Date with a Sissy

"You're talking to someone who most people ignore. And it feels like you're the first person who's cared about me. Like, just being able to talk about movies with someone who doesn't consider Shrek one of the all time greats is so nice!" I said and couldn't help but laugh along with Lorelei, delighted by my own joke. Once the laughter faded, I dredged down and started speaking from the soul.

"And I don't think I mind? All your warnings don't scare me. I... Like being around you." I said slowly and shrugged, so very tired and a touch warm, the lazily spinning ceiling fan not doing much to cool the small room.

"Can I be honest? Like, scary honest?" Lorelei asked and I nodded, not sure if there was any other answer to a question like that. She leaned forward, elbows on thighs and bare breasts swinging down. The stone glinted red from the meager fire and I, like with the One Ring, felt it inviting me to look once more and resisting took effort. "I was dealing with some gender identity shit when I found this." She tapped the stone and it made that same solid sound, 'tink!'

"I was, am!, happy about how I look now. But it's accidentally changing other people that scares me. And..." Lorelei's eyes dipped down to my junk, then back to my face, green and serious. "Something about your picture made me message you. It was the same feeling that made me put on the necklace in the first place." I swallowed hard, all my thoughts twisted up but there was no revolt, no demands for her to explain what in the fuck that meant.

Instead I continued to listen as Lorelei spoke. "I liked you right from the beginning but seeing you in person, there was this... Aura? Nimbus? Like one of those halos in old Christian paintings around you. I'd never seen anyone else with that before and didn't know what it meant. There's so much about this I still don't understand." She sighed and rubbed the stone in her chest as I just sat there, digesting her words.

"Is it around me right now?" I asked, hoping it wasn't a dumb question. Thankfully, she nodded.

"Not as big or bright but it's there. Do... You want to be like me?" Lorelei finally asked and I shivered, aware of my dick getting rock hard in spite of how tired I was. "Well, I can see part of you finds the idea appealing." She rose from the chair and sauntered over, climbing on the bed and straddling me.

"You can leave anytime." She said and while far from a sexy statement, that's all she managed to say before I kissed her and we were off once more. I ended up on my back with Lorelei laying on top of me, her boobs pressing against my chest and her bigger dick harder, more demanding of attention.

We made out frantically and when I took her ass in my hands, Lorelei demanded I fuck her in a low voice. "While you still have a chance." I moaned at her savage words, a strange, light heat welling up inside me at the words. "Oh? You like that?" I gave a weak whimper as an answer and she nipped at my neck, grinding her erection against mine all the while.

I was tired but the flesh was still willing, Lorelei finding the lube and getting us ready. With me flat on my back and her above me, it was like the first time but she was packing more and me less. And the inset piece of jewelry was a swirling, screaming red that finally captured my attention. I stared deep into those shifting, endless depths as she got into place and settled over me, my dick poking that soft, tight entrance without entering.

"Are you sure?" Lorelei asked and I had to tear my eyes from her chest up, to that beautiful face before nodding. And then she took me in, stealing my breath and grinding thought to a halt. She gave a pleased moan, shifting her weight back and forth before smiling down at me. "I can tell you're smaller now." She said and I whimpered, unable to reply to that. And it made that new heat flare inside me once more.

We went slow that time, Lorelei taking my hands and running them up her hips, to her breasts and I ran my thumbs over the hard pebbles in the midst of such softness while she rose and fell. I felt the firmness of her balls, the tap of an eager erection against me and took that length in my hand, giving it a few strokes and breaking her rhythm.

"I'll be able to fuck you soon. Wouldja like that?" She asked in an uneven tone and I shivered, my dick giving a jump that Lorelei clearly felt. "Mmm, if you want the D then give it to me!" Lorelei pressed down on me and all talking stopped. Instead there was only the frantic breathing of sex and the quickened tempo of her riding me. And I didn't stop stroking her, the head peeking out from my curled hand but I barely noticed it even when liquid heat poured forth on my stomach, shooting out with a force and vigor it hadn't before. No, I was too taken by Lorelei and when I finally reached that apex, I gazed into the solid scarlet on her chest as my exhausted body was racked with devastating pleasure.

