My name is Emily, I am 14. I have 3 sisters; Amy is 15, and I have two younger ones. I go a private girl’s school so I don't see many boys during school naturally but I do have many boys I am friendly with and see them quite often.
 
I guess we are reasonably liberal around our home in that nudity has never been a problem. We certainly don't all walk around naked but do see each other as we walk to the bathroom etc or have a spa. My parents have discussed sex education with all of us and have shown us a couple of sex education videos and books. We have seen them naked when they told us about our bodies.
 
I have been very self conscious about my body as I am a late developer and I am small. It has been awful to watch others at school and see them develop and not so me. I have no cunt hair yet and it's humiliating to have the other girls with their full bushes see me. My mother is small so I guess I am going to be small always.
 
I had not had all that much sexual experience until this year. Up until this happened I had seen one of my best friend's brother naked when she, me and he all showed each other our bodies. I was 13 and he was 14. There was no touching but we did open our legs up wide for him and then our cunts so as he could get a good look at us and he showed us his cock and balls.
 
When Mom and Dad gave us sex education they told us that it was us that would make the decision when we wanted to have sex. They told us that while it may be best to wait until we were older if we decided that it would be soon then it was ok with them. Mom did say that our first time should be special and that if at all possible it was her and Dads opinion that it would be best if an experienced guy was our first, as he would know what was he was doing and prepare us properly. She also took Amy and me to family planning where we had a discussion with a nurse educator about sex and contraceptives and had our first full medical with a doctor. That was both exciting and very embarrassing. I felt like a real woman but lying on my back, my legs spread being held in place by the stirrups, and having the Doctor REALLY look at me was an experience I could do without.
 
Ron is 38 and is a family friend; he is single and owns a business in our town. Both Amy and I work for him after school and on Saturdays when he needs us. He often has a meal at our home and is sort of like an uncle to us. We all like him because I guess he has always treated us like grown ups or at least after we were about age 12 he has. He's quite tall and we think he is ok looking, perhaps a little thin but that’s ok.

A few months ago, when both Amy and I were working with him, he told us we had both grown into great looking girls. It's the sort of thing that I liked to hear. It does embarrass me in a way but it is still neat to hear. About a week later when the 3 of us were having a break he must have guessed that I was little down and asked me what the problem was. We ended up having a really cool discussion where I told him things I had never told anyone else other then my sisters. We talked mainly about my size and how I wish I was bigger and I even told him how I was not developing like some of my friends. It was cool because he just sat and listened. Amy is also a little conscious about her size but she has developed more over the past few months so she doesn't really have that "little girl" look anymore. She was there also added some comments and again he just listened. I think the best part was that when he did talk to us he told us that he understood what we were saying, especially me, and that it was a difficult time for us. "Growing up is sometimes like that," he said. He didn't talk down to us which some adults are good at doing. He told us that in his opinion we both looked great and he would like to have us for girlfriends, which made me blush. He said things like he preferred smaller woman and that we were fine as far as he was concerned. It made me feel very good.

Afterwards both Amy and I talked about what he had said. I'm not really sure what we said. I guess little things like he was the first person to call us women and how we both felt how cool he was, as a guy. It wasn't one of those "Wow! He's hot!" type of conversations but we both said how much we liked him.

Nothing more happened that week. About a week later, as he was driving us home one afternoon, he just came straight out and told us that if there was ever anything we wanted to know about guys or about growing up, including sex then we only had to ask. He told us that he had had plenty of experience with young girls when he was younger and that he was sure he could help us if we needed him.

When we got home, Amy and I discussed what he had said. To be honest we didn't really know what he had meant. I remember we talked about whether or not he meant just having a talk or did he mean that he would teach us about guys and perhaps sex?

Two days later we decided to get up the courage and ask what he meant. When we arrived at his business we told him we wanted to know him what he meant by his statement. Both of us were really uptight about how we would ask him but Amy just came out and said, "When you told us you would tell us about growing up including sex what did you mean?" I almost died at her direct approach but we did want to know.

He said that it could include just talking about issues or, if we wanted, he would be ok with showing us about sex. I probably turned bright red. I recall I didn't know where to look and felt quite uneasy and yet also I feel it was what I wanted to hear. We had a little conversation and nothing more was said.

