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The Melancholy Pleasure Of Longing

"An unexpectedly romantic encounter between and older man and an escort in a hotel room"

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Author's Notes

"This is a fantasy I have harbored for many years and have rewritten and edited for at least two of them. It's time to turn it loose on the world and move onto the next one. <p> [ADVERT] </p>The man is perhaps an exaggerated self-portrait, the woman the synthesis of everyone I have ever loved."

Turning off the water, he stepped onto the mat warmed by the heated floor, a luxury he did not have at home. The man stood for a minute as the water trailed down his body before reaching for a towel.  He pressed his face into the soft terrycloth before he ran the towel over his head, drying his short thinning hair while absent-mindedly watching his shadowy reflection in the fogged mirror.  He wiped the glass with his bare hand and leaned forward to examine his face.

“I should shave,” he muttered as he rubbed his hand across his jaw.  He leaned forward again to study his reflection; dark eyes deeply set in shadow above high and prominent cheekbones. It was the face of a lighter and lither man than his barrel chest and wide shoulders deserved. He watched the shadows on his face as he turned slightly in the mirror.  Too late now, full steam ahead? he thought and then sighed. 

After shaving, he stepped into the cooler and dryer air of his hotel room and put on boxers, black pajama bottoms, and a long-sleeved white tee-shirt he had laid on the bed.  Once dressed, he pulled his wallet from his suit draped across the desk chair, and counted out the bills. These he slid into an envelope, wrote “Lily” on it, and placed it on the bedside table.  He grabbed his book and sat on the loveseat by the window, pressed his index finger between the pages to the bookmark, and spread the book open. He began to read, though he could not concentrate. He overturned the volume on his chest after a few minutes, not caring about the opaque paragraphs he had read. 

He looked at the bottle of Moet and two flutes beside the loveseat, and considered pouring a glass, No. Wait.  She‘ll be here soon

He got up, paced to the window, and pulled the drapery back to look down the glistening avenue below.  Taillights and neon refracted on the rain-streaked window.   Small figures on the sidewalk hustled bent against the rain.  Even on a night like this, he loved this city. 

Though he had moved away years before, it still felt like home to him. He adored its complexity, its artistry, the constant whirl of change, the demolition and construction, and the constant reinvention.  The best entertainment was to walk the city’s streets, long swings to the north or south, or to take a subway to a distant spoke and wander back to the center, noting the changes since he had last been there and nodding in recognition at the places that remained. 

As he stood by the window taking in this sliver of a view of a place he intensely loved, there was a soft knock on the door.  He waited and it repeated, a little more insistent this time. He dimmed the lights slightly before opening the door against the chain to see a dark-haired woman of about thirty standing in the hall, her black raincoat damp, an umbrella in her hand.

“Robert?”

“You must be Lily, please …come in,” he stammered a little nervous.  He realized his hands were shaking slightly.  He loosened the chain and swung the door open.  She stepped into the room, shook her head and a fine spray of rain droplets surrounded her like a halo. She laughed a deep full delightful laugh.

“Here, let me take your coat.”

“Yes, of course, Jeeves.” She grinned a crooked smile and her eyes narrowed with laugh lines, hinting at the shapes that would emerge as she aged.

He paused, then turned slowly, raising his eyebrows while straightening his back, he languidly stretched out his hand and in an abysmal impression of an English butler replied, “Of course, Madame.” 

She laughed again, and turned so he could help her from her coat. She was taller than he expected, and as the coat slid from her shoulders, the body revealed was slight, almost waifish.  She had a long and elegant neck just brushed by the tips of her straight black hair and he leaned toward it to inhale her scent; faintly floral, but with an undertone of something darker and feral.  He had a fleeting desire to kiss the back of her neck, but held back.

“There is a gift for you beside the bed,” he said as he hung her coat in the closet. 

She walked to the end table, opened the envelope, thumbed the bills, and placed it in her bag.  They turned simultaneously across the room to face each other.  He gave a little smile.  “You’re taller than I expected,” he said.

“No, I’m not.” She kicked out of her heels and lost altitude fast.

“Wow, how do you walk in those?” Robert said, pointing at the black stiletto heels on the carpet.

“It’s an art, and one I’ve mastered. If you’re a good boy, I’ll demonstrate later, you can choose the rest of the outfit. Or not.”

“Oooh! The possibilities are tantalizing.”

