Self-Sucking Sissy 2

Self-Sucking Sissy 2
by DirtyMindedMom

Brandi, my sex-crazed step-mother, was expecting me to be out on the patio in less than an hour. That’s where my command performance was supposed to take place. She was basically blackmailing me into demonstrating how I was able to suck my own cock. My dad was away at a film festival “scouting talent,” leaving his cosmetically enhanced trophy wife free to indulge her kinky curiosities with me. If he ever knew what I had done with Avery, my step-sister, he would kill me. If he ever found out about what I was about to do with his wife, he’d bring me back to life just so he could kill me again.

The day had arrived quicker than seemed possible. I had been racking my brain trying to come up with a way to get out of having to put on a private sex show for my step-mom, but every time I started thinking about it, I got a raging hard-on and ended up jacking off to thoughts of those ridiculously large breasts my dad had bought her.

I hadn’t actually given myself a blowjob since that day with Avery, but I had been doing my yoga exercises and making sure I stayed limber just in case I wasn’t able to get out of this. Last night I realized that maybe I really didn’t want to get out of it. Now that the moment was upon me, I wasn’t so sure anymore.

I finished drying off after my shower and pulled on a pair of basketball shorts, not bothering with underwear. I did a dozen push-up to pump up the few muscles I had before putting on a t-shirt and heading downstairs and out to the pool on unsteady legs.

When I got out the patio, she wasn’t there. The mix of relief and disappointment had me confused. What was wrong with me? There was obviously something seriously fucked up about a woman who was willing to threaten her step-son into performing deviant sex acts for her pleasure. And yet, I wanted to show off my new found talent despite the shame I felt for even wanting to suck my own cock in the first place, much less going through so much to be able to actually do it.

I wondered if I should wait, or if should assume she forgot about our appointment and get out while I still could. Yeah, this was all too weird, even for me. Time to split.

“Sorry, I’m late, hon.” Her bubbly voice sent a tingle up my back. “I couldn’t make up my mind what to wear…or, not wear.”

I turned and saw my step-mother walking toward me on a pair of silver high heels, holding an appletini in one hand and a smoldering cigarette in the other. She never smoked when my father was around, but I guess when the cat’s away…

“You like?” She did a turn in front of me to show off her outfit, what little there was of it.

She had on a neon yellow micro-bikini, the kind I thought only existed in porn videos. Two strips of thin fabric that couldn’t have been more than two inches wide came over her shoulders and down over her breasts. They weren’t quite wide enough to fully cover her nipples and I could see a hint of her brown areolas peeking out either side. The strips stretched down over her surprisingly flat tummy to meet at her crotch. Just like her daughter Avery, she also seemed to be a big fan of the camel toe. The big difference was that my step-mother apparently didn’t share her daughter’s preference for a bald pussy. There was a neatly-trimmed fringe of pubic hair visible both above and to the either side of where the scant bit of fabric disappeared between her legs.

When she turned, I could see how the single strip was wedged up the length of her ass crack. I didn’t know if my step-mom had butt implants or not, but her ass was as smooth as a teenage girl’s. The sheer “cover-up” she was wearing did nothing to conceal any of this. The fact that she appeared to have an all-over tan didn’t escape my attention. When Brandi had completed her second turn she looked at the front of my shorts and smiled.

“I’ll take that as a yes.” She was more than happy to let my boner do the talking when it came to my opinion of her outfit. She flounced past me and took a seat in one of the cushioned patio chairs under the shade of a large tiki-style umbrella. She set her drink on the table next to her and took a drag of her cigarette as her eyes devoured me.

“I’m sure it’s much too hot for that shirt, isn’t it?”

I pulled off my t-shirt, wishing I wasn’t such a lazy bastard and had spent more time with the weight set my dad had bought me for Christmas. Funny how I didn’t worry about impressing Avery like this, but for some reason it was different with her mom.

“Ooo, Momma like.” She took a sip of her drink without taking her eyes off me. “Nice and smooth.” She was referring to the fact that my father was pretty much hairy all over, whereas I was just the opposite.

“So, um…you want me to just do it right here or something?”

