Sissy Awakening Ch. 03

Story Info
Sissy gets fucked by Sarah's bull and learns about pain.
12.1k words
4.45
43k
24

Part 3 of the 4 part series

Updated 06/10/2023
Created 10/13/2020
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- Sissy Meets Sarah's Bull -

Standing at the living room window with the windex and paper towels, I teetered on the ridiculously tall Mary Janes. It were as though I were standing on the balls of my feet and toes only. There was no relief. My other pumps felt like heaven compared to these!

She said to wash inside and out, and not to miss a spot. That meant I'd have to go outside. It was still only mid afternoon so I had a lot of daylight left. I either had to buck up and just get it done, or avoid the outside windows until after dark.

I didn't want to be washing any damn windows let alone until after dark. I'd fantasized about being a sissy maid before, but it was a lot sexier in my fantasy. This... as it turns out, was just a whole lot of work! None of it made even the slightest bit easier with these long ass nails. Or these super sexy pumps. Hell, when women wore shoes like these, it was really only to take them off, or they were on their backs the whole time! I wish I were on my back, taking a nap maybe!

3 hours into cleaning the house and Sarah had woke up from HER nap. She was ready for dinner, and I hoped she was going somewhere else to eat. At least then I could get out of these god forsaken shoes!

"Hey, how's the cleaning going sissy?" She asked me yawning and stretching at the same time.

"Um... yeah, this sucks!" I said.

"Well, this is what happens when a man wants to wear lingerie sissy!" She quipped.

"What's the worst part of all?" She asked while taking a seat at the kitchen table.

"These pumps, they are killing my legs, I can barely walk, my toes are on fire, and they just suck!" I said agitated.

"I'll tell you what, if you want to endure something else, you can switch to more comfortable pumps." She consoled. "But choose yes or no, now."

"Yes! I choose yes!" I sighed, stepping out of the shoes.

Tall pumps had to be torture devices made by men for women. Maybe they were meant to punish them for being beautiful. Maybe they were meant to keep women in control. I would do anything to get out of those shoes!

Sarah stood, and walked to her bedroom. I figured she was going to get the crop to whip me numerous times. That'd still be better than wearing those shoes. At least it'd be over with. Coming back in the kitchen, she held a black strap with a buckle. It was too small to be a whip, it almost looked like a hobble one might put around a horses legs to slow its speed. Stepping behind me, she had me kneel in front of her and open my mouth. She then brought my trade off into view just before she placed it in my mouth. It was a penis shaped gag. It looked like a real penis! It was about 1.5" in diameter so I had to stretch my mouth open to get it passed my teeth, and it was about 3.5" long so it rested right at the back of my throat. When she pulled the straps tight around my head, it was dangerously close to gagging me.

The gag, was still better than those damn shoes and I was happy I'd made the trade.

"There you go sissy, is that better?" She teased.

"Mphph... mphh... mmmphmm..." I tried to speak but couldn't.

"I'll take that as a yes." She replied.

"What's for dinner sis?" Sarah, forgetting she had JUST gagged me, asked.

"Mmmph, mmmmp, mmpmpmh." I mumbled. She couldn't hear what I really said. I'd have gotten a beating for that. I really said, make your own fucking dinner but she couldn't hear that.

The cock shaped gag was not a bad size at all. The only real issue was saliva management. I didn't have a good way to swallow and my saliva began building up immediately. If I tilted my head back, I could get a bunch of saliva to pool back there and swallow it all with a bit of effort, or just stand there and let it drip all down my chin, and onto my chest. Mmm... that sounds hot unless you actually have to do something. Well, I went with the third option. I simply carried a rag with me to wipe up my little dribbles. I felt like such a slut with my ass and my mouth filled at the same time, and with a little imagination, I could pretend my saliva was a man's cum dribbling down my chin. I could be that lucky again!

To ease Sarah's appetite I made a quick PB&J and some potato chips for her, after that I threw a roast in the crockpot with some cut up potatoes carrots and onions with quite a bit of salt and pepper. I left that to cook over the next four hours. The dinner would require minimal effort with the greatest prize. That's probably why women cook meals like that!

The cleaning all went a lot faster now that I could move around freely. While we weren't the most tidy couple in the world we definitely weren't slobs either so cleaning up the house was not much more than picking up clothing, washing the dishes, wiping down countertops, dusting and vacuuming. For brief moments during my cleaning I even forgot that I was wearing a sissy maid uniform. But the gag was a constant presence in my mouth and with the drooling I could not ignore it away.

