The Task Pt. 04

The bathroom was pretty over the top as well - more floor to ceiling mirrors and a glass box of a shower that was definitely big enough for two. Or more, really. After taking care of business I washed my hands and took a close-up gander of myself in the mirror over the sink. My makeup was holding up surprisingly well, given that I'd gotten a little sweaty - sorry, I began to glow - in the bar. My lipstick was pretty much gone and though it took a few tries and some exasperated blotting I got my lips back to their full plumped and painted glory. I had no idea what to do with the tube - again, why no pockets? - so I just left it on the counter and headed back into the room.

Cass was sitting on the edge of the bed, clad in a thick white terrycloth robe that must have come with the room. Her orange dress was in a heap on one of the tables and my cock started to rise again at the thought of what she might - or might not - be concealing. She rose as I approached, nodding.

"Good work on the lipstick. It can be tricky when you're first learning." Grabbing a gym bag off the floor - she must have brought it up here when she checked in because she definitely didn't have it while we were making out in the elevator, and I doubt it walked up by itself - she took a few steps toward the bathroom before stopping and turning back to face me. "How are you holding up with all of this? You okay?"

"It's been a blast. I had hoped it would be survivable with a slight chance of a little fun but it's been kind of awesome." I rubbed my hands on my hips. "I'm a little sad it's taken me this long to be willing to try new things."

"About that." She looked down, pressing a finger against her lower lip. "I was hoping to keep expanding your horizons a little more, but I want to make sure you understand that you shouldn't do anything you don't want to. 'No' is a word I understand and respect."

"I appreciate your concern and want you to know I trust you. I absolutely will say no if you present something to me that I'm not ready for. Or interested in. Or afraid of, even."

She looked up and met my gaze. "In addition I may get a little... salty with language, and while I don't think it will be a problem for you I can't ignore the possibility that it might be. To be sure we're going to add a safe word, like when I tied you up that time. At any point if anything I say or suggest is too much, I want you to say 'rutabaga.' I'll immediately back off. Does that sound good?"

I laughed. "Should I be nervous?"

Cass pursed her lips and shrugged. "For me to know, and you to find out. I won't be but a minute. If there's a knock on the door it'll be a couple of the financial guys from the bar, just let them in." She only lasted about three seconds before cracking up. "I think you believed me for a hot moment. I'll be right back. You might want to save me some time and lose some clothing - the shoes and the bolero should go, but I'll leave the rest up to you." With that she headed into the bathroom, the sway in her step leaving me drooling with anticipation.

I shed the sweater and kicked off my shoes, leaving them by the table with her dress. Checking myself out in one of the mirrored walls, I absentmindedly rubbed my now completely hard cock over my skirt as I contemplated what else should go. Not the stockings, of course, and I felt like the skirt was still a fun layer for her to leave on or take off at her whim. The shirt, though... yeah. I felt almost disconnected from myself as I watched me pulling it loose from the skirt and beginning to unbutton it, starting at the bottom, at a very slow and deliberate pace. When I reached the final button I slid it off my shoulders and tossed it on the table, never taking my eyes off my now almost-naked upper body. The black lace stood out as it held my breasts and for a moment I thought about ditching that as well but I decided that might be something Cass would enjoy doing herself. Also, though they looked to be doing okay it would be a pretty heavy buzzkill for me to take it off and have one of my boobs go with it.

"You left your lipstick in here." Cassie's voice, muffled through the bathroom door, snapped me out of my literal navel-gazing.

"Yeah, I had nowhere to put it. Besides," I said with a smug grin, "I kept thinking it would be awfully nice to see that shade being transferred from your lips to my cock."

Cass pulled the door open and stepped out. The robe was gone, and in its place were several items that appeared to be made from some sort of shiny black leather: greaves that ended by her wrist; a vest engaged in a valiant but doomed battle to contain her breasts; high-heeled boots that almost reached her knees; and a mask that covered her eyes.

Oh, and around her waist was some sort of harness, from which jutted a large pinkish dildo.

"Funny. I was just thinking the exact same thing."

