Pretense (closed for cnuveau)

Jacob wondered, if they hadn't walked in when they did, how long it would have been before they'd really walked in on something. As it was, he knew what Brittany wasn't wearing under her dress and didn't seem that far of a stretch to think that Will might take advantage of that fact and sink himself deep inside her. Jacob shook his head trying to cast the images that he was finding all too appealing out of his mind. Perhaps it was the residual heat from the kiss that allowed him to so easily let himself imagine such things.

If there was any doubt in his mind about whether Jenna was interested in something beyond just the ruse she'd concocted, the banter between Jenna and Brit had removed it. It wasn't so much what Jenna had said but what she didn't say. Each of Brit's comments were met with a telling silence that told Jacob everything he needed to know.

Though it was clear the attraction between them was mutual the wrinkle of her past challenges with men told him that he probably needed to approach things a little differently than he otherwise might. He wasn't content to just not fall into the traps that the others had. If he was going to pursue her he was going to do it in a way that fully explored the power dynamics that she seemed to be drawn to.

"That's probably a good idea. I'm free tomorrow night. I'll pick you up at 6:00." he replied taking the opportunity to be decisive about his suggestion.

When the waiter returned with his card Jacob signed the check then led Jenna out of the club into the warm morning sun.
 
Jenna nodded as Jacob told him the time and followed him out giving him her address. They walked hand in hand as they strolled and she found herself really enjoying his company. He wasn't a bore and while they had different points of view on some topics, he was mature enough not to get into an argument with her as she was with him.

In fact, she enjoyed it so much that it had taken an alarm to remind her that she had other tasks she set in the day not assuming that it was going to be a short meet and greet with Jacob.

"I'm so sorry. I have to get my dry cleaning before they close. I didn't even realize we've been talking for hours!" Jenna smiled apologetically. "Thank you so much for this. You have no idea how much I appreciate this...even agreeing to other fake dates..." Well, it didn't feel fake to her, at least not the time she spent just talking and strolling the club aimlessly.

"See you at six tomorrow!"

----

5:50

Jenna had 10 minutes and she wasn't as prepared as she looked at her choices of clothing. She could feel the decision fatigue setting in after a whole day of work. It was the reason why she told people to give her the important decisions she had to make in the morning if they can help it. By afternoon, she felt drained. Sure she can still call the shots but it was absolutely draining.

5:54

Fine! She took a red dress and put a jacket over it to dress it down a bit. And then the shoes.

For goodness sake! Another decision! Flats for comfort or heels for style? And what color goes with...forget it! She grabbed the nearest black heels, put on some lip gloss and fluffed her hair a bit just before the doorbell rang.

As she ran to the intercom of her flat, she instantly regretted the 4-inch Louboutins she randomly took. There was a reason she barely wore them.

"Hey! I'll be right down!" Sighing, she just went with it and rode the elevator down to meet Jacob.
 
Perhaps it was the complete lack of expectations Jacob had in meeting Jenna that allowed him to enjoy the time he spent with her so much. On any typical blind there always seemed to be pressure to quickly establish romantic feelings or come to the conclusion that there were none there but with Jenna, it was just two people getting to know one another. The only expectation was that he'd play the role she needed him to play and given how well they got along, that seemed like it would be no problem. When she finally excused herself at the club Jacob couldn't help but feel like neither of them required the guise of the arrangement to show interest in one another.

It wasn't typical for Jacob to leave the office with most of the rest of the staff at 5:00 but the next day he did so eagerly. After making his way home he changed out of his suit and into a more casual pair of slacks and a polo. He already lamented the impression Jenna had early on that he was someone who wore his wealth so something more casual seemed in order.

Just before 6:00 he arrived at the address Jenna had provided and rang up to her apartment. When her voice echoed through the intercom the anticipation he felt only seemed to intensify. Jacob took a step back from the callbox and leaned against the wall of the entryway while he waited for her to come down.

