Becoming A Sissy Slut Part 1
- 2 years ago
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Becoming A Sissy Slut (part 2) free porn video
I awoke Sunday morning alone in Kassy’s bed, still in the tight mini skirt, my ass was deliciously sore bringing back a flood of memories from last night. I had spent the evening in full drag dressed as a slut and serving my mistress’s rubber cock followed by swallowing my own cum. It was hands down the best night of my life, I had never came so hard, and the rush I felt while serving her was a high that I’d never known.
I rolled out of bed and stood up, my wig had fallen off in the night and my mini skirt was wrinkled and riding up. I decided I probably didn’t need to be wearing it anymore and pulled it off up over my head. At the foot of the bed I noticed the clothes that I had worn to Kassy’s house the day before were neatly folded. Along side of them was a separate stack of clothes; a hot pink pair of yoga pants, a black pair of panties and a white Victoria’s Secret t-shirt. ‘That’s weird that she left her clothes here next to mine’ I thought to myself. ‘All is her other laundry is put away.’
I put my jeans and hoody back on then stepped into the master bathroom to take a look at myself. I looked like a wreck, my make up was smeared everywhere and I had a few cloudy black streaks running down my cheeks from when she gagged me with her cock and a few tears ran from my eyes. I scrubbed and scrubbed with soap and a wash cloth and got the majority of it off then decided to head to the kitchen and see Kassy.
“Good morning sweetie” she said over a cup of coffee.
She was sitting at the kitchen table wearing a pink hooded sweatshirt and the same extra short maroon shorts that she had been wearing the first time I was in her house.
“Have a seat Ryan, we need to talk” she said calmly as she pushed a chair out for me with her foot across the table from me. “Did you enjoy yourself last night?”
“Umm yes I did, very much so actually” I replied while looking down at the table, half embarrassed from last nights events.
“I know you did sweetie, I’ve never seen someone enjoy that so much.”
“You’ve done that before?” I asked her.
“Well a few times, why do you think I already had the strap on? Ryan, I have a confession to make. In the last few years I have developed an infatuation with owning and training a little sissy. It consumes me. I think about it night and day. That’s why I sat next to you in the bar when we first met. I spotted you from across the room. Your small frame, cute face and delicate features make you a perfect candidate. I was just hoping that it would be something you enjoyed and I would that say last night is clear evidence of that.”
“Yeah I guess...” I said unsure of myself “But I mean what more is there to do? What do you mean own and train me?”
“Ryan I want you to live with me for the next month. You are laid off from work, you don’t have any family or friends here, all of your bills can be paid online. My salon pretty much runs itself so I’m only there 5 or 6 hours a day. I can help mold you into the perfect sissy and you will find it so much more fulfilling.”
“Really? You want me to stay here for a month? A like, be your boyfriend?” I asked her in amazement.
“No Ryan, you will not be my boyfriend. You will be more like a girlfriend who’s only job is to serve and obey me” She said matter of factly.
“Well I don’t know...”
“Remember last night? Wouldn’t you like that all day every day?” She asked eagerly.
“Well yeah, I really would. It was pretty incredible. I guess that would be fine with me” I said, tentatively accepting her offer.
“For real?” She asked with a huge smile.
“Yes, yes I’ll stay here with you for the next month.”
“Great! I’m so excited!” She almost jumped out of her chair with joy. “I was hoping you would agree so I took the liberty of printing this off for you to look over, this is a list of rules for the next month.”
She walked over to the counter then returned with a piece of paper and handed it to me. It read as follows:
*SISSY SLUT RULES*
-Sissy will always address master as Mistress or Ma’am
-Sissy will not wear any male clothing or ever refer to themselves as a male
-Sissy will remain plugged and caged at all times unless master states otherwise
-Sissy will obey all commands from master without question, complaint or hesitation
“What does plugged and caged mean?” I asked her after reading the list of rules.
“Plugged means you will keep a butt plug in your sissy hole, this will help to train yourself to take more and to keep you ready at all times. Caged means I will place a chastity cage on your little dick, it’s just a small device that will keep you from cumming too quickly and ending our sessions before we are ready to be done” mistress answered my question.
‘Well, that doesn’t sound too bad I guess’ I thought. “Okay, this works for me” I said.
Before I could even blink she unleashed a powerful open hand slap across my left cheek. It startled me and stung like hell. I stared at her with my mouth open in shock.
“Rule number one, always address me as mistress or ma’am!”
“Yes ma’am, I’m sorry” I said while rubbing my cheek.
“Now, I want you to take all of your clothes off and follow me.”
