virginity. Please, before everyone wakes up and we all have to leave.”

He ran his fingers through his hair and looked out the window. We only had a couple of hours before dawn; a couple of hours before we moved on. I could see in his eyes the exact moment when he decided to make me his.

“Ok, I’ll do try. But Jess, you’re so fucking tight… I don’t know if this is going to work.”

I nodded. “We’ll go slow, and we’ll just try our best.” I said, grabbing his hand and sliding it into my panties again. “At least we won’t need any lube.”

We both moaned as his fingers found my dripping wet pussy, and he took my mouth as we both frantically worked my shorts and panties off and threw them in the front seat.

He laid me down across the backseat, and pushed my knees up on either side of his hips. Then, staring at my pussy in the dim moonlight, he backed down off the seat and kneeled on the floorboards instead. I began to sit up to ask what he was doing, when I felt his mouth on my pussy.

Holy fuck. Holy fucking shit. His rough tongue felt like lightning on my sensitive clit. He licked, slowly, up the length of my pussy, then circled my clit and gave it a little kiss. I let out a laugh that came out like a sob. He smiled up at me, then went back to work, licking and kissing and even biting my throbbing cunt. Then he began to focus on my clit, as I felt my orgasm getting closer and closer. I put one hand on the door frame and clutched his hair in the other. Suddenly, he thrust a finger into my wet, tight hole. I clenched around him and started to come. He inserted another finger, and then another, driving me into an unbelievable orgasm that seemed to never end. When I finally got my breathing back under control, Jake still had 3 fingers inside of me, grinning from ear to ear while he gently stretched me and prepared my body to take him inside.

He got back up on the seat, positioned his throbbing cock between my limp legs, and waited for me to look him in the eyes. “Are you sure?” He asked, giving me one last chance to keep my virginity.

“Fuck me. Please, fuck me,” I whined, barely recognizing my own voice.

He leaned forward, pushing his tip just barely inside me. I held my breath, not sure if I was feeling pleasure or pain.

“Relax,” he said, reaching forward to hold my hand. He inched forward a little bit more, stretching my pussy with his massive cock. With his other hand, he squeezed my breast and played with my nipple. I began to wiggle against him, feeling his dick slide a little bit deeper.

“Fuck yes, that’s right,” he said, pinching my nipple before moving to the other breast. I gave his hand an appreciative squeeze, then let go of his fingers so he could mold both of my tits while slowly impaling me on his cock. I reached down to rub my clit, while his rod inched deeper and deeper inside of me.

“You’re killing me, Jess. You’re fucking killing me,” he said, looking down at where I was touching myself as he struggled not to thrust.

“You’re so fucking tight.” He pushed forward with a groan. “You’re so fucking wet.” He pushed again. “You’re going to take this cock,” he growled, “and you’re going to fucking like it.”

The dirty talk put me over the edge, and I clenched around his dick, pulling him closer and closer until I had all of him inside me. He squeezed my tits and continued to talk dirty until my orgasm began to fade; then he pulled out and slowly thrust in again for the first time.

Holy god that felt so good. We moaned in unison, and he reached for my hands again. We held hands and I lifted my legs up to his shoulders as he fucked my virgin pussy, grunting and sweating and whispering “Jesus” “fuck” and “unbelievable.”

“I can’t last,” he said, as his thrusts became erratic and rougher. “You’re too tight. Can I really cum inside you?”

“Fill me up,” I begged, letting go of his hands and running my fingers down his back. I wrapped my legs around his hips and pulled his ass in toward me. “Give me everything,” I whispered.

“Take it,” he groaned, thrusting deep and hard, spurting his cum into the wet, tight pussy that had been waiting just for him. Feeling his cock jerk inside me, feeling the warmth of his cum spreading in my unprotected pussy, hearing him groan as he emptied himself inside of me— it was all too much, and I came again, gently milking his rod and pulling his cum deep into me as his body collapsed on top of mine.

We must have drifted off to sleep for a while, because next thing I knew the sun was rising. I tapped Jake on the shoulder and told him we had to get up and get going. He blinked a couple of times, then kissed me deeply until I felt his cock hardening again.

“Can I come visit you on Fall Break?” he asked, brushing a lock of hair out of my eyes.

“Only if you promise we can do this again,” I said, feeling so happy my heart might explode.

“I promise we can do this again,” he said, kissing down my neck, “and again,” my breasts, “and again,” and my tummy, until we were both gasping for air and ready for round two.

Source: reddit.com/r/gonewildstories/comments/qacrpj/my_first_kiss_and_my_first_time_on_our_last_night