I was eighteen, yet to lose my virginity, and fairly inexperienced when it came to girls. In fact the more I fancied someone the more shy and nervous I would become with them. Amy was the same age as me and part of my group of friends, she was a friendly bubbly blonde who everyone seemed to like but nobody seemed interested in sexually probably because she was a little over weight. We got on well together, and I liked her a lot as a friend, but didn't really fancy her which strangely meant that she was a girl who I could talk easily to and be relaxed with.
This evening a group of us had been out late and I'd missed the last bus home. Amy shared a flat with some others and said I could sleep on the settee in her room if I wanted to which I happily agreed to. The flat was in a large old house which had been divided up, and Amy's room had a single bed, settee and some other things crammed into it with not much space to spare. She made a bed up on the settee for me and then disappeared to the bathroom. When she returned I saw she'd got changed ready for bed and was wearing a large baggy T shirt which covered her to just above the knees. She'd obviously taken her bra off as the shape of her full breasts and the little bumps of her nipples were clearly visible under the T shirt, I couldn't tell whether she'd removed her panties too.
I started to undress, stripping down to just my boxers, which is what I'd decided to sleep in. When I'd finished Amy came up to me and said 'big hug' holding her arms out. 'Big hugs' were one of Amy's little traditions and she would often ask for a hug when meeting or leaving someone. I'd had plenty of hugs with Amy and they were always enjoyable little cuddles but nothing more.
We put our arms around each other and hugged each other close, Amy not in any rush to let go. I could feel her breasts squashed against my chest separated only by the thin material of her T shirt and was also aware of how little material separated my crotch from hers. I could feel her hands on my bare back and our bare feet touching, and that combined with the warmth of her body and smell of her perfume made the inevitable start to happen, I could feel myself beginning to get hard. Just in time we started to part but she then asked for a goodnight kiss so we were back together again for a final hug and kiss. The kiss was nothing erotic but it was on the lips and that was the final straw for me. As we finally parted I had a full blown erection which promptly popped out of the gap in the front of my boxers into Amy's full view. In truth she must have known already as I'm sure she must have felt it pushing into her thigh as we hugged the final time.
Embarrassed I started to apologise and tried unsuccessfully to get my penis back into my boxers, but it just wouldn't stay inside despite my best efforts. Amy was all giggles and said she was sorry she'd done that to me and that she'd have to take care of it for me as there was no way I could get to sleep like that. She told me to take my boxers off and lie back on the bed. Still feeling embarrassed I didn't argue and slid my boxers off and got on the bed my erection pointing proudly upwards. To my surprise Amy lifted her T shirt up, over her head and off, leaving her naked too as I finally found out that she wasn't wearing any panties. She then sat on the bed next to me. Although I'd never really fancied Amy before the sight of her in the nude made my penis stiffen even more in excitement. Her breasts were large and swayed delightfully as she moved, her bottom although on the big side was soft and inviting and at the top of her thighs was a neatly trimmed bush of fair coloured pubic hair. As her legs parted slightly I saw my first glimpse of the moist lips of her pussy.
Her hands took hold of my erection and she pulled the foreskin back and started to stroke slowly up and down my shaft. Despite my best efforts I knew I wouldn't last long and within no time at all was shooting my sperm into the air to land on my stomach in a messy warm puddle. Amy loved it and after wiping me dry with a tissue said it was my turn to do her. We swapped places with Amy lying on the bed, knees raised and legs spread wide. I'd never masturbated a girl before and was not sure really what to do. I squeezed and played with her lovely soft breasts, feeling her nipples harden and become erect and stiff under my touch and then I started to rub her pussy, which felt warm and wet to my fingers. I think Amy realised my inexperience as she took my hand and showed me how and where to touch her to make it feel good. With both our efforts she finally had her orgasm with her juices squirting out over my hand as her body tensed and then relaxed.
We both squeezed into her single bed that night, naked side by side, and masturbated each other again the following morning. I would have loved to have lost my virginity with her that night too but neither of us had condoms so that had to wait until a little while later. Yes we ended up going out together after that, and are still together now, and we still look back fondly on that first night of masturbation together.