Cassidy's Tale Pt. 01

Part One

My name is Cassidy and I'm a 21 year old cross dresser. I am very comfortable with my androgyny and live my life in cute feminine clothes. I've kept a steady regimen of electrolysis on my face and keep the rest of my body hairless. I have long light brown hair with a slight wave to it. I am 5 foot 6 and weigh 130 pounds, so I definitely pass as female.

My parents both passed away recently and since I was their only child I inherited a small amount of money and the small family home: a suburban 2 bedroom rancher. I moved there shortly after I took possession.

Due to the money left to me, I can take a break from working for a living and set up how I plan to live my life. I find myself lounging around the house quite often in my favourite outfit, thigh high stockings, denim miniskirt and a black camisole. I keep my penis locked in a chastity cage, as I like the restrictive feeling of it. I'm also usually wearing one of my butt plugs. I've gotten very used to the sensation of feeling filled all the time.

Recently, a new tenant has moved into the rental house next door: a man named Reese. Reese is around 40 and is tall, slightly overweight but in decent shape. I often see him unloading tools from his pickup truck when he gets home from work, so I believe he must have a job in construction or maintenance. He is usually unshaven and comes home dirty and sweaty. I find him somewhat repulsive, but still, there's something compelling about him.

I like to sit on my back patio in the evening, lounging on my porch swing, with my stockinged legs dangling over the side. The other day, Reese was out mowing his back lawn. He was wearing dirty jeans and an old t-shirt with the sleeves cut off. I saw him stealing glances at me several times. This gave me a slight feeling of revulsion, knowing this sweaty older man was trying to gawk at me. But then I felt a slight twitch in my caged penis. Was I attracted to this man? I decided to go inside my house and forget about it.

Two days later as I'm headed out to the store, I see Reese pull in to his driveway, home from work. As he gets out I catch the smell of his body, sweaty from a long day's work. Again, my penis twitches in its cage as I watch him lift his tool box from the back of his truck. He spots me gazing at him and gives me a smile. I awkwardly wave and go on my way. I wonder what is happening to me.

A few weeks later I was doing laundry and my dryer suddenly stopped working. It was a Sunday, and I knew I wouldn't be able to get someone out to fix it until the next day. It had been raining all day, so I couldn't hang my clothes up to dry. I really needed this machine fixed. I heard Reese's garage door opening. I got an idea. I go outside in the rain and ask Reese if he knows how to fix a dryer. One look at me with my cute outfit clinging to my soaking wet body, and he eagerly agrees to help me out.

Reese brings his tool box into my house and quickly finds the problem with the dryer. He says he can fix it. While he goes about the repair, I dry my self off nearby with a towel, taking note of Reese's casual glances in my direction. Once he finishes the repair, I thank him and ask how I could repay him. He says not to worry... it's what neighbours do.

After he leaves, I can still smell his scent lingering in my house. I close my eyes and inhale deeply. I nearly swoon as the smell enters my nasal cavity. My penis now strains against its cage. I'm definitely changing my opinion of Reese.

The next time I hear him mowing, I make a point of being out on my patio again, wearing my favourite outfit. When he stops for a moment, I make a comment about how hard he's working. I invite him to over for a cold beer. He accepts.

When he arrives, I show him to the couch. I grab a beer bottle from the fridge, making sure to band over as I reach in. When I hand it to him, I lightly stroke the condensation off the outside of the bottle neck. He takes the beer and easily twists the cap off. I gently sit down on the floor nearby. He asks if I'm having a beer as well, and I tell him I don't drink beer. I bought them for him. He keeps looking down at my short skirt barely covering my stocking tops. He says "nice outfit ". I tell him how it makes me feel cute. He tells me it does make me look cute. I get up from the floor and sit beside him on the couch. I thank him again for fixing my dryer. Looking into his eyes, I say that I'd really like to do something in return. He takes another drink and ask what I have in mind. I lean in and kiss him. The feel of his stubble against my face and his manly scent send my penis into an uncomfortable state. I pull back and ask if it was ok to do that. Reese looks a little startled but tells me it's not a problem, but he should be getting back to his lawn. He leaves, and I sink into the couch. I need to plan my next move.

