by K. J. Ward
Cherry on Top
It was definitely not when Lisa O’Neil thought she would be having sex for the first time, but it was absolutely the right time to do it. She was right in the middle of studying for her finals that semester, and she knew Richard, her boyfriend for the past year and a half, was just as busy. Both of them were strapped for cash thanks to the college raising tuition, which had not been factored into their student loans, so the last thing she expected that evening was a romantic dinner at a nice restaurant. But Richard had a way of surprising her, and he’d surprised her that day when he told her to wear something nice later because they were going someplace special for dinner. At first, she wanted to tell him no, to hold off until after the semester had ended… But truth be told, she needed the break from studying. So she stopped studying a couple hours before it was time to go so she could get ready. As she did so, she realized that that night could be the night – the first time they were going to have sex, and the night she could put her plan into motion.
After Lisa joined her sorority as a freshman, many of the girls she’d joined with wanted to have sex – or already had with their high school boyfriends. Naturally, since it was college, many of the guys on campus were more than willing to have one night stands. But Lisa wanted more than that. Most of her sorority sisters thought she was insane. Those that had already had sex for the first time told her it was just an awkward experience that was never romantic, and to just get it over with. Her sorority sisters who had not had sex yet all said that the first time’s not important – aside from, of course, making sure to have a first time as soon as possible. But she wanted more than that typical, awkward experience, and she was sure that after a romantic, special night with a man she loved that she could get that. Certainly, she didn't want a one night stand, and after meeting Richard that was no longer an option anyway. All of those people telling her that her first time wasn’t important and wouldn’t be romantic only solidified her belief that it could be romantic with someone special – and Richard was her someone.
Lisa made sure to stop studying early so she would have a bit of extra time to get ready. It was a special night, potentially the night that she would put her plan for her first time into motion, and she wanted to make sure that she looked special for the man she loved. She took a long shower, taking the time to shave extra carefully. She had a bad habit of getting nicks and cuts but she wanted none of those on a night like tonight. For the first time in quite a long time she shaved her womanhood completely, going with a hairless look – the last time she'd tried that was in high school but quickly came to the realization that the time it took wasn't worth it if she didn't have a good reason to keep it completely hairless instead of trimmed. Today, that was time well-spent as she prepared for what she thought could be her first time with a man. After she'd showered, she dried off except for her hair, which she blow dried and then spent quite a bit of time styling, more so than she would have at any other time. She had beautiful dirty blonde hair, and she made sure to curl it just a bit so it flowed down her back in luscious waves. She finished it off with just a bit of light makeup, eyeshadow and mascara, nothing too prominent or over the top. After putting light blue nail polish on her finger and toe nails, she pulled on a black bra and thong – one of the few thongs she owned – and put on a sleeveless black dress she'd been saving for an occasion like this, and completed the look with a pair of black heels and a pair of gold stud earrings. She took a moment to look in the mirror, liking what she saw. Spending time on yoga each day and watching her diet had paid off – her body was sleek and athletic, yet soft and supple as a woman's body should be. Her confident smile turned into a broad grin as she heard a knock at her apartment door – Richard was there to pick her up.
She opened the door to see her boyfriend wearing a suit and tie – it must have been quite a restaurant that he was taking her to. Lisa's eyes met his and she leaned in to kiss him softly, “Hi sweetheart.” As she spoke he wrapped his arms around her and returned her kiss, “Hello my love.” He took her hand and led her out to the elevator and then out of her building to his car. She didn't even bother asking where they were going – she trusted that it would be some place good. Soon enough he was driving and asking her how exams and studying were going – as he always did. He always expressed concern for her and how she was doing, both with school and simply in life. It really showed her just how much he loved her. Studying was going okay, of course, but could always be better. It never felt like there were enough hours in the day – something she knew he felt as well with the engineering degree he was pursuing. Of course, she was just as concerned about his studies, but he said that everything was going okay. He'd had one of his exams already, and though he didn't have the result yet he was sure that he'd done well on it.
Eventually their conversation turned to less serious things than their classes and exams. Lisa lost track of how long they'd been driving but she guessed it was about twenty minutes before they pulled into a parking lot and Richard parked. She recognized the restaurant immediately and shook her head, her eyes wide, “The Chateau? Richard, you didn't!” The Chateau wasn't the most expensive restaurant in the area, but it was certainly up there with fine food. Considering the Chateau's dress code, it was one of the more upscale restaurants in town even if it wasn't the priciest.
“I know, I know... It's a little pricey, but you're worth it,” Richard told her as he turned the car off and leaned over to kiss her cheek gently. He got out of the car and walked around to open her door like a gentleman, before walking into the restaurant with her, holding her hand as they made their way inside. As much as he'd surprised her by taking her there, Lisa could tell that her boyfriend had been planning this – he had made reservations, and already knew the restaurant's wine list because as soon as they sat down he got them a bottle of wine. As soon as she had an opportunity to look at the menu, she could see how long he must have been saving to take her out to dinner that night. She decided to try to mitigate the damage to his bank account a bit and order a salad, but when she told him that he told her that she should try the steak. She decided to do so, and after ordering Richard poured her a glass of wine and one for himself, and then had some of the bread that the waiter had brought out to the table.
