Inside the Mind of a Cocksucking Sissy
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Self-Sucking Sissy 3 free porn video
My step-sister Avery was dancing around her bedroom in a red thong and a lacy red bra when I peeked in through her open door. She checked herself out in the mirror, struck a few sexy poses, then danced around some more while looking into shopping bags and rummaging through one of her drawers. Even though I just blew a huge load outside with her mom, I was more than ready to go again. The only problem was that I was worried about how much of my dignity it would cost me along the way.
Avery was checking herself out in the mirror again. She pulled the front of her thong up, causing it to wedge into the crease of her enticingly bald pussy. Seeing her floss her cunt like that convinced me I was willing to pay whatever price she had in mind for any chance to play with her again. I stepped into her room and cleared my throat.
“It’s about time, my sissy little brother.” She fixed her thong, digging the moistened fabric out from between her pussy lips. “So, bitch boy, did you enjoy sucking yourself off in front of your mommy?”
“Step-mom,” I uselessly corrected her, knowing it wouldn’t do any good to insist on that distinction. “But, yeah, actually. I liked it more than I thought I would. Even though they’re fake, your mom has fantastic tits.”
“You mean the only man-made objects you can see from space?” she sneered as she laid out some delicate lingerie on her bed.
“Ha, yeah. Also, did you know your mom is a big time squirter?”
She looked at me like I was a clueless idiot. “There’s not a lot about my mom that I don’t know.” Avery picked up a pair of blue panties, then came to me and held them up by my face. “These go nicely with your eyes.” Out of nowhere she slapped me across my cheek. She wasn’t playing, either, it fucking stung. “This is my playtime now, I don’t want to talk about your slutty whore of a step-mother anymore.”
“You brought her up,” I complained and nursed the side of my face. The pain faded quickly when she turned and I got a good look at her pretty much perfect ass with nothing but a thin strip of red filling her cute butt crack.
“Get rid of those ugly shorts,” she ordered.
I quickly did as she told me, happy to once again put my erection on display for my super sexy step-sister. It’s funny how just having her seeing my dick was almost enough to get me off.
“Turn.” She came up from behind and reached around me.
I could smell her perfume all of the sudden, or maybe it was just her body wash – whatever it was, I loved it because it was her smell. Her soft skin brushed against mine, causing my dick to flex with urgent desire. I thought back to when she actually put me in her mouth. I prayed she would do it again.
“Hold out your arms.” She slipped the shoulder straps of a brand new, powder blue bra over each of my hands in turn. This was what I was afraid of. She settled the bra over my chest then fastened it in the back. “Let me see.”
I turned around, feeling my cheeks grow warm with embarrassment.
She fidgeted with the bra. “Pretty good fit.” Avery fussed with the front, reaching in and pinching each of my nipples really hard, then shifting the bra again. “I thought you’d fill out those A-cups a little more. I’ll have to talk to Mom about getting you on estrogen.”
I scoffed at that, but the serious look she gave me made me wonder if I should be more worried.
“Put these on, cum sucker.”
I took the blue panties she handed me and put them on. They were way too tight. My balls were getting mashed mercilessly, and I had to try three times to get my hard-on to stay in and not pop out over the waistband.
“I think they’re too small,” I suggested.
“No, they’re perfect.” She walked around behind me and pulled them up, giving me a wedgie.
“These aren’t supposed to be a thong,” I pointed out, trying not to let the discomfort pitch my voice up too high.
“They are now.” She smacked my ass before coming around in front of me, then standing back and looking me over. She didn’t look happy. “You really are quite disgusting, you know that?” My evil step-sister made up her mind about something. “Take everything off and follow me.”
I did as I was told and followed her into her bathroom. I was once again jealous that she got the room with the private bath, while I had to use the one in the hallway. She had me get wet in the shower, then she lathered me up with foam. It felt nice, but I didn’t know what she was up to until she reached for the razor.
“Whoa, what’re going to do?”
“We’re getting rid of all that ugly hair. I want my sissy bitch to be as smooth as the little girl that you are.”
I was going to protest, but she started right in on the faint signs of manliness I had on my chest. Her hands on my body were enough for me to let her have her way. It was only a little hair, after all. It would grow back…eventually.
