Inside the Mind of a Cocksucking Sissy
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My step-sister was back to her normal bitchy self. I thought things might be different after I had sucked my own cock in front of her while she finger fucked herself. Apparently not. When she wasn’t ignoring me, she treated me like something she found stuck to the bottom of her shoe after walking through the dog park. I was sore as I’d ever been and could barely move my neck, but no one in the family seemed to notice.
I had made it a point over the next few days to be out by the pool at the time when Avery and I usually did our yoga stuff, but she was never anywhere to be seen. I tried jerking off out there one day when our parents weren’t home, but I was pretty sure she wasn’t watching, which took a lot of the thrill out of it. It was a couple days after that when I came out onto the patio and Gold-Digger Barbie, a.k.a. my step-mom, was there lying on one of the lounge chairs.
Yeah, she was older, but she managed to keep her body pretty tight. Especially those factory-grade tits of her. She was wearing a shiny black one-piece bathing suit that was cut very high on her hips and very low in the front. I did my best not to stare at her cleavage, but she probably noticed me stealing looks. I’m sure she was used to it since she was always showing off plenty of boobage wherever she went.
“Good afternoon, Paul,” she purred. “What brings you out here?”
Don’t flatter yourself, lady. “I don’t know. A swim, maybe.”
“If you were thinking of skinny dipping, don’t mind me.” She sipped down the last of her pina colada through a long, purple straw. “I can keep a secret.”
The way she winked reminded me of her daughter. I just stood there like a dummy not knowing what to say or do. In the two plus years that she had been my step-mother she had never once acted flirty like that around me. Maybe she was drunk.
“Avery and I had an interesting chat last night,” she set her empty glass aside and looked over the top of her big sunglasses at me. “Your name came up.”
Oh, crap. What was my conniving step-sister doing to get me into trouble this time?
“What, um...what did she say?”
“She stopped by my bedroom last night to borrow my AstroGlide – you know what that is, don’t you, Paul? It’s a brand of lubricant...for sex. It’s the best. I wouldn’t use anything else for doing anal.” She pushed her glasses back into place after savoring the shocked look on my face. My step-mom settled back in her chair, arching her back just enough to insure that I’d notice how her nipples had become hard since we started talking. This was getting too weird.
“Okay, well, I should probably get going—”
“I gave Avery one of the fresh tubes that I had just bought, and we got to talking. She mentioned something very interesting about you.” Our maid, Camila appeared out of nowhere to take away my step-mom’s glass and replace it with a bright red margarita. “The rumor is that you can suck your own cock. Is that true?”
Camila looked at me with a strange mix of embarrassment and wonder, before resuming her professional expression of impassive invisibility. She moved back toward the house, the rubber soles of her white shoes allowing her to leave as silently as she had arrived.
“I...I don’t know why she would say that…”
“Don’t bother playing dumb with me, Paul. I know what you kids are like these days. Now that the internet is everywhere, you little fuck monkeys are into all kinds of kinky shit that we never would have thought of when I was your age.” She took a sip of her drink, allowing some of the condensation to conspicuously drip between her exaggerated breasts. “So, can you?”
“Um...yeah, I guess I sorta can.”
“Nice,” she declared with a lascivious smile. “You must either have a huge cock or be exceptionally flexible.”
This was the last conversation I ever expected to have in my life. “A little of both,” I said with a helpless shrug.
“Mmmm, I never told anyone this before, but that’s something I’ve always wanted to see. There’s something so deliciously depraved about the idea of a man performing oral sex on himself.”
Depraved. That was a word Avery liked to use. I was beginning to suspect that these two shared a lot more than I would have ever guessed.
“I’m sure you wouldn’t mind indulging your dear mother and giving me a private demonstration of your cocksucking abilities, would you?”
“Uh...I don’t know,” I looked around to make sure we were alone. Yes, for an older lady she had a smoking body, and I guess she was pretty if you liked that sort of overly made-up cougar style, but this was still my step-mom – my father’s wife. “My back is kinda stiff, and—”
She held up a hand and laughed. “Not right now, silly boy. Although I like the way you think.” She looked me up and down with a hungry gaze. “Your dad is going off to one of his film festival fuck fests in a couple days. You can do your act for me once he’s safely away. There’s no need for him to know about this, or about any of the other naughty things you’ve been up to lately. Shall we meet back here, say, Friday around seven o’clock?”
