The First Timers Club - Cover

The First Timers Club

Copyright© 2022 by Alex Weiss

Advanced Manipulation

Coming of Age Sex Story: Advanced Manipulation - 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  

Waking up with Brittney had troubled me for the familiar intimacy of her embrace. Waking with Ashley left me with no such regrets. I felt pressure on my cock and hair on my thighs and when I opened my eyes, I found her smiling at me from between my legs.

“Good morning,” I said, and then clapped my hand over my mouth when her eyes widened.

She lifted her head and stroked my cock and mouthed the words ‘good morning’ and then went back to work. I found my phone and quickly typed her a message, turning it to face her so she could read it.

Me: Lick it please

She grinned and did as I asked, sliding her tongue over the bottom of the shaft and teasing the frenulum. She watched me type another message as she cleaned my cock with her tongue.

Me: You look so fucking sexy doing that.

She grinned and then shivered and resumed licking. I tossed my head back and gasped.

Me: Suck the head and jack me off

Me: Soft and slow

Her lips closed over my glans and she slowly rolled them over the ridge while her hand moved up and down the shaft. Despite herself, she moaned softly. My eyes shuttered and I breathed out deeply. My god, her mouth felt wonderful.

Me: 69?

We pleasured each other with our mouths, taking our time, exploring every inch of the other’s sex. I wanted to know her pussy. Every soft fold, every crevasse, every bump and wrinkle and mole. Her clit became my pal. My buddy. My best friend. I teased her and kissed her and sucked on her until she sent a signal to Ashley’s brain that she should probably have an orgasm now, so she did. Then I received a similar message from my cock and I thought, why the hell not?

When Ashley kissed me, I tasted my cum on her lips. I could tell she was already eager for more sex.

Me: Is your dad still home?

She found her phone and read it and nodded.

Ashley: 1-2 hrs

We fucked for one to two hours, I’m not exactly sure. I came inside her pussy twice more, but the second time I did it, I saw a pang of fear in her eyes. Despite her reservations, however, she still held me inside of her until long after my cock had softened. When I finally pulled out of her, she reached between her legs and rubbed my cum between her fingers.

Me: You won’t get pregnant

She read my message and wiped her cummy fingers on her nipples before replying.

Ashley: How can u b sure?

Me: I can’t have kids

She stared at me, studying my face, and her perfectly sculpted eyebrows parted.

Ashley: I’m so sorry

I chuckled softly and sent my reply.

Me: Don’t be

Me: My choice

Me: I can cum inside you every time if you want

Her cheeks lifted when she read my message.

Ashley: I love it when u cum inside me

Me: I love it too

Ashley: Will you cum inside me again?

Ashley: Please?

Me: Put your bustier and boots on and go stand against the wall

Me: I want to fuck you standing up

Ashley leaped off the bed and quickly put on her outfit. When she put her palms flat against the wall and stuck out her large ass, I couldn’t believe how quickly my erection returned. Her boundless enthusiasm and creative lovemaking turned me on so much. I felt sore from fucking her so many times already, but I had to have her again.

I moved behind her and guided my cock into her pussy and fucked her harder than I probably should have. My hands moved from her wide hips to her small tits and everywhere in between. Then I heard a rumble of footsteps in the hallway and a deep cough from Clay as he walked past on his way to the stairs.

My head moved to follow him through the wall as I fucked his baby daughter two feet away and the thought of it made me cum. I squeezed Ashley’s breasts and thrusted my cock inside of her pussy and groaned in her ear. She cried out softly and I clamped my hand over her mouth.

“Ash?” Clay called from just outside the door. “You say something?”

When I uncovered her mouth, she yelled back, “No, dad.” I thrusted inside of her several more times as the last of my cum flowed into his daughter’s pussy.

“Okay. I’m heading out.”

“Bye, dad.”

I slapped her ass and she turned her head and gave me a harsh look. When his footsteps faded down the stairs and the garage door opened, she pushed me backwards onto the bed and jumped on my waist.

“I can’t believe you did that!” she hissed, beating on my chest with her fist.

“It felt good though, didn’t it?”

She tried to hold on to her scowl, but it turned into a huge shit-eating grin. “Really fucking good! Oh my god, we were having sex right in front of him!” she whispered.

“I know.”

With enough rest and water and lube, I could have fucked her all day. But text messages from her three friends to both our phones told us that our escapades for the morning would have to come to an end.

She talked me into taking a shower with her. I told her I didn’t have the strength for another round so quickly, but she insisted it would be strictly business. When one soapy finger found her asshole and another found her pussy, she grabbed my wrist and coaxed me to rub her clit. One last orgasm before sex school.

