Almost Damsel Almost in Distress Ch. 05

I was sweating profusely and breathing hard around the bit. Oddly, I didn't feel tired, I was so thrilled and excited to be training that my clitty was steadily dripping down my legs. The constant pull of the bells on my nipples and the fullness of the plug had me getting more aroused with each step.

We took a quick break, and Alex gave me some water, "You're doing good, girl. But you need to keep those knees up high. We'll also do some other steps and in the future, maybe we'll see about getting a cart and having you practice as a working pony. But with how lovely you are, you should definitely be a show pony."

I snuffled softly and nuzzled him with what little I could move my head. I bumped my ass against his leg, trying to get his attention. This earned me a smack on my ass, which just fueled my fire even more.

"Is my pony a little worked up?" Alex teased and hit my ass with the crop hard.

I snorted and shook my ass more. He took my reins and unhooked me from the trainer. He walked quickly back to the barn making me clomp along as fast as I could. I was dripping sweat and out of breath once we got back into the barn. Alex hustled me over to the stall. He opened the door and led me in, the hay rustling under our feet, the cool air making the sweat on my skin dry quickly.

"Are you horny, my little pony girl?" Alex asked leaning in close to my ear. "Well, maybe we'll see if we can find you a stallion to breed you. I'll be right back," he grinned and closed the stall door.

I could see him walk back to the other side of the barn. I could only stand there with my bells and plug driving me absolutely mad with lust. I hoped he was coming right back, or was at least going to put the vibrating plug back and let me get off that way.

I'm not sure how long he was gone, it felt like an hour, but was probably only about five, maybe ten minutes. When he came back, I felt my heart race. Then I saw he had more leather. What did he have planned now?

He walked over to me with a wide smile on his face. He turned me around and pulled my arms behind my back. He put cuffs on my wrists and hooked them together. Then he put cuffs on my elbows and hooked those together. Damn! That really pulled my shoulders back. My elbows didn't quite touch, but with the hook between them they were still pulled pretty close.

He then pushed my shoulders and I had to bend over. He then did something and my arms were secured putting me into a serious strappado. I really hoped this meant I was getting fucked!

He then smacked my ass with the crop. The line of fire burning across my cheek. The sting made me gasp around the bit, but the feeling burned out to the rest of my body making me even hornier, if that was possible.

Alex then proceeded to smack and crop my ass brutally. Between his hands and the crop, I was dancing and trying to avoid the strikes, but he found my tender ass and thighs pretty much every time. Even as I twisted and turned, the crop drew a line of fine on my sensitive and tender skin. I could feel I was covered in red lines and wondered if I'd have any welts. I certainly earned them. It was a painful and thrilling experience that had me gasping for air until I was a sweaty, dripping, horny mess.

Alex came around to my front, "Still horny, girl?"

I nodded and snorted, shaking my ass. If I wasn't so into the pony idea, I would have started begging for him fuck me. As it was I pleaded with my eyes. I couldn't believe how horny I was.

Alex grinned, and slowly stepped around me, running his hands across my bound form, until I was quivering with anticipation. He stepped behind me and ran his hands across the stripes and welts on my ass, the pain flaring and making me shake, so that my bells rang as he did it.

Finally, he pulled out my plug and slid himself deep in my ass in one quick thrust! I moaned around the gag with relief. Alex then proceeded to start pounding my hole hard. This was pure animal fucking and it was so much what I wanted. Between my grunts, the bells, the clicking of my chastity lock and the smack of flesh on flesh there was so much going on my brain basically went to mush.

Alex pounded on and on like a man possessed. My grunting growing louder and louder as I built up and it didn't take long before I was squirming and squirting my way through a powerful sissygasm. It felt like fireworks going off in my head.

Amazingly, Alex kept going right through my shaking and convulsing until I was biting on the gag and having a second orgasm. This one was strong enough to set Alex off and he buried himself in my ass, cumming deep in me.

I hung there, panting and feeling so much better as I slowly came down. Alex unhooked my arms and I collapsed into a heap in the hay. Alex gently pet my head as he took the bit gag out. He gave me some water and I sipped it as he released my arms, taking off the gloves. He started taking off the rest of the gear as I undid the headpiece and the posture collar.

