Not Quite Right

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Jason isn't quite right and a visit triggers a major change.
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Calandria
Calandria
336 Followers

Introduction

You've read the stories, I'm sure. The young guy who is rather 'girly,' doesn't like sports, plays with the girls, likes to dress up in his sister's clothes, and so on, and so on. Jason wasn't like that, not really. This is his story. It really begins when he is at University.

Jason Harding was a decent athlete. More than decent, it's fair to say. He had been captain of his school at cricket, and was still an outstanding batsman, playing for the University's first XI, though still a freshman. A nifty wingman on the rugby field too, he had been 'on the bench' for the University's last two games of the season. Medium height and slim, he was a good-looking lad, with a dark complexion, black hair and brown eyes he owed to his mother's Punjabi father. His sporting ability had more to do with his father's genes - James Harding had been a Minor Counties cricketer and played rugby for a good club.

Now it's better if Jason takes up the story:-

Jason 1

I had enjoyed a reasonable season of University cricket, scoring three half-centuries, and getting a few wickets with my leg-breaks, but was looking forward to the long vacation as it approached, and exams were over at last. My chosen sphere of biology was animal behaviour, and posed some complex problems - a rest was going to be welcome. The last days of term were quiet, and I had time to dwell on something that had been troubling me. Somehow, I was 'not quite right.' Hard to put my finger on, but there it was, I'd admitted it to myself! I'd had a normal enough childhood, played with the other kids, and was considerably above average at sports - had been since as long ago as I could remember. I'd had a girlfriend, Sarah, a pretty blonde now doing a secretarial course, we'd kissed, and I'd got excited when she let me touch her tits, but it had never gone further than that. So what was my problem? I was coming up to 19, and had almost no facial hair, nor hair anywhere else except on my head. If I was honest, my voice had hardly broken either - I thought I sounded...well, feminine. I liked girls, of that I was quite sure - had fond memories of Sarah, even though I had heard she was 'going steady' with a neighbour's son, George something. I was musing over these things when my phone rang. It was my mum.

'Jason, Sarita, has asked me if you'd like to go and spend a few weeks with her.'

I thought of my mother's doe-eyed younger sister and had no reason whatever to say anything other than yes. 'When do I go?' I asked.

'Next Thursday,' she said, 'That okay?'

I agreed, and she told me she'd already bought the ticket. My mum!

I spotted Sarita as soon as I emerged from the baggage reclaim. She stood like a model, I thought, one foot in front of the other, wearing a grey pencil skirt and a pale blue silk blouse. God, I thought, how she looked like a younger, slimmer version of my mum, big brown eyes, long, shiny black hair and all. She hugged me in a cloud of perfume.

'Looking good, Jason,' she said, as we walked through JFK's terminal to get a cab to her home in Queens, and it felt good to be with her. When we arrived at her neat wood-framed house, she installed me in the neat, rather flowery, fragrant spare bedroom, and showed me how the shower in the tiny ensuite worked. when I had freshened up, and changed into a tee shirt and shorts, I went down and found Sarita in the kitchen, preparing dinner.

'Hope you don't mind, darling,' she said, 'I've a friend coming to dine with us tonight, but I suppose you'll want to get some shuteye soon after dinner - I know what that journey's like. Then tomorrow is Saturday, I don't have to go to work, so we can have a nice long chat.' She was right about one thing, I was really drooping, as my body told me it was well past midnight. As to the chat, I knew that Sarita was a psychologist, so wasn't sure it was a great idea. But I nodded and asked if I could help. She smiled and declined, so I sat and watched the drivel that passes for American television, until the doorbell announced the arrival of my aunt's dinner guest. I had assumed it would be a boyfriend, or at least a prospective one, as my mum had often said, jokingly, that her sister was a 'man-eater.' So I was surprised when a long-legged, willowy blonde walked in. She didn't look that much older than me, and wore a navy blue, pleated miniskirt and a silky, long-sleeved beige shirt. She had a high pony-tail and wore long silver pendant ear-rings. Sarita introduced her as Caitlin, and their body-language, at least to me, suggested some kind of intimacy.

We sat down to a nice, fairly light, dinner, sharing a bottle of white wine, but I was too tired to take much part in the conversation, and gratefully accepted Sarita's suggestion that I went and got my head down, as soon as we had finished eating. I slept like the proverbial log, but awoke early, sun streaming through the curtains. I took a shower and slipped into shorts and tee shirt again. There was no sign of life downstairs so I went back to my room and sorted out my scant selection of clothes, putting them in the wardrobe, alongside a rail full of dresses and skirts which must have been 'overflow' from Sarita's closet.

