A Family Affair
Copyright© 2022 by Master Jonathan
Chapter 21
Romantic Sex Story: Chapter 21 - A divorced woman is doubting her value since the divorce. With three kids, she knows that finding love will be next to impossible. But she doesn't realize love is right there beside her - in the form of her son. He shows her that she has worth and value and when her two daughters learn what's going on they want the same sense of belonging their mother has!
Caution: This Romantic Sex Story contains strong sexual content, including Mult Consensual Romantic BiSexual Heterosexual Fiction Sharing Incest Mother Son Brother Sister Daughter BDSM MaleDom Rough Spanking Harem Polygamy/Polyamory Anal Sex Analingus Exhibitionism First Masturbation Oral Sex Sex Toys Squirting Voyeurism
“Where did you learn to do THAT?” he asked as soon as he’d gotten his breathing under control enough to speak in full sentences again.
“Mom showed me,” she giggled, “She showed me how to give a proper blowjob and what you liked her to do. She let me watch a few porn movies on the Internet too, so I could see how they do it.”
“Well remind me to thank her for your lessons! You were amazing babygirl!” he said, pulling her up to snuggle with him.
Jenny fell asleep in his arms, Daddy’s cum in her belly and a big smile on her face.
It was a couple days later when Tommy would fulfill his promise to take Jenny shopping. He’d already taken his mother and Diane shopping, so now it was Jenny’s turn. Tommy and Jenny headed off to a place he’d found searching the Internet for women’s costume shops.
The website showed hot girls in sexy schoolgirl, cheerleader, little girl, and other bedroom fantasy outfits. Just the thing for his babygirl. On the way to the costume shop, Tommy talked a little bit about what she would be shopping for.
“Okay babygirl, today we are going shopping for your outfits and for some other things we will need. I took Mom and Diane shopping when they first started with me and since you are my girl now too you will get the same.
“I am giving you $500.00, the same as I did for them, to buy your things. Now, I seriously doubt you will be able to spend all of it – Mom and Diane combined couldn’t spend $500, but we will put whatever is left away for future shopping trips.”
”$500 DOLLARS? OH DADDY!” she exclaimed.
“That’s right and I want you to get several outfits and all the accessories. I want you to think along the lines of a little girl so schoolgirl outfits, princess outfits, little girl type outfits, that’s what I want you to get.
“This is a pretty good-sized shop from the looks of it on the website so I’m sure you can find a few selections. Make sure you get the shoes, stockings, and gloves, or whatever else completes the look.
“As a little girl, you won’t need as much makeup as Mom and Diane – they are my sluts and have a different look. But you will need to get a few things, like light blue eyeshadow, mascara, blush, and that cherry lip gloss that makes you so tasty!
“And we will see what kind of perfume we can find to make you smell little girlish too. And I haven’t forgotten about the pigtail hair stays either,” he said.
“Oh Daddy this is going to be so much fun! Thank you, Daddy, thank you for taking me shopping!” she said, hardly able to sit still long enough to get to the costume shop. After an aggravatingly long time (at least for Jenny!) they arrived at the shop. Tommy offered her his arm and she smiled broadly as she slipped hers under his.
“Oh, Tommy! Oh look at all these wonderful things!” she exclaimed in awe. She remembered to call him by name when they were in public. She walked slowly through the racks and racks of costumes, oohing and ahhing at them as she passed. Tommy let her look around, but gently and subtly tried to steer her to the outfits he wanted her to pick from.
“Look at this one Jen ... I think you would look hot in this!” he said, trying to be as inconspicuous as possible. He moved from one outfit to another showing her what he thought she would look sexy wearing for him. “Check this one out, Jen. Now, this is what I’m talking about!”
After a minute or so Jenny caught on to what he was doing and began to focus her attention on what she was there to look at. She picked out a few different costumes for his approval and took them over to him. “I found these, Tommy, what do you think of them?” she asked.
He looked through the costumes. There was a sexy Catholic schoolgirl one, another sexy schoolgirl one with a shockingly short plaid skirt, a cheerleader outfit sure to win at any game, a little girl princess outfit, and one that resembled Dorothy from the Wizard of Oz – only a whole lot more “adult orientated”! Tommy approved each of them, smiling as he pictured Jenny in the bedroom wearing each of the costumes.
After he had approved the outfits she chose and made sure that all the necessary accessories had been found to go with them, they took all of their treasures up to the counter to pay for them.
Jenny could hardly wait to get her new outfits home and try them on. She knew her sizes and knew they would fit her, but she wanted to show them off to him and see his reaction to the flirty, sexy clothes.
They pulled into the driveway of the house and Tommy stopped the car, got out, and came around to help her out of the car so they could take the packages inside. But before he was able to open the back door to get them, Jenny pushed him back against the car door.
“Tommy ... Daddy ... thank you so much for taking me shopping today. You are the most wonderful amazing Daddy a girl could ever have,” she said, looking up into his eyes. She pulled him down to kiss him long and passionately.
Tommy helped Jenny carry her new treasures to her bedroom and left her to put them away. Jenny laid all of her outfits out on her bed and put the accompanying accessories alongside them.
She studied each outfit carefully, examining the possibilities for each before gently putting them away. She hung each outfit with all the love and care of a bride-to-be putting away her wedding dress before her big day. She could hardly wait for the day she would be able to show her new clothes to Daddy ... and see what he does next!