Alex undid my boots, while I gently reached to the nipple clamps. As I took the first one off I hissed in pain and Alex gently took my nipple in his mouth. The mix of sensation made my head spin. Then he quickly pulled off the other clamp and I squirted a bit with mix of the pleasure and pain.

Alex petted my head, as I collapsed in a heap in the hay. I must have dozed off because I woke up later with a start. All the gear was gone and so was Alex. I lay naked in the hay feeling a wonderful soreness in my legs and especially my deeply tanned ass.

I made my way to my feet, and saw my femme clothes hanging outside the stall. I got dressed quickly, but realized I probably needed a shower. I was also really hungry.

I set out to find Alex, but he was right on the other side of the barn in the workshop. I came in and he smiled at me. "Hey, sleepy head. Feeling better?" Alex smiled as he looked up from his phone.

I nodded, "Yes, but I could use a shower, and something to eat. I got a real workout."

Alex laughed and showed me a few of the pics on his phone. They were me done up in the pony gear. Oh wow! They looked really hot. He even got a few pics of me bound in the stall and my ass showing the fresh stripes and welts.

I hugged him close, "That looks amazing!"

Alex nodded, "You make everything look good. So, you enjoyed the whole scene?"

I nodded, my eyes lighting up with excitement, "Oh my, yes! I hope we can make that regular thing. Did you really want to get me a cart?"

Alex nodded, "You bet, I hope to see you become a good show and work pony, but let's get to the house and clean you up."

We went to the house and I took a quick shower, then we headed out to grab some lunch. We headed back towards the city. We pulled into a familiar place for lunch. I wondered if Jan was working. Sure enough, we came in and Alex asked for Jan to be our server. So, we were seated in her section.

Jan came up and was very excited to see us, "Hey, you two! Glad to see you back again."

I beamed, "Its nice to see you, too."

Since we'd been playing so much in the morning, it was a little late in the afternoon, so the lunch crowd had started to clear out. I was famished. Lots of exercise for the morning, I guess. While we ate, Alex and I chatted a bit about the pony scene and how we felt about it. We'd enjoyed it, but clearly it was physically draining for me.

"It was also emotionally a lot for me, too," I noted.

"How so?" Alex asked, cocking his head to the side.

I tried to explain, "It was a bit like being out en femme. When we first went out of the barn, my heart was racing. I felt like the world could see me and were laughing at me for being dehumanized."

"So, would you be okay to do it again?" he asked.

"Oh, hell yes!" I added enthusiastically. "Its just that first time freaked me out. I'll need to be mentally ready for those doors to open. I will say, seeing those pics made me feel a lot better about it."

"Was the food okay?" asked Jan as she came up to checking on us.

"Fantastic!" I said. "I was really hungry."

"It was great," added Alex.

"What did you feel better about?" asked Jan. "Something that worked up an appetite?"

Remembering Jan's handcuff earrings, I said, "We had a fun, and new, scene this morning. It was physically a lot for me."

Jan smiled with a twinkle in her eye, "He wore you out, huh?"

"Yes, but not all that way. I... uh... I got to be a pony girl for the first time." I blushed a bit. I'm not sure why I told her, I guess knowing she was a fellow kinkster made me more comfortable.

"Oh awesome!" Jan gushed. "I've only gotten to train a few ponies, It was always a lot of fun. I loved getting to wear my riding outfit for it."

She pulled out her phone and scrolled for a moment, then showed us a picture of her done up as in a riding outfit with jodhpurs, a riding crop and riding boots. She would have looked like dressage rider if not for the naked girl in a bit and bridle next to her.

"Wow! You look amazing. So, does she. Would you like to see me?" I blushed deeper.

Jan eyes lit up, "Oh, yes. Can I?"

Alex pulled up his phone and showed her my pics.

"Oh wow! Girl you look amazing," she gushed. Then quietly added, "I'd love to put you through your paces sometime."

My cheeks went beet red, but I squeaked out, "Thank you, Ma'am. That would be... amazing."

"I would love to see that," Alex added, his eyes sparkling as well.

"I'll bet," said Jan, giving me a wink.

"You should come out tonight if you're not working. We're going to a local gay and trans friendly club called Lucy's. Someone is going to have a special outfit tonight," Alex grinned at me.

I blushed even deeper, looking down at the table. It felt like my face was on fire, but my clit was absolutely throbbing in its cage.