“So, where did we go wrong?” I asked the girls after we’d all disrobed and settled into our familiar spots inside the pool house.

We’d managed to get ourselves back inside when Ashley found a spare key in the junk drawer. I didn’t know who had locked it or why, but I would make sure to ask Erin about it when I saw her later. Everything inside looked to be in order, exactly as we’d left it. Together with my dead car battery, that made two strange occurrences in a row. I didn’t believe in coincidences.

“Well, I sucked a dick,” Kayla said, sounding far less remorseful about it than she pretended to be. “So there’s that.”

I couldn’t take my eyes off her bald pussy, and she couldn’t stop touching it. Her hand had formed a near-permanent connection to her smooth vulva and her fingertips constantly brushed over her clit.

“Yeah. That’s a biggie for sure,” I agreed, “but not quite what I was looking for.”

“We gave in,” Ashley said.

“Give the lady a gold star. You are correct.”

“How do you know Denise?” Courtney asked.

“Actually, it’s a really interesting story because it’s none of your fucking business.”

“She’s very pretty,” she continued, not taking the hint.

“I’ll let her know you said that. I think she liked you too.”

Courtney narrowed her eyes. “Have you fucked her?”

“Courtney...”

“I’m just asking you a simple question, dude. You know, one friend to another. Have you and Denise had sex?”

“I’m not going to talk about this with you, so drop it.”

“Fine.”

“Anyway,” I said, picking up where I left off, “as I was saying, you let the guys take control of the situation and, at the end of the night, not a single one of you had an orgasm, but two guys got to cum, one of whom even had his load swallowed, and another guy got to cop a feel.” I held out my hands in front of me, palms up, and mimed a balance, dipping one hand way lower than the other. “Not a very good exchange.”

“It’s just ... she’s so fucking gorgeous!” Courtney blurted, a touch of anger rising in her voice. “Like, a ten in my book, easy. Maybe an eleven. How many other women like her are out there?”

I slicked back my hair and sighed, utterly exasperated with her outbursts. “Where is all this coming from?” I asked.

“I’m just trying to figure out who you are, dude. We got one teeny glimpse of your life outside of this pool house and I feel like I don’t even know who you are. That dope ass apartment. Drop dead gorgeous Denise hanging all over you. Do you even work? I mean, what are you? Some kind of gigolo or something?”

I took a seat on the edge of the coffee table in front of her and rested my elbows on my knees.

“I’ve told you a hundred times, I don’t talk about my sex life. Yes, I work. I’ve made some good investments and I’ve been very lucky. I bought my apartment years ago when the market wasn’t so insane and I’ve been lucky there, too. What other non-sex-related things do you want to know about me?”

Courtney fumed but didn’t take the bait. She’d removed her makeup before she’d gone to bed last night, per Denise’s instructions, and her face looked redder than usual. I touched her cheek and she slapped my hand away.

“Is this what’s bothering you?” I asked.

“Fuck you!”

I stood and went back to my spot in front of the TV. “There’s nothing wrong with you, you know? I don’t know how many times I have to tell you that.”

Courtney exploded.

“Shut the fuck up, okay? Just shut up! Look at them!” she said, pointing to her friends. “They all look amazing still. Fucking Brit’s perfect hair and Ash’s perfect skin and Kay’s ... perfect twat! And Denise, with her perfect body and gorgeous smile and cool hair. And then there’s me! Look at me! I look like shit, just like I always do. It’s not fair!”

Her lips trembled as she fought to hold back tears, angrily swiping at the ones that tried to escape.

“Denise is a lesbian,” I said, and Courtney lifted her eyes and opened her mouth. “I’m only telling you this because I know she’d want me to. I’ve never fucked her. We’re just good friends. We just happen to share the same taste in girls.”

Courtney sniffled. “Oh. Well ... was that so hard?” she asked.

“I wasn’t kidding when I said she likes you. I mean, she likes you likes you.”

Courtney’s face froze and her eyes widened.

“Yeah. Gorgeous Denise with the perfect smile and the cool hair who’s an eleven out of ten in your book? She likes you.”

Courtney blinked a couple times. “How do you know?”

“She told me. She said, and I quote, ‘I got wet waxing her pussy,’ end quote.”

I didn’t think Courtney’s face could get any redder, but somehow it did. Where just moments before, she’d fought back tears, she now battled to keep the smile percolating on her lips from overtaking her face. She just barely managed to tamp it down.

“She even asked me to give you her number,” I said.

