The First Timers Club Pt. 05

The combined stimulation of her mouth and hands soon had me approaching my climax. I moved my hips against her, gently sliding my cock in and out of her open mouth, and I thought to let her take me all the way to the finish, but this part of her fantasy entailed taking me only to the edge and no further, so I alerted her to my imminent orgasm.

"If you keep doing that for much longer, Mistress Ashley, I'm going to cum in your fucking mouth."

It took a couple seconds for her to respond, but when she did, her body stiffened. She rose back up onto her hands and knees and paused there for a moment.

"I'm, uh...I want to fuck you now, okay?" she asked, her tone uncertain.

"Yes, Mistress Ashley," I said softly, straightening my legs. When she didn't move, I prompted her. "Please allow me to guide your movements," I said, and she breathed a relieved sigh.

"Um, yes. Thank you, slave."

"Move forward until your knees are straddling my thighs," I told her. "That's a little too far. Come back a bit. That's good. Brace yourself on the floor between my legs and sit your weight down on top of me."

She did as instructed, dropping her ass down on my pelvis, trapping my cock against her pussy.

"Wait! It didn't go in, did it?" she asked, and I suppressed a chuckle.

"No, you're just sitting on it. It's pressed against your pussy, see?" I flexed my pelvic floor, causing my cock to surge against her. "I want you to slide your ass back and forth, okay? Just a little bit. You're going to drag your pussy over my cock. Just like that, nice and slow."

I lifted my head to watch her movements, and the view of her backside was breathtaking. Ashley's wide hips bunched against her tight bustier as she ground herself against me, and each time she slid forward, her glutes flexed, forming small dimples on her ass which then relaxed when she slid back. I wished my hands were free to touch her and guide her movements. The lack of control frustrated me, but it also excited me because I could only spectate while Ashley explored me and discovered how best to use my body to pleasure herself.

My cock soon found its way between Ashley's labia, and the head and shaft furrowed into her moistened slit. I listened to her breathing and the tenor of her moans and sensed that she was ready.

"It's time, Mistress," I said softly. "Get on your knees and reach back. You're going to guide my cock into your pussy. That's it. You're right there. When you're ready, set your weight back onto it. Just go slow. Nice and easy."

My cock head passed the threshold of her well and opened the passage leading to her vagina. Like Kayla, the sudden pressure alarmed her and she backed off.

"I-I don't know if I can do it," she stammered.

I dropped the roleplay. "You can. You just need to take it slow," I said, encouraging her. "Try again."

"O-okay."

She leaned back and set her weight on my cock and it stretched her pussy again. She hissed but kept going until she had the head mostly inside.

"Ow, it's hurting," she said, but then I felt her pussy abruptly relax and I slid in a little further. "Oh! Oh! You went in!" she cried.

"You're okay. Just relax and take me inside, okay?"

"Okay! Okay! I-it doesn't hurt as much anymore," she said breathlessly.

"Good. Nice and slow. That's it. Take me in."

I couldn't tell if I'd ruptured her hymen or if she had simply relaxed her vaginal muscles. I hadn't felt one when I'd fingered her the day before, and I wondered if she'd ever had much of one to begin with. As far as I knew, she didn't masturbate with a dildo like Kayla did, but perhaps she'd put other things inside her pussy before today.

Ashley gradually eased herself down my pole a couple inches, until her pussy touched her hand, then she let go to brace herself on the floor and started to move up and down.

"That's it. Fuck me, baby. Fuck me," I whispered, encouraging her.

Each downward movement brought me deeper and deeper into her pussy. She felt incredibly tight, but not nearly as tight as I'd expected, and I realized that her pussy really wasn't as small as I'd originally thought. It only appeared that way when compared to the rest of her overdeveloped lower body. After several more bounces, Ashley's large ass touched down on my pelvis.

"You did it! I'm all the way in," I reported, but Ashley wasted no time dwelling on her achievement. She continued riding me, her breathing elevated but not rushed. She seemed driven and focused, the way Kayla had been when she sucked my dick for the first time.

I wanted to say something to her, to ask if she felt okay, but I decided against it. She'd gotten herself into a zone, so I let her continue without interruption. Instead, I offered feedback in the form of moans and encouraging words.

"That feels really good, Ashley. Mm...fuck me, baby. That's it. Fuck me faster. Ride my cock. Oh god, your pussy feels so good."