The following week, I approach Reese as he arrives home from work. I'm carrying the pizza I just ordered pizza and tell him I'd be up for sharing with him if he's interested. He says sure and invites me in. We sit at his dining room table, and I look around his place, taking note of the slight disarray. I tell him I'd be happy to help tidy up for him, in exchange for his continued help with any household repairs I might need. He admits he's not the tidiest person. His sister used to come by to help with that, but she's gotten too busy with her real estate job. We make an agreement to help each other out. After our meal, I go home feeling like my plan is set in motion.

I arrive a few days later to clean Reese's house. He finds me at the door wearing a pink crop top, denim "daisy duke" shorts with sheer tights and ballet flats. I'm carrying my cleaning caddy. I explain that before my parents died and left me the house, I worked as a house cleaner, so I'm well equipped to keep his place in order.

I first set about washing his dishes and cleaning the kitchen. I see him watching my body as I scrub his dishes. Then I go around picking up his pieces of clothing that he's left lying about. I make sure to bend over as I pick up each article. And I lean over as much as possible when putting them in the washing machine. Next I tidy up the piles of car and motorcycle magazines littering his living room. I make a special effort to brush my silky hosed legs against his every time I move past. Eventually, as I'm picking up a stack of magazines, I pretend to lose my balance and I fall into Reese's lap. I giggle and say it must be time for a break. As I sit there, I can feel his erection under my thigh. I look into his eyes and reach down between his legs. As I gently run my fingers along the crotch of his jeans I ask playfully "is that for me?". He looks a bit bashful. I grab his face and kiss him long and hard. I then drop to my knees in front of him. I give him an innocent look and ask if there's anything else I can clean for him? He looks at me with a stunned expression which turns into a slight smile. He says quietly "yes?".

I slowly reach up and unfasten his jeans. He helps me pull his pants and underwear down to his ankles. I lean in and take his swollen manhood into my mouth. As I begin to move my mouth back and forth I inhale a big waft of his man scent. My penis strains hard against its cage. I continue to move faster and faster until he begins to moan. I slow my pace slightly and start to use my tongue. I slide along and around his stiffness and then engulf his entirety with my mouth. I feel his body shudder as he explodes into my mouth. I savour his salty discharge for a few moments before I swallow the whole load. I sit at his feet with a contented smile on my face, then I quickly stand and say "well, back to work" and go back to doing his laundry. When I'm done with the chores and about to leave for home, Reese approaches me to say it was amazing having me there. I told I'd be back anytime he needs me. He asks if I can come back that night. I smile and say "I'll be here at 7".

After returning home, I flop onto my bed and can't help but smile. I can't believe what I just did and I can't believe how amazing it felt. Now I have to decide what I'm going to wear for our evening appointment. I look through my closet and pick out a slinky red top. I then grab my leather miniskirt. I know I need to be ready for anything, so I take a brand new pair of black stay up stockings out of my drawer. I place these items on my bed and remove my clothes I wore to clean in. I hop in the shower and make sure I am clean shaven everywhere. After drying off, I remove the plug I was wearing and replace it with a larger one, to ensure I can fit in anything that might be required later on. I sit at my dressing table and meticulously apply my makeup. I give my eyes a sexy cat eye swoop. My lips are coated in bright red lipstick. A quick spray of perfume and I'm ready to get dressed.

Next I put on my nicest pair of black panties. I then slide my new stockings up onto my freshly shaven legs. The soft sheer fabric gliding along my legs makes my penis convulse in its cage. I then put my slinky top on and pull up my miniskirt. I look in my full length mirror and make slight adjustments. I'm ready to go. The last thing I need are my red stiletto heels. I tell myself I look like sex personified. I hope Reese thinks so too.

I step out into the early evening air and take a deep breath. I feel like my life is about to change. I'm ready for it.