Why is it always teenage girls & horses? Part 1 of 2

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Why is it always teenage girls and horses?

For the last few summers, only girls had been on the Riding School courses. Was Jack going to be an exception?


My name is Jenny. I help my parents with the local riding school. I liked Jackie the first time we met. I was slaving away as usual at the stables, getting ready for the new summer season when she bicycled in that first day. I had the list of names on the clipboard and I was allocating the ponies to the different girls. My best friend, Alison, was helping me while Laura was round the back of the stables finishing with the mucking-out.

All I could see was the expected jodhpurs, t-shirt and helmet. I called out, "Come on over and see me, please." As she came over, I could see that she was about the same size as Alison - about five foot three - and quite slim. I find it quite irritating how jodhpurs make your bum look so big, but both Alison and this new girl had nothing to worry about. Horribly slim.

She took her hat off as she same up and I realized that she would never be mixed up with Alison. The new girl had short mouse-brown hair, almost boyish while Ali's sandy-blonde tresses were almost long enough for her to sit on. I waited a moment for her to speak then began myself. "I've got to guess that you're the only new name on this list - it says Jack in the little box so I guess that's short for Jackie. There's going to be nine of us on the course and I'm really glad that for another year we're all girls. This means that we can keep the same rules for the whole gang as for the previous five years."

I noticed a frown and that Jack was about to say something but Laura shouted for me to come and sort something out at once, so I dropped everything and ran off to help. As I left I yelled, "Ali, you sort out things with Jackie. Show her where everything is."

So I left the two alone. I didn't get back for ages. When I did there was a message saying, "Had to scoot off to help Jackie get some things for the first day. May not be round until about 9.30 tomorrow instead of 9.00. Ring if this is going to cause chaos." Ali's note was over the top as usual. Half an hour wasn't going to matter this early in the season. I did wonder what Jackie was missing, and why it needed two of them to sort it out. Oh well. Time would tell. I'd wait until tomorrow.

I suppose the real story belongs to Ali so I'll let her tell all about that summer from her point of view. It took ages before I knew what was happening, but then I've had that happen to me before.

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Golly, Jenny is so dim. I couldn't believe that she saw Jack walk up to her and then go bright red when Dimbo started warbling about 'how nice it was that the whole class was going to be full of girls for another year'. I saw Jack's eyes and ears go on stalks like nobody's business. It was so obvious that one of the people listening to this fandango wasn't in total agreement. Then Jenny had to run off burbling like the March Hare about 'so much to do, so little time to do it'. I turned to the person beside me who was stood there resembling a traffic light stuck on red.

"What we going to do about this, then - Jackie?" I emphasised the ending. "Do we have a class of only girls or what?"

"Heck, I dunno. I've never been mistaken for a girl before. What do you recommend?"

It was my turn to be speechless. This was a cool cookie for a mere boy aged about 14. I wouldn't have had the style to deal with an offer that strange as if it was an everyday thing. "Um, er. You heard her. She thinks you're a girl. I'm rather certain that you are not. But, since you'll be wearing those ultimately unisex jodhpurs just like the rest of us - we've got a gorgeous opportunity to get our fuhreress beautifully wound up. Are you game?"

"What do you mean? Am I game? I'm not at all sure what you're offering - let alone whether I should accept what I think I think you're offering."

I grabbed his arm and dragged him to a corner of the yard. "Yes, I'm giving you the chance to learn more about girls in one summer - from the inside - than you'll ever get in your life. Jenny thinks you're a girl, so she'll tell all the others. At the moment, I know you're a boy, but, if you trust me, we can cover that up quite easily. You have no hair on your face, you'll be wearing these ultra-non-sexy jodhpurs, just like the rest of us. If we can make your face and general appearance fit, then you'll be 'one of the girls'. I think it would be a real giggle, what about you?"

Jack pondered for a moment. "If you really believe we can get away with it, I'm game. It'd be a laugh. I shall tell myself that tho' I'm a rough, tough 15 year old and so, of course, too macho to want to be mistaken for a girl, on the other hand since it's just a subtle ploy so that I will understand them better and be more, erm, friendly with them then that's good tactics."

"Good thinking. That sounds neat. I'll give you all the subtlety you desire." I was a bit annoyed at his clear intention to learn enough so that he could score with other girls - I'd give him ploys and tactics. So he didn't want to be mistaken for a girl. I'd fix that too. And my guess that he was only 14 showed that he was lagging behind in the puberty and growth stakes - a definite advantage for me and only a potential disadvantage for him (if he ever realized.) It was only when I looked back a long time later that I realized that much of the impetus for actually making Jackie into a girl, rather than just learning about girls for a while, came from that first angry response.

I decided that we couldn't begin this exciting game in the publicity of the stable-yard. Tomorrow, I would bring back a much improved Jackie to meet the rest of the Riding Gang. "Okay, come with me and we'll decide how to begin this so-called subtle ploy of yours."

Jack followed eagerly as we disappeared off to my parents' house. Mum was out but Dad saw us disappear upstairs. "When you're finished gossiping with the girls in your bedroom, come down. I need to ask you a few things, young lady."

