The First Timers Club Pt. 02

I pulled my finger out a little bit until she relaxed, and then very slowly pushed it back in. This time, she didn't protest, and I was able to slip past the second knuckle and sink it all the way inside of her.

Courtney responded my rocking her hips back and forth, causing my fingers to slide in and out of both her pussy and asshole. I leaned my head back to rest my tongue, using my thumb to massage her clit while she fucked herself with my fingers. She whined and moaned at the sensation of both holes being penetrated simultaneously, and the continuous stimulation of her clit.

She grew increasingly frantic, quickly bobbing her head up and down. My sensitive cockhead slid rapidly between her soft, wet lips, while her hand pumped synchronously up and down over my shaft. My breathing intensified, and I felt my orgasm slowly build, a rising pressure that boiled up from my base of my aching cock.

I spread my legs and lifted my hips to match Courtney's rhythm, gently thrusting my cock up into her mouth. She responded by rocking her hips back and forth to match my movements, my fingers plunging in and out of her pussy and asshole faster and faster.

"Fuck, Courtney, don't stop. Don't stop. I'm going to cum, baby."

Courtney whined and bobbed her head faster, her urgency reaching a frenzied pace. I lifted my head and took her swollen clit back into my mouth, sucking and licking it as hard and as fast as I could.

We were manic for each other, driving ourselves ever closer to the edge of bliss. I wanted her to cum with me, to share in my release. I became highly attuned to her actions, the tone and pitch of her vocalizations, the intensity and speed of her fevered movements, and I adjusted my own to match.

I lingered so close, and I didn't want it to end. I wanted to stay in that moment with her as long as I could. I considered slowing her down to draw it out, to edge myself closer and closer, to take my time and revel in the delicious agony of denial. But I knew I didn't have the strength to do it. I had denied myself enough, and I was ready to release the pent up frustration that raged and roiled in my balls.

Courtney whimpered, and her sphincter fluttered and tightened around my finger. An instant later I erupted, ejecting a thick rope of hot, sticky cum into her open mouth.

"Oh god!" I gasped.

My vision blurred and I groaned loudly, ejaculating a second, smaller load of cum. I thrusted into Courtney's mouth several more times before finally lowering my hips back down onto the bed, but she didn't stop. She kept her mouth on me, sucking on the head of my cock and jerking me off. She'd slowed the rhythmic rocking of her hips, but hadn't stop completely, and continued to slowly fuck herself with my fingers.

When she'd finally milked me dry, she took her lips off my cock, and I heard her struggle to swallow my cum. After several aborted attempts, she managed to get it down, gasping and swallowing repeatedly.

"That was a lot more than I thought there'd be," she said.

I absently moved my fingers in and out of Courtney's pussy and ass while she stroked my sensitive cock and massaged my balls. The feeling was exquisite, and I took a deep breath and slowly exhaled.

"Wow," I said quietly under my breath.

Courtney gave my deflating cock a gentle squeeze and licked the small amount of cum that flowed from the urethral hole. Then she kissed around the base of my shaft and dragged her tongue over my balls. She was insatiable.

"I loved that we did that," she said finally, and I couldn't disagree.

My cock had deflated enough than Courtney could take me all the way into her mouth. She closed her lips around the base and slowly lifted her head until I popped out of her mouth. The incredible sensitivity of my glans caused me to jerk involuntarily from the intense sensation. Courtney giggled and did it again.

"Please. I can't," I said to another one of her mischievous giggles.

"Sorry, I can't help myself."

When I slowly pulled my fingers out of her, she spun her head around and whined. "No, please. Not yet," she cried, but it was too late.

I pulled her hips down until her pussy rested on my face and I kissed it several times. Then I let my arms fall to either side of my body, utterly and completely spent.

We laid like that for a while, until Courtney lifted herself off me and sat on her haunches near my hip. She stared at my deflated cock as if it were a wounded soldier and appeared contemplative. I put my hand on her leg and she turned and smiled.

"Can we do it again?" she asked, and I laughed.

"I don't think I can tonight," I said, though for an instant I considered it. But no, I felt way too fucking tired.

"I know," she said, wistfully.

She became pensive again and I wondered what she was thinking. Would she ask to spend the night with me? If she did, how would that play out with Ashley and the other girls? Did they know she was here with me right now? They had to know, right?

