The Sissygasm Bet

I was standing in front of the mirror in my bathroom, doing one final touch-up of my hair and makeup, hardly able to believe this was finally about to happen. My shaved little sissy-clitty was twitching in my panties as I thought about it, the sexy red see-through ones that I’d bought special just for tonight. I’d been chatting with this guy online for a little over two months now, but tonight was going to be the first time we’d ever met up. The first time I’d ever worked up the courage to do this with any actual human being, in fact, though the growing collection of toys I kept in a tub under my bed had long since become part of my nightly routine. I didn’t even know his name. He’d told me to call him ‘Nine’, but from the pictures and videos of that huge, thick cock he’d been sending me, I thought his nickname might actually be an understatement.

Then came the knocking on my apartment door, and the time for second thoughts was past. I scurried out to meet him, my sexy new four-inch, ruby-red pumps still unfamiliar on my feet, making me daintily mince my way. They’d been expensive, but I hoped they would be worth it, that he would like the way they looked on me. He’d insisted I buy a pair with an exactly four inch heel, the same length as my sissy-clitty. He hadn’t been wrong, either, when he’d told me how hot it would make me feel, just walking around like that on the symbolism of them!

I glanced through the peep-hole and let out a breath of relief. At least it really was the same guy from the photos. I took one more, a deep one to steady myself, then opened the door wide, showing myself off.

“Nine,” I smiled my welcome, my voice pitched as girlishly as I was able, looking him happily up and down. He was more than twice my age, about forty-five or so, with a thick salt-and-pepper beard I found really, really sexy. He really was six-foot-four like he’d said, and built like a damned truck, too! Even in my heels he was still a good three inches taller than me. “Please, come in. Can I take your coat?”

“Emma,” he smiled back, making my insides go all aquiver at his use of my chosen name for myself. He was looking me up and down as well, and I could track his leering approval at every stop along the way. From my artfully tousled, shoulder-length red hair and bright red cock-sucking lips, to my tiny little A-cup titties stuffed into my see-through red bra, to my small, pierced belly, my tiny, shaved little sissy-clitty, and my slender, stocking-covered legs and sexy red pumps. He liked it all, I could tell, making me feel so sexy, and proud! “Your pictures don’t do you justice.” He stepped inside and closed the door behind him, handing me his coat.

“Thank you,” I replied bashfully, my cheeks burning, quickly hanging his coat in my closet for him. “Would you like a drink, or anything, before we…”

“I’m good,” he grinned wickedly, shaking his head. “You did everything I told you to?” I bashfully nodded that I had. “Then I think you know what to do.”

I stepped closer, tentatively placing my hands on his hips, needing my grip on him to help me sink to my knees in my heels. I slowly undid his belt and jeans, my hands shaking with either nervousness or excitement, even I wasn’t sure which. I pulled them down, biting my lip as I stared at the thick bulge under his boxer-briefs. Then those came down too, and I couldn’t help but gasp. The pictures and videos had been wonderful, but they hadn’t prepared me for the reality!