Date with a Sissy

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The crotch fit snugly and I pulled the one piece up, finding it was riding up my ass some while trapping away my clit. My hips were exposed and the only piece of lingerie I owned was slightly heavier than I expected but I put my pink adorned arms through the straps then had to tuck my breasts into the bodice.

And finally, I stood wearing that quintessential female garb and nothing else. It fit perfectly, holding me close and while it was riding up my butt, I found even that enjoyable. Slowly, I walked to the bathroom, letting my hips sway and feeling the slight bounce of my breasts. Flipping the lightswitch, I saw myself as I wanted to be: Soft.

No bulge gave me away, no outline of something mindlessly demanding attention. Just curves and softness and pink, my breasts straining against the velvet, the peek of light from between where my legs came together. Just as Lorelei had been a knockout from the first time I'd seen her, I was now too.

Then I started crying, standing half naked in my bathroom with a dull pink gem laying upon my chest. I'd never expected to be here: Beautiful, soft and with someone waiting for me. Life had changed and seeing myself freed from the miserable fucker I had been was a liberating shock I came to terms with alone. Even with Lorelei waiting for me later that night, I still needed this quiet time to at least say goodbye to who I used to be.

Blowing my nose and washing my face, I smiled in the mirror at the soft, innocent woman who was looking back before returning to the living room and redressing. Pulling on Lorelei's jeans over my one piece felt naughty and I left her bra on the floor, my new garment not giving me as much support but it was more comfortable so I went with it.

Still feeling those pangs of hollow loneliness, I passed the time by watching video essays until needing to leave for work. Heading out to my car, I ignored the eyes on me and drove to the familiar campus, my short, pink hair not as much of an outlier here. But with it being 5 pm, not too many people were left to notice me and I was fine with that. I went along my usual route to the janitor's office/boiler room/supply closet, finding no notes which meant it was Monday as usual. A locker had a few heavy blue shirts and I took one, doing the buttons from the bottom but stopping under my bust, leaving my cleavage uncovered.

Smart? No, absolutely not. But I confirmed in a bathroom mirror later that I did look damn good and such a feeling was so new to me that I reveled in it. And the shift started, with me changing the bags in trash cans in the English building and I couldn't help but watch as students walked by, seeing the haze that glowed with unnamed colors rising off them and noting how, male, female, or anything else, they checked me out too.

One guy, shorter than me and wearing a shirt with a dragon on it, asked me if I'd seen a text book around as he'd misplaced it. I hadn't but invited him to walk with me to the unofficial lost and found where the janitorial staff dumped off their findings while cleaning the campus. The guy was so close to me as we walked down empty hallways and I wanted to take his hand, to see if that haze could be felt, if it was warm when I was so desperate to not be alone.

"I haven't seen you around before." He said as I unlocked the door to the janitor's office, taking a moment to gather my thoughts.

"I'm new here." I undid a button on the heavy work shirt, the cutie with glasses and dark hair noticing, color starting to rise in his face and that aura about him also deepened at the edges. "But I know a place in the back that might have your book and there's no cameras." I undid another button and he swallowed hard. "Interested?"

He nodded and I took his hand, just that simple action making me bite back a moan. He was warm in a way Lorelei wasn't and I hurried him along to the tucked away desk where all the paperwork was done. And the camera had been torn down so the boss could smoke while swearing at the constant flow of requests we received, meaning I was free to indulge.

Not even bothering to fight with the rest of the buttons I pulled the work shirt over my head and tossed it aside, facing this cute guy who slowly let his backpack fall to the ground. He took a step and I matched it, taking one of his so damn hot hands and placing it on my ass. Getting the hint he grabbed hold of me and I gave a little squeal, his heat easily bleeding through the layers of clothing.

I leaned in to kiss him, this cute guy I didn't know the name of, an unthinkable act on my part back when I had still been shackled to masculinity. My eyes closed as my lips met his, the blaze of wonder coming off him banishing that isolating suffocation I'd encounter in my apartment. I didn't care if his lips weren't as soft as Lorelei's or that he was shorter. And, getting a gasp from him, I found out he wasn't packing as much either but he was hard and so hot...

Sinking to my knees, I unbuttoned his shorts and pulled plain boxers down, freeing my desire. Yes, even this part of him had that almost without color haze rising off his straining length and I needed him all the more. Taking hold of his slim hips, the sort I'd had not so long ago, I opened up and teased the head with my tongue, his gasp almost lost in me basking in that primal, furious heat. Leaning in, I got a taste, my guy having more of a musky tinge than Lorelei did. But he burned so sweetly and my lips brushed pubic hair as I took him in easily. Sure, he was smaller but...