Avery quickly finished my chest, then did each of my legs. My dick bounced, conspicuously inviting her to grab it, as she worked her way up. Instead, she moved around to my backside and shaved my butt. It was more than slightly humiliating when she pulled my cheeks apart to get in my butt crack, but I also kind of liked it. After finishing, she came around and gripped my erection. Yes! It was handjob time!
“Stay still,” she warned and went for my pubes.
“Whoa, hold on! I’m not letting you near my dick with a sharp blade.”
“You let me shave yours, and I’ll let you shave mine.”
It only took me a second and a half to do the risk-reward analysis on that deal. “Okay, fine.”
She smiled, having known what my answer would be long before I did. My gut clenched up as she began clearing away my sparse showing of curly pubes. I relaxed a little as she worked. She held my hard-on down out of the way, sometimes shifting it to the side when she needed access to a particular area. I was doing my best not to blow my load, but there was a good chance I wasn’t going to be able to hold out. That’s when she lifted my dick and my fear of spewing too soon went away in an instant.
The blade moved along the wrinkled skin of my scrotum and every part of me tensed up. One wrong slip and I’d be bleeding from my nutsack. The idea of the pain was bad enough, but the embarrassment of facing all those emergency room nurses would be even worse. I held my breath as she rendered my testicles hairless one quick stroke at a time. She wasn’t taking this nearly as seriously as she should be. It was as if she didn’t even care if she accidentally sliced off my balls. Or maybe that was her intention!
It seemed like forever before she was done, but in reality it couldn’t have been more than a few minutes. She pushed my nuts around, feeling for any spots she missed. It was weird, and scary, and amazing all together. Avery grabbed my bald sack and squeezed.
“Smooth as a baby,” she said.
I didn’t know if I should be turned on by that, or deeply disturbed. She rinsed me, dried me, then yanked the panties back up into place. Even with my cock half soft, it was still too tight. She pulled them up into my ass crack again, and made sure my balls were fully crammed into the tiny garment proportioned to fit a pussy and allowed no space for a cock.
My step-sister led me by the hand back into her bedroom. She sat me down at her vanity table. With deft quickness she pulled my hair back and fastened it with a couple hair clips. She surveyed my face with an appraising eye. I wasn’t sure what she was up to until she plucked something from a drawer and began dabbing it on my face.
“What’s that?” I objected.
“It’s foundation, moron. Now stop moving.”
“Cut it out!”
She pinched one of my nipples and twisted. “Shut up and sit still, bitch.”
I did as she said. I wasn’t happy about it, but I was banking on the payoff being worth whatever hell she was putting me through.
Avery found a wedge-shaped sponge and began buffing the stuff she’d put on my face. Her motions were quick and practiced. I held still, my eyes cast down so I could admire her modest cleavage. After getting off to her mom’s huge fake tits, it was a real turn on to see what I could of her small, natural titties.
“If you want to be a sissy little slut, you’ve got to look like one,” she said as she applied some other cream under my eyes and to a few spots on my face. This she buffed out using a big, round, soft brush.
I couldn’t help but wonder how that brush would feel on my balls. “What are you doing?”
“I’m making you pretty.” She continued to work, then switched brushes and selected some kind of powder stuff. “I only fuck hot chicks. You should know that by now.”
I let her pat the brush over up along my nose and across my forehead as I struggled to interpret what she meant by that last statement. I hated the idea that she was putting makeup on me, but I had a breathless feeling in my chest that I didn’t want to go away. Giving myself over to my evil step-sister was making me feel high in a way I never felt before. I didn’t want it to end. “I want to fuck you so bad,” I confessed out loud.
“No duh, dicktard. Why wouldn’t you? My pussy is fucking amazing.”
“Most guys would think it’s weird to want to fuck their own sister,” I responded lamely.
“Yeah, right,” she scoffed. “Close your eyes.” I felt another brush working lightly over my eyelid. “My guess is that every brother wants to fuck his sister. Every dad wants to fuck his daughter. And every boy wants to fuck his mom. Guys just want to fuck every female they know. It’s disgusting, but that’s human nature, I suppose.”
“Girls are probably just as horny as guys, only they don’t want to admit it.” I was expecting her to call me an idiot for that, but she didn’t make an argument against what I’d said. “I mean, you want to fuck your brother. And maybe your dad, too…” I may have gone over the line with that.
