This story has been written from what I have been told to me by a very close (and intimate) friend- it was her first experience and I have used her story and written it in the first person as she related it to me – we are now bi-sexual and share sexual experiences together quite often. I may write something about how we started one day.

The first time I had sex was just after I turned 16. I had always been interested in sex but never game enough to go the whole way. I learned how to masturbate when I was 12 and did that a lot. I had a few opportunities to sleep with a couple of boys but I always chickened out at the last minute.
My best friend and I had two boyfriends and they both wanted to fuck us and we always said we would let them ‘one day’ and they always said ‘soon we hope’.. We had often got nude with them and we had let them play with our tits and finger us and we had masturbated them. Once I had actually put Tony’s cock head in my mouth for a moment but pulled it out after a few seconds – I was scared about doing that too.
On this particular day we were all in our secret place in a bushland clearing where we all ran round in the nude with our boyfriends Tony and Mike, who we had known for a few weeks. They were great and whenever we were all together they always teased us about wanting to be fucked but we always said one day soon, they lived in hope. This didn't stop us fooling around and feeling each other up and we often jacked them off. We had always said no but Jan had told me the day before she was getting gamer and she said I am going to do it with Mike probably tomorrow. I cant delay it any longer I really want to. Jan said if I do it will you let Tony do it with you.. I was a bit hesitant but said yes.
While we were playing about Mike said to Jan is it going to be today – will you fuck me. Jan said yes immediately – today is the day. Jan said to me don’t forget you said you would too. I wanted to but still wasn’t sure and said I would after I saw them do it. It was going to be our first time. Jan said straight away she wanted to do it right then. I asked if we could watch them and Jan said only if you promise to do it and we can watch too. We all agreed we would watch each other and she got down for him to fuck her. Tony and I held hands and stood there ready to watch and he said I am so happy you and I are going to make love together too. I looked him in the eye and said me too. Just looking at her laying there waiting for him to put his cock in to her cunt really got me excited and I almost lay down next to her and do it together with them. She looked so happy and really wanted to be fucked.
Watching them get ready I still wasn’t sure I could go through with it – I wanted to but I had this funny feeling in my tummy and was a bit frightened about getting pregnant and I would chicken out again. I was holding his hand and he said – you are still not sure are you?
I said I promised so I will – I will be ok.
He said I am glad we will be a while I cant get my cock hard enough, even though he was playing with it with his hand stroking it to get it up. I thought he was a bit frightened too but he said it was because he had cum a few minutes before when I jacked him off. He told me quietly that he wasn’t sure he could do it.
I said lets wait – I am sure we will be ok.
Lets wait till they have done it, he said and that made me fell better. I had a feeling he wanted it to be really good and he wasn’t sure it would be if we rushed it.
Jan was ready and Mike has this really great looking hard cock sticking up all ready for her. He got down and we watched her pull her legs back. She looked beautiful laying there with her legs spread apart and her vagina had her fair hair all showing, she was smiling and I was sure she really wanted to enjoy herself. Mike got down and lent down and gave her a quick kiss right on her cunt then got between them and he put his cock into her cunt and pushed it straight in. They both wanted it and they couldn’t wait.
She let out this cry of pain and said…… Ohhh shit…..she started to cry. Obviously his cock had hurt her. She screamed at him to take his cock out of her. We were watching and saw it all happen and then we saw blood all around her cunt. When he took his cock out his was all covered in blood too. When I saw what had happened I said no way to my Tony- I am not going to do it.
Jan sat up and I got down and cuddled her. It felt strange with me cuddling another girl when we were both naked. I was hugging her while she cried and said I really really wanted to but it hurts so much. Even I had tears in my eyes, I really felt sorry for her as she wanted it to be good. We held each other and cuddled together and after about five minutes she stopped crying said it was feeling better and stood up. The bleeding had stopped- but there wasn’t much blood anyhow and it was just around the lips of her vagina. She went to Mike and said she was soooo sorry, he said don’t worry we will do it again one day, I will wait till you are ready.
