My Friend Jane

I was a shy little boy and had little self-confidence when younger. When I was about ten years old my family moved cities due to my father’s job. This meant I had to move school which was a horrendous trial for a kid with no self-confidence. I was bullied at my new school due to my strong Northern accent; my family had moved from Manchester to London.

The only positive thing about the move was the girl next door called Jane. She was the same age as me and the prettiest blonde girl on the planet. Jane was also extremely self-assured and simply oozed self-confidence. We got on extremely well, I was the subservient admirer and Jane the boss. Due to her being one of the most popular girls at school she sorted my bullying out, and due to my friendship with Jane, I then became popular too. Our parents got on really well, so we ended up spending loads of time together.

In the summer holidays, about three months after the move to our new house, Jane called around to play. We had constructed a den of blankets, sheets and chairs in my bedroom. She was wearing a pretty white summer dress and white sandals. As she was laying down I caught a glimpse of her knickers under her dress; Jane caught me looking!! I was mortified at the detection and said sorry. Jane then asked if I wanted to play doctors and nurses. I didn’t know what that was about but always agreed to everything she ever suggested.

Jane asked me to take my jeans off and lie on the floor to be examined by the nurse. I complied and when lying down Jane pulled my underpants down and examined my cock. I was embarrassed as it grew big; I didn’t understand at the time why it kept doing this, and my parents just fobbed me off that it was just ‘natural’ Jane explained that the reason my willy, as I called it then, got hard was so that it could fit into a girls ‘foo foo’. Now I’d heard that girls had something different between their legs but I’d never seen a ‘foo foo’ so Jane took her knickers off and showed me hers.

I was fascinated! Her pussy was quite large and had the start of some soft blonde pubic hair; I was embarrassed as I didn’t have any hair down there. Jane let me touch her foo foo and she gave me a tour around it. These doctor and nurses sessions happened quite a lot over the coming year, all very innocent and I loved them (and Jane)

When we both hit puberty we stayed close friends but the doctors and nurses sessions stopped. However, when we hit our teens they taught formal sex education in Biology class. Jane and I were in the same class and every boy was looking at every girl in awkward silence, and visa versa, as the teacher explained the birds and the bees. When I got home Jane called around to do some homework. I was more of an academic than Jane, and I now helped her with some of her homework. In my bedroom, we got to speak about the sex-ed class and some of the terminology used. We laughed that Jane used to call her pussy a foo foo and my cock was my little willy. There was a sexual charge to the conversation and we agreed to play doctors and nurses one more time to check out the Sex Ed class.

I went first (at Jane’s request) and she inspected my erect penis. Thankfully, I now had a full bush of pubic hair. After examining my member she put it in her mouth and see what ‘oral sex’ was like. The feeling was incredible!! I did masturbate in my teens, however, this felt better than anything I’d done to myself. Whilst she was playing and sucking me I put my hand up her skirt and pulled her panties off. Her pussy looked very different than it had as children. She now had a neat thick Hollywood strip of blonde pubic hair and her pussy wasn’t as smooth as I remembered. One of her pussy lips seemed to be longer than the other and stuck out. I examined her as she was examining me; this included licking her pussy. We ended up in the sixty-nine position and I felt like I was floating. The sensation of having my cock sucked whilst enjoying the taste of this Goddesses pussy was heavenly.

Three years later after a party, we lost our virginities to each other. I loved Jane, and as first experiences go I can’t think of a better one. She was perfect and it all felt so natural. We properly dated for about a year and then it fizzled out. We went to different Universities, although we did speak at least twice a week in the first year, and then usually once a month thereafter. Our parents still lived next door to each other and during holidays we would always hang out. I still loved her, and I know she loved me, but we were young. One Christmas Eve we did hook up again and had a wild night of sex, we must have fucked each other half a dozen times that night.

Jane’s father died in her twenties, and as she only had a sister and aunties, she asked me to give her away at her wedding. This was one of the hardest things I’d ever done. The guy was a doctor and destined for wealth and greatness, I was very jealous. Jane was the ‘best woman’ at my wedding five years later. A break with tradition but it went down well, she was my oldest friend and we live in different times now; her best woman speech was hilarious.

So, what’s my confession? Well, after Jane’s divorce I took up a supportive friend role. Jane was devastated by the breakup. Idiot doctor had found somebody else and dumped my lovely Jane. I was in full rescue mode and we ended up sleeping together again. In my heart, I swear it was to comfort her and make her feel wanted again. The thing is I love my wife and she would never understand, nor should she have to. I can’t stop sleeping with Jane though, she has a hold over me like no other person ever has. I wish I could split myself in half and keep both my fabulous wife and Jane happy. I know this is all going to end in heartbreak for somebody, my best guess is it will be me.