update and re-write

I now have a better handle on the events that happened all those years ago, my memory was somewhat clouded by the progress of time but now I think I have it together better.

The events happened between my 10^th and 15^th year, I now know how it started and have decided to rewrite history as it were getting the time lines and the facts right, there is no doubt that it happened but it is only now that I fully appreciate what occurred and that I wish I had taken more out of it than I did.

With her husband my granddad being away for years at a time I used to spend most of the holidays with her as we didn’t live too far away.

I first went to stay with Nan soon after she moved, really to help her to settle in and as I was her favourite as it were (plus I was a good bit older than my brother).

Most of her stuff had been in storage so there were lots of boxes to sort out and unpack. The bungalow she had bought was new and all her furniture had been moved in before we got there so there was no heavy lifting.

My parents and brother left early afternoon just after lunch, so we decided to do some unpacking, she decided that we would start in the bedroom as she need to sort out where to sleep.

The bed was as yet unmade so we put the boxes on top of it so we didn’t have to bend down, I opened my first box and it was full of Nan’s clothes, I started to take them out and lay them on the bed, dresses, skirts, cardigans and then petticoats, I looked up to see Nan looking at me and smiling, she was looking down at the front of my shorts where a large bulge had appeared in the front.

I have always been able to talk to my Nan I started to tell her about my love of ladies clothes and that while she was staying with us and I was in the house alone I would put on her night dress and get into her bed and wallow in the fragrance and feeling of femininity, I probably didn’t use those words but that was the gist of it.

She asked me if I would like to dress up now for a bit of fun, and I couldn’t say no to that could I. She started pulling thing out of her box and told me to look through mine and see what I wanted to wear, I asked her what to look for and she said panties, bra’s, girdles anything I fancied.

Before I continue I should say that my Nan was a very slim lady looking back she was also very attractive and I suppose she was early 50’s, so her stuff would just be a shade big.

I found a lovely lavender bouffant petticoat and said to her that could we start with this, so we went from there.

I undressed and as I go to my underpants I started to blush at the thought of her seeing my with an erection, she smiled and urged me on.

I dropped my underpants to the floor and stood there naked and probably looking stupid, but I was beyond caring. I should say at this point that I knew nothing of the facts of life and the erection I had I did not know what to do with it, all I knew was that by groin used to ache sometimes after the erection had subsided.

Nan asked me if I wanted to wear stockings she was holding up a black suspender belt and stockings  this was an item of clothing that I had never seen before, I was curious so I asked what was it for so she lifted her skirt and petticoat and showed me. What do you think I said so I walked round to her side of the bed where she proceeded to put the suspender belt on me and then had me sit in the bed while she put the stockings on me and clipped them to the suspenders as I chosen lilac as the colour I wanted to wear we had to have matching underwear to go with it fortunately she had an extensive collection of everything, after the suspender belt came the French knickers lilac with a white lace trim at the leg, lilac bra and then the petticoat. Finishing it off with a satin skirt and white frilly blouse.

She took me to the mirror and I looked at myself and felt amazing my erection although still there was hidden because of the bulk of the petticoat, she made me do a twirl and lift up my skirts to see underneath and I felt a million dollars as they say.

Eventually my arousal subsided but not the ache, we continued to work away at putting the cloths away in drawers and hanging them in wardrobes. She set aside a wardrobe for me together with a couple of drawers she told me that they were for all the lovely clothes she was going to buy me.

 We finally reached the end and I helped her make the bed, I was supposed to sleep on the sofa in the front room as there was not a spare bed as yet, Nan asked me if I wanted to sleep in her bed and I said yes.

When we had finished we needed a bath as it had been a long and busy day so I bathed while she made dinner, she came in to was my back and bring me clean clothes, a pair of white cotton panties a pink nylon layered nightdress with black lace trim and a matching negligee.

I got out of the bath dried myself, washed the bath out and started to fill it for her while it was filling I dressed and again got an erection, this was starting to get painful.

When it was full I called her and she asked me to stay and wash her back, so I sat on the closed toilet and watched her undress and get in the bath, a strange sight but pleasant, one should not be acting like this either of us it is wrong, but who cares I should imagine that there are a lot of you reading this who wish it was you.

