Self-Sucking Sissy free porn video

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My cock was already hard as I strode naked into our huge living room. I finally had the house to myself and I was going to take advantage of it. My dad had taken Bimbo-Barbie (a.k.a. my step-mom) to Tahoe for the weekend, and my step-bitch – sorry, step-“sister” – was off with her vapid pack of friends doing who cares what. She was only sixteen, same as me, but she always acted like she was one of the grown-ups around here and I was just some stupid kid.

I walked around the living room, not caring that the curtains on the three floor-to-ceiling windows that overlooked L.A. were wide open. Bimbo-Barbie had picked out the fanciest, most expensive décor dad’s money could buy. It seemed a waste to hide in my bedroom and whack off when I could make use of these fine furnishings to assist my masturbatory endeavors. I had one particular sexual experiment in mind for the evening.

I selected the white sofa with the over-sized cushions for my experiment. Before settling in, I bent down and touched my toes and did a few side bends. That should do the trick. I went around behind the sofa, which was set in the middle of the room facing the big windows so you’d have a view of the city, and sat on the back of it. I then let myself slowly fall backward so that I was “sitting” upside down. I regained my balance, then brought my legs up and over, curling my body back on itself.

It was embarrassing that I was even attempting this, but it wasn’t like anyone would ever know. My hard cock dangled about six inches above my face in this upside down position. I was about to find out if I could suck my own dick.

Or, at least, lick it. I’d heard that some guys could do it, but I didn’t know if I was one of them. My dick isn’t porn-star huge, but it’s long enough that it doesn’t seem impossible. I was fairly sure I could probably get close. I pulled my hips down and watched my cock descend toward my face. The world suddenly began to spin and I found myself tumbling off the sofa, hitting the floor, and banging my shins against the glass coffee table. Ouch!

I got up, moved the table out of the way, and tried again. I used a couple throw pillows this time to help stabilize me, and I managed to stay on the sofa as I brought my dick down toward my mouth. Problem was, I was a good three inches short of my goal. I stuck my tongue out, but this did little to close the gap. I took a deep breath, let all the air out of my lungs and gave it another go. I might have got a half inch closer. Not great, but it was progress.

I relaxed for a minute, then went for it again. This time I pulled myself down harder. The muscles in my back began to hurt, but I kept going. The extra effort helped, but I still had a ways to go. I got another pillow and propped it under my head before rolling up onto my shoulders and forcing my hips down toward my head. My neck was in pain along with my back and I couldn’t breathe, but I swear I was only an inch away.

After walking around for a few minutes, twisting my neck from side to side, and doing a few more toe touches, I gave it another try. I pumped up my cock as hard as I could get it and curled over on the sofa. I crunched myself into as tight a ball as I could, then grabbed my dick and pulled it toward my mouth. Almost! I stuck my tongue out. Almost!

With one final all-out effort I pulled harder and I felt the tip of my tongue against the tip of my cock. Pain stabbed up my spine and I couldn’t hold the position for more than a second. I pulled back and sucked in a shallow breath. I did it! I wasn’t able to suck my own dick, but I did make contact. I was so fucking psyched that I started whacking off like crazy.

I stayed upside down on the sofa looking up at my cock and balls as I clumsily beat off with my arm wrapped around in an awkward reach. I was so turned on by the idea that I’d accomplished something so freaky that I was dying to cum. As I began to get close, I realized that if I came in that position that I’d end up jizzing all over my own face. I decided that it didn’t really matter. I’d gotten my cum on my face before when I came really hard and so it was no big deal. I was alone, no one would ever know but me, so why the fuck not?

This all made me want to cum even more. I stroked as fast as I could. I loved how my balls felt hanging upside down and how they jiggled every which way as I jerked it. I was almost there.

“Oh, yeah!” I moaned as I watched my cockhead swell and saw the first spurt of cum shoot out. It landed on my lips and I clamped my jaw tight to make sure I didn’t get any in my mouth. More cum flew out of my dick and spattered on my nose and forehead. I closed my eyes, worried I’d blind myself, and kept stroking. Warm jizz splattered over my face and it felt great. I could smell it everywhere.

When I was done, I flipped my legs down so they hung over the back of the sofa. It felt awesome to let my back relax and to be able to fill my lungs. I opened my eyes without getting any spooge in them and laughed. That was pretty fucked up.