"Uh, oh. That means I'm in a small trouble. At least, if he only calls me young lady, I know I can worm my way out of it. It's funny that he thought you were another of the girls. I suppose it's the clothes mostly."

We zoomed into the bedroom and I told Jack what I was going to do. "First off, you're absolutely safe in riding clothes - so that just leaves your face and hair. Your hair is very short so we can't do much with it except a tiny trim here and there. Then we let it grow out for a couple of weeks."

Jack interrupted, "What, you reckon we'll be able to keep this going for the whole summer?"

"What did you think. This isn't just so you can have a day of 'learning about the girls' and then we all have a laugh. This has to be done as well as you possibly can. From this minute, you are a girl for the summer. At least at the riding school anyway." I already had a few plans of my own to keep Jack in disguise for much more than just at the school. At that moment, I really wasn't planning anything beyond the summer break. Truly.

"So, we can't yet do much with the hair. The face is more difficult. You're an ordinary teenage girl - so you can't wear makeup in the daytime, or at least not so that anyone will notice. However, we've got to give you a little emphasis. I might just use a tiny bit of eye-lash mascara. You've got lovely long lashes but it would help if we made them more visible. Calling you Jackie is obvious too. That's a perfectly ordinary girl's name - hey, it gave us both the idea didn't it. I saw Jenny's list - you're shown as Jack squiggle - so she just guessed. You'll have to learn some new catchphrases. If you eliminate 'magic', 'yukky' and any boy-type words and use 'pretty' and 'lovely' instead. You know, what you'd call girly words. That'll help you be more convincing. What do you think, Jackie girl? You still keen?"

"I think so. After all, you can't do much without my parents getting some pretty strange ideas."

"Don't be silly. It would be awful if anyone else got involved. This is a game just for us girls at the riding school." Ho, ho, just a little lie, Pinocchio.

I spent a while combing Jackie's hair this way and that way. Nothing made much difference and, as she said, her parents mustn't notice. I was making an effort to use 'she' and 'her' so that I wouldn't make a mistake. I did try the mascara too. Jackie pulled faces and muttered, "Careful you don't stick that thing in my eye. I hope you know what you're doing."

"Don't be so silly. How many girls have you ever heard of who blinded themselves doing their makeup. Don't be so daft. Anyway, you'll be able to do it yourself after a couple of practices. I'll get you a stick tomorrow."

"Don't be silly, yourself. How am I going to explain makeup in my own bedroom?"

"Yeah, s'pose that would be a giveaway. Oh well, we can find some way of keeping you looking pretty. I've got an idea though. Since we've knocked off for the afternoon, let's sit you in front of the mirror and give you a proper makeup treatment - just so you can see how pretty I could make you."

"Why not. If I'm going to be called Jackie all summer, then I ought to know what Jackie looks like. But don't do anything silly."

I spent quite a while with my limited set of paints and potions. I was just finishing when Dad shouted from downstairs, "Hey, where have you been all afternoon. I still want a word with you. You two come down. Your friend can go into the garden while we have a little chat."

This sounded worse. I grabbed Jackie and we ran downstairs. I was about to push her into the garden when Billy Goat Gruff said, "Well introduce me to your friend before you push her out. I can see you've been practising with your makeup, she looks very elegant for a little lady." I didn't think much of this cumbersome flattery.

I sneaked a glance at Jackie. She wasn't keen on her first exposure as a girl. "Come off it, Daddy. This is Jackie, She's just joined the riding school so I was telling her about some of the fun times we've had in previous years and then she wanted some tips on makeup."

"Hello, Jackie. Pleased to meet you. I don't reckon you need many tips - you already look much too pretty to need makeup." and the giant held out it's paw.

Jackie smiled and murmured, "Thank you, Alison's been jolly helpful. I'll go out now."

Dad smiled. "There's something about that lass. She reminds me of someone. Well, I hope she helps keeps you in order. I want to speak to you about going out with boys till all hours, wasting hours on my phone and generally not doing your share around the house. I don't mind you spending time with the riding girls - but that's enough for the moment. I'm going to be much happier if you stay with ponies, saddles, crops, reins and barrows full of muck for at least one more summer. If this Jackie can get you spending more time with that, then I'll be able to relax a bit. You've no idea how much anguish a busy young teenager can cause an ordinary parent. And you, young lady, are going to be a lot less busy, please."

Dad didn't often say please like that. It meant something special in our family language. I suppose I had been a bit over the top in the last few months. But Robert and Jim had been fun. "Okay, Dad. I'll try to spend more time with Jackie and the other girls. Even though she's new, I think she'll fit right in." Only Jackie and I knew how 'new' she actually was. I scuttled into the garden. Jackie was sitting on the swing and I had a quick memory of the photo by my bed of me on the same swing - although I was wearing a pretty white cotton dress instead of jodhpurs. I'd use my own subtle ploys to fix this boyish figure. I liked the idea of having a matching photo of him in the same dress. Meanwhile I sat on the grass and we talked about the next day.

