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House Sitting for the Holidays (part one)

"A favor for a friend turns into a sissy adventure."

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My friend Teresa was planning her summer holidays but was beginning to stress about leaving her home unattended for such a long time. She lived with her husband in a large house in the middle of nowhere and the two of them were planning a cruise, which meant the house would be left empty for the next eight weeks.

She invited me over for lunch and after the meal, we sat down in the front room for some drinks. She didn't seem herself so I asked her if she was ok?

"We really need this," she said. "Me and my husband have been having problems and we've saved up to go away on this holiday hoping to put the romance back into our marriage. We don't have much money left to hire a house sitter and I'm just so worried about leaving our little house empty for so long."

She started sobbing so I put my arm around her for comfort. "It's ok," I said, "I can house sit for you. Besides, I'm unemployed right now so it would save me some money while I'm looking for work." 

Her face lit up. "Really?" She said. "Oh my god, that's so kind of you. Thank you!" She screamed as she pulled me in for a hug.

A few weeks later I drove over to her house, pulled up in her driveway and wandered up to her door. Her face was beaming as she welcomed me into her home. Her husband shook my hand briefly, then began picking up the suitcases and loading them into the car.

Teresa handed me her door keys and a note with a list of contact numbers, in case of emergency and told me to help myself to anything I needed. "Mi casa es su casa," she said, as she grabbed her bag and coat. She gave me a quick hug and rushed into the car. I waved as the two drove off into the distance leaving me in the house alone.

The first night I began to settle in, figuring out how to use the cooker, where the food and coffee was, how to work the remote for the cable and after a few hours, began to relax. I went to sleep and woke up feeling refreshed, then wandered downstairs to make breakfast before heading to unpack my things for the weeks ahead.

The first few days went by pretty fast, and I felt really comfortable in the house on my own. Every morning I woke up and did the same routine, searching for jobs on my laptop and then hanging around watching TV for the rest of the day. I was struggling to find work and was getting really bored being in the house all day on my own.

I think it was the sheer boredom that led me to go and look around in Teresa's bedroom. I opened the door into a large room, in the middle was a king-sized bed with silk sheets and pillows all over it. There was a huge mirrored wardrobe that ran right the way along one side of the wall making the room seem twice the size. Beside the bed were two large sets of drawers and there was a long ottoman at the end of the bed.

I sat on the bed facing the mirror and pulled open one of the drawers, inside were some of Teresa's undergarments and an assortment of lingerie items. I opened another drawer to discover even more skimpy garments, some French lingerie, silky lace bra and thong sets and a variety of pantyhose and stockings.

As I opened another drawer I felt a sensation in my groin, my penis hardened slightly as I saw more and more lingerie. I rubbed my fingers across the material feeling the soft and silky touch of dozens of sexy bras, Basques and corsets, making my cock stiffen in my jeans.

I pushed the drawer in and opened another. My heart skipped a beat as I slowly opened it up to reveal an array of sex toys, from vibrators to dildos, cock rings, butt plugs, love eggs, lubes and lotions of all kinds. My cock pushed harder against my jean zipper and I noticed how turned on I was getting looking through all of her unmentionables.

I remembered Teresa's words, echoing in my head, 'mi casa es su casa', my house is your house. Before I knew what was happening I had torn off my jeans and shirt, pulled down my boxers and was ripping off my socks. I raced through the drawers picking out a scarlet red lace push-up Basque set and slipping it on over my ass and up my body.

A chill ran down my neck and made me shake with excitement as I pulled out a thong and some sheer black stockings, rolling them up my legs and fastening them into the suspender clips. I could see myself in the mirror and began to move like a girl, enjoying the way the lingerie accentuated my shape.

I felt so alive as I pranced over to the mirror wardrobe almost entranced by my reflection. I slid the mirror door across revealing a huge collection of suits and dresses, immediately fixating on how many dresses there were. As I slid open another door my heart skipped again as I revealed even more dresses and a collection of sexy costumes.

As I slid across another mirror, revealing even more garments, every dress imaginable from sequin to lace mesh, wet look to club and party dresses, cocktail, bodycon and so many more. I had never seen so many woman's garments outside of a store. My cock sprang into action pushing the lace thong aside, quivering and swaying in the air.

