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The Together Plan By Eva Dell --- DISCLAIMER. This story is fiction and is intended solely for the entertainment of adults as defined by the reader's society or culture. If you shouldn't be reading this legally, or you are offended by material of a sexual nature or themes of cross- dressing, bondage, domination, or sexual activity then please stop reading this now. There is no intended similarity in this story to any person, place, organization or event and the author does not condone any action or behavior described here. Fantasy should never be confused with reality. You may distribute this work of fiction, but only in its entirety, unchanged, without charge and you must include this disclaimer. Please ensure that if you do archive, copy or distribute this story you must meet your responsibility to protect the young, the innocent and the vulnerable. This story appeared in ASSTR's Tented Skirt but has been expanded and corrected. --- Sandra Carter reached across the restaurant table and took her lover's hand, giving it a reassuring squeeze. 'I know I said I would leave him, but we both know I can't,' she said gently. 'As much as I love you Jon, I also have to do the right thing for my family.' Jon Murray studied the woman's hand before he answered. 'I know it would be hard for you, but we love each other -' 'We always knew it would be hard,' interrupted Sandra. 'We talked about it before and you knew all the things that go on in my life. But, I just didn't realize how hard - not until I sat down and thought it all through. The children, Robert's job, my inheritance: I can't walk out on all that.' The 32 year old woman, slim, attractive and well-dressed, offered the man opposite her a smile and squeezed his hand again. 'But we can still be together!' 'How?' Jon shot her an anguished look. 'You told him about us. Now he knows, we can't even continue meeting, even like this.' He sounded bitter. 'Before - before you told him - we could meet openly, find a place to make love. Now...' He paused and looked round the near empty restaurant, 'We have to watch out for someone following you, checking up on you. Your husband could have had you tailed here.' He looked round again, trying to see if anyone was watching them. 'He hasn't. I was very careful getting here.' 'But you can't be sure, Sandra.' The man, almost ten years younger than the woman, creased his face in anxiety. 'Now he knows, Robert isn't going to sit back. He will have you watched. You might escape someone following you this time, but next time? When you get out to go shopping he will check up on you. You'll have an hour but no longer. How can we meet and make love then?' 'We can't,' admitted the woman sadly. 'So why did you tell him? If you weren't going to leave him, why spoil our limited time together?' 'Because there is a better way,' she said, a slow smile growing on her face. Jon saw the smile and shook his head. 'There isn't a better way, and you know it. It has to be over.' He sounded crushed and tried to withdraw his hand, but Sandra held it tighter. 'No, listen to me!' Even though there was no one near them in this corner of the restaurant, she still dropped her voice to little more than a whisper. 'If you do what I say, if you follow my plan, we can be together every day.' 'So you will leave him?' Jon sounded incredulous, but hopeful. 'No,' Sandra was firm. 'But you can be with me at Northwood, every day.' Despite how he felt, Jon gave the woman he loved a grin. 'It's a big house, but not that big. What are you going to do, smuggle me in and hide me in the basement?' 'Interesting, but no. If you do what I say you will be able to move round openly. In disguise, true, but you will be able to be near me. And when it is quiet we can make love.' Jon shook his head again. 'Now you've told your husband about us he's going to be suspicious of any man in the place, no matter how well disguised. Shit, I bet he even watches the gardener closely from now on.' 'But he wouldn't suspect a woman!' Sandra had leaned closer, her voice urgent but barely audible. 'Sure, but I'm a man, right? That's why we make love - or made love - remember?' 'But you could be a woman. I could dress you up, get you a job as a maid. Robert wouldn't suspect a thing.' Jon stared at the woman disbelievingly. 'Are you crazy?' He managed to say after a moment. 'I'm not a woman... I have a dick, remember?' 'But you could be a woman, if you trust me.' Sandra was excited, beaming at her lover. 'You could act the part - you always said you could act well. You've done it before.' 'That was college,' Jon Murray shrugged. 'A couple of plays... it's not real life.' 'I could teach you how to be feminine. Anyway, Robert's going to be on the look out for a man, not a woman. He won't be aware of how masculine you are under all that feminine get up.' Jon looked bewildered. 