Ginger Goes All The Way

I guess I knew it would be a good day the night before, when she told me to lay out her clothes for her. I chose a mid-thigh black skirt, a silky cranberry blouse, black jacket, and textured black stockings. She came in as I was choosing her shoes, cranberry pumps that complimented the blouse. She crossed her arms and sighed heavily.

"What the fuck is this?" she said, walking to the bed and picking up the stockings.

Her tone caught me off guard, and I felt a not at all unpleasant "thud" in my chest as she turned her eyes to me.

"Uhhh...they look great on you baby...they're sexy."

Lame. I hadn't expected the tone. She smiled...no...she grinned, and stepped toward me.

"Baby..." she whispered as she drew near, "I can't look like a total slut at work...you know that by now. Subtly slutty...isn't that what we say? Save these for another day, OK?"

Her tone had softened, her eyes danced...she knew what she'd done to me, and she knew we both loved it. I went to the dresser and chose plain back stockings, lace topped at least, and put the others away.

"Nice baby...thanks."

She planted a soft lingering kiss on my lips. My cock bobbed in my shorts...I wondered if she knew the power she held over me.

She was up before me in the morning, I heard the alarm through the morning haze, the shower running. Smelled her perfume as she moved about getting dressed. It was Friday drinks at her work that evening, they did it once a month, and she'd go in early to get a jump on the day since they'd leave the office a bit early that night. She'd never had me lay out her clothes for work drinks, but our play had been escalating over the past several months. She was learning to pull my strings, gauging the effect. No sex last night, she'd claimed the early morning as her excuse with a wry smile, then slid over and pressed against me, feeling my stiffness. She knew, because I'd told her, that little things like last night's harsh tone would stay with me and inflate my cock throughout the day as my mind inevitably drifted back to the moment.

"Really??" she'd asked, not quite believing.

"Really" I'd said.

"Hmmm." she'd said, a thoughtful smile on her lips, and I'd enjoyed a flurry of those moments ever since.

Drifting back to sleep, I jumped slightly as she touched my stomach, thought she was leaning down for a kiss goodbye, but then felt her nails trail lower, inside my shorts as she began to stroke me. I stiffened, and she withdrew her hand. I watched in the dim light of the clock LEDs as she hiked up her skirt and slipped out of her panties, then straddled my head and lowered herself over me. She pushed my shorts down and took hold of me as I sprang in to the cool air. She smelled great...soap, perfume, the delicate rosewater drawer liners, all mixed with her scent.

She was wet already and I groaned involuntarily at her taste as I pushed my tongue into her slit. She sighed, stroking me softly, as I pushed my tongue inside, flicked it over her clit, and found a rhythm. She began to pump me as I worked at her now slippery lips and I felt her legs tense against my sides as she drew closer. She cried out softly when I nibbled her clit, then sat upright and let go of me as I sucked it between my lips. She always came easily when I licked her and I had her at the brink now. I released her clit, pulled my tongue back, planted a soft kiss on her lips, teasing her back for her letting me go. I felt, more than heard, a low growl in her throat, then her hand on my head, nails scratching my scalp as she pushed her ass more firmly on to my face. Holding my head in place, she began rocking, and I obligingly replaced my tongue on her clit. She came hard after only a few fervent thrusts of her hips.

Ginger isn't a regular squirter, she's more of a flooder because her pussy seems to flood inside when she cums, her juices ultimately dripping or splashing out depending on her stance. She's squirted on occasion, but this was a flooding orgasm. I heard my name, she always says my name when she cums and I love it. I lapped at the juices that dripped from her as she tensed and relaxed above me. She lifted her ass and sighed. I let my tongue slip over her asshole, evoking a giggle and a shudder, then she was up and standing next to the bed. My cock still throbbed, bobbing loosely in the darkness. She pulled on her panties...me wondering what was going on as she'd never left me hanging before. She leaned down, stroked my cock as she kissed me deeply, running her tongue over my lips as she pulled away.

"Mmmm...I taste good." she said, then "I'm late...you'll have to finish yourself, you lucky cuck."

And she was out the door. I lay there a little stunned, turned on beyond belief, and savored her lingering scent and taste as I quickly brought myself off.

