Experience is the Best Teacher (CLOSED for Sidney_1)

“Okay, Jason,” Jessica said slowly, testing out the sound of it. She still couldn’t believe that Dr. Matthews found her physically attractive. There were tons of beautiful women at her alma mater, and many of them dressed in a much more striking or revealing way than she did. Why her? She wasn’t ugly, but it wasn’t as if she was anything special…

“I’d love to go on a ‘date’ with you,” Jessica replied, mimicking the air quotes. “What time would you like me to be ready?”

She could barely believe that a suppressed fantasy was coming true. Spending more time with a professor, and well, the opportunity for much more with an experienced man. Was it the idea that he might be her first? Or, had her openness revealed how utterly horny she was. . .and maybe that was a turn-on?

Stop it, Jess, she said to her inner critic. Just enjoy the moment.

Jason spent only a little time deciding where to take Jessica on their date. He, himself, hadn't been to a really nice restaurant in over two years; he didn't have anyone to go with and it made no sense to go to such a place alone. He had heard his co-workers, and even some of this students, talk about fancy places where they had been. He picked Ostra, the white-tablecloth, Mediterranean seafood restaurant right on Charles St. in the heart of Boston. He texted Jessica with his choice in advance so that she would have some idea of where they were going and what to wear.

Most of the day Saturday Jason thought of little but their date. He had chosen the restaurant and made reservations for 7:00 p.m. Clothes were a no-brainer for him, given his very limited summer wardrobe beyond khaki shorts, light-color jeans, and polo shirts. The only thing that he owned classy enough for going to the Ostra was his all-season sports coat, light-weight, cotton dress shirt, and cotton pants. Too hot to wear a tie, he dressed with an open collar.

Driving in his car to pick up Jessica, Jason again thought over the one big remaining question: What to do after the dinner was over. Given the context inviting Jessica back to his house on some pretext would probably seem like an overture for sex, even if he didn't intend it to be that way. First-date sex didn't seem to be the way to go in this instance for either of them. Dropping her off at the curb in front of her apartment, however, seemed rather cold and abrupt. Finally, he decided that he couldn't figure it out in advance. He decided to just see how the evening played out and play it by ear. Always careful, though, he had grabbed a packet of condoms before leaving his house.

Parking the car and striding up to the entrance to Jessica's apartment building and ringing the bell for her apartment, Jason felt the jitters. Shit! He felt a little like a teenager. He tried to calm himself as he waited for her to appear by imagining what she might look like on their date.

“You’re going out, again? First formal date in a fancy restaurant? Whoa . . . I can’t believe you said yes,” Kate said, laughing at her roommate.

“Yes, but now I’m worried that I won’t . . .be ‘fancy’ enough. You know I rarely go out!”

Jessica had been rummaging in her closet, mixing and matching, before she finally relented and allowed Kate to “dress her up”.

They had found a light purple fitted dress with spaghetti straps and circular cut-out at her décolletage. Kate had insisted this was IT. Jessica had butterflies, she did look so grown up. . .sexy, even. . .but, still tasteful.

Kate had helped her with her hair, she had put a few waves into it and then made a loose bun at her nape. Between the make up, and the shimmery jewelry, she felt transformed into someone that she’s see out of a fashion feed. Surprisingly, it felt good to ‘dress up’.

“Jess, you look great. I don’t know why you don’t . . . you’re really very striking when you want to be. Ok, best of luck tonight, he’s the lucky one, just be yourself, and try to actually have fun! And I want to hear about it, tomorrow!” Kate said, knowing that Jess would not want her present when her date arrived.

-

Jess was busying herself with cable news when the doorbell sounded. She couldn’t believe she and Dr. Matthews were going OUT. It was going to be strange, but it’s like her latent fantasy was coming true. She would have him all to herself for the evening!

Jess tucked her purse under her arm, turned the lock, took a deep breath, and smiled as she opened the door.

“Well, hello again, Jason,” she said, nervously, but with eagerness. "It might take me a few times to get used to calling you by your first name," Jessica said, winking.

