Ash's New Career Pt. 16

Chapter 22

It took Ashley a couple of minutes of just sitting there on all fours with Bruce's rock hard cock right up against her puckered hole while his mouth was paying all kinds of loving and lustful attention to her neck and back. It was amazing and got her quite a bit more worked up than she had already been to the point where she finally decided to take the leap and push back a little, driving up the pressure with her slippery butthole against his slippery cock bit by bit. It wasn't nearly as easy as she had imagined it to be, mainly due to how woefully unprepared her ass was, never having had more than a finger or maybe two up there when she had been feeling daring before.

Pushing a little harder and harder each time, the moment her ass finally gave way arrived as Bruce's cock slid inside, getting a loud shocked, slightly pained gasp out of Ashley. Despite the fact that she had been pushing, the effort needed still made it a surprise when it finally happened. She could feel her ass burn a little, the sheer size of Bruce wildly uncomfortable, stretching her beyond what she had ever been stretched before. Bruce who had been moaning up until now as he had felt Ashley try and take his cock, couldn't help but be taken by a wave of worry upon hearing that pained gasp. He instantly pulled his head away from Ashley's neck, about to ask if everything was okay, not really knowing what to do with the head of his cock buried up Ashley's butthole, not wanting to hurt her while realising that simply pulling out would hurt as well. Even the slightest movement got a few more grunts out of Ashley which only fuelled his worry.

"B... Bruce please remain very still, I... I've might have bitten off a bit more than I can chew. I guess I need a little time to adapt." Ashley gasped with bathed breath, her ass slowly stretching to accommodate the cock inside of her while Bruce tried to remain as still as he possibly could, not wanting to screw this up. It made for a very awkward few minutes where the both of them didn't really know what to do while Ashley's ass slowly adapted the pain of first entry dulling bit by bit as her ass stretched a little to a point where it was just a little uncomfortable rather than painful. Ashely realised full well that it was probably the right time to pull out now that her ass wasn't hurting as bad anymore, to take it as a sign that it was probably best to try this another time.

At the same time though she could really appreciate that this was actually happening, here eyes wide with awe, that she could actually feel Bruce's cock inside of her. It had something magical about it, making her feel so much more connected to him and she kind of didn't want it to end. She knew full well that this was probably a bad idea, but she wanted to feel more of this, not less. She had gotten this far after all and she was too stubborn to quite. Surprising the both of them Ashley actually ended up pushing back a little further, impaling herself one inch more on Bruce's cock, whimpering slightly as it grew a little more uncomfortable once more. This time she didn't let it get painful though, instead breathing heavily as she tried to allow her ass some time to get used to it once more.

Bruce for his part, tried to keep as still as possible, yet when Ashley slowly slid back, taking more of his cock, he couldn't help but let out a soft moan. She was just so very tight and it felt so very good, making his cock involuntarily throb inside of her which got a grunt out of Ashley who was still trying to adapt to the sheer size of him. "I... I'm sorry, I didn't mean to. Wouldn't it be better to, you know pull of?" Bruce stammered, feeling awful for what was essentially a natural reaction he couldn't help no matter how he tried. He didn't want to hurt Ashley, but if she kept this up he couldn't stop his cock from throbbing again.

"P... Probably yeah, but I want to do this, I can do this, please just give me a little time and don't be sorry, I know you couldn't exactly help that. It's on me." Ashley voiced through heavy breaths, not having accounted for the throbbing which would happen. It did make the bigger discomfort shift to a short surge of pain, but she also had to admit that it did make her feel great in a sense. Afterall it was one of the most sincere outings of Bruce's enjoyment and she loved knowing that he was also enjoying this. It made her all the more determined to make this work, despite it turning into less and less of the sexy scenario she had initially envisioned during dinner, she still really wanted to do this. Once she got used to Bruce's size she could focus on making it sexy, but right now she wanted to take all of his cock if for no other reason than to somehow prove to herself that she could.

Bracing herself Ashley pushed back a little more, only to pause yet again. At least the very generous amount of lube made it as easy as it could possibly be as she doubted she could have done it otherwise. Inch by inch Ashley moved back slightly, trying the best she could to deal with the throbs of Bruce's cock which added to her discomfort while simultaneously motiving her and getting her all the more eager to actually be able to properly fuck him like she had wanted. It took a lot of time and effort, but in the end she managed to touch Bruce's hips with her butt cheeks, having taken all of his cock.

