That first night, after I’d watched Josie swallow my cum, we kissed as s(he) stroked my still-hard cock, until I told her Katie might wonder where I was if she woke up to find me gone. Josie looked up at me, still standing there in that schoolgirl outfit, now covered in saliva and cum.

"Will you dream of me, Daddy?" s(he) said softly.

"I don’t think there’s any way I could not princess," I said as I reached down and caressed her smooth ass.

I gave her perfect cheeks one last squeeze, kissed her lips, still tasting of my seed, and snuck back down the hallway and into Katie’s room. After I pulled back the sheets and squeezed into bed next to Katie, I lay there in the dark, looking up at the ceiling. I had to fight the urge to reach under the sheets and play with my cock as images of Josie's hungry mouth and pleading eyes replayed in my mind. I knew that nothing could ever be the same after that night.

The next day I woke up late to find that Joe had already gone out to meet some friends. I let out a silent prayer of thanks for this as came downstairs to eat breakfast with Katie and her parents. I didn’t think I’d be able to sit in the same room as Joe and not either go red-faced or get an immediate hard-on. Probably both.

We headed back to university that morning, Katie’s parents apologizing to me that Joe had rudely left before I’d had the chance to say goodbye. My mind flashed back to the night before, Joe dressed up as a slutty schoolgirl, hungrily taking my cock between his lips. That’s ok, I told them, we’d gotten to know each other even better this trip and I assured them I’d be messaging him soon. Very soon, I thought as we reversed out of their drive.

I dropped Katie back off at her house, kissed her goodbye, and told her I’d see her the next day. Afterward, I drove back to the house I shared with two other guys, went to my room, locked the door behind me, and turned on my phone. The minute I saw I had unopened messages from Joe I felt instant heat in my groin.

"Fuck, Daddy, I’ve been licking my lips all day trying to get every taste of your perfect cock that I can," one message read.

"I’m out with my friends, and I’m still wearing the panties you made me cum in last night," another one said.

I messaged him back and got an instant reply. He was with his friends, they’d headed to the cinema and so he couldn’t send me any new photos, but that didn’t stop him from telling me where and how he wanted my big dick inside him. I stroked my cock to Joe’s messages, turned on even more by the fact that he was sex chatting with me whilst sitting inches from his friends.

I made myself cum to his messages and for a brief minute my lust abated afterward, I marveled at the fact that this boy was making me so unbelievably horny. I wasn’t gay, I had never thought sexually about men in my life or ever found a man even remotely attractive. Yet, when Joe text me later that night, looking irresistible in a pink babydoll, with the caption, ‘This little slut misses her Daddy’s dick,’ my cock was instantly hard.

I started messaging Joe every day. In classes, when I was out with friends, even when I was with Katie. The minute I saw a reply from him my cock twitched in my boxers. I’d open the chat to find another image of him wearing one of Katie’s lingerie sets, along with pleading messages asking me to fill him with my cum.

His messages would make me so horny that I'd often have to go and lock myself in the bathroom of whatever establishment I was currently in, and stroke myself to the pictures he'd sent me. Photos of him in make-up, dressed in a sexy outfit, posed on his knees looking up at the camera pleadingly or bent over spreading his perfect ass, or lying on the bed with his legs spread.

Joe liked to hear about how he’d made me so hard that I’d had to pause my gym workout to go and make myself cum to his pictures, or how I’d been out with friends and had to excuse myself to disappear into a bathroom stall when he sent through more pleading texts. He especially liked to turn me on when I was over at Katie’s house, knowing that his sister was sleeping inches from me as I read his filthy messages.

One night, after we had made each other cum for what felt like the hundredth time that day, I asked how this had all started. When had he begun dressing? Had he been with a man before? Had he meant for me to walk in? He replied that my walking in was just an accident, he had never been with a man before and had never really intended to.

