Getting Sis Pregnant - Cover

Getting Sis Pregnant

Copyright© 2021 by Master Jonathan

Chapter 1

Romantic Sex Story: Chapter 1 - His sister is a model who wants to quit the business. Only problem is she needs to get pregnant to break her contract. She asks for his help in getting her pregnant. Will he accept? Will her plan work to get her out of her contract? What will Mom have to say about this?

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Heterosexual   Fiction   BDSM   MaleDom   Lactation   Masturbation   Oral Sex   Pregnancy   Tit-Fucking   Illustrated  

Mom had always had trouble with men. Her first marriage, to a man I knew only as Paul, lasted only two years. Mom was only seventeen at the time – she’d had to lie about her age even to get the license – and she was far too young to take on such responsibility.

From what Mom told me about it, they seemed happy at first. But then Mom got pregnant with me and about six months after I was born, Paul decided he wasn’t ready to be a father and split. With no place else to go, Mom returned home, with me in tow. Grandpa went to court and got the marriage annulled so Paul couldn’t come back and try to take me away. Mom never blamed me for the breakup, although I’m fairly certain my birth had a lot to do with it.

Mom didn’t try the marriage thing again until she was twenty-four years old. By then I was about five and a half and she wanted me to have a father figure around to help me grow up. Grandpa lived about 225 miles away in another town – too far away to be an effective father figure. Besides he was getting too old to play catch and the other things young boys like to do.

But this marriage too, was destined to fail. His name was Allen and I remember him being nice enough but very flighty. It was like he didn’t know what he wanted from one moment to the next. I’m actually surprised, looking back on it, that they stayed together as long as they did, except that neither had the money right then to leave. Neither of these failed marriages was Mom’s fault – except that she sucked at picking good men. I tried to be the “man of the house” but at only ten and a half, I’m afraid I wasn’t a whole lot of use. Certainly not the “man” she needed.

Mom and I did the best we could. I learned how to cook a few things and do the laundry and some of the other life skills I would need. Plus it took some of the load off Mom. She worked as a bank teller at a local bank and standing all day made her tired. So the more I had done when she got home, the more she could rest. I was no world class cook by any means, but I could whip up enough to stave off starvation! And Mom always smiled when I made dinner, even if it was just TV dinners!

Mom waited six years before trying the marriage thing again. By now she was thirty-six years old and tired of sleeping alone. She also knew I wasn’t going to be around for much longer and she was scared of living all by herself. Working at the bank she had her own “clientele” so to speak – people who, when they saw her working the teller line, wouldn’t go to anyone else. One of these loyalists was name Michael and he and Mom would always chat a bit while she was tending to his business.

One day he asked her if she would like to go out with him. She liked him and they had known each other for a couple of years by now so she agreed. He was a widower and had a daughter a couple of years younger than me. Things worked out for them and about a year later, he became father number three for me. Mom was thirty-six by now and I was seventeen and getting ready to graduate high school that coming spring. I had been working after school as office help at a construction company. Because of insurance regulations, I couldn’t operate any of the heavy equipment like dozers and graders and things until my eighteenth birthday. So I helped around the office after school and washed the equipment when it needed it. But what I wanted was to operate the heavy equipment!

Mom did okay with this third marriage – like they say if you kiss enough toads, you’ll find your prince! And heaven knows Mom had gone through the swamp more than once to find Michael! For the next ten years, we were a “normal” family; I graduated high school and got a regular full-time position with the construction company, my stepsister Anna continued to go to school eventually graduating herself. And Mom and Michael seemed happy. It seemed as if we had finally got life figured out. Or so we thought. But it’s just when you think things are going smooth that you have to watch out for that other shoe!

Michael had just gone to the store for a couple of things for dinner that night. That’s how Mom explained it to me. But on the way home, Michael’s small Toyota car was T-boned on the drivers’ side by a semi driver who was trying to beat the light. Michael’s Toyota didn’t stand a chance and neither did Michael. He was pronounced right on the scene – he didn’t even make the hospital. Michael was 47, two years older than Mom. I was twenty-six and Anna was twenty-three.

