Stepmom's Club Ch. 01: Candace

Harpoon Estates is one of the most exclusive neighborhoods on the California coast, embracing all the stereotypes of rich excess: Large mansions, lush lawns and deep pools amid an arid landscape, BMWs and Teslas with obnoxious personalized license plates, yachts in the local marina, and of course, a bevy of second and third wives living lives of idleness.

These women have their own little society, which mostly takes place amid social gatherings and status competitions. Unlike the enclaves of Beverly Hills and Orange County to the south, the citizens of Harpoon Estates have managed to avoid being home to a Real Housewives franchise, as traditional mores and local homeowners association codes have managed to keep the reality show set at bay. The people proudly keep up the image of an aloof and insular community of affluence disinterested in the affairs of the common folks. Their merely-rich inferiors and the reality TV and influencer set have the strong belief that they are a culty and incestuous enclave dabbling in all manner of private decadence (as opposed to their public decadence). Nothing could be further from the truth. Well, the incestuous part anyway.

The topic came up in the course of the normal gossip when three of the second wives met for lunch at one of the grand homes. The hostess Candace, age 44, was the elder stateswoman of the group, though plastic surgery assured she didn't look it. She had the bottle blonde bimbo look favored by her 70 year-old husband.

Her guests that day included Mary, the second-youngest at 27, married to a man in his late 50s. She too was a blonde, though natural, and bore a striking resemblance to a younger version of her husband's first wife. Their relatively modest age gap, and the resemblance to the first wife, was considered romantic young love by the standards of Harpoon Estates,

Her other guest Jasmine was the baby of not just the group, but the Estates as a whole. At age 25, with her hopes of marrying a particular movie star behind her, she had settled down as the new wife of a serial entrepreneur with a penchant for fighting the SEC and investor lawsuits over his many schemes.

The gossip that day came from Ivy Vine Manors, the main rival to Harpoon Estates as the leading social elites. Ivy Vine included the most audacious social climbers, and rightfully earned the nickname "Poison Ivy" for the internal feuds and toxicity of personalities. The latest gossip to come out was an affair between the wife of a prominent and vain local ambulance chaser lawyer and her stepson.

"Can you believe the nerve of her?" Candace asked when discussing the shamed woman, "She always just so happened to schedule her parties the day I did, and always tried to steal away my caterers and entertainers for her events."

"Imitation is the most sincere form of flattery," Mary said.

"I guess that is why she banged the son that was the spitting image of her husband," Jasmine said.

"We know she doesn't spit," Mary said.

They all had a laugh at their fallen rival.

"Still, though, it doesn't help us all. It only reinforces as false notion that affluence comes with sexual depravity," Mary said, "Sure, there is infidelity, and people flip spouses like homes, but we have certain lines we don't cross here."

"I could never sleep with my stepson," Candace said, "There is just so much wrong with it. I helped raise him, even if his mother wouldn't ever credit me."

"Have you ever..." Jasmine began, but let it die.

"Ever what?" Candace asked.

"Sorry, it's a silly question," Jasmine said.

"Have we ever cheated on our husbands," Mary asked.

"Ignore that, I shouldn't have asked," Jasmine said.

"Are things not so good in your marriage?"

"No, they are fine!" Jasmine said, "It's just, you can't look around this neighborhood or listen to the gossip and not wonder."

"Well, we're not having sex with our stepsons, but we're not all Puritan moralists either," Mary said, "It's not like our husbands aren't taking what they can on their business trips."

"How often does a man need to go to Las Vegas and come back smelling of the same perfume?" Candace said.

"Honestly, I feel better when my husband comes back smelling of a different perfume. It means he's not falling in love," Mary said.

"Oh, I hadn't thought of it that way," Jasmine said.

"Maybe your man is being faithful, or at least only with women who share the same scent," Candace said.

"They are still in the honeymoon phase," Mary said, "Let her have her romance."

Mary placed a supportive hand on Jasmine's shoulder.

"We'll be there for you when the shine wears off," Mary said.

"I hate to think it will," Jasmine said, "How did you both come to the decision to do it?"

Mary and Candace looked at each other.

"As host I suppose I should go first," Candace said.