"I want to have sex with you," Courtney said, her expression perfectly serious.

"Isn't that what we just did?" I asked, but she already shook her head.

"No, I mean for real. I want you inside me."

I lifted my eyebrows. "Oh."

"Unless you don't want to," she said hastily. "If you only want to do oral, I'm totally fine with that. Honest."

I sat up and rubbed my face, smelling the scent of her that lingered on my fingers. I smiled at her weakly. Fatigue gripped me. I needed sleep.

"I'd love to have sex with you, Courtney, but are you sure you're ready for that?"

"Why? What do you mean?"

How could I tell her what she needed to hear without saying too much or, worse, hurting her? I looked deeply into her large, brown eyes, and I saw it there, written plain as day on her sweet, young face. The post-orgasmic exhilaration, the eagerness and craving for more that comes from impassioned desire, and the expectant hopefulness and excitement at the prospect of a potential new relationship.

"I mean, I might not be the right guy to share that with."

Something like anguish flashed across her face, but so fleeting that I nearly missed it. "I don't understand. Why wouldn't it be you?" she asked uneasily, and I detected a slight tremor in her voice. I felt selfish for being so aloof.

Oh, for chrissakes, stop treating her like a child! She can handle it. Just be fucking honest with her.

"Because there could never be more between us than that."

She blinked and swallowed hard as reality bullied past her fantasy. I pressed on before she could respond.

"I like you a lot and I enjoy being with you like this, and I'd love nothing more than to fuck your brains out whenever you wanted, as often as you wanted. But I'm not looking for anything deeper than that.

"I enjoy being your friend and I love having sex with you, and as long as that's enough for you, then this could work. And if you feel you need more than that, I completely understand, but this is where it would end for us. At least as far as sex goes. I'd still be your friend, of course." I smiled. "And, of course, we'd always have tonight to remember."

Courtney nodded her head and chewed on what I'd said. She didn't appear ready to cry, so I was grateful for that, but her expression remained inscrutable. She glanced at my cock and idly played with her hair while she mulled it over.

"So, we'd be friends?" she asked, and I nodded. "But we'd also have sex?" I nodded again. "And we could have sex whenever we wanted?"

"Well, as often as our schedules would permit."

She nodded her head again, contemplating the proposal. "So, we'd basically be friends with benefits?"

"If you want to call it that, though I've never really liked that term."

"Fuck buddy?"

"Sure."

"Hanging and banging?"

"What?"

"Netflix and chill?"

"Okay..."

Courtney smirked. "What if I wanted to have sex with someone else?" she asked, and I cracked a smile.

"Oh, so now you're a player, huh?"

She laughed, but then grew serious again. "No, really."

I suspected that she hadn't been asking about herself, but it was a fair question, and she deserved a straightforward answer.

"What we do when we're not together is our own business. That said, I'm always down for a threesome."

My answer must have surprised her because she cocked her head and lifted an eyebrow. "I'll think about it," she said finally, and I nodded. Fair enough. Then she narrowed her eyes slightly. "When do you think you're going to wake up tomorrow?"

"I don't know. Why?"

"Because I still want to have sex wih you."

"Really? Are you sure?"

She chuckled. "Am I sure? You made me cum three times, my dude. If this is going to be a one night stand, might as well make it one I'll never forget. Now, get some sleep," she said, crawling under the covers and turning off the television and lamp. "I want to get started as soon as you're awake."

Even though I'd finally found release, sleep still proved elusive. I pressed myself against Courtney's back to spoon with her and tried to behave myself, but my hand inevitably found its way to her breasts, and her responsive movements and soft moans quickly had me hard again and poking her bottom.

She asked if I wanted to have sex, and I did, but I demurred and told her I just wanted to hold her and try to sleep. When I poked her in the butt again, she reached back and angled my stiff cock between her legs, then pushed her ass against me until it nestled firmly against her pussy.

I found her aroused and eager, and the head of my cock glided against her wetness. Courtney arched her back and rocked her hips, sliding her pussy against my cock.

"Oh god, I want you to fuck me," she whispered, and I gripped her breast and pulled her tightly against me.

I wanted her in the worst possible way, but my body had other, more urgent needs. I kissed her shoulder and the back of her neck, then settled my head onto the pillow and promptly fell asleep.