I went to the bathroom, grabbed a towel and wiped my face off. I was feeling pretty silly at that point. Did I really just do that? I didn’t have a girlfriend to suck my dick for me, but did I need to resort to that? It was just a one-time thing I told myself as I checked in the mirror to make sure I didn’t miss any stray spooge.

That night, as I lay in bed, I thought about my mildly successful gymnastic efforts from earlier. I was so close. I’m sure with some practice I could do it. As I jacked off for about the tenth time that day, I knew I would have to attempt to suck my own cock again – and probably soon.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~

I stood in the kitchen in my boxers and a t-shirt the next morning waiting for my Pop-tarts to pop. My back was sore and my neck was worse. What was I thinking? I was worried that I might have done permanent damage to myself. What if I had broken my back? How would I explain that to my family?

Avery, my stupid step-sister, came into the kitchen in her pink Hello Kitty pajamas and went straight to the Keurig machine. The toaster clicked and my Pop-tarts appeared.

“Morning, Paul.”

She barely ever acknowledged that I existed, much less talked to me when she didn’t have to.

“Mornin’” I grumbled back, thinking that I should take some Advil for my aching back.

I noticed Avery looking at me funny as I put my tarts on a plate.

“If you want, I can help you,” she said as she got a coffee cup out of the cupboard.

“I think I can handle putting Pop-tarts on a plate.”

“Not that, stupid, the other thing.”

“What other thing?”

“Sucking your own cock.”

I knew I didn’t just hear what I thought I heard. No fucking way.

“Whaaa…?”

“Don’t even try to deny it, loser. I saw you in the living room last night.”

My brain was in too many pieces after its rapid implosion to be able to form a response.

“Remember? Naked on the sofa, trying to lick your own dick.” She checked how her coffee was coming. “You ended up jerking off all over your own face. I’m sure you must remember that.”

“What are you? Some kind of pervert, spying on people?”

“You sure you want to be throwing around the pervert label like that, dick sucker wannabe?”

“Yeah, well… fuck you.” It was lame, but I had nothing better.

“Oh, don’t be like that, little brother.”

“You’re only two months older than me, Avery.”

She shrugged and sipped her coffee. “Which makes me your big sister.” She still had that funny look in her eyes. If I wasn’t completely freaked out and humiliated I might have noticed the look was more one of intrigue than disgust. “I meant it when I said I can help you.”

“So now you’re going to blackmail me or something?”

“I’ve been doing yoga for two years,” she said with a coy smile. “I could show you some poses that would increase your flexibility.”

“Ha, ha, very funny.” God, she was such a cruel bitch. I guess when you’re a hot chick, you feel like it’s your birthright to make other people feel like shit.

“I’m not joking, perv boy.” She moved a little closer and I could see that her nipples were sticking up under her PJs. “It looked like you got pretty close yesterday. I bet if you worked out with me we could get your cock in your mouth by the end of the week.”

I couldn’t tell if she was for real or yanking my chain.

“Or, you can just stand there with that boner and stare at my tits like an idiot for the rest of the morning.” She said this in a tone that wasn’t nearly as mean as the one she usually used when speaking to me.

I did feel like an idiot for getting a boner in the middle of all this, but there was nothing to be done about it. She’d apparently already seen my cock in all its demeaning glory, so what was the point in trying to hide it? And she didn’t even really seem to care that I was staring at her tits. My world was taking a total one-eighty.

“You’re full of shit,” I accused half-heartedly, hoping I was wrong.

“It’s just a matter of stretching out the right muscles and getting limber.”

“Why would you even want to help me with… you know… that?”

She seemed disappointed that I didn’t even have the balls to say it out loud. “To be honest,” she took another slow sip as she decided how much to reveal, “seeing you trying to suck your own cock yesterday made me kind of horny. I ended up thinking about it last night while I was masturbating with my vibrator.”

“You have a vibrator?”

“Two, actually. One that I got for my sixteenth birthday and the other is one of my mom’s old dildos that she didn’t want anymore. Your father bought her a bunch of new toys after the wedding, so she let me have the one she knew I liked to borrow when she wasn’t using it.”

I couldn’t believe she was talking to me this way. No girl ever said stuff like this.

“But, you… you said I was a pervert and all… ”

“Yeah, so? Ever stop to think that maybe I’m a pervert, too?” She pinched her own nipple through her Hello Kitty top as if to prove her point. “So, do you want my help or not?”

“Um, if you’re serious, then…” I knew this was the moment of truth. Something totally unexpectedly cool was about to happen or I was about to get punked hard, “yeah, I’ll do it, I guess.”