I was distracted all day, thinking about last night and the morning, anticipating tonight. Ginger had been promiscuous, to say the least, after her divorce and still so after we'd met. I made no secret of liking it, even encouraged it, while we got to know each other. She had not fucked another man since we'd started dating seriously though, and had resisted my pleas to do so steadfastly. The topic came and went over the 3 years since we married, always a nice way to spice up our sex life, but always limited to naughty talk between the sheets. I looked forward to more of the same tonight, counting myself lucky to have such a beautiful partner to indulge me. Our play had escalated recently as I mentioned, however, and my curiosity at what tonight would bring filled me with a pleasant anxiety.

My mind drifted back to the early spring. The air smelled of sex, of sweat, faintly of whatever the cyberskin dildo that lay by my leg is made of. It had arrived that day. She'd made a real game of it, first suctioning it to the wall and kneeling before it, her brown eyes locked on mine as she sucked it. It's slightly bigger than me and her lips looked amazing stretched around it, sliding over its veiny shaft.

"C'mere baby..." she'd whispered, beckoning with a lacquered nail as she took it back in her mouth, parting her knees to show me where to go.

I lay back and slid beneath her, looking up as she sucked it and lowered herself on to me. Things got really good after that.

Later, as we lie panting, the sweat drying on our skin, she propped up on her elbows and asked,

"So how would we go about finding someone to fuck me, anyway?"

It wasn't a sincere question, rather a chiding one, as if it couldn't happen. I laughed involuntarily. Ginger is 5'7 and about 155 pounds, a nice full C cup and ass. Not skinny, curves in the right places including a bit of a tummy that I find incredibly sexy. She complains about it, but she's 36 to my 39 and all in all I think we look good for our age and sizes. Dirty blonde hair naturally, which I find gorgeous coupled with her dark brown eyes. She dyes it now and then, another change to add some spice, but then it was her natural color. She laughed with me but cocked her head questioningly.

"Sweetie, you could get just about any guy, any time you want." I'd said.

"Riiiiggghht."

"Well," I said, thinking about it, "There are probably a dozen ways to go about it..but for me, the best way, the sluttiest way, would be for you to pick up a stranger in a bar and take him somewhere."

She shook her head.

"Guys think it's so easy...I didn't get laid every time I went out to a bar, you know..."

"But you could have."

"No way." she retorted.

We went back and forth a bit, ultimately making a bet of it. We'd go Saturday night, hop around to a few bars, and see how many guys she could leave with if she were so inclined. I secretly hoped this would be "it", that she'd really do it, but it turned out pretty well regardless.

That Saturday night was the first time she had me pick out her clothes. She'd been doing some web reading on cuckolds and found this was something that some guys who were in to it did for their women. She was duly impressed with my work. She looked great and it was all I could do not to call the night off and take her for myself before we left. At the bars, I'd go in first, she'd come in a few minutes behind and go to the opposite side of the bar. If someone hit on her, she'd play along for a drink, then we'd exchange texts and she'd beg off to meet a friend she was expecting. If the guy said anything about the two of them getting out of there, a point for me. Otherwise, a point for her. Honor system.

After one drink or the proposition to leave, she'd text me, pretending to text the friend she was waiting for. I'd reply and she'd beg off as if her friend were just arriving, then we'd move on to the next bar.

In the first two places, two guys approached, she had two drinks, and I scored two points. In the third, someone approached her, but she abruptly stood and walked toward the ladies room, nodding at me to join her and leaving the guy standing there. In the restroom hall, she claimed that I'd obviously picked three meat-markets as the last guy hadn't even offered her a drink, just asked if she wanted to go someplace more private. I laughed and shook my head, but agreed to move on and picked a string of rather sedate pubs to put an end to her argument.

After five more places, we tallied the score as I started the car. My lead was insurmountable, six propositions to two "nice guys", as she called them. She was drunk. She'd taken to sipping her drinks and had only a club soda for her last drink, but she'd had plenty. She eyed me in the dark car, placed her hand on my crotch.

"One more place, one more guy..double or nothing." she said.

She hates to lose.

"I don't know...six to two...I think I need odds here babe." I replied.

"Odds? You fucker." A slight slur in her voice.

"OK...you can do what you want for the next week...anything you want."

