Loving His Little Sister
by Curbstonesetter
Copyright© 2025 by Curbstonesetter
Incest Sex Story: Description: He begins making love with his sixteen year old little Sister on their spring break. They continue to make love with each other through both his and her college careers after which she moves in to live with him. She later demands to have his babies.
Caution: This Incest Sex Story contains strong sexual content, including Ma/ft Consensual Romantic Heterosexual Fiction School Incest Brother Sister Cream Pie First Pregnancy .
Author’s Note: This story is a complete work of fiction from the get go and is intended solely for the readers to enjoy. My thanks to Easyspeak for the work of editing this story so that it makes sense and makes it easier to read and understand.
My name is Milt which is short for Milton. And that is a name I hate with a fucking passion. My Mom told me, “Honey, you were named after your Dad’s uncle. He helped us pay our bills and get on our feet when we were really struggling to put food on the table and keep a roof over our head.”
I replied, “Aww, well, Mom, I guess I can be damn thankful that Dad’s uncle wasn’t named Shitface. It couldn’t have been much worse.” Damn, I think I went a little too far with that last remark because she went into a hellacious rage that I had never seen before and she threw everything she could get her hands on at me before I could get the hell out of Dodge.
Mom ran my ass out of the house and I was afraid that she wasn’t ever going to let me back in again. I had visions of having to live in a homeless shelter with old down and out assholes wanting me to suck their dicks when I was trying to sleep on a damn narrow uncomfortable cot and a stinking previously used blanket that smelled like aged horse piss.
But, that’s another story for another time. I’m not going to go into it now. I’ll not bore you any further with my personal trials and tribulations. But, I digress to the body of my tale.
I had gotten home on spring break from my first year at the university. I was in my bedroom working on a report on my computer that was due after spring break. I knew my little Sister; Jenna was home on spring break from her sophomore year in high school. Mom and Dad were at work and Jenna and I were the only ones in the house.
Jenna is sixteen years old and she has a very pretty face. She seems to have started to mature early. She is about five feet five and 120 pounds with really nice hips and her boobs have really blossomed out for her age.
I could hear her moving around in her bedroom because her bedroom is right next to mine. Every once in a while I’d hear her bedroom door open and she would go elsewhere in the house but, I didn’t pay much attention to what she was doing since I was too busy working on my report.
There was one time I know she went into the bathroom and took a shower because I could hear the shower water running in the bathroom. I just kind of thought that she may be going out with some of her girl friends.
I looked up at the clock and it was about 2:00. I really wanted to get as much work done on my report before evening time because I wanted to turn it in right after I got back to campus. I went back to work on my report and I got the feeling that someone was looking at my back. I turned around and looked at my bedroom door and there stood, Jenna.
She had a serious look on her face and I figured she was wanting to talk to me or to ask me a question. I said, “Hey, Jenna, What’s up?”
Her facial expression changed to one of hesitation and she said, “Can I come in, Milt?”
“Yeah, come on in. Wha-da-ya want, Honey.” She and I had been fairly close with one another and she came to me from time to time to ask for my help and ask me questions. Sometime I got to calling her Honey and she never did object to it. Jenna would occasionally call me Big Brother as she hugged me and pressed her soft titties into my chest after I helped her.
She said, “I want to ask you a question, Milt.” as she turned and closed my bedroom door.
Since I didn’t have a chair other than the one I used when I was working on the computer, I got up and sat down on my bed at the center of the length and I told her, “Ok, sit down here on the bed with me and tell me what’s on your mind.” I patted the bed right beside me showing where I wanted her to sit
Jenna stepped over to my bed and very cautiously sat down beside me kind of like she thought I was going to bite her. I said, “Ok, Jenna, you’re on, what do you want to ask me?”
“Milt, I really don’t know just how to ask you this or even if you will answer me when I do ask you.”
“Well, Honey, you can’t find out if you don’t ever tell me what’s on your mind.”
“Milt, you know how girls like to talk among themselves and I was in gym class the other day and a few of the older girls were talking. I overheard what they were saying and they said something I have never heard before.”
“Ok, but, what’s your question?”