“Nice.” Her smile appeared genuine. “Meet me out by the pool in an hour. Wear something loose.”

Avery winked and skated out of the kitchen jauntily on her stocking feet. That didn’t just happen, did it? I picked up one of my cold tarts and bit into it. My mind was so turned inside out that I didn’t even taste it as I went over the whole conversation ten more times to make sure it had been real. I wasn’t entirely convinced that she wasn’t still planning something evil, but I couldn’t pass up this chance if she was legit.

Two dildos? She wouldn’t have admitted that if she wasn’t being honest with me about everything. Would she? Well, there was only one way to find out.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~

An hour later I was standing by the pool in a pair of basketball shorts and a t-shirt all alone and feeling like a chump. She was probably watching me from a window and getting a good laugh out of her loser step-brother waiting around to get dick sucking lessons. I resolved never speak to that stuck-up bitch again and was about to go inside when I saw her coming through the sliding doors.

Avery was in a neon blue leotard and carried two pink yoga mats under her arm. I’d never seen her wearing anything like that before, and it was tight. And I mean super-tight. When she got closer I could see that she was rocking a camel toe like nothing I’d ever seen before in real life. I wouldn’t say that my sister was the prettiest girl in our school but now I could see that she definitely had the hottest body of anyone in our class.

“Ready, perv boy?”

I just nodded and kept staring at her curves with a leer that should have earned me a slap in the face. Instead, she handed me a mat and then rolled hers out. I did the same. We stood facing each other, each on our own mat.

“Let’s start with some light stretches.”

It was difficult to concentrate on her instructions. Avery had decent sized tits, but nothing most other girls didn’t have. One thing I had quickly learned about my step-sister was that she knew how to dress so they looked almost a size bigger. Sometimes I almost resented her and her mom for walking around showing as much cleavage as they did, but I also didn’t want them to stop doing it.

Avery had me roll my head around, put my chin down to my chest, then tip my head back as far as I could. We sat and, with feet together, reached for our toes. I was already sweating under the warm sun shining down on the patio. She then spread her legs and had me do the same. Then we did more toe touches. Her camel toe was staring me in the face as I reached forward. I could see the tendons standing out at the tops of her thighs, along with the smooth hollows above and below that framed her barely hidden charms. All it would take was for the crotch of that leotard to slide one inch to the right or left and I’d be seeing naked pussy lip. She apparently took good care of her bikini line because there wasn’t any hint of hair.

“You can take off your shirt if you’re hot,” she offered as she had me stand up to do our first actual yoga position.

I was on the basketball team, second string, but I wasn’t much of a jock. Even so, I had a pretty okay body so I didn’t mind taking off my shirt in front of her. When I did, she just looked me over and smiled mysteriously. I had to wonder what she was really up to with all of this. I glanced back to the house, suspicious that maybe she was getting this on video and was going to somehow use it against me.

She led me through a couple poses that looked simple but were harder to hold than I expected. I’d always thought yoga was a lot of bullshit, but I was getting a pretty good workout. When she turned around and showed me downward dog, I nearly creamed my shorts. It was the first time I’d seen her outfit from behind, and her leotard had worked its way into her butt crack so it looked like she was wearing a thong. Her whole ass was right there! Then, when she bent over and stuck it up in the air, I practically started drooling all over myself.

I reluctantly got into the same position, which made it impossible for me to continue gawking at her hot little ass. She could have worn anything for this lesson, like a pair of baggy sweat pants, but she chose this outfit that she’d clearly outgrown a couple years ago. She was torturing me on purpose.

We went through three or four more poses with me trying to get as many looks at Avery’s practically naked butt as I could. My shorts were loose enough that my boner wasn’t totally obvious, but I’m sure she could tell I was sporting wood the whole time. She led me through some cool down stretches.

“Okay, perv boy, that’s enough for today. You’re going to feel sore tomorrow, but that means it’s working. You should probably hit the shower.” She nodded toward my crotch. “I recommend a cold shower.”

She rolled up her mat and headed into the house. I watched her flawless ass sway from side to side the whole way. I loved how she didn’t bother to pull the wedgie out of her butt like most girls would.

Even if this was all an elaborate prank on her part, it might very well be worth it if I got to see her like that a few more times. I wondered if she was in her room right then firing up one of those vibrators. I was about to run to my own room and whack off, but then thought better of it.

