Becoming Katie Pt. 02: Going Live

Story Info
As Katie grows more confident she decides to show off online.
2.2k words
4.63
4.9k
12

Part 2 of the 3 part series

Updated 11/05/2023
Created 10/30/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Four weeks of lockdown in London, and strangely I had never felt so free. I wasn't stuck as boring old Lee Smith any more - I was Katie Lynette Chadwick whenever I wanted, a tall, shy, curvy girl with shoulder length blonde hair who loved high heels and short skirts.

I had a full feminine wardrobe, containing everything from sexy underwear and slinky dresses to comfortable jumpers and jeans. I'd even invested in a sex toy, a gorgeous dildo that I had nicknamed Pedro. I shaved regularly all over to maintain my femininity, grateful for my limited body hair and slow-growing facial hair.

As Katie, I felt more comfortable, content, and sexual. I regularly joined chat groups and swapped risqué messages with anonymous strangers and admirers.

My online conversations often quickly gravitated towards requests for photos beyond the few I'd uploaded of my legs and butt, but I was far too nervous to show my face.

That was until one happy accident. It wasn't happy initially - in fact it was excruciating. My sister video called me one afternoon, and although I was in boy mode she saw one of my dresses (the white calf-length one with a colourful floral pattern) hanging up in the background and asked whose it was. I'd been single for a while, and the pandemic had nixed any chances of dating.

I was initially hugely embarrassed, but my sister's gentle tone put me at ease. I muttered that it was mine and tried to change the subject, but she smiled warmly and told me it was pretty. Which it was. I didn't know what to say, but after a brief pause she asked what else I had, reassuring me that she supported me and understood my nervousness. It would stay our secret, she said.

I showed her a couple of other outfits, and I started to open up. I told her my new name and admitted that I had no idea what to do about makeup.

"Don't worry," she said. "It's not as daunting as you might think. I'll send you some tutorials and recommendations."

She did more than that. Two days later a package arrived for me containing lipsticks, mascara, eyeliner, eye shadow, foundation, and several brushes, small mirrors and other essentials. I was bowled over - and so excited!

For the next couple of evenings I experimented with my new makeup, watching videos and reading up on how to use everything properly and make my face more feminine.

On the third day of experimenting, I finally got the eyeliner just how I liked it, with little cats eye flicks. I put on some deep red lip gloss and stepped back to assess my work. I barely recognised myself. I was - dare I say it - pretty!

I ran into my bedroom and threw open my wardrobe. I couldn't get into my floral dress fast enough.

After a quick video call to my sister to show her what Katie looked like - she squealed with excitement - I logged on to one of my regular chat rooms and straight away turned my webcam on. Grabbing a bottle of wine and a glass, I settled down.

Within a few minutes I had a couple of messages from other girls like me complimenting my makeup, which was enough to have me grinning from ear to ear.

Soon after, the more lurid comments and requests started coming. Usually I ignored these, but today I felt empowered - and horny! I gave a few admirers a little of what they wanted - feet, legs, ass and panty views - and answered a few questions about sexual fantasies.

One guy, Ricky, was much less creepy and far more interested in me - Katie - as a person. I accepted a friend request and read his quite detailed profile. The site flagged that he was "in my area", and when I saw his topless pictures I knew exactly what areas I wanted him in, if you get my drift.

We swapped a few messages about how we were both coping with lockdown and what we missed doing. Ricky missed dating and watching sport, while I sympathised only with the latter. Dating wasn't on my mind when I still had to get to know myself!

Ricky signed off and I returned my attention to the various horny guys begging for me to show more on camera.

I selected one lucky guy, a stocky but fairly attractive man in his 40s who had sent me a picture of his half-erect cock. I decided I would give him a personal show. Turning my camera to private, I began messaging him.

- Hey handsome. I see you've got a present for me. I like it a lot.

After a moment, his camera came on and an American accent I couldn't quite place came through the speakers.