She quietly tended to my other eyelid for a few long moments. I felt a sudden jab of pain and realized she’d just plucked one of my eyebrows. “Hold still, you sissy fuck face.” She plucked a dozen more times, each one hurting as much as the last. “It’s not so much that I want to fuck you. It’s more just because I’m bored.” She jabbed at my eyebrows with some kind of pencil. “All the guys I usually fuck are too manly to let me dress them up and put makeup on them like a little bitch.”
I noticed that she didn’t deny wanting to fuck her dad, but I probably couldn’t get away with getting her to talk more about that. Besides, I wanted her to be thinking about my dick, and no one else’s.
“Lips,” she said and nudged my chin up. “How about a nice slutty red.” She worked the lipstick around my mouth, then applied what appeared to be some kind of gloss over that.
She sat back and assessed the results with a self-satisfied smirk.
“I’m guessing I make an ugly girl,” I said.
“I hate to say this, but you’re almost cute. Take a look.”
With her permission, I turned and looked in the mirror. I didn’t recognize myself. It only took a little bit of makeup and ten minutes to transform me into something else…someone else. It was freaky, but also weirdly exciting. Although I didn’t dare say it out loud, I was one sexy bitch!
“Stand up,” Avery ordered. She adjusted my thong again, squishing my balls and giving my shaft an encouraging pat. “Now walk around for me.”
She leaned back and watched me do a circuit. “No, all wrong. I didn’t say tromp around like a retarded ape. Walk like a girl.”
I did my best, but she still wasn’t happy.
“Hold on, I know what’s missing.” She left the room and returned a minute later with a pair of her mother’s heels.
I should have protested, but I kind of wanted to see what it would be like. It took some work to jam my feet into my step-mother’s high heels, but I managed it. After a few teetering steps I found my balance. I did an ungainly circuit, feeling less and less sexy by the second. Avery gave me a few tips, and my next effort was better.
“Now you’re getting it.” She watched me experiment some more. “Nice, now get those hips into it. Put some wiggle in that walk.”
I felt ridiculous, but the more I practiced the harder my cock became.
“Ah, you like being a sissy girl, don’t you?” Avery taunted. Strangely, there wasn’t that usual cruel edge to her teasing, but an undercurrent of arousal.
Was this really turning her on? I focused and made a real effort to be as feminine as I could. I felt foolish, but at the same time it was freeing in a weird way. I swished my hips, stuck out my butt, and pranced on the high heels as I moved around her room. In my mind, it wasn’t just her there, it was a whole audience of people watching and cheering me on – all turned on by me, every one of them wanting to fuck me…the women and the men.
It’s not like I’d turned gay or anything like that, but the lines felt like they were being blurred further than before. I’d had a cock in my mouth – my own – but would it be much different if it was someone else’s? I’d had my dick sucked and if felt amazing – but would it matter if that mouth belonged to a man or a woman? My sister had pushed me to jam my finger in my butt hole, and even that turned out to feel pretty nice. Did I really care what else got put up my ass, or by whom? I stopped my parade, afraid of what I might be becoming.
“Very nice, sissy. You have got to be about the biggest freak I’ve ever seen.”
When I mustered up the courage to face her, I saw that Avery had her hand down the front of her red thong, her fingers working quickly beneath the thin fabric, and her other hand was up under her frilly bra. My cock pulsed and burst out of the panties she had me in. Instead of yelling at me she smiled and shifted her hand to the other titty.
“You like this?” I asked as confidently as I could, cocking my hips to the side in what I thought would be a sexy girlish way.
She nodded. “Yes.” She said it quietly, almost in a whisper, as if she didn’t really want to admit it out loud. “I don’t know why, but I do.” She moved to her bedside table, opened a drawer and pulled out a large, transparent rubber dildo. It was shaped like a real dick, with balls and everything. I watched with a racing heart as she pulled down her thong, fell onto her bed, and spread her legs. “I like girls.” She rubbed the tip of the bendy dildo along her wet slit. “And I really like men.” Avery nudged the head of the nearly invisible cock into her pussy hole. “But I never thought I’d get so turned on by a sissy little bitch like you. A boy and a girl all at once.” She slowly fed the remaining length of the fake dick into her cunt. Her face registered alternate looks of pain and pleasure as she forced it all the way in. When it could go no deeper she shuddered and fixed me with a hungry look of lust. No female had ever looked at me like that before, and I was pretty certain it would never happen again. “Do something,” she said softly and pulled the disembodied cock all the way out of herself before inserting it again to the hilt.