I pulled my cock out right there on the pink yoga mat my sister had lent me and began stroking myself openly in the sun next to the pool. Avery had already seen me do the most embarrassing thing imaginable, if she wanted to look out her bedroom window and watch me jerk off, what difference did it make? The idea that she might be watching made it even better, and I came all over my chest and belly in no time.

Who would have guessed that trying to suck my own dick would have led to this?

~ ~ ~ ~ ~ ~ ~ ~ ~ ~

I was out by the pool again the next day after school, waiting. My dad was still at work and Avery’s mom was off shopping, or getting her hair done, or having her fake boobs rotated. My back and neck were sore as hell, partly from when I tried to suck myself off, but mostly from yesterday’s workout. My heart started beating faster when I saw my step-sister appear with her pink mat.

This time she was wearing a pair of white yoga pants – again, super-tight. She had on a white sports halter that left her midriff bare. I was surprised to see she didn’t have a pierced belly button, which I automatically assumed a girl like her would have. Her tummy was too sexy to ruin with tacky jewelry.

“Back for more, pervert?” she greeted me.

“Yup.”

“Boy, you really want to suck that gross cock of yours, don’t you?” She rolled out her mat and turned to face me. Her signature camel toe was proudly on display once again.

“Guess I do,” I admitted, playing along and wondering if maybe she secretly wanted to suck on it, too.

We went through the same warm up routine and poses as the day before. When she got into downward dog, the fabric of her yoga pants stretched so tight that they were practically see-through. It became obvious that she had nothing on underneath, and that she shaved more than just her bikini line.

Avery added a couple more poses to the routine and I managed to catch her checking out my boner a few times.

“Whew, good job today, little brother,” she said after we finished our cool down. “You’ll be licking your dick before you know it.”

“Maybe I wouldn’t have to if there was someone else around to do it for me.” These words were out of my mouth before I realized what I was saying. My gut clenched. Had I overplayed my hand.

“If I meet any girls desperate enough to hook up with a complete loser, I’ll let you know.” This was said with a friendly smile.

I let that pass. “Want to jump in the pool to cool off?”

“Nah. Maybe next time.” She picked up her mat and was ready to head inside. “Oh, and by the way, Mom won’t be back for about an hour, so you can go ahead and jack off out here like you did yesterday if you want to.” With that she sashayed into the house, giving me a lovely parting view of her ass as she went.

I guess that answered the question as to whether or not she saw me. I pulled my shorts off, faced the house and went ahead and beat off out in the open. The way the sun was reflecting off the windows I couldn’t tell if she was looking, but I pictured her watching me and fingering herself. I blew my wad in no time flat. I remained there on the pink yoga mat and fooled around with my balls for a while, letting my cum drool down my sides. I liked the way it tickled my skin. It was nice not having to hide in my bedroom when Avery was home and I wanted to jack off. If only she felt the same way.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~

Other than during our workout sessions, Avery pretty much treated me like she always had, which means she mostly ignored me. Mom and Dad didn’t seem to notice that anything was different between us. My father would have straight up killed me if he knew what was going on. He wouldn’t want anything to mess up what he had with his D-list trophy wife.

My cockteasing step-sister showed up for our next session in a skimpy string bikini. I was glad to see she was sticking with the camel toe theme, and when she turned to spread her mat she flashed me a nice view of her nearly naked ass. I’d never seen her around the pool in that thing before or I would have remembered. And there was no way her mom would allow her to have anything that revealing in her swimsuit collection. I wasn’t complaining.

We went through the stretches and poses. It was actually getting a little easier, and I wasn’t as sore as before. This tree-hugging new age shit might actually work. It was hard to concentrate with all that naked girl-flesh on display, but I managed somehow.

When we were done, Avery dropped her mat by one of the lounge chairs, then dived into the pool. I debated whether or not I should join her. Two seconds later I was jumping into the pool naked. Avery did a lazy lap up and down the long way, while I just goofed around near the edge trying to figure out if I should try anything, or just play it cool.

She climbed the ladder to get out and her ass looked even better all wet. I almost choked when I saw her go to one of the lounge chairs, sit down, and take off her top. I was staring straight at my step-sister’s naked tits! She leaned back in the chair like it was nothing and closed her eyes. I slowly made my way to the ladder and climbed out, moving carefully so as not to spook her.

I settled down on the chair next to her. I tried to think of something to say that wouldn’t sound lame. I kept glancing over at the droplets of water trickling over her tanned breasts as she dried in the sun.

