Date Night 49

The hotel bar was dimly lit. There was a hush over the place, a generic jazz was piped into the place that acted more as white noise than entertainment. The thick crush of the carpet muffled the sound of footsteps as a man entered the bar. It was a week night and the bar contained only a handful of patrons and a bored looking bartender. The man walked over to the bar, near where a petite red headed woman was already seated and asked, "Excuse me, but do you mind if I sit here?" She looked up from the book she had been reading and an almost empty drink to reply, "Sure. No one's sitting there."

He looked her over as she turned to speak. She was a very attractive woman, probably in her mid-forties. She had a pixie-like hair cut and wore an elegant black skirt that went almost to her knees, a white blouse that revealed a bit of cleavage, a silver pendant around her neck and rectangular glasses with turtleshell frames. Her appearance would have been considered prim, much like a librarian, were it not for the bright red lipstick on her full lips, expertly applied eyeliner, black, fishnet stockings and black stiletto high-heels. Her scent was subtly sweet, like orange and jasmine. "I hate drinking alone.", he stated, motioning to the bartender, "Let me buy you drink."

It was her turn to take stock of him. At about 6' and 200lbs, he could have been a wrestler with his build, but in simple slacks, a collared shirt and sports jacket, he gave off more of an aura of a professor or an academic. His hands, large and strong, were unadorned by rings. He had dark, full head of hair, peppered with a little grey along the sides, dark, piercing eyes and gave off an aroma of spice and coconut. "Thank you. I'll take a side car.", she said.

"Please forgive my manners. I'm Tom." he extended his hand towards her.

"Lisa." she replied, "Very nice to meet you."

She enjoyed the way the hand enveloped her, strong, powerful, yet restrained. His grip was firm, but not overbearing.

"What are you reading?"

She held up the book to show him. "Hmm, Brian Lumley," he scrutinized the book briefly and then looked back at her, eyes meeting momentarily, before his gaze was drawn down, to her lips, her slender neck, returning to her face, "dark stuff from what little I've read. Not at all what I imagined a pretty young woman such as yourself would be reading."

"And what would you imagine me reading?" She met his eyes, smiling and the allowed her eyes to wander, as well, visually tracing his soft lips, firm chin and wide, solid shoulders.

"You strike me as one for the classics, like Hemingway, or Shelley's

Frankenstein

, or maybe even a nonfiction, like

A Brief History of Time

." He looked down again, first studying her pendant, but eyes helplessly pulled toward the neckline of her blouse and the cleavage it boasted.

"Does anyone really read those books, or do they just say they do to sound erudite. The only time I've ever read anything that would be considered "classic" literature was when I has made to in school." She began absently playing with the pendant, drawing his gaze up to the outline of her delicate chin, to her ear lobe with a single, elegant pearl, then back down to the smooth, white skin between her breasts. "What about you? What do you read, Tom?"

He looked down in thought for a moment. "Nothing that could be considered great literature. Mysteries mostly." He looked back up, "Lee Child, his Jack Reacher series, Michael Connelly, stuff like that. I don't think I'd read anything down here though. How could you, its so dark."

"Oh, its okay for me." She cast him a playful look and then turned back to the bar and sipped her side car, "I can read just fine here."

"Thats right, You like the dark." He reached out and traced a slow pattern along her shoulder.

She looked back at him, smiling, "Buy me another drink, would you? Mine seems to be all gone." Lashes fluttered as she turned back towards him, stockinged knees grazing his.

He smiled back, holding her mischievous stare for a second, and the drained his drink. Catching the bartender's attention, he said, "Two Angel's Envys, each with one rock."

"Whiskey, huh? Changing things up a bit?"

"Hey, you don't complain about a free drink. I feel like drinking whiskey and I already told you that I hate drinking alone." The bartender soon set two short, round glasses with a rich amber fluid and single large ice cube in front of them. Tom took one of the glasses and holding it aloft in front of him said, "To the dark!" She followed suit and clinked his glass, ice rattling musically. "Now, drink your whiskey.", he ordered, looking her in the eye as he drank a healthy swallow.

She took a sip, the flavor of the whiskey filling her mouth. It was cold, because of the ice, but burned, as well. The taste was rich, almost overpowering, and then came a warmth that started in her throat, travelled down to her stomach and the even lower, to someplace deep inside her.

