Almost Damsel Almost in Distress

Finally! I had the day off from work and I planned to spend it indulging two of my favorite activities... crossdressing and self-bondage! I've been dressing since I was 10 years old, and about the only thing that was more exciting than getting all femmed up... was locking myself into some strict bondage and struggling to get free!

I lived in a small apartment complex on the edge of town. Being on the outskirts meant I was able to get a place on my own, finally! After college I got a nice job and was making some decent money, sure I was mostly paying my college loans, but I could afford to have my own apartment. After having roommates all through college, this was my first time really living on my own. So, I was able to get dressed whenever I wanted, which was just about any time I was home!

While I thought that much time en femme would finally sate my cravings to dress, it really only began to whet my appetite! Also, since I was getting so much practice with my make-up, my mannerisms and my voice, I was finally feeling comfortable going out dressed, too. I'm kind of a shy person, so unlike some of the girls who are comfortable right away, I've really needed some time to get used to it. I'm not ready to do a drag show or anything, but I think I've finally got the nerve to start hitting some of the clubs and bars in girl mode.

Sadly, it's a fairly rural area, so there aren't a ton of gay or trans friendly places nearby, but its not too far a trip to some nearby cities which have a decent nightlife. So, mostly that's left me dressing in my apartment and occasionally venturing out in my car, usually at night, to drive and just enjoy being a girl!

I made my way into the apartment, dropping my keys on the table by the door and looking over my place. It wasn't huge, but it was a good size for me. It had a main room that was the main living area and a sliding glass door to a small patio. The main room was where the TV and couch were. It had a small kitchen and a bedroom which was where the bathroom was, too.

"Home sweet home," I muttered to myself as I flipped on the TV. I just put on some music since I didn't really want to get involved in anything. I first went out onto the balcony looking at the sun starting to set and knowing I had the whole night and all day tomorrow to do whatever I wanted. I felt really alive for a moment, and just took a few moments to breathe in the cool late spring air. I was too worked up and couldn't really relax, so I made my way back into the apartment.

I made my way into the bedroom and took off my work clothes, getting excited already! However, I wasn't going to get too excited since I was locked into my chastity cage! Sadly, I didn't have anyone to hold the key for me, so I usually kept it frozen in a block of ice. That way even if I was "in the mood" I'd have to wait for the ice to melt to get relief! I'd actually gone two whole weeks without cumming, and after the first few days, I found it was much easier to keep from unlocking myself. Of course, I was also SUPER horny, so I was really looking forward to getting dolled up.

I decided to indulge myself and take a nice warm bubble bath first. This not only helped me relax and take my mind off my clitty, but also gave me a chance to check my shaving. I usually keep pretty clean shaven all over except for a small patch over my clit, so it didn't take long to check I was smooth and hairless all over. I emerged from the tub feeling very femme, though I did hear the next door neighbor on that side through the wall. It sounded like she was in her bathroom.

The one major problem with an apartment is how close your neighbors are! The neighbor on that side was elderly lady who was apparently a widow and didn't have many relatives in the area. So, I would help her out with things like carrying in groceries. She was very nice, but she also had a tendency to go on and on about her dead husband. She never even usually called me by my male name, she usually just called me "Dearie."

I did take a few minutes to moisturize and lotion up. Mostly in case she heard me and needed some help with anything. Thankfully there was no knock on the door, so I went to the dresser where I kept most of my femme stuff and started looking through everything. I had started to accumulate a pretty decent collection of girls' stuff. I'd always had a decent collection of lingerie, but since I was on my own I'd really started to get some great outfits, too. I had simple stuff for just hanging around, like a nice chemise and some silky pajamas. I had outfits for going out and just being girly, like if I was running errands. So, some cute shorts, tops and such. I kept the nice dresses and outfits in the closet hanging separate from my guy clothes. I had a couple nice dresses that could work for dinner or even a semi- formal occasion, I even had a killer business suit that I was dying to wear to work, but I wasn't out of the closet for that yet!

