Date with Anne

Jacob quietly and meekly looked around the restaurant. Not that he wanted to be meek or look meek but he was never very good at putting on a confident front. Ordinarily, he would be used to it but today was a very different day than most or perhaps any other day in his life. It was the day of his first date and he’s quite a bit more nervous than usual.

So far, it was a regular day for everyone else in the dining establishment by appearances. Some couples and some families having family dinners. No one really bothered to look at him but it didn’t help calm his nerves much. He tried taking deep breaths and looking out of the window at his side but none of it helped.

Part of him hoped she wouldn’t show up. Then he could just get a drink or perhaps nothing at all, apologize to the waiter who showed him to his booked table for the waste of time, and leave. Then he could be done with this and resume his normal, boring, non-romantic life. Not that he wouldn’t be humiliated if anyone noticed he was stood up but it’s not like he’d see any of these people again. He can just forget about this day and most definitely forget about any future attempts at having days like this.

“Hey! Sorry, I’m late. The train was a nightmare.”

His heart felt like it jumped in his chest when he heard her voice. A voice he did not expect to hear and now that he was hearing it he was not sure how to react. Looking at her wasn’t helping either. She was still as beautiful as ever with her long red hair, freckled but not too freckled face, large circular glasses that highlighted her deep blue eyes. Her smile was warm and inviting. She wore a simple green jacket with a white shirt and light blue jeans. Not exactly formal but it was their first date after all.

“Oh, uh, it’s fine,” said Jacob as he tried not to stare. Unfortunately, it was her face he tried not to stare at and he did not want to appear rude by looking away from her completely by looking at the wall or some other person in the room which she may have found offensive so he looked a little lower and kept his eyes there.

“Um… those aren’t my eyes, Jacob,” she said with a smirk. Jacob quickly looked at her eyes with a reddening face and a heavy eagerness to apologize.

“Oh! I’m so sorry!”

She giggled at his hasty apology. Jacob felt the heat on his cheeks getting higher.

“Don’t worry about it. It’s kind of cute.”

Jacob felt his heart sink at the comment. “Cute” Was never a good sign. At least not according to what his co-workers at the office told him when they found out about this date. He felt that this could be their first and last date together thanks to that first impression.

“I’m not really that hungry so I guess I’ll just order some soup.”

Jacob looked at the menu while Anne kept looking at it. As he scanned the available dishes, she put hers down. He felt a little relieved that he would not have to pay much if that’s all she was getting.

“Hmm. Well, I guess I’ll just have soup too.”

“Wow, a copycat.”

Jacob gulped before looking back at the menu.

“Ah, well… I guess I’ll get-”

“Relax! I don’t mind. Get what you want.”

He nodded before looking back at the menu. Some of the starters seemed appealing. He wasn’t really in the mood to have a main dish let alone dessert. He supposed that his nerves were affecting his appetite too much.

“Uh… soup and… bread sticks.”

Anne shrugged at his choice.

“I guess I’ll have a couple if you don’t mind sharing.”

Jacob tried to politely smile as he placed the menu down.

“Oh, of course. It’s no problem”

They waited at the table in silence. After a few minutes, Anne looked at Jacob with confusion being clear on her expression. Jacob could not deduce why she was giving him that look. He felt himself being hypnotized by her face. Her pale skin seemed to glow against the sunlight coming in through the window. Her glasses gleaned from it. She was quite distractingly beautiful. So much that he didn’t notice her gesturing her head toward something.

“Soooooo, aren’t you going to get the waiter?”

“Huh? Oh! Uh, right.”

Jacob raised his hand to beckon the waiter over. The waiter was young, tall, dark-haired, and quite attractive. Jacob noticed Anne’s welcoming smile at him as he arrived. He could not help but feel a little put down knowing that he was likely being compared to this man even if it was just in thought.

“Your orders?”

“Uh, two bowls of soup and breadsticks. Creamy prawn for me and he’ll have…”

“Uh… tomato.”

“Right. Creamy tomato and that’s it.”

The waiter silently noted the orders in his notebook. Then he looked at Anne with a smile. She smiled back. Jacob wasn’t sure if the feeling behind the smile was mutual or if she was just trying to be polite.

“Well, may I say you look quite attractive, ma’am?”

She giggled while slowly scanning him. Jacob wanted to shrink back in his seat.

“Thank you,” She said politely.

“Would it be any trouble if you could provide me with some service?” Asked the waiter as he slowly pulled the zip of his dark pants down and exposed his growing cock to her. It grew to an impressive size. Jacob examined it and could not tell exactly if the waiter’s was bigger than his. He supposed they were too similar to tell.

“Oh, well. I’d like to but this is my date.”

“I see. My apologies,” said the waiter before he left them to be called over by a young, blonde woman. Jacob watched the waiter present himself to her as she smiled flirtatiously to him. Jacob looked at Anne nervously as she shrugged.

