Date with a Sissy

"I wanna go again." I said, giving a moan as she took hold of me, giving slow, long strokes while still speaking in my ear.

"Do you want me to shut up?" She asked and I shuddered before answering.

"Keep talking. I..." And that's all I could say, choking on new desires when I'd taken Lorelei's dick so easily. How's that for the human condition?

"I getcha, you like being called a girl, right?" Another shudder racked me as the slow hand job continued, her recovering insistence pressing once more against my leg. "Maybe you like that your dick is shrinking?" I gave a weak, wavering moan, the heat within roiling at her loudly whispered words. That I very much sounded like a girl wasn't helping. "And I bet we're going to find out if you're an ass girl in more ways than one." She humped my leg a few times before laughing lightly, guiding me to the bed and I sat, gasping for air.

"Lay back, I'll go reverse cowgirl this time so you don't gotta deal with a dick bouncing all over the place for what might be your last time." I gave another weak moan but otherwise didn't protest as I laid down, finding it hard to see my now much diminished friend with newly formed breasts in the way. And that was just another perk, a new wonder to marvel at as Lorelei knelt on the bed with a wicked grin.

"Mind if I really fuck with you?" She asked too sweetly and I responded with breathless resilience.

"Bring it. Seen all Hellraiser movies, remember?" Lorelei gave a bark of laughter then produced a clear plastic ruler, setting it down on my squishier than I remembered crotch, right by my penis and I saw it was standing barely over 4 inches. Thinner too and all I could do was give a weak groan, head flopping back down to the mattress as Lorelei gave a little chuckle.

"I'll stop if you tell me too." Her teasing voice rang out and I shook my head. "Alright then my little dinky darling." I heard the lube being opened with a harsh 'crack!' but was shocked by a sudden shock of warmth about my lesser prick, Lorelei having taken me in her mouth and gave a few vigorous sucks before sitting back up.

"Ohh, not going to lie, that's the smallest one I've ever gone down on." I whimpered again, shaking as her now wet touch covered all I had and it wasn't much. Laying there while Lorelei took charge, feeling my nipples poke out nearly to the point of pain, I embraced what was happening. Despite what Lorelei had told me, I wasn't leaving here the same person I'd shown up as. I'd gotten laid, which was pretty fucking great, and was slowly losing any trace of the nothing guy I'd been. Even my dick was ditching me and none of this was bothersome.

I know how strange that must sound and sure, before meeting Lorelei I'd been confused by it as well. But there was a peace with being with her and the shining, shifting jewel had something to do with it.

Catching a glimpse of it, a rose red shot with streaks darkest crimson, I closed my eyes as Lorelei swung a leg over me, once more lining up the connection that had taken my virginity and a unique toll each time. She held the slicked up part of me steady and then that intimate heat was about me, Lorelei's weight returning as my back arched at feeling her like this again.

"Oh... I'm sure this is going to be your last time." Lorelei said as I gasped, seeing her sitting on me and from the back there was no telling she was packing. Not quite because I felt a heftier presence on my balls, her own set now settling on mine as Lorelei got comfortable.

"To be honest, I feel you but... Not very much." She said while turning to look over a slim shoulder back at me, those sharp green eyes sparkling, challenging. I took hold of those damn fine hips and thrust, getting a surprised 'unf!' in return.

"Prove to me size doesn't matter." She growled, maybe taunting or offering encouragement but I followed that direction. Being told this might be the last time I'd be able to experience this, Lorelei's glorious ass, motivated me more than anything else might have. As we got to it, I kept sliding out and blindly humped a cheek for a few thrusts before she retook me and the cycle continued until we worked it out: Shorter, more shallow thrusts that didn't reach as deep as previously but I didn't care as I was moaning with each impact of her ass against me.

"Oh, oh God this is it!" Lorelei called out and I held her hips tight, if only to keep her from getting up. I slammed against Lorelei, abandoning any pretense of care or tenderness, giving in to base urges. And one of those was to finish this, to see if she was right and I'd lose what was currently fucking her. My feminine voice was going ragged and my nipples hurt as I screamed, heels digging into the bed as orgasm flooded my being. Vision failed me then, my head whipping to and fro as Lorelei's heat held tight to me as she kept moaning and grinding, asking for more I just didn't have.