'So I act - and dress - like a woman and everything just... just works out?' 'That's the plan.' The young man finally extracted his hand from the woman's grip. 'No way, Sandra. It's the craziest idea ever.' 'That's why Robert won't suspect anything!' Sandra raised her voice slightly, more in eagerness than frustration. 'In fact, he'd welcome a woman round the place. Someone who could go out with me, keep an eye on me. Sort of a chaperone who'd make sure I didn't meet anyone. Don't you see how it would work?' 'I can't believe you even think he'd fall for that.' 'Look, he's busy. Robert wants to concentrate on business. If I had a chaperone, he'd leave me - and us - alone. Alone to do what we want.' She took his hand again. 'Think about it, for our sakes!' Some emotions flickered across the young man's face before he growled: 'I've thought about. I can't and won't. You know that.' 'I know you want to be near me, with me. I know I want to be near you, make love to you when I can.' 'But as a woman... that's crazy. You want me to be a lesbian?' 'Hell no! I want you to be a man. Under a skirt, you'd still have a cock. A cock that gets stiff when I put it in my mouth.' Sandra licked her full red lips seductively, knowing how it excited her young lover. Jon stared at her and wriggled a little in his seat as his penis hardened in his pants. 'Shit, Sandra, not here.' 'Then at my place, at Northwood. You like me in a skirt so you can get your hand up quickly. Well, maybe I can return the favor.' Her eyes twinkled and Jon felt his cock stir more. Despite himself there was a certain forbidden excitement about this. 'Sandra... I don't know.' He felt himself blush - more as Sandra rubbed her foot against his leg, under the table. 'I can show you and make love to you in wild ways, believe me! All I have to do is lift your skirt and lift mine and... you know what we do then.' The man shifted himself in his seat as his dick grew harder. 'I don't know,' he groaned. 'I mean, a woman! In a skirt and... well, blouses and stuff.' He blushed. 'Couldn't I wear pants?' 'No, the more feminine the better.' Sandra gave a small laugh. 'We could even go shopping together, choose things for you - and me. That's one thing about Robert: he gives me a really good allowance.' Jon stared at the table and then at Sandra. His face showed the turmoil in him, how much he was considering about this. 'People would see that I wasn't,' he hesitated. 'I wasn't, you know, a woman.' 'You're slim, you naturally move elegantly. Believe me,' Sandra nodded. 'When I've finished with you, no one could tell. Only we will know that under all that lace is a wonderful cock that's itching to get in me.' The woman paused. 'I can imagine it rubbing against some delicate lace under your skirt so it stayed semi-erect and you know how that drives me crazy, seeing it almost ready and I have to tease it some more.' Jon took a deep breath. He wrestled with the idea for a few minutes. Then he took a deep breath. 'Okay, I'll try it. In a hotel room first, and if I look convincing then...' 'Then we'll do it,' grinned Sandra. --- 'You already bought the stuff?' Jon's jaw dropped at the sight of all the parcels on the bed of the hotel room, boxes with labels on from lingerie stores and clothes stores. 'You knew I'd say yes?' 'I knew you'd say no, but I also knew I could persuade you. So I figured, why wait?' Jon snorted, and the reached for Sandra. He caught her and drew her to him, putting his arms round her. 'Well, as you're so clever, tell me what's going through my mind.' 'Sex, and this isn't the right time.' She struggled out of his embrace, but with a smile. 'Right place,' he said, nodding at the bed. 'Wrong time. I don't have enough time, as much as I'd like to fuck you.' She looked wistfully at him. 'It's been a few weeks but...' she snapped out of it. 'We have to see if we can make you what we want you to be.' 'What you want me to be,' he reproved. 'I'm happy to be a man. Let me show you.' He reached for her again but she ducked away. 'And you will be, under the clothes. You can show me later.' Sandra scooped up one of the boxes, marked Lady Special, and tossed it to the man. 'I'd open that one first,' she said with a smile. 'If you aren't going to go through with this you had better make your mind up about that one first.' Carefully Jon opened it, pulling out a black bra. 'Hell, a bra?' He exploded. 'But surely I don't need one of -' 'You need one if you are going to be convincing. A woman without a bust is rare. Too noticeable. Oh don't worry, it's not something like a 36D. You won't be out to draw admiring whistles from men.' He read the label. '34B. Is that my size?' 'I guess.' The young man held it up, against the light from the afternoon sun glowing through the gap in the drapes. 