My Older Sister and Her Small Friend - Cover

My Older Sister and Her Small Friend

by Curbstonesetter

Copyright© 2023 by Curbstonesetter

Romantic Sex Story: Description: Flo and Nate make love and then Flo brings her BFF, a very small woman into their love circle. They have a threesome with her small friend. The women eventually move in with Nate and the love making continues.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Lesbian   Heterosexual   Fiction   Workplace   Sharing   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 older Sister Flo, short for Florence, is more than two years older than I am. We were always pretty close to each other all during our childhood and through our school years. We looked out for one another during the time we were in high school and to a lesser extent while we were in college, too. We were still close though even after we both graduated from college as well.

After we graduated from college, we both found very good paying jobs in the same city. I followed along in my big Sister’s footsteps. Even though I didn’t realize it at the time I really loved Flo very much probably because I always looked up to her ... I thought it was just because she was my Sister that we were so close to each other but, that was likely the biggest reason for our closeness to each other.

After high school, Flo went to our local community college for two years and then she transferred to the state university where she finished the requirements for her degree. When Flo received her degree she was offered and she accepted a job in a metropolitan city not all that far from our hometown. Our parents were happy where her job was located because they thought she would be able to visit with them often.

I did the same thing that Flo did and after high school I went through our local community college. Then I went on to the state university where I received my college degree.

Coincidentally, I was offered and accepted a job in the same city where my big Sister had gotten her job. However, when I moved to the city my job was with a different company and located in a different area of the city from where my Sister’s job location and her apartment were located.

Flo lived in an apartment not far from where her offices were located. I then found an apartment to live in not far from the location of my job facility. The trip from my home to Flo’s home was nearly an hour’s drive clear across town and we certainly did not want to make that trip every day or normally not even every week either. The drive time was even longer during rush hour.

Neither one of us wanted to have to drive through the heavy cross town traffic any more than necessary. That was especially true during rush hour times when the traffic was even heavier than the normal traffic flow. Rush hour traffic was a pain for me and I’m sure that Flo regarded it as even more of a pain than I did.

There were quite a few miles between our homes and we were only able to see each other about every other week or two and sometimes even longer depending on our work requirements and work schedules.

It wasn’t like living just a few blocks apart. Even though we couldn’t see and visit with each other all that often, we did regularly talk on the phone or see each other on Facetime or on Skype.

Our Mother had taught Flo well with regard to keeping house and cooking. Flo turned out to be a great cook and her home was always immaculate. She would make someone a great wife, homemaker and cook and probably Mother of their kids, including me. I knew she liked kids and she always wanted to have kids very much. And when the time came I’m sure she would make one great mother to her kids, too.

Every couple of weeks or so Flo would call me and invite me to come over to her home and she would cook supper for us. I think that her main purpose was to have me there to help eat her cooking. And damn good cooking it was, too. She told me it really wasn’t worth her time to cook a nice meal just for herself and then have to eat the same leftovers for a week or more after that.

Of course, I was always quick to accept Flo’s invitation to come to her house for supper. Flo was such a great cook and it was a legitimate excuse to make the trip across town. I always liked to come to her house to see her even though it was a long drive through heavy traffic.

I really enjoyed her cooking and I enjoyed seeing my sweet Sister in person as often as I could. Flo always liked to invite me to come over for supper with her on Friday evenings. I guess it was a kind of celebration of the end of the work week and a great prelude to our weekend.

Since Flo was doing all of the work of the cooking for us, I always brought a couple of sacks of groceries for her. I knew that she would end up feeding much of those groceries to me anyway.

I also brought along a bottle or two of her favorite wine to go with our meal. Since I certainly didn’t want the entire burden of our meals to be on her, I thought that it was only right that I bring her some groceries each time I came over to have supper with her.

Not only that, when I brought the groceries and wine in the door she always put a great big bear hug on me and kissed me very tenderly. I think that is probably another reason why I always eagerly accepted her invitation to come to supper at her apartment with her.

The hugs and kisses by themselves alone were almost worth my drive across town to see her anyway. What red blooded man wouldn’t like to have her big soft titties pressed against his chest when she put her bear hug on them.

