Like a Sir

Was shocked by how quickly she’d come to this point. When she’d brought herself here before, alone, in her room, it had always taken quite a bit of time, and a lot of concentration, and she’d never really even found the appeal in that part of it, either. It seemed like far too much work for a just a few seconds of feeling good. But now, god, this was so different, she’d hadn’t even reached an orgasm yet, and it still already felt better than anything else she’d ever done to herself, or her ex had ever done to her for that matter, but now was no time to think about that. Every time his tongue flicked at her clit, she’d gasp again, clenching the blankets. Her orgasm was building already, and her body was still trying to wriggle away from him, trying to shy away from all the things he was doing. 

Ashley let out a moan louder than she’d been expecting as his tongue entered her, not expecting the sensation. “Cal,” she gasped when he added in the use of his thumb. One hand sliding to grasp onto the arm that was still holding her hips in place, every time his thumb would start, her body would react, soft moans escaping her, only to be followed by a groan when he’d stop. She could feel her orgasm coming so close each time, and then it was gone. Ashley swallowed, trying to catch her breath, but now she’d come close a few times, and and each time she felt closer and closer, and she didn’t know if he realized how close she really was, if he wanted her to come this early. “Cal, I’m really-” She gasped as his thumb started to move on her again, her knees starting to shake as he did, luckily they weren’t supposed to be holding her up right now, “I’m really close,” She gasped, her hand clenching onto his arm even tighter. 

It was no shock that Ashley seemed to be thoroughly enjoying herself, with the way her hips rocked and hands clenched onto the fabric of his sheets. Her body wiggling and turning, as if being overwhelmed by what he was doing to the point of not being able to stand it anymore. That’s exactly how he wanted her, Cal thrived on situations like this, when his partner couldn’t with hold how he made them feel. It being Ashley gave this entire situation a whole new meaning. Her moans were different, the way she whimpered and gasped out his name, even the way her skin felt against his felt almost cosmic. As if this is how it was supposed to be all along. 

There was no way she could put what she was feeling into words, she was nervous, excited, eager, afraid. There were so many things going on, all she wanted to do was shut down her mind and enjoy the things he was doing to her. Things had barely started, just his lips on her neck, and she already felt like she was being swept away. Maybe that was the excitement, she didn’t know. With her ex, nothing about sex had really felt great. Everything leading up to it was okay, but none of it made her feel like this. Like every inch of her body wanted to be touched, the way her whole body reacted his soft bite on her neck, she had to wonder what else he could do to her, what other reactions he could pull out of her. She needed to stop thinking, because she didn’t want to get her hopes up, this could have all been her nerves, and she didn’t want to be disappointed. 

Yet, as he kissed down her body, her breath hitched, her whole body tensing with her nerves. He was between her legs, and suddenly she was in completely new territory, because this was something her ex had never done for her, not that this felt like the time to tell him that, and as he pulled her underwear down, she pulled her feet out of them, her breath growing more and more shallow while she waited for his next moves, not even knowing what to expect. When she heard his words, she opened her mouth to respond, but his breath hit her sensitive skin and she gasped, goosebumps rising on her entire body, and the kiss that followed made her grab the blankets on the bed below her, clenching them tightly at the feeling of his tongue on her. She was glad he had a grip on her thighs, because her body wanted to wriggle away, not because she didn’t enjoy it, but just because she wasn’t expecting the suddenness of the feeling that spread through her. Ashley gasped again, but it quickly turned to a moan as his tongue continued. She’d had a few orgasms before, but only ever on her own, and as she could practically feel the beginning of one starting to build in her already, her back arched slightly off the bed, feeling slightly embarrassed by how quickly she was feeling this way, she had no intention of telling him to stop. 

Now, there are things that humans are good at, the list could go on forever, but one of the things that Cal had perfected in his lifetime was eating a woman out. It was one of his favorite things to do if he were being honest with himself. That’s not to say he had a slew of sexual partners, but the ones he did have--well, lets just say they all started and ended with the tip of his tongue. Though, none of that mattered at the moment. What had been apart of his past was of no concern to him when he had Ashley like this. How he has thought about having her so many times before The sounds she was igniting were driving him wild, if she only knew exactly what she was doing to him.

