Becoming A Sissy Slut part 2
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Becoming A Sissy Slut (Part 3) free porn video
I heard my mistress leave the room as I tried to catch my breath, still on my knees with my head down on the carpet. My ass was still gaping wide open from the rough anal fisting I had just received, I reached back with one hand to feel my sissy fuck hole. I easily slid 4 fingers into my ass, almost without even touching the edges of my entrance.
‘Holy fuck I’m a complete anal whore’ I thought to myself. ‘I would do anything for that every day...’
Slowly I got back to my feet and walked to the master bathroom. I fixed up my make up and touched up my wig. On my way out of the bedroom I grabbed the large butt plug that had previously been tightly inserted in my ass. I grabbed it and easily pressed it back in, I had to stay clenched to keep it in I was so loosened up.
I made my way down stairs, still completely naked besides my tiny pink chastity cage and stainless butt plug, to find mistress Kassy grabbing her purse. She had already changed into a black pair of yoga pants and a short t shirt that showed just a hint of her washboard abs.
“I have to run to the store and swing by the beauty salon to do a few things. I will be back in a few hours. Here are some clothes for you to wear and a list of chores you need to have done when I get back. Have a good afternoon Rachel” she said sweetly, kissed me on the forehead then walked out the door.
I slipped on the white short shorts, a spaghetti strap tank top and 6” clear high heels that she had laid out for me and looked at the list of chores.
Dishes
Sweep and mop
Vacuum
Fold and put away laundry
‘This shouldn’t take long at all’ I thought to myself.
It was now 4 pm, I could have the work done by 5 and get a bit of time to relax.
Within a half n hour I had the dishes done and floors cleaned. I folded the laundry and carried it into mistress’s bedroom to put it away. When putting away her socks I stumbled across a tiny key in the corner of the drawer. My chastity cage key! I had only been wearing it for a day but after todays events I greatly wanted to cum.
I immediately unlocked the tiny padlock and removed the cage. Within seconds my tiny cock was at full mast, I sat on the corner of the bed and began rocking back and forth on my butt plug, replaying mistress’s fist forearm deep in my ass. It only took about 30 seconds of feverish stroking before I was spurting cum into my left hand. I quickly lapped it up like a dog, savoring the salty flavor of hot cum, relishing in the flavor.
Satisfied, I put my chastity cage and clothes back on. I sat the key on the dresser and resumed putting the laundry away. Soon I was relaxing on the couch watching tv.
A few hours later I got a text from mistress that read “When I get home come help me unload the car sissy.”
‘She wants me to go outside like this?! Oh well, nobody knows me anyways ‘ I thought.
A few minutes later I heard mistress Kassy’s car pull into the driveway, I walked out to her car sheepishly, embarrassed of being seen.
“You need to walk like a girl Rachel” she said loud enough for anyone nearby to hear. “Shoulders back, back straight and ass out.”
I obliged and helped her bring the groceries into the house. I began putting groceries in the fridge when she went into her bedroom. I heard drawers opening from the bedroom. ‘Fuck! I think I forgot to put the key to my chastity cage back into the drawer!’ I thought to myself, an empty feeling of anxiety and nerves in the bottom of my stomach. ‘Maybe she won’t notice and I can sneak back in to put it away’ I tried to reason with myself.
Mistress returned a few minutes later with a large cardboard box. “Come here Rachel, I can put the groceries away myself but I would like some entertainment while I do it.”
I walked over to where she was opening the box in the corner of the kitchen. I started to read the box she was opening to myself:
-Mr Ed’s Anatomically Correct Horse Dong
-Over 20 Inches of Insertable Fun
I stood there in shock while she continued opening the package and removed the giant rubber dildo. She firmly pressed the suction cup base onto the hardwood floor of the kitchen then asked “Well, what do you think my little slut? I’ll go get you some lube.”
She disappeared down the hallway while I got a better look at the massive black toy on the floor. It was so tall...it came up above my knees as I stood next to it. The head was flared out even wider than my fist, the shaft was about as big around as my forearm and about 12 inches down it was the mock sheath of a horse where it got even more girthy. The bottom half was roughly as big around as my bicep, the very bottom 6 inches flared out to the base and was almost as big as my thigh.
