When I was fifteen my mother left my dad and me. It wasn’t her fault; my dad was such a hound dog. As much as my mom and I wanted to live together, she told me that she had almost no money, seeing as how my dad made her sign a pre-nuptial agreement when they got married, leaving her with little money of her own. My mom and I are still really close and we typically see each other at least once a week.

Within a year my dad found the perfect kind of wife for himself: a gold digger by the name of Cindy that didn’t care about his cheating as long as she was well taken care of. She still signed a pre-nup, just like my mom did, in order to protect his first love: his money. Still, the financial freedom he afforded her was more than worth it to her.

Dad met Cindy at this club, Fire Cats, which he would often go to after work with the rest of his buddies at the law firm he worked for. Cindy was one of the VIP hostesses that took care of my dad and his group from work, and pretty soon she started taking care of my dad in ways that did not fit into her job description. It wasn’t long after their first few private ‘VIP sessions’ together that my dad told me that he was getting married to a girl from the club.

I couldn’t believe my dad! Not only did he try to drive my mother, the sweetest woman in the world, out of our lives simply because she challenged his dog-like behavior, but now he wanted to bring home this woman from the club, who likely was only really interested in his money. My dad was fifty-one with grey hair, and while he stayed in fairly good shape for his age, what were the odds that a woman from the Fire Cats club truly liked his dismal personality?

Shortly after my sixteenth birthday, my dad brought Cindy home to meet me for the first time, and once I saw her there was no doubt in my mind; this woman is not interested in my dad’s looks, or his personality. Cindy was twenty-eight, 5’ 10” with long, flowing black hair, milk chocolate-brown skin, hypnotic green eyes, flawless white teeth, an angelic face and an amazing body. She had long, slender legs, C cup breasts, and despite only seeing her from the front, I could tell by her hourglass figure that she must have had a fantastic ass. She was wearing a short, hot pink dress that exposed her great rack, and a pair of black high heels. I bet she got a LOT of tips working at the Fire Cats club.

“Michael, this is Cindy, my bride to be, and Cindy, this is my son, Michael.” My dad introduced her and then opened his hand in my direction as he introduced me.

Cindy walked towards me, one high-heeled foot in front of the other, as if she were walking the catwalk in a fashion show. She extended her hand towards me and I weakly shook it.

“Hi, Michael, it’s great to finally meet you. How old are you?”

“Um, I’m sixteen,” I awkwardly squeaked out.

“Wow, only sixteen and looking so fine. I can’t imagine how amazing you’re going to look when you turn eighteen,” Cindy said as she fumbled with my shirt collar

I blushed and looked away, embarrassed to have such an attractive woman say such a thing about me. I also put my hands into my jeans in an attempt to hide the growing erection that was forming below. Not only did I get turned on by Cindy’s comment of how fine I looked, whether she meant it as a joke or not, but when she stepped towards me to play with my collar I also managed to briefly look down her dress at the melons that were her breasts.

My dad looked slightly annoyed at Cindy’s attempt to get friendly with me by flirting like I was a customer of hers at the club, so he reached over and gently pulled her over to him.

“Hey, hey, hey, don’t go stealing my future wife, son. Come on, Cindy, we’re going to be late for our reservations if we don’t get moving. You’ll be ok fixing yourself something for supper right, son? We have reservations at Mario’s tonight.”

Typical dad; if a hot woman was involved he’d dump me here by myself with no warning at all. I told him that of course I would and he started walking towards the front door with Cindy on his arm. As Cindy was walking, she turned back to look at me and gave me a little wave, the kind where someone bends their four main fingers, but leaves their thumb in place. As soon as she and my dad left, I bolted up the stairs to my room.

As a sixteen-year-old boy, I naturally had a lot of sexual energy stored up inside of me, and learning that I was going to get a hot stepmom that seemed to enjoy flirting with her future husband’s son, definitely added fuel to the fire. I practically jumped onto me bed, laid back, and pulled down my jeans and boxers. I gripped my cock and started masturbating furiously at the thought of my new stepmom.

As I stroked myself, I thought of Cindy slowing pulling down her dress, leaving her in a matching black lace bra and thong. Slowly she would walk towards me as she undid her bra.