Finishing up I stood at Sarah's door quietly knocking. I couldn't tell her I was done cleaning because of the plastic cock jammed in my slutty mouth so I simply curtsied and displayed the house with open hands. I found it's kind of hard to show any kind of smile with a 3.5" dildo strapped in your mouth. I did get used to liquids pooling in my mouth and dripping out the sides though.

I followed Sarah through the house as she pointed out little discrepancies or the slightest bit of cleaning that I had missed. I either took note of the items or took care of the problem immediately.

Standing in my room knowing that the house was clean because I did that gave me a great sense of accomplishment and I felt pride in my work. Grabbing the 6 inch tall Mary Jane's I nonverbally asked Sarah if I could switch the gag back for the shoes and simply by closing her eyes and nodding I was given permission. Stepping into the shoes and buckling the ankle strap I could immediately feel my calves tighten back up and the pain returned to my toes again. I pulled the gag out of my mouth with my head tilted back so I didn't drip my saliva everywhere and I swallowed all the spit from the cock shaped gag as though it were my lovers cum.

I really did hate the shoes but I couldn't prepare dinner as I drooled all over everything. So I had to endure the discomfort of the shoes and try to put the pain out of my mind.

After sitting down for a nice dinner, I cleaned up the dishes from the night and put away the leftover food. Sarah told me that she had called a friend to come over and watch a movie with her. But she didn't tell me was her friend was a man and that they would be watching a porn movie right in the living room! She did have me prepare some light snacks and put some beer on ice for him if he wanted.

I answered the door when Jake arrived. I curtsied deeply, and said 'Welcome to our home, I am Sarah's sissy slut. May I offer you a beer sir?' As Sarah had instructed me to say. I think it was meant to completely humiliate me because, well... that's exactly what it did.

He was however a gorgeous man that even I liked looking at, with well-defined muscles. I'd be willing to bet he made his living making celebrity impersonation appearances as Josh Holloway. He was tall, blonde, tanned, and masculine. I used to have a man crush on Sawyer from lost so he was easy on my eyes too!

Sarah had me sit in the corner of the room. I could both watch the movie and watch Sarah with her friend. I'd only ever seen Sarah with one other person, that was just recently and I spared myself the discomfort of watching. Tonight I sat, on a cold metal fold out chair in the corner watching everything. The movie wasn't bad but it was very fitting that they would be watching cuckold porn. I focused on the movie for a bit, and I briefly forgot I was the cuckold in my relationship, until Sarah startled me out of my daze. Jake's pants were pushed down to his ankles, and his cock lifelessly lay over his leg. Even soft he was 6 inches long and somewhat thick.

"Sissy, come get Jake hard so he can fuck my wet pussy!" she said, mimicking the porn movie we had all been watching.

I knelt between Jake's legs, and grabbed his penis. I flipped it back-and-forth momentarily feeling the weight of it in my hands. Looking up into the eyes of the Sawyer lookalike, I imagined I were on the set of lost, and I had to make sawyer cum in my mouth or I would be stuck on the island alone for ever! Jake look down at me indifferently as I opened my mouth and placed his cock inside. At 6 inches it filled my mouth completely. I sucked on the tip until it engorged itself and became fully hard. This was the first time I had taken a soft penis in my mouth and made it grow to full length and hardness. I felt accomplished and sexy at the same time, but my sissy slut side just wanted to choke on his dick and drink his cum! Applying gentle suction I would bury the cock as deep as I could then pull my mouth away with a loud popping sound and quickly drive my mouth back down over his cock I would attempt to swallow the entire length. I would gag and produce long sticky strings of saliva that were suspended between his cock and my sissy mouth.

"That's enough faggot!" Jake said pushing me away.

I sat on the floor at their feet. I felt a little hurt that he just pushed me away before I got my reward but he wasn't there to fuck me anyway. I was lost in my own feelings and thoughts before I realized I had been dismissed. By the time I got up Sarah was bouncing on his cock in much the same manner I imagined myself doing. I became jealous of her situation. It was like she was trying to make a show of it. She was trying to show me that she could take a cock like a woman only can.