I washed her back and helped her wash her hair then helped her to dry off after, I then went into the front room while she dressed, she was wearing a long cream silk nightdress with matching wrap it looked amazing.

We had dinner and she said she would clear up so that I could watch television, in those heady days of the early sixties we only had 2 channels and they went off the air round about midnight, I was so tired that I was falling asleep and as there was nothing on worth watching I went in to the kitchen and told Nan that I was going to bed I kissed her on the check, as I was leaving she asked me to sleep on the far side of the bed.

I got into bed lifting the sheets so that the nightdress was not pushed up, I lay there with the smell of scent on the pillows and started to drift off my hand strayed towards my groin and started to rub my cock, the response was almost instantaneously liquid started to shoot out of the end as my muscles convulsed more and more squirted out into my panties and on to the nightie. I had no idea what was happening but it sure felt good a release of months of tension and aching ball.

I call out for Nan and as I stood by the side of the bed watching the damp patch spreading over my lovely nightie. She came in a looked at me and said that I should not worry that it was quite natural, she did not appear surprised but said that I should change, she got out a lemon brushed nylon nightie, white nylon directiore bloomers and some other bits.

I took off my damp clothes and gave them to her she held the panties to her nose and smelled the ejaculation she made me smell it as well not a bad smell at all.

 She wiped my knob with the damp panties and proceeded to help me dress. She explained that as I was always in such a state of arousal most of the time that I needed to wear a sanitary towel (Dr. Whites) to catch any more mishaps, she held out this elastic belt and told me to put it and pull it up to my waist, she then attached a pad affair that had loops at each end first the back and then the front she gave me the bloomers to put on and when I had done that she told me to keep my knob behind the pad I put on my nightie and got back into bed.  She told me to wait a minute, she went to the bathroom and I could hear doors opening and closing she came back with a tin of Johnson’s baby powder, came round to my side of the bed and pulled back the sheet lifted my nightie and pulled my bloomers down just enough to expose my knob at which point she shook a load of powder over groin, that smell of baby powder to this day can give me a strange sexual feeling.

 Putting myself back together and settling down, I quickly fell into a deep happy sleep and only stirred when Nan got into bed and snuggled up to my back.

I awoke in the morning with a stiff throbbing cock sticking out from behind my sanitary towel and pushing out my nightie. As I walked into the kitchen she noticed that there was a bulge protruding from the front of my nightie, she asked me if felt uncomfortable and it did so she took me back to the bedroom and sat me on the end of the bed she sat opposite me on a stool, first she told me pull my nightie up and pull my bloomers down and there poking out from behind the sanitary towel was a hard throbbing cock. She looked at me and smiled and told me to take my cock in my right hand and start moving it up and down, I could see from the smile on her face that she was enjoying watching me, she held in one hand the pair of knickers I had soiled last night the other hand was on my knee, as I stroked my cock I could feel my heart start to thump and my breathing get faster and in no time I gushed into the knickers that she held.
She held the knickers there until my cock started to go down, she had taken her hand off my knee and was running her fingers through the mess in the knickers, when it was over she made me pull my bloomers up making sure my cock was behind the sanitary towel to catch any drips, and we went and had breakfast.

Over breakfast we discussed what we were going to do for the rest of the day as there was still so much sorting out to be done. Her thoughts were that I should be a little girl whilst we were together in the house when my family came to stay then we would revert to a normal relationship. To this end she said that I had to act totally as a girl even to the extent of sitting to pee and powdering between my legs afterwards.

I needed a bath after last night’s episode, so she decided the we would have one together For the first time I bathed with her which was a strange experience to say the least she first of all washed me all over and I mean all over, then I washed her all over as well, she dried me and I dried her. Naked we walked back into the bedroom where I waited for what was to come next.

I was to wear a corset and stocking same as any other girl, first of all she put on a negligee not that it did a lot for modesty, but was lovely and so feminine.

 She helped me to put on the corset and did up all the hooks and pulled the straps over my shoulders she then gave me a pair of stockings and I pulled them on but she connected the suspenders, next came the panties but before that she asked me if I needed to wear a sanitary towel or was I ok for the moment the reason being that my cock was growing, but I was ok for now.

