The First Timers Club Pt. 05

"That was different," I told her. "I knew what I'd taken then."

Erin didn't seem to hear me. "Wow, you're actually...quite lovely," she said to Courtney, shaking her head as if to clear it. "Nice tits."

I waved Courtney closer and motioned for her to stand next to me.

"We're fucking," I said. "I figured I'd tell you now, in case you were tempted to drug me again."

"Good for you, honey," Erin said the Courtney, ignoring me. "I hear he's very good."

Courtney stood with her legs together holding her arm, completely befuddled. She looked disoriented and didn't respond.

"She's speechless!" Erin laughed, and then became more serious. "You're obviously here for a reason, dragging her along with you like this. What do you want?"

"We need to borrow some things from you," I said, and Erin's eyebrows levitated.

"Oh? Like what?"

"Lube, for one. As much as you can spare. And a dildo, if you have one. A normal-sized dildo," I added quickly. "And a butt plug. A small one."

Courtney whipped her head around to stare at me and her mouth opened in shock. I ignored her and kept my eyes on Erin.

"Courtney Bellinore," Erin said, affecting a shocked tone. "Are you really planning to let this man fuck you up the ass?"

Courtney turned back to Erin, wide eyed, and shook her head vigorously. "I-what? No!"

"Have you seen his cock, honey? It's huge." Then she laughed. "What am I saying? Of course you've seen it."

Courtney moved her mouth but found no words. She looked to me for help, her eyes pleading, as if to beg me to put her out of her misery. I put my hand on her ass and squeezed one of her ample butt cheeks. She jumped.

"Don't worry about us. We'll be just fine," I assured both of them. "Can we borrow the stuff, or not?"

Erin lifted her eyes, as if considering the request, then nodded. "Of course. I'd be delighted to help. You want to wait here, or would you like to come up with me to get it? Courtney, honey, you can wait here till we get back, right?"

"We're both fine, right here," I said, my voice low.

Erin's lips lifted and she shrugged. "Can't blame a girl. Wait here, then. I'll be right back."

When Erin had left us alone, Courtney exhaled the breath she'd been holding and clutched my arm with both hands. "What the fuck are we doing here, dude?" she said in a harsh whisper. "A dildo? A-a-a butt plug?"

"Relax. I already told you, she knows everything. We need this stuff."

"She-she fucking talked about my tits, dude. Ash's mom complimented my tits!"

"Would you please calm the fuck down?" I asked, annoyed. "I already told you that too."

"Told me what?"

"That you've got great tits."

"You're not funny, dude! I've known her since I was eleven."

"I don't know what to tell you. Get over it. This isn't the last time she's going to see us naked."

"What does that mean?" she asked, alarmed by how casually I'd said it.

"I don't intend to hide in that pool house anymore. I wasn't joking about what I said to Ashley. I plan to fuck you all over this property, inside and out."

Courtney's jaw dropped and she yanked on my arm. "No! Are you fucking kidding? Please tell me you're just fucking with me."

"I'm not fucking with you. And what's your problem? Why are you acting like this?"

"My problem? Acting like what?"

"Like a fucking child."

She stared open mouthed. "How can you say that?"

I yanked my arm away from her. "Because it's true. You don't think Erin knows what time it is? Wake the fuck up, Courtney. She knows everything, okay? She and Clay are a couple of fucking swingers. They host orgies, right here in this fucking house."

Her head snapped back as if I'd slapped her. "What?"

"Yeah, you heard me right." I took a deep breath and leaned closer, fixing her with a hard look. "You want to be the perfect girl for me? You want to do anything I want? Well, this is it, baby. This is your moment. I want to fuck the shit out of your little pussy right out in the open. I'm tired of hiding. You're not up for it? Fine. But don't fucking bullshit me again about you being completely honest with me, and not caring about what other people think, and blah blah blah and all that other shit, because at the end of the day you'll just be another spineless virgin girl with a horny twat and a head full of lusty ideas, but no balls to do anything about either."

"Should I come back?"

I turned. Erin stood in the doorway holding her cocktail in one hand and a black sinch bag in the other. I wasn't sure how long she'd been standing there, but I couldn't have cared less.

"That it?" I asked, and she handed the bag over to me.

"Everything's been sanitized. If you need anything else, let me know," she said. "I've got all kinds of really good stuff up there. Maybe you and I can browse through the collection later and see if anything strikes your fancy?"

