Chapter 11

Ashley was just brushing out her hair, the slightly sore throat being the only evidence that was left of her blow job training as she once again looked immaculate. When all of a sudden the door bell rang making her nerves reach an all time high. God she still couldn’t believe this was actually happening, that she was going on a date with an actual guy. Yet she was sure to meet him at any moment now. Hopefully he was at least handsome.

That wasn’t the biggest of her worries however. She worried more about the fact that this guy would actually believe she was a girl meaning that she could under no circumstance let anything on about the fact that she wasn’t really a girl, no matter how much she would like that. The thought of being found out was a terrifying one only enhanced by the fear that she could pass no where near well enough for this. Sure out shopping no one seemed to have noticed or cared much, but going on a date with a guy she would be inspected way closer, that and a guy would definitely care if he found out.

Within seconds Keira barged into her room throwing a small white leather purse Ashley’s way. “it’s time to go and greet your date. I’ve put everything you could possibly need in that purse so I guess that means your ready. If you need to touch up you makeup, there’s some lipstick and powder in there as well. Now let’s go!” She said not really waiting for a reaction as she just grabbed onto her brother’s elbow and dragged him along with her.

“Now remember this well, you are Ashley, you are my niece from upstate and you are just here to visit. If you just stick to that you’ll be more than fine, oh and if a guy goes on about sports or other things you know nothing about, just smile giggle and nod occasionally. You should always giggle whenever he tries to make a joke. Guys love that and it’ll distract from seeing you for who you really are.” Keira said on the way down.

There was no chance for Ashley to reply or verify anything with her sister as they soon arrived at the door which Keira quickly opened, forcing Ashley to drop into her role right away. A role she nearly instantly dropped out of as she instantly recognised the guy on the other side of the door as Bruce the asshole of a boyfriend her sister always complained about. This was so wrong on so many levels, she had been set up with her sisters boyfriend by her sister. Wasn’t that cheating?

“Wow someone doesn’t look happy to see me.” Bruce joked trying to break the ice as he noticed the shocked face of this pretty girl next to his girlfriend. Keira knew he cheated and seemed to be okay with it yet it had still come as a complete surprise to Bruce when she suggested he’d take her niece out for a date. Hell she had even gone as far as to say that if he managed to get her to blow him with a picture as evidence that he’d be allowed to take her ass like he had been nagging her about for forever. She stimulated and even rewarded his cheating and he was all too happy to agree.

He had feared that it would be one ugly girl, after all if Keira was so desperate to get her niece some fun then she had to be one hopeless cause. Still getting to take Keira’s ass in exchange for a blowjob he could just enjoy while he looked away from it would be so very worth it.

Much to his pleasant surprise however that wasn’t the case at all. If anything this girl looked like she was a real catch, she could definitely get a spot among the top five pretties girls he had cheated on Keira with. There was something innocent about her, but that only made her all the more desirable to him. It made him wonder why she wasn’t a model yet, having an aunt with an agency, and Ashley looked way better than Keira, way girlier as well in her heels, dress, hosiery and with her long hair. He was instantly looking forward to this date beyond the prospect of getting to take Keira’s ass.

“Bruce this is Ashley my niece, Ashley this is Bruce. Please forgive her for gawking like that, I’m sure she’s just shocked to see such a handsome guy. She’s a small town girl and she’s always complaining about how there isn’t a single cute guy living anywhere around her isn’t that right Ashley?” Keira casually said covering her brother on this first hurdle.

“Uhm, yeah…” Ashley spoke softly in the feminine voice she had often tried to practice, her cheeks were bright red being put on the spot like this.. She couldn’t believe this was really happening, and then she realised that Keira and Bruce never let on that they had a relationship. Given how she was being set up she could only conclude that Bruce thought she thought he was single. That was one messed up relationship he and her sister had Ashley thought, but she could do nothing about it now. Bruce would probably be as mad as any guy if he found out, and Keira was sure to ruin her life if she messed this up. She was trapped.

“Well in that case colour me flattered Ashley.” Bruce said as she made a deep bow before her, gently taking her hand and planting a kiss on top of it like some sort of gentle man in the movies. Uneasy, but admittedly slightly flattered as she saw Bruce obviously checking her out while he treated her like a lady. Ashley quickly let out a nervous giggle, hoping it was the right thing to do in this kind of situation. Keira just stood off to the side and smirked. Ashley was acting perfectly like the innocent girl next door she was dressed up as, this would show her being a girl wasn’t just fun and games.

