The First Timers Club
Copyright© 2022 by Alex Weiss
Courtney the Whore
Coming of Age Sex Story: Courtney the Whore - Ashley and her three best friends are high school outcasts. Four virgin nerds who have never dated or even kissed a boy. At Ashley's sixteenth birthday party, the four girls strike up an unlikely friendship with a new acquaintance of Ashley's parents. A handsome older man with a dark past who agrees to become their sexual mentor. But Ashley's mom has plans of her own for the mysterious new stranger in their midst.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Ma/ft ft/ft Fa/ft Mult Teenagers Consensual Drunk/Drugged Reluctant Lesbian BiSexual Heterosexual Tear Jerker MaleDom FemaleDom Light Bond Rough Spanking Group Sex Anal Sex Cream Pie Double Penetration Exhibitionism First Facial Massage Masturbation Oral Sex Sex Toys Tit-Fucking Voyeurism BBW Menstrual Play
“So, how come it’s okay for you to call us sluts?” Courtney asked me.
She’d politely waited to ask the question until after Brittney and I had both rinsed off in the shower to rid ourselves of the dried blood and sweat that still clung to our bodies. We all lounged together on the sectional while porn played in the background, though the sound had been muted. I sat with my arm over the seat back, still feeling soreness and stiffness in my shoulders from being tied up and holding Brittney’s hair for so long.
“When any of us calls someone a slut,” she continued, “you get all pissed off and high and mighty and shit. But then you’re all calling Brit a slut and a bitch and slapping her around and stuff, and that’s somehow okay? Why? Because you’re a dude?”
I shook my head. “No, of course not. I only did it as a sex thing, because I thought that’s what she wanted. I’d never call her those things any other time, and if it bothered her, I wouldn’t do it ever.” I turned to Brittney, realizing I hadn’t talked to her about it. “Did it bother you?”
She laid reclined like a Titian Venus on the chaise, still naked and dewy from her shower, her long damp hair flowing around her. She thought about it and shook her head.
“No, it kind of turned me on, to be honest,” she said. “But I definitely wouldn’t like it if you said it now,” she added after a moment of reflection.
“Why do you think it turned you on?” I asked. She’d been more open about her thoughts and feelings regarding sex since our encounter, and I wanted to encourage her by giving her every opportunity to talk about it.
“I’m not sure. It was pretty demeaning the more I think about it. Like, if someone else had talked to me that way, you know, like during sex, I’m not sure I would have liked it as much. But the way you said it ... I don’t know, it was like you only said it because you were...”
“Because I was what?” I asked when she trailed off, prodding her to finish her thought. She tilted her head and sighed uncomfortably.
“This is going to sound super conceited,” she said.
“So what. Tell me anyway.”
Her face flushed and she played with her hair. “I don’t know. It was like, you were hot for me or something,” she said, gauging my reaction, “and I think the reason I liked it so much is because no one’s ever thought about me that way before.” Her voice trailed off again and she looked away. “God, that sounds so pathetic.”
Kayla looked at her friend and nodded slowly, as if in commiseration.
“Well, you’re exactly right,” I confirmed, and Brittney’s eyes came up. “I was hot for you, and I still am. I keep trying to tell you, Brittney, you’re sexy as hell.”
The smile that warmed her face panged me, and part of me regretted saying that to her. Not because it wasn’t true. I did find her sexy and she did turn me on. But I didn’t want her to get the wrong impression about what that meant or how I felt. I thought fondly of Brittney, and I appreciated her kindness and her willingness to explore herself with me, but my feelings for her were strictly platonic. I strongly suspected, however, that hers had become increasingly romantic. I changed the subject.
“Speaking of sexy as hell, how is everyone feeling right now?”
I scanned the couch, observing their faces. Brittney appeared the most relaxed, still glowing from our romp. Kayla sat cross legged next to her with her hands folded in her lap, still naked from the waist down. She smiled and shrugged when my eyes passed over her. Despite how uncomfortable it looked, Ashley still wore her fantasy costume. She seemed pensive, though, and her face showed traces of worry. I furrowed my brow.
“What’s wrong, sexy?” I asked.
“Nothing,” she said, trying to cover her emotions with a weak smile. “Just thinking.”
“About what?”
She glanced at Brittney before responding. “I don’t know. I guess I’m still a little freaked out about ... you and Brit.”
“Because of the blood?” I asked, but she shook her head, addressing her concerns directly to Brittney instead of me.
“No. Well, maybe a little, but we all get our periods, right? So I get that. It’s just ... the way he treated you and those things he said, and the way you were screaming and crying. It was just so awful, Brit, and I wanted to help you and make it stop, but Kay told me not to, and then I heard you say how much you loved it and ... I don’t know. I just wanted to know that you were really okay.”
Ashley lifted her glasses and dabbed at the wetness forming in her eyes. Brittney looked at me, astonished, but I did my best to disguise my thoughts and said nothing. With no prompting from me, she sat up onto her hip.
“I-I’m sorry, Ash. I didn’t mean to scare you,” she said.