Lisa and Richard talked quietly as they waited for their meals to be brought out. The Chateau was certainly a romantic setting. It was dimly lit, and there were candles slowly burning on their table so they were eating by candlelight. In addition to the candles, the table was decorated with flowers. Combined with both of them being dressed as nicely as they were, it was turning into a very special date indeed. Soon their dinners were brought out and Lisa enjoyed her meal with Richard. The possibility of that night being her first time was still on her mind but very much on the back burner as she simply enjoyed herself with her boyfriend. When the meal was over and they'd finished their wine, the conversation was great and neither wanted their time at the Chateau to end, so they each decided to have coffee. Afterward, since neither wanted dessert, Richard paid the bill and then took Lisa's hand on the way out, kissing her cheek on the way out of the restaurant, “I love you, Lisa.”
“I love you too,” Lisa told him with a smile as they headed back to his car. She decided to make the first move after their romantic dinner, so she added, “What do you say we head back to my place? My roommates are going to be out late studying, so we'll have the apartment to ourselves.”
“I'd like that,” Richard told her as he turned the key and then started to drive, “What were you thinking? A movie on Netflix?”
“I was thinking something more than that,” Lisa replied with a coy glance, a broad smile and a wink.
“Oh? Are you sure?” Richard asked her, glancing over at her as
he drove. They'd had discussions about sex before, and he knew about and respected her desire for it to be special and to wait. He had assumed that would mean waiting until marriage, though that wasn't exactly what she'd said. That discussion had been relatively early on in their relationship, perhaps a few months in, and Richard hadn't mentioned sex to her since. He was content to wait, because he needed to focus on his studies as much as she did, and on top of that he'd had sex before, and while it had been good in his previous relationships it had tended to become the reason to be with someone. He'd wanted something more than that, an emotional connection and bond like he now had with Lisa. Of course they'd made out, felt each other up... but never anything beyond that. They'd fallen asleep in the same bed, but had never even seen each other naked yet.
“I'm sure,” Lisa answered with another smile as her eyes met his for a moment. The look on her face said it all – she wanted him, right now. He didn't say anything further about it, he simply drove to her home, perhaps a bit faster than he might have if Lisa hadn't said anything. She felt on some level that it should be an unplanned kind of moment in which her first time happened, but the night already seemed perfect. She was in love with a man who loved her in return – she was certain that because of how she felt about Richard, that it would be the special experience she planned for it to be. She took a deep breath to steady her racing heart as he pulled up to her apartment, feeling a bit nervous despite wanting to be with the man she loved. It helped that there was no pressure, only the pressure she was putting on herself but none from him.
Once Richard had parked, he opened the door and she got out as well. He took Lisa's hand but did not lead the way in – he wanted to take away anything that could be construed as pressure to do something sexual if she decided she did not want to. Lisa didn't hesitate, however, holding his hand as she walked in and, once they had arrived on her floor, she opened the door to her apartment. After closing the door, she wrapped her arms around him and looked in his eyes lustfully, leaving him with no doubt that she did indeed want this. She kissed him deeply, her tongue slipping into his mouth as her hands moved up and down his back. Lisa was honestly surprising herself a bit. It was as though waiting to make love for the first time had been like building a dam within her that her feelings had steadily built up behind. Now that she had opened the floodgates of her passion it was impossible for her to hold herself back.
Richard immediately saw the change in her and felt it in the way she kissed him, no longer as timid as she had been throughout their relationship, but with confident desire that this was right and she was meant to be his. She broke their kiss after a short time, but only to pull his jacket off, toss it on the couch, and then pull him back toward her bedroom. His only response was to grab her and literally sweep her off her feet, carrying her in his arms to the bedroom, kissing her cheek and lips softly as he did so, before he put her down on her feet once they were inside her room. She pushed the door closed and then kissed him passionately once more, starting to unbutton his shirt as she did so. Her hands shook with anticipation even as she'd started making out with him as she unbuttoned his shirt. She didn't want to just be kissing him like this – she wanted him inside her.
As she pulled his shirt off she realized that he had reached behind her and was unzipping her dress as they kissed. Her heart skipped a beat as she suddenly realized this was really happening. It wasn't that she didn't want it to happen – she simply wanted it perfect and to go as she planned, and that led to nervousness. He broke the kiss after a while, sensing her distraction as he finished pulling down the zipper. His eyes met hers once more and he smiled reassuringly, “Lisa, relax. You look so worried. I know you want it to be perfect, but trust me, it'll be great for you if you just relax and let it happen.” He tugged up on her dress and, when he met with no resistance from her, pulled it up and off of her.
