Dear Auntie Helga,
After the incident with mummy's knickers I was always sent to spend the school holidays with my auntie. Whether this was because mummy knew what I'd done I never knew, but that was what happened from there after. Auntie was a lot different to mummy, she always seemed to have more expensive looking clothes, and a lot more of them. She was divorced, and had two daughters, one slightly older, and one slightly younger than me, and they lived with their mother during term time, but went to stay with their father during the holidays. I often used to wonder whether it was auntie missing her daughters which made her do the things she did to me when I was staying there.
Anyway, being the foolish boy that I was, and not even thinking about the reasons that may have got me sent there in the first place, the very first time auntie went out and left me on my own, I was unable to resist the temptation to head straight for her underwear drawer. What a revelation that was, she had so many things, lots of silky and lacy bras and knickers, really sexy things that would turn a sissy boys head in an instant, and that's just what they did. Within a matter of minutes I had picked out a bra and panties, stripped off, and proceeded to put the panties on, and struggle into the bra.
This was followed by my gazing at myself in her dressing table mirror. I was so excited that as you can imagine my little penis was as stiff as it had ever been. I stood there, looking in the mirror, seeing the bulge in the front of her panties, and thinking that if this was how it was going to be staying with auntie in the holidays, then I was all for it! That was my first big mistake, because the next thing I heard was "What on earth do you think you're doing?". I spun round to see auntie standing in the doorway. I hadn't heard a thing. Before I could do or say anything, she was across the room, and leading me by the ear to the bathroom. I was told to take her things off, and then shoved into a cold shower, accompanied by lots of muttering from auntie. Once the shower was over I was sent to bed, and told not to come out until she said so. It was about 3 o'clock in the afternoon....
I stayed there, eventually drifting off to sleep, only to wake later needing to go to the toilet, so I got up and went. That got me a sound spanking on the bottom for getting up without permission. The next morning I found that all my clothes had been packed up into my suitcase, so I thought I was being sent home, and the realisation dawned that if I was, then mummy was certainly going to be finding out what I had done, which wasn't something that I was looking forward to. I asked auntie when she came into tell me to get up, and she said that if I wanted to stay, there would have to be some changes. That was the start of it.
She said that if I liked wearing women's things so much, I could be a girl instead of the dirty boy that I was, and so from then on I was dressed in her daughter's clothes. Because I was so tiny in stature it was mostly the younger girls things, and although I was about 11 years old at the time, by the time I was dressed I looked about six or seven at the most. My hair was allowed to grow out all the time I was there, and with the addition of hairbands and ribbons etc I looked a proper little girl. There was only one problem, shoes. I just couldn't fit into either girls shoes, my feet were just too wide. That meant it was time for my first trip out. I was terrified. Luckily auntie lived far enough away that I was unlikely to meet anyone I knew, but I felt sure that everyone was going to know that I was a boy dressed up in little girls clothes. Strangely though, as frightening as that thought was, it was also terribly exciting.
Things weren't going to go well though. I don't know if you are aware, but shoes used to be trial fitted with the purchaser sat on a chair, with their foot on a sloping stool in front of them, and the shop assistant kneeling next to the stool. I knew that the assistant (female of course) could see right up my dress, and not only that, I could see her eyes moving backwards and forwards and she looked at what she was doing, and then back to my knickers, the front of which were visibly growing into a little tent.
The assistant brought lots of shoes, all fitted in the same way, with her glancing at my panties all the time, followed by me walking up and down the shop to see if they were comfortable. After what seemed like ages of this, I began to feel that tingling "down there", and as I sat there with the assistant in front of me, I came in my knickers. The assistant just looked at my auntie and said "oh dear, I think she's wet herself". With that, shoes were quickly decided upon, and I was taken home to get cleaned up, and get another spanking afterwards.
This was the first time that auntie pulled my foreskin right back as she was cleaning me, and I can say that it was very painful, but like so many other things strangely enjoyable as well. Hearing her making remarks about "how dirty it was in there" and "don't you ever clean yourself properly down there you dirty little boy?" just added to the excitement and embarrassment. I was worried it wouldn't go back, but auntie just seemed to be able to do it without any problem at all. Not without any pain to me I might add, but definitely without any problem. If auntie ever inspected me down there and found the foreskin retracted, she knew I had been playing with myself, and another spanking was administered immediately.
Subsequent trips to buy shoes involved me wearing what I later found out to be a large sanitary pad. Presumably auntie wasn't prepared to be embarrassed by me on any other occasions. From then on it was not Nicholas, I became "Nicola" and there wasn't a thing I could do about it. If she had visitors I was introduced as her niece, staying during the holidays. It was always exciting to hear her saying to people "This is my niece, Nicola, she's staying with me for the holidays. Say hello Nicola", which I duly did, accompanied by a little curtsy that auntie had taught me.
I was always dressed and treated like a girl, never as a boy. I don't know what would have happened if I had to go to the doctors, but that never arose. At home I was masturbating 3 or 4 times a day, but at aunties I didn't at all, or at most rarely. That's not to say that I wasn't almost permanently aroused, because I was, and that I didn't cum, because I did, just not by masturbation. A lot of the time I used to cum as auntie cleaned my penis, that combination of pain as she retracted my foreskin, and the pleasure as she gently cleaned me was almost always enough to make it happen.
