My third year in college I had a roommate that you could say wasn't really too shy about being nude. The second morning after she moved in she came back from the showers and laid around in just a towel for over an hour not seeming to care that it wasn't completely covering her. By the end of the week she didn't even bother about the towel anymore, just laying around nude until she had to dress for class.
Being sort of a prude at the time I commented about her nudity a couple of times but she said it was just skin and it didn't make any difference if I saw her nude or not. After a few weeks I guess I got used to her and it didn't bother me anymore. Then one day she asked how I liked her new look and she dropped her towel and I saw that she had shaved completely. I was stunned, this was back in the sixties and I had never heard about shaving that much. I had trimmed myself a couple of times when I got to bushy for certain swimsuits but to shave all of it off wasn't anything I had even thought of.
From then on for some reason I just couldn't seem to not look at her anymore. Her pussy seemed beautiful compared to my own. She basically just had a vertical slit with slightly bulging outer lips, whereas mine seemed to me ugly with my inner lips protruding and always darker in color.
I started fantasizing that mine looked like hers and at night in bed I'd push on myself trying to make everything stay inside. Believe it or not I even taped myself for awhile hoping that would do something but it didn't help. Pretty soon the fantasizing turned to masturbation and I'd lay in bed at night playing with myself but never having a real orgasm.
One Sunday morning after we woke up my roommate was laying in bed nude as usual reading a book. I was on my bed studying for an exam I had on Monday and I glanced over and saw her scratching her hip. When she was done she left her arm on her hip and I saw that her finger tips were right above her slit. Next thing I noticed was her fingers lightly moving along the top of her slit making small circles around the area of her clit. I pretended I was reading but I was watching every move she made.
Pretty soon she put the book down and concentrated on what she was doing. She had her eyes closed and her other arm over them, but with her other hand she started rubbing up and down the sides of her pussy and occassionally sliding one finger up the center. I still made believe I was reading but now one of my hands were under the covers mimicking every move she made. Soon her middle finger disappeared inside her and she seemed to be pressing the rest of her hand hard against mound. I did the same thing and for the first time in my life had a real orgasm, it was unbelievable.
When I finally opened my eyes and looked back her way she must have came to because now she was on her back with her hand still over her pussy and her finger still inside. It was like she was asleep because she stayed like that for quite awhile before finally getting up and getting dressed and leaving the room saying she was going to the student union for the rest of the day.
I laid there acting like I hadn't seen anything, but as soon as she was gone I started over and in the next couple of hours came three more times. From that day on I knew what to do and didn't have any trouble getting myself off when I wanted to. We never did anything to each other but a couple more times that year she masturbated while I was in the room, but I never let her see me doing anything.