Date with a Sissy

With only a candle still burning, Lorelei came closer to the bed and once more I caught a fleeting shine upon her chest, as if the meager flame was reflecting off of a necklace but no, she was naked and standing there. Waiting.

"You don't have to-" She started saying but I rose and sat on the edge of the bed, silencing her with a look, a power I didn't know I had. Scooting off the edge, I went down to my knees and just that action made her moan, Lorelei's breathing giving away how eager she was for this. And once more I was struck by how much she wanted me and how damn good that felt.

Those broad hips were before me and Lorelei's still not visibly excited nub seemed to both invite and mock me. I knew how dicks worked, well mine at least, and hers wasn't following the script. Strange, but enticing, like a certain forbidden fruit. And so I leaned in to get a taste.

Lorelei gave an honest to God squeak as, without much effort, I had all of her meager length in my mouth. She didn't weigh heavy on my tongue like I'd read about in certain spicy stories and my lips were against her smooth skin but she still took hold of the back of my head. I lapped at her with my tongue and was rewarded with a taste of salty something. And that was it. No hardening, nothing resembling an erection, just her remaining soft and limp.

With those facts established in my brain, I finally started sucking, stretching her out but she refused to keep that shape. But Lorelei quaked under my touch, her hands now cradling my head as I navigated something I thought I knew and had to be doing a good job considering the sounds she was making. That loose bit of skin was brushing my lower lip and, with minimum effort, I opened wider and took that in as well.

I had what a charitable soul could call dick 'n' balls in my mouth and there was still room to spare. That there didn't seem to be any balls in her sack made it easier and I didn't question it. Lorelei's gasp was worth it, her hands tightening for a moment as she cried out. Her delicate parts were just that: Soft and touchable, making no demands and so I learned at my own slow pace. No bobbing of my head but rather using my tongue, sucking every so often.

"Ahh! Stop! Sttttnnn!" Lorelei said but I didn't listen, didn't even understand why she was making such a demand. Stopping was impossible, her hands were still holding me in place and then a thick, salty shot fired off, followed by a second and then only a slow, weak dribble. Sure, this was a known quantity but so little? And it was no effort to swallow that down, only then being able to sit back and heave a sigh.

Lorelei extended a hand that I took, getting hauled up to sit on the bed, my erection fully recovered from losing my virginity and eager for more attention. And this time it was Lorelei who dropped down on her knees, brushing red hair away from burning cheeks as those lips that had been moaning thanks to my actions opened and took me in.

Lorelei gave a long, pleased moan, one that I felt and joined in on as she took me in. There was resistance but Lorelei kept going and then her lips were on my skin and all of me was now in her mouth. Green eyes looked up at me and I stared back, shocked and panting. A hand rose to hold me about the base and she slid back, her tongue working like mine had and I couldn't believe how close I was already. My first bout of head was going to be over too fast but she was so good at this, her tongue going around and around and...

I threw my head back and lost the fight. Spasms of orgasm racked me as Lorelei gave short, approving moans as I saw naught but the darkness and unnamed colors behind my eyelids. Having someone else in control of my pleasure was so new and damn good that it was little wonder I couldn't last very long. Opening my eyes, I saw Lorelei appeared to be wearing something but a few blinks cleared my vision, with her only letting loose of me when our eyes locked. I gave a weak moan then fell backwards and almost instantly passed out. Yeah, I'm a great guest, I know.

Some time later I woke up to a candle still casting flickering light in an unfamiliar room and pieced together where I was and why I was naked and horny. "Good morning." Lorelei said, scaring me as I turned to find her sitting in an ancient stuffed chair in the corner, wrapped up in a sheet and with phone in hand. "It's 1:30 am, in case you care." I shrugged and sat up, finding I was unexpectedly tired and, perhaps more understandable, thirsty.

"So, I'm going to be honest with you if you're honest with me, kay?" She said and I nodded, a slight bit of dizziness not at all welcome right then. "How ya feeling?"

"Kinda weird?" I said and she gave me a wan smile, setting the tone for what was coming.

"I'm sorry, I shouldn't have done that last bit with you but... Ah God, it was so nice!" She said and sighed, a tinge of desperation entering her voice. "Look, this is going to get weird and I'm sorry, okay? If you leave now, I'm not going to blame you." And now it was misery, loud and clear, being spoken by Lorelei.