She raised a riding crop that had been hidden behind her thigh and twirled it by the wrist strap. "I see you can look all sexy and slutty. Been teasing me all night with it. But when it gets right down to it, are you my prude or my whore? I'm hoping it's the latter because let me let you in on a little secret - my definition of a whore is not the usual one. To me, a whore is someone who can't get enough sex, loves to do things prudes would consider dirty or perverted, and is all about sharing pleasure with others. Not sure I'm actually 'taking it back' because I think it's always been derogatory so I guess I'm just well, 'taking it.' Being my kind of whore is a whole lot of fun." She pointed the tip of the crop at the carpet in front of her. "Come on over here. Already have your shirt off, I see. That's a good start."

I did as told, my nerves jangling with a mix of nervousness and excitement. My eyes kept straying back to her cock, wondering what she had in mind.

"Look at you, eyeing my big, beautiful cock. Is that what I look like when I see you naked? Hungry, but a little wary as well?" Cass laughed. "Let me put your mind at ease, lover - I have no intention of trying to fuck your ass with this tonight. That would be a pretty huge step for you and more than you're willing to try, am I right?"

My nostrils flared at the smell of her leather as I nodded.

"Understood. Alas, I can't make the same promise about a different orifice because, as I mentioned before, I've really been looking forward to watching you smear your pretty lipstick all over my cock. That's what whores do, you know." She set the end of her crop against my left knee and began dragging it upward. "These stockings? Wonderfully whorish. I see someone like you wearing them - and wearing them as well as you are - and I say to myself, 'Cass, I bet that's a filthy whore who enjoys sucking cock.' Do you think I'm right?" Sliding under the hem of my skirt, the crop crossed the welt before slipping to the middle and resting under my balls. Cass grinned at the hiss the warm leather drew from me, lifting a bit before continuing forward. Without even thinking about it I rose to my tippy toes as Cass let out a low, lewd chuckle before pulling the crop back again.

"So skittish. Perhaps one day we'll visit that arena, but not tonight." The crop began moving toward my upper body again, exposing my throbbing cock as it lifted the skirt. "Happy Birthday to me! Looks like my little whore is having a good time." She leaned in, her lips close to mine. "Is that safe to say, Leia? Are you having a good time?"

"Uhm. Y-yes," I managed to stammer out as my entire body fairly trembled with sexual energy.

"Good, good," Cass answered in a low, sultry tone. The crop began moving again, the skirt falling back in place as the tip traced a path over my solar plexus and between my breasts. "These are holding up well, I see. I like your tits, Leia, and the fact that you seem to enjoy showing them off is wonderful. A whore should be proud of her body. Are you proud of yours? Do you like the way you look tonight?"

I was dying to lean forward and kiss her - absolutely dying to - but instead I nodded. "I am. I look sexy as hell. I am *fucking* hot."

She gave another one of those deep, throaty chuckles, her eyes sparkling with amusement. "You're *going* to be fucking hot very soon. I'm the 'hot' in that promise, in case you were wondering. The thought of being with a whore like you, well..." Cass held up her empty hand and wiggled a glistening index finger. "Makes me behave like a whore as well, it seems." Her eyes never left mine as she popped the digit into her mouth and sucked it clean. "Mmm. You've had me slow cooking the entire night so it's not surprising things have turned out so... delicious. But I'm getting distracted."

The crop pressed under my chin for a moment and I thought she was going to push my head back, but instead it shifted to the top of my shoulder. She tapped it a few times before exerting significant downward pressure, which I responded to by dropping to my knees and finding myself face-to-face with her dildo - well, face-to-cock. I discovered I was filled with trepidation - was I really going to do this? The thing looked enormous up close and... and I realized that the scent of my wife's arousal was thick as hell down here. She really was on fire about this, and, well, what was the harm, right?

"You seem pensive, my little whore. It's like you've never been on your knees with a cock in front of your face before."

That drew a chuckle from me, some of my tension melting away. "Weird, right? It's just so... big."

"Oh, you dear sweet thing." The dildo bobbed as she shook with laughter. "You know your own cock is bigger than that, don't you?"

"No, it's not. Is it?"

"This is a six-inch dildo. You are both longer and girthier than this is, something I'm looking forward to confirming in the very near future." She rubbed her hand against one of my cheeks. "If this is something you don't want to OHHHHHH FUCK!"