Ashley could hardly believe that it had really happened, that she had really managed to take all of Bruce's cock. She was still struggling to adapt to the entire length now buried deep inside of her, but she had done it. While Bruce might not be huge, he definitely felt huge to her. She might feel uncomfortably stuffed, but not only feeling him inside of her, actually feeling his hips, and even his balls resting against her made her feel all the closer to Bruce. It took her a while of just sitting there, keeping all of Bruce inside of her before she finally was accustomed enough to his length and grith to slowly started pulling out. It felt weird, pleasant, but empty as more and more of Bruce's cock left her bottom until just the tip remained inside and she started pushing back against it again.

Staying still for a couple of moments every so often along Bruce's shaft was one thing, but taking him nearly out and all the way back inside in one slow, yet smooth motion was a whole other beast. It was hard, but incredibly satisfying to think that she was actually fucking Bruce. It was a wildly different sensation, other than any she had ever experienced before, weird, but good. Good enough to do it again, after a small pause of letting his cock rest all the way inside of her again. It went a little easier this time, as she did it again with a smaller break, then again, and again until she wasn't even taking a break in between anymore, fucking him in slow, but continuous back and forth moments as her ass continued to adapt. It was weird, but very addictive, completely different from her romanticized fantasies regarding getting fucked, but she was really getting a taste for it.

Especially now that the discomfort was slowly decreasing and that weirdly pleasant sensation turned to being actually pleasurable. There was one sweet spot, that just felt so nice when Bruce's cock pressed into it, making her own rock hard cock throb every time it happened. Luckily it was carefully hidden underneath her so she didn't have to see it or think about it, able to just enjoy the sensation of fucking herself on Bruce's cock as she chased the pleasure of him pressing into that sweet spot time and time again, motivating her to really start fucking herself on his shaft, picking up the pace slowly but surely.

For perhaps the first time in her life she felt truly complete. Her earlier insecurities when it came to stripping down were mitigated by all of Bruce's loving encouragement and not seeing the parts which actually made her feel insecure. Hearing him moan behind her as she fucked his cock also really fuelled her confidence. With the sensation of her lingerie she could feel sexy again, and the fact that she was actually fucking a handsome guy like she had often dreamed of, completed the picture. This was nothing but amazing and she was so glad that she had pushed through to actually fucking Bruce. Her own cock was leaking profusely over the building pleasure deep inside of her. It was a weird pleasure, vastly different than what she built up through masturbating her cock in the past and she loved it. She might have no idea what being an actual woman felt like, but for the first time she really did feel like a woman as her own moans mixed with those of Bruce, her breathing only becoming heavier as she pushed back harder and faster, her cheeks making a loud slapping sound each time they smacked into Bruce's hips. It was mesmerising and so very hot to hear mixing with both their moans.

With how vigorously Ashely was now fucking his cock, it became pretty much impossible for Bruce to gently bow over her back and nuzzle her neck. He needed to get up on his knees for more stability, and as he did, he gently placed his hands on her hips, doing nothing, but just resting them there. Ashley for her part interpreted his actions a little differently, consumed by lust and in the heat of the moment, she moaned out loudly. "Mmmm fuck yes Bruce, fuck me, make me yours, please just take me like you mean it." she cried out, loving how his hands felt so warm on her hips. She loved teasing, she loved taking charge like she had with the blowjob, but there was something about surrendering herself to Bruce and the pleasure of getting fucked that was also incredibly hot, and now that she could take his cock, she couldn't wait to feel just that.

Bruce for his part wasn't about to say no to that. Feeling Ashely's tight ass massage his cock had been downright amazing, especially when she had started picking up the pace. If she hadn't blown him earlier he would have lost it already. In either case, doing absolutely nothing, leaving it completely to Ashley to do at her own pace on her own terms had been incredibly hard to restrain himself from even the slightest bit of involvement, especially when she had been getting really into it, but the last thing he had wanted was to trigger anything bad within Ashley. Now that she was asking for it though he was more than happy to oblige. The words had barely left Ashley's mouth when he tightened his grip on her hips, taking charge of her movements rather than letting her continue to use him as a living dildo like he had up until now. With a firm grip keeping Ashley in place, Bruce quickly slammed his cock into her ass, only to pull back out and slam it back in. Rapidly building up towards the pace in which Ashley had been fucking him. Aside from the fact that it was now him fucking her instead of the other way around, not a lot had changed at all.

