Loving My Older Sister, Jenny - Cover

Loving My Older Sister, Jenny

by Curbstonesetter

Copyright© 2023 by Curbstonesetter

Romantic Sex Story: When he was born his Older Sister took charge of him from their Mother like he was her own personal Barbie Doll. Her love for him lasted throughout their years in school and later in life. They moved in together and she makes love with her Brother with a big surprise.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Heterosexual   Workplace   Incest   Brother   Sister   Cream Pie   Oral Sex   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 Sister Jenny Marie is a few years older than I am. I really don’t remember how much older but, whatever it is, it really doesn’t matter. Suffice it to say that she is my older Sister.

When I was born, Jenny thought that I was her own personal living doll for her to play with and play Momma to. It was much like Barbie dolls are to little girls these many years later. Jenny really loved me and she took care of me with all of the love she could give me.

I know Jenny loved me just as much as a Mother loved any of her own children. She couldn’t do enough for me all during the time I was growing up until she graduated from high school and left home. She was nearly as much my Mother as my own Mother was.

Mom has told me that each morning when I awoke Jenny would come into my bedroom and pick me up out of my crib, take me into the kitchen and feed me my breakfast. Then later she would dress me for the day. After she dressed me she would carry me around, entertain me and play games with me.

She was constantly with me. Each afternoon Jenny would tell my Mother she would put me down for my afternoon nap. And when I awoke she would get me up and take care of me just like my Mother would.

I think that I may have loved her as much or maybe even more than I loved my Mother. There were times when she heard me crying or coughing in the night and Jenny would come into my room and take care of me letting my Mother get a little extra needed sleep.

Of course, everyone else loved Jenny, too, because of her sweet, loving and caring nature. When she started high school she really became a beautiful young woman. She was about 5 Ft.-6 in. tall and about 125 pounds with an hour glass figure. Her frame was well filled out but she was not considered to be fat or even plump just well proportioned.

Jenny was considered to be very pretty with her beautiful, long blond hair, her pretty face and her gorgeous sky blue eyes. Those blue eyes could look right through a person to the depth of their very being. She always used her eyes to please others with her loving nature and her sweet disposition.

How could anyone not love this gorgeous young woman, especially me? I just loved it when she wrapped her loving arms around me. She enveloped me in her arms when she held me tightly and kissed me on my forehead, my cheeks and my neck.

Jenny was so soft and warm with those lovely, soft breasts of hers pressed tightly up against me. Of course, for as young as I was and I had not even gotten close to reaching the age of puberty. I had no understanding of sex at that time or any ideas of what having her two lovely breasts pressing against me could mean.

I just remember having her soft titties poking into my chest or clasping around the back of my neck when she held me in front of her on her lap. My neck just fit in between her breasts like a hand in a glove when she held me with my back to her, I would learn how good it felt to have her soft breasts wrapped around my neck and poking into my chest.

Jenny continued to look after me and take care of me like I was her own baby all through her school years until she graduated from high school. I was only about 10 or 11 years old when Jenny left home and I was still in middle school. I remember being upset and I really missed Jenny very much when she left home to go to the city and found work.

After Jenny graduated from high school she found a job in a large city about an hour’s drive away and she moved out of our parents’ home to live in an apartment in the city. I was always very excited to have her come home to visit us on the weekends. I think that she was nearly as excited about being home with us as I was to have her there. I loved having her hug me and kiss me like she had always done in the past.

When she got home she would say, “Hi, Matt. I’ve missed you and it is really good to be back home and see you again, Honey.”

“Hi, Jenny. I’m so happy to have you back home with us, too. I’ve really missed you, Jenny.”

Then she would ask me, “Have you been a good boy while I’ve been gone, Matt?”

Of course, I always responded, “Yes, Jenny. You know that I’m always a good boy especially for you.”

Then she would just grab me wrap her arms around me and kiss me very sweetly. I think that she just liked to see the delight on my face when she held me and kissed me. When she held me, I would always throw my arms around her neck, hug her and kiss her cheek. She would hug me tighter pressing those lovely breasts against me and tell me, “I love you, Matt.”

