Chapter 9

When they arrived both Ashley and her mother were all giggles. It took them multiple trips to bring all of Ashley’s new clothes up to her bedroom by which time the floor was literally littered with. They were so consumed by the fun atmosphere that remained after their shopping trip that they didn’t even think about Keira.

Of course it helped that Keira was nowhere to be seen. The moment she had heard the garage open she had rushed up to her room and locked herself in. If yesterday had proven anything it was that her mother was completely on Ash’s side, hell she and her brother had even embraced the name Ashley she had tried to taunt him with. If she wanted to get back at who she still considered her brother she would have to catch him alone so her mother wouldn’t interfere.

All Keira’s plans to humiliated her brother and get back at him for being the torn in her side, had back fired completely. That would all change soon though, or so she hoped at least. Her day home alone had been spent plotting to get back at her brother in ever growing frustration. If Ash liked being a girl so much she would show him. He didn’t even know half how lucky he was getting to live his best life without having to be that girly model her mother and boyfriend pressured her too be.

She should have dumped Bruce’s ass long ago, and while she could have done so she would have had to put up with way too much bullshit because of it. She didn’t want to ruin her mother’s business by destroying the bond with the biggest investor they had. Let’s see how much her brother would like being a girl if he had to put up with her demanding asshole of a boyfriend. Bruce would certainly fall for it as she knew he cheated on her with more feminine girls. She didn’t mind as all those girls did for him she wouldn’t have to do anymore. Ashley was pretty and girly enough for Bruce to fall for her, that much was certain. Keira thought with a devilish smile as she had already sent a few pictures of Ashley to him, telling him her cousin was in town.

Her brother had a girlfriend so clearly he was straight. Having to go on a date with her boyfriend would most definitely teach him a valuable lesson of how lucky he was to be a guy, it would certainly humiliate the living shit out of him and Bruce alike. Oh he would be so mad when she would reveal he had kissed and dated her brother, surely he would want that news to stay under wrap so she’d have something against him as well. She just hoped that Ash was still scared enough of her to be forced into the date.

While Keira was awaiting the moment to spring her devious trap Ashley and Beatrice were going through the time consuming task of reorganising Ashley’s closet. After spending all of yesterday modelling outfits and today dressed in an old outfit of her mother, shopping for more girly clothes it was a bit awkward to see her closet filled with all guy’s clothes. Her guy’s clothes seemed more like a bad memory after these two long exciting days.

Still it grounded Ashley back in reality as well. No matter how she looked at it she was still a guy, she had friends, a girlfriend and they only knew her as a guy. These last two days had been a dream once she had gotten over the awkward bit, but now the doubts that had plagued her returned. She didn’t know if she was ready to show Ashley to all her friends and her girlfriend yet.

No matter how much Ashley wanted to never end this day, to keep on living her life as nothing but Ashley and throw out all of her old clothes she still decided to keep about a dozen of her favourite outfits from when feeling more comfortable as a girl had been her biggest best kept secret. These dozen guy outfits were pushed to a far corner of her closet while the rest got filled with her new purchases and some of her mother’s old clothes.

It was a dream come true as she opened her closet now, being greeted by colourful clothes, dresses, skirts, lingerie instead of her dull boring guy’s clothes. Those were rather hidden from view now, a lot like his small girly stash had been hidden before. Ashley couldn’t wait to try on all of the new outfits she had bought today, but right now it was bedtime. Having spent their day at the mall until the last possible moment and this big reorganisation of her closet it was getting very late. “Thank you so much for the amazing day mom, I loved it. I’m spent though and I can really use a good night’s rest.” Ashley giggled as she gave her mother a tight hug and a kiss.

“You’re very welcome sweetie, goodnight! Just so you know tomorrow I will probably be out for most of the day, I’ll go to that big client to discuss you replacing our injured model and make some visits to present your portfolio to some other clients I just know will love working with you. Goodnight!” Beatrice beamed before leaving the room with a smile, she had had an amazing day herself, but she too was tired.

Ashley felt great as she was alone now, taking a moment to admire today’s look in the mirror. She looked amazing even if she did say so herself and now that the cat was out of the bag she had the freedom to be her real self a lot more often. Right now when her mother had told her about her work for tomorrow she was excited rather than nervous. The more she thought about it, the more she warmed up to the idea of doing some actual modelling. She was really starting to hope that her mother would succeed.

