Gloria's Daughter Ch. 03

"Three hours, chime. What else?"

"I'm going to do things in stages, okay? I'm going to start off as Nice Dennis, and hopefully when we've done a round of that, you'll be comfortable enough that I can switch to Demanding Dennis. Then if that doesn't scare you off, I'll eventually get to Dick Dennis."

"You act like a dick to my mom?" A little heat colored the question.

I raised a hand to placate her. "Not very often, and the key word there is 'act.' Sometimes we role-play. She'll pretend to be," you, "my boss, dressed up in a business suit."

"Your boss is a chick?"

"Yes, my boss is a woman. And she's kind of a bitch. And she's my boss, so I don't get to be a dick to her. But Gloria can put on a wig and a suit, and then I get to tell my boss the things I'd like to tell her and order her to do the things I'd like her to do to make up for how she treats me at work."

"Huh." She thought for a second, then said, "I guess I get it."

"So here's the really important part," I said. "If we get that far - hell, even if we don't get that far, but something's happening and you need me to stop, you're going to have a safe word. And if you say it, I'll stop, no matter what, right then and there. Okay?"

"I know what a safe word is," she said, a bit bristly. My eyebrows went up, and she bristled even more. "From reading smut stories online, not from being a perv myself."

"So pick one. What's your safe word."

She considered for a moment.

"Asymptote."

"No, something simpler, something you can say quicker. And something that doesn't start with 'ass.' You may be saying 'ass' for some other reason, and I don't want to have to wait and see if you're going to add 'ymptote' every time you do."

"Scorn."

I laughed. "Sure, that's good. What else? Oh - boundaries. The customer is the customer, and if you're too picky about what you will and won't do, he's not going to want to pay you. But you get to say going in what you're willing to take and what you're not. Gloria doesn't let most guys do her in the ass, for instance -"

"But you, she does?"

"- but if you're okay with taking it there, that's up to you. To start off, I'd say you should be hesitant about letting anybody tie you up. And you should definitely insist on condoms, every time for every hole. And no kissing unless you want mono or something."

"Duh. But you didn't answer my question."

"And I'm not going to. You can ask your mom if you really want to know; I'm not going to piss on her privacy."

She tilted her head a little. "Damn. You really are a nice guy, aren't you?"

"Doesn't Gloria keep telling you that?"

A shrug was all I got in response. "So what else?"

I didn't have any other instructions, but I still chewed on my lip a second. "Just ... when you open that door and let me in, remember that I'm acting, okay? Even when I start off as Nice Dennis, I'm role-playing for you, and only because of what happened to Gloria. I'm not saying I won't start enjoying things at some point; I'm not saying it's going to be a chore. But I'm nervous as hell, and I really don't - I don't want you to come out of it hating me."

"Fuck," she said, blue eyes widening, "are you going to ask her to marry you or something?"

I scowled. "Just get inside and get changed. I'm ringing the bell in fifteen minutes."

* * *

When she opened the door, I saw Kaylee completely transformed. For one thing, she was eye-level with me in a pair of three-inch white sandal heels that matched her camel-toe-tight white denim shorts. She had on the blouse, too, and I stared at her tits in it for longer than I should have. They filled the top out lushly behind the neckline fringe, pert and proud and clearly unhampered by any bra. Only as an afterthought did I look to see that the cum-stain had definitely washed out.

Her face ... well, every time I'd met her before, she'd had on very little makeup, just enough to accentuate the natural perfection of her features. Now she'd vamped it up - not in a tacky or sleazy way, but enough to make her lips a searing red and bring out the full vivacity of her eyes. I puckered as if to let out a whistle, but didn't.

"Wow. You look fucking hot, babe."

She got a smile on at that, with only a twitch of awkwardness. "Um, thanks. I guess ... you're not looking bad yourself."

A little forced, but she seems to have the idea.

"So, I guess - come on in, right?" she stepped aside, holding the door wide, gesturing into the boudoir. The move looked natural enough. But before her hand dropped, I thought I caught it shaking.

"Sounds good to me."

As I walked past her, I caught a whiff of freshly applied perfume, something fancier and more intoxicating than the light scent I'd caught from her back in the car. It occurred to me that the earlier smell must have been her deodorant, not perfume. The state she'd been in, she obviously wouldn't have gotten up and put on perfume to start the day. Duh.