With me always responding, “I love you, too, Jenny.” Of course I didn’t really know what all that really meant but, I knew it was what I was supposed to say to her and she really liked to hear me say it.

As time went on and I got older, Jenny didn’t come home as often as she had before. However, Jenny always got home for holidays and special occasions and when I got into high school naturally I had reached puberty and began to grow rapidly toward manhood like all other teenage boys. By the time I was a junior in high school I was six feet tall and weighed about 190 pounds. Nearly all of my weight was muscle and not fat.

The significance of having her luscious breasts pressed tightly against my chest was immediately recognizable, undeniable and irresistible. Or, I guess it is better said that the little man in my jeans could not resist the feeling of those soft breasts pressed tightly to my chest. And seeing her beautiful breasts standing up so large, so perky and so proud on Jenny’s chest did similar things to me, too. Or maybe it was the same thing.

When I graduated from high school I went to college out of state and I was able to see Jenny even less often then. But, that didn’t diminish my feelings for my beloved older Sister. I still loved coming home on holidays and seeing her there and visiting with her. I think that she even grew more beautiful than she was before.

I still loved hugging her and feeling those luscious breasts pressed against my chest. When I was a senior in college I was crushed to find out that Jenny was going to get married. I didn’t think that there was anyone who was good enough to marry my beautiful, sweet Sister, Jenny.

When I met her fiancé I really didn’t have much use for him and later I really didn’t like him at all. I thought he was a real dick head. He was a smart ass and I really didn’t like the way he treated Jenny either.

He could tell that I didn’t have much use for his smart ass. He never attempted to challenge me because I was about three inches taller than he was and I was about twenty pounds or more heavier than he was.

In addition to that, I had played sports in high school and college and I was in really good physical shape and it showed. However, I really didn’t want to hurt Jenny’s feeling or piss Jenny off so I pretty much kept my mouth shut about him.

But, if he had challenged me I would have decked his smart ass in a heartbeat. Jenny got married to that bum before I graduated from college and I saw very little of her or him after that.

After I graduated from college I got a job in the same city where Jenny and her dick head husband lived and worked. I got my own two bedroom apartment and pretty much kept to myself away from them. Occasionally, Jenny would come visit me after work or on the weekend. Once in a while she would stay the night with me in my extra bedroom.

I really got the feeling that she was not too happy in her marriage to the dick head. I don’t know what made me think that. It was just a feeling I got from Jenny that she really wasn’t happy about her marriage to the dickhead. And her unhappiness came right through to me. I just had a strange feeling that she was not really happy with him.

Sometimes I would take her out to eat and then to a movie and other times we’d go out to a club for drinks and dancing. Then one Friday evening Jenny called me and asked me, “Matt, can I come over and see you, please?” Her voice sounded a little shaky and a little nervous. It kind of sounded like it was urgent that she come over and see me immediately.

So I quickly said, “Sure, Jenny. You know that my door is always open for you. You don’t even have to call me. Just come on over, and if I’m not home use the door key that I gave you when you first came over to my apartment.

Just don’t ever let him know you have my key and don’t ever give it to him, either, no matter what else you do. If you give it to him, Jenny, you know I’ll have to take it away from him and he sure won’t like me taking it away from him.”

About thirty minutes later she knocked on my door and when I opened the door for her she stepped inside with a small overnight case in her hand. Her eyes were kind of red and puffy like she had been crying.

I immediately put my arms around her, pulled her to me, kissed her cheek. And then I asked her, “Ok, Honey, tell me what’s going on?” She laid her head on my chest and started crying with tears streaming down her pretty face and soaking my shirt.

She said, “Oh, Matt, there is a lot that has happened but, first before I tell you, I want you to promise me that you won’t fly off the handle and go do something that we’ll both regret. I came to you because you’re my Brother and my best friend and I don’t want anything to happen to you on account of me.”

I knew that something really dire had already gone down. “Ok, Honey, I’m not going to do anything that you don’t want me to do, alright? All you have to do is tell me you don’t want me to do something if it upsets you.”

She said, “Give me a couple of minutes, Matt, and I’ll fill you in.” as she continued to sniffle, blot her eyes and blow her nose into a tissue.