She asked me to look at her vagina and see where she was bleeding. She lay down and spread her legs open and I opened her vagina with my fingers and looked in her and couldn’t see where the blood had come from. Mike bought over a bottle of water and she lay down and I washed her vagina and still couldn’t see where she had bled from. She was all clean and wet inside her vagina and it actually looked nice. I was curious as I had never seen inside myself or any other girl. After I had washed her vagina she said she felt better and it wasn’t hurting anymore and said she wanted to try again. We all talked about it and Tony said he thought all girls bleed the first time a girl had sex. I said it was something to do with being a virgin.
She said he had to be gentle and put his cock in gently. He had rushed it the first time and if she hurt again or started to bleed he had to stop. He said he was sorry and he wouldn’t go in so fast this time. She said ok but was still a bit worried. He was happy to do that and seeing he had pushed his cock in so hard the first time he said he would go into her slowly and gently but thought it would be ok this time.
Then they both got down again and he put his cock just inside her, then she said for him to put it into her a bit further. He went in a bit and she said it was feeling ok but she was still a bit sore and to wait a minute. After a few seconds she said to go a bit further in and his cock went in really easily and she said it was still a bit tender and she could feel it, but it wasn’t as bad as the first time and she said just do it slowly until I get used to it. Mike put his cock in as far as it would go and he was right up inside her and he just lay on top of her for a minute. She said it felt much better and he could start.
He began to fuck her slowly and we watched and it was awesome watching him on top of her and her legs right back on his shoulders, I thought that looks good I wan to do that. Then we watched him slip his cock up and down inside her and after a few minutes she said that it was now feeling really good. Jan said this what I had hoped it would feel like. Tony started to masturbate himself and I played with my nipples which were really touchy and it felt great playing with them. We watched Mike fuck her for about 7 or 8 minutes and he said he was going to cum. Jan said please don’t cum inside me so he took his cock out and finished himself off by hand and when he came he spurted his cum all over her tummy and cunt hair. We all laughed at her laying there covered in his cum. She didn't mind and played with it and got some on her finger and rubbed it on her nipples.
She said now she was happy – she had done it and felt really good and actually liked it.
Then Tony said he was ready and could we do the same. I knew I really wanted to this time and said yes. I said I would let him fuck me but he couldnt cum inside me and he could do what Mike did and wank himself off on me. He said I would do anything I asked – he just wanted to make love to me. That made me feel good.
He was standing up slowly stroking his nice big hard cock to keep it hard and his cock looked wonderful. As I got down I was so close to him and something inside me got me all excited and without saying a word put his cock into my mouth. He was surprised and Jan and Mike just looked and Mike said shit – look at them – Wow. How is it. Tony said fucking fantastic. Tony was loving it and the other two were watching and talking and telling me what to do and I could not believe that I was actually doing it, having his cock in my mouth and actually enjoying the feeling of actually sucking it. The feeling of it in my mouth was really nice. I did what I thought was the way to do it and sucked pretty hard but my cheeks got sore so I just slipped my lips up and down and I asked him what should I do. The three of them were telling me to do this and that and he was loving whatever I did and telling me he loved me and I was the best cock sucker on earth. I felt really good. After a while Mike and Jan decide they would do it too and the two boys were standing up with Jan and I kneeling between their legs sucking them like mad and having some really great fun in the process. At one stage Jan asked me if I wanted to swap and see if Mike tasted any different.
I said only for a minute so we swapped and sucked their cocks for a few minutes and it didn't feel much different. Then we went back to our own guys. Tony whispered I like you better.
I was sooooo happy.