Next the panties a pair of French knickers frilly black satin ones, she then gave me a negligee and told me to wear that for now as it was her turn and that I was to dress her the same, this was the mistake I just about managed to get my negligee open and panties down before I came again just managing to catch most of it in my hand and hers.

When I had finished I had to make adjustments to my underwear to accommodate the sanitary towel, so I had to release the stockings and roll up the corset to get the belt underneath, that done she connected the pad and I finished dressing.

Dressing her was so exciting I helped her into the corset and did up the hooks and laces next the stocking this meant that I had to kneel in front of her with my face inches from her crotch, I know what you are thinking this was my Nan and I was 10 going on 11 but what the hell. Next French knickers pink ones, then a long white slip and floral house dress.

My turn to finish off I was given a black full length slip black flared skirt and a red blouse, and I felt great.

We went into the front room and started to put stuff away while we were doing this she was telling me about the things we were going to be doing and how I was to conduct myself in company. The only people that would be allowed in whilst was dressed this way would be people who would not cause a problem.

We finished in the front room and moved to the bathroom  where I saw many feminine things including more of the towels, I went next door for a pee and she called out to me to remember to sit and powder, now I have always been used to standing a peeing, sitting was another issue, this would have been ok had I been wearing a little less that I was at this time having to hold up the skirt and petticoat pull down the panties and get my knob out from behind the sanitary towel was not easy, I think she heard me struggling  and came to the toilet to help me I had not bothered to shut the door what was the point, she held up my skirt and petticoat so that I could concentrate on getting my knob to pee into the bowl rather than up in the air, because with all the messing about I had got an erection again. Finished powdered and sorted out we went back to doing the putting away.

We finished just in time for lunch soup and bread, my turn to wash up  it was while I was  washing up in the kitchen wearing the obligatory apron there was a visitor a lady friend of my Nan, I was a little concerned as what to do so I waited in the kitchen for my Nan to tell me what to do, I had finished the lunch dishes so just sat and waited, Nan came in to make tea and said her friend wanted to meet me and that I was not to be concerned about my appearance, so in we went and her friend was rather taken aback by my appearance but quickly recovered her composure and we related to her some of the events that lead to this dressing up but not everything.

When her friend had gone we sat in the front room and Nan got out a pen and pad so we could make a note of what we were going to do tomorrow. Mainly buying clothes for me.

She said that I would need an almost complete wardrobe but was quite happy to share hers. She phoned her corset lady and made an appointment for early next morning and continued to make out the list. Panties, girdles, bra’s petticoats and nightwear plus more sanitary towels

Nan let me stay up with her so that we could go to bed together we undressed and got into our nighties me with the sanitary towel and panties though. We got into bed and she turned off the light and put her arm around me and drew me to her breast, she whispered in my ear that if I wanted to relive myself it was ok and she would just hold me whilst I did it, this was an offer that I was not going to refuse so I did, didn’t take long though as I was so turned on from the day, after I had finished she said to me that is was ok to sleep with the damp towel and panties and that tomorrow we would go shopping for the clothes and undie’s we had talked about and on that happy though.

The morning started with great expectation we got out of bed and as she went to the kitchen I ran the bath while it was filling I took of my nightie, panties and towel and put on a pink negligee that I was to wear all the time rather than walk about naked, I went into the kitchen where Nan gave me an approving smile and passed me my tea, I returned to the bathroom to wait for the bath to fill, I sat on the closed toilet lid and drank my tea, Nan came in having also undressed and had on a red chiffon negligee that looked amazing.

She saw me looking and told me to wait as there was going to be a surprise later that I would enjoy.

We got in the bath but this time I washed her first then she washed me we dried each other put on our negligees and went into the kitchen for breakfast. She left me eating in there for 10 minutes and then called me into the bedroom. She had laid out the clothes I was going to wear today for our shopping trip which I was really looking forward to.