‘What does she want me to do with this thing?’ I thought to myself. ‘There’s no was I can even take half of this thing.’
Mistress Kassy returned with a bottle of lube and handed it to me.
“Take your time Rachel, I don’t expect you to be able to take very much of it but it doesn’t hurt anything to practice.”
“Yes mistress” I replied while still staring down at the massive rubber horse dick.
I poured a tremendous amount of lube onto the flared head and began rubbing it all over. The head was huge, definitely bigger than my own fist on closer inspection. I worked my way down the shaft adding more lube as I went, once I got down to the bigger sheath part I couldn’t even fit both of my hands around it. I applied more and more lube, even down onto the base which was absolutely enormous. Just to check and see, I put my knee next to the base for reference and it was absolutely bigger around than my thigh. Though the rubber dong was soft on the outside, it felt like the center of it was very firm which held it perfectly upright while I lubed it up.
“Better get to it sissy, I didn’t get it out just for you to stroke it” mistress ordered me sternly while she was putting items in the cupboards. “And leave your shoes and tank top on, its sluttier that way.”
I stood up and removed my short shorts over the clear high heels then slowly pulled the large stainless plug out of my ass. I was still a little sore from mistress’s fist earlier in the day but definitely still loosened up from having the plug in all day.
Crouching above the horse cock, I reached down and held the flared head in place. As I lowered myself onto the tip I could immediately feel how wide the head was, it was touching both of my ass cheeks before it even started to touch my entrance. Gradually I put more and more pressure down onto it as I began to feel my sissy fuck hole stretching around it. I could feel my face wincing in anal pain as I tried to swallow it with my hungry ass. Bit by bit, it began making its way into me, I started to moan in pain as I stretched all the way around the flared head.
With a sharp pop I felt myself take the head in.
“Oh fuuuuck!” I whined aloud as mistress walked over to inspect my progress.
“Good girl Rachel!” She exclaimed as she knelt down next to me.
I held myself still for over a minute, panting aloud while trying to give my ass a chance to get used to the massive member inside of me.
“Reach back and put your hands on the ground behind you sissy. Ride it reverse cowgirl for me” mistress suggested.
Very carefully I reached both arms back and down to the floor, I placed my palms on the ground and was on my tippy toes with my feet. Ever so slowly I began lowering myself down onto it a few inches and then back up. Once the pain from being stretched so wide by the head subsided I was once again in anal ecstasy. I felt so full and my hole was stretched to the max. I started to work up a rhythm of up and down, slightly deeper with with thrust until I could feel the head pressing my insides and causing slight discomfort. Mistress stayed knelt next to me, watching closely as I bounced up and down on the top 8 inches of rubber horse cock.
She stood up next to me and asked “How are you enjoying your chastity cage sissy?” She said with a squint in her eyes.
I felt my heart sink to my stomach and I stopped dead still from my riding. I knew that she knew I had found the key. I decided to lie.
“I love it mistress” I lied through my teeth and slowly began riding the monster cock again.
“Oh, so you don’t ever feel the need to take it off and touch your useless, pathetic, tiny little sissy clit?” She fired back.
“No mistress I don’t” I lied again.
Without warning, in one swift motion mistress kicked me in the back of the calves and knocked my legs out from under me. Within a second 20+ inches of massive rubber horse cock was fully inserted inside of me. The flared and firm head had forcefully went full depth inside of me, shoving all of my internal organs aside on its way in. The girthy sheath was just a minor speed bump as the massive base had ripped my ass completely apart.
I let out an ear piercing scream of pain as she immediately placed both of her strong hands on my shoulders and pushed down, holding me firmly in place. Tears were flowing down my cheeks leaving trails of eye liner and mascara, it felt like the head of the dildo was touching my throat it was so deep in me. I sat there sobbing and panting as I realized dildo was so far deep inside that the head was likely right around my nipples.