Five minutes later and a glass of water and she started, “Well, Matt, when I got home from work this evening he was home (meaning the dick head) and he’d been drinking heavily.

He hadn’t been working very much lately and I was bringing in most of the money for us. I was paying the rent and buying all of the groceries. He was drunk and he got to yelling at me and calling me all kinds of nasty names.

You know that we weren’t raised using that kind of language and I told him to stop it. That pissed him off royally and he came over to me and slapped me and then he told me not to tell him what to do and to shut the fuck up.

You know that I wasn’t going to put up with that so I went into the bedroom and put some clothes in my overnight case and I called you. I’m not going to go back there and live with him again, Matt.”

“Did he hit you with his fist, Jenny?”

“No but, he clinched his fist like he was going to. And I told him, ‘If you hit me with your fist, Mister, I’ll have you in jail before nightfall’.”

I was so pissed off when I heard that I told her, “Jenny, I’m going to go over there and I’m going to do a whole lot more than slap him.”

“No, Matt, you can’t do that. You promised that you wouldn’t do anything like that. If you go over there and whack on him he’ll have you in jail before nightfall. I think that is what he’d really like to do to you just to spite me.”

“Ok, Jenny. I promised you I wouldn’t do anything you didn’t want me to do.”

“I love you, Matt. I have always loved you since the day you were born, ‘Little Brother’.”

“I love you, too, Jenny. And I’ll always love you, too, Honey. I’ve loved you as long as I can remember. And I’ll certainly never do anything to hurt you either. Well, what are you going to do now, Honey?”

“Tomorrow I need to go over there and get the rest of my stuff and bring it over here if you will let me bring it here and I can stay with you. Is that Ok with you, Matt?”

“Absolutely, it’s Ok with me and I’m going to go over there with you to help you and to make sure that he doesn’t hit you or bother you again. If he does, I’m going to flatten him and make sure that he never touches you again.”

“Ok, but, you just remember what you promised me about not doing anything to him.” Jenny had always been my protector until she left home and now it was my turn to become her protector. And that sure as hell was what I intended to do for my sweet Sister whom I loved so much and who I knew loved me, too.

At nine o’clock the next morning we went over to that apartment and Jenny opened the door to the apartment with her key and let us in. The place smelled like a distillery. We walked into the bedroom and he was passed out on the bed.

Jenny started cleaning out the dresser drawers and putting her clothes in sacks and gathering her personal items. When he woke up and heard her, he looked up at her and said, “What the fuck are you doing in here, bitch?”

Before Jenny could answer, I spoke up and told him, “Shut up and lay there and leave her the hell alone, jerk. Don’t you twitch a muscle until we have left here, comprende, pendejo?” He looked at me standing in the doorway through his bleary half drunk, hung over eyes and he didn’t say another word.

He understood my insult and he could see the venom in my eyes. I think that he knew that I wanted to flatten him and he really didn’t want to provoke me and give me a reason to do so which could be considered to be self-defense.

Jenny went through each room and got all of her possessions and we were about ready to leave. I stopped and asked her, “How about the big flat screen TV, Jenny?”

“Oh, yeah, I almost forgot that’s mine. I paid for it. He has a little one he uses back in the bedroom.” We loaded everything up into my car and I told Jenny, “Let’s take one last look around in each room and the closets and see if there is anything you might have missed that’s yours.”

She did and she found a few more items that were hers and said, “That is about it, Matt. If there’s anything I have missed it probably ain’t worth the time and effort to get it. He can have them. He’s welcome to them.”

We loaded up the car with all of her stuff and returned to my apartment. I helped her bring everything into my apartment and we began to put it away in my spare bedroom. Just afternoon we stopped and we made our lunch. Then we went back to the bedroom and put the rest of her stuff away.

Good lord, I didn’t know that a woman could have so much stuff. It was a good thing that I lived in a two bedroom apartment otherwise we would have had to store a lot of her stuff in the living room.

