I caught my babysitter
By: Date: 2023.01.15. Categories: Sex Stories Tags: , , , , ,

I caught my babysitter masturbating one night when I came home after training. She hadn’t realised I had come in. I had never seen a girl do it to herself. She must have been about 18 and had taken all her clothes off. After the initial shock of being caught I told her I did it too, it was cool.

Then she asked me if I would do it and show her. She had not seen a boy masturbate before so I did.

I told her I had not fingered a girl before and I asked if I could touch her and she let me do it to her. She showed me how and I got her to cum. Then she did it to me. She liked the feel of my cock in her hand and was fascinated when I came. She had not done it to a guy before and was proud of herself when she got me to cum.

After that whenever she was going to sit for my baby sister I made sure I was going to be home and we masturbated together. She was a red head and I was fascinated with her red hair around her pussy. I asked her if I could fuck her but she always refused. She told me she had a boyfriend, so I couldn’t.

I used to skinny-dip a lot with Dianna, the girl next door. Her parents had a pool. Both our parents enjoyed nudity it was nothing unusual for us all to be nude together in the pool area. One afternoon Dianna rang and asked if I wanted a swim. It was just the two of us.

As usual we never wore swimmers. I noticed she had trimmed the hair around her pussy, but not cut it all off. I said it looked nice. I told her about the babysitter and her red hair around her pussy.

Then I asked her how often she masturbated. She was a bit embarrassed but wanted to know how I knew. I said I just assumed everybody did. I then told her about the babysitter and me.

As we talked we both got a bit worked up and I got a hard on. She was fascinated with it, as I had never had a hard on when we were all together with our families. Then I asked her if I could suck her nipples and she agreed if I let her play with my cock and stroke it.

After a while we started to kiss as she stroked me. Eventually she let me put my finger into her like she did when she masturbated. I showed her what I did to our babysitter and she liked it and I got her to cum. We were soon both quite comfortable with me kissing her and sucking her nipples while she played with my cock and letting me put my finger inside her.

That was the beginning of us getting together a lot. Every time we met we masturbated each other. Then one day she asked me if she could suck my cock I said yes, if I could lick her cunt. We both agreed we would do it but we were reluctant to start and said who will go first. Then we both agreed we would start together. Neither of us had heard the term 69 until much later, but that’s the position we got into.

I started on her at the same time she started on me. She had shown me her clitoris and how sensitive it was and how it made her cum. I used my fingers to open her cunt up so I could lick her clit. She was so happy for me to do that and then didn’t hesitate to suck my cock. I was thinking about what I was doing to her and didn’t take much notice of her sucking my cock. Then she told me how good it felt and I went down licking her cunt hard. She responded on my cock and without either of us realising what was happening we both came at the same time.

She was shaking and bucking about and I was trying hard to finish her off and keep my mouth on her cunt. I was so distracted I hadn’t realised I had cum. I had actually ejaculated straight into her mouth. She hadn’t realised what I was doing and actually swallowed my cum.

We were both confused. It was an amazing experience which I enjoyed. She had never cum before getting licked out – in fact she had never been licked out before. I had never ejaculated in a girls mouth before and she had swallowed it all without realising what was happening. She then accused me of pissing down her throat. I explained that I had not pissed, I had cum. It was different.

The two of us then spent a few minutes talking about what had happened as it was new and strange to both of us. Neither of us had done anything like it before. She had never been licked out before, and said it felt amazing when she came. I had never ejaculated in anybody’s mouth before. I said I was so busy trying to make her orgasm great I didn’t realise what I was doing and was too busy licking her clit.

She said it tasted funny and I said I had seen another girl sucking her boyfriend off and swallowing his cum and she seemed to like it.

After a while she asked me to masturbate again and I ejaculated for the second time only this time I came on her tummy. We both looked and played with it with our fingers and wondered how much I had, and how I made it.

She said I can never fuck her as she will get pregnant if I do that inside her.

A week later we were doing it again and she said she had told a friend what had happened. She found out she can’t have babies till she has periods and she hadn’t started them yet. Foolishly she told me so I said I could fuck her and she couldn’t get pregnant. It took a bit of talking and at first I said I would pull out before I came inside her. We did it a couple of times and I got it out in time and I came on her tummy each time. She wouldn’t suck my cock after it had been inside her, but I managed to get her to suck it first before we fucked.

Just in case she wouldn’t get pregnant I said I would let her know when I was cumming and take it out and she agreed. She had learned that you could get pregnant if you fucked during the month before she had her first period. We did that a few times and then one day I was fucking her and I said I am cumming and she said “DONT TAKE IT OUT – DONT TAKE IT OUT- LEAVE IT IN ME”

That was the first time I had actually cum inside a girl and it felt awesome. Afterwards I was a bit concerned about cumming inside her, what if she got pregnant? She explained she had heard about a rhythm method of contraception and had looked it up on the internet. She said I have worked it out and I am having a safe day.