“My, my, you’re in a hurry.” She leaned back and adjusted one of her boob straps, giving me a quick flash of nipple as she did. “Sit down, Paul, relax. Let’s get to know each other a little better before we jump to the main event.” She pushed a chair out for me with a high-heel clad foot. “Would you like a drink?”

“No, I’m good,” I lied as I sat down, not sure if I should do anything about my hard-on. My step-mom seemed to be enjoying it, so I didn’t bother trying to hide anything.

“I think you’re a sweet boy, Paul. I liked you from the first time we met. Remember, back when I first started dating your father?” She crossed her legs, making me realize that I’d been staring at her crotch. “What I can’t figure out is why you don’t like me.”

“I…I never said I didn’t like you.”

She nudged my knee with the toe of her shoe playfully. “Then why are you always avoiding me? And you always have that look on your face when I’m around.”

“What look?”

“You look at me like I’m some kind of prostitute that your dad hired for the night.” This was accompanied by an enigmatic smile. “A high-class prostitute, obviously, but still…”

“Oh, um, sorry. I didn’t mean to…y’know, make you feel like that.”

“That’s okay, hon. I know it can’t be easy seeing your father with a woman who’s not your mother. Especially a woman that looks like this.” She flipped her cover-up open so that there was nothing between me and her naked body except a couple flimsy strips of shiny green Lycra. “I’m guessing your mom didn’t have tits like these.”

“Uh, no. No she definitely didn’t.” I spoke as if in some kind of trance.

“I know I can’t replace your real mother, but I’d like for us to be friends.”

I’d seen my step-mom in one-piece swimsuits around the pool, and slinky dresses when she went out on the town with my father, but I’d never seen her practically naked before. I’d always sneered at her fake boobs, and her just-from-the-movie-set style makeup, but there was no getting around the fact that for a forty-something year old woman, she was downright sexy.

“Friends?” I murmured before forcing myself to look up from her epic rack. “Like…friends with benefits?”

Brandi laughed and took a long drag on her cigarette. “Your words, not mine, kiddo.” She didn’t bother to turn her head away from me when she blew out a long stream of smoke from between her painted lips. “All I was looking for was a chance to see something I’d never seen before – and, believe me, I’ve seen a lot.” She uncrossed her legs. “But, if that’s what you’re into, fucking your step-mother, I might be willing to consider it.”

“I wasn’t…I mean, I didn’t mean that…I was just trying to understand…”

“Calm down, darling.” She was clearly enjoying my awkward discomfort. “Let’s see how today goes, and then take it from there?” She flicked a bit of ash carelessly to the side and took a long sip of her drink. “How about we start by getting you out of those shorts so I can see what you’re working with, big boy.”

“Are you sure we should be doing this?” I hedged. I was at the point where I was more than willing to do whatever this living sex-bot told me to do, but it still felt wrong on all counts.

“Were you sure when you molested your sister?”

“Step-sister,” I corrected emphatically. “And it was all her idea.”

“I doubt your father will see it that way. Especially when he hears the way I tell it.” Brandi’s nipples stiffened under those two thin strips of material. Blackmailing me seemed to be turning her on. I never knew what a freak family my dad had married us into. “Now get those shorts down and let Momma see that virgin cock.”

I didn’t like her calling it a “virgin cock,” even though that’s what it was. The good news was that between my step-mom and my step-sister the chances were it wouldn’t remain that for long. I stood and dropped my shorts, kicking them off to the side. My cock stood straight, pointing right at Bimbo Barbie’s almost naked body.

“Not bad,” she said, running an appraising eye up and down my hard shaft. “Not bad at all for a young man your age. One more good growth spurt and you might top eight inches.” She sat back and took a drink. “You must take after your mother’s side,” she said with a devilish glint. “You’ve got at least two inches on your father. He knows how to use what he’s got, but sometimes a lady needs something more to be truly…fulfilled. That bad boy looks like it could do the job nicely.”

I felt oddly proud that not only did I have a bigger cock that my dad, but that his faux-glam wife was licking her lips and lusting for me to stuff her pussy with it. A dribble of pre-cum drooled from the tip of my dick. My step-mother just smiled and watched it fall to the cement of the patio in front of her as she finished her cigarette.