"Daddy's right, Jackie. You do look pretty and he's right too that you don't need much makeup. You've got a good strong cheekbone. Mind you, that does prove how easy this whole job is going to be. If you can fool my Dad at arms' length, it should be easy from the top of a horse."

"In the morning, you come over here first. Then we can both stroll down to the stables. I need to check you over and give you a few hints. And I can tell you about some of the other girls too. But, for now, you'd better scoot upstairs so that I can get off that makeup, then you must beetle off home."

That was it until the next morning. About 8.30, there was a knock on the door and Jackie's standing there. Fully kitted out in standard riding gear. I sped upstairs with her in tow. I had got a couple of things ready. "First, to embellish your new self, here's my most feminine necklace. There's a bracelet to go with it but you can have that some other time. I don't want muck and straw all over it. And here's a little carry-can of deodorant. It's called Pretty Pink, so it will suit your new image better than your typical 'Boy Washed Yesterday' stuff. If I can think of anything else then we'll add it later."

Jackie said, "I've been thinking too. What is it that makes the difference between a young teenage boy and a young teenage girl? Clothes and necklaces are the most obvious, but there must be more. You say that my hair is too short and I can't use makeup. I'd feel more confident if I was being reminded that I'm not a boy when I'm at the stables. What do you think?"

"Yes, we can try ribbons as well as the necklace. Your hair may be short but we can still give you that as a bonus. Ain't no way a boy has a ribbon. We can use it as a sweat-band sort-of-thing but it will make you look much more definite."

"Okay, what have you got," she said and we dived into my wardrobe to see. All of a sudden, I realized that I was letting a boy rummage through my most intimate stuff and it seemed completely ordinary. I watched as Jack pushed my bras and panties to one side. "Hey, don't do that. If those get crumpled, I'll have to iron them again. Just because you've never had the chance to rifle through a girl's panties. You may be Jackie for the summer but that doesn't mean you can rumple and crumple mine like it was boy's stuff."

"Ooops, sorry, Ali. I'll be more careful."

I noticed that she didn't stop fingering my things.

"Here's a good one," I said. "It's a lovely pink, it just matches your cheeks when you blush." As I said this, Jackie did blush - confirming the accuracy of the comment.

The transformation was remarkable - just by adding a necklace and a ribbon, there was so much more Jackie than Jack. I added a small squirt of perfume too. Jackie complained about this but I said, "It'll remind you now and then that you are a girl."

We ambled down to the stables, talking about how much riding we had each done, where and when, who we had met, ordinary riding chatter. The stables were less than a mile away so we soon got there. Jenny was already there, of course, with Emma, Jane and June, the tiresome twins and Sandy. That meant that only Laura, Michelle, Anna, Pam and Pat were missing.

I introduced Jackie to the gang and we went through all the usual rigmarole. "How long have you lived round here?" "Are you a good rider?" "Do you have a pony of your own?" and so on. No one had any idea that the person beside me was anything but a pony-mad girl. Stage one - passed with flying colours.

For the rest of the day, we slaved away getting the stables ready for the summer hordes. We'd do our share every morning so that we could have as many afternoons riding in the hills. Like the rest of the horse-mad world, we would swap hours of work for free rides. Jackie fitted in easily. For the morning, she worked with me. In the afternoon, she was with Pat and Pam. They weren't there every day like the rest of us. They were sisters, aged about 15 and 13. Their parents took them off on jaunts around the local area. Sometimes one or two of us would get invited too.

Jackie came home with me at the end of the day. Neither of us had done much more than warm up a few horses and practice a few gymnastics in the saddle - but we'd both worked hard. For the first day of the season, we were quite tired. As we walked home, Jackie talked about her day.

"It was fine with you, but Pam and Pat just kept talking. They went on about the best place to buy saddles and this for horses and that for horses. Once they exhausted the topic, they went onto ordinary clothes. Did I prefer cotton for summer wear, how many dresses they had and how many did I have. What was my favourite colour and on and on and on. Then Pam started talking about bodies. How the other girls at school teased her for having the largest breasts - I absolutely know that I was bright pink. After spending far too long on the topic, she then started talking about how hard it was to find a bra that kept its shape after a few washes. Then it got worse, and she started asking if I was just a late developer and whether my Mum had small breasts, was it hereditary or what. I didn't know what to say. I just grinned and said, "No hurry."

Pam giggled and agreed, "Yes, that's true, Once you've got them they're not going to fade away are they. And, too, if you don't react to being teased then most of the girls stop after a bit."

I couldn't tell her that my tits were the special non-existent variety used by boys, could I. I kept on with the 'grin and bear it' routine. After a while Pat said, "Is that all you do, smile and mumble. Pam loves a good listener, you'd better run while the going's good."

I grinned again. "No, I do speak sometimes. I'm just learning who's who, y' know."

"Okay, then. But you'll have to put up with Pam and her constant boasting about having the biggest tits in class. She says she's embarrassed about them and then never shuts up. I'd call it boasting if I wasn't her baby sister." She smiled as she said this to show that she actually didn't mind. "Though she is right. So far I'm so flat-chested, I don't even need a training bra yet, and I can't wait for something to happen. The boys tease me, the girls tease me and my Mum just says, 'wait and see'. It drives me potty. Are you the same?"