I was sucking his cock and doing what he wanted and what I thought he would like for another five minutes or so and then he said quick I have to take it out – I am going to cum – and went to pull back. I don’t know why – possibly because I was so worked up and I hadn’t really thought about it but I hung onto it and he came in my mouth. Why I did it I have no idea. He moaned once or twice as he spurted and was obviously enjoying what he was doing. I had no idea what it would be like but he spurted a couple of spurts into my mouth and I could feel his warm slimy cum on my tongue and as I sucked more out it filled my mouth up and I had to swallow it. The other two stopped sucking and watched him cum in my mouth and what I was doing. Some had leaked out the edge of my mouth and was running down my chin and dripped onto my tit.
I had swallowed one lot and was about to swallow the next lot and Jan said what is it like – believe it or not – I hadnt really thought about it – it was warm and slimy but it was only then I thought about the taste of it, I was enjoying the sensation of his cock in my mouth and the fact he was cumming. It had a strange taste not bitter or anything a bit salty perhaps or a taste like vinegar – I wasn’t sure but I didnt really like it or dislike it – it was something I would have to think about.
After I had sucked him dry I took his cock out of my mouth and licked my lips and then began to think about the taste of his semen.
I said to Jan that was amazing – I never realised what sucking a guys cock would be like but I really enjoyed it.
She said what was the taste like – this was the second time she had asked me.
I still had the taste of him in my mouth and then thought about it. I said it was ok – not brilliant but it had a strange taste unlike anything I could liken it too but it didn't have a bad taste – just unusual.
She said would you do it again.
I said for sure – I really had fun with having his hard cock in there and the cum is ok.
Then Mike said to Tony – have you ever tasted your own.
He blushed and said once – I jacked off and lay on the floor with my feet over my head and when I came it spurted everywhere but I got some in my mouth, it tasted weird.
Mike laughed and said I have done the same thing – I cant say I liked it either.
Tony said neither did I – I came into my hand once and tried to swallow some but I couldn’t bring myself to do it.
Mike said shit I have done the same thing but I got it down and I could taste it for ages.
Then Jan said have either of you tasted a girl.
They both said no.
Jan said well we have something to learn don’t we.
Then Tony said to me – are we going to do it that way first or do you want to fuck first.
I said seeing Jan and Mike have done it – I think we should do it too then we can work out what to do next.
He said do you want to do it now.
I said why not – I hadn’t thought about it but I was feeling better about it and then said – come on lets do it.
I got down and Tony got ready and Jan and Mike went back to cock sucking.
In between sucking him they watched us as we were almost ready for Tony to fuck me.
Jan said what happens if it hurts you too –
I said we can do the same – he can pull out and try again later.
Tony was ready and pushed my legs right back and onto his shoulders and then put his cock head against the lips of my vagina opening.
Jan said take it easy – don’t go in too fast – thats what happened to us.
Tony said are you ready.
I said I cant wait – do it.
He pushed his cock into me slowly and it went in without any problem. I could feel the thickness of his cock going in and spreading the lips of my vagina.
He said god it feels good.
He was going further and further into me taking it slowly, and I wasn’t having any pain at all – it was fine.
Jan said by now I was screaming – it was really hurting.
I said it feels great – I love it.
Tony said so do I – she is so wet and warm in there – I cant believe it feels this good.
Jan said isn’t it hurting you at all.
I said no – I cant believe how good it feels. I don’t know what I have been worrying about I could do this forever.
Tony then began to fuck me slowly and as he did I began to really enjoy the feeling even more and Jan and Mike were saying shit why did Jan hurt and bleed.
Jan said are you sure this is the first time you have done it.
I said positive – but I have been masturbating and putting things inside me for years maybe that has made a difference.
Jan got down close to where Tony had his cock inside me and said there is no blood.
I said probably thats what happened a couple of years ago – I slipped while riding my bike and hurt myself on the saddle and I bled from my vagina then – come to think of it it was a bit like you – not a lot of blood – nothing like a period. When I told my mother she said – it is ok it I will explain what has happened when you are a bit older – I guess she hasn’t considered that I would be having sex at this age.
Tony was concentrating on fucking me and enjoying himself and at the same time I was getting into the swing of it and I was moving around a bit to get the feeling of his cock where it felt good at my opening and also inside me. He had been fucking me for about 5 minutes when I felt the same sensation as when I was about to cum when I masturbate.