Joe told me that around six months ago, he’d been on a sex chatroom late one night when someone had been posting sissy caption porn. He said that the effect had been immediate. The minute he saw the images he felt a stirring in his crotch and he sent the poster a private message begging to be shown more. He’d made himself cum looking at gifs of tiny blonde gurls getting fucked hard in the ass by muscular men, under captions that read ‘the only way for a sissy to cum,’ and ‘how a sissy pays her rent.’

He'd gone back to the same chat room the next night, and the night after that, seeking out sissy captions and stroking himself to the thought of feminine-looking boys dressing up as slutty girls, to be used as sex toys by strong alpha men. What really surprised Joe as he watched those sissy gifs, was that the thought of being one of those girls in the clip, and not the big men fucking them, was what turned him on the most.

After a few weeks of seeking out sissy captions, he realized he needed more. He stroked himself to videos where fembois in sexy lingerie sucked cock hungrily and begged to be used. The more he watched, the more turned on he got, and the more he fantasized about dressing up in one of those sexy outfits.

After three months after his initial introduction to sissy captions, he was watching sissy hypno on his laptop every night. He trawled compilation videos that showed nubile fembois getting fucked in slutty lingerie, as captions reading ‘you need this,’ and ‘present your hole for Daddy', flashed on the screen. Playing over the top would be a husky voiceover continuously reasserting how badly the watcher needed to be feminized into a little cock hungry whore, that that was the only path to true happiness.

It wasn’t long before the thought of being one of those gurls occupied his every waking hour. He would ride the bus to work, listening to sissy hypno on his headphones as he sat next to other commuters, thinking about the videos he’d watched early into the morning and struggling to hide his arousal when he stood up to get off. He became obsessed with the thought of feminization.

Soon he decided to obey those husky voices, the ones that told him he was already in training to become the girl he’d always wanted to be. He found a list of tasks online called ‘The Complete List of Sissy Milestones’, which detailed how a boy could gradually turn himself into a girly little slut. He skipped the first few steps that instructed him to start wearing plain bra and panty sets and went straight to the section about wearing lingerie, a thought that instantly excited him.

Joe worked as a barista at the time, and money was a bit tight to be splashing out on a whole wardrobe of new outfits. Luckily for him, the bedroom next door to his contained a dresser full of sexy underwear. When he opened Katie's drawers and saw her selection of lingerie, he had been shaking in excitement.

The first set he tried on was a pink satin bra, matching thong, garter belt, and white stockings. When he looked at himself in the mirror, the effect was better than he could have hoped for in his wildest dreams. He didn’t look like a girly boy wearing his sister’s lingerie, he looked like a girl, a real girl, a girl who was so sexy, men would fight each other to fuck her. That first time, stood in front of the mirror in Katie's lingerie, Joe was so turned on that he came in her panties without even touching himself.

The day I’d walked into Katie's room to find Joe looking irresistible in that maid’s outfit, he’d been dressing up as a girl whenever he found himself alone at home. He had learned how to put on make-up and do his hair in order to look even more feminine. He’d even started going to the gym to flatten his stomach more and work on rounding out his ass and hips through endless squats.

The funny thing was, despite looking a little feminine before all this and getting teased at school for being gay, Joe insisted he wasn’t. Or at least he hadn’t been before seeing that first captioned gif. Even as he made himself cum to captions of boys being turned into girls and used for sex, and fantasized about being one of those girls, he told himself he wasn’t gay. Although all the hypno and dressing up made him unbelievably horny, he still didn’t think he would ever go through with any of the stuff he had watched online. That all changed the day I walked in and found him posing in front of the mirror.

Hearing about the story of what Joe had been doing in secret, and realizing that my walking in on him had been a complete accident, made my cock rock hard. That unintended encounter could have ended in a million different ways, with us both refusing to speak about it again, or Joe deciding what he was doing was wrong. But it had ended in the best way possible, with Josie soaking my shaft and balls in her spit before swallowing down my cum.

"So where in your training are you now princess?" I messaged, after hearing the story of how Joe had ended up standing in front of me wearing nothing but a slutty maid’s outfit.