That night Amy and I talked about what we would do. We both decided that he was cool and that we should include him in our "education". Even then we didn't know what we wanted him to do but we were both comfortable with him.

The next day, after we had finished work, we told him that we wanted him to show us about guys. We really meant sex but neither of us knew how to put that. He said that we had made the right decision and that he would show us plenty. Again our conversation ended with nothing more being said.

The next day at school we were both wondering what we had let ourselves in for. I was actually shaking a little when we arrived at his business. He was real friendly and after a while I relaxed. When we stopped for a break we began talking resuming the conversation from yesterday. Both Amy and I found ourselves a little tongue tied and didn't quite know what to say so at first we just listened.

He said that we should discuss what we were going to do and how we should go about it. He told us that he was relaxed as to whether or not we both wanted to be with him at the same time or that he see us by ourselves. He also just came straight out and said that it was our decision as to whether or not we wanted to have him fuck us. He told us that when he was younger he had lived in a Nurses' hostel at a hospital and that he had "broken in" several young girls. He also told us how he would take care with us and how it was such a special event for a girl. Really he was saying everything I wanted him to say.

I said I might be more at ease if Amy was present and she agreed that all 3 of us should be together. He asked about contraception and we told him that we had started to take the pill about 6 weeks earlier, our nurse educator had told us it was best if we had 2 periods after first taking the pill and we had both had 2 periods with mine just finishing. I suppose we were both a bit naive on this subject, but he told us how he was std free and that if we were safe there was no reason why he shouldn't be condom free as it was important that a virgin feel a guys cock.

He then said that we all should all decide on where and when. He suggested that we go with him on a Saturday to his home. We thought that was a great idea the coming Saturday being the day. We thought the topic was done but he had a few other surprises for us.

He got up from his seat and asked Amy to stand up. She had no idea why but did as he asked. He took her, held her, and then kissed her hard on her lips. I was in awe! After a few minutes it was my turn and he kissed me and straight away he pushed his tongue into my mouth. I had been really worried about what I should do when I was first with a guy and how I would know when to do something but it just came naturally to me. After a little while I found that my tongue was in his mouth and it felt great to have a guy hold me and kiss me - everything I thought it would be.

He moved one of his hands to my tits and started to massage them through my uniform. Then his hand traveled down to my skirt and up under it. I was afraid but at the same time didn't want to stop him. He was sort of feeling my cunt through my panties. I knew that I was wet and he said that he could feel my wetness. I have to say it all felt so cool. It ended before I wanted it to.

What he said next was a huge surprise and a shock. He told us felt that it would be best if we told our mother about what was to happen to us. Both Amy and I gasped at the same time. We didn't know it then but he had joined our parents for sex on many occasions. He had talked to them about us girls and our mother and said that Ron was an ideal guy to fuck all of us. We did know that he sometimes stayed the night at our house and that our parents often visited his home but we certainly didn't know that they were all fucking together. Before we could question him about us talking to our mother about him he announced it was time to go back to work.

When Anna and I talked later about what Ron had said, we recalled that we were told that it was best for an experienced guy to be the first to fuck us. Later that night we decided to talk to our mother. We were very nervous but Ron had asked us to. She told us then that she and Ron had already talked. We both were surprised! She also revealed her "secret".

Once the initial shock was over, she continued. She was so supportive of our decision. She told us that Ron was very good at having sex and that she had been fucked many times by him. Her feeling was that he would show us much and would fuck us properly. She said that with a younger guy he might only think about getting his cock inside us. Often a younger guy would cum too early. With Ron, he would ensure that he prepared us well. She said when it came time for him to mount us he would not spare us but he would ensure that he took our hymens quickly and then give us a nice long fuck before he came.

On Saturday, we got up and our mother was fussing over us. She told us to have a nice long shower and to make sure we gave our cunts a good cleaning. Both Mom and Dad told us to have a great time and then Mom drove us to Ron's home. She talked to us all the way and telling us we would both be glad that we had been fucked and would enjoy sex for many years to come. Our knees were shaking when we arrived at Ron's. Mom said her goodbyes and then left.

