I was 13 and that day comes back to me vividly and this experience was the start of a desire for women’s clothing. We were a slightly unusual family due to a few things. It was the funeral of my mother’s estranged sister, they hadn’t spoken to each other for years and Angela had not been well for some time, this my mum Christine had not found out but another relative mentioning Angela’s illness. My mother hardly ever spoke of her. They were powerful but feminine women from all accounts, similar in many ways. They had both modelled in their early days, both loved being eye catching.

The family had fallen out and to save face there were lies told between them about all sorts of stuff, this is perhaps one of the biggest lies in this story! I was the lie. My mother had said somewhere in the past that she had 2 daughters not a boy and a girl. Why I’m not sure other than we knew Angela had 3 daughters and perhaps Christine wasn’t going to be outdone!

The funeral date was set for tomorrow and both my sister Juliet and I only found out that day! My mother told us over breakfast we had to go to the funeral. Juliet dashed out the door to meet friends on the way to school and I was left alone with my mother. ‘Simon, you know you love acting and playing parts at school, well could mummy ask if its alright to play a part tomorrow?’... ‘What do you mean?’... ‘Well, eh, could you dress up and pretend to be someone? You wouldn’t have to speak or be on show, just there in the background where no one else will really even talk to you’... ‘ Ok but what am I going to be’. Now suspicious at what this was going to be. ‘You are going to be Sarah’... ‘A girl?’. ‘You are going to be Sarah tomorrow, I really need you to do this for me Simon, I promise we are only going to the church service’. I said ok quietly. I was very unsure. My mother was authoritative, but this time she spoke gently and persuasively. ‘We’ll take a look at your outfit tonight’.

That evening I came home from school and had forgotten what my mother had said as it had been a long day and an after school club. I opened my bedroom door and looked down at my bed immediately as something was on it. I looked closer and thought it strange my sister’s clothes were laid out on my bed. Then I remembered! It was the funeral tomorrow and I had to go as a girl. My heart skipped a beat with the recollection. I sat down on the bed, my mother wasn’t home yet. She had laid out everything, I mean everything. There was note next to the clothes, all I partly read is hast was ‘I have left you your outfit to try on’. Oh no she was serious. I especially noticed the black tights (I live in the uk, so these would be pantyhose if in the US). These tights were about 15 denier and what I considered frightening to step outside in. I had a thing for tights from an early age but never imagined putting some on in front of anyone. I now felt embarrassed as I looked at the little black dress and strappy sandal shoes... even black knickers. I stalled a bit and looked at the items. I decided to go for it and no other people were in the house anyway. I had a bath first as I knew my sister wasn’t home for a while and I didn’t want to get the clothes as if I had been wearing them, odd but I felt cleaner about it.

Back in the bedroom I dried myself and slipped the knickers on, they were small, I know now why this was so. I then had trouble getting into the tights as I hadn’t been shown how to do this. I slipped the dress over my head. I suddenly noticed I knew this dress from my mother’s photographs, it was hers from the 1960’s when the fashion must have suited a slim stick young girl aged 14, fitted and quite much of the time, it was from a fashion shoot. I put the shoes on last and decided to risk going across the hall into my mothers bedroom to look at the full length mirror. I felt very exposed thinking I would have to go to the funeral dressed like this. I knew it all fitted so well though at least, and I did think she had chosen the outfit very well.

The door slammed down stairs and in a short while my sister came running up the stairs as she always did. My panic at this sound was still there despite being back in my room, I’d just got back in there in time. ‘Oh god NO’ I said. And quite unbelievably Juliet without a knock opened the door! ‘What are you doing Simon?!’ ‘I... I’m trying on a costume for a play’. Really!? Yes really, go away! I’m not sure how mother would take this!