"Money," I said flatly.

She sighed. "Talk to Ashley. I already gave it to her."

"Great. Thank you. Let's go, Courtney."

Courtney gave Erin one last gawk and turned to follow.

"If you really are planning to fuck outdoors," Erin called after us, "please remember to use sunscreen. Especially you, honey. You don't want to burn those tits. Believe me."

Chapter 27 - Courtney's Porno

When we'd made it back to the side of the house, Courtney grabbed my arm to stop me.

"Dude, what the fuck, man? What was that?" she asked.

"What was what?"

She pointed back to the house. "That! We just walked naked into Ashley's house and asked her mom for dildos and butt plugs, and she just handed them to us like it was no big deal!"

"Are you not paying attention to anything I've been telling you?" I asked, and turned to go, but she pulled me back.

"Would you hold on for just one second? Please!"

I stopped and turned to face her. "What, Courtney? What?" My annoyance with her peaked and it showed on my face. She rubbed my arm.

"Just...talk to me, okay?"

"Talk to you about what? There's nothing to talk about."

Her eyebrows parted and her face became a mask of glum emotions. She looked scared and confused and unsure of what to do or say. I put my hands on her shoulders and leaned forward to touch my forehead to hers. I closed my eyes and sighed.

"You frustrate the hell out of me sometimes, you know that?" I said under my breath, then pushed her back to hold her at arm's length. "Do you want this or not?" I asked.

She stared at me and thought about it, but she didn't seem nearly as certain now as she'd pretended to be in the pool house. Two small tests had shaken her resolve, and I could tell she wondered if she could go through with it at all.

"You wanted to be my dirty little whore, Courtney. You wanted me to fuck you any and every way possible, and you didn't care what anyone else thought anymore. That's what you said to me."

"I know!" she whined. "I just didn't think..."

"Because you don't know anything. Look, I don't want you to be my whore, okay?"

She looked devastated. "Why not?"

I chuckled and shook my head. "Because, you're not a fucking whore, that's why. It's not in your nature to be one. You're...something else."

"What, then? What am I?"

"I don't know yet, because you won't tell me. You keep trying to be something you're not, and it isn't working. I've asked you countless times to tell me what you want. What you really want, not what you think I want to hear. So, tell me the truth this time. What do you want?"

"I want to be with you," she said, and I knew, if nothing else, she'd told the truth that time.

"You are with me. We're together, right now."

Frustration showed on her face. She wanted something else too, she just didn't know what. Either that, or she didn't have the words to tell me. I held her firmly.

"You're a leader, Courtney. You're not a follower. Those girls in there look up to you. They respect you, and they rely on your strength. You're a fighter and a protector. Like me."

Her eyes widened with realization.

"Maybe you should be my protégé," I said impulsively, and she looked confused. "You know what that means?"

"Like a student?" she guessed.

"It's more than that. As your mentor, I can teach you all the stuff I know about sex. Not just how to do it, though. I have a lot of other experience that I think you could benefit from too. Stuff that goes in here," I said, tapping her temple. Then I lowered my hand to brush her pussy. "Not in here. Knowing how to read people and situations, knowing when to talk and what to say and when to shut up and when to listen. Being savvy, street smart, patient, adaptable, those kinds of things."

Her face filled with wonder and her mind raced. She seemed energized and excited by the prospect of deeper learning. Then her eyebrows closed in.

"Would we still get to have sex?" she asked.

I laughed. "If you want," I replied and she breathed a sigh of relief. "So, do you still want to be my little whore?"

Courtney cast her gaze aside and smirked. "Not...really," she admitted, then looked at me and added, "Unless you want me to." When I tilted my head and frowned, she backpedaled. "I mean, no. I just want to fuck you. A lot."

"Do you still want to try anal?" I asked, and she paled.

"I don't know. I only said that because I know you really like it, but I'm kind of scared it'll hurt too much."

"Yeah, you do have a tiny asshole. I've seen it. Do you like it when I put my finger in there?"

She smirked and said, "Yeah, that feels really good."

"Alright, we'll start there and see where it goes. Is there anything else you told me in there that you want to take back?"

She thought about it for a while and shook her head. "Look, I just want to make you feel good, okay? And I want to be open to trying new things. So, most of what I said in there still holds as far as I'm concerned."

