Seeing from the expression on my face that I really wasn't understanding where she was trying to go with all of that, she told me "What I'm trying to say is that as good as you made me feel earlier from that brief encounter, now I want to find out if you can help me learn to loosen my sexual restraints, too."
From the faint blush I could see on her, I knew that she was a bit embarrassed; but the expression on her face told me that her determination was even greater.
The idea of getting intimate with her again certainly had its appeal, but I wasn't sure that I understood just what it was that she wanted from me. The only thing I could figure to do to try and settle the matter was to say "Katherine, you're a lovely woman, and I'd consider myself fortunate to share your company. But I'm afraid that I'm not entirely sure how I can help you."
Realizing that I was generally agreeable, but that she hadn't really given me any indication of what she wanted, she told me "My upbringing was rather… conservative. While my parents weren't particularly religious, subjects like sex were only spoken of very infrequently. Similarly, the schools I went to weren't inclined toward liberal teachings, either, so the little bit of sex education that I got was pretty much limited to explaining what a menstrual cycle was, and how babies are made – using animations, no less. I was a virgin up until my wedding night; my husbands history wasn't all that different from mine, so neither of us was particularly experienced or adventurous. The entire time we were married, the only sex we had was either with him on top of me, or the way you and I did it. There wasn't a lot of foreplay, and only rarely did we ever see each other actually nude. The pleasure I had today… it made me realize that there is a lot that I've missed out on, for one reason or another. I know that I can't learn everything all at once; but as much help as you've been, and after how good you made me feel, I would like to start learning from you."
"Are you sure you really want to do this? And with me? You understand that there are going to be… challenges?"
After she'd taken a deep breath and released it slowly, I could hear the certainty in her voice when she said "Yes, to all of that. I'm nervous, and even a little bit afraid – but dammit, I want better!"
I scooted toward her, then reached out to take one of her hands in both of mine before telling her "If it helps any, Katherine, I'm not going to try and force or push you to do anything; and I'm not going to do anything that you really don't want me to. All I ask is that you be willing to at least try something before deciding whether or not you like it. The very definition of discovery is to go beyond what's already known, right?"
Somewhat reassured, she managed to smile at me as she nodded her head in understanding and agreement. Lifting her hand to my lips, I kissed it before telling her "There are a couple of things you've said that caught my attention: that you've held in your desires, and that you and your husband almost never saw each other nude. If you've been holding those desires in, then I'm taking that to mean that you haven't taken care of them yourself – or at least, not often, anyway."
Seeing the uncertainty on her face, I elaborated "You don't masturbate?"
The resulting blush was something to see before she got control of herself enough to answer "Uh, no, not… not really."
"That's okay, Katherine. You told me how you grew up, and I can understand that it would be a little embarrassing to talk about it."
"Try a lot embarrassing!", she declared, before I continued "What you need to understand is that not only is that a perfectly healthy and reasonable thing to do, it's also something that everybody does."
She looked at me a bit uncertainly, and I told her "Okay, then, how about if we start out by taking care of a couple of things: nudity and pleasuring yourself?"
The first reaction I saw was reluctance; but after a few seconds, she realized that she had to start somewhere, and nodded her acceptance before asking "Will… will it just be me?"
"If I'm not there for the nudity part of it, you aren't actually accomplishing anything, are you? As for the rest, that's really up to you. I think that I can probably help you, but if you're really that worried or nervous, then I can leave you alone. Or, if you think it would help, I'm perfectly willing to be nude and masturbate with you, to show you that it really isn't something you need to be embarrassed or ashamed about."
She considered that for a few moments before responding "I think I'd like that – you being there, too, and, um, doing it with me. I think I'd like to see how you, I mean, a man… does that."
I waited a bit, and finally realized that she was going to need a little help getting started. After standing up, I gently guided her to stand with me before moving behind her and slowly unzipping her dress, then slipping it off her shoulders. That done, I slid it down past her hips and carefully guided her to step out of it. Then I had the pleasure of rolling her stockings down her legs before I finished up by slipping my thumbs under the waistband of the panties she had on and slipping them down her legs, too.
With her standing there nude, I moved back around so that I was standing a few feet in front of her before calmly taking my own clothes off just as I would at home. I noticed, but didn't comment on, that her nipples erected as she watched me undress.
Once both of us were ready, I stepped forward again and gently guided her to sit on the couch again before taking a seat next to her. Her legs were closed, and her hands were fidgeting slightly in her lap; knowing that I needed to settle her down a bit, I took her hands in mine and held them before looking into her eyes and calmly telling her "Katherine, it's okay – really. I'm here to help you, just like you said you wanted me to. I'm not going to push you, but I'm not going to let you give up, either, okay?"
Slowly, she nodded, and finally answered "Yes, thank you, James."
Still looking into her eyes, I said "You told me that you're nervous, and even afraid – and I can understand that. I'm not going to just start grabbing you, or poking at you, or anything like that. Instead, what I want is for you to tell me what you feel and what you like, and I'll help you make it happen. If you can let go of some of that, I can help you learn to give yourself pleasure. If you can stay with me, we can help you learn what feels good and how to make yourself feel good. Do you think you can do that?"
Realizing that I was willing to take things slowly seemed to give her some comfort, and even confidence: she managed a weak smile and nodded again before closing her eyes.
"When you think about having sex, what's the first thing you notice about yourself?", I asked.
"My breasts; I can feel them get tight, and my nipples get hard."
"Do you like to have your breasts touched? How? What about your nipples?"
"Yes – I want to feel his hands on my breasts; just holding them at first, but then caressing them, and squeezing them."
I released one of her hands and moved it to her breast, cupping it from underneath, and heard her say "Yes, like that."
"Go ahead and put your hand on mine, and move it. Show me what you want", I suggested. A moment later, her hand was on mine and she was guiding my hand around on first one mammary, then the other. I continued to softly talk to her, directing her to guide my hand and change how and where I touched her. It didn't take long before we had both of her silver-dollar-sized areolas puckered, and her crayon-diameter nipples standing erect in response to the caresses and soft squeezing of her breasts, and the gentle tweaking and pulling of her nipples.
I maintained an almost continuous soft patter with her: offering encouragement, seeking and offering guidance, and giving and receiving feedback as I slowly and carefully drew out more and more detail, and helped her move along the path toward higher and higher arousal. She didn't hesitate in the slightest to let me know when she took notice of the area between her thighs, and readily parted them so that we could include her vaginal opening and labia and clitoris in her ministrations; when my hand left her breasts, she didn't hesitate to replace it with her own.