I closed my eyes and drifted on the surface of sleep, that deep and placid body of water. Lorelei rose and said something, with my attempted reply being lost. There was the shine of the gem but even that couldn't get me to rise. Lorelei was wearing something but I couldn't make out what before a blanket was placed over me and I went under, going to the depths where dreams can't occur and real rest is obtained.

Real life once more butted in, my work alarm for the rare Sunday evening shift going off and I blearly rolled to the edge of the bed to find my pants, knowing things were different even freshly roused. I shut the alarm up, found I had no texts waiting for me and sat up, finding there was far more weight on my chest, the promise of boobs now ripened into the real deal. Sure, still not as big as Lorelei's but they felt better. Yes, they were round and had heft but my psyche was deeply pleased at the developments, the sort of quiet satisfaction I rarely got in life.

And you bet I got a feel, cupping them in my hands and lifting, amazed at how much there was and that this was me now. A little gasp escaped me as my nipples kicked on, bigger still and brushing one with a finger made me shiver. I was turned on but not, the usual male indicator for being horny not following the script.

Throwing the blanket aside, I looked at what I had left with fading afternoon light that was bleeding through the blinds. There, in the middle of a bunch of pale and smooth skin I'd shaved before my date, stood what remained of my manhood. Yet that wasn't the right thing to call it but that was surely the last marker of me having been male left. My trusty joystick, my personal passionate pole that I'd jacked hundreds of times to all sorts of written, drawn and recorded porn was now far closer to what Lorelei had been packing when we ducked into the alley together. Not much in the way of a shaft left and girth was lacking, balls a shriveled pouch that didn't seem to be containing anything.

Touching it resulted in some of that familiar pleasure and it wasn't fully soft but not hard like Lorelei when I'd blown her. I stroked myself with two fingers and when I let loose, it remained sort of standing upright. There wasn't enough dick left for it to hang down as it had most of my life, instead stuck in some sort of half chub form while still being flaccid. And I was slowly leaking clear stuff from the tip, something Lorelei had warned me about.

With all of that accounted for and my sanity intact, I stood and stretched, joints cracking as I prepared to take my first steps as... Not a woman but certainly not a man as I'd never really meshed with manliness at all. Whatever I was, it was going to be naked as I couldn't find the shirt Lorelei had given me. So I headed towards the sound of a movie playing, aware my gait had changed slightly more since that morning to find Lorelei lounging on the couch. Draped in crimson, I blinked and found she was just as naked as I was, with only her red hair being splayed out in natural, messy curls.

"Hey there sexy! Come take a seat, I've got Face/Off locked and loaded." She patted the couch cushion beside her and I did just that, thankful for her presence if only to make me feel more secure in not being the only naked person here. "Sleep well?"

"Yeah." I said, snuggling up close as she reached right for the goods and I heard her inhale of surprise.

"Man, I hope you're okay with this..." Lorelei trailed off and I kissed her, once more silencing those constant doubts and worries I was tiring of.

"I am." And this time it was my turn to reach for what she had and that was far easier to find, as big as it was. "And I want more." Any protests she had vanished when I started stroking, Lorelei laying back with her head on the armrest, allowing me full access to her raging hard on. She might have been as big as I used to be but it was hard to tell as I'm sure my hands had become more fine and delicate. All that mattered is that she still made those wonderful sounds as I took her in my mouth, those legs stirring as I worked.

Holding and stroking the base, I bobbed my head and fell into that pace, that rhythm I'd seen men, women, and others fall into. I rubbed myself with my free hand, unable to dedicate the mental processes required to grab hold of my junk and instead just did what felt right. And taking all of Lorelei as I'd done before felt just as right, even if it took more effort to get her down. Her 'Ahnngh!' of utter astonishment was absolutely worth it but I pulled back before she could shoot right down the hatch, instead using my tongue on that sweet spot where the underside of the head met the shaft to get Lorelei to that temporary, fleeting nirvana.

Struggling to swallow all of Lorelei's load was an experience, even if it didn't taste all that great. Plus the sounds she made, the involuntary motions born from pleasure, and the tired yet loving expression she aimed my way after, I'd given those to her and that I was able to do so filled with an euphoria that mingled with the still fluttering heat. And that was a potent mix.

