The First Timers Club
Copyright© 2022 by Alex Weiss
Jacking and Jilling
Coming of Age Sex Story: Jacking and Jilling - 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
I collected myself and gestured to Brittney. “You’re up, hot stuff.”
She tore her eyes from Kayla and then stood with somewhat less certainty than she had the first time I’d called on her. Her eyes drifted to my cock, and I looked down to see a string of precum dangling from the tip. I looked up again and our eyes met.
“Precum,” I said, answering her unspoken question. “When I get really turned on or stimulated, it starts to leak out. Sometimes, a lot. It’s like when you’re pussy gets wet when you’re thinking about sex.”
Brittney gawked at me with an astonished look on her flushed face. Her chest had similarly reddened, and her lips were the color of ripened strawberries. She was incredibly turned on. When she realized that everyone was waiting for her to speak, she cleared her throat.
“I, um ... I don’t really like anything about myself,” she said at last, casting her eyes to the side. Eventually, they drifted back in my direction, and I could tell she was looking at my dick again.
“What do you dislike the most? More than anything else?” I asked. Her eyes lifted and she shrugged her broad shoulders. “There must be something.”
“I’m too big,” she answered, her face reddening even more.
“And why does that bother you?”
“Because I’m huge. I’m bigger than all the boys in my class, except a couple of the football players. I mean, I’m even bigger than you! And everyone thinks I’m a lesbian because of it. I get called a dyke or a huge bitch and people make stomping noises whenever I walk by. I’m just a big, tall, fat, ugly girl,” she said bitterly. Then she looked away again, trying to hide her face and the tears that brimmed in her eyes.
Fucking fuck these fucking asshole pieces of shit! Was that the legacy that Clay and Erin and their friends had left behind? A gladiator school, where the strong picked on the weak and you found pleasure in tormenting teenaged girls? I imagined slowly peeling back a finger and hearing the bone snap.
“Dude, are you okay?” Courtney asked.
I flicked my eyes to hers and saw the concerned look on her face. I hadn’t realized that I’d balled my hand into a fist and clenched my jaw into a grim visage. I relaxed and took a deep breath, affecting a serene smile. I even managed a small laugh.
“Yeah, I’m fine. I was just thinking about my kiss with Brittney in the pool.”
“Really? Because you looked fucking pissed,” Courtney said, unconvinced.
“I feel things very intensely,” I said by way of a lame excuse, then addressed Brittney. “Okay, so you’re tall. But the way you’re put together and your proportions are just right. Don’t forget, I’ve seen you naked. I know what you look like under that baggy hoodie and those sweat shorts. You’re the one who made my cock hard, remember?”
At the mention of it, Brittney lowered her eyes again. I had started to soften but remained mostly erect. She nodded dumbly.
“A lot of guys prefer tall girls and, personally, I love them. Especially ones with curves like yours. You’ve got everything you need to be one of the hottest girls in your school. I’m not joking about that, Brittney. You’ve got the face, the hair, and the body. You just need the confidence to tie it all together.”
Brittney looked at me and smiled weakly, appreciative of the effort, but she remained unconvinced. I don’t know if it was because I’d said something upsetting, or if my angry scowl beforehand had spoiled it for her. I wouldn’t dwell on it, though. A plan for Brittney formed in my mind. One that would convince her once and for all that I’d spoken the truth.
“Courtney, you’re up.”
Brittney slumped down onto the couch and Courtney popped to her feet. She seemed to have become invigorated by my little show with Kayla, and she smiled mischievously.
“Well, if you’d asked me this question yesterday, I would have given a totally different answer. But that’s kind of changed now, so I’d have to say my acne. I fucking hate it. It’s all over me. On my face, my shoulders, my chest, my back, my butt. Ugh! I keep hoping it’ll go away on its own, but it just seems to get worse every year. I know I should probably be taking Accutane for it or some shit like that, but it’s so expensive and I don’t want to have to live inside all the time like a hermit, so...” She shrugged her shoulder. “Yeah. That.”
I’d already had a discussion with her about that topic, but for the sake of the others, I repeated most of it again. Plus, she already knew how attracted to her I was despite it. I also pointed out that it was likely a transitory issue, but even if it wasn’t, it was certainly treatable.
“Plus, I hear cum is good for your skin. Not sure if that’s true or not, so maybe that’s something we can test out,” I said.
Courtney smirked. “Hm, maybe,” she said before sitting back down.
“Okay, so, inhibitions,” I said, launching right back into my discourse. “Another type of inhibition that controls our lives and is definitely not a survival instinct is shame. Shame is something we totally made up as a way to control people’s thoughts and actions by setting up arbitrary rules. And it’s always socially enforced too. You know, the pack attacking anyone who strays too far from what’s considered acceptable, and it’s total bullshit.”
Kayla leaned back into the sofa cushions and spread her legs a bit. The wetness of her pussy glistened beneath her thick, dark bush and I felt a twinge in my cock.
“Being free from shame is hard, though, because it means not giving a fuck about what other people think about you. And that can be lonely sometimes, especially if you prefer spending your time hanging out with a bunch of prudes who want to police your behavior and gatekeep your life. Personally, I prefer to spend my time with the freaks on the fringe. They’re a lot more fun, they don’t treat you like shit, and you get to have a lot of hot, sweaty, guilt-free sex.”
This comment elicited smiles from the girls, especially Courtney and Kayla.
