It was six years ago that I met Helen, then a thirty-seven-year-old widow with an eighteen-year-old daughter, Alice, in the sixth form at a private school, soon to sit her A-Levels.

Seven years before that, Helen had lost her husband, and Alice her father, in a tragic car accident. Helen had struggled to bring up Alice on her own. The struggle wasn't a financial one, as Helen had benefitted from a substantial life insurance policy, as well as being a partner in a thriving advertising agency. No, the struggle had been more to do with juggling a successful, but hectic career, with bringing up a young daughter, emotionally troubled from the death of her father. With work consuming much of her time, Helen's solution had been to throw money at the problem, meaning paying tutors and others to lavish attention on Alice, and then spoiling Alice with gifts and treats on the odd days that she had free. The result, predictably, was a daughter who had grown up spoilt and rather strange, but more about that as my account proceeds.

As for me, well, after surviving a messy divorce, I had waited a couple of years before seeking female companionship. Something in me suggested I should seek adventure and new experiences. Since being a teenager, I'd had submissive tendencies and had had fantasies of being controlled by an attractive and domineering woman. My ex-wife had never shared my passion but, now she was in the past, I decided the time had come to explore my subversive interests. I had no intention of becoming a full time submissive, but I hoped that I would at least gain enjoyment from fun and games with a like-minded individual.

What harm could come from it? After all, I might discover that the fantasy of being dominated, and its reality, were at odds with one another—in that case, I would walk away, having learnt something about myself.

With my mind settled, I paid a hefty fee and joined an online dating website specialising in those looking for kinky relationships. Jokingly, my profile described me as a "wet behind the ears" submissive, keen to meet a strict woman of similar age who had experience of dominating men and getting her own way. My hope, I stated, was to go on dates, leading to weekends spent together to explore mutual interests. This seemed to provide me with an escape route if my fascination with female domination was all in the mind.

After a few weeks of getting nowhere, I found Helen—or perhaps she found me. We were soon in contact, first by secure messaging and then by phone. She spoke in a sophisticated manner, with a sense of authority, and I felt that she was a naturally dominant woman who was used to getting her own way with others. Whereas this might put many men off, I found her tone of voice sensual, so it seemed that there could be a match between us.

After speaking on the phone a couple of times, we began meeting up for dates, although that did mean me travelling forty miles each time into the London suburbs, rather than Helen ever journeying out to me, living in the sticks. But this seemed fair enough when I learnt that she had a dependent daughter, whereas I was single with no commitments.

The first few dates were evening affairs in restaurants, but they enabled us, very discreetly, to explore each other's interests and decide if there was any spark of chemistry between us. Appearance wise, Helen was exactly my type—she was slim and about the same height as me and had beautiful blue eyes and blonde hair. Her hair was not especially long, yet it was often tied back into a short ponytail. That look in a woman always appealed to me. She was also well-dressed, and expensively so, despite her style being largely chic-casual. Usually, she wore tight-fitting jeans or trousers, with a close-fitting shirt or jersey which accentuated her breasts. While she was quite small-boobed, they were firm and pert, and were what I preferred in a woman. I guessed she could walk around braless without her breasts flopping around or drooping down to her navel!

The public environment of a restaurant didn't provide an opportunity for intimate discussions but, for our fourth date, Helen invited me to her house, explaining that Alice was at a friend's home overnight, so we would not be disturbed. This occasion allowed us to explore our mutual fancies. It also allowed Helen the opportunity to exercise her dominant side, and for me to be put in my place. And my position was clear from the start when Helen said she would cook the dinner, but I would be washing the dishes. Such assertiveness towards a guest surprised me a little, but I meekly agreed because it suited my submissive nature, which was bubbling over in the presence of this gorgeous woman.

As we ate, Helen told me about her former marriage and the games that she and John, her late husband, played. I was getting turned on from the conversation. After dinner, Helen sat on a sofa, sipping a dessert wine, while I cleared the table and sorted out the dishes before joining her. She smiled and said, "I think you should get undressed." I instantly felt a stirring below and I hesitated for a moment. The smile went from her face as she responded, "Are you going to disobey me?"