“Do…what?” I replied lamely, knowing I had to come up with something or she’d scream at me to get the fuck out.
“Surprise me,” was all the help I got.
I minced around her room in a circle, my mind racing trying to come up with something to do that would turn her on. I hit on something. It wasn’t the best, but it was all I could come up with in the moment.
With my back to my kinky step-sister, I hunched down and tucked my cock and balls between my legs. It hurt some, but it didn’t matter…the show much go on. I brought my legs tightly together and turned to face her. Then, pulling down my panties, I displayed my “man-gina.” It was like the psycho from that Jodie Foster movie. With my dick all tucked away out of sight, it looked kind of like I had a pussy – a shaved one, at that. Granted, it was more of a Playboy view of a pussy than anything else, but from what I saw in the mirror the effect was pretty convincing.
Avery sat up and made a face of disgust as she glared at me down there. I’d obviously screwed up. This was a bad idea. I was about to undo the illusion when a smile broke across her classically beautiful California-girl face. “That is so fucked up,” she stated in an almost reverent tone. “If I didn’t know you were a boy, I would totally think you were a chick. A very fuckable chick. Don’t move.”
As she grabbed her phone and switched it into camera mode, I suddenly feared this secret would get out. I’d never survive if people at school knew I was like this. Not only was I done up like a sissy bitch, I was doing it if hopes of getting some kind of sex from my step-sister. The words “Would you fuck me? I’d fuck me. I’d fuck me hard.” Bounced around in my head, drowning out my fear of being found out with the fear that I was more of a freak than even I realized.
Avery took a picture, the flash brought me back to reality – a reality that I barely recognized anymore. “That’s it slut, turn to the side and show me some ass.” I followed her direction without thinking. What was she going to do with these pictures? Use them to make fun of me? Blackmail? If I had pictures of her I’d be using them for jack off material. There was no way she was going to masturbate to pictures of me done up like this…was there?
“That’s right,” she went on, leaving the dildo behind and taking on the role of a famous fashion photographer. “Gimme a sexy look…almost…let me see sultry.” She moved around me taking shot after shot. The fact that she was naked and being so totally casual about it was keeping me rock hard. My cock was going to spring out of hiding if she kept up with that. “Here we go…give me a nipple…nice…pucker up, I want a pretty little kissy face…oh my God, this is too much…just a couple more with your dick out…let me see that sissy wittle wee-wee of yours.”
It was a big relief to release my hard-on and let it spring into its natural position. I struck a few more poses – not even trying to act like a guy, instead using the kind of poses that women did in all the porn I’d ever seen. I wanted to grab my cock and jack it like crazy right there, but I resisted and continued playing my sister’s game.
I bent over and she moved in to get a close up of my ass. On impulse I reached around and spread my cheeks. I expected her to recoil and tell me to stop being gross, but she continued to snap away, making small grunting noises of approval after each shot she clicked. She was really into this. I leaned forward and put my hands on her nightstand to balance myself. I went down into a half squat. My balls were hanging loose and I thought this would give her a good view of them from behind. From the faint grunts I was hearing, I was right. That’s when I looked down into the drawer she had left open.
It was full of dildos and different sex toys. It was a collection I might expect to find near at hand for a middle-aged sex addict, not for a popular high school girl. When we started, she had admitted to having a couple vibrators, but this was far beyond that. I guessed that maybe only two of them vibrated and the rest were dongs (big and small), or butt plugs, or…or whatever that thing was.
I had the sense that Avery was going to lose interest soon if I didn’t do something else, and a flash of perverse inspiration came upon me. I grabbed one of the thinner ones – a long, bullet-shaped, pink vibrator with bumps around the shaft. I didn’t know if it was one of the toys handed down to Avery. Had this thing been in my step-mom’s cunt? I put that thought aside, went for the nearly empty tube of lube, and quickly greased it up.