Ashley was nervous, she wouldn’t deny that, she was scared, too, though not of Cal, or of being hurt, but just of the situation in general, part of her was scared that she wouldn’t like it again, that maybe sex was just something she didn’t enjoy, and that really scared her, considering how important it seemed to be in relationships. She knew that Cal would never rush her, and that he’d wait patiently for her to be ready, but what about if he waited all that time, and she didn’t want to do it again? She didn’t think it was really possible to be with someone long term without it. Ashley tried not to think about that, she was getting much too far ahead of herself, and needed to focus on what was happening now, and hopefully enjoying it. She wanted to enjoy it, she wanted Cal to enjoy it, too. She wanted this. 

As she stood in front of him, goosebumps rose all over her body, from the way he looked at her, causing her to blush and look away from him. She’d never been one to think of herself as anything special, she was pretty enough, and she took care of her body, but she would never use the words beautiful, or breath taking to describe herself, and yet, when Cal looked at her like that, she felt like maybe she could be beautiful, or maybe he thought she was. When he picked her up again, she laughed, though it wasn’t funny, but when she was nervous she couldn’t help but giggle. Ashley laid back on the bed when he placed her there, watching as he began to kiss her, every where his lips landed her skin burned, under his touch, causing her breath to grow shallow and fast. 

She wanted this, she definitely wanted this. Every move that he made made her realize more and more that she did want this, not just for Cal, but that her whole body genuinely wanted this. As he moved up her body, his arms pulling her closer, she gasped at the feeling of lips on her neck, chills shooting down her spine at the feeling. It was when he gently bit down, that her whole body jerked, a soft moan escaping her before she could stop it. One of Ashley’s hands rose into Cal’s hair, combing through it, the other sliding down his side until she reached his boxers. She slid her hand over his hip, the tips of her fingers just inside the band of his boxers, but not dipping in too far, she didn’t want to rush anything, she wanted him to be in control, since she didn’t know what she was doing. 

Callahan was in his element right now. He was never one to think that sex was a key component in a relationship, but that didn’t mean he couldn’t appreciate it whenever the moment struck. All in all, with Ashley it had been a completely different story, while he didn’t mind waiting for anyone perse, it was extremely important to him that she felt safe. Though, at the place that they were in right now, Cal was more than certain that his girlfriend was at a proper place to enjoy herself or if the situation were to arise--to tell him to stop. It’s never about a quick fix for him, he has never seen it as something to gain but more as something to experience together. 

Here she was, exposed underneath him and he couldn’t seem to get over the fact of how radiantly beautiful she was. Those eyes that he could fall into and that smile that always seemed to catch his breath. It was bizarre and almost unexplained sometimes but God was he about the rush that she gave him every moment of every day. The way she reacted to his kisses only telling him that it would be wise to continue and of course Cal was more than eager to please her. At times he wondered what had compelled her to wait for so long and he knew certain sides of the story, but something told him this needed to be handled with care. Well, as much care as as Ashley wanted, the ball was in her court, though she was wanting him to take the full reigns. 

callingcallahan:

Ash pursed her lips together as he mentioned her being comfortable, trying to pause for a second and see if she really was, but then she saw that he was reaching for his pants. The last time she’d done this, it was just awkward, and painful, and rushed, and uncomfortable. This didn’t feel rushed, or awkward or uncomfortable. She was nervous, but she felt comfortable with him. Ashley let her hands fall from his shoulders for a few seconds, her fingertips just barely grazing the skin on his chest, before looking back up at him, her hands sliding back to their original position around him. 

She smiled again when he asked if she wanted this, his hands grazing her body, left little wakes of chills that went through her, and she didn’t know how he could even think she didn’t want this, all he was doing was touching her, with her clothes still on and he had her body shaking with excitement. Pulling her arms away from him, she reached down to pull her own shirt off, tossing it to the side, trying not to feel self conscious in her bra, before reaching down to slide her skirt off as well, pulling her legs out of it one by one before dropping it in the same spot on the floor. She’d never really been in front of someone like this before. “I do want this,” She nodded, but frowned for a second, “And I appreciate you wanting to make sure I’m okay, but I also don’t want you to spend this whole time worrying about me. Just do what you’d normally do, okay? If I want you to stop, or stop feeling okay, I’ll tell you, okay?”