Jason greeted Jessica warmly, trying to hide the excitement and the little bit of nervousness that he felt. Seeing no sign that her roommate was in a line of sight, he leaned in and gave Jessica a small, tender kiss on her lips. Laying his hand lightly on the small of her back, he escorted her to his car.

Dinner at the Ostra was as lovely as the restaurant's ads promised. The couple ate slowly, engaging in animated conversation over dinner. As a professor Jason had worked hard to master the "keep your eyes on her face" posture so as to not make his women students uncomfortable or to invite the criticism that he was a lecher. But Jessica was no longer a student. He allowed himself the luxury of running his eyes over her gorgeous body on several occasions. He wasn't sure if she caught him looking, but he really didn't care. After all, they had essentially both admitted that they were physically attracted to each other. So, why hide the interest?

Even by the time that their desserts had arrived Jason had not made up his mind about how to end the evening. He had decided to play it by ear, but the answer had not yet arrived. Then, it struck him. They were only a block from the Boston Commons park. They could take an after-dinner stroll through, or around, the Commons. This would allow for holding hands as they walked, or just walking closely to each other, or, perhaps, for a kiss in the shadows. Yes! That was it! They both would certainly understand that they were not going to have sex in a public park. So, even a fairly passionate kiss would be suggestive of what was to come in their dating relationship without causing Jessica to feel that he was pushing for first-date sex.

Smiling broadly as he signed the check and readied to leave, Jason said, "So, Jessica, this has been wonderful. It's a beautiful summer evening. How would you like to cap off our date with a walk around, or through, the Commons?"

Through the dinner, Jessica could sense that Dr. Matthews was treating her differently, more casually. They laughed easily about some of their more obscure childhood interests and curiosities. Unsurprisingly, they were both big readers, and came from parents that had some colorful story-tellers.

Jessica could sense other patrons glancing at them, although she wasn’t sure why. They both looked like they were in their twenties, so it couldn’t be an age difference. Did they sense that this was a first date? She could also sense . . . Jason looking at her as she drank her wine, and not just her face, but the whole of her. It was a nice feeling, and it made her feel glad that she had put effort into her appearance.

She really enjoyed being around him, too. . . but, she knew she’d lose her composure if she allowed herself to look too long at him. She was still replaying the soft kiss and tender touch when she greeted him at her apartment. He had smelled so clean and fresh, too!

“A walk and some air would be great. This was a great dinner and a real treat. I hardly ever dessert, either! Thank you, Jason,” Jessica said, smiling.

“I’m just going to use the restroom and I’ll meet you up front, okay?”

Although dinner was lovely and he was ecstatic that Jessica had accepted his invitation for a walk in the park, Jason couldn't help but laugh. Why did all women have to use the restroom at least once on a dinner date? If this had been a double date the two women would have gone together. Guys never did that. Go figure!

Jason left his car in the Ostra parking area; the Commons was just across the street. By the time they got to the corner of Charles and Boylston, diagonally across the street from one of the park's entrances, the "Do Not Walk" sign was lit, prohibiting their crossing. Jason took the opportunity to take Jessica's hand as they proceeded.

The soon-to-be lovers walked slowly through the park, speaking only occasionally, simply enjoying each other's presence. Walking past the Old Burial Grounds Cemetery they arrived a the Parkman Bandstand, which was lightly lit by the evening sun. No one was in viewing distance. Jason turned to face Jessica while still holding her hand as he spoke, "I've had a delightful evening with you, Jessica. I hope that you will agree to see me again real soon. Now, I'm going to kiss you. Oh, not like the perfunctory kiss that I gave you at your door when I wasn't sure that your roommate was there. No, this will be a nice, first-date kiss. And, depending on how you decide to respond, I will kiss you again."

Jason cupped his hand behind Jessica's neck and pulled them in to a closed mouth kiss, not overly urgent, but firm enough to make clear that he wanted them to be lovers. Given the way that his body was already reacting and even though he knew that they were not going to have sex in the park, Jason knew for certain that if Jessica gave him even a little encouragement, he was sure to kiss her passionately, leaving no room for any misunderstandings as to his ultimate desire.