When I said I could never sleep with my stepson Derrick, I meant it. The feelings against it are too much, no matter how handsome or how much he resembles his father.

That said, as a popular and social kid, he has a lot of friends, equally as popular and handsome as he is.

This includes his friend Charlie. Charlie is good looking, but he's also from new money. I've met his father, and his father is still married to his first wife. Now, new money is nothing strange out here in California, but you have to understand, his father had to really fight to make it up from poverty. His father is very Midwestern, and his values and chip on his shoulder have passed down to his son. So there is this feeling that the world won't automatically see him as good enough, and that means girls also.

Charlie's Dad is okay looking, certainly not the worst. But he married very well, looks wise, much better than he could have pulled in Iowa. Charlie has the look, but in a world of type A alphas, he's a beta. Despite everything going for him, he's a little shy around women. Not awkwardly shy, but just short of the confidence to get the women he wants. He is probably the only student at his college who is still a virgin.

Now, we all know we love our older, more established men, but never forget there are some young men who love an older woman as well. In fact, I'd argue most of them would be better off having a woman with experience to help them out.

Certainly Charlie wanted that, even if he couldn't articulate it. I could see it when he interacted with the other Moms. There was just a closeness. I don't doubt many of them thought the same thing, but they weren't willing to act on it. Why risk a stable husband for the young man? At least the pool boys don't speak English, so who cares if they blab?

I dismissed my own thoughts, until I saw him interacting with Derrick's Mom. Now, Derrick's Mom and I don't see eye to eye, but I respect Derrick needs a good relationship with her. Well, Charlie was clearly flirting at her, and I could see Derrick's Mom was interested.

There are few true taboos where we're at, but you don't sleep with your best friend's Mom or son's best friend. But Derrick's Mom had been single for a while, and it's tough when the men her age want someone younger. I could see the temptation.

So when they finally separated when Derrick came in, I decided to make my move.

"Charlie," I told him.

"Oh, hi," Charlie said as innocently as a horned up 18 year-old with a boner could be.

"I saw you and Derrick's Mom flirting. That's dangerous stuff," I said.

"We weren't!" he said, with his voice cracking.

"Honey, I know what I see. And I get your feelings, but you need to consider Derrick's," I told him.

At this point he knew he was caught.

"Well, look, there's nothing wrong with being into an older woman," Charlie said, "And it's not like the girls my age are trying to do anything."

"I've seen them look at you. And you've taken some out on dates. What's the issue?" I asked.

"I...just can't close. I know that sounds transactional, but it's real. I get stuck on second base, and I just can't get them to go any further. They slap my hands like a nun in Catholic school," he said.

I could tell from the desperate tone what his issue was.

"Look, Charlie, I could tell you what your issue is, and how you can get to that next level, but I need you to promise you won't hook up with Derrick's Mom tonight, okay?" I said.

Charlie reluctantly agreed. I knew the fear of being exposed was the only thing keeping him from getting what he could get.

Derrick's Mom saw me talking with Charlie and throughout the night shot me dirty looks. She didn't like that I had her ex-husband, and I was taking her chance for a new man. I felt no shame, I was doing her a favor. Now I just needed to do Charlie one.

It was two days later. My husband was at work, and Derrick and his girlfriend were out on a camping trip. I told Charlie to come over and I would give him the secret he needed to know.

He did. To my happiness he managed to dress up some, as much as an 18 year-old can be expected to. He no doubt spent the last two days fantasizing, but I could tell from his body language that he didn't really believe it would happen.

"Good morning, Charlie," I said.

"Hi," Charlie said.

"Rule one, Charlie, don't greet a woman with such low enthusiasm," I said

"I don't. When I am on dates I totally step up," Charlie said.

"Fine, show me. Good morning, Charlie," I said.

"Good morning, Mrs. Carr," Charlie said.

"Candace. You use your date's first names," I said.

"Sorry. Is this a lesson or roleplay?"

"You're here because you can't woo a woman enough for her to let you in her pants," I told him, "You need to learn to close, for her sake as much as yours."

"I don't get it. If we both want to have sex, why all these steps and rules? Why do I have to do everything right?" Charlie said.

