“I just loved to take care of him, to cuddle him, to protect him. And, despite his initial resistance, Bobby loved to be diapered by me. Just lying on his back with his legs open his member would grow in anticipation of me softly applying baby powder and folding the diapers tightly around his legs.”
You will find the preceding chapters of this story in “topics” under “Redemption”, with the different chapters in reversed order. To find the first chapter you just have to scroll down to the bottom.
Or you can go to the “index page” where you will find a link to the first chapter of Redemption (and then at the end of each chapter a link to the following)
After I broke up with Jenny I moved to the west coast where I found a job in a market survey company. I started as a data entering clerk but soon became a research assistant. I then went to college in the evenings and week-ends. It was hard to combine work and studies while living on my own, but I got my degree without any problem. At work my boss encouraged me to enlist for a master course in market intelligence. But it would be impossible to combine that with a full time job. When I told him I couldn’t afford to do a full time master study he offered me a loan. He would pay me for the two years of my studies, and then rehire me as a consultant, which would make it possible for me to pay him back. Although I realized that I wouldn’t be free for many years I accepted his offer.
At uni I kept mostly to myself. Being 25 years old I was only slightly older than most of my school mates but I really felt much older, which made it hard to make friends. But then I met sweet Bobby. He was a waiter in the coffee shop where I liked to go to read. Although he was much younger, – he had just turned 19 – we connected.
The fact that he was gay helped probably, because I had grown very wary of all people who might get sexually attracted to me. However, I have often wondered if he didn’t start chatting with me because he was attracted by my androgynous looks. I still had almost no breasts, wore my dark hair very short, and since I had become a full time student, dressed always in black, tight fitting, jeans and vests.
We soon grew very close and spend a lot of time together.
He told me had always felt different from the other boys. His parents had worried about that and he had been faced with a lot of hostility in his environment from a very early age, which caused him to be rather insecure and guilt stricken. No wonder we became soul mates. And I told him, little piece by little piece, about my childhood, being diapered by my mother, and all the things that happened afterwards. Even telling it only in very broad strokes caused me to shed a lot of tears. And Bobby, despite his own insecurities and being so much younger, was extremely supportive and kind. From my side I was proud to have someone confide in me. He would tell me when he fell in love with some good looking fellow and I would encourage him. Most of the time he was turned down, often having to bare insults in the process, and he would then come to me and looking for comfort which I was glad to give
One day after we had had dinner at my place, and had emptied two bottles of wine, I invited him to stay for the night. That first time he slept on the coach. But then he began to sleep over regularly and, as the coach was extremely uncomfortably, I proposed to share my bed.
Of course I had told him I wore diapers to bed and wetted them almost daily, but the first time I felt very awkward about wearing diapers with him next to me. And once again, he helped me overcome my insecurity asking me in his simple straightforward manner, why I didn’t put on my diapers. I blushed but did go to the bathroom and put on diapers. I normally only wear pajama’s on very cold winter days but at first when Bobby slept next to me I wore pajama pants to cover my diapers. It must have been the third or 4th time when in the middle of the night I woke up feeling to warm and decided to take off my pants. In the morning I had completely forgotten about it and coming out of bed I was standing in front of my friend wearing nothing but diapers underneath a T-shirt. When I realized what happened I blushed and pulled the bedcover over me, but Bobby smiled and in his kind voice told me I looked lovely.
The next time it was an even hotter day and Bobby asked me gently if I planned to put on my pajamas again. I hesitated but couldn’t decide not to. But this time Bobby insisted, telling me I couldn’t just go on being ashamed for the rest of my life for having a bladder problem, and that anyway it looked cute. Having a sudden inspiration I threw a diaper in his direction and told him mockingly that if he liked it so much he should wear one too. For a fraction of a second he hesitated but then smiled once more:”Ok, I will!”, and taking off his boxers, unfolded the diapers in front of me. When he had opened the diapers on the bed and sat on it, trying awkwardly to fasten them around his legs, I was suddenly overwhelmed with love. I walked over, kissed him on his forehead, and pushed him on his back: “Let me help you!”
Him doing this for me made me love him very much, and having him lay on his back with his legs open, waiting for me to help him, made him look very vulnerable. I bent over and kissed him passionately, and one thing leading to the other, we made love.