“You can go ahead and jerk off if you feel like it,” she said without opening her eyes. “Just don’t get any of your stuff on me.”

“Seriously?”

“You’re just going to spank it later thinking about my tits anyway, so you might as well take care of it while they’re right here in front of you.”

I had to take advantage of this opportunity. Who knew if I’d ever get another chance? I took a hold of my dick and started stroking.

“You’ve got a really hot body, Avery.”

“I know.” She opened one eye and took a peek at me working my hard-on. “You’re not so bad yourself. I’ve seen better, but you’re not totally disgusting.”

“Thanks, I think.” My dick felt good in my hand as I watched my step-sister’s nipples stiffen. “You can go ahead and play with yourself too, if you want.”

“Eww, don’t be gross, pervert.” She adjusted her bikini bottoms, pulling them up snug and accentuating her camel toe even more. “You’d love that, wouldn’t you? Watching me spread my legs and finger my wet pussy right in front of you while you beat off like a degenerate freak. You shouldn’t be thinking that way about your own sister.”

“Step-sister,” I corrected as I stroked my dick faster.

“Same thing.” Avery tilted her face up to the sun and arched her back slightly. “Just be happy that I’m letting you jerk off to my tits and don’t get greedy, little boy.”

“Your tits are awesome. I want to cum all over them.”

“Try it and I’ll cut your balls off.” She gave me a look to let me know she was serious. Her eyes then drifted down to my hand pumping up and down on my cock.

She watched without saying anything, clearly intrigued by what she was seeing. I didn’t know what I wanted to do more: stare at her naked tits, or watch her watching me. Her hand meandered slowly up her body as if acting on its own. Her fingers slid over the still moist swell of her breast and navigated their way to her nipple. A single fingertip casually circled the light brown prominence at the tip. That was all I could handle.

“I’m cumming,” I blurted out and spewed a fat load onto my belly.

My step-sister playfully pinched her nipple as she watched me milk the semen out of my cock.

“Cute,” she said once I’d finished. Her hand fell away from her breast. “You’re not going to let all that go to waste, are you?”

“What do you mean?”

“I assume you want to suck your own cock because you like the taste of cum.”

“Oh… no, that’s not really why I wanted to do it.”

“Step one, suck cock. Step two, get a mouth full of cum. What am I missing here?”

“I guess I only thought about how good it would feel to get my dick sucked, even if it was only me doing it. I didn’t think much about step two.”

“Even after you jizzed all over your face the other day?”

All I could do was shrug.

“Have you even tasted it yet?”

“My own cum? No.”

“Well, what are you waiting for? Try it.”

“Nah. I don’t feel like it.”

Avery reached over, scooped up some of my load on her finger and held it up to my mouth.

“C’mon, perv boy, eat your cum.”

I ducked my head to the side. “Seriously, I don’t want to.”

She pulled her hand back, then shocked me by wiping the dollop of jizz she’d collected over one of her nipples.

“How about now?”

“You want me to… ”

“Lick your cum off my titty, perv. Offer expires in 3…2… ”

I lunged toward her and ran my tongue across her proffered nipple. I was vaguely aware of the taste of semen, but I was more focused on the feeling of licking a girl’s tit for the first time in my life. I licked again and again, then started sucking. She let me go for a few seconds before smacking me hard upside the head. I pulled back. I started to go back in for another try and caught another whack to the skull. I sat back a bit sulkily.

“Now eat the rest of it,” she instructed, pointing at the mess on my belly.

“Forget it,” I pouted.

“Okay, fine,” she leaned back and closed her eyes. “I’m not the one who needs self-sucking lessons. I’m sure I can find something better to do with my time than waste it helping my creepy brother get his cock into his mouth.”

There was the evil bitch that I knew so well. I hated her for manipulating me like she was, but I couldn’t deny that she had all the leverage. I swirled my tongue around in my mouth. It didn’t taste all that bad. I couldn’t pass up a chance to see how far things might go. I just had to suck it up, literally.

“Alright, you win, weirdo.” I got some spooge on my fingers and brought it up to my mouth. I’ve had the urge to eat my own cum while I’m jerking off and really into it but, soon as I bust my nut, the urge disappears instantly. I was repulsed by my own slimy goo at that moment but I silently counted to three and licked it off my fingers. It was nasty but tolerable.

“All of it,” Avery insisted as she watched with a wicked grin on her face. “It’s an acquired taste, but you’ll learn to love it… just like I do.”

