Down the Sissy Rabbit Hole

(M+/t -- chastity, oral, bondage, anal, forced)

I stared at the soft light from my laptop screen as I watched a sissy girl in a homemade porn video. I dreamed about what it would be like to be her, locked in chastity and forced to take a real cock up my sissy ass. I rubbed my small clitty inside the pair of panties I was wearing enjoying the smooth feel of the satin material.

I was debating if I wanted to cum yet, when the video ended. I really wanted something kinkier, so I found one with a tied up sissy girl getting face fucked and then having her ass mercilessly railed.

I was just starting to really rub my little clit when a message notification popped up for a chat message. I figured it was some fake or scammer trying to get money since it seemed like that was most of what I got these days.

I was a bit surprised when it was a from a Dom guy that I'd viewed some of their posts and liked the style they had. They were part of a group that went for a strict sissy approach where sissies only served as chastity locked sex toys for their Masters and Mistresses. Slutty clothes, bimbofication, body modification, tattoos and piercings were also very heavily emphasized.

Of course, I assumed it was all just fantasy and fun like so much of porn, it wasn't real, just something to get off with.

The message from Master Clancy was pretty simple, "Hello Alice, you make a very pretty sissy girl. I love your French maid look."

Okay, with some of the sexy, slutty, sissy girls they'd had on their videos, he was complimenting me? I replied back, "Thank you, Sir. I try to look my sexy best when I dress. I've loved some of the videos and photo shoots your group has done."

His reply came back moments later, "I know, I've been watching you for some time now. You've liked and commented on a number of our videos. Many of them mentioning that you'd hope it would be you someday."

Oh wow. He really had been watching me. Was that something I should be worried about or be complimented by? "Yes, I do love the fantasy of some of the wild sexy stuff the girls get put through, but I'm hardly the same level as them. They're so gorgeous and sexy."

"Don't sell yourself short, baby girl. The only thing you're missing is some quality wigs and a good photographer," came his reply back.

Well, he was right on the wigs certainly. I had a few cheap wigs I'd gotten online that were okay, but not something that would really look good. I'd been growing my hair out for some time now, and it was getting to a length I thought I might be able to do something with it, but I really didn't know much about doing a feminine hairstyle, so I still used the wigs in my femme photos. I had considered investing in some quality wigs, maybe with real hair instead of the synthetics I had. I just hadn't done it yet.

Also, taking your own pics is a bitch. Even with a decent camera you never know if the focus is in, or if you're in the frame, if the lighting is good, anything like that. I mean, digital photos make it pretty easy, but I still only seemed to get one out of every ten pictures to actually come out.

"I don't know, Sir. I really don't think I'm ready for something like that. I'm still very in the closet," I replied back. On the one hand, I loved the idea of getting dolled up and being a sissy fucktoy. On the other hand, my fantasies could go to some dark places and I was a little scared of how deep down the sissy rabbit hole I could go if I tipped over the edge.

"I fully understand. Lots of girls are a little unsure at first, but once they do a couple photo shoots and see how amazing they can look, they really get into it," came the reply.

I had to admit this was tempting, but I figured they were nowhere near me either. That was the other issue I ran into. I'd find someone that I really gelled with whether another sissy, a Domme or even a Dom guy and then they'd be halfway across the country, or on another continent. Though as it turned out, his group was only about a 20-30 minute drive away for me.

"That sounds tempting, thank you. I'll keep that in mind if I decide to go further, but I'm not sure I'm ready for that," I said back.

"Okay, if that's how you want to play it," he came back after a slight delay. "Please keep us in mind. You mind if I chat with you some more again? I'd like to get to know you better."

"Yes, Sir!" I replied quickly. "I'd really like that!"

I was so worked up from the idea of being one of their sissy fucktoys that I diddled my little clit until I shot in my panties. I quickly cleaned up and went to bed. I did have work in the morning.

You see, most of my life is pretty mundane. I work for a contracting and consulting company, so most of my work is done remotely, but I do go into the office once or twice a month for our team meetings and such. The money I make from the job is pretty considerable and gives me a lot of freedom, but it does require working a lot of hours, especially if we have a big proposal or launch.