Jan frowned, "Damn, I wish I could. I'm going out with a friend to a BDSM club a few towns over. Its called Crimson. I've never been, but I've heard good things about it."

"Oh, Alan, the guy who did the leather work for her outfit talked about Crimson," Alex said.

I looked sideways at him, "Oh?"

"What? You think I'm revealing everything? I've got to have some surprises," Alex grinned.

I leaned in and kissed him on the cheek, "Please keep surprising me, Sir."

"Well, I'll let you know how Crimson is next time I see you both," Jan added.

I smiled, "Sounds great!"

Alex nodded, "Yeah, we'll come in for lunch soon."

We chatted a bit more, exchanging numbers with Jan so we could keep in touch more. We made our way back to our apartment complex and I started getting nervous. I realized I was going out tonight in a latex dress. While I was excited about the idea, I was also more than a little nervous about it, too.

Alex walked me to my place. He kissed me at the door, taking my breath away. As we broke the kiss, he smiled at me, "Are you ready for tonight?"

I nodded, then shrugged, "I am, I'm just..."

"Nervous," he finished for me. I nodded and he said, "Its okay. You'll look amazing."

"Thanks, that's sweet, but its not about how I look. Its about how I feel. And I'm going to feel like everyone is looking at me showing up in that latex dress," I explained.

"I've got news, girl, everyone IS going to be looking at you in that dress," he said smiling.

"That's not really helping to settle my nerves," I grinned back, in spite of my nerves.

"And they're either going to want you, or want to be you," he finished.

I smiled and nodded, "Now that thought does help. Thank you."

He kissed me on the cheek and smacked me on the butt cheek, "Now, go get ready. Will you need help getting into everything?"

I nodded, "Yes, Sir. The corset if nothing else. Come over in about an hour?"

He nodded, "I can't wait."

I turned and headed in. I was amazed at how light my heart felt with Alex. As I hopped in the shower to shave, well... everything. I mean, let's be honest, wearing that much latex, I didn't want any body hair getting in the way.

As I lathered up and re-shaved, I made sure to pay special attention to any of the areas that would be in or passed over by the latex. While running the razor over my skin, I thought back to earlier at the house. I recalled Alex mentioning two people could be very comfortable in the house. Was he really asking me to move in with him? Was I ready to move that fast on something like that? I guess one thing at a time. Get latexed up and maybe we could talk about it at the club. Or tomorrow. There was no need to rush, I still had my lease for several months.

I stepped out of the shower and lotioned up. I figured I should start my make-up since I was probably going to get sweaty getting into the latex. I wanted to go basic with my make-up, since the latex dress was already going to scream 'look at me!'

I started with some light foundation and powder. Not a lot, just enough to tone down my highlights on my chin, nose, cheeks and forehead. I spent a good amount of time blending all that in to get a nice even tone.

Next, I went with the eye shadow. I just went with a nice pink color. I did mix in some red on the outside to give a blended color that went from light to dark. I'd been playing with colors like that, so I thought this might be a fun way to dress things up. I then did my mascara. I wanted a heavy look there. I rolled the brush slightly as it went on my lashes to get a nice thick look, basically painting each lash. I debated trying false eyelashes, but I figured the latex was enough experimenting for one night.

Once I had the mascara where I liked it, I did my eye liner. I really hated the feeling of doing eye liner, but the effect was so amazing. Especially if I could get the nice flourish at the edge of my lid and trace the outside of the eye shadow. This look came out pretty good. It wasn't quite the look I had hoped for, but it was still very dramatic. I guess I still needed to practice my eye liner.

I put a bit of the pink from the eye shadow on my cheeks and used that for a matching blush. I spent some more time getting the pink nice and blended. It gave a nice highlight of color. I then did my lipstick in a pink hue to match the inside color of my eye shadow. I was pretty happy with the look, but I wanted a different effect, so I did a layer of lip gloss in a shiny pink. That gave my lips a shiny look like the latex. I was pretty happy with how the whole effect came off, so I moved to getting dressed.

First, I powdered up all of the skin that was going to be touching the latex. I was soon doing my best ghost impression with a light cover of white on most of my skin. The plume of powder in the air told how much I had used.