"I’m not sure, Daddy, I think you might have made me skip a few steps;)," Josie replied.

"Well princess, although I loved every minute of having your slutty little lips around my dick, now that I own you, I’m responsible for your sissy education, and I don’t want you missing any important lessons;)" I told her.

"Which lessons have I missed, Daddy?!" she asked, along with a picture of her dressed in that schoolgirl outfit, finger on her lips and looking at the camera quizzically.

"First of all baby, we’re going to have to get you some outfits of your own." I wrote, trying to keep control of the conversation despite desperately just wanting to ask for more images of her all dressed up for me.

"I don’t know if I can afford to do that, Daddy:(," Josie replied apologetically.

"Don’t worry about that, princess, Daddy will always take care of his gurl," I reassured her, my cock twitching at the thought that I was about to buy this little slut a whole new wardrobe to dress in for me.

When I was eighteen, my grandfather passed away and, seeing as I was the only living relative he still spoke to, I’d inherited almost everything. That money, coupled with the fact that I’d been laboring on building sites every summer since I was old enough to push a wheelbarrow, meant I had quite a lot of savings.

The next morning, I wired Josie £200 with the instruction to, 'go buy some outfits that Daddy will like.'

Josie messaged me immediately.

"Omfg, Daddy, is that all for me?" she asked.

"The money is for you to spend princess, but remember, anything you buy belongs to Daddy," I told her.

"Yes, Daddy, of course. Does that include me too?" she asked coyly.

"Daddy doesn’t need to buy you, little slut, you’re already his," I replied.

I spent the whole day sitting in lectures, unable to concentrate on anything, unable to think about anything other than what Josie might be buying to show off to me later. I felt a vibration in my pocket and my cock got hard instantly, thinking it must be Josie giving me a sneak peek of her purchases.

I looked at my phone, it was Katie.

"Do you want to come over tonight?" she messaged.

Since that night with Joe, I’d seen plenty of Katie, at least as much as I had done before I’d ended up cumming down her brother’s throat, but I could tell she was worried my mind was elsewhere at times.

"Sorry, babe, I can’t tonight, I’m playing football and then out for drinks afterward," I replied.

I felt bad lying to her, but my lust for Joe had long since overpowered my feelings of guilt. I wanted the night free to view the private show Josie was going to put on for me. As if to affirm my decision, a minute later I got a message from Joe.

When I opened the message, I let out an involuntary moan and had to look around to make sure no one had heard. My cock was instantly hard and straining against my jeans. Josie was in what was unmistakably a shop changing room, standing in front of a full-length mirror in a strappy black lingerie set. Her nipples and ‘tiddies’ as she had called them were barely covered by delicate black lace. The V-string panties she was wearing accentuated her hips perfectly, and more black lace barely hid her excited bulge.

"What do you think, Daddy?" read the message attached to the image.

"I think I’ve never wanted to fuck anything as badly in my entire life," I replied, shifting awkwardly in my seat to hide my growing erection.

"So, you like it?" she asked again, this time attaching an image from behind, a tiny black thong running up between those perfect ass cheeks, and her smooth pale back completely exposed except for a few strips of black material. She was looking over her shoulder at the mirror seductively.

"Princess, it’s lucky I didn’t come shopping with you, because if I was there, I’d be in that stall with you, and we’d be getting thrown out very quickly for making too much noise," I told her. "Now send me more, my little slut, Daddy’s greedy," I ordered.

"Daddy will have to wait! I need to get out of here before I get caught! But I’ll be back home in two hours, and then you can see everyyyyyything;)," She replied.

"Mmmmm, ok princess, I can’t wait. Just so you know, there might be a package waiting for you when you get home." I messaged back.

"Oooo, what is it, Daddy?!" she asked excitedly.

"It’s a surprise baby, you’ll have to wait and see. Don’t open it until Daddy says you can, and make sure you wear that outfit when you get home, it’ll go with your surprise perfectly…" I text back.