“Come on, Michael. Your dad can’t give me what you can. I need young, hard cock in my pussy, just like yours. Come on, Michael, fuck me.”

That was as far as I got into my fantasy as a burst of cum flew straight up like a fountain and arced before landing on my stomach. Another two small spurts also came out, one landing in my pubic hair, while the final one dripped down the length of my shaft. I lay on my bed, my lower body still covered in cum as I fought to regain my breath. Over time I would keep imagining my stepmother coming on to me, and each time I would build up a resistance and get further into the daydream, until finally I came in Cindy’s pussy and she thanked me so much for giving her what she desperately needed.

I would have similar fantasies for the next two years until I turned eighteen.

By the time I turned eighteen, I had changed a lot since I first met Cindy. I put on a good deal of muscle being on the school’s wrestling team, and with that came a big boost in my confidence. I had been in a few relationships in the past two years, all of which turned sexual, mostly thanks to my position on the wrestling team, my muscles, and having an almost seven-and-a-half-inch dick didn’t hurt either.

My dad was still with Cindy, who was now thirty. I figured my dad would have tossed Cindy away by now, but for some reason he kept her around. I guess it’s easy being married to someone who doesn’t really care if you show up late at night smelling of booze with another woman’s lipstick on your collar. As for Cindy, as long as she got her weekly ‘allowance,’ she was as happy as a dog with a bone.

As for turning thirty, Cindy still looked as amazing as when I first met her. About the only things that really changed were that she now wore her dark black hair in a short, curly bob that ended at her neck, which actually looked pretty hot, and she had taken to wearing simpler clothes around the house, like tank tops and short shorts. The exception was in the morning when Cindy woke up; she would always come downstairs barefoot wearing an open light pink silk robe that would display some of the sexy lingerie that she owned.

Cindy’s state of dress in the morning always kind of irked my dad; he felt it was inappropriate for anyone but him to see what his wife was hiding under that robe of hers. That was the thing about my dad, he was a typical misogynist in that he wanted the freedom to hang around loose women all the time, but he didn’t want his wife to flirt with or tease any other men, myself included.

I think Cindy liked teasing other men besides my dad, it was simply in her nature. In addition to walking around the house in various states of undress in the morning, she would also do so when my friends came over. In fact, she would especially do so when my friends were over. There was one time where I was hanging out by the pool with two friends from the wrestling team, along with their girlfriends and my girlfriend at the time, Stephanie. Apparently right around the same time we were using the pool, my dear, not at all old, stepmom decided she really wanted to get some sun out by the pool, even though she had been home alone all day.

Cindy came out of the house wearing a purple two-piece string bikini with black zebra stripes on it that left almost nothing to the imagination, especially the thong back of the bikini bottom. As she strolled out into the backyard, she smiled at all of us and lowered her sunglasses.

“Hey boys, and girls,” she added belatedly, as if to show her preference for the boys in the crowd, and her contempt for the girls. “I’m just going to catch some sun on the other side of the pool. Don’t pay any attention to me.” Clearly though, she wanted attention on her.

As she sat on a deck chair on the other side of pool, Cindy began to slowly, erotically slowly, oil herself up. Even though I had seen such things hundreds of times already in the nearly two years that she had lived with my dad and I, I couldn’t help but stare at my stepmother. Both of my friends were staring at Cindy too, with their mouths slightly open, much to the chagrin of their soon to be ex-girlfriends. When she finished oiling herself up, she laid down with one leg flat and the other one bent at the knee and slowly moving back and forth, almost as if she were motioning all of us boys over to her. Cindy loved nothing more than to be the center of attention, likely something that carried over from her time at the Fire Cats club.

Due to all of our staring, all three of us guys found ourselves without girlfriends after our little dip by the pool. I was really pissed off, since I had spent almost a month trying to get into Stephanie’s pants, and now it was all ruined because of Cindy! Even more annoying, my two fellow teammates had taken it upon themselves to tell everyone else on the wrestling team about how I had a smoking hot stepmom. As a result, I was constantly being inundated with sarcastic questions like whether they could come over for dinner to meet Cindy, or whether I had ever seen her naked; they even asked if I ever jerked off while thinking of her.