I saw swirls and whirls, shapes that had no name and even while I was in the midst of an orgasm so powerful it hurt, thoughts, emotions were clarified in my head. Angst and loneliness, a simmering outrage at how I'd ended up alone and boring and, deep down, how I didn't like my appearance... All of those poisoned pillars that had taken root in the Temple of Me were whittled down to sharp little slivers, much more manageable but still dangerous.

And yet I'd found someone different, who didn't fear but instead was trying to live her best life despite all that was stacked against her. Look, I know it wasn't just the sex that helped me figure some shit out, the gem inset in my lover helped, but only when I was balls deep in Lorelei's ass did things come into focus for me.

Laying there under her, gasping, unable to speak and reduced to weak spasms, I gave a sigh as she rose off me and almost instantly passed out. Epiphany had been placed on hold and dreams couldn't find purchase as I slept in a foreign bed. And when I woke, I found someone snuggled up close and that was another nice, new experience to add to the list.

"Hey there sexy." I heard Lorelei say, voice dusty from sleep. Laying on my side, how I usually slept, I found one of Lorelei's hands resting against my front and I took it. This quiet, tender moment was delicate and beautiful to my still waking mind. The day wasn't fully formed yet and sharing this transitory slice of the morning with someone instead of muttering to myself was a nice change of pace.

"Do you remember last night?" She asked and I nodded, those fresh memories ready to be recalled and, of course, my dick was the first to shake off the shackles of sleep and rise. Yet something was different down there and Lorelei was tipped off to it. "Do you remember all of last night?" Then I became aware of something pressing against my ass, hard and long.

I knew that Lorelei had what might very well be a window into her soul that I'd gazed in and found parts of myself there. Then her words about me being smaller and the almost growled promise about her being able to fuck me, that memory making me shiver. What was I anticipating more? Lorelei packing or me not? Whichever it was, that new light, fluttering heat was back, making thought even more difficult.

That involuntary reaction had made things jiggle in places that hadn't before and that stalled out my breathing. "I cleaned you up after and napped on the couch. I didn't want to spend too long near you but... I think things are already happening." My stomach spoke for me, interrupting our very important conversation with a loud growl and Lorelei laughed, rolling out of bed and digging around in the closet that didn't have any doors before tossing me a worn white t-shirt.

"Here, get dressed and I'll order pizza." I sat up, postponing looking around as I had to examine my chest, which had decided to leave behind being flat in exchange for getting pointy in the nipple region, with gently sloping mounds under those peaks. Sure, they weren't anything close to what Lorelei boasted but boobs! I had the beginning stages of boobs! My erection raged on, ignored, as the new heat rose along with the exalted joy I felt. And, bizarrely, my next thought was that they weren't big enough. I'd gone from no tits to instantly wanting more but it was a deep seeded desire, one I'd come to terms with looking into that scarlet stone of Lorelei's.

Slowly leaving the bed I'd lost my virginity on, I pulled the baggy shirt on and wore only that as I left her bedroom, covered up but not exactly classy. Lorelei's apartment in the clear light of day was grungy in that 90's movie way, as if film grain was baked into the walls and worn hardwood floor. Lorelei was in the living room, lounging on a couch so beige it only could have come out of the 70's. With the curtains thrown open to flood the place with light and her flat screen TV showing Blade Runner, her place was an anachronism, belonging to no one era.

"Yeah, I know it's not great but it's cheap and the internet isn't bad." I shrugged and joined her on the couch as she fiddled with her phone. "You really don't mind?" She asked, her red hair a sexy mess and I leaned in to plant a kiss on her cheek, Lorelei's astonished expression wonderful.

"Why would I?" Talking with confidence, I glanced at Lorelei's chest but the stone was covered so I carried on. "I've been alone for years and I'd rather be a hot chick than, well, me." Lorelei sat up, legs curling under her as she leaned in and kissed me on the lips, the first more chaste but she came back for more, a deeper, searching kiss that left me breathless.

"I admire your honesty but you're still gonna be you at the end of this. Whatever the end is. I'm still the loser I was, only now people pay attention to me cause I'm hot. Which is kinda fucked up when you think about it!" She said and I offered no explanation. "Alright, time for the big question: You cool with pineapple on pizza?" I told her I was before leaning my head on her shoulder as she got the pizza ordered and we started chatting about what to watch, enjoying each other's company.