It was phrased as a question, but the veiled threat that preceded it made it clear I had no choice but to accept her invitation.
“Okay...seven o’clock,” I half-heartedly agreed, before ducking my head and escaping before it got any worse. I had four days to figure out how I was going to get out of this mess.
By the time I got to my room, my dick was hard as a rock. Not the reaction I wanted. I paced my bedroom a few times before giving in and peeking out from behind my curtains. My step-mom was still out by the pool. Even at that distance I could see her nipples poking up from under her bathing suit. Un-fucking-believable. No matter how much I disliked her as a human being, those were still some insanely hot tits. I pulled out my cock and started stroking.
“God, you’ll jerk off to anything, won’t you, perv boy?”
Avery’s voice whispering in my ear made me jump and trip over my shorts that were around my ankles. I attempted to cover up, but it was no use. Especially when I noticed that my step-sister had on a teensy white bikini top and nothing else. The bottoms were dangling from her index finger as she looked down at me and shook her head in mock disappointment.
“I was going to let you jack off on my pussy, but it looks like you’d rather beat it to your mom, so I’ll just leave you two alone.” She gave me that infuriating wink again as she turned and walked out of my room, shaking her hot ass the whole way like the cock-teasing bitch that she was.
I had to figure a way to get out of sucking myself off in front of my step-mom without getting into trouble. I stood up and peeked out the curtains. And I’d get started on that right after I finished whacking off to those pontoons she calls tits!
~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Brandy, 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 find a way out. 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 a neon green 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 bright yellow micro-bikini, the kind I thought only existed in porn videos. Two strips of thin fabric that couldn’t have been more than a couple 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 devoted 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 actually cover up any of this. The fact that she appeared to have an all-over tan didn’t escape my attention. When Brandy 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 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 yellow 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?”
Brandy laughed and took a long pull from her cigarette. “Your words, not mine, kiddo.” She didn’t bother to turn her head away from me when she blew out a 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 lingering 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.” Brandy’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.” Brandy 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 pièce de résistance. Let’s see this nasty little 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 ended up 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’d 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 gone home by now! Of all days for her to be working overtime. I can’t believe Brandy 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.
Brandy picked up a pink toy that had several oblong bulges and was 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 the 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 covering 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 the kind of things 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.
Brandy 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!” Brandy must have been talking during most of that, but I only caught 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, wasTo continue reading this story you must be a member. Join for FREE here.
I had made it a point over the next few days to be out by the pool at the time when Avery and I usually did our yoga stuff, but she was never anywhere to be seen. I tried jerking off out there one day when our parents weren’t home, but I was pretty sure she wasn’t watching, which took a lot of the thrill out of it. It was a couple days after that when I came out onto the patio and Gold-Digger Barbie, a.k.a. my step-mom, was there lying on one of the lounge chairs.
Yeah, she was older, but she managed to keep her body pretty tight. Especially those factory-grade tits of her. She was wearing a shiny black one-piece bathing suit that was cut very high on her hips and very low in the front. I did my best not to stare at her cleavage, but she probably noticed me stealing looks. I’m sure she was used to it since she was always showing off plenty of boobage wherever she went.
“Good afternoon, Paul,” she purred. “What brings you out here?”
Don’t flatter yourself, lady. “I don’t know. A swim, maybe.”
“If you were thinking of skinny dipping, don’t mind me.” She sipped down the last of her pina colada through a long, purple straw. “I can keep a secret.”
The way she winked reminded me of her daughter. I just stood there like a dummy not knowing what to say or do. In the two plus years that she had been my step-mother she had never once acted flirty like that around me. Maybe she was drunk.
“Avery and I had an interesting chat last night,” she set her empty glass aside and looked over the top of her big sunglasses at me. “Your name came up.”
Oh, crap. What was my conniving step-sister doing to get me into trouble this time?
“What, um...what did she say?”
“She stopped by my bedroom last night to borrow my AstroGlide – you know what that is, don’t you, Paul? It’s a brand of lubricant...for sex. It’s the best. I wouldn’t use anything else for doing anal.” She pushed her glasses back into place after savoring the shocked look on my face. My step-mom settled back in her chair, arching her back just enough to insure that I’d notice how her nipples had become hard since we started talking. This was getting too weird.
“Okay, well, I should probably get going—”
“I gave Avery one of the fresh tubes that I had just bought, and we got to talking. She mentioned something very interesting about you.” Our maid, Camila appeared out of nowhere to take away my step-mom’s glass and replace it with a bright red margarita. “The rumor is that you can suck your own cock. Is that true?”