"No," I stammered, "Sorry, I'm just surprised at the pace of things!" I started to take my clothes off, but stopped when I saw she wasn't doing the same. "Aren't you going to get undressed?"

"Only after you," she firmly replied.

I felt my face redden. This was embarrassing but, at the same time, very arousing and I felt my penis pushing against my boxer shorts. I continued to strip off as she watched me. Wearing just my underwear, I paused for a moment to assess the situation. I looked at her face, waiting for confirmation. "And those," she insisted, with a glance down at my boxers.

A smile returned to her face as I pulled them off, allowing my penis to spring boldly upright. "Someone is keen," she intoned, "now turn around."

I did so, and I sensed she had stood up. The next moment, she grabbed my wrists and pulled them behind my back. From somewhere, she had produced a pair of handcuffs and deftly she wrapped the cold steel around my wrists, snapping the locks shut. I panicked and started tugging to separate my hands, but to no avail. I immediately regretted this development and began to fear for my wellbeing, or even for my life. Yes, I'd often fantasised about being secured in handcuffs, but, now it was happening, it was scary.

"Calm down, Julian," she implored, softly, "I'm not going to hurt you! But we both want some fun, don't we? Now breathe deeply and try to relax and enjoy yourself."

This was easier said than done, but the soothing tone of her voice was reassuring. Slowly, I regained a sense of calm. My penis, which had gone limp in record time, started to stiffen again. "That's encouraging," she said with a giggle. With those words, she tied a blindfold around my head and then she gently guided me out of the room and up the stairs into a bedroom. She directed me backwards, towards a bed, and I fell over onto the sheets. "Stay there, don't move and don't speak," she ordered.

I could hear activity and deduced she was getting undressed. Very soon, her lips engulfed my swollen penis and, with an expertise I'd never experienced before, she brought me to the brink of ejaculation, not once, but several times in a row. I moaned and implored her to continue, but she reminded me to be quiet. The climax never came, and the next thing was that her sex was over my mouth. Her juices dripped onto my tongue. I knew what she wanted, and my tongue explored her labia, searching for her clitoris. Tantalisingly, I stroked her with my tongue, feeling her twitch when I hit the right spot.

I soon discovered what she found sensual and what she found to be indifferent. Slowly, her jerks increased in frequency and intensity and, had she not been pressing down on my face, I would have lost contact. As we proceeded, so her spasms began to be accompanied by murmuring, which, over a few minutes, intensified, until I could tell she was approaching the point of no return.

Suddenly, with a piercing scream, she climaxed. For a few seconds, I couldn't breathe as she pushed her vulva into my face. Then it was all over. Except that she had climaxed, and I hadn't. She understood my disappointment. "Maybe it will be your turn next time, Julian?" she quiered, But the way she phrased the question made it clear that nothing was certain.

I was left lying naked, handcuffed and blindfolded, on the bed for what seemed to be an eternity, my erection coming and going during that time. Fleetingly, the thought occurred to me to turn over and hump the bed to bring myself to a climax, but I immediately dismissed that idea as ridiculous, knowing it could only annoy her to discover I'd soiled the sheets. So, I lay there, thrusting in vain against the air, any friction denied to me.

I knew she had left the room, and I could hear a shower running, but she was in no rush to return to me. When she did come back, she took off my blindfold. I screwed up my eyes as I struggled to adapt to the light, but I could soon see that she was fully dressed, confirming that there would be no relief for me that night.

On the floor, besides the bed, were my clothes, brought up from downstairs, except that I couldn't see my boxer shorts. In their place was a pair of pink knickers, in boy-shorts style, and made of silk with lace panelling. "Sit up," she commanded. "Alice is away for the night, and I don't know what time she'll be back in the morning, so you need to leave now. Besides which, we both have work tomorrow." Looking at my puzzled expression, she explained, "It's just gone midnight. Now sit up and I'll remove the cuffs."

With my arms free, I sat on the edge of the bed and stared at the pile of clothes. "Yes," she laughed, "You're going home wearing my briefs—the ones I’ve worn all day."

My penis was stiffening again. "I see you like the idea, Julian! When you get home, you are going to jerk off into these knickers and send me a photo of the soiled garment to prove you have done so. Then you will hand-wash them and, the next time we meet up, you'll be wearing them. Is that understood?"