By mid afternoon we had finished so we sat down and put our feet up and watched a little TV. About 5 o’clock I began to get hungry and I said to Jenny, “Honey, we have had a busy day so why don’t I take you out and buy us our supper?”

Jenny quickly replied, “I was hoping that you would say that because, I knew that you probably didn’t want to fix supper and I didn’t really feel like doing it either, at least not this evening anyway.”

Then she turned to me, put her arms around me and kissed me on the lips, not like I was her Brother, but, more like I was her lover. Holy shit, that made my little man jump up in my jeans just about as much as having her luscious titties plastered on my chest or around my neck. And damn did I love that. Somehow I got the feeling she loved it, too.

After she kissed me, Jenny said, “Thank you, Matt, for helping me get my stuff from that apartment and bringing them over here today. I’m not ever going back there to live with him again. I probably should have called the police and had him charged with assault.”

I took her out to a restaurant that she chose and we had our supper there. When we left the restaurant I asked her, “Would you want to go see a movie this evening, too, Jenny?”

She turned and looked me straight in the eyes with her piercing blue eyes and said, “Sure, Matt, I always did like going on dates with you. Let’s go. And it will get my mind off of that mess with him.” When we got to the cinema, we looked at the choice of movies and Jenny picked out a romantic comedy for us to watch. We went in and found the seats that she wanted and we watched the movie she chose.

Jenny really got into the movie and she snuggled up to me and grabbed my arm and draped it over her shoulders. Then she turned to me and kissed me on the lips again like she had done in my, now our, apartment earlier. My little man really took notice of that again. And I sure didn’t mind it at all.

After the movie, Jenny kissed me and said, “Thank you for the supper and the movie tonight, Matt. I don’t remember having had such a nice night out in a really long time.” Then she kissed me again. I was hoping that we would get home without me getting a galloping case of the blue balls.

When we got home we both had a glass of wine and watched a little TV. When I had finished my glass of wine, I was tired and told Jenny that I was ready to go to bed. I got up and headed for my bedroom. Jenny said that she was going to stay up for a little while longer to watch TV a little bit more and unwind from the day.

I went into my bedroom, shucked off all of my clothes like I normally did and got into bed. It felt like I had just gone to sleep and I felt my bed move. When I became awake enough to understand what was happening I recognized that it was Jenny. And she was in her night gown. Of course, she only had her night gown on with nothing else on under it as she usually did.

She had pulled back the covers and crawled into the bed beside me. She rolled up on her side and laid her big soft titties on my chest and kissed my cheek and neck. Her hot titties felt even softer that night, probably because she always takes her bra off before she puts her night gown on.

Then she caressed my face, laid her hand on my bare hairy chest and slowly slid it down across my belly. When she reached my crotch she found that I didn’t have any briefs on and she quickly grabbed my half hard dick. She must not have been having sex with the dick head because she appeared to be very horny that night.

Jenny then whispered to me, “Good Lord, Matt, I didn’t know that you had that monster down there. If I had known that, we would have done this a long, long time ago.”

I reached up and took one of her big, soft titties in my hand and I remarked, “Well, Jenny, I knew that you had this monster and the other one too and I would have loved to have done this a long time ago, too.” She continued to hold my dick in her hot delicate hand feeling it grow to rock hardness and to its full hard length.

I just had to reach down, grab the hem of her nightie and pull it up and over her head. There wasn’t any objection from my luscious, hot body Sister. I tossed her night gown down on the foot of the bed where it was out of the way.

I could have left her nightie on her but I wanted it out of the way so I could easily fondle her soft titties with my hands and gently pinch and twist her nipples. I wanted to kiss them and suck on her nipples and feel them pressed against my chest.

After I got her nightie off of her she leaned down and kissed me passionately with her soft, warm titties pressed tightly to my chest. Holy shit, that felt so good feeling her soft titties and her hard nipples pressed tightly into my chest. I wanted that to continue for a long time or at least until we woke up in the morning.

Jenny then threw her leg over the top of me and straddled me. She settled her warm wet pussy on top of my hard dick. She wanted me to feel how warm and wet her pussy already was. I put my arms around her and told her, “I don’t know what has turned you on so much like this tonight, Jenny, but, I love it and I love you, too, Honey.”