I hoped so.

Gradually she got a lot more adventuresome and regularly sucked me off and let me cum in her mouth. She said she didn’t like the taste much so she spat some out and swallowed the rest. We really tested those safe days and fucked a lot on them and I came inside her because we both liked doing that. On the other days I pulled out – and came on her tummy, if I got out in time.

She had heard at school that it doesn’t do any harm to swallow cum. evidently a few girls do it for their boyfriends. Dianna stared to swallow it more often and soon got used to the taste and swallowed it all for me. Jan was shocked when Dianna admitted she swallowed my cum and wanted to know all about it.

The next week Jan was at Dianna’s when I went to her place to fuck Dianna. I wasn’t expecting her to be there as we had planned to have sex together. We talked for a bit and Dianna agreed to suck me let Jan watch us. I managed to talk Jan into undressing with us. Dianne and I started to 69 in front of Jan and she started masturbating.

After a few minutes Jan asked if she could swap places with Dianna. She wanted to suck my cock and see what cum tasted like.
I agreed as I didn’t mind who I sucked or had suck me. Dianna said she didn’t mind. Jan agreed before we started I could cum in her mouth. Dianna wanted to watch her.

When the time came for me to cum, I said I am cumming and Jan had changed her mind and wasn’t sure she wanted to. Dianna wouldn’t let her take her head off my cock and held it down on me. I came in Jan’s mouth. She gagged a couple of times but she swallowed it all. She said it wasn’t as bad as she imagined, and it didn’t taste like piss. I had to explain once again it isn’t piss.

After that we talked about fucking and sucking and we all wanted to do it again. Jan had never seen anybody getting fucked before so I fucked Dianna while Jan watched. I came in Dianna and Jan wanted to see it inside her cunt.

We both looked into Dianna’s cunt to see it leaking out. I don’t know why I did it, I was absolutely mesmerised. I looked for a few seconds and her cunt looked beautiful all puffy and wet after our fuck. Before I realised what I was doing I was down on Dianna sucking her cunt which was almost full of my cum. I was licking my own cum out of her cunt. I sucked on her until she came again. It was amazing and both Dianna and Jane were squealing like pigs with the excitement of it all.

They were right it was very salty and a bit like vinegar after it came out of her.

Then Jan asked can I do it to her the same way. Cum in her and suck her afterwards and make her cum. I wasn’t going to miss that opportunity, and I agreed to do it again with her.

She got ready and I started to fuck her. As my cock went into her she gave a yelp and she said it hurt. What did I do?

It was only then we all realised it was Jan’s first fuck. She had heard about girls losing their virginity and said that’s what it must have been.
Dianna then said it was my first fuck too back a few weeks back, but it didn’t hurt her.

Anyhow Jan said it was feeling better and she wanted me to finish and cum inside her. I continued to fuck her and the longer I went then more she liked it and the two of us were having a ball. Dianna was amazed that we were having so much fun and it was Jan’s first time. Anyhow it didn’t take me much longer and I came into her. She was so proud of herself her first fuck and her first cum inside her. We were all so happy.

As soon as I pulled my cock out of Jan I got down to lick my cum out of her like I promised. It was great but it tasted a lot more salty than it did when I licked Dianna out. When she came and I got off her Dianna looked at me and said YUK, what is that around your mouth. It was actually Jan’s virgin blood, not much but a little bit. I had sucked my cum out of her and some of her virgin blood as well. I was a real vampire.

I went to kiss Dianna and she ran away, I then went to kiss Jan and she came to me willingly and kissed me – blood, cum and all. She said she could not thank me enough for doing what I had done with her. She would remember me and our time together all her life. She said I am a real woman now – I want to tell the world. Maybe I will have a baby.

I laughed and said if you do it will be in my mouth, that’s where all my cum is.

Dianna then went for a piss.

When Dianna came back she saw Jan and me kissing really hard – French kissing with our tongues and in the nude and me with a hard on. It must have turned her on because the next thing I realised she was down and taking my cock into her mouth. It still had all the cream from Jan’s cunt on it.
From that day on we all said we were blood brothers and sisters.

We fucked together every few days. Jan and Dianna and me. During the school holidays our parents were at work so we fucked nearly every day. Neither Jan nor Dianna got jealous. It was almost the end of the school holidays and Dianna got her first period. Jan was quite happy as she was getting all of me. A few weeks later Jan got hers. For a while I could not fuck either of them anymore as they could both get pregnant now. We could suck and did suck a lot.

We all wanted to fuck so I promised to pull my cock out before I came. It wasn’t as good, but not bad. A couple of times I just made it.
After Dianna got her periods, she also got bad acne a few weeks later. Her mother took her to the doctor. Believe it or not he prescribed the birth control pill to fix her acne. Her mother explained she must never use that as an excuse to let a boy have sex with her.

