saracaptions: [i’m very proud of the story and hope everybody enjoys it] Fetlife Sissy Fantasy(MM, S

saracaptions: [i’m very proud of the story and hope everybody enjoys it] Fetlife Sissy Fantasy (MM, Sissy, sex) I opened the front door and he walked into the house like he owned the place. His expensive dress shoes tapping softly on the white faux-marble tile of my foyer. He stopped, turned to look at me, and inspected me up and down. The maid outfit is my favorite. The black patent leather high heels fit me well and I love how wonderful they feel on my stocking feet. The stockings, white cotton lace with little pink and blue roses stitched into them, ran up my shaved legs and disappeared underneath the frilly black satin skirt with the white ruffling that flowed out from underneath. Tied around my waist and hanging down the front of the skirt was a matching black satin sash that read “Room Service” in white letters. Above the skirt I wore a matching black satin top coat with red lace trim running around the neck and down the front paralleling the buttons that held the coat on. My hair, which I had been growing long for months, was pulled up in a bun at the back of my head and on top of my hair was a white with black trim maid’s hat. I wore just a little eyeliner, a smidgen of blush, and a layer of bright fire-red lipstick as he had requested. I looked every inch a proper French Maid. If, your idea of a proper French Maid is a 19-year old boi slut with a 6-inch rigid black dildo up his ass. “Get me a drink.” It wasn’t a request. I bowed my head meekly and walked towards the kitchen, my 4-inch heels clicking on the white tile. He followed, and I could feel his eyes on me as I walked. We entered the kitchen and I stopped, turned towards him, and extended my arm towards the bar area like Vanna White showing off letters. “What would you like Sir?” “Scotch. With ice.” Opening the ice bucket, I placed two cubes in a glass tumbler and poured him three shots of my best scotch. $120 a bottle, but I was sure this night would be worth it. Handing him his drink I raised my eyes from the floor and looked at him. He looked even more handsome than he had in his photos. He was at least 6’2 and trim. With greyish-green eyes, a strong chin, and a graying goatee that extended slightly below his chin. He wore a black dress suit that was obviously expensive and tailored to fit him perfectly. His tie was as red as the sun and I couldn’t help thinking how beautiful he looked. And he was standing in my kitchen! And… if I was a very good girl and passed his inspection, he was going to fuck the hell out of me. “What is your name?” “Claire.” I said softly. “Well, Claire, you have a terrible house. It is cheap and garish, and I am not sure what kind of girl would live in it, but I imagine she is cheap and garish as well.” “Yes Sir.” “Are you cheap Claire? Are you a cheap girl?” “No Sir.” “You think not? Well, I think that remains to be seen. Let me ask: are you a good girl Claire?” He walked closer to me with each question he asked. I began to tremble with excitement. “Yes Sir. I am a good girl.” “Really? Let me check and see. Are you wearing underwear?” “No Sir. You instructed me not to wear any.” He was standing right in front of me now. His cologne, a strong and fragrant sandalwood, filled my nose. “Lift the front of your skirt Claire and spread your legs for me.” I spread my legs as he asked and lifted my skirt up for him to see underneath it. My tiny 2-inch cock, caged and locked in pretty pink plastic and tied up with a bow around it, was easy for him to see. “Well… you are certainly a girl. That is plainly obvious.” He smacked my face. Softly, but hard enough to leave a little mark. Precum dribbled from my dick. “I told you to lift your skirt and then spread your legs. Not the other way around. Claire, you will obey my directions exactly or be punished. Do you understand?” “Yes Sir. He walked around behind me. His eyes roaming up and down my outfit. He stopped directly behind me. “Walk to the kitchen island, grab it, bend over at the waist, and let me see what your ass looks like.” I walked to the kitchen island, placed my hands on it, bent over at the waist, and my ass cheeks popped out from under my skirt for him to see. “Well, Claire, this certainly isn’t the ass of a good girl.” He walked over to me and put his right hand onto my bottom. I could feel him massaging my smooth hairless skin and, for a moment, all felt right with my world. Then his hand left and returned with a violent smack on my exposed ass that pushed me forward towards the island. “Ooh…” I said in shock. “Shut up until told to speak.” His hand massaged the skin on my ass again and then again drew back and smacked me with enough force to bring tears to my eyes. He did this five times and by the end of the fifth one I was choking back little cries of pain. He put his glass of scotch, now half empty, onto the island beside me and placed both hands on my ass. He peeled apart my cheeks to find the black dildo I mentioned earlier. He knew it would be there. He had ordered me to go to the local sex store, buy this exact model, and have it inside me when he arrived. He had planned everything for tonight. But I only knew he was coming over. Not exactly what he planned to do. “Look at this. You followed directions. But this… this is not a thing that a good girl would wear. Good girls