Jessica was still smiling at Jason’s formality, as if she should be warned about a kiss, when his warm lips pressed gently against hers.

She shut her eyes, and let her head rest against Jason’s palm, as she focused on enjoying the sensation of his lips on hers. His lips were warm and welcoming, and Jessica kissed him in return, lightly, against his soft, upper lip.

She liked the feeling of being close to him, in an embrace, ignoring the world around them.

Jessica turned her face a bit to the side, and wrapped her arms around Jason’s waist.

“That was really nice. . .” she whispered.

That was really nice. . .

Jason couldn't have agreed more. Her return kiss and having her arms wrapped around his waist was, definitely, "nice". Their immediate interactions warmed both his body and his soul.

Although Jessica had returned his kiss with only a light one of hers, Jason self-servingly saw that as a message from her that a second kiss would be welcome. That and the fact that their bodies were now pressed lightly together with her arms around his waist stoked his arousal to the point that he couldn't resist offering a more passionate kiss.

Keeping her neck cupped in his hand Jason folded his other arm around her waist, pulling them even tighter. "Second kiss time," he whispered, as he pressed his mouth to hers, this time in an open-mouthed kiss. Slowly, but firmly, he slid his tongue into Jessica's mouth, searching for hers in return, to start the universal lovers' dance that foreshadows the movements that will some day be shared.

Jessica let her body melt into Jason’s as he pulled her into a closer embrace. She loved the way he held her face as he kissed her, and she eagerly accepted Jason’s second kiss, closing her eyes, as they kissed more intimately. First, just teasingly at the tips of their tongues, and then their tongues swirled around each other, and Jessica couldn’t help but press herself against Jason even tighter. It felt so good.

Jessica withdrew by kissing Jason on the lips, their mouths parted. She had forgotten how fun it was to kiss a new person, and it felt even more magical that they were kissing in a public place, yet in their own world.

“Not bad for a second kiss,” Jessica said, with a warm smile, as she looked up at Jason.

Not bad for a second kiss.

Jason kissed Jessica lightly on the forehead in response to her comment. "I agree," he said returning her warm smile, "I think that it might be a little dangerous to do any more serious kissing on our first date, if you know what I mean. But, I'm looking forward to another date, if you'll have one with me. And, we could see then what a third serious kiss might be like ...and, where it might lead. What do you say?

Jessica pulled away and dropped her arms to her side.

“Sure, of course. I don’t want to rush anything, and I’m not looking to just . . . you know. I’m going to need to feel very comfortable with you. . . Jason. Anyway, this isn’t the place to talk about it, not that we need to talk about it.”

Jessica could feel herself blushing as she realized how insecure she felt as a woman. Dr. Matthews had been with women who had really turned him on sexually. She was still getting used to the idea of dating her secret crush.

“I’d love to have another date with you and get to know you better.”

I’d love to have another date with you and get to know you better.

Jason smiled, "Well, Jessica, I would like to get to know you better, as well." He meant it, too. Although he could feel his body reacting to the possibilities that a second date might bring, he wanted to know her better. Likely, they would only be involved with each other for a few months at the most until she took off for one of her "youthful adventures", but this would still be a "relationship", nonetheless.

Jason took Jessica by the hand and led them back to his car. The couple chatted warmly as they walked. Arriving at her apartment building Jason deliberately pulled in to the curb cut pull off at the front door, rather than parking on the street. He wanted to communicate that he was not looking for her to invite him in.

Laying his arm warmly on Jessica's shoulder Jason kissed her lightly on her lips. "Next Saturday?", he asked hopefully. "How about if I cook dinner for us at my place? Then, maybe we'll watch a movie on cable or Netflix. Sound good?"

“I’d love that. But, don’t feel pressure to cook, seriously. You’ve already treated me tonight. There are a lot of good places that have take-out/delivery. . . I can order from there, if you like. But, yes, dinner and a movie sounds great. That’s one of my favorite things to do, actually. To relax. . .”

