On the ride back from Frankie’s studio, Kelly stayed mostly quiet. So many thoughts racing through his mind. The photo shoot went well, wait, who was he kidding, he loved it. Frankie was so helpful, he made sure Kelly was relaxed and coached him on posing, how to play to his camera, plus he was true to his word, he never had to take off his clothes. Well, he was dressed only in those panties and nylons, but he never had to take them off. Even now, as he rode along with Marcy, he wore those panties, under his jeans and they felt amazing. He didn’t have a single thought of needing to be extra careful about it. After all, it was Marcy and Frankie that thought he’d look great wearing panties.
‘So.. what did you think?’ Marcy finally broke the silence.
‘About, all of that? what we just did?’ Kelly questioned.
She nodded without saying anything.
‘I liked it, I mean, that was the first time anybody has ever seen me wear panties before, and it was kind of exciting.’ he confessed.
‘You look really good in them Kelly, you saw some of the photos Frankie said he would be uploading to the website, what did you think?’ she looked at him briefly before turning back to watch the road.
‘Part of me couldn’t believe that was me, it looked like I was in a dream world or something. The photos were getting me umm.. you know.’ he trailed off.
‘Horny? the photos of you in those sexy panties and those nylons made you horny?’ Marcy asked, her voice had lowered some and sounded thicker.
Kelly nodded silently.
‘Okay, well we’re almost to the house. So here is what I’m thinking.. We get you squared away in one of the rooms, there’s plenty of food in the fridge, there’s going to be some of my girls there, I’ll introduce you. Depending on how many are there, you may have a roommate, but I promise you’ll be fine. I’ll have someone go down to the Evergreen and get your things from your room.’ she pulled the BMW up to a beautiful home, and drove up a long driveway, past the house, and parked next to an in-ground pool that had several women laying out sunning themselves.
She reached into her purse, and counted out $500, then handed it to him ‘We’re square on the $500 you owed me for your special night with Anna, and this is extra, for doing so well at the photoshoot with Frankie.’
Kelly looked at the handful of bills, then back to Marcy ‘Umm, thanks, wow, I wasn’t expecting..’
She stopped him ‘Next steps for you.. get settled in, relax, make some friends..’ she paused and then grinned ‘oh, and don’t worry, if you play with any of my girls, there won’t be any surprise charges, okay?’ she held out her hand to him.
Kelly shook her hand ‘okay, deal.’ he looked past her, and let his gaze move to those beautiful girls in the tiny bikinis sunning themselves. Marcy laughed, and opened her door, turning back and curling her finger, as she had done several times in the past, and Kelly followed.
She took him inside the house and showed him around, pointed to a room he could stay in, and then took him out to the pool where the women were talking amongst themselves while soaking up the sun.
‘Hello girls, I want all of you to meet Kelly.’ Marcy said.
All of the girls smiled at Marcy, and then gave Kelly the once-over, dipping their sunglasses down the noses a bit and taking in the young man. All of the attention from the three women caused an already shy Kelly, to squirm and look away.
‘Someone needs to take a dip in the pool.’ a particularly beautiful blonde woman said. Kelly looked at her and immediately felt himself falling for her. She had the slightest tan, her body appeared to be very toned. Her breasts weren’t huge, like the other two women laying there, but they looked perfect on her. He wondered what they’d look like without that bikini covering them up.
‘Come on, I’ll join you!’ she got up and beckoned him.
‘Um, I don’t have a, um, I don’t have any swim trunks.’ Kelly said.
‘So?’ she laughed. ‘Just wear your boxers, or better yet, don’t wear anything at all.’ and with that, she dove into the pool, and swam to the side nearest him. She flashed him a million-dollar smile and teased ‘I’m lonely in here. join me.’
Kelly began unzipping his jeans, and would just join her wearing his boxers, that wouldn’t be too uncomfortable.. Then he remembered he wasn’t wearing boxers, he still had the g-string on from Frankie’s studio. He froze in place, his eyes had gone wide.
‘Well go on Kelly, Beth’s waiting for you..’ he heard Marcy say.
He looked at Marcy, then at the woman in the pool.
‘Go on Kelly, I’ll bet she’d love to see your panties..’ Marcy purred.
‘He’s wearing panties?!’ the women chimed.
Kelly’s face went bright red, and he was about to run away when he heard the woman in the pool say ‘God, that’s so sexy.. show me.’
He played that back in his head a few times to make sure she’d just said that, still unconvinced, he didn’t move.
‘You heard the lady..’ Marcy said ‘show her..’