“In any case let’s get going shall we? I’ve booked us a restaurant and afterwards we’ll have plenty of time for me to show you what the big city and if the mood is right I have to offer. I’m certain you are going to love it.” Bruce smoothly said, making his intentions clear from the start much to Ashley’s shock, this was shaping up to be a very awkward date, even more so than she had anticipated.

While Bruce was rather good looking, his body a little average in shape, but not muscular, at 6’1” quite tall, he had broad shoulders, short brown hair, brown eyes and a handsome face, Ashley did worry about the asshole his sister had made him out to be. Then again Keira was just as much of an asshole with how she had treated her, and seemingly she was okay and even encouraged Bruce’s cheating so she could hardly use that excuse. She guessed there was nothing wrong with cheating as long as they were both into it, but still if she was in a relationship she would prefer a monogamous one, which sadly wasn’t possible due to Keira. Ashley didn’t want to cheat on her girlfriend even though she knew their relationship wouldn’t last, but right now she had no option.

A quick shove from Keira alerted her to the fact that Bruce had held out his arm for her to take, a hint she hadn’t picked up on as she was too wrapped up in her thoughts. Blushing fiercely she put her daintily manicured hand in the crease of Bruce’s elbow as she joined him at his side. “Thank you Bruce I can’t wait to get to see the city, I’ve heard so much about it, but I’ve never really been out to these parts.” Ashley spoke softly, trying to get into her cover as the innocent small town girl.

She had the feeling that she was the only nervous one here Bruce seemed to be very eager and excited about this date while Keira wore a big grin herself as Bruce guided Ashley down to his car, slowing his pace so she could easily keep up with him in her heels. It’s one thing she had to give to him, he was a real gentle man, slowing his pace, opening her door, helping her in the car and closing the door for her. If the situation had been any different she would have loved to be treated like this, like a real lady, but the stress of having to keep up her cover while going out with her sister’s boyfriend made it hard to really feel at ease.

Bruce quickly got into the driver’s seat and took off as Keira waved them out. Just like that she was on her own. As bad as Keira had been she had proven to at least feel like some sort of support when it came to meeting Bruce, protecting her cover and making her see the hints she’s missed. Now that was gone as well. “So Ashley, what’s it like living in a small town? Doesn’t it get a little boring being around all the same people day in and day out, without any real big events to go to?” Bruce asked casually striking up some small talk as he felt Ashley’s nerves. Having seen Ashley he really wanted this date to work out for more than just getting to take Keira’s ass. He and Keira had an understanding, but he definitely wouldn’t call it a good relationship. They basically wanted opposite things, their relationship just happened to look good to the outside world. Ashley was a lot more his type if he was being honest.

If anything the small talk only made Ashley more nervous though as she had to imagine a whole new life for herself on the spot. “Uhm, it has it’s perks I guess, I mean knowing everyone can be a bit boring and it also sucks if you try to do anything no one should know about, but it’s also nice to really belong to a community I guess. If I’m honest I’m more interested in what you’re doing, what’s life in the city like?” Ashley said, trying to get Bruce to do the talking instead.

It caught Bruce completely off guard as he was used to showing a deep rooted interest in girls in order to charm them. It often worked way better than bragging about himself, but if Ashley insisted then he didn’t mind talking about himself. In fact it was rather nice to get to talk about himself for a change and Ashley seemed to hang on his lips which was nice. She attentively listened to everything he had to say, mixing in an occasional nod of acknowledgement, a giggle or a few words here and there.

The more he talked the more passionate Bruce became, he didn’t think he had ever connect with a girl as much as he connected with Ashley, at least not so straight of the bat. Ashley for her part managed to relax a little more. Just listening was so much easier than having to keep up her femme voice and keeping her story straight while constantly adding to it. besides, it was also rather nice to hear the passion in Bruce’s voice as he talked.

In what seemed like no time at all to the both of them they reached the restaurant, an upscale place that even had a star. It instantly made Ashley worry that she was way under dressed, but then again, with a pair of black jeans and a white polo shirt Bruce was dressed rather casually himself. If anything she looked more formal than him which at least eased her worries a little. Then it hit her, she had been so invested in Bruce’s talk that she had felt relaxed enough to worry more about the way she was dressed than about the remainder of her date. He didn’t seem like the worst guy making Ashley wonder why Keira made him out to be such an asshole.

Bruce carried on being a real gentleman throughout, quickly opening the car door for her, offering his arm to escort her inside, a very welcome gesture considering how uneven the ground was in some places. Without his arm walking through the gravel parking lot in her heels would have been a very tall task. As necessary as it was Ashley blushed fiercely nonetheless when she had to hold on tight to her sister’s boyfriend’s arm. Their conversation had been nice to the point where she nearly forgot about it, but now that realisation came back full force.

