I consider this my first sexual experience.
My first two years of high school were spent at an all-girls Catholic boarding school. The summer before I arrived I had discovered masturbation. I got into the habit of pleasuring myself every night before I fell asleep in my bed. At the time I wasn't sure if it was normal or not, but it felt so good I didn't care. However, when I got to boarding school I wasn't sure I could keep my routine since I had to share a room with three other girls. After about a week I couldn't take it anymore.
I came up with a plan. I waited for at least half an hour after lights-out to make sure everyone was asleep. I would reach between my legs and pleasure myself as I normally did before I came to boarding school. This became my nightly routine, and I was satisfied.
However, one Sunday night, after walking around with damp panties, and turned on most of the evening, I could only wait for fifteen minutes before I started stroking my nipples through my cotton nightgown. They were very stiff and so sensitive, that as I flicked and rubbed them I felt as though I could cum without even touching my womanhood. Underneath the covers I removed my nightie and continued to touch my breasts. As I got more turned on, I accidently let out a soft groan. I remember feeling my heart start to beat really fast and getting really nervous that I would be discovered. After a short time I gave in to the wonderful feeling that pinching my nipples was giving me.
Suddenly, a whisper came from the bed next to mine; 'Why don't you let me watch you while you watch me?' It was my roommate, Carla. I had thought of her as very chaste and proper, because she was always telling us how she wanted to be a nun. She was lying on her side facing me, and I could see by the two little night lights that she was nude. Her hand was very busy between her legs. I was scared, nervous, excited, and aroused all at the same time from the prospect of doing it with someone else. I carefully slid the covers down and pulled down my panties exposing all of my body for her. I couldn't get over how wet I was becoming.
I had begun to develop that year, but my breasts were quite small with my nipples sticking upward, and my womanhood was covered with soft curly pubic hair. Carla was more developed than I was having good sized breasts with long nipples, and dark brown areolas the size of silver dollars. Her pubic hair was shaved at the bottom with a patch of reddish-blond hair at the top.
I leaned to the edge of my bed and whispered for her not to rub so fast so I could catch up. She lay back and circled each of her stiff nipples with her thumbs, moaning softly, watching me. I reached down and began to massage my clit and sliding a finger between my swollen wet lips. It was more erotic than anything I had ever done. Just knowing she was watching me as I masturbated made my clit throb. I looked over to see if she was watching as I touched myself round and round on my clit, while my index finger was pressing inside me.
With our eyes glued to each other's crotches, we picked up our tempo. I felt my legs stiffen, taut with my pelvis moving up and down. I felt my orgasm start and she quietly moaned at the same time and nodded her head. At that, I let myself cum, juices covering my fingers while I watched her arch her head back and cum with me.
Throughout my two years at that school, we had many more nights like that. Today, over 20 years later, Carla and I frequently exchange e-mail and get together at least once a year, although we don't do what we did when we were teenagers.