My penis was as hard as a ramrod, but my face was burning with embarrassment. What she was expecting me to do was demeaning, yet exciting at the same time. "Yes," I stuttered.

"I'm sure you can be more polite than that—say ‘Yes, Ma’am’."

"Yes, Ma’am," I repeated.

"Yes, Ma’am, what though?" she challenged.

I deduced what she was expecting me to say. "Yes, Ma’am, thank you for allowing me to wear your panties and for permitting me to relieve myself into them."

A large smile flashed across her face, and she clasped my hands in hers. "Good boy, Julian," she said. "I think you will look lovely in my knickers. And Ma'am is how I always expect to be addressed in future, just so you remember your place."

Two hours later, I was home, and fifteen minutes later Helen received the photo she had asked for. She texted back a smiley face!

oooOOooo

My next date with Helen was dinner in a London restaurant. As she instructed, I was wearing her pink silk knickers, hand-washed by me. Putting them on had been exhilarating—I loved their softness, their tightness, and the way they caressed my penis. Yet I also had a powerful sense of trepidation because, while I'd secretly worn female underwear before, it had always been indoors. This was my first trip out while encased in such obviously feminine attire.

I feared that the train might crash on the way, and I would end up in hospital. I told myself that this was too improbable to contemplate, yet a more realistic concern was that I might get an erection on the journey, visible to all. Fortunately, the trip was event free, and I got to the restaurant 5 minutes before Helen. I sat at the table, waiting, and stood up as she came in. “Good evening, Ma’am,” I said, very softly, so as not to be overheard.

She smiled and, as we exchanged kisses on both cheeks, she whispered into my ear, "Show me your knickers!" I blushed and felt my knees wobbling. The restaurant was busy, so what did she expect me to do?

I didn’t need to ask before she passed me a note. I was to go to the toilets, lock myself in a cubicle, drop my trousers, pull up my shirt and take a selfie. Seeing the expression on my face, she quietly said, "You have three minutes, which I'm timing from now!"

Much to the likely bewilderment of other diners, I raced to the men's toilets and luckily found that the only stall was empty. Quickly, I complied with Helen's instructions and took the selfie with my phone. Only as I took the picture did I realise that I'd not disabled the shutter sound. As I came out of the cubicle, I was embarrassed to see a man standing at a urinal, and he glanced around at me, eyeing me suspiciously. I had no intention of trying to explain myself and I hurriedly left the toilets.

I got back to the table slightly breathless, causing me to get some more strange glances from others in the restaurant. As surreptitiously as possible, I passed my phone to Helen, with the photo on view. "Very nice; well done," she smiled, her face displaying a look of satisfaction at my obedience.

I started looking at the menu, but she told me, "You can put that down because I'll be ordering for you."

In response to my puzzled expression, she gave me a whispered explanation. "If you want to enter into a submissive relationship with me then you need to expect that I will be taking control of certain aspects of your life." I was left feeling stunned and nervous at how quickly she was exerting her authority.

She perused the menu while I sat quietly, not sure where to look. When the attractive young waitress came to the table, as expected she turned first to Helen, who immediately responded, "Neither of us will be having a starter, but, for the main, I'll have the steak, medium rare, and my partner will have the mushroom risotto. Thank you!"

"And anything to drink, Madam?" the waitress enquired.

"I'll have a large glass of this Merlot, please," she replied, pointing to something in the wine list, "and my partner will have a sparkling water." The waitress grinned at me as she wrote down our order. I could feel my cheeks reddening.

The rest of the meal passed without incident and the conversation was restricted to matters that were without any eroticism. I paid the bill, as I’d done on previous dates, and we then stood up to leave. Helen thanked me for a lovely evening, and then said that we would meet the coming Friday at her house as Alice would be away again.

The thought of being alone with Helen, where I felt anything might happen, caused butterflies in my stomach. “But there are a couple of tasks you will need to complete before Friday.” With that statement, she passed me a sealed envelope. “Open that when you get home, and not before,” she informed me, in a no-nonsense voice. Nervously, I took the envelope from her and kissed her goodbye.