A Family Affair
Copyright© 2022 by Master Jonathan
Chapter 15
Romantic Sex Story: Chapter 15 - 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
“Oh God, Tommy! Oh, your cock is so deep inside me! Ohhh yes, baby, fuck your baby sister, show her how you like her to fuck you! Teach me how to please and pleasure you Tommy, I want to do all the things you like! Oh God yes!” she moaned as she squirmed and writhed under him. She may have been new to all this, but she was taking to it like she’d done it all her life!
As for Tommy, he liked the way his little sister was enjoying herself. While her words may have been a bit startling at first, Tommy now liked the fact she was able to talk dirty. He was concerned he would have to work at getting her to talk dirty – she was only 16 years old and he still pictured her as that little girl who giggled whenever the word poop was said! But now she had a vocabulary any good porn star would be proud of and she wasn’t shy about using it!
Tommy continued to pound his little sister with the same ferocity but he also knew that his time was drawing to a close. He’d already given Jenny her first oral orgasm and he was holding out until he could give her her first deflowering orgasm.
He wanted to make sure she came good and hard this first time so her entrance into womanhood would be something she could relive with fond memories – he knew she had more than enough bad memories already!
But judging by Jenny’s moans and cries he wouldn’t have to hold out for much longer. Jenny was quickly building up to an earth-shattering orgasm ... one that will go down in her diary as the greatest thing ever to happen to her.
Tommy was intent on delivering that earth-shattering orgasm too. His thrusts grew harder and more intense, bordering on savage, while the rate he was delivering them also increased. Jenny could tell the difference and it only made her more aroused and eager for it to arrive.
“Oh God, Tommy please, please make me cum! Make me cum for you, baby! Please, I want to be your woman – claim me as yours!” she cried.
“No. Not yet,” Tommy said, thrusting harder and deeper into the young girl’s tight hole.
“Ohhh, God...” Jenny moaned her disappointment. She writhed and struggled harder, trying to get him to make her cum. But it was no use – she would have to learn she was on his timetable and he would determine when and if she came.
Tommy’s assault continued and a few minutes later Jenny once again entreated him. Please Tommy please I need to cum! Please make me cum Make me cum all over that beautiful cock! Please I want to be a real woman for you!” she cried.
But Tommy’s reply was the same. “Not yet, Jenny. I’m not quite ready.”
Jenny groaned in sullen resignation. Her release would have to wait, despite her burning need.
Tommy knew his baby sister was suffering – he knew that she needed to cum badly ... he could feel her pussy walls grasping at him and trying to milk him of his seed. He could feel her body tremble under him and he could hear her labored panting as he thrust into her over and over again. He knew that she was on the cusp, but if she really wanted to be his girl, she would have to learn to control her urges better.
However, Tommy wasn’t cruel and he didn’t intentionally do things just to see her suffer. So as soon as he felt he was ready to join her, he said so.
“Okay, Jenny I’m getting ready to cum. But since this is your first real woman’s orgasm, I want us to cum together. Can you do that for me?” he asked.
This lit the young Jenny up. “Oh yes, Tommy! Oh, I would love to cum together with you! Oh, that would make it sooo special! Yes, please, make us cum together!” she said, almost cumming just from the excitement of it.
“Okay then we will cum together, but I want you to keep your eyes on me. I want to see your face when you cum this first time, okay?” he said.
Jenny nodded her head vigorously and then put her arms around his neck preparing for what she wasn’t sure.
Tommy gave a couple more strokes and he was there. He pushed in deeper and harder than ever and held himself there as he unloaded. The feeling of his cock so deep and his cum splashing against her pussy walls was all it took to push her headlong over the edge.
“OHHH GAAAWD, TOMMMEEE!” she screamed as her back arched, her eyes rolled back in her head, and her whole body stiffened up like she had rigor mortis. She stayed like that for a couple moments, her body shaking with the supreme effort as every muscle in her body fired off at once.
She couldn’t hold that position for long and after a couple moments, she dropped back onto the bed. But her ordeal wasn’t over just yet. Tommy continued fucking her through her orgasm until his cock softened to the point he couldn’t any longer and he pulled his sticky cum-covered cock out of her, laying down next to her and holding her as her orgasm slowly faded away.
When she finally returned to him and was lucid enough to talk he rolled her to him and looked down on the sweat-drenched form below him.
Jenny didn’t say anything at first, she just reached up and softly stroked his cheek with her fingertips several times as she looked at him. Her eyes were teary and her lip quivered and she stroked her brother lovers cheek.
Tommy waited for her to say something, anything, and finally, she found the words. “Oh, Tommy ... Oh, that ... that was the most beautiful, wonderful thing ever! I love you so much, Tommy. Thank you for making tonight so very, very special. This night couldn’t be any more perfect.” she said her voice shaking as she spoke.
“You’re more than welcome, honey. You deserve to be happy, and I’m just glad you enjoyed yourself tonight,” he said.
