The First Timers Club Pt. 05

Chapter 24 - Mistress Ashley

Ashley and Brittney exchanged looks and Ashley said, "So, Kayla gave us all the details about last night when we went out earlier."

I looked at Kayla and said, "Oh, she did, did she?" and Kayla looked away and flashed an embarrassed smile that revealed some metal.

"Yeah," Ashley confirmed. "And we think it's a little unfair."

I lifted an eyebrow. "How so?"

"Well, we don't think it's fair that she got to, you know, have sex, real sex I mean, but the rest of us didn't. Not that the other stuff isn't great too. Not at all! The other stuff is amazing. But, like, we're all supposed to be in this together, right? So, we were wondering if maybe we could, I don't know, maybe, If you wanted to, I mean, would it be possible..."

"Ashley, you're fucking killing me, girl. Just spit it out, okay? What are you asking?"

"We want to fuck you, dude," Courtney blurted, glaring at Ashley, who breathed a sigh of relief.

Ashley pointed at Courtney and said, "Yeah, that."

I rubbed my face and scratched my jaw. "Okay...so, before I speak to that, I need to check in with Kayla, first. Was there anything about last night you didn't tell them?"

The question jarred her. "W-why? What do you mean?"

"I mean, did you tell them everything that happened?" I lifted my eyebrows a couple times. "Like, everything?"

She shifted her eyes around and shook her head.

"Woah, wait a second," Courtney said. "Are you holding out on us, you little twat? Spill it."

I flashed her a disapproving look, but she ignored it. Kayla squirmed and looked to me for help.

"She didn't have to tell you shit," I said. "I'm curious what she did tell you, though."

Courtney eyeballed Kayla and said, "She told us she went down on you at first, and then you guys had sex with her on top, and supposedly it was amazing. Then you went down on her and you had sex again, but this time from behind, and it was even better than the first time. Then you guys watched porn for a while and had sex a third time where you did a bunch of different positions, and apparently that was even better than the first two times. Does that about cover it, Kiki?" she asked Kayla, who slowly nodded and smiled sheepishly. Courtney scoffed. "So, what did she leave out?" she asked me.

"Not for me to say."

Courtney blew a raspberry. "What a gyp," she spat. "This is bullshit, you know? We're all in here, baring our souls and sharing everything we do, but then she gets to sneak in by herself and do shit behind our backs."

"And you've never done anything like that before?" I asked, and she closed her mouth and smirked.

"That was different," she said quietly.

"For you, maybe, but not for them," I said. Courtney scrunched her brow and breathed a frustrated grunt but didn't have a response. I addressed the group. "Alright, I'm down for this. If we're lucky, I might even be able to get to all of you today, but it's probably going to take all day. So, who wants to go first?"

"Me!" three girls said at once, with Kayla the lone abstention. I'd done a number on her pussy the night before and didn't expect she'd be up for very much today.

"Okay," I said, "let me ask the question this way: who wants to go first, right now?" and again, three voices spoke as one. I lifted my eyebrows and sighed and tried again. "Who wants to go first, right now, in front of the others?"

No one spoke up this time. At least, not at first. Then Ashley raised her hand.

"Can't we do it in private, like Kay did?" she asked. "We can use my room."

I tilted my head and said, "Sure, we could do that..."

"But what?"

"Well, if we're alone in your room, that means everyone else has to hang out somewhere and wait till we're finished, which might be kind of boring. Also, we could only use your room until your dad gets home, right? So we'd have to do it now, but there's one problem."

"What?" Ashley asked.

I jerked my thumb toward the house. "Your mom's in there."

Ashley frowned. She hadn't thought about that.

"I've got one other tiny little issue with using your room like that," I said, holding my fingers close together, and Ashley gave me a quizzical look. "I'm not an escort. I agreed to teach you guys about sex. All of you, together, as friends, and I don't want to end up as just some dick for you to fuck, okay? And I hope that's not how you see me."

"Of course not!" Brittney said hastily. "I know I don't, and I don't think anyone else here does either."

"No, not at all," Kayla agreed.

"Okay, so that idea's out, then. Another option would be to wait until it's late and do it here, after everyone else goes to bed, but then it's going to take a few days to get to everyone and there's that whole escort thing again," I said.

"I don't want to wait that long," Courtney said, and the other two agreed with her. I looked between them and held up my palms.

