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House Sitting for the Holidays (Part two)

"The sissy adventure continues..."

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By the end of the first week, I had completely transformed into a girl. I no longer wore men's clothing and my daily routine now consisted of showering, shaving and practising my makeup techniques before deciding on what outfit I was going to wear next. I had completely succumbed to feminization and needed to dress slutty in order to feel fulfilled.

On this morning I rifled through the wardrobe looking for a sexy outfit, holding my breath as I came across an inappropriately short sequinned blue mini dress with ruffled hem. "Oh fuck me," I mumbled with girly surprise.

I was already wearing a sexy black three-piece set, complete with matching silk bra, thong, garter and stockings as I pulled the dress from the hanger, excitedly slipping it on over my lingerie. I stood back in my high heels and admired the slutty whore standing before me in the mirror.

"I need your cock!" I mouthed seductively, dropping to my knees and reaching for one of the many toys that lay strewn across the floor. I picked up a rubber cock and licked the suction pad base, sticking it onto the mirror and running my tongue up the length of it. Staring into my reflection as I began to roleplay.

"Do you want me to suck your dick, baby?" I whispered, dreaming of the real thing as I quickly sank my mouth over the rubber cock, gagging as I deep throated it. My mouth salivated as I bobbed my head over the cock, feeling the dress rub against my stockings, the thrilling sensation as it pulled tightly against my ass.

My eyes flickered in excitement as I watched myself sucking cock, the dress riding up my legs, exposing my garter belt and tops of my stockings. I closed my eyes and thought about Teresa, imagining her sucking her husband's cock.

The fantasy sent a rush of heat down to my crotch, lifting my dress further and picking up a large vibrator before slowly easing it into my pink boy pussy. "Oooh yes baby, you want to fuck me, don't you?" I squealed as I began slowly riding it. "That's it, baby. I'm your sissy slut."

I screamed with pleasure as I rode and bounced onto the vibrator, speeding up and leaning forward as I continued sucking the rubber cock dangling from the mirror. It felt as if I was being double-teamed and sent rushes of tingling sensations through my body. Had Teresa ever been this naughty? I thought to myself. 

My tiny clitty was oozing pre-come into my silk thong that stretched across my ass clinging to my hips as I pushed myself deeper onto the vibrator. I let out an orgasmic scream, sinking back further. "Take me," I moaned. "Fuck my pussy baby!"

I was edging closer to a full-blown orgasm, freeing my nipple and squeezing it tightly, bouncing onto the vibrator as my ass cheeks slammed harder against the floor. I took one more look at myself in the mirror, watching intently as I felt a rush of anal orgasm vibrate against my g-spot, cum trickling from my soft clitty.

"Yes, baby!" I screamed, feeling the vibrator deep inside me as I continued fucking myself harder and faster until I came to a climax.

After a quick shower, I towelled off and slipped back into some pretty pink lingerie. I decided to take a picture of myself standing against a cupboard in the hallway. I looked at the image, noticing how slender my body was, how sexy my legs were and how feminine I had become.

Teresa's name lit up on the screen, startling me. 'Shit,' I thought, suddenly conscious of what I was doing. "Hello," I answered timidly.

"Hi sweetie, how are you?" She shouted down the phone, the sound of loud chatter and music blaring in the background.

"I'm fine," I replied.

"How is everything in the house, you making yourself at home?' She inquired.

"Oh yes, everything here is great," I replied, looking down at her pink stockings and lingerie stretched tightly against my body. "I'm settling in ok."

"Oh, good, glad everything is going well. Listen, I gotta go, this call is costing a fortune. Lots of love, help yourself to anything you want and remember, Mi casa es su casa," she said, quickly ending the call.

I wandered downstairs and into the kitchen, enjoying the sound of my high heels clicking on the tiled floor, searching for something to eat for breakfast. 'Dammit,' I thought. There was barely any food left in the house. I stopped and thought for a second when suddenly the idea popped into my head.

Why not just go shopping dressed en femme? The thought both scared and excited me at the same time. Adrenaline pumped through me as I quickly tiptoed up the stairs to see what kind of outfit I could put together.

