Almost Damsel Almost in Distress Ch. 05

By Shawna Summers

(M/t -- bondage, anal, pony play, latex, oral, water-sports)

I awoke slowly, feeling something hard against my back. I came to with that delightful feeling of being in bondage with Alex snuggling against me, his cock hard and digging into me. Of course, as the obedient little slave girl I was, I positioned him against my ass and began grinding on him.

I'm not sure if he was deeply asleep or just enjoying my playing, but it took him several minutes to be aware of my moving around. Eventually Alex maneuvered himself enough to slip my plug out and slide his cock into my ass. I mmmpphh-ed in pleasure around the breather gag I had in.

I heard his voice, husky and quiet from sleep, in my ear, "Does my little sissy slut like that?"

I nodded and pushed myself deeper on him, groaning with lust as I did. Alex pumped me slowly, letting my bound and gagged form stew as I groaned and pleaded around the gag as best I could, "Pwesh, fwck meh!"

"I am fucking you, slut," he reasoned.

If I asked for it harder or faster, he'd do it for a couple strokes, then he'd slow back down and let me stew more. Eventually he took pity on me, he rolled me onto my stomach, climbed on top and began to really plow into me.

I groaned and pushed back as best I could, but in that position, I was pretty much at his mercy, and of course, I loved it. Being held down and taken so thoroughly just tickled my little submissive heart. Hearing him growling and panting in my ear really also did it for me.

I built up but I didn't seem to quite get close to the edge, no matter how hard I tried. After some time of plowing my ass, Alex whispered in my ear, "You okay?"

I nodded my head and thrust back on him. "Are you going to cum?" he asked grunting.

I tried to shrug my shoulders, but with my hands behind my back, that was a little tough. I think he got the idea. "Want me to do something else?"

Damn, he was sweet. I shook my head, thrusting back and said through the gag, "Fwck meh!"

"Your wish is my command," and he began plowing me mercilessly. After several minutes of pounding my ass, he grunted and groaned as he came deep in me. Feeling him cum was pretty amazing. I realized most of the times he'd filled me previously, I was deep in either subspace or sissygasm, so I hadn't really experienced feeling his orgasm. The warm, wet feeling of his cum filling me was one I hope to never forget.

We flopped onto the bed into a sex puddle, trying to catch our breaths. Once Alex settled down and began slipping out of me, he slid the plug back into me. He then pulled my helpless form tight against him and wrapped me in his arms until we both drifted back off.

I awoke when Alex got out of bed to go to the bathroom. I squirmed to the edge of bed and managed to get most of the way into a sitting position when Alex came back in. He smiled seeing me up, "You have to go, girl?"

I nodded, and then waited for him to come and free me. Instead he just looked at me sideways and said, "Well, you better hurry, you'll get in trouble if you pee the bed."

He then laid back down on the bed and watched me, clearly enjoying himself. I gave him a pleading look, but I could tell by the smug smirk he wasn't letting me out any time soon.

So, I got to my feet and half-hopped, half shuffled to the bathroom. Getting myself onto the toilet was a task with my hands behind me, but I managed. Then getting back up was pretty tough. I tried pushing off the tank to get some leverage, but I couldn't maneuver myself enough. So, I had to get my legs off to the side and partly under me, then push myself off. It was tiring. I then hop-shuffled my way back to bed and sat down as best I could.

Alex reached over and pulled me close, asking teasingly "Would you like me to release you?"

I shrugged as best I could, and snuggled into his shoulder. So, we dozed for a bit like that until Alex released my hands. I undid my gag as he freed my ankles. He smiled up as me, "I'm going over to my place and grab a shower. I want you to get cleaned up and ready to head out for some lunch."

I grinned at him, my eyes wide with excitement at going out with him en femme. "How should I dress?" I asked.

He smirked up at me, "How would you like to dress?"

I made a face back at him, "Well, I'd love to go in a latex dress, but I'm not sure where we're going. So, I'd like to make sure I'm not over, or under, dressed."

"We're just going for a drive and then to get some lunch, so whatever you think would be appropriate for that," he laughed at me.

I took my time getting ready. I did stretch a bit in the shower since I was still a bit sore from being bound most of the night. I touched up on my shaving. I wondered about getting laser treatments, or at least waxed. Maybe I'd talk with Alex, he seemed to know someone who did everything.

