A sissy has arranged to finally lose her cherry to a sexy older man she met online, and they have agreed to a little 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! I took him cautiously into my hands, my very first time ever touching another man's dick. He was hanging softly, but still so thick, and heavy, and hot! It was the heat of it that surprised me most. For whatever reason I'd never really thought about that, when I'd fantasized about what this would be like.
I started with just a kiss, slow and gentle on his crown. He smelled incredible, the cleanness of fresh soap, mixed with a heavier, thicker scent all his own, just the barest hint of salt on his skin as I began to lick. I could barely even fit him in my mouth without scraping him on my teeth, and it only became more difficult as he soon began to swell. I did what I could with my mouth, sucking and slurping, trying to get him good and lubed up for what was about to happen, but he was just so big, and thick, I mostly had to rely on my hands. He finally decided he was ready, helping me back to my feet.
“Over here,” I swallowed nervously, leading him over to my desk by my grip on his cock. I wiggled my mouse, the screen coming alive, the video already cued up and ready. Nine had chosen it for me, just like he'd dictated everything else; it was a sissy-challenge video, with heavy, throbbing music, videos of gorgeous girls and sissies sucking and fucking big cocks, and a pulsing beat to which you were supposed to fuck yourself with a toy. The goal was to make yourself sissygasm, to cum without ever touching your sissy-clitty, only stimulating yourself up your ass. I'd tried over and over, but I'd never been able to do it, always eventually breaking down and having to touch myself to finish. But Nine was confident in his skills. So confident, in fact, that he had bet me that if my tight, virgin sissy ass could make him cum before I did, he would pay me five hundred bucks! I had nowhere near the spare cash to cover that sort of bet myself... but he had suggested a different arrangement, if I came first, a way to pay him off without costing me a cent, and eventually I'd agreed.
I climbed up into my chair on my knees, leaning forward and wrapping my arms around the back. From here on out I knew Nine would be taking control. He pulled my panties halfway down my thighs, and I spread my knees apart to keep them there. He'd told me, during one of our many chats, how much he loved the look of a girl or sissy with her panties stretched between her thighs, and I wanted to look my best for him. Next he removed my butt plug, making me wince and causing an audible pop, but after seeing just how thick he was in real life I was grateful he'd ordered me to use my biggest one. He set the plug on my desk and picked up my lube, applying a generous portion to both himself and me. I'd already done myself before the plug had ever gone in in the first place, but I figured you could never have too much lube, especially for my first time! I felt the hot, spongy firmness against me then, and he began pushing forward. I whimpered pitifully, biting the back of my chair, hating that I was being such a coward but unable to stop myself, willing myself to relax. Once he finally got the head in the rest wasn't nearly so bad. That was how it always went, using my biggest toys, though this was even more of the same. The pain hadn't faded away completely yet, but I was even starting to enjoy myself a little by the time he'd worked himself all the way inside. He held himself there for a minute, pressing tightly against me, caressing my ass and fondling my tiny little titties through my bra. Then he reached out to start the video, and began thrusting to the beat.
The thing about this video was, the pulse changed as the music did. One moment you'd be taking deep, slow strokes only once a second or so. Then all of a sudden you'd be getting it hard and fast, several all together one after the other, then slow again, only to then swap to a mid-range beat, then fast again, then slow, constantly varying patterns and numbers of strokes, never letting you know quite what to expect next, but somehow all working perfectly with the music and the images on the screen. When doing it to myself with a toy, or sitting on one and trying to bounce along to the beat, all those changes were actually kind of distracting to pay attention to. But when I was just kneeling there, arching my back and presenting my ass, and he was the one having to pay attention and doing all the work, it meant I could let my mind go and concentrate on just enjoying it for once! It felt incredible, honestly, taking that huge, hard cock, pleasuring him the same as all the girls and sissies on the video were doing. I fucking loved it! Whether he would actually be able to make me cum this way or not, I still wasn't sure, but either way this was amazing!