She said that although I was to dress outwardly as a boy I would wear women’s underwear, a roll on girdle with suspenders, stockings, panty and the sanitary towel. She helped me on with the sanitary towel belt and attached the towel to the rear hook whilst I did the front we didn’t want me getting excited and having an accident whilst out and about, she connected the suspenders to the top of the stocking telling me that later I would have to do this myself and she would show me, we topped off this with a pair of frilly white panties, the bulge in the front of the girdle was not only the sanitary towel. She saw this and told me that it would subside and to just relax.

I remained like this as I helped her dress first doing up her corset, I watched as she pulled on her stocking and connected them to the suspenders, next I held her panties while she put her legs in the and pulled them up, finally he petticoat a sheer black full length one with frills round the bust and hem, this was not helping my situation one bit I thought I was going to explode.

Finally we both finished dressing I wore jeans and a shirt she wore a lovely black dress and fur stole.
We got in the car and as we were driving into town she started to tell me what she thought had happened to me.

She said that I was developing early and that I was a little on the girly side as I clearly enjoyed wearing women’s clothing, a comment that I could not disagree with. I told her that I couldn’t wait until we got to the shops and asked if I might choose some of the cloths for myself and she agreed.

Our first port of call was the corset lady, she specialised in corsetry and underwear, the lady was expecting us and as Nan had explained the situation she was not surprised,  as we walked in she put the closed sign on the door and pulled the blind, she led us into a back room and Nan told be to undress as far as my undies, I did this with a little trepidation as I was not sure about other people and remember this had happened so fast I was still trying to come to terms with it myself.

Having got down to my undies she proceeded to measure me for a full corset with hook and eye gusset and detachable suspenders on white, she had one in stock that would just need to have suspenders attachments added as said it would be ready in 1 hour, we also bought me some directiore knickers and a bra. I got dressed and we left to go and get the rest of my clothes, the next place was a shop that sold ladies undies and nightwear so it would be where we would get most of what I needed.
I chose for myself a pink suspender belt and matching bra, some pink panties really nice frilly and flimsy,

Nan chose my petticoats one bouffant in white with lots of frills and one full length pink one with lots of lace round the bust and hem just like hers, a few extra panties and then it was onto the nighties I said to her quietly that I really liked the feel of the brushed nylon so she got me two one pink and one lilac, also got a nightie and peignoir set in pink with black lace trim and finally a baby doll in baby pink. One last thing was an evening dress and shoes, she said that I would look good in one and that we could dress for dinner so I got a lovely yellow and black full length with a flared skirt and black shoes (had to guess the shoes as trying them on would not look right.

Just before returning to pick up the corset we popped into the chemist to get me a supply of sanitary towels and an extra belt.

We picked up the corset and set off home as it was about 1pm and the pubs were still open she fancied a drink and the sun was out so we could sit outside, she returned with the drinks and started to chat about what we had bought, I was still in an advance state of arousal having been hard for hours and was beginning to ache, I told her this and she said that if I could I should go to the toilet and sort it out, I said that I preferred to do it sitting at the table next to her, as there was no one about I undid the fly on my jeans and slid my hand inside and quite literally just rubbed the front of my girdle and ejaculated into the sanitary towel, and did that feel good.

We arrived home without further ado and she asked me if I wanted to change to which I replied that I did but only into a nightie as I felt tired and wanted a lie down, she agreed and said why did I not try out the baby doll s off I went into the bedroom put my newly acquired clothes away stripped off my undies cleaned by self and put on the baby doll looking at myself in the mirror I couldn’t believe how I looked and felt, but I was tired so got into bed.

It must have been about an hour later that I felt Nan get into bed next to me and cuddle up to my back and push her breasts into me. I went back to sleep contented.

When I woke she was not there but laid on the bed were the clothes she wanted me to wear, the new stuff we had bought today, I thought I could hear voices coming from the front room so cracked open the bedroom door and sure enough there was a strange female voice.
Staying quiet I started to get dressed belt and towel first then the corset and stockings managed ok with front suspenders but couldn’t do the back ones, put on the panties I had chosen frilly pink and flimsy and the full length pink petticoat, topped off with the baby pink dress with lots of frills and finished with the shoes, sensible shoes low heels.