He pulled off his shirt, and tossed it on the lounge chair Beth had been stretched out on, then unzipped his jeans, and pushed them down his legs, showing off the salmon-colored panties, then tossed the jeans by his shirt.
‘Oh shit that looks good..’ one of the women still sunning herself said. He looked at her and she licked her lips as if she wanted to devour him.
Kelly couldn’t figure it out, he loved wearing panties, but he knew it was wrong, guys don’t wear women’s undies, panties had caused all the trouble that led to him leaving home, but ever since he had left, he’d only found people that seemed to enjoy looking at him wearing girly underwear. Maybe this wasn’t as ‘wrong’ as he’d been thinking. He smiled and relaxed just a bit, and Marcy immediately picked up on that. ‘Go on Loverboy, someone’s waiting for you in the pool.’ she said, then gave his mostly bare ass a playful slap, and turned to go into the house.
Kelly grinned and ran to the edge of the pool, jumping into the air and splashing into the water, he could not have imagined how great this day was turning out to be.
Marcy had Frankie on the phone as she entered the house, and continued to chat as she made her way into her office ‘He’s definitely legal, did you get the photos uploaded?’
Frankie let her know that he had, but that she needed to get the rest of Kelly’s details before he could get the profile completed and posted on the site.
‘I’ll have the talk with him tonight, Beth seems to have a little crush on him maybe, so I’ll work around that. I’ll call you when I have the details.’ and she hung up.
‘So, Marcy said you’re Beth?’ Kelly asked the beauty he was sharing the pool with.
Her eyes sparkled and she nodded her head ‘it’s nice to meet you, Kelly.’
‘You’re, um.. well, it’s just that, well.. you’re gorgeous.’ he stammered, he knew it would be difficult to say, but he had to let her know how beautiful he thought she was.
Beth’s cheeks flushed, and she reached out her arms to hug him ‘That’s so nice of you to say!’ her eyes kept sparkling, and they were quickly making short work of Kelly.
‘You don’t think it’s weird I have on panties? I mean, I don’t wear panties all the time or anything..’ he said ‘I just had them on for this..’
‘Photoshoot?’ Beth finished for him.
‘Yeah.. but, umm how did you know that?’ he asked, puzzled that she would know.
She moved close to him, her beautiful eyes staring steadily into his, and she moved her mouth near his ear and whispered ‘I did a photoshoot with Marcy and Frankie before I came here too.’
Kelly nodded, and said ‘Did Frankie put you in panties and a bra for your photoshoot?’
‘Just panties… and some stockings.’ Beth smiled.
‘Wow, I wish I could have been there to see that!’ he said, his confidence starting to rise a bit, he let his eyes drift from her beautiful face to her perfectly proportioned breasts, straining against the thin fabric of her bikini top. He could see the outline of her nipples pressing against the material, and the unmistakable outline of small rings, the same kind Anna had going through her nipples. His eyes widened, and he looked back at her face.
She grinned at Kelly and purred ‘See anything you like?’ then without waiting for an answer, she lifted her hands behind her neck and untied the bikini top, and peeled the material down, teasingly slow over her firm tits, exposing her pierced nipples. They stiffened a bit more being set free in the air, and Kelly wanted to take in his hands, and then in his mouth. He couldn’t imagine his luck, this was the second naked pair of tits he’d seen in 24 hours. While Anna had huge knockers, Beth had much smaller, better-proportioned breasts, however, both had pierced nipples, and while he’d seen photos, he’d never actually seen real, pierced nipples before yesterday. He decided at that moment that he loved them and that any breasts he’d ever see in the future would be incomplete unless they were similarly adorned with jewelry.
Marcy came out to the pool a few minutes later, and asked Kelly to join her in the house. He looked at Beth with a pained expression, and she giggled and gave him a soft kiss on the cheek, reassuring him that she’d catch up with him soon.
‘So Kelly, it seems like you and Beth are getting along pretty well.’ Marcy said with a grin.
‘She’s beautiful.’ he nodded.
‘Kelly, I just finished talking with Frankie and we’re going to get your photos uploaded onto the website, but I have to ask you some things first, is that okay?’ she paused.
‘Sure, I mean, yeah why not?’ Kelly shrugged.
‘Kelly, it’s really important that you’re honest with me, okay? I don’t want you to feel like you’re too embarrassed to answer something if you’re totally honest with me, I know I can really help you, I mean, in a life-changing way, so do you need a bit to think about this, or are you okay for us to start now?’ her face looked very serious.