"Ohh, you are good at that." She said after some time, still laying even after I squirmed under her legs to sit on the couch, with Lorelei laying as if posing like a French Girl. I noticed that even semi hard Lorelei was still bigger than I was. And that was an unexpected thrill.

"You know..." She said, green eyes finding mine, one of her hands covering the catalyst for all of this idly. "I just had a very naughty idea." Her grin was wicked and my excitement resulted in a few warm drips from below, Lorelei feeling it and her grin only widened.

"I'm pretty sure trading... Sperm? Jizz? Baby batter? Stuff!" I giggled at her searching for a non-gross term and she gave me another smile before carrying on. "Trading stuff makes things happen faster. It's why I was so worried when you went down on me because that's a one way ticket to tits." I snorted with laughter while having some naughty thoughts of my own. "If you want, we can see how big I can get." Lorelei sat up and leaned in for an insistent kiss, her breathing harsh when we broke apart. "And we can see how small you can get. "

Well, when an offer like that is spoken, what else is a girly shaped person to do aside from whisper 'Yes?' Lorelei stood and I bounced to my feet, breasts moving slightly and that was a nice reminder I had those.

"Just so you know; Your ass is amazing." And then she was behind me, that impressive tower I'd sucked off back to full power and I blanked at feeling it pressing into that last personal space I had. "These are too." And Lorelei's hands closed about my breasts and her touch was gentle, fingers running circles around my areola, nearly causing me to melt into a puddle right there. No sensation of an erection but there was that new heat running rampant within, approving of every perversion Lorelei and I could do together.

With Lorelei still molded to my backside, we waddled a few steps towards the bedroom before she gave a growl. With a shocking display of strength Lorelei picked me up, the expression on her face feral and filled with want. Laying in the cradle of her arms, I saw dark streaks on either side of the fiercely shining gem and my first thought was that Lorelei had been badly injured and was bleeding somehow. Those smears became more defined as I watched, barely aware of Lorelei carrying me away at the sight. Two slashes that seemed to be squirming into new, more complex shapes flanking her personal light, under the collarbone, with me confirming it wasn't blood before I was carefully laid on the bed.

An oval of solid red was the only source of light in the room and I didn't see those dark designs anymore, only the hunger on her face thanks to that tempting illumination. "I've never tried to actually drain a guy before." She said, voice lacking that growling demand and I exhaled shakily, not sure what that flash of savagery had been. "I don't know if I can." Her fingers reached down and with the same delicacy she'd shown my newly developed chest, rubbed what was barely sticking up.

In short order I was gasping, my hands going to my breasts without any conscious thought on my behalf. "Just got to get your cute little clit ready..." Lorelei said and I pinched my nipples too hard in reaction to her tease, moaning embarrassingly loudly. "Oh, like that?" There's no telling if I nodded or shook my head or responded at all. I was utterly lost and the light that was shining forth wasn't helping. Lorelei's pale skin was tinted by it, the sheets, ceiling; all red. Only closing my eyes brought any escape from it but that wasn't totally true; it invaded there as well, losing shades of its bloody coloration but none of that alluring potency.

"Then you'll love this." Laying on the edge of my bed as I was, I saw Lorelei step closer, her dick in prime shape as it rubbed against my semi-hard leaking nub, lording her power over me. That silky hard heat felt just as good against what little I had left as it did in my hand and mouth. And I had no doubt that trend was going to hold when Lorelei inevitably slipped that living iron into me.

And I wanted it. But speaking was impossible, with Lorelei working her awakened and proud erection over me, all I could do was feel and react. I was leaking, unable to offer any sort of resistance against her numerous inches that I was getting to know very well. Only when Lorelei gave a slight spurt that splattered over my now wider midsection did she stop, breathing harder as she went down on her knees between my spread legs.

"Just a little bigger than I usually am." With two fingers she took hold of me by the base and started stroking, further reducing me to a whimpering mess. "After this you're never going to get hard again." She must have seen a question, some objection I couldn't voice cross my face as Lorelei's grin transformed into something beautiful and terrible by the light being cast from under her features.