“Damn straight, Jeeves.”

He chuckled at her response. Probably just 30, she was substantially younger than he was, but she had a worldly self-confident manner and moved with the straight-backed grace of a dancer.  Her lips were full, with a slight overbite, something he had always found very sexy.  She had a subtle Roman nose, not large, but distinctive and proud.  Her eyes were dark under a prominent brow, and they glowed with mischief and humor.  Her soft black cashmere turtleneck clung to her breasts. 

Well, they’re not waifish, he thought.

Her waist was small, her hips a little wider and her ass, at least the curves that could be seen beneath her black wool slacks, shapely and he found his heart quickening and he contemplated cupping it in his hands.

“Wow, you’re beautiful.” 

She laughed again, a slightly absurd little giggle, and her nose scrunched up, “Thanks,” she said with a little snort.

“Hell, you’re even beautiful if you if you do snort; it’s charmingly goofy.”

“Oh, now I’m goofy?” Lily said in mock indignation.

“Only in the most adorable way. Would you a glass of champagne?”

“Sure, lead on.” 

He held out his hand and she promenaded around the other side of the cocktail table, let go of his hand and gave an exaggerated curtsy before sitting.  He laughed for the first time, a deep genuine, heartfelt laugh.   Robert found as his nerves were settling, enjoying the flirtation.  He handed her the flute of champagne and leaned back against the sofa to watch her.  She might have been a real beauty, but her silliness, wit, and obvious intelligence suggested something he had not expected, or at least a depth that would be revealed so freely.

“Whatcha lookin’ at, Big Boy?” she said impersonating a classic gangster’s moll.

“You.”

“Like whatcha see?”

“Yes.  Very much.”

Their eyes met, and the B-movie character dropped away.  Her expression became softer, shyer, and she looked down, suddenly a little breathless.

“That’s good, isn’t it?”

She reached her hand towards his across the seat and his fingers closed over hers gently. His fingertips brushed up and down the inside of her arm and she felt a whisper of arousal.  She looked up and saw expectancy as his eyes widened.  She felt an unexpected impulse to kiss him at that moment.

That’s weird, she thought.  She was a little giddy, like she had met him before and knew how it would feel to be in his arms.  She looked back at him, and he smiled. His dark eyes questioning, as longing crept around the edges of his humor. She looked down again to compose herself.  She liked most of her clients.  She had had laughs with a few of them, and had even enjoyed the sex usually, but she had never allowed herself to feel anything more than fleeting affection.  But the moment he had opened the door and she had seen him standing in front of her, she had felt her heart wallop in her chest and she caught her breath in a kind of mystical recognition, What the fuck was going on here? Shit, girl, you’re not in tenth grade and he’s not the hot teacher.

“I’m going to go freshen up.  She stood up and walked to the bathroom with the lingering humidity of recent his shower still heavy in the air.  Well, at least I don’t have to ask him to shower.

She peed, grabbed a fresh washcloth, and washed between her legs. At the sink, she looked in the mirror, What’s going on, you?

She wasn’t afraid. Not of danger, but she felt unsettled, guarded, a little unsure of herself.

 As she came out of the bathroom, he was still on the loveseat.  “Come and sit with me.  Let’s talk. I’d like to get to know you a little.”

“Just a little?”

“Well, we did just meet. I think ‘a little’ might be a good start.” 

He held up the champagne bottle and inclined his head to silently ask, “More?” 

She held her glass forward to be filled.  He poured himself a glass and sipped.    She leaned back and watched him. Christ, he’s old enough to be my father.

“How old are you, anyway?” she blurted out, not realizing that she spoke her thoughts out loud at first.

He nearly spit champagne into the room, “Old enough to be your father?”

She paused a beat, smirked to herself as he said the same words she was thinking before replying, “Mine’s sixty-one.”

He looked down, curled his lip, made a non-committal grunt.

“So, your answer is ‘yes’?”

“Are you trying to make me feel old?”

“No.  I was just curious.  Honestly, I’m not sure how old you are. And I really don’t care.”

 “Your father and I could have been schoolmates.  Well, not literally, since I don’t know him, but… well, yes.”

“You look younger,” she smiled.

“…For an old man…”

“No, you have a handsome face and you look like…” she searched for the right words, “…you enjoy life.  And I’ll bet you were a smart-ass as a kid and you haven’t lost that.  I’ll bet you were always in trouble and deserved a good spanking.”