‘Let’s just do it, why do I suddenly feel like this isn’t going to be okay?’ he looked back at her, equally serious.
‘It’s just that, well.. let’s just get started.. So Kelly, about the panties.. Tell me more about you wearing panties.’ she let that sink in with him.
Kelly thought a second and considered the fact that none of these new people he’d met had given him a fraction of the shit he got back home when his mom had found his pantie stash. These people, who barely knew him, were totally cool with him wearing panties, so he decided to just be honest with his answers ‘I like how they look, I like how they feel, I like how I look when wearing them. he shrugged ‘I don’t know why I like them, but I do.’
Marcy continued ‘So, just panties? Or?’
‘Well, I’d only ever worn panties until earlier today, those nylons felt incredible, and looking at the photos Frankie took, it felt like it was someone else in the photos’
‘So, you liked them.. Thanks for being honest Kelly, I’m asking you these questions because I want to have the best idea of how I can really help you, so please, let’s continue being honest, okay? she asked.
Kelly nodded.
‘What about bras? Do you like wearing bras?’ she paused.
‘I never have.’ he said ‘I just had panties at home.’
‘Would you like to wear a bra? she asked.
A knock at the door surprised Kelly, but Marcy kept her gaze fixed on Kelly ‘Come in Beth.’ she said.
The door opened, and Beth walked in, smiling at the two of them. She’d changed out of her bikini and was wearing a pink shirt and sweatpants. ‘Is now a good time?’ she asked.
Marcy gestured for her to sit down, and sad ‘I was just asking Kelly if he’d like to wear a bra..’ she said, not having taken her gaze off of Kelly since Beth entered the room.
‘Ooo, I like wearing bras, I like how the material rubs against my nipples with them being stiff all the time now.’ she softly said, her voice dripping with sex.
Kelly swallowed hard and watched Beth as she lifted he fingers to her nipples that were pressing against her shirt.
‘Kelly?’ Marcy brought him back from his stupor.
‘Yeah.. I think I’d like to see what a bra would feel like, how it would look.’ he nodded, he glanced at Beth and saw her eyes sparkling once again.
‘Okay Kelly, so we know you like wearing women’s underwear, you like stockings, what about women’s clothes, I mean generally.. skirts, dresses, blouses?’ she asked.
‘I’ve never worn any of that like I said, I just had some panties..’ he suddenly felt like he’d wished he had more than just that little stash.
‘That’s fine Kelly, but do you think that would be something you’d like. Let’s say, for example, we took you into one of the bedrooms, and there were piles of women’s underthings and many different outfits that would fit you, do you think getting dressed up would be something you’d like to do? she pressed him.
Kelly thought about the photos that Frankie had taken of him earlier in the day, how Franke had made him look, almost like a woman, sure, a flat-chested woman, but he looked far more female than male, at least from the neck down. He wondered what photos of him would look like if he had a complete outfit on.
‘Yeah, I’d like to try that.’ his voice was just above a whisper. He looked from Marcy to Beth, who was looking at him with a familiar smile.
‘Okay, just a couple more Kelly, you’ve been great with your honesty, so please let’s keep it up, okay Hon?’ Marcy said ‘Let’s assume you have a beautiful outfit on, and that you’re wearing a sexy matching bra and panty set underneath. how would you feel about wearing makeup, to complete your look as a woman? Let’s say a professional makeup artist would put your face on for you, and let’s say after she did, that Frankie would want to do another photoshoot with you. How would you feel about that?
Kelly could feel his penis filling with blood, he could now clearly picture himself dressed in a sexy outfit, with makeup on, being photographed, and having his photos uploaded to the web so that everyone could see just how beautiful he was.
‘Yeah, I’d like that.’ he said, the vision in his mind was exciting him more than he would have ever expected, he blamed Frankie’s photography skills.
‘Okay Kelly, last question Hon..’ Marcy knew this one was the toughest, she paused a moment then continued. ‘Let’s say you were all dressed up, and you had another photoshoot with Frankie, and the pictures looked better than you ever would have imagined.’ she hesitated before continuing, but could see the young man breathing quickly as he listened to her words ‘Kelly if all of that happened, do you think you might like to dress like that all the time? I mean, instead of dressing like a guy, do you think you’d maybe like that?’ there, she’d done it, she asked him.
‘Yeah, I think I’d like that..’ he heard himself say before he was even aware he was speaking.
‘Yay!’ Beth squealed and clapped her hands excitedly in front of her.
The noise brought Kelly back to reality, and he looked at Beth and gave her a weak smile ‘I mean, I could never be beautiful like you, but I think it would feel nice, it would feel sexy to try.’