Feeling on top of the world Ashley decided to take a relaxing bath before going to bed, with all this shopping she had worked up a sweat and she didn’t want to soil her brand new satin sheets straight from the start. At least that’s what she argued, all she was really looking for was a reason to test out all her new bathing products. It was silly really, these were her products now and she shouldn’t have to justify using them. She should just take a bath because she wanted to and so she did.

Pampering herself had been great, after her long fun, but exhausting day. Her bath had left her feeling very refreshed and relaxed, surrounded by all the wonderful smells of the products she had picked from her body wash’s to her lotions. Selecting one of her new pyjama’s, a pair of short baggy blue satin shorts with a blue lace trim and a matching spaghetti strap top, Ashley crawled into bed, she loved the feeling of satin all over her body, and the fact that she was now wearing her very own cute pyjama’s, no more borrowed or stolen stuff, this was all hers. Thinking back on the events of today and yesterday Ashley slowly drifted off into a peaceful wonderful sleep.

Chapter 10

Since her mother would be out all day and she had nowhere to go or to be Ashley hadn’t bothered setting an alarm. Besides these past two days might have been amazing, but the constant battle with her insecurities had also taken their toll, nothing a good long night’s sleep couldn’t help though. Keira had other plans though she had set her alarm very early, not wanting to be surprised by Ash being gone before she could get to him again.

It was still early morning, Keira had patiently waited for her mother to be gone from the house so she’d have free reign. It was clear her mother wasn’t on her side, but she was determined to make Ash pay, so far her revenge on him had backfired so she needed to step up her game big time, oh she was quite positive that he would never come back from what she had come up with.

Barging into his room, not even trying to Keira shouted. “Good morning sissy, rise and shine as you, my pathetic excuse for a brother have a date and you are nowhere near ready yet.” She loved the way her brother nearly fell out of bed, completely startled by her loud obnoxious entrance, just like she had hoped shocking him was just so much fun.

“K…keira, what the hell, what are you doing? Could you please leave my room right now? I’m trying to sleep and I’m done taking shit from you.” Ashley said, slightly bolstered in confidence from the shoot and the shopping trip, yet faced with her mean vindictive sister she couldn’t help but feel a little nervous as well. Shocked out of her sleep and still a little groggy, Keira’s words hardly registered, but when they did Ashley’s face turned to shock, a date? What was that supposed to mean?

“That’s where you are wrong sissy brother of mine, you might think you are done with me, but I am no where near done with you yet. You might have mom on your side, but news flash, mom isn’t here and she won’t be for a very long while, at least most of the day if all her previous contract negotiation are something to go off meaning you are stuck here with me.” Keira announced with a big shit eating grin.

“Now I can be wrong, but does your girlfriend now you’ve always wanted to get into her panties literally rather than as a figure of speech? Or your friend do they know you’ve been more interested in their cute butts and big bulges rather than in their friendship?” Keira asked trying her very hardest to play on all of her brother’s insecurities, his fear of coming out was still her largest bargaining chip and judging from how pale he was suddenly getting she knew she hit the jackpot. This was bound to get him a little more pliable to her demands.

“T…that’s not true, I don’t care for my friends in such a way and I am going to tell Kelly eventually that I feel more comfortable as a girl.” Ashley stammered scared to death, it was true what she said and yet she could already imagine the devastation on Kelly’s face and the disgust and hurtful words his friends would have plenty of for him.

A fear Keira expertly kept playing into. “Yeah, like they’re going to believe that? I don’t even care if your gay or not, what do you think your friends would say if they saw you in your cute pyjama’s? What would Kelly think if I told her you came to me asking if I didn’t know a cute gay guy from one of my modelling job cause you were in desperate need of cock and she simply didn’t cut it for you? If I showed her your shoot and new wardrobe who do you think she would believe no matter what you say?” Keira asked menacingly, going in for the final blow. The look of shocked horror followed by defeat on her brother’s face told her all she needed to know.

“I thought so, now I promise to keep quiet so long as you do exactly what I say, mom will never have to find out about this, you tell her, I’ll tell your friends and girlfriend, it’s that simple. Anyways, we’ve wasted more than enough time, it’s time for action now. Like I said you have a date to go on, a lunch date to be more exact. Now follow along, I readied a bath for you.” Keira said as she held the door open for Ashley like a mock gentleman.