"Try me." I said and Lorelei gave me this look, as if she couldn't believe what she heard. "I've seen ALL the Hellraiser movies! You think you can get weirder than that?!" And she laughed hard at my boast which, in my defense, is pretty sound. Fuck, Revelations was bad. Has any movie with revelations in its name ever been good? Probably not.

"Okay, challenge accepted." She said with mirth dancing in her green eyes and a smile. "So, about two years ago I'm out exploring this burnt down house in the middle of nowhere. Bored and broke, had nothing better to do. Place used to belong to rich people in the 80's and now it's supposedly haunted. So I go check it out and I find a jewelry box and it isn't burned or anything. Looks new." She pauses, brushing hair behind an ear and Lorelei's mirth is missing when she resumes speaking. "That should have been my first clue something was up."

"Anyway, I expect it to be locked but nope, it opens up and there's a necklace inside. A big red stone on a pendant. I'd never seen anything like it before. And... I don't just look at it but into it. I saw... Something in the stone. Then I put it on, I don't know why." Another pause. "No, it wanted to be worn." I didn't question it and only nodded, thinking of Tolkien's One Ring and how it had a will of its own.

"I leave wearing it and on the drive home the necklace falls apart. I've still got the pieces around here somewhere. But that stone..." And then Lorelei let the sheet about her shoulders fall and I saw, above her breasts, an oval stone maybe two inches tall and one wide seemingly inset into her skin, shiny and dull red. "That freaked me out but then my body started changing and I had to act fast." She gave me a wry grin as I found it hard to pull my attention away from what was shining in the flickering light of the room, the thing I'd caught glimpses of all evening.

"I used to be a guy a lot like you. But a few days after this," Lorelei tapped the stone and it made a faint 'tink', "I ended up like this." She gestured to her breasts and I looked, if only to be polite. And yes, they were still superb, if you needed reminding. "I move, blah blah, buy new clothes, start living as a chick and hook up with a guy, that goes great until I notice he's starting to change. Like I did." A deep sigh as Lorelei shakes her head.

"Here's what I've figured out: If I'm around a guy too long, he starts... Turning into me. This." I nod, following the logic if not exactly believing her quite yet. That she appeared to have a precious stone embedded in her chest helped me buy in, however. "And condoms actually protect against it! Somewhat. It's why I hoped you were okay with me cause I can at least have one night stands. The uh, blow jobs, nice as they were..." And then she flipped the sheet off her legs and allowed me to see the rest.

That cute, innocent little nub I'd taken in my mouth was at least three inches long and thicker, the skin under it now fuller, Lorelei's works now appearing more typical if still on the smaller side. And she was hard whereas before that had been impossible. Without needing to be told, I checked out my own goods and found that I had an erection, unsurprising, and that it was smaller. Not by much but I wasn't as long or wide, not even when I gave it a few strokes, it felt just as good but my dick had shrunk over the course of a few hours.

"I'm sorry! I... Look, I really like you, okay? And I don't get to date because any guy I'm around loses his dick then gets tits and so far I haven't found anyone who's into that so I get sex, which is nice but I want something more!" Sighing, Lorelei flopped back in her chair, legs spread and showing off her newly enhanced assets. I was still mentally fuzzy from sleep but was coming to terms with this. I felt my chest and found little give there... But were my nipples just that little bit more pointer? They felt tender, with me giving a little gasp at just touching them.

"I don't know how it works exactly but I shouldn't have swallowed." Another heavy sigh as she kept talking up to the ceiling, with me listening while admiring her. "I just wanted to thank you cause no one ever goes down on me and Mmngh, it was good..." That's when my mind was made up. To be honest, hearing Lorelei utter such a deep, moaning call was probably the most flattery I'd ever received in my life. Carefully, I slipped out of Lorelei's bed and a few steps got me to where she was sitting, once more slinking down to my knees.

She jumped when I touched her leg, looking down at me with raw panic before I rubbed her thigh, her breathing getting back under control. "Sorry." I whispered and she swallowed hard.

"Wha..." Lorelei said, not able to finish her question before I moved my hand from her leg to what was sticking up now. She was hard, more familiar and was making me very aware I was touching someone else's dick, silky smooth and almost filling my hand. "Didja not hear me?"

