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First Time With My Sister

"I have my first sex with my older sister."

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7.0k words 7.0k words

Author's Notes

"Submitted 10/1"

Our family is a little unique.

My father is a mining engineer and spends two weeks on-site and one week at home. We live on a small acreage and when he is at home, he spends most of his daylight hours working around the property.

My mother is a Registered nurse. She has been working twelve-hour shifts following Covid.

I am seventeen. I have two sisters. Jan is twenty-one, and Sue is nineteen.

We have been nudists all our lives and maintain a property and venue for nudists to visit at weekends. There is a large outdoor pool, acres of grass and shady bushland which is remote and secluded.

The nudist club activities within the general area are always conducted with dignity and respect. Many members have children. Social activity is always undertaken in the spirit of family nudity and visible sexual behaviour is not tolerated and is controlled by the committee.

We also have a private homestead well away from the public area in which the family can enjoy themselves away from the other guests. There is an outdoor area, pool, gym and cabana where we can enjoy ourselves privately.

Dad and Mum have two very good friends, Dianne and Bill who have no children. They live on the property in another house and act as caretakers/managers and maintain and look after the main nudist area. As kids, we knew them as Uncle and Auntie. Now we address them by name.

Dad and mum together with Bill and Dianne occasionally engage in sexual intercourse openly and without any attempt to be private as they have done for as long as we can remember. We are aware of and have witnessed their intimacy all our lives and accept it as normal behaviour between them.  The facts have been discussed and explained to us. The three of us have never been approached to engage sexually with them.

To all of us, it is a family affair not to be discussed with others.

Our mother has always encouraged us to discuss sexual affairs openly and without reservation with her. There are no secrets, and the girls always contribute without embarrassment to any discussion when the subject is raised.

To my knowledge, no others in the nudist community are aware of our parent's intimate activities with Dianne and Bill.

…………….

Dad was away working, and mum was at the hospital. Jan was home from University and we were sitting by our pool talking. I mentioned that I had seen and heard her having sex with one of her boyfriends the day before. The sight of them both as he fucked her and her cries of joy had been rather arousing.

Jan laughed “He is one of the lecturers at Uni. There is something to be said about an ‘A’ for a lay. How long did you watch us?”

“Long enough.”

“Did we give you a good show?” she joked.

“You were doing it doggy; it was fascinating. I had to wank myself afterwards.”

“Have you ever tried it?” Jan asked.

“Sis, I have never even had sex with a girl yet. I thought you were aware of that.”

“I thought you were on with Claire.”

“I wish.”

“How would you like to have your first time with me then?”

I was stunned. “You are kidding. You would let me fuck you?”

“Believe me I am in the mood for something right now. I have had half a dozen guys before you, it’s only sex. I can hardly believe you haven’t done it with Claire yet.”

Claire has been my girlfriend since we were in junior school.

“That’s not for the lack of trying. I got close one night, but she said no. She is frightened of getting pregnant.”

“Hasn’t she heard of the pill? How old is she?”

“Sixteen, almost seventeen. Her mum says she is still too young.”

“Old enough,” Jan commented.

 I can't believe it; you are my sister. Isn't it wrong for families to fuck each other?”

“Not this family. Mum and dad don’t have any problems with Dianne and Bill,” Jan commented.

“They are not family.”

“Close enough.”  

“You ARE serious?” I questioned her again.

“I would not offer if I wasn’t. You are my little brother I would love to share your first time with you. I am more than happy to do it right here and now if you want to. I might not offer it again.”

“What if somebody comes home?”

“Mum is working, and dad is on-site. Sue is at a friend's place for a sleepover. There is nothing to worry about.”

“Shit I would love to, but I don’t know, that has come as a bit of a shock.”

“Come on, it will be your first time and doing it with an experienced woman will be far better than doing it with some girl frightened of getting pregnant.”

“I don’t believe this. What happens if I goof up and cum too quickly?”

“We will keep doing it until I am happy. It wouldn’t be the first time a guy premmied with me.”

 I laughed, “Maybe I should make sure I cum quickly.”

“Mike I am happy for you to have sex with me any time you feel like it. After this, all you will need to do is ask.”

“What will happen if mum and dad find out?”

“Nothing. He fucks Dianne. Bill fucks mum. They have been fucking each other all their lives. You know that. There are no secrets there.”

“Yes, but they are friends.”

Jan laughed, “As they say; Friends with Benefits.”

“That’s a wonderful way to put it. They sure don’t worry about us seeing them.”

“Bill was Mum's first lover, and then she met dad. Mum and I have talked about it often, particularly when I started having sex. I had a lot of questions. She helped me a lot.”

