I was 18 and troubled
As an only child in a dysfunctional family I got beaten up a lot by my dad and ignored or scolded by mom. By the time I reached my mid teens I had a serious masturbation problem only then I didn't realize how bad it was. I masturbated frequently and compulsively, and was also an exhibitionist. All I got was punishment.
My only friend was my aunt Marge, who was in her early fifies then. I would have liked to visit her more often, only she lived too far away to permit more than the occasional visit. But when I was 18 and having constant fights with my parents, they both needed to visit my uncle who had taken ill interstate, and as they couldn't afford to bring me as well, they dropped me off to stay with Marge for a week.
Marge was a few years older than my parents but seemed much older to me at that age, almost a grandma. She was an outspoken, practical lady who smoked and didn't stand for any nonsense, but nevertheless treated me kindly. She had a sense of humour but I was too shy and immature to know how to respond. She dressed casually and I enjoyed looking down her cleavage, which she didn't do much to hide. The first night, while I was masturbating in the shower, she asked if she could come in and get some underwear she had hung up to dry, promising not to look at me. This turned me on, and I kept doing it with my back turned to her. I heard Marge's voice saying 'Don't break it off now.' She must have guessed.
The next morning, while she was out shopping, I stole into her bedroom as I had done to Mom a couple of times, and found where she kept her underwear. I pulled out a pair of black panties and began masturbating. Some hours later, after I had done her chores, she came up and wanted to know exactly what I had been doing in her room. I couldn't answer her at first, but she finally extracted the truth. Instead of screaming at me as I had expected, all she said was 'Well, you must have been desperate to do that.' I felt so low, I began to cry. Aunt sat down, put an arm around me and we talked about sex a bit. How did she understand me so well? 'next time you feel lonely and upset, tell me.'
That evening after dinner, Marge announced she was going upstairs to have her bath. When she came back down I was expecting to see her in her nightgown and slippers, but instead she had put on lipstick and mascara and wore a black lacy top, black stockings, high heels and no skirt! I could see black lace panties. Though a bit on the plump side, her effect on my young hormones was incredible. 'Do you like me in these panties?' she smiled. 'Go, on, enjoy the view.'
I was flabbergasted. Marge sat down, lit a cigarette, crossed her legs and undid her shirt so her breasts plopped out, her nipples bigger than I imagined. I think she was slightly drunk too. 'Come on, let's see your equipment too.' I was too embarrassed to show her. Marge said matter-of-factly, 'Don't think you're the only one who does it.' She hooked a finger inside her panties and began feeling inside herself. This was the first time I had witnessed this and was shocked. 'It feels good,' Marge reassured me. She looked at my crotch. 'Show me how you do yourself.'
First I reluctantly put my hands down my jeans, but as we got more aroused, I ended up masturbating in plain view of my aunt, while she did the same. She took her panties off, sat with her thighs wide open in front of me and fingered herself as vigorously as I did, leaning back and thrusting her hips at the same time. I was fascinated by how wet and pink she was inside her dark hairy bush. She grunted and talked dirty the whole time, finally closing her eyes and shuddering through her orgasm. We almost climaxed together and I really came strongly.
Afterwards, Marge grinned at me, asking 'Did that feel good?' She obviously did. She made me promise not to tell my parents what we had just done, and for the rest of my stay with her we would masturbate regularly, as well as do other things which are outside the scope of this story. Marge told my relieved parents how well-behaved I'd been, and they never even suspected. A few years later, when I was living closer to her, we took it a bit further until I started going steady with my fiancee. But Marge sure taught me a lot.