As her reaction might indicate I decided that for a number of reasons I wanted to have that cock in my mouth and so, while she was reminding me that I had the option to back out, I opened my mouth, leaned forward, and wrapped my lips around the head. The taste of the silicon wasn't my favorite thing in the world but was tolerable. Remembering the countless times Cassie had given me fantastic blow jobs I set about putting her techniques to work. I slid the tip out of my mouth and began tracing along the edge of the head with my tongue. After a couple of circuits I trailed down the underside of her cock, feeling it tremble as her knees gave a bit of a wobble.

"Oh baby," Cass moaned, her hands on the sides of my head. "Look at how much you learned from me. What a g-good little whore you are, so filthy. That's right, w-work my cock. I think you - ohhh - I think you like it."

In response I shifted position and once again took the head in my mouth. This time I decided to see just how much of her I could handle, taking my time as more and more of her dildo slid down my throat. The sensation of being filled was new and exciting, and feeling the dildo moving in and out, the ridges and contours against my cheeks and tongue... it wasn't what I'd expected and far more enjoyable than I could have anticipated.Her groans increased as her grip tightened on my wig, and I could sense she was barely restraining herself from ramming it in as far as it would go. Closing my eyes, I drank in her intoxicating aroma as I waited for the moment my gag reflex would get triggered and I'd have to back off.

Instead I made a muffled noise of surprise as my nose bumped up against her belly. Maybe I have a big throat or it's just really relaxed but either way I had six inches of cock buried inside me with no problems encountered. I felt Cass buckle at the knees for a second and I slid my hands around her waist, getting a firm grip on her magnificent ass both to help support her if she needed it and because why wouldn't I want to grab it? I caught a movement out of the corner of my eyes and realized I was able to see myself in what must have been a reflection of a reflection and... woo. I watched my wife's cock vanishing inside my mouth as I swallowed her whole, and as it emerged, glistening, only to be enveloped again. Between that and the makeup I feel almost unrecognizable, a random whore giving a blow job. That view... yow. I'm not sure if my own cock had ever been harder than it was at this moment.

"Oh holy fuck you're fucking deep-throated me, you're deep throating me oh fuck oh fuck oh fuck!" She pressed hard against my face for a moment before I felt her shuddering as she let out a wordless cry, and I realized with a bit of surprise that she was coming. I knew this was exciting her but I didn't think that would happen and I felt her sag a little in my grip before recovering. When I heard her take a deep intake of breath I slid her cock back out of my mouth.

"You okay?"

"Oh, I'm *definitely* okay, you wonderful little whore."

"I have to say I didn't think that was something that could happen but am happy that it did."

She sniffed, cleared her throat. "Yeah, I forgot to tell you that this harness also has an attachment on the inside in the form of a smaller but evidently no less effective dildo currently buried in my cunt."

"I see. So you felt me taking all of your cock into my throat deep inside your pussy and it made you come."

"Mmm yes," she said, her voice ragged. "Indeed, it did.."

I looked at the dildo wavering in front of me, shiny with my saliva, before looking up and catching her eyes. "So what do you think would happen if you grabbed the sides of my head and fucked my face? Like, really fast and really hard?"

"Oh." While seeing my wife turned on wasn't a new experience, this level of naked lust was unprecedented. Her voice was a little thick and syrupy, as if she were dazed. "Oh. Uhm, I'd probably come so hard that I'd fall down. Which I'd be willing to - oh!"

I shifted my hands to her hips and did some twisting and pushing until her back was up against one of the mirrored walls, feeling as much as hearing her gasp at the contact against the cool surface. "And now?"

"I... I think it would be AHHHHHHH!"

Yeah, I didn't wait for her to expound, instead swallowing her in a swift motion before retreating again. She cried out again before snarling and digging her fingers into my wig. "Oh, is that what you want, you little whore, you want me to fuck your face hard?" She started pounding her hips against my face and a little tickle warned me that I did indeed have a gag point and that it was right about there. It wasn't enough to be debilitating but I felt tears spring to my eyes as Cass continued yanking and thrusting. "You like it, don't you? You like me fucking your face like this, you like a cock being rammed down your throat, yeah you do, yeah YEAHYEAHYEAH OHHHHH FUCK!!!"