"This is hard, my sweet sissy. Compared to what's coming. What you're asking for." I swallowed hard but didn't call her off, to try and salvage what I could from this. I was too turned on, even if it was difficult to tell by usual means. "Well, do you want to try fucking this last load into me? Because this is definitely going to be your last chance to." I nodded at the offer, unable to stop a light, wavering cry from escaping as Lorelei produced the lube and slathered some on me.

"You've got a cute little chub, not quite a clit yet. But close." I gave a slight moan at that even as Lorelei helped me on my feet before going on all fours on the bed. "Now come on, fuck me. That is, if you're man enough." I gritted my teeth at the way Lorelei issued the challenge but she was too busy lubing herself in preparation to notice.

Breathing hard, I looked down through the valley of my breasts to what didn't seem very excited at the prospect of one last ride. All it took was a few strokes to realize this endeavor was hopeless: No further growth, increased firmness, nothing.

Still I climbed on the bed behind Lorelei, admiring the view even as my shaking hands took her by the hips. Scooting close, I found that adding to the impossibility of the situation was thanks to my back arching, my junk was deeper between my legs now. For ten years I'd gotten used to good old Pokey being in the same place and now it wasn't by just enough to frustrate when I already had plenty working against me. I ended up mashed against Lorelei's oh so touchable ass, blindly trying to find the entrance I'd been able to reach before and, with her help, felt that familiar give.

I felt where she was tightest and nothing more. Shaking and trying to work with a prick that wouldn't stand any taller or strain outward, I felt that inner heat radiate a surge of deep gratification which permeated my body. Lorelei rocked back, nearly knocking me over but I weakly returned the favor, to no noticeable result. Trying to adjust led to me flopping out altogether, having only just barely managed to achieve penetration but that was a tease at best, nothing fulfilling. What I'd done before so easily was now impossible.

Falling back on my haunches, I heard Lorelei speak but my breathing was so loud and then a series of shivers racked me. My breasts quaked along with the rest of me and I wrapped my arms about myself, radiant with heat which rendered me unthinking, unspeaking as it burned. I'd asked for this and here I was, all slicked up and unable to perform. Yet I felt no resentment for my now useless protrusion as this was my doing and not ole Pokey's fault.

"Are you okay?" I finally heard Lorelei ask and I nodded, looking up to see concern aimed my way. She was sitting on her haunches right in front of me but I hadn't noticed, too wrapped up in how I felt. "I didn't mean to..."

"I-I'm fine." I said and giggled at her surprise. "Thanks for letting me try but I guess you were right, earlier was my last time." I shivered after saying that, drawing my arms tighter about me but still not done. "Please... Don't call me a man." Fighting to say those words, I sucked down a deep breath after, the very foundation of who I was now altered.

"Oh shit, I'm sorry!" And she sounded it too, tucking strands of hair sticking to her sweaty face behind an ear. "I got carried away. But what would you prefer?" She asked and a shudder ripped up my spine as I panted in the light of a sun that refused to set or dim.

"What you've been calling me." I got that out and then speech failed me, instead all I could do was fight for air as Lorelei took one of my hands and slowly brought it to her lips, planting a kiss on the still trembling limb.

"Of course. You are my girl, after all." Another light, delicate kiss and then Lorelei rose, walking about the room until she found the wet wipes. That done, she returned to me, cleaning off the lube while holding me close all the while. "I'm sorry, I just thought it was worth a shot while you still have some Unf! left." Resting my head against one of her breasts, a pillow without equal, I dug deep for what had bothered me so.

"Failing wasn't the problem, just how you said it." I finally replied and Lorelei hugged me closer, a sigh ringing out.

"Sorry, my sweet sissy." She said and I gave another shudder in her strong arms, clinging to the center of Lorelei's hourglass figure else I would be washed away by a tempest of my own creation. "So how about you lay back and let me finish the job?" Another shudder tore through me and Lorelei remained until I was ready, resuming my passive position as she took her more active role of stroking and reducing me to a quivering mess.

"This was a good ride but, as we both know, all good things come to an end." She rubbed her thumb on the underside of the shaft, not that there was much to work with but I felt the warm, slow dribble resulting from her actions falling down on me. "And now it's just going to be stuffed into panties instead of my ass." That fluttering, ethereal heat had nothing but blind praise for her words, burning all the brighter while I just lay there, moaning and playing with my boobs.