Through the entryway glass Jacob watched as the elevator doors slid open and Jenna strode quickly out of it. The red dress she wore instantly caught his eye as he took in the sight of her then noticed the tell tale red soles of her Louboutin heels caused him to raise a brow. "So not that frugal." he thought to himself as she stepped out to greet him.
"Stunning." Jacob said as he greeted her with a casual hug and kiss on the cheek. The feeling of her warm skin against his lips seemed to calm the subtle case of nerves he'd been having as he took her hand and they started down the block. "I thought we'd try Giovanni's down the block." he continued as they walked. He wasn't quite sure if it was a place she frequented when he scanned the area around her flat for options but had positive reviews and it seemed like the kind of mom and pop place that she noted she liked to frequent.
 
Jenna felt his warmth wrap around her and she couldn't help but breathe a sigh of relief when he heard his comment. Maybe the shoes weren't such a bad choice after all. Hands locked in his, she felt how large and strong his hands were. It was... comforting.

And...oh they were walking. Of course they were walking. Damned time to actually have these heels on. What did she want to do? Impress him? Okay, she probably did on a subconscious level.

"Sure. Giovanni's sounds great!" It was a great local haunt for her, and it wasn't so far that she did not constantly say 'ow, ow, ow' in her head because she was stupid enough to just grab the stilettos.

And just before her toes started to feel the pinch they were there and they were seated quickly.

"Buono sera, Natalie!" Giovanni's voice boomed from behind the counter. "Bringing a friend?" He wiggled his eyebrows at her.

"Please don't embarrass me!"

"Yeah yeah. I have other clients too. Gotcha." He winked and went on to say something in Italian to the back of the room.

"So, how did you know about this place?" Natalie asked after thanking the staff who got them their seats.
 
When they entered it was clear that Jenna had not only been there before but also seemed to be quite the regular. It seemed like a stroke of luck that Jacob had settled on a place she seemed to know so well. He listened to Jenna and the owner exchange pleasantries before he turned back toward the kitchen and said "Quindi immagino che non sia lesbica."

Jacob wasn't by any stretch fluent in Italian but he knew enough to be able to piece together what it was the owner had said about her. Initially he found the comment to be offensive but it was also telling. It was clear that, as many times as she seemed to have been there, it was seldom with men. Whether that meant she would go there alone or with girlfriends, it wasn't clear. The pattern was certainly enough to cause the Italian man, who likely leaned toward being a misogynist, to form some opinion about her sexuality.

"I just scanned around what was nearby your flat and the reviews looked good so it seemed like a good choice. Had no idea you were such a regular." he said, putting the comment from the man aside.

When the waiter arrived he hovered over Jenna's shoulder as he took their drink orders and told them about the day's specials. As the waiter spoke Jacob's eyes moved from the menu up to the waiters to find his gaze fixed down the front of Jenna's dress which seemed to have fallen away from her chest as she sat. He watched as the man held his gaze there then finally looked away when Jacob asked for a glass of wine. "Very good." he said before turning his attention back to Jenna to take her drink order.

When the waiter left a broad grin stretched across Jacob's face as he leaned across the table toward Jenna. "Seemed like the waiter was quite captivated by what he saw down the front of your dress." he told her, curious to see the type of reaction the realization might elicit.
 
Giovanni's was a place she frequented because she often got what felt like preferential treatment none the wiser about what the men thought about her whenever she came by. Nothing about their extra attentiveness was a red flag to her, absolutely oblivious to what the men in the restaurant thought about her.

"Oh, yeah. It's on the way to and from work. I usually have their meatball sandwich in the morning on the way to work and have dinner here on the way back when I'm too pressed for time to cook at home. Or just plain lazy." She smiled and took the menu from the waiter. Leaning on the table provided the waiter a view he couldn't resist looking at.

"Oh, just orange juice for me, thanks." She smiled up at the waiter and handed the menu, still utterly oblivious.

"Seemed like the waiter was quite captivated by what he saw down the front of your dress."