“I know you found the key you sneaky little whore!” She yelled at me. “Sit there impaled on that horse cock and think about what you did! If you don’t want to be my sissy then get the fuck out of my house but if you want me to train you to be a slut you have to obey the rules! And rule number one is that your sissy fuck hole and your throat are entrances for cocks, your clit is only for you to piss out of. Do you understand you fucking whore?!” She continued yelling to me.
“Yes ma’am...I’m so sorry...I’ll never do it again, I promise...” I said through the tears.
“I know you won’t, and do you want to know how I know?” She replied.
She took the key from her pocket, inserted it into the padlock on my cage and snapped the shaft of the key off.
“Now you don’t have a choice slut.”
I couldn’t have cared less about the broken key at the time. My internals felt like a boxer had just punched me in the guts and my asshole felt like a car had just drove up it.
“How does it feel sissy? How does it feel to have 2 feet of horse cock in your ass? Does it turn you on to be such a loose slut?” She asked mischievously.
Even with the tremendous pain in my stomach and ass I felt my cock strain against the cage when she talked down to me.
“Yes ma’am...” I sobbed.
“Good. Your such a fucking slut.” She said sternly while taking her hands off my shoulders.
She hooked her arms under my arm pits and began slowly lifting me off the dildo that had me impaled on the kitchen floor. I got my feet underneath me and very slowly helped to lift myself off. When I got to the top and had to get the flared head out of me, I let out an audible cry of pain as it popped out of me. As soon as mistress let her strong arms go from me I dropped to my hands and knees, exhausted from the trauma that my body had just went through. Mistress helped me to the spare bedroom where I crawled into bed and drifted off to sleep.
When I awoke mistress was already gone but left a list of chores for me, I went through my morning routine of shower, shave, enema, make up and wig. Very very gently I re inserted the butt plug into my tender ass and went through my day. I was sore and mistress knew it, she gave my ass a break for a few days though she still throat fucked me on a daily basis with an ejaculating dildo, either filling my mouth or covering my face with hot sticky fake cum.
It was now Friday evening, I had gotten the last 3 days off from anal training besides constantly wearing the plug, and the tenderness in my ass had finally gone away. I had just finished my chores and Mistress was sitting on the couch reading a magazine. I entered the living room to let her know I was done with my chores for the day.
“Sissy, do you think you are ready for your first test?” She asked me while still flipping through the pages.
I had no idea what the test would involve but I had grown quite horny in the last few days.
“Yes ma’am, I believe I am” I replied while standing in the doorway.
“Good. I’ve laid some clothes out for you in the bathroom, I want you to put them on and fix your make up so it’s even more skanky.”
“Yes ma’am” I said as I turned and went to the bathroom.
The clothes she had laid out for me were a black mini dress and black high heels, no panties or bra. I put them on to find that the dress barely covered 1/2 of my ass cheeks, no matter how hard I pulled it down. The bottom of my pink cage was visible if you knew what to look for.
I touched up my make up and added more eye liner and mascara then topped it off with thick bright red lipstick. I returned downstairs to find mistress standing near the front door with her keys in her hand.
“Mmmm Good girl, you look like a cheap whore, just what we’re looking for tonight” she said with a devilish smile.
‘What the hell does that mean?’ I wondered to myself.
“Let’s go” She said as she turned and walked out the door.
Under the cover of darkness we got into her car, I was not worried about people seeing me because I was a sissy, I was worried because the majority of my ass was visible!
She drove us out of town a few miles then took an exit, in the near distance I could see a restaurant/convenience store with a parking lot that must’ve been over a square mile that was completely full of semi trucks. It was clearly a large truck stop for truckers.
We drove back behind the restaurant and to the very far end of the parking lot where she stopped and put it in park then turned the headlights off.
“Here you go sissy” she said, handing me a tiny black handbag. “I want you to walk down the aisles of these trucks. When you see a truck with a red light on inside the cab I want you to knock on their door. If they answer then you are to go inside with them and do whatever they want. When they ask you how much, tell them one dollar, that way I’ll know how many cocks you pleased tonight.”
‘What the fuck?!’ I thought in amazement. ‘My first test is being a prostitute at a truck stop?! For multiple guys?! This is insane! I’ve never done anything with a man!’