Since I was pretty comfortable financially, I owned my own home, had a nice car and was even able to afford to buy a nice wardrobe, including a full closet of female clothes. I also had a decent supply of toys as well, even some bondage gear. I loved bondage, but practicing self-bondage was tough. Especially without a back-up or someone to bail you out if things go wrong.

Since I lived on my own, I had time to indulge my love for cross dressing and kink. I loved to lock myself in one of my chastity cages and pretend my Master or Mistress was making me dress up slutty for them and play with myself, teasing myself with a vibe or filling my ass with a big dildo.

For me personally, I wasn't really much of a looker. I was pretty average as things went. I was about 5' 6", so I was on the short side as a guy. Not real short, just enough to be below average. The same with looks. I wasn't ugly or handsome, just kind of plain. About the only thing stand-out for me was my eyes. I had really pretty, bright blue eyes. The kind that photograph well, especially with lots of eye make up.

I also wasn't real muscular, but I wasn't thin either. Again, just kind of average. I had muscular legs and thighs from the bit of running and hiking I did pretty regularly, but I never got into weights or being a gym rat. Mostly I preferred being on my own.

That was partly why I was still single in my mid 30s. I had dated a bit, but when it came time to reveal my femme personality, the girls would usually bail pretty fast. I did have two girls that stuck around since they liked the cross dressing to an extent, but neither were really into the kinky sex, and neither wanted to be dominant. So, I'd learned to be very up front with my kinks and that left very few girls wanting to date.

Fortunately, internet dating had changed things up a little bit. Also, as I got older, I began to get a bit more experimental with my sexuality. The idea of being gay or bisexual had always freaked me out more than a little. Especially growing up in a small-town, rural community where anything vaguely resembling a little out of the norm got you mocked, ostracized and possibly attacked.

So, that stigma has always been with me. Even after I moved away and lost contact with my family and most of my old friends. As I began to explore, I started chatting with other crossdressers and trans girls. Eventually talking with some guys and ultimately, meeting up with a few for some fun with me dressed and being their sissy girl.

Overall it was fun, but I was looking for something so much more. Most of the guys just wanted oral and maybe anal. I wanted lots of heavy kink, and not many of the guys would be into that, or only a little. Or they wanted me to be versatile and top them as well.

The real pain was the number of guys who flaked or bailed on me. I know, its a part of meeting up with people you don't really know, but it was something that never failed to bother me. I always took it very personally and actually cried the first few times it happened. I know I shouldn't have taken it so personally, but I did. I'd get really depressed and swear off meeting up like that again.

Still, like dressing, the desire would come back, but after a while I dropped off on the meets, since they just weren't quite scratching that itch. I'd been looking closer at Professional Dominatrices and Dom guys, but so far I hadn't had the guts to go through with something like that, yet.

Most of not following through came down to me being too scared to go forward. I was just a little too comfortable in my world and I didn't want to disrupt it. Even the idea of going out dressed was fun, but so far I'd only done it on Halloween and my few outings as a sissy. I did have a few girls in my area that wanted me to come to club nights and such, but I always had some lame excuse about why I couldn't go.

That's why I liked chatting online. It let me dress in private, maybe show off a few pics or my video cam and have a fun, sexy time without worrying about anything crazy happening. It seemed like Master Clancy wanted to do the same thing, since he was messaging me more frequently over the following weeks. However, he also kept hinting about me coming down to their studio, doing a makeover and then photo shoot. We'd been chatting for weeks and the conversation would always go back to that.

"You really are a super cute sissy girl, you'd be amazed what a makeover and some quality photos could do for you," he messaged me.

"I know, Sir, and I love the idea, but it really scares me, too," I told him. "I just don't know that I'd ever have the guts to go through with it."

"Well, what would motivate you to come down? Some girls just like the transformation and are happy with that. But most of the girls love the experience so much, they come back for the full sissification experience," he explained. "That's why we do the first transformation and the pics, its to get you comfortable."

Of course, all of that had my little sissy clit rock hard, but even that wasn't enough to convince me, "I think that's the problem, I'm just too comfortable. I don't know what would move me out of my comfort zone."