Courtney coughed to cover a little laugh. “She did?”

“Yeah. May I continue now, please?” I asked.

She sank back into the cushions and wiggled her fingers at me. “Carry on.”

“Thank you. So, as I was saying...”

“Maybe you should give it to me,” Courtney said. “In case I need another treatment. On my face, I mean,” she added quickly. “Not the whole ... waxing business.”

“For fuck’s sake, here,” I said, handing her Denise’s card.

Courtney held up the elegantly designed business card, then flipped it over to find Denise’s hand-scrawled cell phone number on the back. She flipped it over a few more times and then tucked it away in her purse. I stared at her until she grew uncomfortable.

“What?”

“Are you done now?”

“Yes! Sorry! Please, continue.”

I gave her one last glare and then a quick wink and a smile before continuing. “There’s nothing wrong with sucking a dick,” I said to Kayla, “or giving some guy a handjob,” I said to Ashley, “or getting felt up. Those are all great things. But that wasn’t the point of last night. The point wasn’t to see if you could get laid. The point was to see if you could maintain control of the situation when you needed to, and you all failed at that.

“If you’re not able to get what you want from a man when that’s your sole purpose, then how do you think it’s going to be when it’s just a casual encounter or the beginning of a relationship? How long will you allow someone to use you before you wise up and think to yourself, why do I keep giving and giving and never get anything in return?

“The point of the exercise, Courtney, wasn’t to arbitrarily set some stupid rules about what you should and shouldn’t do. The point was to illustrate just how easy it is to let yourself be taken advantage of by men who have a lot more experience getting what they want than you do.”

Courtney avoided my look. She stuck her tongue in her cheek and tapped her fingers together and slowly nodded. She got it. At least, I hoped she did.

“So, that guy wasn’t really in pain?” Ashley asked, and I nearly wept for her naivety.

“I’m sure he wanted to get off really bad and was jazzed to have a hot girl jack him off, but no. He wasn’t in medical pain. He lied to you. He was just horny.”

The surprised look on her face morphed into disappointment and betrayal and then resentment in rapid succession. She stared straight ahead and scoffed as she came to terms with her own gullibility.

“Don’t beat yourself up. It happens to everyone at some point. Even me.” I thought about Erin and how effortlessly she’d manipulated me and I began to share Ashley’s resentment.

Brittney shifted uncomfortably and said, “I don’t want to get used by some guy, but I’m starting to think I wouldn’t even know it if it happened.”

“You’d know,” I assured her. “Maybe not right away, but eventually. And it can be damaging to your self-esteem if it takes you a really long time to figure it out. And the more subtle the manipulation, the longer it takes to recognize it and the worse you end up feeling.”

“So, what do we do?” she asked. “We can’t have you chaperoning us for the rest of our lives.”

I lifted my lips and chuckled. “No, you can’t. Part of it you’ll figure out with experience, but wisdom comes with time. Being able to recognize some of the more obvious red flags is a good place to start, though.”

“Like what?” Ashley asked.

“Take last night. You asked someone to finger you to an orgasm. The moment they started negotiating, that was a red flag. Not a deal breaker, but definitely a flag. When they insisted you go first, that was an even bigger red flag. Obviously, when they got what they wanted and didn’t even bother to reciprocate at all ... well, that was the biggest red flag of them all, wasn’t it?”

Kayla, who had seemed unperturbed by her conduct the night before, suddenly furrowed her brow. “Wait. Oh damn. That guy said he would go down on me if I sucked him off first, but when I finished, he looked at his phone and said his ride was leaving and he had to go.”

My sympathetic smile told her all she needed to know about her sudden revelation.

“Oh my god, what a fucking asshole!” she spat. She looked at me. “Why are men such pigs?”

I didn’t have a good answer. I shrugged my shoulders and asked a rhetorical question. “I don’t know, Kayla. Why is the sky blue?”

“Because of the scattering of light in the upper atmosphere,” Ashley said, then quieted and turned her head away.

“How do we know you’re not manipulating us right now?” Courtney asked. She didn’t sound confrontational. Her expression showed a genuine trepidation. “You’re way smoother than any of those d-bags at the arcade. Would we even be able to tell?”

“That’s a fair question. Probably not, if I’m being honest.” I held up my hands again, mimicking a balance. “I guess the best way to judge would be to look at the evidence and weigh it. Have you gotten at least as much from me as you’ve given? If you have, then I’m probably worth the risk. If not, then why are you still talking to me?”

She nodded, and I could tell she was taking stock. I looked around the room and they all appeared to be thoughtfully tallying the credits and debits of their sexual ledgers.

