Almost Damsel Almost in Distress Ch. 03

Five he stepped up the swing, it may have only been half or maybe two-thirds power, but it stung! And the paddle covered a lot of ass-cheek with each hit. Then next few really took some breaths, and I kinda lost count. I was saying numbers and thanking him, but it was mostly automatic, I was more focused on my breathing and working through the pain.

"These next ones are going to hurt... really bad," he warned me and I could hear the paddle whoosh in the air. But nothing happened? I was tensed like a coiled spring, and nothing. I started to relax a little, and then I heard the whoosh again, before I could tense, he hit my ass with a blistering force! I hissed, squirmed and then remembered, "Nine, Sir! Thank you, may I have another?" though my heart really wasn't in asking for more of that.

"You sure, you want more, girl? You didn't sound like you meant it," he teased, rubbing the cool paddle lightly over my warm ass-cheeks.

Dammit! He was actually making me beg for more punishment? And the bitch was, because I knew it pleased him, I really wanted to! "Yes, Sir! Thank you, Sir! May I please have another?" I asked enthusiastically.

"Since you asked so nicely, how could I refuse?" He paused, gave me a moment to relax again, then hit my other cheek with a smack that sounded like a gunshot. I cried out with that one, but after a quick breath, I remembered, "Ten, thank you, Sir! May I have another?"

"Good girl, but not yet, I think we should let you have a break and switch implements," he then lightly kissed my lower back, softly rubbing around. The tender caress was such a change of sensation, that my body didn't quite know how to react. I was tensed and geared for more spanking, so the soft kisses and caresses kind of blew my mind. Then he started kissing down and was softly kissing my hot skin where he'd been beating me. That felt strange, but when he pulled the plug out and kissed between my cheeks then started licking my asshole, I almost lost it! My clit raged back up in my cage and I was moaning like mad, trying to push back against him for more of that!

He rimmed me for a few minutes, really getting me worked back up, then stopped suddenly. My body was quivering with need, but he was playing me like an instrument again. I thought he was going to plug me again, but he moved on instead.

"I think the tawse next," and he gave me several quick smacks with that. It was similar to the paddle in how stingy it was, but it hit a lot less skin. He built me up, but didn't have me count those. So, it was after a dozen or so, that he switched again.

"Now, let's see how you like the riding crop," the light stings with that weren't bad at all, but the hard swings were intense! Especially since they hit just a small concentrated area. One strip across my ass was on fire with each one, and it sure felt like he was leaving bruises or something.

He made me count those, and I lost count at one point. "Seven! Thank you, Sir! May I have another?"

"Seven, girl? Are you sure?"

"Yes, Sir... I thought so, Sir," I mumbled. "I'm not sure, Sir."

"Yes, I know since it was six. Normally, we'll start over from the beginning, but since this is your first time, I'll just add two more."

I shuddered, but managed, "Thank you, Sir. Sorry, Sir."

He then gave me twelve instead of just ten. As he inspected his handiwork afterwards, he laughed, "Your ass looks like you have grill marks."

I laughed, and could imagine it, but I'd have to wait to see.

"I've been looking forward to showing you the flogger, I probably should have started with this one, but, oh well," he then lightly whipped me with the tassels which stung pretty bad. He thought we should start with this?

Then he got it going, spinning it rapidly and lightly hitting me with it. The light strokes almost felt kind of... nice? Like a rough massage, it hurts, but feels good, too. Yeah this was fucking with my brain, too. And when he stopped and then did a heavy smack with it, my brain kinda turned to mush. I don't remember too much after that, though I know we went through a couple of the other items I had, but I was lost in a haze of pain, pleasure, obedience and arousal.

I was beyond horny at this point! When I heard his voice ask me a question that cut through the fog, "Well girl, what do you want?"

I squirmed my ass, "Please, fuck me?" begged. "That was so sexy and wild, and I love being your little slave girl, please take pity on me? Please take me, Sir! I want to be yours!"

He started kissing my really sore ass again, quickly moving between my cheeks and rimming me more! That was nice, but I wasn't going to cum from that! I think he knew that since after a few minutes more, I felt something cold pushing at my hole.

Suddenly, he slid into my ass, and I groaned with relief.

"Oh Sir! Thank you, Sir!" I almost screamed!