2

By the time I had my clothes hung up, I could hear movement downstairs, so I went down and found Sarita, wearing an absolutely gorgeous silk negligee over a long silk nightdress, both ivory, or so I thought the sort of off-white shade would be called. She hadn't heard my arrival, so I paused and watched her for a few moments from the doorway, as she rustled her way around the kitchen. Then I felt guilty, and said, 'Good morning, Sarita.'

She started slightly, then turned and smiled her lovely white smile at me, 'Hey! How did you sleep?'

'Fine, thanks,' I said, and had to work hard to shelve the desire to touch her, to stroke that lovely silk - was it Sarita, or was it what she was wearing? God, that awakened something, didn't it? A dream? A fantasy? I didn't want to put a name to it, but perhaps it was something to do with the intensely feminine ambience of this house, even permeating my bedroom, with all those dresses hanging in the wardrobe...something had jogged a sort of feeling that...that, well I couldn't really admit, could I? Perhaps it was all part of that...'not quite right' thing I felt. And now Sarita was looking at me strangely.

'Are you alright, Jason?' she asked, 'You look pale, as if you've seen a ghost.'

'I'm okay, just hungry, I suppose,' I said.

'You poor dear,' she said, 'I'll get some breakfast moving right away, then we can have our chat, eh?' I liked the first bit, but wasn't at all sure about the second, knowing that she was altogether too good at what she did for my liking.

Sarita got changed while I was tucking in to bacon and eggs, and maybe it was just as well, I thought, when she reappeared in cut-off jeans and tee shirt - at least I should be able to concentrate on something other than her silken lingerie. She herself had a coffee and a slice of toast, claiming that she seldom ate much for breakfast.

'Come and sit beside me,' said Sarita, when I had helped her clear the breakfast things away, patting the sofa. I meekly obeyed. 'Your mum is a bit concerned about you,' she began, 'Does she need to be?' Her big brown eyes searched my face - she could see into the depths of my soul.

'I...I don't know. I don't think so. I got good grades, and I'm playing reasonably well at cricket, so I think...'

'You know what I mean though, don't you, Jason,' she let a long-nailed hand rest on my bare knee, 'Is your life all it ought to be at 19? Or do you feel that something is missing?'

Unaccountably, I felt myself begin to tear-up, and almost before I knew it, I was sobbing into Sarita's shoulder, as one of her hands stroked my back, the other gently massaged my neck. 'Oh Jason, my darling, you are not quite right, are you? There's something amiss in your life, and I have a terrible feeling I know what it is.'

'Tell me then,' I said, 'because I wish I knew. I have these strange feelings - feelings I can't understand, much less talk about. Tell me!'

'I don't believe I should, but I promise I'll help you address those feelings, in my own way. Just be patient, and we'll work it out together.' I nodded.

3

Sarita helped me forget everything by taking me into Manhattan for most of the day. We did 'touristy' things, like going up the Empire State building, and walking around Chinatown, and had a good lunch in a typical New York burger joint. We got back to Queens at around seven, and had a light dinner. It was then that Sarita sprung the first part of her 'plan' which was to 'help me address my feelings.'

'Come on,' she said, 'I have an idea you may find odd. Up to your room.' I went upstairs and she followed me. 'I want you to have a shower,' she said, and come out with just a towel around your...er parts.' I did as she suggested, wondering what on earth she had in mind. When I had dried off and got back into my bedroom, dutifully wrapped in a bath-towel, she was standing there, a pale blue silky garment folded over her arm.

'Now,' she said, 'Put this nightie on, and try sleeping in it tonight - nothing else.' She handed it to me - it was a floor-length silk nightie, with short cap-sleeves. I started to protest, 'I can't...' But she'd gone. I shrugged and, letting the towel drop, slipped the nightie over my head, and shivered as I felt the exciting whisper of soft silk as it fell about my body. I couldn't deny, it felt good...well, better than good! However, it had been a long day, and jet-lag still had its effect - I fell asleep quickly.