Reading the situation it was clear to see that Ashely  was definitely seeming more and more comfortable as the night went on. Even know that he had undressed around her, her hands didn’t fail to make contact with his skin and in Cal’s eyes this was a very good sign. It showed that the woman in front of him was eager for more or at least willing to attempt going further than their usual sexual endeavors and Callahan was expecting to guide her as much as she needed. Sex wasn’t just about someone getting off and leaving it at that, it was about two people experiencing sexual arousal and finding their peaks of ecstasy together. Not as two separate beings but as a whole. Where you were your most vulnerable with someone, showing them sides of you that not everyone got to notice. 

callingcallahan:

She was used to guys her age, always pushing for more, always expecting something, and it was honestly strange that Callahan wasn’t like that. In fact, when they first started dating, she’d convinced herself that he was entire unattracted to her, because why else would he make no efforts try for more, when that was what she was so used to now. Still, the pushing always just made her uncomfortable, and it was because of that that she was so inexperienced, only really letting herself that close to one person, and it had been a mistake. Callahan just seemed so different from all of that, and all she could do was trust him, and hope for the best. Hope that she was right about him, but for some reason, she wasn’t worried about being wrong, something about him told her she was right to trust him. 

Ashley watched as he began to unbutton his shirt, trying not to laugh at him telling her to relax. As if relaxing were even remotely possible in this situation. She slid her shoes off as she watched him, laughing at his comments, though her eyes wouldn’t seem to meet his, but that didn’t stop her from staring at the muscles he’d just revealed. She knew they were there, she’d felt them under his clothes various times, wether it was just making out on the couch, or giving him a kiss and hug goodnight, but it was an entirely different thing to see it. She tried to find some nerve, and as she dropped her shoes to the floor, she rose up to her knees, shuffling closer to him as her hands grazed over his shoulders, finally meeting his eyes. Ashley pressed her lips to his, kissing him more passionately than the last few kisses he’d placed on her forehead and lips, her arms wrapping around the back of his neck, and clasping together before she pulled away. “So, if I’m following your lead, does that mean I should take my shirt off now, too?” She asked, raising an eyebrow at him.

While this wasn’t a first time for Cal. he wanted to make sure that no matter where this led that Ashley knew she was safe here. It was light, carefree. They were chuckling and laughing, even now with his shirt on the floor as he looked at her. When she mentioned taking her shirt off as well,Callahan raised his eyebrow at her. Their kisses were a lot more passion driven, less light and sweet. Knowing that they were going to lead to a lot more than a make out session before ultimately going back to their usual nightly routine. “If you feel comfortable taking your shirt off, then yes. I for one, felt comfortable taking my shirt off with you” Cal stated simply, which in truth he did. In public, he was a  lot more reserved, never really bringing too much attention to himself, it was usually just thrusted upon him. Well, in the bedroom, he exuded a completely different kind of confidence. “So, I’ll continue with--” He trailed off, unbuckling his pants and slipping out of them slowly. Of course, he was wearing boxers, it was no different than any other night Ashley had stayed over, but he was testing the waters still. 

She tried not to look to deeply into the fact that Cal seemed to know her so well, already. That him telling her she was worth it, it was exactly what she needed to hear. What she’d been needing to hear for so long. Ashley smiled at him before speaking, trying to pick her words carefully. Truthfully, a part of her didn’t even know how they’d ended up here, she was so afraid to jump into a relationship, and yet Cal made her so calm, it was easy to see why she’d been so willing to do something that otherwise scared her. Instead, she decided to stay silent, leaving the conversation there, rather than turning it into something else, not wanting to make things too deep when it wasn’t where she wanted the night to go. 

As he lifted her, she let out a small laugh, her own arms wrapping around the back of his neck, nodding at his words. She knew that she didn’t have to worry about that, that he would never cross any boundaries she set, even if she didn’t know what those boundaries were just yet. As he sat her down, she blushed at his kisses, reaching up to comb through his hair again, as she kissed him back, before sliding back further onto the bed. She hated that this situation was making her awkward, because usually with Cal she was so comfortable, but this was just unfamiliar territory for her, and she knew that he knew that, but it didn’t make it much easier. “I know that I’ve already told you that I don’t have much experience with this stuff, but -um- just, I mean, just tell me what you want me to do.” She said, looking up at him, hoping that he was more interested in taking charge, rather than wanting her to. 

