An Interesting Offer Pt. 01

Hi, my name is Roolk Bennett. I am 20 years old, 5'8" with light black hair and a slim build, the kind of frame that slips easily into shadows or, as I prefer, into silk and lace. My hair's always been a bit of a mess, falling just past my ears in soft, uneven waves that I've never bothered to tame. I am currently in university, slogging through late-night study sessions and endless lectures, and still live with my parents in their cramped, beige-walled suburban house. Let's just say that neither they nor I are particularly fond of that fact--Mom's tired sighs over dinner and Dad's gruff "When you moving out?" remarks hang in the air like stale smoke, while I dream of a dorm room or an apartment where I can lock the door and be whoever I want.

My mother is Skye Bennett. She is 46 years old, 5 feet 5 inches tall, with black hair and a 36C cup size, her figure still curved in a way that turns heads at the grocery store. Her hair's a glossy cascade, always swept back with a clip or left loose to frame her sharp cheekbones, and her hazel eyes catch the light just so. I am aware of her cup size because I have been trying on her lingerie, bras, panties, tops, and dresses since I was a child, sneaking into her room when I was barely tall enough to reach her dresser drawers. I enjoyed dressing up in my mother's clothes and feeling sexy when everyone else in the house was away, twirling in front of her full-length mirror, the rustle of satin against my skin drowning out the world outside.

My aunt, Daisy Bennett, is my father's sister. She's 39 years old, stands 5'7" tall, and has brunette hair that falls in loose, effortless curls down her back. With a great physique and a 36B cup size, she radiates confidence, her posture straight and her stride purposeful, like she's always on her way to conquer something. Since the tragic passing of my uncle in an accident a year ago--a rainy night, a slick road, and a truck that didn't stop--Daisy has found strength in reinventing herself, shedding the quiet widow's shell for a bolder, brighter version. She dove into learning the art of makeup, her nimble fingers mastering brushes and palettes, and now has her sights set on building a successful career in the salon industry, dreaming of her own little shop with a neon sign out front. She is a pretty fun-loving person, her laugh loud and infectious, and always encouraged me to explore life, have fun and go on adventures, tossing me winks and wild ideas like road trips or sneaking into concerts.

My aunt and my Mom were close, thick as thieves since I was a kid. My mom would let my aunt put on makeup on her and encourage her in her career pursuit, sitting patiently in the kitchen while Daisy experimented with smoky eyes or bold reds, the two of them giggling over wine. I was always jealous in this matter, hovering in the doorway, watching their easy bond and wishing I could join in, brush in hand, instead of just eavesdropping on their laughter.

Now, to the time where my time turned around, it was March, the air crisp with that early spring bite, and my mother's side of relatives had a family gathering to which my parents were attending to, a noisy affair upstate with cousins and casseroles. I couldn't go as it was exam season in 10 days, my desk buried under textbooks and highlighters, but the real reason is that I would love some alone time to spend with my mom's delicate, sweet sweet, silk and lace garments and makeup, a secret stash I'd memorized down to the last thread.

I often had wet dreams about my aunt and how I would love to fuck her, her body a vision in my restless sleep--long legs, soft curves, that teasing smile. She always wore delicate, elegant clothes like pantsuits and sundresses, tailored blazers that hugged her waist or floral skirts that danced in the breeze. I always wanted to try her clothes on but never had the chance to, her apartment a distant temptation I'd yet to breach.

On the first day my parents left, their car rumbling out of the driveway just past dawn, I quickly locked all the doors to make sure even if they came back, I would have time, double-checking the deadbolts with a jittery thrill. I don't just like women's underwear--I crave the intimacy of it, the forbidden rush. I love it even more when it is worn and not washed, the faint musk of skin clinging to the fabric like a whispered secret. I love the fact that my dick is where her pussy was in, the thought alone enough to make my pulse race. I like to sniff worn underwear while masturbating, letting the scent flood my senses as I lose myself. I went into the bathroom and found some used pair that was in the laundry bag, a crumpled heap of cotton and lace tucked beneath a towel, but before slipping them on, I took my mom's razor, its pink handle cool in my grip, and shaved my body clean everything eyebrows down, the blade gliding over my legs, arms, and chest until I was smooth as glass.

Then I slipped on the teal lace panty that was in the laundry basket, worn by mom, merely 2 hours ago, still warm with her presence, the delicate edges hugging my hips. This excited me and I started to stroke my now erect cock, standing there in the bathroom's dim light, the tiles cold under my bare feet. It took me about 5 minutes to climax and then I cleaned up, wiping away the evidence with a trembling hand. I then put on a matching padded bra and stuffed socks in them, the weight a clumsy mimicry of Mom's curves. I wore a black polka-dot button-up blouse, its fabric soft against my skin, and wore a teal skirt that came up to my knees, the hem swaying as I moved. I loved the look and put on some wig and makeup, a cheap blonde bob from a thrift store and Mom's cherry-red lipstick, smearing it on with unsteady fingers.

I decided to spend the rest of the day in the same outfit as I had no other work outside the house, lounging on the couch, the TV droning faintly in the background. Then, I got a call from my mom checking in on how I was doing, her voice crackling through the line, and informed me that my aunt needed a specific makeup kit for practice and she would pick it up from our house in the morning, a sleek black case I'd seen Daisy tote around. This got me thinking, "My aunt is an adventurous person, should I tell her about my crossdressing secret?"--her free spirit flashing in my mind like a dare. I came up with a plan and couldn't wait to execute it; tomorrow can't come soon enough.