Evolving Tina Ch. 02: The Neighbour

I stared at the gorgeous bimbo in front of me.

"Mum?" I asked as I hastily tried to cover my body with my arms.

The woman in front of me gave me a puzzled glance, but instead of answering, she gently pushed me aside and walked briskly to the next room.

She closed the door behind her, leaving me standing there completely befuddled.

Unsure of what had just happened, I considered following her for a second, but then I realized it couldn't have been her. I shook my head, walked outside, and closed the barred metal doors behind me.

Immediately, I grabbed my phone and texted Daddy, "I'm done for the night."

No reply.

"Not surprised," I whispered.

I slowly raised my hands to scratch my itchy earlobes and started walking home through the fairly rough neighborhood.

At this point, there was barely anyone awake anyway, I thought. I took a deep breath and tried to relax as I walked through the dimly lit streets.

I kept thinking about the woman from before, and that's when I started to realize how much I missed my mum. She left us abruptly after my dad told her about the arrangement he'd made with Wesley, who I now call my pimp Daddy. I'd tried to call her multiple times over the past few weeks, but her sister, where she was staying, always said she wasn't available and to try again later.

I kept thinking about my mum and how she'd be a terrible whore since she was so assertive, and I started to giggle.

At this point, I'd already left the rough neighborhood behind me--if you can really call it that. I've lived in the suburbs all my life, so anything else feels "rough" to me.

As I walked home, I passed a shady-looking guy dealing drugs on the corner of the street.

"Hey baby, want some X?"

"No, thank you, Sir," I answered.

Daddy would be furious if I ever ruined my body with hard drugs.

In the distance, I could see the next street didn't have any streetlights, and I remembered I still had the keys to my butt plug.

I grabbed the keys out of my little pink purse and stared at them as they lay in my hand.

"I could unlock myself, finger myself, and finally have an orgasm. Nobody would ever know."

After a few seconds, I snapped out of it, decided not to risk it, and quickly put the keys back in the purse.

"So, this was number two on the list of clients," I whispered to myself.

Eight more to go, and then my escorting ad goes public. I can't imagine things slowing down when that happens. My heart sank at the thought of whoring myself out every day until my dad's debt was repaid.

"I wonder how much he owes? It can't be that much, right?"

Suddenly, I heard a car honk on the other side of the street.

The driver slowly opened his window.

"Damn, I'm glad you're okay, baby."

He pressed a button near the steering wheel, and one of the car doors opened.

"Get in, baby," he said.

I've got my own driver these days for clients who live far away. His name is Sam, the local scout leader who made me deepthroat his dick, dress up like a slutty scout girl, and lick his cum off a lollipop.

I know pimp Daddy is a fire safety inspector, so he hired Sam to work for him in exchange for dropping all the fire safety charges against him.

I slid into the backseat and exhaled deeply in relief.

"What the fuck, you smell like piss and cum."

"Just shut up and drive me home," I replied, rolling my eyes at him.

He checked me out in the rearview mirror.

"You know, I tried to copy our little session with other girls, but sadly they aren't quite..." he paused for a second.

"You," he finished.

"Just get me home. You need to ask Daddy in advance anyway."

"I know. But I'm broke, and I sure can't afford you anymore."

I stayed silent and stared out of the car window as he kept eyeing me through his rearview mirror.

The car seat felt cold against my naked bum.

As we drove onto the driveway, he opened the car door, and I stepped out as he rolled down his window again.

"Can I at least have a looksie?"

I glared at him.

You know what? Fuck it, I thought.

I slowly turned around, bent over a bit, and gave him a good look at my bruised, locked hole.

"You know, I'm still bummed I never had a chance to fuck that."

I turned around and winked at him.

"Talk to Daddy."

"Maybe I will," he replied with a wink, then sped off the driveway.

I grabbed the house keys and opened the front door. After entering, I stripped off all my clothes immediately and dumped them in a laundry bag next to the entrance. My father had put the bag there and told me to drop my clothes in it after "work." I was now completely naked except for my collar, cage, and plug.

