The chapter list
Chapter 1
I had just finished college and found myself a job and even that turned out embarrassing as I applied for a job in an office. Nothing strange in that except people gets preconceived ideas about who is going to show up when your name is “Kelly”.
It would never have been my choice but my parents had decided that would be the name no matter whether I was born a girl or boy.
I showed up for the job interview and was told they thought I was a girl but it did not matter, they just did not get many male applicants. I did not care and was just happy to be leaving college and getting a job. I met my girlfriend while on the job hunt one day in a coffee shop, she was having a break from work and I was looking through the adverts. We chatted and hit it off straight away and thing were perfect.
I had been planning to get married to Hannah, my girlfriend for some time now but things in life do not always work out as you planned. We had been saving but with me losing my previous job prior to the pandemic, our savings had now started to dwindle somewhat.
We had always been experimental in sexual things, both loving to dress from time to time, something that I had done a lot more of in my younger years, loving the feeling of dressing in my older sisters clothes when I got the chance. She had some cute stuff and that is what I always tried on in secret, always wanting my own things but never building up the courage to buy any.
She would give me thing to try on for her, some grown up but some that looked far younger in style that I was unsure about, but my girlfriend had always wanted to take the more dominant role in things so I went with it. She was slightly older than me, well ten years actually so it really did not bother me that she wanted to take charge, it just seemed natural.
My girlfriend had a really good job, something which seemed to run in her side of the family as her mother also ran a successful clothes shop in the village where she lived. We had tried our best to find a house of our own but it soon became evident that we were going to have to move in with her mom in her large house.
Now when I say she had a large house; that was a bit of an understatement. It was more like a mansion with six bedrooms, three bathrooms and even some work rooms for her mum to mend and alter clothes for the ladies that came to her shop. We had stayed there several times before and I had explored the entire house but was told the attic rooms where off limits to me, something I found curious but it never really bothered me.
“Well it is nice to have you staying” said Valerie, my girlfriends mum, “I just wish that things had worked out better”.
“I am sure that they will improve” said Hannah to her mum. When I looked at her I could have sworn that she gave her a little wink afterwards but I could not be sure so left it at that.
“Well you know where your bedroom is so take your time unpacking” said Valerie, “I will let the removal people know to store everything else in one of the garages out back”.
So there we were, back in Hannah’s mothers house once again, the place she had moved out of when we got a flat together. We collected the boxes of things we wanted to go in the house and I moved them upstairs to the first floor while Hannah started to unpack.
Valerie stopped me while I was still downstairs to give me a drink after noticing how hot and tired I was looking.
“So I hear that you are still struggling to find a new job” she said handing me the glass, “I might be able to help if things do not work out”.
“I can’t seem to find the same sort of job that I left” I replied, “It was nice”.
“Well sometimes you just got to do what is necessary” replied Valerie, “I know you can’t be that happy having to move in with me”.
I could tell that she was trying to be nice but at the same time she was having a little dig as well, trying to make me feel a little inadequate. That was something that she had always done to me, never thinking I was the one for her daughter with both of them being so successful.
“Now while you are hear I think we need to sort something else out” said Valerie, now looking a bit more serious,
“I think you need to call me mum rather than Valerie”.
“I know you would want you to after getting married so you might as well get used to it now, ok”.
That last part from her was more of a statement than a question, so I thought the best thing to do was just to agree.
“Yes mum” I replied, still feeling a bit unsure but not wanting to upset her.
“Good boy” she replied, ruffling my hair with her hand before patting my bum, “Now off you go, get finished unpacking”.
I went back upstairs with the last of the boxes to find Hannah still unpacking our things into the walk in wardrobes and en-suite bathroom.
“Hi hunny” she said, “Did I hear you chatting to mum”?
“Yeh” I replied, “She told me to start calling her mum”.
“Ahhh that’s mum” she said, “Always wanting to make you feel at home with her, I think she likes you”.
I did not want to say anything to upset her but was not convinced about the “her liking me” part yet.
“Yeh I guess so” I replied tentatively, “I think she sort of offered me a job as well”.
“Oh that sounds promising” she replied, “She did say she might have something to help you”.
Chapter 2
Over the next few weeks, things settled down into a routine between the three of us. Hannah would go to work and most days Valerie, or mum as I was still getting used to calling her would either be at her shop or doing things in her workrooms for her business.
For me it was a case of job hunting with very little success and turn down after turn down. I was looking for something that a lot of others were and I got the distinct impression that all the businesses wanted a female doing the job and not me.
I eventually found myself getting more and more dejected and wondering if I was ever going to have any luck. To help out I started doing little odd jobs around the house for mum, anything from lawn cutting to doing the washing.
As I sat down to lunch one day with mum she began chatting but this time asking me how the job hunting was going. So after I explained all the troubles I was having she seemed quite satisfied that I was actively searching.
“So do you have any plans for this afternoon” she casually asked me, knowing full well that I was hardly going to say yes.
“Not much that can’t wait” I replied, “why do you ask”?
“Well I am trying to adjust something for one of my clients but need a little help getting it just right” replied mum.
That should have set off alarms bells in my head because I knew the sort of things that she made and altered for people, nothing remotely male and very much female. But instead I barely thought about it.
“Sure thing mum” I replied, “I will give you a hand if you like”.
My reply seemed to bring a very large smile to mum’s face which sort of pleased me but more so meant that I would be kept in the good books of my girlfriend. She had made it quite clear that I was not to upset her mum for all the help that she was giving us.
