Leah, Locked

This is a re-post. The first time I uploaded it something went weird and it only got the first few pages. This is the whole story. There is more to tell of these two, so if you're into this stuff, stay tuned. If you aren't into sissies and chastity, you should probably go read something else. Constructive criticism is always welcome. I hope that you like it!

I was trying so hard not to be nervous. I'd checked into the hotel a few hours ago, and I knew I was early, but I was still terrified that the person meeting me would cancel. That all the anticipation, time getting to know each other, the trepidation, and all the planning would be for nothing.

We met online, of course. A couple of strangers who had similar interests connected and became friends, then decided to take the plunge and meet. I sure hoped this person was who they said they were, but I was still nervous.

Some of that was my choice of attire. I had on my favorite sundress, my makeup was as close to perfect as I could get it, my hair was great, and I had on underneath the dress my favorite corset. Clipped to that were eight garter straps that held on my expensive, brand-new white stockings to match, and at the end were my pretty white pumps with four-inch heels. Topping it off was the pair of satin crotchless panties, pulled over the garters, that let my cage free.

Oh, yeah. I forgot to tell you: I'm a sissy in chastity. I'm genetically male and live my life outwardly as a man, but underneath the trousers and business shirt is usually at least a pair of cute panties cradling my caged cock, most of the time my panties are accompanied by a (very understated, of course) bra, garter belt, and stockings. I keep myself hairless from the neck down, too.

When I'm at home, a lot of the time I'm wearing feminine, often frilly or silky or sheer, things. I just feel so much sexier that way, that's all. Especially when I'm plugged, which is most of the time.

So why do I lock myself up? Well, the short answer is that nobody else has offered to. But there's so much more than that. I don't think I'm gay in the traditional sense, but I have always loved wearing women's clothing, the more obviously feminine the better, and feeling smooth and soft. I freely admit that I've had a cock or two in my mouth, so that probably doesn't help my case, but all but one of those were attached to someone who was dressed in a similar way as I was then in the room. Don't get me wrong, cock is awesome, but I much prefer when it's attached to someone who's as feminine as possible. Ideally, I'd find a transwoman who was into sissies like me who was a dominant top, and we'd live happily ever after. And life is rarely ideal.

So I found myself drifting into the world of sissies. Guys who loved to dress in women's clothing in a very sexual way, and who wanted to be as feminine as possible but to still be able to live their outwardly male lives for a variety of reasons, which I don't need to go into right now. The point is that I've become a sissy and if I can't find a domme top transgirl or a genetic woman who's into dominating a submissive (mostly) bottom sissy like me, then I could at least find some companionship with someone else like me. Is that gay? I don't think anything about human sexuality as ever that cut-and-dried, so I don't care. I'm me, and I like what I like. If I found a female partner who loved dressing me up, caging my cock, fucking me senseless with a strap-on—or having me use it on her!—then I'd propose marriage soon after we met. I'd be happy with that, especially if she really got off on having a caged sissy husband who adored going down on her. As happy as I am sucking a cock, I really, thoroughly enjoy eating pussy and the way it makes me surge and leak in my cage.

But I haven't.

I'll bet that you're still wondering, "Why the chastity cage?"

It's complicated. Of course I love penile stimulation! It's fantastic! But I also have a submissive side that loves giving up control, even if it's only to an ice cube in my freezer that acts as my keyholder, and chastity is a perfect way to do that. I can't describe it exactly, but there's something that makes me feel so submissive and safe when there's a plastic or steel sheath around my cock and balls not only keeping me from getting fully erect, but makes it so that I can't feel much stimulation on them, either.

But I've started monologueing, so I'll get back on track: So there I was, waiting for Amanda. That was her femme name, anyway. Mine's Leah. As I said, we met online and that had culminated in this meet. Well, hopefully a meet. Anyway, we're both femmed-out sissies in chastity who're into being dominated, or at least penetrated. We'd come up with a rather sexy idea or two on how we could get together and--

There was a knock at the door. I froze, panicked all of a sudden. What am I doing?!

After a deep breath that I hadn't realized I was holding in, I walked to the door and looked through the peep hole. There was that weird fish-eye view of a fairly pretty, if a little mannish, woman standing there.

I let out another breath, one I hadn't realized I had been holding in again, took another deep breath, and pulled the door open, stepping back to stand behind it so even if someone else was in the hallway they couldn't see me.