Jenna blinked in surprise. She looked down at her chest as she felt her face flush from embarrassment. "Ah...I'm sorry. I wasn't aware..." She moved to close the buttons of her jacket but realized the buttons on this one were non functional. Damn her choices for the evening! "I swear I don't dress like this all the time..."
 
Jacob let out a small laugh seeing just how flustered that Jenna became when she realized what it was he was saying. "No need to apologize at all. I'm actually a little envious of the guy if I'm being honest." he replied before folding his arms on the table and leaning in a little further as he lowered his voice to a whisper. "Ok, so be honest with me, how does that make you feel that he couldn't help but look? Knowing that he's probably thinking about what he saw right now?"

Jacob knew that instinctively Jenna would likely go to her grave saying that she didn't like it at all. Deep down though he knew there had to be at least some small part of her that had to be a little flattered. It was that part of her that he hoped to coax a little to the surface than see just how open she was to embracing and owning it.

It was all a very calculated risk. There was the obvious risk that she'd find his whole line of questioning objectionable and think he was a creep but he didn't sense she'd go that route. She'd endured Will and Brit and they had said far worse. He also knew that she was kind of relying on him for the upcoming trip and that alone might provide him a little latitude to explore with her.
 
Jenna flushed a deeper shade of red and couldn't help but give a little shiver of excitement when Jacob admitted to being envious. He continued leaning in close, his voice low and sultry that Jenna bit her lower lip in response, her skin tingling with every word.

"That's..." She didn't know what to say to someone thinking about her breasts. It was definitely flattering but, that was improper, wasn't it? "Um...the wrong kind of attention."

And then a thought came to her. Did Jacob think of such things as well? Part of her wanted to know, but she couldnt get the words out. As her brain warred what to do, her body leaned over to him a bit more, the subtle shift giving him a show as well, as she acted instinctively.

"Do...guys really think that way?" She whispered back. "I mean, what about you? You said you were envious..."
 
The hue of her cheeks and the subtle bite of her lip told Jacob everything he needed to know. How much the idea excited her he wasn't sure but he knew that it was at least a little. "Is it though?" Jacob asked as he gave her a questioning look. "Admit it. You love the idea that you can turn a man's brain to mush so easily. I have to imagine you might even find it a little empowering." A devious grin stretched across his lips just as she leaned in toward him, offering him his own glimpse at the pale globes hidden beneath her jacket.

Jacob's eyes came to rest on the sight for just a moment as he slowly drew his tongue across his lips then lifted his gaze to hers. "You've met Will right?" he replied with a laugh. Before Brit, Will was notorious for ogling women and didn't shy away from letting it be known that he was.

Glancing over toward the bar Jacob noted the waiter putting in the order for their drinks then looked back at Jenna. He knew that if he was going to get her to open up it had to be a two way street. After considering his next words for a brief moment he continued. "I'll admit when I'm at the gym in sweats I've caught the occasional glance below my waist from women and I didn't hate it. It's fun to be a little bit of a tease sometimes." Jacob took a sip of his water letting his admission bounce around in Jenna's mind for a moment. "The question is, now that you know you have his full attention, what are you going to do with it? Are you going to pull that jacket tight around you or are you going to have a little fun with him? I think you should have some fun with him."

With his challenge laid out Jacob leaned back in his chair with a wry grin then folded his arms across his chest as the waiter began to make his way back to the table. "Moment of truth." he whispered.
 
Did she? Did she like how she could distract men with her body? She caught him glancing down, his tongue gliding across his lips as if he wanted a taste, and her breath hitched. Did she want Jacob's brain turned to mush around her? But more importantly, did she really have that power?

"You've met Will right?"

Jenna couldn't help but laugh. Will, it seemed had always been the exception. He wasn't covert when he saw something he liked. More than once he had commented on her legs, but she just chalked it up to Will being Will. But did guys actually have the same thoughts and not say anything aloud?

Hearing how others stared at him below the waist was an unassuming plant in her head. Now she couldn't stop thinking about looking that way too--when the table was out of the way of course.