“Couldn’t he tell that we’re on a date? Kinda insensitive.”

“Uh, yeah,” Said Jacob before he looked back at the waiter and the blonde woman who now has her hand wrapped around his thick cock and busied herself with jacking him off at her table. Jacob shrugged at the sight before turning away. Now he could focus on the date without having to worry about competition.

“So, you told me you work as a computer repair specialist? With your own shop?”

Jacob nodded. Feeling a little more comfortable that the topic was about something he could discuss easily.

“Y-yeah. In a pretty big shopping center. People can buy stuff from there too but it’s mainly advertised as a repair store so they usually just come in if something is broken.”

“Like physical broken or software broke?”

“Well, people tend to drop their phones a lot so physical I guess.”

“I dropped mine a couple of ties so I just keep it in one of those case things.”

Jacob looked to his side to notice the blonde woman was now sucking on the waiter’s cock. She moaned on him as he tightly gripped her hair. Everyone else within the restaurant barely noticed this and if they did, they would immediately turn their attention back to whatever conversation they had. Jacob did the same as them and looked back at Anne who was currently showing off her thick, baby blue case for her phone.

“Like this. I thought of getting a pink one but I’m not really that girly.”

“W-well good thing not a lot of people think to buy them. I might get put out of business if it wasn’t for them being lazy.”

“Good point. Though my phone does have something wrong with it. Not that it’s really broken. Just kinda slow.”

Jacob immediately got curious. He wondered if this was a problem he could solve. Usually, it was and he already felt a small boos tin confidence he hoped to increase if he managed to fix this.

“Well, let me take a look at it.”

Anne handed the phone over to him. He glanced over at the blonde woman again to find her happily wiping her mouth with a tissue provided by the restaurant. The waiter re-zips his pants and nods to the woman in a thankful gesture before being called over to another table. Jacob turns his attention back to Anne’s phone and opens the case. He powers it on before presenting it back to her.

“There’s a lock screen.”

“Oh, I’ll take care of it,” said Anne as she takes it back from his hand and makes some motions on the screen with her finger before giving it back to Jacob with a smile. The tech enthusiast only had to examine the phone’s properties before concluding why it’s slow.

“Wow, this thing is old. Did you ever update it?”

Anne shrugged as she dipped a breadstick in her soup and swirled it around.

“I don’t know. I don’t think so? I never really got a notification or anything like that.”

“Well, you just…” Jacob trailed away from speech when he saw Anne take the breadstick out of the hot soup and slowly sucked the wet, flavourful juices from it that very much reminded him of a certain act he’s used to seeing on the internet.

“Just what?” asked a confused Anne.

Jacob immediately shook his head to regain his focus.

“…just uh go to the update menu here. Select confirm and I’m updating the phone so it will go faster.”

“Oh,” said Anne with a smirk. She takes the phone from Jacob’s hand when he gives it back to her.

“It should take a few minutes so you don’t need to use it right away.”

She nodded before putting the phone on the table beside her. She began to eat at the same breadstick she sucked some of the soup from.

“So, uh… how’s college?”

“Great. I’m almost done with my studies for this semester and then I can finally be a certified Pharmacologist.”

“So you could have your own pharmacy?”

“Someday hopefully,” said Anne as she stared into her soup while sipping from it. Jacob could see that she was daydreaming a little.

“Thinking about helping yourself to the inventory?” Jacob jokingly asked.

“Oh, no! Wouldn’t get away with it anyway. I’d probably have co-workers to keep an eye on me,” Said Anne with an amused smile. “Besides, no reason to risk my future license.”

“True. Not really worth it,” said Jacob as he continued to eat from his soup and breadsticks. Anne looked at him curiously as she slowly drank from her soup.

“So, do you intend to stay in that shop for the rest of your life?” Asked Anne. Jacob could not help but feel a little nervous when he started to wonder where the question came from. He guessed it must have been one of those really “Testy” questions.

“Uh, well I don’t really see myself doing much else but the business is doing really well. If I wanted to I could probably get another shop or two open somewhere.”

“Oooohhhhhh, expansion,” Anne said with what Jacob was pretty certain was feigned impress but it was not anything in her body language or smiling face that gave that way. It was more his doubt that anyone would be impressed by a fairly small-scale operation.

“Well, not too fast obviously but in a year or two then maybe it could start being an actual thi-”

“Ah! Ahhh! Ohhhhhh, yeah!”

Jacob quickly turned to look over his shoulder when a sudden sound from behind startled him. He could feel a little more relaxed when he saw that it was just a dark-haired woman in a black dress having her young male date’s cock pumping in and out of her as she lay on the table. Her black panties were hanging onto one ankle while they swung back and forth. Her man’s hands pushed up the hem of her dress exposing the lacy hem of her black stockings.