“Yes ma’am” I said somberly, standing up and disrobing in the kitchen, I placed my clothes on a chair and followed her into the bathroom.
On the bathroom counter she had the wig I had worn the night before, and an entire make up kit sitting there along with a lap top.
“This is for you to use sissy. In the shower you will find razors, shaving cream, and an enema bulb. You are to shave everything below your eyes every day, no exceptions. I also expect your sissy hole to be squeaky clean inside and out. I want you to go on YouTube with my laptop and learn to put on and remove your make up. You shouldn’t have any problem finding some tutorial videos.”
“Yes ma’am” I replied while looking everything over. I had become fully erect while standing there in the nude, I was hoping she would see it and we could have some fun but she didn’t appear to notice or care.
“I’m going to go shopping, there is a lot we are going to need. I took your debit card out of your wallet, you will be funding this transformation. When I return I expect you to be ready for my inspection.”
“Yes ma’am, I will be ready” I replied. This was all happening so quickly. How much money is she going to spend? What all supplies could she possibly need?
“Okay Rachel, I’ll see you after a bit.”
“Umm Mistress? Rachel?”
Before I could flinch she slapped my hard dick straight down with full force. “Ouch!!” I yelled as I dropped to my knees.
“You are not to question me you little slut! You are a slut now, not a boy. You will answer to Rachel” she spoke so sternly she was almost yelling, she turned and slammed the door then walked off. A few minutes later I heard her car start up and pull out of the driveway.
‘I guess I need to shower first’ I thought to myself and turned the water on. Once it was warmed up I got in and immediately started stroking my cock, replaying the events of the night before. The fullness of mistress’s cock buried in my ass was memory enough for me to cum almost immediately. Out of habit I shot my cum into my left hand and then poured it into my mouth, I swirled it around with my tongue and imagined making out with Kassy.
I shaved my entire body, which didn’t take long since it had just been done the night before. I found the enema bulb and quickly figured out how to use it, it didn’t take long to get myself clean however my cock was twitching with excitement every time I inserted the stem of the bulb into my sissy hole. Even though I had just came, the sensation of having something inside me turned me on so much I couldn’t help myself.
Next I fired up the laptop and quickly found some makeup tutorials, it took me a long time to get everything applied, and when I was finished I didn’t look bad at all. Not as good as when Kassy applied it the night before, but still quite passable. I put my wig on and fitted it then gave it a few strokes with a brush to get any tangles out. ‘Good work!’ I thought as i looked at myself in the mirror, still completely naked.
Once again my cock twitched with excitement. I was unrecognizable, I looked like a sissy slut ripe for the fucking. I instantly got rock hard once again. I decided to go jack off on Kassy’s bed since there was lube in the nightstand and being on that bed again would make the memories of last nights fucking that much stronger.
I laid down on the bed and grabbed the lube out of the drawer, poured some into my right hand, and began stroking my hard 5 inches. I had my eyes closed and was moaning lightly, writhing my hips up and down while fantasizing about my mistress pumping her hard cock in and out of my sissy ass. I nearly screamed when I heard the bedroom door swing open.
“What the fuck do you think you are doing?!” Mistress yelled at me.
“Well I was just-“ I tried to get the words out in a panic but she cut me off.
“Get over here, right now!”
“Yes ma’am” i replied as I scurried off the bed towards her.
“On your fucking knees sissy” she said with a scowl on her face.
Obediently I dropped to my knees on the carpet in the center of the bedroom. She took a few steps back and leaned her shoulder into the inside of the door frame. “So, you want to jack on your little sissy clit do you? Well then, get to jacking sissy.”
“What Mistress? I don’t understand?” I questioned.
“You heard me” She said with authority in her voice. “Get back to jacking off. I want to watch how a sissy strokes her pathetic. Tiny. Worthless. Little. Clit” she said putting a pause between each de***********ive word.
Slowly I began stroking my dick again, looking down at the floor, humiliated.
“Look up at me sissy. I want to see the shame on your face while you try to pleasure yourself. You probably can’t even cum while looking at a woman’s body can you? You can only cum if your thinking about big. Hard. Throbbing. Cocks.”
I began stroking faster hearing her insult me with her dirty talk.
“You know what sissy? I want to hear you talk about what a slut you are while you jack off, tell me what a filthy sissy you are while you rub your pathetic little clit. Then I want you to cum in your hand and lick it up like a fucking dog” she ordered me.
“Yes ma’am” I began stroking even faster now. “I’m your little sissy slut ma’am, I’m a cock loving sissy faggot, please give me cock ma’am! Stretch my sissy holes with your cock mistress! Ohhh fuckkkkk!”