And how does one actually be a tease? She squirmed in her seat and looked at Jacob and something fluttered in her stomach as she saw the way he looked at her--expecting to take his suggestion and have fun flaunting her assets. As if it wasn't a suggestion.

"Moment of truth."

She looked back at the waiter hearing his steps behind her and she felt herself straighten in her seat. She drew her hair to the side exposing her neck and leaned over to him so he had an lmost direct view down her neckline. What am I doing? This is outrageous! It's not going to work!

"Thanks Nico," she said despite the protest inside her brain. She took the glass he was offering her, but his eyes were focused below her neck and as soon as her hand brushed his, he jumped and the plastic glass slipped from both their fingers and going all over the floor.

"Are you okay?" She bent down more focused on the spill as Nico bent over take the plastic glass...until he looked up at her his mouth hanging open for a few moments before he cleared his throat and mumbled excuses and apologies to get the mop and scuttling away. Only when she straightened back in her seat did she realize that she had given him an even better show bending over when she didn't even try having fun with him.

She buried her face in her hands, her embarrassment showing. "What have I done...?" She opened a hole through her middle and forefinger peeking at Jacob's expression. "Was that bad?"
 
Nico had been working at Giovanni's to pay his tuition since he'd arrived his freshmen year. The small restaurant was a fun and fast pace environment that suited him and was helping him develop the social skills that he'd always found himself lacking. Though he tried to emulate the machismo of Giovanni and the kitchen staff that worked alongside him he was still very much the awkward kid that walked in the door to apply for a job all that time ago.

Over the years he'd seen Jenna there a lot and had developed what might be considered an unhealthy infatuation with her. To him, she was the picture of perfection. Always well put together and in control, she was the type of woman he could see himself settling down with after graduation. He'd spent many nights in his dorm while his roommate was out imagining what it would like to be with her. He'd memorized every curve of her body and those images fueled those moments in the dark that often left him breathless and soaked with his own seed.

As he approached the table he took a sharp breath as he watched her seductively tucked her hair to one side of her neck, exposing her supple skin. It was as if she was calling his lips to it. The subtle lean in his direction offered him a perfect view of the treasure that lay beneath the delicate fabric of her dress and it took his breath away. It was as if she was doing it just for him. That she wanted him to see. The brush of her fingers sent a jolt of electricity through him and sent the glass tumbling to the ground.

"Oh my god, I'm so sorry." he stammered out as he quickly bent over to pick up the glass and sop up the juice that was now soaking the floor. Looking up again Nico was greeted with a full view of her breasts as she leaned over to help. His eyes widened as they fixed on her firm nipples now visible as the support of her bra fell away. Even through his panic and embarrassment he could feel his desire for her begin to manifest. "I'm sorry, I'll get you another." he continued when he finally broke his gaze from her then hurried off.

Jacob watched all of this play out with an amused fascination. When he challenged her he didn't quite know what to expect but what she did exceeded all his expectations. The fact the boy actually did melt down was amusing enough but when Jenna leaned down, offering him a full view it almost looked like the boy was going to explode. It was all Jacob could do to suppress the laugh that so desperately wanted to escape as the boy scurried away.

When Jenna parted her fingers to peak through her hands Jacob met her gaze with a broad grin. "See what I mean? Mush." he said before leaning back across the table toward her again. "You just made that boys night." He considered for a moment continuing and calling out exactly what he expected the young man would be doing with the images that were now firmly planted in his head but decided to leave it unsaid. "Now you have to admit, you like that you had that effect on him don't you?"
 
Jenna groaned. "Oh come on...you're just enjoying our discomfort," she pouted. "I mean, yeah, you're right. That kid looked like his brain flew out the window, but he's a kid. But look at you all smug and grinning and finding enjoyment in this. It's so...schadenfreude of you."

Of course, her annoyance wasn't at all just because he looked to be enjoying their mutual embarrassment. But it was also because he seemed like he was immune to her. But then again, unlike either of them, Jacob definitely had more experience. Which meant that he was probably bored with the likes of her and preferred more exciting women.