don’t put sex toys into their pretty little asses. Only a bad girl does that.” When he said “bad girl” a little more precum leaked from my caged cock and it strained against the plastic holding it. I felt his thumbs touching the dildo and he used them to push it a little further into me as deep as it would go. “Do you like that girl? Do you like me playing with the big toy I ordered you to shove up your ass?” I opened my mouth the speak and then shut it again. I hadn’t been given permission yet. “Ah… smart little one aren’t you. You may answer me.” “Yes Sir. I love it. I love you playing with the big toy in my ass.” “Good. That is good. Let me tell you Claire…” he said as he walked around to stand beside me “That will not be the biggest thing going in your ass tonight. You know that right? You may answer.” “Yes Sir.” “Good. I now give you permission to speak. You may answer any questions until I say so. Understand?’ “I understand Sir.” “Show me to your living room.” I stood up and bowed. Then, with him following me and his drink in his hand, walked back out into the main hallway and down into the living room. He stood looking around at the room for a few moments. “Open the curtains.” My living room windows face out onto the front yard and, even though it is December and cold outside in Northern Virginia, I knew that if the curtains were open anyone walking by would be able to see in. That scared me to death, but I opened them anyway. “Now come here and face me.” I walked over to him. As I said he was easily 6’2 and towered over me at 5’4. “Look up at me.” I did so. “Good. Now on your knees, mouth open, tongue out.” I followed his directions exactly. I got to my knees, opened my mouth, and extended my tongue out for him. He stepped a foot closer and shrugged off his suit jacket. He tossed it on a nearby chair. “Remove my shoes.” I untied his dress shoes and helped him slip them off his feet. I placed them off to the side. “Remove my pants. Gently place them over the chair on your left.” With my hands shaking and my mouth dry, I reached up to unfasten first his belt, then unbutton his pants, lowered his zipper, and pulled his pants down so that he could step out of them. Then I leaned over and draped the pants across the chair carefully so that they wouldn’t wrinkle. Only then did I turn and look up into his crotch. It was big. Bigger than I had expected it to be. His underwear was tight and could barely contain it. The head was clearly standing out against the fabric and the length of it ran down almost out the bottom of his boxer briefs. And he wasn’t even hard yet! “Remove my underwear.” Hooking my fingers onto the sides of his underpants I pulled them down in one smooth motion just like I had seen girls do in porn videos. And, just like in those videos, his cock sprang free and actually was long enough to brush against my face leaving a trail of his precum from my lips up to my eye lashes. It wasn’t a “porn cock.” Nothing like the 12-inch monsters we all see in videos. It was flaccid, but I estimated it to be at least eight inches long and thick enough that I wouldn’t be able to put my thumb and index finger around and touch them. “Good. Put your hands on my ass, lean forward, and swallow it as deep as you can like a good girl.” My little cock jerked, and I came against the plastic cage that held me. I could feel it dripped down and onto the floor below. I ran my hands up his legs, grasped his ass cheeks, and leaned forward so that my tongue touched the tip of his cock. Angling my head up I leaned further forward and sighed as his cock rode up my tongue and as deep into my throat as I could take it. Which, since I have been practicing my Sissy Exercises with a 7-inch dildo, was pretty deep. Once he was as deep inside me as I could take him I stopped. I was following his directions. “That is good Claire. I know you want to close your mouth. I know you want to run your tongue around me. I know you want to suck. That is what girls like you always want to do. Nod if I am right.” I gently nodded. “How does it feel Claire? Does it feel as good as you thought it would? On your knees in your pretty sissy clothing and kneeling before a real man? His big dick in your mouth? Does it feel good?” I nodded again. “Then blow me, Claire.” He was barely hard when I started but I closed my mouth around his dick and began to suck him off. Moving my head back and forth, tilting it side to side, sliding my mouth up and down the length of him. My tongue fliting and jerking over his head as I worshipped him orally. I did exactly as I had seen and practiced while watching porn. “Mmm… that is very good Claire. Are you enjoying this? You may nod.” I nodded enthusiastically and resumed my work. His dick grew in my mouth. “I am sure you are. My big dick in your mouth. The window blinds open so that your neighbors can look in and see you dressed like the pretty little bitch you are. I bet this makes your little boi clit just leak and leak.” He was right. My cock was straining against the pink plastic cage and I was certain that I even grazed it I would cum like crazy. I took my mouth off of his cock and began to lick it. First the sides, then the bottom, like an ice cream cone. He was fully erect now and I was right about it being eight inches, but wrong about the thickness. It was even bigger! Like a potato chip can! Despite my deep throat practicing on