As I travelled back home, I was nervously excited to know what tasks Helen had set me, but, as she had instructed, I didn’t look until I was in my flat, whereupon I ripped open the envelope. Inside was a folded sheet of paper, from which drifted the delightful fragrance of the perfume Helen had worn that evening. My fingers were quivering as I opened the paper up to read what it said. It held simple, yet worrying, instructions:
1. Visit a supermarket and buy a multi-pack of plain, cotton knickers, paying no more than £5 for the set. Purchase nothing else and, on Friday, wear a pair of these panties. Bring along the receipt to show you have obeyed my orders.
2. Write out one hundred times, in your best handwriting, and without any mistakes, the following sentence: ‘I, Julian Fyodor Moriarty, enjoy wearing knickers.’ Bring those on Friday as well.
Reading these orders caused a wave of nausea to sweep over me. I could barely hold the paper because of my trembling hands. One part of me felt intense excitement, while another sensed danger. How was I to purchase the underwear without, at best, experiencing acute embarrassment and, at worst, being found out? I would much rather have been told to visit a luxury lingerie shop with instructions to buy an expensive item—at least I could then have plausibly pretended that I was purchasing something for a girlfriend. But no way could a £5 pack of cotton knickers be justified as a gift. Clearly, humiliation potentially awaited me if I accepted the challenge. Yet, not rising to the quest, was unlikely to be received well and could end our relationship, a prospect that appalled me.
And then there was the writing out of the sentence. I’d not had to write lines since I was at school. Writing that sentence one hundred times would be boring, but what really worried me was having to include my full name. I’d told Helen what it was to make light conversation about my ridiculous middle name, shared with the novelist Dostoevsky, and my laughable surname, with its Sherlock Holmes connections. There can’t be many men named Julian Fyodor Moriarty and, most likely, I was the only one. Was I opening myself up to blackmail by copying this line and then handing the output to Helen? Was it a trap? Would I make a total fool of myself?
My brain told me to call it a day and move on, while my heart, and another part of my anatomy, were aroused at the prospect of playing with fire. I had just three days to decide whether or not to proceed and to complete the tasks. That night I barely slept, tossing and turning, imagining the worst possible outcomes, but experiencing powerful erections at the prospect of the humiliation involved. By sunrise the next morning, my decision had been made—I would undertake the tasks and hope that Helen was playing a psychological game and nothing more sinister.
After breakfast, I drove to work on autopilot, and continued in much the same way for the rest of the day, unable to think of anything other than the tasks I had to complete. I decided to buy the knickers at a large supermarket around twenty miles from work and twenty-five miles from home. After all, the chance of anyone I know seeing me there was remote in the extreme. So, after work, I drove to the store and proceeded to the clothing section. From a distance, I worked out the area I needed to aim for, and then I did a fast walk past to confirm I was right.
I retired to a safe distance, and pretended to browse some men’s shirts, while waiting for two or three female shoppers to move from the lingerie zone. With the coast clear, I made my move! Simultaneously taking in price, material, quantity, and size, I snatched up a pack of five bikini-style cotton briefs in pastel colours and priced at £4.99. I double-checked they were definitely the correct size and then headed for the tills.
I did contemplate using an automatic checkout, but I wasn’t sure whether the receipt would make that obvious, so I went instead to a till with an assistant, as I thought Helen would expect. I’d read many stories where guys in my predicament had been openly laughed at by the staff, and even forced into a changing room. As I’d hoped, this worry proved to be unfounded but, all the same, my heart was pounding as I approached the checkout. I chose one operated by a middle-aged woman, and I dropped the package onto the conveyor belt without comment. I had no wish to engage in conversation and, happily, neither did she. Most likely she was as embarrassed as I was and wished to complete the transaction as quickly as possible.
As soon as I got home, I tried on a pair of the briefs and felt a sigh of relief when they were a good, albeit tight, fit. With the first of the two tasks accomplished, I then set about writing out my lines. Because my hands were shaking so much, it took several attempts to get past the second or third line without making a mistake. Knowing that Helen was expecting error-free work, I tore up any sheet containing an error, and it took a while to calm down sufficiently to write out one hundred faultless lines.
Satisfied that I had done all I could on Friday, I presented myself at Helen’s front door. She beckoned me in, and we exchanged kisses on the cheeks. Then, without further ado, she asked me for my receipt and for my lines.
“Hmmm... A penny under the £5 limit, Julian—that was lucky!” She smiled, in a manner that emphasised just how lucky I had been.
Looking at my written assignment, she commented, “Well, I think these could be neater, but there are no crossings-out for which you would have been punished—a pity in a way!” She giggled at her little quip. “But why haven’t you numbered them from 1 to 100, Julian? Can’t you see that this makes it harder for me to check?”