Gently, I opened the door to the living room and noticed my father sleeping on the couch with the TV silently playing some random football game.

I softly closed the door behind me, and as I did, the cat jumped onto Dad's lap. He slowly opened his eyes.

He looked at me and smiled.

"Hey, buddy, how did it go?" he asked, tapping his lap to beckon me over.

"It was fine," I lied as I shuffled to the couch, rubbing my tired eyes.

"Keys," he ordered, holding his open hand in front of me.

I turned around to grab my purse and pulled out the keys to my plug. I walked over, climbed onto the couch, and rested my head in his lap.

He took the keys and quickly slipped them into his pocket. As he ran his fingers through my hair, I felt myself falling asleep.

The next morning, I woke up groggy, still naked on the couch but with a blanket over me and the cat purring beside me. I immediately reached for my neck and noticed my collar was gone.

I stretched and yawned so loudly that the cat got scared and jumped away. My skin stuck slightly to the warm leather couch; it was a strange feeling. I stared blankly into the distance for a bit, then remembered to start my daily chores.

I looked at the clock and realized I still had time. Sleepy-eyed, I entered the kitchen and opened the refrigerator. There was a special shelf for my food now--a bowl of low-fat food labeled "Sunday."

I put the dish in the microwave and sat on one of the stools near the kitchen island. I stared into the garden as I reminisced about everything that had happened over the past few weeks. People might think my life was thrilling--and I'm not saying it isn't--but it's mostly just routine now. Mostly self-care, dress codes, and updating the website. For some reason, I'd barely had any actual sex at all; the gangbang yesterday evening was the first in weeks.

My father said Wesley was busy doing stuff for me in the background, and I could only imagine what he'd been up to all these weeks. He hadn't even fucked me in weeks--not even with toys--and for some reason, that made me even hornier.

As a matter of fact, I'd never been this horny before.

Suddenly, the microwave beeped loudly. I opened the door, grabbed the food, and started eating while staring at the garden. Then I felt something between my legs near my cage. Once again, there was a little puddle of clear liquid on the stool. This had been happening lately--I was constantly leaking something. I sighed, trying to remember what an orgasm felt like. I shrugged it off and finished my breakfast. After grabbing a handful of supplements and washing them down with water, I knew this was the only food I'd get today.

As I put the dirty dish in the dishwasher, I noticed I still smelled like piss, cum, and sweat.

I needed to start my daily healthcare routine anyway. So, I rushed upstairs, entered the bathroom--now filled with healthcare products--and began.

A short cold shower, followed by skincare routines, various perfumes, and lotions. I couldn't clean my bum since my dad was nowhere to be seen. I'd have to do that later. It was always so humiliating having to ask permission to poop and clean myself, I sighed.

I carefully checked my body for stray hairs, but after the laser treatment a few weeks ago, there wasn't a single hair follicle left. Still, Daddy told me to inspect every day anyway. Must be some strange power play, I thought, but I did it anyway to avoid angering him.

"Not a single hair on my entire body," I said to the full-length mirror in front of me.

I turned around, glanced at the clock, and realized it was time to check my schedule for today. I entered my bedroom, now completely transformed into a teenage prostitute's room.

I sat down at my desk and opened my glittery pink booklet.

---

Sunday:

- Hot pink ultra-cropped mesh top

- Hot pink wet-look micro skirt

- Website picture

- No appointment

---

"No appointment," it said. I was a little disappointed by the words.

I put the booklet away and walked over to my wardrobe to grab the items. First, I picked up the mesh top, then the micro skirt. I vividly remembered the first time I had to wear this top. Daddy put it on me and took me shopping for shoes. I was so embarrassed because it was completely see-through. I could still recall all the looks I got from people. It feels strange being a scantily dressed boy in public, but I was accompanied by a huge, towering hulk of a man, so nobody dared to speak up anyway.