"I did." Said while stroking her, it was amazing to hear her heavy breathing, how her legs were stirring while I was working. Cause I'd gotten good at working my own meat and now that Lorelei had something approaching an erection, I knew how to make her feel good. "But what if I don't care?"

"Ah! You'll end up looking like me!" She gasped out and I gave Lorelei a good examination, seeing nothing but beauty. "And! Oh God stop, please, just for a second!" Her voice was strained, urgent so I followed her request, Lorelei panting for a bit before speaking in a slightly calmer tone.

"This, the length I accidentally took from you, it doesn't last. But your changes will. I don't want to ruin your life for one good night." My eyes wandered down her frame and this time I saw the gem on, in?, Lorelei's chest. And I had been wrong, the color wasn't static but shifting, swirling, a storm of crimsons contained therein.

"Okay?" Lorelei said, as if trying to reason with someone who had none but I wasn't listening. I heard the loneliness in her words, how she was trying to find happiness and meaningful contact while not inflicting herself on others. Looking into that shining stone of so many shades of scarlet clarified all of that for me.

And my answer was to open my mouth as if to speak and instead descend down upon Lorelei's erection. She tensed under me and the moan was just as good as feeling that wonderful living silk with my tongue. While still too short to re-enact the sort of blow jobs I'd seen in adult features, she pulsed, jerked, moved about as I gave her all the attention I knew how to give. The thick taste of salt mingled with her moans, thick thighs threatening to smother me as her legs draped over my shoulders, pulling me closer.

With a shuddering, light pitched moan, I felt Lorelei's end. Her stubby length didn't swell that much but the amount of heavy heat had increased from last time, something I didn't mind. It took some time but eventually her grip on me loosened and I was able to sit back and breathe, noting the stone upon her chest was both brighter and more vibrant, those interior clouds moving faster in never ending spirals.

"Oh, you are the best." She said, sitting up and facing me, flushed with color. "I don't want to pressure you into anything and I need to go get more condoms..." I glanced at the gem, in the gem, and found waiting to be an impossibility. So very slowly, I shook my head to that second prospect and Lorelei responded after a moment of looking down at me.

"If you want..." Low, breathy, and inviting, that was said while rising to her feet, with me still on my knees. And gazing upward, Lorelei was a towering monolith of near absurd curves and a sizable erection, face almost hidden behind the swell of breasts. Yet I still saw her eyes and they sparkled brighter than the now hidden gem in the candle's flame. A single step and Lorelei was beside me, another hushed step then I heard the mattress creak.

Slowly I rose, naked, excited, scared and having bought into what my date had told me. Turning, I saw Lorelei with her back to me, having reached two fingers from each hand under a hefty cheek and gave them a few bounces.

"If you want." I nodded, unable to look away even knowing what going to Lorelei meant. But I took that step and she handed me a familiar bottle that I dropped. "Easy." She said in a kinder voice as I picked up the lube and took a deep, steadying breath. Popping the lid open, I poured a small amount in the palm of my right hand and started getting myself ready.

"So I guess you're a dick and ass guy now?" Lorelei said with a smile, back still to me and her ass on display. I gave a weak laugh, too worked up and mentally preparing to do much else.

"I think I'm your guy now." I said while jacking off my slightly smaller self, ready. Lorelei turned towards me, smiling, that gem almost glowing in the candle light. A step, then a second and Lorelei was close enough her erection brushed my own. Slowly, she leaned in, letting me feel her newfound need and those dark lips found mine.

"Thank you." A whisper and the bottle was taken from my numb fingers, with Lorelei pressing against me while murmuring I should get her ready. More liquid chill was poured forth on my fingers and then I was reaching around, not to grab her ass but instead go right for the prize. Lube smeared on her cheeks as I slipped between them, rubbing blindly before Lorelei muttered for me to move down and there I felt give.

She gave a brief inhale and I swallowed hard when my finger entered, Lorelei pressing against me while demanding I go all the way in. A moan came from me as I felt her erection pulsing on my leg, so eager and alive as I buried my finger up to the knuckle. Her lips met mine but I couldn't return the passionate kiss and Lorelei understood, telling me to prepare for the real thing. I withdrew my digit from her and Lorelei squeezed more clear lube from the bottle and got ready far faster than I had before turning around and bending over slowly.