The stuff I really loved though, was my fetish gear. I had always had a thing for girls in leather, PVC, boots, corsets and such. So, now I had a nice collection of kinky clothes. I figured if I was going to be a bondage babe, then I should go full fetish slut. I pulled out my red PVC panties and black seamed stockings. Then, I also grabbed my opera length vinyl gloves, PVC mini-skirt and baby doll top. Then I grabbed my two favorites: my thigh high boots and my heavy steel boned corset. The boots were 6" with a 1" platform and the corset was thick PVC with a dozen heavy steel bones so it was VERY strict. Just wearing it was bondage by itself! I was getting excited already, so I went back into the bathroom to do my make-up.

I was doing bondage, but I was hoping to get some pictures, so I decided to go very heavy on the make-up. Full blown fetish slut coming up! I was giggled as I pulled on the panties to keep my cage from bouncing around too much. If nothing else, the lock clicking on the cage could get a bit annoying, so I was able to focus that way. Thankfully, I've really been working on my make-up and was getting good at various styles. Simple for going out, stylish for getting dressed up, subtle but sexy for nice occasions, or heavy duty glam to show off. Guess which one I was planning on!

I started with the base foundation. Since I was doing pictures, I went with the liquid since that seems to shine a bit less than the powder. I'm pretty fair skinned, so this was a light cream. After getting it nicely blended in so that it was even all over, I looked over my eye make-ups. I decided to try a new color and went with a dark green. I'd never tried this color, so I was curious to see how it came out in pics. I was figuring I'd probably be gagged, so I wanted something that would show against the straps and gag. I blended the green, starting in close to the eye with darkest part, then using a light gray about midway across to lighten the color towards the end of my eye. It wasn't truly a "smoky" effect, but it looked pretty good. I wasn't sure about the color, but I didn't hate it, so I wanted to see how it looked in the pictures before I decided.

I put on the mascara and I went really heavy with the darkest one I had. It was one of those plumping mascaras, so my lashes looked very heavy. They almost looked like I had fake lashes on! I thought that looked good against the green, so I was feeling good about the choice. I put a bit of blush on my cheeks just to give a touch of color. I lightly blended that since I didn't want to mess with the foundation too much!

Finally, I looked over the lipsticks. I was debating going with a light color, but I really wanted something to show around the gag, so I opted for the dark, heavy red. It was almost a light crimson, like a blood red color, but looked very bright when on. I painted my lips and debated if I wanted to put on lip gloss, too. Since I was doing pictures, I didn't want my lips to shine too much, so I decided against it. Besides, the lipstick was supposed to be the "non-smudge" kind, so we'd see how it did after some time around a ball gag! I looked over the make-up and was quite happy with how it came out! I looked pretty good! Who am I kidding? I looked like a complete wanton slut who was on the prowl, which was pretty much the look I was going for!

I then looked over my bondage gear. I wanted to get everything out before I got dressed, since once I got in my corset, getting anything out wouldn't be as easy! I pulled out my leather cuffs, my bright red ball gag, my blindfold, my handcuffs and fairly heavy posture collar. I also selected a large butt plug, my jet black wig and my breast forms. I debated going with one of my dildos, but the plug vibrated and I was looking forward to the buzzing. I was also debating what to do with my chastity key! Should I get it out, so the ice was melted by the time I had escaped? Or would it be better to have to get the ice out and still wait after I was done? I decided to leave the key for now, I could always get it out before I fully locked myself in.

So, I finally got into my slutwear! I loved the feeling of sliding the stockings over my smooth legs. I was in heaven already and I had just started. Next I slid on my thigh high boots. I so loved wearing these boots. Sliding my foot into the super high heel then pulling the zipper closed. Just that sound was amazing. The boots hugging every curve of my leg was also delicious, too. I did the boots first since experience had taught me that putting them on after the corset was something of a challenge!

I figured I should take care of my plug, now too. So, I got out the lube and after greasing my backside, I slid the plug slowly in. Even though I used one of my toys just about every night, I was still amazed at how tight I could get. I took a few minutes of lubing and pushing, with a break to let my ass stretch, but I was able to get the medium plug seated. Once my cheeks closed around the flanged base, I felt nice and full. I also felt very naughty and even hornier. I wasn't sure I could get much hornier! I was tempted to pull out the plug and go to town with one of the dildos, but I still wanted to get pictures. I'd have plenty of time to be a wanton harlot later! I had the whole day tomorrow, and I planned to indulge myself.