I shut the door, looking at the floor, then looked up. And there stood Amanda, just like in the pictures she'd sent me of herself. She had a wry grin on.

My stomach wasn't doing somersaults, it was a full-on gymnastics routine. Olympic level. Mary-Lou Retton would've been jealous.

I realized again that I was holding my breath and let it out slowly, then took another slow one. You can do this, Leah, I told myself. "Amanda? I'm Leah," I introduced myself, extending a shaking hand out. Christ, I was nervous! I was sure that my voice was way too masculine.

"It's so nice to meet you in person, Leah," she responded with a warm smile. Her voice was kind of deep for a woman but was very feminine. She took my hand and instead of shaking it, raised it up to her painted lips and planted the gentlest of kisses on my knuckles. I blushed, totally flustered that this confident, put-together woman was treating me like I was a lady. "You're very pretty," she added, releasing my hand.

"Uh...I can't look anywhere near as good as you do," I stammered.

"Nonsense," she retorted. "You're cute as hell. You're even cuter in person." She winked. Winked!

I let out a nervous laugh that probably sounded forced. "You're just saying that," my insecurities and internalized shame forced my mouth to say.

She took my chin in her hand ever so gently and brought it up to look into her eyes. "No, I'm not. You're a very pretty lady, Leah."

My skin felt so hot I could start a campfire. "T-t-thank you. You're gorgeous," I gushed. I had apparently forgotten that she was about ten years older. And therefore had a lot more experience. No wonder she didn't mind coming to my room.

Her smile was radiant. "Thank you, sweetie. And thank you for arranging this, it's so nice to meet you in person. You even have great taste in perfume," she added.

I blushed again. I don't know what kind of script I had in my head for how this was going to go, but this was definitely way out into improv territory. "Thank you. Again. I feel cute when I think I smell nice," I admitted in a voice that I had to also admit that wasn't as mannish as I had feared. "Thank you for coming over and being willing to be seen...out."

"Honey, I've been out so many times I can't even count, and I can't remember the last time I got made. People are way more self-centered than you think, even you: You're so wrapped up in being worried about being outed you forget that most people barely look at anyone else on the street, from what I can tell. You're pretty, young lady! All most people are going to see is a pretty girl doing whatever she's doing, sweetheart," she explained, then topped that off with a soft kiss on my lips that set me off, surging in my cage. The cage that I'd been so nervous about I had forgotten, since I was super nervous, and therefore flaccid as I could be. Until now.

"Mmm..." I murmured as our lips separated. "Thank you," I said, feeling the butterflies settle in my abdomen. "I really appreciate it, and I'll try to keep that in mind."

She was already smiling but at that Amanda had the sweetest smile I could imagine. "It's part of why I agreed to meet you, Leah. You're so young and pretty but you're so high-strung! And that's adorable, don't get me wrong, but it would really help if you could loosen up, sweetie! Life's too short to worry about what other people think.

"The whole walk here from my place in these heels," she began, glancing down at what had to be outrageously expensive Louboutins, "I could feel the padlock on this thing," she indicated, lifting the front of her dress up to show an expensive pair of tasteful but sexy panties that caressed a high-quality cock cage, "bouncing a little with every step I took. Yeah, maybe someone hears a click or something, but do you think that the first thing they're going to think of is, 'That middle-aged woman must have a cock and must also love to have it stuffed into a cage and that's not really a woman anyway because she has a cock, and...' I don't know, whatever else? They'll probably figure that it's a thing nearby like a car that someone shut off recently or something else that's just as innocuous. So I walked like the lady I am, secure in knowing that I was secured," she told me, laughing at her own joke at the end.

I couldn't help but giggle myself. "I guess I never thought of it that way."

With the gentlest of caresses to my lightly-blushed cheek, she smiled a sad smile and said, "You never do until you do it enough to get comfortable."

I closed my eyes and nuzzled her palm with my cheek. Even as I settled down and was therefore getting turned on, I couldn't believe how fortunate I was to have this older, more experienced CD here to guide me. If what we'd talked about took place, or anything like it, this had a chance to be an epic time.

"Now, let's get comfy," she said, taking my hand and leading me back into my own hotel room.