I feverishly tugged on my tiny dick while it spewed a few spurts of hot cum into the palm of my left hand. Without hesitation I began lapping up my cum while looking up at my mistress.
“Fuckin pathetic” she yapped then turned and left the room.
I gathered my composure and washed my hands when I heard mistress call for me.
“Yes ma’am?” I responded as i entered the living room, my head hung low and both hands covering my genitals.
I couldn’t believe my eyes when I saw the living room, there must have been 30 shopping bags from all different stores. Mistress was sitting on the couch and had already opened a few packages and was removing their contents.
“Come here sissy, I thought it went without saying that you are not to try and get pleasure from your little clit, but I guess I was mistaken. This should prevent any future incidents.”
She grabbed me hard by the head of my dick and pulled me close to her.
“This is a chastity device, it will prevent you from having any masculine urges and will train you that your only source of pleasure now comes from your sissy fuck hole.”
The device was tiny and made of hard pink plastic. First she clasped a small hoop snugly around the base of my balls, then pressed a small pointed hood over my dick that attached to the hoop. The hood was so small and constricted that I wouldn’t have been able to get even 1/4 of an erection, yet it was open at the end so I could go pee. A tiny little metal padlock connected the hoop and the hood together, which she locked with a small key then put in her pocket.
“There we go” she said with pride in her voice and a smile on her face. “That will prevent you from any future urges you might have.
“Thank you ma’am” I said in my most obedient and feminine voice.
“Next I want you to take these into the bathroom sissy. When you have the largest one inserted, you can come to my bedroom” she said as she handed me a small bag.
“Yes mistress” I took the bag and headed to the bathroom.
Once in the bathroom I opened the bag to see what it contained. Inside I found a 3 pack of assorted sized stainless steel butt plugs and a small bottle of lube. I looked closer at the plugs, they were perfectly smooth steel and the flared end that stays outside was decorated with a pink heart shaped jewel. I took the smallest one in my hand, the widest point of the circumference was roughly the size of a quarter. I dropped down to my hands and knees on the bathroom floor, poured a bit of lube onto the pointed tip and touched it to the entrance of my sissy ass. As soon as I relaxed my ass and put the slightest bit of pressure on it fell right into place. I toyed with myself for a few moments then removed it and grabbed the next size up. It was a little tighter going in but similar results. I toyed myself a bit longer with this one as I was beginning to feel that insatiable hunger to have my ass filled. Last was the largest plug, and it was large for sure. The widest part was close to the size of a soda can and as I smothered it in lubricant I wondered if I could take it inside of me. More importantly I wondered how good it would feel once I did get it inside. I reached back and began inserting the tip, which was quite easy after the first 2 plugs. Once it started getting very tight I really focused on relaxing my entrance, focusing on how badly I needed something to fill the void in my ass. The stretching feeling started to hurt quite badly but as soon as I thought I couldn’t take anymore, POP, and it was inside of me. I sat there on my hands and knees for a minute catching my breath and enjoying the fullness. I stood up and checked my make up and hair in the mirror then opened the door to see what mistress had in store for me.
Mistress Kassy was standing in the middle of her bedroom clad in black shiny leather; she had on thigh high black leather boots that were skin tight, coming up to her mid thigh. A black leather corset had her tits pushed up to the extreme, showing every inch of her upper breasts besides the nipple. Her jet black hair looked even more shiny and spiked and leather gloves stretched from her finger tips to her mid bicep. Yet what caught my eye most about this incredible dominatrix was the 9” black cock strapped firmly around her waist. Similar to the dildo she had used on me previously it was extremely life like with a head, veins and a large set of balls below.
“On your hands and knees slut, crawl to your mistress” she said in a dominant yet calm voice.
“Yes ma’am” I replied as I dropped to the floor and began crawling towards her.
“Back arched sissy. You need to show off that little ass of yours so that it’s readily available for any cock.”
I obliged and arched my back as far as I could, trying my best to sway my ass back and forth as I crawled to my mistress then bowed at her feet. I could feel a tingle begin to grow deep inside my ass in anticipation of the upcoming events.
“Good girl Rachel, now I want you to run your tongue from the toe of my boots, up my leg and suck on these big black balls.”
Immediately I placed my tongue on the tip of the smooth leather then slowly began working my way over the top of her foot, up her shin, and along her thigh. When I reached the middle of her muscular thigh I got to the top of the leather then ran my tongue along her bare skin.