“Do I deserve a spanking now?” he smirked.

“I do not believe you ordered that from the menu, Sir. However, the management may be able to make adjustments.”

“I’ll be very happy with what I ordered.”

“Very good, sir. One ass fucking coming up.”

He spit champagne back into his glass. “Holy shit! Do you always just blurt stuff out?” he laughed.

She laughed again, “I really should learn to watch what I say.”

“No, don’t. You make me laugh.  I’m having a lovely time.  And It’s good to know that delicious ass of yours is still on the table.”

“I expect it will be on the bed soon enough, Sir.”

She smiled back at him, leaned back on the loveseat to take him in. Yes, he was older, but his youthful manner made him light on his feet and he moved like a younger man.  There was a quickness to his motions and speech, as though he were bursting with ideas and could not wait to get them all out. As she watched him, her first impression held:  his face was kind, but his eyes, when she looked into them, had a glimmer of sadness close to the surface and incompletely masked.

They talked for about fifteen minutes. He told her about his work, and why he was in the city, combining a board meeting with some research into a book he was writing.  When he spoke about his work, he became animated as though his thoughts were competing to get out.  His eyes glowed wide and his passion and intellect charmed her. She could see how he must have been when he was younger. He had not lost his sexiness, but as he spoke, his shyness faded and she leaned in to listen more closely, enjoying his enthusiasm.

He in turn was captivated by her manner as she listened.  He wanted to sink into her, ached to kiss her lips, relished each time her eyes widened at his words. 

She, in turn, spoke of her parents, her education, her own professional life in as she termed it, “The Real World.”  She mentioned the books she had read and worked on in publishing.

“I couldn’t make a living in this town in publishing. It’s what I loved, but a girl’s gotta eat.”

“Thus…this?”

“Well, I do enjoy my work, but I’m not sure this is so important in the Grand Scheme.”

“It’s important to me,” he squeezed her hand.

She spoke crisply as though language were a laser and each word that she uttered hit its precise target.  As she talked with her arm up on the back of the loveseat; he stretched out his hand and caressed the inside of her wrist with his fingertips. She felt a sensual shiver across her shoulders.  He listened intently, focused on her face, and smiling with each of her humorous asides, laughing fully at her stories.  They fell silent, sitting side by side, peaceful in the moment, fingers entwined on the seatback.

She stood up, “Well, Sir, if you want to enjoy the special on tonight’s menu, the chef needs to start prep.” 

She reached into her bag and pulled out bottle of lube and a polished stainless-steel jeweled butt plug. She saw his widening eyes and big boyish grin.

“Would you like to help?”

“You bet!”

He slid across the loveseat so that he was eye level with her waist.  She reached to the side and slid down the zipper on her slacks, letting them fall to the floor, stepped from puddled wool and with a simple motion pulled her turtleneck over her head and threw it playfully at Robert. She stood in front of him, letting him take in her body. She wore black-lace boy shorts that clung to her curving hips and small black lace balconette bra that struggled to contain her luscious breasts.   Through the lace he could make out the shadow of dark pubic hair, neatly trimmed, but still luxuriant as a few strands sought the clear light of the hotel room. Her nipples were dark, the areolas large, peeking over the top of her bra. Lily looked at Robert as he took in the view. She grabbed her breasts from below and looked down on them. “I think my nipples are too large and my tits too big.”

“Oh, dear god, no. They’re breathtaking, Lily.  Are you insane?  I love them.  I’ve been crazy about boobs since I discovered girls and yours are...” he thought for a moment, “Magnificent.  Just perfect.”

She turned around quickly, leaned forward pushing her ass towards Robert.

“However, I think I have a decent ass.”

Robert moaned, “No complaints here.  I feel a little dizzy actually…vertigo, from the glorious majesty of the view.”

Lily laughed and straightened up and placed her thumbs on the sides of her shorts lowering them to the floor, wiggling her butt for Robert as she did so.  He moaned again.  She picked up the lube and the plug, poured a generous dollop on the metal head, and turned to Robert with a lascivious grin as the gel slowly slid down the bullet-shaped head and dripped onto the flared base.

“Would you like to assist, Sir?”

“I believe I already made my… my position clear on that subject.”

