I've never ever mentioned this to anybody before!
When I was 8 years old my mom and dad got divorced. I lived with my mom from then on. Besides being my mom, she became my best friend. We did everything together. She had me when she was just 18 years old, so although she was much older than I, she wasn't THAT much older.
When I was about 16 she tried telling me about the birds and bees, but I already had learned all that stuff. That conversation didn't last long and she said she figured I had already learned most of it. I had already been jacking off for probably 3 years by then!
Honestly, who among us has never had at least ONE sexual fantasy about a parent? When I learned about sex I was constantly trying to catch a glimpse of my mom in her bra and panties or less. I certainly was curious. She always looked pretty good, not overweight or anything. I had my share of jack off fantasies about her as well as every other girl at school I knew.
One afternoon my mom and I got into a conversation about sex. I was probably 17 then. She asked me if I was still a virgin. I sheepishly admitted I was and she told me she was glad I still was a virgin. Then I was shocked and blown away when she asked me if I masturbated. That is something most of us would be embarrassed to admit to our parents. I said 'No!' She smiled and she said she knew I did. She said 'everyone does.' She said not to be embarrassed. She said 'I even do it.' I said 'really?'
She told me how everyone had needs, it felt good, it was normal, it wasn't dangerous, and everyone did it. I then sheepishly admitted I did it. Well, I KNEW how guys did it, but I didn't quite know how girls did it back then. I said 'mom ... how exactly do girls do that?'
She proceeded to tell me about the female anatomy and how manual stimulation in kind of the same way could give them orgasms too. As she was telling me about 'vaginas' and using some of the medical words, I started getting a bit turned on. I guess it showed.
She asked me 'are you getting an erection?' I was embarrassed as Hell. I was probably bright red in the face. I told her that trying to imagine what she was telling me just affected me that way.
What follows here I will never ever forget. She looked right at my crotch and said 'let me see it.' I was fidgeting and getting nervous. She said 'really, let me see it.' I stood up and pulled my pants and underwear down in front of her. My dick was rock hard. She told me she was impressed and I was all grown up. 'I'm proud of you,' she said. I just stood there. I didn't know what to do!
Then she said 'let's do something once that will never happen again.' Now she used the street word ... 'if you'd like to jack off I'd like to watch you.' Thoughts of some of my jack off sessions fantasizing about my mom flew through my head. I was so hard as I stood there with her looking at me. She said 'you need to learn a few things. If you'll jack off, I will show you how women do it.' How could I pass this up?!!
I told her that would be OK with me. She said 'come on, let's go to the bedroom.' In the bedroom, she started getting undressed and she said 'take your pants off.' As I removed my pants and underwear, I watched my mom strip totally naked. I had only caught glimpses of her in bra and panties a few times but never totally naked. I was mesmorized by her hairy bush and the nipples on the ends of her medium sized boobs. She laid down on the bed and opened her legs giving me my very first close up look at a woman's bare pussy. She used her hands and identified the parts she had told me about, like the clitoris. I couldn't take my eyes off her pussy.
She told me to get on the bed and get in a comfortable position where I could watch her. As she began masturbating she was explaining feelings surging through her groin and body. I was so mesmorized I wasn't even jacking myself. I stayed rock hard though. She eventually stopped talking as she really got into it, occasionally fingering her pussy, but mostly stimulating her clit. She finally had a big orgasm and I was almost frightened by the way she tensed up and gasped. She was finally done.
She looked at my dick and used her finger to wipe up a huge amount of pre-cum rolling down my dick. 'Now I want to see you jack off,' she said. I laid down on my back and she laid beside me with her head propped up on her hand. She was on her side. I remember this like it was yesterday.
With my right hand I started jacking my dick. She asked me a few questions like if I usually did it slowly or fast, and if I came in a tissue or shot it on my tummy, stuff like that. She watched me intently as I jacked. I was so turned on by what I had just witnessed, and the excitement of doing this in front of a woman, that I didn't last long. I suddenly started shooting cum all over my lower stomach. Afterwards, she got up and got some tissues and she wiped all my cum off of me. She then said that was a learning experience for me, to enjoy my masturbating in the future, and we wouldn't do this again.
For a year after that I jacked off constantly remembering that day. I wanted to do it again badly with her. I was afraid she would say no, and I was really afraid she might get mad if I asked her. One day I was so turned on in my room. I wanted to jack off badly. My mom was in the living room watching TV. I thought 'what the Hell.' I walked into the living room stark naked and raging hard. I came up behind her and she didn't hear me coming. I stepped in front of her and her eyes popped out. I really surprised her.
She said 'what are you doing!' I said 'Mom ... I want to jack off so bad right now ... would you watch me again?' I could see the indecision in her face but she said 'OK ... and this is the last time.' I asked her if she would masturbate with me but she said no. Then I got my courage up and I asked 'would you jack me off?'
She told me to bring her some tissues. As she sat in the chair in the living room, she took my dick in my hand and started jacking me off. She told me I was really very hard. I don't think she jacked me 3 minutes and I was ready to cum. I told her and she held the tissues near the end of my dick and I started cumming into the tissues. She held them so she could still see me squirting though. 'Now go get dressed,' she said!
That was the last time this ever happened. I continued to beat my meat for years, actually to this day thinking about those two incidents. She and I never discussed those incidents again.