"Well, you can see that I've got nothing to put in a bra either." I was finding that if I spoke quietly and used a faint lisp, I could feel my voice sounding higher and more girlish.

"That's alright then. We can gang up on Pam if we have to." With that, she leant over and kissed me on the cheek. "Ooh, I like that perfume, what is it?"

I had to think for a moment before I remembered. "Ali lent it to me, I think it's called Pretty Pink." That was about it for the day then. Pam bullied us into doing yet more leather polishing so we sat in the sun to do that. Then you came along and dragged me away. Well, I don't really mean dragged. I've had a lot of fun. I had no idea girls talked about things like that in such a casual way. It's lovely, gorgeous, pretty, delightful, whatever other words you want me to use. I'm having fun. And Pat said my ribbon suited me too."

I was pleased both at how Jackie was making such an effort to use a more sensible vocabulary and at how she was proving to have an almost feminine ability to skip from subject to subject. Her throwaway comment about Pat liking her ribbon was a definite proof that she was enjoying the masquerade. "I thought you'd have fun. We've got weeks and months to go now. What do you want to do for tomorrow. We'll have a chance for a good long hack along the top of the hills. Hey, I've got an idea. It's late night shopping tonight - shall we go out and get you some ribbons and things of your own. I don't have enough of my own. We can keep them at my place so that your parents don't find out (too quickly')" - I added to myself.

"I don't have much cash with me. But if it's only ribbons, I should have enough."

Jack might only have enough for ribbons on this trip, but he would be spending a lot more over the next few weeks. After all, there was the end of summer Ball and I was going to get Jackie into a dress for that if it was the last thing I did. I carefully said nothing.

It was fun going shopping with Jackie that first time. At my house, we both changed into jeans and t-shirt. Yes, she borrowed some of my clothes. There was no deliberate effort to avoid stripping off in front of each other even though she was a boy and I was a new friend. Somehow, it worked out that neither of us were embarrassed. She had a shower while I made the drinks, then she tidied up downstairs while I got dressed.

When we were both ready I could see her looking at me in the mirror. Once more, we looked like sisters. We were wearing identical clothes but one of us had a full chest, the other was flat. One of us had long hair, but it was the same colour for both and both of us had only a smidgin of makeup. My nails had some polish still showing despite two days at the stables. Jackie's nails were plain, of course. I didn't complicate things with lipstick or anything but I did put another ribbon in her hair.

It had been so obvious that simple accessories were a key to the Jack/Jackie transformation that I was determined to get more. We zoomed around the shops getting the most deliberately feminine jingles and jangles that I could find. We didn't spend much but Jackie had a pocketful of necklaces, bracelets and so on as well as one pair of clip-on earrings. The other pair were in use, the long hoops dangling from her lobes, clinking and tinkling as she walked along.

"Wearing things like we've just got you, no one is going to see anything but a pretty girl. You'll do fine with that. But I do have one or two questions for you."

"Whaaat. Don't think I like the sound of that," said the nervous sort-of girl beside me.

"Nothing special, but I did see the pleasure you got in rummaging and scrummaging through my undies. My question is - If I buy you your own undies, will that stop you from wanting mine."

"Guggugug, y' what ?"

"I said, I could tell that you were fascinated by my undies so did you want some for yourself." I was deliberately twisting the poor dear's actions - but was it fair to let a pretty girl like her spend in summer wearing boy's boxer shorts. I'd seen them in the shops and they didn't look nearly as comfortable or nearly as pretty as what I wore. "I'm offering to buy you some panties of your own so that you can see how much nicer they are. Nobody will know. You wear jodhpurs or jeans all day. I can put them through with my washing. I'll even iron them for you, if you ask me prettily."

"I wasn't even thinking about it. Not even when we stopped in the lingerie department or whatever it's called, so that you could look at the sale specials." The poor girl pronounced it 'lingery' instead of the lanjerie. Had she learnt no French at school. There was so much to teach her.

"I wasn't looking for me, dear. I was looking for you - and you must have been thinking about something the way your hands were caressing and stroking some of the things. If you want to admit that you have a, shall we say, interest in wearing panties like mine, then I'll buy you your very own."

"You're a bully, you are - and a snoop."

"Don't be daft, you weren't trying that hard to hide it."

"That's not fair. What am I supposed to do when you tell me to look for a ribbon in a drawer full of underwear. Tho' I did notice that they were much softer and slinkier than my ordinary pants – but why you need all those frilly bits and lace and stuff, I can’t guess.”

"Well of course they’re prettier and softer. They're designed for girls instead of boys. We are expected to like, if not deserve, attractive clothes in gorgeous materials and a wide range of colours. We can be like birds of paradise instead of drab and dull animals like you boys. So that includes frills and lace – and silks, and satins and, oooh, oh so slinky and sexy when you get older."