Nan must have heard me for she called for me to come to the front room and not to worry about the visitor as she knew about us. I timidly walked into the front room and there sitting on the sofa was a woman about 40 or 45 very attractive and well dressed she introduced herself and asked if I was ok, my shaky reply must have given my nervousness away but she soon put me at ease when she said that her son was the same as me but a good bit older and that he liked the same things. Nan asked if had been able to dress ok and I said yes except for the rear suspenders she asked me to lift up the back of my dress and she would take care of it, I lifted my skirt and petticoat so that she could connect the stockings when she had finished the other lady asked me to give her a twirl so she could have a proper look at me, I obliged and she said how nice I looked. She asked me to sit next to her.

When Nan went to get the tea she put her hand on my thigh and started to move it towards my private parts, she could see me squirm but continued, whispering in my ear that she wanted to look under my dress and that Nan said it was ok. I felt weird and scared but at the same time elated so I stood and lifted the front of my dress and petticoat so she could see my panties and stocking tops, she put her hands in the elastic of my panties and pulled them down to my knees and could obviously see the sanitary towel inside the corset and the bulge of my hard knob.

With that she stoked the bulge of the towel and knob and in no time I was shaking with pleasure and ejaculated into the towel, she asked me if that felt good and I said it did, to say that I felt good was an understatement, I had felt good two days ago when this started but now this was something else. I was getting comfortable with dressing and being a girl.

 Nan came back with the tea and we chatted for a while and I said that it would be nice to be a little girl rather than dressed as a woman for a while to see what it was like, they both jumped at this and plans were made for the following day.

She only lived up the road a little way, too far to walk dressed as a girl but Nan could drive me there. Her name was Liz, and she said that she had lots of little girly clothes that were left over from her son and wanted me to visit tomorrow with Nan and I could try them on. It was planned that we would go round after breakfast tomorrow.
Mornings were a source of great joy even in such a short time we had fallen into a routine, she made tea

I filled the bath, we bathed and breakfast and dressed, Nan told me not to wear a girdle just panties, bra and slip I could dress as a girl because we would only be going to Liz’s house and like Nan’s it had a drive way.

I said I wanted to wear stocking and the rest but she said that I would only have it in for a few minutes, at the my curiosity was roused so I asked why and was told to wait and see, so I topped off my undies with a pink summer dress.

We arrived at Liz’s place about ten and when she opened the door dressed as nurse I had a feeling this was going to be a good day. We went into the front room where we sat and she explained what was going to happen.

First of all I was going to spend today as a baby girl of 2 who was being potty trained so I would have to wear a nappy but not to use unless told to. Then tomorrow as a 4 year old then 6. And finally as a little girl of 8 and that went with it. If they had looked at the front of my dress they would have seen that my expectations were very high. The only thing missing was being a real baby but that was a step too far.

She took me by the hand up the stairs and into a small bedroom that was all done out in pink all different shades but really nice with frills everywhere this she said was her son’s room when he was little.

She asked me to undress, this I did but was slightly ashamed by my erect penis but she said not worry as she had seen it all before. As I stood there naked not knowing where to put my hands she asked me to lay on a plastic sheet that was spread on the bed so she could put on the nappy, she creamed my bottom and round my penis and finished off with a good powdering even to this day I find the smell of baby powder quite powerful. The nappy was followed by a pair of frilly pink plastic pants for the tights I had to sit on the edge of the bed while she put my feet in them and I stood up so she could pull them all the way up finally a lovely pink frilly dress I felt that I was in heaven, I really wanted to get my hand into the nappy but I held back, Liz now told me that for today I would do what she said and that if I needed to use the toilet she would help me.

We went back down stairs where Nan said I looked beautiful and we sat in the front room where I played with a doll and they chatted.

Nan left soon afterwards saying she would be back for me at 6 o’clock that evening, I played while Liz made lunch, before lunch she asked if I needed to use the toilet  I said not now so we had lunch, on finishing lunch she said it was time for my nap and I would have to go to the toilet first, we went upstairs and into the bathroom where I pulled up my dress while she pulled down my tights and knickers and undid the nappy she sat me on the toilet and waited for me to pee when I had finished she wiped me between my legs and told me to follow her into the where I took off the dress, we went through the same process with the nappy and knickers but now I had to wear a little pink nightie, she tucked me into bed and left the room I lay on my back and took in the room and it was so girly I could stay there forever, I was getting the feeling back in my nether area so rather than use my hand I turned onto my stomach and just slid up and down rubbing my erect penis against the inside of the nappy and it did not take long before a wave of relief swept over me.