Next, I grabbed the pink custom-made micro skirt and slowly slid it over my smooth, hairless legs. I looked in the mirror, happy with the result, then took a picture that automatically uploaded to my website. It didn't take long before the first likes started coming in. I smiled, wondering what the hell I was supposed to do all day dressed like this.

As I stared at myself, I suddenly noticed my father standing in the doorway of my room, holding the keys to my plug and a big pink bag.

"Say it," he said.

I sighed and answered.

"Can I please clean my bum, Sir?"

"Of course, buddy," he replied.

He left the room, and I followed him slowly to the bathroom. I walked over to the toilet and held out my hands. He dropped a key into them.

"Be careful it doesn't fall in the toilet," he joked.

I rolled my eyes as I maneuvered the key into its slot on the plug. As I turned it, I felt the plug's mechanism shift; the four latches holding it in place receded, making it possible to pull it out. Slowly, I removed the giant plug from my bum, feeling a bunch of cum from yesterday leak into the toilet.

As this happened, my dad just kept staring at me with a proud smile on his face.

Next to the toilet, fixed to the wall, was a flexible douche for cleaning. I slowly inserted it into my sore hole, squirming a little from the tenderness after yesterday, then turned on the tap.

Gradually, my belly filled with a special mixture of warm water and strawberry-scented lube. When I started to cramp, I quickly turned off the tap. After a few seconds, I sat down and let it all out. Once every drop was gone and I'd cleaned my hole with a cloth, I reached for the plug, but my dad stopped me.

"You've been a good boy lately; I want to reward you with something!"

"Oh, what do you mean, daddy?"

He held the pink bag in front of him and pulled out a giant black dildo with a little wire attached. But this wasn't a normal dildo--it had the base of a butt plug, like a mix of the two. I'd never seen anything like it before.

Noticing my confusion, he beckoned me to turn around.

"Put the toilet seat down and get on your knees on top of it."

I turned around, lowered the seat, and crawled onto it.

"Put your hands against the wall and don't move."

He pressed the tip of the dildo against my open, stretched hole and slowly inserted it without stopping.

It was an incredible feeling, being filled by something that large--especially after weeks of barely any action. As it was almost fully inside, he gave it one final push, and it popped into place. I let out a soft moan as a thin stream of liquid leaked from my chastity cage again.

"There you go, buddy. How does it feel?"

"It feels so big," I grunted.

"Lovely to hear. Now sit still for the next part."

The next part? What was he talking about?

He grabbed the little wire and plugged the other end into what looked like a TV remote control. He powered it up and pressed a few buttons.

"This is your reward for being so good," he said, pressing a button on the side of the remote.

I immediately felt the dildo vibrate, and I let out a soft, drawn-out moan. After a few seconds, it started to squirm ever so slightly against my sweet spot.

Again, I let out a soft moan.

"Alright, get up. How does it feel?"

I stood up, turned around, and before I could speak, I saw my dad laughing. He placed his big hand on my stomach.

"You can clearly see the outline of the dildo on your belly--it's so cute!"

He grabbed me by the shoulders and guided me toward the mirror. I looked at myself, and he was right--you could clearly see the giant dildo's outline protruding from my belly next to my belly button piercing. It was slowly vibrating and squirming.

I loved how it looked and felt.

"Thank you, Daddy," I softly moaned.

"My pleasure, buddy," he smiled, grabbing the little wire and unplugging it from the base of the dildo.

"So, I have the afternoon shift today. Mind taking care of the garden?"

I looked at his reflection in the mirror, puzzled.

"Uh, mowing the lawn and weeding dressed like this? With this thing inside me?"

"You've got this, buddy. I'll be home around eleven tonight. I expect you to do your chores, okay?"

He didn't wait for my answer and walked out of the bathroom.

I puckered my lips, raised my eyebrows, and stared at the absolutely ridiculous sight. I let out a little moan and started to feel lightheaded from the dildo so deep inside me. I tried to snap out of it and began my chores.

After heading downstairs in my little sissy outfit, Dad had already left for work, leaving me home alone.

