Lessons for My Son

When you've been doing this for awhile, and you both feel comfortable with where it is going, you might be ready for something else, and this something else can be a pretty big step. Don't even think of suggesting it until you have firmly established a baseline of sitting with her and occasionally cuddling.

Okay. Remember how you sometimes brush your fingers through her hair when you're cuddling? Well, women love to have their heads scratched. It does feel good - why do you think so many men fall asleep in the barber chair? So, do that more. Run your fingers through her hair, rubbing her scalp. Use your fingernails and lightly make long scratching rubs on her scalp. Don't make it the focus. Do it as if it's just something you're doing absentmindedly. If you're in the right moment and you have a firm foundation, she's liable to start purring like a cat.

If she says, "What the hell are you doing?", then you know you acted too soon. Immediately stop, act as if nothing happened, and back up a step. Don't be concerned if she acts a little cold with you for awhile. It's no big deal. It's not a show stopper. You just got a little ahead of yourself, and you need to spend more time establishing the basis of touching affection in your relationship. I should mention that recently I commented that she should teach you how to scratch her head. She said something like, "Oh, he'd never do that," and then kind of muttered, "Besides, that would be kind of creepy." I think that means a lot. First, it means that she never expects you to show her that kind of affection. But second, it means that she considers it a level of intimacy that might not be appropriate. So I'm telling you, if you get to where you can do this with her, it will mean a lot on several different levels.

If she does give you indications she likes it, then ask how you can do it better. You might even tell her that you want to be the best damned head scratcher in the world for her, and you can't do it if she doesn't give you instructions. What does this do for you? You're emphasizing that you want, more than anything, to please her. You're also indicating that you want her to teach you. There may come a time in the future where she's teaching you how to do other things that please her.

Make this a common pattern. Every time you sit with her and she's cuddling into you, rub her head. Make sure she likes it. Make sure she is comfortable enough with you that she wants you to do it. This will take time. Remember, this is not a horse race. This is a long journey, and you have all the time in the world. Spend time at it. Set a baseline.

Now the best position for a good head scratch is for her to rest her head in your lap so you can use both hands on her. She might suggest that, but chances are she will not. That is a pretty big step, isn't it? Having your Mom's head resting on your lap? (Stop. Close your eyes, and visualize that for a minute. Your Mother's head in your lap.) So, she might likely be very shy about bringing it up. If she doesn't suggest it, then you can prompt it by stopping rubbing her head - and you want to do this when she is clearly enjoying it in the moment. Tell her that the position cramps your hand, grab a pillow and put it on your lap, and she will get the idea. I think she'll plop her head right down on the pillow and you can give her the best head rub she's ever had.

If she does not go for it, or shows resistance, then that's okay. You'll get there. Don't make a big deal of it, but in the future just shorten the head scratching. Every time you quit - right when she's in the middle of enjoying it - say your hand is cramping. And occasionally put that pillow in your lap and suggest she just lay down for a minute so you can do it right. She'll get there.

When she does, concentrate on what you're doing. Your focus should be on her.

And look where you are. You have your Mom's head in your lap. The mental images that brings up are rather mind-blowing, aren't they? Did you think, in your wildest fantasies six months ago that you would be sitting there with your Mom's head in your lap?

You will be, I suspect, as hard as a diamond-cutting drill bit under that pillow. You could drive nails with that thing, you'll be so hard. Don't worry about it. That's what the pillow is for. You know it's there and, believe me, she will know it's there. You know what? Even with the pillow, she will be able to feel it. But the pillow allows both of you to act as if it's not there.

Your hard dick under that pillow will be the elephant in the room, so to speak. Neither of you will mention it. Neither of you will acknowledge it. But it's there, and you both know it. You can spend weeks or months at this step, and I suggest you do because it will be the most delicious part of your journey. It's the anticipation, isn't it? She will know what you want, you know very well what you want, and if you spend enough good time nurturing your relationship with her, the question becomes not if, but when.

After a lot of times at this you might, one night, just not put the pillow in your lap when she wants her head scratched and see if she goes for it. She might just put her head right in your lap, or she might say, "Get the pillow, Buster." If she tells you to get the pillow, laugh, and say, "Well, it was worth a try." See how she reacts to that. If she laughs with you, then you're in, because essentially what you just said to her was that you wanted a blow job. Wow. That came out of the blue, didn't it? But I know your Mother, and I know that's how she will interpret it. You're in. It's just going to take time now, but you're in.

When she rests her head in your lap, even with the pillow, notice what she does with her hands. At first, she will put her hands on the sides or in front of the pillow. She might, after several sessions, put her hands on the pillow and rest her face on them. It's all about details, so let's look at this. She'll start by putting her hands on the pillow in a position that she rests her face on the palms of her hands, but that's a little bit awkward and unnatural. The natural and more comfortable position for her hands is to place them on the pillow, palms down, and rest her face on the backs of her hands. When she does this the first time, she'll carefully position her hands so they are to either side of your...well... your dick. Take your time. Do it enough times and, I promise you, her hands will be resting on the pillow, right over your dick. She will be acutely conscious of that, but you must make no overt gesture that you're even aware of it.

Give it enough time, and eventually she will either go for it without the pillow, or she'll put her hands under the pillow and rest her head directly on the pillow. The first couple of times, she'll likely again position her hands on either side of your dick, not touching it. But believe me, she'll know it's there and before you know it her hands will be resting on your dick. At that point, you're pretty well progressed and how you handle it will be up to you. Again, I tell you, remember: Love. Respect. Trust.

As you're rubbing her head, make it as loving as you possibly can. Sometime after you have her comfortable, try this: Pause your rubbing and gently grasp her head with your hands. Later in this phase, and I mean much later, when you do this you can gently press her head into your lap. Gently, dammit! What you're telling her is that your dick is there, her head is there, and you'd like her to put the two together. Let's just get it out in the open. When you do that, you're asking for a blowjob. Don't say anything, just let her process it in her head. I assure you, though, she knows as well as you what that gesture says.