She was tall, even in low heels. In my four-inch heels I stand at six foot one, and she had several inches on me with lower heels. But that just made her statuesque. Like me, she didn't have very pronounced hips (damn XY chromosomes!) but she did have a nice, if subdued, hourglass figure. Her bust was prominent but not ostentatious. I found out later she had large C cups or small Ds.

Her face was kind, first of all. She went for a kind of classic vampy look, I guess? Bob haircut or wig, fairly heavy but very feminine makeup without seeming like an obvious drag queen, while retaining a few aspects of that sub-genre. She had full lips, soft, honey-brown eyes, a strong jawline that I saw she used skilled makeup to hide, and what I can only try to describe as an average nose.

"So. Tell me about yourself, honey," she said as she set her large Coach purse down on the bed.

"...Um..." Great start. "I...uh...what do you want to know?" I replied. A lame attempt, I knew.

"Well, we already know your a caged crossdressing sissy, so what don't I know about you? What music do you like? Do you have any hobbies?" she inquired in the most conversational tone that you could imagine. Meanwhile, my face was on fire.

I swallowed hard, the embarrassed feeling quickly extinguishing the nascent erection that was trying to come into existence.

I gulped. "Uh...music. I love music. I'm a huge fan of..." I rambled, going into a bunch of music that I enjoyed and how I loved to sing along, veering off into the fact that I do IT professionally and play games, and then...I realized how uncomfortable I didn't feel, and stopped mid-sentence.

"You bitch, you did that on purpose!" I exclaimed with a laugh.

A grin without malice spread across Amanda's face as she poured me a glass of wine into a plastic cup. "Guilty. Honey, you were so high-strung when I walked in that door that I could've played you like a banjo," she declared, a trace of a southern (probably Alabama or Louisiana) accent tinting her cadence. "We're here to have fun, right? So let's both acknowledge that we're both caged crossdressing sissies and figure out to have fun with that, why don't we? After all, didn't you have a pretty good idea about that?"

I blushed again but not because I wasn't comfortable with myself, but because our society conditions us to feel like sex is dirty, but hey: we all got here because our parents had sex, gross as we may find the concept. Sex literally is how life begins, but...I'll get back to the story, now.

"I figure things out for a living, I guess," I said, sipping—no, taking a gulp, I was nervous—of the wine. It was pretty good.

"You guess? They haven't fired you yet?" she asked with a raised eyebrow.

I had to chuckle at that. "No, I don't guess. I'm just not a hundred percent comfortable with this," I explained as I sat and crossed my stockinged legs as casually as possible. I had to give it to her, Amanda was amazing at putting me at ease.

She smiled. "I'm not, either. I've lived with feeling like this long enough that I've learned to stop giving a fuck what people think of what I might do and just go do it and to hell with whatever they may think," she declared, and took her own not-small-enough-to-be-a-sip.

I laughed, "I hope I can be that OK in my own skin someday."

"I think you're more comfortable than you think," she said. "You're here in a hotel room with a stranger you met on the Internet. You're a dude to most of the people in your life, yet you're here with what feels like expensive, sexy lingerie on under a pretty sundress, made up and with either one hell of an expensive wig or hair to die for, your makeup's on point, and your naughty clitty is locked in a chastity cage. You're sharing all of that with a stranger. That takes quite a level of comfort to even walk through the door, never mind open it when I knocked," Amanda told me.

Holy shit. She was right. Every step I had taken that led up to that moment had been one of a long string of affirmations that I was OK with what I was doing, I realized.

"Son of a bitch," I whispered.

She laughed, a warm, welcome sound. "Now you're hearing what I'm saying."

"So," she said, standing up and walking up to me, stopping right in front of me. "Now we can get to why we're here. Right?"

I swallowed, hard. "Right," I affirmed in a tiny voice. "I think."

"I think you know, Leah. Don't you?" she asked, her eyes locked on mine.

I took a moment and realized, yes, we can. I cleared my throat. "Yes. We can."

"And what's that?" she asked, her voice suddenly dripping with sexiness.

My little friend woke back up, starting to fill my cage back up. "Have some fun sissy sex while we're both locked up," I said in a quiet voice. I managed to maintain eye contact. My mouth was dry, though, so I took another sip of wine.

