Date with a Sissy

So I continued doing that as Lorelei lowered her head and took what was left of my dick, my only constant friend that was leaking all over the place, in her mouth. There was no stopping the pitiful sounds I made or my fingers from teasing newly sensitive nipples. She sucked hard, like I had with her my first time, stretching me out and then sitting back with a 'pop!' And my wang quickly fell back into its new habit of sort of standing at attention but keeping the stoic act, even after being in Lorelei's mouth.

It's too much to say the fucking thing had failed me because it wasn't even a thing that could fuck anymore. My unfucking dick just sat there and seeing it like that, in Lorelei's crimson glow, should have been ominous. Maybe it would have been for anyone else but I was utterly enamored with the idea presented on the couch, of total surrender, of absolute shrinkage.

"I know what a sissy-to-be needs..." She said and scooped up the lube off the bed as I remained in place, needing release and the metamorphosis that would follow. The sound of the lube container being opened didn't worry me, I'd reached some sort of fucked up Zen that involved trusting Lorelei utterly. Her wet, slick touch was now at that final bastion of personal space I owned and it was going to fall to Lorelei. I wanted her to take me and when a finger invaded, I gasped, back arching and called out in a voice that seemed made for such a thing.

"That's right, gotta get you warmed up for the main event!" She said and then Lorelei was descending, her lips about me and tongue rubbing that delightful place that still existed, all the while finger fucking me. 'Throes of lust and madness' is probably the closest I can come to describing what I felt right then because I knew what was happening.

Lorelei was getting me ready to be fucked while sucking away the last erection I was going to have, as weak and pitiful as it was. And I wanted all of it. The warnings and threats were all encouragement and, bathed in crimson, I reached orgasm thanks to Lorelei's efforts. All I'd done was play with my titties but what else could I do? She was the one in change, giving a pleased moan as the physical evidence of my climax was offered up to her. Don't be surprised when I inform you it wasn't much.

"And there it is." She said, not even bothering to wipe her mouth, instead squirting more lube to her hand and then easily adding another finger inside me. A weak, clear spurt from below and an equally weak moan from above all I had to offer on current events. "Goodbye boner and hello big boobs with a cute little dick! Or, sorry, clit!" I tried to bite back a cry but Lorelei's fingers were too talented and I clawed at the bed, calling out to an uncaring ceiling.

"Wanna know something? I don't know if I can turn you into a chick. I kinda don't want to!" Her fingers were moving faster, making 'come hither' motions that were driving me insane, a constant leak happening in place of the erection I'd bid farewell to. "I hope you keep this leaky little clitty. Would you like that?" I moaned nonsense, thrashing back and forth in rapture, lost in all Lorelei had introduced me too. There was no stopping it, another wave of pleasure had been building and then, all at once, Lorelei was too much for me to deal with. For the first time I reached orgasm without my dick being touched, with only Lorelei's fingers fucking me and her words urging me on. And the seeping crimson glow that had crept into my thoughts and found those deep buried desires, the sorts that had been happening here with her, shone on all the while.

Maybe I passed out from euphoria or drifted off naturally but I don't remember how that encounter ended. I was snapped loose from the tethers of consciousness and only then did that unnatural light dim. I rested but even in slumber, I knew some line, a threshold had been crossed.

I'd willingly given up my ability to be a man in bed. And Lorelei had been mostly right, I'd traded it for two good nights, maybe even the best ones of my life. Was it worth it? Well, yes, for me it was. Because at some point changing became part of the enjoyment. The sex was mindblowing, the companionship refreshing, life sustaining and losing my previous boring form to gain curves... I made that trade then and typing this now, I still would make it. Again and again and again.

Waking up took time, remembering I was still at Lorelei's place and then she'd fingered me. That's a strange second thought upon rousing from that so comfortable body of water, that lake of slumber. Blinking, I looked around the room that was just about as familiar as my own by now, seeing Lorelei once more in the chair, wrapped up in a sheet, the blinds over the window admitting slants of pure LED light.

"Hey there sexy." Lorelei said, voice low and more controlled than the last time I'd heard it. "I... Want to apologize." I said nothing, still fighting for the ability to think as I rubbed my face, finding those contours had changed as well.