Both of were nervous as we knocked on his front door. He answered the door we went into his kitchen where he had a coffee pot on and we all sat down and talked. It did allow us to relax and there was no talk about sex. After about 30 minutes he said we should start and he took us to his bedroom. He had a huge bed and it was a neat room. I must admit that I did think when I saw the bed that my mother had been on it and had been fucked by both Ron and Dad.
 
Ron told us we would take our time and there was no rush. He went over to Amy, held her, and kissed her as I watched. After a while I could see him moving his hands over her body and it did look cool. Soon he was touching her tits and he would say things like "Do you like that Amy?" She would answer, "Yes!"

It was exciting to watch them. I could feel that my cunt was getting wet, especially when he moved his hand down to between her legs and was feeling her cunt. After a while he moved to me. It did feel so neat when he kissed me and touched my tits and cunt. At first he was touching my cunt through my panties. I then felt him push his finger under my panties and for the first time I could feel his finger touch my cunt. He moved straight to my clit and was gently rubbing it and I couldn't get enough. He did this for about 15 minutes. I'd never been so hot. He then announced that it was time that we lost our clothes.

To be honest this was the part I was dreading. As I have already said I am so self conscious about my body. I was not looking forward to having a guy see me naked for the first time, even if we were being prepared to be fucked. Ron was so kind and said nice things the whole time he undressed me. He took his time as he pulled my t shirt off [I was not wearing a bra] and saw my tits. He touched them and bent down and kissed them and sucked on them. My nipples had become very hard. They are a little upturned and they seemed to get huge. He would say things like "They are beautiful!" and it did feel great when he touched them. I liked it when he gently flicked his finger on my actual nipples, it felt real good.

He then moved to my jeans. As he was undoing my jeans he got me to sit on a seat. He undid my sneakers, took them and my socks off and then told me to raise my bum. He slipped off both my jeans and panties in one go. I was now naked and he parted my legs and just looked at my cunt. His comments were like before. He kept saying how neat I looked and he couldn't understand what I was worrying about as my body looked great. He told me how many guys like their woman to be clean shaved and I shouldn't worry about having no cunt hair. He moved his hand up to my cunt and ran his fingers over it. He then pushed one finger inside me until he reached my hymen where he gently pushed against it before pulling out and again very gently rubbing my clit. It did feel so good and when I looked at my clit you could see that it had grown bigger. He began rubbing it faster and it felt even better. He stopped and said that he should pay some attention to Amy. I was disappointed but we had agreed to do this together.

He undid her blouse and then her bra and kissed and sucked on her tits before unbuttoning her skirt. As she stood there he pulled it down followed by her panties, for some reason he didn't take her sneakers off but I guess that it didn't matter. I think she looked fantastic, her tits are a little bigger then mine, her nipples are slightly upturned like mine [all of us have nipples like that including Mum] and her cunt had a thin covering of hair. He knelt down in front of her and parted her legs a little. Slowly he placed his finger up to her cunt and pushed into her a little until like me he reached her hymen. Now he was fingering her cunt like he had mine. At times he would ask if it was nice and Anna kept saying it was great, keep doing it. I was looking at what he was doing up close and you could see how wet her cunt was.
 
He stopped and told us it was time he stripped off. While he had been touching us I hadn't even thought of his cock. Over the past few days both Amy and I had talked about his cock and cocks in general. While we had seen Dads, his had never been hard and we had talked in general terms about what an erect cock would look like. Nothing really prepared us for what we saw when he took his pants off. His cock was huge or at least that is what we thought. Later on when we talked to Mom she told us that he did have a big cock. She said it was between 7" and 8" but measurements weren't what we were thinking about at the time.

Anyway back to what was happening. He stood there and his cock was standing out from his body and pointing upwards. There was a small amount of liquid seeping from it. He said we could touch it and I can remember thinking how hard it felt. Next he took Amy to the bed and they both laid on it as I watched from my chair. He held her and over about 20 minutes he kissed her, sucked and felt her tits, and at times placed his fingers to her cunt and felt her. Next he parted her legs wide and moved between them and started to lick her cunt. She was reacting by moving around and it did look like she was enjoying what he was doing to her. After he had spent a long time between her legs he told me to get up on the bed.