The couple of years before that I had had a number of dates and some of those had pleasantly ended in my bed or that of my date. But there had never been any passion. Now with Bobby I was surprised to discover I felt so passionate, as much as I had had with Lewis. But the passion was clearly not reciprocal and the love making resulted kind of disappointing. Bobby knew it and apologized, explaining with a wry laugh that he was used to be on the receiving side. I shrugged and said it didn’t matter, that the next time would be better. But it wasn’t.
Becoming lovers changed our relationship completely. I loved Bobby passionately but Bobby, although I know he loved me very much, never really desired me. And I just could not accept that. Unconsciously I began taking revenge on him, little by little.
The first thing was that I insisted he wore diapers every time he slept over, which he accepted light heartedly. But in the morning coming out of bed I resented that his diapers, contrary to mine, were not wet. So I told him, laughingly, that we were not going to throw away a non-used diaper and that he would have to keep it on until he peed in it. The first time he had been surprised but again he had shrugged and, laughing, he had opened his legs and wetted his diapers while I watched. This again made my heart overflow with love and taking him by the hand I led him to the bathroom where I washed him.
From then on it became standard for him to keep his diapers on for breakfast and then wet them so that I could help him take them off and wash him. Of course I would scold him for being a little baby.
And of course that didn’t change the unsatisfactory sex. As he used as excuse that he preferred to be on the receiving side I bought myself a strap-on dildo. When I put the thing on and made Bobby bare his bottom and bend forward a sudden exhilarating feeling of power got in to me. For the first time ever I was in charge of a relationship, I was the dominant partner. I’m still very ashamed of what happened from then on, but I couldn’t stop anymore and abused my power over poor little Bobby ever more.
Today I realize that Bobby, insecure Bobby, forever looking for parental approval, had become very dependent on my caring, loving and supporting him. If I had realized it at the time maybe I would have acted differently but as it was I just loved to have someone depend so much on me.
I soon had him diapered and babied 24/7, much as my mother used to do to me, or as Alistair did. I still don’t understand I didn’t realize what I was doing.
On a typical school-day the alarm would go off and we would both wake up – of course he had moved in full time with me because not only was that a cost saving, but little kids can’t live on their own can they? – and I went to the bathroom to quickly take off my diapers. While he waited in bed I prepared a mug of milk for him – cold in summer, hot in winter – which he drank while I washed and dressed. Next I prepared the breakfast table and told him to get out of bed and join me so that I could spoon-feed him his cereals. When we both finished our breakfasts I took him to the bathroom where I took off his wet diapers and told him to relieve his bowels on the toilet while I did my make-up. Next I washed him and helped him dress.
To go to school I had him wear baggy, low hanging, jeans under long T-shirts. Although his diapers showed above the waistband of his trousers the shirt safely covered everything up.
It was surprising how easy it was to make him do all this! Looking back I realize I used a cunning combination of charm, playfulness and …. pure blackmail.
Bringing him milk in bed in the morning was of course a kind gesture as he always had a hard time coming out of bed and really loved to drink milk. But when one day he spilled milk on the bed I scolded him like a little kid, and the next day, serving his milk in a cup with a beak, I repeated the reproaches of the previous day, accusing him of being sloppy and careless. But then, adding with a playful smile that “baby cups come with baby bibs” I bent over and put a bib around his neck.
When he wanted to be kind and insisted on helping with the household I told him it was not necessary, that he just had to relax and let me take care of him, because “it was the first time in my life that I could take care of someone”. I insisted, but from time to time I couldn’t prevent him to do something. When he did I always found fault with what he had done, or how he had done it, scolding him for being clumsy, and repeating in an annoyed voice that I preferred to do it myself. Having undermined his confidence this way he soon stopped proposing to do anything on his own and let me help him with almost everything.
Getting him to wear diapers to school however was more difficult. At first he refused categorically but I didn’t relent, appealing to his sense of guilt: “I like you to be my little baby, and you refuse to give me that pleasure?” When that didn’t work I tried to force him by a combination of hygienic reasons and guilt: “Besides, you always leave yellow stains in your boxers. It’s not very clean and it’s no fun for me having to wash them.” He still refused but I saw his resolve was disintegrating so I went for a little blackmail “Well if you don’t love me enough to do that for me we can as well break up” That did it. He cried hot tears and accepted to wear diapers to school and to his job.
After breakfast we drove together to school except on the – frequent – days that I had no classes. Those days I drove him to the bus stop as he didn’t have a driver’s license. The bus stop was only 1 or 2 miles from my place but, as any over protective mother, I preferred to drive him and wait with him for the bus to arrive.
