Almost Damsel Almost in Distress Ch. 04

"You know what do, right?" he asked. I could almost hear the huge grin on his face.

"To beg... for permission... Sir," I stated between grunts.

Alex smacked my asscheek and said, "Good girl!"

Again, I thrilled at him calling me that, and that pushed me right up there. I was close, on the edge, but I couldn't quite seem to peak. I don't know why and I was getting a little frustrated. I started grunting and moaning, trying to get a little bit more to crest that horizon, but it wasn't happening.

"You close, girl?" Alex asked, picking up his pace.

"Yes, Sir, but I can't quite seem to..." I hesitated.

"To get there?" he finished.

I nodded and he gripped my shoulder, pulling me even deeper into him with every thrust. I was hovering oh so close to the edge, when I felt Alex doing something with his hands along the back of my neck. He wasn't grabbing as much as... exploring? It felt a little weird honestly, not bad, just not something I'd ever had done before. I was a little unsure where this was going, when he got through the wig and to my real hair. He then wrapped his fingers in my hair and started pulling... hard. Holy shit! It felt like he was going to rip my hair out, and he was pulling my head and body back into him as he slammed away at me.

As you can imagine, that was all I needed and I screamed, "Please, Sir! Please may I cum?"

"Not yet, slut, not yet. Hold it, girl!" he growled as he yanked even harder. I was actually seeing stars the pain was so intense and directed, but it was getting me off quick! I wasn't sure I could hold back now. I was on the edge so long.

"I'm not sure I can, Sir! Please?" I pleaded, trying to sound desperate. I was.

"Not fucking yet, you hold, or I'll spank your little sissy balls black and blue," he growled in my ear.

Wait, was that supposed to be an incentive to not cum? Because that idea was turning me on even more. Now I was stuck. Did I want to be good or be a bit of a brat and get a real punishment?

"That sounds yummy, Sir!" I purred as best I could while having my head yanked and my ass pounded.

"You really are a kinky bitch," he said, and yes, I could hear the smile. "Fine, if you cum, no dick for a week," he growled.

Oh fuck! Was he serious? He could just jack off, but I'd have to use a toy or something to relieve some stress. Well, that decided it and I pinched down and held my orgasm back as best I could.

He continued pounding me, while talking in my ear, "So, my little sissy likes to get her balls spanked? I will remember that." It sounded like both a threat and a promise. Help me, that turned me on even more.

"What else do you want, cunt?" He knew how the names got to me, so he was calling me all kinds of dirty things.

I moaned loudly, then gasped out, "I want to be a total bimbo sex toy. Giant tits, huge lips, tats, piercings, slutty clothes."

"Very hot, my little cock sleeve, what else?" he was loving this.

"I want to be whipped, flogged, my ass beaten so red, I can't sit for days," I breathed, trying to think of something that didn't scare the complete fuck out of me. Just admitting the bimbo thing was a bit intense. My mind would go to all sorts of dark places, and a lot of them scared me.

"I already know that, you ditz. What do you really want?" he growled, really yanking on my hair.

"I want... to have a three-way with a trans girl. I want to be gangbanged, with just cock after cock taking my mouth and ass. I want to be the center of a dungeon sex party, tied down and spanked, pinched and tormented made to serve any cock or pussy that wants to use me. I want to be a ponygirl with a bit and bridle and tail plug, I want to be in the sissy version of House of Gord, I want to be whored out, dropped on a street corner and degrade myself for tiny amounts of money... Please may I fucking cum? Please?" I stretched the last word out to four syllables.

"Cum for me my little latex whore," he purred.

I fucking exploded. I came in wave after wave, my clitty spurting all kinds of my sissy cum. My ass thrusting back wildly on Alex. My body shaking with each wave. My mind kind of shut off at some point, maybe I even blacked out for a moment. I came back with Alex gently lowering my head down and sliding his cock out of my well-stretched hole.

"You okay, girl?" he asked quietly.

I nodded, trying to form words, "Oh yes, Sir. Just... a little... dizzy."

Alex laid me on the floor, where the cool floor met my sweaty latex body and that woke me back up a little. I looked up at him and smiled brightly. The care and concern in his eyes evident. My eyes also drifted to his rock hard cock and I reached up to stroke him.

"Ready then, girl?" he smiled down.