I tucked it back under the lace and flicked through the dresses trembling with excitement. I wanted to try on every single one. Each one I pulled out made me dribble a little pre-cum into the lace. I stopped suddenly as one of the costumes caught my eye. It was a sexy red shiny strapless bodycon 'Jessica Rabbit' style costume complete with gloves and a long wavy red wig.

I snatched it off the hanger and immediately began pulling on the tight bodycon dress over my stockings and Basque. I slid on the gloves one by one and donned the wig, sitting crossed legged on the side of the bed, watching myself as I brushed my hair. There was still something missing I thought, standing up and wiggling over to the mirror doors.

Neatly arranged along the floor of the wardrobe was a wide range of ladies shoes. I pulled out a pair of red ankle-strapped platform pump high heels to match my outfit. They were a size too small, but I managed to squeeze them on and loved the way they made my feet look so petite.

I stood back and stared at myself in the mirror, barely able to recognize the slutty girl standing in front of me. Beside the bed was a vanity mirror and an assortment of makeup items. I dabbed on some foundation, applied some lipstick and did my best to use the mascara for extra effect. 

To improve the experience, I stood up and started practicing walking around the house in high heels. The dress clung to my body and I noticed how moving my hips helped me to balance. As I teetered around the house I began to feel more feminine, swaying my hips and arching my back to accentuate my ass and tiny tits. 

Determined to explore my new found femininity I tottered back into the bedroom, enticed by my reflection as I strutted past the mirror and bent over to open the bottom drawer. Inside I picked out a realistic six-inch dildo and a tube of tingling lubricant lotion. I lifted the dress up and pulled the thong to one side, using the lube to loosen up my bum before gently running the head over my hole and slowly easing it inside.

Laying on my back I quivered as my virgin ass began to tingle from the sensation, easing it in further and feeling a new pleasure in my erogenous zone. Swiftly, I rolled over onto my side, watching in the mirror as I pushed the dildo deeper; letting out an unexpected girly moan as I enjoyed the climactic sensations. 

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After several minutes of erogenous pleasure, I sat up and grabbed some pillows, kneeled on top and faced the mirror as I slowly eased myself back on top of the dildo. My body looked slim and sultry as I began to bounce onto the pillows, the dildo sliding in and out of my tight pink hole.

As the dildo pressed against my g-spot I let out another uncontrollable girly moan. "Oh baby, yes. That feels so good," speeding up as the pleasure increased. "Fuck me like a slut," I moaned. Every time I looked over at the mirror I felt a hot flush run over me as I stared at the reflection of the slutty girl performing sexual acts in front of me.

The dress was riding up over my hips revealing the garter straps and tops of my stockings. I looked down thinking about how sexy this made me feel and noticed a trickle of cum oozing from the tip of my soft penis as it slapped against my lower abdomen.  I leaned back to allow the dildo to penetrate me further moaning in ecstasy.

The movement must have jolted the dildo which suddenly began to vibrate. "Ooooh, my gosh!" I shrilled with surprised delight, rubbing my pelvis harder against the bed as I pulled the dress off over my head and threw it on the floor. 

The bed was shaking as I began to thrust faster, pulling down my Basque and pinching my nipples as I bounced on top of the vibrating cock. "Ooooh shit," I screamed, fucking my ass harder, my hair swaying across my back. Cum began dribbling from my tiny flapping penis and I could feel an orgasmic sensation building inside me. 

'What was happening?' I thought, feeling dizzy from the experience. My stockings were sticky from all the cum that continued to dribble out of the tip of my penis as I pounded the dildo, taking all 6 inches deep into my ass. As the cock vibrated against my prostate shuddering my g-spot I felt an intense orgasm.

Cum began to gush all over my stocking-clad legs as my orgasm climaxed. I screamed out like a girl in satisfaction as I coiled over into a fetal position, shaking and trembling with contentment. The reality of what I had just done hit me and I quickly hopped off the bed panicking at the sight of all the stains on the silk sheets.