This was all new territory for Ashley and he could see it written all over her face. She was nervous but he could tell that apart of her really wanted to delve into this new area of their relationship. Of course, even from the beginning, Cal knew where she stood and never once forced her into anything that Ashley seemed even remotely uncomfortable with. It just wasn’t the type of man he was and he would never be. It was important to him that she felt safe and comforted at all times because if not, then what was the point of wanting to be together in a relationship. Things weren't always meant to be sexual and Callahan made it a point to tell her that. He would be patient for her. Always. 

callingcallahan:

She couldn’t help the blush that rose on her face. Ashley had had a boyfriend before, and sure, he had said sweet things to her, especially when they first started to date, but it wasn’t the same. Cal was so much more genuine, telling her that he wanted her around was on an entirely different level than telling her that he thought she was pretty, which was what she was used to. Still, when he said there was no need to thank him, she disagreed, but not because she somehow felt she owed it to him to move any faster, but because he didn’t feel she owed him anything, either. Something that she wasn’t used to, not in what seemed to be a world of guys who felt that they deserved something just for being nice to a girl. Or guys who thought girls were someone they weren’t, and thought that meant they could have whatever they wanted. “The fact that you’re more than happy to do it is the exact reason I do need to thank you.” 

Ash was enjoying where they were, she honestly was, but she felt a comfort in Cal that she hadn’t really been expecting, a safeness. She didn’t feel rushed, and in turn it made her want to move forward faster, knowing that he would never let things go further than she wanted them to, or never make them go further, for that matter. Ashley shivered against his touch, as his hand ran down her body, pulling her closer. She couldn’t pretend like she didn’t notice how strong he was, the way he pulled her closer, the feeling of his body against hers, it was easy to feel that he spent more than enough time in the gym, and that only made her want more, made her want to touch him without their clothing in the way. A feeling that she didn’t usually have. Her skirt seemed to have slid up quite a few inches as he pulled her closer, and she made no move to fix it. She pulled her lips away, staring at him again for a few seconds. “Do you want to-” She started, but wasn’t really sure what to ask, she just wanted him to know that she was ready for more. “I mean, would you rather we moved to your bedroom?” She asked, her cheeks turning a dark red with embarrassment for her awkwardness. 

It was quite adorable how Ashley tended to blush about things that most woman would have brushed off. She was always appreciative of his kindness and it wasn’t that he did so to be noticed, but it felt nice when the person you cared about, knew you cared about them in return. So of course when she had given her spoken thank you, Cal wasn’t having it by any means. He was more than happy to wait for her,be patient with her, and whatever else she needed. Callahan was not in this for the so called ‘benefits’. He was here because there was no way he could have forgiven himself if he had let someone like Ashley walk away from his life without trying. “Well, I will never deny your thank you, but rest assured, I am doing this because I want to. Because I know that you’re worth the wait and so much more. I need you to know that, Ashley. You are more than worth it.” 

Things were definitely getting a lot more heated as time went on. Their bodies getting incredibly close together and Cal realizing just how badly he wanted to have his hands all over her. It was never in a ravenous manner. It was always to that degree of sensuality where Cal just wanted to take care of her in everyday possible. But, as they continued their endeavors, he was starting to see that Ashley was becoming a lot more open with him in more ways than one. When she spoke up about the bedroom, he took a moment o look at her and sort of gauge if she was absolutely sure. She seemed to want him to take that extra step so, with much care, Cal smiled brightly at her and scooped her up in his arms. “We can stop whenever you want” He whispered to her softly as he made their way from his living room to the bedroom. That was when he set her down gently kissing her forehead, cheeks, and lips a few times for comfort. 

callingcallahan:

It was incredible the way her heart raced, just from the way he looked at her, the way he smelt, the way his fingers grazed over her skin. If such a simple touch could send chills through her, what else could he do to her? She blushed at his comment, giving him a small smirk. “Be careful, you might never get me to leave if you keep saying things like that to me.” She said softly, her own hand reaching up to comb through his hair gently. Ashley shifted her body as he kissed her, facing him now, one leg bent in front of her, the other stretching out to lay over his lap. It was a bold move for her, not by normal standards, but certainly for her. She pulled away from his lips, her eyes staring into his. “I just want to thank you, for being so patient with me.” She whispered, hoping he wasn’t getting tired of it, but deep down knowing he wasn’t, he wasn’t the type, not in her opinion. 

Ash pressed her lips back into his, her hand resting on his shoulder now as she slid her body closer to his. She wasn’t used to this, she wasn’t one to try and make the next move, so trying to signal for him to go further, well, she just didn’t know how to do that, so she just tried to do what felt natural. 

It was a nice combination of playful of serious, Cal seemed to find himself with her. It was never too much or lacking anything, Ashley was indeed in his opinion, the perfect woman. While yes, we all had our faults to a certain degree, Callahan was a mine who never judged a character by there inability to do but by how they did said things. He could look into those eyes and a smile would immediately spread across his face. It was just that affect that she had on him. “I believe you are under the impression that I want you to go anywhere”  Cals voice soft as he closed his eyes, letting the sensation of her fingers through his locks over come him. Ashley picked up on it instantly that he enjoyed having his hair combed through, it relaxed him in a way. Now, with one leg cross his lap, Cal was easy with her, never moving too fast in hopes of letting her know she was safe with him. His movements were slow, sensual, just enough. “There’s no need to thank me for something that I am more than happy to do” His smile was soft as he looked at her. 

