(note: I am not the author. I have no intention of trying to plagiarize or take credit. When the real author, LesLara84, finally posts this story without any HTLM codes, I will delete this. I apologize for any harm or anything, I'm just doing this because this seems like a good story. I added limited spacing but did not change any grammar, punctuation or spelling.)
Vacation with my family
Hi everybody! I am Stephanie or just Steph like all my friends call me and this story is about the first sexual vacations with my family. But first of all let me introduce you to my family. There is my dad Peter, my mom Cynthia, my little brother Chris, my little sister Sarah and of course me.
For being 39 my dad is still a hot looking man. Being 6 feet and 1 inch (for metric readers: 1.86m) and having well shaped muscles he looks marvelous. But the best parts are his deep blue eyes and his short blonde hair.
My mom looks like being 25 although she is 36 and has a breathtaking body. Although she is rather short (5 feet 4 inches [metric: 1.63]) her legs are longer than everything. She is proud of having a nice firm round butt and really nice 36C boobs. She has an angelic face surrounded by straight long blonde hair and deep blue eyes.
Chris (15) is a younger version of his father and if you compare pictures of him and my father when he was 15 you can‘t see any differences.
Sarah and me are younger copies of our mother with only small differences. Sarah has curled blonde hair while mine is straight as well. For being only 13 Sarah has developed nice and firm 32A cups. She is a little smaller than me but an eyecatcher like our mom or me.
And last but not least it’s me, Steph. I am 16 but as developed as my mom having a 36C and her long legs. By only being 5 feet 'tall’ these beautiful firm tits are more noticeable than my mom‘s. But enough of us, our vacations waits...
It all started on the last school day before the summer-break. All of us were looking forward to our summer holidays at a sunny beachside. 3 weeks of laying in the sun, swimming, surfing and barbequing. What a paradise...
When the school bell rang the last time I sprang up and headed towards my car in no time. As usual I had to wait until Chris came out of the building followed by a whole bunch of girls. You have to know that every girl in his class and even girls form my class wanted to date him. He is in the football team and plays very well. Even his coach says that he will get a stipendium for university. Because of this and the fact that he is good looking and kind to every person, all girls want to date him.
After saying „good bye“ and „have nice holidays“ and a lot of hugging we finally drove off to Sarah’s school to get her as well.
When we arrived at home mom and dad had loaded dads truck with all our luggage so that we only had to take our stuff. Our parents waited until it was evening so that we did not get any trouble with traffic jams and we headed towards our beach-house.
During our long drive through the night we kids slept, heard music or relaxed until we arrived there in the afternoon. Chris, Sarah and me helped to get everything in and started to unpack our stuff. Mom and dad of course got the master’s bedroom, because Sarah and me had to share a bedroom we got second biggest and Chris got his own.
Sarah and I helped each other putting our stuff into the wardrobes when some little black thing dropped out of her luggage. I saw it only for some seconds because Sarah quickly picked it up and put it back while she got bright red.
“Sarah what was that?” -
“No... nothing special, only a ... a waterproof purse...”
“Oh come on Sarah, that didn’t look like that. More or less it looked like a little thing with which you can have much fun.” - “No Steph, it’s only a purse...”
“If this is a purse you can show me.”
Turning red again Sarah shook her head. “I don’t want to. It is ... it is...” -
“It’s O.K. Sarah I know that this isn’t a purse.”
Ashamed Sarah sat on the bed almost crying. I sat next to her putting my arms around her.
“Sarah everything is fine. I don’t want to have this little pocket rocket back. Take it as a little gift. I don’t want to see my little sister ashamed or crying so stop it, please. There is nothing bad about using such devices, it absolutely normal.”
Sarah looked at me “Really? You are not mad that I stole it from you? I... I just wanted to try out but I had not the heart to do so. Do you really think this is normal?”
“Of course. It is not evil and you are no pervert to do that, it is completely normal and one of the best things in the world. Trust me you will love it!”
“Steph, when did you start to play with yourself?”
“I discovered this pleasure when I was 12 while I was showering... This warm water and the massage of the water-streams... it was amazing. Since there I started to masturbate.”
Sarah watched me shocked. “Shhhh... don’t call it this way. Mom and dad could possibly hear us!”
“But that’s how it is called... Masturbation. But if you feel better with ‘pumping the pussy’, ‘fingering’, ‘jill off’ or ‘beating the bean’ I will call it that way.”, I smiled.
She once again turned bright red: “Stop it, please! Call it ‘masturbate’ but please don’t use the others again, O.K.?”
“As you wish, my little prudish sis. By the way when did you start to ‘masturbate’?”
“I think I started with it when I was 12. My friends told me that they have done it and that they liked it. The only topic they chatted was 'playing’ and I wanted to chat with them as well. At first it was strange but after some practice it got better and better.”
“Sarah, please be honest. Have you ever tried some objects or did you always use your fingers?”