"Come off it. If you're going to treat me like a boy some of the time and like a girl at others, that's not what we agreed. You said I was to pretend to be a girl at the riding school. I agreed to that and only that. Now you're trying to get me to be a girl much more of the time."

"Now Jackie, be sensible. What I said was that it would be fun to have you as one of the Riding Gang. You said 'Yes'. Since we are all girls, you therefore agreed to become a girl when you are with us. I didn't say anything about 'pretending' and I certainly wouldn't have said 'just at the riding school'. What on earth did you expect? That when we go out as a gang in the evenings, that you could turn back into being a boy? As far as I'm concerned, you agreed to be a girl for a very large part of the summer. I'm trying to make this easier for you. As an example, I think that having panties of your own will give you an extra and necessary insight into being a girl. After all, that was your motive for agreeing."

"Yer, um, I'd forgotten that. I'm sure you're twisting things a bit though. But, alright then, let's go and buy me some pretty panties. But we'll have to find a way for you to wash them and so on."

"I think you'll enjoy wearing panties every day. I've never worn boy's pants but they look much heavier, much coarser, just horrible in fact. I saw the prettiest pair in the sale. They're white with a lovely bright red scallop stitch all along the hem. Would you like to have something like that?" I smiled as she tried to hide the pleasure in her eyes.

When we searched through the sale racks, we found much more than we expected. We grabbed the last two pairs of the scallop-edge panties but then I found matching knickers, a short petticoat and a bra. Jackie went scarlet when we found the last item. When I insisted several times that it might be necessary for her to wear one at some time in the summer, she eventually agreed to the purchase. I could tell that she saw this as one of the biggest steps she had taken in the last two days. As we left, I also noticed that there was a gorgeous body-form in the identical pattern. I didn't dare make Jackie buy anything else yet, so I just noted it as a possibility for some future expedition.

"What sort of shoes do you wear? Have you got anything faintly unisex? You know, moccasins or canvas sailing shoes, or even some flat style sandals. Do you want to try on some new shoes for your new image? You can't wear riding boots all day." We looked down at her chunky trainers. "You can't wear those every evening."

"What, you mean we'll be going out in the evening sometimes?"

"Of course we do. We're not hermits. The Riding Gang try to go out at least one or two evenings a week. There's not that much to do because we're all very underage - but there's a few events to go to over the summer."

"You're going to have to teach me an awful lot of things, you know."

"If you learn fast enough, I'll try to teach you what I can. I think it'll be fun."

"Come on, let's go back to your place. You can show me how to put on that silly contraption. I may have nothing to put in it, but I suppose I'll have to get used to the thing."

"Yeah, let's go. I'm quite looking forward to helping my friend Jackie put on her very first bra and panties. I think I'll introduce you to stockings as well, would you like that?"

"I refuse to answer on the grounds that I might incriminate myself."

"Is that so, well, wipe the silly smirk off your face then."

"Don't be so mean. How can I help it if I'm enjoying parts of this game so much."

We got back to the house quite soon. As far as I could tell, nobody else was around. We ran upstairs and Jackie calmly stripped off when I told her to. She left on her pants so I told her to flip them off and put on her new panties. She turned her back while she did so. I was pleased that she was so easy about it. I was quite prepared for a hasty scuttle into the bathroom or some panicky excuse. I made it clear that I didn't have a problem so Jackie took the same approach.

I was just helping Jackie into her first bra when the damn door opened! My mother barged in to find me helping another girl get dressed. At least, she had the decency to apologise. "Sorry, dear. I just came in to pick up your duvet cover for the washing. I've got time for an extra load. Who's your new friend?"

"Mum, this is Jackie. She's just joined the Riding Gang. We were having some fun swapping clothes and stuff."

"Don't worry dear, I won't interrupt and I wouldn't dream of interfering. Nice to meet you, Jackie." With that, she departed and we both drew a deep breath.

"Golly, that was bad timing. What was she doing in the house? I thought you said the place was empty?"

"I dunno. The car isn't there so I assumed she was out too. Sorry, Jackie. Let's get on with this. Lift up your arms, swing them round a bit, there that looks okay. It's a real shame that you won't ever have your own tits and there'll never be any need for you to wear a bra for real. Perhaps for now, we can invent something else. After all, I've seen girls at school filling their bras with cotton wool, tissues, anything. Why should our Jackie be any different?"

"What d'you mean. Are you going to stick things in that bra. It'd be gross. What on earth am I going to do?"

"Look, Jackie, you're a girl for the summer. All the others are going to expect a girl and a girl has breasts. If a teenager like you doesn't have any then it is absolutely standard practice to add a little pretence. In your case, there is just a lot more pretend than my other friends - but they won't know that will they?"

Once I had padded out the bra with some foam rubber wrapped in some old pop-socks, Jackie looked much better. She stared down at her new frontage with a puzzled expression. "It feels really strange. I can't even see my feet now without leaning forward. I'll never get used to this."

"You will, dearie, you will. After a little while you might even get to like it that way."

"No way."

"Let's wait and see," I thought to myself - and maybe not for the first time. I didn't nag Jackie about trying on a bra again, well not for a couple of days anyway.