I nodded and rolled to my back. I slid over to place a kiss on his cockhead and then wrap my lips around him, taking him as deep as I could. He moaned and I blew him like that for a few minutes until I started pushing down as far I could deep throat, milking his cock with my throat. Then coming up for a quick breath and going back down again. Soon, he was pounding away at my mouth, sliding pretty much all the way down my throat with each thrust. It was hard to breathe, but I really wanted to pleasure him, so I just tamped down that part of my brain. It only took a few more minutes for his pace to pick up and he was slamming into my mouth, fucking my face hard. Soon, he pressed all the way down, driving completely in my mouth and throat and he came, bucking and groaning, shooting straight down my throat. It was so hot, but after a few seconds, I was starting to get desperate for air. Thankfully, he pulled out after he felt me squirming.

As soon as his weight was off my, I sat up and kissed him as hard as I could. Showing him how I felt about everything. He kissed me right back with the same passion and ardor.

"Sorry if I was choking you there," he said between kisses.

"Its what I wanted, Sir," I replied smiling like a love-struck teenager.

"You wanted me to choke you?" he asked, raising his eyebrows.

I nodded and bit my lips shyly, "Yes, Sir."

"Just with my cock or my hands, too?" he asked seriously.

I shrugged, "Both, either. I just want to be controlled by you."

"You really are the sexiest thing ever," he smiled and kissed me again.

"Does that include some of my... fantasies," I hesitated bringing it up, but some of those things scared me, I didn't want to freak him out.

"Are you kidding? I love those fucking fantasies! They are some of the hottest things I've ever heard. I'd love to do any and all of that with you," he held me close, looking tenderly at me, with just a hint of unbridled lust. It was making my clitty and my heart throb.

"You're dripping," he pointed out. There was another puddle of my cream inside, plus I was adding fresh pre-cum.

"Sorry, I'm a bit of a mess," we broke and went to clean up. As we did, we talked more about my fantasies.

"Do you really want to do those things?" Alex asked. "I think they're super hot, but I don't want to push too far either. Just the way you asked afterwards, you sounded a bit... hesitant."

"I do, its just some of them... scare me. I mean, I love the idea, but what's the reality going to be?" I shrugged.

"I get it, its like what will it be like being in charge of someone else, tying them up and holding everything about them in your hands. It can be an incredible rush, but it can also be scary as fuck." He looked at me smiling, his eyes bright. "Its a lot of responsibility. And constantly trying to keep things exciting without pushing any boundaries, or at least not going full-bore loony, and just pushing the envelope a little."

"Like yanking your partners hair?" I grinned.

"Exactly! How was that?" he asked.

"Oh my fucking God," I replied. "I won't lie, it hurt like a sunovabitch, but it was so fucking hot and was exactly what I needed then."

"Okay, so a good thing, but not too much. Maybe only at certain points?" he wondered.

"I think that's about right. Do you want me to stay in the dress?" I asked, realizing I was a complete sweaty mess "Oh, and what do you think of latex stockings?"

"If you'd like to stay in it, if not, we can get you into something else," he pressed up and kissed me running his hands over the dress on my back and ass. That was just a heavenly feeling. "And I love the idea of latex stockings, I wasn't sure if all that latex would be too much for the first time."

"It might have been, but now I want to know. Also, you keep rubbing me like that, and I'm going to want you to fuck me again," I purred.

"I know," he kept rubbing and pressing against me, before finally picking me up and carrying me to the bedroom.

Hours later, I woke up with Alex's arm resting across my back. Somehow, I was just wearing my stockings. I laid there feeling warm and cozy nestled up with him for a while, until nature got the best of me and I had to pee.

I'd get a little twisted around at Alex's since his apartment layout was backwards from mine. So, I walked into the kitchen first by mistake, then made my way back to the bathroom. I was a little chilly being out of the covers now. As I peed and cleaned up, I realized the only clothes I had over here were made of latex. I guess I was going to have to squeeze back into the dress to go back to my place. I still had a few hours before I had to get ready for work, but I didn't want to leave yet.

I crawled back into bed and Alex woke kissing me softly before he went to go pee. As he came back, he kissed me and nuzzled into my neck. I debating asking for another round, but he'd already fucked me several times and I didn't want to be greedy.

"What time is it?" he groggily asked.

"Its about 5, almost 5:30," I replied. "I have to get ready for work soon."