"I've never had this much... Stuff at once before." I took a second to recall 'stuff' was 'my sperm' and then I remembered her picking me up with no visible effort at all. "And it's fucking with my head. I went too far earlier, with the shit talking and... I knew you couldn't fuck me but I wanted to see you try." She frowned as I blinked sleep out of my eyes, not sure what to do with that information.

"I don't expect you to understand but I'm on a power trip over here and still trying to get a hold of myself." I nodded and sat up, not bothering to cover my breasts as it was still warm. Besides, it wasn't like having them showing was going to offend Lorelei.

"I don't mind." I said, pausing to brush something off my arm only to find it was an errant shadow. "Mind clarifying what a sissy is though?"

"Oh yeah, not everyone is as perverted as I am." Lorelei said with a smile. "A sissy is a person with boobs, preferably big, and a dick, preferably small enough it looks like a clit. It's a, uh, gender identity? Lifestyle? Whatever, it's popular in certain corners of the internet that I frequent." I nodded, having seen the word around when searching for that night's adult entertainment, usually a story but sometimes a video.

"So why are you apologizing? I fit the definition you gave." I said a great deal more calmly than I felt. Because she was right, I now very well could fit into the one sissy story I'd checked out, some contest winner that was well written but not what I was after that night. I bailed in favor of finding some romance, wanting the mushy touchy feely stuff over the action. Ironic, I know.

"Yeah but sissies are submissive and..." I stared at her, not even needing to say that I'd been exactly that this whole time. Lorelei gave me a very grumpy look before flipping me off for good measure. "Look man, I want to have a good time but it's getting hard to know where the line is. I-" She raised a hand, fingers splayed out and palm up, a rose red glow flaring from under the sheet covering her. I saw crimson flow in her skin, as if new, shimmering veins were being opened. Lorelei closed those fingers into a fist, trembling for a moment until opening. Those crimson ribbons remained and her fingernails were now a dark, sensual red. Nothing was said as she set her hand on the armrest, resuming her searching look at me and I saw the green was missing from her gaze.

"I don't want to get away with ignoring what you want because I'm stronger." Lorelei finally said and I nodded, knowing it was true. Her crimson eyes alone informed me of that.

"Well, right now all I want is a Coke." Her smile eased the mood and Lorelei rose, keeping the sheet about her as she left. Attempting to leave never occurred to me, I'd bought in and was here until the end. Besides, my clothes certainly wouldn't fit anymore and braving the city streets naked, at night, wasn't even worth considering. Lorelei returned with two cold Cokes, handing me one with what looked like a red gloved hand and I drank half of mine down fast, the fizzy sweetness all the more delightful due to the late hour.

"Being honest?" I threw out and Lorelei nodded, sipping on her can of caffeine while retaking her seat. "I liked it. All of it. Including me not being able to fuck you. " I took a deep breath after that sentence and silence reigned supreme for a few beats of my heart.

"I dunno." Polishing off the last of my Coke, I felt that fluttery heat going strong, encouraging me to speak my mind and so I did. "No, I do know. I'm going to ask you to go down on me again and then, if I can still talk, ask for you to fuck me." A shuddery exhale followed by a brief inhale. "And please keep talking. I like it even if I don't know how to respond."

"Oh, you've been good at that." Lorelei said, embracing the change in mood to where it was going to end up anyway. "It's all over your face or how you moan and squirm. And, hmm, how to say this delicately... Start getting wet instead of hard." My face must have given me away, desire showing through as Lorelei stood and let the sheet fall.

Naked, Lorelei stood in the darkness, no, she cut through the night which had invaded our space with the shining stone upon her chest. Crimson light poured from that single spot, showing her statuesque body and revealing I hadn't been seeing things.

Just as with the gem, I'd been seeing red on Lorelei and now it was free. What might have been vines of pure scarlet had burst free from the illuminating, swirling oval and overgrown her body. And all that color curved, like the pattern in her lace panties I'd felt in that dark alley and standing in this small, too warm room. The designs spilled forth all over her, spirling about nipples, winding about Lorelei's upper waist as if attempting to be a garterbelt, covering forearms and hands like ladies evening gloves, creating an imitation choker around her neck. Those marks glimmered like wet ink, not casting light but insisting they be noticed.

