Dear Auntie Helga,
When I last wrote, you kindly published my letter in Dummy Discipline Digest and asked me to write again soon. Unfortunately, it has been more than a year since then, so I hope you will forgive me for the delay.
As I outlined in my last letter, Margaret was my first long-term girlfriend when I was a rather naive teenager. To my shame, she managed to get me back in night-time nappies and plastic pants and made me move in with her and her parents and even use a 'tommy-tippee' cup in front of them as part of what I now realise was her complete domination and control over me. I loved her dearly but I recognise now that I perhaps should have stood up to some of her more extreme forms of controlling me, but simply didn't feel able to at the time. Simply by looking at me in a certain way even in a room full of people, Margaret would require me to go to bed early every night. She would then bring me my 'Tommy Tippee' cup full of warm milk, watch me drink it before tucking me in extremely tightly making sure my hands were under the covers with only my head sticking out! After a while, Margaret preferred to feed me my milk after she tucked me in meaning I was unable to use my hands to control the cup. As I struggled with the milk, Margaret would slide her hands under the blankets to check that I was properly attired as required, before she would lift her dress or skirt and expect me to kiss her panties goodnight.
From start to finish of the entire bedtime ritual, Margaret uttered not a word... occasionally I would be blessed with a 'good-boy'... if I failed to get any part right, Margaret would instantly stop and simply walk away. Usually, however, it was a very pleasurable experience. Unfortunately, one day the stains on the sheets were noticed and commented on by her mother, causing enormous embarrassment to me, but not of course to Margaret who was never suspected by her mother of playing any part in causing the offending stains.
Margaret's solution was to insist that if I wanted the bedtime ritual to continue (which I assured her I did!!), then I must wear protection in the form of clear plastic pants 'to prevent any little messes' and although I refused for a while, I eventually reconciled myself to wearing whatever Margaret required as a small price to pay in exchange for the joy of her nightly visits.
Normal service was resumed until one morning Margaret discovered that I was in the habit of easing myself from under the covers before going to sleep so I could take off the plastic pants. She hit the roof and made me feel like a very naughty boy. Margaret said she wasn't only annoyed because I had taken the plastic pants off, but also as there was no point in her spending time tucking me in if I was then getting out of bed. I found myself promising Margaret not to get out of bed once I was tucked in and begging her not to stop her nightly visits. But she felt very let down that I was risking more stained sheets by removing the plastic pants which she had provided to offer full protection and avoid her mother discovering my 'dirty boy' emissions.
I rather inadequately tried to explain the reason I took the plastic pants off was that they were rather uncomfortable and sweaty and tight around my thighs, leaving soreness and red marks. Margaret told me I was being very silly as the plastic pants were supposed to be tight to form a proper seal to stop any nocturnal leaks. But she offered to do something to address the sweating issue - and to my horror, a couple of nights later a toweling nappy and pins appeared on my pillow.
I ignored them and got ready for bed as normal. When Margaret came with my warm milk, I told her in no uncertain terms there was no way I would be wearing a nappy to bed as it made me feel very babyish. I expected she would be angry by my reaction but in fact she was very sympathetic and assured me it wasn't really a nappy but simply a single layer of fluffy toweling to protect me, absorb the sweat, and barely noticeable under my pajamas, and in any case it was our little secret, so would I now be a good boy and agree to try it? Well, I was already wearing sweaty plastic pants, so I figured there was no point fighting it any longer and accepted that the toweling liner might be more comfortable overnight than plastic pants with nothing underneath. I suppose I should have been stronger and stood my ground, but I adored Margaret and didn't want to lose her - or find myself homeless again. So I relented. Despite protesting, I had to admit I slept better and inevitably I was soon fully compliant and not objecting to wearing the protective towel as a matter of course. All went well for quite a few months until one night Margaret and I were at a friend's 18th birthday party and I had too much to drink, leading to a very small damp patch in my protection during the night.
I tried to hide it from Margaret, but needless to say there was no escape and she discovered it during her morning inspection of my protection before I was allowed to take it off and dress for work. As usual, she plunged her hand into my plastic pants and realising I was slightly damp, teased me relentlessly and made a huge deal about how fortunate it was that I was in a nappy and plastic pants otherwise she would have had to tell her mother I had wet the bed etc. I protested and reminded her of her assurance that it wasn't a nappy, but she merely laughed more at me and said if it wasn't a nappy how come I had wet it like a baby, to which there was of course I had no argument.
When I came home from work that night, instead of my normal thin toweling protection on my pillow, there was a much more bulky bath towel, neatly folded and with four big nappy pins placed on top. I was mortified. Margaret didn't say anything, but I knew I was totally defeated and there was no point in arguing. I pinned it on and pulled my plastic pants over it as best I could and crawled straight into bed. A few minutes later, Margaret arrived with my warm milk, and when she put her hand down the blankets and felt the extra bulk, she told me how proud she was of me, which made me feel much better, specially when she continued to caress me to a lovely finish while I tried to drink my milk followed by licking Margaret's fingers clean before kissing her panties goodnight.
