Becoming Katie Pt. 03: Real Life?

Dating was never my thing in the past, but that was when I was trying to date women.

Now, as Katie, I had slowly grown in confidence to a level I never thought I would reach. After a few weeks of online chatting (and occasional web shows for lucky gentlemen) I felt I wanted to meet someone in real life. I was ready.

But was I?

Physically, I felt ready. I had a wide range of outfits, from comfy to cute, from smart to slutty. My makeup game was on point. I shaved regularly to keep myself smooth. I'd even mastered walking in heels, something that had felt impossible a few weeks earlier.

But as soon as I had resolved that I was ready to leave my flat as Katie for the first time, I was filled with terror. I didn't really know anyone in the area, but what if someone recognised me? What if I wasn't as passable as my online admirers would have me believe?

Worrying about this kept me awake one night, and I decided to go online to seek some support. I visited a cross-dressing forum I had found helpful in the past, and after a few minutes had received several reassurances - but little in the way of useful advice.

Suddenly, the answer was presented by a user known only as PandaGurl. "You're UK, right? So it's, like, 2am there? Can't you go for a walk round the block now while it's quiet?"

How had I not thought of this myself?

After thanking PandaGurl profusely, and with several others sending messages of encouragement, I skipped to my wardrobe.

Slipping out of my wine-red silk pyjamas, I selected my favourite black bra and panties set. I opted for my figure-hugging jeans and a simple black tshirt. My dusty pink flats were next, and to keep warm I slipped on a cute leather jacket I'd just bought myself.

I kept my makeup simple, with eyeliner, mascara and lip gloss applied quickly as my heart beat faster. Satisfied with my cute but understated look, I tiptoed towards the front door. Unlock, put keys in pocket, I tell myself. Don't lock yourself out!

And suddenly, there I was. Outside. My shoulder-length blonde hair blew gently across my face. I was exhilarated. But still terrified.

Taking a deep breath, I crossed the road, watching carefully all around to check for anyone else. I walked quickly down a well-lit pathway between some houses and the park fence. There was a wooded area just beyond another road that I knew I could walk through at leisure without being seen.

I focused on relaxing my shoulders and swinging my hips slightly as I walked. Pausing under a streetlight, I took a couple of selfies to share with the online friends who had urged me on.

Satisfied that I looked sufficiently relaxed (and quite pretty, too, I assured myself), I looked towards the woods.

I had just barely stepped off the pathway when I heard the sound of footsteps. I froze. A shadow came closer - then I saw him. A young, well built, clean shaven man with black hair appeared. He jumped back, obviously startled by my presence.

Someone who wasn't worried by me was his little Jack Russell terrier. The little dog ran past its owner and started sniffing around my feet, occasionally looking up at me expectantly.

I crouched down and fussed the dog as a way of steadying myself a d calming my nerves.

"I'm so sorry," the man said. "I didn't expect to see anyone else out at this time."

I sensed a hint of a Spanish accent. As I looked up at his face he smiled sweetly at me, and I almost sat right down on the path. Now I could see him properly, he was gorgeous. A slight hint of stubble, strong cheekbones, and kind eyes... I had never noticed a man in this way before.

I stumbled to my feet and he caught my arm. My legs nearly gave way again as he gently placed a hand in the small of my back.

"Are you okay?"

"I... uh... yes, yes, sorry! I was startled too... Your dog is cute!"

The man flashed me that smile again. My god, he was handsome.

"He's such a flirt. Always introducing me to pretty women!"

I didn't know what to say, so giggled and tried to hide my blushing face.

"Um, well..." I screamed internally at my brain's inability to find words. "I'm, er, glad he came to say hi, and introduced me to a handsome gentleman."

I sounded so awkward and stupid, but the young man seemed flattered.

"Thank you! Are you okay out on your own? Do you need some company?"

For a moment I considered this, and pictured ripping his clothes off in my hallway, falling to my knees and taking his cock - no, that was daft. Hot as fuck, but I decided not to try to run before I could walk.

Instead, I spluttered out something about needing fresh air and being on my way home, but maybe another time...?

"I'd like that. And so would Bobby here. I'm Diego, by the way."

Why did even the sound of his name make my stomach flip? I was like a teenager with a crush.

"Katie," I smiled, and bent down to fuss Bobby again - this time trying to push my butt out slightly towards Diego.