“Well... at the beginning I only used my fingers. Some month ago my friends started to speak about the objects they sometimes use. They spoke about candles and even some vegetables and I was shocked. On the other hand I wanted to know how it feels but even after days and weeks of thinking I had no idea until I remembered your little pocket rocket. That was two weeks ago but until now I was too frightened to try it.”
“One last thing I would like to know, after that you can ask whatever you want. Did you ever had an orgasm?”
“I don’t know, how does it feel? Is it good?”
“Oh yes, it is the best feeling in the world. But I think that you had none until now otherwise you would know what I mean. But I think you will soon feel it. So now do you want to know something?”
“Is it really no problem for you that I stole your pocket rocket? I mean you couldn’t use it...”
“No, since I started to use that toy I bought some others so it is not a problem.”
Sarah got big eyes by her surprise. “You have more than that thing? What is it? How does it look? Is it ‘good’?”
“Slow down a bit little Miss Masturbation. And yes, I have more than that one. At least I have four more. Two of them are vibrators and the other two are normal dildos. Both vibrators look like the pocket rocket you have but are bigger. One of the dildos looks like a real penis with the head and even balls and the other one looks like the vibrators but without the vibration. And another time ‘Yes’ they are really good.”
Sarah’s mouth dropped down as she heard about my little collection. She even did not say anything to the name I given her.
“Do you have one with you? I would like to see it.” -
“Of course I have two of them here. One vibrator and one dildo but I don’t show them to you now. You have to wait until tonight.”
“Please! Show them to me now.”
“Sorry for that sis but you have to wait and maybe you will get a bit excited. We have to unpack our stuff and after that I want to go to the beach. You can come with me and maybe we will continue our little chat.”
After some minutes in which Sarah tried to convince me to show the toys to her we continued our work. We finished everything and got ready for the beach but mom told us that lunch would be ready soon so we changed our plans and went to our Jacuzzi. Sarah wore a nice black swimsuit and I chose a light blue monokini. As soon we got in, Sarah started to chat again.
We chatted at least for one hour about masturbation, toys and other fun until our mom called us in so we dried us and went in. After dinner mom and dad had to go shopping because they realized they forgot most of our food and Chris went out to the beach for some surfing. As soon Sarah and I were alone she came to me asking if she could see them finally.
“Sarah calm down. This isn’t a big thing. I will show you my toys but you have to promise one thing. You will not tell anybody anything about this. Is that OK for you?”
“I swear that I will not tell anybody anything.”
“Good little Miss Masturbation.”, I smiled. “Now come with me.”
We went to our room and Sarah sat on the bed while I picked my backpack and took out my toys. “Here they are.” I laid them onto the bed and Sarah almost collapsed.
“Ohhh... my... gosh... These ones are soooo huge... Actually I was afraid to try your little pocket rocket but seeing these giants I’m really afraid.”
“Oh little baby sis, there’s nothing to be afraid off. They are bigger than yours but they are average-sized. They are only 8 inches long and 2 inches thick. There are even bigger and longer ones available.”
“Really? Doesn’t it hurt as hell? When I masturbate I sometimes put my finger into me and at the beginning it hurt. Now it doesn’t hurt anymore but it feels so tight. I can’t imagine how this should fit in.”
“You are right Sarah. It is tight but after some practicing your pussy is stretched enough so that you can put these into you. It doesn’t hurt but gives you the best feeling on earth.”
“Steph, as long as you don’t prove this I can’t believe you.”
“What? Are you kidding Sarah? I will not ram that dildo into my pussy as long you are watching.”
“But you could possibly show me how I have to do that. If I watch you do it my fear will be gone and I will try it as well. And by the way, didn’t you tell me that this is the most natural thing in the world? Why would you be so cruel not to share your knowledge and techniques with your little sister?”
“You won. I will give you a little show but you have to do one thing. You have to turn me on a bit by fingering your little pussy in front of me. Just close your eyes imagine you are alone in your room and you want it.”
Sarah got bright red: “I... I’m not sure if I can do that. It is difficult while you are watching me.”
“For me it’s as difficult as for you plus I will use my little purple friend.” ,with that I raised the purple dildo.
“Fine, I will try it.”
Sarah lay back on the bed, closed her eyes and started to slide her fingers over her breasts. In no time I could see her hard nipples poke through her swimsuit. Her left hand started to caress them while her other hand ran down her belly and landed on her crotch. With two fingers she started to pinch her nipples. Her breathing became flatter when her fingertips met her slit and started to massage it. She shoves the material of her swimsuit into it and I could see my sisters beautiful camel toe the first time. After some minutes of doing so her fingers reached under the fabric and pulled it away. Her wonderful naked pussy appeared and she dug her fingers deep between her outer lips.
Within seconds I noticed that I was getting wet as hell and I immediately pulled away the fabric of my monokini and started finger-fucking me. After some more minutes Sarah finally pushed one finger into her lovely fucking hole which gave me another kick. I entered my dripping pussy with two more fingers and stretched it more. I grabbed my dildo, shove it into my mouth and sucked it a bit. Then I noticed Sarah looking at me with her finger still inside.
