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My Step-Sissy

Post #1

My Step-SissyThe Step-SissyI attached the brand-new leash on her thin, pale neck. The word "Slut" in fake diamonds adorned the front. My sissy was on all fours, wearing her favorite pink wig and a leopard body stocking. Her shapely little ass beautifully complementing the outfit. Between the cheeks and beneath the leopardskin, is the visible outline of a small dildo inside. Done up in full make-up, flat-chested, with her fake thick-rimmed glasses on. My nerdy sissy girl. She liked being walked around the house with her toy in her hole before we fuck. I gripped her leash and guided her towards the upstairs bedroom for her daily dicking.I always tried to instill manly values in my son. I tried taking him out to baseball games, to wresting matches and all that...But he never took to any of it. He just spent all his time sitting on his ass on the computer. I always thought he was a nerd. A nice, smart boy sure, but still nerdy. He had a skinny, even feminine body, I thought it was pretty sad at first. I'm 36 now, 220 and fit like an ox. Never have had a better period in my life. My step-son is 22 now. I married his Ma about 6 years ago. Met her at a hot nightclub in the city. Figured she was slutty from square one, turns out she fell for me hard and she was. She loved anal, got dripping wet from it. We're divorced now and the k** is living with me now. Has been for 4 months.My son always had the vibe of being a pushover, sort of a weak k**. But he was socially active and sometimes had friends over. I was fine with that. Until he started smoking weed in the goddamn house. After I divorced his mom, I got a little harder on the k**. I didn't want to hit him when he fucked up, but I wanted to discipline the stupid twerp properly. So I took to doing to him what my dear old dad would do to me when I fucked up. The next time I caught him and his friend smoking in the bathroom, I kicked his stupid nerd friend out and threw him on the couch. "You're a fucking immature k**, so you're going to get it""Dad, you can't throw me like that! That's abuse""And you're doing d**gs in the house"I pulled down at the waistband on his pants hard, he grunted in pain but I didn't give a fuck. "Dad, what the shit"Now this stupid asshole is cursing in my house. I pulled off his little undies and pushed his back down, completely in control even if the skinny k** struggled. I slapped his right cheek with excessive force. "Agh!"Then the other little white cheek. Harder this time."You still want to curse and do d**gs in my house you little shit? I'm tired of this."Whap. Whap. His pale ass started to turn real pink and he even stopped struggling. Started crying into the pillow on the couch. Four more even slaps on each cheek and I ceased. He got the point. He didn't sit right the whole next day. He straightened up for awhile after that, he wasn't allowed to have anyone over and I was done with that smoking shit. Of course he fucked up as teenagers do and whenever he did I spanked him harder. He may have turned into a good boy all of a sudden, however I noticed he never hung out with any girls. Not even a date. And he has been locking himself in the room, almost all of the time...The next morning he was off to class, so I decided to check out the search history on his computer. Turned it on, got on his browser and then...I found some freaky shit. I said the searches in my head. "2 BBC fuck white boy" "Sissy gapes" "Sissy gangbang black" "Big black daddy fucks white boy" "Daddy fists sissy boy" "Daddy son anal".I feared that my son was in fact turning into me at that age...Because I was a pretty slutty k** back then, I was always playing with myself and trying to find things to use as sex toys around the house. Was too shy to buy a dildo. I was always bisexual, however I found a exhilaration in being with other men even from an early age. I couldn't resist the temptation after I found a tape of Leather Hunks 3 among the straight porn in my father's stash. My first encounter was with my high-school coach. The guy was a balding 40-something. He was a total bear. I was in the 11th grade at the time, hadn't done anything with girls yet. I was just like the k**. Watched a lot of gay videotapes at home, got some real crazy ideas that swam around in my young promiscuous brain. I had a fight with another k** in gym. Some jock guy who bullied me sometimes. Had to stand up for myself, the coach even said so. Then he said that I should let him know if he could do anything to help me take the edge off. Looking at me up and down the whole time as I sat in his office. I caught on to his signals and before I knew it, I walked over to coach and smiled at him, when got up from his seat and smiled back, I knew what I got myself into. Before I knew it I had coach's 9 inch jammed in my mouth. Even let him blow his load on my face like in the movies. Loved that shit. There were still 10 minutes left in class, he was giving me some tissues when he said "Lemme get you off, baby, get on your front, stick that beautiful butt at me." I was worried we would get caught, but I obediently did as told. On all fours with my stiff young cock throbbing madly. I could feel the precum leak like a faucet. I could feel him gently lick my ultra-sensitive cockhead. He took his grasp on my cock even further by pulling it backward between my legs. "Are you flexible?" He asked. I gave him a sultry "mmm-hmm". He pulled it back slightly and started