Sitting back down in the cold metal chair my butt plug clanked softly below me. Watching Sarah bounce on Jake's cock I began moving my butt around on the chair. If I moved just right I could push the butt plug even deeper and it put pressure on my prostate. I started imagining myself in Sarah's situation, how I would be bouncing on Jake's cock. A little wetness formed at the tip of my clit as I bounced my butt on the chair. I was lost in my fantasy when Jake picked Sarah up without pulling his dick out of her and started carrying her to the bedroom. Sarah was acting the part maybe a little over the top saying things like 'Oh my god you're so big' and 'You're fucking me so hard' thrown in between loud moans and screams of pleasure. Once they were in her bedroom she started yelling "fuck me Jake fuck me hard I want you to come inside of me!" She was doing that for my benefit more than anything.

I didn't really know what to do so I just stood outside her door listening to the theatrics and the sounds of sex. Their session ended with loud grants and screams as I can only assume he did finally come deep inside her pussy. I could hear quiet conversation followed by loud giggling. After which I was called into the room.

"Come here sissy!" Sarah shrieked, laughing a little afterward.

I love Sarah, but her acting was a little much for me. I guess I deserve it though. I did fuck 4 guys the other night and take another 8 in my mouth at the sex shop.

"Come clean us up slut." Sarah cooed

I started with Jake I found cleaning a cock was much easier than cleaning a pussy with Jake's cock I simply sucked up any cum that had fallen from the tip and lick off the pussy juice from his balls, giving his cock a final deep throat, I felt satisfied all that remain on Jake's cock was my saliva and maybe a bit of Sarah's pussy juice. I moved on to clean out her pussy. Cleaning the cum out of her pussy required a lot more time and patience. If she were to straddle my face and let gravity do the work the cleaning would be much faster and more efficient but now she was laying on her back legs spread and a big rope of come dripping down between her ass cheeks. Kneeling between her open legs I stuck my tongue out as far as I could and licking from her ass crack up toward her clit. I scooped up as much of the cum as I could and swallowed it down. The taste of his cum didn't register immediately but I imagined liquid hand soap coating my tongue and throat. I wondered to myself what he ate to make his cum taste like that. I mixed deep licks inside her hole with short little flickers at the button of her clit. That made her head fall back and she pushed her pussy pushed up into my face.

I felt Jake behind me he had pulled my ruffled panties down exposing my caged sissy clit and the jeweled plug buried in my ass pussy. He pulled my legs from the kneeling position on the bed causing me to fall jamming my caged clitty into the bed painfully. He then yanked the plug out of my ass pussy and dropped it noisily on the nightstand beside the bed. I was glad I had the large plug in my in my pussy all afternoon because Jake's cock was even bigger than the plug was.

"You ready for my cock little girl?" Jake breathed into my ear as he placed the head of his pecker right onto my asshole.

All I could do was moan a, "mmm... yes Daddy!"

"Daddy is going to rip your little asshole open slut!" He said through gritted teeth as he pushed his cock into my slutty hole.

His cock was much larger that the plug that'd been in my ass pussy all day and my insides screamed in pain as he pushed. Reaching back, I spread my ass cheeks as wide as possible but nothing helped until I pushed my insides out as though I were taking a huge shit.

"Yeah, take all of Daddy's cock you fucking slut!" He grunted into my ear.

Here I was living out a long time fantasy to get fucked from behind while I licked a woman, while I licked Sarah. Jake pounding me wildly. His body was slapping into my ass loudly each time causing me to bury my face deeper into Sarah's dripping wet pussy. Time melted away, my body melted away and all I could focus on was the cock pounding deep in my sissy pussy and my tongue on Sarah's cunt. I don't know how long it had been by the time Jake started tensing up but my tongue hurt! My jaw and neck were throbbing in pain. I was pulled back to reality just as Jake started shooting hot streams of cum into my bowels. When he pulled his cock out of me, I felt a long hot stream of cum hit my sissy balls and drip down my leg. He then shoved the plug back inside my well fucked hole and slapped me on the ass.

"She's a good fuck." He said while wiping his cock off on the petticoat of my sissy maid uniform.

Sarah leaned close to my face, pecked a kiss on my cheek and whispered,

"Thanks sis, I'll see you in the morning!"

In my room, I could hear the couple sharing a shower. She hadn't even unlocked me yet so I couldn't even get out of my uniform. I pulled the petticoat off and looked at the mix of blood cum and feces. I tossed it in a pile in the corner. The noises droned on until I drifted off to sleep still wearing my shoes and the plug holding Jakes cum inside my pussy.