She tastes sweet, like a delicious tropical lotion has just been applied, and her skin is almost as smooth and tight as the leather boots. Continuing to work upward I tilted my head to the side and began tonguing her huge black rubber balls. Soon I had one of them in my mouth, sucking on it while swirling my tongue then doing the same on the other one. I couldn’t help but notice that mistress had no panties on, the strap on harness was covering her pussy but there was clearly no panties beneath it.
“Good girl, now open your mouth. Your throat needs practice” mistress said sounding pleased with me.
I sat back on my heels with my hands folded in my lap and opened my mouth, looking up at mistress with hungry eyes. She wrapped her strong hands around the back of my head as she had done before then began feeding me rubber cock, inch by inch.
This cock was much thicker than the one she used before, a dark chocolate color and ultra veiny. I noticed a small hose that ran from the base of it to a small rubber bulb that was attached to her hip. Before I could wonder what it was for she began thrusting 6 inches in and out of my mouth, touching the back of my throat with each thrust. Soon I was gagging with every other thrust and had spit running down my chin but mistress didn’t let up. She wrapped her hands around my head tighter and began pumping deeper, the head was forcing its way into my throat, cutting off my breathing with each thrust.
I could feel my stomach starting to tighten every time my gag reflex went off. I began frantically slapping my hand against mistress’s thigh in an attempt to ask for mercy.
“Take it you little sissy fuck!” Mistress exclaimed.
Right as I felt my stomach churn, out of the corner of my eye and through the tears I saw mistress reach for the rubber bulb on her hip. I gagged from deep in my stomach spitting thick bile and saliva around the rubber cock, coating the balls and my chin, running down onto my chest. Right then mistress pulled out and started rapidly stroking the big black dick. I was trying to catch my breath and gain my composure when I felt a shot of thick warm gooey liquid hit me in the forehead and start running down my face. I looked back up to see a second huge rope of cum shoot out of the rubber cock and hit me in the face; instinctively I opened my mouth to catch the rest.
More cum came out than I’d ever seen in my life, it completely coated my entire face. When it finally stopped spurting mistress looked down at me with a smile.
“Good girl! Do you like your reward that’s covering your face? Now, on to the next one” she pointed to the wall across the room.
I had failed to notice 2 more similar dildos suctioned to the wall across the room. Eagerly I began crawling towards them, I was in a hurry. I began craving having them in my throat, looking forward to a creamy reward on my face or in my throat.
I began sucking the cock on the wall to the right first, I was in a cock drunken haze, fake jizz dripping off my face, but all I cared about was pleasing this cock, even if it wasn’t attached to anyone. I heard mistress leave the room but I didn’t slow down, this wasn’t for her anymore in my mind, it was for me.
While she was gone I had began stroking the other cock with my left hand, lost in the moment. I heard mistress return to the room and walk up behind me.
“That’s a good slut Rachel...take all the cock...all you are good for is pleasing cock...take any dick that is offered to you...you are a worthless sissy fuck hole Rachel” she said into my ear in a low soothing tone.
For a split second I pulled my mouth away just long enough to say “Yes ma’am, thank you!” Then back to sucking.
Next mistress began slowly working the plug out of my ass, gently turning it back and forth before getting it out.
“Look at that gaping sissy hole...” mistress said. “Wide open and ready for any cock that wants to enter.”
I could feel mistress stand above and straddle me, the insides of her calves along my sides. With one hand on my shoulder and the other gripping the base of her big black rubber cock, she touched the tip to my gaping entrance then slowly started pushing it in.
I could feel the tip press in followed by the head, then the familiar POP sensation as the head made its way in and my ass accepted the black invader.
“Mmmmmm!” I moaned around the rubber dick in my mouth, half in pain, half in sheer ecstasy.
Gradually she kept feeding cock into my ass inch by inch. I felt the tip touch my inner walls, my bodies sign that this was deep enough, but she didn’t seem to notice. She kept pushing forward until the whole thing was buried in me. This time there was no warming me up to it, within 3 pumps she was thrusting 9 inches at a time into my sissy ass and I was loving every minute of it. I had a muscular tanned goddess crouched above me, slamming a black cock into me while pushing the back of my head forward onto the cock that I was sucking.
I was accepting the pain in my bowels as part of my job as a sissy slut, how I feel doesn’t matter as long as the cocks are happy. I could feel my tiny sissy clit pressing with all its might against my chastity cage but it was fruitless.
I was beginning to moan like a whore while my mistress pounded away on my ass. Even my voice sounded more feminine as she fucked away my manhood.
“Are you ready for your reward you fucking slut?” She nearly yelled at me.
“Yes ma’am!” I moaned back to her around the wall mounted dick in my mouth.