I wiped up the rest of my load and fed it quickly into my mouth through a pure act of will. My thoughtful step-sister pointed out a few stray drops that I’d missed, then seemed rather contented with herself once she’d gotten me to eat my entire load.

“Mom’ll be home any second,” she said with a hint of that taunting tone of hers. “You'd better not let her catch you out here jacking off your filthy boner over her sweet, innocent daughter while she’s asleep by the pool.” She leaned back and closed her eyes, knowing she was in complete control.

I wasn’t so much worried about her mom as much as I was over what my dad would do to me when Mommy McBoobs ratted me out for supposedly perving on Avery. No one would ever believe the real story. All I could do was gather my shorts and t-shirt, take one last, lingering look at those sweet titties, and hurry inside.

I knew I was acting like a little bitch, but it was so worth it.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~

We had three more sessions after that. Our Sunday workout was later than usual since Avery had something else to do during the day. Our parents were off at some stupid Hollywood award dinner, leaving the two of us alone in the house for the night. She came out to the pool in baggy shorts and a frumpy t-shirt which was a bummer after all the other hot little outfits she’d worn all the other times.

We went through the usual stretches, and my step-sister was forcing me to really push my limits. She was usually pretty tough on me, but she had even less mercy than normal. After all that stretching, I wasn’t sure I’d be able to do the poses. Luckily, I didn’t have to worry about that.

“You ready?” she asked with a gleam in her eye.

“I suppose.” I got down into position for the first pose.

“No, dummy, not for that. Are you ready to try sucking your cock?”

“Oh. Um, I don’t know... I guess.”

“Let’s go into the living room where I saw you trying it the first time. I think using the sofa like that was a good idea.”

She headed to the house expecting me to follow. Which I did. I was feeling pretty nervous. It was one thing finding out after the fact that she saw me attempting “that,” but it seemed weird that I was going to try it in front of her on purpose. No matter how much of a loser it would make me look like, I knew I was still going to end up doing it anyway.

“Alright, pervo, get naked and assume the position,” she said when we arrived in the living room. I undressed, sat on the back of the sofa, and dropped back.

I felt the need to make something clear before we went any further. “I want to make sure you understand that even though I’m doing this that I’m not gay or anything.”

“Obviously,” she shot back, rolling her eyes. “You’ve been drooling all over me for the past week.”

“So, then, you don’t think me wanting to suck my dick is gay?”

“If you gave a guy a handjob, would that be gay?” she asked.

“Yeah, I’d say so.”

“Aren’t you basically giving a guy a handjob every time you jerk off? That doesn’t make you gay, does it?”

“Well, no… ”

“If you suck another guy’s dick, gay. Suck your own dick, same as jerking off.”

“Okay, I guess that makes sense.”

“Now stop stalling, and get those legs up and over.” I did as I was told and swung my legs above me. “Fuck,” she commented as she looked me over, “this actually does look pretty damned gay after all.” With a devilish smile, Avery stepped in close and grabbed my ankles before I could lower them down. “Take a nice deep breath.”

She was practically straddling my head. I could see up one leg of her shorts. It was dark up there, but I could tell she had no panties or anything on underneath. I filled my lungs through my nose and slowly let the air out through my mouth like she taught me.

“You need to be all the way hard for this.” She let go of one of my ankles and grabbed my dick. She began yanking on it. It was a bit rough, but it still felt good. It only took me about ten seconds to get a full-on stiffy, but she kept going for longer than she needed. “There we go, that should do it.”
 
“Thanks,” I muttered, not knowing what the proper etiquette was.

“How’s your back feeling?”

“Fine.”

“Then let’s get your legs down lower.” With both hands back on my ankles, she guided my legs, pushing slightly so my knees bent as they went. “Just relax into it. Bring your hips up over your head. That’s good. Let your own body weight do the work for you. And there’s my brother’s hairy asshole,” she announced with a certain amount of distaste.

“Sorry,” I said lamely.

“I’ve seen worse.”

My cock dangled just above my face. I was encouraged to see that it was about as close to my mouth as I’d gotten on my first attempt, and I wasn’t even trying yet. My dick pulsed with excitement as I realized that this might actually work.

“Hold here for a few more seconds,” Avery instructed as if she was taking me through one of her yoga poses and all this was perfectly normal. “Good… put your legs up and relax.”

Neither one of us said anything while I let my back and spine uncoil. I could see that her nipples were hard under her t-shirt. She was pretty much staring at my dick the whole time, which was enough to keep me good and hard. I wondered if this was making her wet.

