Her: I’ll be in the city tomorrow.
Him: Oh, will you?
Her: Yes– just for a night, though.
Him: And would you like some company for that one night?
Her: I would.
Him: Whose company would you like?
Her: My old high school teacher, Mr. Spencer’s, I think. I’ve always wondered what would happen if I ran into him at a bar, and caught him looking at me. He’d be confused because he would know that I looked familiar, but he also wouldn’t be able to think much beyond how hot I looked. And when I went up to him to say hi, he wouldn’t be able to look away from my tits.
Him: Mr. Spencer sounds like quite a few men I know.
Her: Well, my tits are certainly something to be admired.
Him: That they are. And what is the name I call my dear, newly found student?
Her: Sharon. And you know, I think I was a naughty student. One that needed to be punished, a lot.
Him: I wouldn’t expect anything less.
Her: I’ll see you at the bar on Jones street. Ten O clock?
Him: I look forward to seeing you again, Sharon.
Her: I’m excited to see you too, Mr. Spencer.
Sharon bent down to look at herself in the window of her car, studying her reflection carefully. She swept a lock of her new blonde hair back behind her ear and pursed her lips to check her bright red lipstick. Satisfied, she smiled and turned around, walking through the parking lot towards the bar door. She was wearing a skirt that came to her mid-thigh and while it wasn’t tight, her hips stretched at the material. Her deep blue sweater was tucked into the skirt, her blonde hair curled and falling over her breasts. She looked good, and she knew it.
This wasn’t the first time she had been to the bar on Jones street. She had been to it a number of times before, though this was the first time wearing this wig and with the name Sharon. She wasn’t sure if the bar’s regular patrons ever recognized her in her various disguises and identities, but they certainly never bothered her, and that was really the only thing that mattered. She had been visiting Jones Bar for about five years. It had started when she was there on a week-long business trip once, and she had run into a man with dark eyes and dark hair and a desire that matched hers. Every night for that entire week, she and the man would meet at Jones Bar with wigs and new outfits and new names and new stories, pretending to meet each other for the first time and having amazing, different sex every single time. Ever since that week, the two of them had been meeting up whenever she came to the city. She would text him when she found out she was coming and would tell him how she wanted them to meet up, how she wanted them to act. Then, when they had realized he had family in her hometown, he would message her when he was visiting them so that he could pick how he wanted them to meet up and act. It was perfect. She could be anyone and everything she wanted; she could explore a new kink with every visit, and she never had to worry about judgment. She and her partner understood each other. They knew each other. All she ever wanted to was give him pleasure, and he wanted to do the same for her. It was like a long distant relationship, with all of the benefits and none of the setbacks.
And tonight, as “Sharon, the returning high school student,” she was definitely going to take advantage of those benefits.
She stepped into the bar and headed straight for the bar, pulling a twenty out of her purse and holding it between two fingers slightly aloft, so that the bartender could see it. When he came over to her, she ordered a vodka cranberry. Sipping at it lightly, she turned around to face the rest of the bar and leaned back with her elbows. Her eyes flicked over the room, looking. She caught the eye of a man wearing dark-rimmed glasses and thick dark hair combed back from his face. He was wearing slacks and a lightly striped blue button-down and was sitting alone at one of the booths that lined the bar walls. He was looking at her with a slight furrow in his brow, as though trying to place her. Sharon bit back a smile and took a long pull from her drink before pushing away from the bar and starting to walk forward. There he was. And now the night could begin. She came to the edge of the booth, and he gave her a startled, unsure smile.
“Hey, there,” she said, and his smile wavered, as though he had realized something.
“Hi– sorry, I– I just thought that you looked so familiar, and–”
“I was thinking the same thing,” she said, cutting him off with a smile. “Mr. Spencer, right?”
He blinked, and then his face cleared into a surprised smile. “That’s right! And… Sharon, if I’m not mistaken?”
“You are not.”
“Well.” His eyes dragged up and down her body, stalling on where her hips stretched the material of her skirt, and where her braless tits rose and fell with every breath. “You’ve definitely grown up since I saw you last.”