Beth looked at Marcy, and Marcy just nodded to her. Beth stood, walked to Kelly, held out her hand to him, and said ‘Come with me, I want to show you something.’
He took her hand and let her lead him up a flight of stairs to one of the bedrooms, he opened the door and looked back at him saying ‘This one’s ours.’
‘Ours???’ he said trying hard not to choke out the word.
Marcy was back on the phone with Frankie. ‘We’re good, you can fill in the details, Beth is upstairs with him now, so I’ll have the last bits needed for potential Sponsors tomorrow, I’ll talk to you then.’
Upstairs, Beth was showing Kelly the dresser and closet filled with women’s clothing ‘Marcy guessed at some of the sizes, but you’re just a bit taller than me, so I think we should be in good shape. She checked him out again in his jeans and shirt ‘You like going commando? Or do you maybe want a fresh pair of panties to wear?’
Kelly had dropped his jeans without giving it a second thought while Beth picked through the panties drawer, she stopped and let her eyes settle on his crotch, which had been shaved just before the photoshoot earlier in the day ‘Sexy..’ she said.
At that, Kelly gained a bit more confidence ‘Yeah? Do you think so? I mean, you’re the sexy one..’ he said.
‘Okay, well, we’ll both be sexy then.’ she smiled back at him.
She went back to picking through the panties and settled on a pair that were white cotton. She looked at him and smiled ‘these will do nicely for our sexy Kelly.’ She spun him around, then squeezed in behind him, holding the panties in front of him to step through. As he did, she felt his legs brush against her arms, and as she helped him get the panties situated, she turned him and said ‘Tonight, I’m going to show you how to shave your legs.’ she pushed him away with a smile and said ‘But for now, get your pants on, and let’s go downstairs and get something to eat.’
They made their way down to the kitchen and Beth made a couple of salads for them to snack on. Kelly was famished and had hoped for a burger or something, but he didn’t want to complain, as they ate Beth asked ‘You were hoping for a steak or something? and giggled.
‘This is really good.’ he said ‘I don’t usually eat a lot of salads, but this is really good.’
‘Well you’re probably going to be eating a lot more in the future.’ she grinned at him.
Why would he want to eat a lot more salads? Sure, they tasted okay, but he’d rather have a burger any day.
Beth caught the look on his face and laughed ‘Yeah, I thought the same thing, salads? how about some pasta? or a burger!’
Kelly nodded then chuckled ‘I mean, this is really delicious..’ then continued ‘You thought the same thing?’ he asked.
Beth nodded ‘Yeah, when I first came here, I thought the same thing, what’s up with all the salads..’ she studied Kelly, waiting to see what he’d say next.
‘So, just to be clear, earlier you said you had a photoshoot with Frankie..’
Beth nodded.
‘And now, you’re saying when you first came here, you were eating a lot of salads, like we’re doing right now.’ he continued.
Beth nodded again, waiting.
Kelly scratched his head, then putting that thought from his mind, he shook his head and began thinking of some other, more logical explanation.
‘Say it.’ Beth said.
‘Say what?’ Kelly asked, looking at her. Her eyes were sparkling again, but her expression was more serious now.
‘Say what you’re thinking.’ she stated.
‘It doesn’t make sense, I mean, I know why I’m here, there’s no way you’d be here for the same reason.’ he scratched his head again, looking for some other explanation.
‘Kelly, say it.’ she was keenly focused on him now, waiting.
‘Well, I just got into town, and I ended up at a hotel, and then didn’t realize that the woman I met was one of Marcy’s girls, and next thing I know..’ he paused.
‘You owe her $500.’ Beth finished for him.
He scratched his head again, was it possible that Beth was doing the same thing to other guys that Anna had done to him?’ He couldn’t imagine Beth doing that, but nothing else made sense, there is no way Beth showed up and foolishly confused a night of sex with a prostitute as just some dumb luck, she could easily have her pick of partners.
‘It doesn’t make sense, there’s no way you could have owed Marcy $500 as I did, and I don’t believe you would have been running the same kind of game that woman Anna ran on me.’ he shrugged.
‘It wasn’t Anna, but yeah, same deal.’ she kept her eyes riveted on his.
‘Impossible, you’re gorgeous, you’re not clueless like I am, there’s no way you stumbled into the Evergreen and..’ he tried making sense of it, but she just slowly nodded her head.
‘Kelly, do you remember when we were talking about our photoshoots with Frankie, and you asked me what he had me wear?’ she asked.