As anxious as Jenny was to show off her new wardrobe and as eager as Tommy was to see it, they would have to wait a few days for the big unveiling. There were two other girls who were in line to see him again and the first of those was Diane the older of the two sisters.
It was the following weekend, Friday afternoon when Diane’s “date” with Tommy was to take place. This was an especially important “date” for Diane as she had something very important to talk to him about.
She took off work a couple hours early just so she could get home and get prepared for Tommy. She wanted to make sure everything was perfect for him tonight – it would make what she had to say easier for him to take and hopefully agree to.
Diane showered and shaved making sure she was perfectly clean in all the places she should be. When her shower was done she went in and got dressed in her favorite lingerie – a sexy black lace bra/panty/garter belt set.
She didn’t wear the panty because of his rule against it, but it didn’t detract that much from the overall look. The bra was a shelf-type bra with half-cups that held her tits high and easily accessible to a hungry mouth or playful fingers.
And the garter belt served not only to hold up her thigh-top stockings but perfectly framed her naked slit, already damp and shiny with her juices.
She put on her stockings and then her high heels. Dressed now, she went into the bathroom to put on her makeup. Diane knew that Tommy liked her to wear that dark, dramatic evening makeup – the “smoky eye look” that made her look sexy and sultry ... like a porno star.
She put on her eye makeup followed by her lipstick – he liked red glossy lips and she wanted to look stunning for him tonight. Finally, she ran a brush through her hair to make sure there were no stray flyaway hairs and she was ready. She came out of the bathroom and took up a position sitting on the edge of her bed to wait for him.
She rehearsed what she wanted to say to him, going over how she would say it and changing the wording around to try different tactics. This was an important night and she didn’t want to sound like an idiot when she talked with him. She needed to get out what she wanted to say in a sensible, adult manner, not like some whiny kid or an imbecile!
Diane didn’t have to wait long for him. Tommy knocked on the door to her bedroom surprising her. “Come in,” she said, almost in a gasp.
Tommy entered her bedroom and smiled. “Hello, Beautiful. You are looking particularly fetching tonight. What’s the special occasion?” he said as he approached her.
“Can’t a girl get dolled up for her man?” she asked coquettishly.
“Yes, but there’s usually an ulterior motive,” he said.
“Well, I did want to talk to you about something...” she said.
“Ah, see what I mean? So what is it? What could be worth all this cloak-and-dagger nonsense?”
“Sit down Tommy, please.”
“Uh-oh, this does sound serious,” he said, pulling up a chair.
“It is. Tommy, I’m feeling a little left out of things around here and I don’t know why or what to do about it,” she said. “I mean Mom is your slut, the one you go to for wild hot adventuresome sex. She is your ‘do anything if it feels good’ girl. And I get that. It’s good to have someone so free-spirited and playful like that.
“And Jenny is your sweet little girl ... your babygirl who has Daddy fantasies and that is fine too. Both of them have found a niche with you – a place where you can call on them alone when you are feeling that way. I get it.
“But I don’t have a niche, I don’t have a place with you. I’m just Diane, your sister, and occasional sex playtoy. I don’t have a ‘role’, for lack of a better word. And it makes me feel like a third wheel ... a tag-along ... the plain sister to your hot girlfriend.”
“Wow, Diane I didn’t know you felt this way. I never want any of you to feel like you don’t belong or that you are second to anyone. You girls are the most important people in my life, honey, all three of you. What can I do to make you feel more like part of this setup?” he asked.
“Give me a role to play. Make me something that stands out, that sets me apart from the other girls. Something that you come to me for. As I said, the other two have their parts in this play. I want one too.”
“Did you have something particular in mind?” he asked.
“Yes, I do. Now, this is going to sound kind of strange, coming from me, but I’ve been thinking about it for a while now. Tommy, you have already started by taking charge of the house and of us and you like us to call you Sir – well, except for Jenny who calls you Daddy.
“And you’ve already set up the rules against wearing panties and masturbating without permission. But I want to take it further. Tommy, I would like to be your sex slave ... you know, the whole BD/SM Master slave thing,” she said.
“Whoa! Hold on a second, Sis! Are you sure about this? Do you know what this entails?” he said sitting up in surprise.
“Tommy, I’ve been doing some research on this online and I’ve seen what kinds of things this ‘entails’ as you put it. And yes there is a lot of stuff out there that I don’t agree with, but there’s also a lot that I find very beautiful and very ... sexy.
“And from what I’ve read and seen BD/SM can be personalized into whatever the two parties want. It doesn’t have to be hardcore, whips and chains, ‘you do as I say or else’ stuff. It can be quite beautiful and emotionally satisfying if that’s what you want. Some of the poetry and stories I’ve read bring me to tears!” she said.
“But I don’t know much about this stuff ... about being a Master or having a slave or anything,” he said.
“That’s okay because I don’t know much about having a Master or being a slave. But I do know that being an outcast is no fun. I’ve been one for too long as it is. I want to belong ... to somebody,” she said, looking down at the floor.
Tommy could see this was important to her. He could see the way she looked when she was talking to him, He could hear the defeat and sadness in her voice. It was almost more than he could bear. He loved his sister – he loved all three of his girls and he couldn’t stand to see any of them sad like this. His decision was an easy one.
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