"Sorry, girl, but after two rounds today, that's not me, but I will fuck you," he said, and I realized he was using a dildo on me. I didn't care, I needed something and this was hitting the spot.

He still played me though. Long slow deep strokes that had me quivering with anticipation of each one. Strong, rapid strokes that left me breathless and everything in between. I guess all the action had an effect on Alex since I felt the dildo pull out, and suddenly he grabbed my hips and slid his cock into me, and he went balls deep in my ass.

I groaned with relief and he began fucking me hard and fast. Yeah, this wasn't the tender love-making from earlier, this was fucking, pure and simple. It only took a few moments of that pounding flesh-on-flesh before I was begging, "Please, Sir? May I cum?"

"Not yet, girl, hold onto it," he growled. He continued plowing my sissy ass like crazy. That just drove me even further up into arousal, until I was sure I was going to explode!

"Now, girl! Cum for me!" I'd been holding so long, it took me a moment to push over the edge, but when I did it was like water rushing over a dam.

It was another extended, mind-blowing sissygasm, my clit just spasming and squirting inside my cage while Alex filled my ass with another load of his cum.

He quickly pulled out and collapsed onto the bed next to me. I continued twitching in pleasure for some time after that until I settled back down.

Alex rubbed my arm softly, "You really are something else."

"Thank you, Sir, that was amazing!" I smiled back.

"I do want to let you know, I'm not releasing you yet," he added.

"Oh, yes, Sir. Whatever you like," I smiled happily.

"Good," he said. "I'm going to put you in more bondage and torment you while I clean up."

"Yes, Sir!" I replied, grinning happily, giddy as a schoolgirl! "Can you please be sure to get some pictures?"

"Of course!" he laughed. "I'm going to gag you, too."

"Ohhh, yes Sir. What kind of... gurk!" I started asking what kind of gag it was going to be, but he demonstrated instead! Shoving it into my mouth with no warning. It was deep in my mouth and was stretching my jaw wide open. It was pretty big, too. My tongue felt around it and I realized it was a cock gag! The phallus in my mouth was really wide around and it went just deep enough to tickle my throat, but not enough to make gag or block my airway. It did tickle my gag reflex slightly when I'd swallow, so that was weird. I felt him pulling on buckles and wrapping a harness around my head. And yes, he locked this harness gag on, too.

"And let's fill your other slut hole, too," He then slid what I guessed was the butt plug back in me. I was kind of relieved! I was getting used to being full.

"And let's get some use out of this," he unlocked my wrist cuffs, but just long enough for me to stretch and then he slid something over my arms and started to buckle me in. He was putting the armbinder on me! Oh, I had wanted to be put in one of these for the longest time!

He then did something with my ankles and pulled me up to the middle of the bed. Next, he pulled my feet up, did something and I could fell my ankles were hooked to the single sleeve D ring. Yup, I was basically hogtied! He then went a step further and did something so the gag harness was pulled back from the top. I assumed a D-ring or hook of some kind and I was stuck in a pretty awkward position.

So, naturally my clit started leaking like mad!

He then did something to my chest, and when I felt the flash of pain, I knew he was nipple clamping me again. Then he turned the vibrator on in the plug! My body was so confused, I didn't know which way was up. The real bitch was he turned the vibe on low. Not enough to get me off, just enough to be a tease.

"I'm going clean-up, but I'll be right here watching you," he said as put ear buds in my ears. He then turned it on, and I could hear a soft feminine voice, telling me over and over, "You are a sissy slave. You love your Master. You will do whatever he wants. You want cock. You want cum. You want to please. You exist only to please others."

I'm not sure how long I stayed like that. Maybe fifteen minutes? After a while my arms were cramping, my legs were getting sore and I couldn't keep my head up. So, all the straps were digging in where I couldn't hold that strenuous pose anymore. The vibe did change speeds a few times, but it only went from slow to off and back to slow. So that was mostly frustrating! But I was loving every minute of it!

At some point, Alex started rubbing something cold onto my ass. It stung at first, but as he rubbed it in, it helped soothe the burning and throbbing from my tanning. He then turned everything off and released me from my bonds.

"Can you get undressed from there?" he asked.

"Yes, I'm good," I replied smiling as he kissed me on the head.

He climbed into the shower and I took everything off, setting the sweaty pieces aside to clean up later. I really wanted to wash my face. The dried spooge was getting crusty! Plus there was my girl cream all over my thighs.

