Outing Sissy Pinki

My virgin mate needed a woman… so I became one.

I’d known Eddie since we were fighting over action figures. We’d grown up in the same neighbourhood, gone to the same schools and quite often fancied the same girls. He wasn’t a handsome guy, but was by no means ugly, so I could never really understand why he’d never had a steady girlfriend. 

He ‘talked the talk’ when he needed to fit in with the lad banter, but I was pretty sure he’d never actually slept with a woman. At least, he’d never told me about it when we wasted hours talking. And I’m pretty sure he’d have been keen to brag about that one.

Eddie had never really outwardly come on to me, but we’d flirted as part of our own unique banter. We’d joked about kissing as teenagers and we’d often fallen asleep in drunken states, only to awaken cuddled up on a sofa, before awkwardly pulling away.

As children we’d played the usual boyhood games of ‘you show me yours and I’ll show you mine’, so I knew he was considerably better hung than me. I’d often thought about how it would feel to touch it when we changed in front of each other, or stood together at the urinals. I loved to sneak a cheeky look at it, but he’d never called me out for doing so.

As close as we were to each other and as honest as we’d been throughout our lives, I’d always had one secret I’d never told anyone. Not even Eddie. Since as young as I can remember, I’ve always fantasized about being a girl. Not forever, just for a night. Just long enough to experience what it feels like to really be a woman. To feel the soft, pretty clothes. To feel the lipstick on my lips. To walk about in public and feel men look at me, and undress me with their eyes. I’d never admitted it to anyone. But lately, I’d been getting brave. Having my own place, having a disposable income, it gave me the freedom to start experimenting. And I loved it. 

I’d become familiar with the right styles to compliment my figure. I’d found my ‘look’. And I’d practiced for so many hours in front of the mirror that my hair and make-up were pretty professional looking. I’d even shaved off all my body hair. The smoothness of my skin made me feel incredible. I loved how I looked as a woman. How I felt looking back at my reflection. I’d have jumped through and fucked me if I could have.

It was a weekend in May if I remember rightly.

Eddie had suggested we meet at my new place and have a few drinks to ‘break it in’ before heading out to hit the town. I knew he’d been feeling down about his lovelife, or lack of. I knew he felt frustrated that he’d still not found someone to share any sexy moments with, let alone romantic ones. I felt for him. I knew it must be hard on his confidence, and I wanted him to feel wanted. That week, I’d bought a bottle of gin for us to christen the new flat.

That wasn’t all I’d bought.

I had enough left over from the move to treat myself to something new. Something silky. Something sexy. I bought the sexiest, skimpiest knickers I could. Tiny black lacy ones that arrived in a discreet but oversized package just a few days before. Together with my favourite stockings and suspenders, they accentuated my figure better than anything in my wardrobe. And they slid perfectly underneath my best little black dress. My legs looked twice the length in that little number.

 It was a boring Saturday. I knew we weren’t meeting until seven, but the bottle of gin on the shelf seemed to sing to me that afternoon. I only snuck one or two, but as always when I have a few drinks, I felt the urge to dress up. I took my time to bathe; shaving my legs, my armpits and my ass. I shaved the pubes above my little dick into a girly little triangle. I left just my forearms and my hands, just enough to hint at the man that was hidden deep beneath my rampant girly desires.

I took time to dry myself slowly in front of the mirror, staring at my long smooth legs as I wiped away the remaining drops of water. It made me sticky to see how much of a woman I could be. To see how accustomed I’d become to the lifestyle. How much I desired to dress in the sluttiest of outfits. How much I craved my first proper experience as a serving sissy.

I moisturized my legs from top to bottom, then sat before the mirror putting on eyeliner, eyeshadow and mascara. I applied a deep red lipstick, which matched my nails perfectly. Then I sat for a while, dreaming about being held by a man. About being undressed by a man. About being with Eddie.

I put on my new knickers, tucking myself away so as not to stretch the material out of shape, then slowly, carefully slipped on my stockings. That was one of my favourite bits of dressing. Feeling the soft silk roll gently up my legs to sit firmly on my thighs. I put on my pink wig and played with the hair for a while until it was just right. I stepped into my little black dress and pulled it into position, aligning the straps with my bra. And then I sat, waiting and watching the hands on the clock creep closer to seven.

I’d been thinking about opening up to Eddie for years now. ‘What the hell’ I thought. It’s make or break. Either he wants me or he doesn’t. I reassured myself that if I’d got this all wrong, at least we could laugh about it in years to come, over a bottle or two. Best-case scenario – I get to touch that beautiful cock of his at long last.

The doorbell rang.  The fear struck me like a lightning bolt. But I wasn’t going to back down now. How could I? It would take me an hour to get all the make-up and clothes off anyway, and I couldn’t leave him waiting on the doorstep.

This was it. I had to do it.

I took a deep breath, puffed out my chest to show my cleavage as best I could, and slowly walked to the door.  I froze. I was shaking with fear. And I was sticky, oozing a little into my new knickers. Had I lost my mind? Was I really going to show myself as a woman for the first time? And to one of my best friends?

The doorbell rang again and I felt my arm rising, shaking towards the latch. I felt the air rush in against my smooth thighs as the door swung open…

I nearly fell to my knees there and then. I felt giddy. I felt terrified yet hornier than I think I’d ever been in my life. Standing before me on the doorstep was not just Eddie, but four of his mates. Everyone stood, jaws open in complete silence. There I was, fully dressed in my sexiest outfit, in front of five tall, strong men. Vulnerable and on display. It felt like time stood still.

It was Eddie that broke the silence in the end. And I’ll never forget a single syllable of that sentence and how amazing it sounded to my ears.

“You going to invite us in then slut, or what?”