I sat there in shock holding the hand bag and staring at the dash.
“Well sissy, do you want to be a true slut or not? Remember, if you don’t want to continue you can quit at any time.”
“Yes ma’am” I replied with a shaky, trembling voice.
“And don’t forget to tell them what you are before you get inside with them.”
“Yes ma’am” I nodded.
I opened the car door and climbed out. I opened the handbag to find a small bottle of lube to be the only contents, no condoms. The night air was cold on my arms and legs, I was so nervous I didn’t even feel like myself. I took a deep breath and started walking towards the first line of parked trucks. It felt like I could see myself walking I was so uneasy.
‘Maybe none of the red lights will be on. It’s awfully late, they’re probably all asleep’ I tried to calm myself down with wishful thinking.
I walked past the first 5 trucks, taking a huge sigh of relief with the sight of a dark, unlit cab. When I reached the 6th truck I lost my breath, clear as day was a bright red dome light inside the cab of a white semi truck. I thought about just walking past until I remembered the punishment mistress had gave me the last time I had disobeyed and lied to her.
My hands were shaking and my knees were wobbly as i slowly walked over to the drivers door of the truck, my heels clicking audibly. I very lightly tapped on the door then stepped back, hoping whoever was inside wouldn’t hear me. It was only a few seconds until the drivers door swung open. The man inside was a white man in his mid 50’s, he was overweight, unshaven and had a greasy appearance. He was wearing grungy sweatpants and a loose fitting t shirt with the neck hole stretched out. He looked like a pig.
“How much” he hollered out the door as he looked down at me.
“Umm...uh..one dollar. As long as your ok with a little extra equipment” I said meekly as I stared at my high heels.
“Ok get in” he said as he turned away from me in the truck.
With trembling legs I climbed up inside. The interior was filthy, garbage and food wrappers. It smelled stale and dirty. I made my way between the drivers and passenger seat into the sleeper area where it was even dirtier. There were clothes and garbage all over the floor, the walls were covered in dirt and grime. The driver was sitting on a filthy mattress that didn’t even have a sheet on it. It was covered in stains and food crumbs and wrappers.
“What will you do for a dollar” he said bluntly in a raspy smokers voice.
“Whatever you want...” I replied in a shy voice while still staring down.
“Good!” He spat back at me.
He leaned forward and pulled is sweat pants down to his thighs then lifted his feet and took them completely off. I glanced up at his flaccid cock then immediately looked away. It was the first guys dick I’d ever seen besides in porn.
“What are you waiting for whore. Get on your knees and suck it” he shouted at me, spitting while he talked.
I instinctively obeyed him and got down on my knees between his legs, me knees on top of the floor of garbage. His dick looked disgusting, it was dark brown in contrast to his white legs. He didn’t appear to have ever trimmed his pubic hair and his belly hung down so far it was almost touching his dick.
I placed my hands on his thighs and moved my head closer. His flaccid penis was a few inches long, thick and uncircumcised. I couldn’t believe what I was about to do, I was about put some filthy truckers cock into my mouth for money.
I placed my lips around the tip and took his soft dick into my mouth. The taste was awful, a combination of sweat and grime. I could smell a pungent odor coming from his ass and balls, I nearly gagged just from the taste and smell. I took my right hand around the base of his soft dick and held it upright so I could begin bobbing my head up and down.
In just a short time I could feel his cock growing in my mouth. Even in this filthy truck, sucking this foul man’s grimy cock, I felt an inner sense of accomplishment; I was pleasing cock just as my mistress has trained me to do.
“I said suck it you stupid cunt!” He hollered in his gravely voice.
He wrapped his arm around the back of my head and forced my head down onto his crotch. It surprised me and I gagged hard on his dick, which had grown to a heavy and thick 7 inches.
He continued holding my head all the way down on his cock, my nose was buried in his pubes and I had no choice but to sit there smelling his greasy odor, my tongue was touching his hairy balls and the head of his cock was buried securely in my throat. After probably 30 seconds he finally let me go, I quickly ripped my mouth off his cock, leaving long strings of saliva from my lips to the head of his uncut dick as I gasped for air.
