Tales From a Nascent Dominant

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.

For instance, the first time she knelt at my feet she was fully clothed. I taught her the posture I wished her to use - butt resting on her heels, torso upright, palms up on her knees, chin slightly down, eyes looking at my feet. We chatted while she was thus posed for a while, then I asked, "How does this pose make you feel? Don't give a snap response, Jilly. Consider your answer."

She thought about it for a while. "At first, it seemed just strange, and a little uncomfortable. But now it's rather peaceful and calming - like it's the right way to be."

"Suppose we were in a room filled with people, and we were like this. Would that change how you'd feel, do you think?" I asked.

It was wonderful, seeing a pink blush appear on her cheeks. "It'd be embarrassing, Sir," she replied. Yes, she'd instinctively begun calling me 'Sir' when she was alone with me. "Oh!" she exclaimed.

"Oh? Why did you say that?" I inquired.

Her blush deepened. She stammered a bit, trying to respond. "I... I... umm... when I imagined kneeling at your feet, with other people watching..."

"Yes?" I prompted.

She whispered, "I got wet."

"You mean your pussy started to leak?" I asked, grinning. She nodded, getting a bit redder. "You want to show me how wet you are, don't you?" I asked. She was motionless. "I think that deep inside you is the desire to display your wetness to me." I let her consider that, then continued, "You have my permission to stand up, and show me."

She trembled in a most fetching fashion, debating internally. Even though she'd posted pictures of herself dressed in slutty outfits, I'd never seen her cunt or breasts naked yet. Finally, she rose slowly to her feet, and, not making eye contact, raised the hem of her skirt. Holding it up, her other hand hooked into the leg hole of her wet panties, and drew the material sideways, exposing her labia and slit. She was indeed wet and aroused.

"I think you should take off those wet panties, Jilly, and give them a chance to dry off before you return home later," I suggested.

She bit her lip charmingly, and a few moments later, tugged her panties down, and stepped out of them. To my surprise, after spreading her panties out on a nearby table, she returned to step in front of me and used both her hands, raising her skirt to give me an excellent look at her cunt.

After giving it due admiration, I looked up at her face and caught her warily watching my expression, perhaps fearing I was judging her negatively. Feeling the need to reassure her, I stated, "Jilly, your pussy is beautiful. I see no reason why you should ever hide it when you're with me."

A smile burst out on her face that reminded me of a glorious summer sunrise. Without speaking, she unhooked and unzipped her skirt, and stepped free from it. Bottomless, she stood before me, even shyly opening her thighs a tiny bit to enhance her display. But I saw a fleeting expression of concern on her face now.

"Yes, my dear? You're worried about something? Speak freely," I said.

"Well, Sir, it's just that I feel weird only wearing a top like this." Her blush deepened as she boldly asked, "Would it be all right if I took the rest of my clothes off?"

I suppressed an impulse to laugh. As if I would ever refuse letting a lovely woman strip for me. With a magnanimous wave of my hand, I told her, "Jilly, when you're here with me, you never have to wear a stitch of clothing. We can make that a rule, if you find it exciting."

As she unbuttoned her blouse, and removed it and her bra, she again looked toward my feet, and stated, "You told me to speak freely, Sir. So I'd like to tell you that there is one item, at least, that I'd like to wear when I'm here."

Curious, I asked, "And what is that?"

She unconsciously put both her hands in front of her pussy in a protective gesture. "A collar, Sir. Your collar. I've seen pictures of women wearing them online, and I'd like to see what it feels like to wear one. I'd like to feel like you 'own' me, if that makes any sense."

"Would you like to beg me for my collar, girl?" I asked her, letting a mild imperial tone color my voice.

She immediately dropped to her knees, close enough that she could place her hands on my knees as she looked earnestly up into my face, pleading, "Please, Sir. May I wear your collar? I want to be yours."

"So, are you asking me for an exclusive relationship, Jilly?" I inquired softly.

She swallowed hard before answering. "Not exactly, Sir. In my heart, I feel that you may own as many submissives as you wish. I don't feel jealous. But my heart says that it only feels right to me to belong to one person. And I'd like that to be you."

This was an interesting statement for her to make. I had no intention of having a 'stable' of submissives, but it was nice to hear her distinction that I could have many D/s relationships, but she only wanted one. "Very well, girl. I'll find a collar for you," I told her, watching the joy spread across her face.

The next time she visited, I showed her the collar I'd procured. It was basically a black leather collar, with an inconspicuous steel loop in the front and in the back. With those loops, I could attach a leash to the front if I led her, walking upright. Or I could attach the leash to the back loop if I decided to have her crawl at my side. The front center of the collar had a lovely cameo as decoration, giving it the appearance of an elegant choker. Jilly knelt naked before me, shedding tears of happiness, as I fastened the collar around her neck. It emphasized the long grace of her neck magnificently, and I told her so. "You'll only wear this when I'm with you, my girl," I stated. I heard her gasp.

"You called me 'my girl' Sir!" she whispered. "That sounds so lovely to me."

"And you are now my girl," I assured her. After a pause, I said, "Speaking of what I call you, Jilly. I've noticed that at least some forms of humiliation seem to turn you on, and we'll examine this more closely. But humiliation can take a verbal form. Suppose during our interactions, I decide to call you 'slut' or 'whore' or 'bitch' or other names, as I feel moved to do. Would these offend you, or excite you, do you think?

"Just hearing them out of context, they appear to be just words, Sir. Please feel free to use them as you see fit. If they start bothering me, may I tell you?"

