The First Timers Club - Cover

The First Timers Club

Copyright© 2022 by Alex Weiss

Kayla’s Daddy

Coming of Age Sex Story: Kayla’s Daddy - 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 lifted her by her pigtails until she stood, then laid on the edge of the sofa. “Get on top of me, okay?”

Kayla crawled onto the couch and lifted her leg over my waist until she straddled me on her knees. My cock surged and lifted to press against her wet pussy from below and she looked down to see it.

“Kayla, listen to me, honey,” I said, and she lifted her eyes to mine. “You need to go slow, okay? Don’t rush. You’re going to put me inside of you. Put your hand on my chest and lean forward. Good. Now, reach back and take hold of my cock. That’s it. Pull it up and lean back until it’s just touching your pussy. That’s it, right there. Just hold it there. Rub my cock against your pussy, nice and slow. Oh, wow, that feels so fucking good.”

Kayla’s body vibrated, frantic with anticipation, but her eyes remained pinned to mine.

“Does that feel good?” I asked.

“I want it,” was all she could say, and I knew there would be no more holding her back.

“I know, baby. I know. It’s going to happen right now. Lean back just a little and try to get the head of my cock between your pussy lips. Now, just keep leaning back until I’m nestled into your little well. That’s it! You’re right there. All you have to do now is set your weight down.”

Kayla dropped her weight and then immediately bobbed back up onto her knees when she felt her vagina expand. “Oh god!”

“Easy. Just go slow. There’s no rush. We have all the time in the world. Sit back down and get into position again. Now, ease me inside of you, slowly. Let gravity do the work. My cock is going to open you up. Try to relax your muscles down there and let it happen. That’s it! It’s going in.”

A cry of joy escaped her lips at the sensation of my cock sliding into her vagina, even if only an inch.

“Okay, you don’t need to hold it anymore. Put your hands on my chest and brace yourself. You’ve got all the control you need. If it starts hurting, just lean forward. When you’re ready for more, lean back. It’s that simple. Just look at me, okay?”

Kayla’s thick eyebrows lifted and her mouth hung open in astonishment as my cock worked its way inside of her. Slowly, inch by inch, she sank further down onto my shaft, controlling her descent and letting her vaginal walls stretch and expand to accept my girth. It took a while to even reach the mid-point, but it was enough.

“How does it feel?” I asked and Kayla’s expression became what I could best describe as cautiously ebullient.

“Amazing,” she said, her voice filled with wonder. “I’ve never felt so full down there.”

“I’m glad. I want you to do something now, okay? I want you to start rocking back and forth on my cock. Not too far, though. Just a little bit. Try to keep the head inside your pussy. That’s it. Perfect. Nice and easy.”

“Oh my god,” she breathed at the sensation of my ridged cock head sliding against her vaginal walls. I smiled at her.

“You’re doing it. You’re fucking me, Kayla. You’re fucking me right now.”

The awareness of it dawned on her like a revelation from heaven and her face split into a wide, metallic smile.

“How does it feel?” I asked. “Good?”

“So good,” she said, panting slightly.

“You’re pussy’s so fucking tight, baby. Oh god, you feel good. Just keep fucking me. Try to take me deeper if you can. Just watch me, okay?”

Kayla nodded and settled into a slow, methodical rhythm. Her small breasts hanged like cones from her chest and jiggled softly with each bounce off my cock. I wanted desperately to pull her down and take one into my mouth, but that would have to come later. Instead, I focused on her face and the expressions I saw there.

Even though I’d done none of the work, I found myself growing breathless. The continuous friction of her tight pussy gripping my cock felt immensely pleasurable, and I focused on maintaining my poise for as long as I could. I felt more of her pussy lower onto my cock and realized that she had steadily worked herself nearly all the way down my shaft. After a few more ups and downs, her soft ass touched down on my pelvis.

Kayla’s eyes flew wide open, and she stopped. “Was that...?”

I nodded. “I’m all the way inside of you. How does it feel?”

“Filling,” she said, and I laughed, and her eyes got wide again. “Oh my god, I felt that! I felt you laughing. Inside of me!” I flexed my pelvic muscles, causing my cock to surge and her mouth turned up into a smile. “Do it again!”

We rested momentarily while she got used to having me inside her. I told her to flex and relax her vaginal muscles several times, squeezing and releasing them around my cock. We took turns, me expanding, her squeezing, and it felt remarkably good.

“See if you can sit up, okay?” I said, and she did, slowly at first, before rising to her full height. She looked down at me imperiously and grinned. “Move around a little. Just kind of rotate your hips against mine.”

“Oh, wow...,” she said, savoring the new sensation.

“Yeah, that feels really fucking good. Go ahead and play with yourself while you’re doing it.”