Ashley felt more like a mouse backed in a corner by a cat than anything else though as she got out of bed with her head slumped in defeat. She didn’t want to play her sister’s games, but she could let her ruin thing with everyone she had ever cared about like that. With what she had just said Ashley was convinced that she could and would do just that, she had no choice here, she just hoped that it would be the last of Keira’s shit she had to put up with and although she would never admit it, somewhere deep down she also hoped it was a handsome guy she was set up with.

The bath Keira had drawn for her filled the room with a strong flowery smell. The smell of the products she had bought yesterday. She didn’t really mind taking a bath, hell she would have probably taken a bath anyways, and she had selected these products herself so she didn’t really mind that either. The only thing she didn’t like was that it was a bath with the intention of getting ready for a date Keira had set up for her. It distracted from the relaxation a bath was supposed to be. At least Keira hadn’t entered the bathroom with her, she had just locked the door and told her she had 30 minutes.

In the end the warm water and amazing smell managed to sooth some of her worries, but they came back full force when Keira opened the door. She didn’t look inside, just put her hand trough the doorway and threw some stuff on the floor. “Time’s up sissy, it’s time for you to get that ass out of the tub and get dressed. I’ll be waiting with the rest of your stuff in your bedroom.” She said commandingly as Ashley got out of the bath with a loud groan.

Drying herself off Ashley first lotioned up her body then went over to have a look at what her sister dropped in for her to wear. Much to her surprise it wasn’t nearly as bad as she thought it would have been. A simple pair of white lace bikini styled panties with a matching bra, her breast forms and a pair of glossy nude pantyhose. It was rather modest as far as lingerie went that while she had expected her sister to pick out the most outrageously sexy set she could find. Not that she minded as she put on the lingerie, tucked away her cock and put the breast forms into her bra before returning to her room.

“Alright little brother, time to put on your dress. Put your hair into a nice ponytail and put on some subtle makeup, now chop chop.” Keira ordered as she stood to the side with a big grin spread across her face. On Ashley’s bed there was a simple baby blue summer dress with a white lace Peter Pan collar and a skater skirt next to a pair of white leather pumps.

They didn’t have the tallest of heels and the skirt only came a few inches short of reaching her knees. It wasn’t exactly prudish by any means, but not too revealing either. Paired up with her sister’s instructions for her makeup, some soft pink lipstick, lip gloss, a little bit of eyeliner, mascara and some foundation, but nothing more. That and her hair tied off with a baby blue ribbon left for her, she ended up looking modest, dressed up nicely for sure, a little cuter and more playful than just casual, but nothing too much. It actually was an outfit she was rather comfortable being seen in, even for a date.

Then again all the clothes she had bought yesterday were clothes she wouldn’t mind being seen in after seeing how well she had been able to pass. It was just that some of the sets especially with some sexier lingerie were definitely racier. Paired with heavy makeup she could definitely be made to look like a complete slut, giving any guy she would be set up with the wrong idea. Surprisingly enough her sister hadn’t opted for that which was very strange given how she had made her dress up for the shoot.

Although she was suspicious of her sisters intentions Ashley wasn’t about to complain. After all if she had to go out with a guy she really preferred to be dressed somewhat modestly. The last thing she wanted now was for her sister to change her mind on her outfit.

“You look very pretty little brother of mine, very pretty indeed. I have to give it to you, you did win the bet, you can make a prettier girl than me, but that’s only because I’m not trying, I don’t want to look like some prissy sissy girl.” Keira spoke, her tone betraying that she was still salty about having lost the bet. Under any other circumstance Ashley would have put up a triumphant smile, but not now, now she was too nervous for the upcoming date Keira had fixed for her.

“I do have to warn you though bro, when guys see a pretty girl their blood usually rushes to places other than their brains which leaves just enough blood for them to think about the fastest way into your panties. Guys are animals like that, but I don’t expect you to know, you aren’t a real guy after all. You’re probably more interested in the clothes than the actual girl although I guess that means you are thinking about getting into their panties, only literally instead of figuratively.” Keira mocked her brother loving how his blush was dark enough to shine through the light foundation. He should feel at least as embarrassed as he had made her feel during the shoot.

“On their quest to get into your panties guys can get very pushy, or aggressive even. I wonder what one of those guys would do if they found out you’re not really a girl. I don’t think those guys take the fact that they are tricked lightly. “ Keira continued fuelling Ashley’s fear for her upcoming date. She didn’t want to go anywhere with a guy, especially not the date Keira had arranged for her, but what if the guy would force himself on her like Keira claimed could happen? The thought made her shudder. If she ended up in the hospital because of this, their mother would be royally pissed and Keira screwed, but not as screwed as she would be.