Jessica was already wondering how she’d be able to wait a whole week. He was so easy to talk to, and he had keen insights. Thankfully, the awkward moment of saying goodbye, was not awkward at all, as Jason put no pressure on her to invite him to her place.

Jason was inclined to spurn Jessica's offer of getting take-out and paying for it. First, although as a single man he didn't cook much, he prided himself on being a reasonably good cook. He had a few favs that he liked to prepare. And, clearly, he was in much better shape to pay for food than was his intended lover. But, on quick second thought he decided to accept her offer. It had the effect of making them seem more equal than would be the case the other way around.

"Wow, Jessica. I love it! Sure! I'm an omnivore, so you choose. Pizza. Chinese. Kentucky Fried, I don't care. Just show up at my door at 7:00, if that's OK. We'll plan the movie for 8:00 or so."

Having taken care of the details for their next date, Jason kissed Jessica sweetly on her lips as he said "Goodnight" and she got out of his car to walk to her apartment.

The week sped by for Jason. His summer class was going well. He had lots of time to relax. Jessica, however, was never very far form his mind. He went to sleep every night with images of her and him in erotic embrace. Intellectually, he knew that they should not have sex - and have Jessica lose her virginity - on what would only be their second date, but he wasn't sure that he could wait. Could she?

Jessica kept herself busy between work, volunteer work, and her social engagements. But, at night, she found herself fantasizing about Jason. . . about the two of them kissing, the way he had cupped her face -she knew she’d be in good hands with him when she was ready to share ALL of herself with him. She fantasized about herself on top of him, clothed in a silky negligee (Why was she never naked in her fantasies?), rising and falling with him inside of her as he held her hips and encouraged her to let go of her fear of doing it wrong. Jessica became wetter than ever as she caressed her breasts and that special place, and her clitoris would feel very tingly, but she just couldn’t quite get herself over the edge to orgasm. Fuck! How was she ever going to do this with Jason? Why did she have to be so uptight?

***

As she thumbed through the options for take-out, Jessica realized that she should have/could have written restaurant reviews for take-out! On a whim, she decide to order from The Smokehouse. The next best thing to having grilled food, was to order it. Besides, it was delicious; and their delivery was reliable.

Jessica placed an order – spareribs, wings, grilled eggplant/squash/peppers, corn, coleslaw, spinach salad, and a French baguette. She had picked up a strawberry cheesecake from the coffeehouse near her apartment, too. Thankfully, Kate had given her a bottle of red wine to take along! She had blown her food budget, but she wanted to reciprocate the meal.

Jessica had decided to take public transportation, as Jason was just a few blocks from a stop. She had worn her casual light blue, high-waisted, flared leg jeans, open sandals, and a simple, white cropped top. She had left her blonde hair down, wavy. Uncharacteristically, she had painted her toes and given herself a manicure. Kate’s boyfriend has whistled as she left, and Jessica took that as a good sign.

Nevertheless, Jessica was nervous as she rang the bell to Jason’s place. She pushed her hair behind her shoulders, and attempted to look relaxed, as she waited for him to greet her.

Remarkably, the takeout order from the Smokehouse had arrived just before Jessica herself did. Jason was seriously impressed. He had expected pizza or a bucket of chicken from this young woman; instead, she had ordered a huge, full meal.

The image that he got when opening the door when Jessica rang his bell fed two different hungers of Jason's: his gastronomic hunger for cheesecake and his sexual hunger for Jessica dressed in such a hot outfit. He wasn't sure how much he could contain either one.

Controlling himself, Jason laid a hand gently on Jessica's shoulder, leaned in, and gave her a warm, gentle "hello" kiss. "Hi, and welcome," he said as he broke their brief kiss and took an additional opportunity to look her up and down quickly. "Surprise! Your food order from Smokehouse has already arrived. You outdid yourself. I'm very impressed."

Clearly with the amount and type of food that Jessica had ordered, they couldn't eat on paper plates while sitting on the sofa. Jason guided her to sit at his table while grabbing plates and utensils, and pouring a large glass of wine for each of them from the bottle that she had brought. As he sat down across from her, Jason noticed that his left knee accidentally was bumping hard on the very narrow space between both of Jessica's knees. With a mischievous grin he said, "Oh, excuse me...or, maybe I don't need to excuse myself."