Before she could say anymore, Lana, Giovanni's daughter, came out with another glass, sidestepping the spill and standing near Jacob. "The usual? Chicken Parm?" She asked Jenna with that patented server's smile.

"Yeah, but not too much sauce today." Jenna said.

As soon as the words left her mouth, Lana turned to Jacob and her whole demeanor changed. She was more...Jenna can't put a word to it. Softer? Sultrier? With Lana half turned away from her she couldn't be sure.

"And what can I get you?"

There! Yes, sultry. She voice dropped lower and there was a huskier quality to it. Maybe that was the kind of girl that got Jacob's blood boiling. Someone more...flirty.

Why was she so annoyed?

Someone else, probably a new guy, came to mop up the spill, but Nico didn't come back. Oh no...what if he got it from Giovanni? Oh, that was definitely her fault. Poor kid...
 
Jacob shook his head. "It's only schadenfreude because you're choosing to be uncomfortable with it instead of allowing yourself to enjoy the power you have over men." he replied. He could understand Jenna's discomfort with what had happened but it did seem, to him, that it was her choice in how she viewed it. Under any other circumstances he'd have never considered pushing her to it but so much of what they'd talked about so far centered on power dynamics that he thought it would be interesting.

Jacob's attention was drawn from Jenna to the new server that had come to take their order. He imagined that poor Nico probably begged someone else to take the table to save him continued embarrassment. A part of him actually felt sorry for the kid but he kind of brought it on himself with his roaming eyes so he didn't allow himself to feel too bad.

When the new server turned her attention from Jenna to Jacob the shift in her tone was unmistakable. Had this been any other normal date, Jacob would have brushed it aside and pretended not to notice but, given what had just happened, he decided to lean into it to further demonstrate his point.

Jacob looked up from his menu at the woman "I don't know, it all looks so tempting." he said, letting his eyes bounce subtly down from hers for just a split second as his voice picked up the seductive undertones that she'd initiated.

Lana's cheeks instantly reddened at the thinly vailed compliment.

Though Jacob was tempted to carry things further but he knew he was probably already approaching the bounds of what Jenna might find amusing. There was also the risk with something this overt that Lana would carry things further herself making the whole seen that much more awkward. Jacob looked down at his menu again, considering his options then looked up again. "I think I'll follow my girlfriend's lead. Chicken Parm." he said glancing over at Jenna as he handed the menu to Lana.

"Oh! Um, ok." she said, jotting his order down on the pad before turning and retreating back toward the kitchen.

"Hope you don't mind. Thought I should get used to throwing that in every now and then." he said to Jenna when Lana was out of earshot.
 
Jenna shook her head at the whole scene but when he called her his girlfriend, her chest tightened. She realized she didn't even have the courage to call him her boyfriend when Giovanni asked.

"Hope you don't mind. Thought I should get used to throwing that in every now and then."

Jenna sighed. "I don't even know how easy that is for you...or her. I know you were only demonstrating but...I guess Will had a point when he said I was frigid." She sat back and crossed her arms under her chest highlighting her cleavage for him as she took a more defensive stance.

"Is that a turn off for you?" She cocked her head to the side and noticed him glancing at her chest. Part of her wanted to uncross her arms and save her the embarrassment, and the other half just wanted the attention.

In the back of her head she knew he was right. She liked to be looked at, but not just by anyone and everyone. And, honestly, she liked looking at him too.bthe playfulness of his grin gave him a boyish feel while the set of his jaw and the ease of his stance made him all man.
 
“I think frigid is a bit reductive.” Jacob protested. “I don’t get the sense that you’re frigid at all. Maybe you aren’t necessarily who you want to be but someone frigid is perfectly content with the way they are. I think the person you want to be is inside you, you just need to learn how to let it out.” He realized that he was running the risk of sounding too philosophical and presumptuous but it was a genuine observation.