“Well.” she said kind of nervously and she had a little blush on her pretty face. “They said they love it when they were out with their boyfriend and he got to, uhh. Well, what is motor boating, Milt?”
I kind of knew what her question was but, I came back and told her, “Honey, motor boating is someone who takes a boat out on the water with one or two outboard engines for fishing or water skiing or other water sports or just traveling across the water like a lake or a river.”
“Yeah, Milt. That’s what I found on my web browser on my computer but that’s not what they were talking about. They were talking about their boyfriend motor boating them.”
‘I thought, Holy shit, this is my opportunity to see her nice young titties.’ So, I said, “Oh, Honey, I think I know what you are talking about and I can’t really explain it to you. I’ll just have to show you.”
“How are you going to show me, then?”
“Are you really sure you want me to show you, Jenna?”
“Yeah, I really want to know what they were talking about. So, show me what it is, Milt.”
“Ok but, you’re going to have to take your blouse off.” And she started unbuttoning her blouse. When she got her blouse off that gave me a close clear view of her really nice titties cooped up in her white lacy bra.
Then she said, “Now what do you want me to do, Milt?”
“Ok, now I’m going to reach around behind you and unclasp your bra if you agree, Honey.”
She very nervously said, “I really don’t know if I should do that, Big Brother.”
“Ok, Jenna. But, if you don’t want to take your bra off that’s all I can do for you, Honey.”
“Oh, I guess I can take it off to let you show me what it means since you are my Brother. Ok, Milt, you can take it off of me.”
I reached around and unclasped her bra and I pulled the straps down her arms and laid her bra on the foot of my bed.
When I laid her pretty bra on the foot of my bed and I turned back around to look at her, I thought my eyes were going to pop right out of their sockets when I saw her big beautiful titties without her bra on.
Jenna had the most beautiful pair of titties I had ever seen. They were round and firm and they stood up proud on her chest without any hint of sagging. Her nipples were long and they pointed slightly upwards. Seeing her magnificent titties brought me an instant hard-on.
After I had pulled her bra off of her she asked, “Ok, Big Brother, what are you going to show me now?”
Barely able to speak I said, “I want you to lay down here on the bed with your head on the pillow.” Once she had laid down I leaned over her, kissed her and softly asked her are you ready for me to show you now, Honey?”
Jenna had an expression on her face like I can’t believe I’m letting my Big Brother see my titties and then do something to me. Her eyes looked like she was thinking, ‘Holy shit what have I gotten myself into? I sure as shit don’t want Mom to come walking through that door right now. We’ll both be in deep shit if she does.’
Then she said, “Ok, Milt, show me what motor boating is.”
I leaned down over her, put my face in her cleavage and blew on her chest and her titties as I held them close to my face and mouth. I tried to make the sound of a motor boat as I did that.
She just kind of giggled, squeaked and then said, “Is that all there is to it, Milt?”
“No, I haven’t finished yet. There’s more to come. Just lay there, relax and let me finish what we have started, Honey.”
Jenna just quietly laid there with an expression on her face like, ‘Holey shit, I had to ask a question like that and that’s all it is?’
Leaning down over her I started kissing one of her titties in a number of places around her sweet soft globes. From there I licked around her areola with the tip of my tongue. Jenna was kind of purring to me as I was doing that. Continuing, I took her long hard nipple in my mouth and began sucking on it vigorously.
She was softly moaning to me as I was sucking on her nipple. I moved over to her other tittie and repeated what I had just done to her first tittie. As I was kissing, licking and sucking on her other tittie her moaning became a little louder.
When I finished making love with her titties I kissed her and said, “Ok, Sweetheart, now you know what motor boating is all about. Did you like what I just did for you?”
“I thought when you were blowing between my titties was kind of silly but, when you started kissing, licking and especially sucking on my nipples I really like that, Big Brother. Now I can see why those other girls like for their boyfriends to motor boat them.”
“Ok, Honey. Do you have any other questions?”
“Yeah, those girls were talking about something I’d never heard of before. They said, ‘After motor boating they really liked for their boyfriends to go down on them.’ What does that mean, Milt?”
