No Title

A Night with Zachary

©Tianna Filley, 2017

This is a work of fiction. Names, characters, businesses, places, events and incidents are either the products of the author’s imagination or are used fictitiously and are not to be construed as real. Any resemblance to actual events, locales, organizations, or persons, living or dead, or actual events is entirely coincidental.
A Night with Zachary Copyright ©2017 by Tianna Filley.

All Rights Reserved.
No part of this story may be used or reproduced in any manner whatsoever without written permission from the author.

A Night with Zachary

A Night with ZacharyPlease Be Warned: This short story has an Adult Rating! This story does contain some strong language! Must be 18 years of age or older!

A Night with Zachary

By Tianna Filley©


I enjoyed our chat last night. Think the other guys did too, if their comments were any basis to judge by. Bet you got a lot of offers after I left the room, but hope I’m the only one who got your email address. Sorry that your husband doesn’t have much time for you anymore. You sound like a beautiful lady, and beautiful ladies should never be ignored. Wish I could do something to make you feel better (no, I’m not asking to meet you in real life). I’m happily married, in the same boat as your husband, and understand what he is feeling about the situation.

Chat rooms are so public (but I guess that’s the point), so why don’t you return this email with some more of your witty conversation. I’ll reply to you, you to me, and so on. Who knows, we might become good friends. At least you’ll have someone to tell about your troubles, and I’m pretty good at listening.

Looking to hear from you,


Hannah had clicked the envelope in her inbox, realizing this was the guy she had chatted with last night. She had been home, alone, again, while Gregory was at work, again. She trusted Gregory , but lately, his job had been consuming more and more of their time, and she was getting tired of putting herself to sleep with late night reruns of old “B” movies. Their love life had gone to shit, and whenever Gregory was home, he was so tired they just stayed in. She longed for a night out, away from the kids, maybe dinner, dancing, and a late nightcap in the back booth of some dark, little bar. She could take the lack of sex, although that was getting harder lately, but she needed some spice in her life. Then she had discovered the single’s chat room.

She was always careful not to give any true information about herself, and didn’t even talk much unless a person really sounded interesting. She spent much of her time, in fact, telling the horny guys that she didn’t do that sort of thing, and trying to nicely fend off women with desires on her bi-sexual virginity. Every once in a while, though, she found some man with interesting things to say, who was polite, and seemed to appreciate her company. She could talk for hours, too many really, but since virtual reality had to substitute for a social life, she thought, “what the hell do I need sleep for?”

Gregory knew about her chat room sessions; they had always been up front with each other, and she had told him what she was doing. She told him which chat room she frequented, but didn’t explain that she chose “TinyRedRose” as her nickname because she was, after all, only 4’11” tall, weighed 95 pounds wet from a shower, and had flaming red hair. Somehow, it didn’t seem as neat now as when she had first signed on with it, but the few friends in chat she trusted knew her by that, and if she changed it she would have to start all over.

Last night, Zachary had said “hi” when she signed on, and they had a marvelous session that probably had entertained the rest of the horny guys in the room as well, but it had felt great to have a nice guy be sympathetic to her loneliness without asking for her phone number, or telling her how good she would feel riding his 12″ cock. “Talk about virtual reality!” she laughed to herself over that one, and giggled as she typed “doubt it sugar, I’m tiny remember”. She had privately given him her email address, on a whim, and now regretted it a little.

To: Zachary


Subject: How are you tonight?

I thought about this a lot, and decided that email is probably a safe way to converse on a personal basis. I loved chatting with you, but afterwards, I realized that I said a lot of personal stuff, and I wish I hadn’t. I need someone to talk to, but don’t like the world to listen in, so I’ll try this for a while, and we’ll see what happens.

Husband is gone, again, and I’m here alone, again, watching old horror movies, again. Kids are tucked in, and I’ve only made two trips to settle bedtime giggles, so tonight is about average. I love my husband deeply, but honestly, I can’t take much more of this. He’s gone until all hours of the DAMNED night, working at that DAMNED office on DAMNED stuff that can never wait. He’s told me they “de-layered” the organization, which he says means fewer people do more work in the same amount of time, but I guess he hasn’t figured out how to be that efficient yet. Just wish we could have a quiet night out sometime, like we used to.