About ten minutes later Liz came in and seeing that I was still awake told me to use the nappy if I needed to do toilet as she wanted to change me properly before I left for the night.

I thought about this and a wee would be enough so I left it for a while until I felt like I needed to which was not too long as I had had quite a lot to drink. I was laying on my back and just let it go, and what a feeling that was the steady trickle of warm urine across my tummy and down between my legs was amazing and so warm and wet, I squirmed a bit so that the feeling spread round my bottom and I just lay there and reveled in it.

I must have fallen asleep for the next thing Liz was giving me a shake and waking me up, she asked if I needed changing to which I said yes, so out came the plastic sheet and I got out of bed and discovered that I had not only filled the nappy but some had leaked out onto my nightie and into the bed, she said not to worry as she had expected this to happen. I took off the nightie and lay on the plastic sheet she pulled off my knickers and undid the nappy, she looked at me and at the inside of the nappy and I could see from her face that she knew that it was not only wee that was in there but she said nothing.

She cleaned me off and started to put the barrier cream on all round my bum and between my legs moving my knob with her hand that was a good feeling put the nappy liner in and pinned up the nappy. As I squirmed into the plastic pants she asked me if I wanted to be breast fed as only today was I “old enough” for that and I jumped at the chance.

We went down stairs and she sat at the end of the sofa and undid her blouse and exposed her breasts she asked me to lay on the sofa with my head in her lap, I did this and it must have made a strange picture me laying there looking up at her breasts.

She  lifted my head and guided her nipple into my mouth, I had not been here even as a baby as my mother was unable to breast feed not that it would have made a difference I couldn’t remember that far back. Her nipple went hard in my mouth just as my cock was doing the same in my nappy.

She said that when baby’s breast fed they held onto the other tit so she put one of my hands on the breast that I was not sucking on, this nipple started to get hard as she lead my hand in a rubbing motion over the nipple.

I continued to do this without her guidance and slowly I felt my dress being pulled up and a hand sliding down inside my nappy, her fingers surrounding my knob started to move up and down and with all the cream down there the greasy feeling was out of this world. I ejaculated in no time flat but that did not stop her from rubbing my knob now even greasier, she just kept on and on until it went hard again, how long that took I can’t say as I was too busy sucking a tit and then I came again, and all the while I am sucking away on her tit.

After the second time she removed her hand and asked me to sit up, she was looking rather flushed and breathing a little heavy so was I for that matter. I sat next to her and she wanted me to remove my plastic pants so she could take off my nappy as I stood in front of her, she asked if I wanted to pee and I did, she said not in the nappy and for me to wait, she got me out of the nappy and from the side of the sofa produced and oversize potty she held this in front of me with one hand and aimed my knob with the other.

I was beginning to wonder where all this stuff from inside was coming from when I had finished I sat next to her on the sofa as she looked inside the nappy at the vast amount of sticky fluid that was in there and then she did the strangest thing she rubbed her face in it, odd I thought, but who am I a young boy dressed as a little girl.

We went upstairs where she cleaned herself and me up and I dressed ready to go home. Liz asked me not to tell anyone not even Nan about what she had done.

While we were waiting for Nan to come and pick me up she explained about tomorrow she had all the clothes ready, from dresses to pajamas and little cotton knickers, boy was I in for a treat.

Nan came they chatted for ten minutes or so and we left. There was a bath ready when I got home and my new baby doll ready on the bed, when I had finished I went a joined Nan in the front room where we watched a bit of telly and had a bite to eat.

I could hardly believe what had happened over the last few days, here was I a boy approaching eleven sitting on a chair wearing a baby doll nightie with my Nan (my mother’s mother) sitting right there with me. And she a willing party to all this.

I have over the years regretted that I did not take more notice of what went on I do occasionally have flash backs but I am sure I am missing a lot but I will try to get it all down so that you can read it, there is a lot more to go but this no gets the record straight.