Even though I knew I wasn’t going to get any more images for the next few hours, I had to leave class and head home after that exchange. I was so turned on that there was no way I could concentrate, and the hard-on I had just thinking about what I was going to make Josie do later was making it impossible for me to sit still.

While I waited for Josie to tell me she was home, I looked through the pictures that she had been sending me over the last few weeks. She looked so fucking hot in the outfits she posed in for me, and I couldn’t believe that, under that make-up, this perfect little slut was my girlfriend’s little brother. I stroked my cock slowly to Josie’s picture while I waited for her to message, so turned on that I was already leaking pre-cum.

Finally, my phone vibrated and Joe’s name came up on my screen.

"Sorry I was late, Daddy, I had to wait until the parents has gone out to put my make-up on before I could show off for you." the message read.

The next message was a picture of Josie (that’s how I thought about her when she was made-up and looking girly like this) in the little black lingerie set she’d been wearing in the changing room stall. Her hands were on her hips, she looked so pretty and feminine, I wanted her so badly it hurt. Instead of messaging back, I pressed the button for a video call. Josie answered on the second ring.

"Hello, Daddy." She said softly in a perfectly girly voice. "Did you miss me?"

"So fucking much, princess," I replied. "This much in fact." I panned the camera down past my naked abs and showed her my hard cock.

"Mmmmm, fuck, Dadddyyyyy, that looks so tasty," she said with a whine, the camera was held above her, looking down at her perfect body, and I could see her rubbing her bulge through her little black panties.

"Do you need Daddy’s cock, princess?" I asked her, stroking the length slowly on the camera.

She moaned again and rolled her eyes, "It’s ALL I need, Daddy, I literally can’t think of anything else."

"Mmmmm, good gurl, Daddy can’t wait to give it to you again, princess," I said as she moved the camera to show me up and down to show me her body, from her smooth pale shoulders, down her flat tummy and curved hips, all the way down her long stocking-covered legs.

"When, Daddyyy," she moaned, rubbing her bulge a little faster.

"Soon, princess," I replied. "But in the meantime, Daddy got you a little something to make up for his absence. Did you get my package baby?"

Josie nodded and went over to her bed, picking up the cardboard box.

"I did!" she said excitedly as she held it up to the camera.

"Open it, little slut," I commanded.

Josie propped the phone up so she could use both hands to open the box and gasped in excitement when she saw what it contained. Late last night, after wiring her the money to buy lingerie, I’d gone online to get her a present, not quite believing what it was possible to get through Amazon next-day delivery.

Josie took it out of the box and held it up so I could see. It was a peach-colored dildo, about ten inches long. It looked so realistic, veins running down the shaft under the bell-shaped head, all the way to the textured balls at the base, under which sat a rounded suction cup. The hand Josie was holding it with was literally shaking in excitement. She looked at the camera, awaiting my instruction.

"Suck that cock like it's Daddy’s, princess," I instructed. "Make it cum in that slutty little mouth."

She obeyed immediately, looking up at the camera as the tip disappeared between her lips. She started to bob her head up and down as she rubbed the front of her panties, moaning softly as she did so.

"Show Daddy how much you want it, princess, show him how hungry you are for his cum." I told Josie as I watched.

She started bobbing faster, dipping her head down deeper each time so that more and more of the shaft disappeared into her mouth. She was whining unconsciously as she fucked her mouth, and my cock was aching as I watched her saliva soak the toy and dribble down the rubber shaft.

"Tell Daddy how good his cock tastes, baby gurl," I ordered as she started to speed up.

Josie slid the cock out of her mouth.

"It tastes so fucking good, Daddy!" she moaned. "I need it! Your little slut needs to have it in her mouth."

"Do you need it in your little pussy too princess?" I asked quietly.

Josie moaned again and I saw her shake involuntarily.

"Oh my god pleaseeeeee, Daddy," she begged. "I need it in me, please please put it in me."