“Speaking of positions…” Lily bent over, supporting her hands on the coffee table and pushed her butt toward Robert.  He grabbed the lube, poured out a portion and spreading her cheeks with one hand began to make small circles around her anus with his finger.  It was small and pinched into a tight pucker with a lighter tint than the deep reddish brown of her areolas.

“My Dear, you have a very pretty asshole.”

“Uhh,” she exhaled slowly, enjoying the deft swirl of his fingertip. “I’m glad you…uh...uh…pprove.”

The second sigh punctuated the insertion of the tip of his finger into her ass. He pulled it out, added more lube and pressed in again, gently fucking her ass with his fingertip.  He reached around with his other hand, brushing into the thick hair of her pussy and teasing the lips around her clit. 

“Mmm. Retro-bush.”

She stiffened a little, “I don’t like shaving down there.”

“I don’t like it when women shave down there.” Robert replied, “I grew up in the Seventies. You have a spectacular bush and I am in nostalgic heaven.”

He pushed a second finger into her ass and continued to rub her clit gently.  He started to put a third finger into her. 

“Whoa, we aren’t shooting a German Porn!  The plug and then your cock in my ass, we don’t need to try for an Olympic record.”

“Too bad, Liebchen, the East German Judge was going to give you a ‘10’.”

“I’ll be happy if the East German Judge gives me a good ‘6’.”  She turned to look at the bulge in Robert’s lap, “It looks like the East German Judge is going to give me a good ‘6’!”, she laughed, “Put the plug in me now.”

Robert placed the stainless-steel point against her anus and rotated it gently as he pushed it in, feeling the pressure of her sphincter contract.  He paused and waited a moment and pushed gently again.  She moaned and he was more aroused with each sigh and moan she made.

“Oh fuck! That feels good!”

“You are a dirty little girl, aren’t you?”

“Oh…I have …my moments.” She breathed out as the rounded bulb was swallowed into her rectum.

She wriggled her ass before his face; he was entranced by the glinting red jewel protruding from her asshole, just above her luxuriant pussy. He stood up and leaned lightly against her ass, his hard penis pressing his pajama bottoms against her bottom.

“Hey, handsome, sit back down, I have a treat for you.”

She stood, pressing her hand against his chest to make him sit back on the sofa. He sprawled backward, legs apart and she knelt between them.  Her mouth hovered above his crotch and she rubbed her hand up his chest and back over the bulge below his waist. She pulled at the sides of his pants and as they cleared his crotch his erect penis sprung out. 

“Whoa, well, helloooo, Big Boy!” she laughed.

“I bet you say that to all the boys.”

“Well, sure I do, but I don’t usually mean it!  You, sir, have a very nice cock.”  She wrapped her fingers around it lightly.

“Uh…thank you?”

“I always believe in giving well-deserved compliments. And your friend here deserves a few.  And a kiss.” With that, she lowered her mouth over the head and gently kissed the tip. “I’ll bet it tastes good too!”  as she lowered her mouth over it, engulfing the head and he moaned softly.

What the fuck are you doing, girl? the thought passed through her mind.  She lost herself to the moment and began to slowly fuck him with her mouth. She was swept up in the rhythm as she timed the movement of her head to the subtle rise and fall of his hips.

“Oh, I’m gonna cum if you keep that up.”

He ran his fingers through her hair, careful not to press down too hard. He ached to push deeper into her mouth, but had no idea of how she might react.  He wanted to explode into the warm and moist space seeking to suck his soul from him.

She felt a tenderness toward him that she did not expect.  She wanted to please him, to make him want her, to make him want her mouth, to make him want to possess her as she suddenly wanted to possess him.

She pulled off him, “I want you to cum in my mouth.”

He looked frantic. “Are you sure?”

“I want it, Babe.”  “Babe?  Did I just call him ‘Babe’?”

She looked up into his eyes. They were filled with a gentle longing.

“Please.” That was all he said, and she bent over his cock again and fucked it slowly with her mouth, increasing the rhythm and going as deep as she could. He was lost in pure feeling and desire and a strange sense of familiar comfort. 

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The whirlwind was building as he edged closer. The universe spun in his head and he was reduced the wonderful warm sensation of desire in the middle of his body. Her mouth was deep on his cock as he began to come; he held her head more firmly trying to lose himself in the moment without forcing her down. The first spasm of cum jetted into her mouth and she pulled to the tip as more of his seed was expelled onto her tongue. 