I just couldn’t believe my ears. I think I’ll be able to eat her pussy this afternoon if I want to but, we may not have time enough to do that before Mom and Dad get home from work. I couldn’t believe she really wants me to eat her pussy. I had thought about that for the last year but, I never really thought I’d ever get the chance to lick her pussy and suck on her clitoris.
“Well, Honey, this is like what we just did”. I said, “Like motor boating I can’t really tell you it’s best that I show you wat it means. Like you just did earlier you are going to have to take your slacks and your panties off for me to show you. Do you want to take your slacks and your panties off for me, Jenna?”
She thought for a moment and said, “Milt, I’m scared to do that. Taking my blouse and bra off was something but taking my slacks and panties off will show you everything I have.”
“Ok, Honey, that’s up to you but, I really have to show you. So we’ll just have to leave it at that.” as I kissed her and started to get up and return to my computer and my report.
As I was attempting to get to my feet, Jenna reached out, put her hand on my arm and said, “Milt, I really want to know what it means so I guess I’ll have to do as you have asked me to do.”
“Ok, Sweetheart, even though you will be showing me your most private parts you know that I’ll never tell anyone what we have done here today or what I have seen. And I hope that you won’t ever tell anyone either.”
Jenna got up off of my bed and began to take her slacks off followed by her panties. Like earlier, as she stood there this time completely in the nude, my eyes bulged out at the beauty of her hips and her cute bush, guarding her sweet pussy.
I didn’t know if she had ever had her hymen broken but, I knew that I would soon find out when I slipped down to her pussy and could see it before I began to lick her outer and inner lips and suck on her cute little clitoris.
She looked at me with a look of apprehension in her eyes and she asked, “Now what do you want me to do, Milt?”
I responded, “Just lay back down on the bed where you were earlier, Honey.” I picked up where I left off by kissing her titties and sucking on her nipples. Jenna resumed softly moaning as I was sucking on her nipples.
She softly said, “That feels even better than it did the first time, Baby, and I wouldn’t mind if you did that for me every day.”
I really like doing that for you, too, Sweetheart, and I’d love to do that for you every day if I can.” I kissed my way from her titties down to her tummy button and kissed all around it dipping my tongue into it. I twirled my tongue in it then I started tongue fucking her tummy button.
Jenna really loved me kissing her tummy button and dipping my tongue into it. But, she giggled as I was tongue fucking her tummy button. She said, “Baby, if you keep doing that you are going to make me pee in your bed.”
I quickly resumed kissing all over her lower tummy down to her beautiful bush and nuzzled my nose in the tight little curls of her bush. I could smell the scent of her body wash and she smelled fresh and clean from her shower as I started kissing the thigh crease next to her bush. I knew I was really going to love licking her pussy and sucking on her cute little love pearl.
Jenna gasped when I kissed her thigh crease and I kissed her bush across to her opposite thigh crease. When I got to her opposite thigh crease I kissed her there and she gasped again and gave me a low moan of pleasure.
Lifting her legs I kissed the cleft between her outer pussy lips from the opening of her pussy all the way up to the top of her cleft. She continued moaning her pleasure to me and I slipped back down to her little pink rosebud and licked it and around it and across the area between her rose bud and her pussy opening.
Once I got down to the opening of her pussy, I plunged my tongue into her pussy as deep as I could and licked all around the opening. Her moaning became even louder as I was licking her pussy opening.
Moving further up her love cleft I kissed, licked and sucked on her inner lips all the way up to her little pink love center and I began to suck on her hard protruding clitoris. Her moaning became even louder and she was squirming and moving her hips underneath me as I sucked her clitoris.
After I had been sucking on her clitoris she put both of her hands in my hair and grabbed a double hand full of my hair. She pulled my face and mouth into her pussy and told me, “Don’t stop, Sweetheart, you’re about to make me cum. A few moments more she squealed to me, Oh, Sweetheart, you have made me cum.” as she shuddered and collapsed on the bed beneath me breathing very heavily.