Little did she know Dianna and I had been having sex for months now and we were about to start again.

Jan had also heard that if you complained of really bad period pain, and pre-menstrual stress, which she didn’t have (but claimed she did) the doctor would give her birth control pills to stop the pains. The doctor must have known too as he told her she had to come back after a few months for a check up. The sister of one of Dianna friends at school worked in the pharmacy and really looked at her when she went to get the pills. Dianna just said – for my acne. Jan just gave her a knowing smile, when she bought hers.

I said to Jan maybe I should ask her for a fuck. She hit me.

The three of us were fucking like rabbits again and I was getting my cock sucked regularly by two women and occasionally by another – the babysitter.
We got hold of a few sex books and we copied the ways they were having sex in the books. It was so much fun. We learned from the books that what we were doing a lot was called a three-way.

All l three of us had no problems licking one or other out after I had cum in them or them swallowing my cum right out of the eye of my cock. It was a wonderful way of life.

I shaved both the girl’s pubic hair and left some above their pussy and they looked beautiful. It was much better when I licked them after that as they were nice and smooth. Even Dianna’s mother complemented her on how nice it looked and said I might try it like that. I don’t think she realised it was me who did the trimming.

It was quite common for Dianna or the three of us to fuck a few times a week after school. One afternoon we didn’t realise her mother was home and she caught us in the middle of a fuck. Lucky Jan had her periods otherwise she would have been with us. She told us to get dressed and see her down stairs.

We were shittng ourselves.
Her mum made the two of us sit down and talk to her. I sat next to Dianne and we held hands.

She said I have a feeling that wasn’t the first time we had done it. We had to admit that we had been doing it for a couple of months – since she got the pills. She was pretty cool about it and did not yell or scream or say anything nasty to either of us. She said thank heavens for those pills. Her mum was also happy nobody other than Jan knew we were doing it.

Then she asked me if I had done it with Jan too and I had to admit I had. She said I hope Jan’s parents are as understanding as I am when they lean about you all. That was going to be our next challenge. You realise I will have to discuss this with your parents as she looked me in the eye.
Now I was getting worried.

Then she surprised us both by telling us that she was NOT going to tell us to stop doing it. She said I know you will go behind my back and do it anyhow. I don’t want the police on my door step telling me they found you somewhere having sex together. I want you to promise me that when you do it together it is inside this house and nobody other than your parents and Jan knows anything about it. We promised her nobody else knew what we were doing. She said thank god you are all 16 and can do it legally, but she was afraid if anybody else found out she could be in trouble for not stopping us and letting the three of us do it in her house

It took a few weeks and everything settled down. We didn’t do it as often but we still did it. Jan’s parents and my parents had evidently had a meeting with Dianna’s mum to discuss it. They agreed with the rules Dianna’s mum had laid down and accepted that we could do it in Dianna’s bedroom. She was an angel as far as we were concerned.

By then had Dianna moved down to the guest room. We realised her mum could hear us in her bedroom which was next to Dianna’s. After that Jan had joined in with Dianna and me quite often. Her mother soon became quite accustomed and casual about seeing us, knowing what we had done, or were about to do. She said nothing when she saw either of us going to the bathroom. We didn’t lock the door anymore and Dianna’s mum began to get around the house more often in the nude. It was quite common to see her nude around the pool.

Her mother was calling me ‘the stud’ and the three of us rabbits. Sex and our relationship was openly discussed and I had quite a few meals at their place and occasionally slept with Dianne overnight. Obviously my parents became aware of everything and whilst not quite as forgiving as Dianne’s mum, slowly accepted the fact.
On one occasion we were
all going to a party and I went to pick Jan up from her house. Her mother said to me – I hope you are looking after Jan, she is precious to us, please be careful with her. No baby’s please. I said and precious to me too. I am not sure she was as forgiving as Dianne’s mum.

As the weather got warmer we began to skinny-dip a lot more in their pool which was private. After a couple of times her mother joined in with us after school. It was only a few days later Dianne’s mum appeared with her pubic hair all trimmed, and looked slightly embarrassed. We all complemented her upon how nice it looked. By now were all very good friends and there were no problems. The relationships could not have been better. The sex between Dianne, Jan and me was now a common occurrence and had no significant effect upon our relationship with her mum. It was quite normal.
A few months later Dianne and I were making love in the pool as we did occasionally. Her mum walked out and lay on one of the lounges.
Carry on – have fun, she said, and giggled.

We did.

After we finished our lovemaking we joined her and we chatted. We were all very relaxed.

Later on after her mum had gone inside – I said to Dianne that I wouldn’t mind asking her mum if she would like to know what it was like to have sex with a ‘stud’.

Dianne said you never know your luck – look at us.

I live in hope but It will never happen.

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