Once we'd both cleaned up, Alex pulled me back into bed and snuggled me, kissing me over and over. I felt so warm and safe in his arms. We both dozed off, and when I woke up, Alex was snuggled against my back breathing softly in my ear. I managed to get myself out of bed and I grabbed a quick shower and shaved. I still felt kinda weird about having any stubble for him. I get the feeling he didn't really care, but I liked the illusion myself. One thing I forgot about was the ass beating. The hot water in the shower sure reminded me quick. Holy hell did that hurt! It was kind of nice in a weird way, reminding me of what he'd done to me. I tried to see if I had any marks, but couldn't really tell. I'd have to try and grab a picture later.

He woke up as I was climbing into the bed, and started kissing me, deeply and passionately. "So, how was today?" he asked as he broke the kiss.

"Fucking intense, but holy hell was it amazing!" I gushed.

"You sure? The spanking and everything wasn't too much?" he rubbed my sore ass.

"Well, yeah, it was pretty intense, but I was into it. I kinda enjoyed the flogger, that was actually kinda nice at some points. I'm not too sure about the crop, but I guess that's what makes it an effective punishment, right?" I smiled.

"Well, its supposed to be fun, too. We'll need to make sure to find your limits, see what you're comfortable with," he replied.

"Anything you really liked?" he asked.

I gasped, "Oh yes! The 'blowjob bitch' thing, that was... holy wow, I could do that all the time!"

"Blowjob bitch, huh? You did mention that earlier, didn't you? Okay, so I know what makes your motor rev! And I will remember that you said, 'any time'," He smiled and winked, then paused. "Anything you didn't like?" he wondered.

"Hmmmm, well, the crop was pretty intense. I wouldn't say I didn't like it, but it wasn't my favorite either. So, I can't really think of anything, it was just an amazing day," I smiled from ear to ear.

"Good, well, don't be afraid to tell me if you don't like something, its not a bad thing. We just put it aside, and its off the list," he explained.

I nodded, "Okay, like I said, there's pretty much nothing I wouldn't try at least once. I mean obviously anything like permanent or serious damage is out, but anything else."

"But you're okay with permanent marks? Like a tattoo?" he grinned.

"Well, yeah," I blushed at how wet that idea got me. "Or piercings."

"But piercings aren't permanent. Those holes can close up eventually," he said.

I nodded in agreement. "Do you want me to make something for dinner?" I switched up the conversation.

"No, I thought we'd go out, I want to enjoy a special little time with you," he said.

"Oh yeah, back to work tomorrow," I complained.

"Actually, I work late shift, I have to go tonight," he laughed a little.

"Oh, well, shouldn't you be getting some sleep?" I asked.

"I'd rather be with you, besides, I gotta eat, too," he got out of bed. "I'm going to run to my place and get dressed."

"Okay, what should I wear?" I asked mischievously, winking at him.

"Well, if you're gonna be flirty like that, then you better wear something slutty," he said sternly.

"Yes, Sir!" I replied.

He laughed and shook his head as he went out. I heard the front door close a moment later. I hopped out of bed. So, what should I go with? I wanted to look super slutty for him, but I wasn't sure how much time I had.

When he came back in to my apartment about 20 minutes, I was nervous that I might have gone too far with the slutty, but I figured I could always change!

"Chrissy? You ready? I'm curious to see what you went with," he called.

"Just about done, I'm in the bathroom, touching up my make-up," I called back.

"Okay, let me know if you need anything," he replied.

I smiled at myself in the mirror. I couldn't believe I was planning to go out in this outfit! Now, to gauge his reaction.

I stepped out into the Living Room and said, "So, what do you think?"

He turned and his jaw fell open. He was speechless!

I slowly walked toward him on my thigh-high boots, letting him drink in every inch. The sheer black stockings just peeking out of the tops of the boots, disappearing up into the PVC minidress and topped with my long black wig and super slutty make-up.

I figured I might as well go full tramp, so I used blue eye shadow, and I'd done my best to get a smoky eye effect. I'd also gone fire engine red on the lipstick. I did go with a liquid foundation and concealer. I was doing my mascara when he came in, so that wasn't as thick as I wanted, but I didn't want to mess it up either.