“I like to think so.” She tilted her head towards the booth seat next to him. “Mind if I take a seat?”
“No, please do. I’d love to catch up.”
After that, it didn’t take long for them to leave the bar and head back to her hotel room. They fell onto the bed, scrambling to take each other’s clothes off. Sharon couldn’t catch her breath, her panties flooded with wetness as she kneeled in front of Mr. Spencer, his cock bobbing in front of her.
“You know,” he started, his voice thoughtful, “you never wore a god student. I had to give you so many detentions… you know what I wanted to do, though?”
Sharon licked her lips and held back a whine. “What? What did you want to do?”
“I wanted to spank that tight little ass of yours so hard, make it nice and red. Really teach you a lesson. Of course, I couldn’t do that in school, but now…”
“You going to punish me? Teach me how to be a good girl?” Sharon bit her lip and wiggled a little where she kneeled, knowing how it made her curves jiggle deliciously when she did that.
“I think that’s exactly what I’m going to do. Stand up, and lean over the bed.”
Sharon jumped up and quickly did as she was told, leaning on her forearms over the bed and letting her hair fall over her shoulder. The position opened up her pussy, and she shivered, feeling the air against her sensitive, wet flesh. Mr. Spencer moved to stand beside her, and he placed his hands on her waist, squeezing at the curve of her body for a moment before dragging his hands further down her body so that he could grab at her ass, massaging it.
“Fuck, you feel good, Sharon,” he breathed. He leaned over her to press his mouth to her back. His cock rubbed at her pussy from the back as he did and she whined, squirming back to find more friction against him.
“Please, Mr. Spencer,” she whimpered. “I’ll be good for you. I’ll learn my lesson.”
“Sure you will.” One of his hands moved from her ass to her clit, which he squeezed and rubbed at. Sharon moaned, her legs shaking as heat pulsed through her from the sensitive nub. “But first, I have to discipline you for all the times you’ve been bad in the past. I think five spanks should do it, don’t you?” He leaned away from her. “I want you to count them as I go. Got it?”
“Yes.”
“Good.” He squeezed her cheek one more time, and then lifted his hand and let it fall on her with a loud smack!
Sharon gasped and jerked forward, her face twisting slightly at the pain even as she felt her pussy dampen. “One,” she breathed and gasped as he did it again. “Two.”
He rubbed at her slit, feeling how wet she was. He laughed.
“Look how wet that made you. I guess I can’t say I’m surprised you grew up to be such a dirty slut. In school, you always were so desperate… staying after class, trying to convince me to raise your grades…” he curled a finger into her cunt, and Sharon moaned as he pressed against her clit at the same time. “Tell me, Sharon. What would you have offered to do to raise your grades?”
“I…” she took a deep breath. “I would have walked into your office, and asked if I could talk to you. And I would close the door behind me, and would make sure you couldn’t see that I locked it. I’d walk up to your desk and lean over it, and pretend that I was just being curious, so I could see what you were doing on your computer. But really, I just wanted to let you look down my shirt.”
“I would have liked that.”
“Then, I would walk around the desk so that I could lean against it and face you. My nice, long legs would be stretched right next to your body in my short little skirt. You wouldn’t have had a choice but to look.”
He moaned a little, and then spanked her again. She jerked forward with a gasp.
“Three.”
“Then what?”
“Then, I’d ask you if I was really so bad that I deserved an F in your class. And then I would tell you that I could be bad for you in other ways. In better ways. In ways that would make you feel so good, so good.”
Mr. Spencer groaned and spanked her again, barely hearing her choked out “four” as he pushed his finger into her cunt from behind, his cock hard and leaking against his hip as he felt how tight and wet she was.
“Fuck, you feel good,” he muttered. Juliet clenched around his finger and whimpered.
“Please,” she begged. “Please don’t make me wait anymore. I want to fuck you so bad, I’ve always wanted to fuck you so bad. Please, just fill me up, let me make you feel good. I just want to make you feel good.”