Sifting through a few ideas I slipped on a cute light grey pencil skirt and a black ribbed long sleeve crop top that matched my heels. I brushed my long brunette wig and took my time applying makeup to make sure I looked convincingly feminine, before leaving the house.

After a short drive, I arrived at the local supermarket. I felt so self-conscious as I stepped out of the car and teetered across the parking lot into the store. I felt as if the whole world was watching me, nervously grabbing a trolley and heading down an aisle. A few men seemed to be staring at me as I shopped and one woman gave her husband a dirty look as she caught him staring at my ass.

A young guy in his early twenties seemed to be following me around the store. I couldn't tell if it was just coincidence so I decided to loiter around the canned goods aisle. Scanning the items on the shelf, I casually glanced over and saw him subtly watching me. Something came over me and I felt the urge to tease him, bending over to pick up a can from the bottom shelf, ensuring he got an eyeful of my tight ass.

Slowly bending back up, I looked over my shoulder, seeing his eyes wild with delight and his mouth wide open in awe. A tingle ran up over my body and back down again, making me smile gleefully. Strutting further down the aisle, I swung my hips and tiptoed in my heels, stopping to look up at a shelf and exaggerating as I struggled to reach something from the top.

He motioned over and reached up to assist me. "Here, let me help you," he said, grabbing the item and handing it to me.

"Thank you," I replied, raising my tone in a high pitched girly voice.

"No problem, I'm Jackson." His response shocking me as I struggled to think of a name.

"Melanie," I replied mousily.

"I'm so sorry I never do this but I'd hate myself if I didn't ask you. Is there any chance you'd like to get a drink with me sometime?"

I blushed at his invitation, blood rushing to my head and making me feel faint and stupid. "Umm, ok," I replied sounding like a bimbo. I gave him my number and asked him to text me later as I waltzed away and finished shopping. I was giddy on the drive home, reflecting on the experience of being chatted up by a cute young guy.

A hundred questions ran through my head. How did I feel about this? Did he know I had a secret tucked away behind my thong? Was I really going to meet him and how far would I let it go if I did? I pulled up in the driveway, feeling dizzy and lightheaded. I rushed inside with the shopping, dumping it on the side and heading upstairs to lay down.

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When I awoke, my phone was flashing. I reached over feeling the skirt rub against my stockings and checked the text message.

'Hey, it's Jackson. It was great meeting you today. Fancy a drink later tonight? I could pick you up or meet you somewhere.'

My heart raced, was I actually going to do this? I thought, shaking as I hovered over the reply button. 'Ok,' I typed, 'where and when?'

His response popped up on the phone almost immediately, 'Mario's Bar 7 O'clock, want me to pick you up?'

'No,' I replied, 'I'll meet you there.' 

'Can't wait, see you soon.' He texted.

The realization hit me with panic and excitement, 'what was I going to wear to a bar?' I thought as I hopped off the bed and over to the wardrobe, sliding the pencil shirt off over my ass and down my legs, freeing it from my high heels as I tore the crop top off and threw it on the floor.

My heart pounded heavily in my chest as I searched through the range of sexy dresses and intimate garments, considering each one's shape, colour and sex appeal. Trying on several options, eventually, I decided upon a red sleeveless, strappy spandex dress with a long back zipper and criss-cross neckline.

I squeezed myself into the tight fitted dress, the spandex stretching over my every curve and accentuating my slender figure. "You dirty girl," I said out loud, staring in the full-length mirror as I turned around admiring my new look. I kicked off my heels and slid on a pair of shiny red platform pumps, further adding to the slut appeal.

It was almost 7 o'clock so I touched up my makeup, styled my hair into a ponytail and headed out the door. As I pulled up the parking lot behind the bar, I shook nervously, desperately trying to summon up the courage to open the car door. The car park was dark and quiet which helped me to pluck up the nerve to step out one foot at a time and slowly walk around to the entrance.

I took a deep breath before pushing the door open and taking my first step inside. As I entered the bar I scanned the room nervously, catching the attention of a few guys who made no attempt at hiding their opinions on the way I looked. Staring and mouthing the words 'damn' as I strutted past the bar.

The attention made me feel a little more confident about myself as I looked over to see Jackson sat down at a booth in a dark corner of the room. He stood up and ushered me over, watching me intensely as I flounced across the room towards him, grabbing my hand and kissing it to greet me.