'Lot of lace,' he said quietly, glancing at Sandra. 'You don't wear bras with as much as this, right?' 'Sometimes I do. But before you ask, you have to feel feminine all the time. The lace does that. If I gave you a bra like some I wear you might not think you were a woman.' 'I think I'd feel pretty much like a woman if I was wearing a bra. Period.' Sandra sighed. 'This is crucial, Jon. You have to be reminded all the time that you are a female. That's why the rest of the stuff,' she indicated the pile of boxes, 'is very feminine.' 'Meaning?' Jon dropped his hands but didn't put down the bra. 'Meaning plenty of very sexy lingerie. Garter belts, lace panties, satin slips with lots of lace trim. Blouses and skirts, dresses - and shoes to match your outfit.' Jon stared at her and then at the unopened boxes. 'You just used a lot of plurals. You mean, there are lots of things for me to wear?' Sandra gave him a grin. 'Eventually we'll have a closet full of stuff. A good woman has lots of clothes to choose from. For now, there's enough here for you try a couple of things on.' She paused, looking him up and down. 'You know, this wouldn't have been possible if you weren't a little ladylike already in the way you move.' Jon colored up. 'I'm not... I'm not gay, you know that.' 'Oh I know,' she smiled at a delicious memory. 'I didn't say you were. But there is a female side to you. That's what's so appealing. Now, let's get these things on you and we can see how good you look.' 'You think I'll look good? If I don't, I won't go through with this. You know that.' 'Sure. We won't go through with it. I'm not exposing you to ridicule. I just want you in my house.' 'In your pants,' said Jon wickedly. 'Well, my pants would probably fit you.' Before he could object, Sandra laughed. 'I know, I know. But look, honey, we have to get on. Tell you what, once you're dressed, I'll show you a real treat.' Sandra scooped up a couple of parcels. 'In this one is a garter belt and stockings. Panties, too.' 'They match my bra, I guess.' The woman nodded. 'That's very important,' she added, soberly. 'I don't want a woman around me who doesn't know how to dress herself.' 'Himself,' corrected Jon. 'By the way, you can't call me Jon, can you?' 'No. But I can call you Joan.' 'Joan! That's not the name I would have chosen for me.' 'Which would be?' Jon shrugged. 'I'll think of something. When I have all this on.' --- Sandra insisted he put the clothes on himself, watching him struggle with the bra, the garter belt, hooking the stockings to the garters. She offered no advice as she watched. 'It doesn't take you this long,' he said, flustered at his lack of progress as he strained to twist and fasten the last of the garter tabs. 'I'm used to it. You have to get used to it, too.' 'Shit, I don't think I ever will,' he grimaced as with one last effort he fastened the fourth and final garter. With a sigh, he straightened up. 'I think I look stupid, but tell me how you think I look.' Sandra regarded him. 'Stocking on your left leg isn't pulled up properly. And you put a run in it,' she said gravely. 'Women try not to get runs in stockings as they put them on. You have to roll them up your legs, not drag them. Dragging them off for passion is one thing, putting them on is quite something else.' Jon blushed slightly, recalling how he had once torn the stockings off Sandra, early in their relationship. 'Okay. But I look what - reasonable?' 'Not the way you're standing, all hunched up. Stand up straight! You're a woman, honey, proud of it. Push your chest out.' 'I don't have a chest,' he said sourly, indicating the slightly crumpled lace cups of his bra. 'But you will have.' Sandra smiled and reached into a box. She held up a pair of soft plastic false breasts. 'Inserts,' she explained. 'I can't wear those!' The young man took a small step backwards, almost in fear. 'Why not? You plan on growing your own?' Sandra was clearly enjoying this. 'Course not! It's just that...' 'I know, you're a man. Men don't have breasts and if you did, you think it would replace your cock.' Sandra shook her head. 'Primitive instincts, man versus woman.' 'No. I just reckon they would look too obvious.' 'They won't, and no one will know. They will look perfect. After all, no one's going to feel them. Though I have to say they do feel quite realistic.' She offered them to her lover. Reluctantly Jon took them and started to say something about men and breasts but she ignored him, turning away. When she looked back he had slipped them into the cups. He was, she noted, even standing up better, actually pushing his chest forward. She also noticed that the bulge at the front of his black lace panties had grown that little bigger. Casually, Sandra asked: 'You enjoying this?' The man in the black underwear and stockings shrugged. 