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Like Mother, Like Daughter (Part 1)

"After I fuck Diane, she hooks me up with her daughter"

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Author's Notes

"Based on a true story"

I used to play cards with Diane and her husband, Jeff. My brother and Jeff went to high school together, attended a couple of years of college together, and joined the military together. My brother made a career out of serving in the military. Jeff met Diane while serving and got out after his first hit hitch. They had a daughter, Sherrie, and settled into routine married life.

When my brother would come home to visit our parents, he would go by and see Jeff and Diane. They liked to play cards and one night he invited me to go with him. I took a liking to Diane and I would play cards with them even when my brother wasn’t around. We would have a few beers and eat pizza while we were playing cards.

Sherrie, and sometimes her friends, would hang around and eat pizza with us. Almost always wearing just a T-shirt and panties. Usually no bra either. I took plenty of notice and would later jerk off thinking about them.

Diane was pretty, with nice boobs and a nice ass. She didn’t dress provocatively so I didn’t get to see a lot of her body. But I still got aroused thinking about her.

I worked near where she worked and pretty soon I started joining her and some of her coworkers for lunch. Sometimes, it was just Diane and me. Occasionally, we would have flirty conversations. I would tell her how nice she looked.

One day at lunch, she asked me, “If I wasn’t married, would you want to date me?”

I said, “Of course. You are very attractive. I think we would do well together.”

Then she asked me, “Do you find me attractive enough that you would have sex with me even though I am married?”

I think I sort of shocked her when I replied, “Yes. I’d have sex with you anywhere, anytime.”

She said, “You say that but you would probably chicken out at the last minute.”

“Try me,” I replied.

“How about next Wednesday night,?” She said. “Jeff is working late shift and Sherrie is going to a sleepover at a friend's house. You can come over after work.”

“It’s a date then,” I said. My cock was getting hard thinking about fucking Diane. I could hardly wait for Wednesday to come.

We talked a couple of times in the days leading up to Wednesday.

“Are you sure you are coming? You won’t back out on me?” She said.

“Diane, I am looking forward to it. Nothing will keep me from coming.” I replied.

Wednesday finally arrived and I headed to Jeff and Diane’s house. I had spent the whole day thinking about fucking Diane. Imagining how she looked naked. Wondering if she had a hairy pussy or whether she shaved. Not that it mattered. I was ready to fuck her no matter what.

I arrived at their house around 7 p.m. Diane had told me that Jeff would have left for work by then and Sherrie would be at her friend’s house. Diane had just gotten home from work, still dressed in her business attire. When she saw me at the door, her eyes lit up and she pulled me inside.

“I really thought you would stand me up,” she said.

“Not a chance,” I replied. “I’ve been waiting all week for this.”

Hardly inside the door, we kissed passionately. I let my hand slide down to her ass and gave it a squeeze. My cock was getting hard and I’m sure she could feel it, pressed against her.

“Let me put on some comfortable clothes,” she said. “ And then we can have some fun.”

She kissed me again, then released me and headed down the hallway. A few minutes later she came back, wearing a thin top and a pair of panties. I could tell she wasn’t wearing a bra. Her erect nipples poked out from the top.

We kissed yet again and she put her hand on my crotch, feeling my very hard cock.

“Let’s sit on the couch and talk a bit,” she said. “Jeff always calls me on his first break so we can’t do anything until then.”

She told me that she loved Jeff but that their sex life was pretty stale. “We rarely fuck anymore. He is always tired when he gets home from work. And he never wants to eat my pussy.”

I said, “I can’t wait to be between your legs, licking your pussy. And to do anything and everything with you.”

She smiled and said, “I can’t wait either.”

Just then the phone rang. It was Jeff. He and Diane chatted for a few minutes about their day and about their plans for the weekend. Finally, Jeff had to go back to work and they ended their conversation.

Diane leaned over and kissed me and said “Now I’m ready for some fun.”

We continued kissing and I started caressing her tits through her shirt. I could feel her nipples getting harder. She started rubbing my crotch through my pants and I became hard as a rock.

“Let’s get this shirt off,” I said and lifted it over her head. Her tits looked incredible. Perfect C-cup tits that hung just right. My mouth went directly to her left tit while my hand found her right one. I kissed her tit and sucked on her nipple. Then I switched to her other tit, giving it the same attention. Diane was obviously enjoying this and her breathing started getting heavier.

“You promised you would lick my pussy,” she said. “I’m ready for that now.”

I reached down and slid her soaking-wet panties down and off. Her pussy was beautiful. A nice tuft of dark pussy hair. I put my face right down to her pussy, inhaling the wonderful aroma. I parted her lips with my tongue and nuzzled her mound with my nose. I licked and sucked on her swollen pussy lips and inserted a finger into her wet cunt. She gasped as I continued to lick her especially when I licked her clit. She writhed and spread her legs even wider. I could feel her spasm as she had her first orgasm.

“Fuck me now,” she demanded as I continued to lick her pussy. “I want your cock inside me.”