She put her hand on my face and smiled. "And I do trust you. I really do. I know you're looking out for us and I appreciate it and I know we don't say it nearly enough, but thank you for everything you've done for us so far. It really means a lot. To all of us."

I put my hand over hers and sighed, grateful for her appreciation. She rubbed her thumb over my cheek and her smile faltered.

"Dude, would you mind doing me a favor?" she asked.

"What's that?"

"Would you please shave? The stubble looks hot and all, but it's scratchy as hell when you go down on me."

I rubbed my cheek. I hadn't shaved in a day and it felt like sandpaper. I realized I needed a touch up down below as well. I reached down and rubbed my hand over Courtney's vulva, causing her to jump.

"I will if you will," I said. "It's like going down on a hairbrush."

Her mouth came open and she slapped my arm and we laughed together. Then I had another idea.

"Actually, have you ever had your pussy waxed?" I asked.

"No...why?"

"How do you think everyone would feel about having a spa day?" I asked. The idea intrigued her and she lifted her eyebrows. "Brittney needs a haircut bad," I said, "and Kayla needs some serious trimming of her own. You can all get hair and eyebrows and facials and manicures and pedicures and bikini waxes and all that good stuff. What do you think?"

"I think that sounds fucking awesome!" she said, excited. "But isn't all that stuff super expensive?"

I grabbed her hand and led her back to the pool house. "Don't worry about that," I said. "We're venture backed now."

Back in the pool house, I tossed the sinch bag onto the coffee table and went for another glass of water.

"What's this?" Ashley asked, picking up the bag.

"Some of your mom's dildos and butt plugs and stuff," I said between chugs of water.

"What? Ew!" Ashley shrieked, tossing the sack down like it was full of snakes.

Courtney laughed as she fell backwards onto the chaise with her arms outstretched. "You wouldn't fucking believe what we just did, Ash," she said.

"My mom had these?" Ashley muttered to herself.

Courtney flipped over onto her stomach and rested her chin on her laced fingers, kicking her legs. "We walked in there, buck naked, and asked your mom to give them to us and she fucking did! Can you believe that?"

Ashley's head popped up and then she turned to look at me as I refilled a second cupful. I leaned against the countertop and gulped it down.

Kayla opened the bag and pulled out a six inch, flesh-toned dildo. She shook it and the tip wobbled a bit. She set it down on the table and pulled out a small red butt plug, about an inch in diameter. Then another one, nearly twice as big. Then she lined up bottles of lube on the edge of the coffee table. Five in total. No, four. The fifth bottle contained isopropyl alcohol. Erin had come through.

Brittney picked up the dildo and examined it with fascination. She pressed her finger against the tip and bent it over a bit, testing its material properties. Ashley withdrew onto the cushions and hugged her legs to her chest.

"There's no way I can use those," she said. "Ew, Kayla! Stop touching that. It's been up my mom's..." She couldn't bring herself to finish the sentence.

"Probably your dad's too," I said. "She sanitized them, though."

With my stomach pleasantly full of water, I went to the table to examine the bottles of lube. I picked one up to read the label. Cherry. Fuck.

"Ugh! I don't care! It's fucking gross!" Ashley whined, cringing behind her arms. "Kayla, stop that!"

"Ashley!" I snapped, and she whipped her head around. "Get over it, for fuck's sake! If you don't want to use them, fine. But shut the fuck up about it, already. I'm sick and tired of all your whiney ass, pearl clutching, overwrought drama bullshit!" I said, slamming the bottle of lube back down onto the table.

Everyone grew quiet and Ashley peered at me over the top of her eyeglasses. I stared her down for a second, and then picked up the small butt plug from the table.

"A few of you want to explore anal sex," I said, "but you're not going to get my cock in your ass on the first go. It's too big. These butt plugs will help you train your assholes to accept larger things." I set it back down and picked up the dildo. "This is for everyone to practice different techniques or simply to masturbate with. I also got it in case anyone's interested in trying double penetration, so you can have two cocks inside you at the same time." I picked up a bottle of lube. "And we need to keep everything nice and slippery so no one hurts themselves. You all have fantastic, wet pussies, but everyone has their limits and my cock is starting to hurt from all the friction."

I put everything back on the table and sat down next to Kayla, who picked up the small butt plug again and examined it closely. I reached over the table and grabbed a pump bottle of anal lube and handed it to her.

"Use this. It's thicker and better for anal insertions," I told her. "You want to try it?"

"Now?" she asked, sounding nervous.

