Only Ashley Ch. 02

As lovely as vacation was, it was also wonderful to be home.

To Ashley's joy and surprise, her holiday fling had led to a kind of friends-with-benefits situation, and Steven had kept in touch. He was so good at making Ashley feel sexy and wanted, though it was strange on a couple fronts. First of all, it was strange to be intimate with someone so connected to her past -- not just her past self, but her past relationships.

To a lesser degree, Ashley felt how strange it was to be sleeping with a fan. She was pleased to see that, even though he had been welcomed into her bed, Steven was still an active subscriber to her paid sites. He commented regularly and tipped her regularly. When they'd talked about it, he reassured her that he was just supporting her the way he had before and would have kept supporting, even if he'd never gotten to see her in person this way.

As comfortable as home was, it also meant the return of real life issues, like rent and shopping bills, not to mention that feeding the beast she had created with her full time online life required more money spent on lingerie, beauty products, equipment and even props. Ashley was having the time of her life, but it was not without pressure. Even so, things seemed to be continuing to go very well, at least until the letter from her landlord arrived in her mailbox.

With about as little warning as was legally permitted, the letter informed her that she had 30 days to move out, as the apartment she'd lived in for years was needed for an immediate relative of the landlord. She read it over and over, trying to find a way out of it, but it seemed hopeless.

Steven offered to take her out for a drink that evening. She appreciated it, even if it didn't really get the issue at hand out of her thoughts.

"I was just getting to feel good about doing this full time, but I can't afford a new place right now -- not like what I had, with space for costumes and sewing, and now for photoshoots."

"Can I help you?" Steven asked.

"That's sweet -- it really is -- but I can't take your money. This doesn't work for me if I can't support myself."

"I get that," Steven said. "Don't take this the wrong way but, uhm, isn't having men give you money kind of the way you are supporting yourself?"

"That's different. I'm posing for photos for them. I know what they use those photos for, but it's not the same as borrowing money from the man I'm dating and sleeping with."

"No, I mean, why don't you get those men to give you the money that you need. Have a special fundraiser, or offer some custom photos. I'll bet there are lots of your fans who would love to help out."

"Do you really think so?" Ashley asked. "I get kind of nervous that even at the rates I set now, they might think it's too much."

"I'm sure there are always going to be some men who drop off, or don't want to give even a dime more -- but there are also men who'd give much more if it meant they were helping you out."

"Do you think I'd have to do more stuff for them? Or show more?"

"I'm not going to lie -- I think that there would certainly be some value if they were getting something new, or something that you haven't posted before. I'm certainly not suggesting you do anything you're not comfortable with, though."

"I guess. I'll have to think about it."

The whole idea made Ashley nervous, but she also couldn't think of anything else to do. She let herself imagine what kinds of things she might want to put in "bonus" content, or how far she might let herself go. Somewhere around the second page of notes, she realized that she was going to do it, and she let herself take a break and start looking at apartment listings.

Steven was proven correct. It seemed that mere minutes after she uploaded a post about her predicament that tips and gifts started arriving in her inbox. She was amazed and flattered and in awe at the generosity she received. By the end of that first day, she started looking at larger apartments.

Just a few short weeks later, she was all moved into an amazing new loft with a very pretty bedroom, a second bedroom she could fill with clothing and supplies. She loved everything about it, including the location, the space and light. The funds from her crowdfunding more than paid for her first and last month's rent.

She also found that she was actually enjoying the increased level of interaction she now offered as part of a second tier of ongoing subscriptions. She had been a bit worried about a second level of photos, so she'd decided to offer up more personal messages and chatting time as a kind of compromise with herself.

As well as things were going, she also realized that the new bills weren't going to stop. Rent was covered for now, but it was needed every month. One thing she heard over and over from her new inner circle was how much her transition turned them on. It wasn't just that she was pretty and sexy and dressing in revealing outfits, but it was also that they could see how she was changing. These men had been fans for years in some cases, and they loved how her hair was longer and her hips were filling out, not to mention her breasts.