It felt amazing to Ashley to let go of all control and simply give in to her carnal desires, the desire to get fucked hard and fast. The sheer pleasure of it all and the fact that she didn't really have to think about anything anymore, that she could just give in, relax and enjoy the pleasure to the fullest was downright amazing. It didn't take very long after that for her to have an actual orgasm, an orgasm getting fucked long and hard by this hot guy she was most definitely in love with. Her own cock spraying cum all over the sheet underneath without ever being touched, allowing her to nearly forget that it was there to begin with. It was fantastic and there was no place she would rather be right now. Nothing she would rather be doing than being here in Bruce's bed getting her ass pounded while loving the sensation, and most importantly she had nothing left to worry about. All obstacles to be who she wanted to be were out of the way, enabling her to give in to the sensations and relax all the more.

From how hard Bruce was fucking her she could most definitely feel that he was very into her as well, that he wasn't faking a thing to save his own skin in front of his friends earlier. With the orgasm rolling through her body she was even able to forget her earlier doubts and insecurities about this all and it was great. At least until Bruce changed things up a bit while her head was still swimming with orgasmic bliss. He pushed her down only to flip her onto her back, moving her legs over his shoulders to start fucking her in missionary position. Bruce wanted Ashely to feel amazing and he had waited every step of the way, letting her do everything at her own pace, not taking the slightest initiative of his own until now. He feared it might backfire, but he wanted Ashley to show that he loved her even if he could see her flat chest and cock, that she had nothing to worry about, nothing to hide from him. He couldn't even imagine how hard it had to be to deal with the things she was dealing with, to be this mortified over her own body, and now might not be the time to do this, plus it might not be his place to initiate it, but he wanted to help, and with his own mind severely muddled by the pleasure of Ashley's tight ass, he had taken the leap anyways. At worst it might kill the mood and end with him denied, as she had already had her orgasm, he figured and that was a risk he was willing to take, if it potentially could make Ashley more at ease, at home around him. Failing to think on how it might be breaking trust stemming out of his over stimulated brain out of nothing but good intentions.

Ashley loved getting taken charge of until Bruce decided to flip her over. In the heat of the moment she hadn't fully realised what it had been he was doing, until she found herself right on her back only to realise that Bruce could now see the parts she was most self conscious of. She couldn't help but squirm, feeling that this whole amazing thing she had going would collapse now that Bruce saw those parts of her. It made her want to hide, especially when she saw the look of worry on his face, but much to her surprise, he ended up just leaning forward and kissing her full on the lips, while he pumped his cock deep inside of her. "You're stunning Ashley, I can't believe what a lucky guy I am. I'm sorry for flipping you on your back, but I just couldn't help but want to see that pretty face of yours. Can you forgive me?" He whispered in her ear, trying to sway her mortification into confidence. He finished his little speech by giving Ashley yet another passionate kiss.

Despite all of Bruce's confirmation Ashley still couldn't help but feel a little squeamish. She could see Bruce meant very well and that he really meant what he said, but still she couldn't help but squirm, knowing full well that the issue was mainly between her own two ears, but she couldn't help it. She didn't blame Bruce at all and his words really did make her glow, but she was feeling anything but at ease. She really didn't want him to feel bad about what he had just caused though and she didn't want to deny him to look at her face either, despite her own discomfort. She knew she was being silly and that it wasn't fair to ruin Bruce's mood while she had already managed to get off, so trying her best she put on a bright smile and tried to act as if all was great, leaning up to engage Bruce into another kiss as she gushed out. "I definitely do Bruce." It was a little awkward and she was a little tense, but luckily Bruce was turned on enough to buy her bad acting of feeling more comfortable already, and a lot of kissing also made it easier to keep the act up as it distracted Bruce from seeing her awkwardness.

The kisses not only distracted Bruce, but Ashley as well, feeling Bruce continue to fuck and kiss her while she was trying to act like her insecurities were gone, actually helped her forget about them, allowing her to get way more into it again as slowly but surely she was actually making it through faking it and it was liberating as she slowly but surely worried less and less, enjoying herself all the more now that she could actually see Bruce and kiss him while they fucked. It was so much more intimate and so much more intense as they slowly but surely moved to a mutual climax together.