As if forgetting she had that option available, Kayla looked down and pressed her fingers to her clit, rubbing it softly as she gyrated her hips against me. She leaned her head back and closed her eyes and soon lost herself to the motion and sensation. I placed my hands on her hips and began to coax her upwards.

“Start bouncing up and down on my cock, baby. Nice and slow. Oh fuck yeah. That’s it baby. Rub your clit and fuck my big cock, okay? Oh god, that feels so fucking good. Fuck me, baby. Fuck me with that hairy little pussy of yours.”

The words sent her careening over the edge of a cliff in a flaming school bus full of crippled orphans. She climaxed almost immediately. I felt a flush of warmth around my cock and the friction instantly diminished as her vaginal secretions lubricated my shaft. I couldn’t help but chuckle when she cried out so quickly and waited for her to regain focus and look at me again.

“Oh my god, I came!”

“I know, I saw. And I felt it.”

She breathed rapidly, her voice high pitched. “Oh, wow. That feels so good!” she said breathlessly, the final word coming out as a trill. She bounced up and down faster, more confidently. I kept my hands on her hips and guided her movements, lifting and falling along with her. Then I moved my hand to her pussy and rubbed my thumb over her clit.

“Hold on to your tits, baby. I want you to cum again.”

Kayla reached her hands up and mashed her tiny breasts against her chest and bounced rapidly as my thumb worked over her swollen, sensitive clit. She closed her eyes and arched her back, opening her mouth wider as the pace of her breathing increased. Then she reached down to take control of my wrist, bidding me to rub her faster. I pressed the flats of my fingertips against her clit and moved them quickly back and forth. She scrunched her face and, in no time at all, climaxed for a second time.

“Ah!” she gasped, and I put my hand back on her hip. She smiled at me with a flushed face and glittering eyes. “Oh god, I don’t want to stop,” she said between excited, panting breaths.

“Then don’t. Just keep fucking me, baby. Fuck me with your tight little pussy.”

Kayla smiled and bit her lip. “Mm hm. I love fucking your big cock,” she whispered.

Oh god, she was so fucking hot. My hips rose to meet her, and the abrupt change of rhythm caused her some initial distress, until she realized I could go no deeper and that by coordinating our movements, we could fuck faster.

“Lay back. Put your hands on my legs. Oh yeah, that’s it. Ride me baby. Ride that fucking cock.”

Each little change brought with it a fresh batch of sensations for her to savor. She quickly discovered she could alter my angle of attack my varying the position of her body. Leaning forward to create a straight line motion or leaning backwards to glide my cock along the front of her vagina.

We became fluid in our motions and rapid in our pace. We urged each other on, encouraging and directing one another, and as her confidence grew, she became more insistent and ribald.

“Oh god, you feel so good,” she said softly. “Don’t stop. Just fuck me, daddy. Fuck my little pussy.”

I thrusted into her again and again, moving as fast as I thought she could take.

“You’re pussy feels so fucking good. So fucking good.”

Her eyebrows drifted apart, and she whimpered. “I want you to cum.”

My climax was imminent, and we hadn’t discussed this part yet. What to do with my cum? I’d had a vasectomy, so there would be no risk of impregnating her, but she didn’t know that, and I didn’t want to tell her because I’d known a few women with a pregnancy fetish. They loved to take risks, and I was only too happy to indulge that kink, filling their pussies with my cum, then savoring their grateful relief when their next period started like clockwork. I tested Kayla’s predilections.

“I’m going to cum. It’s almost there. Where do you want it? Where do you want me to cum?”

“Just cum,” she said at first, then abruptly added, “On my face. I want you to cum on my face.”

I thrusted my cock inside of her a few more times. “Okay, get on the floor, baby. Get on the floor. Hurry!”

She dismounted and the sensation of my cock pulling all the way out of her pussy was glorious. She scrambled to the floor, and I stood in front of her and stroked my cock.

“Open your mouth. Stick out your tongue. Here it comes, baby. Here it comes.”

A jet of cum erupted from the tip of my cock and painted a thick line across Kayla’s face, from her chin to her forehead. Her eyes reflexively closed, and she flinched as a second shot landed almost perfectly inside her mouth, while a third ended up splattered onto her chest. I moved closer and gripped one of her ponytails, milking the last few drops of cum into her open mouth.

“That’s it. Oh fuck, that felt good. Wow. It’s okay. You can swallow it, if you want.”

She did, grimacing slightly, then used her finger to wipe the cum from her eyelid. She looked at it, rubbing her fingertips together.

“How does it taste?” I asked between breaths and she shrugged her shoulders.

“Like snot,” she said, and then giggled. “Okay, maybe not that bad.” She licked her finger, testing its flavor again. “It’s fine.”