I awoke with a raging hard-on, and touched it through the silk - Oh God! I was leaking pre-cum, making a wet patch on the nightie. I got up, went to the shower room, held the nightie up with my left hand and it took a couple of strokes to cum like I'd never done before. I lifted the silky garment over my head, cleaned up, and slipped on a towelling robe I found hanging behind the door. Then I sat on the bed for a long time, wondering what had just happened. Eventually deciding not to overthink things, I went downstairs and found Sarita sitting in the kitchen, again in that negligee, with a cup of coffee. She pointed to the cafetera, and said, 'There's toast if that'll do, or you can have eggs, but I'm afraid I've not much else in.'

'Toast'll be fine,' I said, and put a couple of slices in the toaster.

Sarita looked at me then, the tiniest smile playing on her lips, 'How was your night? Sleep well?'

'I was very comfortable, thank you,' I replied.

'Yes, I thought you would be,' was her knowing comment, the smile a little broader now. As I was buttering my toast, Sarita stood up to pour herself another cup of coffee, but came up close behind me, and put a silk-sleeved arm gently around my neck, so that my head nestled for a luscious few moments in her cleavage. My breathing quickened, and she chuckled at the effect she had on me. 'You're definitely not gay, are you Jason?' she said.

'Oh no,' I said, 'I don't fancy men at all.'

'Okay,' she said, 'I have a much better idea of where we go from here.' I only wished I had.

4

Sarita went upstairs as I was eating my breakfast, and when she returned, she was dressed in a cotton print summer dress and sandals. She said, 'I've taken your nightie for washing,' she wagged a finger at me as if to say she had seen the stain I had left on it, 'And I wondered if you'd let me help you try for a new image?'

I looked up from my almost empty coffee cup. 'New image?' I said, 'What had you in mind?'

'Come talk to me,' she said, sitting on the sofa, and patting the seat beside her. I did as she asked, and found her nearness, as ever, intoxicating - her flowery perfume, the smoothness of her skin as she seemed unaware that our thighs were touching, her short skirt having ridden up, and my towelling robe not exactly designed for modesty. I gave an involuntary little shudder.

'What's up, love, don't you like being here with your aunty?' she teased, and actually stroked my thigh with the back of her hand. An erection threatened.

'I love being here,' I said, 'but I don't know what you're trying to do to me, Sarita.' That hand was still playing around on my upper thigh, driving me to distraction.

She half-turned to look at me. 'Look, Jason, I grew up with your mum, as you know, and we have no secrets from each other. She told me she is worried about you. Does she have reason to be?' I looked away and mumbled, 'I suppose.'

'Oh darling,' said Sarita, 'You can tell me anything, you know. I think you really liked wearing that nightie, didn't you?' When I just looked down, and didn't reply, she persisted, 'You don't have to be ashamed of showing your feminine side, darling, I know you aren't gay, and even if you were, then so what? If it helps at all - and you may well have guessed anyway - I have something a little more than friendship with Caitlin, so I won't judge you whatever your inclinations.'

'So you are...lesbian?' I asked

'Don't pigeonhole me, darling,' she said, and as she spoke, I felt her hand move smoothly to my stiff rod, which she began to caress gently.

'Oh my God!' I moaned, and felt an impending orgasm welling up in my balls, but she gave my cock a swift squeeze, and left it alone. She gave a little laugh. 'I shouldn't have done that - not the sort of thing that aunties do, is it?' She smirked, 'But I hope it helps convince you that you mustn't put people into slots. We are all different.'

I had just about recovered, but I said, 'Sure, Sarita, I get that, but where does it leave me?'

'Come upstairs with me, and we'll see,' she said.

5

I followed her meekly upstairs, and she led me into her spacious bedroom, then literally shoved me into her en suite bathroom. It's bigger than yours, so have a nice shower and shave your legs - and anywhere else you've got hair.' She grinned, 'No hair below your eyelashes, eh!' When I began to protest, she said, 'Trust me, you'll love the result.' I wasn't at all sure, but did the best I could with the two plastic razors she's left ready for me, still in their wrappers. To tell the truth, I had never been very hairy, had no chest-hair at all, and very little around my pubes, but it was an odd feeling removing the soft fluffy hair from my legs, comfort¡ng myself with the knowledge that cyclists do it all the time. When I'd done, I emerged with a towel around my waist, to find Sarita sitting patiently on the bed. Wordlessly, she handed me a pink folded garment. When I took it from her I found I was holding a pair of lace-trimmed satin panties. I looked from them to Sarita. 'But I can't wear these!' I protested.

'Just try them on,' she said, 'You'll find them very comfortable.'