Out of the shower I took my time getting femmed up. Lots of lotion on my freshly shaven skin, so I was nice and smooth. I did my make-up light. Nothing too crazy, just a little powder on my highlights, some tan eye shadow with a nice pink lipstick. It was subtle but still said, 'Look at me!'

I went the same way with my outfit. Nothing too crazy. Just a nice mid-thigh length blue skirt and an off the shoulder tan top paired with some strappy wedge heels. Just enough to be sexy and flirty, without being completely slutty. I did go with a strapless bra just so I could put in some falsies and have some tits. I wore a g-string just so I could be a little slutty, though the chastity cage and butt plug probably said slutty more than a g-string.

Alex came in, smiled and kissed me on the cheek. I did a little twirl and enjoyed his eyes roaming over me. It was fun to be so girly and sexy. Having my guy's attention made it even more fun.

We hopped in his car and took of for a nice little Saturday drive. It was a gorgeous day, sunny and warm, but still nice enough to have the windows down and the radio up. It was hard to talk with the windows down, so we just enjoyed the radio.

We'd been on the road for a while, when I realized we were heading out of the city and into the suburbs. I tried asking where we were going, but Alex couldn't hear me over the wind. I'm sure he was intentionally being mysterious about the whole thing, so I just enjoyed the ride.

My suspicions about our mystery destination were confirmed when we turned into a driveway. We went past a high hedge and into a large yard. There was a decent sized house and a separate barn. The house was an old farm house that had been converted to a family home some years earlier.

Alex parked the car and we got out. As I came around, I looked suspiciously at Alex, "So, you want to tell me where we are?"

Alex grinned and pulled me into to kiss him. He then turned me to the farm house and gestured, "This is my house."

I looked from him to the house and then back to him, waiting for an explanation. When he didn't say anything else, I inquired, "Your house? What do you mean, your house?"

He then explained that when his folks passed, the house was left to him and his siblings. Since they lived out of the area, he took the house and bought them out of their part.

"So, you've had a house, and you're still living in your apartment?" I wondered.

He nodded, "Yeah, since my folks died, I didn't really feel right living here. I was still in my lease, so I figured I'd wait to move in here... besides, I wanted to meet the cute girl next door."

I gave him a sideways look and smiled, "So, this is why you're moving out of your apartment? You're coming here?"

"Yeah, I've been cleaning it up a bit. It still needs some work, but its pretty homey. Its got a lot of space. Two people could make a nice home of it," he said quietly, almost a little embarrassed.

"Well, are you going to show me around then?" I took his arm.

So, we toured the house. It was a little odd since you could see where he had cleaned up and moved stuff out, but in some places there were old pictures and things. He took me around and showed me the kitchen, which as you'd expect was pretty outdated. As was the furniture, and the wallpaper. Yeah, the whole thing had clearly been done a while back, but nothing had been updated since.

The layout was also odd since some renovations had moved doors or added walls. There was a nice screened in patio on the back that looked like it was part of the additions. We went upstairs and there were four bedrooms with two bathrooms, one in the Master Bedroom.

"Which was your bedroom?" I asked.

He gestured to one room, "That one, but we moved here when I was 15, so I really didn't live here that long."

"Oh that's kind of good. Honestly, I was thinking having sex in the bedroom where you were conceived might have been a little weird," I said. He was about to reply when I added, "I'll bet you jerked off in here a lot though, huh?"

Alex grinned at me, "You are bad."

"Oh, does that mean you're going to spank me?" I batted my eyelashes.

"Damn straight, girl," he said forcefully. Then softly added, "But not yet, so behave yourself."

My clit throbbed when he called me 'girl'. It was amazing how much just a word could impact my psyche. So, I reigned it in. Overall, it was pretty big, yeah, the house. I was a bit surprised they would have moved to this large a house when their kids were almost grown.

I mentioned that to Alex when we headed back downstairs. "Yeah," he sighed. "Dad always wanted to have a workshop and mom always wanted some farm animals. They'd gotten goats once we moved out, but they only had the animals for a few years before they both got sick. Dad did repair the barn and they had the goats out there."

"Do you still have the goats?" I asked curious to see them.

