Sam, Ollie And Me

This is not so much a confession as a fond memory that even now, as an adult married woman, I sometimes let my hand and memory recall.

My best friend as a kid was Sam, who lived next door. We played together for years in each other’s gardens, our parents took us on their respective family holidays, and as our birthdays were within days of each other, we even had joint birthday parties rather than competing for the same weekend slot and the same classmates. We were very close; unsurprisingly, when puberty hit, we went through it together. Although the same age I went through a little earlier than Sam, he soon caught up.

It started at about eleven with the provable doctors and nurses games. I was very interested in the difference between our bodies and would watch enthralled as Sam got an erection and then went soft again. I discovered very early that I enjoyed Sam playing with my girly bits. I would lie in my knickers and bra and let him explore my body. It usually started with looking at my small boobs; I would always have to take my training bra off as he could never figure out how to remove it!! He knew how to get my knickers off, though. I loved him separating my pussy lips and exploring what was inside my pussy, I knew what my clitoris was, and Sam soon discovered that I enjoyed having this diddled between his figures. He told me when I developed pubic hair, and we looked in astonishment using a mirror as we ran our fingers through the new hair. I loved the feeling when he eventually slid his finger into my young pussy. I never got bored of that feeling, and after Sam had done this, I soon followed suit by fingering myself and then using brushes, toys and one of my older brother’s drumsticks.

Sam would also lie on the bed as I explored his cock. I also spotted when he developed hair around his cock; I was fascinated by the different parts of the male genitalia. His small, eventually furry balls, pulling the foreskin back and examining his bell end or, as I later discovered, the glans of his penis. I had my first orgasm with Sam’s fingers, and he had his first orgasm with my hand wrapped around his little cock. It was so strange as the first couple were dry orgasms! Yes, he would have all the physical reactions of an orgasm, but without any of the mess. He did warn me years later when puberty changed things, and I was shocked by the mass of white stuff that shot out, which went all over my school jumper and hit my face.

We were teens when Sam’s cousin Oliver started staying at his house during the summer holidays. I think Sam's parents were concerned that his best friend was a girl and Oliver’s parents were going through a divorce that upset Ollie. We included Ollie in our sexual play on one hot summer's day. He had more pubic hair and a bigger circumcised cock, which, when erect, fascinated both me and Sam. We would lie naked on one of our beds, and I would wank them both off to orgasm. Due to the amount of sperm they were producing, we used socks as condoms lol. However, the bit I loved, and even now decades later, still causes me to put my own hand down my knickers when I was naked, and Sam and Ollie would explore my body.

I loved having them both explore my pussy and seeing if they could get a figure in me simultaneously. Ollie was the first to lick my pussy and clit; that was one hell of a feeling. Oral became part of our play; they licked and stuck their tongues up my vagina, and I would suck their willies. Some of my favourite memories were when one boy would be sucking my breasts as the other licked my pussy. I also loved when they undressed me; my skirt pulled off, my bra always was a joint effort between their two intellects and the glorious moment they both had their hands pulling my knickers down my legs. Then came that fabulous feeling of having my legs parted as their eager hands made their way to my secret feminine place.

The closest we ever got to fucking was both lads rubbing the cocks through my pussy lips. I would sometimes grab their cocks and rub it around my clit until I came. Both boys occasionally orgasm whilst rubbing their cocks through my pussy lips; the first time this happened, we all went to the library to find out if there was any risk of pregnancy. After a couple of summers, I allowed both to use my favourite masturbation brush on me. They were special times, and I would have one pushing a brush into my pussy, as I sucked the other off. I would cum out of my brain!

It all stopped in our mid-teens when Ollie and I started to date, and Sam got his first official girlfriend. Ollie eventually took my virginity, and a decade later, we married. The only problem we had at the wedding was Ollie wanted Sam as his best man, and I wanted him as my ‘man-of honour’ along with my bridesmaids. Sam was the best man and made several jokes about being both the best friend of the bride and the best man and cousin of the groom. He did cause me to catch my breath at one point as he intimated he had been my first, only to finish the sentence with first to play football and cricket with him, and he to play in my dolls house and plat my Barbie’s hair. Happy times.