“A turn on?” Jacob considered the question for a moment as he took a sip of his wine and noted the way her folded arms pressed her cleavage up exquisitely. “Yeah, I guess you could say it is. For me, sexy is a state of mind. It’s about owning and embracing who you are and being unapologetic about what you want. I’m sure you’ve seen people that nobody would consider pretty under conventional terms but are still sexy.” Jacob pointed to his head, tapping the side of it with his finger as he grinned “It’s the state of mind.”

He of course realized that the message that Jenna was likely hearing is that he didn’t find her sexy. Though it might be true, sexy wasn’t necessarily the only thing that he found to be a turn on. He knew explaining it would leave him walking a fine line but he decided to try anyway. “The thing is though, sexy isn’t the only thing that’s a turn on. Intelligence, sincerity, beauty, sexy, they’re all turn ons. Different pathways to the same place and all just as vulnerable to fatal flaws that can completely negate them. Can be as sexy and pretty as you want but if you’re ugly inside it doesn’t matter.”

Jacob’s eyes again moved to Jenna’s breasts being pressed up by her arms then nodded towards them. “That makes you feel sexy doesn’t it?”
 
Jenna blushed as he noticed how her breasts were pressed up. "I..." She stalled as their food arrived, Lana giving a wink at Jacob before she got got back to her duties.

Jenna ate a little mechanically as she considered what she really wanted, how she really felt and whether she should be saying any of it to Jacob. The truth was, she did want to feel wanted, but it always felt so...difficult.

The silence was deafening, and a quarter of the way through her food she finally decided to just go and say it. "I'm glad that you let me think through it, because honestly, it's all a jumble in my head."

She ate another piece and she knew she was just stalling. She drank a bit of her juice before finally gathering up her courage. "You're kind of right. I...want to be wanted. But I don't want to be looked at like a slut. Or an easy woman. That's not the kind of man I want to attract. I mean, you know what they say about attracting the wrong attention? I want to be careful about that but I also want to drive the right kind of attention wild."

Looking down at her food, she poked at the chicken with her fork. "I mean I know you said confidence and intelkigence are sexy, but in my case, it makes men run for the hills or, in the case of others, ask me to be their dominatrix." She rolled her eyes. "And when I say no, they leave. Like I let them down."
 
Jacob knew that he'd thrown a lot at Jenna so when she fell silent for a while, he let the quiet persist between them for a while as they started on her dinner. He also understood how difficult it was for professional women like Jeanna to be able to strike the delicate balance that he spoke of. For those resigned to a life of domesticity it was slightly easier. For professional women, though, they were expected to be: competent but not threatening, intelligent but not overbearing, sexy but not slutty then at the same time be seen as someone that could also be domestic and maternal. It was an absurdly delicate balancing act when some of those things didn't just come naturally. He'd seen, however, how the right partner could allow a woman to be everything she wanted to be.

"Completely understand. Like any other power, it's definitely something that you want to be selective about how you use." he agreed. It felt a little odd for him to frame it as a power but, in his mind, that's exactly what it was.

Though she didn't say it directly it almost seemed as if Jenna was asking him for help in how to navigate striking the balance that she was seeking. It was a curious notion given his own developing interest in her. It almost felt like if he did, he'd be training his own potential girlfriend. "Maybe while I'm pretending to be your boyfriend I can help you out with that." Jacob continued, not really sure what she'd think about the idea.
 
"Maybe while I'm pretending to be your boyfriend I can help you out with that."

Jenna paused and continued to eat. Considering. Would it be a good idea? Every fiber of her thought so. It was just the reliable, professional, good sister example persona she had built over the years that was holding her back.

Some sauce dripped on her lower lip and she licked it off slowly. She glanced up at him watching her and she shivered as his eyes looked at her lips and grinned at her. Maybe he was the right kind of attention she wanted.

"Teach me..." As soon as the words were out of her lips, the persona balked. How could she ask such a thing? But the woman inside her screamed rebellion. She wanted to be with a man who knew what he was doing. Who could show her what could be and what she yearned for. "Please?"