Before I had time to think through what I was doing, I reached around and poked it into my asshole. This could be a huge mistake and end whatever was happening, but I was too horny to stop and consider it one way or the other.
“Oh, fuck…” I heard her say, sounding more incredulous that anything else. “I was thinking of trying that on you myself, but I wasn’t sure you’d go for it.” I glanced around just in time to see her lean in and take a picture. “You aren’t fooling around, are you? You’re all in.”
I guess I was. I pushed the toy farther and it slid in almost effortlessly. I was trying to relax everything back there, but couldn’t help clenching. Even so, the lube did its job and before I knew it the whole thing was in my butt with just enough sticking out to hold onto with my fingertips. Yeah, definitely all in.
“Go on,” she said behind me in a hushed voice. “Go ahead and fuck yourself…I want to see you do your own ass…fuck your asshole, bitch.”
Once again, I did as I was told, unable to resist…not really wanting to. It was humiliating, for sure, but more than that it felt good. Not only did if feel good to fuck my own ass, but what made it better was to have my harshly judgmental sister watching me. I looked back and saw her staring with slack-faced awe. It may not have been honest-to-God awe, but I don’t know how else to describe it. When her hand went back down between her legs and her fingers began working her pussy, I felt somehow honored in a strange way.
Not only was I turning her on, but she was more than willing to openly show it in front of me. In that moment, I wasn’t her annoying step-brother that she couldn’t stand. I was the object of her sexual desire. Yes, I was nothing more than a plaything to her, but I was getting something out of it, too.
“Shit,” I moaned. “I think I’m going to cum.” But that was impossible, I wasn’t even touching my dick. My balls tingled in the way they only did when I was about to shoot my load. “Oh…fuck…” I had no idea what I should do. Avery quickly came to my rescue.
“Don’t stop! Keep fucking your ass just like that. Turn around so you don’t cum all over everything, and keep fucking.” By “everything” she meant her assortment of rubber cocks and plastic dicks that she masturbated with (on what I could only assume was a nightly basis).
She messed around with her phone. “Okay, video mode. Don’t touch your cock!”
Pictures were bad enough, now video? I wanted to tell her no, but I was too far gone to care. “I’m fucking my ass,” I blurted out nonsensically. It turned me on saying it, but it turned me on more hearing it. So fucking weird. “My sissy asshole is getting fucked by a cock.” My voice sounded too high. “My pretty little ass wants to get fucked with a big, hard cock!” Yep, I was talking in a girl’s voice now, and I’d lost the ability to censor my words before saying them aloud. “I want to suck a cock, and eat cum, and get fucked in the asshole like the horny little bitch that I am.”
Avery’s hand was moving faster between her legs. She was humping her fingers as she stood with wobbling legs and filmed my shameless display of self-abasement. I didn’t need her to tell me I was a perverted freak, I was doing it for her. And she seemed to be loving every second of it.
“Ahhh…I want cock…!” I cried out and began spewing semen. I didn’t know how it was happening, but a steady stream of cum flowed out of my dick onto the floor of my sister’s bedroom as she filmed and ravaged her own cunt.
“Oh, fuck! Oh, fucking fuck! Fuck me, fuck me, fuck me!” she chanted and began to spasm. Her whole body shook, but she didn’t take her eyes off the fountain of white jizz spilling from my pisshole. I never let up on my ass the whole time, fucking myself as fast as I could and wishing I’d selected a thicker toy to shove up there. “Ohhh, fuuuuck,” she sighed when her orgasm finally began to stall out.
After several orgasmic convulsions of my own, I stopped railing the vibrator into my asshole and tried to catch my breath. Avery, stood in front of me, hand pressed to her side as if she had a cramp, and labored to catch her breath.
“What a mess,” she gasped with a slight giggle. “There’s cum all over the tip of you dick. Clean it off.”
I looked around for something to use to wipe up with and reached for the tissue box on her nightstand.
“No, no, no,” she scolded. “With your tongue, perv boy.”
I nodded, feeling foolish for not picking up on the obvious. She didn’t care about the mess, she just wanted to see me doing something nasty. I began to get down on the floor so I could assume the position.
“No.” Avery came to me, reachedTo continue reading this story you must be a member. Join for FREE here.
Lauryn
- 25.08.2020
- 39
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- Category:
- Incest