As I stood up I thought I saw him quickly divert his gaze from my rear, and smiled to myself. I'd never felt so desired, and this was barely anything.

I took a deep breath. "Well, Diego and Bobby, it was really nice to bump into you both like this. I hope it happens again."

"How about I give you my number and we make sure of this?" Diego said.

Getting a stranger's phone number at 2am in the middle of nowhere hadn't been on my mind, but I felt a little rush of excitement as he entered his name and number into my phone and handed it back.

"Call me," he said. "I'd love to buy you coffee sometime."

Buy me coffee, wine and dinner, please, I thought to myself, and I will do anything you want.

"I'd love that. Thank you. Have a nice walk boys!"

Without letting myself think about it, I leaned forward and kissed him on the cheek, before making my way off towards my destination. As I crossed the empty road I looked back to where Diego was still watching me. I waved, he waved back, and disappeared up the path between the houses.

I almost squealed with happiness. Katie really was pretty, he'd said so! I skipped a few steps before calming myself down.

I stepped off the main path onto a dirt track, grateful for the recent dry weather. The darkness was like a comforting shield from any unwelcome eyes - although part of me secretly wanted Diego to still be watching.

I smiled to myself at the thought if the handsome Spanish man and skipped along the path, enjoying the breeze in my hair. For a moment I regretted not wearing a skirt to feel the fresh air on my bare legs. Then I thought to myself: why not...?

Shivering in anticipation, I leaned against a tree and began to wriggle out of my jeans. I folded them neatly behind the same tree, and glanced up and down the path. The coast was clear, so again I skipped a little way further through the trees, thrilled by the feeling of cool night air on my bare skin.

Next I took off my jacket and left it in the same place. I skipped away again, this time holding my arms out and spinning round, forgetting myself in the moment.

Crack.

I was brought out of my reverie with a shock that sent an ice-cold chill through my body. Someone else was here.

I immediately ducked behind a large tree and tried to silence my breathing. My heart hammered in my chest.

Now I could clearly hear someone walking the way I had come. They must be in between me and where I had left my jacket and jeans.

Then I heard it: a man's gruff, low whisper.

"I know you're here. Don't worry, I won't hurt you."

It wasn't Diego. Instead, the gravelly English accent immediately put me in mind of the opening scene of a murder series, with myself cast as 'victim number one'. I'd be lucky to get so much as a line of dialogue, I thought, before meeting a grisly end.

The man spoke again, and it was as if he'd read my thoughts.

"I know that probably doesn't sound very reassuring," he said, slightly louder this time. "But I really mean it. I can't sleep, and this is where I always come for a midnight walk. You startled me as I've never seen anyone else here at this hour. I'm guessing I terrified you. I'm really sorry. I'm rambling now."

He sounded sweet, if a little uncertain. I steeled myself, and peered round the tree.

The man was dressed for running in shorts and a tshirt, which even in the dim moonlight showed slight patches of sweat. He was slightly taller than me with a bit of a paunch, and was quite hairy with it. He wore glasses and hadn't shaved his face in a few days, I estimated.

He spotted me, and waved awkwardly. "Hi," he said.

"Hi," I murmured, "I'm sorry I spoiled your run."

"Not at all," he smiled, "it's not often I see a cute young woman dancing in her underwear like that. I kinda wish you hadn't stopped."

In my head, I was foing cartwheels. In the space of a few minutes since leaving my apartment, not only had two men seen me, but they both thought me, Katie, attractive. I buzzed with excitement. Maybe I could really become a woman in the real world?

"I... uh... thank you!" I stammered, shaking with cold and, probably, shock. "I think I need to get my things and get home now."

There was a pause. As I watched, still half hidden behind the tree, my inadvertent accompanist edged back, placing himself between me and the rest of my clothes.

"I would very much like to see you again before you go," he said. "Don't be shy."

His left hand slid inside his shorts and started rubbing his crotch.

Okay, I thought. Katie, you can get out of this. I could have run, but it was likely he could too, and I'd have had to get past him first. I briefly considered using force, but didn't feel confident in my strength given I was still shaking from the shock of being discovered.

There was only one thing for it, and once I thought of it I realised I was going to enjoy it.

I stepped out from behind the tree onto the path in front of the runner. His mouth opened as he stared at me, his eyes moving down my body to my legs, and up again.

"Well, what do you think?" I asked, clasping my hands together behind my back and biting my lip. I made a show of spotting where his hand was. "Ooh, is that what you do on your walks? Naughty!"