'It's okay, but I'd rather be screwing you,' he said as he gestured towards her and the bed. Sandra shook her head and found another box. 'This one is a slip. Now, just to demonstrate the importance of matching clothes, I didn't buy black. Because the blouse I bought you is pink I figured a peach slip would be better.' Confusion flickered across Jon's face. He'd never thought about such nuances before. 'I don't get it... Why?' 'Oh really, Jon. Think! Black shows through lighter colors - only sluts would want that. The peach slip will hide the black of your bra, okay?' Jon thought about insisting he wasn't even thinking of any color of underwear but could only nod meekly. He got the slip on, pulling it over his head and shrugging it down his body. 'Seems to fit okay,' he said, more to himself than Sandra. The blouse came next, a candy pink satin blouse with wide lapels and long, baggy sleeves. Sandra watched silently as the man slowly and awkwardly fastened the small buttons. He grumbled about the number but Sandra ignored him, readying the midnight blue skirt for when he had finished. He made no objection when she handed it to him, stepping into it and closing the zipper at the side almost as if he had done it before. He smoothed the skirt down over his hips, and suddenly Sandra laughed. 'You've done this before, haven't you?' Her laugh rang round the hotel room. 'No... well, yes. But it was a long time ago.' The young man flushed crimson. 'Go on, tell me more,' invited Sandra, settling herself into a chair. 'I don't know,' said Jon distractedly, fussing at the front of his blouse. 'Maybe it, uh, doesn't matter.' Sandra stared at him, waiting for him to go on. He shook his head, and then said: 'I was 14, maybe 15. My cousin, Lana. She wanted me to do it. She made me put on some of, well, my mom's things.' His blush grew brighter, and he looked away from Sandra. 'Made you?' enquired Sandra, delighted at what was being revealed. 'So how old was this Lana?' 'Younger than me,' Jon grudgingly said. 'How young?' 'Um... Twelve.' A pause while he smoothed the skirt again, and he finally looked at the woman in front of him. 'But I had to. She threatened to tell my mom about me.' 'Wow, three years younger than you. So how come she had this hold over you?' There was a silence before he said: 'She caught me... Lana found me wearing a pair of my mom's pants. She said she'd tell everyone unless I put everything on.' 'I see. And how did that make you feel?' 'Look Sandra, it was a long time ago. I was stupid, I guess.' 'Maybe, but you wore your mom's pants, right? So you had done that a few times.' Jon shrugged, blushed a little more. 'Yeah, well... and her bra a couple of times too.' Sandra laughed again. 'Her bra, that's great! What was it about it? All red lace and see through?' 'No, nothing like that!' the man seemed offended. 'My mom wouldn't have any underwear like that!' Then he took a deep breath and continued: 'Just white. Kinda everyday sort of underwear. I just wanted to see what it was like to wear it. You know, get the feel. I figured the girls at school were getting real big breasts and I just wanted to see how they felt, wearing a bra.' 'But that doesn't explain the panties.' 'Ummm, they were sort of there.' The man in the pink blouse and blue skirt looked away. 'It was just for fun.' 'And don't tell me, let me guess, this Lana found you with your hand down your panties, whacking off, right?' Jon spluttered a "no" but at Sandra's steady gaze he relented and nodded sheepishly. 'So, what exactly did she make you wear?' Sandra was grinning. 'Tell me all about it.' 'Just some of my mom's things. You know, pantyhose, slip, dress, shoes. I had to parade for her, like it was a fashion show.' Jon blushed an even brighter red. 'Look, can we drop this?' 'Drop what? Getting dressed up now or talking about getting dressed up then?' 'Back then,' said the man. 'I'd rather not talk about it any more.' 'Huh-uh. So something else happened, right?' 'Sandra, nothing happened. I'm just embarrassed by it, okay?' The woman stared at her lover and finally nodded. 'Okay, that was then and this is now.' 'You said I could have a treat, once I'm dressed.' Jon started to move towards Sandra but she was on her feet, sidestepping his hands. 'Sure. Something really special,' she gave a small laugh. 'You gonna suck me off?' 'Oh no, better than that.' The woman reached into her purse and drew out a small, thin pink object. Jon's eyes widened. 'Is that what I think it is?' 'And you think what?' 'A dildo of some kind.' He gave a small gulp. 'Is that for you?' 'No, little too narrow for me. It's for you.' 'Me?' Jon's jaw dropped. 'What the hell do I do with a dildo?' Sandra twisted the end of it and the thin dildo began to vibrate. 'It's a vibrating dildo. An anal dildo. You put it up your asshole,' she added with a smirk. 