I spent school time at home, and holidays with auntie right up until I left school for university. Then, as auntie was close to my chosen university, it seemed only natural to her that I stay with her during term time, and go home in the holidays, as this was what was happening with her two daughters. They went to university close to their father, and stayed with him during term time. Looking back now it seems like there was some sort of divine intervention going on, the purpose of which was to keep me in panties for as long as possible. I did get more free time then though, so much so that I even managed to get a girlfriend, albeit a secret one, for I didn't think auntie would approve, and more to the point, I thought that if I came back with a girlfriend in tow, auntie would tell her exactly what had been going on for the previous ten years or so.
A couple of things spring to mind about that relationship, firstly my tiny penis never managed to satisfy her, (yes, can you believe it, we actually had sex!!!!!!) and I was always trying to get inside her knickers, but not in the way that most people would think. When she was a bit drunk one night I did manage to have sex with her while I was wearing her bra and panties, and luckily enough it was such a non event that she didn't even remember about it the next day. I did though.
Of more interest, she worked in a Launderette, and used to do "Service Washes", where people would bring in their washing, and she would wash, dry and iron it. This gave me the opportunity to meet her from work, arrive early, and sort through the bags of washing in the back room waiting to be done. It had the added bonus that I could masturbate into anything nice that I found, knowing that it was going to be washed anyway. After a while the owner asked if I wanted to earn a bit of money as well, and he got me servicing the dryers, and that involved getting out items of laundry that had worked there way around behind the drums. Mostly small items, socks, knickers bras etc. Anything found went into a box which was there if anyone came back for them, or that's what was supposed to happen, needless to say, the items of female underwear I found didn't go into the box while I was there. That was the start of my collection.
We were together for a couple of years, but if I'm honest I think she was sleeping around during all that time. Certainly when she dumped me she went into great detail about how her new boyfriend had a great big penis, and that he made her cum from the minute that he was inside her. I on the other hand hadn't made her cum in all the time we were together. Not good for my confidence, but it's nothing but the truth I suppose. She obviously didn't know about my panty wearing otherwise she would have undoubtedly brought that up. After it ended I was obviously spending more of my free time with auntie, and so it wasn't all bad I suppose. From then on I suppose I resigned myself to living with auntie as her niece, and that has continued more or less continuously since.
It's been a long time that has seen me fall further and further under her control. After leaving university I got a job, which was also close to where auntie lived, so I continued staying with her. Over time I began to dread going to work because it involved me wearing male clothes, I had become conditioned to wear women's clothing. I had enjoyed doing so as a boy, but had thought it would end as I grew up, but it wasn't to be. Fate once again took a hand in the way things were when auntie had a bit of an accident.
Once a week she would go horse riding, and a fall from her horse caused her quite a few injuries (luckily only minor, but bad enough to cause her a great deal of pain and affect her mobility for quite a few months). It was decided that I should stop working to look after her, which I did without hesitation, even though part of that care was bathing her, and attending to her toilet hygiene. I do think that this time in particular strengthened the relationship between us, even though afterwards, once she was recovered, she did take even more control over me and my life. (Possibly because she had had to relinquish some of that control while she was injured).
I wasn't allowed to return to work, which was perfectly acceptable to me. It did mean that because I was there all of the time, that I was introduced to more and more of her friends who would visit. It was embarrassing every time someone new visited, but they all seemed to take it in their stride that auntie had her "niece" living with her. It became more difficult going out though, as I had become far less able to "pass" as a woman, but some of her friends would help with makeup, and for the most part I escaped without being found out most of the time. Strangely, when I was it was always by women, they must have a sixth sense for these things.
The fact that I wasn't 100% passable did cause problems though. Auntie had taken me out from when I was a child, and if I needed the toilet then she would take me in the Ladies with her and no one batted an eyelid. As an adult that couldn't happen, if I went into the ladies toilets everyone would have known I was a man and I would have been arrested, but there was no way I could go into the Gents. I probably wouldn't have been arrested if I did, but I have no doubt I would have been beaten up or worse. As always auntie had a solution, but it wasn't one that I wanted in any way. She decided that if we went out I would have to wear a nappy and plastic pants so that in the case of the need to go to the toilet and not being able to hold on, I could wet myself without it showing.
Sometimes there were leaks and I think she enjoyed seeing me humiliated that way but most of the time it worked well. She would always buy the disposables, and always with me in the shop with her, making sure the assistants knew that they were for me to wear. On a few occasions I actually messed myself as well. At the time I just couldn't understand how that happened, as it was never something I had a problem with, I could always hold on until I got home, but when it did happen I seemed to lose all control and there was no way I could stop myself. It was only years later that she told me that when she felt like it she would add a dose of castor oil to my breakfast before we went out, just so she could see me struggle and squirm trying to hold it in. In fairness she did always clean me up on our return home, and although it was unpleasant and embarrassing, as with so many other things with auntie, it was also strangely sexually exciting.
I've never had another girlfriend and after the experience of that first one, and the long period under the control of auntie, I have to say that now I wouldn't want one. I get a great deal of pleasure from being denied masturbation, my foreskin is still so tight that if I got carried away and pulled it right back she would know, and I would be punished, but she still cleans and inspects me down there, and even all these years later that is enough to make me come a lot of the time. I have found cumming without masturbation or deliberate physical stroking far more enjoyable. Far, far more enjoyable actually.
Now I don't see any other life for me other than living with auntie, and attending to her needs, and living exactly the way she wants me to. I don't have to work, my whole life is to make her life more enjoyable, and that's just how it should be.
Thank you for your letter Nicola and for sharing your amazing and wonderful childhood, your aunt is a real treasure and certainly due your respect and submission. I imagine that truth be told, she enjoyed teaching you about being a girl and is delighted still by your friendship and love. Hope to hear more another time.