Mr. Spencer moaned and braced himself behind her, lining his cock up with her hole and just barely pushing the head in. Her vision went hazy with desire as heat poured over her, her pussy desperate and clenching. She wiggled back against him, trying to pull him deeper, as he squeezed teasingly at her hips.
“Please,” she begged, one more time, and when he was finally inside her. His cock filled her, her hot inner walls enveloping him and squeezing around him. He throbbed inside of her. Her legs spasmed as she gripped the bedsheet, and Mr. Spencer tightened his hold on her hips,
keeping her steady. He pushed in slowly, deeper until he was buried to the hilt inside of her. She moaned and whimpered, pushing back to meet him, to draw him deeper into her.
“Fuck, Sharon, so tight,” he gasped. “ I didn’t even need any lube, you’re already so wet. How does it feel, baby?”
“God, so good,” she moaned. “Please, please fuck me.”
He laughed, breathlessly. “Alright, babe. I’ll give it to you.” He lifted his hand and let it fall on her ass, and Sharon groaned.
“Five.”
Him: I’m in town for my sister’s birthday this weekend. Are you up for grabbing drinks?
Her: Hm. Depends. Who am I?
Him: I think your name is Jessica. You have long brown hair, a blue dress, and the reddest lipstick I’ve ever seen. You’re going to be at the hotel bar; it’s known for having a thriving escort business.
Her: Escort? Interesting. And am I supposed to want to be hired by you?
Him: Yes, you tease. Although you’ll be working, so if someone else comes up to you, you’ll have to play along. At least just to talk. It is your job, after all.
Her: Yeah, right. Anything else I should know?
Him: That should be all.
Her: In that case, turns out I can’t get drinks this weekend. Looks like I’ll be busy working instead.
She was sitting at the bar when he came in, a martini at her lips. Her curves were on display in a tight blue dress that plunged deep in the front. Her red, red lipstick left a mark on the martini glass. A portly man was standing next to her, obviously trying to chat her up, though it seemed he couldn’t take his eyes off her tits to actually say something to her face. She was indulging the man, it seemed, but she was clearly getting annoyed.
He bit back a laugh and walked across the hotel lobby to the bar, where he went to stand at her other side. He felt her look at him, but she didn’t say anything, staying in conversation with the other man. He orders some whiskey and took a sip of it before finally turning to look at her. His eyes flicked down to her glass– she’d finished her martini.
“Come on, man,” he said, interrupting the two’s conversation. “If you’re going to talk to such a beautiful woman, you should know at least to buy her a new drink.” He gestured to the bartender, as the man next to Jessica sputtered.
“I– well I wasn’t–”
‘“My name is Jessica,” she said quickly, twisting at her barstool to shake his hand. She blinked flirtily at him. “It’s nice to meet you.”
“And it is so nice to meet you,” he replied, taking her hand and pressing a soft kiss to her knuckles. “You can call me Jared.”
“Nice to meet you, Jared.”
The other man seemed to realize he had lost his chance and turned away grumbling. Jessica took a moment to glare after him, her face twisted in annoyance before she carefully suppressed it.
“So,” Jared started with a grin, “come here often?”
“I do, actually.” She took a delicate sip from her drink. “I’m here a lot on business.”
“Oh? And in what business would that be?”
“Hm.” Her eyes flickered down his body. “Sales.”
“That sounds fascinating.”
“Oh, trust me, baby,” she whispered, leaning closer. Her eyes glinted. “It’s way more fascinating than you’d ever imagine.” She placed her hand on his thigh and squeezed a little.
He swallowed.
“Well, if you have time, I’d love to hear more about it.”
“I can do better than that,” she promised. “I can show you.”
Tomorrow. At eight o’clock. A reservation is at the French restaurant on the river. Be there. We’ll be Shane and Juliet. Juliet wears a red dress– she’s a sweet girl from the South, new to the city and new to dating. Shane is a confident businessman who knows what he wants and knows how to get it.
What will we be wearing?
Juliet will be in a red dress. Shane will be in a suit. With a white handkerchief in the pocket.