We used to go dancing after dinner, and end up at two in the morning in some little bar, sipping nightcaps, just talking boy/girl stuff, and kissing. Then we would go home and … well, that’s a little too intimate for this email; let’s just say, we both felt really …”relieved”.

Write and tell me about your day, if you want. It must get boring listening to me bitch about my life all the time.

Thanks for listening



She had run the spellchecker and re-read the text four times before getting enough nerve to click “send”. She didn’t want him thinking she was just some dumb broad looking for someone to listen to her. “Strange,” she thought, “I really am trying to impress him. It’s almost like when Gregory and I were first dating, when I wanted to come off as intelligent and sophisticated.”

They had been returning daily emails for three weeks now, and both of them had relaxed a lot. She described herself to him, leaving out the slight droop to her breasts and the little post-pregnancy tummy that would not go away (“no need to tell him all my secrets”). She told him what city she lived in and discovered he lived nearby. She had decided that the city was big enough that he could never find her anyway. She had even told him about the little things that aroused her, things that made her crave Gregory ‘s body next to hers, things that made her want him inside her.

As always, Zachary replied with his polite, gentlemanly comments, saying that she sounded like a woman who was at ease with her sexuality, at ease with her body, and knew what she liked and needed. She felt better for telling him that; she always felt funny talking to Gregory that way, like she was a little slutty for a wife and mother of two. Zachary’s reply to that statement was that if women were a little sluttier in the bedroom, marriages would probably last longer, and the birth rate would increase exponentially. She laughed out loud when she read that one.

The next email from Zachary left her sitting at the computer, her whole body tingling in fear and anticipation, and her mind reeling from the excitement of the possibilities.


From: Zachary

Subject: My special treat for TinyRedRose

I don’t want to insult you, or drive you to end our conversations, but I would like very much to meet you in real life. I hope you can tell, by now, that I deeply love my wife, and would never hurt either her or you, but you are such an interesting person. I would love to treat you to dinner, dancing, and that nightcap you seem to love so much. We don’t have to kiss, and as for feeling …”relieved”, afterward, well, I would never presume so much from so nice a person as you.

I won’t ask you to accept by email; I have reservations at Restaurante’ Vitale for eight o’clock next Monday. I shall be there, waiting; ask the hostess for “Zachary “. She will know who I am. If you decide not to accept, I will simply have a nice dinner, by myself, and then go home and email my apology to you for being so forward. If you decide to accept, I also have reservations at Bailey’s (excellent jazz, R&B, and some nice, slow, intimate dancing music, by the way), and know of a little corner bar that stays open ’til three. Please allow me to be your Zachary for one night.

Waiting at Vitale’s



She went to bed that night, and lay awake in thought. “Even if nothing happens, it would be kind of like adultery, wouldn’t it? But it would be exciting, and fun, just like Gregory and I used to have. Zachary sounds safe; he wouldn’t hurt me, would he? We will always be in a public place; that’s what the dating sites tell you to do, always be in crowded public places the first few meetings. If he tries something, I can always scream, but would I have the nerve? It would embarrass me so much, to say nothing of Zachary. What if it was only an offhand comment or if he was trying to be funny and I misunderstood? No, I could tell the difference. God, I really do need to get out, I’m starting to talk to myself.”

She called her sister on Monday morning, after Gregory left for work, and asked if she would watch the kids for the night. She used the excuse that she was meeting some girlfriends for dinner, and wouldn’t be home until late. She would pick them up on Tuesday afternoon. Her sister said yes, just bring them a couple of movies and a pizza, and they would be fine. She raced to the video store, agonized quietly while the kids looked at every kid’s movie before selecting two, and then dropped them at her sister’s house along with two large pizzas. A quick trip to get her nails done used up the early afternoon.