Ashley fed off their comments, using their interest and lust to inspire her photo shoots for the inner circle and for all the men who subscribed. As a strategy, it was working, and she'd never had this level of engagement online before. It was perhaps that mixture of excitement, enjoyment and financial uncertainty that led her to accept the offer.

Her biggest online patron, a generous donor to the crowdfunding as well as a regular tipper, had included a unique suggestion into their latest chat. She knew him as Grant, and he offered her a regular stipend, paid directly to her -- avoiding the percentage lost to any hosting site -- if she would be willing to essentially accelerate her transition. He wasn't asking for anything unsafe, or anything beyond her doctor's recommendations, but he loved watching her become such a sexy woman, and was willing to fund it.

"That's very generous," Ashley had replied, feeling nervous but also in a bit of awe at the amounts of regular, stable cash that the proposal would mean. "I want to be clear though, about what you'd want in return."

"I wouldn't want anything more than we've talked about. I'd like to see you continue to become more feminine and more sexy. I'd like to see you in pretty and sexy outfits as you do so. I'd love to see you do more sexy things on camera, but I also can accept that if you were comfortable doing that, you might have already done so -- and I don't want to push you. I see your joy, which has grown so much since you started doing this, and I'm in a position to be able to help."

"Purely altruistic, then?" Ashley joked.

"Not purely," he replied. "You must know that you turn me on. Seeing you in the kinds of photos and videos I'm asking for will only do more of that."

"You want to jerk off and cum, thinking about me?" Ashley asked.

Of course she knew it was true. She knew that was the case for probably every one of her subscribers and followers, but it never stopped amazing her. She too, back before any of this, was as much "one of the guys" as any of the other men in her fraternity. She would make suggestive comments about the women in the sororities, around campus, and in the movies they saw. She had spent as many nights as any of them alone, looking at porn, and creating a secret folder on her laptop full of images of the kinds of women that got her worked up.

When she looked back at that folder, she was finding herself looking more and more like those girls every day. It was an incredible feeling to actually remember the feeling of wanting to fuck the girls in those photos, while realizing that the model in the photos was now her. The men watching her clips and visiting her site wanted to jerk off, but probably wanted to fuck her too. More and more, Ashley loved those thoughts. She wanted men to fuck her. Maybe not every man who paid their monthly fee, but definitely some of them. This was a detail she wasn't quite ready to confess to Steven, even if they had both made it clear that what they had wasn't exclusive.

Ashley, still reveling in how much she enjoyed her new apartment, changed into a new lingerie set that had just arrived. It was a full kit of panties, bra and thigh high stockings, all in white with the prettiest lace trim. She fluffed out her hair with a blow dryer and brushed it out, then did her makeup. She'd set up lights around her bed earlier, so all she had to do was put on music, get her camera on its mount and take its tiny remote shutter in her hand.

She started posing for the camera, taking photos with every pose and angle. She could almost feel her new patron watching her, touching himself, and wanting to touch her. She hadn't really planned for the shoot to get x-rated, but she reached into her panties nonetheless. Her cock had shrunk, especially while soft, thanks to the treatment, but it still felt so good when she touched it. She rubbed and caressed herself, feeling the warmth rise and the tingling intensify.

She posed for the camera still, tugging her panties down just enough so that it saw everything, including the oozing flow of precum that leaked from her as she got increasingly hot and bothered.

"Fuck it," she whispered to herself, and dug out her favourite dildo vibe.

She coated it with lube, making sure to capture shots of her caressing it suggestively. She switched the camera to capture video, wanting her hands free, but she never forgot the eye of the lens, watching her and seeing all.

She moaned and caressed herself, stroking and tugging, while spreading her legs and giving the camera the best view she could of the dildo pushing inside her tight ass. She was both photographer and model, posing while considering the shots she was getting, all while rubbing and fucking herself. She posed on her back and on all fours. She knelt in front of the camera, trying to seduce the man she imagined behind it.

One advantage of her transition in this situation was that it took so much longer for her to rub her cock to orgasm, which left her so much more time to play upon the dildo. When she could finally hold off no longer, she pushed the vibe up to full and fucked herself mercilessly. She came hard, gasping and panting, and making such a slutty, sticky mess of herself, all over her fingers. She felt so naughty and slutty, looking right down the lens as she licked them clean.