It was a long video. I'd watched the whole thing, at one point or another, but never actually all in one go before. But that seemed to be what Nine was going for as I watched the little indicator at the bottom of the screen slowly crawling closer to the end. We were about three-quarters of the way there when something started to change. I'd been floating along pretty well for a while already, making all the little whimpers and gasps to let him know how much I was loving what he was doing to me. But all of a sudden it was like somebody had turned my internal thermostat up to max, and then broke off the knob! There was this heat, or pressure, or something, building up inside! It makes me feel so ridiculous to admit, looking back, but at the time I honestly didn't understand what was happening, since it had started deep inside of me instead of in my sissy-clitty like I was used to. But the feeling just kept building and building, robbing me of my breath, until suddenly I was squealing my brains out, pearly white sissy-cum squirting out the end of my clitty, splashing against the back of my chair!
Oh my God! I'd actually done it! My very first sissygasm, from getting fucked by that huge, amazing cock! And God, was it ever good! So, so much better than doing it with my hand! But I wasn't done yet, every thrust of Nine's cock making me whimper and moan in my overly-sensitive state. And fuck me if I will ever understand how he was able to time it so close, but he didn't cum himself until the video was only thirty seconds from the end, his hot, thick seed blasting into my formerly-virgin depths. So... no five hundred bucks for me. But I was so satisfied and proud of what he'd just made me do for him, in that moment I didn't even care.
He withdrew and stepped away for a moment, probably to go pour himself a glass of water, I thought. I could really use one too, but I wasn't feeling quite able to move just yet. It wasn't until I felt his fingers on my limp, spent little clitty and balls that I remembered the other half of our bet. I stared down between my legs, watching as he eased the small metal ring down over my clitty and tightly against my base, making me gasp and wince as he used his thumbs to force one ball then the other through as well. It was a tight fit, not quite enough to cut off circulation or anything, but easily as tight as some of the cock-rings I'd tried using back before I'd finally made my peace with what I truly was. A second, smaller ring came next, barely wider than my clitty and fitting snugly into the attachment points on the first, pinning my sac through the small gap between the two and using my balls as an anchor point to hold the whole contraption securely in place. Lastly the cap, a metal dome the same diameter as the second ring, with a single hole in the center. I couldn't see the details from my position, but as I felt something being inserted into my urethra I realized this one must have been quite a bit different than the ones I'd seen when I'd been looking them up online. I whimpered as the cold, thick metal tube slid further and further inside of me, reaching right down to my base as Nine squashed my clitty uncomfortably inside its new tomb, then finally produced a key locking it all tightly in place. The whole thing now extended barely an inch from my base... Oh my God! From the size of it, it looked like I finally had a clitty for real, now!
“What do you say, Emma?” he asked, giving me a firm spank on my ass.
“Thank you, Nine,” I obediently replied, my cheeks burning as I realized the full impact of what I'd agreed to with our bet.
“You're welcome, little girl,” he chuckled, tightly squeezing my ass where he'd struck me. “And Nine is still acceptable, by the way. But now that I've bred you, you may also call me 'Daddy'. Let me hear you say it.”
“Thank you, Daddy,” I murmured.
“Good girl!” he praised. “I'll be by tomorrow night, but let's make it seven o'clock. I want to make sure I can both breed you again and cum in your mouth next time, before I have to be getting home. You are so fucking hot... make sure you dress yourself up for me just like you did tonight! I'll message you a link to which video I'll be wanting to use, once I decide.”
“Yes, Daddy,” I timidly agreed.
“Good girl, Emma! See you then,” he said. And with one more swift, hard smack on my ass, he was gone.
I finally eased myself off my chair, and went to go look at myself again in my bathroom mirror. My makeup was a mess! It seems somewhere along the way I must have started crying, though I had no memory of that. And when I looked down... God, I really did look like a girl now, with such tiny little thing between my thighs! Not that four inches had been all that impressive to begin with, but seeing myself looking like this was really just something else! I chewed my lip, thinking it over, poking and flicking at my new cage; there was no way in hell I'd be able to get myself off, not with this thing on! I had no choice but to wait until tomorrow night, now completely dependant on Daddy's thick, amazing cock to make me cum! It made me shudder, just thinking about it. The terms of our bet were that he could lock me up for one full week, and that he could come over and use me at any time and in any way that he wished until that week was up, unless I was currently at or getting ready for work.
I smiled, a quiet, guilty little smile just for me, as I looked myself up and down. A week was good. But something told me it wouldn't take much to convince Daddy to repeat our little bet, once the week was up!