The bulky toweling became the norm after that, which caused numerous problems and embarrassments and despite it being less comfortable than the single layer of toweling protection. Now, once dressed for bed I had to be very careful not to be seen by anyone - other than Margaret of course who I had to report to each morning for inspection, which involved me checking the landing was clear before furtively waddling like a toddler to her bedroom from my 'nursery' as my room was known, as it was still home to the cot used by Margaret as a baby and was still decorated with pink nursery wallpaper, adding to my humiliation...
Despite my many attempts to revert to the thinner less-obvious protection, Margaret remained adamant. To placate me, she suggested that I might only have to wear the bulky nappy for a short period, but it became a permanent fixture and things actually became worse, not better. For example, after a while, my pajamas disappeared and apart from my nappy and plastic pants, I was only permitted to wear a plain white tee-shirt at night which I was thankful for, as it at least partly covered the new plastic pants that Margaret bought me and gave me, wrapped in a ribbon as a birthday present which I had to thank her for, despite them being hideously large, almost up to my chest, and much more rustling and noisy with every movement. Margaret was upset that I was not thrilled with my present, saying she was only thinking of me by getting the supersize, to amply accommodate my bulky nappy - and hopefully less tight on my thighs.
With the benefit of years of hindsight, I now realise I was rolling over every time Margaret increased her control over me. I had seemingly become a most willing submissive to her completely Dominant nature, largely because she knew I totally adored her and the fact that I believed that our relationship was entirely normal and that this was what happened whenever boy meets girl.
Margaret made me tell her about my nocturnal habits and one night after I had been using my tongue on her special place, she made me cum inside my nappy. Afterwards, she started talking down to me like I was a little boy. She said I now had a big 'choice' to make - going back to my 'before Margaret' DIY ways and moving out of her parents' home, or becoming her Obedient boy allowed to cum only in my nappy in future, and of course only under her strict supervision. The sweetener was Margaret explaining that I would normally be allowed to orgasm after pleasuring her at length with my tongue. Immediately, I made the choice she knew I'd make. What followed was another lengthy period of my tongue being used for her pleasure.
Despite my initial reluctance, in time I came to realise that any sign of non-compliance with what Margaret wanted would result in her going into a foul mood for days at a time, lengthy withdrawal of all treats, with the ultimate threat always hanging over me of eviction onto the streets. So I had little choice but to be her good boy. I also became totally addicted to Margaret's special very personal perfume. She skillfully started what I now realise was a deliberate process, by having me say good night to her special place by kissing the tops of her legs and then her panties, and encouraging me to give her panties a persona by talking to them submissively and pledging my Obedience not only to Margaret but also to her panties.
After a while, Margaret developed my addiction by talking to her panties herself, telling them to make sure I behaved myself, before taking them off and placing them over my head and telling the panties to protect me in the night and to stay firmly in place, with the dirty gusset over my nose. As you can imagine Auntie Helga, this was not always pleasant and took some getting used to, specially during Margaret's special time of the month. While seriously reluctant at first, in the end I found that I couldn't sleep without a pair of Margaret's dirty panties to comfort me, again, much to her delight and her endless good night baby-like-talk.
Things took another leap (not sure whether forwards or backwards!) one Saturday when we were getting dressed for a friend's wedding. We were late, the taxi was waiting outside and there were no clean underpants in my drawer. With hindsight, I wouldn't be surprised if Margaret had hidden my male underwear, but of course she had a solution and quickly handed me a new pair of her cotton school girl styled panties, still in the packet and told me to hurry up. I snapped that I wasn't about to wear girls panties, specially not to a friend's wedding. Margaret calmly pointed out that firstly the pastel coloured green pants were unisex (she seemed to ignore the slightly frilly lace round the legs!) secondly that if I preferred, I could wear girly pink ones! And thirdly, no-one would know what I was wearing under my suit!
She gave me a choice, I think half in jest, of putting on the new panties or being pinned back into the bulky nappy I had just taken off. As usual, I didn't have much choice but to comply, so I put the new panties on, much to Margaret's delight and encouragement that I looked just fine. But to my acute embarrassment, by this time I had an erection which I quickly tried to hide and was sure Margaret had not noticed.
All day at the wedding, Margaret repeatedly asked me how I felt, her words of 'reassurance' that I was now in unisex panties being anything but reassuring. I felt very small when she remarked that my erection when I put them on earlier showed that despite my protestations, I obviously liked being in the same style of panties as she wore, and that they must be naturally unisex as we were both in them! But Margaret's most worrying observation was that she felt I was behaving much more docile and respectful while wearing panties and that male underwear must have a bad effect on my behaviour. As she felt this was obviously pleasing both of us, she declared that we needed to develop this aspect of our relationship further.