"That right there is your issue. How are you going to get sex when you don't appreciate the process? If all you do is race to get between her legs, you disrespect her. She's trying to appreciate you fully, while you ignore her for your own needs," I say, "Maybe this was a mistake."

"Well, maybe you should have let me fuck Derrick's Mom. She seemed more than willing," Charlie said.

"She was desperate, there is a difference. If you hooked up that way she would regret it. And if Derrick found out, it would be the end of your friendship. Then you would be the guy who managed to fuck up three relationships the first time he got laid. You think any girl wants to touch you with that taint on you?"

"I... I didn't think about it that way," Charlie said.

"Exactly. And as long as you only think of yourself, you're never going to get laid, which is also going to deny girls your age an otherwise good guy with a great body," I said.

The compliment took him off guard.

"I'm okay looking..." he said.

"Take your shirt off," I said.

"What?"

"Take your shirt off. I'll not ask again."

He complied, taking off his shirt. He had a well sculpted body. Not as good as Derrick, but he went along with them to the gym. Also, unlike his friends who felt the need to shave their chest, he let his grow. It gave him a more mature look, which I could give him an edge with certain women.

"You got the shape, and you can grow decent chest hair," I said, running my hand up his body.

"Mrs. Carr..." he began.

"Uh-uh," I said.

"Candace. What are you doing?"

"Showing you what you have to offer. You need the confidence if you want women to trust you. That is the sexiest thing you can have to offer," I said, "But that's not all."

I slid my hands down his back and gave his ass a squeeze.

"That's firm too. Women want a strong man, top to bottom," I said.

Then I moved my hands to the front of his pants over his bulge.

"I haven't had the pleasure of meeting this guy yet, but neither had any other woman," I said.

"You can have it," he said nervously.

"You gotta do better than that," I said.

"I thought you said you wanted it," he said.

"I said no such thing, I said most women would want it. But you need to do better convincing them of that."

Regardless of his social shortcomings, I unzipped his fly, because there was nothing shortcoming there.

His eyes widened as I took his cock out. It was an impressive piece of anatomy, though I had to handle it with care. With an inexperienced virgin like him, it was like handling nitroglycerin.

"So what do you want me to do with this?" I asked him.

"Suck on it," he said.

"And how would you like me to do that?"

"With your mouth?" he said, uncertain.

"I'm glad you got an older woman, because you don't even know what you really want," I said.

"Yes, I do!" he said defensively.

"I'm sure you love it when those young girls in the porn videos do this," I said.

I took his cock in my mouth and went down on him for a few strokes. He gasped, excited at finally getting what he'd spent hours watching and hoping for.

"However," I said, having taken his cock out of his mouth, "That's only for the camera. The best girls can blow your mind with other tricks."

With that I began to show him worlds he couldn't imagine. I used my tongue in various ways: Up and down his shaft, around the head of his cock, on his balls. I kissed him on his cock, balls, and inner thighs. I used various stroking techniques he could never have thought up. All the while I played safe, keeping him from blowing his load before the lesson could sink in.

"Your cock is a Swiss Army knife of pleasure. There are more ways to use it and have it used for pleasure than you know," I told him.

I meant what I said to him, but I also knew as an overeager virgin he didn't have the full set of tools that a Swiss Army knife would imply. I had the goal of getting him laid and his mind off my stepson's mom, and only pussy would do that.

"Let's see what you can do with your mouth," I said.

I moved his face to my chest, and he was eager to get my top and bra off. He was aggressive with the groping and sucking of my breasts. It lacked skill, but his eagerness counted for something. I began to show him ways to grab and play, and he started to get better.

He moved his hand down to my pussy on his own. He rubbed all around, still unsure of what he was doing. I moved his hand to my clit and got him to do smaller circles over it.

"Yes, you're getting it," I told him.

This foreplay was getting me wet and I was starting to enjoy it. I didn't have any expectations from his upcoming performance, but I could replay this in my mind later during self-service.

I moved his head down, and I swear, I've never had a more eager mouth down there. To his credit, he took the lesson and took time to focus on my clit, while his hands worked their way over my thighs and ass. I put my hand on his head and directed, and began to really build to an orgasm. I started moving my hips and grinding all over his face.