When Bruce had given her a warning that he was about to cum, Ashley had thrown her legs off of his shoulders and flung them around his back, pulling him in very close, clearly wanting him to finish inside of her, and while Bruce had wanted to leave her to choose what she wanted, he couldn't be any happier with the choice she had made or the way she had made it clear for that matter. So just like that he had kept his deep inside Ashley's ass, spewing cum while Ashley's cock was spewing cum all over her own stomach. Both were way too wrapped up in the moment to care about any of it though as they just carried on with their heavy kissing and cuddling throughout their orgasms and long thereafter.

Neither of them knew exactly how long they had spent just laying there, cuddling and kissing as they enjoyed the aftermath of their intense orgasms, but neither of them cared. It had felt like an eternity, yet at the same time, like it had passed by in the blink of an eye, but one thing was for certain they had both enjoyed themselves to the fullest. In the end both were completely spent. The rollercoaster of stress and emotions that today had been paired with the long physical exhausting sex they had just had, had inevitably taken its toll. Bruce's limp cock had long since slipped out of Ashley's ass which felt kind of sore, but it had been so worth it, she thought as Bruce finally rolled off of her. By the end she had forgotten all about her insecurities, too wrapped up in bliss and deeply in love. She might not have liked Bruce's sudden well-meant push to be face to face, but she had ended up appreciating it big time with a huge smile on her face as he gently nuzzled her neck from the side. "Mmm that was spectacular Ashley, downright perfect. Hell you're amazing and downright perfect and I just have to be one of the luckiest guys around to get to be with you, to have met you." Bruce gushed his sincere amazement, telling Ashley that the love was very much mutual between the two of them.

Ashley was beaming with joy and love. What had started out as one of the most stressful days of her life, one of the many as of recent, had turned out into the best day of her life so far. Despite her slightly sore ass she couldn't think of a place she would rather be right now than next to Bruce in his bed after some amazing sex. For the first time in her life she had all she had ever dared dream off and so much more still. "Mmm, you're amazing Bruce, will you hold me through the night? That's about the only thing I can think of to make today even better." Ashley gushingly asked while scooting closer with her back to him as Bruce couldn't help but chuckle a little as he eagerly took the big spoon position only to wrap one of his strong hands over Ashley's torso, pulling her close as he kissed her neck tenderly.

"Mmm, of course, I wouldn't want to have it any other way." Bruce grinned as she continued nuzzling Ashley's neck while gently caressing her body with the hand embracing her. Ashley for her part just nuzzled a little deeper into his embrace, getting really comfortable in his arms and it felt amazing to just close her eyes, rest her head and get loved feeling Bruce's body press into hers as he turned off the lights. Neither of them was able to tell who the first one to drift off to sleep was as they peacefully remained huddled up together feeling absolutely fantastic. They both were exactly where they wanted to be and they didn't see that change any time soon as they started a long blissful night filled with amazing dreams.

In the meantime back at Ashley's house Keria was still nervously keeping an eye on her phone, hoping against all hope for a message from Ashley, or maybe from the girl who she had dated. She had tried sending a few more messages, trying different platforms each time but whatever platform she tried, the message that her message couldn't be delivered popped up on her screen making her realise that she was just getting herself blocked on every single platform. Meanwhile no matter where she tried to reach her brother, there was radio silence. She didn't know if Ash was ignoring her, or if he just hadn't seen her messages yet. She desperately hoped it was the latter, but after all the things she had done to him, she couldn't help but fear it was the former. On the one hand her plea had not been shut down, and she hadn't been blocked yet, so there was hope. On the other hand she had no idea where she stood and it kept her on maddening edge.

Whether she liked it or not, it wasn't changing one bit, and with Ashley already asleep it wouldn't change in the near future either. She was doomed to head into a very long restless night, the kind she had forced Ashley to have for a while with all her cruel manipulations. As she continued to wallow in self-pity, she couldn't help but blame herself for her situation. She hadn't regretted it right until now when it had blown up right in her face, but she most definitely regretted it now. Self-centred as she was her first instinct had been to blame Ashley to ruin her date with what he and Bruce had arranged behind her back, but she was smart enough to realise that was hardly rational which didn't ease her anxious waiting for some kind of news one bit.