She imagined herself a kept woman, performing on demand, a kind of virtual captive of the men who watched.

Even long after she came and had cleaned up, she still felt the power of what was happening. She selected a couple of photos, barely editing them at all, and sending them back to Grant, along with the words "I accept."

As the months went on, she could feel everything accelerating. Every time she looked in the mirror, she felt a bit prettier and a bit curvier. Her breasts were definitely coming in and filling out. She found that she needed to wear a bra all the time now. It wasn't just a prop for cosplay or sexy shoots, but she needed them to feel comfortable. It was the same with panties. Boxer didn't feel right on her body anymore, so she switched over to panties entirely.

She used to think of the "everyday" version of Ashley as something less than the fully glammed and made up girl who posed for the photos she posted online, but as time went on and her confidence grew along with the changes, she began to see even that version of herself as sexy. She had more confidence just going out into the world as herself, whether it was out for coffee with friends or for walks on her own. She began to notice men looking at her, even flirting with her. They would open doors for her, and sneak looks at her cleavage when they thought she wouldn't notice.

Grant had loved everything, from those first photos she'd sent with her acceptance, and everything since. He had sent along a very generous tip, over and above the agreed-upon stipend. When she hesitated to accept more money, he would send gifts instead, including gift cards that she could use to buy more lingerie and more sex toys.

As generous as Grant was, he was not alone in his support. The new content was proving to be very successful. Men were amazed with how increasingly sexual she had become and seemed to be flocking to her sites. The upper tiers of her subscription sites were booming and profitable, which only meant that more men were seeing Ashley pose in smaller and sexier outfits, and witnessing her pleasure herself for their enjoyment.

She'd never quite have imagined that men would want to see her naked, but at the request of no small amount of her followers, she found herself daring to cross that milestone as well, and her fans went wild for it. They loved her breasts and her hips and her ass, and even her tiny little cock, as soft and humble as it was.

Steven was benefiting as well. Ashley so often found herself intensely aroused by her photo shoots or by the arrival of a new round of packages, and he was her most reliable source to release that passion. They went on dates, to be sure, but Ashley would also call him out of the blue and ask if he was busy. Once he realized what these calls were, he would quickly and eagerly agree to come over as soon as he could, no matter the time of day or night.

She loved having him over to her loft, in this place that her feminization had funded, and wearing the sexy outfits that men had purchased, just to see her wear. She didn't share those thoughts, but they were often in her mind.

Not so long ago at all she had been a man -- a confused man perhaps, one with an ass that had always looked suspiciously round in tight jeans -- but still a man. From those first moments she'd experimented with dressing up and sharing those photos, there had been men to encourage her to go farther. They had been with her, in her mind, as she dared to dress up more and show it all off. Their comforting and encouraging voices had been in her ears when she'd walked into her doctor's office and announced her desire to start her transition.

She liked to play in her mind, now and again, that they had pushed rather than just encouraged. Had she really intended to go this far? Was it really her plan to become a woman, and such a sexy and playful and sexually adventurous woman at that? She wasn't just becoming a girl, she was becoming a model and a sex symbol. These men dressed her up. These men bought her toys and had her fucking them while they watched. Every time her breasts grew another cup size, she fantasized about her body being moulded by the fantasies and desires of these men.

There really was no going back. Becoming and being Ashley paid her rent and financed her life. It funded a lifestyle she could have never afforded before. Ashley was richer and happier than the previous version of herself had ever been, so it was no wonder she was happy to go along with the lusts of these men online, but that didn't mean that, in a way that only made her increasingly mad with lust, they owned her too.

These were the thoughts in her mind when she met Steven at the door, letting her robe fall from her body as soon as the door closed behind him. She was dressed in red lace, with garters and a corset added to the already sexy bra and thong. She felt his eyes on her, feeling how much he lusted after her too -- wanting this body that she imagined that men online had convinced her to obtain.

This time, she had an additional surprise for him -- a surprise and a request.