A few weeks into the extra-long summer holiday things got more complicated. Jackie and I spent hours working out a plan to deal with it. Finally, I took a deep breath and just asked my parents straight out. "Jackie's dad has just had this wonderful offer to go to Iceland for a short contract, and of course, he's taking his wife for the trip. But they can't take Jackie with them except for a week at the end of August. Would it be alright if we offered to put Jackie up for the rest of the summer?"

"Of course, dear. Is this what you've been building up to ask. I could see that something was bothering you for the last day or so. Of course you can have friends to stay - I know this is going to be more than just a weekend - but I can't see a problem. You weren't worried about the money or anything were you. You girls only eat like sparrows anyway. I'll just ask Jackie to keep a note of anything large - like competition fees and so on. I think it'd be alright to ask her parents to look after things like that. Perhaps they'll leave her a small amount of cash. Well, I can sort that out with her parents."

I wasn't keen on the way the conversation was going but fortunately Jackie and I were already a step ahead. "Mum, there won't be time, they leave tomorrow. I was more worried about the short notice they gave us than anything else, and they are leaving Jackie some dosh to pay for special extras. I think they almost expected Jackie to be paying some rent or something."

"Like I say, I'll only ask for help if she needs something unusual. If she's on a diet of lobster and steak - that might be too much for my wallet. But I can easily feed an extra sparrow on more breadcrumbs. Alright, dear, you seem to have it already sorted. I'm not very happy that there won't be time to talk to Jackie's parents before they go - but that's history now."

Jackie and I were both very happy that she wasn't going to talk to her parents. This game was getting more and more complicated but so far we were both enjoying it. The end of summer was still ages away. We'd cross that bridge when we came to it. Introducing the parents to each other would set fire to the bridge long before we were ready to cross it.

Jackie had been much more worried than me about her parents getting involved. In fact, she'd been so worried that she hadn't worked out some of the effects of coming to stay with me.

"Are you telling me that I have to wear girl's clothes even when I'm not at the riding school?"

I hadn't actually said anything of the sort, but I wasn't going to miss an opportunity like this. "Sure looks that way. Mum and Dad have only met you as Jackie. They'll flip if they find out that you're a boy. I think you're in a bit of a fix and the only way out is pink and frilly."

Jackie took a deep breath. I noted the way her meagre temporary frontage rose and fell as she sighed. "I can't argue much, can I. If I'm staying with you I'll have to spend even more time as a girl. I really can't be a boy at all if I'm staying here. I'm not sure this is a good idea, 'tho at least I'll be able to stop changing clothes so many times a day. Every cloud has a silver lining."

"In your case every cloud'll have a pink and frilly lining. You'll soon get used to it."

"That's what worries me. It sure as socks isn't what I was planning to do this summer."

"Stop complaining - and you should now be talking about tights and stockings instead of socks, silly. Didn't I tell you that you'd learn a lot about girls this summer. You've learnt that we're really pretty similar to boys - we worry about the same petty things, we misunderstand each other's motives, actions and reactions. That's a pretty amazing thing to find out about for both of us. I know you haven't been, in quotes, going out with a girlfriend - but you've actually done better than that haven't you. Well, say something."

"What y’ getting all scratchy about - I can't disagree with you. And a lot of it has been fun. It's just the all day every day thing. But I can't avoid it, can I, so I'd better get going."

It was fun with Jackie. Gradually I introduced her to more and more feminine garb. Since it had started with those extremely unisex jodhpurs and moved on to jeans and shirts, it took quite a while to get her into a dress. It was no problem getting her to wear a nightie. Conveniently, when I unpacked her suitcase I couldn't find any pyjamas so I had to lend her something - and, of course, I only had pretty nighties. She said much later that she was certain that I had deliberately lost her pyjamas and I denied this in my best Pinocchio fashion. Actually, her suitcase had contained almost nothing except riding clothes and jeans. She couldn't bring any shirts because they all buttoned the wrong way - or the right way - depends on your point of view. She had the panties and things that we had bought together - but those were already in the house. To all intents and purposes, she 'hadn't got a thing to wear'. So she had to borrow quite a lot of my stuff at first.

Mum commented on this after a few days. "Doesn't Jackie have anything of her own to wear except riding clothes. I seem to recognise almost everything that she wears the rest of the time."

We had a quick excuse for this. Jackie hesitated so I answered for her, "Well, it's summer and she's grown so much in the last few months. She didn't ask her parents for anything new because she knew she'd be at the stables almost every day. If she's still growing it'd be a waste of money."

"That's remarkably thoughtful of you, Jackie dear, and generous of you, Ali. But I think we should be able to get you a few things for the summer. Are you still growing? I haven't seen much change in the last month. Anyway, I think we can stretch to a buying a few new things for you when we next take Ali on a shopping trip. Will you be able to tear yourselves away from the horses for a day out sometime soon? I'd love to see you both in something new for the summer."