I slipped up to lay beside her, took her in my arms, kissed her forehead, her cheeks and her neck. I whispered to her, “I think my little Princess has reached an earth shaking orgasm and I’m very happy that she has and I was the one to make it happen for her, too. I’ll do it for you whenever you want it and anytime we can, too, Jenna.”
Jenna laid there in my arms looking into my eyes catching her breath when her breathing nearly returned to her normal rhythm. She whispered to me, “Oh, Honey, I know I loved you as a Brother before but, today I have begun to love you more than that, Milt. You make me want to marry you if you would do this for me very often, Honey.”
“Now you know why I said that I really needed to show you what these things meant rather than try to tell you. I think you know you would never have gotten the same pleasure out of this if I had only told you about it and I hadn’t shown you, Jenna.
Now has that answered all of your questions, Honey?”
“No, it hasn’t, Milt. I have one more question to ask you and I may have others after that. And I know after this afternoon that you will tell me that you want to show me rather than just trying to tell me the answer to my question...”
“Well, Ok, Baby. What’s your next question? I’ll tell you if I can but, I suspect that I’ll have to show you.”
“Those girls I heard talking just kept saying things I didn’t understand and this is another one of them. I heard one of them say that she was really happy that her Brother popped her cherry and the other girls all flocked around her asking her questions and saying that they wished they had a brother to pop their cherries. They just had to let their boyfriends do it for them.
All the other girls said that it hurt when their boyfriends did it for them but, the one who had her brother do it for her said it didn’t hurt her all that bad and she would let him do it all over again.
She went on to say she really liked it and she wanted to have him do it for her many more times. In fact, she said he did it for her again the next day and it didn’t hurt her and she wanted him to continue to do it for her. She said, it felt really good each time her brother did it for her.
That’s when I thought about you, and that you could tell me or show me what it meant. I thought if you were like that other girl’s brother you could do the same thing for me.”
I looked at the clock and it said it was 5:00 and our Mom and Dad Normally got home at 5:30. I told her, “Jenna, you’re right I’ll really have to show you but it is getting really late in the afternoon and Mom and Dad will be home soon.
You know we can’t let them find us doing something like that. So, we’ll just have to do it tomorrow morning or tomorrow afternoon while they are at work. Can you wait that long to finish what you want us to do Honey?”
“Yeah, I think we’ll just have to wait until tomorrow to do that, Milt.”
Jenna put her arms around me and kissed me saying, I can’t wait for tomorrow, Honey”
She put her clothes on and sat down on my bed with her back propped up against the wall as I went back to my computer and continued working on my report.
About, 5:30 we heard the garage door go up and Mom and Dad’s car pulled into the garage. A few minutes later the door to the garage shut and we heard Mom say, “Kids, where are you?”
A couple more minutes and Mom stepped into the room and said, “What are you two doing in here?”
Jenna just said, “Mom, Milt is working on his report on the computer and I have been reading and asking him questions about some of the things I have been reading.”
“Well, on our way home your Dad and I were talking about some of the things we wanted to have done and we wanted you two to do it for us tomorrow morning.”
I piped up and asked, “What do you want us to do tomorrow, Mom?”
“There’s a list of things we need to have done on the fridge. It’s very likely to take you both the rest of the morning to get it all done. And then tomorrow afternoon you two can have the time to do what you want to do. But, for right now, Jenna, I want you to come into the kitchen to help me make supper for us.”
Jenna said, “Ok, Mom. I’m coming.” as she got to her feet, looked me in the eye, dropped her book on the dresser and followed Mom out to the kitchen to help her make supper.
I understood the look in her eye and knew that our little session was postponed until tomorrow afternoon after we got our work done for Mom and Dad.
After Mom and Jenna went to the kitchen I gave a big sigh of relief that I had the good sense to postpone any further show and tell for Jenna until tomorrow. I sure as shit didn’t want either Mom or Dad to come waltzing in and catch us in the middle of something they really didn’t want us to be doing. Or at least, not in their house anyway.
I knew that Mom would come down hard on Jenna for what we were going to do but, I knew they’d both come down a whole lot harder on my ass than they would on Jenna. I really didn’t want to put her in that kind of jeopardy. I knew that she was still an innocent little girl and it would break my heart if I did something to cause her that kind of grief. I guess, I really loved her more than a Brother loves his little Sister.