I didn’t know how, but one day I was going to make Cindy pay for embarrassing me like she did. It was bad enough that she tanked my chance at getting it on with Stephanie, but giving everyone on the wrestling team ammo to ridicule me was not something I was going to let go. Lucky for me, a few weeks later my chance at not only revenge, but also taking care of a two-year itch, would finally present itself.

It was a Friday afternoon and I arrived home shortly after school ended. When I opened the front door, I could hear my dad and stepmom arguing. Apparently, Cindy had spent her entire week’s allowance before the weekend had actually begun, and now she wanted a bit more to go on a trip to Las Vegas with some of her friends from the club. My dad wasn’t having any of it. As much as my dad loved beautiful women, he loved his money more, and there was no way in Hell he was going to give Cindy another dime before Monday.

Eventually the fight ended and my dad said that he was going to the club and he wouldn’t be back until very late. Cindy huffed and stood in the kitchen with her arms folded.

“Oh, hi, Michael. Uh, did you hear any of that?”

“Yeah, I did. Sorry, but you know how strict my dad is with money.”

“Ugh, I know, but I REALLY want to go on this trip with my girlfriends to Vegas and I just need a couple hundred, maybe a thousand bucks for the weekend.” She sighed. “Well, I guess there’s nothing I can do. I’m going to take a shower and then we can decide what to do for dinner, your dad clearly won’t be joining us.”

I acknowledged Cindy and sat on the couch in the living room while I thumbed through a sports magazine on the coffee table. It had been about six minutes, but I still didn’t hear the water start running. I did, however, hear a fair bit of rummaging going on in my dad’s room. He and Cindy slept in different rooms, as neither was interested in sleeping together, only doing the dirty deed and then going their separate ways for the rest of the night.

Eventually my curiosity got the better of me and I quietly snuck up the stairs to see what Cindy was up to. I carefully cracked the door to my dad’s room open slightly so I could peek inside. I saw Cindy, bent over at the waist with her ass pointed towards me as she rummaged around in one of my dad’s drawers for something. Without even thinking, one of my hands found its way to the stiffening cock in my shorts and began rubbing it, just I like I had done many times in the past when I was able to peek at Cindy without her noticing.

‘Damn! What a great ass!’ I silently mouthed to myself. Since Cindy was bending over at the waist and looking into the lower drawers of my dad’s dresser, her ass was pointed straight towards me, straining against the super tight, super short jean shorts that she was wearing. The beginnings of the curves of her ass were actually able to poke out from underneath the material of the jeans due to how they were riding up her ass. She was also wearing a pink, tight spaghetti-strap tank top that showed off her pierced navel and her ample cleavage, and a pair of high-heeled, cork wedge sandals with silver straps.

There was little reason for Cindy to be looking for anything in my dad’s room, as she didn’t keep anything in there of hers, so I took out my cell phone and started to record her in case something suspicious was taking place. A few seconds after I began recording, Cindy pulled a plastic card out from underneath one of the drawers and held it up between her fingers.

“Jackpot baby! Vegas here I come!”

It turned out that Cindy was holding up one of my dad’s debit cards. Dad didn’t like carrying his debit cards around in case his wallet was stolen and someone could gain access to one of his bank accounts, so he usually only carried one or two credit cards on him and stashed everything else in his room where he thought no one would find them. It looks like Cindy found one of his cards though, and she clearly planned to use it to bankroll her little girls’ weekend in Vegas.

Cindy’s plan was actually pretty smart too; my dad had a lot of money and loathed going over financial documents like credit card bills and withdrawal statements. For someone so rich, and so in love with his money, my dad was kind of lazy when it came to the fine details of his finances. However, while Cindy may have started out the weekend lucky, I was about to get lucky myself.

I opened the door and walked into my dad’s room, causing Cindy to jump at the sound of the door creaking open and stuff the debit card into one of her pockets, which hardly fit given how tight the shorts were.

“Michael! What are doing in here?” Cindy asked nervously.

“Oh, well I heard noises coming from in here and I was curious about what was going on. I thought you said you were going to take a shower, but I didn’t hear the water turn on.”

“Oh, well, I got a call from your father and he said he forgot his VIP card from the club and he wanted me to read him the number on it so he can get into the VIP lounge. I just came up here to find it.”