Lorelei approached me with head held high, slightly parted lips a deep, rich red, matching her hair, fingernails, eyes, skin etchings, the furious source of light in her chest. She was beautiful and barbaric, elegant in her nudity, all those feminine curves enhanced by wetly gleaming strands of crimson that hid nothing. Lorelei offered no explanation and I didn't want one. Her erection, inlaid with that deep color of love, wobbled as she walked over, throbbing in the open air and that was where my eyes rested.

"Come on, show me how far you've come." Lorelei demanded as I tossed the blanket aside and scooted closer to the edge of the bed, to her and the certainty of what was going to happen. Sitting there, I kept my eyes on that large and inviting dick as staring at her body decoration seemed rude. Yes, in case you reading this didn't know what kind of person I am, when faced with a beautiful woman lit up like a Red Light District and marked with what looked like Elvish script lingerie, I instead settled on checking out her dong. Because I have all the personality of stale, unbuttered toast. Or was just so very thirsty in a way no Coke could quench.

"You've seen mine. Now show me yours?" I heard both question and command but I spread my legs and, as one, we looked down. Awash in red, I swallowed hard when beholding what remained. Without thinking I scooped my breasts closer to me with an arm to get a better look, to make sure this was real.

Sticking out and towards the left, it looked like my penis had taken the world's longest, coldest shower for how lesser it was now. Sure, it was small but that it had been more and was that no longer... That was making the interior heat rise, pleased beyond words at seeing it. And I was too. This impossibility was another to add to the list, along with my boobs, hips having moved enough to cause me to stumble, the ass Lorelei said was fine, all of which I loved.

"Yep, that there is a sissy clit! And I speak from experience." Lorelei said in a kind tone, ruffling my hair as if I'd done good in a Little League baseball game instead of being the owner of a thing so small and powerless. I shuddered, arm over my bust controlling the jiggle some but my remnant didn't do much of anything aside from dribble out some clear stuff Lorelei's all natural, organic light dyed crimson.

"I told you." She continued, pressing my face against one of her breasts and holding me tight. "Oh, I warned you but I guess you're into this. Welcome to being a sissy." My moan was deep, approving as I latched onto her nipple, looking up into that red, all consuming light. I ran my hands down her figure, finding she was just as touchable even with those new flowing ribbons of red adornment. But my body was acting on instinct while I dealt with her words, finding an awed warmth at being called a sissy.

"Wanna see how much you have left?" I gave another moan, trying to tell her yes with just that and she got the message, letting loose of me and stepping away. I saw the wetly gleaming vine-script run along her back as if trying to form a corset, winding and weaving down before thin lines flowed down her thighs, the garters holding up stockings that were made of scarlet and mystery. Seeing all of that turned me on all the more and I was ready when Lorelei turned around with the ruler that had informed me of my 4 inches back when I could still fuck her.

I fell to my back, awash in interior heat and knowing the number was going to be much smaller this time. There was no reply when I gave the command to stand upright, to strain towards the heavens and impress Lorelei or at least prove her wrong. Instead there was the cool touch of the ruler beside what had been so proud and ignored by the world.

"Just over an inch." A strained moan came from between my clenched teeth at the announcement, eyes closing but unable to escape the truth of her words. Wet heat spluttered down on my pubic plain and the ruler was tossed aside, it's job done. Instead I was back in the pink, waiting for what came next.

"That's my usual size." A pause and I cracked an eye open, curious as to what the hold up was. Lorelei was gnawing on her lower lip, obviously conflicted and staring at what I had left. "What?" I asked and she shook back to reality, actually blushing and averting her eyes.

"I... I've never been with another sissy before. And can you please try screwing me again?" I opened my mouth and Lorelei gestured with her red clad hands, cutting me off. "I know! I just... Please?" Her asking was so genuine and bashful, contrasting being doused in threads of raw sunrise.

"Sure?" I said, slowly rising to a sitting position as Lorelei took up the lube, smoldering red eyes glancing up at me, the burning in her cheeks having nothing to do with the gem. "Here." She handed the bottle over to me and I poured some in the palm of my right hand before finding I'd vastly overestimated the amount required. Spreading thicker thighs, I brought the cool slick puddle to my junk and gasped while rubbing it over the reduced length. There wasn't a trace of anything hard there now, my nub soft and squelching, defying the call to action as I got ready.