They could kick my sweet ass out of the house and I knew that I would be able to survive and get along. I made up my mind that if they ever came down on her for any reason I would take care of her no matter what I had to do to give her the care she needed and rightly deserved.
I guess I really came to the realization that I loved her this afternoon. She really became more than my little sister this afternoon, she became the little girl, almost a woman, who seemed to want to be my lover. I was not going to disappoint her either, whether we had sex or not.
I knew that tomorrow afternoon she wanted me to pop her cherry even if she didn’t know it right then. I’m pretty sure she had some inkling of what popping her cherry really meant. I was going to do my best to make it as pleasant for her as I could and do my best not to hurt her in any way.
I went back to my bedroom and continued to work on my report after supper and at bedtime Jenna stepped into my bedroom and said, “Good night, Milt.” Then she stepped over to me, kissed me and whispered, “Thank you for all that you did for me this afternoon. I love you, Milt.”
Quickly responding, I said, “Sleep well, Baby. You know we really need to get up early and get all of the things done Mom and Dad have on their list. I want to have it all done by or before noon so we can take our showers and then do the things you want us to do. Good night, Sweetheart.” like she did I whispered to her, “I love you, too, Jenna.”
I was hoping that she went to bed with a wet spot in the gusset of her panties thinking about the tittie sucking and the pussy licking and pussy sucking I had done for her this afternoon. That thought gave me a rock hard dick and I left a wet spot in my briefs.
Jenna and I got up just before Mom and Dad left for work. We got dressed and went into the kitchen and quickly ate our breakfast. Before breakfast Jenna stepped over to me, threw her arms around my neck and kissed me.
She softly said, “I could hardly go to sleep last night thinking about what you did for me yesterday afternoon, Baby. And you made me love you very much, too. I can’t tell you how wet my pajama bottoms got just thinking about you last night before I finally went to sleep.”
I replied, “I thought about you last night, too, Honey, and I’m glad you enjoyed what we did yesterday afternoon. Now we really need to get around and get all of the things done on Mom and Dad’s list by or before noon.
We got the list off of the Fridge and agreed on the things that I could do alone and the things she could do alone. Then we had a couple of things that she was going to need my help to get done.
Jenna said, “Milt, I want to take my shower first but, I said, “I think you need to wait until we have gotten our work done and then take our showers afterward. That way you can shower and get dressed in clean clothes for the remainder of the day.
As we got the items on the list taken care of we marked them off of the list and we had everything done just before noon. I took Jenna into my arms, kissed her and said, “You know, Honey, the way we got things done we make a pretty good team working together don’t you. Now you can go take your shower and then I’ll take mine.”
When I got out of the shower Jenna had her bedroom door shut and I went into my bedroom, got dressed, opened my door and sat down at the computer to do a little more work on my report.
About a half hour later I felt a pair of arms being draped over my shoulders and around my neck. Jenna kissed my cheek and my neck and then she said, “Are you ready to show me what it means to pop a girl’s cherry, Baby?”
I thought, ‘Jesus Christ and General Jackson, Now, she wants me to fuck her. I’ve kissed her titties, sucked on her nipples and eaten her pussy and now she wants me to slip my hard dick inside her virgin pussy. Holy shit, have I died and gone to heaven? Of course, my ass could still end up in hell if Mom or Dad walk into the room and catch me with my dick balls deep in our little Princess.’
Then letting my dick do my thinking for me I said, “Ok, Honey. Do you think you are ready to have me show you what it means?”
“Yeah, I am, Milt. That’s part of what I thought about last night. I was wondering if it was going to be something like what we did yesterday.”
“Well, Honey, yes it is, kind of. But, it is going to be very different. And this time we are both going to have to take our clothes off for me to show you what you want to know. Do you think you are ready to take your clothes off like you did yesterday and do you think you are ready to see me without my clothes on?”
“I have thought about that and since I took all of my clothes off yesterday it isn’t going to be any different today.”