"How about a girlfriend? Genetic or trans? Maybe if you had someone to come down and hold your hand?" he asked helpfully. Adding a little wink emoji afterward.

"That's a great idea, but I'm not seeing anyone, and I haven't really gotten to know any of the girls in my area," I explained.

"Well, you should get to know some of the girls," he stated. "We've had a few girls here that would be happy to meet with you and have some drinks, then come down. I could see if there's any of my girls nearby that would get together with you."

I thought for a moment, that did sound pretty reasonable, but I still couldn't see myself doing it, "I'm just not sure, that sounds like a nice idea, I'm just not sure."

"Well, what would motivate you?" he asked.

"I'm not sure," I replied. "I can't think of anything."

"Well, I might be able to come up with something, you see, I really want you, and I think you'd be one of our best sissy girls, and for me, I think you'd be perfect as my personal sissy slut," he stated.

Whoa, okay, that was getting a bit real for me, and I definitely wasn't ready for something like that, "I'm sorry, I just don't think I'm ready for that."

"Okay, baby girl," he started. "I didn't want to go this way, but I think I can find a way to motivate you, Alan."

"You mean, Alice, Sir?"

"No, I mean, Alan," he explained. He then proceeded to list my full name, address, home phone and even my work phone number and address. Holy fuck! How did he have all that? Oh hell, no! What was I supposed to do?

"I'm sorry, I have to go," I quickly replied and disconnected before he could message again.

I sat panting starting at my laptop in pure terror for a moment. Of course, the thing bothering me most was that my clitty was even harder than it had been before. Was the idea of being blackmailed into being a sissy slut, really turning me on?

A moment later, my phone buzzed and a text message showed up from an unknown number, "Do you really want to play it like this? Maybe I'll message your boss instead." This was followed by a picture of me with my made-up face showing me playing with one of my dildos. Wait! How did he have that picture? I'd never even sent this one out? Had I been hacked?

I sat panting, my breath coming in short gasps. Was he serious? Would he really send that to my boss? He had my personal information, how much damage could he do? I thought about it, unfortunately because my job did government and corporate contracts, they had a pretty heavy morality clause in our work agreements. I wasn't sure if this would mean I'd lose my job, but they'd definitely be watching me, if they didn't just fire me outright. It was a fairly moderate company, so I doubted there would be much room for anything with them. I mean, we'd never really had anyone come out or transition or anything, but I also didn't go into the office much, so I'm not sure I'd know if anyone did.

Did I take my chances? I could probably find a new job, but they'd want a reference from my previous job. I guess he was getting impatient because another message came in, "No? Nothing. Okay, I guess I'll just hit send."

I quickly replied, "No! Please don't!"

"Oh, now I have your attention?" the message blinked on my phone ominously.

I hesitated, and reluctantly, "Yes, you have it."

"You mean, 'Yes, Sir', right slut?"

"Yes, Sir. Sorry," I replied nervously.

"Good girl, now get back on the chat before you piss me off," the message dinged back quickly.

I reluctantly logged back into the computer. The message on my phone had made it pretty clear he really did have my number, literally. I was hoping maybe the rest was just a part of a game, and he wouldn't really release my information. Or he was just teasing me.

I realize I was trying to delude myself, but it was helping me to keep from freaking out. I brought the chat back up and logged in to reply to the last message.

"Hello Sir, I'm back," I typed.

"Good girl," came the reply back.

Okay, well he didn't seem mad, that was helping my mental state.

"Here's what you're going to do baby girl. I was going to move you slowly, but clearly you're going to try and run away every time. So, you need to convincing that you are ours," he messaged.

"Please Sir, I'm so scared," I replied.

"I know, baby girl, but you will love being a sissy slut, and hopefully you'll gel with one of our Masters, I'm really hoping you and I will hit it off. I know I'm looking forward to trying you out," he messaged. He then continued, "So, first you're going to get that throbbing hard clitty of yours down. Get it down however you need, but you are NOT allowed to cum? You understand, slut? That's part of your punishment. Use ice if you have to."