Jenna didn't know if they could be anything more than pretend lovers, but she did find him attractive and something else she didn't know, but she felt safe. She felt as if she could trust him. He hadn't judged her thus far and neither did he run for the hills. Not for the first time, she wondered what made Will choose Jacob out of all his friends, but maybe that drunken night of her spilling her heart and guts out was a big factor.
 
Jacob watched as she continued to eat and consider his offer. The fact that she didn't scoff at the notion instantly told him there was at least some interest there. In the moment, her tongue snaking out to collect the sauce from her lower lip seemed to take on far more seductive undertones as he considered more thoroughly the possibilities of the offer that he'd made.

On the surface, it seemed innocent enough. A friend offering an outsiders perspective on the things Jenna felt were holding her back. Jacob knew that most of the challenge would be quieting the voices that have guided her so far and replace them with his own. He wondered if she trusted him enough to let that happen and just how willing she'd be to give up the control she kept over herself.

"Please?"

A broad smile stretched across his lips when her internal struggle resolved into acceptance. "I'd be happy to." he said offering her another reassuring smile.

Their conversation was interrupted when Nico returned to the table and asked if there was anything else they needed. "No, I think we're good right now. Early morning tomorrow so just the check." Jacob replied.
 
Jenna smiled apologetically at Nico who blushed and scuttled off. Inwardly she knew she had to make it up to the kid somehow.

As they left the restaurant, Jenna wondered if she had made a mistake asking him to help her explore her sensuality. There was no denying that she wanted to have sex just like any other person, but after her odd conversation with Jacob, she was left wondering if she was unconsciously rebuffing men who couldn't take the lead because she was scared to lose the persona she built over the years.

She wasn't sure. But as she walked and talked a bit more with him, pinched toes and all, the night truly was coming to a close and she felt her feet giving up in her ridiculous shoes.

"Mind if I hang onto you for a bit?" Jenna asked not waiting for an answer as she clung onto his arm, her softness pressing against him. Her feet were beginning to hurt a lot more. "I swear I am never wearing these again. I bought them to celebrate my promotion and wore them on the company award night. Instant regret. Now I remember why."

She sighed as they neared her place and in that moment, it didn't feel like they were pretend dating. It felt like they really were dating, getting to know one another, hoping it would lead to something more. But it wasn't possible, was it? She was just another normal corporate slave while he sat high in the sky, flying private jets and having the fate of thousands of employees like her at the palm of his hand.

Cinderella fantasies don't happen to her. So as they paused in front of the building, she wanted to build a memory of that fantasy.

Even with the heels, the height difference lingered. Wrapping her arms around his shoulders, she pulled him down for a tender kiss, pressing herself up against him. She took the moment in taking in his masculine scent and the way his muscles felt under her touch. Ending it with a playful little nibble on his lower lip, she stepped back with a smile on her face. "Thank you for tonight. Good night."

She went back to her apartment kicking off the damn heels and plopping herself on the couch. She touched her lips at the memory of their kiss, grinning like an idiot. What would it be like to really have a boyfriend like him?

Just then Will's voice interrupted her thoughts. Maybe you'll finally be rid of the V-word.

Jenna bit her lip and shuddered. It did look like they were headed that way...
 
Jacob gladly accepted the weight of Jenna's body leaning against his as they walked. Had it not been for their meeting being orchestrated as a ruse there would be no doubt that what was happening between them was the result of genuine attraction. The lingering pretense seemed to cast a shadow of doubt over it all though. To Jacob, it seemed easy enough to dispel the doubt but at the moment it seemed to add a layer he couldn't quite describe.

When they reached her door he was unsure how to proceed. They'd shared a kiss the day before but again, it was under the pretense of their arrangement. He wasn't left unsure for long though when Jenna surprised him, wrapping her arms around her shoulder then pulling him down for a kiss.

Jacob's hands slipped from Jenna's hips around to her back as the sensation of her soft body pressed against his sent a chill through him. He allowed himself to get lost in the moment until show slowly pulled away then dragged her teeth over his lower lip. "Thank you!" he whispered as she pulled away and he watched her walk into her building.

