Chapter 4: Kate’s First Masturbation Lesson

It was almost three weeks before I heard anything again from Kate. There were a number of times when I was tempted to call her and find out how she was doing but I forced myself to set the phone aside and be patient. Maybe she was more freaked out by the day at the mall than I had thought. As innocent as that day had been, at least from my perspective, I knew it had most likely blindsided her out a bit - or maybe even a lot. It was killing me not knowing how had things gone with her husband. Did she have the nerve to show it to him? Did he like it? Did it “motivate” him as we had hoped?

It was almost got to the point where I was afraid she had chickened out or something else had happened to stop her from carrying on any further with me. Then one morning my phone rang and my heart jumped as I saw who it was that was calling me - Kate!

“Hi Kelly, sorry I haven’t gotten back to you sooner but with holidays and all ... well, you know how it is,” she apologized.

Trying not to sound as anxious as I was feeling, I assured it that everything was fine and for a few minutes we discussed our Christmas gifts and what we did for New year’s Eve, that sort of trivia. Finally, just as I was starting to wonder if we would ever get to the point, she asked me if I could stop over for some coffee and lunch, that she wanted to talk to me about some “things”. This wasn’t the time to tell her about my passionate dislike for coffee so I simply agreed to come over in a little while.

After hanging up, I had to wonder what Kate had in mind. Did this have anything to do with her original phone call and request to me? Maybe it was nothing beyond some more clothing advice. She hadn’t mentioned a word about her husband - was that a good sign or bad? I threw on some comfortable jeans and a t-shirt, nothing sexy or special, and drove over to her place, arriving a few minutes after the noon hour.

Kate must have been watching for me because she greeted me at the door as I approached up the walkway. Once I stepped in, she closed the door behind me, talking my coat and hanging it up in the hallway closet. I noticed she was dressed in jeans as well, but with a nice shirt on that she had left hanging out. It gave her an authentic “mom at home” look.

“Sorry, I didn’t ask if you liked coffee,” she said, leading me into the kitchen.

I apologized as well, telling her I never drank it but a diet soft drink or even just water was fine with me. Fortunately, she had a couple cans of Diet Coke in the refrigerator which was perfect for me and we sat at the kitchen table while she mixed up some cream and sugar with her coffee.

“Well, so how did things go when you got home after our shopping trip?” I finally had to ask after we spent the first ten minutes or so talking about TV reality shows and local gossip.

Kate’s smile suddenly changed to a frown and I worried that I may have asked the wrong question.

“Oh Kelly, I DID try ... I really did!” she said, her eyes starting to tear up. “Bruce was surprised ... to say the least, maybe more like shocked but still I think he liked it on me. Then he asked me whatever possessed me to buy such an outfit and when I tried to tell him what happened he turned away and acted like he didn’t want to know. Then he got mad at me for `wasting’ so much money and even accused me of unfairly taunting him when I knew there was nothing he could do to respond properly.”

Naturally I was more than a little surprised to hear all this. Sheesh, what a jerk! Here his wife tries to do her best to seduce him and all he does is lay a guilt trip on her for HIS malfunctioning dick - IF it was malfunctioning in the first place.

Kate continued, reaching for a Kleenex on the kitchen counter, “So needless to say, we didn’t do anything. God Kelly, I guess I can say this to you ... I was SO damn horny. I felt like going out on the deck and just screaming, the frustration was THAT big in me. It was so much fun and I came home feeling soooooo good after being out with you and then WHAM, it was all over, just like that.”

Kate sat there quietly, not saying another word and the room was deathly quiet for a few minutes, so quiet I could hear the fizzle of my Diet Coke. All I could think about was what I should say next - and maybe what NOT to say.

Then I recalled why she had gotten in touch with me in the first place and how maybe it was even more important now than ever for her to find the proper outlet for her sexual frustrations. Reaching over the table, I took her hands in mine and our eyes met as the silence continued. It was like she was silently pleading with me, her eyes imploring me to help her, to take that first step that she knew she never could - but wanted to do so badly.

“Kate, do you still want me to help you masturbate?” I finally said softly, figuring it was better to just get straight to the point and not fool around with silly euphemisms.

“I guess so,” she replied, so softly that even in the awkward silence I could barely make it out.

“What do you say we go to your bedroom, OK?”

She bit her lower lip, almost like it was back in her teenage days and it was the first time she was considering going to her bedroom with a boy - or wherever it was that she had her first sexual experience. Finally she just nodded silently and led me up the stairs into the master bedroom. It was nothing TOO fancy but at the same time, just right for someone like her. A queen sized bed with cherry furniture that looked pretty well made. There was a door that looked to lead to a master bathroom and I could just make out the entrance to a large walking closet at the back of it. At first we just stood there, maybe a foot or so apart, our arms to our sides, each waiting for the other to make a move.

It didn’t take the genius of a rocket scientist to realize that Kate was never going to initiate anything. As for me, this was all new territory as well. I’d never been in such a position with a woman older than me, for that matter not with one younger than me either! Really, where do you start I a situation that’s practically like having to teach you mother to pleasure herself?

“SO have you ever seen anyone masturbate?” I asked her, trying to break the ice.

“Well, I told you before that I’ve seen my husband doing it,” she answered. “I thought it was disgusting.”

OK, so I worded THAT question wrong. “I meant ... have you ever seen a WOMAN masturbating?”