stroking downward, my first milking. I let out gasps and light moans as he expertly and rhythmically pumped my cock. Just as I felt I was going to reach my limit, I felt, for the first time, a tongue encircling my virgin pink hole. It tickled, I let out a little femmy giggle like, "What are you doing?" But he kept at it, pumping me while practically making out with my asshole. His tongue started going deeper. I realized this was starting to feel really fucking good and started getting loud with my moans. "Shhh, baby we gotta go, you're gonna cum now okay?""Awhh, mmm, okay sir."He pumped my shaft harder and faster, my cock was completely on edge when suddenly he said,"Shoot in my hole, put it in boy"I stood up without saying anything, I never, ever, did this before. He was bent over his desk now, his athletic thighs spread like he was getting searched. His tan skin contasted his paler, finer smooth butt. I rubbed my leaking boycock on his asscheek, guiding it toward his brown manhole. I spit on my cock like I learned in the pornos, he fingered with three fingers, spreading his entrance. It went in easy. He grunted as I put one inch and another up his tight sexy butt. Then I pulled and pushed his warm hole loose. I was closer than ever and didn't want to stop but before I could ease up, I shot hard. Pushing even deeper, with my coach who I saw everyday, grunting and moaning like an a****l. His asshole tightening as I went deeper, almost seeing how far I get my load up his sexy ass. He turned backward and grabbed my neck. Kissing me hard and wet, our tongues practically dancing. My cock flopped out of his butt, my cum followed. He was limp on his desk, still bent over. He pulled his cheeks apart, presenting. Now every stud I fucked had to take my load up his ass.It was late at night, the door was cracked...Which I found to be very strange. When I looked in, his eyes were closed, legs spread in my very direction, his right hand working his stiffy while he rubbed his asshole with the left. I thought back to my method of discipline I had relied on for so long...I remember when I caught him smoking in my bathroom, door open, not even trying to mask the smell. First fuck up in months. Pulled his pants down to find a rounder, shapely butt underneath. I hesitated and had flashbacks to the twinks and the sissy boys who I watched in my pornos. His ass was pretty sexy like theirs. Then I shook myself out of my daze and laid the hammer down. He stuck his face in the pillow, didn't scream or flinch as the blows landed on his cheeks. They were a brighter red than they have ever been and yet I could feel his ass push up against my hand, I could recall a slight moan beneath the pillows as I rubbed his baby-soft bottom to relieve some of the pain. I decided to figure out for myself at last.He left the door open, again. This time I knew exactly what my son had transformed into. It was 1:00am. On a school night and I hear some creaking upstairs in the guest room. I could see that the light was on. I crawled on my hands and knees so that he wouldn't see me. Got right up to the door and peeked ever-so-slightly. There he was.He had a shiny ebony big black dong, attached to the bed via a suction cup. He was on all fours, wearing a blue bra and panties. His mother's I know. And a blonde wig...I continued watching to my own confusion. His computer was open in front of him. Recording. He guided the exceptionally long dildo into his entrance and with surprising expertise, sank the cock deep into his hole in less than a second. Then he pumped forwards and backwards. Over and over. I was shocked. I watched with a massive hard-on. I had always known that I secretly enjoyed spanking him but...He was my step-son. I figured, whatever, he isn't my blood and that boy has gone completely sissy.I pushed the door open slowly. He looked up faster than a deer in headlights. He slid away from his sex toy and it popped swiftly out of his bottom. "Oh my fucking god dad!"He said in an obvious feminine voice. He was caked in make-up. I was startled at how passable my boy turned out to be. He even stuffed the bra to make his "tits" look huge."I'm so sorry dad, please"Like magic I turned into my young self again, forgetting all about my step-son. Only seeing the slender, shapely sissy girl in front of me. "Get on your fours, stick your ass up, girl. I know you want to be spanked you little sissy slut!"I had this delicious butt all to myself. On all fours, his ass was particularly round, both cheeks had smooth dainty white skin. His boypussy was shaven bald, he laid still but his hole seemed to be energetic enough. Lube flowed lightly from his velvety pink hole as he continually winked his asshole. Whap. Whap. Whap. I slapped him so hard he let out little tiny yelps, just like the sexiest sissy boys do. He was really getting me hard and passionate. Another last smack, the cheek stopped jiggling. I grabbed his big black cock toy and shoved the head right in his butt. "Mmmmmm, Daddyyy, please stretch it, stretch it daddy"His sissy voice needed work but he would be taught soon enough. I gave me another inch, then another. He groaned as it sank deeper and deeper inside. I could feel his asswalls tighten, his prostate pushing my efforts back. "Loosen up. You're my toy now, get this dildo."He continually pushed. Smacked his stupid ass and pushed in harder. "Ogh, mmmm fuck, daddy! That hurts..""Shut up bitch..You were taking that big black cock like a pro when I was watching.""yes..sir...hmmm...oohh..."He