We sat closely together and made small talk for a while when a barmaid approached to take our orders. She flirted with Jackson and gave me a look of disgust, obviously jealous at how good I looked before leaving us alone to fetch the drinks. Jackson looked really well presented in a crisp white Ralph Lauren shirt, clean-cut black jeans and tennis shoes.

As he complimented me, I noticed his dark soft skin, his deep brown eyes and jet black hair. I loved the way his carefully trimmed facial hair ran down his chiselled jawline and shaped his mouth and big juicy lips. When he smiled his face lit up and sent shock waves down the back of my neck, making me tingle all over.

Time raced past as we enjoyed each others company. He was a complete gentleman, making sure I felt safe and secure, occasionally making contact for a short second, touching my arm or leg as he asked questions. Nothing too overbearing or inappropriate, just enough to make me feel comfortable.

People began to leave and the bar was getting quieter. I excused myself and popped to the ladies to relieve myself and check my makeup. I exited the restroom and started walking down a dark hallway back to the bar when suddenly Jackson appeared, pulling me into a corner. He wrapped his arms around me and pressed his lips against mine, kissing me passionately, his tongue wandering into my mouth momentarily before pulling away.

"I'm sorry, I've been wanting to do that all night long," He said apologetically.

"It's ok," I replied sheepishly, "I like it."

Again, he kissed me, more passionately this time, French kissing me as he explored my body, running his hands over my spandex dress and squeezing my ass cheeks tightly. We had somehow moved back and pushed through a door into an empty men's room. Continuing to kiss, Jackson motioned me into a cubicle and locked the door behind us.

Any fear I felt was overtaken with lust as my hands pressed hard against his chest pushing him back and pleading, "I want your cock," dropping to my knees and quickly unzipping his jeans. He grabbed hold of the cubicle walls and stared down at me as I pulled his jeans down releasing his dark meat. His giant hard cock sprang out in front of me and stood to attention.

"Oh yes baby," He panted heavily.

I reached out and held his big hard cock in my tiny hands, feeling it pulsate as I slowly rubbed and massaged it with my fingers. Mesmerized by how pretty it looked, my mouth watering at the sight. I instinctively licked the head with my tongue, watching him writhe in pleasure. He looked down, an expression of desperation on his face as I stared back up at him, gently easing his foreskin back and tonguing the tip of his penis.

His eyes grew larger as he watched my mouth open, slowly guiding his length between my wet lips and into my moist mouth, jerking his cock with both hands. "Oh baby," he grunted clinging to the cubicle walls as he tried desperately to hold his weight up, his knees buckling beneath him as I took him deeper into my throat.

He moaned while I continued sucking his cock, speeding up and bobbing my head, jerking his cock faster with my hands. "Oh shit," he mumbled, pushing his cock deeper down my throat. "I'm gonna come!" He blurted out. I couldn't believe it. 'Already?' I thought. 

He pulled his cock out my mouth and started jerking frantically in front of me, suddenly exploding streams of come all over my face. I flinched and closed my eyes as his spunk burst onto my face, his moans echoing around the restroom. After several hot sticky shots splatted onto my face, I opened my eyes.

"Oh shit, oh fuck," he said softly. "I can't believe I just did that. I'm so sorry."

I grabbed a piece of toilet paper from the roll and dabbed the come from my face, trying not to smear my makeup. "It's ok," I said. "I don't mind."

He helped me onto my feet, pulled his jeans up and headed out the door, quickly checking that no one was around. "It's ok, you can come out now." He motioned to me.

I stumbled out the toilet feeling like a cheap nasty slut, quickly leaving the restroom and back into the dark hallway. Jackson seemed embarrassed about his performance and grabbed my hand, "I'm really sorry," he said. "That's never happened before. Can I see you again sometime?" He asked.

I was still really apprehensive about his offer. A blow job was one thing, but I wasn't even sure if he realized what was hiding under my dress. I looked into his deep brown eyes and replied. "'Maybe. Why don't you send me a text sometime and we'll see what happens?" Shooting him a naughty wink as I watched his face light up.

To be continued...

 

Published 
Written by MirandaGreen
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