“Ooooh fuuuck!” he almost shouted as his body jerked upward and his cock continued to shoot sperm into her open mouth. As he fell back down, she pushed her mouth, full of his cum, back down onto his cock, and he moaned again,

“Oh, my fucking God!”

She pulled up slowly and settled down on her knees to look at him.  He opened one eye, “Ummm.”

She smiled at him, her mouth still full, and wiped an errant stream of semen from her lips and sucked it off her finger.

“Jesus, that was hot.”

“Mumph.”

“Cat got your tongue?” he asked lazily.

“Muh uh.”

She opened her mouth to show him, and then she swallowed dramatically.

“You tasted so good, I had to swallow”

“This is now officially the hottest time I have ever had and we’re just getting started.”

She had fun and lost herself in the moment. She did not give clients blow jobs without condoms, and was feeling a bit of regret tinged with an unexpected satisfaction. It had felt so intimate; she had wanted to do it, and she was thoroughly aroused now herself.

He caught her eye as she played with his softening penis, “Babe?” He asked with a smirk.

“I don’t know what happened there.  I don’t think I’ve ever used that word in my life. It was the moment.  I’m a little embarrassed.”

“Don’t be. It was lovely and it made me feel special.  And if you are interested, I would like to return the favor, because I’ll need a bit of time before Round Two.”

He stood up and placed his hands on her shoulders and with light pressure guided her to sit on the bed. He knelt between her legs and nuzzled her breasts, slipping a bra cup to one side to lick her nipple, circling his tongue around her large dark areola, and puckering a kiss as his lips closed over the tip. She sighed softly and he reached with his hand for her other breast.

Under his breath, he muttered, “Oh, my God, I have missed this.”

“What did you say?’

“That ‘I’m having fun.’  Though not in those words exactly.”

“Well then, keep going, Buddy.” She fell backward onto the bed and he kissed his way past her belly, and brushed his lips across the top of the thick triangle of black hair.  He circled his nose in her dark fur and moved lower, exhaling a slow warm breath upon her pussy as he passed by. He began to kiss the insides of her thighs, moving closer to her pleasure point but grazing it as he moved from side to side.

She was feeling warm waves of pleasure and a building ache, Christ, Mister, get on with it, I’m dying here!

But not wanting him to move too soon, she gave in to his pace. As he passed from side to side, he lingered a little longer over her labia and with his first gentle lick of the button of her clitoris, she let out a deeper moan, FINALLY! Oh Jesus!

He flicked his tongue gently over her lips and settled into a light rhythm around her clitoris. He then spread her labia and eased a finger into her vagina. 

“Damn, your pussy is wet.”

“Mmm.”

”Just ‘Mmm'?”

“Mmm Mmm.”

He reached his finger in and touched her G-spot, and her back arched off the bed.

“Ooh, you liked that!”

“Oh, God, my pussy feels so good. Don’t stop.”

“Oh, I fully intend to take my time.  I want you to enjoy this.”

He continued licking her clitoris in slow circles and pressing her G-spot with his finger.  Her hips were rising and falling in a slow circular motion and he loved the feeling of his nose buried within her pubic hair while watching the slow rise and fall of her body, her stomach muscles contracting and releasing as the pleasure built within her.  With his other hand, he pulled gently on the knob of the butt plug, and she let out a deeper moan.

“Oooh fuck! Oh fuck, ohhh fuck! Oh, God! My cunt, my ass, Ooh God it feels so good! Don’t stop!”

I wouldn’t dream of it he thought.

“Put another finger in me!”

He reached in and pressed her G-spot with his fingertips and the rhythmic rise and fall of her hips became more intense.  He pulled the plug from her ass and inserted a finger. As he licked her clit, her fucked her pussy and ass with his fingers. Her first contractions were gentle rolling waves and then a massive spasm began to build in her abdomen.  He felt her ass contract and then expand around his finger in as she arched her back a foot off the bed. “Oh. Oh. Oh. Oh oh fuck! Oh my fucking God! Do it! OH MY FUCKING GOD!”  

He thought she would want to stop, but the pleasure continued and she pushed down on his hands.

“Oh God, my ass! Your fingers in my cunt and asshole! Oh God I’m coming again!” she started yelling and covered her mouth with the back of her hand.  The spasms stopped and she pushed him away. “Stop, I can’t take anymore!”

She lay back on the bed with her forearm on her forehead, catching her breath as the room swung back into view. He pulled up and lay on his side next to her.  “That was fun,” he said.