It was fun that first trip. Jackie tried as hard as possible not to be interested and excited. But it was too hard for her since we were all having such fun. It was a chance for Mum to spend a day doing things with me, which didn't really happen often enough. It was a chance for me to buy a few things I had been eyeing up in the shops for the last few months and it was a chance to get Jackie deeply entwined in the delights of lace and cotton, light summer dresses and swirly skirts and the whole wide and delightful world of feminine clothing.

We didn't empty the shops but we had a good try. The full bags and the empty wallet eventually called a halt to the proceedings - but I had some really lovely new things and Jackie had a complete wardrobe at last.

But getting her into her first dress was a major step. She had been staying with me for almost a week when Mum said, "Are you never going to get out of jeans and tomboy clothes, Jackie. I thought you were a good influence on this daughter of mine. There's people coming for tea and you could make a bit of an effort. After all, we did buy you several pretty things last week. I know you refused that lovely green and white summer frock but it would be nice if you did dress up once in a while."

I leapt at the opportunity. "I'll wear a dress if you do too. Come on Jackie, since Mum insists, we've got to get changed."

Jackie stormed up the stairs after me. "How could you," she hissed. "You've stitched me up properly. Now I've got no choice. Alright, then I'll wear that pink flowery dress of yours." She must have known that this would annoy me as that was about the only really feminine dress I was willing to wear.

Once the big step had been taken and she had let me slip the dress over her shoulders and then do the back-zip, she was much happier. "I wasn't going to volunteer to put on a dress but I'm almost glad that you've forced me. I actually rather like the feel of the built-in petticoats and the way they swish against my stockings. These bouffant arms are rather fun too. I'm not surprised you like this dress - if it makes me feel more feminine then it has to do the same to you."

"Well, you do look awfully good in that. Your waist is smaller than mine after all so it fits better. I suppose the top needs a bit of filling out.”

Jackie blushed.

"Oh, does that interest you? You've worn a bra a few times now, but Mum has commented how unlucky you are to have nothing chestwise. Would you like to see how you feel with a little more padding? It'll make such a difference."

Jackie swung round and hugged me tight. "I've been waiting for you to say something. I knew that a decently filled bra and my first dress were steps I would have to take sometime - but I wasn't going to ask. I couldn't find the words and I didn't want you to guess how exciting I'm finding all this."

"Are you really enjoying this now?"

"Ooh yes. Every day in every way I enjoy being more of a girl. It was getting so difficult at home. It was beginning to feel wrong when I couldn't put on nice soft panties. I'm almost glad that my folks have had to go away. It is just so much fun being a girl. And your help is almost the best bit."

"What d'y mean - almost the best bit. Alright then, Miss, you'd better give me a satisfactory answer about what you actually do think is the best bit. Chop, chop. You've obviously been thinking about this a lot.

"Not consciously. It's been just over four weeks now since this all began. There's several things which all make up the best bit. I'm getting to be more and more comfortable with wearing pretty clothes. They’re so soft and the feel of them against my skin compared with the roughness of what I’m used to – well, it’s a sort of constant woo lovely. I realize more and more how dull and boring my old things were. I love being with all the girls in the gang. I even enjoy talking with them about the boys we meet. It's rather strange, when I'm with the gang I now look at boys completely differently. I don't mean that I fancy any of them - but, I can't explain it properly. I love wearing stockings and feeling the pull and stretch of the suspenders you insist I use. I'm sure that tights would be easier - but now I'm used to the things, I do enjoy them. I love the crinkly feeling of the makeup and I adore lipstick. I feel all wriggly when I've put on some extra-glossy evening colour. When I sip my drink and see the marks, my marks, on the glass - I love it. You've watched me every step for the last few weeks. You can probably tell me things that you've seen me enjoy."

"Oh, I have, darling, oh I have. You may say that you've got no interest in the boys, but I've seen you flick your hair and fiddle with your earrings when we're in the cafe and some of the boys come in. You may have started by copying me and Michelle, but you've learnt pretty fast how to flirt and preen. It's rather fun actually. Now that you're willing to dress up a bit more thoroughly we can have a lot more fun. You do want to, don't you? You're not going to back out after admitting that you're having 'such fun'."

"Can't really, can I. I mean, even though you can't say much without revealing your part in the dastardly deed, I can say even less. Oh, let's get on with it. I want to see how different I feel with a decent-sized chestful. What are you going to use - there must be something better than a rolled up pair of panties."

"Oh, there is. I asked around. Paula had a pair of foam rubber cutouts - but her friend Sal said that a bag full of liquid is even better. It gives a bouncy sort of effect that's much more realistic. I've had these sitting in my drawer for three days ready for you to say you're willing. So, let's try them. Let's get that dress off, you can put it back on in a moment. Sit down and I'll drop them in." Pause. "Oh yes, I can tell from your expression that you like the feeling. Now stand up and you can put the dress back on. Don't flutter your hands like that, of course I'll be careful not to muss your hair. Now, stand up in front of the mirror - don't you look so much better. I think you look wonderful. Let's go downstairs and show Mum."