"Hey darlin'. Fuck, but if you ain't the prettiest thing. I would just love to bend you over and fuck you senseless."

He pushed his chair back so I could see his whole body as he stroked his cock.

I suddenly realised I had never actually spoken as Katie. Well, no time like the present, I thought to myself. I took a sip of wine and adjusted my voice to a higher tone. I settled for a prim, slightly posh version of my English accent.

"Thank you so much," I smiled, biting my lip briefly. "That makes me feel very sexy."

I took another sip.

"But, you know what?" I continued. "If I really was there with you, I wouldn't just bend over and take it."

"Uhh... you wouldn't?"

"Oh no. There's much more to sex than that, sweetheart."

"Call me Daddy."

I shuddered. I hated the idea of calling a sex partner 'daddy' - it was yucky. But I'd made my decision. I'd actually surprised myself with how eager I was to please this total stranger.

"Mmmm," I sucked my finger. "Want to know what I would do for you, Daddy?"

"Oh fuck yeah." His cock was rock hard now, and looked quite tempting.

I smiled demurely. "Well, first I would slip into something a little more revealing. If I do that now, do you promise not to disappear?"

"I'm not going anywhere, you little cock tease!"

He was gagging for it. I practically sprinted to my wardrobe and stripped off my dress. I opted for my red bra and panties, red fishnets, and black heels. As an afterthought, I grabbed Pedro, my 8" dildo, from the drawer under my bed. After a quick check of my hair and makeup in the mirror, I walked back to my desk.

My admirer was still there. He was a little flaccid, but his eyes boggled when he saw me. I adjusted the camera so he could see me in all my glory.

"Yes, fuck yes you slut!" He started jerking off again. "Show me your ass."

I turned and bent over, sliding my hands down my legs. As I stood up I flicked my hair back and parted my lips, licking them slowly.

"What do you want me to do next?" I asked. "Daddy," I added as an afterthought.

"Is that a dildo?" he asked. "Show me what a good little cocksucking whore you are."

"Yes Daddy." I adjusted the camera down and knelt before it. I smiled at Pedro as I started licking and kissing him along the length of his shaft.

"Suck it, bitch!" my watcher shouted. He was getting aggressive, but I didn't mind as he was thousands of miles away. I briefly worried about what he was like in person, but quickly put it out of my mind and focused on sucking Pedro.

Pedro the Penis, my first and favourite sex toy. I had sucked him so many times, often trying to mimic the technique of porn actresses. I had ridden him several times, getting used to the size and feel of it in my ass - and loving every minute.

"Oh yeah, you're a good little cocksucker bitch," the man said, snapping me out of my reverie. "Now ride that dildo like you'd ride my cock. Do it now, slut!"

I can't lie, I thrilled at being shouted at like that. "Yes Daddy," I purred, "Anything for you Daddy."

I placed Pedro on my chair and straddled him, using some saliva to add at least a bit of lubrication. I slipped my fishnets down and pulled my panties aside. Facing the camera and putting on my best 'erotic ecstasy' face, I slowly pushed down on the dildo.

"You're a whore, aren't you? What are you?"

"I'm a whore, Daddy." I moaned as the dildo slid into my ass.

"You're Daddy's little slut aren't you? Say it!"

"Uhhh... I'm Daddy's little slut! Fuck!" Pedro felt so good inside me as I started moving my hips. My cock was straining in my panties, a small precum stain darkening the material.

"Turn around so I can see your ass, slut. And take your panties off."

I did as I was told, manoeuvring to show my ass to my online master, as I'd started to think of him.

"Daddy's cock is good in your ass isn't it, bitch?"

"Oh yes, so good!" I rocked my hips faster. Fuck, it was good. And being watched and bossed around - so hot.

I peered over my shoulder at the screen and saw the man's face contorted in his own sexual lust as he jerked himself off.