Mum got home after 7 p.m. and after some shopping was dropped in the kitchen I heard her walking up the stairs and then the knock I was dreading. ‘Simon can I come in dear?’... ‘Yes ok’... ‘ have you had a good day at school?’... ‘Yes’... ‘Did you find the outfit on the bed?’... ‘Yes’... ‘And, did it fit?’... ‘Sort of’ ‘Sort of?’... ‘Yes it did’... ‘Well how about you show me?’ So I got dressed up again and she came back in. I was sat facing away from her in shame and quite upset about having to dress like that. I remember there was a bit of time and talk before I got up and stood for her to look at me. I was so embarrassed! ‘You look nice Simon you really suit that outfit, your tights need adjustment but nice’... ‘I’m not doing this!’ ‘Yes you are, for me you are doing this. I promise I’ll make it up to you and it won’t be for long’. She was sat on the end of my bed looking me up and down in her business suit, usual sheer tan tights and heels. She always looked very hot if I was to be honest. She was made for skirts and fitted outfits. It did make me feel strangely excited because she was more comforting as well as looking more attractive than usual. She was wearing her shortest skirt with the blouse that matched so well that day. ‘Yes, you have nice legs for a hem above the knee and those black tights go well’... ‘I feel scared of what others will say’... ‘No need, we all act parts in life and this is your first major roll, and its only a walk on and stand around one’... A bit more conversation went on. I’d never been quite so confused, I found her strangely attractive. She went out the room and came back with a hat ‘Here put this on’...’Its a woman’s hat I’m not wearing that’... ‘ Simon, go on put it on. It will hide your face through the mesh face cover. Its a funeral hat I’ve borrowed off a friend for your head size and me and your sister will be wearing one as well. I tried it on and my mother walked me to her room to look at myself in the mirror. I must say I looked passable, in fact I felt attracted to myself. I remebered a couple of girls at school where I envied their outfits, but now I could be them. Then she handed me a long dark grey overcoat to wear over the top and it looked even more right. The overcoat and shoes were my sisters she had outgrown, she was nearly 17.

To explain, this was a funeral in an affluent area and it was the late 80’s where fashion and the social standing of especially the other half of the family meant making an effort of a high formal look.

By now I was feeling more comfortable and more up for the part. I even could feel how the girls acted at school coming across me. Could this be true, my mother had turned me onto tights and a dress as well. I found the experience erotic. My sister went out 20 minutes after she had walked in on me so the anxiety of the experience wasn’t that bad. I asked ‘have you told Juliet about me going to the funeral as a girl?’ I even felt good about asking that question. ‘I will tell her when she gets home dear’ All the time my mother was being very feminine and comforting making a fuss over me.

My sister came home later that evening from a friend’s house and not long after my mum had the conversation. I had put my outfit aside and now felt more ok about sitting in front of the TV downstairs. I turned the sound down and listened intently. I recall a bit of a giggle and 1 or 2 louder words saying ‘you have to go along with this Juliet.’... ‘But mum you are lying and its making me look bad, I have to stand next to my tranny of a brother!’ That evening ended by me not seeing Juliet and so that bit of the experience was edgy for the next morning.