I said shit I think I am going to cum – go a bit faster and he did and the sensation really came upon me and I said go –go – go and then the sensation of the orgasm began to overwhelm me and I was having a really great orgasm and cumming really hard. I felt completely different to the orgasm I have when I masturbate – his cock was doing all the stimulation and it was a bit like when he had fingered me off a couple of times only better. I was laying down and my legs were right back and his cock was really rubbing on my clit and giving me the most wonderful feeling – I was grunting and moaning as he continued to fuck me and I was making the feeling in my clit make my orgasm last as long as I could. I was pulling on my nipples as well to make it better. This had to be the best orgasm I could remember ever having.
Jan watched as I went through the ecstasy of my orgasm and she said you lucky bastard – cumming and getting fucked. I have got to do that – it looked fantastic.
I said it was believe me – it was the best.
Tony looked into my eyes as I was smiling with the satisfaction of having one of the best orgasms I have ever had. While it was happening I was screwing my face up during my orgasm and I had nothing on my mind other than enjoying the wonderful sensation.
As he looked into my eyes he mouthed the word – ‘I love you’. I had this warm feeling inside me – he was making love to me, I could feel his wonderful big hard cock stimulating my insides – it really felt good. I had responded by showing him how much I loved the sensation of him on top of me and his penis inside of me and the feeling of his beautiful cock slipping up and down inside me – – already I had an orgasm and I was so happy. I must be pretty tight in there because I could tell how thick his cock is and the feeling of him moving it inside me.
He started to go a bit harder I thought to try and finish himself off and as he did my tits began to shake just a bit, they are still pretty tiny but big enough just to move a bit. We could hear a slapping noise as he went into me hard and his pelvis was bashing into mine. It felt and sounded great. I held onto my nipples again to make them feel better. As I did it felt better inside my tummy where I had tightened up the muscles to also make it feel good as well. Getting fucked is the most amazing sensation- we were going to do this a lot more now that we knew how good it was.
Jan and Mike heard us both grunting a bit and stopped kissing and both started to watch us. Then Tony started to go really hard and fast and then quickly slowed down with this funny look on his face. I could feel him sort of squeezing the cheeks of his ass together as he was fucking me. Then he started making grunting sounds and he was obviously really enjoying fucking me, as much as I was enjoying being fucked. I looked up at his face and I could see he was a bit like me and screwing up his face. I said hey are you going to cum and Tony sort of grunted yeeeessss.
I said quick take it out before you do – but he left it too late and a lot of his cum went inside me and as he was pulling his cock out of my cunt it was still spurting out of his cock and went all over my hair and legs.
I said ohhhh shit – did it go in me.
He was panting and shaking – then he said and said I am so sorry, I came just a bit in you – I thought I could get it out in time — I am really sorry, ohhh shit what have I done.
Mike and Jan said fuck what do we do now….. what if she gets pregnant.
I said – It wont happen – I am sure it wont happen – I had no idea but I didn't want to even think about it.
I sat up and there wasn’t much cum that I could see around my slit – it was more on my hair and legs. I said it looks ok.
He said no I did some in there – I know I could feel it spurting out in there – oohhh shit I am sorry.
I said lets not worry about it – I was bit worried but I knew that you didn't get pregnant every time you fucked. We had started sex-ed at school and I had a feeling the teacher had mentioned something about safe days and fertile days on your monthly period cycle. I said look lets not worry now – I will look I up on the internet when I get home I have an address about getting pregnant.
Jan said how cum much is in there.
Tony said a bit, like one spurt maybe two. I usually spurt four or five times when I wank off so it wouldn’t be a lot.
Mike said what happens if you are pregnant.
I said well lets face that when the time comes.
Jan said when is your period due.
I said next week – Wednesday if its on time.
God she said – I hope you aren’t.
Tony said so am I – I will marry you if you are.