He on the other hand was more than happy, it was nice to have a girl really hanging on his arm for support, something that rarely happened with Keira given how she preferred sneakers over heels and even when he got her to wear heels they were always a pair made for comfort rather than to look pretty and sexy like the pumps Ashley wore.

When they got seated and handed a menu Ashley couldn’t help but gasp when she saw the prices of the food. “Oh my god, this place really is expensive isn’t it?” She had never eaten at such an upscale restaurant before as her mother only went to such places for business, business Keira as a model sometimes got invited on.

“It’s definitely one of the fancier restaurants in town, that’s for sure. I would feel bad if I wasn’t able to offer the best to one of the prettiest girls I’ve ever seen.” Bruce cockily replied with a wink, smirking as Ashley instantly buried her head in the menu, obviously very embarrassed. It was kind of cute, he had never dated such a shy country girl before, neither had he ever dated a girl he clicked with this well.

“Well uhm, thank you for the compliment. I can hardly imagine anything when reading all the items on the menu so I’ll be following your lead I guess.” Ashley shyly said after finally regaining her composure. It seemed to please Bruce to no end as he wore a cocky smile ordering for the both of them when the waiter arrived. His view on being the man might have been a bit outdated for his young age, but Ashley didn’t mind one bit. It made her feel like a princess not having to call any shots as she let ‘her man’ take care of her. It was this old-fashioned stance that what a relationship should be like that clashed heavily with Keira’s fight for independence and her loathing of just being a pretty thing though.

Like she had expected she didn’t recognise much of what she found on her plate when it arrived, the dishes looked more like pieces of art and were very tasty. Although she focused more on eating elegantly than she did on the food itself while also trying to carry on the conversation they had had in the car. It all took a lot of multitasking, but she managed quite well, quickly getting the hang of it as she once again managed to relax rather easily, forgetting all about how messed up this was.

As their lunch progressed Bruce was slowly getting more and more insistent about learning more about her making Ashley slightly nervous again. She had liked her time with him so far, but keeping up a lie, especially with potential dire consequences if she failed was hard and stressful to say the least.

Then an idea hit her, maybe she could talk without having to share much on the persona created for her and so she started talking about her dreams instead. “Living in a small town has its ups and downs, but it’s really boring really quickly, after all these years I’ve really had it there. I dream to one day make it big in the modelling world like Keira, to move here to the city and lead a more exciting life you know? My aunt has been great about it, she even helped me create a portfolio and is actually out seeing if she can get me a contract at the moment. I never thought my dream was realistic, but now it might very well happen.” Ashley spoke passionately and genuinely despite how awkward it was to call her mother aunt.

“That’s great news, if you come to live here we might even get to go on a second date some time. I would most definitely like to pull some strings to make that happen.” Bruce said slightly cocky as he winked yet behind his cockiness there was also a genuine excitement for Ashley which instantly got her to blush first then to worry. Shit if her dream really did come true then she would be stuck in the persona of Keira’s niece for forever and she was bound to make a slipup at some point. She had just doomed herself, but she couldn’t pull her words back, the best she could do now though was roll with it and hope for the best.

“In all seriousness though, why do you think your dream is so unrealistic? I mean if Keira can make it as a model so can you for sure, you are definitely prettier, and actually elegant. I’m sure you would be a joy to work with for any photographer, if I see the grace with which you carry yourself I would say you were a natural, camera and catwalk ready.” Bruce continued, gently stroking Ashley’s hand on the table as she turned all shades of red.

The compliments did sound genuine, but at the same time that made them all the harder to deal with. She couldn’t believe that’s really how Bruce thought and if she was honest she was quite flattered as well. If her mother and now Bruce told her she was a natural then there must be some truth to it right? God why was he getting to her head like that? How should she react, she was so overwhelmed that she would nearly certainly slip up or at least stumble over her words like a fool. She really needed to calm herself down.

So with that in mind she awkwardly pulled her hand back. She didn’t want it to stop, but she needed it to before she messed up. “Uhm if you’ll excuse me, I really need to go to the bathroom.” Ashley awkwardly explained, doing her best to keep her voice nice and feminine as she spoke before rushing off as fast as her heels could carry her without waiting for a reply.

Bruce was left behind a little confused did he say or do something wrong? He really thought they were starting to have a moment. Oh well girls would be girls he guessed. He doubted he would ever truly understand them.