Starting with her blouse, she began to remove her clothes. Then she looked at me and said, “Milt, I thought you said we were both going to have to take our clothes off. Are you going to get undressed or are you just going to stand there and gawk at me?”
She was right; I was standing there and staring at her. I wanted to see those fabulous titties of hers again as she took her bra off. Then I realized that I had a hard-on in anticipation of seeing those fabulous titties of hers and the rest of her body. Of course, I’m sure she really wanted to have a peek at my dick when I dropped my pants and slipped my briefs down my legs to the floor.
I stepped over to my bedroom door and closed it and locked it as she continued to remove her clothes. I quickly got out of mine but, I was able to admire the beauty of her body as she took the rest of her clothes off. And I know she was staring at my body at the same time. I fully expected her to stare at my dick as I took my clothes off.
I softly said to her, “I guess I was staring but, I just wanted to see your fabulous titties and your beautiful body as you took your clothes off, Honey. You are just so beautiful and I want to always remember you this way.”
After we had gotten all of our clothes off Jenna stepped over to me, wrapped her arms around me and pressed her entire body next to mine with her hard nipples poking into my chest and the mound of her pussy pressed against my dick. She softly giggled for a brief moment with a look of intense desire in her eyes.
Then she looked up into my eyes and whispered to me, “When I press my breasts against your hairy chest it tickles them and it sends an electric shock clear through my body and it ends up in my lower tummy and between my thighs and inside me.”
Jenna didn’t say anything about my hard-on poking into her lower tummy but, she reached down and wrapped her small delicate hand around it. She gently squeezed it and hesitantly said, “This is the first time I have ever seen and much less ever held your thing, Milt. I didn’t know that it would get this big and hard. Does it always get this big and hard, Baby?”
“Every time I see you like this it always gets this big and hard, Honey. That’s a sign of how much I want to please you. I want to be very gentle and very careful with you today when I show you what popping a woman’s cherry really means.” as I steered us over to my bed.
Very gently and carefully I laid her down on my bed and I laid down beside her. Jenna cuddled up next to me with her pretty head laying on my shoulder, her soft titties pressed against my side with her tummy and the rest of her warm body as close as she could get to me.
I whispered to her, “Honey, you know I love you and I really don’t want to hurt you but, I hope you know when I show you what popping your cherry means, it is going to hurt at least a little bit. I don’t want to hurt you any more than is necessary but there is no way to prevent it from happening.”
“I know, Big Brother. That’s why I asked you about this since one of the girls said it really didn’t hurt her very much when her brother popped her cherry. And I knew that my Big Brother would do the same thing for me.”
“Are you ready for us to start you on your journey to finding out what this is all about, then, Honey?”
“Yes, I am. I thought about it all night and it went through my mind over and over again wondering what would happen between us this afternoon.”
Holding her tightly and very lovingly in my arms I started kissing her forehead, her cheeks, behind her ears, her neck and her throat. Finally I kissed her very tenderly on her lips and she tenderly returned my kiss as a brief shiver went through her entire body.
She briefly shivered again, softly giggled and then she said, “I loved it when you did that yesterday afternoon for me but, I didn’t know you were going to do it again this afternoon, Honey.”
“You know I liked doing that for you yesterday and I know you liked it, too, so I wanted to give you that same pleasure again this afternoon. Plus it really helps relax you and tells you that I want you to enjoy what we are going to do further today. It helps get you in the mood to accept what you are going to receive as we continue and know that what I’m going to do for you is an act of showing you that I love you, Honey.”
Jenna wrapped her arms around my neck, pulled us very tightly together and said, “I love you so much, Baby, and I’m ready for you to do anything we both want to do, Sweetheart.”
Moving on down to her sweet soft titties I began kissing one and licking around the areola of it while I was fondling and gently squeezing the other one and running my finger over her now hard erect nipple.
Jenna was softly purring to me and then she switched me to her other tittie and her purring to me got a little louder. Taking her nipple in my mouth I began sucking on each of them as she continued to purr to me and tell me, “I loved it when you sucked on my nipples like that yesterday and I love it even more today, Honey.
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