When I was 19 I was going out with a 20 year old girl by the name of Kim. I had met her in a pub about a year earlier. She was out with an old school friend of her's and an ex girlfriend of mine, Sandra.
I'd bought the girls a drink and got chatting. Still friends, but no way Sandra and I would be an item again as her new boyfriend was the best thing since sliced bread! I did have sex with her again some time later but that's another story! When Kim went to the ladies, Sandra asked me what I thought of her friend. I said that she was good looking with a good body but a bit shy and quite. Sandra told me to bring her out of her shell as there weren't too many 20 year old virgins left! Sandra had lost her cherry to me and I remembered how enjoyable taking it had been some 2 years before. The chance to deflower her friend did appeal to me! Kim returned and Sandra took the chance to nip to the toilet and we got talking I ask her if she was dating anyone and was told no, so I asked her out. She accepted but told me that she had not been out with many boys and was shy.
To cut a very long story short, I started going out with Kim and after several months of careful coaxing and slow move touching, I managed to break her open and even cum in her on her first fuck! (I still have both the panties she wore before and after, the latter still stained with my cum and her pussy juice plus the blood stain from her broken hymen)! After two nerve racking weeks, she went on the pill.
After about 6 months though she told me after making love one evening, that much as she enjoyed sex with me, she felt left out as I had fucked several girls before meeting her. As some of my relationships had been open, I asked if she wanted to experiment with others. After several minutes thinking, she said that "Yes, I suppose it is."