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But before I was going to fuck her, I wanted to lick her asshole. I pushed her legs back so I could get access to her puckered little starfish. I licked all around it until I finally put my tongue right on her hole. She gasped as I pushed my tongue into her asshole. She tasted incredible.

“You have to fuck me right now. I want your cum so bad,” she said.

I put my rock-hard cock right at the entry to her pussy, rubbing against her wet and swollen lips. Then I pushed the head in followed by the entire length. For a middle-aged woman, her pussy was amazingly tight. She wrapped her legs around me as I pumped my cock in and out of her very wet cunt.

“I’m going to cum,” she said as I pumped her harder.

But I wasn’t ready to shoot my load inside her just yet. I pulled out and flipped her over, putting her on all fours. “I want to fuck you from behind,” I said and pushed my cock back in her. Her ass looked incredible and it felt even more so as I bumped up against her thick ass cheeks. I started rubbing her puckered asshole as I continued to fuck her.

“That feels so good,” she said. “Put your finger inside my ass.”

I inserted my thumb into her asshole and started to move it in and out of her. I continued fucking her too until I finally felt like I was ready to cum. I told her, “I’m going to cum,” and started shooting rope after rope of cum into her pussy.

She gasped and said, “I’m going to cum too. Fill me with your cum.”

I continued to pump my cock in and out of her until every drop of cum was in her pussy. I collapsed on top of her and my cock softened and slid out of her.

“That was incredible,” she said. “ I haven’t been fucked like that in years.”

“I can’t believe Jeff doesn’t fuck you every day. I know I would,” I said.

We lay together for a long time, our naked bodies recovering from the intensity of our fucking. We kissed and I caressed her tits and belly.

“Before we fuck again, I want to ask you a question,” she said. “Would you want to fuck Sherrie? I want you to be the first man to fuck her. She hasn’t had any real boyfriends. “

“What makes you think she would want to fuck a guy as old as her mother?” I replied.

“She is always telling me how much she likes you and can’t wait for card night to come so she can see you,” she retorted. “It’s not a coincidence that she is always running around in a t-shirt and panties whenever you come over.”

“I’ve always thought she was cute and to be honest, I have jerked off many times thinking about her. Especially after seeing her cute butt cheeks peeking out from her panties. I’ve thought about fucking and just about everything else with her. But I never thought I would get that chance.”

“If I set that up, would you do it?” she asked.

“Absolutely!” I replied. “If she is anything like her mother, it’s going to be fantastic.”

“I have an idea about how to get you two together. Give me a couple of weeks and I think I can make it work,” she said. “All I ask is that you tell me about it afterwards.”

I was getting aroused again, thinking about fucking Sherrie. And I could tell that Diane was getting aroused too with the thought of her new lover fucking her only daughter.

We started kissing again, with even more passion than before. Pretty soon, I was on top of her with my cock buried in her wet pussy.

A few weeks go by. Diane and I meet up a couple of times for lunch and she tells me she is still trying to figure out a way for me to fuck Sherrie. Sometimes we meet up in a local park, spending lunchtime kissing and playing. One time, she doesn’t wear any panties so I can easily finger her pussy. We get so turned on that she gives me a blowjob in my car before going back to a meeting at work.

Finally, she tells me she has a solid plan.

“Jeff and I are going out of town to see a show with some of Jeff’s friends from work. It is just overnight but he doesn’t want to leave Sherrie at home by herself. She’s not one to get into mischief but he would rather have someone older around just to make sure. I suggested you could be that person and Jeff agreed.”

“You can spend the night and have plenty of time with Sherrie,” she said. “Just remember that I want to hear the details afterwards.”

My cock was getting hard imagining having alone time with Sherrie. Thinking about all the things we could do.

“When do I get to do this?” I asked.

“Next Friday,” Diane replied. “We leave early afternoon and return the following evening.”

“Perfect,” I replied. “I’m off a half day on Friday and I’ll come by right after I get off.”

All I could think about for the next week was how much fun I was going to have with Sherrie. My cock was perpetually hard, dreaming of Sherrie’s little tits and her beautiful behind.

On Friday, I leave work around noon, grab a bite to eat, and head over to Jeff and Diane’s house. I start to knock on the door when Diane opens it with a smile.

“Perfect timing,” she said. “We were just getting ready to leave. There is food in the fridge. Help yourself.”

Jeff came down the stairs carrying a suitcase. “Thank you so much for agreeing to stay here with Sherrie.” “I don’t like leaving her alone. I know you will keep an eye on her while we are gone.” Little did he know that I had had my eye on her for a long time.

“No problem, Jeff,” I said. “I am glad to do it.”

“You are the best,” Diane chimed in, giving me a wink and a little kiss on the cheek.

With that, Jeff and Diane got in the car and backed out of the driveway. I watched them until they turned the corner and headed away.

As I closed the door, Sherrie came bounding down the stairs, wearing a t-shirt and a pair of panties. No bra.

She gave me a big hug and a kiss on the cheek. My cock stiffened as she pressed up against me.

“We are going to have so much fun,” she said.

To be continued.

Published 
Written by Msh1313
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