I awoke Saturday morning with a bladder that felt like it might burst at any moment, and a pain in my stomach that could only be described as... well, I'll spare the details.

Squatting over the toilet, I pulled the plug, and I'll leave it at that. Once cleaned up I sat to empty my bladder, only it wouldn't come out. I could feel myself peeing but nothing. I pulled at the cage and produced a small stream around the tube but no relief. Checking the end of the cage, the hole at the end had something in it. It looked like dried up cum. Scratching at the surface, the blockage broke free and cum oozed out, followed by a more forceful flow of urine. I had pissed all over myself and around the toilet. That's one more thing I had to do before I could get in the shower.

I spent the next 10 minutes on my hands and knees cleaning the piss off the toilet and the floor well and myself... I had to find Sarah, or the keys to undo the collar on the sissy maid uniform and my ankle and wrist cuffs.

She was dead asleep laying there so peacefully she looked like the woman I had fallen in love with. Even in her sleep, a thin smile rest across her face. She must've been quite satisfied last night. Shaking her arm to wake her she spread her arms out stretching and yawned widely.

"Hey how's my little sissy slut feeling this morning?" She asked looking up at me.

"I need a shower but I can't take this off!" I said pulling at the neck of the dress and displaying my wrist cuffs.

Reaching up behind her she grabbed a chain from the bed post that had keys of several different sizes attached to it. I could see a tiny one and could only guess that it was for the lock holding my sissy clit tight against my body and I wished she would undo that as well. She in locked all the cuffs and collar and I lifted my skirt up pushing my Chastity cage out towards her in a pleading manner for her to unlock that as well.

"I'll help you clean that up after your shower." She comforted me, looking up at me with soft eyes.

Standing in the shower I washed the cum from my face and ass, then I shaved my arms and legs and gently washed my hair. Standing at the mirror I tended to my piercings and shaved my face again. I left the bathroom and just stood in my room in my towel not wanting to get dressed yet. I knew there was a cock hidden underneath that stainless steel cage but she was right... In the state it was in, it didn't look like a cock at all. It looked like a bulbous metal clit.

I tugged on the cage slightly, feeling the tube move around inside my body. It didn't really bother me anymore than the fact that my erection was stopped buy a ring that would squeeze my testicles. I found over the last 24 hours that I just stopped getting hard-ons.

Sarah came in with my wrist and leg cuffs in hand. She instructed me to lay on the bed face up as she attached the cuffs to my legs and hands. She then hooked small chains to the headboard and footboard to my hands and legs spreading me out effectively locking me to the bed.

Once she felt I couldn't move she produced the miniature key put it in the little lock and unclipped it from my chastity cage. She then reached down and pulled the cage and tube free from my little shriveled wiener. Once the tube cleared the tip of my shrunken and deformed penis, a thick mucus like stringer stretched out between the two. She then dropped the cage into a cup containing what smelled to be alcohol. She then unclipped the ring from around my cock and balls and started cleaning my entire package with a warm washcloth.

The warm washcloth and her gentle touch caused my cock to spring to life standing straight up just over 7 inches tall! I was hard as a rock. I was glad to see I could still get an erection, I was glad to see that I had a cock again. She cleaned my cock until she sensed I was ready to come and then stopped. She didn't touch me again until I calmed down and my cock begin to wither slightly.

It was like she invented an evil game that morning. She would wash me until I was right at the verge of cumming and then stop, only to start up again after I had relaxed. After 30 minutes of that, she could have merely blew hot air on my cock and I would have blown cum all over her face.

After letting me relax for a minute, she lubed the tip of the tube up and placed it at the head of my cock, then pushed it in. She pushed the tube all the way inside my engorged penis and it deflated just a little bit. Clipping the ring around my balls she put her palm right on the tip and smashed my entire cock back down inside its cage and slipped the lock back into place. I was so frustrated I just needed to come. I had to come but I couldn't touch my own fucking cock anymore. It was a "clit" again! She threw a blanket over me and walked out of the room.

An hour later I woke to a dull ache in my stomach from the teasing she put my balls through. She was standing over me unclipping my wrist and leg cuffs. Standing up she clipped a collar similar to the one on my uniform around my neck and locked it in place as well, attaching a leash to the other end she walked out of the room tugging me along.