She spent a lot of time getting ready. First a slow soak in the tub, the water was so hot she had to sit down in small steps to get used to the temperature. As she shaved her legs, she thought about how red her bottom would look when she got out. The bath salts penetrated her skin and left her feeling relaxed and smelling faintly of strawberries. She stood in the tub to shave her mound; Gregory had talked her into shaving the curly, red silk soon after they were married, but because he had been at work so much, she had been neglecting it.

She didn’t intend on giving Zachary a peek, but the thought of having shaved lips that he didn’t know about excited her. Her long, red hair came next, shampooed twice, cream rinsed, and conditioned until it fell around her bare shoulders in waves the color of burnished copper that smelled of apricots.

Moisturizer, applied to every inch of her small body she could reach, made her skin feel as soft as silk; her tan glowed in sensual contrast to the red tresses, and as she looked in the mirror at the diminutive, naked person staring back, she decided that she looked good enough to eat, as if that would ever happen. Just to make sure, after the requisite deodorant, she used her favorite perfume between her breasts, inside her elbows, and just to feel really feminine, behind her knees and on her smooth mound. Now she would smell good enough to eat, too.

She strolled, still nude, to the bedroom, stopping to roll her hips as she passed the full-length dressing mirror. “Pretty sexy,” she thought, and cupped her 32C breasts, raising them to build the cleavage she intended to show tonight. She selected the bra she knew would achieve the effect, a cleverly designed wisp of lacy black fabric that magically lifted her breasts to swell over the tops of the demi cups, the nipples almost peeking over the edge of the lace trim.

Panties were no decision at all; only the tiny black, lace thong that barely covered her sweet lips would do tonight. She stood in front of the mirror as she eased the tiny garment over her firm hips. “God, I am slutty. You,” she pointed at the mirror, “are making me horny as hell … but go ahead. It feels great.” She laughed as she thought of what Zachary would think if he saw her doing this. He was so polite and reserved, he would probably just tell her how nice she looked, and not even try to touch her.

She smoothed the black stay-up stockings from pink toes to golden thighs to round out her lingerie selection; she loved stay-ups for the freedom from the creep of pantyhose and the tattletale lines under a dress from the straps of a garter belt. From the closet came the black dress that caressed her curves and accented her bust even more by slimming her waist and hips. The neckline was narrow enough to hide her bra straps, but plunged deep between her breasts to reveal the soft spheres of skin pushed up by the cups. She stepped into black patent leather heels, and inspected the result of her efforts. “Pretty good for a girl with two kids,” she said out loud as she adjusted the bra to even her cleavage.

Back to the bathroom for makeup, from which she emerged with a perfect complexion, large, green shadowed eyes with stunningly long lashes, and pouting lips glossed in flame lipstick. The addition of emerald earrings, and emerald pendant, and a cocktail ring for her right ring finger completed the transformation from suburban mom to sensuous beauty out on the town. She left the wedding rings on; no sense giving any false signals to Zachary.

The cab dropped her at Restaurante’ Vitale at five to eight. She was carefully evaluated by two men waiting with their wives for a table, and was pleased to see them return her smile. The two wives turned their ample asses to her to stare at their husbands, and with one look, the smiles vanished. She chuckled to herself, and swayed her round hips at them as she walked to the reservation desk. “Mr. Zachary is waiting for me, I believe.”

The hostess pointed her way down a list with a bright red false fingernail, and then said, “Oh, yes, right this way.” Hannah followed the swaying bottom in black skirt into the restaurant as the tantalizing odor of Italian spices wafted from the swinging kitchen door.

This had all been a game, until now. She had been so sure of herself, but now that she was going to meet him, her heart was pounding in her ears, and little tiny butterflies were flitting around in her stomach. They turned down a row of tables, the butterflies grew to gargantuan proportions, and even if she hadn’t been wearing heels, her legs would have still been a little unsteady. The hostess stopped at a booth sitting by itself in a corner. “Ma’am, this is Mr. Zachary’s table.”

Hannah didn’t see the ten dollar bill that passed between his hand and the hostess; she was too absorbed in the man as all six feet of his muscular body stood to take her hand. A rich baritone voice spoke from the rugged face framed in dark wavy hair, “TinyRedRose?”, and shook her out of her daze. His dark eyes were engulfing her from head to toe, and Hannah blushed at the pleased look on his face.