She stared at me, and I felt myself redden. Shaking her head, she continued, “If you make that mistake next time, I will tear up your lines and make you do them again. However, as this is your first time, I’ll let you off.”
“Thank you, Ma’am,” I acknowledged, with a sense of relief, although her mention of “next time” was concerning. Writing out lines was not a feature of female domination that I had been seeking.
“Now, show me what you’re wearing.” I undid my trousers and let them drop to my ankles, revealing a pair of mauve panties, which did a poor job of obscuring my aroused penis, by now poking out of the top of the scanty undies. “Nice choice, Julian, a shame they are spoilt by your swollen appendage! In the future, I expect you to always wear knickers when we meet up. Is that understood?”
“Yes, Ma’am,” I replied, feeling simultaneously both aroused and horrified at the prospect.
“Clearly, you relish being forced into female underwear, so it’s not going to be a hardship of any kind. When you need to be punished, I might have to make you wear boxers, rather than knickers!” She smiled slyly at me, well aware of the embarrassment she was causing me.
I didn’t know what to say but reckoned my engorged penis said more than I could express in words.
“But what’s with the hairy legs, Julian? Didn’t it occur to you to shave them, or use hair remover? No doubt, we’ll find your chest is in the same state?”
I nodded and apologised, “Er..., sorry, Ma’am, I don’t... I don't remember you saying I needed to shave.”
“I didn’t say, but it should be blatantly obvious. Use some common sense, for goodness’ sake! As we move forward in our relationship, you will keep yourself completely hairless below the neck. I hope that’s understood, and I don’t need to remind you again?”
“Yes, understood, Ma’am. I’m very sorry. But how do I remove the hair?”
“For crying out loud, Julian, do some Googling and then try out different ways. Creams, epilators, razors... I don’t care, just as long as you’re hairless.”
“Yes, Ma’am,” I replied, feeling chastened.
“OK. Now let’s get your handcuffs and blindfold on, and then we can go upstairs for some fun.”
And, indeed, fun we had, to the extent that Helen gave me a hand job and allowed me to ejaculate. In return, I used my tongue to bring her to two consecutive and powerful climaxes. A great evening for both of us! This relationship was proving exciting, despite the intense humiliation it was so often bringing me.
oooOOooo
Helen and I met up at least twice a week, usually at a pub, restaurant, cinema, or—if Alice wasn’t around—at Helen’s house. The visits to her place were always the best because sex was usually involved, even though I didn’t always get to climax. Helen seemed to have an insatiable appetite for sex, and she understood that keeping me frustrated motivated me to serve her.
She slowly took more control over my life and, over a period of several months, I was sent on more shopping missions, buying cheap knickers in a range of styles, along with equally cheap tights and camisoles but, luckily, no bras. Shopping trips remained challenging, but slowly I developed a coping mechanism and got used to choosing feminine items and then paying for them.
I was then told to wear panties full-time, not just on dates, and to dispose of all my male underwear. I was given instructions on what to wear, even to work, and she warned me that she might text me at any time of the day, requiring a photo to be sent back within five minutes as proof that I was dressed as she expected. It was demeaning but, at the same time, stimulating to be forced to dress in this way, even in the office. There was always the risk of discovery, which meant I had to be very careful when out of the house, especially in the company of others.
Visits to her house increasingly resulted in me being put to work, carrying out chores such as cleaning the bathrooms or doing the laundry, including hand washing her lingerie and other delicate items. It was a huge house, so there was always something to be done. Nevertheless, while I found being treated as a skivvy was demeaning, it was also a turn-on. Helen was well aware of my feelings and reactions, and she knew just what she had to say and do to get me excited.
While sex was so often involved during my visits, she was an enormous tease, and, over six months, I was only allowed to engage in penetrative sex on two occasions. Each time wearing a triple condom which deadened the sensation to the extent that I was unable to climax. Other times, she either used her mouth or her hand to bring me close to orgasm, occasionally tipping me over the edge, but more often leaving me wanting.
A couple of times she gave me a ruined orgasm by stopping all stimulation when I was at the point of no return, causing my jism to dribble out. This was most unsatisfying for me, but she was an expert in tease and denial. Frustratingly, I was never allowed to see her naked or semi-dressed, because she always made me wear a blindfold. Similarly, handcuffs prevented me from exploring her body with my hands. She always called the shots, yet I loved what she was doing, and I was falling in love with her, though I wasn’t sure whether this was reciprocated, despite her obvious enjoyment of our times together.