With the movie picked, Primer as it was on both of our backlogs, she closed the curtains and thus blacked out the room, turning it into a low budget movie theater with seats for two. Lorelei turned the volume up and got comfortable in the worn couch cushions while I nestled in the crook of her arm.

"This is nice." She said while we were half paying attention to Primer, not the best movie to watch with split focus but hey, we were trying. That Lorelei kept rubbing me with her leg wasn't helping, my shirt riding up all the while, exposing skin and threatening to uncover my crotch.

"What, the movie?" I asked and her snort told me I'd guessed wrong.

"No, cuddling, being close to each other. I don't get that cause I don't want to mess with people." She said and I saw her point but couldn't find it in me to care.

"I don't feel like I'm being messed with. I'm becoming something more, something better." My honest, and pretentious, words earned me another kiss which got frisky but the pizza guy arrived so our make out session got put on hold while we ate and were further confused by Primer. After eating I dozed on the couch with Lorelei, waking up hours later to her telling the Nightmare on Elm Street Remake to fuck off.

"The New Nightmare was better." I said automatically, blinking sleep out of my eyes and wondering why I sounded different.

"Hey, it sounds like things are really happening now. If you leave I wouldn't blame you..." I silenced her worries with a raised index finger before asking if she had any caffeine that wasn't coffee.

"Coke in the fridge." She said and I rose, nearly falling on my face and Lorelei was there to catch me. "You okay?"

"Uh yeah." I said in my more feminine voice, standing tall with her help and finding my balance was out of whack. "I... Don't know what's happening?" Lorelei surprised me by raising the shirt and looking at my naked lower half, nodding while trying to hide a smile. I could see mirth and excitement dancing in her eyes but also longing as it took her maybe a second too long for Lorelei to look up from my ass. And I found I liked that as I'd had none such power until meeting her.

"Yeah, I remember this and it's weird. So... Your hips are rotating back and pushing your ass out." She turned to the side and ran a hand along her back, smoothing the shirt out and showing off how much her back arched before flowing into the curve of that amazing ass. "And your hips are getting wider. It takes a minute to get used to." With her help I unsteadily walked to the kitchen and grabbed two cans of Coke, leaning against the counter while sipping on mine.

"Are you-" Lorelei started in but I cut her off.

"I don't want to leave. I want to keep going." I insisted, draining the last of the can and instead of letting loose with something profound about my nature as a person, a massive burp escaped. Despite how my body was changing, I wasn't very ladylike in my actions. Lorelei just laughed before offering up her own, loud enough it echoed in the dark kitchen and we lost our shit. She drew close and started rubbing me in a rather intimate place, stifling my laughter but not killing the mood, instead allowing it to be another version of happiness. And it didn't take long before it was clear I was ready to go again but just like Lorelei had said, there wasn't as much sticking up as before even with the long shirt covering it.

"If you want to keep going then follow me." She walked to the living room and, carefully, I did just that, each step not exactly a struggle but rather a learning experience. Lorelei beckoned as she walked backward towards her room, grinning all the while and I picked up the pace, a few jogging steps and then I was crashing down on the bed beside her.

"Good girl." Lorelei said and I shivered, watching as she rose and closed the blinds, cutting the golden afternoon light down to shafts of speckled amber. That done, she stripped off her shirt, revealing she was wearing purple panties that failed to hide her bigger package. And the out of place oval was in fact giving off light, a tempest of reds that might have stolen my attention away from the nearly naked Lorelei if she hadn't spoken.

"I showed you mine, now show me yours?" That's all I needed to hear and took the borrowed shirt off. Only hours had passed and already that reflexive wish was being granted: My breasts were indeed bigger, the areola slightly larger and the peak poking out more. Down below, my old friend wasn't quite at half the length it'd been since puberty and was lacking girth as well. I took hold of it and found only the head and not much else was peeking out. Like Lorelei's had been last I touched it.