Jessica smiled at Jason’s flirtatious statement. In truth, she knew they’d probably do “something” tonight. It was their third date, they were alone, and there was no doubt from their kissing in the park that there was some chemistry between the two of them.

The wine was warming her cheeks and only helping her to be brave and amorous.

The food was delicious, but the butterflies in Jessica’s stomach, and her desire not to feel overly full kept her from eating more than she normally would. But, the wine. Oh, YES.

Jessica guessed that Jason was ready for so much more. She debated about getting up and stradding his lap and kissing him. . . she couldn’t wait until they could make out, again. But, that was too forward of a gesture. She still didn’t know him that well.

Jessica slipped off her shoes and relaxed her thighs open.

“No you don’t need to excuse yourself. I know there is more to your appetite than just food,” Jessica said with a laugh. She hoped she could live up to the caliber of his ex-girlfriends.

No you don’t need to excuse yourself. I know there is more to your appetite than just food.

Jason could feel his whole body start to flush. Jessica had returned his suggestive comment with one of her own. Thinking ahead about their date and recalling the heat behind their kissing in the park, he had assumed that they would at least "fool around", but how far they were ready to go wasn't clear to him. Jessica's bold retort raised the possibility that they might go pretty far.

Notwithstanding his increasing arousal, they did have a sumptuous meal sitting in front of them. Additionally, they had at least hinted that they might watch a cable or Netflix movie as a part of their evening. Jason didn't want to entirely let go of the steam in their back-and-forth flirts, but he didn't want to stoke the fire too hard either.

"Well, ", Jason replied with a laugh that matched hers, "right now we should focus on our appetite for food. The excellent dinner that you brought is waiting for us to dig in." Having cooled the rhetoric just a bit, he took advantage of the physical opportunity by kicking off his shoes and gently sliding his panted leg between Jessica's knees until his knee was about half-way up her thigh.

Jessica nodded in agreement, as she bit into the sweet and smoky spare-rib, savoring the tender meat that fell off the bone cleanly. Jason’s leg was brushing against hers; she knew he was looking forward to being close to her as much as she couldn’t wait to snuggle with him as they watched a movie. It had been ages since she’d just relaxed with a movie… no less with a sweet date.

“So, how are your classes going? I honestly don’t know how you don’t fall in love a little bit. . . when one of your students is a particularly gifted writer. I find good writers fascinating. And of course, I find good teachers who understand writers, and themes, interesting, too,” Jessica said, with a wink.

She smiled down at her coleslaw. “What a delicious feast this is. . .I was hungrier than I thought I was!”

Jason smiled as Jessica spoke. He couldn't miss the subtext to her message: Did you fall in love a little bit with me?

Grabbing a spare rib Jason bought some time while munching on the tasty meat. "Well," he began, "as you probably know it's completely inappropriate to have an affair with a student. In addition to the ethics issue, you could actually get fired for doing so. Given that, you have to try to stop having your thoughts go down the line of attraction or falling in love a bit from a distance because, if you do, it might be too hard to stop."

Teasing Jessica some with his drawn out response Jason busied himself with eating before saying any more. "Sometimes there's a woman who is attractive and, you know, has a...well...hot body, but is so-so in her work in the class. To be honest, it's hard to keep your eyes off of where they shouldn't be in such cases, but other than that, there's not much attraction." He paused again a bit. "Then there's the really good student, but who isn't all that attractive physically. That doesn't cause a wandering eye problem, and leads to an attraction on an intellectual level that is very nice, and can lead to interesting interactions about her work. But, it doesn't inspire lust."

Jason again busied himself with food. As a grin began to spread across his face he made sure that he was holding eye contact with Jessica before continuing. "Then, only very, very occasionally, there is a woman who is attractive, has a hot body, and is the best writer in the class. Oh, those are the challenges that test one's temptations."

"Know what I mean?", Jason said, returning Jessica's wink.