I picked up the wicked red corset and slightly undid the laces. I then wrapped it around my waist, and hooked the fasteners in the front. Even with the laces undone, I could feel the stiffness of the corset squishing me in. I knew once I was done I'd look like I had some serious hips. I'd even look like I had some cleavage! I grabbed the breast forms and inserted those into the cups. Just with those, I looked I had a C cup. I walked to the closet and tied the lace strings to the door. I pulled them as tight as I could with my hands, then leaned forward and let my weight pull the corset super tight! I could feel the bones and my breathing was reduced, so I knew bending over would be a challenge. I could do it, but not quickly! I undid the laces from the door and tied off the excess, tucking it into the corset. I tucked the garters through my panties, so they were underneath. That way I could pull the panties off without having to undo all the garters. I fastened the garter tabs to the tops of the stockings, loving the classic look of that style.

I felt like sex on heels now! I glanced at the dressed mirror and was amazed at how hot I looked. I blew myself a kiss and giggled a bit. I definitely looked good enough to fuck! I grabbed the mini-skirt and slid it up my legs. It was a bit snug on my hips, but once I got the flared part on my hips the top settled into my much narrower waist! I fastened the back zipper and smoothed it down, then grabbed the top. It was a PVC top with a baby doll neckline and short sleeves, so it managed to be cute and sexy. I slid the top over my head. It took some doing to get it over my now huge tits, but the stretchy material slid down with just a bit of fighting. I grabbed my wig and fastened it to my hair. I had been growing my hair out the past couple months, hoping I could do femme pics with my natural hair, but I knew it would be some time before I could really get a femme style. Besides, my hair was a fairly plain brown. So, if I wanted some color, I'd either need to dye my hair, or keep going with the wigs.

I used a few hair clips to secure the hair band to my natural hair hoping it would stay pretty well. I then took a look and was still amazed at how the transformation could go. I looked like a fetish model! I needed to get some pictures, so I decided to wait on putting on the gloves.

I didn't like to use my camera since I was still pretty in the closet. There weren't many people that looked through my phone. However, after one time someone saw a pic of me done up in my picture list. So that I had to scramble and came up with some lame excuse about a girl I briefly dated, I decided to not take that chance anymore.

Thankfully, my parents were avid photographers and had given me one of their old digital SLR cameras. So, I had an almost professional level camera to take my femme pics! I got out the camera, my tripod and the remote, too. It took me some extra time since the heels and corset meant I was not at full speed. Though I did realize, with the all practice I'd had lately, I was moving very well in the heels. After taking the apartment stairs and driving in heels, I found that I could do damn near anything in heels!

I set-up the camera and took several pictures of myself on the bed, at my little table pretending to touch up my make-up, adjusting my garters and even showing off my bondage gear. Once I felt like I probably had a few decent pictures, I decided it was finally time to become a damsel in distress.

Does it count as distress if you put yourself there? I guess damsel in my own distress doesn't really sound right! So, I moved the camera and all my bondage gear to the main room for the next round of my photo shoot!

I set the timer on the camera, while I put on the leather cuffs around my ankles and my thighs. I'd reset the camera after each time the flash went off. I made sure to get nice and close as I put the ball gag in! I was hoping to get lots of close-ups of the blood red lips wrapped around the bright red ball. I got pics of me fastening the straps in the back of the gag. I also got lots of pics as I wrapped the posture collar on. I made sure the little charm on the front that was attached to the D ring was in the pictures. The "BAD GIRL" charm was definitely how I was feeling!

I got a few more pictures as I worked the opera length gloves up my arms. Then I switched the camera over to remote mode and grabbed the remote in my left hand. I positioned myself and the camera by the couch and made sure I could get a few pics that way. I slid on the blindfold, being sure to get a few pics that way! I already felt completely helpless and I hadn't done anything yet.