Being with him, on my knees and with his dick in my mouth, I felt as if I was kneeling before the crucible where all the universe has been cast and created. His pulse was that of existence, the heat he gave off was enough to make dormant seeds bloom. And I drank it in. He was the warmth of spring that banished a cruel winter and I wasn't ready when he jerked and thick, heavy shots were firing right down my gullet.

I looked up at his almost pained face, felt his hands trembling as he touched my face and I understood so much more about Lorelei after that. Because I didn't want to let him go but he was getting softer and, with a terrible suddenness, I recalled how me swallowing might cause this cutie issues in the future.

I let loose, wiped my mouth and rose, feeling stronger. He got decent as I pulled my work shirt on and, wordlessly, gestured towards the box that acted as lost and found. This story has a happy ending too, as his book was there and he thanked me "For everything." And I told him I was at the college every weeknight, noticing that aura had faded ever so slightly, the color once more vague but he looked so bashful and happy!

After that, the best distraction, I resumed my job but it wasn't easy to focus. It wasn't common for many people to be around this late but students and teachers were still here, each one giving off that heat I desired. Each individual was intoxicating, with unique colors fraying off of them as they moved, each one looking at me while I tried not to stare.

Evening gave way to night and, after cleaning a bathroom, a larger guy struck up a conversation with me, chatting about how much he liked pink as a color. "Some of my favorite organs are pink!" I giggled at his joke and in short order I was on my knees again, basking in the radiant fires of another stranger. He lasted longer but in the end he was panting, unable to crack a joke thanks to my efforts.

"You taking English classes? Cause you're pretty damn good with your verbal skills." I giggled and waved goodbye, the Chris Farley wanna be whistling as he walked out of sight. By the time Lorelei started texting me, I was almost done. And no one had asked where the other boring guy went or why some punk haired chick with pink etchings all over was scrubbing a toilet. Instead I told Lorelei I was going to be done soon, finished my sweeping then clocked out, leaving the stained blue shirt there.

My junker of a car started, another prayer answered, and I made sure I had my new, still unopened stockings with me before driving back to Lorelei's place. Parking outside of her building, I crawled in the backseat and pulled on my new, feminine leg coverings, fighting to get it done in the dark but still loving how they felt on my smooth skin.

Dressed in Lorelei's jeans and shirt but with my own underwear, I walked into the dimly lit building, not fearing for the worst. I felt ready, able to deal if someone decided they wanted to start something. No one wanted to throw down and I navigated the hallways undisturbed, knocking on Lorelei's door and was let in almost instantly.

"Hey there sexy." Lorelei had showered and was wearing only her glimmering scarlet, gem giving off lower light than it had the night before. Without saying anything I pulled off my shirt and wiggled out of the jeans, standing before a beauty with the second biggest dick I'd seen all day. Over the hours apart, she had already started to shrink but was still impressive and all the hunger I'd kept leashed was now unleashed.

"Oh damn! You look-!" I silenced Lorelei with a kiss and that's all it took. Look, I'm sure you can figure out what happened next and yes, it was sexy and hot and all that. During me sucking her off then being on my hands and knees with Lorelei fucking me, I noticed she wasn't warm in the same way those guys I'd blown had been. There was the slightest lack to us being together, even with Lorelei railing me oh so well. After, laying on the couch with a movie playing, Lorelei surprised me.

"I know." She murmured and I jumped, feeling guilty and wondering if she'd read my thoughts somehow. "You're different too. Not cold but not warm like you were before." I finally asked the question that had occurred to me while working.

"What are we Lorelei?" I waited for her to speak and instead just got a shrug. "That's not an answer!"

"You figure it out then. I busted my ass at work today and am trying to make the best of this dick while I still have it!" I gave a shocked giggle at that, Lorelei's eyes opening and I saw the red glow was back, if weaker than before. "I'm on a timer, in case you forgot." And I had forgotten that Lorelei's current big dicked state wasn't permanent and soon she'd returned to that limp nub I'd felt mere days ago, back when I was still just a confused guy.