The invitation was clear and I took it, stepping close and I felt her bare skin against my own, my sex drenched and straining, not showing any of the lingering, gnawing doubt I felt. Sounds were coming from me but I had no control over that, all motor and brain function was tied up in finding Lorelei's inner heat and I felt the entrance. She was soft there and I whimpered, taking her hips in my hands before slowly leaning in.

Lorelei's pleased "Mmmhh..." drowned out the small, gasping sounds I was making as her heat became known to me, more intense without a condom. Shaking and panting, I shuddered when her amazing ass was thrust back, impacting me and swallowing up my erection with seemingly no effort.

"Come on!" She commanded and after a deep breath, I gritted my teeth, spread my legs out and felt Lorelei's cushion smush against me when I thrust. "Nuh!" Light and needy, that sound she made was adorable so I thrust again, holding those hips and was rewarded with another cute gasp.

For my first time not as a virgin and being more active I don't know how good I was. But Lorelei was into it and that's all I cared about. I held onto her hips for dear life and they allowed me to ride her without being thrown back, legs weak for so many reasons but the leading one had to be knowing I was giving up more manpower by doing this. Maybe, probably, that forbidden knowledge made it all the better, along with the vulgar sounds of us fucking filling the candle lit room.

Lorelei's warnings didn't mean much, not when I was getting close, Lorelei leaning over more and making louder, more desperate sounds. Each thrust I felt a little something extra and, pausing to catch an increasingly fleeting breath, I found my balls nestled up with Lorelei's. That didn't stop me from carrying on, nothing could. Holding onto hips worthy of being stared at, pounding an ass that I would have drooled over if seen at work and listening to a voice calling out in rapture, I choked on my own voice as the building pleasure finally broke its dam and flooded me.

Shuddering, holding onto a jerking Lorelei who was calling out, my vision faded out as I let loose into her. There was no rubber to catch my useless spill or to dull her heat that had a hold of me. Or to protect me from what Lorelei said was coming my way but I didn't care about any of that, I was tired and awash with a glow of contentment. I'd had sex for the second time in a single night, I might as well have won at Life, the Universe and Everything for how high I was flying right then.

Finally getting my head out of those obscuring clouds that made all thought stop, I carefully stepped back, pulling out of Lorelei and nearly falling over. The amount of weakness and fatigue that settled over me was appalling, certainly not helped by having fucked on my feet. A sigh from Lorelei summed up all of my current feelings and she rose, kissing me on the cheek then taking one of my hands, leading me to a small, dingy bathroom where we cleaned up in exhausted silence. Her jewel was an exuberant shade of red and it invited me to stop and stare, to find the secrets that lay within but Lorelei said she had to take a leak so I gave her some privacy. Once she was done I did my business then joined her in the bedroom, a cold bottle of water waiting for me on the bedside table. I drank it slowly, sitting on the bed while Lorelei was lounging in the chair opposite me.

Once more that shining, shifting stone was calling for my attention and, being so very tired and sitting on the bed, I gave in. Those interior motions were mesmerizing, deeper strokes of crimson hiding and I shouldn't have been able to see them, the stone wasn't that big but it filled my vision and in the deep I thought I saw something that wasn't red but instead-

Lorelei moaned, snapping me out of that complex world that swirled eternally to the one I was more familiar with, finding her legs spread and in the minutes since we'd banged, she was slightly bigger. I checked my own tool and thought it was smaller but fatigue was fogging my thoughts.

"How big were you before meeting me?" She asked, taking a sip before giggling at my visible confusion. "Oh come on! I used to be a guy, I know how it is!"

"Seven inches." I muttered, face red for reasons I couldn't have explained then and even now I'd have trouble doing so.

"Ohh..." That coo of awe made me shiver and Lorelei knew it. "I knew you were big." She said in an inviting tone with a smile that bordered on dangerous. "But if you hang around, it's going to be gone for good." I took a drink and then shrugged, still formulating how I felt about all of this. I felt something, that's for damn sure, but I didn't know how to express it then.

"I just, I don't want to sound ungrateful because this is the best date I've ever had!" I'd forgotten all about supper and the walk after. My first date had led to me losing my virginity and maybe an inch of my penis. Now there's something you don't hear every day. "But I don't want to pressure you into anything either because it has permanent consequences." Another sigh from her and I rallied my thoughts, bringing the cool water to rest on my forehead and only after that did I speak.