Chapter 1 – Discovery

Saturday 4th April 2015

Stirling

Scotland

For this week, it was one of my two days off from my job at the local supermarket, and I’d been looking forward to it so much. Wednesday had been my last free day, but I didn’t have the privacy I’d hoped for. My dad and Lauren, my stunning stepmother, had been at home most of the day. Today, however, they were both at work.

Only because I knew I had the house to myself, I spent the first hour on my laptop, mainly on social media. As I sat at my desk in nothing but my short silk robe, I was tempted to browse my favourite porn channels, but I resisted, knowing that I had plenty of time. The thought of them did bring something else to mind which increased the arousal under my robe.

“At last,” I said aloud. “I can investigate Charlotte’s room.”

I went down to the kitchen, fixed myself a coffee and returned upstairs. Although I was alone, it still felt peculiar going into my stepsister’s bedroom. She was at uni doing a course in Fashion Design so was sharing a flat with two other students. Charlotte’s nineteenth birthday had been a few months earlier, in September, before she’d arrived at our house with her mother. After setting up her bedroom, my lovely stepsister returned to the Edinburgh College of Art to continue her studies. She had a part-time job near her flat, so only returned home to Stirling occasionally.

Before touching anything, I stood in the doorway and looked around the bedroom. It was mainly decorated in red, pink and white, with white furniture, but the outstanding feature was how tidy she left it between her brief visits. I sipped my coffee and carefully placed the mug on the dresser.

“What have we in here?” I opened the two mirrored wardrobe doors and stood back. “Oh, thank you, Charlotte.” I stepped forward and moved the hangers along which held jackets, dresses, skirts, blouses, shorts, and trousers. There were a lot of clothes left behind, and she must have taken plenty with her. On the base shelf, I discovered shoes and boots.

I stepped back, knowing that I’d soon be having fun. “Now, my sweet stepsister, what would you keep in your dresser?” I pulled open the top left drawer to find makeup of all sorts, and it had to be spare, because I couldn’t imagine a girl living without her makeup. The other drawers contained bras, knickers, tights, and incredibly, a basque, and stockings. I went through the three drawers on the other side to find costume jewellery, hairbands, ribbons, nighties, scarves, and gloves.

I went through the lingerie, selected items, and placed them on the bed. As I gazed at the black babydoll nightie, black knickers, and sheer, black hold-up stockings, my cock stirred under my robe. I was aroused by handling the soft feminine garments.

“If I get dressed how long will I last before giving myself a handjob?”

I’d heard the slight tremor of excitement in my voice, and I played my fingertips over the sheer fabric of one of the stockings. I thought of something that Charlotte had said the last time she was home for a couple of days.

“Apart from your chest, you and I are almost the same size, Greg, and you’ve got nice legs for a guy. If you ever want to borrow anything, have a close all-over shave so that you can enjoy the fabrics.” She’d laughed, and winked at me when I gasped. “I’m only kidding” she’d continued, “but I’ve heard that some guys like dressing up.”

I still hadn’t shaved or showered yet, and the more I touched the soft garments, the more I wanted to enjoy the sensation of wearing them. I sat on her padded dresser stool, sipping my coffee and gazing at the items on the bed. I thought of the porn sites I’d visited and imagined what it might feel like to have a fetish, or even to be a crossdresser, presenting as a girl.

Five minutes after finishing my coffee, I was standing in my en-suite. I shaved my face as usual, and it didn’t take much consideration before I shaved the few hairs from my chest, pubes, and legs. The mere fact that I was making myself smooth all over before wearing Charlotte’s things had my cock erect and throbbing. I stood there for a moment and as I undid my long ponytail, I noticed the soft tufts of fair hair under my arms. Two minutes later, those hairs were gone too, and I stepped into the shower.

I was about to use my regular gel, but instead, lifted Lauren’s gel which would smell nicer. I wasn’t sure if it was the simple action of spreading the fragrant substance on my smooth legs that was exciting me, or because it belonged to my sexy stepmother. I stepped away from the hot spray, and bent forward, before reaching back to add a large dollop of sweet-smelling gel between my buttocks. I slipped a finger into my crack, and pressed lightly on my tight rosebud. I thought of scenes of anal toying in the porn videos, and probed with my slippery fingertip.