I had one of my lighter corsets on and garters connected to the stocking, too. I filled the corset cups with some of bigger falsies, since I figured a C cup would really show in the skintight dress. I decided to go with black panties, PVC as well! I topped the whole thing with my 'Bad Girl' choker. I did have one that said, 'Sissy', but I wasn't sure how much I should advertise that, yet.

"Damn! You look like sex on heels!" he was grinning from ear to ear.

"Thank you," I smiled and turned, letting him get a peek from the back, too.

"Well, I know what I want for dinner," he joked.

"Careful, sweetie, we'll never get out of the apartment!" I laughed.

"Oh no, we're going out, I can't wait to show you off!"

So, I took his arm and he escorted me out. Of course, my heart did that jackhammer thing when we first stepped out, but I recovered pretty quickly. Once we were in the car, I was thrilled at being out and all done up! Needless to say, my clit was dripping steadily. I was also worried that Alex was watching me more than he was watching the road!

We pulled into a small shopping center, and Alex parked in front a small pub at the end.

"You ready, girl?" he asked, I realized he was asking if I was getting worked up like last time.

"No, Sir. I'm ready to be shown off!" I smiled at him. I realized being his eye candy was so thrilling it took away all my nervousness.

We went in and it was a quiet, dark place. Also, since it was later on a Sunday, there weren't many patrons, but the ones there all stared at me. They guys were undressing me with their eyes, hell some of them were eye fucking me! Even the ladies were looking closely. I was worried I was going to be made, but I mostly saw either disgust or open appreciation. One lady said to the man she was with something to the effect of, "I should have worn that!"

When we got to our table, Alex even pulled out my chair for me. I was smiling so happily, I felt like my face was going to tear. As we sat, the tanning he'd given my ass earlier reminded me of its presence! Also, the plug made me thankful the seats were nice and cushioned.

Alex ordered some wine, we ate some small appetizers and chatted about movies, music and other pop culture stuff. It was a nice, light, fun date. I was having such a good time, I kinda forgot about everything else.

I didn't realize how much the place had cleared out until the waitress came over and said, "I love your boots, where did you get them?"

"Thanks, sweetie! I got them on Amazon actually," I explained.

"That makes sense, I wasn't sure if they were from that new shop that opened downtown, they seem to specialize in 'exotic' clothes," she said.

"New shop? I might have to check that out," I told her.

Alex commented, "So, we might have some shopping to do?"

"Maybe," I replied coyly.

The waitress made some small talk as she took care of the check, but headed on her way.

"Well, I think they're getting ready to close, so we should get going," Alex stood and pulled out my chair. It was such a simple but romantic gesture. I took his arm as we walked out of the pub. I was surprised when Alex turned and we started walking, not to the car, but to a different part of the shopping center.

It was only when we started approaching the shop that had "Tattoos" in large red neon lights out front did I have a realization what was going on.

"Alex, are we..." I started.

"No girl, you are," he stated simply. He opened the door and held it open for me. I took an uncertain breath and made my way in.

It was simple and nicely appointed. They had lots of papers on the walls with different designs and tattoos on them. I glanced over a few, amazed at the variety of styles. There was a counter with several books that had more tattoos. I also saw one that had actual photos of what I guessed were customers. I could see into the back of the shop, where there were several chairs and tables for customers and artists. The whole place was very quiet. I almost thought they were closed and just forgot to lock the door!

I was about to say something like that to Alex, when a deep voice called, "Be out in a second."

A few moments later a tall, stocky man came out of the back. He was dark haired, and had a large goatee. As you'd expect, he had multiple tattoos and also several piercings.

"Evening folks," he said, getting an eyeful of me, and to his credit, he only reacted slightly surprised. I guess maybe they get all kinds in a tattoo shop? "How are... Alex!"

"Hey Ken, how ya been?" Alex replied.

"I wasn't sure if you guys were going to make it," the artist, I'm guessing Ken, replied.

"Yeah, we were having a pretty nice time at dinner, it was hard to get away," Alex replied.

Ken looked at me, shook his head, "Yeah, I can see why. I... wait... is this the new girl?"

Alex smiled broadly, "Yup! Ken may I introduce Chrissy, Chrissy, this is Ken, one of my former employees."

"Ah, that's how you know each other! Nice to meet you Ken, this a nice shop you have here," I noted.

"Well, I've got your man here to thank for part of that, he helped me navigate all the paperwork to the get loan and the agreements to set-up this place," Ken explained, gesturing around to take in the whole shop.