didn't like it."Fine, push it out boy, push it." Bit by bit the toy slid out. Then it stopped, I saw his pussy pucker and tighten over the cock. It went in slightly and then out slightly as he pushed. An inch inside then out, the end of the dildo bounced and wiggled around until it slid out completely. Shiny with juice. My son's fuckhole was sloppy with lube. His cheeks were recovering already from his spanking, turning it a faint pink now. All this time, obediently remaining on his fours with his slender feminine back arched perfectly. He shook his ass, presenting to me. I put my face right up to his shiny white ass, took a hot breath on his super-smooth pussyhole. He let out a light prissy moan. I immediately dove in as deep as I could with my thick tongue. His asswalls were hard to reach after that toying, but I found everytime I licked them, he let out the softest and the sexiest little noises.I grasped his soft cheeks in each hand, his ass ever-so-slightly wiggled on my face, as I was nose-deep in his crack. Without words, I separated myself, turned him around on his back and moved his panties out of the way. I buried my face between his legs, his big sagging boyballs resting on the bridge of my nose. Gave his thigh a smack while I licked. I was hooked on his moans everytime I went deeper, licked his rim and spit on his pussy. Got a grasp on his cock, felt the pulse inside as it throbbed hard. Leaking tons of sweet cum. Had to separate myself from his sweet asshole to give my tranny boy's big dick some attention. "You got a big dick, boy. Real big balls for a sissy, babe.""I play with them too much.""Fuckin' right you do."Hot breaths on his pink stiff cockhead then I went to work giving this boy his reward. k** couldn't keep his mouth shut moaning like a slut. Loved that. Reached underneath his bra and pinched his little nips. Rubbed his skinny shaven body. Took his pulsing dick out of there, then gave his super tight hole a lick from the end of his crack to the tip of his dick. Cum leaked out of his beating sissy cock. I pumped it while I sucked. From base to head. Long slow sucking, like I wanted to suck the cum out myself. "Mmhmm, mmhmm"I took it out of my mouth. "Gonna shoot?""Yesss, oh my god sir, you make me feel so pretty and sexy. Please make me shoot"After about a minute of stoking his now shiny penis, licking his nips, cradling him in my arm as I use the other to get him off. He's breathing hard now and I feel the cock pulse harder, I pulled the skin down and he spurted all over his jaw, neck and chest. He gasped as if he was going to have a heart attack, real dramatic. Again and again, his cock pushing hard after every shot. I could feel him go soft, he moaned femininely and sucked on my neck. I looked at him in his glitter lipstick, thick makeup and purple eyeliner. His fair skin was shiny and wet with his own load. I looked in his eyes after he separated himself from sucking on my neck and I gave him a wet kiss on his little girly lips. Then a sloppy kiss. Licking everywhere, cleaned his jaw of his load. He pumped my big curved cock then he stopped kissing and used his mouth for awhile, sucked it like a pro. He probably practiced on that giant toy the way he deepthroated my steel-hard dick. I was on edge already, I was about ready to spurt in this little bitch boy's mouth. He tried to mouth something so I pulled out, threads of wet saliva with it. "Cum inside my mouth." He pleaded, with half-closed eyes and a still wide-open mouth. His mouth was almost indistinguishable from his ass, because this boy was fucking excellent. Way too sexy to hold this load in any more, so I spared him his gagging for a moment so I could pull slightly, giving him just 3-4 inches of my cock before blasting my sperm down his throat. "MMMMM, MMMMMMMM" Was all the noise the pretty slut could make. He sucked hard at the head of my dick and took it alright at first, but eventually had to spit. He and I needed to clean up.Took a shower together, couldn't take my hands off his body even without the sissy get-up. He hugged me, rubbed my body and touching my package with his. We had a laugh about it after, considering he told me he was bisexual and had wanted to fuck me since I started spanking him. He really liked being spanked, made him feel like a disobedient girly boy he said. Apparently the way I spanked him kinda, sorta gave away the fact that I actually enjoyed it. So he looked forward to it. Oh well. Told me he had been wearing girl's clothes since he was 10.A year later now. It's close to Christmas and my boy, or rather I should say girl, has really come around. I've never been a more fit top, I make myself hard sometimes. I'm leading a more active sexual life than ever. But my favorite time is at home with her. She's home from her college class now and as we do every day at 5, she dresses up in her pink wig and leopard bodysuit, ready to be walked. We're up in the bedroom now, I'm rubbing my face in her bulge, smelling the sweet strawberry lotion on her skin. I work my way up to her neck. She has two hickeys now from this but that's why she's my sissy. I suck on her neck and stick my thumb in her mouth to suck. The dildo is still in her asspussy, I feel the end through the outfit and push it in and out. We're going to fuck like we do every night. Or so she thinks, because my new black friend with a massive floppy dick is about to meet her acquaintance.
04-07-2021, at 02:30 PM

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