“Okay, now this time visualize your goal.” Her voice was warm honey. “Picture that fat cockhead of yours sliding between your lips and into your mouth.”

I nodded and she helped me bring my legs back over until my cock was once again in position.

“Exhale and curl yourself in tighter.”

I did and was shocked to feel the head of my cock brush against my lips. I let up by reflex, having expected it to be more difficult. Was I really ready to do this in front of her?

“There you go, you had it. Try again.”

I exhaled and curled. Avery’s hand wrapped around my shaft and she directed my cock toward my mouth.

“You’re right there… a little more… good. Now give it a kiss.” She circled the tip of my dick around my lips. “Now stick your tongue out. That’s it. Lick the end… now all around. Good boy. Relax.”

I didn’t want to stop, but I obeyed my coach and flopped my legs over the back of the sofa. My cockhead was shiny with my own saliva. It didn’t seem possible, but it had really just happened… thanks to my snobby, mean-girl, popular clique step-sister. No one would ever believe this in a million years.

“How was that?” she asked, sounding genuinely curious.

“Good,” I answered. “Real good, actually.”

“I could tell you liked it,” She shifted a little, seeming kind of antsy. Avery was on her knees now, her tummy just above my head. If she leaned down she’d be able to smush her tits right in my face. “It’s funny, you actually look kind of cute doing it.”

I wasn’t sure how to take that, so I said something stupid. “Are you getting off on this?”

“Don’t flatter yourself, sicko.” She blushed a little and I knew I’d guessed right. “Let’s go again and make this one count.”

I rolled myself into an upside down ball once more. It was dark outside by this time and I noticed that I could see my own reflection in the big windows. I looked like a depraved freak, but seeing my step-sister right there to help me along made the scene ten times hotter.

“Here we go, crunch down.” She gave my cock a few strokes and steered it to my mouth. “Get it between your lips… nice. Hold it there for a sec.” She straightened up, put her hands on my ass and gently applied pressure.

I felt a slight twinge as my back contorted, but it wasn’t enough to stop me. The head of my cock dropped lower, passing my teeth and finally ending up all the way in my mouth. Holy crap, I did it!

“There it is, now suck it. You got it, suck that nasty cock, little brother.”

Avery took her hands away from my ass. My cock withdrew slightly, but I was able to compensate my curling tighter and straining my head forward a little more.

“God, that is so fucking perverted,” she whispered more like she was talking to herself than to me. “Keep going… suck it harder.”

With great difficulty, I rolled my eyes up and was able to see that Avery was leaning back, on her knees, and had one hand down the front of her baggy shorts. With the way her arm was moving, there was no doubt what was happening down there. My step-sister was masturbating to the sight of me sucking my own cock. Sweet.

“C’mon, suck that cock like you’ve always wanted to,” she commanded when she noticed me peeking at her. “Really get it in there, freak boy.”

I grabbed the backs of my thighs and pulled myself down more. My lips were wrapped around my shaft. I never imagined I could get that much of it in my mouth. I sucked and licked myself. Even though I was somewhat distracted by Avery fingering her pussy just a couple feet away, I was still able to appreciate how good what I was doing felt. The burning pain in my neck and back didn’t matter as I swirled my tongue around the smoothness of my cock head. I could taste the light flavor of my pre-cum each time I licked past my piss hole. I moved my head as best as I could and started giving myself a legit blowjob.

“There you go,” Avery said breathily. “That’s how it’s done. You like sucking that big, hard cock, don’t you? Yeah, you like showing off what a pervert you are in front of your sister.”

She was right. I did like sucking my cock, and I loved doing it in front of her. I would never do this in front of a girlfriend, but since Avery already thought I was a loser, it didn’t matter if seeing me suck my own dick made her think less of me. Besides, she was just as much of a pervert for wanting to see me doing it.

I was getting lightheaded. Being upside down, with my lungs getting crushed and only being able to get shallow breaths through my nose wasn’t allowing for much oxygen to get to my brain. I popped my cock out of my mouth for a few seconds to take in some air. I glanced back and saw that Avery’s shorts had come down over her hips and were hanging at her thighs. One hand was at work on her bald pussy, the other was squeezing a tit through her shirt.

“Don’t stop,” she said. It was more of a request than an order. “I want to see you finish in your mouth.”