Flo was such a good and talented woman and when she hugged me and kissed me she was really a passionate woman too. With all of her talents I knew she would make a good wife and mother someday, as well.

I could just envision Flo holding her baby in her arms and showering her baby with her love, kisses and affection every so often. I had tinges of sadness at the thought that I, as her Brother, could not give her the baby I knew she really wanted.

After our supper I always helped Flo with the cleanup of her kitchen. Then we would retire to her living room, sit on her love seat with a glass of wine and watch a movie on her big screen TV.

Some of the time I would sleep in her spare bedroom rather than make the long drive back home to my apartment that same night. It’s not that I couldn’t make the trip but it gave me a little more time to be with her and visit with her, too.

With Flo sitting that close to me I always put my arms around her, held her tightly and kissed her cheek and her neck. Then I’d tell her, “I love you, Flo. Thank you for cooking such a delicious supper for us. If I could, I’d marry you and make you my wife.

Then she would wiggle in her seat, put her arms around me and kiss my cheek in return and tell me that she loved me, too. She sure felt warm and affectionate next to me when I had my arm around her.

Or sometimes I would take Flo out to see a movie after we ate our meal as my special treat for her. I always liked to take her out to a movie because sitting so close to one another I could put my arm over her shoulders and hold her. I could reach my hand over to her opposite shoulder and pull her tightly to me, kiss her cheek and whisper in her ear.

I usually said, “I love you very much, Flo.” She generally just wiggled in her seat and looked straight ahead at the movie. Once in a while she would turn her head to me, kiss me on my cheek and whisper in my ear, “I love you, too, Little Brother.” I always thought that was so special and so loving coming from my sweet Sister. How could I not love her as good as she always was to me?

I always got a hard-on holding my Sister’s warm soft body like that, whispering in her ear and kissing her cheek. I don’t know just how she felt but, she always shivered a little and wiggled her cute butt a little bit in her seat, too. I wouldn’t be surprised if I made her panties a little damp whispering in her ear.

Needless to say my sweet Sister and I love each other very much. I remember surprising her one time by giving her a “Wet Willy”. That is where I stuck my wet tongue in her ear after I whispered to her, “I love you, Flo.” I knew that had to leave her panties a little bit wet after giving her the “Wet Willy”. Flo just turned to me and whispered in my ear, “I’ll get even with you for that, Little Brother.”

Flo is a good looking woman, not gorgeous by Hollywood movie star standards but, she is very pretty. Her well-kept shoulder length brown hair and her matching color sparkling brown eyes are striking. And when it comes to body shape, Flo has a really enticing hour glass figure much like our Mom has.

They both have a very shapely hour glass measurements on her 5 Ft. 6 in., 130 pound frame that most women would kill for. She just looked like a picture of the shapely maturing woman. And, man, did she really look good in her bikini. When I saw her in her bikini I never failed to get a stiffie.

When we were in high school and in our local community college she kept my dick hard all the time with me wanting to make love with her. So when I gave her a hug and a kiss after our meal it sure as hell made my dick stand up and salute her for her housekeeping and especially her cooking. But, my hard dick salute was mostly for her beauty and her hour glass shape.

I always hoped that she wouldn’t get pissed to see that she gave me a raging hard-on by the huge bulge in the crotch of my slacks. Then I had to think if I could see that, her panties had to be wet and I sure as hell wouldn’t be pissed at that but, that was probably the difference between me and her.

I don’t know if Flo ever dated or not. She never really talked to me about ever having other guys over to see her or going out with anyone. I sometimes got the feeling that Flo was getting really turned on when I hugged her and kissed her.

One night after our supper as we sat on the love seat, I put my arms around her and was going to kiss her cheek as my thank you. She turned her head to me so that I had to kiss her on her lips.

Her breathing became a little shallow and quicker and I could tell that she was very slightly trembling in my arms. She kissed me back and then I told her, “I love you very much, Flo. I really don’t deserve to have such a good and pretty Sister that you are, Honey.”

Flo immediately replied to me, “I love you very much, too, Nate. You are the best Little Brother a girl could ever want to have, Sweetie.”

