Susan was uneasy as she sat across from Andrew at the breakfast table. She'd rehearsed the speech she was about to deliver about a thousand times, but she was still nervous to the max. But now was not the time to back down. She took a deep breath and started.
"Andrew, I need to talk to you about something, and it might seem a little strange at first, so I just need you to trust me. OK?"
Andrew felt an immediate knot in his stomach, but he managed to say, "Sure Mon, I guess so. It sounds pretty important."
"Well, it's about you sweetie, and there isn't much more important to me than you. I hope you know how proud of you I was when you told me what you'd been doing with my panties. That took real courage. And I told you I wanted you to be able to take care of yourself whenever you need to, and that I would always knock before just barging in."
Andrew was definitely grabbing his ass, wondering where this was going. "Sure Mom, I felt better after I told you. I'm glad it made you feel proud of me."
"Well, I'm wondering if you might have misinterpreted what I was trying to tell you. I got to thinking that you might have thought that I was saying what you were doing is somehow a shameful thing that should only be done behind closed doors, and that instead of giving you the freedom to do it whenever you want, I was actually sending a negative message."
"No Mom, that's not the way I took it at all. But what makes you think I did?"
This was the part Susan was most nervous about. "Well sweetie, it's been two weeks since we had that conversation, and I don't think you've done it more than once or twice during that whole time. Such a big change seems too abrupt to a coincidence. And the more I thought about it, the more I wondered if what I said was making you feel bad about it. And that makes me sad and worried."
Of course the real reason Andrew was hardly masturbating at home was that he was doing it (and much more) with Heather almost every day. However, the two of them had agreed not to tell anyone about their intimate relations because they didn't think her parents would approve. But he couldn't play that card now. Instead he decided to go on the offence.
"Wow, Mom, I didn't take it that way at all, but how would you know what I've been doing? Are you spying on me?"
"Oh Sweetie, I just want the best for you, and I couldn't help but notice that there've been way fewer "used" tissues in your trash the past two weeks. I really wasn't trying to snoop, but there was no way I couldn't notice. I debated long and hard about having this conversation because I don't want you to feel like I'm violating your privacy, but I just really, really want what's best for you so I decided to take the chance. I love you so much Andrew!"
"Well, OK Mom, I believe you're not spying on me, but it's not what you think. So just relax OK? I appreciate you're trying to look out for me."
"Thank you for understanding Sweetie. But I've got an idea that I think will make both of us feel better. The message I was trying to deliver is that masturbation is an essential, natural, healthy thing for boys your age. It should be celebrated; not hidden behind closed doors. And I realized that the best way for me to make sure you understand is for you to do it while I offer my support and encouragement. After all, what could be wrong with sharing such a beautiful and important part of your life with someone who loves you?"
Wow! Andrew was stunned. His mom wants him to play with himself while she watches!! The thought of doing so was off the charts exciting. But also really intimidating. Would it cross some kind of line? And what would Heather think? Would she be jealous of his MOM? Emotions were swirling in his brain. Finally he said, "Gee Mom, I don't, I mean, Uhm, I, I..."
"Now Sweetie, I know this might be hard for you, but you might like it too. And besides, it's important to me, and I know you want what's best for me too. I've got it all planned. I've already told them I'm leaving work a little early. I'll be here when you get home from school and we'll have a nice talk, and then you can show me how you do it. Afterwards, I guarantee you'll never feel guilty or ashamed about your masturbating again. And we'll be able to talk about it openly whenever we want. You probably won't even care if I knock!"
Andrew was on information overload. He remembered how thrilling it was when he did it for Heather the first time, but that was a girl his own age, not his MOM! Did normal people do this kind of stuff? He felt like a pervert just smelling her panties; wasn't this worse? Still, the idea of stroking his cock and squirting all over the place while his mom whispers encouraging words in his ear was unbelievably exciting. He needed time to process.
"God Mom, I don't know. I guess I need time to think about it."
"You've got all day to think about it Sweetie, but I know you won't disappoint me. Think about how much this means to me...to both of us actually!"
Andy's day at school was a blur. The conversation with his mom was the only thing he could think about. Fortunately, he knew he'd see Heather in AP Physics and she could help him figure out what to do.
"You should totally do it!" was her immediate reaction. "Tell me it wouldn't be a huge turn-on to do it in front of your Mom! Besides, it sounds like she's only doing it to make sure you're OK. She must really love you Andy. I wish my Mom would do such a thing for me. It'll be so AWESOME!
"So you wouldn't be, like, jealous or something?"
"Jealous? Of you Mom! Get serious Andy. I think your Mom's giving you an amazing gift and you should milk it for all its worth."
"But I've got another idea! If you Mom's point is that touching youself is a natural, beautiful thing that should be shared, you should make her do it too! She can't say it's OK for you to do it, but not her. She'll have no choice! And it's not incest or anything; she's just showing you how she masturbates. Maybe you should even make her go first! Oh Andy, you've just GOT to do this! I wish I could be there too!"
Relief washed over Andy. He had a plan and suddenly he couldn't wait for school to be over. This was going to be a day to remember!
When he got home, his mom was sitting in the living room dressed casually in a pair of shorts and a tee-shirt. He wasn't used to thinking about his mom as a girl, but she still looked great. She was only 18 when she had Andy so now she's just 36. She had intelligent-looking brown eyes and a warm, embracing smile. Her trim body benefited from almost daily workouts and she had large captivating breasts. (Andrew happed to know that her bra size was 38D from a little snooping he had done in her underwear drawer).
"Hi Sweetie, I can't tell you how much I've been looking forward to this afternoon. Would you like a Coke or something?"
"No mom, I'm OK."
Susan didn't beat around the bush. As soon as Andy sat next to her on the couch, she said, "So Sweetie, tell me what you like most about masturbating."
Andy thought he was prepared for this, but the directness of her question took him by surprise.