The boudoir, so familiar, usually so calming to me, seemed to crackle with unexpected static energy, threatening to zap me if I touched anything. My chest felt tight. My pants - in the crotch area, at least - felt even tighter. I put a hand behind my head, scratching the scalp there. It's very strange having to force yourself to do something you're dying to do, but that's what it took for me to turn my head and look Kaylee up and down several times as she stood waiting by the door.

"Yeah, super-hot. This is still kind of weird for me, though. You said on the phone you're taking over for your mom - does that mean you're up for anything she'd be up for?"

"Uh ..."

"No, never mind. I can tell you're new at this - I won't ask for anything freaky."

"You can tell? How?"

"Well, you look like you're about to shit yourself for one thing."

Her face reddened, her mouth opened, and her eyebrows dipped downward before she caught herself and shrugged instead of saying whatever had just popped into her mind. "Okay, yeah. I'm a little nervous. How do we get started?"

"Let's have a drink. Sit down on the couch."

For the second time that evening, I went to the tiny refrigerator and returned with wine - two glasses this time. I found her sitting very straight as far to one end of the little loveseat as its arm would let her go.

"Here." Handing her a glass, I relaxed into the other corner (well, pretended to relax), my legs angled toward the middle of the couch instead of pointing straight out like she'd left hers.

She took the glass and gulped from it.

"Whoa!" I laughed, then reached over to touch her wrist. "Let's not get you too hammered too fast."

Lowering the glass, she twitched a nervous smile my way. "Sorry."

"Don't be sorry." I sipped my own wine, then leaned to set it on the floor as I reached for my shoelaces. "I'm going to take my shoes off here."

"I'll try not to faint."

"Ha, see, that's good." My angle, as I bent, put my head almost level with her flawless white knees. I undid my laces by feel, eyes magnetized by her legs and pulled up along their clean, lush length to the point at which they entered her shorts and framed the denim-tightening curve of her mound. Then I realized where I was looking, turned my face back to my shoes and got them off.

Kaylee had her eyes awkwardly pointed at her lap when I leaned back into the cushions.

"Sorry," I said, before I could help it. "I didn't mean to be a pig. You're just - god, you're fucking amazing."

That made her smile and squirm simultaneously, but at least it got her eyes pointed back my direction. "Yeah, well ... maybe this is going to be a little harder than I thought."

"Drink some more of your wine," I said. Then, out of nowhere, I added, "And I'll tell you about the first time your mom and I did it."

"Jesus, TMI," she said, holding the palm of one hand toward me.

I laughed. "Not the filthy dirty bits. The part like this, where we were sitting drinking wine and one of us was freaking out. But in that case, it was me."

Looking at me suspiciously over the rim of her glass, she tipped it up and drank - then touched her fingertips to her mouth as a little ladylike burp snuck past her. "Oop. Excuse me."

The embarrassment seemed to do her good. I raised my glass toward her, then took a drink myself.

"So ... why were you freaking out."

"I'd never done this," I said. "Paid for sex. My whole life I thought it was sleazy and disrespectful and, well, just plain wrong. But my wife had left me six months earlier, and the sex had been bad for a year before that, and when I went out to strut my stuff with my newfound freedom, I ended up feeling shitty after every one-night stand, because I was still too hurt to go for a relationship and I felt like I was just using women as meatbags."

Her eyebrows furrowed. "Did you lead them on like you were Prince Charming? Or were they just out for a quick hookup too?"

"No, I was pretty straightforward. None of them wanted more than a night in the sack. But I still felt like a user. Like I ought to want to get their numbers, call them again, maybe ask them out for dinner and a real conversation."

Kaylee laughed and shook her head. "Dude, sometimes girls just want to fuck too. Why would you feel bad about it?"

"I don't know." I shrugged. "Maybe I'm just a romantic. Anyway, when a buddy of mine told me about your mom, I decided, 'What the hell.' If I was going to feel like a user, why not go all the way and use someone who definitely, a hundred percent for sure did not want me to call her for dinner and a movie sometime?"

"Not completely illogical, I guess." She tilted her glass up again, getting near the end of its contents. "But you got here and lost your nerve?"

Figuring I'd better keep up with her, I took another swig myself. "I wouldn't exactly say I lost my nerve. But I got pretty close. And I might have, if your mom wasn't your mom."