“Yes, it’s me.” Hannah smiled her friendliest smile, and received a warm one in return.

“Well, you certainly are tiny, and also very red haired. I’m glad you accepted my invitation. Didn’t really know how you would react, but I had to ask. I’ve wanted to meet you for so long.”

Through the excellent dinner, they talked of things general and things specific, about her life and his. They found that they really knew each other quite well, even though their prior meetings had been only electronically processed text painted on a computer screen. As she finished her after dinner amaretto and he his brandy, he asked, “Do you trust me enough to take in a little dancing? I’m not great, but I can hold my own.”

She replied, casually, she hoped, with, “sure.”

Bailey’s was a fantastic place, not uptown showy, and not typical jazz dark and dingy, just clean, comfortable and with a small, but adequate dance floor. They ordered drinks, and listened to the band of mostly older African American musician’s playing the old, standby slow jazz and blues that made her body want to sway sensuously to the beat. They were through their first drink, when Zachary ordered a second, when the music slowed to the tempo for slow, close, intimate dancing.

“May I have this dance?” asked Zachary as he stood and offered his hand.

She snuggled up to him as soon as they reached the floor, and then realized she was too close, at least too close for the first dance of the evening. She backed away to a comfortable distance, and Zachary led her around the floor. He was a wonderful dancer, easy to follow, and he always seemed to keep her at the center of attraction to the people watching from the tables.

She saw smiles as they passed, and smiled back as she enjoyed the attention. As the evening progressed, she danced closer to Zachary , and ended up pressing her body against his with her cheek on his chest as they stood and swayed together, enjoying the contact and nearness of each other. The feel of the muscles under his coat, the rhythmic sound of his heartbeat, and the drinks relaxed her made her feel safe in his arms. As they finished the dance, Zachary said, “How about that nightcap? It’s one o’clock.”

The cab dropped them at a little bar at one end of a block containing the sprawl of a large chain hotel. “I found this little bar when I stayed here once,” said Zachary. “It’s quiet, soft lights, and booths. They stay open late, but I don’t know how they make any money; when I was here last, there was only me, the bartender, and one couple.” He opened the door for her, and then followed her in to a long room with a bar along one side, and booths along the other. Faded pictures of old movie stars competed for wall space with neon beer signs and the short, fat bartender seemed happy to see them as he smiled from behind his tap handles. Zachary selected the back booth, and then asked her what she wanted to drink. He returned shortly with her rusty nail and a scotch neat for himself.

They talked about the evening, how much each had enjoyed the other’s company, and finished a second drink.

“I’m glad I accepted your invitation. I needed to get out, to have some fun, just to feel like I’m still alive. I thank you for that, and for not trying to push me into anything. You’re such a sweet man.”

“And you’re a very sweet lady, TinyRedRose, and quite ravishing too. I have enjoyed our evening, and hope you might consent to another, the next time you feel the need. I’m only an email away, you know.”

The bartender walked to their booth, and said, “Sorry sir, I need to close up; my license, you know.”

“That’s all right; we have to be leaving anyway. Thank you for allowing us to visit your establishment, and I hope we will return.”

Outside, Zachary turned to Hannah, and said, “Well, TinyRedRose, I’ll get a cab to take you home. I’m staying in the hotel here. I’ll go with you, if you wish, but your neighbors might think unseemly things about you if they see me with you.”

“Yes, they might, but I don’t want to go by myself.” She put her arm in his, laid her cheek on his chest, and whispered, “Could I just stay with you tonight, if it’s not too much trouble?” Zachary held her close and kissed her gently.

His room was small; with one king size bed, two chairs, one table, and pictures of tree covered valleys on the print wallpapered wall over the bed. Neither said anything as they entered the room and Zachary took care of the little tasks of hanging the “DO NOT DISTURB” sign, locking the door, and setting the chain. He turned to find Hannah standing close with desire burning in her green shadowed eyes. She took his lapels, and pulled him into the room, and then stripped off the coat in one, smooth, fluid motion. The tie went next, and she unbuttoned his shirt, one button at a time, her nimble fingers moving slowly and caressing his chest as she removed the garment. When Zachary stood bare chested before her, she embraced him and reached on the tips of her toes for his lips.