“She did the same with me, she found me masturbating one day and I was shocked. She just sat and we talked and she told me there was no shame in doing it, she does it herself. I was embarrassed but she treated it as normal.”

“A few months ago she told me Bill told her he would like to fuck me,  but mum said no.”

“How do you feel about that?”

“I wouldn’t mind him fucking me, the only disadvantage is he is almost three times my age. He has a great-looking cock. Mum still enjoys it with him. I am hoping one day mum will change her mind. I don’t think dad would mind.”

“He certainly is well hung; it's obvious mum likes it with him. They are at it often. I have seen her with dad too and she is a real goer.”

“Well do you want to with me?”

“God I can't believe this. My first time, and with my sister. I just hope I can do it well enough for you.”

“As I said, we can do it as often as you like. I enjoy it. Fucking is more than just cumming.”

I could not believe it; she had offered me my first fuck. I could not be happier.

“Come on big boy, let's get started. I can't remember the last time I let a guy fuck me for his first time. It must have been years ago.”

“When did you lose your virginity?”

“I was sixteen.”

“That must be the magic age. How about Sue, I wonder if she has yet?”

“Yes, she has already had a couple of boys. You never know you could get lucky.”

“Your joking, me fuck Sue, I don’t think she would let me near her.”

“You are going to fuck me; I can't see why she wouldn’t let you if she knows you and I have done it together.

“I won't be telling her.”

“I will. Sue, mum, and I don’t have any secrets. We have talked about sex a lot together. It doesn’t bother Sue when she sees dad with Dianne, or Bill is fucking mum.”

“Mum won't like us fucking each other as brother and sister. It is wrong. What they do together is not.”

“Come on help me get this lounge ready and move it into the shade. Doing it in the sun may get a bit hot.”

Jan and I rearranged the furniture and she put a towel over the mattress.

Jan and I had grown up as nudists. Naked flesh was not something that excited me … until then. I was going to fuck her. Just looking at her got me hard. Something that had never happened before. She has a great body with lovely firm tits. She had shaved the hair off her pussy, and it had the bloom of peach skin. I had never looked at her sexily before. Just seeing her bending over, showing all her beautiful sexy bits got my cock stiff.

“Come here, little brother,” she said as she held her arms open to hug me.

We hugged but we didn’t kiss. As I felt her bare skin pressed against mine and her breasts pressing against my chest. My cock oozed a bit of pre-cum.

“I can see it is all ready to go,” Jan commented. “I am going to enjoy this. I never thought I would ever be fucking my little brother.”

As we parted Jan had put her hand around my cock and milked it before licking the pre cum away. Then stood back and admired my cock.

“I have never seen you hard before. You are well endowed, just like dad. I am going to enjoy this. You are bigger than I thought.”  

“Would you fuck him?”

“I doubt it. If mum agrees to let Bill fuck me, he might ask. That will be an interesting conversation with her.”

Jan then lay down and prepared for me to fuck her.

“Is there anything you want to ask me before we start?”

“Can I cum in you? How about a condom?”

“And spoil your fun. No, there is no problem. I am on the pill.”

“I can't believe we are going to do this. I hope I don’t spoil it.”

“Just take your time, we have plenty of it.”

I then proceeded to get myself into position. Jan was laying back and I was going to fuck her in the usual way, missionary. I knew what I had to do. I have seen my parents and Dianne and Bill fucking all my life, so it is nothing I haven’t seen before.

I had never imagined it would be like this, with my sister. I always hoped it would be with Claire.

I looked down at her waiting for me to start. I saw a woman, not my sister with a perfect figure. She smiled and her blonde curly hair surrounded her head making her look like a Greek goddess. It was the way she was laying there with her knees up which displayed her vagina perfectly. I could not imagine a more perfect experience for the first time.

I was looking at Jan in a way I had never looked at her before. She looked stunning. Her all-over tan and firm breasts looked beautiful sitting up on her chest with her nipples hard and bright pink. Her legs were spread, and I could see her bare vagina slightly wet, and her lips spread wider than I had ever noticed them before. It was something I had previously taken for granted. I even noticed she had painted her toenails bright red. She looked stunning. I shivered with anticipation. I looked down at Jan and I panicked a bit, I thought I might cum just looking at her.

I then thought about the other nude women I had seen naked here at our place. Most of them seem to have changed their pubic shape. It was obvious some of the older ones had had breast implant surgery.

Mum and Dianne had a strip. Sue, I don’t think has changed the shape of hers but had trimmed it around the edges. I noticed on odd occasions it may have been a bit smaller than usual but still its natural shape.