“So…now what?” I asked, eager for something to happen.

“Now, you show me your little trick. I’m dying to see how you manage to get your lips wrapped around that nice, big cock of yours.”

“Okay, but I’m only doing this because I have no choice.” I realized how lame that sounded as I was speaking the words. Of course I had a choice, I was just too cowardly to face the consequences. Either that or I really wanted to do this as much as she wanted to see me do it. “Shouldn’t we go inside?”

“Out here is fine. You can bring some cushions over from the lounge chairs if you need to. I don’t want to make a big mess in the house.”

“Why would there be a mess?”

“You’ll see,” she smirked and stubbed out her cigarette butt on the glass top of the patio table even though there was an ashtray within arm’s reach.

I went and grabbed a couple cushions and dragged them over. She indicated where I should perform my show, and then turned her chair to make sure she had the best view. I got down on the cushions, took a deep breath and prepared to get into position.

“We have all evening, Paul, so there’s no need to rush. How about you start by playing with your cock and balls a little before you jump right to the main event?”

I didn’t quite know what to do. I started touching myself here and there, fondling my balls, squeezing my shaft without jerking it too much. I had no idea how to put on a sex show. Even so, my step-mother seemed to be enjoying herself as she watched with her drink in her hand. The silence on the patio made things even weirder. I found myself wishing there was some music playing, although the last thing I wanted was to be ordered to dance.

“You masturbate a lot, don’t you?” She asked. “I’m guessing you jerk off that hot cock at least a few times a day.”

“Um…yeah, pretty much.” Everyone knew that most guys my age jerk off a lot, but it was still kind of embarrassing to admit it out loud. Especially to the woman who was supposed to be like my mom.

“At least that’s one thing we have in common,” she said with a sly smile. “Do you ever think of me when you’re stroking your cock?”

“No, not really…” I muttered.

“No? Not even when you’re peeking out your bedroom window at me while I’m lying here by the pool?”

Fucking Avery. Was there anything she didn’t tell her mother? “Okay, I guess sometimes I do.”

“I can’t blame you, sweetie.” Brandi ran a finger up under one of the thin strips hiding a nipple. “It must be torture for a boy with his hormones going wild to have a woman like me around all the time. I’ve seen the way you look at my tits and stare at my ass when you think I can’t see you.” She squirmed seductively in her seat as she spoke. “I admit that it turns me on to know a teenage boy is lusting after me and thinking about all the things he’d like to do with my body as he jacks off every night.”

I wanted to sneer at her narcissism, but there was enough truth to what she was saying that I couldn’t. Without really realizing it, I had started seriously jacking off as I stared at step-mommy’s crotch. The fabric there appeared to be getting narrower as she squirmed.

“Now that we’ve gotten to know each other a little better, I suppose it’s alright to confess that I’ve had a fantasy or two about you, young man.” She opened her legs wider, apparently noticing where my attention was focused. “I sometimes imagine that it’s you fucking me instead of your father. I pretend that it’s your cock pleasuring me. I pretend you’re on top of me while he stands in the corner and is forced to watch his son give his wife a huge orgasm. If it wasn’t for these naughty little fantasies, I’d never be able to cum while having sex with your father.”

“I don’t really want to know all this,” I complained. The truth was that I wanted to hear more.

“Then it’s a good thing that what you want isn’t all that important.” She closed her legs and leaned forward. “That’s enough foreplay, young man. We don’t want you squirting all over yourself before the [piece de resistance]. Let’s see that nasty trick of yours.”

I adjusted the cushions and got into position. My heart was hammering in my chest for reasons I couldn’t exactly put my finger on. I would have preferred to be doing this for my step-sister, but I liked the idea that someone was watching me. I rolled up onto my shoulders, swinging my legs up toward my head and lifting my hips in the air. My back curled and my hard cock was dangling a few inches above my face. My cockhead looked more swollen and bulbous than usual. I couldn’t wait to feel it in my mouth.

“Oh, my,” my step-mother gasped. “That’s a rather unique perspective.” Her lilting laugh betrayed her honest excitement of what she was about to witness. “Don’t go too fast, now. I want to enjoy this.”