"I understand, Sir. Please give me a few minutes," I replied. I wondered how to do it. I figured a cold shower was a good start, but with how hard my clit was throbbing, I wasn't sure it would be enough. I got in and the cold water helped me to lose some of the edge, but after several minutes of shivering, I was still rock hard.

I briefly considered jerking off since I was so aroused, but I didn't want to risk that I got caught. Somehow, I figured he'd know. So, still dripping with cold water, I went to the kitchen, opened the freezer and pulled an ice pack. I put the freezing gel pack on my throbbing member and wow! That was quite a way to wake up. That only took a few moments before my clit was back under control and going limp.

I got a towel and kept the dripping ice pack on my clit as I got back on the chat, "I'm finally soft, Sir. It took some ice to get me down."

"I figured, that's why you're going to be such a great sissy slut. Now, lock your chastity cage on. I want a picture of the locked cage and the key in a few minutes. Be a good girl."

"Yes Sir," I replied. My heart sank. He wanted me in chastity and I did have a couple cages. Which one to use? I figured I might be in for a long time. Better to go with the lightweight composite cage. I'd worn it for several weeks at a time, and it was almost comfortable. Well, except for waking up in the morning. Morning wood in a chastity cage was one hell of a wake-up call.

I quickly got the cage locked on and took a picture with the cage and the keys next to it. I sent the pics over. My heart was in my throat, since I had a real bad feeling about this.

"Good girl!" came the quick reply. "Now wrap those keys in tape, put your initials on them and send me a picture. Then get on your sluttiest outfit. Be sure to shave everything below your nose, put on your make-up nice and slutty, and then get a nice wig, the blonde one. Oh and be sure to put a plug up your slut hole, and it better be one of your big ones."

"Sir, what am I going to be doing?" I asked, my heart hammering again.

"Do as your told, sissy. Do not question me any more," came the terse reply.

"Yes, Sir. It will be a while and I have to work in the morning," I replied.

"Then you better get your ass moving," was all he said back.

Well, hell. The thought of being forced to slut myself up, had me leaking like crazy out of my cage, but my heart was beating like a jackhammer I was so scared about where this was going. Well, fretting about it wasn't going to get me sissified any faster. I did take a quick picture of the taped up keys and sent that over.

First I hopped back in the shower. I figured I had to shave, and maybe the hot water would calm my nerves a little. The routine of shaving and the steady drone with the spray of warm water, did help me get into a different mindset.

Once I'd shaved and moisturized, I started to get back into my femme mindset. I was starting to throb in my cage at the idea of being a sissy slut. Somehow being forced made it just that much more arousing. It also made it way more terrifying, so I tried not to dwell on that, instead getting into the mindset that I was just meeting up with a Dom and this was exactly what I wanted.

I dug through and found a nice new pair of seamed stockings I'd been waiting for an excuse to wear. I found my red PVC garter belt and slid that on. I opened the pack for the stockings and relished the feel of pulling them up my legs. The silky material clinging to my freshly shaved legs always thrilled me and made me feel so feminine and sexy. Attaching the garter tabs was a pain in the ass, but it was such an alluring look.

I went through my selection of clothes, trying to decide what was the sluttiest look I could go with. I decided to do my make-up first and see if that inspired a slutty look. I started with a nice foundation. I wasn't sure what I was going to be doing or where I might be going, but I wanted to look my best, especially if there were going to be pictures.

I started with the foundation. For my own pictures, I'd try to use liquid foundation since I found that gave me a nice even skin tone. Getting the goopy cream on my face and blended in nicely took a bit of time. I had these special pads that were designed for putting on liquid foundation that let me spread it nice and even and smooth.

Once I had a nice base, I started on my eye shadow. I went with a red on the inside of my eye, then blended in some black on the outside, blending the colors to get that smoky look. The red and black matched the red and black of my garter belt and stockings.

I liked the dramatic smoky look, so I went really heavy with the mascara. I went with the non-waterproof mascara since I had a feeling I was going to become a true sissy slut and the running mascara look was always enjoyable. Well, for the guys anyway. I loved how slutty I looked when my mascara ran while giving head.