"Alright, so that's out too. Since that's the case, let me throw this out there, and then you all let me know what you want to do." They looked interested, so I cleared my throat. "My original goal, if you remember, was to create an atmosphere where the four of you could explore your sexuality. I wanted you to feel a sexual tension permeating the room at all times." I glanced at Ashley. "The Sex Force, right?"

She nodded and a little smile played across her lips. Then I looked down and laughed.

"Speaking of which, why the hell am I even dressed right now?"

Courtney tsked and said, "Exactly what I was thinking. Take it off, dude. Let's see that dick!"

The girls cat-called and whistled, urging me on, and I quickly disrobed to a chorus of applause. Everyone's mood seemed to be lifting.

"Okay, okay, calm down," I said. "Where was I?"

"Sex Force," Ashley reminded me.

"Right. Look, there's no denying that watching other people have sex can be arousing. The sights, the sounds, the smells, they all get us hot. I'll get hard and your pussies will get wet. You'll feel flushed, your nipples will harden, your clit will get hard, your labia will become engorged. In short, it'll make you ready for sex."

As I spoke, my cock swelled until it stood straight out from my pelvis, pointing at the four girls in front of me.

"See what I mean? Watching other people have sex can be, well, sexy. It's called voyeurism, and it's a huge kink, and being watched can be super hot too. That's exhibitionism, and it's also a huge kink. Having sex in public, the thrill you might get caught, knowing other people are getting off watching you, it can all be a huge turn on.

"If we have sex here," I said, "in front of everyone else, we get to explore both aspects of that simultaneously. We get to be voyeurs and we get to be exhibitionists, and that can be incredibly stimulating and pleasurable for everyone, not just for the one's having sex.

"Anyway, just something to think about. Why don't you all take a moment to decide what you want to do, okay?"

It didn't take a moment. Ashley raised her hand again.

"I'll do it," she said. "They can watch. I don't mind."

"You sure?"

She looked around and nodded. "I did Drama last year, and I DM our D and D group, so I'm already kind of used to performing in public. This shouldn't be so different, right?"

"I'm not sure what even half of that meant," I said, "but okay." I went to lock the slider and switch off the lights. "Go ahead and get undressed," I told her when I returned.

Everyone quieted as Ashley rose to her feet. She set her glasses down, then took a couple quick breaths before lifting her form-fitting tee over her head and peeling off her boot cut jeans. When she reached her hand back to unhook her bra, she paused, staring at the ground.

"What's wrong?" I asked.

"I don't know," she said, shifting her eyes around. "Just nerves, I guess."

I rubbed my chin and thought a moment. "That's okay, leave it on for now," I said and she lowered her hands. "When we were all dirty talking the other day, you closed your eyes and did some meditation thing, and when you opened them again, you'd turned into someone else. What was that?"

"Something I learned in Drama," she explained. "it helps you get into the role. You know, inside your character's head."

"Interesting. Okay, let's do this, then...," I said, looking around the room.

Then I saw what I needed and went to the curtains, removing a pair of braided tiebacks securing the fabric panels. I pulled them through my hand to check their length. Yeah, that would do nicely. With my bonds in hand, I pushed the coffee table off to the side to clear the area in front of the sectional.

"What are you doing?" asked Ashley as I looped the tiebacks around the sectional's legs, securing them tightly.

"We're going to act out that fantasy of yours," I said, taking a seat on the carpet, between the two chaise sections of the u-shaped sectional. "Only for real. Kayla, honey, tie my wrists, okay? Not too tight, though."

Ashley gawked at me. "Really?" she asked as I laid back and held out my arms so that Kayla could quickly bind my wrists. "But, I don't have a bustier or boots or anything like that."

"That's fine," I said, testing Kayla's handiwork. The knots were a little tight, but not too bad. Securely bound, my arms spanned across the open middle portion of the sectional, with my feet facing away. "It's not about the costume."

"But, I like dressing up," she said quietly.

"What about that ranger costume you made for Dungeoncon?" Brittney suggested. "That had boots and a bodice."

Ashley's eyes widened excitedly for a second, but then she shook her head. "No, wait, I made that out of buckskin, remember? Not vinyl or patent leather."

"Oh my god, Ash, who gives a fuck? Go get it!"

"Right!"

Ashley threw her clothes back on and bolted from the pool house, returning several minutes later with a bundle of animal skins and fur tucked under her arms.