“I’ve gotten more,” Brittney finally decided, then looked at me and said, “Way more.”

“Me too,” Kayla said, and the others agreed.

“You know what’s funny?” I asked. “I feel the exact same way. You’ve given me way more than I’ve given you.”

Ashley twisted her eyebrows. “How is that possible?”

“Because,” I said, “this isn’t like Magic the Gathering, where there’s always a winner and a loser. If we’re doing this thing right, then everyone should come away a winner.”

I felt the tingling of an emotion that, rather than suppress, I impulsively decided to express. “Being with you guys, teaching you about sex, fucking you and getting fucked by you, seeing the looks on your faces each time you discover some new thing that thrills you and brings you pleasure ... it makes me feel good. Really good. I appreciate that you’ve accepted me into your circle, and I love that I get to be here and spend time with you all. I honestly don’t think there’s any other place I’d rather be right now than here with you four.”

I’d never spoken so openly about my feelings for them, or hardly anyone else for that matter. I tried so hard to stay aloof all the time, to keep my emotions reserved, but for what? I didn’t know. Sometimes, I felt like a miser, saving up his money to spend one day, in some indeterminate future, only to die rich and miserable, and that thought filled me with sadness and deep regret.

The four girls looked at me with solemn faces, uncertain about how to respond. Then Brittney stood up and came forward to put her arms around me and my shoulders convulsed. She held me tighter and soon I felt other arms surround me as they all got up to join her and I couldn’t hold back any longer. A flood of emotion poured out of me in an aching sob I didn’t know I’d been holding in. My tears spread to the others and soon we became a huddled mess of emotional release.

When we finally separated, I wiped my face and laughed softly. “Wow, I wasn’t expecting that,” I said, sniffing. “I’m usually not like this.”

Courtney stifled a cry, her smile a trembling grimace. “Yeah. You can be such a pussy sometimes,” she said and laugh-cried over it.

I begged them to return to their seats while I composed myself and slicked back my hair, taking several deep breaths to calm myself. I thought I’d feel embarrassment for my unexpected outburst, but a great relief washed over me instead, as if a giant weight had been removed from my chest, and I felt an immense gratitude that they’d allowed me that brief moment of unrestrained openness. But the moment passed and I soon felt prepared to move on to other matters.

“You want to take a break?” Ashley asked me, wiping her cheeks with the back of her hand.

“No,” I said. “I’m alright. Thank you.” I considered what I should say next, but my mind blanked. “I’m just not sure where to go from here,” I said at last.

From what I could tell by looking at their faces, they didn’t know either. Then Brittney helped me out.

“I feel like we need to try again,” she said between sniffles. “The arcade, I mean. I hate losing. Especially when I know I could have done better.”

The germ of an idea bloomed in my mind and I nodded. “Okay, I’ve got it. Here’s what we’re going to do. You’re going to take turns propositioning me, right here, right now. Same deal. You have to get me to finger you to an orgasm without offering anything in return.”

Courtney’s mouth turned down into a skeptical frown. “Dude, that’s not really a challenge, though.”

“It’s not?” I asked.

“No. First of all, we fucking know you. Second of all, we know you fucking. You’d do it just to make us happy. I mean, you’d probably go down on us just to see the looks on our faces.”

“You think so?”

“You’re not like those other guys,” Kayla said, agreeing with Courtney. “You’re ... good to us.”

“I appreciate the sentiment, but I think you underestimate me. I can be ruthless when I need to be. I promise, I’ll do everything in my power to turn it around on you.”

Although I hadn’t won over my skeptics, they agreed to the challenge. I told everyone to get dressed.

“How come?” Brittney asked, hiking up her skintight jeans from the night before.

“To add a sense of authenticity,” I said. “You’re not going to be walking in there naked, are you?”

“I guess not,” she said, buttoning the fly, and I thought I detected a hint of disappointment in her voice. Two days ago, she wouldn’t even take off her shirt, and now she looked sad to have to wear anything at all. I shook my head and smiled.

When we’d all dressed, I asked for volunteers.

“I’ll go first,” Ashley said.

“Okay, so I’ll just be some random guy you don’t know. Ready?”

“I guess.”

“Action.”

She took a breath and strolled up to me, an exaggerated sway to her hips and a come hither look on her face. I stood leaning against the wall near the TV, pretending not to look at her.

“Hey,” she said.

I turned to her and smiled. “Hi there, cutie.”

“What’s your name?”

“Chaz Horsecock,” I said, sticking out my hand and she snorted a laugh. “You have such a beautiful laugh.”

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