Amanda smiled at me, a hunger now in her eyes. "Yeah. My Mistress and wife keeps me locked 24/7 and I'm only let out for cleaning unless she wants to fuck me and that's always on her terms, so I have been caged almost constantly for the last year and a half. The only times she lets me cum is when she wants me to, and she gets off on denying me, so I might have had six orgasms in the last year that weren't caged. She also limits how many times I get off when I am caged, and that's only from when she fucks my ass. Or if I'm really lucky she lets me use a vibrator on my cage while I eat her pussy. She does let me play with other sissies and if they can get me off then that's allowed, but that's only if she can do it from fucking my ass, so, I guess we could say," she told me, unzipping her dress, "that I'm one horny caged sissy bitch who's looking to get fucked. How are you going to help me out?"

"I didn't know all of that," I admitted. "I locked myself seven weeks and three days ago, then put the key in a bottle of water that I froze, and I don't know how to have a sissygasm, so I don't know if it's the same thing, but the last time I came was over a month and a half ago," I told her. Her eyes were smoldering.

"Kiss me, you sexy little bitch," Amanda demanded. Her hands were on mine, pulling me to my feet.

Our lips met and she crushed hers against mine, unbridled passion fueling a kiss I'd remember for a long time. My cage, which was fortunately made of solid stainless steel, was up to the task of restraining my very, very eager sissy clit. I felt it brush against Amanda's and a shiver went up my spine. I was making out with another caged sissy and we were going to fuck each other someway or somehow until we ran out of stamina or we managed a sissygasm.

The kiss broke and I spoke first. "The strap-on I ordered arrived yesterday. It's the one you wanted. It's pretty big, I have no idea if I can take it," I told her.

"With enough practice, you can take anything," she said with a slow wink. "I have a smaller one with me in case that one's too much."

"How thoughtful!" I exclaimed, clapping my hands and jumping up and down in a parody of thankfulness.

That's when I really got Amanda to laugh. It came from her belly and she sounded very feminine but the joy and mirth in it was unmistakable. "Oh, shit. I wasn't ready for that," she commented with a chuckle.

"So...how is this going to work?" I asked. "Who goes first?"

"Well...I thought about that on the walk over here, while my cock tried to get hard in its cage,"

she answered. "Have you ever had a sissygasm while you were caged?"

I thought for a moment. "If I have to think about it then no. Have you?"

She shivered. "Not as many as I would like, but I have and it's fantastic. Every time it was my Mistress taking me after she had denied me for weeks," she said as she shivered. Out of the corner of my eye I thought I saw the front of her panties twitch. "Even that one time I agreed to let that guy fuck me even though at first I wasn't into it...oh, fuck! That was hot.

"That makes me think that you should be first, so I can show you what it is that does it for me. Have you been practicing?" she asked as she drew me in for another kiss, one that resulted in the zipper on my sundress somehow coming all the way down so that as soon as she stepped away it fell awa from my body.

I blushed again, feeling exposed. But she was already in her sexy black lingerie, her cage outline visible through her sexy satin bikini hiphugger panties. There was a clear wet spot on her panties where the end of her cage should be. I glanced down and there was a clear bead at the end of the tip of mine, I realized. I flexed my PC muscles and watched my own cage bounce up and down. FUCK, I was horny!

"Yeah, almost every night. I don't know what I'm doing wrong," I said, embarrassed that I could feel myself pouting.

She took my face in her hands and kissed in the softest, most sensual way I had ever experienced. It wasn't rushed, it was just a display of affection and desire, our painted lips caressing each other while her tongue probed into my mouth in a tentative way. Amanda pulled back and smiled, looking into my eyes. "It's an awful lot of fun to practice, though, isn't it?"

I chuckled. "It is but I'm so fucking horny!" I pouted.

"I know, sweetie," she said, kissing me again. "I'll try to help."

I took another deep breath, acutely aware of my denied cock straining in its prison. "Where do you think we should start?" I asked.

I felt her soft fingertips brush my hairless scrotum and sighed, closing my eyes. It felt like her other grazed my own breast through the cup of my corset, too. I think I forgot to mention that on top of all my lingerie—well, underneath it, actually; I mean in addition to—I was wearing a full silicone breastplate that gave me a pair of healthy D cup breasts at the expense of my real nipples being hidden. But I had learned to use makeup to blend the joint around my neck so that it was almost imperceptible to me. I hoped it was the same for Amanda.