“Fuck yeah.”  She turned and smiled at him. He smiled back, then his eyes got a sad expression and his smile weakened. “You are so beautiful.  It makes my heart hurt.”

“Thanks,” she whispered.

He leaned over, kissed her cheek, got up and went into the bathroom.

She looked at the ceiling, the blinking red light of the smoke detector, the lights of the city beyond through the blinds, and felt content. 

That had been nice, thoroughly unexpected, but very nice, she thought.  She understood the sadness in his eyes; she felt the same sad longing, the ache in her chest now that he had left the room. 

The butt plug lay on the bed beside her and she picked it up, looked around for the lube and waited for Robert to come out of the bathroom. Their fingertips grazed as she passed from the bed to the bath and he from the bath to the bed.  They each shyly smiled as the door clicked shut behind her. She peed and then cleaned up after their first encounter.  Looking into the bathroom mirror for the second time that evening and her own questioning eyes, she considered for a moment that she should leave. It was not right to let her emotions get caught up in her work.  But he was kind, and handsome in a classic way, and if she thought of him merely as a client, she had made a promise she did not wish to renege.  But she was beginning to think he felt like more than just a client, and it would be too sad to leave so soon.

Damn, I like this man.

She pushed her dark hair back from her face and looked once more into the mirror before leaving the bathroom.

He was sitting up in bed and had laid one of the hotel’s terrycloth robes across its foot.

“You can put that on.  Come and sit by me, I’ve poured you another glass of champagne.”

She pushed her breasts back into their cups and slipped on the robe and settled in next to him. They sat side by side, their backs against the headboard.

“I’m having a really nice time. I’m glad it was you standing there when I opened door.”

She looked down at her hands and cocked her head to the side to reply, “I’m glad it was me, too.”

He reached his hand out and covered hers. They did not speak, but she laced the backs of her fingers through his covering hand and sighed.  They dozed off to the distant hum of the city below with the intermittent scream of a siren breaking the peace.

She felt herself slowly coming to from a dream of standing on a sand dune looking over a desolate beach in which a man was holding her from behind. She was lying on her side, and slowly recognized the hotel room. Robert’s arm around her as they spooned. She held his hand against her chest and snuggled back against him.  He squeezed her gently. “Mmmm.”

“Mmm, yourself,” she replied.

“I was wondering if you were awake,” he muttered as he pressed his body against her, his erection nestling in the cleft between her buttocks.

“Well, you clearly are!” She turned back over her shoulder to look at him, and whispered, “Hi.”

“Hi.” he smiled back at her and she felt a welling in her chest. 

She wanted this man to be happy and whispered, “I want you to fuck me.”

“There is nothing in the world I want more…could ever want more than you.”

She reached back to pull the plug from her ass, tossing it to the floor. 

“So much for Housekeeping, I better not forget that!”

He slid his hand beneath her robe which had fallen open and cupped her breast as he began to press his pelvis against her soft buttocks.  She arched back and pressed against him and they rocked, rubbing each other as his free hand glided up and down her body to push the robe away. He ran his hand down along her side, across her belly with its delightful little swell, brushing his fingertips into the soft curls at the top of the triangle of pubic hair.  Lily gave a soft moan, and as if encouraged, Robert returned to the soft curls and pressed deeper, his index finger sliding lightly across her clit.

“Oh my, Sir.”

“You like that, don’t you?”

“Oh yeah.”

Robert arched his hips, pushing the tip of his cock into the cleft of her ass, brushing against her anus.  Lily moaned again.  They lay like this on their sides for a while, a slow gentle grind of their hips, his fingers on her clit and the tip of his cock pushing against her puckered ass.  Like the movement of their hips, their breathing was slow, but increasingly deeper, rhythmic, and in synch. His mouth was against her upturned ear and he whispered silent words of longing, words of desire and lust that welled inside him.  She heard the whispered breaths, the words inaudible. She craned her neck back and reached over her head to hold his in her hand.  She had an impulse to kiss him at that moment, to make this intimate moment sacred, but she held back.

“Wait a second,” she said, lifting his arm off her and getting up from the bed.

She turned and saw his disappointed face and laughed. “You look so sad!  I’m just getting the lube!”