After their first kiss, she twisted herself away and picked up a box for him to open.

"Is this a gift?" he asked.

"Sort of," she said. "Open it."

Steven, smiling the whole time, untied the bow and opened the crip black box, where he found a sleek-looking pair of Ray-Ban sunglasses.

"You got me sunglasses? These look so cool. Thank you."

"So you know what kind they are?" she asked.

"What do you mean? The style?"

"No. These are new. They can take photos or record videos."

"Oh, that's wild."

"I want you to wear them tonight. While we're together."

"You want me to record me fucking you?"

"I do, if you're willing. I thought these would be perfect, since you won't have to worry about anyone seeing your face. It's just that lately I've been wanting to do this. The sexy photos are amazing, but I think I'd look amazing sucking your cock."

"You want to put these up on your site, don't you?"

"Not for everyone, but yes I do. I'll tell you what, if you wear them and record tonight, I won't post anything I don't show you first and get your okay on?"

Steven looked her up and down, his eyes finally settling on her crooked smile.

"There's no way I can say no to you -- not like this. How do I start them up?"

Ashley had already linked them to her computer, so all Steven had to do was tap the side arm, and they started recording. Thrilled that it was actually happening, she slid down onto her knees in front of him and immediately began freeing him from his jeans.

Watching the footage alone later, she was aroused all over again. The way they recorded his point of view as he looked down at her was incredible. She could almost feel him staring at her breasts again and then growing distracted and aroused as she used both hands to guide his rapidly thickening erection to her mouth. She heard herself moan and gasp and suck, taking more and more of him with each wet slurp.

His moans joined hers, and her head bobbed up and down enthusiastically. Steven's hands reached out to caress her hair and guide her head. Her lipstick smeared over his cock and found herself looking deliciously slutty and she drooled around him, now and then her eyes rising up to meet his, and then smiling wide with a full mouth.

She remembered feeling that he was perhaps moments from eruption when she stopped and slowly let his cock slip from her mouth. She rose up slowly, taking him by the hand, and led him to her bed. Stopping just at the foot of the bed, she turned, rose up on her toes to kiss him again, then turned her back to him and slowly pulled her panties down, over her round ass and then down her legs and off. She knelt up on the end of the bed, smiled at him over her shoulder, then bent forward and waited on the bed on all fours.

Steven got the message and, thanks to these wonderful glasses, she got to see just what it looked like for him to hold his spit-shined cock in his hands as he guided it to her tight little puckered rosebud. Ashley was rubbing again, watching the recording. She nearly came again just watching him push himself full and deep inside her, making her body open up and stretch to let him inside. Slowly and lovingly he built up his rhythm, plunging deeper with each stroke.

The video made her remember what it had been to fuck like that, and she was so turned on by seeing this slut on her screen take this cuck and moan with delight. The slut was her, and she could remember how each inch of him had felt as she re-lived the experience and sight of it now.

She'd shown Steven enough of the clip for him to give his permission. He'd be relieved to see how little of himself showed on camera, though he was kind of tickled to see his cock have such a starring role.

As she watched herself be fucked to orgasm while rubbing herself to another one, she could already imagine Grant watching it too, and she knew his cock would be in his hands. Grant, and all these other men who had sent her tips and cash and gifts, or who had just encouraged her along this journey with compliments and the most inspiringly lewd comments posted under her photos. She wasn't just an online model anymore, or one of those sexy traps posing in cute lingerie sets.

She was fucking on camera now, for men. She was their porn, pure and simple. She knew she'd made every choice along the way but, right then, as her fingers pushed herself over the edge and into pure pleasure, she was the boy that the internet turned into a girl -- and a damned sexy one at that.

Making that last click, as her orgasm hit hard, the first edit of this encounter was sent off to Grant and to just one or two of her highest level supporters. She luxuriated in the aftermath of her own pleasure and exposure. It was one more step, one more bell that could not be unrung. It only turned her on more, as what was her amazing life now but a series of points of no return.

Just like the men watching, she couldn't wait to see what might be next for Ashley.

to be continued