Chapter 1: Every story needs a start

I’m Tim, and my girlfriend is Rachel. Our story is a bit unconventional, but one I don’t think any of us would change. I have known Rachel since first school. She was petite, clever, and kind, but always quite shy. All through middle school and into senior school, nothing changed. She preferred to stay mostly in the background. Towards the end of our time at senior school, we faced our GCSE exams. The day that all the exams had finished, I met Rachel walking through the park as I was going to an end-of-exams party. We were both (just) sixteen.

Despite her shyness, we knew each other well. I’d always got on fine with her, and we’d often chatted. That evening, she was wearing a short skirt and a stripy top, but she was also wearing makeup. I couldn’t remember ever seeing her wearing that, and I had to admit that it suited her. I told her that she was looking very pretty, probably just out of kindness at first, but the more I looked at her, the more I realised that she really was!

I asked if she wanted to come to the party with me. She was nervous at first, but I told her that I’d love to go out with her. So, we went to the party. We chatted, we danced, we kissed and cuddled, and in the dim light of one room at the party, I fingered her hairy pussy under her short skirt. As she gasped and shuddered, the old Rachel melted away in front of my eyes!

That summer, we were inseparable. We went cycling, walking, to the cinema and ice skating. She made me a better person – even down to getting me to study to prepare for going into sixth form. Then came the day of our GCSE results. Rachel did, as expected, brilliantly, but, very surprisingly, I did much better than anyone expected.

For the final couple of weeks of the long summer holidays, Rachel was going to stay for a week with her grandma, who lived along the south coast. I was invited to go with Rachel, so we made the long trip down south. The trains were on time, and we reached the south coast around 7pm.

Rachel’s gran was an older version of Rachel, just as small and petite. Unfortunately, she’d had a fall some months before and now slept downstairs, as the stairs were too much effort for her. There was a full bathroom upstairs, but also a shower and toilet downstairs, so Gran didn’t even try to go upstairs any more. She was quite hard of hearing, and you needed to ensure you stood directly on her good side to get her to understand you.

Gran told us where to find the bed linen and to make up the two guestrooms upstairs. We made up both rooms, but one had a double bed, and we soon decided that it would be safe for us to share. That night, I undressed Rachel for the first time. She had the tiniest of boobs—30AA— but she loved having her nipples sucked and played with. I had a pack of condoms in my wallet, a pack I’d had, unused, for several years, but we were both still virgins. I undressed and she was amazed by my cock. I too was amazed at how it grew that evening, but I was more nervous that I’d be too big for her. I needn’t have worried. Cocks always seem bigger than they are, and pussies are much more elastic than you’d imagine.

We kissed and I groped her for a while until I climbed over her and put my penis at the entrance to her pussy. She tensed up and I told her that if it hurt, I’d stop. We’d brought beach towels with us, and we put those under Rachel to catch any blood that happened while she was losing her virginity. I think we thought it would be like a period, with quite considerable amounts of bleeding, but actually, there was not that much. In the end, I found her very wet, and I slipped inside easily.

I tried to take my time. It was not simple because the new sensations for both of us, combined with her tightness and my teenage hair trigger, meant that I didn’t last very long. She didn’t have an orgasm, and I was mortified by that. She assured me that all the books say that it comes, if at all, with practice, preparation, and performance. She then lay back on the bed and masturbated in front of me. I’d never seen that, nor even known that she masturbated at all.

Watching her was mesmerising, and as I heard her breath quicken, I found myself standing at attention once more. This time, I lay back on the bed, and she straddled me. I realised she’d done a lot more reading about sex than I had, though I shouldn’t have been surprised. She looked at me as she controlled my strokes inside her. Sometimes she took it slow, sometimes almost maniacally fast, and occasionally she’d drop down hard on me, and I’d push up at the same time, filling her deep. The sound she’d make at those moments was wild and guttural.

She came before me, briefly, and as I pulled out, she lay next to me and masturbated, having at least one more orgasm before we both went under the sheets and cuddled. Sleep came easily, and I woke to find myself spooning her from behind. She was already awake, and my morning wood was pushing her from behind. She reached between her legs and guided my cock into her pussy, still wet from the night before. This was a slower fuck but felt amazing. I reached around the front of her and held her as we screwed. It was only as I came inside her that my mind registered that I hadn’t worn a condom. She told me not to worry as she went on the pill the day after we started to go out!

Her Gran heard nothing and suspected nothing. We had a great couple of weeks and went back home and on to school as a very happy couple. Sex continued between us and only got better and better. Rachel’s parents knew, because she told them. My parents knew, eventually, because they caught us. Cue much merriment from my parents and plenty of good-natured teasing. Both sets of parents were very supportive once they realised we were being careful.

For the next two years, we became stronger and stronger as a couple. Rachel was so good for me; she made me better at school and helped me realise a potential of which I was totally unaware. I was good for Rachel in helping her to be more relaxed and outgoing. She became less nervous and more likely to be a part of conversations with others. As we came up to our final school-leaving exams, we both were sensible and studied properly, even though I’d rather have spent more time with her. Rachel’s final exam was two days before mine, so she had a Tuesday and Wednesday free before meeting me on Thursday night.

On Thursday night, we went out for a meal. Nothing fancy, but not fast food either. Rachel seemed a little preoccupied, but I thought it could be tension following the exams, especially if you think you have mucked up. She said it wasn’t that, but she certainly wasn’t her normal self. We went back to her house and saw her parents before we went to her bedroom for the night.

I never got tired of seeing my beautiful girlfriend, dressed or undressed. My cock appreciated her too, and as it was my turn to choose the first position, I bent her over the bed and took her doggy style up her pussy. She always loved feeling my balls slap against her ass. She didn’t cum with me this time, which I always tried to make happen, and as she turned around, I saw she was crying. If ever anything can turn a moment off, it’s seeing your girlfriend crying.

“What’s up, Rach?”

“I’ve let you down,” she sobbed.

“I’m sure you haven’t. What do you think you’ve done?

She continued to sob, so I held her close to me.

“I was with another guy on Tuesday and with a different guy on Wednesday.”

I felt sick. I thought that this was the end for us, because she was going to leave me.

“So, you’re breaking up with me?”

“No, no! I don’t want to, but you’ll break up with me because of what I’ve done.”

I sat there for a moment, mind just reeling. Was I going to break up with her? I didn’t want to. Did I still want to be with her? Definitely.

She broke the silence.

“Say something, please, Tim. Don’t hate me.”

“I don’t hate you. I couldn’t hate you. I love you. I’m just very surprised and confused, I suppose. Why, Rach?

“I do love you, Tom, but I just keep wondering about sex with others. I’ve only ever been with you... ‘

“ ... And I’ve only ever been with you too!”

“But don’t you ever look at someone else and wonder what they’d be like? I do. I still want you. But I want to go with others too.”