The text message which just landed on David’s phone read:
~ I’ll meet you at Larry’s Bar in town. 8pm. Don’t be late, Karen x
David tucked himself into his lilac cami-knickers before pulling on a pair of jeans and T shirt. There was just enough time to take off the crimson red nail polish before making his way to the bar to meet his friend.
It had been ages since Professor David Forbes had last seen Karen, and he was looking forward to catching up over a meal and a bottle of wine. They both studied at Cambridge and had dated for a while, but the sexual attraction inevitably morphed into platonic respect. Although Karen enjoyed a bit of kinky fun in the bedroom, her repertoire didn’t quite reach the heady heights of dating a cross-dresser. Of course, David at the tender age of nineteen hadn’t intended to reveal his dark side, his ‘Diana‘, to anyone at the university. Despite first acknowledging his feminine side when he was about sixteen, David’s relationship with Diana had still been very much at its experimental stage during his first year in Cambridge.
A compelling urge mixed with curious desire gave birth to many experiments—underwear, dresses, makeup—all strictly between David and the four walls of his student residence. Oh, and the full length mirror he had acquired for next to nothing from the local junk shop.
There was just that one exception.
One evening, Karen had arrived at his room a full hour earlier than expected, only to catch him in mascara and lipstick, together with a black thong and matching cropped top. Shock, horror and yelling eventually gave way to heart-to-heart confessions. David would never deny who he was and who he wanted to be; Karen would never claim she could cope with that.
Karen was not Lucy, the girl who loved both David and that feminine side of his being, Diana. But she was a good friend, and David didn’t have many of those. So tonight David was 100 per cent man, knickers excepted (he did have his limits, after all). He grabbed his keys and headed to the tram. Larry’s bar was on the outskirts of the city so there was time for his mind to wander…
It was Saturday night and sixteen-year-old David Forbes headed to the family bathroom. It had been a long day stacking those shelves at the supermarket, and he was knackered but there was no way this opportunity was going to waste. Mum and Dad were at some classical concert, his older sister had gone for a curry with her friends, and he was alone in the house. Free to do whatever the hell he wanted.
Standing in his underpants in the family bathroom, he pulled the top off the crimson red lipstick he’d stolen from the shop. Well, not exactly ‘stolen’. There was a sale bin at work labelled ‘Anything for a Pound’. It was filled with stock that had been around for too long, and virtually all the staff helped themselves. It was more a case of perk of the job than stealing. And David had been far more scared about the fact he had taken a lipstick than the fact he hadn’t paid for it.
Staring into the mirror, he stretched his lips wide and pushed his jaw forward. Then he dragged the crimson point of the lipstick over his bottom lip. The skin puckered and it was easy to see where the colour had touched and where it hadn’t. Surprised, he ran his finger along to rub in the thick, almost sticky substance. From watching his mother put her lipstick on, he had assumed it would be a creamy texture, easy to smooth over one’s lips. Now, his reflection revealed red streaks with smudges leaking beyond the edge of his lip. It was a mess. He looked like the bloody Joker! No wonder this stuff had been thrown into the sale bin.
Not one to give up at his first hurdle to feeling feminine, David applied more lipstick, and this time continued around the top lip. Okay. He was no Marilyn Munroe, but it felt nice. He ran his tongue over the cosmetic and peered closely at his reflection, the contrast between red lips and white teeth exciting him. With his mouth wide open to reveal more of those teeth, he laughed. Then he pressed his lips together, sucked in his cheeks and blew himself a kiss. Cheeky and flirty!
Giving in to the urge to feel more feminine, he turned his attention to the pink Lycra tights. His sister had thrown them in the waste bin a few days ago, and when David saw them, he hid them in his bedroom, praying that Alison wouldn’t notice they were gone. At last, he could try them on.
He gazed at his reflection once more. He didn’t look like a girl. He looked like a stupid boy wearing lipstick. But he didn’t feel stupid. His heart was racing with an eclectic mix of fear, apprehension and excitement. Would the tights make him more excited or more afraid?
Casting his concerns aside, David sat on the edge of the bath and held the tights up, watching the long legs dangle before him. They’d better stretch a fucking long way ‘cos even though he had skinny legs, there was no way these would reach over them. But glory be to the powers of elasticity. One long hairy leg was steadily hidden by pink Lycra up to his thigh. The empty leg hung down like an unused elephant’s condom. He was about to attempt to insert his other leg when he had an idea. Something that would feel even better.
He slid his briefs down and let it all hang free. Then, sitting on the edge of the bath once more, fully aware of how cold it was, he leaned forward and managed to get his other foot into the tights. He wobbled to his feet and felt ridiculous with one leg covered half way up his thigh and the other half way up his calf. How the hell did girls manage to get these on? With more pulling and stretching, the crotch was now bridging mid-thigh. The hairs pulled and the fabric pinched as it wound up his legs, twisting and tightening, and pulling in opposite directions. Were they on back to front?
In the end, David gave up and peeled the tights off to search for a label. Nothing. It must be pure guess work to determine which way round to put on a pair of tights. Holding them out in front of him, the fabric appeared to be a little fuller on one side. Stood to reason you’d need more at the front for the tackle.
But wait a minute. These were for girls. That extra space was for their backside. David flipped the tights around and tried again, this time squeezing his tackle in between his legs, out of the way.
With the band of elastic finally hugging his waist, and the Lycra clinging to everything, and he could feel every thing, David’s eyes drifted downwards, and he let out a contented sigh. It was as if shackles had been cast off, and eyes opened to a whole new world, a whole new David.
My favourite colour, he thought, unfettered by the natural order of blue for boys and pink for girls. Who the hell’s order was that anyway? With lips and legs tingling, and cock and balls snuggling, David felt…
“Hello, Diana,” he whispered.
The tram trundled along the streets of Manchester before pulling up just a few hundred yards from Larry’s Bar. Sadly,there would be no Diana tonight. Just Karen and David, and a secret pair of lilac lace cami-knickers.