“Now the important part will start.” , I said and lined up the head of the dildo with my pussy.
“I will show you how it will not hurt.”
With that I started rubbing the head up and down my slit a few times. “When your toy is wet enough you can start to penetrate yourself but always start slow.”
I slowly shove half of the head into me and pulled it out slowly again. “You can repeat it as often as you wish and then shove in more and more. But be sure that it doesn’t hurt.”
I repeated it three times and then pushed the cock deeper into my waiting slit. “Push as deep as you like and pull it then almost out again. Do so at what speed you like. That’s it.”
I ended my explanations and started to pump my pussy deeper and quicker. I used more and more speed and power until my hand started to clap against my pussy producing smacking sounds. This kind of fucking I like most, hard, deep and with high speed.
I recognized that Sarah now used two fingers to fuck her pussy which sent a thrill through my whole body. With my free hand I started pinching my nipples and soon felt a rising pressure inside my fuck hole. My breath speeded up and suddenly there was the edge. I pumped my raging pussy with two more almost violent strokes and started cumming.
My legs started to spasm I screamed and my pussy started spraying. Wave after wave of ecstasy shot through me while my body buckled up and down. When my orgasm started to subside I looked to Sarah. She had stopped masturbating and watched me shocked.
“Steph? Are you alright? Did you hurt yourself?”
“Everything’s OK. Hui... that was an amazing orgasm... One of the best I had until now. Maybe because I could watch your finger fucking your little pussy. And no, I did not hurt myself. Sometimes it looks like pain but this was pure pleasure, believe me.”
Still a bit worried Sarah looked at me. “Will this happen to me as well?”
“I hope so. As I said this is one of the best feelings you can feel and I promise you that you will love it.”
“Steph? When you started to go crazy I stopped and now I need a little relief. Could you please give me the little rocket? It is in my backpack in the last pocket.”
“Of course lil baby sis. Can I watch? It makes my so fucking horny...”
I tried to walk over to Sarah’s backpack but had to hold me somewhere several times until my legs stopped to shake.
“Sure. You can watch. I saw you and it would be bitchy not letting you.”
“You are soo sweet.”
Finally I got her bag and found her little vibrator. “Sarah I have a better idea. Please don’t freak out but why you don’t let me play with you a bit? I know exactly what is good and what not.”
Once again Sarah looked at me with a worried face. “I... I don’t know... isn’t this illegal? I mean isn’t this incest or something like that?”
“No, of course not. Incest would be if Chris or dad would fuck you or me. This is more like best girlfriends exploring each other’s body. Playing a bit, training kissing and so on. We can’t get each other’s pregnant so it is not incest.”
“Sounds logical... OK if you want you can masturbate me but please, be kind.”
“I will but this is not called ‘masturbate you’ but ‘fuck you’. It is only called ‘masturbation’ if you play with yourself.”
“Steph, please be kind while you ‘fuck’ me.”
“I will, lil baby sis, I will. Just relax, lay down and enjoy it.”
With that I bent over her body and pressed a soft kiss onto her nipple. With my hands I started to tease her other nipple.
A soft moan left Sarah’s mouth.
My other hand slowly moved down her belly and stopped at the beginning of her public hair. “You should start to shave your little pussy. A bald shaved pussy is far more attractive than a hairy one. If you don’t know how you shave down there, I will show it to you.”
With that I began to tongue her nipple while her other one was a bit twisted and pinched. Her moanings got louder as my fingertips reached her magic knob and started to play with it. Drawing circles around it got it warder and bigger until I thought it would be perfect.
“If you like playing with your nipples please do so I have to concentrate on another important part of your body.”
In no time her hands started to pinch and twist her nipples even harder than I did while my now free hand started to massage her outer lips and slit. Her moans got even louder as my fingertip penetrated her hole. Slowly I shove my finger deeper into her while my other fingers massaged her clit. I have to say that that pussy was tight as hell but after some more minutes of finger fucking and stretching I could shove in another one. Without stopping my finger fuck I positioned myself between her legs so that I could see her pussy clearly. Sarah had her eyes closed so I decided I would do some unexpected. I stopped the clit massage and gave her a big lick right there.
Her eyes shot open and at first I thought she would kill me for that but all she said was “Do it again!”
That was all I wanted to hear so I started to tongue her clit more and more. My best girlfriend taught me how to eat out a pussy in the best way by writing the alphabet with your tongue over the clit and that was what I did.
Sarah started almost screaming when I reached ‘H’ but then I played my last ace. I turned my fingers in her hole and searched her g-spot. I found this soft and spongy area and immediately started to finger fuck and massage it.
This drove Sarah over the edge and she felt her first orgasm. She started to scream and moan uncontrollable, her legs spasmed and her eyes rolled back while a huge amount of cum shot out of her pussy and all over my fingers and face.
I was happy that my lil sis finally had her first orgasm. In that moment I realized that someone was standing in the open door watching us.
to be continued...