“You have turned me on, Matt, and I’m hoping that I have turned you on, too.”

“Damn right you have, Jenny. You knew that you did when you took me in your hand just a few minutes ago.” She just giggled her sinister little laugh back at me like I had just caught her with her hand in the cookie jar.

Her giggle was so cute I just had to pull her to me with her big, hot titties pressed down to my hairy chest. I kissed her passionately and held her tightly to my chest. She just wiggled her whole body on top of me in a tempting display of what she wanted us to do from there.

She put her hands on either side of my head holding my face to her, tenderly kissed me again and said, “I love you, too, Matt. I have wanted us to do this for such a long time and tonight is our chance to make this happen, Honey.”

Jenny rose up on her knees, grabbed my dick and put it in the opening of her pussy and slowly sank down on top of me with my hard rigid dick slipping slowly all the way into her warm, very wet and welcoming tight pussy.

Holy shit, did that feel so good to me and undoubtedly it really felt good to her, too. I could feel her squeezing my dick with the muscles of her pussy showing me how much she loved having my dick slowly slip all the way back and forth into her warm tight pussy. I damn near shot my hot cum deep into her pussy as she squeezed my dick with her pussy muscles.

Jenny slowly got all the way down onto my dick with her bush pressed against mine. I pulled her shoulders down to me with her warm, soft titties pressing tightly against my chest again. I was ready to begin squirting my whole load of hot love cream into her pussy right then.

I put one arm around her waist with my other hand on the back of her head. Holding her warm cheek next to mine, I kissed her and whispered into her ear, “Lay perfectly still for a few moments, Jenny. I just want us to savor this first time you have taken me into your sweet warm love passage for a few moments, Baby.”

“Why do you want us to hold still, Sweetheart? We can savor each other as you are slowly slipping back and forth into me.”

But, Jenny, if you move very much you are going to make me fill your pussy with my scalding hot love cream. I just want us to be one body and one spirit tonight. I can’t tell you how good it felt to have you slipping up and down over my rigid love member and squeezing my member with your pussy muscles, Honey.”

“We have been one spirit since the day you were born, Matt. We were both born from the same flesh and blood that makes us one spirit. You have just made us one body when you filled my pussy with your huge hard love member.

When you fill me with your hot love cream that will bond our spirits together forever. I want you to cum inside me, Honey. I want your spirit to live totally within me for all time and I want my spirit to live inside you for all time also, Matt.”

But, Jenny, we don’t want you to get pregnant. Don’t we need some kind of protection to keep you from getting pregnant?”

“You don’t need to worry about that. I have taken care of that and I’m ready for you to squirt your hot love cream into me right now. Make me cum and I want you to cum into me, too, Baby.” She immediately began to vigorously move her hips up and down to make us both cum.

Within moments I think I squirted more cum inside my loving Sister’s pussy than I have ever squirted into any other woman’s pussy before in my life. I wanted to show her just how much I loved her with my hot love cream squirting deep into her.

Jenny immediately whispered to me, “I can feel your hot love cream squirting into me; Matt, and now we are one both in body and in spirit. We are now bonded together for all time”

“But, Jenny, you didn’t cum and I want you to cum, too.”

“Yes, I did, Matt. You made me cum when you slipped your big hard love member into me when we first coupled a few minutes ago. We are now coupled forever, Baby.”

“I didn’t hear or feel your orgasm and I want you to cum again for me.” Then I rolled her over onto her back and put my head between her thighs. I stuck my tongue between her lips at the top of her pussy and I started licking and sucking very hard on her little pink love bud.

I could taste my own cum mixed with hers beginning to run out of her pussy. Within moments she was moaning very loudly, trembling, gasping for her breath and bucking her hips up to me from beneath me.

Since our combined love fluids were running out of her pussy, I began to lick them up from her pussy opening. Collecting a mouth full of our fluids I moved up over her, kissed her and let some of our love fluids drain into her mouth. As Jenny tasted our fluids in her mouth she softly moaned to me, “That makes us even more one in body and spirit, Baby.”