"Two minutes!" she said breathlessly as she disappeared into the bathroom.

Ten minutes later, when she finally emerged from the bathroom, the three girls turned their heads to look, but I couldn't see over the top of the sectional. I could see Courtney's face, though, and watched her eyes grow wide and her mouth open.

"Ho-ly shit," she breathed.

When Ashley came into view, I nearly choked. Her ornately decorated buckskin bustier, actually an under-bust bodice, sinched her narrow waist and lifted her small, bare breasts high up on her chest. Tightly laced moccasin boots, lined in what looked to be coyote fur, reached just below her knees, and a pair of fingerless buckskin gloves covered her forearms to the elbow. Above the knees and below the waist, she was completely nude.

"What do you think?" she asked, sounding nervous.

"I think you look hot as fuck is what I think," I said and she smiled awkwardly.

"I'm supposed to be a half-Drow archer named Lythrana, but I couldn't find my wig and ears and bow and stuff." She gestured over her shoulder. "I can go look for them, if you want."

"No! I mean, you look amazing just like that. You don't need to be Lythra or whatever."

"Lythrana."

"Whatever. Today, you're going to be Mistress Ashley," I said, and she smiled again and repeated the name. "First things first, though. We need to talk about the rules."

"What rules?"

"The rules for this kind of roleplay. I'm tied up, so I'm entrusting you with a lot of control over me. If I tell you to stop, you have to stop immediately, okay?" Ashley nodded and I continued. "And if I tell you to untie me, you have to do it right away, okay?"

"Okay."

"Good. Now, other than that, you're in complete control and you can do pretty much whatever you want to me." At that, Ashley grinned. "Yeah, I thought you'd like that. When it comes time to, you know, put my cock inside you, I'll talk you through how to do it so you don't hurt yourself."

At the mention of penetrative sex, Ashley became anxious.

"Don't worry, Ashley. You're going to do great. Do your meditation thing and become Mistress Ashley. The rest of you, I want you to watch, but please don't talk or make any comments. Feel free to take your clothes off and masturbate, though, if anything you see turns you on."

Ashley closed her eyes and moved her mouth soundlessly, holding her hands out at her sides, palms facing forward, fingers wiggling. After several seconds, she slowly opened her eyes and a wicked smirk lifted her lips.

"Oh, what have we here?" she asked in a low, sultry voice, approaching like a cat on the prowl. She stopped at my side, feet apart, and placed her hands on her wide hips. "Mm, what they say about you is true. You do have a marvelously large endowment. I'm so glad I was able to purchase you from those Geldan slavers, and I see now that you were well worth the gold they charged me. You'll make a worthy addition to my stable."

Had she cooked all this up on the fly, I wondered? If so, her improvisational skills were top notch. And I couldn't get over the transformation. She looked so fucking sexy, and her demeanor had completely changed. She was no longer Ashley Mitchell, shy nerd virgin. She had become Mistress Ashley, the wicked woodland dominatrix.

I didn't want to wait. I wanted her to mount me right then and there, and my stiff prick showed my eagerness to fuck her. She squatted down beside me to run her fingers over my chest, stomach, and thighs, then reversed course to trail them over my balls and up to the tip of my cock. She looked at me and smiled as her fingers closed over my shaft and she began to slowly jack me off.

"Before I put you to work pleasuring my guests, I need to make sure you understand your place, slave. You will speak only when spoken to, is that understood?"

"Yes."

She squeezed my cock. "You will address me as Mistress Ashley, you insolent slave!"

"Yes, Mistress Ashley," I said quickly, and heard a smattering of soft giggles coming from the sofa above me.

"Mm, that's better," she said, pleased by my obedience. She resumed her lazy handjob. "You're only purpose in this miserable life will be to pleasure whomever I tell you to, whenever I tell you. Understood?"

"Yes, Mistress Ashley."

"Excellent. Your superb body is mine to control. Now, as is customary here, I will need to make certain that you are up to the task for which I have assigned you. I can't have my guests leaving disappointed, now can I?"

"No, Mistress Ashley."

"No is right."

She let go of my cock and stood up, letting her hands drag over her thighs, pussy, and belly, all the way to her breasts. She cupped them and brushed her nipples with her fingertips, teasing them to stiffness. Oh lord, I wanted her to fuck me, and I yanked against my restraints to get at her.

"Why don't you come down here so I can eat your little pussy?" I said.