“Hmm, I saw dad leave his phone on the front table in the charger as he stormed out of the house. How could he call you?”

“Maybe he used a friend’s cell, or the phone at the club.”

“I don’t think so, because I’ve taken his card and used it to get into the club on nights where he doesn’t go out, and I know for a fact that there are no numbers on the card, only a magnetic strip. Sooooo…”

Cindy swallowed discreetly and smiled nervously as she struggled to think up a way to explain her excuse.

“Look, Michael, I can explain-”

“Actually, I think I can explain better.” I pulled my phone out of my pocket and started the playback function. Cindy’s jaw literally dropped. “You see, I have this video here of you swiping my dad’s debit card and triumphantly declaring your upcoming visit to Vegas. Now what would my dad say if he happened to see this video?”

Cindy looked so distraught.

“Ok, I’ll… I’ll give you whatever you want. WE have his debit card, and he’ll never know how much we took. How much do you want?”

I smiled slyly.

“It’s not exactly money I want, Cindy.” I took a few steps towards her. “You’ve been walking around this house wearing next to nothing for the past two years.” I stood about a foot away from her now. “On top of that, you cost me a shot at having sex with a really hot girl a few weeks ago, and now…” I started to gently stroke her left arm. “I’m going to use you to scratch an itch I’ve had for a little while now.”

Cindy looked really worried now.

“Michael, I…” My hand reached around her and I began squeezing her left ass cheek. “Michael, we can’t do this. I know I might not be the perfect housewife, but I’ve never…” My hand came back around to her front and began rubbing her pussy through her shorts. “But I’ve never, ugh, cheated on your daaaahhh!” She was clearly enjoying my little shakedown.

“Then you must really need this as much as I do, because there is no way my dad is giving you what you really need…” My rubbing became faster and more forceful. “What you really want.”

Cindy’s worried look had faded from her face as her eyes closed and her head tilted back slightly.

“You give me what I want, and not only will I let you take whatever you want from my dad, but I’ll also give you something that he can’t with all of his money.” I leaned into Cindy’s ear. “When we first met, you said I looked so fine that you couldn’t imagine what I would look like when I turned eighteen. Well…” I gently lowered Cindy’s head to look down at my crotch. “Now you can see how much I’ve changed where it counts.” I pulled down my shorts and exposed my seven-and-a-half-inch dick to my stepmother and she literally gasped.

“Oh my God! Michael, your cock is at least an inch bigger than your father’s. I haven’t had anyone but your father in so long.”

“Well, if you want to go to Vegas with your friends this weekend, you’re going to make me, and my cock, happy. So, why don’t you kneel on the edge of the bed and let’s get started?”

Cindy did what she was told and got onto my dad’s bed and knelt on all fours at the end facing me. Knowing exactly what I wanted, she reached out and started stroking my shaft.

“I can’t believe I haven’t ever thought to check out what you were hiding down there. I’ve always thought you were pretty cute, and certainly pretty hot the past year, but I never expected you to have such a nice cock.”

I smiled.

“Well if you spent less time teasing my friends and I, you could have been enjoying this even sooner. Now I think the time for talk is over Cindy.”

Without any further dialogue between the two of us, Cindy spat on my cock and began using it as lubricant, giving my shaft a few more pumps with her hand before putting it in her mouth. The warmth of her mouth surrounded me and I moaned softly as I finally managed to get my cock where it belonged: in my stepmom. She jerked the base of my cock gently as she moved her head back and forth, my shaft gliding in and out of her mouth.

“Oh, Cindy. Oh, God that feels great.”

She didn’t even acknowledge me; she was too busy enjoying herself. With an audible ‘pop,’ the head of my dick exited Cindy’s mouth and she began to jerk me off as she sucked one of my balls into her mouth. The heat that was being applied to my balls felt even better than it did on my cock. After a few seconds she went back to sucking me off.

Pushing the envelope further, I gently grabbed Cindy’s head with my right hand and made her deep-throat me. She looked up at me, as if to ask ‘What are you doing!?’ But I didn’t care, I just smiled down at her for a second before releasing her. In need of a breath, she took my cock out of her mouth and jerked me as she gulped in large breaths of air, her saliva coating my dick and allowing her hand to glide seamlessly over my shaft.