She was licking the tip of the soaking rubber cock as she pleaded, and it made me want to get in the car, drive over to her house and fuck her senseless, consequences be damned.

"Show Daddy how you’re going to take his cock in that tight little hole, baby," I ordered her.

She was panting hard, her eyes wide with excitement and she nodded her assent to my command. She lay back on the bed, slid her panties off, and spread her legs wide open. She held the phone over her, giving me a bird’s-eye view of her perfect body. She was looking straight into the camera as she used the other hand to guide the dildo into her ass.

I saw her bite her lip as she slid the toy into her, I knew from our chats that the thickest thing she had had inside her before this had been her fingers.

"Think of this as training for Daddy’s cock, princess," I encouraged. "You need to get used to having your ass filled because when Daddy gets hold of you, he is never going to let you off his big dick."

"Yesssss Dadddyyyyyyy." Josie moaned as she pushed more of the dildo into her. I could see that her little clitty was hard and leaking already.

"That’s it my little whore, take it deep, imagine it's Daddy’s perfect cock," I told her.

She groaned and sighed as she pushed it in further, nearly to the hilt, a full seven inches of cock disappeared inside her little ass.

"Such a good gurllll," I said approvingly. "Now fuck that little ass for Daddy."

Josie held the base of the dildo as she started fucking herself with it, pushing it in and out of her little hole as she moaned. The box I had sent her had contained some lube as well as the dildo, and she reached over and poured some onto her ass and the thick shaft that she was grinding on. That sight nearly made me cum, and I had to stop stroking myself just to be able to hold on longer.

Josie’s eyes were partly closed now, and she was panting with each thrust, lost in a world of pleasure as she fucked her little ass properly for the first time. I watched the dildo slide in and out of her, starting to stroke again in time with her thrusts, imagining it was my cock pumping into her.

"Oh god princess, you look so pretty fucking yourself like that," I said as my hand sped up on my shaft.

"Oh god, Daddy, I wish this was you!!!" she screamed.

"Tell me what you need baby, tell Daddy what you need inside you," I said, panting down the phone.

I had had phone sex with Katie before when we had been apart all summer, but this was on a different level. Where Katie had been shy and a little self-conscious at first, Josie was loud and vocal. Begging me to fuck her, telling me how badly she needed my dick in her and that she was nothing but a dirty little whore for Daddy. Watching Josie, looking so perfectly hot in her little black lingerie set, fucking her ass and begging me to drive over and cum inside her tight little hole, was one of the hottest things I had ever seen.

"I need Daddy’s cock." She groaned as she pumped the thick toy in and out of her. "I need Daddy’s cum, on me, in me, all over meee. Come and breed your filthy little slut Dadddyyy, fill me with your cummm," she screamed.

With those words she closed her eyes and let out a cry, arching her back and pushing herself down onto the dildo one more time as her clitty exploded and she shuddered as an orgasm overwhelmed her. The sight of her cumming so hard with that cock buried inside her tipped me over the edge and I came seconds later, moaning Josie’s name as I did.

I lay back on the bed panting, looking at the camera, which showed Josie still jerking a little in aftershocks of pleasure, her hand still holding the rubber cock that was buried in her little hole. Cum laced her flat belly. Some had even splashed onto her little lace top.

"Oh my godddd, Dadddyyyy," she moaned, eyes still closed. "I have NEVER cum like that.’

"Did you like that, princess?" I asked as I smiled at her.

She opened her eyes and looked at the camera.

"I fucking loved it! Let me get another outfit on and maybe we can go again," she purred.

"Mmmmmm, there’s no maybe about it little slut, you need to show on every single thing you bought for me today," I instructed.

"Yes, Daddy, oh god, yes," she squealed in response. "I might have to leave this in me a little longer before I get up though."

"I’m glad you liked your surprise, baby," I said.

"I did, but I think I’d much prefer the real thing," she replied and looked naughtily into the phone.

"Mmmmm, well that’s lucky, princess," I said back, grinning widely, "because one week from now, you’re going to get it."