"Silence!" Ashley bellowed and bent over at the waist to slap me hard across the face. The sound of it shocked her and she gasped and put her hand to her mouth.

"Oh, shit! I'm so sorry! Did that hurt?"

I stared into her eyes, feeling the sting of her slap. "Did I tell you to stop?"

She lowered her hand and narrowed her eyes. Then she slapped me again. "I said, silence!"

The girls on the couch erupted in soft laughter, and Ashley lifted her head.

"Hush, ye bitches! Do not encourage him," she admonished, then lowered her head and sneered, taking my chin in her hand. "I know how to teach his kind a lesson."

She straightened and began a slow stroll around me. My eyes followed her as she surveyed her newly purchased flesh. The bustier and boots accentuated her wide hips and large bottom, and I found myself unable to take my eyes off of her. She noticed my gaze and smiled.

"Like what you see, slave?" she asked, placing a hand on her behind and giving it a few soft smacks as she made her way around me.

"Yes, Mistress Ashley."

"Yes, indeed. Your fondness for big butts is as legendary as it is baffling to one such as I. Be that as it may, you shall never partake of my oversized ass. However, if you are obedient and pleasure me to my liking, I may perhaps allow you to look at it."

My heart hammered in my chest. How could she be this fucking sexy? I wanted her so badly I could hardly stand it. The veins in my forearms bulged as I strained against the ropes securing me to the sectional, but I could hardly budge. I was well and truly restrained.

Ashley observed my struggle with an amused smile, stepping over my outstretched arm to stand with her legs on either side of my head, her back to the couch. She loomed over me in a pose eerily reminiscent of the one that Erin had held just a few hours earlier, and the view from the ground was equally as spectacular. Ashley's small pussy stared down at me, begging to be fucked, and I so desperately wanted to give it to her.

Ashley looked down with a haughty expression and took a deep breath. "I can smell your desire, slave. You reek of it. When was the last time you laid with a woman?"

This morning. "It's been far too long, Mistress Ashley."

"I see. Perhaps I should wrap my lips around your big dick and favor you with a long, sloppy blowjob. Would you enjoy such a treat, my slave?"

My heart flipflopped. Holy fucking shit. "Yes, Mistress Ashley," I said in a hoarse voice.

"Mm, excellent. I believe Mistress would enjoy it herself as well."

Ashley lowered herself down over me, her hands by my hips, her knees straddling my head, and I was struck once again by the similarity to my earlier encounter with Erin. I tried to push her from my mind, but found myself comparing their pussies, noting how different in shape and color they were. Erin's pussy meaty and dark, Ashley's plump, prim and pale.

"You may gaze upon my pussy," Ashley continued, "and the large butt you seem to covet so highly. I must admit, your strange ways baffle me, slave, but I shall grant you this favor just once, so do not take it for granted. But be warned, neither my pussy nor my butt may you touch. Failure to heed my warning shall result in swift punishment. Do you understand?"

God, I loved this girl. "Yes, Mistress Ashley."

"Good. Now, I shall proceed to suck this big dick, because it looks amazing and I'm tired of waiting."

A warm wetness enveloped my cock and drew me into it. I groaned loudly as Ashley's soft lips moved up and down over my shaft, rolling over the ridge to tease the large domed glans. A few times, her teeth scraped against me, causing me to jump, but each time she held her jaws open wider, and the overall sensation delighted me to my core. I closed my eyes and moaned softly to convey my enjoyment.

The sound of movement on the sofa and a sliding zipper gained my attention and I opened my eyes to see Kayla pulling her shorts off. These were quickly followed by her panties. When she resumed her seat, her hand immediately dropped between her legs to play with herself while she enjoyed the live action porno unfolding before her.

For several long minutes, Ashley sucked my cock in front of an audience comprised of her three best friends, the only sounds the wet noises from her mouth and Kayla's heavy breathing. Ashley dropped to her elbows when her arms began to tire, then eventually settled her entire weight on top of me.

The lower position brought her crotch to my face, and she ground her hips against me. Despite her stern warning, I kissed and then licked my way around her pussy. Based on the low moans and rocking hips she responded with, I gathered that she'd rethought her proscription against such forbidden acts.

Though my arms were bound, my feet remained free and I pulled my knees back to spread my legs. Ashley took advantage of the positional change and the new access it afforded to wrap her arm around my thigh and use her hands to stroke my shaft and massage my balls.