“Enjoyed myself? Tommy, you made me feel like Cinderella! And what you just did ... Oh my God! You were incredible! You are the most amazing, marvelous, wonderful brother there ever was! I can’t wait to tell all my friends just what an incredible brother I have!” she said.
“Hold on a second, Sis! You can tell your friends about the Prom and how much fun you had there, but this little after-party has to stay our secret, understand? I don’t think your friends would look too kindly on having your brother fuck you and I know when their parents found out, there would be problems. So what we did has to stay just between the two of us, okay?” he said.
“I understand. I don’t want you to get in trouble. I’ll keep this our secret,” she said.
“Good girl,” he said. Then he lay down behind her and wrapped his arm around her, pulling her closer and “spooning” her.
The pair lay like that for about 20 minutes, with Jenny’s head on Tommy’s crooked arm as they spooned and his arm held her close to him. Tommy was resting, but thoughts were racing through Jenny’s mind. She had a confession she needed to make to Tommy, but she wasn’t sure she should, or if she even could. She tried wording it in her head every way she knew how, but it never seemed to be just the right way.
Finally, in exasperation, she just blurted it out. “Tommy I have a confession to make,” she said.
“This sounds serious! What is it, Jenny?” he asked.
Jenny rolled over to face him. “Tommy, I know you said that when I came a few minutes ago that I was going to be your girl, and that meant a lot to me, but I want to be a Tommy’s Girl. Please can you make me a Tommy’s Girl like Mom and Diane are?” she asked.
“You know about Mom and Diane and me?” he asked astonished.
“Tommy I’ve known for some time ... ever since I got back from Corpus Cristi. I noticed the change first in Mom – how she was so much happier and had a spring in her step. And then I saw the same thing in Diane. I wondered what went on while I was gone. Mom was spending a lot more time here at your place and making up excuses why she need to ‘go out for a bit’ as she said.
“So one day when she said she was going over to see you about something, I got on my bike and followed her. I know a couple of shortcuts to your place that put me here right after Mom got here. I waited for Mom to go inside and then I crept up to the front door. I know where you hide your key so I snuck inside and followed the sounds to your bedroom.
“I opened the door a crack and saw you and Mom. I left right after that and then later on I confronted Diane and she told me you were doing her too. So I know all about Tommy’s Girls. And I want to be one too. Please, Tommy ... I’m sorry I had to be so sneaky to find out, but please don’t leave me out in the cold. Not after what we had tonight! Please!” she implored him.
“I dunno, Jen. I mean what we did tonight is already gonna be hard to explain to Mom but to do to you what Mom and I do or even what Diane and I do ... you are still just a 16-year-old girl!” he said.
She suddenly sat up. “I am a WOMAN!” she said indignantly, “You said so yourself. In fact, you said I was your woman! Now you told me earlier that you don’t say something you don’t mean, and I don’t have you pegged as a guy who manipulates a girl, telling her what she wants to hear just to get in her pants. Am I wrong on that one? Are you that kind of guy?” she asked.
“You know me better than that Jen...” he started to say.
“All right then,” she said cutting him off in mid-sentence, “you made me a woman – your woman – so now I am asking to be your woman, to be one of Tommy’s Girls. I don’t want to replace Mom or Diane, only to be included. And you can’t use the ‘I’m too young’ bit either – I wasn’t too young to fuck the first time! This is my Prom night, Tommy, don’t end it by turning me away!”
Tommy smiled at her speech. “Okay spitfire – you think you have what it takes to be Tommy’s Girl? I’ll warn you right now that sex as one of Tommy’s Girls is a lot more intense and rough and tumble. And there may be activities or things I may have you do that you won’t find so appealing.
“Tonight, I made love to you because it was your first time and this was your Prom. But if I make you a Tommy’s Girl, we won’t be ‘making love’ – we will be fucking ... hard, dirty, sweaty, screaming to the heavens fucking. Are you ‘woman’ enough for that? Let me warn you – I’ve already worn Mom out and nearly put Diane into a coma!”
“Tommy, I may be young and you may still think of me as your baby sister, but I can take anything you can dish out! I’m not made of china and I won’t break, no matter how ‘rough and tumble’ you get.
“As for those things that may not be so appealing – I will do whatever you ask, whenever you ask, and however you ask. I want to be yours, I’ve dreamed of being yours, and if this is what you like, I want to give it to you.
“Anything, Tommy, and I mean anything. I trust you implicitly – you are my brother, and I know you would never do anything to hurt me. So bring on the hard, dirty, sweaty fucking, and let me show you I can handle your worst!” she said.
“Well, after that little tirade, I can’t exactly say no, now can I? I mean you pretty much painted me into a corner! Okay then, I will give you your chance. But I will be watching out for you and making sure you aren’t getting in over your head here. Being a Tommy’s Girl is something that you enjoy, not something you are afraid of!” he said.
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