"What do you mean by that?" Genuine curiosity had taken over her face by this point.

"Well, she got me drinking and she got me talking ... and she kind of tucked her legs up on the sofa with us like this." I demonstrated, drawing my knees up and angling my hips. The position brought my body perpendicular to the length of the loveseat, so that I faced directly toward her. My right arm went up onto the sofa back. "Only I'm sure she made it look a lot more casual and natural than it looks on me."

The last of her wine drained away and she held the glass idly by its bell, dangling her hand off the arm of the couch. "It's a little girly. But you're sorta carrying it off. So what then?"

"She asked a lot of questions, like she cared about the things I was saying. And every once in a while, she'd shift a little - not a lot, not like she was trying to move toward me, just like she needed to reposition a bit to stay comfortable. But somehow, every time, she ended up an inch or two closer."

As I attempted to show her, she raised an eyebrow. "Dude, that was more like six inches."

"She was way better at it than I am." My hand now rested above her shoulder on the seatback. "And every inch closer she got, I realized a little more how incredibly sexy she was." I scooted again. "I mean, at that point, she was, what, maybe only five or ten years older than you are now, right? So she still had it all. Not as supermodel hot as you are, but hot and sexy aren't the same thing, and she just poured on the sexy."

"And then what?" she asked quietly, glancing down to where my knees all but brushed against her left thigh.

"She kept talking to me, and she got one finger in my hair, like this." I showed her, lazily curling a lock of shimmering red around my index finger. "And she asked me some more questions, and she unfolded her leg across my knee like this." My calf inside my dress pants came to rest at the juncture of her locked-tight knees, and then she let them part, so that my left leg could hook over hers. Her breathing sped up. She looked at my knee atop her own.

"I'm ..."

"Hmm?"

Fragile-looking blue eyes came up to meet mine. "Whooh. I'm starting to think I can really do this."

I brought my hand down out of her hair to brush her cheek. "Of course you can."

Leaning outward, my fingers trailing down her throat, along her collarbone, I set my wineglass as far out from the couch as I could. Then I took hers from her loosened fingers and set it beside mine.

"What do I do?" she asked, trembling.

"Don't do anything just yet. Let me do." I brought my left hand up to rest on her right knee, my right curling the fingers around the nape of her neck, gliding the side of my thumb along her jugular to the hollow behind her earlobe. She sucked in a breath and bit her lip and closed her eyes. "You're a very beautiful woman, Kaylee. You deserve to have things done for you."

With a kneading grip, I slid my hand from her knee along her thigh, thumb questing patiently along a path toward her groin.

"To you." Simultaneously, I pressed the tip of my thumb against the fabric that stretched tight across her mound and leaned in to put my lips against her throat, behind the corner of her jaw. She gasped. I smiled and whispered, "Yes, that's good, right?" into her ear.

She nodded, quickly. I kissed my way down her neck to the graceful slender curve of her collarbone. Lower, my thumb dipped into the right leg of her shorts, squeezed tight between fabric and thigh-flesh, pressing firmly inward, deeper, until I felt the hem of her panties. She widened her legs, slouched her hips down. My thumb rounded the corner between pant-leg and crotch, feeling the soft curve of her mons through her panties.

"Oh god," she said.

Tonguing my way down her breastbone, I tasted the salty skin within her cleavage. My right arm curved around her neck, bringing my hand downward from trapezius to clavicle to the neckline of her blouse and in.

"Aahh ..."

My thumb found the button of her clitoris, rapidly engorging. I massaged it gently, briefly, as my fingers circled her erect nipple within the blouse.

Working my mouth wetly back up to her ear, I said, "In a second here, I'm going to take my hands out of your clothes, and then if you want me to, I can get up and go to that dresser along the wall. It's got a box of oral dams in the top drawer. While I'm getting one, you could get your pants off, and then I'll come back and eat you out through it."

"Oh fuck ..." she gasped. "Are you for real? You're going to pay me for letting you do that to me?"

"What can I say?" I asked, continuing to rub her clit. "Nice Dennis is nice."

"Jesus," she said, then sucked her lip between her teeth a moment. "Okay."