Some of the teenage girls were called ‘White Pointers.’ Their breasts were white triangles like a shark's fin. They must have sun-tanned at the beach in a bikini. The ones with all-over tans looked far nicer.

Jan bought me back to my senses. ”Would you like to have a look inside me?” Jan asked.

Without me replying she said, “Use your fingers to spread my lips and you can see everything, not that there is much to see but at least you will know what it's like in there.”

I did as she told me and parted her labia revealing the wet pink flesh inside her. It wasn’t like a tunnel or anything I imagined. It was all wet and pink. She told me where to look to see where she pee’d from. She told me how to expose her clit and see what it looked like. I was fascinated.

“When you go with other girls you will know what it's like now, and not embarrass them by asking to look.”

I had been overawed by the whole situation, never had I even thought about sex like this.

I had seen Jan and the rest of my family naked for years but never considered having sex with any of them or any of the other women who I had seen here. Mum and Dad had entertained numerous friends here and everybody had been naked. Some had older teenage kids but only a few bought them with them. Kids had a habit of talking and they were not keen to be identified as nudists in public. Once the teenagers overcame the embarrassment following puberty and entered their late teens, they returned and enjoyed themselves. Sexual behaviour was rarely discussed.

I looked at Jan and saw the most beautiful woman I had ever seen. I began to panic. I was convinced I would stuff things up and cum too quickly for her.

My confidence waned and my previously hard, erect cock began to droop.

Jan realised I was having a few concerns.

“Let me hold it for a minute and settle you down. I can see you are a bit anxious.”

Jan took my cock in her hand and stroked it a couple of times and behold it stiffened up and she said, “There is another drop of pre-cum all ready for me. Just take your time,” as she licked it off her finger.

She lay back and made herself comfortable and I didn’t waste any more time I just leaned forward with my cock in my hand.

My cock was stiff and the head of it was all purple. I was ready and took myself in hand and prepared to guide it into her.

Jan replaced my hand with hers. Her long fingers on it felt wonderful. Then put the head of it in far enough to spread her lips.

“Steady … leave it there for a moment. Just leave the head of it in a bit until you get used to the feel of it in there.”

I did what she told me. I looked down and pushed my cock in until I could feel it in her just past the frenulum where the skin changes colour. It felt awesome. I could feel the warmth of her vagina surrounding it.

“That feels great when you are ready, put it in a bit further. Then wait for a moment and then go all the way in.”

The feeling had been amazing, and I have always remembered how she suggested I do it and have done it that way ever since.

“Oh God that feels awesome,” I exclaimed as I slid it into her another inch or so.

Jan smiled which filled me with confidence. She was happy.

This was not like anything I had imagined. I had never thought it would be with Jan or be like this. It was far better than I had ever believed possible.

I did as Jan told me, and slowly pushed my cock as far as I could into her.

The feeling of my entire cock surrounded by her warm wet vagina and not my hand gave me the most amazing feeling.

Once I was in as far as I could get it, she told me. “Just leave it there, don’t move, just get used to it being in me and the feeling of me all around it … relax.”

I felt relieved; I had been unconsciously holding my breath. I relaxed and lay on top of her.

It felt nice. We were both damp with sweat.

“That’s better, I can feel you and I like it, just relax and you will be all the better for it. Your heart is beating like mad. Once you get used to the feeling of it inside me you can begin to enjoy yourself. I am liking it already.”

“Geeze it feels amazing. It's nothing like I have ever imagined. This is heaven, thank you.”

“I am amazed it's your first time, you surprised me. You are doing great, just take your time, there is no rush. I don’t want you to cum too quickly. I want us to enjoy it as much as possible.”

I only rested for a minute as I was anxious to begin. I could feel my cock inside her and it lost a bit of its hardness, so I used my arms to support myself.

“Can I start?”

“Just take it slowly, to begin with, let's not rush it. I want you to last long enough for me to enjoy it as well.” 

I pulled my cock back until it was almost out of her and then went back in a bit faster than the first time. I did that a few times until I adjusted to the feeling of how far I had to move my cock inside her. I had lost the feeling I might cum. Jan didn’t say anything so I began to fuck her as I had seen dad and Bill fuck mum and Dianne. It all started to feel natural and I was doing everything right.

Dianne and mum both had wrapped their legs around them. I thought Jan will do that when she is ready.

The way Jan was directing me showed me I needed to know more than I did. One thing she did was to get me to move occasionally into a slightly different position. I was a bit concerned I might not be doing it right.

“How am I going, are you enjoying it?”...

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Written by Meggsy
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