He began to do the same sort of thing to me as he had done to Amy. He sucking my tits and massaging them and I could feel his finger playing with my clit. It was feeling great but nothing prepared me for what it would be like when he parted my legs and for the first time I felt someone use their tongue on my cunt. It was magic and while it took a little time to get used to it I adored it. He would run his tongue right along my slit and then bury his tongue inside me before concentrating on my clit. Every so often when he was using his tongue to run along my slit he would actually go as far as my arsehole. I never knew that area was so sensitive. I could feel myself getting so wet. After about 20 minutes, I felt my body experience a tingling feeling. I developed goose bumps on my skin and I realized that I was having an orgasm!
 
Ron was now sitting up and said it was time for us to be mounted and broken in. He asked if we had any preference as to who would go first. I had thought it would be Amy as she was the oldest but when we didn't say anything. He said that since I was already spread in front of him he would do me first. I sort of wanted Amy to be the first one as I was still a little nervous.

He got two pillows and put them under my bum. They didn't really elevate me all that much but I was off the bed a little. He told me to spread my legs. He moved up in to place and suddenly I could feel his cock pressing against my cunt and then move in a little until he reached my hymen. There was an uncomfortable feeling as he pushed hard up my hymen but not what you would call pain. He pulled back a little and then I felt him press against my hymen again. Next he pulled out again and quite unexpectedly he thrust into me and ripped my hymen open. It was very painful and I screamed out. He comforted me and told me the worse was done. Slowly I could feel him pushing his cock deep inside me. I had mixed feelings, I was sore but the feeling as he pushed into me was nice. It's hard to explain but it felt like I was being stretched as he continued to push further inside me. When he was completely inside me he said we could stay like that and he told me to get use to the feeling of a cock inside me. For a while he remained motionless.

I felt him move and he slowly pulled out a little before he started a gentle thrusting in and out of me. It soon built up to hard thrusts as he fucked me hard. A couple of times he actually moved me up the bed with his thrusts. He started to move in and out of me gently and then give me 4 or 5 hard thrusts then back to gentle fucking followed by the hard fucking again. Even though I was sore it did feel good as he fucked me.

While most of the time I concentrated on looking at him, it was interesting to watch how much he was putting into mounting me. I did look a couple of times at Amy who was on the bed watching. She was staring at my cunt and his cock at work together. He fucked me for about 15 minutes and pulled out. It was a little off-putting to see my blood had stained the pillow. It was also on his cock. He went into his ensuite to clean his cock.

When he came out he told Amy it was her turn. He positioned her on the bed only this time he positioned her legs high up in the air. Then he moved over her and I could see his cock enter her cunt. He fucked her in a different way in that as soon as he was inside her and without any warning he gave a quick solid thrust and ripped her hymen. Like me she did cry out but he was soon right up her cunt and again after a short rest he started to fuck her in the same manner he fucked me. I liked it when he pushed her legs right back to her head and her whole cunt area was exposed to me as he fucked her hard. He started to say something like 'Yes, yes' and while we didn't know it until he told us he had just shot his semen inside Amy. He pulled out and his cock had traces of his cum on it along with her blood. After a while you could see his semen seep out of her cunt.

We had a rest for a while and he told us that he wanted to show us some different positions. I liked it when he got me on the bed on all fours and he mounted me from behind. I was holding on tight to the bed head as he fucked me. I also liked it when he got Amy to stand beside the bed and then bend over and grasp hold of the bedside drawers and again he mounted her from behind. He also got me to sit on another set of drawers and he positioned himself between my legs and pushed his cock into me and then placed his hands under my bum and lifted me deep on to his cock and walked a few steps holding me on his cock.

After we had finished we all had showers and Ron took us home. My cunt was so sore! I do feel that he was kind in his fucking of us. It did hurt when he penetrated me for the first time but I know that all girls have to be fucked for the first time. He did spend such a long time preparing us before he fucked us. We have both been fucked by him several times since and it feels so good when he enters me, I adore being fucked.