Reluctantly, I slid them up my bare, newly-shaved legs, and found myself trembling as they encased my balls and my cock, which suddenly seemed to have taken on a new lease of life at the touch of the soft satin. Sarita was smiling as she saw my reaction, but tried to play it down, and patted the bed beside her. As I sat down she showed me a packet, which I saw contained white stockings, then took them out, dropped down, knelt on the floor, and said, 'You won't know how to put these on, so this first time, I'll show you.' She rolled the fine, delicate stocking up on her hand, then proceeded to unroll it on my foot, and up my leg, all the way up, past my knee, up to near the top of my thigh, where I saw that the stocking top had a lacy pattern, and seemed to be elasticated. 'Hold-ups,' Sarita explained, as she set about the other leg. Much as I felt I ought to resist these completely feminine garments, I had to admit that the feeling on my smooth flesh was nothing short of divine.

'Now,' said my aunt, 'Stand up, and we'll see how you look in a bra.'

'Oh, come on!' I said, 'You have to be joking - that's a step too far. I really, really can't wear a bra.'

'Okay, Jason,' she said, 'For now, we'll make do with a camisole top - that will feel nice.' She fished a white silky item out of a drawer and passed it to me. I slipped it over my head and found that, as she had said, it felt nice, silky against my skin. But Sarita was sifting through her wardrobe. 'All my dresses will be a bit loose around the chest for you, I guess, so we're going to go for a skirt and blouse, okay?' I was still recovering from the feeling of the panties, stockings and camisole, and hardly in a state to comment. Before I could bring myself around she had found me a long sleeved pale blue silk blouse. I slipped it on, and found that it fitted nicely. How was it that all girls' clothes seemed to be so soft and silky, and nice against the skin, as oppoed to the roughness of men's clothing? But wait a minute, I couldn't get the damn buttons done up - then I realised - women's buttons did up the opposite way to men's! Sarita was laughing at my efforts, but meanwhile she had found me a knee-length, pleated cotton print skirt. I stepped into it, and fastened it around my waist. Looking briefly in the mirror, I was amazed by the change a few clothes had wrought in me, but I still looked like a boy in a skirt.

'I know,' said Sarita, 'We've a way to go. Come over here.' She led me over to her dressing table, and sat me down in front of the mirror, which she turned away. I had a half hour lesson in make-up, which Sarita assured me was 'a quickie.' She said a lot of girls would take an hour to get their face in order, but when she turned the mirror back so that I could look, I was staggered and just didn't recognize the person looking at me - a pretty young girl with a boyish haircut. But Sarita had designs on that too. 'Right,' she said, 'Hair! You have grown it a bit longer since going to University, I see, but it can do to grow more. I have a wig I could try on you, but I don't want to if I can encourage your own hair to look feminine enough. I think I'll try.' After a bit of playing around and styling as best she could , she stood back and admitted that 'although she said it who shouldn't' she'd done a good job, and when I looked again, I was astonished at the change in my appearance. Rummaging around in a drawer Sarita found some clip-on imitation pearl ear-rings, slipped three or four silver bangles on my wrist, then found a pair of Mary Jane shoes with modest heels. 'There,' she said, 'You'd pass for a young girl whose breasts haven't yet started to flourish. Have a walk around.'

6

I stood up and walked about, a little unsteadily at first, even though the heels were quite low, but I was immediately aware of the infinitely pleasant feeling of my bestockinged legs against each other, and of the loose skirt swishing around as I walked, not to mention the soft satin encasing my intimate parts. I exchanged a look with Sarita. 'I think you like the feeling, don't you, Jason?'

'I don't know. It feels wrong.'

'It's new, darling, but come on, admit it, it feels nice.'

I looked down - couldn't meet her eyes. It did feel nice.

'Come on,' she said, 'Let's go shopping.'

'Like this!'

'Of course. You look perfectly normal, and nobody knows Jason here. By the way, what am I going to call you? I can hardly call you Jason.'

'I always thought I'd like to have been Jenny,' I mumbled.

'Oh darling!' said Sarita, and hugged me, so that I felt tears welling up. 'Don't go crying now,' she said, 'Your mascara'll run.' But I saw she had a wetness in her eye too.

When we got into the garage I had my first lesson on deportment, and learned how to get into Sarita's little car without displaying my panties to all and sundry, by putting my bottom in first, then swinging my legs in together. 'You have to do it that way anyway when you're wearing a very tight skirt,' said Sarita, 'I guess you have a lot of learning to do, Jenny.'

Calandria
Calandria
336 Followers