"Let's move to a booth, over in the corner there, and become better acquainted with the darkness." He motioned to a cushioned corner booth that promised privacy. She hesitated for just a moment, and then took another sip of her whiskey, nodding her acquiescence.

"Lead on, kind sir." They walked over and slid into the booth, moving close enough to conspire, too close for a chance meeting, but not the closeness of lovers, not yet. "You're pushing the darkness analogy a little far, I have to point out." She poked his shoulder, as a way just to touch him, under the guise of punctuation.

He ignored the comment, elbows on the table, eyes staring off with a pensive look on his face. "Why are you here, Lisa?" The question was broad, so open ended that she took awhile to process what he was actually asking. Before she could form a response, he continued, "I see you here, alone, and looking quite delicious I might add, just reading your book and I wonder, why here, with the bad lighting and where at any moment some drunken business man, or some stranger such as myself, could bother you."

She saw where he was going. He wasn't entirely wrong, but she still blushed at the idea when presented with it and felt a flush of heat.

"Are you married, Lisa?" He knew the answer; her ring was clearly visible. He allowed his eyes to wander over her, starting with her eyes, but then lowering to chest, where her nipples were now just visible through the thin cloth of her top, and ultimately down to her well-shaped, stockinged legs.

She reddened under such scrutiny. "I am, but sometimes you need to, you know, just get away for a night."

"I think I can help you with what you're looking for. I have a room here." He reached out to softly stroke her cheek, then traced his finger down her neck, before resting his hand on her knee.

"Oh, really?", she said, raising an eyebrow, "And what do you think I'm looking for?"

"I think you play the good girl most of the time, but every now and again you need to cut loose. I think you're looking for a good fuck. Something dirty. Something you can't get at home." His hand began to stroke her knee, fingers occasionally brushing her thigh underneath the hem of her skirt.

"I'm sorry to disappoint you, but I'm just looking for a drink and a little company. You must have me mistaken for someone else." She began to scoot away, putting a distance between them. He placed a hand on hers to stop her and moved the hand that was on her knee further up her leg, underneath her skirt stroking her inner thigh.

"Don't.", he whispered it to her, moving closer, dissolving the distance between them. Leaning in, close enough that she could feel the warmth of him, "I want you. Tonight." He lightly kissed her ear, then nuzzled in close, gliding the tip of his nose along the length of her neck, leaving chills along her skin, despite the heat that was rising within her.

With another light kiss at the base of her neck, he moved away. He didn't move far, he kept one hand on her knee. "I want to play a game. I think you'll have fun, too. I want you to follow my orders and do everything I say."

He held her gaze as he said this, watching her face. He saw a mixture of hesitation and lust, eyes darting around the room, then moving back to him. Her heart raced as she realized she did want this, and the decision made her wet. Biting her lip, she said breathlessly, "Tell me what to do."

"Kiss me." he commanded, and she did. Their lips met, lightly, guardedly at first, then all pretense was gone, as the kiss turned hungry, passionate. Tongues danced together, a mutual give and take of pressure and wetness, as they explored each other's mouths. She bit his lower lip and tugged, as he moved his hand behind her head to pull her in closer. His erection was immediate, straining against the material of his slacks. He was amazed at the desire in that kiss and it stoked his desire in return. They parted reluctantly, but also anxious to see what the next part of the game was.

"Put your hand in my lap and rub my cock." This time he didn't wait for her to respond; firmly grasping her wrist, he guided her hand to rest on the throbbing tent that had formed at the crotch of his pants.

The hardness of it shocked her. Through the fabric of his pants it felt like a foreign object, rigid and springy. The heat of it warmed her hand and she gripped it just to feel how solid it was. As she slowly started to slide up and down its length, he reached up and pinched her nipple through her blouse. He held onto it, tugging it through the fabric of her blouse, not savagely, but not gently either. Once again, she looked around, fearful of being discovered, but no one seemed to be playing attention to them. Her panties felt drenched and her nipples strained against the silky material of her blouse, just as the hard cock in her hands seemed to be trying to burst through his pants. Her hand felt around for his zipper, seeking to release his rigid manhood, just so she could feel the velvety flesh of it.

His hand stopped her, again gripping her wrist firmly. "No, not yet", his eyes smoldered with barely contained lust, "I'm the one in control here. Now, take off your panties."