“Fuck! It’s been a while since I deep-throated a cock. Your father isn’t exactly big enough for me to do this kind of thing.”

“Well I guess we’re going to have to practice your deep-throating skills a bit more in the future, won’t we?”

“Oooh, yeah. I think that would be a really good idea.” With that she went back to sucking my dick.

As I looked down at Cindy, I noticed that her nipples were poking through her tank top, and that she clearly was not wearing a bra.

“Let’s take that top off, shall we? I want to see those luscious tits of yours, mom.” I don’t know why on Earth I decided to refer to Cindy as my mom, especially since I never called her that before. I guess it was just incredibly erotic to being doing it with a woman that was not only hot, but was also a forbidden pleasure: my dad’s wife, my stepmother.

Despite how I referred to her as mom out of nowhere, Cindy didn’t seem to mind it at all, in fact she seemed to really like it. She took me out of her mouth and stroked me as she spoke.

“Yeah? You want to see mommy’s big tits, baby?” I think I nearly creamed myself right then and there, but luckily, I managed to hold out.

“Yeah, I want to see them. I NEED to see them!” I pleaded.

Cindy started removing her top and I helped her to do it even faster. Her tits were perfect, right down to her dark nipples which stood fully erect. I couldn’t control myself and leaned my face forward to start sucking on one of them.

“Oooohhhhh, yeah baby, suck on my nipples.” I did like my stepmother told me as I switched breasts and sucked on her remaining dry nipple. “Mmmmmm, yeah that feels good, but I think I need a little more.”

She got off of the bed and started walking away from me, seductively swaying her hips side to side while walking one foot in front of the other. She stopped a few feet away from me and hooked her thumbs into the belt loops of her shorts. Slowly, agonizingly slowly she bent over and pulled the shorts, along with her pink thong, down her legs before finally letting them drop to the floor, leaving her in nothing but her sandals.

While she was bent over, I could see Cindy’s pussy from behind, and just like I thought it would be, it was completely smooth, no stubble to be found. Clearly Cindy liked to stay prepared. She turned to face me and placed her hands on her hips.

“I know I’m doing this to keep you from ratting me out to your dad, but would you do a favor for me Michael?”

I just nodded, too dazed to remember that I was supposed to be the one in control, the one directing Cindy to do things she might not be comfortable doing to get back at her for embarrassing me and teasing me for so long. It couldn’t be helped though; with all that beauty, I didn’t care how I got with Cindy, whether she was in control or I was, I just wanted to fuck her so, so bad!

“Would you eat my pussy while I suck your cock, baby?”

Again, I simply nodded.

“Then why don’t you go and lie down on the bed for me?”

I removed my T-shirt and lied down on my father’s bed, naked, and Cindy climbed on top of me and placed her pussy over my face while she lowered her lips to my cock. As she started bobbing her head up and down my shaft, I began slowly licking all around her pussy, getting the lay of the land before focusing my attention on her clit. Even with Cindy focused on my cock, I could still hear her moan around my shaft. As I continued focusing on her clit, I also put two fingers in her pussy and began thrusting them in and out faster and faster.

We 69ed for a few more minutes until we managed to cum almost simultaneously. Since Cindy had been blowing me for a while, I came first and sent multiple shots of cum into her mouth, which I could actually feel her swallow as her throat closed around the head of my dick. Shortly afterwards, she came and a sweet gush of pussy juice filled my mouth. We licked up whatever residual from each other for about a minute before Cindy got off of me and walked in front of the bed.

“I hope you’ve got more cum for your stepmother, Michael.” She stood with her feet shoulder length apart with her hands on her hips.

“I’m sure I can supply you with what you need. Although, I could use a little help getting hard again.”

She smiled.

“I think I can help you with that.”

Cindy began swaying her hips as she licked her fingers and brought them down to her pussy. She slowly rubbed herself as she moaned quietly and pouted her lips at me. I was already starting to get hard again.

“Mmmm, getting nice and hard for mommy, Michael? I’m counting on you to give me what I need: a nice, hard, young cock.”