"Does that mean I get to tease you about shrinking and becoming a sissy?" I said with a smile on my face, Lorelei grinning as red light poured forth once more. It was a long night, with her going down on me until I screamed, her head between my stockinged thighs and talented tongue working on my clit until it stopped leaking. Then, pulling down the top part of my bustier thing, I got to do a porn thing: Lorelei laid on the edge of the bed with her legs spread and I cupped my boobs about her erection. A bunch of lube made motion easier and Lorelei encouraged me to keep going, to be a depraved sissy because I was dressed and acting like one.

Lorelei's orgasm fired up into my face and rained down on the slick plain of my cleavage, the process not all that comfortable for me but the end result was worth it. And after that, finally, we cleaned up and passed out.

The next day Lorelei got me up early for some basic shopping before work, Lorelei keeping me close and I was thankful for her. Even if malls were dying, having so many people around was tempting, their trailing nimbus's calling for me to touch, to taste, to raise my hands to the living flame of humanity and warm myself beside that fire. So many attractive ladies asked if we needed help but Lorelei took care of me while I gritted my teeth and tried not to whimper. Our pooled money got me 2 EE cup bras, some deep necked shirts, a package of colorful panties trimmed with lace and two pairs of tight jeans.

After that, lunch in the food court as Lorelei tried to help me. "You had, what, two guys last night?" I nodded, having almost forgotten about them. How quickly things change, I'd gone from being a virgin to blowing two strangers while on the clock! "I had... Uh, a bunch before I got back to normal. Or whatever normal is anymore." She shrugged as I focused on the orange chicken and not the endless demands of those around me. "You need to refocus when out in public like this, think about the goal then get home. Or what movie you want to see next-"

"Movies?! Your telling me to ignore feeling so shitty and think about fuckin' Morbius!" That made her laugh, green eyes flicking to red as she started coughing and then shot me the bird.

"How dare you! I'd never tell someone to Morb out!" She said as I sighed, rubbing my face with a hand that was now partially pink with spiraling designs. Lorelei's own markings were muted greatly while in public and the stone's color dimmer. But all of her color had more luster than mine, so faded and dull. But we finished eating, went back to her place where we got ready for work and that night I went down on two more guys. Another gave me his number, which I kept, and that night I made the best of Lorelei's diminishing goods.

Life went on. As improbable as that may sound, it's what happened. Over the course of that week Lorelei's glimmering skin etchings faded while mine slowly became more vibrant, a brighter pink to match my hair. I was getting plenty of action to make that happen, with heavy petting and head becoming common during my shifts at the college. I worked hard to ensure the jobs got done so questions weren't asked before finally showing up early and heading to HR, informing them I'd transitioned. I got a new badge with my increasingly more familiar face on it, my pink hair still not long enough to be pulled back in a ponytail. None of the questioning looks from the middle aged ladies dampened my mood and besides, no one mentioned my new habit of getting some so I was happy.

By Friday night I'd gotten a handle on my cravings and had a few phone numbers in case I needed a warm touch over the weekend. But during our nightly fun Lorelei was proving to be too small and floppy to give me what I was after, all the wet ink glimmer gone from her faded skin marks.

"Guess my break from being a sissy is over. This is me as I usually am." Lorelei said, flicking her dick and wincing. "Ow! That was dumb!"

"Ah yes, Lorelei being dumb, everything is truly back to normal." I said while giggling,Lorelei shaking her head all the while. Still, I kissed the tip of her little boner to make it all better and ended up getting her off, the load she fired small and telling. We snuggled up and slept, the morning light showing Lorelei back to her usual state of being, an inch and some of limp, silky nub.

"It was fun while it lasted." She said as I rubbed sleep out of my eyes, slowly waking. "At least now I don't have to worry about popping a boner at work." Lorelei stood and stretched, showing off her curves and impotency. Just as before, the first time I saw her like this, I asked if I could go down on her and my voice made Lorelei shiver.

"Of course. After all, you are my girl." So I went to a now very familiar position and took Lorelei in my mouth, finding her soft and undemanding. None of the guys I'd been with were as Lorelei was and even with her lacking that warmth we both craved, I found being with her a thing of beauty.

Lorelei ended up tapping me on the shoulder, asking if I'd be willing to get on the bed for a good cause. So I did, laying on my side and then Lorelei was on hers, scooting closer to me and she was the 6 to my 9. All night, we called each other girls as we were both too small to penetrate and used tongues and fingers to get the job done. She dry humped me as I felt her clit leaking and lacking any sort of power, asking Lorelei how it felt to have such a fine ass ready and waiting for her only to not be able to fuck me anymore. Her moan was desperate and I felt a good deal of wet heat splatter against me, then panting before Lorelei's hand closed over my crotch, finding my clit.