Her thrusts became even vigorous, her toned and defined ass muscles driving cock deep into me. Suddenly my eyes started rolling back in my head and my legs began trembling as I felt her unload a massive amount of hot sticky cum into my bowels. I was on cloud 9 and began sweating and panting even more. Somewhere deep inside of my soul I knew I had found my true calling, my euphoria.
She slowly withdrew her cock from my well used ass, I could feel myself gaping open and air flowing freely.
“Now, please both of these cocks with your sissy ass you little whore” she ordered me.
Rapidly I spun around as quickly as I could and backed myself up on the first dildo. It nearly fell in to my ready hole and I began rocking back and forth on it. Within a few minutes mistress squeezed the rubber bulb attached and dumped another massive load into my ass and the same inner feeling of emotional completeness took over me. At that moment in time there was nothing more in the world I could ask for.
I withdrew the first and repeated on the final wall mounted cock resulting in a third gargantuan amount of cum being deposited into my bowels.
As I pulled away from it and tried to control my body from the high I was on, mistress already had another command for me.
“Center of the room, hands and knees, legs spread wide.”
“Yes ma’am” I moaned as I slowly began crawling to the center of the room trying to keep all of the precious cum inside of me.
I assumed the position asked of me and felt mistress kneel down behind me and place her leather gloved hands on my ass cheeks, spreading them wide.
“This sissy hole looks well used but I believe it’s still hungry for more. Is that what you want you filthy slut? More anal abuse?”
“Yes ma’am, please use my sissy ass as you see fit”
“Good girl Rachel, sissy’s never say no to anything going in their ass, anything...” she said with a friendly tone as she began rubbing her fingers along my boipussy.
She inserted 1, then 2, then 3 fingers of which I could barely feel they went in so easily. Soon she had a 4th inserted and was working them in and out for some time. Slowly she withdrew her 4 fingers and reached over to grab the bottle of lube. She poured a liberal amount all over her entire hand then up her wrist and forearm.
“Relax now whore” she said in that low soothing voice.
I began shuddering with fear and anticipation as I knew what was coming. I tried my absolute hardest to relax my ass as I felt 4 leather clad fingers plus a thumb begin pressing against my entrance. The tight pressure began building and could feel myself stretching further and further as her fist made its way in. I could feel the lowest knuckles of her hand press through as the pressure and pain continued to build. I began moaning and whimpering like a true whore while she kept pressing inward. Forcefully she shoved harder and harder until I felt the pressure subside slightly and my boipussy clench tightly around her wrist.
The pain was intense! Mistress held her arm in place and softly began stroking my lower back with the fingertips of her hand that wasn’t buried inside of me. I was sweating, breathing deeply and nearly crying but I was loving every second of it. 1 week ago I was a normal guy and at this very moment I was a passable sissy slut with a muscular goddess’s fist inside my ass; and I wanted more.
Slowly the pain eased as my ass became accustomed to the girth if my mistress’s wrist. She began slowly opening and closing her fist inside of me, tickling my sissy g spot each time. Then slowly working her wrist in and out a few inches at a time.
“What a filthy slut, an ass completely full of cum and now a fist. Do you like that sissy?” She asked. “Do you like having your sissy hole stretched open?”
“Mmm yes ma’am!” I struggled to get the words out.
Without realizing it I felt my body naturally pushing back into her fist forward and back, essentially fucking her arm.
“Good girl, now that we have your hole opened up we need to work on your depth. Good sissy’s need to be able to take a good deep fucking. Do you want me to go deeper Rachel?” She asked like I had a choice.
“If you think I need it mistress, then yes please.” I said in a feminine voice.
Once again she grabbed the bottle of lube with her free hand and liberally poured it onto the right forearm of her long leather gloves. She began pressing deeper into me, roughly 4 inches past her wrist, her hand in a closed fist. She pulled back to her wrist then pushed in again harder all the way to her toned forearm. I moaned uncontrollably as I felt my inner organs being pushed for the first time. I could feel her fist deep in my bowels. She withdrew to her wrist then started rapidly pumping in and out of my ass from her wrist to her forearm.
I felt so full inside and it still hurt but I was moaning like a whore in heat. I loved my mistress destroying my ass, stretching me beyond my wildest dreams, pumping her arm in and out like she was trying to punch a hole in my intestines.
She kept this up for 5 minutes! My legs were quivering and my sissy clit was leaking a long string of pre cum out of my chastity cage. Gradually she began slowing down then easily removed her hand from my sissy ass leaving me gaping wide open.
“That’s enough for today slut, get yourself cleaned up.” -->
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