I said I don’t think that will happen – I am sure if I am pregnant my mother will get me aborted – she has had one herself. I heard her telling my auntie she got pregnant to a guy she met on a cruise after dad died and she had it aborted. I am sure she will do it for me as well. At least I know my mom and I will have something in common.
Hell said Tony – I hope it doesn’t come to that – my parents will kill me if they know I got you pregnant.
I said lets not worry – if I am pregnant we will deal with it then, I just hope I am not. There is no reason for them to know – IF I am. I wont be telling them and I am sure my mom wont either if I ask her if I ask her. For now I just want to remember how good my first time was and how much I love Tony. Any how I will know next week if my period doesn’t come and I will start working out what I will do then. You will all be told .
After that the four of us sat down and talked about what we had done and how much fun our first time having real sex was. We all forgot for the moment I had a cunt full of cum. We all agreed it was the best day of our lives – Jan and I said we would not want to change a thing we did. Jan said I still don’t know what cum tastes like. Mike said I can fix that and we all laughed.
Tony said shit I am sorry – I never meant to do it in you.
I said forget it- I am not worrying.
We talked about what we were going to do from here on and I said I would be fucking and sucking Tony as often as possible from here on – he was wonderful and I love him. I could not have wished for a better start to my real sex life. Jan and I talked about how we could both get the oral contraception pill. I said I was pretty sure my mom would help me.
Jan said she would have to work it out – her mother would never forgive her if she knew she was being fucked at her age.
Tony said to me you wont tell your mom what we are doing will you.
I said if I have to I will, but even if I do I don’t think she will be too upset. I think she will respect the fact I am honest with her.
Tony said will you tell her its me.
I said sure – I am not ashamed to admit you and I like each other a lot and I respect, trust, and even love you, and I made up my mind that I wanted to do it with you and nobody else. She will be a bit upset at my age but I know she wont blame you and I will make sure she knows it was my decision to do it.
Jan said she was happy too and loved Mike. She said my next ambition is to have an orgasm while Mike is fucking me, and to taste his cum. Watching you was awesome. Then she said I only wish my parents were as understanding as yours – I think my father would go berserk if he knew what we did today.
Mike said god never tell him it was me.
She said I am like Sue – I am not ashamed of you or what we did. I could have said no – but I didn't and I am so proud of what we did.
I said how about we all do it again and then we will have to go – its getting late.
Jan said she wanted to suck Mike and they did that and she found out what it was like to have him cum in her mouth and taste cum. Like me she was not overwhelmed by the taste of his semen but loved the sucking of his cock. She said that she was still sore inside and she wanted to wait for a day before trying to fuck again.
Tony said he wanted to suck my cunt but when I reminded him it had his cum in it he said no – and we fucked again and while I didn't cum he did but this time he took his cock out of me and spurted it all over me. I joked that he now had to lick it off me – but he said some other time – he was still worried about me being pregnant. I thought about sucking his cock again but it was covered in my cunt juice and while I lick my fingers sometimes when I masturbate – it didn't turn me on to suck it off his cock – there was a lot more on his cock than I ever had on my fingers.
Afterwards we all got dressed and kissed for ages. Both Jan and I kept telling Mike and Tony how much we loved them and they told us too. Leaving Tony to go home that day was the hardest thing I had done – he had made me a real woman and I loved him.
My period arrived right on time so I rang Tony and tell him I wasn’t pregnant and he was overjoyed.
When I rang Jan they were together and she was actually sucking Mike and they were both happy for me as well.
They had tried to fuck again the day after the first time, this time at Jans place and Jan was fine. He rang me immediately they did it and again after the second time they did it and she had cum while he was fucking her. We were equal now.They had fucked each other every day since then like us. We had all gone down to the bushland on Sunday and had an orgy and we sucked and fucked each other at least four times. We even did it different ways.