"I know," he replied. "Oh, I didn't get to ask you, do you want to go back to Lucy's tomorrow night?"

"Sure thing," I replied happily. "Tomorrow as in Saturday, right?"

"Uh-huh," he grunted as an affirmative.

"Sounds great," I smiled, thinking about last week.

"Will you wear the latex dress?" he asked, a mischievous twinkle in his eye.

This was him pushing a little. He knew I'd get a little freaked out just being out as a girl, and being dressed sexy only made it more so. So, I needed to push myself, too. Even though the idea of going out in the latex dress freaked me out more than a little, I replied, "Sure, I will."

"Good girl," he replied sleepily.

"Speaking of the dress," I started. "I might need help getting into at least some of it to get back to my place."

"Why?" he asked.

"Well, I need to get ready for work," I replied, wondering if he was already asleep.

"Just wear one of my shirts or my robe or something. I'll get it back later," he replied like I was a complete ditz.

"Oh, right. That's a good idea," I stated, feeling like a complete ditz.

"You don't have to sound so surprised," he joked back. "I have good ideas."

"Sometimes great ideas," I grinned and kissed him on the cheek. "I'll see you tonight?"

"You better believe it, I have exciting news for you," he smiled, closing his eyes.

I really debated jumping on him as he said that. That was just mean. Saying something like that and then just falling asleep? Really?

I grabbed his robe and all the latex pieces, then headed back to my place to get ready for work. Its funny, I was so distracted at work that day, that I was pretty useless. I kept thinking about getting together with Alex and being able to spend the weekend together. I was also really wondering what his exciting news could be.

I had fantasies about him really being a prince or a billionaire or something and whisking me away to a life of being his little sissy sub girl. I knew that was too out there, but it was still fun. I tried to think more practically. I could only think that his lease was up in a few months and maybe he'd gotten a new place. But that wouldn't be exciting, that would suck. Unless he was going to ask me to move in with him? Holy shit! Could that really be it? I mean, weren't we at the way too early stage for something like that? Still, the idea made sense. We could combine our rents into one payment and save a ton of money. We could even still get just a one bedroom place.

All this speculating, had me spaced out at work. Several people even asked if I was okay. I just told them, I'd met someone and while it was early, it was pretty serious. That's when it came to me. It was pretty serious. I was really falling for Alex, and I'd only really just come to terms with the idea that I could be in a serious relationship with a guy. I mean, having sex with a guy was one thing, but actually being together, that was something else entirely. Especially for me, since I wasn't actually transitioning or anything. Did I want to transition? I always wondered what it would be like to live as my femme self full-time, but I wasn't sure I was quite ready for that.

Like I said, I was a space cadet. So, at five, I rushed out and hurried home. I didn't find any notes when I came in. So, I decided to do my usual, grab a quick shower and get in girl mode. Sure enough, by the time I was out of the shower, Alex had come in.

"Hey! Should I wear anything special?" I called from the bedroom.

"Something kinda comfortable would be good," Alex called back.

Hmmm, not the answer I expected, but it did make me wonder what he had planned for me. It didn't sound like we were going out, which to be honest was fine with me. After being at work all day, and probably going out as a latex slut tomorrow, another night in sounded perfect.

I decided to go with something sexy and still somewhat comfortable. I know to most people a corset doesn't sounds that comfortable, but this one was. It was a lightweight fabric brocade corset in black with green detailing on it. It was actually kind of pretty, the boning was fairly light and it was a touch big, so it was quite comfortable, for a corset anyway. I also went with stockings since I always love those. I paired it all with a skimpy thong.

I did a quick make-up job. No foundation, just some powder for highlights, quick eye shadow, no mascara and I went with a dark red lipstick. Still sexy, but more mysterious than a bright cocksucker red. I also donned my short, black bob wig. It was supposed to look a bit like a Betty Paige kind of style.

I came into the living room in my outfit and Alex smiled as he saw me. He came over and took me in his arms, wrapping me up and kissing me deeply. It was amazing how this moment just made my heart skip a beat and I didn't really want it to end. Sadly, he broke apart and looked me up and down.

"This is comfortable?" he asked incredulously.

I gave him a little 'what?' look and replied, "I happen to be comfortable in it."

"Hey, you look amazing. As long as you're comfortable with it, its fine by me. I just hope your prepared to be in this all night," he held up a leather collar.