Ashley scoffed and looked embarrassed. “No, I’m sorry. He warned us that it might be like that, and he said we might not like what we saw, but I just ... I never expected that.” Fresh tears broke free and spilled down her cheeks. She took a deep breath to calm herself and wiped them away. “I was just so scared for you,” she said, and her voice cracked.
The sight of her friend crying set Brittney off, and her eyes welled until tears fell from them. Her lips trembled and she rushed to Ashley to wrap her arms around her and the two friends cried together.
“I just love you so much, Brit,” Ashley said, her words choked, and Brittney hugged her even tighter.
“I know. I know you do. I love you too, Ash.”
Kayla and Courtney looked on, each of them appearing to be on the verge of tears, and even I felt a swell of emotion watching the two friends comfort each other. It reminded me once again just how emotionally vulnerable these girls really were. Despite the bravery they’d demonstrated so far, they were still young and, in almost every way, so incredibly naïve when it came to sex and relationships with men.
The weight of responsibility I felt to not fuck it all up made me question whether or not I was cut out for it. I needed to be a good role model and set an example of what a healthy sexual relationship with a man should look like, but I’d done a piss poor job of it so far and felt to be just about the worst person on the planet to do it. Nearly every relationship I’d ever had with the women in my life had revolved almost entirely around sex. I loved sex and I loved women, and my tastes and predilections ran to the extremes. Restraining myself with these girls had been the hardest thing in the world for me to do, and I grew increasingly worried that it was only a matter of time before I hurt one of them. I wasn’t sure if I’d be able to live with myself if I did.
When Ashley and Brittney regained their composure, they settled back into the sofa next to each other, sniffling and holding hands. Brittney looked at me and flashed me an embarrassed smile.
“Sorry,” she said.
I shook my head and waved my hand. She didn’t need to be sorry. We sat quietly for a long time, not really looking at each other, until Courtney finally broke the silence.
“So ... how about them Mets, huh?”
Ashley smirked and then breathed an amused snort from her nose, which triggered a cascade of tittles from the others until soon they all laughed, as much at the absurdity of the comment as to dispel the somber mood. When their laughter subsided, Kayla drew her knees up and hugged her legs.
“What’s everyone up for now?” she asked, looking at me but addressing the entire group.
“I could eat,” I said when no one else spoke up. I’d barely eaten anything in days, and what little I had consisted mostly of garbage and booze. I’d also noticed that the load I’d dumped on Brittney’s ass was a lot smaller than normal. An indication that I was dehydrated.
“I can make you something,” Ashley offered. “What are you hungry for?”
“Your pussy,” I said, and she cracked an amused smile. “Oh, you mean food-wise? I don’t care, honestly. Anything, really, but something fresh and healthy would be amazing.” I suddenly craved a grilled chicken sandwich piled high with lettuce and tomato and my stomach grumbled.
Ashley got up to strip off her costume and put her street clothes back on, skipping the underwear.
“Don’t move. I’ll be right back,” she said cheerfully and skipped out the slider.
Courtney watched her go, then turned to me when she’d disappeared.
“So, how are you feeling?” she asked, her meaning obvious.
“A little sore, to be honest,” I said, rotating my arm.
The ache in my shoulders hadn’t just been a mild strain, I finally admitted to myself. I must have pulled something when I’d been tied up, and gripping Brittney’s hair had only made it worse. Yet another reminder of my age and the generational gulf that separated me from these girls.
My cock also felt chafed from the near continuous sex I’d had over the past couple days and the lack of lube, but this also underscored just how reckless I’d been. I hadn’t used a condom with any of them, and twice now, poor Courtney had unknowingly sucked my cock straight from Erin’s ass. I had so much casual sex in my normal, day to day life, sometimes with multiple partners in a day, that I routinely got myself checked for STDs, but I hadn’t been tested in weeks. Between myself and Erin, these girls had indirectly been exposed to dozens of dicks, pussies, and assholes.
A true paragon of responsible sex you are, I thought sourly.
Courtney sat up straight. “You’re not ... injured or anything are you?” she asked, her concern as much for me as for herself, I suspected. I chuckled softly.
“No, nothing like that. I just think I might have pulled something earlier. I’m fine though,” I lied.
She looked relieved. “Good, good. That’s good. How’s your, uh...” She waggled her finger at my cock.
“He’s very, very happy,” I said, raising an eyebrow to Brittney. Her face reddened and she grinned.
“Uh huh, yeah, that’s great,” Courtney said quickly. “But you’re still feeling good, right?” She punched her fist into her hand like a baseball mitt. “You’re still, you know, good to keep going?”
I laughed again. “Is your little beaver eager?” I asked.
She scoffed and tried to laugh it off. “Ew, no. No, I just want to make sure you’re not too tired or need to take a break or something like that.”
I sighed, exasperated. “You know, I feel like I keep having this conversation with you guys every other hour,” I said.
“What are you talking about?” she asked, wary.
“I’m talking about you girls constantly tap dancing around the things you want. Just fucking come out with it. Tell me what you want, directly and plainly. Why is that so fucking hard for you to do?”
She shot me a pained look. “Hey, sorry, okay? I just don’t want you to think I’m, like, desperate or something.”