Chapter 11 - Request of the Nerds

I roused in the dim hours of early morning to Courtney's phone buzzing on the nightstand. She groggily reached for it and checked the screen.

"Shit, it's Ash," she hissed. "Should I answer it?"

"Why wouldn't you?" I muttered and tried to fall back to sleep. Courtney sat up, instantly awake, and cleared her throat.

"Hey, what's up?" she asked quietly when the call connected. Ashley's response through the phone's speaker sounded tinny and far away.

"Hey, where are you? Did you leave?"

"No, I'm downstairs," she admitted, then quietly cursed herself for it. She immediately rolled out of bed and frantically rooted around on the floor for her clothes. Ashley's cautious response came after a long pause.

"Downstairs where?"

Courtney held the phone with her shoulder and danced her way into her panties. I head footsteps overhead.

"I'm in the bathroom," she lied, fumbling to untangle her crumpled cami. She dropped the phone onto the bed and quickly pulled it over her head. The stairs creaked.

"Why are you using the downstairs bathroom?"

Courtney snatched up her phone and quickly slipped out the door, blowing me a kiss before shutting it with a soft click. "I got a surprise visit from Aunt Flo," I heard her say as she tiptoed down the hall. Then, before I knew it had happened, I fell fast asleep again.

Sunlight sliced past a narrow gap in the vertical blinds to paint my face, waking me for the second time. I could tell by the high angle of the beam, and a decidedly refreshed feeling, that I must have slept late. My phone confirmed it to be well past noon.

I took the shower I should have taken the night before and redressed in the same clothes. In the vanity, I found a new toothbrush, as well as toothpaste, deodorant, and a comb. Twenty minutes later, I felt almost human again.

I bumped into Erin almost immediately upon exiting the room, hauling a clinking bag of recyclables to the garage. She smiled when she saw me, but I didn't feel in the mood to reciprocate.

"He lives," she said sardonically. "Sleep okay?"

"Fine."

"Fine," she repeated in a mocking tone, and laughed. "You just missed Clay. He literally just pulled away."

"Where are my keys?" I asked, shifting my backpack. I couldn't have cared less about Clay, or her for that matter.

"We're going to have a lot of fun today. Clay won't be back until ten, so we've got lots of time," she said, resuming her journey to the recycling bin. "Ashley's in her room. You should go up and see her. Mommy will come find you later when her pussy needs you."

I called after her, but she had already disappeared into the garage. Goddammit.

I thought about searching for my keys, but I knew that would be fruitless in a house that big. Uber remained an option, but then I'd have to come back at some point with my spare. I resolved to leave the house, with or without my Rover, well before Clay came home. I didn't want to see him again after what he'd pulled the night before.

Regardless of how I felt about Clay and Erin, however, I found my spirits lifting as I climbed the stairs to Ashley's bedroom. I felt excited to see her again, and that surprised me.

Her door stood closed. As I approached, I heard heated conversation coming from inside. Ashley arguing with someone. Courtney. Shit. I knocked on the door and the arguing stopped.

"What?" came Ashley's voice from inside.

"It's me."

The door flew open, and Ashley stood glaring, her face red. "What do you want?" she asked, turning away before I could answer.

Brittney and Kayla sat on the edge of the bed playing a video game, neither willing to look at me, while Courtney stood off to the side with a miserable expression on her face. I could guess what they'd been arguing about.

"I was hoping we could talk," I said, easing into the room and closing the door behind me.

"About what? Having sex with my so-called best friend?" Ashley fumed, her arms crossed tightly over her chest. Courtney looked like she would be ill. I gave Ashley a dour look and shook my head.

"No. That's none of your business."

Ashley's eyes flared, and she jabbed an accusing finger at Courtney. "Why do you always have to be such a slut?"

"Back off!" I snapped, and Ashley shrank back, immediately cowed. The other girls, startled by my outburst, turned to stare. "Sit down."

Ashley dropped her butt onto the foot of the bed, and Courtney sat as well, even though I hadn't been talking to her. I fixed Ashley with a stern scowl but kept my voice calm and even.

"I told you, that's none of your business and it's the last time I ever want to hear you bring it up again. Are we clear?"