Meanwhile Ashley approached the bathroom she nearly slipped up and went into the guy’s room, given how she looked and how she had pretty much everyone fooled that would be a disaster. Then again heading into the girl’s room felt awkward on it’s own. She might look the part, feel the part and want to be the part, but just like in the lingerie store she couldn’t help but feel like she was an intruder of some kind. She really had to think back to Jessy’s words about her worth to push through, at least the girl’s room had private stalls.

Being away from Bruce and the entire situation with him did help ease her nerves at least a little bit. I felt good to have nothing to really worry about for a while, giving her time to get her thoughts straight. Thoughts like why she was enjoying Bruce’s company so much, hell at times she even manged to forge that this was all set up by her sister instead of a genuine date. Bruce his interest in her and his lust towards her seemed rather genuine and if she was honest she was quite liking him as well. He really didn’t seem like much of an asshole aside from the fact that he cheated on Keira, but then again Keira was the one to set this up. He was a little cocky at most, but most of all quite handsome and a real gentleman. If he wasn’t in a relationship with her sister and if he knew she wasn’t a biological girl she could even see herself with Bruce as her boyfriend, but alas he could never find out so that just wouldn’t happen.

After calming herself down and taking care of business Ashley couldn’t help but notice how her lipstick had faded when she went to clean her hands. That simply wouldn’t do she thought as she reached into her purse to grab out a tube of lipstick for a refresher, only to be shocked when she saw a plethora of condom wrappers, lube and tampons alongside her phone, wallet and lipstick. It knocked the fear right back into her, remembering Keira’s words about how guys thought with their cock and only an orgasm would keep them at bay. She really hoped she wouldn’t need any of those things as it would mean her secret would be out and there was no way of telling what would happen then.

Giving her lips a quick touch up Ashley rapidly closed her purse back up, keeping the contents out of sight in the hope they would leave her mind soon after. They didn’t though and suddenly when she saw Bruce throw a big smile at her she became worried all over again. She tried not to show it though as she gave him a polite smile back.

The remainder of their lunch passed by pretty quickly after that, with Bruce paying for their food and leading a slightly nervous Ashley back to the car. He wondered what had gotten into her ever since she went to the toilet, had he really fucked up that bad? It had felt like they had such a good and relaxed connection up until that point only to then settle back into nervousness. Maybe a ride would ease her nerves he thought as he led Ashley back to the car and showed her all the hotspots in the city.

While Ashley knew the city it was still kind of nice to see it from a different perspective, to get Bruce’s input about it all. Yet she didn’t manage to relax fully again, instead she threw an occasional glance down at his crotch to check whether or not she was still safe from getting fucked and found out in the process. If she didn’t have to worry about her secret so much she had to admit that she wouldn’t really mind the prospect of sex. In all essence the date and Bruce had been surprisingly lovely, and she was kind of curious of what it would be like to be with a guy, just one who liked her for who she really was.

Bruce couldn’t help but notice the constant looks at his groin though. They made him think that Ashley might be so nervous because she wanted to ask to blow him. It would explain why she had touched up her lipstick and he would be lying if he said he didn’t want to find her lips wrapped around his cock. In fact it would be perfect. Keira had made a deal with him that if he could get Ashley to suck his cock and make a picture of it as proof that she’d allow him to finally take her ass like he had been asking for for a while now.

He had to admit that he had really been into it for the deal at first as he had no qualms about trying to get a girl to suck his cock. Yet when had seen Ashley and gotten to know her better that had all changed, she was probably the most lovely girl he had ever met and he didn’t want to ruin potentially getting to know her even better for a quick blowjob. If she wanted it though then he had no real qualms about it, it was a win win really. Just thinking about getting so intimate with Ashley made him rock hard.

It wasn’t something that didn’t escape Ashley’s attention either, instantly firing up her worries another notch. Oh god she really needed to do anything to avoid sex so she could maintain her secret was all she could think about as she kept glancing down at his crotch more frequently, willing the erection to go down. If anything it only got Bruce even more fired up and sure she wanted to suck his cock, but was nervous to make the step.

So in order to make things as comfortable as possible for Ashley, he drove off to a calmer lakeside just outside of the city. It was quite a beautiful place and the lake was huge so there wasn’t too much of an issue finding a quite spot where they wouldn’t be spotted. He really hoped that would take away some of the stress Ashley was feeling.