"Anything?" I asked, raising my eyebrows.

"No...I won't fuck another guy...we've covered that...but YOU can do anything you want. To ME." She then added quickly.

Not really great odds, she knows I like to lick her more than anything else, so it was a win-win. But I was getting to see her hit on by a host of other guys, and besides, it was a win-win, how could I refuse?

Inside the next place, I saw the bartender approach her after a while, nod his head across the bar. We both looked as a striking black guy tipped his drink toward her. She was flustered, started to look my way, so I looked away, but nodded my head a few times. I waited a beat, then looked at her. She was looking at her drink, thinking, then she looked up, bit her lip nervously, nodded, and smiled at him.

Ginger grew up and had lived in the south her whole life. She isn't prejudiced toward anyone, but certain things just weren't done in her experience, and flirting with black guys is one of them. Her ex would have gone nuts.

She looked at me as he made his way around the bar toward her, so I gave her a wink and nodded again. A table opened up across the room, so I moved. It gave me a view from behind them, but I looked on at them sideways since they'd turned to face each other while talking.

I texted her as she sipped her drink. "Let's see some leg, sexy..."

I saw her react to the phone, she started to gather her things, probably wondering why I was calling it off early. She looked at her phone and laughed. He had a questioning look, she said something, and they relaxed again. After a minute she shifted on the stool, letting her skirt ride up a bit, glancing at me sideways with a wicked smile as her stocking top came in to view. She really was drunk. He noticed. After a bit, he touched her arm, and she didn't pull away. I saw his other hand slide over to her knee. It drifted higher as they talked. She pulled back the rest of her drink quickly though, then looked over at me, which I interpreted to be surrender and a call to end the bet. She picked up her phone and sent the text, then looked at it to make her point, but she couldn't fake a return message arriving as he'd already heard the tone once. She looked at me again, a beat longer. I just smiled, shook my head. Her eyes narrowed slightly, she turned back to him. Then an almost imperceptible glance at me followed by a slow shifting of her weight, allowing her legs to open further. My cock nearly broke through my slacks as his hand slid higher, fingertips disappearing under her skirt. She looked at me again, so I pulled out my phone and sent the text. She grabbed her phone, touched his arm, and made an awkward exit. He looked shattered.

In the car she growled, "You are such a PRICK!" But not angrily.

I laughed. "Wait..wait...so I guess I win?"

"Fuck you..." shaking her head.

Did I mention she hates to lose?

"Hey", I said, my voice growing serious, wavering a bit.

She looked at me.

"You...uhh...you can if you want, you know. Go back in there."

The car grew quiet, she thought for a beat.

"You really want that...would really like that?"

She stared at me and I didn't reply.

"God..you really would...I can see it in your eyes." She reached over and took my hand. "Baby, listen. We play at this...it's a fun game and I like it, even tonight. It's a game though."

She paused, then continued, "I don't want to go back in there, and I wouldn't even if I wanted to. What I want is for you to take me home and do what you want to me. You did win, after all...you shit."

That was as close as we'd gotten to the real thing, but that night sparked an escalation and the past few months had been all the better for it.

The ringer on my cell brought me out of my reverie. I looked to see Ginger's cleavage on the display screen. Over the summer, she'd come out ready for an outdoor party with a plunging button down blouse coupled with a push-up bra that really showed her assets.

I'd looked and said "Nice cans...", smiling.

"Too much?" she asked, seriously.

"Nahhh...you should undo the top button, in fact."

She sighed heavily, then "Dammit...I'm changing." And she turned.

"Hey, hey...." I touched her shoulder..."Joking...it's not too much, you look fantastic, really."

Later, she gave me a somewhat exasperated look as a friend of a friend openly ogled her tits while we stood talking in a group. I just smiled. Her eyes narrowed (I get that a lot from her), she spun on her heel and excused herself. She rejoined the group minutes later, staring at me for a beat with a smug grin. I looked, and saw she'd undone the top button. I think I saw the guy actually drool a bit after that.

Later that week she called, and there was the picture on my phone. She'd grabbed it at some point, snapped the pic and set it to her name. I love it.

"Hey Gin..." flipping open my phone.

"Hey..." she said, then was quiet for a bit.

I asked "How's your day...everything OK?"