That was enough to inspire me to resume my degrading exhibition of auto-fellatio. I dipped my hips back down and my cock slid easily between my lips. I once again marveled at the sensation of my cockhead against my tongue. I couldn’t tell which part felt better: giving or receiving. I guess it didn’t really matter since I was doing both.

“No more screwing around, little brother. Suck that load of cum right out of those floppy balls of yours.” The wet sounds of her fingers banging into her pussy accompanied her filthy encouragements.

I was just as eager to get to the climax of this kinky endeavor as she was to see it. I sucked my cock in as deep as I could, which was only about a third of my length. I let the edges of my teeth scrape lightly against the soft skin below the crown of my cockhead. When I opened my eyes, all I could see were my balls hanging down just above my nose. I couldn’t help but wonder if I’d be able to stretch them far enough to give those babies a lick as well. I heard myself moaning as the tell-tale tingle started around my asshole.

“Let me see it,” Avery demanded. “I want to see the cum going into your mouth.”

I remained focused on my own cock, praying that there’d be another chance down the road for me to watch my sexy step-sister play with her pussy. I bobbed my head as fast as I could, never letting up on the suction as the ridge of my cap passed through the tight ring formed by my lips. This was it... I was about to blow.

I sucked until the last possible second, then opened my mouth wide as soon as I hit the point of no return. My ass clenched, my cock flexed, and next thing I knew jizz was flowing down into my mouth and coating my tongue.

“Oh shit, yes,” my step-sister cried out. “Cum in your own mouth, you freaking pervert.”

The noises that followed, both vocal and hand-made, made it obvious that she was giving herself an intense orgasm at that moment.

“Don’t swallow yet,” she called out between spasms. “Fill your mouth up, but don’t swallow.”

I remained in position, letting more semen drool from my dick and fall onto my waiting tongue. The flavor was quite familiar to me by this time, but I’d never had a full load in my mouth. I was on the verge of gagging, but I managed to hold it together. Avery then surprised me by coming right up close all of the sudden.

She held my jaw and brought her face right over mine. She was looking down into my open mouth. Her forehead pressed against my cock and balls as she did this, but she didn’t seem to care. I could feel at least one of her breasts touching the top of my head.

“Look at it all in there. Move your tongue around.” She continued to gape into my mouth. The smell of pussy on her fingers was strong. “That is so gross.” She put her nose to my mouth and sniffed. “So gross.”

I might have believed her if right after she said that she hadn’t licked up a drop of stray semen that had fallen on my lower lip.

“Now let me see you swallow it. Nice and slow.”

Her hand moved away from my face. I couldn’t see where it went, but I was pretty sure it was back between her legs. I waggled my tongue around some more, trying to put on a good show. I swallowed a little bit of my wad and opened up to show my sister what was left. I repeated this a few more times until I was able to demonstrate that I had taken it all down.

“That was so fucking disgusting,” she said with a tone that was the opposite of disgust. “Now lick it clean.”

I shifted, bringing my cock low enough for me to lick it. She only backed off a few inches. Her face was still right there with mine; close enough that she could have licked my dick along with me if she wanted to.

“Kiss it.” Her increasing motions left no doubt that she was once again fingering herself vigorously. “Suck it… yeah… ”

Her lips were so close I could practically feel them on my cock. I was sure that was about to happen, but she suddenly backed off and fell into the throes of another orgasm. I tried to see what she looked like when she made herself cum, but she was too close for me to see anything but her old, gray t-shirt.

“Nice going, little brother.” She slapped my ass as she stood. “I told you I could help you suck your own dick. You’re welcome.”

I uncurled my body and my back released a kind of pain that was almost pleasurable. I was going to be sore as hell the next day, but I didn’t care. I slid sideways until I was lying on the sofa and filled my lungs completely for the first time in almost ten minutes. Avery was pacing in a tight circle on the carpet in front of the picture windows, hands on her hips, face flushed with sexual gratification. I was bummed to see that she had pulled her shorts back up.

“How long before you can cum again?” she asked.

“I don’t know. Five minutes, maybe.”

“Good.” She faced the windows, looking at my reflection. “That was good for your first try, but I think we can get more of your cock in your mouth.”

“That was plenty enough for me,” I said, worried the paramedics would know exactly how I’d snapped my spine when they came in and found me upside down and naked with cum on my breath.

“No. Take it from a girl who’s sucked enough dicks toTo continue reading this story you must be a member. Join for FREE here.

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IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

3 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

1 year ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

3 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

3 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
2 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

1 year ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

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