I could see her love for me glowing in her pretty brown eyes. It looked like her eyes were on fire and I think that the fire in her eyes sparked a sympathetic fire in my eyes, too. It also sparked a fire in my lower belly and in my balls because of the way she responded to me after that.

Having said that she got to her feet, grabbed my hand and led me to her bedroom. There she threw her arms around me and kissed me very affectionately and very passionately. Hugging me so tightly, Flo pressed her big titties into my chest and that really made my dick get as hard as heat treated tool steel.

Then she said to me, “Nate, I have begun to notice that every time you hug me and kiss me when we sit on the love seat there’s a big bulge that forms in between your legs and that gets my panties wet, too, Honey.

Along with that, you give me a strong desire in my lower tummy and between my thighs to have you inside me, Baby. I want to have you inside me tonight, Nate. Do you want to put that big bulge in your pants to use into me tonight?”

I couldn’t believe my ears. My head was spinning. My teenage fantasy about my sweet loving Sister was on the brink of coming true. I quickly responded to her, “Flo, every time I have told you I love you it has always been much more than just Brother-Sister love. I have loved you all of my life, Sweetheart.

I have wanted to make love with you since I reached the age of puberty and I was capable of getting a hard-on before I started high school, Honey. If you want us to make love, it would be a long time dream come true for me. I don’t want to force you to do something you don’t want to do but, I still want to slip my hard love member into you tonight, Flo, Ok?”

“Oh, Nate you are such a silly boy. I would never have brought you in here to my bedroom like this if I didn’t want us to make love with each other.” as she began to remove my clothes. When she had removed my shirt I removed her blouse and then I slowly and gently reached around behind her back and unclasped her bra. She let her blouse and bra fall down her arms and she laid her blouse and bra on the foot of her bed.

Flo quickly turned back to me where I could get a good, full frontal view of her pair of beautiful luscious titties for the first time in my life. I kissed each one of them in several places around her soft globes.

After licking around each of her pink areolas, Flo began to squirm a little and hold my head very tenderly. And then I sucked briefly on each of her hard erect nipples as I fondled and gently squeezed the other with my hand while gently twisting her nipple.

She purred softly to me and continued to gently hold my head in her hands as I kissed her soft titties and sucked on her nipples. Flo pulled me closer to her for me to feel her warm soft titties against my hairy chest as I held her and her soft titties tightly against me. Within moments my dick began to drip with pre-cum into my briefs. I knew that her love fluids had to be flowing just as much as my pre-cum was dripping off the end of my dick.

As I pulled her tightly to my chest with her luscious soft titties pressed between us she laid her head on my shoulder. Flo softly said to me, “I love feeling my breasts on your warm hairy chest, Honey.”

When I felt her titties on my chest my heart rate jumped up nearly to the red line rate and I told her, “Flo, having your warm soft titties on my chest is like I’m about to step through the doorway to heaven. I just want to hold your warm soft body like this all night.

I could hold you and feel your warm body against me every day. Holding and kissing you like this has always excited me but, this is the highest excitement of all. I just want to give you that same excitement each time.”

Flo responded to me saying, “I like having my breasts on your hairy chest, too, Little Brother, just as much as you do. I have dreamed of holding you next to my breasts since we were in high school. Now, let’s not quit there. I want a lot more loving from you tonight, Nate.”

She quickly began to unbuckle my belt and unbutton and unzip my slacks. Flo pulled them down my legs to the floor for me to step out of them. I unbuttoned and unzipped her slacks and pulled them down her legs to the floor for her to step out of.

That just left her in her hip hugger panties and me in my briefs. Flo looked at the bulge in my briefs and she reached down and gently squeezed my dick several times while I slipped my hand between her thighs and I found a huge wet spot in the gusset of her panties.

Holding us separated at arm’s length, I softly said to her, “My God, Flo, you are so beautiful to me with those magnificent titties and your hour glass figure. I can’t wait to slip deep into your hot wet love flower and make your head spin and make you gasp for your breath as you reach your orgasm, Baby.” She looked deeply into my eyes and she had a bright smile on her pretty face.