"If you keep being a slut your going to have enough here to fuck me again." Her whisper was harsh, making me shudder and Lorelei, laying behind me with both of us on our sides, start humping me once more. "This might not be so tiny and soft anymore." Her fingers teased my clit and I cried out, grinding back into Lorelei.

"I-I don't want that!" I said, my lover stopping for an instant as I finished my thought. "Not yet. I want to be your girl, your sissy. And I don't miss having a dick." Lorelei thrust harder, her nub slipping from my cheek into the gulf that she had no chance of reaching the bottom of.

"You really do love this, don'tcha?" Her fingers rubbed my clit and I moaned, telling her yes, of course I did! "You love being a soft sissy." Lorelei grabbed at one of my breasts, a touch too rough but I moaned approval.

"Yes!" I cried, grinding into a crotch that should have had nothing for me but with Lorelei's boobs pressing into my back and legs tangling with mine, I didn't care that she wasn't packing. There were other guys for that, other times to get what I wanted. But Lorelei understood me, had been there with the old ways of pleasure were forgotten and I learned these new methods of touch and tease.

"And I love you." She said in a low growl, kissing the side of my neck as her fingers kept stroking my clit, her own pumping away uselessly against one of my ass cheeks and I told Lorelei I loved her.

I loved being here, this place in between male and female where getting hard was reserved for nipples and that slow, clear dribble replaced erections. I loved how we were sexy yet independent, not just brainless fucktoys because we had seen into the depths of our souls and came back wiser. And I loved how such wisdom allowed us to know when a kiss was more useful than a speech, how a hug would reaffirm faith in humanity and sometimes loving someone meant exactly that, to love with them.

And we did just that, with me finding out how well we fit together, how if I wiggled my hips I felt Lorelei's clit move with me and how when she thrust I still moaned. It was the intent behind the action that now gave me pleasure, that Lorelei was willing to made the attempt to fuck me that I loved. Feeling what used to be so demanding reduced so much, made soft like the rest of Lorelei and I, lost in all our curves, was such potent pleasure.

We were both soft, both able and willing to yield to a certain hardness. But together, I was Lorelei's girl, Lorelei's sissy who couldn't get hard, who was leaking and humping back into my love and moaning and pink and soft.

I had been lost in my previous life but looking into the scarlet stone had allowed me to see into myself. It was a mirror of sorts and now, by reading this, you know they exist. Not every person with unnaturally colored hair is going to have one but I don't know how many are out there. Don't go looking for Lorelei and I and don't pressure anyone whom you think might have one of these stones. Because I think we are some sort of succubus and I've held back with all the guys I've been with. If there's a reason to, I'm sure I could actively feed on someone rather than just bask in their heat. And it wouldn't be a pretty sight.

One final thought: I choose this. When Lorelei fucked me for the first time, I welcomed the pink into myself. Or maybe I freed it from inside me? In any case, I know it's possible for someone to give up their shape for a more feminine one and not become what Lorelei and I are. Which I guess is a sissibus? Sissy + Succubus?

Whatever, it's done. I told my story and got the information about the swirling stones out there on the internet where, hopefully, it will be useful. As for ending this story, well...

I think Lorelei humping away at me while whispering such gentle cruelties and playing with my little clitty is a good final image, isn't it? Me with my ass out, boobs bouncing, head thrown back in ecstasy, my pink soft against Lorelei's crimson... It doesn't get any better than that.

1...345678
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
Runner4069Runner4069over 1 year ago

The sex is good, but the plot is more akin to your more rest stories not of Gen and Jamie, aka really strange. The writing is great, the plot and details make it a true story, and the sex is hot so overall I really enjoyed it! Thanks for sharing and I hope all is well!

AnonymousAnonymousalmost 2 years ago

amazing, amazing, amazing. Was an exquisite complement to my own sissy training.

Share this Story

Similar Stories

Pretty boy to Sissy girl Married pretty boy enjoys being cuckolded.in Transgender & Crossdressers
Pursued by a Dominant T-girl Can he resist falling for his gently dominant t-girl friend?in Transgender & Crossdressers
Soft and Hard Chris gets more than he bargained for at the gym.in Transgender & Crossdressers
The New Girl Ch. 01 A straight boy learns to submit to girlcock.in Transgender & Crossdressers
A Bad Bet with a Playful T-girl Will he lose and be feminized by his fun sexy T-girl friend?in Transgender & Crossdressers
More Stories