Ashley gulped and nodded her head. Her anger appeared to have been superficial and probably amounted to little more than petty jealousy and hurt feelings. Still, better to nip it in the bud before it flared into something more. It also wouldn't hurt to establish some ground rules about what was and wasn't out of bounds at the same time.

"You guys are supposed to be friends. You should all be supporting one another, not trying to tear each other down and call each other sluts. You know what I'm saying?"

Ashley glanced at Courtney and her face reddened, but this time with shame. She nodded again.

"Good. Now, I came up here to talk about what your mom said last night." At that, everyone's ears perked up. "Is there somewhere we can go? Somewhere private?"

Ashley exchanged furtive glances with her friends and said, "I told them about it. They know."

Interesting. I nodded and pulled her desk chair over, spinning it around to sit on it backwards. "Whatever. Look, I was pretty fucked up last night, and so was your mom, and she said some really awful shit to you she shouldn't have, and I'm really sorry about that."

Ashley watched me intently, saying nothing, so I continued.

"Anyway, I want you to know that I really don't give a flying fuck what your mom thinks or wants, alright? Fuck that bitch. I only care about you and what you want, and I'm perfectly happy to tell her to go fuck herself. So, if you don't want to take me up on my offer, just let me know, okay?"

Ashley blinked a few times but remained quiet. I nodded, hoping for something more from her, but she gave nothing. I finally slapped the back of the chair.

"Okay, well that's all I really wanted to say, so I'm going to go look for my keys now and get out of your way. I had an amazing time hanging out with you guys last night. Courtney, I'll give you my number before I go, in case you ever want to call me, okay?"

I stood to leave, pausing briefly when I opened the door. "Happy birthday, Ashley," I said, and stepped into the hall.

"Wait."

I stopped and turned. Ashley stood, staring at me intently. "Did you mean it?" she asked, and I furrowed my brow. "About your offer. Did you mean what you said?"

"Yeah, I did."

Ashley looked at her friends and then beckoned me back inside. "Don't go yet, okay? Just sit down. Please."

I did as she asked, closing the door behind me. When I sat back in the chair, Ashley spoke with a tremulous voice.

"We were talking about it earlier, before you came up. That's how that...discussion you saw started," she said, glancing at Courtney.

"My mom's a bitch, but she is right about one thing. I am a loser." When I opened my mouth to object, she rushed ahead. "I get picked on, every day. I get called names, every day. I get sh-shit on, every day. I've done everything I can think of to be nice to everyone, but nothing ever works. Everything I do to try to be accepted only seems to backfire and make things worse."

A tear broke free and rolled down her cheek, but she quickly wiped it away and fought back more. I felt my anger rise again. Another broken finger. I took a deep breath and tried to calmly listen to what she had to say.

"All I've ever wanted is to be normal. To have the chance - just a chance - to have what other girls have, but no one...no boy will even talk to me. I've never had a boyfriend. Ever. None of us has. Only Courtney was ever asked out on a date before, once, and she got stood up."

She took a stuttering breath to collect herself before continuing. "I've been treated like an outcast ever since middle school and I'm just so tired of it. I wanted to know...I wanted to ask if you think you could help me become, I don't know...sexy is probably asking way too much, but at least less repulsive to males? Nothing I've tried so far has worked and I don't know what else to do."

She paused briefly, then sat back down on the edge of the bed. I waited silently in case she had more to say, but it soon became obvious she didn't.

I slowly shook my head, blown away by how sincere and forthright she'd just been. I couldn't fathom the cruelty she'd been forced to endure for so many years and yet, despite all of it, she'd somehow managed to remain so optimistic and kindhearted. The injustice of it made me want to toss the chair across the room and scream, and I took a moment to calm myself down. As the silence dragged on, however, Ashley became increasingly anxious, fidgeting with the hem of her shirt and shifting her feet.

"I promise, I'll do everything I can to help you," I said at last, and Ashley let out a loud sigh of relief. Kayla cleared her throat and Ashley looked over her shoulder and nodded at her. "All of us?" she asked when she turned back.

I looked at Kayla and Brittney, then at Courtney. All three girls nodded in agreement. I smiled. They really were a tight crew.

"Yeah, why not? All of you."

It was Kayla's turn to exhale a sigh of relief. Then the girls shared a look, and I sensed something else brewing.

"One other thing," Courtney said.

"What's that?"

"Do you consider us all your friends?"

"Yeah, of course I do."