“Oh my god, that feels nice.” I added more gel, used two fingers to keep my buttocks apart and probed with a fingertip again, but this time gained entry, and slipped my middle digit in and out of my anus. I imagined doing something similar but when wearing Charlotte’s lingerie.

My next sensual experience was when I used Lauren’s moisturiser on my legs. I’d never seen the point in such a thing, but as I applied it using both hands, it felt amazing, and sexy.

Instead of using a hairdryer, I sat at Charlotte’s dresser naked to brush my long straight blond hair. As I used long steady strokes I gazed at my reflection. I had an athletic build, rather than being skinny, and my complexion was pale. In the mirror I caught sight of the soft and sexy items I was about to try on, and imagined what I might look like as a girl.

“I’ll look like a young guy in girls’ clothes.” I laughed nervously as something came to mind.

I centre-parted my hair, but for a change I didn’t use a rubber band to pull it into a ponytail. The temptation of my new idea was strong, and wouldn’t leave me. I pulled open the top left drawer, and lifted out various items and containers to read the labels.

“Concealer, foundation, blusher, mascara, eye-liner … and it goes on an on.” After reading them, I replaced them and as I did, I spotted one that I recognised. I lifted the small gold cylinder and pulled off the cap. Bright red lipstick, and I felt a fresh stirring between my legs.

I looked down at the dark, glistening, bulbous head of my cock as it started to grow and thicken. “You like the idea of me wearing this too, don’t you?” It took a couple of tries before I was able to use it properly, and the difference was incredible. Against my pale complexion the glossy red substance looked amazing on my lips, and that caused me to smile, which looked even better. I poked my tongue our and licked at the lipstick, enjoying the sensation and the flavour.

“I’ll stop at the lipstick,” I murmured. “Perhaps I’ll try the other things on another day.”

I lifted a black stocking and rolled it between my fingers the way I’d seen it done on videos. I eased the black reinforced section over my toes and gently pulled the sheer nylon along my leg. When I got it all the way up to my thigh, I teased the elasticated lace top up before sliding the fingers of both hands along the stocking from toe to thigh.

“Oh my god, that feels wonderful.” I repeated the procedure with the other stocking and lifted the black lace knickers. By the time I got them up to the top of my thighs my cock was throbbing. I parted my legs slightly, and tugged my balls and cock forward to be cupped and held firmly by the delicate underwear. The snug fit felt incredible, even if my cock was producing a long bulge at the front. When I slipped the babydoll nightie over my head and dropped the thin straps onto my shoulders I became conscious of my heavy breathing.

“Okay,” I said, shaking the short nightie to make it sit properly. “Let’s have a look at you.” I faced one of the wardrobe door mirrors and took a deep breath. “Bloody hell, that’s sexy.” I turned left and right, slightly bending one knee and then the other. I grinned at the memory of Charlotte saying I had good legs. I liked what I saw in the mirror, but there was something missing.

“High heels,” I said, and squatted to look at the selection in the bottom of the wardrobe. I located a pair of black high heels and sat on the end of the bed to try one on but it was no good. “Oh well, it was worth a try.” As I put them back I noticed that there was a black pair which were toeless. “High heeled sandals.” I lifted them out and tried one. “No, good. I’ll never get the straps to buckle.”

I stood to admire myself again, turning this way and that, and a framed photograph on the wall caught my eye. It was Charlotte and her mother, both dressed up for some occasion and they looked more like sisters than mother and daughter. They were both sexy, and as that thought passed through my mind, I had another idea.

I couldn’t remember the last time I was in the master bedroom. As I entered in Charlotte’s lingerie, it struck me that I’d never ventured into this room in the six months that Lauren and Charlotte had become our new family. I wasn’t there for sentimental reasons, and two minutes later, I was trying on a pair of red high-heeled sandals.