I was also amazed at how enhanced my senses were with my sight gone. I could feel all the textures of the clothes, smell the delicious vinyl scent and taste the rubber of the ball gag like it was new! I could even hear everything better, almost crisper. The soft hum of the AC as it rumbled. The music playing on the TV seemed sharper. Even the next door neighbor on the other side closing his front door seemed louder than usual.

That gave me a quick thought... the really cute next door neighbor! He seemed to work shift work or something since I only ever saw him coming or going very late or very early, so I'd almost never talked to him. Also, a few times I'd been coming back late from venturing out, and he was coming home. That was a real thrill and rush, especially the last couple times he gave me these really friendly smiles. I was a bit shy like I said, so I hadn't had the guts to do much more, but he was very good looking. I guessed I was bisexual since I'd never really had sex with a guy, but I sure thought about it.

Who was I kidding? I sucked my dildos and fucked myself silly almost on a nightly basis imagining my neighbor was burying his cock in me. I just wasn't brave enough to make the first move and he seemed like too nice a guy to make the moves on his neighbor.

"Almost there," I thought. I connected the cuffs on my ankles to my thighs so I was stuck on my knees. I then brought the connecting strap from the ankle cuffs that had my metal handcuffs attached to it, so once I cuffed my hands I was basically stuck until I could get to my keys. Which I just happened to leave in the bedroom... on the bed! So, getting to those from the floor was going to be an adventure. I'd done it before, so it was possible, but it would take some work. I'd be a sweaty tired mess when I was done, but I'd be a very happy girl!

I'd probably also spend the night with my leather cuffs on my hands and ankles, maybe even a gag in, pretending my Mistress or Master was leaving me helpless so they could use me in the morning. My clit was already throbbing in my chastity and my plug was driving me wild.

Oh, that reminds me... I reached back to the base of my butt plug and turned it on. Oh, dear fucking me! The vibrating was going right from the plug on my prostate and its even making my chastity cage vibrate which was a really strong sensation. I almost couldn't think for a moment! I just wanted to reach down and start playing with myself. I resisted the urge and instead reached behind me to lock my left hand in the metal cuff. I made sure I still had the remote in my hand and took a couple pictures to make sure it was working. I could hear the click of the camera flash, so I hoped the pictures would look okay. Working with a remote is always sketchy at best since you can't check the focus or framing until later. I know, most people don't care, but I like my pictures to look somewhat professional since I do have a clue what I'm doing!

Okay, moment of truth. Was everything ready? I couldn't think of anything I missed, so I reached my hand in and ratcheted the cuff on my right hand. I could feel the metal tighten on the opera glove and that was it... I was caught in my own web! Oh, that moment when you're fully stuck and there's no escaping! My heart fluttered for a moment and my breath caught. I usually get to a point where I almost panic, but it never quite goes that far. I guess that's just my body reacting to being scared, thrilled and exited all at the same time.

So, I squirmed a bit on the couch to test my bonds. I remembered to hit the button on the remote and take some pictures. Once I had a few, I really started to struggle and realized I was drooling like crazy around the ball gag. I hoped the streams running down to my tits would show in the pics. I always found that hot when seeing bondage models.

I settled in to enjoy being a damsel in not-distress and really enjoying the vibrations from the plug. My goodness! The plug was a new idea I hadn't tried with the self-bondage before. It was almost too much, I couldn't really think straight I was so horny. I tried vainly humping the couch, but with the way I was up on my knees and the chastity cage, that was a useless idea. I also couldn't really push on the plug very well to try and get more sensation, so I was just a mass of frustration. In fact, I was trying to decide if I should go to the kitchen before the bedroom and get my chastity key out of the fridge! I was going to need to cum soon!

I'm not sure how long it was before I decided to start moving. I'd been in my headspace so it could have been a while, but was probably only about 20 to 30 minutes. I decided after getting a number of pics to start making my way to the bedroom to get loose. I'm not sure what happened, but somehow I completely misjudged where I was on the couch and instead of lowering my knees to the floor, I bounced off the arm and flopped to the floor! In the process I managed to hit several decorations and knocked one of my tables over. Damn that hurt! I lay there for a moment taking assessment trying to figure out if I'd actually injured myself or not. My arm hurt a bit where I landed on it, and I guess I hit the table with my leg since that had a sore spot, too.