I was 16 at the time and had only really been interested in sports. Rachel was the same age and good at math, so that evening when my parents were away at a concert, she came round to my house to help with the homework. Sitting on the bed, she spotted a soft porn mag of my father's that I had rescued from the bin. "Do you enjoy wanking?" she asked. I was shy but had to admit that I did, whereupon she asked if she could watch me do it. Surprising myself, I got my cock out, laid on the bed, and started stroking it. She watched with interest and was soon to see wads of come spurting from my dick. She carefully cleaned me up with some tissues and asked if she could touch my now sagging dick.

I had never been with a girl before and the excitement was incredible. She started to stroke me as I had done before, and within a couple of minutes I was spurting more come all over my belly. Once again she obliged with the tissues and asked if I would like to touch her. How could I refuse? She pulled her short skirt up to her waist and opened her legs, exposing her white panties. She put my hand on her crotch. I was surprised because she was very wet and I thought she had peed herself. She was obviously enjoying it with the noises she was making. After a few minutes she asked me if I wanted to do it. She removed her panties and lay on the bed with her legs wide open. She told me to climb on top and do what I read in the magazine.

Getting on top was easy, but I couldn't find her cunt with my cock. After considerable squirming and help from her hand, I was inside her. The feeling was exquisite and I couldn't help but thrust away quickly. I came again within seconds of entering her. All I wanted to do now was sleep, but she undid her blouse and lifted her tits from out of her bra and put my hands on them. Till then I had been shrinking inside her but now things were starting to happen again. My cock was hard again and I started to slowly move inside her. This time I took things a bit more slowly and probably managed to fuck her for about five minutes before coming again. It was only after she had left that I realized that this had not been her first time.

I had a night off to watch fireworks last night guys so got a great story for you about Laila having sex for the first time.

I've never really thought about sex, I wasn't really interested in anyone and when I DID stop to think about it, I thought 20 would be a good age to lose it (I am currently 18, going on 19 in 3-4 months)
It just felt like a good number and I conditioned that if I were dating someone before it, then they would just have to wait.

But I wasn't counting on finding someone I was so comfortable with and was even more surprised to find that I wanted to initiate it.

It was a hot afternoon, the two of us have been dating for 2 months (he is still my current partner) and we typically engaged in mutual masturbating… so we were both comfortable enough with each other, having explored our bodies – just stopping at penetration.
I knew that he was definitely the one I wanted to give my virginity to, the only thing stopping me was my ideal of "20".

After resting from all the touching, him lying on top of me, I stared carefully into his eyes.
I definitely was in love with him (not an emotion I take lightly, nor does he) and I just felt the urge to be… one with him.

So I told him… and he chuckled, a little incredulous but not pushing or pressuring.
For the next 10 minutes he let me lay there deliberating if I wanted to or not – NOT trying to convince me, making sure it was ABSOLUTELY MY CHOICE.
I closed my eyes, took a breathe and said, "Yes, I want to."

I had a condom/lube set aside from a night out with some friends (went to a club for a birthday and a friend had come by having taken all the free sexual goodies in a basket and I took one as a memory of the night). I waited for him to put it on and then he laid on top of me… It was the first push, he slowly put it in – yeah there was pain but I suspected it was the lack of lubrication from nervousness and the friction of the condom, he continued until he was completely in – making sure I was alright.
He took it out, my eyes closed the whole time and said, "I've already put it in… you aren't a virgin anymore."

We searched around for any sign of blood but it was minimal which was a relief (not a fan of blood)… I told him it hurt and we took out the lube to help it slide in better.
He lay on top of me again, slowly inserted – this time easier with a smaller amount of pain and he started moving, faster and faster – holding me close.
It felt so good, even with the pain – I was moaning from the pleasure more than the hurt.

We'd finished, both breathing heavy, he took himself out, we both cleaned up the mess of wrappers and I looked at him, the sweat on his face, wiped it away and kissed him.

We then cuddled, went downstairs to eat (wow, sex takes a lot of energy) then went back upstairs and cuddled more.
There wasn't a moment of regret in my choice and I know I wasn't used so I only feel closer to my partner.

Not a moment of it was awkward, it was completely natural… as if I was crazy for not having done it in the first place.
But that's how it was, the wait and getting to know each other was worth it. Nothing drunken, nothing pressured – ABSOLUTELY MY CHOICE AND MY KNOWLEDGE.