"No, but I have some ideas for the barn, but first I want to show you why I really think you'll like this place," he smiled slyly.

"Lead on, Sir," I looked at him wondering where this was going.

We took the stairs down into the basement. It was cool and a little dark as you'd expect. There were a lot of boxes and things stored down here, as well as the washer and dryer. It looked like they started to finish the basement, but never completed it. Alex took my hand and led me to a small room in the back. It was a decent sized room, but it reminded me of, well, of a...

"What does this make you think of, girl?" he asked right by my ear.

"A dungeon, Sir," I said breathlessly.

"Good girl," he beamed in my ear. "Do you think you could spend a few hours chained to the wall down here?"

"Oh my," I gasped, my clit throbbing with excitement. "Yes, Sir!"

I could see me on all fours, crawling to him with a thick heavy chain collar securing me as he proceeded to bind me tighter.

"Good, it will need some work, but I think it will be perfect for my little sissy slave girl," he pulled me in and kissed me deeply. "Come on, I want to show you something else."

He led me back up the stairs and out the back porch. As we walked towards the barn, he rubbed on my new butterfly tattoo, "How is that healing up?"

"Its going well," I said. "I think it'll be cute when its healed. Of course, now I want more."

Alex laughed, "Well, we can make that happen. I think we should get you some piercings first." He tugged on my earlobes.

"Oh wow, really? Yeah, I guess we should. I've always wanted to wear regular earrings. Clip-ons are okay, but real ones would be great," I said as we strolled across the yard.

"Yeah," Alex noted. "And you can learn how to handle getting other things pierced."

I purred as he said that and wrapped myself around his arm. All this talk of dungeons and piercings had me worked up. We entered a small door to the side of the main barn doors. I could immediately smell the hay and the musty scent of the barn. It was primal and stirred something in me.

"Well, here it is. You might be able to see that it was fixed up a few years ago, so its in pretty good shape. Now, I was thinking we could convert this area to a proper garage." We walked to a small side area with a bunch of tools hung on the wall. "This was my dad's workshop, so this will stay," he explained.

"So, you don't want to keep it as a barn anymore?" I asked a little puzzled.

Alex led me to a divider in the middle. There were more barn doors on this side with several stalls to each side. The smell of hay was even stronger here.

"This side could stay as the barn," he explained.

"Oh," I said, then wondered aloud, "If you don't have goats, why is there fresh hay?"

"Like I said," Alex smiled mischievously. "I have some ideas for the barn."

He walked to one of the stalls and reached in. He pulled out a small bridle gag.

I gasped in surprise and arousal, "Oh my! Am I going to..."

"Be my little pony girl? Yes, you are. Now get undressed, my little filly."

I nervously took off my top and skirt, kicking off my heels. Alex helped me with the strapless bra and g-string, while I slipped out my falsies. Alex took this chance to run his hands all over me, kissing the back of my neck.

"Your panties are soaked, girl. You like the barn and being my pony?"

I moaned as he hit my erogenous zones, "Yes, Sir. I love being your play toy."

"Well, then we need to get you kitted out properly," he held the bridle up to my mouth and I bit down on the soft rubber, taking it in my teeth. Just this act had me feeling very in the role. Alex picked up more leather straps and wrapped a sturdy leather harness around my waist and stomach. The feel and smell of the leather had me falling into a submissive head space.

He wrapped several of the straps around my shoulders and down to my legs, with the straps wrapping around my thighs and shoulders pulling the whole thing tight. Alex then reached into the stall and pulled out two oddly shaped pieces of leather. When he held them up to my face, I realized they were hoof boots. Holy shit! When did he get those?

He smiled at me and winked. He knelt down and put the first boot by my foot, I leaned on the stall as I lifted my foot and slid it in. This was a serious piece of hardware. The arch meant I was almost up on my toes. Since there was no heel, I thought I would have very little support, but the well-designed piece had lots of arch support, but had no give. So, I would be up on my toes like in a high heel, but my foot now looked like a hoof.

Alex transformed my other foot and I was soon balancing in the strict footwear. I was dripping out of my cage I was so worked up. I was busy admiring the shiny boots when Alex suddenly wrapped something around my neck. As he buckled the collar on, I realizes this was a strict posture collar.