the dildo I couldn’t even get halfway down his dick due to the width. “Very good. Now, put my hairy balls in your mouth as well. Use your hands to jack me off.” I did as I was told and began to juggle his balls with my tongue and ran both my hands up and down his saliva-covered cock at the same time. “That is enough. Stand up Claire.” I immediately stopped my work and rose to my feet. “Turn around and bend over the table behind you.” I was shaking like a leaf from the excitement and fear. The moment I had been waiting for and dreaming about for years was about to come true. I was going to be fucked by a real man! There was going to be a dick inside me… pumping in me… squirting cum up into my ass for the first time! I did as he told me and as I assumed the position I felt him lift up my skirt and place his hand on my ass. Then he drew back and hammered his hand onto my ass with a massive SMACK that nearly drove me over the table. “Ooof…” I said as tears came back to my eyes. “Did that hurt you Claire?” “Yes Sir.’’ “It won’t hurt nearly as much as what I about to do to you.” I felt his fingers pry open my cheeks and hook around the suction cup that formed the base of the plug. Without hesitating he yanked it right out of my ass in one smooth motion. “Aasshhhhhh….” “Now spread your legs and get ready to become a woman.” I spread my legs apart as I felt the tip of his cock slide up over my ass cheeks and poke its way between them. He stopped right at the opening and paused. Then I heard the squirt of a tube of lube and I could hear him rubbing it on his cock and the crack of my ass. He grabbed my hips and pulled back while thrusting himself forward. There was some resistance, actually a lot of resistance, but he was a real man and very strong and within two seconds he had popped the head of his cock inside me and driven himself at least three inches in. He was right. It hurt like hell!. But it also felt wonderful! Like I was complete and whole for the first time in my life. He pulled back a little, maybe an inch, and drove himself forward again and this time he didn’t stop at 3-inches. He wrenched and pushed and shoved all eight inches as deep inside me as he could go. This time it did push me up and nearly over the table and I banged my caged boi clit on the edge. And, I was right, just the touch of the edge of the table sent my cock into spasm and I came immediately. “Oh god oh god oh god…” I cried as little squirts of cum leaked through the cage bars and ran down my leg. There was no hiding what was happening as my whole body jerked and spasmed when the orgasm ripped through me. “Oh, there is a good girl. Losing her virginity and cumming at the same moment. I’m proud of you. Now… let’s see if you cum again when I pump you full of jizz you sissy bitch.” He pulled nearly all the way out and drove himself in again, banging me against the table once more. Then out and in again. I braced my hands against the edge of the table and pushed back as he came in for the next thrust. We quickly got into a rhythm with me pushing back and him thrusting forward and the pain that I was feeling subsided a little and was replaced with pleasure. I quietly came twice more as he pounded his cock into my hole with increasing ferocity. After a minute or two (I totally lost track in the haze of pleasure) he spoke again. “I am about to cum. How does it feel to know a real man is about to cum all up in your ass you little bitch?” “It feels great Sir. Make me your breeding bitch please…” And with that he came in my virgin ass. I could feel it as the hot jets of sticky cum sprayed inside me and squished around. He stayed in me for a moment, letting his cock jerk and emptying everything he had inside me. When he was finally done he pulled out with a tiny popping sound (maybe I imagined that) and walked a few feet away. I collapsed across the table trying to catch my breath. I could feel his cum leaking out down my butt and dripping down my legs to mix with my own. “Whew! That was good. You are a good little piece of fuck meat Claire. I’m going to have to come back again and have that ass.” “Yes Sir” I replied. I heard him move off into the kitchen. The fridge opened and the sound of a beer bottle being popping open. He walked back into the living room and I turned and sat down on the floor to look up at him. He had a beer in one hand, and was taking a deep drink, and a dish towel in the other that he was using to clean off his dick. When he was done with the towel he tossed it in my face. “Clean yourself up Claire.” He put his pants back on and took a seat in the chair to watch me wipe the saliva off my face and then clean up the floor where our juices had mixed. When I wiped the cum off my legs he stood up and offered me a hand. I took it and he pulled me to my feet. He put his right hand on my cheek and brought my eyes up to meet his. “Good girl. Now get a new outfit and a bigger plug before I see you next week. I will text you when I am coming.” He turned, walked out of the room, and left through the front door. I went to the bathroom, turned on the lights, and looked at myself in the full-length mirror. What little makeup I had left was smear all over my face. My pretty maid outfit was in disarray and there was still some cum drying on my legs. I was finally a real sissy girl. The End -- source link

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