And is there anything else I should know?
Nothing that you won’t get to find out. Tomorrow. Eight o’clock. Make sure you’re on time.
When she walked into the room, all eyes were one her. She was in a dark, low cut red dress that clung to tight to her hips and folded in a wrap-around her chest, giving just a hint of cleavage at what was obviously an ample amount of tit. Her black hair was curled into tight whorls that fell past her shoulders, and as she walked across the heavily carpeted floor the sound of her heels made dull thumps that matched the tune of the piano.
Eyes followed her as she walked towards the back window, towards a table carefully tucked away to offer some privacy. A man was sitting there, wearing a three-piece suit with a white hanker chief tucked into the pocket. His blonde hair was combed back carefully, his jaw square and cleanly shaven. He was staring out the window, one hand under his chin as the other tapped slowly on the table. She smiled when she saw him.
“I must say, Shane” she said quietly, startling him into whipping around and looking at her. “This is probably the fanciest place I’ve ever been to for a first date.”
He smiled at her and stood, stepping forward to kiss her cheek softly. She shivered slightly at his warm, wet lips brushed over her cheeks.
“Juliet, I’m so glad you came,” he grinned. “I was getting worried that you weren’t going to show. I was here– eight o’clock sharp,” he added, his eyebrows tilting slightly.
“Oh?” she asked, a little airily. “Well, my apologies, Shane. I’m not used to making my way around the big city. But of course, I had to come– how could I not? Sweet things like you. I would never be able to stand you up.”
His eyebrow lifted lightly at the slight southern accent in her voice but didn’t comment. He just went around the table to pull her chair out and gestured for her to sit down, which she did. He took his seat back at the table across from her and quickly gestured for the waiter to come.
“What do you drink?” he asked. “Red or white?”
“Well, to be honest, I don’t even really drink. So I don’t know.”
“Oh?” Shane’s eyebrows lifted, his mouth tilting into a smirk which he quickly suppressed. “Well, in that case,” he turned to the waiter, “I’ll get a bottle of your best bottles, and the lady can decide for herself which she likes best.”
The waiter nodded and promptly turned on his heel towards the kitchen. Juliet watched him go.
“What if I don’t like either?” she asked, teasing, and Shane chuckled.
“Well, I supposed I can order over a bottle of whiskey they have. And if you don’t like that, we can move onto rum.”
“And then?”
“Apple juice, maybe?”
Juliet laughed, and Shane bit back a chuckle. He leaned forward, folding his hands in front of him on the table.
“So, fanciest first date, you said?”
“That’s right. To be honest, I never even knew people when to such nice places for a first date.”
“Well,” Shane drawled, “I thought that tonight needed to be extra special.”
Juliet blushed and giggled. Then the waiter brought the wine back out from the kitchen, and the two of them were giggling a lot more after finishing both of them.
After finishing the bottle of white, and their plates of pasta, they were both full and sated, and their legs twisted together and rubbed against one another under the table. Shane reached across the table, and Juliet reached her hand out as well to meet him. Their fingers wrapped around each other.
“So,” Shane started, “you say this is your fanciest first date?”
Juliet giggled. “Yes, for like, the third time.”
“Well, what do you think? Is it going well so far?”
“Oh, I’d say it’s going very well.”
“In that case,” Shane smiled flirtily, why don’t we order dessert to go, and then maybe we can eat it back at my place?”
Juliet’s cheeks flushed a deep red, and she looked down at the table.
“Well, actually, I… well…”
“What is it?” Shane’s eyebrows furrowed as she blushed deeper.
“Well, I’m– I’m a virgin.”
Shane’s mouth almost dropped, but he quickly bit his lip and held his jaw in place. His heart was thumping. This wasn’t an idea either of them had ever had before, but his cock stirred with interest against his thigh, he realized it was something he was very, very into.
“I must say, Ms. Juliet, that does not look like the dress a woman would wear on a fancy first date unless she knew what she was doing,” he said, and she laughed a little. “And,” he continued, “it certainly doesn’t look like the dress of a virgin.”