Tony and Mike had both bought some condoms to use when they fucked us and we used them all the time. We didnt want another scare. I wanted to tell my mom that I was having sex but could not find a way of doing it, and I had a feeling she was suspicious of us . One afternoon Tony and I were in my bedroom we had just had a good fuck and we were laying there naked when my mother walked in on us. He had taken the condom off and it was on my bedside table and I am sure she knew what we had been doing and waited until we had finished before she came in.
She told us to clean up and get dressed and come down stairs. She didn't seem very happy about finding us like that. Tony nearly shit himself but I was pretty cool about it – I knew my mom would understand – but probably not be too happy about me doing it at my age. When we got there she had made coffee for us and there was cake on the table. She had obviously cooled down.
At first she was not happy and gave us both a bit of a lecture about having sex at our age and the consequences of somebody finding out as we were both too young in the eyes of the law to be doing it. We didn't say much and did not argue with her. At no time did she tell us we couldn’t do it together any more. Then she changed and was her normal happy self and I think she was happy she knew that we knew what we were doing safely. I am happy that you are not taking risks. She told us she had suspected we were having sex for a while. She, like me, was trying to work out a way of discussing it with us and said I was happy to see that condom in your room – I am glad you are taking precautions.. She realised then we were telling the truth about having safe sex. We all talked together for about half an hour about the two of us and we all laughed when I told her about Tony cumming in me accidently. He was so embarrassed about it. She said the same thing had happened to her when my father had done the same thing before they got married. Then she said I wish you had told me then – but no harm has come of it thankfully. Then she wanted to know all the details about my first time and when I told her –(we didn't tell her about Jan and Mike though) she remembered the time I had hurt myself on the bike and had completely forgotten it and said that is why I didn't have any pain, I had broken my hymen then.
I asked her about the pill she said she would arrange a preion from the doctor immediately, and a few days later I had them. She said this is not permission for you to be doing it all the time though. Just enjoy it when you do.
She had imposed a condition on us that if we wanted to have sex we could in my bedroom and use the bathroom afterwards without a problem. She didn't want us doing it around town where we might be seen or caught. We didn't quite comply with that condition as Jan and Mike and Tony and I still had our orgies in our bushland brothel as we called it. Tony was allowed to occasionally slept over and we spent the night in bed together. There were times we had sex at other times and my mother was aware of what we were doing but left us alone. Sometimes if Tony stayed for a meal she would ask how we were going and a couple of times referred to us as rabbits because of how often we had sex. We could discuss sex with her openly and without embarrassment and never denied we were. Tony could not believe how easy it was to talk to her and we could ask her any question about sex and she always answered and never chastised us for doing it. She soon realised we performed oral sex together, and never said anything against it. She was never embarrassed if she saw him naked going between my bedroom and bathroom. One day she saw me in the shower naked and told me how nice my pubic patch looked after I had trimmed it – or Jan and I did it to each other. Occasionally on Saturday nights occasionally Mike and Jan came over and we watched a couple of videos and we would all have sex together. She was never there when we did it, but she told me after one orgy of sex with them she knew because she could smell the scent of sex in the room when she came home, and after they had left. Tony and I realised we could smell it in my room after we had been having sex and had gone to the bathroom and smelled it when we walked back in. I told Jan and she said they knew also as her mother asked what was that smell was one day after Mike and her had been having sex. She hadn’t realised what it was fortunately.
One thing we had done a few times was to swap partners and Mike and Tony had both had sex with us – vaginally and orally. We never did that without the four of us being present – never just two of us. It was fun more than anything as both Jan and I were more than happy with our own guys but it was interesting to know what doing it with somebody else was like.
I don’t know how long we will all stay together as we all grow older – we may find there are other attractions – but we will know what we are doing and the experience we have enjoyed will help if we decide that other fields may be greener. I know I will always be safe – and my mom and I will always be honest with each other.

Post. As I said earlier I met her when she was 18 – her romance had ended with Tony – happily – and they are still friends but he is married now and she wont break that trust between man and wife.

story by: maddie345

Tags: first time teen male/teen female oral sex essay sex story

Author: maddie345

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