She didn't want to leave, didn't want to break contact, but this did seem to be the game. Her eyes returned the look of passion as she pulled her hand away from his lap and began to scoot out of the booth. His grip on her wrist tightened.

"No. Do it here. Take off your panties right now and hand them to me." His tone allowed no refusal. She hesitated, biting her lower lip, deliciously exploring the limits of her naughtiness. As her unconsciously turned to scan the room once more, he brought his other hand up to her chin to stop her. "No. No looking around. Keep your eyes on me and obey. Panties, in my hand, now." Placing one of his hands palm up on the table, he released her, but continued to look sternly into her eyes.

Meeting his stare, she pulled her skirt up and lifted her butt from the seat cushion to get to her panties and slid them down to her knees. As she sat down again, she continued to slide them down her calves and over her shoes. Blushing at how damp they were, she placed them in his hand and began to smooth her skirt down, that was now bunched up by her hips. He stopped her, placing a hand on her bare thigh, the tops of her stockings and garter belt plainly visible. Her pussy was shaved bare, glistening and the scent of her sex rose, exciting them both.

He placed the panties in his pocket and ran both hands up her thigh. The hand on the inner thigh continued up, finger stroking the swollen lips of her pussy, slick with her juices. Moving closer to her, hand still between her thighs, he stood close so he could whisper directly in her ear. "You are the sexiest slut I have ever seen and tonight you're going to be mine." He thrust two fingers into her wetness, brazenly finger fucking her underneath the table. She started to moan, but bit her lip and tried to be as unnoticeable as possible. "You just want to be fucked. You just want a dick inside you, thrusting in and out. Maybe more than one. But I'll be the one fucking you tonight."

Withdrawing his hand from between her legs, his other hand pulled a dark rectangle of plastic out of his pocket. He placed it on the bar in front of her. "My room is 531. This is the key. Go there now. I'll text you instructions. I'm going to finish my drink. I'll be up shortly; make sure you're ready." With that, he turned away from her, focusing on his drink and ignoring her entirely. She picked up the key, stared at it for a moment and then slid off her seat and walking toward the elevators.

It only took 5 minutes to get from the bar to the 5th floor, but time felt stretched from her perspective. She reveled in her excitement, on a journey to a strange room, with the promise of getting fucked. Her nipples still impossibly hard, tingled, the sensitive pink nubs caressed by her silk top. A deep part of her could still feel his fingers inside her. Lost in this feeling, without realizing how she had gotten there, she was standing in front of the door to his room. A part of her actually was surprised when the key opened the door and she walked inside.

No sooner had she walked in, than her phone buzzed. The text read, "The box on the bed contains the clothes you are to wear tonight. You will shower and change into these clothes. They are all you are to wear tonight.You have 15 minutes." On the bed was a large white box, tied with a green, satin ribbon. Within the box was a sheer black G-string, a black push-up bra and small, black buttplug. Looking around the room, she also saw a black, rolling, upright suitcase in the corner, a bottle of scotch on the stand by the bed and science fiction paperback novel next to it. Picking up the contents of the box, she walked into the bathroom, turned on the shower and began to undress.

Exactly 15 minutes later, he walked into his room to see her lying on the bed, in a hotel robe, reading the novel. Looking at her hungrily, he silently took her in as he loosened his tie and hung his jacket in the closet. "Stand up.", he said, sitting down in the only chair in the room. "I want to look at you." She stood up,and removed her robe, standing before him in the preselected lingerie. "Turn around for me." he said, his eye roaming over her body. She complied, blushing as he stared at her so brazenly. A heat intensified deep within her.

After a tense moment or two, he pointed to a desk and said, "Bend over and place your hands on the desk." He stood up to approach her. She hesitated for a few seconds, looking at him, assessing his seriousness, before bending over with her hands on the desk. There is a moment that he just stares at her bent over, appreciating the curve of her buttocks and her long, smooth legs, and then he stands. Walking over to her, he gently caressed the soft swell of her ass before swinging his hand back and delivering a solid smack to one solid cheek.

"You have disobeyed me." Smack, smack, smack; his hand descended on her ass time after time, raining blows upon her full ass cheeks causing her ample flesh to shake. He paused briefly and rumbled, "The robe wasn't in my instructions, and I'm not seeing a buttplug in your ass."