Lorelei had been staring all the while, stroking herself and almost panting, her heavy breathing not distracting me but rather being the background noise to me learning about what I'd agreed to. The shaft was so much smaller and my broader hips and increased thigh size didn't help it at all.

"Ohh..." Her moan was pure sex and I shivered, looking up to find Lorelei telling me to lean back. I did just that and she turned around, those corset lace markings showing on her back and then she sat in my lap. "Ah! Come on, let me feel you!" Her lube slick ass was grinding where I'd once had something worth riding but now had nothing of the sort.

Leaning back further, my weak arms caught me and I thrust upward, trying to get my nub where Lorelei wanted it. Her rubbing me, so eager and forceful, should have gotten me hard but I couldn't. This was the failure I'd agreed to and let happen, unable to give a beauty literally humping away at me any sort of action.

"Oh, you are a good sissy for sure cause I can't feel you at all." She said, sitting in my lap, glancing back at me over a red stained shoulder. "Here, let's try it another way." Lorelei rose off me and laid on her front beside me on the bed. Shaking, I rolled over on top of her and then followed her spoken instructions to lay down with my crotch against her ass. So I did just that while my nub continued to be a nub even when I rubbed it on a gleaming cheek.

"Ah! Still soft huh?" I shuddered at her words, finding this more difficult than expected as my figure had ripened further or maybe just over an inch was smaller than I realized because getting my dick where we both wanted it to be was proving to be impossible. "Like a good sissy should be. Are you a good sissy?" Lorelei asked and that fluttery heat demanded I say 'yes' but I was mute right then, too busy discovering how limited I now was.

Mashing myself to Lorelei's ass, I finally felt her heat but not the hidden entrance, that being out of reach for me now. She gave a cute little coo at that and I was struck by the absurdity of the situation. I was giving all I had, rocking into the prone Lorelei and achieving nothing. This was barely a step above drying humping and it was my future, this. Not going balls deep into a ten out of ten ass because I had no balls anymore, no erection, no way to get Lorelei to aim that slinky, inviting smirk at me again.

"I feel you getting wet." She said and I gasped, my strength giving out and I slowly fell on Lorelei's marked back. "You okay back there?" I moaned, humping at the cushion of her butt and yes, I felt myself dripping. That's the best I had and I shivered once more, the light heat within loving this development.

"Yeah..." I said in a weak voice, finding pleasure in failing here. With little effort Lorelei rolled over and all the sudden I was on my back with her above me, hair hanging down in scarlet curtains with her light shining all the while.

"I told you." She said in a quiet voice, eyes locked onto mine. "There's no taking this back."

"I know." I whispered and moaned when Lorelei's dick poked my nub, then began rubbing it.

"And you want to go smaller?" Lorelei asked and I heard bafflement paired with glee, saw it on her face. With her silky huge cock reminding me of what I'd lost and my failure to get Lorelei to even feel me, I saw little point to keep what I had. After coming so far, why stop here? The point of no return had already been crossed, why not find out what came next?

"Yes." I breathed, barely more than a whisper. Complex, hidden pits of pleasures were being opened in myself, relishing this powerlessness. My nub was a thing of wonder, my breasts an endless marvel and I was lost in the pliability of my being. I could change, shed off who I had been and if I couldn't pop a boner anymore, no big loss.

"Okay." Those red lips met mine and Lorelei kissed me deep, before rising and leaving me breathless. "I'm not sure if I can take anymore." She said and then the light shifted, deepening to some apocalyptic sunset shade of scarlet. "But I'll try." The sound of the lube being opened was no surprise even if I still jumped at her wet touch. The only sound I made when Lorelei slipped a finger in was a sigh of contentment. Any shackle of normalcy had long since been removed, all restraints off.

A second finger joined in and I started rubbing myself, unable to jack off so I instinctively did that instead. "Hands off." And I gave a frankly pathetic moan when Lorelei took my active hand, her fingers still slowly rubbing inside of me. "That's my job." Then I felt her hot breath down below, the tease of her tongue on the shriveled, empty sack that seemingly held nothing then she trailed up, to what I was giving up being here with her.