I wanted to go fast so I could enjoy it, but I took a deep breath and did as I was told. I stretched the muscles of my back, gradually lowering the tip of my cock toward my mouth. It didn’t take long before I could kiss it. The familiar feel of my pre-cum against my lips was a pleasant reward. I backed off until the urge to shove my dick as far into my mouth as I could passed.

I heard a soft moan from my step-mother as I lowered myself for another cock kiss. I reached out with my tongue and swirled it around the head. The taste of pre-cum now accompanied the feel of it. It was surprising how addicted I had become to the flavor of my own spunk in only a matter of a couple weeks.

If I rolled my eyes up, I could see the upside down image of my father’s living sex doll. She had the straps of her flimsy excuse for a bathing suit pulled aside and was running her fingers over each of her large nipples in tight circles. I once again realized too late that I should have set up a hidden camera to capture all this so I could enjoy it later.

“How does that cock taste, Paul?”

I lifted up so I could get enough air to answer. “Good.”

“Mmm, I bet it does. Keep going, sweetie.”

Before I resumed the show, I noticed her pick up her phone and text someone. Geez, A.D.D. much? Screw her, I was going to have fun with myself whether she was paying attention or not. I reached around, set my hands on my ass cheeks and pulled down. My erection came down to where I could lick it, which I did, then I pulled more. My cockhead passed through my lips, pushed over my teeth, and into my mouth. I bounced up, then down again to relive that unique sensation again. It was still mind-boggling to me that I could actually do this.

There was a louder moan from my spectator, but I continued to concentrate on what I was doing. I made a tight seal around my shaft with my lips and sucked. It may have only been my imagination, but I swear I could feel my cockhead get bigger when I did this. I played my tongue around my spongy cap, marveling at how smooth and soft it was. The tip of my tongue teased my piss hole and the area just below it. It was frustrating that my angle and range of motion was so limited. I had to come up for air.

“That has to be the sexiest, most perverted thing I’ve ever seen,” my step-mom said. “God, what a sick freak you are.” This was followed by another moan.

I tipped my head back so I could check out her tits again. I was thrilled to see that she had scooted down in the chair and had her legs spread once again. I was further gratified when I noticed how her hand was rubbing between her legs. It was nice that she didn’t wait for days to get right to it like her daughter had.

“Is that as far as you can go?”

“I can get almost half of it in.”

“Oh, fuck. I need to see that.”

As I began preparing to push the limits of my flexibility, I suddenly saw someone else. Camilla appeared at my step-mother’s side with a silver tray. Oh, shit! She should have left a couple hours ago! I can’t believe Brandi would let our housemaid see all this. Camilla glanced toward me and our eyes met. For the first time in my life I was convinced it was possible to literally die of humiliation. She bent down to offer my step-mom something from the tray. That’s when I saw that there was a selection of dildos for her to choose from of various sizes, shapes and colors. This was getting freakier than I could deal with.

Brandi picked up a pink toy that had several bulges and curved in the middle. She rubbed it against her cheek absently as she considered her other options. She put the pink one down and selected a thick black dong that must have been ten inches at least. Camilla set the tray aside, then produced a tube from a pocket of her apron. She squeezed something out of it onto the black dong and I realized it was lube. She then leaned down, moved the wisp of fabric coving my step-mom’s pussy aside and squeezed another dollop there.

Camilla rubbed the lube around, slipping a finger briefly inside her boss’s pussy before finishing.

“Is there anything else, Ma’am?” she asked as she put away the tube.

“That will be all for now. Thank you, Camilla.”

Our eyes met again and she looked down almost as soon as they did. I guessed that she was ashamed that I had seen what she had to do to make her living. I was the one who should have been more ashamed, but our housekeeper was gone before I could sort it all out in my head. Besides, there was a bigger distraction for me to contend with.

Brandi let out a soft grunt and I looked over at her. The fat head of the fake cock had just popped inside her and she was forcing the thick shaft in after it. She grimaced and moaned with the effort. I watched it disappear inside her inch by inch. I was more convinced than ever that she must have been a porn actress before she trapped my dad.

“There we go,” she said breathlessly. “You don’t mind if I fuck myself while I watch, do you, hon?” All I could do was shake my head in silent awe. “Go ahead, sweetie, let’s see you really suck that lovely cock of yours.”