Anna had gotten a job with a modeling agency right out of high school and was on a modeling shoot when she got the word about her father. When she flew back home I was there at the airport to meet her plane. She had left shortly after graduating to go to a modeling school in New York (much to Mom and Dad’s dismay) and although she was good about calling and keeping us up on all that was happening, we still hadn’t seen her in some time. In fact, I hadn’t see Sis in about four and a half years. It was like she had gone away to college! So when I first saw her at the airport I didn’t even recognize her!

I was standing there in the airport at the gate she was supposed to be at looking for the same pigtailed cheerleader that I was used to seeing. Anna was cute as a cheerleader and I could see how the boys would be interested in her. She had the perfect bubbly personality for it as well. So I was looking for that girl but then this gorgeous blonde came bouncing up to me as if she knew me.

“Hey, Chris! Good to see you again, big brother!”

“Anna? Is that you?”

“Of course it is silly! Do you have any other sisters here at the airport that I don’t know about?”

“Oh my God! What happened to you? You’re ... you’re ... fucking beautiful!”

“Well thank you, Chris. Glad you like it.”

“No seriously, what happened? I remember you as this skinny blonde pig-tailed cheerleader with hardly any ... well you could barely fill out your uniform. But now ... damn!” I tried to be as polite and mannerly as I could but Anna had definitely filled out and I kept tripping over my tongue!

Anna giggled. “Well, it HAS been over four years, Chris. Things change. I’ve changed. I guess I was a late bloomer.”

“Yeah, well, you sure caught up! Holy shit, Anna!”

She giggled again. “Well, are you just gonna stand there ogling me or can a sister get a hug around here?”

She threw her arms around me and pressed herself to me. Damn! she feels even better than she looks!

I tried very hard not to get too “caught up in the moment” and embarrass us both with an inappropriate show of affection (if you catch my drift). But it had been about a year since my last girlfriend and I had broken up and although I dated sporadically, my sex life, if you could call it that, was pretty pathetic.

“Mmmm, it’s good to be home, Chris. I’ve missed this place. And I’ve missed you too.”

“Me?” I said, pulling back to look at her. Anna and I didn’t have the typical brother-sister relationship that most people had. We had different fathers and we came together later in our childhoods – I was seventeen and she was fourteen when our parents married. So we didn’t really “grow up together”. Aside from that, we each had our own lives, our own circle of friends ... I guess you could say we were “paper siblings” – brother and sister in name only. So when she said she missed me specifically, it kinda threw me for a second.

“Sure, knucklehead, you are still my brother, you know!” Anna gave me a smile that lit up the whole terminal, even though it was a bright sunny day and the terminal building had huge glass walls to let in a lot of sunlight.

After that, we went to get her suitcases – and she had brought several of them. “Geez, Anna, how long are you staying? You have enough clothes here it looks like you are moving back home!”

“Sorry, it’s a force of habit anymore. I got to have everything I would possibly need when I travel. I never know what the weather will be like, or what the photo shoot will entail. So it pays to be prepared!”

I wrangled us up a luggage cart and we got all of her things loaded up in my car. “Good thing Mom didn’t come to the airport too – somebody would have had to walk home!”

“Well that somebody would have had to be you – Mom’s too old to walk that far and I can’t with these heels on!” She showed me her five-inch stiletto-heeled Christian Louboutin peep-toe pumps.

“Very nice. But I remember you used to go barefoot a lot as a kid.”

“Oh, that was a long time ago, big brother. I can’t do that anymore. If I hurt my feet and can’t walk, I can’t work! Besides, it’s over five miles to the house from here!”

“Well, sit back and enjoy the ride ... I’ll have you home in a jiffy. Mom is almost beside herself that you are home again so be prepared for the waterworks!”

“I’m afraid it will be a mutual flood ... I have missed her too!” Neither one of us was in a hurry to mention Dad in our conversations, although that’s why she had come home. I guess no one wanted to be the first to bring this reunion down.

On the way home, we took turns asking questions. I wanted to know about her work and her travels and she wanted to know about Mom and home. It seemed like we had just started talking when all of a sudden we turned onto the road that ended with our house.

We lived at the end of a dead end road. The road was three blocks long with the center block on one side containing a small park and playground. We spent many an afternoon playing there and as we passed by it, Anna looked longingly at the site of so many memories. “God, I have missed this place!” she muttered to herself. But not quietly enough.

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