I wrapped my arms around her and dropped my hands down behind her finding the waist band of her panties. Slipping my hands down inside the back of her panties I cupped each of her soft bottom cheeks in my hands and very gently but firmly squeezed each cheek. Pulling her up tightly up against my dick for her to feel how large and hard I was for her.

Flo just sighed and shuddered at my squeezing her bottom cheeks. She wrapped her arms around me and whispered in my ear, “You’re making my heart race, Honey. And you’re making my pussy get very wet with anticipation of having you slip your big hard love member as deep into me as you can get it and vigorously slipping back and forth into my wet love passage.”

“That is what I intended to do for you since you have given me tachycardia many times when you hold me and kiss me and you press your big soft titties and your warm body tightly against mine, Flo.

You think that the only reason I come over here to see you is to eat your great cooking. But, mostly, I come over here to feel your soft body and your big titties pressed tightly up against me and for us to kiss each other so passionately, too, Honey.”

“Thank you, Little Brother, you have a huge beautiful love member and I’m ready for you to slip that big thing into me too. I want to feel you squirt your hot love cream into me, as well. I want to feel every last little drop of your love cream as you squirt it into me. So let’s not waste any more time talking about this.” She softly and somewhat breathlessly whispered in my ear.

With that, she pulled my briefs off of me, laid down on her bed and pulled me down on top of her. I began to kiss her as she slipped her tongue through her lips and into my mouth.

Always accepting her challenge I dueled with her tongue for the mastery of our oral contest. With her arms around my neck and her tongue in my mouth I nearly squirted my hot cum all over her tummy and on her voluptuous titties.

I think she won that oral contest. Then I slipped down, kissed each one of her soft warm titties and sucked on her hard dark pink nipples as she resumed purring softly to me. Flo whispered to me, “Don’t tease me any longer, Honey. I want to feel you inside me please.” So I quickly removed her panties and kissed her bush and the crease of her thighs on each side of her bush.

Flo grabbed the sides of my head with her hands, pulled me up to her face, kissed me very affectionately and whispered to me, “I really have to have you inside of me now, Nate.

Please take me now, Honey. I really want you to fill me with your hot love cream. And I really want us to cum together, Sweetheart. It’s even better for me when we can climax together.”

I asked her, “Do we need contraceptive protection, Honey?”

“No, I already have contraceptive protection inside me, Little Brother.” I really didn’t understand that statement but, I thought she knew what she was doing. And I didn’t think she wanted to take the time to explain it to me right then.

With that, she reached down, grabbed my dick and put the purple bulbous head of it just inside the opening of her sweet very wet pussy. That made my breathing get faster and my heart rate began to elevate again, too.

Flo then whispered to me, “Now, I want to feel your hard dick slowly slip into me and do me fast and hard, Little Brother. And make us both cum now, please?”

With a demand like that, there was no way I could deny her and disappoint my beautiful, anxious and very horny big Sister and I sure as hell wasn’t going to disappoint her if I could help it. I really wanted to bring her to her climax and squirt my scalding hot cream into her hot wet pussy.

Once I slipped into her love flower to our full penetration, I felt like I had just entered heaven. It was so hot, wet and slippery and I began to stroke her slowly at first. Then fast and hard with Flo moaning loudly to me saying to me, “Fuck me, Nate, fuck me fast and hard, Little Brother. Now I want you to make us both cum, Honey. I can’t wait to feel your hot cream squirting to the depth of my love passage, Sweetheart.”

The sound of our bodies forcefully slapping together was so loud it was echoing throughout her bedroom which I think turned Flo on even more. I felt like her pussy was a vise squeezing and relaxing around the entire length of my dick.

It felt like she was trying to milk the cum out of my dick with the powerful muscles of her pussy. When she was doing that I felt like she was saying, ‘Come on, Baby, give me your hot love cream at the same time you make me cum, Sweetheart.’

Within a few moments after that, Flo was breathlessly squealing very loudly. “I reached my orgasm, Honey.” And I began squirting my hot love cream deep inside her pussy. Once I began to squirt my hot sticky cum into her wet pussy we both shuddered for a moment.