"Yea...listen...I'm sorry about this morning..you know, leaving you hanging like that."

"You're sorry?" I stood, pushed my office door closed, then in a lower voice said "You'll make a lousy cuckoldress if you're going to apologize when you're mean to me." I said, trying to impart a smile in my voice.

"So you liked it?"

"Definitely...it surprised me, but it was...it was hot. And I've been thinking of you all day."

"Hmm." she said, then "Well, that WAS the intended effect. I was feeling bad though."

"Well, you shouldn't...no need. I can't wait to see you later. How's my outfit working out, by the way?"

"Ha...well...I'd say it's having your intended effect. Guys stop talking when I walk by."

"Ahhh, nice." I replied, then "Any potential f-buddies in there?"

I heard a deep breath...not quite a sigh of exasperation, then she said, "ANYWAY...meet me at Jake's after your dinner? We should be wrapping up drinks by then."

"Yea, sounds good. See you there."

She whispered, her voice husky..."See you baby...", then click. Such a damn tease.

Interesting choice, Jake's. Innocent enough at first glance, it's a pub in a hotel, one of three bars / restaurants spread around the lobby. Her work drinks were in another of them, a steak place with a bar, big standing tables and good appetizers, and it's an easy walk for me from the place I was taking a client to dinner in. But, she'd picked the spot for work drinks this time, and she knew where I was having dinner. And, Jake's is the last place we went for "the bet" as it has come to be known between us, where the black guy bought her the drink. I think she was playing with my head, and I'd tell her so later. She'd feign surprised innocence, of course. As it was...I never got the chance.

My mind drifted again, the first really nice Saturday of the year, a couple of weeks after the bet. I'd broken out the hammock and set it up under the deck, the underside of which I'd covered to catch and drain the rain to the side yard. We could lay under there all summer, any weather, it was a favorite for me. I was lying there reading when she came down the deck stairs and around the corner. Her hair was up in a cute pony tail, she was wearing one of my white dress shirts, no bra, and short cut-off jean shorts, bare feet. I only knew of the shorts from the dark blue showing faintly through the shirt, as my shirt hung to mid-thigh on her. She dresses like that, wearing barely anything, when she wants sex. She came over to the hammock and told me to scoot over, though, so she had something else in mind.

We'd tried sex in the hammock once when we first got it, and wound up wondering whether we needed to go to the emergency room. She'd fallen and hit her head hard on the patio, bending me sharply as she fell off me. We'd both recovered, but from then on the hammock was off-limits for anything more than heavy petting.

She pressed against me, swung a leg over mine, her head on my chest, and sighed as we swayed slowly. She smelled like vanilla. I was instantly aroused, I couldn't help myself. She has the softest skin I've ever felt. I commented on it after we were together the first time and she told me she rubbed baby oil all over after every shower and bath. When I'm near her, I need to touch her to feel that softness, and it inevitably arouses me.

She seemed a little tense, though, so I just held her for a bit and waited.

She sighed again, then spoke softly. "I have to tell you something, Thomas." Then silence.

"OK..." I said..suddenly nervous.

Another sigh...then "It's just...I don't think it's too big a deal, but..."

"But what baby? You're worrying me here..."

"I'm sorry...it's just...the night of the bet...something happened that I didn't tell you, and then I lied...and...I just wanted to tell you but it didn't seem the right time, and then it was over...but it's just eating me up."

I lifted her chin, looked in her eyes and kissed her forehead.

"Ginger...I don't know what it could be, but we can work out whatever it is so long as you want to work it out."

She put her head back down on my chest...her voice quavered when she spoke again.

"That last guy...he touched me."

I was relieved. "I know he did baby...I saw his hand on your leg, I saw it slide up under your skirt."

She shook her head slightly. "Yea...but you didn't see him move it higher...he slid it up, and I looked at you because I thought you'd like it, but you pulled out your phone to send me that text and you didn't see. His fingers touched me...through my panties. And I was wet, and so they were a little wet from the whole night, and he felt that, and it felt like an electric shock up my spine when I felt him there. We both jumped. And then my phone went off..and that was it."

"OK...ok..." I said. My heart was beating hard.

She was right, I would have liked it...I sort of liked it now, but I didn't know where she was going with it.