I crossed to the bathroom and returned with a hand towel. “Here,” I said, and she used it to wipe her face and chest. I plopped down onto the sectional and rested my forearms on my knees, watching her clean herself. When she finished, she clasped her hands together in her lap and flashed me a metallic grin.

“Did you like that?” I asked and she could only respond by grinning wider and nodding enthusiastically. I laughed.

“I thought it was going to hurt,” she said, “but it totally didn’t. It felt amazing!”

I nodded, leaving space for her to say more but, apparently, that sufficiently encapsulated the experience for her.

“Good. I’m glad. I wasn’t sure how it would go.”

Her expression changed to something different. Something I hadn’t seen from her before and couldn’t quite place.

“I think I understand why you were scared, now,” she said, and then I recognized it immediately. Appreciation. “Thanks for taking it easy with me.”

I nodded slowly and returned a weak smile. When I saw her expression become quizzical, I furrowed my brow.

“What is it?” I asked.

“I know this probably sounds like a stupid question, but would it be weird to keep calling you daddy still?”

“What do you think?” I asked. I hoped it did, for both our sakes.

“I don’t know..., daddy,” she said, then screwed up her face. “Ew, no. That’s weird,” she said and laughed. “I really liked it when you were inside me, though. Must just be a sex thing,” she decided.

Thank god.

She got up off the floor and crawled onto the sectional next to me, tucking her feet underneath herself and sinking into the cushions. I turned to face her and marveled at the change in her countenance in just thirty minutes. She sat taller and her bearing seemed more assured. Her eyes lacked the chronic anxiety I’d noticed when I’d first met her.

“Why are you looking at me like that?” she asked.

“No reason. I just like what I see.”

She seemed perfectly satisfied with that response and turned away before her smile became a grin. When she looked back, a spark had appeared, and she twisted her eyebrows.

“So...,” she said, and I lifted my brow. “What’s up?” she asked, nodding toward my crotch.

“Just resting.”

“Ah.” She smirked, and then after a momentary silence, asked, “How long does it normally take?”

“Depends. Why, what’s up?” I asked, and she frowned. “You waiting for something?” I pressed, and she shifted her shoulders and breathed an exasperated sigh. “Do you ... wanna fuck more or something?”

“Yes!”

“Then why don’t you just say that?” I laughed.

She narrowed her eyes and asked, “Isn’t it obvious?”

I turned fully toward her and reclined on my side, propping myself on my elbow. “I hate guessing games. I prefer it when girls are direct with me. If you want something, then say it. Remember Conan?”

“Grab him! Take him!” she quoted. Even though she’d never seen the movie, she remembered what I’d said.

“Exactly. So, what do you want? Be as detailed and explicit as you can.”

She shifted her weight and cocked her head. “I want to fuck you again,” she said plainly.

“Great. Tell me about it.”

She made an OK gesture and poked her finger through the hole. “Your cock, my pussy. In and out.”

“Ha! No, I said be explicit. What do you want to do, specifically?”

After much more consideration than I would have expected, she said, “Doggy.”

“You want to get fucked from behind?”

“Yeah.”

“Sure, I’d love that. Anything else?”

“Hmm ... can we do it standing up?” she asked.

That seemed an odd request, but she was quite petite, even if a little chubby. “Like, me holding you up off the ground?” I asked, and she nodded. “How much do you weigh?”

“I don’t know. Maybe one twenty?”

I glanced at her small belly roll. Okay, so one thirty-five. “Yeah, we can do that. What else?”

She hemmed and avoided looking at me, which I’d learned meant she wanted me to magically know what she wanted to say because she was too embarrassed to say it herself, which meant it was something twisted and juicy.

“You’re going to tell me eventually, and I’m probably going to love whatever it is, and then you’re going to kick yourself for not telling me sooner, so just come out with it already.”

“Fine,” she said. “You wouldn’t be into, like, doing butt stuff, would you?”

“Anal?” I clarified, and she nodded. “Yeah, of course. Love it. Anything else?”

She shook her head. That concluded her list of requests, apparently, and I wondered where anal ranked. Had she bought a cart full of groceries to hide the hemorrhoid cream? I furrowed my brow. Maybe not the best metaphor.

With her cards on the table, we talked for a while, keeping the locus of conversation on sex, and it wasn’t long before I felt recharged enough for round two. We started slowly, only fingers and lips and tongues at first, as we revved each other up.

After a wonderful blowjob where, after a little instruction, she spent much time licking and sucking on my balls while she jacked me off, I returned the favor and went down on her. My tongue lashed her clit while my fingers wormed their way inside her pussy. The wetness she produced astounded me, and her strong aroma and flavor so intoxicated me that I soon stood fully erect and leaked fluids of my own.

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