Cassie's entire body locked up for several moments as she made 'ah ah ah' noises before she fell back against the mirror and started to slide down. Letting the cock slip out of my mouth, I managed to keep her upright by bracing my arms against the wall and around her. I wasn't going to be able to hold her there for very long but she came out of her orgasm-induced fugue in short order, gathering her legs underneath her. After giving my cheek an affectionate rub, she trailed a finger along her cock.

"Nice and wet. Almost as if you knew what I had planned next." She grabbed me by the chin and gently urged me to stand. "Get into bed and on your back, my delightful whore." When I turned to go she gave me a stinging slap on the ass. "Absolutely delightful."

With a grin I hopped over to the bed, looking forward to having my aching cock attended to at some point. After yanking off the comforter I jumped in and flipped to my back, getting a good view of myself in the mirror directly overhead. My makeup was a little worse for the wear - the tears caused by the frenzied face fucking had left black trails of either eyeliner or mascara and my lipstick was smeared enough to look like I'd been playing a trumpet - but taking in the stretched-out length of my body in a bra, skirt, and black stockings was glorious. I might have gone on eye-fucking myself forever but Cass (now missing her mask) landed next to me, her mouth locking on mine. One of her hands slipped under my skirt, cool as it wrapped around my shaft. Just as quickly she broke the kiss and swung a knee over me, straddling my stomach as my mind whirled. She hooked a hand behind my neck, pulling me up as she lifted her hips.

"A little more sucking, please. And be sloppy about it."

I barely got my mouth open before she thrust her cock into me. This angle wasn't conducive to more deep throating but I took what I could as she started fucking me again, making sure to give her the extra moisture she'd requested. I could feel excess drool running over my chin before she pulled out and sat back on my stomach. I could feel her wetness and heat and my cock bounced in response. She smiled at me - ye gods, my wife is fucking gorgeous - before grabbing my arms and moving them so my forearms were pressed against the outside of my breasts.

"Do your best to hold them there, please. I'm going to fuck your whore tits and enjoy it even though part of me is sad I don't have a real cock so I could explode all over your neck and face and make you lick it up." Her grin became sheepish as she got up on her knees and leaned forward. "Excuse my babbling but I think you scrambled my brains a bit. Anyway..."

Cass lowered her hips and, after slotting her cock between my breasts, nudged my forearms a little tighter. Then she started to move, her hips thrusting to drive her dildo back and forth within my cleavage. As I looked down I was treated to an incredible view - the head of a cock staying just tantalizingly out of reach of my mouth on her up strokes, her own tits swaying back and forth with her motions, her moaning and biting her lower lip as each thrust was echoed by the attachment in her pussy. The imagery over her shoulder was even hotter as I watched her ass pumping away in the mirror. While I may not have been experiencing the same sensations I would have if my breasts were real the eroticism of the tableau was off the charts and my cock throbbed along with every grunt and groan Cassie spit out as she thundered toward what I assumed would be another massive orgasm. As an added bonus her hips kept pressing on the top of my skirt on her downstrokes, to the point I was beginning to have concerns that the contact was going to push me over the edge. I suppose it might seem unlikely to anyone who wasn't a dude having their first teenage make-out session but in my defense I had been perpetually aroused since Cass had first gotten home today.

That potential problem was eliminated from consideration as my wife abruptly put her hands behind my neck again and pulled me with her as she fell off to my right side, shifting to put her cock against my lips. "Open up and finish me off, Leia. Make me come like the whore I am."

I responded with great eagerness, her cock filling me yet again while her voice crumbled into frantic whispering. It wasn't a great angle for me to take all of her but what I could handle was evidently enough as she made inarticulate noises while tightening her grip on my head. Her scent was almost overpowering as her cries rose to a crescendo with each frantic thrust.

"AHHH! L-L-L-eeee AHHHHH" Her fingers dug in hard as her body twitched and jerked for several moments. Her cock came free from my mouth with an audible 'pop' as she collapsed backwards onto the bed, gasping for breath. I used the back of my hand to wipe away my drool while checking the condition of my no-longer-virginal breasts. The left one looked okay, but my right boob had pulled free on the inside. Given how strong the adhesive was I was surprised I hadn't noticed at the time but then again, things had been happening. I started to rise up on my elbows but Cass languidly placed one of her bare heels - where had her boots gone? - on my upper chest.