On the day that I was to meet Jilly for the first time, I arrived at the designated cafe a little early, and positioned myself where I could watch the door. I had a pretty good idea what her body looked like, since she'd posted a few pictures online at a fetish place. But I wanted to see her body in motion - how she carried herself.
When she walked in, I recognized her immediately. She stood near the doorway, turning slowly, scanning the room as she looked for me. This gave me a chance to admire her thin body, with its small breasts and a really nice ass. I've always been somewhat of an ass man, so I took special interest in hers. She spotted me, smiled, and began walking towards me. During this short journey, I managed to look higher than her torso, up past her long, graceful neck, and noted her charming dirty blonde hair, blue eyes, and generous, sensual mouth. Probably in her late 40s or early 50s, she looked magnificent.
For this meeting, she'd dressed conservatively, almost professionally, in a gray tailored pants suit. Perhaps the single concession to femininity was evidenced by the simple strand of pearls around her neck. As she reached me, she extended her hand, saying, "Hello. I'm Jilly. I'm really glad to meet you." Her cool, slim hand felt good in mine, as I introduced myself, shaking hands with her.
"What would you like to drink? And can I get us something to eat?" I asked.
"I'd like a tall latte, please. And perhaps one of those yummy looking pastries?" she replied. I was starting to be enchanted by the tone of her voice.
Retiring to a quiet corner, we sat close side-by-side, drinking our coffee, nibbling on the pastries, and feeling each other out verbally. We talked very quietly at times, if we discussed something sensitive. But first we started with generalities. Jilly learned about my age, my unattached status, a little bit about my work, and my taste in music.
I learned that she was a single mother, raising a 22-year-old stepson, Jim, whose father had died over five years ago. Of course, Jim was old enough to be out on his own in the world, but he hadn't launched himself from the nest yet. She shared that she was 49, also unattached, and ran her own business from her home. Apparently, her business didn't bring in much money, but she was quite frank about the fact that her late husband had provided well for her, both in his investments, and with his life insurance.
The more we chatted, the more we relaxed. It became obvious that our value systems and sense of humor were compatible. We spoke openly and candidly, knowing that clarity was crucial to understanding. Preliminaries established, we moved on to more intimate matters, sometimes speaking quietly into the other person's ear.
"What was it about my online postings that led you to contact me, Jilly?" I inquired.
I saw her blush for the first time. "I saw what you were doing with that other woman in those pictures, and I started fantasizing about taking her place," she began. "You said you looked at my page. If so, you saw that I like dressing up in erotic clothing. Some people might call them slutty outfits. But I've never had anyone tie me up, or do things to me like I saw in your pictures."
I interrupted. "You never did things like that with your husband?"
She smiled a wistful smile. "No. Nothing like that. He was a loving husband, and we had great sex. But we never did anything remotely kinky. We had what you might call a 'vanilla' lifestyle."
I nodded my understanding. "Please continue."
"The more I look at such pictures, the more I feel that I'm missing out on something. I feel a yearning inside me for experiences like that," she said quietly. "I don't know if I'd really enjoy those things or not. But I won't really know unless I try them." She paused, and looked away shyly. In a voice so low that I could barely hear her, she said, "And I think I'd like to try them with you, if you're willing to be patient with me."
Her very lack of experience intrigued me. The fact that she felt drawn to this, even though she'd never experienced it was fascinating. I was flattered that she'd chosen me, and also glad. I was willing to take a slow pace with her. To let her put her toe in the water, so to speak. But I wanted to establish the proper expectations for both of us before we could agree to start.
Very quietly, I said to her, "Let me say this. In many of those pictures, you see women being tied up. Sometimes you see them spanked or paddled. In some pictures, you see them being humiliated, being made to wear a collar, be led around crawling at the end of a leash, even acting like a piece of furniture, like a foot stool." I was watching her eyes closely as I said these things, watching her pupils constrict or dilate. "Sometimes, sex is involved when the woman is bound, helpless and vulnerable. In the past, I've done all these things. But I wouldn't do them with you without your full consent, either overtly or tacitly."
Jilly's cheeks and neck were reddening, and we were sitting so close together that I could feel the heat radiating from those areas. I couldn't tell if her flush was due to excitement, or to disgust at the thought of those various acts. I went on, "To be honest with you, my interests tend more towards a D/s lifestyle, rather than BDSM."
"I know what BDSM means," Jilly said softly. "But what does D/s mean?"
"That stands for Dominance and submission. I enjoy telling my submissive to do things - things that might press gently against her limits. She's never forced to do anything. If she does them, it's because she chooses to do them. Submission is always done by choice," I explained.
"Can you give me an example?" she asked.
I thought for a moment. "Suppose I was going to take you to the art museum. And for this journey, I told you to wear a thin, silky white blouse with no bra under it. You know that the air-conditioning makes the interior of the art museum cool all the time."
Jilly was concentrating, mentally processing my proposed scenario. Her pupils dilated, signifying a mild shock. "But that means that my nipples would stiffen, and poke out prominently against that thin material." She gasped quietly. "Come to think of it, if the blouse was both thin and white, I'm guessing that people would be able to see the darker circles of my areolae around those prominent nipples!"
"Exactly," I stated. "How do you think that would make you feel?"
She swallowed as she considered my question. "I think that I'd feel like everyone walking by us would be staring at my breasts. Some of them might be looking at them with disapproval, and others might be leering at me - and I don't honestly know which would be worse." She shifted back and forth in her seat slightly, then whispered into my ear, "For some reason, just thinking about this is turning me on. When can we do it?"
At that point, I knew that I'd found my next submissive.
It was decided that she'd visit me regularly at my place. A 24/7 arrangement was, of course, impossible, since her stepson Jim still lived with her. During Jilly's first few visits, we treated them as a trial period, since she was mentally attracted to kinkiness, but had no real experience with it.