Jacob momentarily observed the couple as the woman tightly squeezed her arms around the male’s back and her legs around his waist as he pulled in and out of her before turning back to face Anne as she wore an amused smile.

“Good thing they moved all the plates out of the way.”

Jacob nodded with a muttered “yeah” he turned back to enjoy the view a little more but also to gauge the reactions of the surrounding patrons. Most were ignoring the spectacle of unleashed primal desires apart from some giving the occasional glance before having their attention returned to conversing with their dinner companions. Jacob could not help but feel a little self-conscious about being the only one who was giving the couple this much attention.

“Hello? Earth to Jacob?”

Jacob quickly turned back toward Anne with blushing cheeks. She looked at him with clear amusement at his nervous expression.

“You don’t go out much do you?”

“W-well, I haven’t really been on many dates.”

“Really? How many have you been on?”

“Uh…” Jacob tried to think of a response before taking another glance at the sexually ravenous couple over his shoulder.

“Agh! Ahh! I’m gonna cum” the man grunted.

“Do it on my face! Hurry!” the woman ecstatically cried. Her date pulls out and climbs on top of her on the table as he aims his hard, pulsing cock over her face. Spurts of thick white cum shot from the tip as the woman enthusiastically moans at the contact of it striking her face. Some of it getting into her mouth. Jacob looked away once the man’s ejaculation ceases and the woman’s moaning breaths were dying down in volume.

Anne was looking at him with a smirk. A smirk he could only think of as mischievous.

“So… you’re pitching right now?”

Jacob heard what she said clearly but did not respond due to not understanding her and being too nervous to ask what she meant.

“You know… in your pants?”

Jacob looked down and noticed the bulge at his crotch. For a couple of seconds, he observed it before looking back at Anne while shakily nodding.

“Well, better take care of it then. Show it to me.”

“Huh?” said Jacob. He scarcely believed what he was hearing.

“Your dick. Show it to me.”

Jacob looked around nervously. Even after the displays of unrestrained sex he’s seen he was still self-conscious about being the third incident.

“Come on, no one cares. Just do it.”

He took a deep breath before pulling down his zipper. He stayed seated despite knowing what he was asked to do but he just could not bring himself to stand up.

“Come on. Don’t be shy,” teased Anne. Jacob sighed before standing up and presenting his long, erect member to her. Anne’s eyes widened a little behind her glasses when she closely observes Jacob’s long, erect cock.

“Wow. It’s bigger than I thought.”

“Um… thanks but what’s that supposed to mean?” asked Jacob with a raised brow.

“Hey, it’s a compliment just take it,” said Anne.

“Ever had a girl jack you off before?” asked Anne. The question made Jacob blush out of shame.

“Um…”

“So, that’s a no. Ever jack yourself off?”

“Uh… yeah,” Responded Jacob.

“Well, we’ll start with that. Just do what you need to do and we can get on with the date,” she said.

Jacob took a glance at both sides and found no one bothering to look at him. With a sigh, he places his hand on his cock and begins to massage it slowly like he usually did whenever he was starting to relieve himself.

Anne silently watched with a patient smile as Jacob stayed mostly quiet throughout his public masturbation session apart from the occasional grunt. The pace of his strokes increased until he felt a familiar build-up in the base of his cock spreading to the organ itself.

“Ah… I’m gonna cum! Where should I-”

“On my face, duh,” Said Anne. Jacob was a little surprised at her suggestion but he went along with it and unloaded himself onto her bespectacled face. Several spurts of his thick, creamy essence strike her face and the lenses of her glasses. Unbeknownst to both of them, a couple of the spurts made their way into the prawn soup when Jacob had it aimed just a little bit closer to the left.

“Wow… you’ve been holding that in for a while haven’t you?”

“Uh… I guess you could say that,” Jacob awkwardly said before he pulls his pants back up, pulls up the zipper, and returns to his seat in front of Anne. The young college student licked away the cum around her lips before using a tissue to wipe the rest from her face and her glasses.

“To tell you the truth this isn’t the first time I’ve had guys jerking themselves over my face on a date but you gave me the biggest load so far.”

“So… that’s good?”

“Well, I can’t say I’m disappointed,” Said a smiling Anne as she picked up her spoon and put it into the soup. She took a spoonful of it and placed it into her mouth. A wince was clear on her face. She took the spoon out of her mouth and looked at the soup with a contorted expression.

“Tastes a little saltier and thicker than before.”

Jacob nervously glances at the soup before quickly putting his attention over Anne’s shoulder in an attempt to look away from it and to not look at Anne.

“W-well… that’s strange.”

“Yeah. No prizes on guessing where the extra ingredient came from.”

Jacob nervously darted his eyes back and forth while twiddling with his fingers in an impulsive tic under the table.