“Oh, yes.” I had to push my toes as far forward as possible, but the buckle on the strap reached. I sighed as I fastened the sexy strap of the first one around my ankle, and then I fitted the other one. “Now, let’s see if I can walk in these gorgeous shoes.”

It took a few minutes and I had to grab furniture and doorframes to ensure that I didn’t fall, but I got back to Charlotte’s bedroom, and stood in front of the full-length mirror again. My long fair hair looked okay, and if I didn’t look too closely, the bright red lipstick caught my eye at a glance. I held the hem of the short nightie out to the sides as I savoured the sight of my legs in black stockings, and the way those same legs looked so much better when stretched by wearing stiletto heels. I grinned at the reflection of the one thing spoiling my girly look. My cock was stretching the black knickers and I could see a little spot of damp where pre-cum was oozing through the lace.

“No relief for you yet, my friend, I want to savour looking like a girl for a while.”

I was extremely careful as I made my way downstairs to fix a fresh drink.

*

I sat at the desk in my room with my laptop open and in no time I was browsing my favourite porn sites. I checked out my usual categories which were lesbians, and gorgeous girls being taken by one or more well-hung hunks. As I flicked through the options using my right hand, I placed my left hand on my thigh and the sensation caused me to look down. I caressed my thigh and trembled with delight as my fingers crossed the lace top and onto my nylon-covered leg.

“Fetishes is the category I ought to be checking out.” A few seconds later I was flicking from one video to another, taking in the sight of men who were either naked, or wearing feminine underwear. One or two featured men wanking while kissing and licking a shoe. Others featured guys who wrapped their hard-on in a pair of knickers, stockings, or a nightie. Most of them were videos of men, crossdressed as I was, caressing the items they were wearing. In a couple of the instances, they were using one hand to enjoy the sensation of the fabrics, while the other hand was producing a more direct pleasure, sliding up and down a throbbing cock encased in knickers.

I had no recollection of time passing as I scrolled from lesbians, to regular couples, bisexuals, fetishes, crossdressing, transgender, and finally, several anal categories.

As my excitement grew, my breathing became steady panting, and I scrolled back to a video featuring a handsome guy lying in bed with a beautiful woman. Her cock was as big as his.

“I don’t care if people call you a tranny, a she-male, a chick with a dick, a girl with extra, or a transsexual … you are beautiful.” I turned the volume up as she whispered to her partner.

“I’m going to stretch your tight asshole with my girl cock.” She spread lube between his buttocks and slipped one finger and then two inside him. ‘I can’t wait to fill you with cum.’

“Yes, please,” I whispered and focused on her sucking his hard cock as she fingered his hole. I slipped my buttocks forward on my big swivel chair, moved my feet apart and stroked the bulge in my knickers. I dropped my other hand to caress my nylon-coated thighs.

A glance at the sliding bar at the base of the video suggested there were fifteen minutes left.

“I’d never last fifteen minutes with that beauty. Besides, could I possibly take her cock in my bum-hole”

They kissed passionately, before she moved down his body, and went back to sucking his cock. She introduced three fingers in the preparation of his anus, and after adding more lube, she pressed the head of her cock against his hole.

“Get ready lover … oh … you’re hot in there.” She slowly eased the full length of her impressive dick forward, until it disappeared inside her partner’s hole. As she thrust back and forward, she gripped his stiff dick and stroked it slowly. Her balls slapped into her man’s buttocks. “I’m gonna make you come first, and then I’ll fill you with my creamy cum.”

My breathing was out of control, and my right arm was pumping up and down rapidly as I imagined the beauty fucking me and my hand was her hand.

“Yes, yes, yes … oh … fuck yes,” I cried out as I shot my load inside Charlotte’s knickers.

“Yes, indeed,” a familiar voice said from behind me. “That looked like fun.”

My heart missed a beat, and I turned to see my gorgeous stepmother. “Laur … ren ….”.

Her statuesque figure was framed in the bedroom doorway. She wore a short red summer dress, which accentuated her shapely legs in black stockings, and her long auburn ringlets were draped over the front of her shoulders. She smiled as she continued to aim her phone at me.

***