"Legs together, slut, and fuck yourself hard! Smash that pussy!"

I bent over, my bare ass central to the camera, and added a little more spit to Pedro. I reached back and pushed him inside my ass, squealing in a mix of pain and pleasure.

"Faster! And lie down on your back! Fucking now, bitch!"

I almost fell over as I scrambled to move the chair and camera into position. I awkwardly lay on my back, crossed my legs at the ankle, and lifted them up, pushing the dildo back in.

"Now ram that ass! Spank it! You're a bad bad girl! Take that dick!" He carried on with a stream of abusive encouragement, and I worked my ass as hard and fast as I could. It was much faster than I preferred, but Pedro didn't let me down and my ass spasmed with pleasure and it was all I could do not to scream as I drew closer to orgasm.

After a minute or so I heard my viewer groan and swear, and saw a spurt of cum shoot up his chest.

"Yes, slut, you made Daddy cum."

"Ooh Daddy, yes! It looks delicious, I wish I could clean up that cum for you."

"Shut up, you dumb bitch. Now cum for Daddy. Show me your cock, you little ass whore."

I didn't need telling twice. Spreading my legs wide, with one hand I kept working my ass with Pedro, slower now but right on my prostate. With the other hand I stroked the head of my cock.

"Fucking cum, you dumb bitch!"

I jerked my cock a few times and pushed Pedro all the way in. A rush of pure ecstasy flowed through me and cum erupted across my stomach. I gasped as the orgasm shook me, and couldn't help but laugh.

"You took too long, bitch," my viewer growled. "I want you to cum on demand."

"I'm sorry, I guess I was having too much fun!" I giggled, secretly proud of maintaining my feminine voice despite the rest of my body still slightly shaking from the post-orgasm high.

"Well, that's the last time I let you take so long. I'm your master now, and you are mine, Bitch Katie. Your ass must be available to me every day. You'll dance for me, ride that dildo and do whatever I say. Now say 'yes Daddy'."

I thought about this for a moment. I had enjoyed this experience, but regular humiliation was not my thing. I preferred slower sex, mutual fun and compliments flowing between partners. No, this wasn't for me. I said as much.

"What the fuck?! Don't you dare! You fucking bitch! I own you! I'll take your ass if I fucking want it! Your pathetic little faggot cock isn't-"

I ended the conversation.

As I was about to log off, a message popped up. I thought it was going to be more imaginative abuse from 'Daddy', but it wasn't. It was Ricky.

- Hey Katie, you still haven't online?

- Hey sweetie, I was just logging off. You okay? Had a good evening?

- Honestly? Boring and lonely. Maybe next time we can do a video call?

- I'd love that. Good night Ricky! xx

- Can't wait :-) Sweet dreams beautiful! xx

Before logging off, I quickly slipped my floral dress back on and snapped a selfie. I sent it to Ricky with the caption "For you xxx" before I could think too much about it, and exited the chat room.

I pictured Ricky's tanned, hairy chest and defined features. I imagined resting my head on his chest. I imagined reaching down with my hand... No, that was enough for one night. Ricky could wait.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
lovesexyshoeslovesexyshoes6 months ago

Great part two! 5 stars.

I would so like to meet Katie Lynette.

Hopeful for part 3.

Kisses, Stef

💋💋

Share this Story

Similar Stories

Becoming My Sister Pt. 01 A boy's obsession with his sister changes his life forever.in Transgender & Crossdressers
Feminizing First Step Ch. 01 A mother begins to feminize her son. First, a new swimsuit.in Transgender & Crossdressers
Pool Boy Gets Dressed Up Ch. 01 Pool boy gets seduced and turned into a tranny.in Transgender & Crossdressers
Summer to Remember Les gets asked to model. But wait, it's women's clothes.in Transgender & Crossdressers
Wife's Lingerie Man enjoys being a woman wearing his wife's lingerie.in Transgender & Crossdressers
More Stories