"Certainly. What about if I call your body parts things like 'tits' or 'cunt' which some people find offensive?" I continued.

She actually laughed. "I'm not a prude, Sir, although I may dress like one. My body parts have been called much worse terms, I assure you. Please don't stifle your creativity."

"I won't," I promised. "Now, stay as you are." I left the room, returning with sandals, a short black skirt, and a thin, silky white blouse. "Put these on, my girl. Guess where we're going."

Her mouth fell open in shock and surprise, followed by a couple of rapid up and down movements of her jaw as she tried to regain speech. "You mean... you mean we're actually going to do it? Go to the art museum, Sir?"

"Indeed we are. Get dressed."

She stood and slipped on the blouse, buttoning it. Then she pulled on the skirt, and stepped into the sandals. Her darker areolae were quite visible through the material, as planned. "Have a look in the mirror, Jilly. See what an eyeful people are going to get," I directed her.

She looked, and turned a light shade of scarlet. But she didn't refuse to go, or even complain. As we neared my door to leave, she exclaimed, "Oh! I forgot to put on my panties, Sir!"

I looked into her eyes, and said, "Did I give you any panties to wear, my girl?" The widening of her pupils as this sank in was priceless. To add to her excited humiliation, I unbuttoned the top two buttons of her blouse. "There, that'll give people a nice glimpse of your cleavage, as well." Jilly smirked, but turned a pretty shade of pink again.

Our outing at the museum went as expected. The air inside was between cool and cold. Jilly's nipples poked against her silk blouse, and rubbed against its material since her breasts wobbled gently as she walked. If anything, her areolae looked darker in the lighting there. People stared. People gawked. People pretended not to look as they obviously looked. Jilly's cheeks and neck took on various hues of pink and scarlet. But she smiled shyly - oh how she smiled. I had a suspicion.

"Walk ahead of me for a while," I whispered. As she did so, I got a better look at the bottom of her thighs and her legs. Sure enough, there was evidence of a tiny trickle of fluid, visible if a person stared hard enough. To me, Jilly was a more beautiful work of art than anything hanging on the walls.

When we got back to my car, I asked, "How was that experience? Was it as exciting and erotic as you dreamed it might be, the day we first talked about it?"

Her eyes twinkled as she replied, "It was even more so, Sir! I felt very embarrassed at seeing all the expressions on those people's faces. But at the same time, I was so turned on that I almost had an orgasm as I walked. I think my clit was so swollen that my thighs were rubbing against it as I moved."

"I wonder how many people were aware how copiously you were lubricating, though," I pondered aloud, making Jilly inhale sharply.

"You could tell, Sir?" she choked out. "I knew I was leaking on my thighs, but I hoped it was too dim in there for anyone to see."

"Your juices were glistening in those lights, my girl. Clearly visible to anyone who looked," I informed her. Hearing this, Jilly slipped her hand under her skirt, touching her pussy and panting with arousal. "It appears to me that you're so excited that you want to give me a blow job, while fingering yourself. Is that so?"

Jilly's hand moved under her skirt, as she licked her lips and nodded. We were in a relatively isolated part of the parking garage, so I unzipped my pants, and pulled out my dick. "Here, slut. Use your mouth on me and make me cum as you get yourself off with your fingers." Twisting in her seat, she ended up kneeling in her foot well, her hands busy beneath her skirt as her mouth latched onto my cock and bobbed and sucked.

The area was so quiet that I could hear her fingers squishing in and around her cunt. She was bobbing her head up and down so eagerly that sometimes my cock popped out of her lips with a lewd sucking sound. But she quickly engulfed it back into the heavenly embrace of her mouth, and greeted it with her tongue.

A few minutes later she stiffened, and began rocking and shaking in orgasm, a lovely sight. Seeing her climax brought me to my peak. "I'm about to cum, slut," I warned her. "I don't want any semen staining my pants, so you'd better swallow every drop." She nodded her understanding and brought both hands out from under her skirt to brace herself on the car seat.

With a loud groan, I launched my load of cum into the vacuum of Jilly's mouth. I had my eyes closed during this intense release, but I fancied I could hear Jilly swallowing. She kept sucking long after my spurts stopped - sucking until my dick softened. She pressed her lips tightly together at its base, and slowly lifted her head, stripping any remaining fluids up and out from the core of my shaft. When my clean, glistening dick plopped out of her mouth, she looked up at me with a wide-eyed, satisfied expression. "Thank you, Sir," she breathed quietly. "I hope I get more opportunities to do that."

I laughed. "Oh? You like the art museum that much?" I asked.

She laughed merrily, joining me. I mentally noted how much Jilly loved giving blow jobs.

With the sexual barrier breached by Jilly performing fellatio on me, we mutually decided to try cunnilingus and fucking. But I didn't want to approach it the 'vanilla' way - the way she'd done it with her husband. So I tied her up. And I tied her down. To tie her up, I bound her wrists behind her back, and her legs to her thighs - this left her tits and cunt completely exposed and vulnerable. To tie her down, I put a pad on top of a low, narrow table, and tied her leg ropes to the nearer end table legs, and then passed a rope across her torso, just beneath her tits, and secured it under the table.

With her in this position, I straddled the table and fucked her mouth for a while, with her sucking me avidly. Next I spat between her breasts and sandwiched them around my dick as I tit fucked her, with her bobbing her head up to watch my dick appear and disappear between them. By the time I moved down to her cunt, it was literally drooling its juices from her excitement. I nudged her puffy pussy lips aside with my cock, and pressed inward. Jilly thrashed about so violently that I thought she was hurting. "Are you OK?" I asked, concerned.