He nodded, remembering now what she’d said.
‘I told you he had me wear panties, and stockings, just like you were wearing earlier today.’ she watched him.
‘No bra, I remember you said you didn’t wear a bra?’ Kelly began to connect the pieces.
She nodded at him and said ‘I didn’t need a bra, because I didn’t have tits then.’
At that moment, Kelly felt the world begin to spin, he stood, and then quickly braced himself against the large stainless steel refrigerator. Beth stood up and quickly came to him, steadying him. ‘Are you okay Kelly?’ she asked.
He nodded, then looked at her and said ‘there’s no way, there’s just no way.’
She reached for his hand, and slowly pulled it into the waistband of her sweatpants, her eyes stayed locked on his the entire time. She drew his hand down into her sweats until she saw his eyes bulge, then he sank to the floor, nearly taking her with him.
He regained his senses, although he still questioned reality based on what he had just felt, she knelt on the kitchen floor in front of him, this perfectly beautiful woman, who looked like she had been conjured from some artists vision, it wasn’t possible that she, was actually a he, he’d seen her breasts, he’d seen her in her bikini, it just wasn’t possible, it couldn’t be possible.
She stood, and extended a hand, to help him to his feet. ‘Come on Kelly, let’s go upstairs and relax, and let me tell you about Sponsors.’
The room was dark, and they lay in bed next to each other, Beth explained.
‘I’d been wearing my older sister’s panties and bras for a couple of years and then I got caught, I had so much shame I couldn’t bear it, so I took off, and wanted to escape my life until I could figure things out. I ended up in a hotel like the Evergreen, and while my situation didn’t play out exactly like yours, I met Marcy, we talked and I agreed to let them take some pictures of me in women’s underwear, I probably would have done it for free, there’s just something about it that makes me feel complete. Well anyway, they took the photos, and then Marcy asked me a bunch of questions, just like she did with you today. She does this, so they can fill out the information about you and the pictures they upload to their website. The site has a very select, very exclusive customer base, which they call ‘Sponsors’. if one of the Sponsors sees a profile they like, they contact Marcy, who provides some additional details. If things look like there’s a match, an introduction is made between the model, and the Sponsor.’ she finished and waited for his questions.
‘So, what do these Sponsors want?’ Kelly asked, picturing greasy old men, expecting sexual favors.
‘Well, it’s pretty simple really’ Beth went on ‘A Sponsor will basically provide everything you want or need, they have an idea of how far you want to take the feminine stuff, based on your profile. There are some Models that just want to look as beautiful as they can with makeup, shapewear, and the right clothes. Their Sponsor will make sure they have all those things, as well as a place to live, a stocked kitchen, and some spending money.’ she paused.
‘And what do the Sponsors get in return?’ Kelly questioned.
‘Most of them get off on the fact that they are making it possible for the Model to embark on their feminine journey. They get off as much making it happen, as the Model gets off for having it happen if that makes sense.’ she reasoned.
‘So, a Sponsor will pay for clothes, and food, and makeup and stuff..’ Kelly asked.
‘The ones that only want to go that far, yes.’ she answered.
‘But it can go farther?’ Kelly wondered.
‘Yeah, like with me. My Sponsor knew that I wanted tits and a few little procedures, so he paid for all of that, and I think it got him off, that the skinny kid he first met, suddenly had tits, and then a nose job, and then a tracheal shave. I think he got off a little watching that skinny kid become, well become Beth..’ she finished.
‘That’s it? I mean, they just get off paying for everything you want? That’s all they want in return?’ Kelly asked.
‘Some, yeah, mine, he likes to fuck me too, but that’s fine with me, I like getting wild with him.’ she grinned at Kelly.
‘I’m jealous.’ was all he said.
‘Really? Oh my God, that’s so sweet Kelly!’ she grinned again, and then with a giggle ‘Do you wanna get wild with me?’
Kelly was convinced the women on the other side of the house could hear him swallow at Beth’s words ‘Do you? I mean, do you want to get wild?’
she nodded slowly, and added ‘but first, we’re gonna fix you up a bit, and get rid of any yucky hair on your legs, or armpits, or chest, though I didnt see any hair on your chest in the pool..’
‘Yeah, I’m not real hairy..’ he shrugged.
‘Which makes you hotter’ she said ‘So, if you’re into it, we’ll get you cleaned up, then dressed up and done up..’ she smiled ‘and I think after you see yourself like that, you’re gonna have a lot of sexual tension you’ll wanna release.’ she smiled, then licked her lips, knowing tonight was going to be fun.