Oh my! I should have known something like that would be on the agenda.

I gasped slightly, then I looked up at him, "I'm prepared to be yours for as long as you want, Sir."

"Good, then kneel," he commanded.

I trembled slightly with excitement as I fell to my knees. Of course, at that level, I almost reflexively looked at his crotch where there was a very familiar and noticeable bulge.

He saw me looking and admonished me, "Not yet, girl."

My Master then reached down and gently buckled the collar around my neck. "Don't forget, when you're wearing this, you're mine. No back-talk and do as your told, when your told. Don't forget your safeword."

"Yes, Master," I nodded as he locked a padlock on the collar and I moaned softly. Alex smiled triumphantly as he knew he had me.

"Give me your hand," he ordered.

I quickly and obediently offered him my right hand. He reached out with a leather cuff and buckled it around my wrist. My breathing increased rapidly as my arousal took off. Alex looked me right in the eyes and then clicked a padlock on the cuff. I gasped slightly as he did, and he smiled wickedly at me. All of this had me steady dripping in my panties.

Alex grabbed my other wrist and locked a cuff on that one, too. My breathing was ragged as I was so aroused at this point. He pulled me to my feet and wrapped me in his arms, kissing me with utter abandon. I just melted into his embrace, lost in a haze of love-struck lust.

Alex kissed to my ear and whispered, "You ready to be my little bondage slut?"

"Always, Master," I gasped.

"Turn around, girl," he ordered softly. I obeyed and he reached over my head with a large ball gag. I moaned as pulled the bright red gag into my lips and buckled it.

Alex pushed me down to the floor, and I kneeled down. He pushed my chest down, so I was bent over. He pulled my hands behind my back and clicked another padlock on the D-rings, locking my hands together. How many locks did he have? Was he done? I hoped not. Wow, I really was a bondage slut.

He wrapped cuffs around my ankles and then the large cuffs around my thighs. As you can imagine, he locked my ankles to my thighs. I was not going anywhere, not quickly anyway! He reached down and began playing with my ass, teasing me by running his hands all over my cheeks, throwing an occasional smack in just to keep me on edge. It wasn't long before I was moaning and squirming, trying to push my ass back into his hands. When I did that, he would move his hands up to my back, and rub me lightly there.

"Now, let's make sure everything is nice and snug," he then did something to my corset, and in moments was tugging on the laces, pulling it really tight. Thankfully this corset was a tad big, so even at its tightest it wasn't cutting me in half, but it would still make me have to take shallow breaths. He pulled until the back panels were touching and re-tied the laces.

"How's that? Comfortable?" he asked, right in my ear.

I nodded, and mumbles, "Yeth, Thir," around my gag. All I really managed to accomplish was drooling all over my corseted tits.

"Good," he chuckled evilly. "Let's get you completely ready."

I didn't have to wait long as he lowered me face first to the floor, so I was on my face and knees. Not exactly a comfortable position, but he did put a pillow under my chest, so I wasn't right on the floor. However, now my bare ass, was quite vulnerable. He took advantage, and began really playing with me. In this awkward position, I could barely push back, so I was just his toy to play with.

After several minutes of teasing me, I felt something cold at my asshole. At first, I thought he was going to fuck me, but then I realized he was pushing a plug in me. After it was seated, he turned the vibration on low.

He then pulled me back up so I was sitting on my knees. Then, he was doing something with my hands. Before I could even realize they were unlocked, he was pulling something over them.

"About time this item gets some more use, girl," he whispered as he pulled the armbinder up over my arms and buckled it onto me. I squirted a little when he said that. And when he pulled my arms all the way in. And when he... yeah, I was pretty much dripping the whole time.

He let me settle in and I was trying to get control of my breathing, or my libido, or my heart-rate, but I was just a bundle of nerves for him to play with, and that was fine with me!

He now stood in front of me. I was really hoping he was going to let me suck his cock. I wanted him in me so bad, I didn't really care how. And the buzzing from the plug was not helping with that desire. He leaned in close and said, "No peeking now."

He then slid a blindfold over my eyes. It took me a few moments to adjust, but my other senses very quickly kicked into overdrive. Touch being the one that was really going into overdrive, but smell was right there, too. Certainly the smell of leather from the straps, but also the smell of him. I could smell his musk. I could also really taste the rubber of the ball gag.