'Right up inside.' The cross-dressed man stared at the woman. 'Sandra, there's no way I'm going to put that up me. Anyway, why should I?' 'Because it will excite you, keep you on edge. Remind you of me.' 'I can get all my excitement by fucking you. I don't need that... that toy.' 'But you can't fuck me for a while. Not until you're safely in my house.' 'We could have fucked three times here while we've been messin' around, dressing me up!' 'Maybe. But this is a long term plan.' Sandra sighed. 'Sure, we can screw sometimes if you stay a man, maybe once a month if we're really lucky, or maybe have to wait until he's out of the way, gone on business - could be months. But it will be so infrequently it will drive you nuts. Once you are in my home we can screw far more often. But we have to plan and prepare first, okay?' 'And you figure this anal dildo is some compensation?' Sandra nodded and smiled. 'It will keep you hot for me. I guarantee it.' She paused and examined it. 'The instructions say you can set it to random - you could get a real buzz in the middle of some meeting. And oh yes, it's silent, so only you know.' 'This is crazy,' said Jon. 'You can't really think I'd walk round with that up my butt, just to please myself?' 'You would for me, though. Just like you got all dressed up for me. And remember, you like my finger up your ass, when we screw. This is just like that - a nice reminder of what we are going to be doing a lot.' The man considered the options, the memories of Sandra's pleasant finger wedged up his chute while they fucked. He pursed his lips and nodded. 'Okay, if that's what you want.' He took the dildo, reluctantly, examining it suspiciously. 'Huh, long-life battery,' he said as he flicked the small switch to random. 'You want this up me now?' Sandra nodded. He bent forward slightly, hiked up his skirt and slip and eased the panties aside, pressing the narrow to tip to his tight little anus and giving a small gasp as he pushed it in. 'Fuck,' he complained. 'It hurts.' But he did it, the dildo slid up out of sight and he stood up, eyes suddenly widening as the randomized vibration mode kicked in. 'Wow,' the astonished man said after a moment. 'That's incredible.' He stood, swaying slightly on his feet, allowing the sensation to ripple through him for a good minute before a disappointed look appeared on his face. 'It's stopped,' he said, his breathing a little ragged. The man, his face flushed, straightened his skirt. 'It will start again sometime,' laughed Sandra. 'And honey, as well as this, I want you to wear panties every day, get used to the feel of that satin next to you. You can wear them under your suit.' The man stared at his lover, still regaining his composure from the assault in his ass. 'You want me to wear a bra, too?' Sandra laughed. 'Great idea, but not quite practical. Unless you don't mind people seeing your bra straps underneath your shirt.' He gulped at the thought, and then grinned back at her. 'You don't care if they do.' 'Well, I care enough to want you to be happy. You won't mind them showing, too, when we are together at Northwood.' 'Am I expected to make love to you while I'm dressed like this?' 'Maybe. For a quick bang.' She smiled at him. 'Like now.' Jon needed no second invitation. He took her in his arms, kissing her passionately, not caring that under all these female clothes his cock had grown hard, pressing against his panties and slip and skirt, pressing against her belly. She reached behind him as they kissed, hoisting up his skirt, pressing herself closer to him. He broke from the kiss, whispering: 'Let me get my cock out.' She did, and as he screwed her from the rear as she bent over the hotel bed the dildo suddenly started buzzing in his ass again, driving him to new heights of pleasure as he drove his stiff dick into the woman he loved. --- 'Sandra, where the fuck have you been?' Jon breathed down the phone. 'It's been weeks since I saw you.' 'Eleven days,' said Sandra, her voice tired. 'I've been away. With him.' 'Where?' panic edged into the man's voice. 'You didn't tell me!' 'I couldn't. It was all at short notice. He had to fly to Europe on business, wanted to take me along.' 'You could have refused.' 'Jon, get real! I'm trying to make him less suspicious of me, not more!' Jon grunted an acknowledgment. Then added: 'You could have called. They do have phones over there.' 'Time zones don't help, honey,' Sandra sighed. 'I couldn't call your office when I had the chance, and when he was around I didn't want to arouse his suspicions.' 'You could have told him you were calling a friend,' Jon snorted. 'A close female friend.' 'Sure, and if he checked on another line and heard your voice? It doesn't bear thinking about.' She paused. 'I didn't want to go, but it's better like this.' 'I guess,' he conceded. 