 He was surprised at himself, for feeling an aching longing as she moved away for just a moment.  His emotions were bubbling to the surface and he was not sure he wanted her to see this unexpected feeling

She held up a rubber and he took it, opening and stretching it onto his cock.

“I’m back! she settled onto the bed, “Miss me?”

You have no idea how much.  I’ve missed you my whole life.

“Same position?” she asked. He nodded, cast his eyes down so she would not see his emotion.  She sidled back into bed, settled into the crook of his left arm, and opened the lube, squeezing a generous amount into her hand.  “Here,” she said., “You do me and I’ll do you.”

As she handed him the bottle and reached behind to find his bulging cock, covering it from top to bottom with the slick gel.  Now it was Robert’s turn to moan. “Damn, you give the best hand jobs.” 

“Years of practice.” Shit, did I just say that? she thought.

Robert seemed not to notice and his well-lubed fingers made a circle around her anus, and once quite slick from the viscous liquid, pressed one into her ass and began to slowly fuck her with one finger and then two. He was slow, careful, and gentle with an underlying strength, as though holding back from the urgency.

Her hips began to rock slowly in the rhythm of his hand.  She turned her face back towards his, “Fuck me now.”

“Now?”

“Now.”

“Damn, I wish we had a towel, he said holding up his hand.”  Lily grabbed a pillow, smeared her hands on it, and handed it to Robert, who laughing, did the same.

“Well, Housekeeping is going to wonder about that. too!”

“Let ‘em.”

Robert, rolled toward Lily and spooning with his hand spread across her ribs, just below her breasts, pulled her body toward his. She reached behind and grabbed his cock and positioned it against her anus. He pushed slowly and gently, feeling the compression of her sphincter tighten. He paused, and then pushed again, feeling the pressure loosen.  As the head of his penis pushed past the first ring, her moan turned into a grunt, “Uhh.” Followed by a quick intake of breath. He paused.

“No, keep going, it’s…Uhhh…good.” He pushed in and then withdrew, each stroke infinitesimally deeper so that after several minutes, the full length of his cock was sliding in and out of her ass. She ground back against him as he reached again for her clit, pushing his middle finger through her wet lips and into her cunt.  She moaned a deeper feral sigh of desire.

She had never had an orgasm with a dick in her ass but, Holy shit, this could happen!

The heel of his hand pressed back against her pubic bone; the fingertips a light pressure rubbing her clitoris as their hips rocked.  His breathing became deeper and more frantic and she pushed back harder against him, loving the sensation of the dick in her ass.

Robert rose above her, leaned against her back with a firm pressure and she splayed onto her belly as he rolled onto her.  She was face down, legs spread and he hovered over her. She grunted as his cock pushed to its full depth in her asshole.  He loved the feeling of her butt against his pelvis, a luxuriant fleshy splendor enveloping the raging sensations around his cock.

She arched her back pushing off the bed with both palms, “FUCK ME! OH GOD FUUUCK ME!”

He pushed harder into her ass and her moan ended with an animalistic grunt. She fell forward into the sheet and reached under her pelvis to rub herself furiously.  Robert leaned forward over her back as he drove his cock repeatedly into and out of her ass.  Her ass rose to meet his thrusts and they found a surging rhythm, hard, methodical, precise and her fingers skittered across her clit. 

She felt the familiar tingling that started in her toes, Oh, shit, it’s happening, It’s REALLY HAPPENING!

The convulsions rocked her upward, her back meeting Robert’s sweaty chest, and then she fell hard back onto the bed again, “OH MY FUCKING GOD!”

She spasmed, forcing Robert’s own orgasm and he imagined his cum shooting into the deep recesses of her ass instead of confined by the rubber. His body shook and trembled and then was still.

He lowered himself against her, careful to keep his weight from fully pressing against her back.  He reached both arms around her just above her breasts and rested on his forearms, nuzzling the back of her neck. She reached a hand up and caressed the side of his head. Lily started to cry.

“Hey, are you okay? I didn’t hurt you, did I?” He turned her head to look into her eyes, concern and worry on his face.

“No, not all.  I’m just feeling …a lot.”  She paused wiping a tear from her cheek and considered what to say.  “Sometimes I cry after I come.  Not always, but sometimes it’s too emotional.”

“I’m sorry, Lily.”

“Oh, God, no, don’t apologize. That was wonderful. Not what I expected, but unexpectedly wonderful.”

“It was pretty special for me, too. I don’t think I’ll ever forget you, or this night.”