I could almost hear him drool. "Uhh... no... I mean, sometimes..."

Almost as an afterthought, he pulled his hand out of his shorts and mumbled an embarrassed apology. I smiled. He most certainly wasn't any danger - but he could be in for some fun, I thought.

"That's okay, honey," I purred. "I was scared what you might do, but I can tell you mean well. Rubbing your cock like that does make you look a bit pervy, you should know. Maybe best not to do that next time you meet a semi-naked girl in the woods. That okay?"

He nodded, sheepishly, and stepped back to let me pass. But I had other ideas.

I walked confidently forward, pulling off my tshirt as i did so. "It's okay. I think you and I are going to be okay."

I stood in front of the man in just my bra and panties, and let my top fall to the floor. I could see him clearly now, and he was likely in his mid-forties, with red cheeks and a receding hairline. Not exactly the dashing handsome prince I had imagined for my first blowjob (Diego, I sighed to myself, would have to wait), but I, as Katie, knew that dirty was every bit as fun. I put my hand on the man's chest.

"Now, me show you what I do for proper gentlemen," I whispered, sliding both my hands into his shorts. He moaned quietly as I found his erection. "Do you promise to be a gentleman?"

"Yes. Fuck, yes!"

I dropped to my knees and pulled down his shorts and boxers. His cock was rock hard, probably about 5 inches so a little shorter than mine.

I was about to give my first blowjob, I thought to myself, thrilling at the circumstances. I'd been caught in the woods semi-naked on my first time out of the house as Katie. I'd openly stripped off further and was about to suck off a stranger.

I was grateful for the dim light that meant my gentleman wouldn't see my growing erection stretching the cotton of my panties. I gazed at his cock for a moment longer, then took his head in my mouth.

I heard him gasp and tense up. I licked around the head a few times, then up and down the shaft like a lollipop. I sucked briefly on each of his balls while stroking him slowly, exhilarated by the thrill of pleasuring a man for the first time.

"Fuuuuck yes..." he whispered, "that's so good!"

I looked up at him from under my lashes and thanked him, before taking him in my mouth completely. I slowly moved up and down, relishing that salty taste and musty smell.

He groaned slightly louder and placed his hands roughly on my shoulders. I didn't need any more of a signal, and grabbed his ass with both hands. I doubled my speed and moaned slightly, trying hard to emulate the porn stars I'd watched while practicing on my dildo in my bedroom.

This was different, though. The man was seemingly having the time of his life, and held my head with both hands. He increased our speed again, face-fucking me as I dug my fingers in his ass cheeks.

"Yes, baby, suck it!" he growled. I felt precum soaking my panties - this was everything I wanted and I didn't even know it.

"You sexy, sexy girl... you're gorgeous... you're so good at this... I'm going to cum..."

Before I could properly relish those compliments, he thrust into my mouth and hot cum spurted into the back of my throat as he groaned loudly.

As he released his grip on me I slurped his cock a few times, taking all the cum I could. He moaned again as I licked the last little drop from the head of his cock.

Immediately, I grabbed my top and stonod up, spinning round quickly so as to hide my own erection.

Taking a few steps towards where I'd left my jeans and jacket, I looked back at my new friend over my shoulder, and smiled. He was staring at my ass.

I wiggled it, teasing him. "Maybe you can try this next time, big boy," I purred.

He watched as I dressed, and I made sure to show off my bum as much as possible. By the time I was fully clothed, my erection had subsided and I could turn around.

"Thank you for my treat," I said. "It was totally unexpected, but I enjoyed meeting you. I hope you had fun too?"

He nodded, opened and closed his mouth a couple of times, and swallowed. "Umm, yes... I... err... I'm sorry for..."

He took a deep breath.

"It's been a long time since I had a, err, experience like that. It was wonderful. Thank you."

I giggled. "Spoken like a true gentleman," I said. I trotted over to him and kissed him on the cheek. As I turned around he stroked my ass, then I felt him pull away.

I look d back over my shoulder. I smiled, and bit my lip. "Go on, grab some. A little treat for being so sweet."

He grabbed my ass with both hands and squeezed. "Oh baby, you're gorgeous."

I stepped away, and looked back one last time. "Thank you, handsome. You've no idea, but you made me feel so sexy and desirable tonight. I won't forget you in a hurry."

I blew him a kiss and hurried home. My first time out was one evening I will never, ever forget.