When I was fifteen my mother left my dad and me. 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: She still signed a pre-nup, just like my mom did, in order to protect his first love: 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. 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? 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. 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. How old are you? I also put my hands into my jeans in an attempt to hide the growing erection that was forming below. 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.
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. I need young, hard cock in my pussy, just like yours. Come on, Michael, fuck me. 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.
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. 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. 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.
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. As she sat on a deck chair on the other side of pool, Cindy began to slowly, erotically slowly, oil herself up. 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.
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. 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. 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.
Cindy huffed and stood in the kitchen with her arms folded. Uh, did you hear any of that? Sorry, but you know how strict my dad is with money. 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. 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.
What a great ass! 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. 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.
Vegas here I come! 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. What are doing in here? I just came up here to find it. How could he call you? Now what would my dad say if he happened to see this video? How much do you want? Knowing exactly what I wanted, she reached out and started stroking my shaft. Now I think the time for talk is over Cindy.
The warmth of her mouth surrounded me and I moaned softly as I finally managed to get my cock where it belonged: 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, God that feels great. 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. 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.
I think that would be a really good idea. 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.
I want to see those luscious tits of yours, mom. 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: She took me out of her mouth and stroked me as she spoke. I NEED to see them! 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. 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.
Clearly Cindy liked to stay prepared. She turned to face me and placed her hands on her hips. 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. Although, I could use a little help getting hard again.