When Jacob arrived at his apartment he poured another glass of wine then spent some time going through the emails that had accumulated over the evening. As he did his mind continued to be drawn back to their conversation over dinner. Leaning back in his chair he closed his laptop then pulled out his phone and started typing a message. "Had a great time tonight. I'm sure you're going to bed soon. When you get there, you should send me a pic."

Jacob grinned as he hit send. He expected that Jenna was the type of person that had likely sworn she'd never do something like that and his request might cause her some anxiety. That was the point to it though. He'd left it open ended enough that she could choose any number of ways to find her way to yes. Which she'd choose was the question he was eager to learn the answer to.
 
A quick shower later, Jenna was brushing her teeth when hthe podcast on her phone quieted. her mouth clean, she wiped her lips on the towel as she grabbed her phone seeing the window message from Jacob. She clicked on it and looked at herself in the mirror in her oversized shirt and boyshorts, then back at the message.

There was always the option of going under the covers and sending a photo. She looked back at the mirror and wondered what he would like. Maybe a shot in a pretty chemise? She didn't have those. At home, she dressed how she thought was the most comfortable for her. Not that she knew how comfortable nightwear lingerie was but huge cotton shirts were always her go-to.

She did have a pair of PJs when she was on hotel business trips. It was very handy for when she needed room service. But she didn't want to bother putting them on and getting back into her shirt.

As she contemplated, she walked to her bed typing to stall for time. "I had a great time too. Sorry about the kiss...I got carried away..."

Sending, she sighed and scooted over the middle of the bed still wondering what kind of photo she should send. In the end, she realized it didn't matter what her decisions were at this point. She has had one disastrous decision after another, from the dress, to the shoes, to flashing Nico, and kissing Jacob. Her brain was well and truly turned off.

Screw it! Sitting on the bed, her legs folded under her and to the side, she leaned on her left hand and took a selfie. She laughed at the headless selfie and pressed send. What was one more bad decision in a series of bad decisions?
 
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Jacob waited for a few minutes then noticed the indicator that she was typing a reply. A second later her message popped up.

"I had a great time too. Sorry about the kiss...I got carried away..."

Jacob grinned then started to type out a reply.

"I'm not sure there's anything for you to be sorry about. We do need the practice so it seems natural right?"

Just as he hit send Jenna's picture popped up on his screen. Jacob took a moment to take in the picture that she sent noticing the strands of wet hair that draped down over her loose fitting tee shirt. It was certainly far more conservative than it could have been but he liked the fact that she found her way to sending something instead of dismissing the idea out of hand.

"That's my good girl! Very nice! I see I just missed your shower. Next time you shouldn't make me ask." he replied before getting up to head to bed himself.
 
Jenna didn't know why but being called his good girl made her feel good. Her belly tingled imagining how his voice sounded as he said it. It didn't escape her that he said 'my good girl.' As if he claimed her. She felt slight tremors all over her body and felt her face flush.

She licked her lips tying, erasing and retyping over and over before she finally settled on a response. "Okay, I'll send you a photo of me every night until we meet. And what if I miss a night? Are you getting ready for bed too?"

In the confines of her room with no one to hear, she said aloud. "I'll be your good girl, but sometimes, even good girls want to be naughty." Slowly her fingers found her way down her panties as she lay on her bed the sensuality of the entire evening getting to her.

That was another good thing about oversized shirts. She could touch herself easily. As she glided her fingers over her panties, she wondered if she should get better nightwear for the trip as well.
 
Jacob had just slid beneath the sheets when his phone buzzed again with a reply. He hadn’t expected her to offer up a nightly pic but he wasn’t about to tell her not to.

“I’m sure you wouldn’t disappoint me like that. It’d probably take a lot for you to make it up to me. Yup, just getting in bed.“ he replied then paused for a second before hitting send.

Jacob was never one to ask something of someone he wasn’t willing to do himself so before sending he pulled his sheets down exposing his boxer briefs the showed the distinct outline of his bulge then snapped a picture to attach then clicked send.
 
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