This happened when I was about 16 or so.
I was at my friend's house spending the night when we started getting a little punchy. He mentioned that his dad had a good collection of porn in his bedroom. We went up to the room to root through the tapes and magazines. He mentioned that his mom also had a few secrets. He opened her dresser drawer and moved some things to reveal three sex toys. Being somewhat sheltered I'd only actually seen these in a magazine once before. There before me were three imposing looking dildos / vibrators!
That night we went downstairs and watched some porn. Really this was my first experience watching with someone else, and I was getting into it, but my mind kept going back to those toys in the drawer of his mom's dresser.
When my friend fell asleep I snuck upstairs and took out all three dildos. I ran to their bathroom to take a closer look. The first one was one of those standard white vibrators that you see everywhere. It had a number of sleeves that could fit over it to change it's texture. The second was a thin, but long attachment that fit over the white one. Finally, the third was the most impressive. This was one of those 10' pliable flesh-colored dildos. To a 16-year-old boy, absolutely huge. I was terribly turned on by just holding this huge rubber member in my hands thinking about my friend's mom shoving this into herself. I had to relieve myself right then...
The next morning my friend's mom had returned from work and went upstairs to head to bed. My friend had to leave to go to some event, so I was getting ready to leave. At this point I was left by myself in his house since he'd left and his mom was upstairs settling in for bed. Being a sick little monkey I snuck upstairs to peek in on his mom. In some weird way I had hoped that she'd pull out her toys to play before sleeping. Of course, that only happens in magazines, so all I saw was her laying in bed in her nightgown. She wasn't a bad looking woman. Fairly thin for her age, early 40's, black hair with a few specks of grey. She was tall with long legs. I'd never really liked her much. Somewhat of a bitch really. I peeked around the door to try to get a glimpse of her when the door squeeked. She looked right over at me and asked me, in a stern voice, if she could 'help me'. This was my chance...
I walked in slowly and asked her to explain what these things in her drawer were for. I opened the drawer and tossed two of the sex toys onto her bed. She was absolutely shocked. She just sat there with her mouth open. I know she wanted to ask me about why I was in her drawer in the first place. Not to mention how I had the gall to confront her on it's contents. (honestly it was the bravest moment of my life) The fact was clear though. She was caught and I was in a position to embarrass her greatly. She was a local business woman and area political office holder. I knew this and took the risk of my life.
I told her to show me how she uses them. She reluctantly removed her gown to reveal a nicely toned body for a 40-year-old. Her tits were small, but surprisingly firm. She reached into her bedstand and pulled out a tube of lubricating jelly. She applied some to the tip of the white vibrator when I stopped her. I told her to use the monster 10-incher. She protested that she doesn't really use that one unless she's really into it. I wasn't in her bedroom to see her play with herself, I wanted to see what she could really do. I tossed her the 10' cock and she started to lube it up heavily. She slowly crept the thing into her pussy, taking special care to show me exactly what she did with this thing. I stood at the end of the bed, fully clothed, watching as she steadily twisted and pushed the big rubber dick into her waiting pussy. She started to moan softly as instinct took over as she was pumping the thing in and out of her now sopping cunt. She was really getting into it by now and her long legs started to lift off the bed so I could get a direct view of her ass. I reached back into her drawer and pulled out that long thin attachment and affixed it to the vibrator. She was too preoccupied to notice that I'd lubed it up and was poised to assist her in her efforts.
Her gasp was priceless. While she was literally fucking herself with a giant rubber dick I'd lubed up a thin vibrator and positioned it just above her asshole. I slowly slid the phallus into her ass. She opened her eyes wide to see me on the bed, inches away from her pumping hand, smelling her dripping cunt. She hesitated for a minute, but went right back to what she was doing. I started sliding the length of this thin dildo in and out of her ass while she rammed the 10 incher into herself. That was it. She started to shudder and her breathing became much more shallow. She ordered me to 'shove it in all the way', so I took the vibrator and pushed it deep until it stopped. She gave herself a few more good thrusts until she just clenched up. Her whole body tightened as she had an intense orgasm. When she could finally breathe she gasped and screamed as the orgasm pulsed through her body. This was absolutely intense. I was experiencing my very first live female orgasm, and it was coming from my friend's mother.
The pool of sweat and juices were covering the sheets and making her skin glisten as she came down from her O. She was so embarrassed by what she had done. She grabbed my shirt and pulled me toward her. I had thought that she was going to kiss me, but it was more to threaten me. She told me that if I were to tell anyone that she'd tell my parents what I had done. We agreed to make this something that stayed between us. Fine by me since I had to dash home before I exploded in my pants. I left her lying there with a vibrator in her ass, juices flowing out of her pussy, and an exhausted look on her face.
I'd seen her in public a few times since then. Usually it is one of those awkward moments where we see each other and immediately look away. That was about 13 years ago and I still swear I can smell her scent. I never told anyone about this, and I assume that neither has she. It is still one of the most vivid memories that I have from that time in my life.