Saturday arrived and I was nervous. I had half the morning to go out on the park and hopefully get lost forever. Juliet was sent out looking for me and we both walked back in silence except for ‘I can’t believe mum is going to do this, you better not embarrass me!’ Mum was upstairs when we got in ‘She found you then, where have you been?’ I went upstairs where her bedroom door was open and there she was quite unashamed pulling her sheer black tights on under her very eye brow raising short dress. I hadn’t seen her in this black dress before. She adjusted her tights top seam under her dress as she said ‘Well come on dear get changed we have to leave in 20 minutes. I went back into my room and found the clothes replaced onto the bed. I felt now my fate was sealed! I was going to become a girl. I felt nervous all over again as my mum followed me in seconds later ‘Right Simon I’ll help you out with your tights in a minute, advice from a woman who has worn them so many times’. I got into my knickers while she turned her back ‘My those work a treat’ She rolled up the first leg of the tights and put the right leg over my foot and pulled them up to below my knee. ‘Now you try the left leg’. I rolled up the other leg as she had done and put it over my left foot. ‘You see its just like putting your socks on but these go all the way up your legs. Be careful though as you don’t want to run them’ She then proceeded to help me up with the rest and adjust everything into place. I noticed they were different tights at that point ‘I bought you a new pair to wear that are a little thicker, sheer and have compression in them to keep them up’ She helped me into the dress and shoes. My sister then walked in and I felt ashamed again. She looked me up and down. ‘So what’s her name then?’... ‘Eh... Sarah’... ‘God embarrassing!’... ‘Look just go and get on with getting changed if you are going to be like that!’... ‘I am!’ She was stood there in her equally revealing little dress and sheer tights, a dress that was more fit for the night clubs she wasn’t yet meant to go to. ‘Well I think Simon can play this part very well today.’... ‘My brother is dressed as a girl, I mean is his voice going to work’... ‘Well he doesn’t have to say anything’... ‘You think that’s true then you’re wrong SARAH!’ I recall my sister being a bitch that morning. We got to the front door where mum adjusted the hat on my head. The hat I realised was the key to it as it had the fishnet covering that helped me stay hidden. I also remember there was a wig but it never got used as it didn’t look right. I had longish hair that mum slicked down in a way that look feminine at the time.

We got into the car and drove off. Luckily the driveway was mostly covered from the street by cars. Luck had it to school friends did walk past and look over for 2 seconds. I sat in the car mind racing they would recognise me. It was a bit of a cold day and my legs were exposed apart from nylon. I replacing the overcoat back over my knees. The car heating was on and the warmth made it a nice experience feeling the air up my legs. I appreciated the feel of the tights and because I was sat alone on the back seat I touched myself up. I had recently started to change and go into puberty. I was getting turned on and wet by sliding my hand up my thigh and touching my tight silken crotch. I loved the silky knickers that were now pulling with the weight of my erection. The dress also holding me tightly around my body. I couldn’t believe how I felt.

We arrived at the church where there were a few people arriving. I put myself right and panicked at the same time. We had pulled up next to a car full of people and I held off getting out until they were in front on the pavement. My sister and mum had gotten out and were standing waiting. Mum then opened the door for me. ‘Come on Sarah dear’. Then I realised the other car next to us had drawn up. 2 old couples looked at me getting out the car. ‘They then walked up behind us, the old ladies kept looking at us. We entered the church and walked forward by 20 rows or so before sitting 3rd back. We pushed along into the middle of the bench and we sat next to a family. My mother sat me in the middle to avoid to much contact for me. A few minutes and she realised we had sat behind her brother-in-law. I could see her change and bite her lip. She looked over at me and away again. Then he turned around and glanced at her and me briefly. Apart from this the ceremony went ok. All I could think about was my own enlightening religious experience stood and sat in the service. My excitement hidden under my coat. We had to leave the church and talk to a few of the guests, worst of all the brother-in-law shook my hand. I wish I’d worn black gloves as my hands were surely male. He was quickly moved on to my sister who got embellished about here gymnastic and horse riding achievements. I got a foot note as to my ambition as a scientist.

We then did as my mum promised and we went home. It was excepted we wouldn’t be more of a good family and go on to cremation and wake. And more importantly for me it was excepted I passed as a girl. We got home and then my mother got upset, Juliet and I sat at the kitchen table with a late lunch and my mother started to explain her relationship with her sister. She had forgotten I was sat there being her daughter instead of son, so did my sister who was more concerned about mum. I then saw the other side to a woman who cares. She was full a regret I think because she then got up and said ‘Come on, we’ll catch them at the wake!’

Yes here I was sat in the car again being driven off to play act 2 as Sarah. I dare not say anything as she was full of emotion. We drove for about half an hour to the house of the brother-in-law. My mum got out of the car and stopped and said ‘Oh sorry Simon you’re still dressed up. Could you do this again for me?’...