“Kind of similar to shame is taboo. They’re like the yin and yang of inhibition. You can think of a taboo as the rule, and shame as the tool of control and punishment. Now, taboos are also made up, but not all of them are bullshit. In fact, some of them I happen to agree with. You know, like not eating people and things like that. But most taboos are total bullshit too.”
“One taboo, in particular, that really pisses me off and, quite frankly, makes absolutely no fucking sense to me at all, is society’s crusade against masturbation.”
At the mention of the word, I noticed several changes of expression and uncomfortable shifts in posture.
“I see you’ve heard about it,” I joked. “First thing to know: everybody masturbates. Everybody. Everyone in this room has probably masturbated in the past couple days, maybe in the past twenty four hours. I did, just before I came to the party. So, the question isn’t whether or not you masturbate, because you absolutely do. The only question is, how often?
“But there’s a bit of corollary taboo in there too, because if masturbating is bad, then masturbating a lot must be worse, right? Or so they’d have you believe. But the fact is, how much you masturbate depends almost entirely on your sex drive.
“Some people have a really high sex drive and need to masturbate or have sex more often, and some people have a low sex drive and need it less. It’s all biological and has nothing to do with morality. It’s just another stupid fucking rule to control your life and make you feel ashamed for engaging in perfectly normal behavior.
“Just like before, we’re going to go around, and everyone is going to say how often they masturbate. I’ll go first. I have a really high sex drive so, for me, it’s usually a couple times a day, but sometimes more if I’m really fucking horny.” I pointed at Ashley. “What about you?”
She looked nervously at her friends and hesitated to answer. I held up my hand and nodded.
“Yeah, I get it. Those inhibitions run deep and they’re really fucking strong. I totally understand. But we just established that everyone in this room masturbates, okay? Ashley, I know for a fact you masturbate. Courtney? She masturbates. Kayla masturbates. Brittney masturbates. I masturbate. We all do it. So, it makes no sense to feel embarrassed about something you, and literally everyone else around you, does.” I pointed at her again. “Quick, yes or no. Don’t think about it. Do you masturbate?”
“Yes,” she said, quicker than even she expected.
I pointed at Courtney next. “Yes.” Kayla. “Yeah.” Brittney. “Yes.”
I swung my finger back to Ashley. “Once a day. More, less, or the same?”
“More. No, less. Wait, the same,” she finally chose.
Courtney. “Less.”
Kayla. “More.”
Brittney. “Same.”
“Okay, so Kayla, you’re like me. We’re both high libido. You said more. How many times a day would you say? Twice? Three times?”
“Three or four. Sometimes more.”
Wow.
“Ah, so you might be what’s known as hypersexual,” I said, and Kayla’s eyebrows knotted together. “You ever hear the term ‘nymphomaniac’ before? Same thing. I’m borderline myself. Let me guess. You probably live in a state of near constant arousal, am I right? Even if it’s just low level?”
Kayla thought for a moment and nodded. Then she spread her legs a little wider, and I could see a large wet spot had formed on the cushions of the sofa. My cock throbbed at the evidence of her arousal.
“Okay, good. Courtney, you said less. Would you say once every couple days? Once a week? Less?”
“Maybe a couple times a week. It depends. Sometimes it’s more if I’m in a certain mood or depending on my cycle.”
“Makes sense.” I pointed at Ashley again. “Fingers, vibrator, or dildo?” When she hesitated to answer, I added, “Don’t think about it, just answer. Fingers, vibrator, or dildo?” I already knew the answer, and she knew I knew, but I wanted her to say it out loud so the shame of it wouldn’t have any hold on her.
“Vibrator,” she blurted, and then added, “And fingers.”
I nodded and pointed at Courtney. “Fingers.”
“All,” Kayla said, “but mostly dildo and vibrator.”
“Fingers,” Brittney said. “But I’d like to try a vibrator sometime.”
“Don’t worry, you will. You’re all going to try all of them. In fact...” I looked at Ashley. “Can she borrow yours?”
Ashley reddened and made a face that said she thought the idea was gross.
“What’s wrong?” I asked. “You just said you use a vibrator, so you must have one.” Hidden in your dresser where you thought Erin didn’t know about it.
“I don’t know. It just seems kind of...”
“Kind of what?”
Ashley looked at Brittney, who blushed so much her face turned red. “Wouldn’t it be weird?”
“Yeah. Super weird,” Brittney agreed.
“Only because you guys are making it that way,” I said, and they looked at me like I’d hurled an insult at them which, in a backhanded sort of way, I guess I had. “If I had a fever, and you had a thermometer, would you think it was weird if I asked to use it?”
Ashley thought about it a second and said no. Brittney was forced to agree.
“What’s the difference? You clean your thermometer after you use it, right? Nobody ever has any qualms about using someone else’s thermometer, even if it was up someone’s ass at some point. What’s so special about a vibrator? It’s a plastic tool. You see what I’m getting at here?”
“I guess so,” Ashley said.
“So, can she borrow your vibrator?”
“I guess...”
“Awesome. If you wouldn’t mind, would you please go get it?”
“Now?”
“If it’s not too much trouble. You know where it is, right?” You know, in your dresser.
“Yeah.”
“Okay. Thank you.”
She sat perched on the sofa, waiting for me to say more. When I didn’t, she got up and left the pool house again.
“So, while she’s gone, is anyone ready to get naked with me yet?”
The three girls looked among themselves, then Kayla leaned forward to pull off her shirt. Her bra quickly followed. She leaned back into the cushions, completely nude.
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