I raced to undress, trying desperately to put everything back so it wouldn't be noticed. A few hours later, after I had cleaned up the mess and washed the bedsheets, I crept back to my room and lay in deep thought. "What the fuck?" I mumbled to myself. "What would Teresa say if she knew what I had just done in her bedroom?"

The sexy thoughts kept me awake for hours laying in bed, imagining all the lingerie and dresses in the room across the hall. I couldn't take it any longer, tearing back the duvet and jumping out the bed. I headed straight for Teresa's room pulling off my PJ's before sifting through her bedside drawers again looking for something sexy.

My eyes fixated onto a slutty red and black silk lace chemise which felt so smooth against my fingers. My cock spasmed as I stepped into the chemise, feeling the silky material rub against my skin, pulling it up over my ass and sliding it over my shoulders. "Oh baby," I muttered under my breath.

Frantically, I rushed to put on some sheer black hold up stockings and a pair of strappy black stiletto heels. Inside the wardrobe was a collection of costume wigs, I reached in picking out a long curly center-parted brown wig that matched my natural hair color. After sliding onto the bed, I rolled around feeling the silk lace rub against my skin, reaching into the drawer for some lube.

Over the next few hours, I explored my body using a variety of sexy toys, determined to find the perfect way to orgasm like a girl. Eventually, tired from all the erotic play, I fell asleep on the bed, still wearing the chemise and stockings. In the morning when I finally awoke, I felt a new sense of identity.

Nothing had ever made me feel this way before and I wanted to remain en femme for as long as I possibly could, jumping out of bed and into the shower still wearing the long curly wig. After rinsing myself off, I picked up a pink razor and began to shave off all my body and facial hair, enjoying the feel of the warm shower water.

Stepping out the shower I wrapped the towel around my body, covering my stomach and chest and wiggled back to the bedroom. I spent an hour or so preparing myself, brushing my hair and applying makeup until I was happy with the results. The bedroom was a mess and I knew exactly what to do about it. 

Inside the mirrored wardrobe was a beautiful black and white French maid outfit with lace trim and choker. After adorning a black see-through lace bra and panty set, I stretched the Polyester dress on and found some appropriate stockings and black and white heels. 'What a pretty girl,' I thought as I admired myself in the mirror, pausing to take a picture on my phone.

I set about cleaning the house, hoovering, dusting and doing the laundry, all while dressed as a slutty maid. Once I'd finished the chores I sat and pondered what to do next. I thought about Teresa's husband and what he would think if he saw me like this, dressed in his wife's slutty French maid outfit.

Feeling especially naughty, I decided to go back upstairs and head into Teresa's room in search of a realistic cock. Among the various toys and dildos, I found one that took my fancy. It was an eight-inch black cock complete with a sturdy base and realistic balls. I laid it upright on the edge of the bed and kneeled down in front of it.

I visualized Teresa wearing the same outfit, desperately trying to bring the romance back into her marriage as I sank my soft lips over the head of the cock. My tongue moving up and down the silicone cock while I dreamed about how wild this might have made a real man feel. Sucking passionately on every inch as I gagged and choked.

My ass began to yearn for cock, quickly tearing off my panties and straddling the saliva soaked dildo as I eased it into my boy pussy. I tried to picture Teresa hopelessly fucking her husband, trying to make him lust for her once more as I bounced on the bed. "Fuck me," I shrilled, "Fuck me with your big black cock!' 

Orgasmic vibrations ran across my body as I frantically fucked the dildo harder and faster, making the bed creak and shake beneath me. I knew I was about to cum and quickly pounced off the dildo just as cum began to burst out of my tiny penis. I tried my best to direct it over the dildo, covering it in fresh sticky cum.

Sliding off the bed, I kneeled back down and watched myself seductively lick my lips at the sight of the cum drenched cock. I knew I wanted a taste and eagerly performed fellatio, sucking the dildo and swallowing every drop. 'Good sissy slut,' I mumbled under my breath.

Finally, I stood up in my heels and looked over at myself in the mirror. What would they say if they saw me now? I thought. 'Mi casa es su casa.' I smiled.

To be continued...

 

 

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Written by MirandaGreen
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