“Well. I was thinking that tonight could be a special night.”
She grinned at him, and Shane shifted in his seat, heat curling low in his belly as her blue eyes glinted at him.
“Let’s be sure to make it one then, shall we?” he said and waved to the waiter.
“We’ll take the check, please,” he said, and Juliet grinned, pressing her leg harder to his beneath the table.
Shane opened the door to the hotel room for her grandly, bowing and holding his arm out. Juliet laughed and stepped inside, letting her coat fall to her elbows and then dropping it onto one of the hotel room’s sofa chairs. She sat on the bed and pulled her heels off, slowly, as Shane closed the front door. His eyes trailed the drag of her fingers over her are leg.
“Is there anything I can offer to get you?” he asked. “Another glass of wine, some water…?”
“Actually,” she said, biting her lip, “I think that maybe you should just come over here.”
Shane grinned, his lips curling up and his eyes flicking over her body as he went to sit next to her. She smiled shyly at him, shifting where she sat.
“I don’t… I don’t really know what to do,” she said, her eyelashes fluttering. “Will you
show me?”
“Of course.” He lifted his hand and brushed her hair back from her face, over her shoulder.
“And… will you teach me?”
“Fuck, Juliet,” Shane breathed. He leaned his forehead against hers, inhaling her scent deeply. She smelled like vanilla and fruity white wine. “Yeah, babe. I’ll teach you.”
Juliet put her hand on the inside of his leg and slowly moved it up towards his crotch until her fingers were just barely brushing over his hardening cock. He groaned low in the back of his throat as she pressed down harder and shifted to press her lips against his neck, and started to kiss up to his jaw.
“Is this right?” she whispered. Her tongue flicked out just barely tip against his lips. “Does this feel good?”
“Fuck, yeah, yeah, that feels really good,” he grunted. He leaned back, bracing himself with his hands, as Juliet stood and then fell to her knees, moving to kneel between his legs. She undid his belt and unzipped his slacks, licking her lips as the bulge of his cock pushing against his boxer briefs was revealed.
“Wow,” she murmured. Her eyes glinted with amusement, and she looked up at Shane. There was a joking look in her eyes, the closest he had ever seen to her breaking character. “Are they always so big?” she asked, and he let out a startled laugh but didn’t bother to reply, and she didn’t wait for an answer.
She pulled his cock out, and Shane took a deep breath as she leaned forward and pressed her lips to the shaft. Her tongue pressed against the vein that ran down its underside, and her hand teased at his balls, squeezing them lightly and massaging them.
“Is this good?” she asked. Her mouth was at the head of his dick now, her lips wet with saliva and his precum. “Am I doing good, Shane?”
“You’re doing so good, Juliet,” Shane breathed out. He ran his finger down her cheek and down to the back of her head, threading his fingers through her hair. “So good, babe.”
Juliet wrapped her lips around his cock and sucked at it a little, swirling her tongue around the head. Shane shuddered violently beneath her, his hips twitching forward just barely. Juliet moaned around his organ, and Shane’s eyes clenched shut in pleasure.
“Make sure you get those balls too, babe,” Shane ordered, and Juliet obediently moved her mouth to suck on his sack, her hand continuing to pump him up and down.
She continued to suck on him for a minute or two, his vision getting shakier as pleasure-filled every part of him until suddenly Juliet pulled off of him. He looked down at her, panting. She was breathing hard too, her jaw hanging open. Precum and saliva was at the corner of her mouth, her eyes filled with tears from having sucked his dick so hard. Her cheeks were red, her lips redder. She looked absolutely filthy. Shane wondered if he’d be able to come just by looking at her.
“What is it, Juliet?” he asked. “Why’d you stop?”
“I, I had to,” she gasped, blinking prettily. “Your cock feels so good in my mouth, I just want something more, but I don’t– I don’t–”
Shane groaned and grabbed her arms, pulling her up into his lap so that she was straddling him. He fisted his hand in her hair and pushed his mouth against hers, biting at her lower lip to ask her entrance. She opened for him readily, grinding down against him and pushing her tits against his chest. His cock pushed against her bare thigh, exposed by her dress hiked up to her hips. One of his hands crept down her back to squeeze at her ass.
