I was lucky to have an aunt, Lilly, who taught me to not feel guilty when I masturbated. She was my dad's older sister but they really did not get along very well. My family was, and still is, rather conservative and she was more of a free spirit. I had just begun to experiment with masturbation but was told by my parents it was a sin.
I never met her until I was 13. She had been very sick with cancer and came to visit us for a few days. Lilly asked if I wanted to visit her in Boston during March break, although my parents were not too hot on the idea, it was hard to argue when she sent me a first class ticket for Christmas.
Lilly had been a professor of literature at a university but was still on leave when I visited. We had a great time, doing all the tourist things she never did event after living in Boston for years.
She lived in a small older home in a area where all the students seemed to live. On the Friday of my visit, Lilly had a cocktail party at her home for about 20 people. We worked together in the afternoon making dinner and preparing drinks. Lilly kind of warned me that some of her friends were 'different' and asked me not to judge them. I was really not sure what she meant but just said; 'OK'.
The party was fun. The guests included students, artists, two men who were very gay, and some of Lilly's close friends. I was treated like an adult for the first time in my life. I sat at the end of the big table and was able to join in with the adult conversation.
After it was getting late and all the guests but one, a woman friend, had left, Lilly took me aside and said it was time for bed. I was in the spare bedroom when she knocked and came in wearing a very thin nightgown. I could see she was naked underneath. She sat me down on the corner of the bed and started to tell me how proud she was of me and how much all of her friends were impressed by my maturity. She went on to tell me how she saw much of herself in me and that she understood that becoming a teenager was a hard time but I could always call her for advice.
The whole time she was talking I was staring at her shaved pussy and trying to hide a growing erection. After a moment I realized she was talking about masturbating, how it was normal and not to be ashamed if I did it.
Lilly then went to a bookcase in the corner and picked up a large wooden box, and said goodnight.
I was very horny when I got into bed and found my surprise.
Under the pillow, wrapped in a towel were several porno magazines and a tube of KY type jelly.
The pornos were all 'color climax' from Europe, one had entirely Asian women, and another was all teen girls, not much older than me, getting fucked by older men. The best was a book of photos of young men each explaining how they jerked-off.
I spent the whole night masturbating. After quickly coming several times, I tried one of the methods described in the magazine; where you slowly stroke yourself and stop when you feel you are about to come. I was still jerking-off when the sun came up but finally passed out exhausted.
When I awoke, around noon, I had a hard-on, so I jerked-off again.
I had just come when I heard a knock on the door. It was aunt Lilly. She came in, still wearing the see-through nightgown and asked me if I was hungry for breakfast as she replaced the wood box on the bookshelf. I was sitting in the bed with the sheet pulled over my cock. She sat down and gave me a knowing smile, kissed me on the forehead saying she hoped I enjoyed myself last night and not to worry, it was our secret.
That day, we were both tired and returned to the house in the early afternoon. As soon as I was alone again I jerked-off. Afterwards, I recalled the wood box. I opened it to find it was full of hand-made glass dildos, vibes, and a strap-on harness. I realized that as I was masturbating, my aunt and perhaps the friend had been doing the same.
For the rest of my trip, I masturbated each night many times, trying all the methods in the book.
When I was packing to return home, Lilly warned me not to take the porno books but gave me a large tube of the lube, saying it looked like toothpaste.
From that day I never felt any guilt about my sexuality.
Lilly died the following year when her cancer returned. I never saw her again.
20 years later, I was helping my sister move and saw the wood box again. I asked where she got it from and she said 'nowhere'. Months later, when we had a moment alone I told her I knew where it came from and what was inside. I told her the story of my visit with aunt Lilly. She confessed that after Lilly's death the box, and contents had been left to her in her will. She said that she was shocked at first but Lilly had included a long letter explaining why she wanted to ensure she received them. My sister and her husband use them as part of their regular sex life.