I got my red latex corset. I knew it would be better if Alex could really cinch me in, but I'd get it as tight as I could now. I used my old reliable method of tying the strings off to the door handle and pulling forward to get the laces nice and tight. I felt so cinched in, it was delightful. I loved a nice tight corset. It was like wearing bondage. If Alex came back before I got the dress on, maybe I'd have him tighten it. Until then, I wrapped the strings around my waist and tied them, so I could keep the wrap as tight as possible by myself.

I next pulled on my red latex garter belt and wrapped that around my hips. The delightfully cool and slick feeling of the latex making my clit twitch in its cage. I slid the latex stocking up my leg. The smooth feeling making my head swim a little.

I pulled my red latex thong out, but before I slid that up, I reinserted my plug. It felt so good to be filled again. As I slid the thong up to encase my locked up bits, I delighted in the slick feeling of the latex there, too. I was getting worked up again from the second skin feeling and having my hole delightfully filled was getting me very worked up.

I grabbed my largest falsies and slid them into my corsets cups. The D sized inserts made me look like I had pretty large tits. I glanced in the mirror at the effect. The hourglass of the corset with the falsies made me look like I had some Jessica Rabbit level curves.

I eyed the red latex dress and grinned as I prepared to wrap myself even further in the second skin. I smelled the dress, reveling in the heady smell of the rubbery material. I slid the dress on and a shiver ran down my spine as my pleasure centers spiked. As I wriggled the dress in place I smoothed out the areas that had bunched up, delighting in the rubber on rubber from the corset and the dress.

Once I had the dress straightened up, I looked through my wigs. I debated going with the black since that was my favorite, but I figured I was going with a theme, so I grabbed the extra long pink wig. I liked this one because it hung down to about the middle of my back. The bright pink was a fun color, too. Once I had the cap adjusted, I hooked in the hairpins to connect the wig to my hair. It made a nice and secure way to have the hair on.

I looked over myself in the mirror, the pink and red was very eye-catching and made for a nice color palette with my skin tone, just as I'd hoped. I grabbed my red pumps and slid my feet into the four inch heels. Yeah, those added a whole new level of sexy to the equation. I was getting worked up just looking at myself. I decided to do something a little different and put a black latex headband to wrap up my long hair. It was different kind of look, but I liked it. It also had the bonus of keeping the long hair out of my face.

I flashed myself a smile since I knew there was one thing missing from this outfit. I powdered up my hands and forearms. I grabbed the red latex elbow gloves and worked them onto my hands. The bitch of wearing latex gloves was putting the second one on. Once the first was on, your dexterity was a bit limited. I could still do things like pick up a glass, but doing detailed things could be tough. It was possible, you just had to be patient. That's why getting the second glove on was such a pain. Trying to get each finger into the latex and get everything smoothed out was a time consuming task.

Once I had it done, I checked myself out again and I was now horny as fuck. I packed up a few things into my purse. I was just walking out into the Living Room when Alex came back into my place. I struck a quick pose as he came in. He caught sight of me and his eyes lit up.

"Holy shit, girl!" he grinned from ear to ear. "They're not going to know what to do with you!"

I smiled and acted a little shy, "Really? You think so?"

Alex pulled me in, his hands rubbing along the shiny material making me shiver with excitement. He kissed me on the neck and I smiled at him.

"I know so, also," he pulled something out of his pocket. "I have a present for you."

Alex held up a small swath of red latex. It took me a moment to realize it was a latex collar. And it had 'SISSY SLUT' emblazoned across the front of it. I gasped and squirted a little into my panties.

"So, you like it?" Alex smirked.

I nodded, "Oh, yes Sir! Its perfect."

"So, you'll wear it for me?"

I smiled, squirting more into my already wet latex panties, "Oh, hell yes!"

Alex held my hand, "Good girl, get on your knees."

I knelt down, the latex making it feel odd to be on the floor, but I was steady dripping into my panties with how fired up I was. I looked up at Alex, smiling brightly.

Alex reached down and had me kiss the collar. I smiled up as he buckled the latex choker around my neck. The hair band making it a bit easier for him to wrap it around me. It felt odd having the stretchy material on my neck, but I liked having the collar. Being owned made me feel reassured. Knowing how it advertised me was beyond thrilling

Alex looked at me, smiling as I licked my lips and looked at his cock through his pants. Looking back up, I bit my lip. He shook his head, "Not yet my little sissy slut, or we'll never get out."