“That’s better” he blurted out. “On the bed cunt.”
“Yes sir” I responded meekly, climbing up onto the filthy mattress on all fours.
I took the bottle of lube from my hand bag and sat it down behind me. I watched as he took his stained t shirt off revealing his huge greasy belly and big man boobs. He wrestled himself up onto the bed and I could hear him breathing hard behind me. He lifted the bottom of my dress up to my lower back and poured half the bottle of lube into my ass crack, I felt the cold liquid run all the way down over my balls and onto the mattress.
With his left hand on my lower back I felt the tip of his swollen sweaty cock touch my entrance. I couldn’t believe it, I was about to get fucked by a man for the first time, and here it was in a filthy sleeper of a semi by a fat, stinky trucker.
He pushed the head in about an inch, and then plunged his entire cock balls deep into me!
“Fuck!” I shouted out as his hips slammed into my ass checks with full force.
He instantly started pumping into me with everything he had, I could feel my chastity cage swinging back and forth as I tried to focus on the cock. It was so much different than my mistress’s dildos, it was less rigid and the temperature of it felt hot in my ass.
Soon I was feeling that euphoria that only getting fucked in the ass could give me. I began moaning in pleasure and pushing my ass back into him. I was in heaven getting fucked as a cheap whore. After a few minutes of fucking me doggystyle he slammed into me and then put all his weight onto my back, causing me to fall face and stomach first into the nasty mattress with 350 lbs of man on my back. He kept thrusting into me, keeping me pinned into the mattress. His face was right next to mine and I could smell his cigarette breath. He was wheezing and grunting in my ear with every thrust.
Soon he began thrusting even harder.
“Oh yes sir! Please breed my ass!” I moaned.
He began wheezing even more when he slammed into me and I felt shot after shot of hot cum hit my insides. My eyes rolled back in my head and I felt butterflies in my stomach. I had just served my first real cock!
As soon as he was done cumming he pulled his cock out and sat back on the bed, still wheezing and breathing heavily.
“Get the fuck out whore, here’s your fucking dollar!” He hollered at me as he threw a wadded up dollar bill at me.
I stuffed the dollar and my bottle of lube into my handbag and scurried out of the truck back into the parking lot. I couldn’t believe it, I had just let the first ever man inside of me, and let him finish inside of me, and he threw me out like a piece of meat as soon as he was finished. ‘Am I truly just a worthless sissy fuck doll?’ I wondered.
I tried my best to straighten my hair back out and get my dress back in order.
‘Maybe the next guy will be better’ I thought as I started back down the aisle of trucks. I had more confidence this time. I was still nervous but I was excited, still half cock drunk from my last fucking, and wanting to get another dick inside of me.
After a few minutes of walking down the aisle I found another truck with a red light on.
I bravely tapped on the door and immediately it swung open. This guy looked completely normal, he looked like he would be your next door neighbor. Blue jeans, white sneakers and a polo shirt.
“Wanna get in sweetie?” He asked.
“As long as your ok with special girls like me.” I replied confidently.
“I prefer them” he said with a smile.
Soon I was in the sleeper with him, him butt naked and me with my dress hiked up above my hips. We were rolling around together making out and dry humping, he was treating me like a real girl! He laid me on my back, kissed me softly and slid his 6 inch cock into my freshly fucked hole missionary style. Slowly he slid in and out of me, kissing and sucking on my neck the whole time. After a bit we rolled over and I was on top of him, straddling his waist with my knees on the mattess.
I couldn’t get enough of it! I was rocking my hips back and forth, feeling his cock inside of me at every possible angle while I moaned like a sissy whore. Soon I could feel him tensing up.
“Can I cum in you?” He asked politely.
“Please do” I said as I leaned forward and kissed him deeply.
I felt him begin pumping harder into me and soon that wonderful feeling of hot cum shooting inside of me was back. We kissed each other tenderly for a few more minutes until he went fully limp and his cock slipped out of me. Once we were dressed he offered to give me more money but a dollar is all I would accept. Soon I was back in the parking lot, nearly running to find another truck with a red light on. -->
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