It was a struggle to take my eyes off my step-mom, and what she was doing to her cunt, but I had the sense that this wouldn’t be the last time I’d get to see her in that way. I turned my attention back to the tip of my cock hovering about six inches above my face.

Deep breath. Relax. Closer. Move slowly. Stretch. Closer. Open mouth. Lick the fresh pre-cum. Take it in. Suck. Taste. Shiver. Pull. Ignore the burning sensation in my back. Pull more. Lips around my shaft. Further. Past my teeth. More. Suck. Suck. Suck. Damn, that feels good.

“…so fucking dirty. Ahh!” Brandi must have been talking during most of that, but I only heard the last part of what she’d said. I heard that and what I presumed was the sound of a massive dildo being pistoned in and out of her well-lubed pussy. No wonder my father’s cock wasn’t able to satisfy her. I was pretty sure I couldn’t either…if it ever came to that.

“That’s it, darling, suck it. Avery said you eat your own cum. Let me see it. Cum in your own mouth and swallow it all down for Momma.”

Geez, I thought her daughter was twisted, but this woman was truly a perverted freak. Did my dad have any idea she was this extreme? Or, maybe the question I should be asking is, was my dad just as much of a freak and that’s why he was with her? These questions would have to wait because I had that familiar tingle starting at the base of my balls and spreading.

I sucked harder. I didn’t have much range of motion with my head, but by bouncing my hips slightly I could more or less fuck my own mouth. The distraction of the increasingly sharp pains in my back and neck competed with the impending sense of my orgasm, delaying it longer than if I what been jacking off by hand. But, as it turns out, I didn’t mind sucking my cock a little longer for the payoff I knew was very near.

“Do it, you cocksucking whore,” my step-mom cried out, sounding like she was as close as I was to getting off. “Take that cum like the hot little bitch that you are!”

If I was paying attention, I might have wanted to be offended by the things she was calling me, but instead I brought myself to and just past the point of no return. My orgasm was inevitable, but still two seconds away from actually happening. I lifted my hips, pulling from between my lips, and opened my mouth wide.

Without touching it, my cock flexed and jizz began flowing. I had the urge to grab it and beat off to intensify the sensation of my climax, but I wanted to put on a show for Brandi more. My cock pulsed again and again. Each time a stream of white goo poured out and into my waiting mouth.

I swallowed each spurt as it came, savoring not only the taste, but the feel. And by the feel, I mean both the physical sensation of it in my mouth and going down my throat, but also the mental sensation of knowing I was doing something so unquestionably depraved. I’m sure there are plenty of guys who’ve tasted their own cum, and many who like to eat it, but how many have done it in front of their family?

“Oh, fuck! Eat it! Eat your own fucking cum, my sick beautiful sperm whore! Aaaaiiiiieeee! Ah! Ah! Ahhhh!”

That’s when the spray hit me. I thought someone had turned a hose on me, but it didn’t smell like water. I looked and saw a fountain of fluid erupting from my step-mother’s pussy. The spray arced across the five feet between us and doused my cock and face. Holy fuck, Brandi was a squirter!

And not just that, she was a friggin’ projectile squirter. She tensed up and sent another eruption at me. I was in no position to dodge it, so I had to let her soak me in the pungent deluge gushing from her pussy while she strummed her clit with demonic fervor and screamed like a banshee. There was a third squirt that only got the top of my head, then a few more that just splattered to the cement between us.

I sputtered, then carefully uncoiled myself, lying flat on the cushions, my chest rapidly rising and falling as I replenished my oxygen-starved lungs. Whatever it was that shot out of her cunt had a foul taste, spoiling the flavor of my cum. What I didn’t get is why I so badly wanted to taste more of it. I didn’t think it was pee, but as disgusting as it was I kind of liked it.

“Now I see why you wanted to do this out here,” I chuckled and rolled over onto my belly. The way that made my back feel was almost as good as the orgasm I’d just given myself.

“I knew I would probably squirt over this, but that was about twice as much, and as far, as normal for me. Wow, kid, you really fucking did it, didn’t you?”