“Please, please,” she gasped into his mouth. “Fuck, Shane, I need you so bad. I need you to fuck my tight, virgin pussy. Please, please, Shaun, I need you.” she pulled me back and looked at him, her chest heaving. He stared at her, his pupils blown. “I need you to be my first,” she whispered.
Shane grabbed her waist and flipped her over so that she was lying on her back on the bed. He grabbed her dress and tugged at it, and she quickly pulled her arms through the holes so that he could pull it over her head. His eyes lit up as he looked at her body. She wasn’t wearing a bra, her tits exposed and shiny, covered in a light sheen of sweat that David couldn’t help bending down to lick at. Juliet moaned, her legs wrapping around his waist and pulling him closer.
“Stop teasing,” she gasped. “I’ve waited a long time for this moment. To become a real woman. Take me, Shane, fuck me, please.”
Shane slipped a hand beneath her panties and rubbed at her slit, grinning to himself when he found it nice and ready for him, dripping wet. He pressed his thumb against her clit while pushing a finger into her hole, curling it slightly to rub at her hot inner walls.
“God, that feels so fucking good,” Juliet whimpered, her hips curling up to meet his hand as her neck and face flushed a deep red.
“Let me hear you,” Shane whispered. “It’s your first time, isn’t it? It’s never going to feel like this again. You’re never going to be able to lose it again. So c’mon, babe. Let me hear you.”
And so she did. The room was filled with the sounds of her moans and her whine, her hand fisting in the bedsheets and her toes curling. Shane pulled her panties down the rest of the way, and her legs scrambled to help him get them off.
“Get your clothes off,” she ordered, and he quickly did as she asked, throwing his shirt off and kick off his pants. Their bodies melded together, hot and flushed. Shane’s cock rubbed against her pussy, the crown of it pushing against the tight ring of muscle at her entrance.
“Do it, do it,” Juliet gasped. “I have to know what it feels like. Please, fill me up. Take me. I want to… I want to know what it feels like.”
Shane positioned himself over her and bent down to press his lips to hers. “
“You’re never going to feel something like it again,” he promised, and then he was entering her.
She gasped as he filled her, spread her, her legs quivering and tensing as her back arched.
“Oh, god,” she cried out, and Shane moaned as he pressed into her deeper, his hips meeting hers as he went as far as he could.
“How’s that feel?” he panted. “Have you ever been filled like that before, baby?”
“No, no,” she gasped. “Fuck, it feels so good, please, harder, more, more!”
Shane kissed her quiet and then started to fuck her, his thighs pounding against hers as she moaned with every thrust, her hips snapping up to meet his, pulling him even deeper. Her cunt clenched around him, heat curling low in her belly, and he closed his eyes and grunted as he felt himself getting closer to the edge.
“I’m almost there, baby,” he warned, and Juliet whimpered, her face scrunched tight in pleasure.
“Good,” she gasped. “I want to feel you cum inside me.”
That was enough. With a low moan, he came, splashing his seed inside of her. At the feeling of him throbbing inside of her with his orgasm, Jessica came too, her back curving up as her hands scrambled at the blankets.
“Fuck, fuck, fuck,” she gasped, as Shane shivered in the pleasure of post-orgasm bliss. He stayed inside of her as she came, his eyes clenched shut as her pussy milked his spent cock. When she finished and lay exhausted, he pulled out of her and collapsed beside her.
“Damn,” he murmured. “That was…fuck.” He rolled over to look at her, his eyes sparkling with amusement. “So? How was that for your first time?”
“Hm,” she said, twisting her lips thoughtfully before grinning. “It was so so, I guess.”
Shane laughed, surprised, and moved so that he was hovering over her. He grinned down at her and then bent to press his lips to her neck.
“Well, I’ll just have to make the second time even better,” he murmured.