She breathlessly squealed, “I can feel your hot cream squirting into me, Baby. It feels like boiling oil being squirted inside my love passage. I have to have you do that for me again. You’re making me cum, Nate. Hold me tightly, Honey, and fill my pussy with your cream. Don’t stop, Sweetie. You’re about to make me cum and I’m cumming now. You’re making me love you more. I love you so much, Sweetheart.”

I immediately leaned down and kissed her and later laid down beside her until we both could regain our breathing. As soon as I could, I took her in my arms and told her, “I love you, too, Flo. I love making love with you and squirting my hot baby making cream deep into you, Honey.

This has been my longtime dream come true, Baby. Having my hard dick slip deep into your sweet hot pussy is so beautiful. It makes me love to squirt all my love into you with each squirt of my cream into you. There is nothing that feels better than slowly slipping my hard dick all the way into your velvety soft love flower, Flo.”

“That’s the best feeling of my life, Nate. To have your hot cream filling my pussy coming from someone who I know really loves me. That’s what made me start cumming. I want you in my pussy many more times than this, Honey. You’re such a good lover. I love you very much, Little Brother. I want to have your dick inside me again many more times after this, too, Sweetheart.”

“And I want to be back inside your sweet, velvety smooth love flower again, too, Flo, to have my hard dick inside you each time we make love.”

We laid there in each other’s arms and later I told Flo, “Honey, I need to get up, get dressed and go home.”

“No, Baby, I want you to stay here and sleep with me tonight. I don’t want you to go just now. Tomorrow is Saturday and we don’t have to get up and go to work in the morning anyway.

Please stay and sleep with me tonight, Nate. I want you to hold me until I go to sleep in your arms. And I want to wake up and see you laying here beside me in the morning, too, Baby.”

I knew there was an ulterior motive in her mind. Flo wanted me to stay there and fill her pussy with my hot cream again later in the night or early in the morning. And I wasn’t going to disappoint her by leaving before morning.

I wanted to make love with her again, too, and I wanted to hold her until we both went to sleep. I also wanted to wake to see her pretty face in the morning, as well, sleeping so peacefully beside me.

Flo and I repeated our love making in the morning and two or three more weekends after that. And then one Friday night when I arrived at her apartment I knocked on her door Flo called from the kitchen for me to come in. I walked into her apartment and into her kitchen. I noticed that there were three place settings and three wine glasses on the table but, I chose not to question it.

There were two candles placed on the table, too. I didn’t know just what she had in mind but she said, “Supper is just about ready, Nate. Let’s go sit in the living room until its ready” as she handed me a glass of wine and picked up a glass of wine for herself.

We then went into the living room to relax for a while until supper was ready to serve. I thought this was all a little bit unusual and I didn’t know who else she was expecting to join us for supper.

I sat down on the love seat where I usually did and Flow sat in the easy chair opposite from the love seat. I thought that was a little unusual, too, but, I didn’t bother to question that either. We sat and talked and about ten minutes later there was a soft knock on her door.

Flo got up, went to the door and opened it. A very small but very pretty and shapely young woman busted through the door. Flo’s face and eyes lit up and she said, “Oh, hi, Bonnie. Come on in, Girl. I’m really glad you could join us tonight.” Flo leaned down so that they could engage in an intimate embrace with a kiss on each other’s cheeks.

Then Flo brought Bonnie over to me and introduced us and said, “Bonnie, this is my younger Brother, Nate. I have told you about Nate. Nate, this is Bonnie my good friend from work. She and I work in the same office together. She is such a good friend I just wanted to introduce you two. That’s why I invited her to join us for supper tonight, Little Brother.”

I started to put out my hand to shake her hand and Bonnie said, “Oh, no you don’t, Nate. You’re Flo’s Brother and I want a hug from you just like Flo always gives me, not just a hand shake.”

As small as she was I just picked her up to hug her. We hugged each other and I said, “Hey, Bonnie, it’s good to meet you and I know that I’m going to like you already.” As we released our hug I could see over Bonnies shoulder that Flo was smiling from ear to ear. “Since you’re such a good friend to Flo you are my good friend, also, Bonnie. And I have a great amount of respect for Flo’s opinions as you can well imagine.”