I just shrugged, feeling unduly proud of myself knowing my dad could probably never make her cum like that. She patted her pussy as it continued to drip. Her stuff was drying on my skin quickly in the sun, but I was fine with it. I was getting more used to the strong smell.

Camilla came out with a stack of towels. I watched as Brady remained slumped in her chair while the maid dabbed her with a moist towel, paying special attention between her legs. She then picked up the black dildo from where it had fallen between my step-mom’s high-heeled feet. Camilla wiped it and placed it on the toy tray. She then came to me.

I thought she was just going to hand me some towels, but she squatted down, turned me over, and began dabbing me with a fresh one.

“I…I can do that myself,” I stammered.

“Allow me, Mister Paul.” She looked at me in a way I wasn’t sure how to interpret. “Please.”

I just nodded dumbly and she went back to work. She wiped my chest and face with a warm, moist face cloth, then patted me dry. Camilla moved down lower and gave me the same treatment there. She took my cock in her hand and gently cleaned it. It had been slowly deflating, but as soon as she touched it I became instantly hard again. It was silly of me to be embarrassed by this given what she knew I had just done, but our housekeeper gave me a reassuring smile that almost allowed me to believe she was enjoying this part of her job. I know I was fooling myself, but it helped me get through it.

Camilla collected everything and headed inside. I watch Brandi as she fussed with her micro-bikini, struggling to get her most private parts almost covered up by the bright green slivers of fabric.

“Thank you, Paul. That was even more entertaining than I expected.” She sucked the last of her drink up loudly through her straw. “I don’t know how we’re going to top that, but I’m sure we’ll think of something, won’t we?” She gave me a somewhat creepy wink. “I’m so glad Avery shared your little secret with me.” Brandi looked toward the pool gate as it rattled open. “Speak of the devil.”

“Devil, my ass,” Avery said as she strode toward us, her heels snapping loudly on the surface of the patio. “You’re more evil than the two of us combined.” Her mom appeared to take that as a compliment. Avery took in the scene, especially noting the huge wet spot between her mother and me. “Looks like you two had fun.”

“The most fun I’ve had in ages, my angel, thanks to you.”

“You’re quite welcome, Mother.” Avery gave me a look that was something between repulsion and lust. “When you’re done with him, send him to my room. I have a new game.” She held up the shopping bags in her hand, one of which was from Frederick’s of Hollywood. “We’re going to play dress up.”

I watched my step-sister’s tight ass as she strutted into the house. How lucky could one guy get? I finally got to not only see my insanely hot step-mom naked, but also using a dildo the size of my arm on herself, and now I get to see her daughter dress up in some slinky things for me.

“I know you’re young, stud, but you should still take a little time to recover before you head up there,” Brandi advised wisely. “Maybe take a dip in the pool, hon.” She came over to me just as I was sitting up and took my face in her hand. “You’re going to make such a pretty lingerie model.” She kissed me on the lips, slipping me just a little tongue, before leaving me there in stunned silence.

What did she mean by that? Wait. The penny dropped. Avery wasn’t going to be dressing up in the slinky things from Frederick’s…I was!

~ ~ ~ ~ ~ ~ ~ ~ ~ ~

7 Comments

7 thoughts on “Self-Sucking Sissy 2

  1. Rachel,
    Love your stories, I’m on the email list. So much pleasure to be had here.
    Wish Chapter 3 would happen. :-(

  2. I’m new to your blog which I found via literotica. I’ve only read your FAQ and these two chapters of self suck sissy, and frankly, I’m blown away with the excellent writing and the incredibly erotic content. Thank you. I look forward to reading more of your fantasies.

  3. I remember trying to suck my own cock while growing up. I never could reach it though. Now a days I still can’t, I’ve tried.

  4. Positively the best nut busting story I’ve masturbated to in quite a long time.. DMM you hit every damn erection nerve in my depraved mind.. And OMG the cigarette smoking.. My favorite fetish “Sexy Mom’s Smoking”

    Your details and adjectives kept me stroking like a mad man.. My pre-fuck was really flowing tonight.. I edged till there was no turning back and Oh, did the sticky sperm erupt..

    Tasty, Tasty, Tasty.. Thank you DMM

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