My words had the intended effect. Ashley rocked her hips faster and dropped her ass onto me with a little more force. I tilted my head up and checked my cock for blood, but if it were there, I couldn't detect it in the dim light and shadow. The sight of her ass bobbing up and down on my cock, its girth stretching her pussy, sent a surge of desire coursing through my body.

"Your pussy looks so fucking amazing on my cock, baby. So fucking amazing."

"Quiet...!" she said, the word stressed as if uttered with great effort.

"Are you okay, Ashley?" I asked.

"Mm...Mm...Mistress...Ashley!"

She hadn't stopped roleplaying! I laid my head back and groaned. The friction of her pussy gliding up and down on my cock felt so wonderful, and I didn't want her to stop, but I also wanted her to complete her fantasy the way she'd envisioned it.

"Stop for a second, Mistress Ashley," I said, and she came to an abrupt stop.

"W-why? What's wrong?" she asked in a panic, and I remembered that one of the rules had been to stop if I asked.

"Nothing. Nothing's wrong, Mistress Ashley. I just want to know if you'd like to try another position. Something that might feel a little better for you?"

She looked at me over her shoulder. "What position?" she asked. Then, as if an afterthought, she added, "Slave."

"Try to get onto the balls of your feet, so that you're in a crouching position."

That was all the prompting she needed. She carefully balanced on her feet and resumed fucking me from a crouched position. Her soft vocalizations told me she enjoyed the change.

"Unh...that feels...so good!" she breathed. "Mm...it feels...deeper."

It did. The new position spread her cheeks and widened her stance, allowing my cock to penetrate deeper into her pussy. She bobbed her ass up and down quickly, causing her cheeks to rumble with every bounce. I moved my hips to meet her. At first, just an inch or so, but I couldn't restrain myself. Soon I had them thrusting upward, urging her to match my speed until she simply hovered over my cock while I hammered her pussy from below.

Ashley cried out as I fucked her, short rapid thrusts that caused her voice to tremble each time my pelvis crashed into her.

"Oh god, oh god, oh god," she intoned over and over again.

I pushed my cock into her and lifted her body up, then gently lowered her down. When my ass touched the floor, she resumed bouncing on top of me, fucking me as fast as she could.

The frustration of Erin's cock teasing handjob earlier, combined with the incredible friction of her daughter's tight, young pussy, soon had my climax on the rise again.

"I'm going to cum Ash...Mistress Ashley! I'm going to cum!"

I said it urgently, even though I still had a little ways to go. With my hands tied, I wouldn't be able to easily withdraw from her if I needed to, so I wanted to give her time to react. She looked back at me, then lifted her eyes when Kayla squeaked.

"Mm!" Kayla tried to hold in her orgasm as quietly as she could but exhaled a loud gasp at the very end.

"I'm going to cum soon, Mistress Ashley," I said again, regaining her attention. "Your pussy feels too fucking good."

"I...I want you to cum," she said. "Do you want me to suck you off?"

The question alone accelerated my imminent climax, and I hurried to answer her.

"No! I want you to cum first," I said, forgetting to properly address her, but she didn't seem to mind.

"But I don't think I'm that close yet," she said, sounding disappointed.

"That's okay! That's okay! Just slow down. Slow down. That's it. Ah, okay. Good. Just sit on my cock. Oh, wow, that's nice. Mm, okay, just move around a little. Flex your pussy around my cock. Does that feel good?"

"Mm, yeah...that's really nice," she said.

I gathered myself and fought back my climax. Although no longer on a hair trigger, I knew I wouldn't last much longer, and definitely wouldn't outlast Ashley on my own. She would need to bring herself most of the way.

"Reach down and play with your pussy, Mistress Ashley. Play with your pussy. Rub your clit while my cock's inside you. That's it. I want you to get off, okay? If you can. Just use my cock and your fingers together."

She still had her feet on the floor, so I slid my legs back to draw up my knees until the tops of my thighs touched the backs of hers.

"Lay back on my chest," I told her. "All the way back."

She laid back until her head rested on my shoulder. I moved my hips and put my lips to her ear.

"I'm going to fuck you just like this, okay? Play with your pussy while I fuck you, Mistress. Oh god, you feel so good, do you know that? Your tight little pussy feels so fucking good on my big fucking cock."