Then he got really adventurous and one of his fingers. He had been sliding it in my pussy and gotten it lubed up. It traveled back and he started running along my butthole. I was nervous about where this was going, but I was too close to climax too much to risk losing it. He slid it in and began fingering. I hadn't been planning that, but his boldness was a turn-on. Plus, there was a sign of control, where he seemed to be feeling out my reaction rather than just plunging in. There was some hope for him yet, and maybe I could keep him around for more.

With his other hand he took one of my breasts and started playing with it. With several points of stimulation, I finally came. My orgasm encouraged him, and he went in more and more as I came, extending it.

"Charlie, Charlie!" I said as I came.

My thighs closed on his head as I came and I swear I must have been suffocating him, but he could have died happier than ever in that moment. I released him after a few seconds.

I laid back and caught my breath, while I felt his mouth move up my body. He took his finger out of my ass and his hands followed him up.

I was back in my right mind just in time to meet his face. I gave him a kiss, tasting my pussy juices on his lips and breath. His eyes were electric with excitement, and his hair a mess from the grip I'd had.

"Charlie," I said, "You got a lot to learn, but you have the makings of a real Casanova."

"Thanks," he said, "But I have more to give."

He grabbed his cock and began rubbing on my thigh.

"You do," I said, "And it's past time you had someone to give it to."

I repositioned myself and opened my legs for him. He got between them and started rubbing his cock on the outside of my pussy.

"Playtime is over, Charlie. Time to become a man," I said.

With that order, he slid inside me. It was a strange transformation. As he put it in he had a look of determination, a sign of almost real confidence and strength. But as he plunged in his face betrayed his virgin status, as my warm and wet pussy enveloped him.

"Oh!" he said.

"Don't come yet," I said, grabbing his face and making him look at me.

He took a few deep breaths, willing himself not to come prematurely.

"You just feel so good," he said.

"I know. I've had many men tell me that," I said, "But you don't want to blow this."

A few moments later he regained his composure.

"Okay, I'm good," he said.

"Good. Let's see it," I said.

With that he started to fuck me properly. It was slow at first: Back and forth, back and forth.

"Keep moving. Try some angles. Really explore this," I said.

Charlie did. He tried some deep thrusts, some shallow thrusts, feeling out everything.

"There, isn't that good," I said.

"Yes," Charlie said.

He took a few more thrusts and started a rhythm.

"Is this working?" he asked.

"This is all about you Charlie, we'll work on reading me next time," I said.

"Next time?" he asked.

I hadn't specifically thought that comment out, but I had to have been subconsciously thinking it. Charlie was so new, and I knew that I could make something great out of him. But that would require much more than one go.

"Charlie, this isn't porn, where you have to go for an hour in fifty different positions. You've already performed admirably for a virgin," I said, "Now it's time to go all the way. Be a man."

He nodded and took up the challenge I gave him. He found his rhythm again. And it started to feel good on my end too. He got out of his head, and really started to pound. He took my head in hand and pulled me in for a kiss. He was taking control, and I liked it. One day he really would be able to, and I thought how I wanted to be there when he did.

He lasted three minutes or so, a decent run for a newbie. He got distracted as he built to climax. He looked down as it built and watched his cock enter my pussy. That gave me a chance to watch his face as he got closer, seeing so much going through his mind as he was about to make it. This was the moment.

He grabbed my thighs and pulled me for his final, explosive thrusts. He let out a grunt, and I swear his voice may have cracked on one of the thrusts. There were three really deep thrusts, and then they slowed. I could almost imagine his cock exploding inside me just based on how his body twitched.

He paused, half inside me, as he caught his breath.

"Charlie," I said.

He looked up at me.

"You've done it," I said, "Welcome to this side of manhood."

He smiled and pulled out. He pulled me up and kissed me. We made out for a long moment.

"Mrs. Carr..."

"Candace," I said.

"Candace," he said, "That was amazing."

"You weren't too bad yourself," I said.

"What about your husband?" he said, suddenly aware of the situation.

"What about him?" I said, "He's not home."