“Not what you expected from an escort, right?” she joked.

“No, don’t say that. I know that’s what it is, but…it’s not felt it felt like to me.”

“No, not to me, either,” she said wistfully, and folded her arms over his.

They became silent, he rocked his hips and his cock slid gently in her ass and she sighed. She loved the sensation of his body spread along her back, warm and protective, his cock burrowed into her ass. He held her a bit longer and she caressed the side of his head.

 “I guess I should go soon.”

“I know. I wish you didn’t have to.”

“I know. I wish I didn’t have to, either. But I must.”

He pushed off her back, his cock sliding out of her ass for the final time, leaving a slimy trail across her buttocks, glimmering in the dim light of the hotel room.

“Seeing you lying there, spent and wet is just about the sexiest thing I’ve ever seen.”

She wriggled her ass and looked over her shoulder, “Get a last look in.”

She got up from the bed and went into the bathroom to clean up. For the third time this night, she looked into the mirror and wondered about this man and her strange feelings for him. It was as though she had known him in a distant past, and that they had reconnected, familiar and intimate in this small random room.  The ache in her chest was already beginning. She knew she would miss him.

When she came out of the bathroom, Robert was dressed in jeans and pullover sweater and had slipped on loafers. Her clothes were arrayed sweetly on the bed. He sat on the sofa and watched her dress, a little sad that this remarkable gorgeous woman was no longer standing naked in his room.

“I’ll walk you down to get a cab.”

“You don’t need to do that.”

“I wouldn’t feel right if I didn’t.”

She turned to look at him. His eyes were sad again and she wondered if he felt the same ache at their parting that she did.

“Thank you, that would be nice.”

They headed for the door, “Got your key?” she asked.

He waved the plastic card in his hand.  In the elevator, they leaned against the back wall of the cab facing the door, their fingertips brushed and he entwined his fingers in hers. She leaned her head to rest it on his shoulder.  In the lobby, the clerk watched them exit the elevator. “Would you like me to call you a cab, Sir?”

“No, we can manage, but thank you.” The clerk returned to his computer screen.

Lily muttered, “I’ll bet that’s not the first time he’s watched this parade.”

“Well, at least you don’t have to walk back in there under his judgmental gaze!”

The rain had become a fine mist.  Under the hotel awning, Robert lifted his arm to the oncoming traffic. A cab viciously cut across four lanes to screech to a stop at the curb. “Well, this is going to be a little scary,” Lily laughed as Robert opened the rear door for her. They stood for a moment, faces inches apart with the car door between them. “Upstairs, that, was fun,” she said. 

“I’d like to see you again, but I don’t know when I’ll be back in town.”

“I don’t know if another time would feel like tonight.” she looked down.

“I don’t know either,” he said. “But I will cling to the hope that the Universe made tonight happen for a reason.  I had a weird feeling like I knew you-had always known you- when you walked in the room.”

Lily startled and looked up into his eyes.

“What?” he asked.

“I had a similar sensation. But there’s no way we could have ever met, right?” she replied in a soft voice.

“Not in this life.”

“Robert, you don’t believe in that stuff, do you?”

“I never had reason to until I met you.  It’s silly, but I can’t shake this feeling.”

“…Like you’ve known me forever?  I feel it too.”

He nodded in agreement. “I feel as though I’ve finally found you again after a long time apart. And here, now, the Universe is pulling us apart again.  I’ll miss you.  I feel like I’ve always missed you.”

She stretched on her toes and placed a soft kiss on his lips, turned and ducked into the cab. He shut the door behind her and stood on the curb watching the taxi until it turned the corner two blocks down to head east.

Through the lobby and the clerk’s “Good night, Sir,” to the elevator. The elevator cab they had ridden down was waiting and Robert was greeted by her faint scent. 

In his room, Robert sat on the edge of the bed and looked at the rumpled sheets. He grabbed a pillow and inhaled her scent: jasmine, slightly floral, but what was once dark and feral now smelled of loss and longing.

In the back of the cab, as it turned down the avenue, Lily sobbed once to the hollow ache in her chest, closed her eyes hoping the overwhelming emotions would soon recede.  She checked her phone and saw a text from one of her regulars. “Tonight?” with a leering emoji.  She sighed and put her phone back in her bag, not wanting to reply just yet.

 

Published 
Written by The_Hidden_Man
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