In the afternoon we always met at the coffee shop where he worked after classes until he was ready and we could go home together. I went to meet him there even on the days I had no classes. Once at home I helped him out of his diapers and dressed him in function of the plans for the rest of the day.
If the weather was good we often went to the beach which was only a 15 minute drive away. I discarded all his ugly, long, surfer pants and replaced them with cute speedos. They had cartoon figures on them and as I had bought them in a children’s shop they were very small. It looked very cute and sexy at the same time. I loved to see him wear a t-shirt that completely covered his tiny briefs, almost as if he was wearing a little dress. With his slender build he looked very feminine and that of course gave me other ideas.
I had noticed on several occasions that he lingered in front of my wardrobe. I never wore a dress or a skirt anymore, always wearing tight fitting black pants, and very exceptionally, on very hot days, or to go to the beach, I would dress in shorts. But I still had a couple of summer dresses hanging in my closet, and I was sure that when Bobby lingered in front of my open wardrobe he was looking at the dresses. So one day finding him standing in front of the closet I asked him if he wanted to try one on.
He turned around, looking surprised, but blushing slightly, asked: “Try what on?” “One of my dresses, silly.” He seemed flabbergasted and began to stammer: “No, no, not at all, of course not! But, eum, I think, eum, I would like you to wear them. I wonder why, eum you have them so why not, eum I think you would look wonderful in them.” For a moment I hesitated, but then decided I was not going to let me change my mind: “Oh no baby, no more dresses for me’” And then standing next to him I took out a short flower-print summer dress, and held it before him smiling: “Let’s play dress up darling! Come on, let’s have some fun!” Of course he accepted and once he had pulled on the dress I taught him to apply make-up and he spent the rest of the day as my cute little doll. And from one came two, and soon he liked to dress as a little doll.
Having him walk around in dresses or with a short skirt of course was a permanent invitation for me to get my dildo and take him from behind. “Being on the receiving side” didn’t do anything for his passion but I hardly noticed it anymore. He was there to be taken whenever I fancied, never mind what he wanted.
In the week-end we would often assist at cultural events like concerts or exhibitions, or go on long biking trips. I always made him wear very small, tight fitting shorts, putting in evidence his tight little bum and nice tanned legs. On one of those occasions, visiting a photo exposition of male nudes, I noticed how the bump in his shorts grew, making them almost burst open. I was amused but annoyed and jealous at the same time. Getting him into that awkward situation became a little game that amused me a lot and he certainly enjoyed it too despite being very embarrassed whenever he thought somewhat had noticed his boner. I never told him it made me feel jealous.
But telling all this I think I make it sound much worse than it actually was. We did love each other very much and there was a tremendous amount of tenderness in our relationship. I think we both wanted it to last forever.
I just loved to take care of him, to cuddle him, to protect him. And, despite his initial resistance, Bobby loved to be diapered by me. Just lying on his back with his legs open his member would grow in anticipation of me softly applying baby powder and folding the diapers tightly around his legs. And, although he would never have admitted it and always pretended he did it to please me, I knew he adored the dress up games in which I changed him into my cute little obedient doll. We loved to go shopping for new dresses and skirts. He would get all excited going together with me in the changing room where he would be the one trying on the girlie clothes.
But I also knew something was missing for both of us. Not wanting to admit that this was the way it was I decided it would be nice for little Bobby to have a baby brother or sister. Foolishly thinking that that would compensate the missing part of our relationship I stopped taking anticontraceptives and soon got pregnant. I didn’t tell anything to my lover-boy but when I was in my third month one day Bobby walked into the bathroom while I was washing and he started laughing: “It seems you are finally putting on some weight! You are even developing a little belly!” I thought this was so sweet!
I wondered when I would tell him he was going to have a little baby sister, and how he was going to take it. I was afraid he might become jealous but decided that was probably not the case as he was such a sweet little darling. Once he would have seen his little baby he would love it.
But it never came to that. One day I stupidly stumbled from a stool on which I had been standing to clean the window and I lost the baby. When Bobby came to the hospital and learned what had happened he was very supportive, but he was also furious that I had planned to have his child without even consulting him. A few weeks later we broke up.
Another relationship I had failed. I felt guiltier than ever and ended my master degree in pure misery, convinced I was an irreparable failure at relationships.
Next chapter: https://clairodon.wordpress.com/2014/10/16/redemption-8/