Camila looked at me with a strange mix of embarrassment and wonder, before resuming her professional expression of impassive invisibility. She moved back toward the house, the rubber soles of her white shoes allowing her to leave as silently as she had arrived.
“I...I don’t know why she would say that…”
“Don’t bother playing dumb with me, Paul. I know what you kids are like these days. Now that the internet is everywhere, you little fuck monkeys are into all kinds of kinky shit that we never would have thought of when I was your age.” She took a sip of her drink, allowing some of the condensation to conspicuously drip between her exaggerated breasts. “So, can you?”
“Um...yeah, I guess I sorta can.”
“Nice,” she declared with a lascivious smile. “You must either have a huge cock or be exceptionally flexible.”
This was the last conversation I ever expected to have in my life. “A little of both,” I said with a helpless shrug.
“Mmmm, I never told anyone this before, but that’s something I’ve always wanted to see. There’s something so deliciously depraved about the idea of a man performing oral sex on himself.”
Depraved. That was a word Avery liked to use. I was beginning to suspect that these two shared a lot more than I would have ever guessed.
“I’m sure you wouldn’t mind indulging your dear mother and giving me a private demonstration of your cocksucking abilities, would you?”
“Uh...I don’t know,” I looked around to make sure we were alone. Yes, for an older lady she had a smoking body, and I guess she was pretty if you liked that sort of overly made-up cougar style, but this was still my step-mom – my father’s wife. “My back is kinda stiff, and—”
She held up a hand and laughed. “Not right now, silly boy. Although I like the way you think.” She looked me up and down with a hungry gaze. “Your dad is going off to one of his film festival fuck fests in a couple days. You can do your act for me once he’s safely away. There’s no need for him to know about this, or about any of the other naughty things you’ve been up to lately. Shall we meet back here, say, Friday around seven o’clock?”
It was phrased as a question, but the veiled threat that preceded it made it clear I had no choice but to accept her invitation.
“Okay...seven o’clock,” I half-heartedly agreed, before ducking my head and escaping before it got any worse. I had four days to figure out how I was going to get out of this mess.
By the time I got to my room, my dick was hard as a rock. Not the reaction I wanted. I paced my bedroom a few times before giving in and peeking out from behind my curtains. My step-mom was still out by the pool. Even at that distance I could see her nipples poking up from under her bathing suit. Un-fucking-believable. No matter how much I disliked her as a human being, those were still some insanely hot tits. I pulled out my cock and started stroking.
“God, you’ll jerk off to anything, won’t you, perv boy?”
Avery’s voice whispering in my ear made me jump and trip over my shorts that were around my ankles. I attempted to cover up, but it was no use. Especially when I noticed that my step-sister had on a teensy white bikini top and nothing else. The bottoms were dangling from her index finger as she looked down at me and shook her head in mock disappointment.
“I was going to let you jack off on my pussy, but it looks like you’d rather beat it to your mom, so I’ll just leave you two alone.” She gave me that infuriating wink again as she turned and walked out of my room, shaking her hot ass the whole way like the cock-teasing bitch that she was.
I had to figure a way to get out of sucking myself off in front of my step-mom without getting into trouble. I stood up and peeked out the curtains. And I’d get started on that right after I finished whacking off to those pontoons she calls tits!
~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Brandy, 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 find a way out. 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 a neon green 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 bright yellow micro-bikini, the kind I thought only existed in porn videos. Two strips of thin fabric that couldn’t have been more than a couple 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 devoted 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 actually cover up any of this. The fact that she appeared to have an all-over tan didn’t escape my attention. When Brandy 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 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 yellow 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?”
Brandy laughed and took a long pull from her cigarette. “Your words, not mine, kiddo.” She didn’t bother to turn her head away from me when she blew out a 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 lingering 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.” Brandy’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.” Brandy 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 pièce de résistance. Let’s see this nasty little 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 ended up 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’d 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 gone home by now! Of all days for her to be working overtime. I can’t believe Brandy 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.
Brandy picked up a pink toy that had several oblong bulges and was 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 the 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 covering 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 the kind of things 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.
Brandy 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!” Brandy must have been talking during most of that, but I only caught 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, wasTo continue reading this story you must be a member. Join for FREE here.
Myra
- 17.01.2023
- 10
- 0
- Category:
- Taboo