Easing my hands from within her clothes, I stood up and looked her over, splayed in the corner of the loveseat, legs now apart and stretched out before her, nipples pressing hard enough against her blouse to be noticeable even through the silky blue frill. She watched me taking her in, and when I smiled she sort of involuntarily followed suit.

The black chest-of-drawers opposite the king bed took me just a couple of steps to reach. I opened the topmost one, where a bowl of condoms and the dental dams and a healthy supply of various lubes sat in neat, orderly arrangement.

"Why don't you stand up and turn around and show me how sexy you can be getting those shorts off? Just the shorts - I'd like to do the panties, if you don't mind."

"Uh, all right."

Muscles glided within the satiny skin of those pale anaconda legs as she rose. Her eyes stayed on me when she turned, face angled my direction over one shoulder - halfway between smolder and mistrust. South of that face and north of those legs, her ass swelled the confining white fabric of her shorts to water-balloon smoothness: taut and full and curved as though the laws of physics could not allow any other shape.

Swallowing hard, I stopped her as she worked at the top button of her shorts.

"Hang on a second."

"What?" The smolder in her eyes tilted further toward mistrust.

"Could you just ... I don't know, bend over for a minute before you take those off? I'm not sure I've ever seen an ass and a pair of shorts that worked together that well."

Her expression did a little sashay of gratitude and embarrassment, but she turned fully away from me and leaned into the arm of the sofa, pushing the white-clad heart of her bottom out even rounder and firmer. If the shorts had split at the seams, it wouldn't have surprised me.

"Wow. Yes. Hold that for just a second." My throat felt dry as Death Valley, and my cock screamed at me to haul it out and jerk the hell out of it right now. But I managed to fumble in the drawer for one of the dental dams and a bottle of lube ... and a condom. "All right, stand back up before I come just from looking at that. Holy hell, Kaylee."

When she looked over her shoulder again, her ambivalence had all gone to a glow.

"So you want me to take these off now?"

"Fuck yes."

Undoing three vertical buttons, she watched my face as I watched her hands slowly release the fasteners of heaven. Her zipper went down so gradually that it ticked instead of zitzing. With her thumbs in the waistband, blocked from my sight by her torso, she tensed her arms to start pushing.

"No, no," I begged, moving my hands in a horizontal circle, "bring them all the way around before you do that."

She did, thumbs sharking between the waistband and her flesh, fingers trailing first down her hips, then across the high slopes of her buttocks, ending pinkie-to-pinkie in a wide-spread clutch like pale honey poured over a double dish of ice cream.

"Whoosh," I said. "Okay, I'm ready to see what you've got inside those pants now."

Nodding, she pushed and wiggled, ass rolling side-to-side as the tight denim crept downward. The hue of her flesh showed only a shade or two darker than the shorts. When her panties came into view, they were ghostly pink.

Her shorts dropped to the floor. I continued to stare.

"You want me to bend over again?"

Yes, until the timer goes off in three hours!

"No ... how about if you sit back down."

"Sure." She pirouetted around and down into the cushions, landing with her legs wide enough for me to see three different colors in her panties - the pastel pink, a textured pink-red shadow where the panties trapped her bush, and an irregular dark patch the size of a quarter, centered on the spot where her cunt pushed into the fabric.

I walked slowly toward her, stepping around our two wineglasses to stand in the V of her spread legs. Her chest moved with fast breaths as I approached. When I stopped, her eyes glanced to my left hand, which held the lube bottle and had the wrapped condom between two fingers. I tilted the hand to emphasize the rubber in its little crinkly foil package.

"I could have pocketed or palmed this while you were turned away and brought it out once I'd licked you senseless," I said. "But I didn't want to spring it on you like that ... our first time."

Her eyes stayed on the condom. Deciding whether to be alarmed? Then she met my gaze and eased her hips lower to hang her ass right at the edge of the couch.

"Thanks, I guess. But you had me at, 'licked you senseless.'"

I grinned, lowered myself to one knee and then the other, set the lube and condom down at the base of the couch. Once I unfolded the dental dam, I brushed the hem of her blouse up along her belly until it bunched together, riding her ribcage right at the breast-line. That cleared enough tummy for me to lay the latex sheet out on. Then I wrapped my hands around the backs of her thighs and leaned deep into her crotch where a few breaths of dank, musky female arousal confirmed the nature of that conspicuously located wet patch.