"I'm sorry, Sir.", she feebly said, the word barely heard over the slapping of her ass. He began to spank one of her ass cheeks four or five times, before switching to the next one. Back and forth, he continued until they turned rosy red. Then, abruptly, he stopped and began slowly caressing the skin with his fingers, once again marveling at the round smoothness of her butt and the now-red, but unblemished skin. He allowed his fingers to wander, tracing lines down the back of her thighs, then to her inner thigh and finally, to trace the outline of her pussy lips. The wetness between her legs was obvious now and he slowly inserted two finger into her. Barely moving the two fingers inside her, he used his thumb to simultaneously rub her clit. After a few moments, he slowly increased the tempo of his fingers, until they were forcefully thrusting in and out of her soaking pussy and the room was filled with wet sounds they made and her quickening breath. Then, he stopped.

She let out a soft, needful moan, as the fingers withdrew and her pussy felt empty. As he stepped away, she began to rise and rub her still tingling ass. "Don't you dare move!", Tom said in a firm voice, startling her. She quickly resumed her position. "I didn't tell you to move. You're going to stay there until I tell you you can move, unless you want an even more severe punishment." Bent over and with her hands on the desk, she couldn't see what he was doing, but it sounded like he was going through his luggage. Uncertain of what to expect next, a shiver of excitement ran through her as she heard him move back to her. "When I give you instructions, I expect them to be followed.", he said, firmly placing his hand at the base of her spine.

A cold, wet sensation shocked her, as lube was poured down the crack of her ass. With his other hand, he began rubbing the lube up and down between her cheeks, slowly homing in on the slightly darker pucker of her sphincter. Slowly, he pushed his index finger into her ass, up to the first knuckle, then the second. There is some slight discomfort at first, her tight asshole unused to the intruding digit, but her passage is so slick from the lube now that this quickly dissipated leaving only a feeling of fullness. Not moving his finger any deeper, he gently swirled it inside of her, internally massaging her sphincter muscle and the walls of her anus. The dirtiness of the act, the strangeness, sent shivers through her body and she felt her legs weaken. The finger began moving in and out, deeper inside her it pushed to the base of the finger prevented it from going any deeper, then it was slowly drawn out, until only the tip remained inside. This continued for a few minutes, at a steady, but teasingly slow pace, sending a warm sensation that spread from her ass and out to her pussy and legs.

She again felt a feeling of emptiness, as he withdrew his finger from her ass, but a second after this, she felt something new, slowly pressing into her. The tip was thinner than the finger and passed through her sphincter easily, but it quickly became thicker, its flared end stretching her wider than before. The butt plug was pushed in quickly and expertly, causing only a second of pain, before her asshole engulfed it around it narrow neck, leaving a feeling of snug fullness inside of her. "Make sure that stays in there, until I say it can come out. Your ass is quite literally mine now and you should remember that. Now, turn around and get on your knees." His voice was both tender and commanding.

She stood up and stretched slightly to uncramp herself after being in one position for so long, then turned around and obediently dropped to her knees. In this position, her face was at the level of his crotch and she could clearly see the bulge in his pants straining the fabric. She looked up at him, eyes seductive and pleading. "Take my cock out." he commanded, gazing down at her in undisguised lust. Upon unzipping his pants, his cock sprang forth, clearly anxious for her. She licked her full, red lips, grabbed the base of his dick with both hands and begin putting gentle, long kisses at the tip. Then, she swirled her tongue around the head and rubbed the length of him across her face, smearing her lipstick slightly. It wasn't until he had reached and almost painfully erect state that she took all of cock into her mouth, lips sucking at the base.

A steady pace was established, her deep-throating him, and holding him deep, tongue playing with the head of cock, before withdrawing and just sucking on the now ever so sensitive head. Back and forth, she worked her mouth like a machine, shoving as much of him as she could into her mouth and covering his dick in saliva. His hands, previously resting on her shoulders, move so that one hand was resting on top of her head and the other at the back of her neck to gently guide her head. He began to set the pace, pushing her face onto the fullness of his shaft, so that he is all the way down her throat. He holds her there for a full second, before releasing his pressure just enough for her to take his cock mostly out of her mouth. This rhythm went on for three cycles before it became too much for her and she began to gag.