Jessica smiled, although she found it hard to believe that she had a ‘hot body’ or was the ‘best writer’. She had always “dressed down”, just to ensure that she would be taken seriously and blend into the background. But, she did know that she worked hard. It was just her nature to be passionate and curious.

“Test one’s temptations,” Jessica repeated, slowly, licking her lips. “I literally like the way that sounds to my ear. But, yes, I understand the need to keep your professionalism . . . I was just curious to hear how you felt, privately. Fortunately, I’m no longer a student, so anything we do. . .is perfectly acceptable.”

Jessica finished her wine and kept her eyes on Jason. “And yes, I know what you mean. I’m attracted to the physical, but the intellectual is what locks me in and takes hold. And that’s why I want to be with you, Jason. And. . .if you are referring to me in your last comment. . . .thank you. I. . .I am glad that I appear hot to you. I’m finally getting comfortable with just being myself. . .as the woman that I am. I . . . I can’t wait to explore that side with you. Do you know what I mean?” Jessica asked, rhetorically.

One day, she hoped she'd be eating breakfast or sipping wine with Jason in far less clothes. Perhaps it would be something sexy, or just a robe. And they would act on their wildest temptations and fantasies. . . .

Jason realized that Jessica wasn't exactly vamping him, but she wasn't letting up on the intensity either. He realized that her statement that "intellectual is what locks me in and takes hold" was a reaffirmation that she didn't just want a quick fuck (or series thereof) to get past her virginity. On the other hand she also said directly that she couldn't wait to explore "that side" of herself with him. There was no doubt as to what "that side" meant. Jason decided to acknowledge the messages that he had just heard without just running ahead full steam unthoughtfully.

Jason reached over and took Jessica by the hand as he spoke. "Well, Jessica, " he said warmly, "it sounds like we understand each other and are both in the same place. So, let's go sit on the couch - we can bring our wine with us - put Neflix up on my flat screen TV, and decide what movie we want to watch." He paused for just a moment as they both rose together. "And, as for exploring, um...'that side', let's take that as it comes naturally to both of us, without feeling that we have to just rush into it."

As they moved toward the couch, Jason stopped them. Turning to face her, he kissed Jessica firmly on the lips, but without urgency, then whispered in her ear, "But, don't worry, we won't be waiting long, either."

Jessica felt grateful that Jason understood exactly how she wanted to take deal with SEX. She wanted her first time to feel natural, to take it a natural pace, although she was very curious and there was a bit of urgency due to her uncertain future.

Jessica chuckled and felt a warmth go through her as Jason whispered intimate thoughts in her ear. It was reassuring that he understood her so well.

“I’m a late bloomer, that’s for sure. Thank you for being patient and understanding me so well. I"m really enjoying being with you."

Jessica slipped off her shoes as Jason fiddled with the remote.

“I’m actually kind of choosy, but I can watch anything except horror. What are you in the mood for?” Jessica asked.

What are you in the mood for?

Jason was prepared for this obvious question, and he had done some research. He didn't want to suggest only romantic movies, although that is where his mind was heading. Lightly throwing his arm around Jessica he said, "OK. So, I've made a list of five movies that I've never seen but that I'm interested in. We could also pick something else if you prefer, no problem. So, how about this. you look up the descriptions on Netlflix, or online if you want, and you decide. How's that? In the meantime, even though we had the wonderful big dinner that you brought, I'm going to make a bowl of popcorn while you do your research."

Jason lazily got up to make popcorn as he handed Jessica a short hand-written list of movies. The list read:

• The Big Short
• Love Actually
• 21
• Take This Waltz
• I Am Love

Jessica quickly read the descriptions for all the movies. They all looked interesting, some more dramatically intense than others. She didn’t want to be sappy with Jason, though.

Once Jason settled back onto the sofa, she leaned into him.

“These all look good. I’ve seen ‘The Big Short’, but I could see it again. It is really excellent and I think you’d like that one a lot. Or, I’d try ‘21’. But, they all look really good, Jason. I’m impressed! We have the same taste.”