When her lips were on his again, he didn’t hesitate in kissing her back, but he did notice that Ashley was pressing in a lot closer than their usual encounters, but he didn’t want to read too much into that. So, he took precaution, letting his hand slide down her curves as he tested out the waters, gripping onto her lightly and pulling her even closer to him. 

Ashley knew that it was ridiculous for her to be so scared of the things she was scared of, it wasn’t as if every time she had sex something would go horribly wrong, but she still couldn’t help but feel her hands shake at the idea of it. Her and Cal had gone out quite a few times now, and she knew he wasn’t a bad guy, but in high school, she never would have thought that her boyfriend was a bad guy either, which is what made this so hard. She didn’t want to hold that against Cal, but it was difficult when that was the only experience you had. Besides, she’d only had sex the one time, and it really was not enjoyable, so maybe the fact that she didn’t understand what all the fuss was about just made her more nervous. 

Still, she wanted to trust Cal, she really did. She wanted to open up to him, she wanted to share that connection with him. They were together now, shouldn’t that mean something? Shouldn’t she be able to be intimate with her boyfriend? He’d been nothing but respectful with her, treating her with care, and he’d been completely understanding of him wanting to wait, but how long did she need to wait? It was going to happen eventually, wasn’t it? And if it wasn’t, if she couldn’t trust him, why was she dating him? Ash sighed, as she looked at herself in the mirror. They’d gone back to his house after dinner, sitting on the couch to watch a movie, and began making out, and she was enjoying it, and she knew he was, too, she didn’t know if he was going to try to push things further, but she needed to decide if she should stop him or let him if he did. She’d excused herself to the bathroom so she could cool down, really let herself think about it, instead of getting caught up in the moment. 

She couldn’t hide out forever, though, so instead she just decided to go on instinct, if he tried to move things along, she’d decide how she felt then. He knew she was pretty inexperienced, though she didn’t know if he knew just how inexperienced she was. She’d only had sex once, and beyond that, she knew next to nothing. Ashley tried not to think about that as she made her way back out to the couch, smiling as she saw him sitting there, her happiness of being with him out-weighing her fear for a few seconds. “I hope you didn’t miss me too much.” She said softly, sliding back into her previous start, “Now, where were we?”

To find himself in this type of position was somewhat of a rare case. It wasn’t that Callahan didn’t have people fawning over him, it was more of the fact that he rarely noticed it at all. But oh, did he notice her. That smile, the way her hair fell over her shoulders. She was completely radiant and it could not be ignored. Of course, he took the first step and properly asked her to dinner. Which happened on more than one occasion. Different events, new areas, they spent plenty of time together enjoying each other’s company. He knew that Ashley wasn’t like other girls. She wasn’t about being over sexual and making him uncomfortable, which in truth, happened a lot more frequently than you might think. Granted, things in the bedroom were a completely different story. here were certain ways he liked things done, nothing wrong with that he wouldn’t say, just rather peculiar to say the least.

 They had gotten passed the dating stage and eventually Cal asked her to be his girlfriend. That was a rather memorable day of course. Neither of them really took it to any other level aside from kissing. While Callahan had done more than his fair share of sexual encounters, he would never push Ashley to do something she wasn’t ready for. So, he told her he would wait until she was ready and that he did. Even when things got a little heated, it was easy for him to pull back because he cared about her and her feelings towards all of this. If she wasn’t comfortable, why did he deserve to be? At this very moment, things were at that heated stage again, she had come over to watch a movie and it ultimately ended up in a make out session on his couch. Which he for one would never complain about, but he supposed it became to much for her, causing her to up and leave to the restroom. So, Cal waited. 

Once Ashley returned back into the room, he greeted her with a proper smile. Never one to be upset with her when she needed time to compose herself. Never the one to be overly impatient and demanding something that wasn’t his. At her response, Cal gave her a toothy grin and nodded. “I always miss, you, sweetheart. Never a moment when you’re away where I don’t miss being around you” He teased her, sipping his arm around her once again. “Wherever you want to be, Ashley” Cal whispered, his free hand coming up to brush a strand of hair away from her face and kiss her softly.