That was all the encouragement I needed to get rock hard again and I was good to go.

“I’m ready, and I’ve got what you need.”

Cindy walked around the bed and climbed on top of me again, once more facing away from me as she lowered herself onto my cock. Although I would have loved to have her facing me as we did it, it was still great to get a view of that perfectly rounded ass as I fucked her.

“Ooohhh! That feels so good, Michael. Teenagers always seem to have the hardest cocks. Your dad could barely keep it up, let alone get hard again to go a second round.”

“That’s why you need to come and visit my room once in a while instead of my dad’s. You need someone young and ready to give you not only what you need, but what you deserve.”

After getting me all the way inside of her, Cindy started moving herself up and down my cock. I still couldn’t believe that I was finally able to fuck my stepmother, and also how amazing it was. A part of me had worried that her pussy wouldn’t be tight anymore, given that she was thirty and had already had a ton of sex with my dad, but she was still pretty tight; not teenager tight, but definitely still pretty good.

As I saw Cindy’s ass going up and down and I reached out and spanked her, not too hard, but enough to let her know I was thinking about her ass.

“Ow! Ooh, Michael, you like your stepmom’s ass?”

“Have I not made that clear enough?” To press the point home, I grabbed Cindy’s ass cheeks with both hands and squeezed them hard and pushed and pulled at them to get her to slide up and down my cock faster.

“Ooohhh, I think you should get on top of me. I want to look into my stepson’s eyes while he fucks me.”

Slowly, Cindy slid herself off of me and turned around to face me. Instead of immediately inserting me back into her, she grabbed my head and forcefully pushed her lips to mine. The kiss wasn’t slow and loving; it was raw, passionate, driven simply by lust, not love. It was pretty clear we weren’t in love, we just wanted to fuck.

After Cindy ended the kiss, she took hold of my cock and pressed it to her pussy lips. She started going up and down me again, but apparently it was easier for her to move faster in the position than in reverse, as she was moving much faster than before. Her back was arched and her head thrown back as my cock slammed her pussy, causing her breasts to bounce up and down, giving me a sexy show.

“Fuck, fuck, FUCK! Come on baby, mommy needs this so bad!”

I increased my own thrusts so that I was pounding Cindy the hardest I could. In fact, I was pounding her so hard my dick was actually starting to get a little sore from repeatedly slamming into the back of her pussy.

“Aaaahhhh! Fuck me, fuck me, fuck me! OH GOD I’M GONNA CUM!”

Shortly after declaring her own orgasm, I answered with my own, shooting four blasts of creamy white cum into my stepmother’s chocolate pussy. Cindy was so out of it after we both climaxed that she collapsed on top of me as she took in deep breaths. After a minute, she raised herself off of me and curled up in front of me as she spoke.

“Oh, Michael. Oh God, Michael, that was the BEST! Oooh, you have no idea how much I needed that. I think getting caught trying to steal from your dad was the best thing to happen to me in the past two years.”

“Agreed! I did promise to delete that tape I took of you, and I’m a man of my word. Still… I hope this doesn’t mean that we can’t do something again in the future.”

“Michael, I think we need to keep doing this.” She casually zigzagged a finger over my chest and stomach. “I mean, it’s just not healthy for us keep all of this mutual lust for one another bottled up. I think, we need to keep doing this on a regular basis, if nothing else but to make sure that we maintain a healthy stepmother-stepson relationship. Don’t you think, son?”

“Absolutely, Cin, err, I mean, mom.”

“Good boy. Now if you’ll excuse me, I need to pack for Vegas. Oh, and clean this all up will you? I don’t want your dad seeing all of this mess we made, and when he asks where I went, tell him I’m spending the night at Clarice’s. Do this for me…” She used a finger to scoop some of my cum out of her pussy and proceeded to slowly lick it all off. “And I’ll do to you whatever you want.” She got out of bed and left, looking over her shoulder as I stared at her ass as it exited the room.

Even though I started out trying to get back at Cindy for teasing me for so long, everything still ended with her telling me to clean something up, but I didn’t care. As long as Cindy and I kept having sex, I would clean the whole damn house if I had to. Needless to say, we repeated what happened in my father’s bed for the rest of the time my dad was married to Cindy.