Flo immediately told us, “Bonnie, you can sit down there on the love seat beside Nate, and I’ll get a glass of wine for you. Then I’ll have supper ready for us in a few minutes. I hope that you two are hungry.” Bonnie and I both responded we were very hungry.

We were about to sit down on the love seat and I had a good look at Bonnie. She was very pretty with her flashing, sparkling brown eyes and her well styled shoulder length brown hair.

Bonnie could not be much over four feet tall maybe 4 Ft. 6 in to 4 Ft. 8 in. tops. She was nearly a foot and a half less than my six foot height. But, goddamn, did she have one hell of a figure with a pair of bodacious titties and an hour glass figure. No wonder she and Flo were such good friends.

Except for the height difference and the proportionality, Flo and Bonnie could very well have been taken as twins. Almost certainly they could have been taken as Sisters. And Bonnie had an ebullient personality like she has never met a stranger in her life. She sure as hell didn’t regard me as a stranger when Flo introduced us and I liked her very bubbly personality at the get go.

I began to speculate to myself. ‘Maybe those titties look so big because they are sitting on the chest of such a small short woman. Oh, fuck, that don’t make a damn. I’d sure love to fondle and suck on each one of them if I got the chance.’ She sure made my dick sit up and come to attention just like it does with Flo.

After Bonnie and I hugged, we sat down on the love seat; Bonnie took my hand in her tiny little hand and said, “Well, Nate, Flo sure didn’t exaggerate when she told me about you. She told me that you were tall dark and handsome and she sure didn’t lie to me. I think that you sure are just yummy.”

I had never been called “yummy” before but, I thought it was really cute of her to use that word. I really didn’t know what it meant to be “yummy” but, she apparently thought it was a very good quality. So I chose not to question her use of the word “yummy.” I kind of thought that Bonnie was “yummy”, too, if she meant what I thought she did. I kind of thought her big titties were “yummy” if that was what I thought she meant,.

Whatever that meant, I kind of thought maybe it meant she wanted to suck my dick. If that is what it meant I thought I’d kind of like to have my lips and tongue on her little pussy. I wanted to see if I could give her multiple orgasms with my mouth and tongue while she was doing her damnedest on my hard dick. There sure as hell wasn’t anything wrong with another fantasy along with wanting to kiss and suck on those big soft titties of hers.

“Thank you for the compliment, Bonnie. You’re really very pretty and very ‘yummy’ yourself.” Having said that, Bonnie squeaked, squeezed my hand and I squeezed her hand right back.

Bonnie just kind of wiggled in her seat and moved over closer to me like I had just asked her to be my girlfriend and to go out with me. I don’t know if I have ever met a woman that was as forward and as ebullient as Bonnie was but, now I figured I just had.

Bonnie looked deep into my eyes with laughter in her eyes and said, “I don’t know if I could get used to being around you all the time, Nate, but, I sure think that we could have a really good time and a lot of fun trying.” I think she could see the bulge forming in my slacks.

I sure enjoyed her flirting with me and I decided to flirt right back with her. Well, Bonnie we’re just going to have to hang around together to find out aren’t we?” I said with a broad smile on my face. Bonnie just squeezed my hand again and wiggled a little closer to me in her seat.

About that time Flo called, “Bonnie, Nate, you two come in here and let’s have our supper. Make sure you bring your wine glass in with you, too.” Flo refilled our wine glasses and we ate our supper.

I could tell the wine was just beginning to get to Bonnie as she had gotten giggly and even cuter. Flo sat at one end of the dinner table and I sat at the other end where we usually did. I helped Bonnie into her chair at the side of the table between Flo and me.

When I lifted her into her chair she looked into my eyes with what appeared to me to be a bedroom look as she licked her lips and blew me a kiss. I took that as an implied gesture that she would like to have my dick in her mouth and she would like to suck the love cream right out of my dick. Licking her lips made the bulge in my slacks grow just a little bit bigger.

 
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