All Ashley could think about however was that Bruce took her here to fuck her. With her stress of being discovered growing to a climax she remembered her sister’s words of guys just needing to get their rocks of so before he could get too touchy she blurted out. “Can I suck your cock Bruce?” Her face instantly turned beet red as she clasped her hands in front of her mouth, not believing she had really just said that, but she needed to protect her secret at all costs.

Bruce for his part was completely taken aback by Ashley’s sudden aggressive request. He had thought he would have needed to ease her into this a little, to tell her it was okay, but the fact that she instantly asked for it the moment they had some privacy had to mean that he was right and her nervousness had stemmed from her dying to suck his cock. “Uhm, yeah sure you can.” Bruce stammered not as smooth as he would have liked.

It didn’t seem to matter much though as after a brief moment of hesitation Ashley went right to unbuttoning his pants. She feared that if she waited too long Bruce might get impatient and try to fuck her instead as she believed Keira when it came to guys. After all she was the more experience one by far and there were plenty of stories on the news as well. No she had to get this over with quickly and hope that Keira’s lesson’s had been good preparation.

As Ashley fished Bruce’s rock hard cock out of his pants she let out an involuntary gasp, it looked slightly bigger still than the dildo Keira had taught her to suck a little bigger than eight inches of cut, clean shave cock and it was scary to say the least. Yet despite the less than ideal situation Ashley also had to admit it was magnificent. She couldn’t believe she was really about to suck a guy off, which was kind of thrilling as well. She didn’t want Bruce to think that anything was wrong though so she covered her shock up with a compliment, after all guys loved that right? “Oh my god, it’s huge.”

The compliment was followed up by a lewd sloppy kiss right on top of Bruce’s swollen throbbing head. Just like Keira had said there would be, a drop of precum had formed at the tip of Bruce’s cock. While his cock smelled pretty much like his bodywash the precum did have a distinguished musky scent to it. It tasted kind of salty as well as she licked it off with a long lap like Keira had told her to do with the dildo.

Keira’s lessons sure seemed to work as it instantly got a loud moan out of Bruce, one that made her heart flutter in excitement. As much stress as it was to suck Bruce’s cock in order to keep her secret, it was also great to hear how he was enjoying it. It made her a little more confident that this would work, emboldening her efforts as she slowly rolled her lips around the swollen head, getting out a series of moans as she circled the sensitive gland a few times with her tongue, making it throb in her mouth, before she forced her head all the way down with her nose pressing into Bruce’s shaven pubes, before slowly coming back up. It was hard to take him all the way in her throat which was somewhat sore still from the aggressive practice with the dildo Keira had put her through, but at the same time it was also very rewarding as she earned herself a loud gasp from Bruce.

Only looking up in Bruce’s eyes was an impossible instruction to follow while giving head in the car, not that Bruce minded at all if his moans were anything to go off of. All Bruce could really do was marvel at just how good Ashley was at this, he couldn’t believe his luck, this was by far the most amazing and eager blowjob he had ever gotten. Ashley really seemed to be loving his cock where most others, Keira in particular saw it as more of a chore. He really couldn’t wrap his mind around how amazing this girl was. If she ever planned to move here then he was sure to try and take her more often, he would rather be with Ashley than with Keira. Nevertheless he did sneak a quick picture while Ashley was in full action before putting his phone away, feeling kind of like an asshole for doing it, but just in case Ashley was going to go away anyways he would have a reminder and a bit of extra fun out of this.

In the end Ashley didn’t need to bob up and down Bruce’s cock all that long as about five minutes in Bruce lost himself to the pleasure. “I… mmmm I’mmmm going to cummmm.” Bruce warned knowing how most girls hated when someone came in their mouth. Much to his surprise however, Ashley was eager till the end, pulling all the way up to his head, but not off his cock as she teased the head with her tongue until he sprayed her mouth full off cum. She just kept it there, taking each and every spurt, only pulling off when she was certain there was no more too follow.

When she did finally pull off she didn’t spit either, she just swallowed and said. “That was delicious, now if you wouldn’t mind, could you please take me home?” Ashley asked, nervous that he might be getting hard again and wouldn’t take just another blowjob. All in all despite the stress she couldn’t say she had really hated it, getting a guy to cum was pretty fun. The taste and texture weren’t great, but not too bad either, and Bruce’s cock looked great with lipstick rings all over it, still one time was more than scary enough.

“Uhm yeah, yeah sure, we’ll go home, that was amazing Ashley, wow.” Bruce replied somewhat stunned, still riding his post orgasmic high as he got his cock back in his pants and drove off while Ashley started retouching her lipstick, really not wanting her sister to know that she had actually had to suck a cock.

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