I've had many experiences in my life and this one is near the top of my list!
When I was 18 and still living at home, we had a family friend stay with us for two weeks. She was a longtime friend of my Mom's. I had known her for many years and I always thought she was pretty hot.
During the two weeks she stayed with us, it was common for her to come down to the kitchen for coffee in the mornings just wearing her night time sleeping clothes. When the light caught her just right one could see through her nightie easily. I was in a tizzy every morning, trying to steal glances at her. She was about 42 and divorced, medium sized breasts and perky nipples, and at times I could see a darkish patch between her legs through her nightie.
My mom took about a week off from her job to stay home and entertain Wendy (not her real name, of course) but my Mom had to go back to work the second week. My Dad also worked everyday. It was in the summer before my freshman year at college and I was just taking it easy that summer, not working because I knew I had lots of work to do in college when school started.
During the week I was left alone with Wendy. She continued to come downstairs each morning in her short nightie and fix her coffee and she would sit on the couch and talk with me. Boy oh boy. I couldn't help looking at her nice looking legs as she sat on that couch. Her nightie didn't go down much past her upper thighs.
The morning I'll never forget was the next to last day that second week. As she sat there, I must have been too obvious scoping out her body. She told me she noticed I had been checking out her legs every morning. I told her they were great looking and I was sorry. She told me it was OK, that it made her feel appreciated. So, I asked her if she didn't really mind me looking at her and she said 'no!' OK, I just STARED at her legs then. She was playing with me in a way, saying she had just shaved them the night before and she stroked her legs saying how smooth they were ... then she smiled at me and asked me if I'd like to feel them.
I moved to her side and sat there and slowly stroked her legs and her upper thighs. They seemed incredibly smooth. Honestly, my dick went straight up in the air. As I rubbed her upper legs she told me how nice that felt. I'm sure she had noticed my hard-on. There was no way to hide it. Her pussy was hidden just inches above the hem line of her nightie. I ran my hand up her thigh again and as I got to the top of her thigh I just pulled her nightie up above her pussy mound. My gosh, she had a pussy with a thick crop of black or dark brown hair that wasn't overly long, but not overly close cut either. I just sighed and took my hand and stroked her thick pelt. She reached down and took my hand and pushed it hard against her pussy. She then used her right hand to grasp my aching hard dick through my pants. She was amazed how hard I was. Her breathing became choppy and she kept pushing my hand hard against her pussy with one hand as she mock jacked me through my pants with her other hand.
'I want to pull my dick out' I whispered.
'Yeah, pull it out' she panted. I took my pants off and was naked from the waist down. Her hand found my dick and she started beating me off with gentle but dedicated strokes. I hiked her gown up and leaned over and sucked her nipples and felt her breasts, then she parted her legs wide and I found her wet slit and inserted several fingers and started fingering her, then I'd rub her clit for a while, then I'd finger her more.
My heart was pounding wildly. I felt myself about to cum and she told me to stand in front of her. I quickly stood between her legs and she pulled her nightie way up. I squirted my cum all over her stomach and tits. She then used her own hand and finished herself off.
The next morning was her last morning there. My Mom and Dad said good bye to her when they left for work. Then we were alone again, for one last time. In the kitchen she hugged me and kissed me deeply fully on the lips with her tongue exploring my mouth. Without saying hardly a word, we both got totally naked and she jacked me and I fingered her again until we both came.
This incident with my Mom's friend goes down in my little book of memories as the absolute most exciting sexual experience of my life, and I'm 49 with many memories! I have jacked myself off a thousand times over the years thinking about it.