I grabbed my MP3-CD player from the shelf, attached it to my skirt, put on my headphones, and started playing my hip-hop playlist. As Dr. Dre blasted in my ears, I slipped on some pink slippers and walked to the garden shed where the lawnmower was stored. At this point, I didn't really care how I looked anymore--just an effeminate boy with long blond hair wearing a pink mesh crop top and a short pink skirt.

I opened the shed door, brushed away the spider webs, grabbed the lawnmower, and pulled it out. As Dr. Dre's "Fuck You" started playing, I began mowing the lawn in a straight-line pattern. Boring, I thought. About halfway through, I noticed the reservoir was full, so I bent over to empty it. In the shed window's reflection, I saw my next-door neighbor staring at me through his window. I froze for a second--I'd never thought he'd be interested in me. He's a ninety-something veteran who barely gets outside anymore. I glanced at him in the reflection; he had no idea I'd noticed him, and my heart started beating faster.

"This day might get fun after all," I giggled.

Knowing he was watching me mow the lawn in this outfit, with the huge vibrating dildo up my bum, I decided to have some fun with him.

I stopped mowing for now and went to get a drink. With my heart racing in my little chest, I ran inside and grabbed a glass of water. After finishing it, I excitedly ran to my bedroom and opened my closet.

"So many choices!" I smiled.

After a few seconds of browsing, my gaze landed on the perfect item.

"Oh my god, this is perfect!" I shrieked.

I grabbed it and giggled to myself. Then I took my phone and sent a text to Daddy.

"Possible client."

It's something he told me to send whenever I had to change my routine for a business opportunity.

It didn't take long to get a response.

"k"

With a big smile, I tossed the phone onto my bed and thought about all the ways I could tease my dirty, staring, pervert neighbor.

I laid the item of clothing next to my phone on the bed and giggled again.

It was a glittery, pink two-piece micro bikini, modified to fit my body type--complete with a tiny pouch in the front for my chastity cage.

I quickly removed my mesh top and skirt--careful not to damage anything--grabbed the ridiculous hot-pink two-piece bikini, and put it on.

I admired my gorgeous, milky-white sissy body in the mirror as the dildo kept vibrating, and I realized exactly what I was going to do!

I grabbed my jewelry case, picked out a cute silver belly chain, wrapped it around my tiny waist, and locked it in the back. Next, I took a silver necklace with a red heart-shaped locket and put it around my neck. Finally, I grabbed my pink, heart-shaped shaded sunglasses and slipped them on. I looked in the mirror.

I looked perfect for a sissy sunbathing session!

The outfit was something else--the tiniest bikini I'd ever seen, complete with pink nails, pink toenails, and cute jewelry.

"One more thing!" I said to myself.

On my desk was an assortment of lipsticks. I grabbed the glossy hot-pink one and slowly applied it to my lips. I looked so pink and utterly ridiculous; I'd drive any man insane.

Next, I grabbed my huge pink beach towel and draped it over my shoulder.

Then I walked downstairs, slipped on my flip-flops, put on my headphones, and stepped into the garden. I walked straight to the middle of the partly mowed grass, glanced at the shed window, and noticed he was still sitting there, staring, now with a big grin on his face.

I chuckled and decided to give him a great view of my little bubble butt as I laid the towel down. Without turning around, I lay on my stomach, giving him an even better view of my bum.

The tiny string of the bikini bottom wasn't nearly large enough to cover the base of the dildo plug, so he--or anyone else--could obviously see something lodged up my little bum.

I tried to catch his reflection, but at this angle, I couldn't see him. Still, I was pretty sure he was watching.

"The pervert!" I giggled.

For some reason, the thought of him staring at me with that big grin made me extremely horny and lightheaded. Or maybe it was the vibrating dildo?

I raised my left hand, slowly reached for the base of the dildo, and gently pushed it deeper in a rhythmic thrusting motion. After a few minutes, I was so entranced that I started fantasizing about him fucking me right there in the middle of the garden like a cock-addicted sissy slut.

