This happened just the day I turned 20. I had started to explore my feminine side. My partner in crime was my friend. We were roughly the same age.
It had been some time since my friend and I were involved. We started out exploring each other's bodies as would anyone else. He also knew my inclination towards getting dressed. Times alone with each other were spent in playing house. I was the wife and he would be the husband. I would be the young wife waiting for my man to come home. Ready to receive him at the door. Make a cup of hot coffee for him as he relaxed. He would bring flowers and "surprise" me (We did this every week) and finally we would find time for a little romance and end up in bed.
Since we were of the same age and our parents knew one another, there was no restrictions on meeting up - Except for his sister. My guess is that she suspected what we were up to. Sometimes in fact he used to bring me her clothes to wear and I guess she had her suspicions. But as long as we were together she could never find any "proof". With time, we had learnt how to evade her very well. During the vacations is when she would really become a thorn in our side. We just could not evade her "Eye of Sauron". So as an alternative, we decided to meet up at my place. Parents never had a problem with that. They in fact thought we were studying together. So every now and then when he stayed back they weren't suspicious. We of course had some time at night - after they went to bed to play under the covers. Sometimes he would manage to smuggle his sister's clothes, so I could wear those for him. But most times... well we had to make do with our fertile imaginations. Most of the time, we would spend reading soft core magazines - especially the "Questions and Answers" section to see what other people "did" and how we could adopt those for our own purposes.
This incident happened on a day we had some guests around. Some of them stayed back overnight, so we had to make do with camp beds for everyone. He was around to help me out with my chores. Just that since we were amongst the last ones to wind down, we were asked to sleep on the roof. We had a few other people as well. He had very strategically put our bed around a corner on the roof. It was later I realized how strategic that was. But at that time I was just too tired to notice anything.
Anyways it was down to our shorts and vests (It was a very sultry and humid night around 100+ Fahrenheit or 38 degrees Celsius). We dispensed with the bed sheet and curled up. I guess I was asleep in the first two minutes.
It was around midnight when I felt him nudging me. I was just too deep in sleep to wake up. The nudging continued for a while and I slowly opened my eyes. He was right there next to me. Trust me I almost yelped and jumped up. My first thought is if someone (and there were at least 6 other people on the roof with us) - If only someone had seen us, it was game over.
I guess he saw me and quickly clamped his hand over my mouth. Put a finger to his lips to calm me down. Slowly as my breathing returned to normal, he slid down on the bed with him spooning me. He told me he just wanted to cuddle a bit. I too had missed him during the day and didn't mind. Sweet nothings, pillow talk, spooning all started to happen. I was enjoying this little rendezvous and that too under a clear night sky. He started to kiss my cheeks every now and then. First I was not too sure but then let him carry on as long as he kept the noise down. He was kissing my neck and shoulders while I pushed myself back towards him. He started to grind me and I turned my neck around to kiss his lips. All this very slowly and very silently.