“Luckily there are ways to prevent them from getting into your actual panties. You see if you give a guy a good blowjob and make him cum you can prevent him from going further. That is if the blowjob is good which is a big if. I could teach you how to give a good blowjob just in case you’d need it, but you’ll have to ask me. You need to ask me to teach you how to become a good cock sucker.” Keira said with a huge shit eating grin as she watched the shocked horror on Ashley’s face.

Ashley didn’t want to ask such a thing, let alone be taught such a thing by her sister, but despite that all she feared that it was in her best interest. If it really came down to it then sucking a cock was definitely preferable to potentially ending up in the hospital like Keira had made her fear. She was also kind of curious what sucking cock was like, but she would never admit it, and definitely not to Keira.

It was the fear that inevitably made her give in as she softly spoke up. “Keira, could you please teach me to become a good cocksucker?” The words instantly made her blush and shudder. While she was kind of curious asking it out loud was horrible, but she knew Keira enough to know she wouldn’t yield on that front.

A point that quickly got proven when Keira spoke up. “What was that sissy? I couldn’t hear you? I could swear it was something about helping you become an even bigger sissy, but I couldn’t tell for certain.” She had heard Ashley full well, but teasing her was way too much fun.

Knowing Keira wouldn’t drop the case under any circumstance Ashley groaned loudly before repeating herself in a raised voice. “Keira could you please teach me to become a good cocksucker?” She ask, still unable to ask it without shuddering. God this was embarrassing. Then again better some embarrassment now than real trouble later.

The fact that Keira stated laughing loudly wasn’t helping either. “Of course sissy, of course I’ll help you. I thought you would have been a pro by now. It’s better to start late than never though so lets get started shall we? I had a feeling you would ask me that, typical sissies, tell them they have a date and all they can think of is cock. In any case I put up a training corner, now follow me.” Keira taunted as Ashley momentarily thought about arguing that that was not true. In the end she decided to just keep her mouth shut and avoid the argument though. If thinking that made Keira happy then so be it. it wasn’t worth her energy and she knew it was not true.

With a deep sigh Ashely strutted behind her sister, following Keira to her room only to surprised upon entry by a life sized print of some kind of rugged naked blond haired jock with a rough stubble adorning his face, a muscular body and an ample amount of chest hair. What shocked her most of all however was the eight inch realistic looking suction cup dildo stuck to the crotch of the poster.

A huge smirk broke out across Keira’s face as she saw Ashley’s shocked look. “Tada, I wanted to make your experience as authentic as possible so here you go this is the best I could do without involving a real guy. After all we wouldn’t want a guy to get upset if you do a poor job and try to search your panties instead. Just for your info, this is what a real man looks like, not that you could know unless you got a little too antsy looking around in your gym classes.” Keira taunted.

“In any case let’s get started shall we? If you truly are new to this then we still have a lot to do before your date arrives. So walk up to your lover, pay him a compliment, something about his cock, guys love it when you compliment their cock. While you do that, sensually grab onto the base then get down on your knees before him.” She commanded as Ashley could only look shocked.

“Keira, you can’t be serious, this is going way to far.” Ashley complained as she looked at the poster with he cock attached then back to her sister. Her deep bright blush was shining through her makeup even. She had to admit that the guy Keira had selected on poster was a hunk, but this was too much.

“Oh is it Ashley, is this going to far for your poor sheltered sissy fantasy. I doubt that is going to work on a guy, but you can always try if this is making you too uncomfortable. You don’t have to do this you know, you asked for it, but if you want to try your luck without my help then sure don’t mind me. It’s not my ass on the line after all.” Keira said half irritated only further driving up Ashley’s fear to achieve her goal.

As much as she didn’t want to do it, she realised Keira was probably right, she could walk away now, but that wouldn’t be so easy with a pushy guy. Going through this training was sadly her best bet and while she would have preferred to practice on a cucumber or a banana. She knew like with all thing Keira wouldn’t compromise on this either. She might be the one forcing her to go on that date, but in order for the date not to become a complete disaster she sadly needed Keira’s help now.

Bracing herself Ashley walked up to the poster with a light shudder and exclaimed. “Your cock is big.” She awkwardly said as he blush deepened further. She couldn’t believe she was really doing this, but just like Keira had instructed she grabbed onto the base of the rubber cock. The fact that it felt shockingly lifelike and considerably bigger than her own cock had ever felt didn’t go unnoticed as she slowly sunk down to her knees.