"No, next week. Yes, now. You asked me to fuck you in the ass. This is how we do it. Stop worrying about them!" I yelled when she glanced around at the others.

I pushed up from the couch and paced around the room, slicking back my hair with my hands. I felt so agitated and impatient with them, and it bothered me to be that way but I couldn't help it. Why did I have to be such a fucking prick to them all the time? They're only eighteen, I reminded myself. They don't know any better.

I turned to face them, my expression contrite. "I'm sorry. I shouldn't talk to you guys like that. You don't deserve it. I'm just not cut out for this, okay? I'm too fucking selfish. I'm used to getting what I want all the time, and it's not fair to you, and I forget sometimes that you asked me to teach you this stuff because you don't know anything but you want to learn and I need to be more patient with you. So, yeah...I'm sorry."

Ashley lowered her legs and Kayla set the butt plug and lube back down on the table. Courtney looked at her friends and stood up to speak for them.

"We know you're doing the best you can, dude, and no one's expecting you to be perfect all the time, okay? But we're new to all this. I know you're this fucking Jedi sex master and shit, but we're not. We're trying really hard, though, and we trust you and all, but maybe cut us a little slack, okay? Some of this shit's a lot harder than it looks. Especially for girls."

I laced my fingers behind my head and nodded. "Yeah. Fair enough," I said and Courtney sat back down.

Ashley leaned over the table and gingerly picked up the dildo with two fingers. Then she gripped it by the shaft and shook it the way Kayla had. She set it back down.

"I'll try to be less whiny," she said when she'd leaned back into her seat. "I just never knew...my mom..." She shook her head, astounded by the revelation of her mother's sex life.

There was so much more I wanted to tell Ashley about her mother, but what good would it do? It would only traumatize her more. No, some things were better left unsaid. She already had plenty to process.

The sun had descended rapidly and would set soon enough, but I figured we still had about six hours before Clay returned. Plenty of time for more instruction. But first, I needed to assess our financial position.

"Ashley, your mom said she gave you some money. Is that right?" I asked.

She sat up straight. "Yeah, sorry. I meant to tell you about it when I brought you your food, but I got kind of distracted."

"Did she give you cash or something?" I wondered.

"No. I'm an authorized user on one of her credit cards. She said I can use it to buy whatever you thought we needed."

"What's the credit limit?" I asked, but she shrugged her shoulders. "I want us to go out for a spa day tomorrow and do some clothes shopping. Then we're going on a field trip," I said with a sly grin.

"Field trip? Where?" Brittney asked.

"It's a surprise, but you guys will have fun, trust me. Is everyone free tomorrow?"

"I have to go home tonight," Kayla said, disappointed. "My parents haven't seen me since Friday, so they're kind of insisting I come back, at least for a night. I'm free tomorrow, though."

"My mom's been blowing up my phone too," Courtney said. "I was going to head back home tonight as well, but I'm totally down to hang tomorrow."

"You want to borrow my car?" Brittney offered. "I don't need to go anywhere tonight. You can take it and bring it back tomorrow. If it's okay for me to stay here again, Ash."

Ashley grinned and scootched over to hug her friend's beefy arm. "Of course it's okay. We can play Genshin tonight after my dad gets home."

"Speaking of that," I said. "We still have quite a bit of time left before he gets back. What do you all want to do with the rest of the day?"

Kayla sat up on her haunches. "I believe you mentioned something about going down on me earlier? If the offer still stands."

Courtney jumped to her feet, slicing her hands through the air. "No fucking way, you cows. I'm next."

Brittney snorted and said, "I just realized, Court. You're the only one of us who's never had sex."

Ashley and Kayla joined Brittney in a good-natured laugh at their friend's expense. Courtney glowered.

"Ha fucking ha, bitches," Courtney jeered. "You were a virgin two hours ago, Brit, so don't act like you're hot shit now."

"Jealousy," Brittney tsked, shaking her head. "It's so ugly.

"Me? Jealous of you? Ha! Hardly." She lifted her breasts in her hands. "Check these babies out."

Brittney lifted hers as well, saying, "I've got two of my own, Booberella, and I've been told their perfect."

Courtney narrowed her eyes and huffed. "Yeah. They're pretty fucking great," she admitted, and dropped hers back down, ending the standoff. She turned to me and asked, "So, how 'bout it, dude? Are you finally going to fuck me now, or what?"