I returned to licking and sucking on her clitoris and momentarily she cried, “You are going to make me cum again, Matt.” That made me suck on her clitoris even harder and more vigorously and very quickly she squealed, almost screaming, “I’m cumming, Matt, I love you, Honey.”

I continued to suck on her clitoris as she continued to tremble and shake until I thought that she had reached the end of her orgasm and, she continued to squeal, “I’m cumming, Matt, I’m cumming.” She moved her hips almost violently beneath me and she began to squirm, pushing my head away from her pussy with her hands on the top of my head.

Believing that she’d already reached several orgasms; I moved up over her and kissed her forehead and her cheeks as she was really gasping for her breath. She laid there for several minutes cuddled in my arms next to my chest recovering her breathing and looking deeply into my eyes.

Then she whispered to me, “You are the best and most ardent lover I have ever had inside me, Matt. And I want us to do this again from now on. Now I know why I love you so much, Honey, and why I have loved you ever since I was a little girl. I never want us to be separated again, Sweetheart.”

“Your love makes me want to love you and please you in every way and as much as I can, Jenny. You know, Sweetheart, I have been inside other women but, I have never felt so good cumming inside them as I have felt inside you tonight, Baby.” I kissed her very sweetly and we both drifted off to sleep with her pretty head laying on my chest as I held her in my arms tightly to my chest.

Just after the sun came streaming through my window that next morning I felt a pair of soft, warm titties on my chest and sweet, loving kisses on my forehead, cheeks and neck. When I opened my eyes I found my beautiful, beloved Jenny looking into my eyes. She said, “Good morning, Sweetie. I hope that you slept as well as I did after we made such sweet love last night, Honey.”

“I did, because of the beautiful love you showed me last night with that tight hot pussy of yours firmly holding on to and gripping my hard love member too, Jenny.”

“I want us to make love again this morning, Matt.” Jenny pulled me over on top of her and put my quickly hardening dick inside her warm, wet pussy. She made my dick get rock hard within a few moments. And much to her delight she giggled about how quickly and how hard it got in her soft, delicate hand.

Within a few minutes we were both gasping for our breath and she was squealing that she was cumming. She was shaking and she squealed even louder as I started squirting my scalding hot cream deep into her sweet pussy again this morning.

Jenny breathlessly whispered to me, “I love you, Matt, and I love you squirting your hot cream into me where I could feel every ounce of it flowing into me. I could feel your sweet love in every squirt you delivered deep into me, Honey. It felt like it was so hot it was like you were squirting boiling oil into my pussy.”

“I love you; too, Jenny, and I really love having my hard member inside you to fill your pussy full with my hot cream. With every ounce of my cream I left inside you I left more of my love in you.” Then it occurred to me that we didn’t use any protection either last night or this morning either.

A little later, I asked her, “Jenny why haven’t we used any protection when we have made love, Honey?”

“Because I’ve had an IUD inserted inside my uterus. The IUD keeps me safe and keeps me from getting pregnant. However, if it was anyone else but you I would have made them wear a condom. I made him (meaning the dick head) wear a condom from the get go because I felt like I really couldn’t trust him. I was not going to let him or anyone else give me an STD.”

“But, why do you have the IUD then, Jenny?”

“Because not long after I married him I realized that he was no good and I wasn’t going to have his baby. So, I went to the doctor and I had this IUD inserted and now I can make love with you. I really don’t have to worry about you getting me pregnant with that IUD inside me, Matt. Besides that, Honey, its long term – it will last at least 10 years before it has to be replaced.”

“Well, why didn’t you tell him to hit the streets a long time ago, Jenny?”

“Because, I didn’t want Mom and Dad to worry. I knew that they didn’t really like him all that much and you didn’t have any use for him at all, either. I could see it in your eyes and on your face. And thank you for not making a scene in front of Mom and Dad about him, Matt.

You know what Mom and Dad think about divorce. Now that he has turned into a drunk and has misused me I have ample grounds for leaving him and divorcing him. And Mom and Dad will not complain about that since he has mistreated me. Dad would probably want to kill him or beat the hell out of him just like you said you wanted to do, Matt.”

 
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