“Oh… well I can only apologize.”

“Don’t worry about it. Not like it’s gonna poison me,” said Anne as she consumed another spoonful of the soup with a shrug. Jacob sighed in relief when he heard her understated reaction and resumed eating his soup and breadsticks. For the next half hour, they ate and resumed discussing their career paths.

Jacob got a little more enthusiastic when they discussed the possibility of expanding his phone repair business which gave him a bit more confidence. He was glad to feel relaxed again after the uneasy masturbation and especially the accidental soup tampering.

They finished their meals and placed the bowls to the side. Anne shrugged when Jacob asked her about the soup.

“That was okay but it was a little too bitter for me,” said Anne.

“Well… yeah. Sorry about that,” said the still apologetic Jacob.

“I told you. Don’t worry about it. It’s not like I never tasted it before today.”

Jacob shrugged. He supposed that she was right. If she told him she had not consumed semen before he doubted he would have believed her. In a way that made him feel more comfortable with someone who was experienced than someone just as experienced as him. At least he did after seeing that she seemed satisfied enough so far so he could not have been all bad.

“I think I’ll have a drink. Maybe wine,” said Anne as she took the drink menu. Jacob waited for her to make a selection as he heard a slam behind him. As if a table was hit with something hard.

“Did you hear that?” he asked.

“Huh? Yeah looks like someone likes it rough,” she said as she peeked away from the menu. Curiously, Jacob turned back to see quite a primal scene that stood out against the civil restaurant even compared to the previous displays of sexuality.

The first thing he noticed was a woman’s legs raised in the air encased in sheer nude stockings with black high-heeled pumps on her feet. She wore an elegant black silk dress with a short skirt so her lace panties were exposed for the whole restaurant to see. Towering above her was a man who seemed at least ten years her junior dressed in a well-tailored dark suit. That man currently had his hands tightly enclosed around the woman’s throat.

She filled the restaurant with the sounds of her strained choking. Her pale white face steadily grew redder as her legs flailed around while smacking at the man with her hands. She even managed to get a few slaps on his face.

Jacob wondered if he should intervene until the man leaned down toward the woman and released his grip around her neck to pull down her panties with one hand while cupping her back with the other. Roughly and quickly, he enters her while they passionately kiss.

As the man roughly thrusts in and out of her as they keep their lips pressed together. Jacob was surprised to find that the sight was not all that arousing to him. He supposed that he had already expended all he had when he ejaculated all over Anne’s face which did not make him feel secure about his stamina.

He turned away from the couple to see Anne turning red.

“This is starting to get to me. Uh… do you mind?”

Jacob felt a slight tingle go through his body when he realized what it was she was planning to do. He knew he would not be having sex with her this early but he would never think he would get to witness her preparing to expose herself this early either. He could hardly believe his luck.

“Uh… no of course not,” he said while trying to act nonchalant about it.

“Cool. Thanks a lot,” she said before removing her jacket and shirt to expose her white bra. Jacob could already tell she had c-cup sized breasts and immediately he contemplated looking away from her or at least try to maintain eye contact to avoid offense. Though considering her attitude throughout the past couple of hours he was not so sure he had much reason to be concerned.

“Oh, feel free to get the drinks. I’m gonna be a little pre-occupied.”

“Uh, sure.~” replied Jacob before he picked up the drink menu and read it while trying to keep his attention on it. Over the obstructing printed paper in front of him, he could hear Anne’s soft sighs of pleasure. Jacob called over the waiter and requested a bottle of red wine while trying to ignore the masturbating red-haired woman opposite him.

The waiter was a different waiter than the one who took their meal orders and did not spare a glance to Anne at all. Jacob guessed he must have been working here for quite a while. He admired the steel will the waiter seemed to possess and instantly wished he had that level of self-control because soon after the waiter left he found himself looking at Anne’s large, round breasts being massaged as well as her pink hardened nipples being squeezed by her fingers.

“Mmm… can hardly wait for that wine.”

“Uh… yeah,” said Jacob while not being able to think of much else to say.

He watched her pleasure herself while feeling increasingly comfortable with doing so the more she did it. Anne soon moved her hand down her pants and began to stroke herself at the crotch. Though no one could see it, her panties were growing wet underneath the table to the point of leaving a small wet spot on her jeans.

“Mmmm… ahhh, yeah,” she moaned before shuddering. It was clear to Jacob she had reached her climax.

“Mmmm… that hit the spot.”

The waiter returned with the wine bottle and placed it on the table before politely bowing with a smile. He left as Anne put her bra back on.

“Mmm but not as much as this will.”

Jacob may have seen women have sex and pleasure themselves before but never this close and never while he was on a date with one. He smiled as he opened the bottle. He could get used to this.

Source: reddit.com/r/Erotica/comments/uvism6/date_with_anne

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