I tried to answer, but she indicated I was to be quiet and with one of her hands inside my trousers, she slid her tongue deeply into my mouth and gave me one of the most passionate kisses I have ever had the honour to receive (I knew better by this time than to respond in any way and was acutely aware I had to keep totally passive in these moments, and keep my lips and tongue absolutely still). But all this excitement couldn't stop an instant erection. Margaret just smiled and said 'I'm glad my little man agrees with me...'
For the first time that night, despite their bulk, I couldn't wait to get my big nappy and outsize plastic pants on and get into bed ready for my treats... in fact after Margaret kissed me goodnight, she told me to come to her bedroom and what followed was one of the best nights of my life, as Margaret took my virginity. The following week, every pair of my male underpants disappeared and were replaced with seven pairs of new so-called unisex panties -; a different pastel colour for every day of the week.
I knew it was not worth arguing, and in any case, Margaret was right that no-one would actually see them and if every Saturday was like the last one, I really would do whatever was required to make it happen again. One of the most humiliating experiences was hearing Margaret tell her mother that 'I' had decided that my old y-fronts were out and that I wanted to wear 'unisex' pants like Margaret's.
Margaret was happy with the new arrangement for a few months, although we only once again had full sex, but the second time she made me wet my nappy in front of her before taking me, which although bizarre and not easy to achieve, I eventually managed to comply to Margaret's wishes and I felt very loved afterwards when she said I was her special boy.
One morning Margaret called me into her bedroom for my inspection. (I was only ever allowed to enter if I was wearing nappy and plastic pants, tee shirt and nothing else). I knelt at the edge of her bed as she had taught me to do, and she said she had something very important to tell me. She asked how much I loved her and if would like to feel closer to her every day, which of course I did. She teased me a little before asking what I would be prepared to do to show my Devotion and Obedience to her. These were words she had not used before, but of course my answer was that I was prepared to do anything to get closer. She made me repeat it and made me swear 'Devotion and Obedience'...
Margaret then told me to give her special place a long passionate good morning kiss, which I eagerly did, even though I thought it strange that she still had her panties on. After I was finished (or rather after she was finished!), she just said 'good boy' and slipped off the rather dirty panties she had been wearing since the previous day. She handed them to me and after a pause, just said 'Well... I thought you wanted to be closer to me...' I thought she wanted me to put them on my head as usual, but a glance of her piercing eyes told me I was wrong.
It took a minute for the penny to drop and I was taken aback when I finally realised she wanted me to actually wear her dirty panties... I said I couldn't as I was wearing a nappy and plastic pants and after feeling inside to see if I was wet, she told me I was a good boy, pulled down my plastic pants and unpinned my nappy so it fell to the floor. I couldn't help it Auntie, but I had an erection as she wafted her panties under my nose and told me to worship them as I worship her and I had to talk to her panties telling them I loved them and was devoted to them... I look back now Auntie Helga and realise that was probably one of the biggest moments of my life, even more special than going to sleep every night with her dirty panties on my head. Even though I was used to wearing unisex panties, up to that point, they had been 'my own' clean ones! This was a huge step-change and I was starting to have serious doubts about what I was doing - and where it was all leading. But slowly, with Margaret looking directly at me, I found myself putting her damp dirty panties on and pulling them up over my erection. As she brought me to completion inside the panties, she simply whispered into my ear: 'You are mine now'. She was of course totally right.
After that, I spent every day wearing the panties she had on the day before, ultra sensitive that their often strong feminine perfume might be a giveaway in the office. I can tell you Auntie, it was not always pleasant, but again I didn't feel I had much choice and Margaret said that as well as bringing me closer to her, wearing her dirty panties would also ensure i was faithful to her as it would be unlikely that I would wish to reveal to another Lady what I had to wear under my trousers and that I should be grateful that she did not send me waddling off to work in bulky nappies and plastic pants for all to see! Of course, Margaret was right. But please believe me Auntie, I never had any intention of being unfaithful to Margaret.
Although sadly things fell apart after about four years, due to my own stupidity, my experience with Margaret in my formative teenage years shaped me forever and is still an indelible part of my life. All these years later, I still find it difficult to achieve any sexual gratification unless wearing a bulky wet nappy and plastic pants in the style Margaret would wish. And naturally thinking fondly of serving my true love in life.
With warmest regards
Thank you for your letter Baby Mac. I'm sure the readers find your letter as fascinating I do, sharing what was obviously a very formative experience from your youth. Margaret's personality being the stronger at the time combined with her vivid imagination, along with you, her 'captive' boy toy provided through these incredible explorations an opportunity for you to change your perceptions and alter your own personality that continues to define you today, quite profund when you think about it as I hope the readers will.