The kiss took his breath away; she was open mouthed and searching for his tongue almost before their lips made contact. Her eyes closed as his lips caressed her bottom lip, rolling it and gently pulling. His mouth found hers again, and this time two searching tongues found each other and played gently, each filling both owner and playmate with pleasure and the promise of things to come. As her small hands traced the muscular outlines of his chest, Zachary found the zipper on the black dress, and slowly pulled it down to its origin at the swell of her hips. His hands slipped inside to the small of her back, and gently rubbed the smooth, tanned skin of her back, then the even softer hips.

Hannah pulled away gently, and let the dress slide from her shoulders, down to her hips, and wiggled seductively to shake it to the floor. Zachary watched as she unhooked the bra and let it fall on top of the dress. She stood before him in stockings and the tiny thong. Zachary felt the stirrings of lust in his crotch. The body was small, but proportioned for a model, large breasts with already hard nipples that were long and thick. She ran her hands over her breasts, letting the nipples flutter as her open fingers stroked up and down. Her eyes became even more sultry, as if willing him to take her, now.

Her small hands unbuckled his belt, undid the catch, and slowly unzipped the zipper. The pants slid down his legs and ended up in a pile around his penny loafers. She led him to the bed, threw back the covers and pushed him down. Hooking her fingers in his shorts, she pulled them down to his ankles, and then over the shoes he still wore. She pulled off the shoes, letting each fall where it would, and then crawled up his body on hands and knees, her nipples dragging over the hair on his legs, and her thong clad ass swaying from side to side. She stopped at his cock, and looked him in the eyes, the dark pupils speaking of untold pleasures waiting.

A small hand gently cradled his balls, feeling them for size, and slowly rolling them in her palm. The fingertips pressed on the area between his balls and his anus, and the feeling caused a small groan to escape his lips. His eyes closed when soft, wet lips caressed the head, and then took it in, and he groaned again when her small pink tongue swirled around it, then found the small slit and tried to enter. He didn’t have time to think about another groan before she took him all the way into her mouth or at least as far as her small mouth would allow.

Her saliva covered his cock now, and her lips slid easily across his sensitive skin as she worked her mouth over his length. Her tongue teased the underside of the head with every stroke, and he had to pull her off to avoid cumming. He pulled her to his chest, and kissed her, hard this time, as his fingers hooked the string of the thong, and pulled it over her firm ass cheeks. She rose to help him, lifting each knee in turn until she could kick it to the floor. She spread her thighs to straddle him, and rubbed her pussy over his belly, her free flowing nectar wetting the arrow of dark hair that pointed the way to his cock. He could feel her clit touching him, and reached to fondle it with a fingertip as his other hand began kneading her breast.

When he pinched the erect nipple, she whispered a small “mmmm”, when he found her clit; she gasped, and pushed her pelvis into his hand. She rode his hand until he gently pushed her up, and inserted two fingers into her, stroking them in and out against the soft, slippery pad that covered the bone. His fingers plunged deep, and then curled up inside her as his thumb rubbed her wet clit. She was shaking with the pleasuring of his hands, and shrieked as the fingers found the special spot high in the front of her passage. He moved his thumb from her clit to her belly and gently but firmly pinched thumb to fingertips, massaging her special spot, and eliciting a series of shrieks and moans from Hannah. He returned to massaging her clit and nipples until she was panting out moans and humping against him.

“Oh, Zachary, fuck me, mmmh … please fuck me … mmm … now!  Now, oh please … inside me, I … ohhh … need mmmh … to feel you inside me!”

He lifted her easily to his erect cock, and toyed with her by rubbing her clit with the head. She was clawing at his chest, leaving red welts when he finally allowed her to settle her swollen lips over the head. He held her up, not wanting her to impale herself, not yet, and let her juices run down his length.