Ashley closed her eyes and let out a long sigh. Her fingers moved swiftly and purposefully over her clit. I didn't fuck her hard or fast, just a slow, lazy fuck to stimulate her vagina while she took care of her clit. The combination proved effective because, in no time at all, her breathing accelerated and became punctuated by soft, throaty moans.

"How are you feeling?" I asked her.

She turned her head and brushed her lips against mine. "Call me Mistress," she said quietly.

"How are you feeling, Mistress?"

"I don't want to stop," she whispered. "I just want to keep fucking you."

"I know, Mistress. I know. I love the way you feel right now. The way your pussy feels on my cock. I want you to cum for me now, okay? Tell me what I can do to help you cum."

"I don't want to cum," she said, though her hand never stopped moving. "I don't want it to be over yet." She wore a pained expression on her face, both from the intense stimulation of her pussy and her desire to never stop.

"We're just getting started, Mistress. We're going to fuck again. And then we're going to fuck again after that. And I'm going to keep fucking you over and over. I don't ever want to stop fucking you. But I need you to cum now. Cum for me, Mistress. I want to feel you cum all over my big cock."

Ashley whimpered and cried out softly. Her orgasm was imminent. I wasn't sure I would make it. I stopped moving my hips and just left my cock inside of her while she brought herself over. She lifted her head and flexed her diaphragm and I felt her pussy squeeze around my cock as her climax finally arrived.

"Oh god!" she cried softly, followed by a large exhalation of air.

I nuzzled her cheek and kissed the side of her face and she turned her head to kiss me back. I resumed fucking her, eager to finally release the pent up frustration that had been building all morning.

"I'm going to cum, Mistress. I can't hold it back much longer. Where do you want me to cum?"

Ashley's eyes opened wider when she realized what I'd asked. "Where do you want to cum?" she asked.

"I want you to tell me, Mistress. I'm your slave. You control me. Tell me where you want me to cum, and I'll cum for you there."

"Do you want to cum in my mouth?" she asked, and I breathed out deeply, trying to cover my annoyance.

"Command me, Mistress!"

"Right!" she said excitedly, then repeated it more confidently. "Right." She sat up and rolled off my stomach, extracting my cock from her pussy. Kneeling at my side, she said, "I will suck your cock and you will cum in my mouth, slave. Do you understand?"

"Oh god, yes, Mistress."

Ashley gripped my cock and leaned over my hip to take me into her mouth. It took only a few seconds before I came, and the ejaculation was so powerful, it almost hurt. Warm, sticky semen flew into her open mouth in several agonizing spurts until, at last, I was completely spent. Ashley milked my shaft, the way she had seen the others do, to coax out the last few drops of my cum. Then she lifted her head and quickly swallowed it down.

With my cock still in her hand, she turned to face me and made a loud slurping sound.

"Yum!" she said, with a huge grin on her face, before doubling over in fits of uncontrollable laughter.

Chapter 25 - Riding Brittney

When I'd been liberated from bondage, I went immediately to the kitchen to chug water and make a snack of leftover Lucky Lucy's while the girls huddled on the sofa to discuss the play by play like a team of ESPN analysts rehashing a football game. My shoulders and upper back ached, and I realized I must have been flexing and pulling nearly the entire time. I rotated my arms to work out the kinks, but knew I'd be sore the next morning.

When I returned, they were deep into a discussion about costume ideas.

"You should totally dress up as Lady Dimitrescu!" Kayla said to Brittney, who made a sour face at the suggestion.

"Her boobs are way bigger than mine," she said, shaking her head.

"You could totally pull it off," Ashley countered. "You could wear a corset and I would totally make that dress for you but, like, make it way sexy!"

"What are you all talking about?" I asked, dropping onto the chaise beside them.

"Don't you think Brit could totally pull off a convincing Alcina Dimitrescu?" Ashley asked, excitedly.

"Who's that?" I asked. "Sounds like the wife of a Serbian dictator."

Courtney made a face. "What century were you born in, dude?"

"Not this one."

The conversation continued without me. Besides costuming ideas, they also discussed the activity itself in excruciating detail, comparing it to Kayla's recounting of her time with me the previous night, all of which I thought would be arousing, but turned out to be almost clinical in its presentation. It made me happy, though, that they could all learn from Ashley and Kayla's first times. It would give Brittney and Courtney more confidence and help to alleviate some of their anxiety when their turns came.

After a while, Kayla broke away from the group to sit next to me, still naked from the waist down.

"What's up, baby girl?" I asked.