Mum quickly cleared away our lunch things, something that I normally did but I got the impression she wanted to make sure that I did not start doing something else. Now I guess I should mention that compared to Hannah and her mum, then most other people come to that, I am was would be described as quite small.
I never grew much past 5ft and always remain quite thin; something that Hannah said attracted her to me, loving how I still looked young and innocent. I had soft blonde hair that had never really been styled into any sort of shape; I just kept it relatively short and let it do what it wanted.
She took my hand and led me to one of the work rooms, opening the door and ushering me inside. Inside was a mass of shelving and racks of materials in all manner of styles and types. But standing in the middle of the room on a little pedestal was a mannequin of sorts, covered in some sort of pink shiny material.
Only when I got closer could I tell more about it. The material looked like some type of pink satin, but there were lots of lace trimmings around the edges. The legs on it were very short, almost nonexistent and the crotch had little buttons across it. There was a small zip in the back of it that went down most of the back, but when zipped up it was barely noticeable.
“It is nice isn’t it” said Mum, “I am making it for a lady who wanted a little fun with her husband at a fancy dress party”.
“Oh right” came my reply with me still unable to take my eyes off if it.
“I can see you like it sweetie” she said, “The lady’s husband is dressing as a little baby and she is going as a nanny”.
Mum walked over to a curtain and pulled it back to reveal the nanny costume, perfect in every detail to match that of a old fashioned nanny outfit, but a little shorter in length so that her stockings would show under it.
“Now I just have one little problem with the outfit” said mum, coming back over to where I was still standing.
“It needs to be big enough to carry lots of padding inside of it”.
I must have looked a bit confused about the padding part until she explained fully, only then did I get some sort of idea what she was thinking.
“She needs it to cover the very thick nappy that her husband is going to be wearing underneath it, that is why I need your help”.
“Are you asking me what I think you are” I said to her tentatively,
“Yes sweetie” she replied, “Do you think you can do that for mum, can you be a big boy and help me out”?
Her voice and demeanour was now changing and I was beginning to regret agreeing to help her out, especially as she was planning putting me in that outfit and putting a nappy on me.
“But do I really have to wear a nappy Mum” I wined, almost like a little child; “I am a grown man now and have not worn one for a long long time”.
“I really need you to” she replied, “It is the only way that the outfit will look and sit correctly”.
I knew I really did not want to but the outfit looked kind of fun and cute, but most of all I did not want to upset her or my girlfriend, so with some reluctance.
“Ok I will do it” I replied, “What do you need me to do”?
“Oh thank you sweetie” she said giving me a big hug, “I will try and make it fun for us”.
She took me out of the work room to another empty spare bedroom and asked me to undress and lay down on the bed for her. There was no duvet or anything on it, just a towelling cotton sheet. It was strange to undress for her, but I was soon laid down in my little briefs on the bed. It felt funny when I laid down, something making a light crinkling and rustling noise, but I was not sure what.
When she reappeared, mum took one look at me and had a little giggle.
“I think you need to remove those as well” she said pointing towards my little briefs, “I can’t put a nappy on over the top of them”.
“What do you mean” I began to protest, “I thought the nappy was part of the outfit so it would be better that way”.
“Oh there is a thick cloth one to go with the outfit” she replied, “But I think a nice thick disposable one will be fine for you so I can get the fit right”.
With some reluctance I removed my briefs and lay there now naked in front of her, that crinkly rustling noise still evident. It only seemed to happen when I moved so I slid my hand under the edge of the sheet and soon found it touching a smooth rubber covered sheet.
“I see you have worked it out” said mum, “There is a waterproof mattress cover on the bed, it was put there to protect it when I have had visitors in the past”.
She said no more except for getting me to lift myself up so she could slide the nappy under my bottom. I was not expecting what happened next when she started to sprinkle baby powder on my front and then lifting my legs to put it under me. The cream she then applied to my more sensitive bits caused a reaction that I was not wanting.
I could feel her rubbing it around my private parts and then down around my little botty hole, but my body was betraying my first thoughts and seeming to enjoy it. My little cock was starting to grow in front of my eyes, I was trying my best to control it but I could not stop it.
“Oh dear” said mum, “I seem to be having some sort of effect on your body sweetie”,
“Are you enjoying being put into a nice thick nappy by mummy”?
I could feel the heat burning in my blushing cheeks now, but I could do nothing to stop what was happening, but worse was happening as after her last comment I was now fully erect and hard as a rock in front of her.
“Oh my sweetie” said mum, “You are enjoying this but I think we had best get you fastened in before you have a little accident”.
I just laid there as she pulled the nappy up between my legs and pressed it down firm on top of my hard cock before taping it shut nice and tight. Once done she rested her hand on top of the nappy and rubbed it slightly just to make sure that I stayed hard as a rock.
“Just one more thing” she then said as she reached down to the side of the bed and pulled out a pair of plastic panties in a pale pink with a nursery style print all over them.
In no time they were pulled up my legs and I was standing up while she fitted them over the top of my nappy.
“Perfect sweetie” she said taking my hand and leading me back to her workroom, “Now we can get you all dressed”.
She went over to the mannequin and removed the mass of pink satin and frills and brought it over to me. She unzipped the back of it and then told me to carefully step inside and so she could see how it looked. I remained still while she did the zip up and only then did it become obvious how well it fitted me and showed off the bulging nappy in the back. I heard a little click in the back and did not know what was going on.
“There we go, all nice and secure” said mum, “It fits far better than I ever thought it would without measuring you myself”.
“What do you mean” I shouted out in shock?
“Exactly what I said sweetie” said mum, “It fits you just as it should do, perfect for the little sissy baby girly you are going to be”!