Movement from Lorelei got my attention as she stripped off her last scrap of clothing, an impressive boner springing up with an eagerness I knew all too well. Just from looking I knew she was now bigger than me in all aspects. Length, width, girth and even her balls were filling out, looking far more normal than before.

"Unh! I forgot how good this feels!" Giving her erection an idle swat, it jostled back and forth but stayed firm. My own tool gave a slight jump and I let loose of it, looking at the one thing that'd given me so much pleasure in my time alone and finding I might prefer what was going to happen more. A glance at the chaos of crimson Lorelei wore confirmed it. I don't know why that was able to clarify such tangled thoughts but it was. Sometimes answers are simple and unsatisfying.

"So I've finally got something... Substantial for you." She said, walking over and my attention was split between shifting colors, boobs and dick. That is quite the list and one of those things is not like the others! Once more I went to my knees on the floor as Lorelei approached, her expression softening while looking down at me. "I don't want to make a habit of this, you going down like-" And I rendered her speechless by reaching out and touching what promised to be more substantial. Still silky but filling my hand more, even the amount of heat pouring off her had increased.

"Let me be your girl for now, okay?" I asked, that light, fragile fluttering going strong inside me. At what I'd said or the far bigger dick I was now stroking, there was no telling. This whole situation had smashed my life's desires into so much chaff and being presented with Lorelei and her strange quirks was intoxicating. I'd been here twice before but even kissing the head, running my tongue around it, I knew this time was going to be different.

She was hot and slightly musky, tinged with some sort of coconut lotion or soap but that didn't matter. Lorelei moaning, her hands going to the back of my head, tensing and shaking, that mattered. Opening wide so my teeth were out of the way mattered. Feeling that blind, idiot desire hot and heavy on my tongue, making oh so real all those stories I'd read, that mattered. Stroking what wasn't in my mouth before holding the base like Lorelei had done for me then seeing how much I could take, that mattered so very much.

Finding that she had the length to invade all the way to the back of my mouth, that mattered. Fighting the urge to gag and winning, that mattered! And when I took all of Lorelei into my throat, the startled gasp she gave, the buckle in her legs and the pulsing pillar of life I now held within? Lips in an 'O', hiding away a dick that could no longer be considered small, a tight bundle of balls against my chin, hearing her moan, that meant everything to me right then.

I tried to look up at her face but the heft of her breasts hid Lorelei away from me but that didn't matter, not when I felt what was all the way in me twitch, the only warning I got. She tensed up, those now full balls tightening, then loosening as I felt her fire load after load down the hatch as I pulled in air through my nose, attempting to make some sort of noise all the while but was able to produce a muffled 'mmmfph!'

Only when I felt her start to soften did I let loose and sit back, gasping for air as she panted along with me. "Okay, I thought it was just me!" I wiped my mouth and looked up at her, feeling a more substantial heat sliding down to join that fluttery one which approved of what had just gone down.

"Wha?" Look, a poet I ain't, especially after going all the way down on someone.

"I did that too, with the first guy I was with after finding the necklace." Lorelei helped me to my feet and pulled me into a hug, her very generous breasts now pressing into mine. "And I did that too." She gestured behind me and I saw a little puddle where I'd been kneeling, shame heating my cheeks.

"Better get used to that." Picking up the shirt she'd dropped to the floor, she tossed it over the wet spot as I touched my chest, finding it had far more give than before yet was still firm. Like Lorelei. "And you'll get used to that as well."

"Really?" I asked with such incredulousness that she burst out laughing, slinging an arm about my shoulder and pulling me close.

"Really. It'll catch ya off guard at times but give it a few months of putting on a bra every morning." She said and I then understood I was going to need new clothes and maybe even new everything. If I showed up with boobs to do my job at the college, what would everyone say? Then it hit me: What everyone? I only saw my boss maybe a day out of the month! I was ignored to the extent that if I put on a Michael Myers mask and danced the Thriller down the hallways I'm not sure anyone would notice!

"Doing okay?" Lorelei said and I nodded, not wanting real life to intrude into this beautiful, fragile dream I'd found. "Still an ass girl?" I shivered and she laughed, nuzzling up to me. "There's always other things we could do..." Her dick being pressed against my leg made it very clear what she was after.