Lisa realized quickly that he was right – her body felt stiff and every muscle was tense, not with desire but with worry that it wouldn't be perfect or special or that her plan wouldn't go off without a hitch. There was no way it would be special if she didn't relax – she didn't want to remember it this way. She took a deep breath before she kissed him deeply again. She moved her hands down over his chest and abdomen, unbuckling his belt as her tongue jousted with his. It took her a bit of time fumbling with it, but she finally got his pants unbuttoned and unzipped. Meanwhile, Richard got her bra unhooked and pulled it off of her. A slight blush appeared on her face as his fingers hooked on her panties and broke the kiss, his eyes moving down her body as he pushed her thong down. She stepped out of her panties and kicked off her heels, naked for the first time before the man she loved.
Richard gave her body a quick look before his eyes met hers, the lustful gaze telling her that he liked what he saw. He pushed off his pants and underwear, his cock fully erect and fairly large. She knew on some level that it would fit, but it was definitely intimidating considering that it was her first time and she didn't know how it would feel. But she pushed those thoughts from her mind, focusing instead on the heat within and the desire she felt. She wanted something memorable; she was going to get that giving into the passionate love she felt for Richard. She wrapped her arms around him and kissed him deeply, her hands moving over his naked body, exploring his muscular arms, every part of him. He moaned into their kiss when one of her hands strayed over his cock and then ran up and down the length of it, gently stroking him. As she touched him, Lisa felt his hands moving over her body, gently caressing every inch of her form. He ran his fingers softly over every curve, spending quite a bit of time on her breasts. Richard gently pinched her nipples, rubbing them between his fingers causing her to moan loudly into the kiss. The way he was touching her was making her even wetter than she already was, considering how romantic the dinner had been.
As they kissed and felt each other up, eventually Lisa pushed him down on the bed, breaking the kiss as she did so and moving to lay over him. She looked in his eyes and kissed his cheek, smiling lustfully as she put her plan for her first time into action, “I want to be on top, and I want you now.”
“I'm not going to argue with that,” Richard said with a small chuckle, running a hand through her hair. It wasn't a bad idea for her to try it that way, considering it was her first time – it would allow her to control the pace, how hard the thrusts were, and the angle that he went in at. He hoped it would increase her pleasure and make it more enjoyable for her. She moved to her feet, squatting over him as he stroked his cock lightly to keep it rock hard for her. She shifted her body downward so his cock was pressed against her entrance. It took her a bit longer than she would have liked but she positioned him and slowly slid him into her.
The feeling as he penetrated her was absolutely amazing. It took her breath away, though she wasn't sure whether to call it pain or pleasure that was doing it. Her core felt completely full and only his tip was in. She slowly lowered her body so more of him slid into her wetness, causing a low, long moan to escape her lips. Richard was able to keep himself from arching his back and rocking his hips, letting her control the pace, but he was barely able to do that as he throbbed a bit in her, his excitement having built over the course of not only an amazing date but over their entire relationship. That excitement and desire was the same for her, having built up over time. Perhaps it was that excitement and desire but she didn't feel the pain some of her friends had described during their first times. Then again, that could also have been how slowly she lowered her body and took him into her.
She wasn't sure how she knew when she was full, but she somehow knew. Lisa rocked her body a bit, letting him slide out before she lowered herself again. His cock slid in and out of her slowly as she moved, finding a pattern and rocking her hips. She moaned as she realized that it wasn't just about the rhythm but also about the angle his cock entered her at. She could reposition her body and make him enter differently, and trying that she was able to make him hit a certain spot that felt ab
solutely amazing. She moaned loudly, arching her back and looking down at her love to see his reaction. He was moaning as well, obviously enjoying the experience. She hadn't even realized it in the midst of all that she was feeling with his cock in her; his eyes were moving over her body, admiring her as she moved up and down on his shaft. She realized how much her breasts were bouncing as she rocked her hips at that point and that he seemed to be enjoying seeing them move. She pushed that thought from her mind, realizing she didn't care if he was admiring her body, only about how much she wanted him and how much pleasure he was making her feel.
She felt lightning surge through her body from her core, much like she'd felt before when masturbating but on an entirely different level. She reached down to play with her clit as she rocked her hips, screaming his name with pleasure as she ran her finger gently around that pearl of pleasure between her lips. She could feel him throbbing within her with every thrust, which seemed to be much faster now than they had been when she'd started. It was as though her instincts and her body took over and freed her mind to focus on how much she loved him and the pleasure she was feeling. Shock waves surged through her body as she cried out his name once more, becoming aware that he was cumming within her as her own juices flowed around him and her muscles clamped down. Her hips kept moving, her body bucking on top of him for a time before she finally let him slide out of her and moved to lay beside him on the bed, breathing heavily. Though she'd masturbated and experimented with certain toys, she'd never penetrated herself before. She'd heard that some women couldn't orgasm at all when they were having sex. She'd just had her first truly mind-blowing orgasm while having sex for the first time.
“So?” Richard finally spoke beside her as he put his arm around her and leaned in to kiss her cheek. The combination of his speaking to her and the physical touch brought her out of the trance-like state her climax had left her in, “Was it as special as you thought it would be?”