Mum smiled when she saw us coming down the stairs. "Oh, that's so much nicer. You both look lovely. You especially, Jackie. I know it's a bit rude to comment but it's only us girls here; you do look so much better with a bit more chest. Don't you like the feeling? When I was a girl, I was so desperate for a bit of cleavage. I think that looks just right for you. You looked almost boyish before and that would never do, would it?"

Jackie's face was in flames and I wasn't much better. "Hush, Mummy. Don't be so awful."

There was a short silence. "Don't be silly dears, I was just enjoying remembering when I was young and these things were as important to me. You must realize that every generation has most of the same problems. Do I look nice in this dress? Does this hairstyle suit me? Did that handsome boy notice me, and so on. You're not the first and you won't be the last."

Mum chose that night to come along to my room while Jackie was having a bath and getting ready for bed. I froze at her opening words - "Jackie isn't quite what we thought, is she? Though she does look wonderful. In fact, I can only think of her as Jackie, anything else would be completely false. Whose idea was it, yours or hers. I think she's one of the most beautiful young 'girls' I've ever seen." Her voice put quotes around the word.

After a moment I got my breath back enough to gasp, "Mother. I don't believe it. You don't mean that you know about this sort of thing. But it's only a game."

"My little pet, you may think that this is a game, it may have begun as a game - but Jackie doesn't think it's a game any more. You can see in the way she walks, the way she talks. You might even say the sway she walks. This is not a game any more." The strength of feeling behind her words and the emphasis she used made me realize how much she meant what she was saying.

"I suppose I hadn't thought about it much. It was fun when it started - it's still fun. But I hadn't thought about the long term at all. Do you really think that Jackie no longer sees it as a game. I don't know what to say. I don't know what to do. What am I going to say to Jackie when she finds out you know. When she finds out you knew. Oh, Mummy," and I, tough young maiden, burst into tears.

She hugged me tight and I felt her heartbeat against my cheek. "If you want, I'll tell Jackie myself. I'm sure that I can tell her without any drama or theatrics. Are you willing to let me do it my way? Not that I'm actually giving you a choice."

"I don't know what to say to you, so I haven't a clue what to say to her. Mum. You won't tease her or embarrass her. She's one of my best friends. I've really enjoyed this summer, more than last year in fact. I couldn't bear it if you hurt my Jackie."

"That's part of the problem, dear. She's not your Jackie. She's just Jackie. No one belongs to anyone else and you have to learn that lesson. She may be your best friend now. If you're both lucky, you'll be friends for many years. But you need your beauty sleep. I'll just pop next door and tuck Jackie in. Then I'll go downstairs and sort out a few things. I don't want you popping next door and spending hours whispering secrets to each other. I may be decades older than you two - but my ears and eyes still work. I've noticed you two - so tonight, get a good night's sleep. I'll say the same to Jackie. Fortunately you both look more tired than usual - so I expect you to behave. By which I mean, until I have made some decisions – you will not be sleeping together."

I gasped, “Mummy, we’ve never …. I mean, how can you suggest … I mean ….”

My protests trailed off as she put her finger to my lips. “I’m not worried and I haven’t been worried. I just need you to be more aware. And by that I mean you’ve got to do some actual grown-up thinking for a change. But don’t worry – I’ll help you. I’ll help you both. You're too involved already. But you have to realize that it has gone far beyond a game, don't you. And you and me and especially Jackie and then her parents have to face up to it and deal with it."

With that, she kissed me again and flowed away through the door, her lovely gown sweeping behind her. A faint trail of perfume lingered. Despite a residual frown, I fell asleep almost at once. I expected to dream that night. But I remembered nothing. No dream of Jackie in a beautiful dress or doing girly things with me. No nightmares of Jackie in a dress and it all going wrong. No remembered dreams.

But I woke with a frown.

--------------------------------------
Next (and last) part coming soon. AP

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Comments

Mothers see EVERYTHING!

My5InchFMHeels's picture

I'm sure I could get a "few" things past Dad, not many, he was always pretty sharp, but Mom? No way, Mothers see Everything. I almost wonder what secrets I had that my mother knew about before I knew it was my secret? Appears Ali's Mom is the same.

Thank you for

' a delightful story with the lovely twist of mother getting involved and being so understanding and accepting of
our boy who has just found herself .

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It's not Jackie's mother yet

It's Alison's mother ...... you don't know what's coming soon, heh heh cackle. Might be good, might be appalling.
AP

I get the feeling this isn't

I get the feeling this isn't the first boy she's dressed up

Well, now the 'secret' is out

Well, now the 'secret' is out, hopefully Ali's Mum will be able to actually do some helping of the two of them as Jackie strolls/sways her little tush into a more feminine lifestyle. Shall be interesting to see how Jackie's own parents respond to all this, especially 'her' Mum.

Jackie is...

...engulfed in being a girl and no longer pretending. I think her arrival came step by step and getting into first pretending and then into being. I love how this story has taken time in developing, it lends to the authenticity of it all. I'd like to hear more about being with the group of girls and experiences they have.
Mom too has been brought into the event at a good time. I wonder when she caught on and why she wasn't bothered more?

Hugs, Jessie C

Jessica E. Connors

Jessica Connors