“Oh my god, Courtney.” Ugh, these girls frustrated me to no end. “In fact, I want all of you to listen up,” I said, and the three of them leaned forward to give me their undivided attention. “I like you guys, okay? A lot. All of you. And I love fucking you. When you tell me you want to fuck me, it’s like the greatest thing in the world. You guys could never want sex more than I do. Well, okay, maybe Kayla could, but that’s only because she’s my sexy little nympho.”
Kayla flashed me a steely grin, and I continued. “I should probably wait for Ashley, but I suspect I’ll be repeating this again several times, so I’ll just say it. Everyone wants to feel wanted, okay? Even me.”
This brought them up short, and I laughed. “Yeah, that’s right. You’re not the only ones who want to feel good about themselves, and it makes me feel really good to know that I’m desired. It’s thrilling and it excites me, and it only makes me want you more.”
“But dude, you could get any girl you wanted,” Courtney said, and I choked out a laugh.
“Yeah, hardly.”
“Hardly? What the fuck, man? You’re, like ... And, I mean, you always know exactly what to do and say all the time!” she said, sounding agitated.
“You’re kind to say that, but I’m not nearly that smooth. I’m just like you, making it up as I go.”
“Dude, just shut the fuck up!”
“Why are you getting so angry?” I asked.
She stood and tossed her hands out. “Because, I don’t fucking believe you! You are so unbelievably hot, you don’t even seem like a real person! And you’ve got this, like, huge dick that you obviously know how to use really fucking well, and everyone’s totally into you and wants to fuck you and...” She bore her eyes into me. “It just insults my intelligence when you deny it, okay? That’s why I’m fucking pissed.”
I lifted my eyebrows. “Wow, okay. I’m sorry. Thank you.”
Courtney plopped back down onto the sofa and crossed her arms in a petulant pose. “Yeah, don’t mention it.”
“Told you,” Kayla said to me, shrugging. When Courtney looked at her confused, she explained. “I told him pretty much the same thing last night.”
“So?” I asked Courtney, regaining her attention.
“So, what?” she asked testily.
“So, what is it you want from me?”
Her frustration with me erupted. “Dude! I want to fuck your brains out, okay? Is that clear enough for you?” She pantomimed speaking in sign language. “I. Want. To. FUCK! The. Shit. Out. Of. You.”
I stared at her and shook my head. “I don’t understand. What are you trying to say?” Her eyes bugged out of her head and I stuck out my tongue. She screeched.
“Argh! Oh my god, I’m going to fucking kill you!” she screamed and lunged at me, leaping on top of me and grabbing my wrists. I let her wrestle me down onto the cushion and she attacked my face with her lips. Her tongue shot into my mouth and she ground her crotch against my growing erection.
When she had me firmly under her control, she pulled her head back to look at me, her expression serious. “I want you bad. You have to know that, right?”
“How bad? Tell me. Please.”
Her jaw flexed and she shook. “So bad that I can hardly stand it. So bad, that my f-fucking pussy constantly aches for you. So bad, that I have to stop myself from just throwing myself at you every time I see you.”
“Courtney...”
“I’m not done yet, mister, so you just shut your perfect fucking mouth and let me finish, because I have a lot more to say to you and I’m going to be completely honest because I don’t give a fuck what anyone else thinks anymore.” She looked up at Kayla, “Not you.” She shifted her eyes to Brittney. “Not you.” She looked down at me. “Not even you.”
She moved her face closer. “I want you to use me every way possible. I want you to put your cock in my mouth. I want you to fuck my tits. I want you to fuck my pussy. I want you to fuck my ass. I want you to fuck me and fuck me and then, when you’re done fucking me and I’m lying on the ground shivering and covered in your cum, I want you to fuck me some more. I want to go to sleep tonight still feeling your cock inside me because you fucked me so much. Do you get it now? Is that plain enough for you?”
Although sore from overuse, my cock throbbed and surged against her weight. She glanced between her legs and nodded. Her trembling intensified.
“Good. Now, since everyone else got what they wanted, let me tell you what I want. You’ll tell me what to do, and I’ll do it because I trust you completely. I don’t care what it is, I’ll do it and I won’t question it. You won’t hurt me, either, okay? You can’t hurt me. I’m strong. I can handle it, and I want it. I w-want it more than I’ve ever wanted anything before in my life.”
She exhaled a sharp stuttering breath. “I don’t want to just be your slut, okay? That’s not nearly enough for me. I want you to treat me like a dirty little whore because that’s what I am. I’m desperate for it. I want you to slap me, spit on me, call me names, piss in my fucking mouth for all I care. You can do anything you want to me because that’s what I want. I want all of it. So don’t hold back, okay? I want to be the perfect girl for you, so please use me any way you want, okay? Will you do that for me, please? Say you’ll do that for me.”
She quivered like a violin string, awaiting my response. I stared into her large brown eyes, so filled with anxiety and wanton desire, absolutely speechless. I’d never been propositioned like that before, and I felt conflicted because it had come from her. Courtney Bellinore. A virgin who couldn’t possibly know what the fuck she wanted. Couldn’t she?
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