Corporal punishment was also introduced in the form of a thick leather tawse, which she used on the fingers and palms of my hands when she judged the occasion and demanded it. The advantage of a tawse, she explained, was that it could be applied in seconds, whereas spankings or canings required undressing and took more time to administer. How practical, I thought! Well, I can certainly vouch for the effectiveness of the tawse, which left my hands stinging, and almost unusable, for several minutes afterward.
When I wasn’t on a date with her, I was sometimes subject to what she called cyber discipline, where, in my flat and watched over by a webcam, I had to write lines or stand in the corner. She never visited me at home, but I was expected to keep the flat clean and tidy at all times, and Helen would expect me to demonstrate I was doing so by giving her a videoed tour of my rooms, using my phone camera.
Our relationship was getting stronger, and we were both relishing our time together, in our own ways. Yet, always, the potential fly-in-the-ointment was Alice. I’d never met Alice and, I was told, Alice was unaware of my existence. It was difficult to see how my relationship with Helen could progress further with her daughter in the background. Certainly, I could see no way that Helen and I could permanently live together in the female-led relationship that was evolving.
Yet this dismal outlook was set to change following a major upset in my life. As they say, as one door closes, another opens. The company I worked for had been struggling financially and, in April, I was made redundant. This was a body blow at the time. Despite receiving a modest payout, I calculated that unless I found another job within three months, the mortgage company would repossess my flat. Naturally, this thought thoroughly depressed me, and I spent many hours discussing options with Helen. Jobs at this time were difficult to come by, so my prospects didn’t look good.
One evening, out of the blue, Helen said she had been working hard on a solution that might suit us both. The remedy she laid out was a bold one, and left me stunned. She proposed that I should sell my flat and move in with her and Alice, becoming what she called the “housekeeper”, which would mean doing all the cleaning, laundry, shopping, gardening, etc. I wouldn’t receive a salary, other than a small allowance, but I could take over Alice’s old bedroom and no rent would be charged. Helen, it was explained, would continue to work, so for much of the time I would be in the house on my own, or possibly with Alice if she wasn’t on vacation from school or (later) university.
It was pointed out to me that the housework had to be done to a high standard or there would be consequences, which she left to my imagination. The whole idea very much appealed to me, partly because of the submissive nature of what was proposed, and more so when she added that I would be required to wear a uniform.
“It won’t be a kinky uniform,” she explained, “We’re not talking French maid, but it will be feminine!” Again, at this stage I was left to envisage what this might consist of, but, as I was sitting at that time on her sofa wearing panties, tights, and a camisole under my trousers and shirt, I had a good idea. The thought of being forced to dress entirely in female clothing, at least in private, had always aroused me, despite the terror that it also induced at the thought of being made to dress that way in public.
I thought over what she'd told me. “But what about Alice, Ma’am? I know you don’t want to do anything that might upset her in any way,” I remarked, wondering if Helen had thought this through.
“Quite right, I certainly don’t,” she replied. “That’s where I’ve had a brainwave! We need a backstory to explain why a man is living in this house dressed as a woman. The idea forming in my mind is that you are a distant cousin who wants to transition from male to female. You’re down on your luck, and I’ve taken pity on you, allowing you to live here, doing the housework in exchange. As far as Alice is concerned, there will be nothing openly sexual between you and me, so hopefully she’ll just come to regard you as a man dressed up as a woman who is employed here as a housekeeper. To be honest, I think she will be genuinely curious about you because she’s very much into psychology and trying to understand human behaviour. That's a bridge we'll have to cross in due course.”
“But you won’t be telling her the complete truth, Ma’am? Is it wrong to keep secrets from Alice?”
“I don’t think so, Julian. Everyone has secrets, and children don’t need to know everything, no matter how old the child is. Besides, she will learn more as time goes on. Let’s do one step at a time, eh?”
I was told to think about Helen’s proposals for a week or so, and I found myself conflicted. Clearly, this was a move that would involve cutting ties with the past—for a start, I wouldn’t be able to keep my flat, as I wouldn’t be able to pay the mortgage. But, my love for Helen was growing and the thought of spending every day at her beck and call was appealing. On the other hand, I was very nervous about being forced to pass myself off as a woman by wearing female clothing in front of her daughter, who, I’d been told, could be inquisitive.
Consequently, at our next date, which was at her house on a Saturday with Alice away, I agreed to Helen’s proposal, but I suggested that dressing completely en femme should be introduced slowly, to give me time to adapt and for Alice to come to terms with the weirdness of it all.