“I’m going to stop you right there, do you even believe yourself with such a tone and word choice? I am certain you can do better, so try again, try so sound surprised, amazed and a little excited. Boys like to feel special so make your imaginary lover feel special.” Keira ordered while Ashley groaned in response. As if what she had just done wasn’t bad enough already.

She was fully aware that Keira wouldn’t go forth until she carried out this first step to her satisfaction so with a deep sigh Ashley got back up and approached the poster again. This time she tried to see it as an act with an audience she needed to convince to make it a littler easier. “Oh my god, it’s huge. I’ve never seen one this big.” Ashley gushed enthusiastically as she once again grabbed onto the base of the dildo and knelt down before it.

“Great, that’s a lot better, now pucker up those lips and give the head a kiss, take your time, make it long and sensual. Look up into the guy’s eyes and add a little moan. Make him believe it’s a pleasure to be allowed to worship that cock.” Keira ordered, loving how mortified Ashely was doing as she did just that. She might have her brother looking like the innocent girl next door, but she was definitely teaching him to suck cock like a slut.

“You can follow that up with a long lap, to catch that pearl of precum which is sure to have formed by now. Make sure to act like it’s delicious and never break eye contact. Once you did that you can kiss it again, but this time part your lips as you press them to the head of his cock, let them slowly roll over the head until its completely in your mouth then proceed to circle it with your tongue.” Keira instructed.

Ashley couldn’t believe her sister’s instructions, but she knew better than to defy them as she gave the rubber cock a lick. It tasted weird and plasticy, making her wonder what a real cock would taste like. She had to admit that she was somewhat curious. “Mmmmm” Ashley said as she licked her lips up at the poster, trying her best to put down a world class act, which was all it was, an act she once again tried to convince herself of just to make it all a little easier to deal with. It was still plenty of embarrassing, but as she slowly wrapped her lips around the head and started circling it with her tongue, it did take the worst edge off the shame.

“There you go, you’re a real natural, are you certain this is your first time sucking cock cause you are suspiciously good. In any case the next part will require some practice. You are going to deep throat that cock, go all the way down on it until your nose is pushing against the pubes on the poster and your chin to the balls on that dildo. Do it slowly and steady, then suck hard when you pull back to the head, but don’t pull off, just circle it with your tongue once and go back down.” Keira instructed, relishing how degrading it all was for Ashley.

Wanting this to end as soon as possible Ashley just went ahead and lowered her mouth on the shaft of the dildo, working it a little over half way down before being unable to continue. With it hitting the back of her throat taking it further down just seemed impossible. How could anyone do this? Ashley wondered as she was just about to pull back up, but that was without taking Keira into account. Without a warning what’s however she pushed down on the back of her head, forcing the about two inch dildo deeper down Ashley’s throat making her gag violently.

Keira Mercilessly kept Ashley’s head down on the dildo to the point where she feared she planned to choke her to death on it. Try as she might Ashley simply couldn’t push back against her sister, but then not a moment too soon Keira luckily released her head. “Not bad for a first try, now do it again, we won’t stop until you can take the whole thing.” Keira said not waiting for Ashley to act as she just once again force her head down, smirking with delight as her brother gagged.

Over the course of the next half an hour this cycle repeated time and time again. Keira kept hammering Ashley’s throat down on the dildo until she could push her nose against the poster. In time even the gagging was slowly going down, but it never quite disappeared. Eventually Keira even let Ashley take back control and she made full use of it by continuing to deepthroat afraid that Keira would take over again otherwise. Luckily she could manage to take it all with no help by now although it remained difficult.

This blowjob training was put to an abrupt end when Keira suddenly got a message ping. “That was your date sissy, he’ll be here in 15 minutes go freshen up your makeup and hair cause it’s really needed. Oh and remember, when a guy cums, pull all the way up so he can cum directly into your mouth, once you are certain that he’s done, pull off, show his load to him, then swallow. Remember all these things and you’ll be fine.” Keira explained.

She didn’t need to tell Ashely to go touch up her makeup twice. She was more than happy to get away from this awful training set up. Her head burned bright red as she noticed Keira hadn’t been kidding. The somewhat innocent subtle look she had applied now looked more suited for a ravaged whore. Shuddering lightly Ashley realised she had no time to waste with only fifteen minutes to her date’s arrival. In a hurry she cleaned up her face and started reapplying the makeup like it had been before.

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