She tugged on one of her pigtails. "Is it okay if I use your laptop?" she asked.

"Knock yourself out," I said.

She flipped on the TV, and the porn site still showed the last video we'd watched. Kayla began browsing videos, and Courtney got up to join her. The two girls set to adding several dozen videos to a playlist, a gangbang being the first to play.

The actress in the scene proved to be quite limber and extremely vigorous in her attempts to take on a half dozen well hung men all by herself, with predictable results. By the end, her face resembled a Krispy Kream donut.

As videos continued to roll, the girls became more and more distracted by the on screen happenings. The playlist included an odd mix of gangbang and BDSM, intermixed with more erotic couplings, often between same sex actors and actresses.

Kayla's hand frequently dropped to her pussy during particularly hot anal scenes, but only for a few quick rubs now and again, as if to amplify the visual stimulation, forgetting about it to rejoin her friends in conversation, only to start again later.

Ashley still wore her Drow ranger woodland costume getup but seemed less interested in porn than discussing the real sex she'd just had. When her friends became too distracted to hold a conversation with her, she finally accepted defeat and settled in to watch with the others.

Brittney and Courtney each split their attention between the television and me, and it became obvious they were monitoring my recovery. A short movie played next, and when a particularly spirited scene between three stepdaughters, their stepdad, and his two buddies concluded, Courtney determined that my rest period had come to an end.

"Whew, that was pretty hot," she said, directly to me. "My pussy got totally wet."

Brittney gave her a scornful look and pushed on her arm. "Ew, did you really just say that?"

"It's alright," I said to Brittney. "We're literally here to have sex. Your pussy's allowed to get wet. It certainly makes my job a whole lot easier." To Courtney, I asked, "So, you really liked that, huh?"

"Mm, sure. Hot older guys with big dicks fucking younger girls half their age? What's not to like?" she asked with a knowing smile.

I knew exactly what she was doing, but I liked it. "Yeah, pretty fucking hot," I agreed. "What part did you like best?"

Put on the spot, she tried to recall a specific scene. "I liked in the beginning, when they were all sneaking around, giving their dad's friends blowjobs and having sex behind his back," she said.

"Why?"

"I don't know," she said, struggling to articulate what she liked about it. "Maybe because they were doing something wrong, you know? Like they weren't supposed to be doing it, but they wanted it so bad, so they did it anyway? Does that make sense?"

"Are you talking about the girls or the guys?" I wondered.

She thought about it a second. "I was talking about the girls, but I guess it totally applies to the guys too, right? Like, they're getting their dicks sucked by their friend's daughters, and totally banging them, all while his back is turned. Kind of fucked up, but in a totally hot way."

"Oh yeah, I totally agree," I said.

I wondered how much of that she actually believed and how much of it she thought I wanted to hear. I also wondered how much I'd care if it turned out to be more of the latter than the former. I liked Courtney a lot, and she clearly had a fondness for me, so it made sense we'd express interest in anything that excited the other. Besides, I would never openly challenge her on it, since that would serve no purpose other than to antagonize her, but it would be easy enough to test if she really thrilled at the notion of sucking a dick out in public.

"What about you, Brittney?" I asked, and she reddened.

"What about me?"

"Anything about that turn you on? Or anything else we've watched?"

She avoided looking at me and appeared deeply embarrassed by the attention I'd thrust upon her. "I don't know," she said quietly.

"You don't know if something turned you on or not?" I asked. Perhaps a bit harsh, but I really wanted her to overcome her inhibitions, and of the four girls, she was still by far the most reserved.

"No," she said, then realized her mistake. "I mean, yes."

"Okay, then. Of everything we've watched so far, what's turned you on the most?"

She lowered her eyes and hunched her shoulders in that particular way that absolutely irritated me and shrugged.

"I get off on the anal scenes," Kayla volunteered, much to my surprise, and her friends turned to gawk at her.

"Really?" Ashley asked, surprised.

I could tell Kayla's confession had been spontaneous and calculated to embolden Brittney, because when she saw the looks on her friend's faces, she immediately backpedaled and tried to laugh it off.

"Anal sex is one of my favorite things too," I said, backing her up, and they all shifted their attention back to me.

Courtney moved her eyes between us, and her mouth formed a shocked o-shape as she made the obvious connection. "Oh shit! You guys did it in the butt, didn't you?" she asked bluntly, and Kayla looked like she wanted to melt into the couch.