“Nonsense, you’ll be fine, and so will Alice,” she reposted, dismissing my concerns with a wave of her hands. “You won’t be trying to deceive anyone that you’re a real woman. You’ll be a man transitioning to become a woman. Stop dreaming up problems. Leave it to me to sort everything out!”
I swallowed hard and nodded, but felt that the pace of what she called my transition would need to be raised again when she was in a more amenable mood.
She continued, “But I’m pleased you like the idea of being my housekeeper. You’ll need to sort things out with your flat. Put it on the market, and put whatever you can into storage, because I don’t want you turning up here with more than two suitcases. This is a fresh start for you. But remember to bring all your female attire because you’ll need that. If you’ve not so already done, and you should have done so, dispose of all your male underwear because you won’t be ever wearing that. Understood?”
I nodded and she continued, “I’m aiming for you to move in and assume your duties four weeks from today, but, before then, you’ll need to meet Alice, just to make sure that she gets on with you. I’ll arrange a get-together for the three of us.”
She reached behind and pulled something out of a drawer. It was a deep pink colour and I instantly recognised it to be a chastity device. A shiver went down my spine. I’d always wanted to wear one, but wasn’t sure I would cope with the frustration. Furthermore, being so often denied relief by Helen had meant that I had frequently been masturbating in private, and I could see that coming to an end.
“This was John’s,” she explained, before adding, for reassurance, “but don’t worry, it’s been thoroughly cleaned!”
I gave a faint, nervous smile before she continued, “When you’re living here, you will be permanently locked up, apart from short periods of release for vital functions. I doubt you were expecting anything different, but also, and this is important, it gives me reassurance that Alice will be safe.”
“Please, Ma’am!” I said, feeling disgruntled. “I’ve no interest in having sex with children! She will be a hundred percent safe with me, whether or not I’m locked up.”
“I believe you, but she’s eighteen, so not a child in the eyes of the law. You could legally have sex with her, so you’re going to be locked up 24/7. Actually, I'm sure she’s too naïve to be interested in having sex with you, but let’s not put temptation in the way.” At the time, I accepted what Helen said about Alice being “naïve”, but those words would return to haunt me.
“Now, I appreciate it takes time to adapt to a life of chastity, so I’m giving you this device, with a padlock and key, to use over the next four weeks. Use the time wisely, and try to get as used to wearing it as possible and take it off only when it becomes unbearable. Remember, you have just four weeks to acclimatise yourself to wearing it full-time.”
I gulped, and nodded, taking the device from her, thinking how small it looked. I knew I would have to shrink my penis with a bag of ice cubes to squeeze it inside.
“Oh, and in case you’re wondering, when you move in the padlock will be changed, so don’t waste your time getting the key copied. Not that you would dream of doing so, I’m sure!” She smiled, coyly, and I gave an unnatural smile in return.
“And a couple more things, you need some C-cup bras to wear here. Get four or five underwired white ones, as plain as possible, and the cheapest you can buy from a supermarket. The cup size is important because I’ll be providing falsies to fit snugly inside them.” A wave of fear passed over me as she stepped up the pressure. Was I going to bite off more than I could chew? I was just hoping I would be able to cope.
She waited while I took in what she was saying, before continuing, “I hope you’re not getting cold feet?”
The simple answer to that question was “yes”, but I didn’t want to say that because my feelings were too confused to be summarised in a single word. So, I took a deep breath and replied, “I’m getting very nervous, Ma’am, and I may struggle, but I’m also excited. I hope I perform to your expectations.” My stomach was starting to feel queasy, but my manhood was having the time of its life.
“You also need to get your ear lobes pierced, both sides. These are the earrings that you will be wearing at all times. I bought these yesterday because I was convinced you’d say ‘yes’ to being my housekeeper, and you’ve not disappointed me.” She passed me a small box and I opened it to find a pair of stud earrings that combined the male and female gender signs. I later found that this combined symbol stood for bisexual, another humiliation.
“Thank you very much, Ma’am,” I said, genuinely pleased that she had given me a gift, yet feeling embarrassed at the thought of wearing the present.
“Oh, and one last thing, sell your car. You’ll be allowed to drive mine when you’re here and I don’t want yours sitting on my driveway taking up space. Besides, Alice has passed her test, so she’ll be getting a car soon.”
“Yes, Ma’am.”
“Now let’s have some fun. Strip off while I get your cuffs and blindfold.”
Were things now going too fast? Was I making sensible decisions? I didn’t know, but soon my worries were cast aside as I brought Helen to a shuddering crescendo with my tongue, while she fondled my erect penis, bringing me ever so close to ejaculating, but just stopping short. I went home and did what I usually did—I jerked off, thinking of Helen, while also being aware that my freedom to masturbate would soon be curtailed.