“Oh noooooo, never,” she said softly. “I remember back in my youth camp days some of the sluttier girls would put their hands in their panties at night but it’s not like I really WATCHED them or anything like that.”

I smiled at the way she referred to them as “the sluttier girls”. No doubt that description would have fit me had we gone to camp together!

“Well then Kate, do you think it would help if maybe you watched me do it first?” I offered tentatively, still not really sure how to play my hand.

“Oh I don’t know ... I’m not sure I could watch that,” she said, retreating just a bit at just the suggestion of seeing another girl having sex with herself.

Nonplussed at her initial rejection, I patted the edge of the bed towards the foot. “So why don’t you just sit here and don’t say another word ... just watch me. Remember - not a word.”

Kate started to say something but I knew it would just be more reasons for NOT watching me so I shushed her and patted the bed again. This time she listened to me and took her seat. In the back of my mind I was a bag of mixed emotions. As much as I LOVE to masturbate and as much as I LOVE to have someone watch me, this was completely different from turning on a boy in the front seat of his car. It was a bit frustrating because I don’t think Kate saw me in any sort of sexual way, at least not in terms of being turned on by me. If she was so straight, how would she react to me doing anything in front of her? Heck, for THAT matter, how would I react to someone with her attitude watching me?

Well, there was only one way to find out. What the heck, what was the worst that could happen? So I took a deep breath and undressed in front of her. When I started, my intent was only to lower my jeans enough to rub myself but then I suddenly changed my mind and decided to go for it all - be totally nude.

From the way Kate was looking at me, I suspected she had also expected a more minimalist approach and when she realized that I was stripping down all the way, her eyes widened and I thought I could see some redness on her cheeks. It was then I realized that she had not seen me undress during our day at the mall and so she hadn’t seen me nude since the party which was now a couple of months in the past. Even then, I hadn’t technically been nude but given what I was wearing at times there wasn’t much difference. Also, when I model at parties I try not to make it overly sensual, at least not in the way I would’ve had I been trying to turn on a partner.

When I was naked I got up on the bed and arranged the pillows so I could lay back against them and be propped up enough to see what I was doing. At first I just laid back with my legs outstretched in front of me, my bare feet just a little bit away from where she was sitting. The room wasn’t what I would call cold but then it wasn’t exactly hot either and I could feel a few goose bumps rising on my legs and arms. My nipples were already at attention and I hadn’t even touched them yet!

“Are you cold?” Kate asked, a note of concern in her voice, “I can turn up the thermostat if it would help. Bruce keeps the house so damn chilly all the time.”

I assured her that I was just fine and besides, I was expecting things to heat up nicely on their own in a few minutes anyway! There was no sense in delaying any further so I started to talk to her, to explain what I was doing.

“I guess every woman does it a little different,” I started off, “Some like to use toys, others just their fingers ... Me ... I’m a finger girl all the way. I think that toys are something you can try after you’ve mastered using your fingers.”

As she watched I pulled my legs back until my feet were flat on the bedspread with my knees together. Then I slowly spread my legs apart, keeping my knees straight up which effectively parted my thighs, giving Kate an unobstructed view of my freshly shaved crotch. Seeing her looking at me made me feel excited yet strangely nervous. After all, as much as I loved to have someone watch me masturbate and as many times as I’ve done so in the past, especially as a high school teen on dates, usually it was as much watching the other person getting turned on by seeing me masturbate as much as it was what I was doing to myself that got me going.

In this case, while I was hoping Kate would get at least a little bit turned on by me, it was almost clinical rather than being erotic. Sort of like those sex-ed videos they showed us in grade school where someone took extraordinary effort to make sex as unexciting as possible. My hands cupped my boobs, hefting them a bit and then I started to gently massage them.

“Usually I like to start out just touching myself - you know, massaging my boobs, feeling myself all over,” I explained softly as my fingers pulled gently on my stiff nipples, then letting them snap back in place before I put my fingers around them again as my hands covered my breasts.

I’ve always enjoyed playing with my boobs, even when they were barely bumps on my chest. As I went through puberty, there would be those days when they would hurt as they grew (slowly I might add) and I learned that by playing with them, it helped them to feel much better.

As I touched myself I remembered how I use to wish I could lick and suck on my nipples the way my best friend Beth could when she was getting herself off with me. Unfortunately, I was years behind her before I could finally do that to myself. Now I bent my head down and pulled my breast to my mouth, taking my hardened nipple in my mouth and feeling it’s stiff yet soft feel on my tongue. God it felt so good! My eyes looked up at Kate as I suckled my own breast and I felt a twinge between my legs at the sight of her staring at me, not moving or doing anything but at the same time unable to take her eyes off of me.

Sighing softly, I released my nipples and leaned back, allowing my hands to roam all over me, feeling the light touch of my fingertips as they traced lightly over my sensitive skin as they traveled down from my chest, over my smooth belly, and then down along the tops of my bare thighs, only to return along the same path to my breasts. The goose bumps raised even more and this time I couldn’t blame the thermostat setting! Each trip my fingers would dip just a little bit further between my thighs until finally I was drawing an imaginary line just at the outskirts of my shaved pussy slit, coming as close as possible without actually quite touching myself there.

“You don’t have to rush into anything,” I explained to her gently, trying to remember that this wasn’t just for my own pleasure and I needed to explain things to her, “Just relax ... enjoy the feeling of your body, admire the softness of your skin, concentrate on how it feels to touch yourself - as only YOU know how you want to be touched.”