“Ohhhhh, put it in. Damn you, fuck me. Oh please, let me go. Ahhhhm … ahhh … ahhh …”

Suddenly, he let her drop; let her drop over his cock until her lips smashed wetly into his pubic bone. Her voice was a whimper as she writhed on his hard shaft, her hips jerking back and forth, pulling herself off of him, and then pushing back on. She leaned forward to grind her clit into his shaft as she stroked, and Zachary began meeting her with deep strokes that pushed deep against her soft womb.

Hannah was no longer in control of herself; her mind, hot with passion, concentrated on her turgid nipples, throbbing clit, and the large cock that filled her. As each stroke pushed against her insides, uncontrolled ripples ran down her soft belly and ended as contractions of her passage that milked Zachary’s cock for his sperm. Her cries were low, whispered moans of ‘mmh …mmh …’ that gained volume as her hips rocked faster and faster. Her whole body contracted on top of him, and then spasmed with her loud Ummmmmmmmhm and Zachary erupted a stream of white cum that splashed against her womb. “Oh, Yes, yes … yes…”

Another spasm of her body, and she ground down hard, forcing him into her as deeply as she could. His second splash filled her and began leaking around her pussy lips onto his pubic hair, as she rocked back and forth on his cock in quick hard jerking movements. “ahh … ahh … ahhh … ahh … ahh …”. A third shrieking spasm sent her falling to his chest as he stroked deep for the last time, his splash more of a trickle of cum this time, and her sounds returning to a whispered “mmmmmmmmmmmh”. She tried hard to keep him inside her, but when his cock finally slipped out of her sopping, grasping passage, she climbed up his chest, pressed her nipples into him, and nestled her cheek on his shoulder. After she fell asleep, Zachary gently rolled her off him, and gazed on her still stocking-clad body once more before pulling the sheet over her.

She awoke to find him staring at her. Through sleepy eyes, she stared back, and then smiled. Last night, she was TinyRedRose and he was Zachary. Before, it had been Temptress and Sultan, HoneyBuns and CubbyBear, during one particularly unique exchange, ChainLady and Slave. It had been her idea, the first time; Gregory laughed, but started playing the game to please her. He had become extremely good at it, and she loved the suspense, the guesswork, and the anticipation of what would come next. They had worked out keywords to let each find the other in the chat room, she at home, and he at his computer at work.

It was the only way they could be together when he worked so late, and figuring out what nickname the other had chosen was half the fun. Sometimes one would “hide out”, not saying the keyword that would reveal their true identity for a few nights, and the other would make bungling attempts at contact with chatters who sounded right; the result was hilarious, like watching a movie where the amateur spy tries to exchange code words with an innocent bystander, but they would eventually find each other, progress to email, then to a meeting, then to the exquisite role play that kept their marriage young and fresh. She only hoped no one monitored his email at work. Some pretty hot stuff had been sent and received between them.

“Good morning, my Zachary. You were wonderful, as usual. I needed to be fucked so badly.”

“When do you have to pick up the kids?”

“Not until this afternoon. When do you have to go back to work?”

“Well, I was supposed to be there this morning, but fuck’em. Hell, I manage the damned place, and I put in enough hours last week. I deserve some time off with my little TinyRedRose.” He grinned and reached over to tweak her nipple, loving the feel of it thickening under his fingertips.

Hannah chuckled, hooked her soft thigh over his body, and rubbed her soft, bare lips against his leg. She whispered, “Well, you can fuck’em if you want, but since we’ve only got this room until noon, I’d much rather you fucked me again instead.” 


A Night with Zachary
©Tianna Filley, 2017

This is a work of fiction. Names, characters, businesses, places, events and incidents are either the products of the author’s imagination or are used fictitiously and are not to be construed as real. Any resemblance to actual events, locales, organizations, or persons, living or dead, or actual events is entirely coincidental.
A Night with Zachary Copyright ©2017 by Tianna Filley.

All Rights Reserved.
No part of this story may be used or reproduced in any manner whatsoever without written permission from the author.

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