Chapter 23

Ashley had a better night than any she could ever remember, especially as of late with how stressful Keira had made her life, all those troubles were gone now though, taken care of for better or for worse, there was nothing Keira could do to screw either her or Bruce over anymore and it was freeing. Rather than the nightmares about being outed, or Keira screwing things up with Bruce making him disappear for good from her life, her dreams were now filled with great prospects for the future. In them she had perfect breasts and a figure to match them as she spent every single minute of every single day with Bruce, having fun dates, naughty dates, romantic moments, hot ones, traveling around the world, running fashion shows. It was downright amazing, and although her life wasn't perfect yet, how she was still struggling from huge insecurities about her body, her relationship, not fully able to believe that it was all real just yet. She did blissfully feel like she woke up in a dream as a few rays of sunshine shone into the room through a slight slit between the curtains. Bruce's arms were still wrapped around her, his warmth radiating on her, his body pressing into her back and her breath gently caressing her neck. It felt great and she didn't want this moment to end, and right now it didn't look like it would end too soon either, as she just snuggled a bit deeper into his embrace, thinking about how lucky she was.

As Ashley was shaking off the slight sleep grogginess, her feelings of bliss were getting slightly obscured by her insecurities again. She became fully aware that she didn't have the breasts, nor the body of her dreams and her morning wood throbbing beneath the sheets was also bothering her big time. It did give her a lot of pleasure, but she couldn't help but worry that it would be too much for Bruce and that he would dump her over it. Despite all Bruce's reassurances and the fun they had had last night, Bruce potentially dumping her over who she was remained a worry for Ashley making her cherish this moment even more. Rationally speaking she knew that it was something she was unnecessarily worrying about, that if he hadn't dumped her yet, that he probably wouldn't do so now, but she just couldn't help it, her insecurities were bigger than her rational mind, it didn't spoil the bliss, but it definitely took away from the care free nature of it.

She tried hard not to think of it, to just enjoy the moment, even clinging onto the reasoning that how kind of sore her ass was, was prove of just how much Bruce liked her. It was sore for sure, but she had no regrets about it at all, if she could do it all over again she most definitely would, and even now she was playing with the idea of positioning herself so that Bruce's morning wood would slip into her, the idea of fucking him awake, both naughty and absolutely thrilling. Yet she couldn't bring herself to do it, what if Bruce wouldn't like it, what if he would get mad? No, right now she decided to just enjoy his embrace which was honestly great as well as she snuggled into it a little more.

Ashley had no idea how long she ended up laying there, slightly pondering, but above all loving Bruce's embrace, but she did know she was in heaven when Bruce finally woke up only to kiss her neck with a soft moan as he groggily spoke. "Mmm, you have no idea how good it feels to wake up with the girl of my dreams in my arms. Good morning Ashley, I hope you had a good night." With how he sounded like he was still half asleep it sounded all the more genuine and Ashley couldn't help but feel overjoyed about it.

"Mmmm, trust me Bruce, I think I have a pretty good idea of how that feels cause waking up in your arms has been pretty similar. I could stay here with you forever, and right now I don't see why we should be getting out of bed yet, but maybe, just maybe we can fill our morning with something even more fun if you catch my drift." Ashley moaned in response, kind of wanting to turn around to be face to face with Bruce and kiss him for real, but scared that she might hit him with her cock and freak him out in the process. She wasn't too shy or scared to push her ass back and rub it straight up against his morning wood though, it felt thrilling and so very powerful, especially when it made Bruce moan right into her ear. God she loved this man and she loved teasing him to no end. With her insecurities hidden under the covers, she had the confidence to do so as well.

With all her teasing Bruce was all too happy to take her up on that offer, catching her slightly off guard when rather than sliding his cock into her ass, her flipped her onto her back, inadvertently making her insecurities peak once more as she knew her cock was poking right up against him. It made Ashley squirm awkwardly, wanting to apologise, not knowing what to do with herself only to be calmed down again when Bruce completely unphased by what he was feeling kissed her full on the lips as he started gently guiding his cock into her slightly sore ass. It was a bit uncomfortable at first with how sore she was from the day before, but it quickly started feeling good on a physical level again mentally it had been amazing from the moment Bruce had pressed his lips to hers, not caring about her lack of breasts or her cock for that matter. His lack of care and the passionate way in which he made out with her really helped her forget about her own insecurities for a while as he started to slowly but surely fuck her at a steady pace as they both lost themselves to the pleasure like what had happened last night. Ashley couldn't think of a better way to spend her morning, and at the moment she couldn't think much at all, she was just lost to pleasure and passion, enjoying herself rather than thinking about all kinds of things.