I felt my little cage straining again. The sensation caught me off guard, and I stopped touching the dildo--cumming was strictly forbidden. I wondered if he was still watching as the huge black dildo continued its assault on my sweet spot.

At this point, I was so horny I decided to flip onto my back to see if he was still there--I needed to know!

I slowly turned over and froze as I saw him standing right in front of me, jacking off.

He couldn't see my eyes through the sunglasses, so I played along, pretending I hadn't noticed him. He must've had quite the sight--a little sissy on the ground, looking like a total slut with the visible outline of a giant dildo in her belly.

Barely containing my smile, I continued sunbathing with my arms resting by my sides.

I could tell from his demeanor he was about to cum, and then I realized he planned to cum on me!

Seconds before he climaxed, I decided to drive him wilder, opening my lips and sticking out my tongue as a clear invitation.

Then he started to cum--spurt after spurt after spurt. I'd never experienced a load this huge. It went everywhere--my chest, my belly, my legs, my feet, even some on my sunglasses and in my eager, open mouth.

I was now effectively covered in cum from my old, pervert neighbor.

The sheer amount took me by surprise, but I absolutely loved it.

As he stood there, dick in hand and panting, I noticed a look of regret on his face.

I raised my hand, rubbed his cum all over my body, and swallowed the bit that had landed in my mouth.

It tasted sweet, like cranberries. That was strange.

He quickly pulled up his shorts and slipped through the little gate between our gardens to disappear.

With a huge smile, I put my hands behind my head and stretched my body.

"This was fun," I said to myself.

I lay there for a few minutes as the dildo's humming gave me a fantastic feeling inside. Then I decided it was time to finish mowing the lawn.

I chose not to change and finished the job dressed as I was, with dried old-man cum all over my body.

After completing the chores, I was in the mood to watch some of the porn Daddy had carefully selected for me. Though it was strange, it was the only thing I was allowed to watch.

I went to my room and noticed my phone light flashing as I walked in. I grabbed it and saw a text from "CashDaddy1."

Christopher? The rich guy who whipped me until I came in my cage a while back? Frowning, I opened the text.

"I booked you for tonight. Be here at 6 o'clock, don't be late."

That's strange, I thought--clients never text me directly when they want to meet.

I promptly sent a message to pimp Daddy for more information, but he didn't respond.

Not wanting to risk Daddy's anger, I decided to comply. The sooner this stupid debt is paid, the sooner I can return to my normal life.

I quickly removed the bikini and took a short shower to wash off all the dried cum.

Standing in my bedroom, I grew frustrated at the lack of instructions. But I seemed to recall Christopher really liked "girly girls," so I dressed accordingly.

I slipped a short, white frilly sundress over my body, paired it with white frilly ankle socks and matching white pumps. I went from looking like a complete street whore to marriage material in just a few hours, I laughed.

I accessorized with some jewelry around my wrists and neck, then completed the look with two ponytails tied with white ribbons. Happy with the result, I decided to take my bike.

I locked the front door behind me, grabbed my bike, and cycled to Christopher's house. I didn't need Sam to drive me this time--it wasn't that long of a ride.

There were more people outside today than I'd expected, and dozens stared at me--some even shook their heads. But I didn't care; I knew I looked amazing. Plus, the still softly vibrating dildo kept me focused as sitting on the bike seat intensified its assault on my insides.

After a short ride, I arrived at Christopher's mansion. I rang the bell next to the gate, and after the camera scanned me, the gate slowly opened.

As I neared the house, I remembered how massive it was--not a house, but a mansion!

I parked my bike to the side--no need to lock it here--then walked up the stairs to the front door and rang the fancy doorbell.

I took a deep breath, thinking about the events from my last visit here.

The door opened quickly, but to my surprise, it wasn't Christopher standing in front of me.

It was a teenage girl who could've been my twin. Despite our different outfits, her body, face, and hair looked eerily like mine, with only a few minor differences.

Then I realized it was his daughter, Stephanie.

She slowly parted her lips and spoke in the softest voice I'd ever heard.

"Hey, Tina, can we talk?"