I could barely move my neck. What little movement I had let me watch as Alex pulled out another bundle of leather. Did he have a bottomless bag of leather gear? He took my hand and started sliding a leather glove up my hand. The elbow length gloves ended in a small ball at the end, so I had to make a fist in it. The glove as you can probably guess ended in a small hoof. Alex transformed my other hand a moment later.

I also realized this had the effect of rendering my hands almost useless. Alex took each hand and hooked them to my harness with small clips, so that my hands were held near my shoulders and I had extremely limited movement. All this bondage and gear had me horny out of my mind.

Alex grinned as reached into the stall and pulled out a set of blinders with a large brown plume of hair on the top, trailing down the back. He set the blinders on my head, limiting my vision to the side. I could only see straight ahead and with the posture collar I could really only look in a limited view. Alex then straightened the plume of hair so it trailed down my back like a mane.

I was trying to take in my transformation, when Alex smiled in my limited vision, "You okay?"

I nodded and whinnied. With the collar and bit, it was hard to move my head or say much.

"Good girl," he petted my flank tenderly. "We're almost done, just a few more additions."

What else could he do? Oh, I had a pretty good idea actually. My thought was confirmed when a moment later he showed me a large butt plug with a brown tail sticking out of it. Naturally, it matched the plume on my head, and both were very close to my natural brown.

Alex reached behind me and pulled out my current plug. I grunted and bit down slightly on the bit in my mouth. Alex then bent me over and leaned me over the low wall of the stall. He then slowly pushed the large plug into my already open and greased hole. I was a bit surprised how much I stretched with the plug. This thing felt huge! It was really only slightly larger, but it still made me groan when it settled in and my ass closed around the flared base.

"Oh, very lovely, my good little pony girl," Alex said, rubbing my sides and patting my ass.

He stood me back up and walked around me, inspecting me. I hoped he was going to take some pictures, too. It felt amazing, I wanted to see how I looked, as well.

When Alex walked back in front of me, held up two small bells. Bells? Well, I guess they have sleigh bells, or something. I thought he was going to attach them to the harness, but when he grabbed my exposed nipple and began pinching, I realized they were going directly on me.

Sure enough a moment later, pain flared in my nipple as he clamped the bell onto my little nub. He started playing with my other nipple while flicking the bell on the first nipple. The mix of the pleasure and pain had my head swimming. The flash of pain told me he clipped the other bell on. He shook both of them, making them ring and causing ripples of sensation to roll through my body.

I was so hoping he was going to take me now. I was pretty sure he couldn't add anything else. I really didn't have anything else available to cover, tease or torment! Alex reached up and attached reins to my gag, then started pulling me forward. Wait, where were we going?

Sure enough, he was pulling me towards the large barn doors. Was he really taking me outside? I clomped over towards the door as Alex leaned in close, "I know what you're thinking, girl. 'Are we going outside?' Don't worry, my pet. There are almost three acres of land, its about a half mile to the next house and the lane is covered by woods and there is a hedge around this part of the property."

I snorted softly and nodded my head, in response. He leaned in close and whispered, "And I have a little surprise for you out here."

Oh boy... He opened the barn doors, took my lead and led me nervously out into the warm sun. Never mind the fact that I was half-naked, bound in leather with a giant tail plug up my ass, I felt very nervous, like everyone could see me. Not quite the near panic I'd get going out dressed, but similar.

As we walked to the side, into a shady spot, there was a small pole there. It looked a bit like an old laundry pole or something. I had a feeling we weren't going to do laundry though.

Alex walked over to the pole and turned it a little. There were two bars sticking out of the top of the pole making it into a t-shape. As he took two leather straps and hooked them to my harness, I realized I was being put on a walker. Apparently, we were really going to do some pony training. Alex talked me through the exercises we were going to do.

"And since you're practicing to be a show pony, you'd better keep those knees up. Now, walk, girl!" He smacked my ass with a riding crop he must have pulled from the bottomless bag of leather.

I hopped forward and began walking the circle the trainer would make me follow. As I walked I tried to step my feet high, but Alex wasn't satisfied and smacked the backs of my legs with the crop. Each smack, I'd get my legs up higher until it felt like my knees were hitting me in the chest.