'Are you still dressing up at night, trying on those things for us?' Sandra suddenly brightened. 'You mean the skirt?' 'And the blouse and the dress - both of them.' Jon took a deep breath. 'Yeah. All of it.' 'And the underwear? It is important, honey.' 'Why?' 'So it feels natural. You have to feel at home in it all, that you've been wearing it all for years. That way he won't think there's anything wrong.' 'How wrong?' Jon was suspicious. 'I don't want him thinking you look uncomfortable in it all. If he thinks something's wrong then he'll...' She trailed off with an ominous shrug. 'Okay, okay. I've been wearing the bra and the garters. Just like you showed me. Panties to work too.' 'Good. And you've been wearing the makeup at home, practicing putting it on?' 'Yeah,' the man sighed. 'Lipstick, eyeshadow. Even that foundation cream stuff.' 'I bet you haven't had the nail polish on.' 'I have,' he exploded. 'You don't trust me, right?' 'I do. You know I do.' She sighed. 'I love you, Jon. But I have to check, right? To be successful we have to be prepared. That means you being convincing.' Jon grunted. 'And at night,' continued the woman, 'you had the sleep bra and the nightie on?' 'I don't see what that stuff has to do with what we are doing.' 'It's part of you being so good, playing the part fully. You have to think and act like a woman all the time.' Jon hesitated, and then said: 'I wear them most nights.' 'Jon! We agreed!' 'Okay! I'll make sure I go to bed in them every night from now on.' 'And you'll do your hair, like I showed you? Put it in curlers.' 'Of course. You think I wouldn't?' 'No, honey, I think you would. But I have to check. It's for our future together. We have to get it right.' Jon sighed at what seemed an ever growing list of demands. She hadn't asked if he kept up shaving his body and legs, at least not yet. He had no doubt she would and he'd have to tell her how he'd removed all his hair below his neck, shaving every day. He put the thought aside of him standing in the shower with the woman's razor in his hand. The one she'd bought him, saying his old razor was no good for such a delicate task. 'When do I see you again?' he asked. 'It has to be two weeks,' the woman replied. 'What?' 'At the moment, the longer the better between us meeting. Sometimes I think he may have me followed.' 'Two week's too long. I have to see you!' 'Be patient, honey. Soon, I promise.' She paused. 'I'll send over the present I got you from Rome.' 'You bought me something?' 'Yes. A really nice flared skirt and matching top. You'll love them.' Jon was taken aback though not as much as he might have expected. 'You sure about that?' 'You will if you think of me while you're wearing it, especially when your dildo starts twitching,' she said and blew a kiss down the phone. --- Jon opened the door of his apartment and stood in his new skirt and top, blushing. 'Jon, you look wonderful,' cried Sandra, stepping in and giving him a hug. She pulled away in a second. 'Let me look at you in that skirt!' The man stood back and allowed Sandra to look him over. 'Do a little twirl for me honey,' she begged. He hesitated, saw the look of delight in her eyes and did as she wanted, despite his embarrassment at being seen in full attire. He turned on his high heels so the full skirt flared out gently. 'Sandra, can we...' he began but she cut him off. 'I knew that outfit was just right for you the minute I saw it,' she enthused. 'And your hair! It's perfect. And I love those earrings and the necklace. Your lips look gorgeous, honey, and I like the way -' 'Sandra!' Jon snapped. 'I'm not a fashion show!' 'I know, darling. I'm sorry, I just got a bit carried away. It's been ages since I saw you and I wanted you to really get into this.' He pulled her to him, pressing her slim body to his. 'I think we can talk in bed, don't you?' She felt his cock, hard and strong, pressing against her belly. They kissed, full red lips to full red lips, the scent of each other's perfume in their nostrils, their hands running across the other's back, feeling the bra straps through their respective tops. 'Let me get out of this, now you've seen it,' said Jon, breaking the kiss. 'Then we can screw.' 'We can screw with you like that,' breathed Sandra. She ran her hands down his back and over his skirted rear. 'Such a great ass. What color panties have you got on? Let me guess... either the red ones or the black ones.' Jon grinned at her. 'Yellow. I went out and bought some, just to prove I could.' 'Jon, that's wonderful!' Sandra giggled. 'And I don't suppose you bought anything else for me to admire you in, did you?' He blushed a little. 'I'll show you later.' They resumed their kiss, long and hungry and wet. 'Let's go to bed,' said Sandra as they surfaced. 'Now.' 'Like this? In all our clothes?' 'Oh yes, it's going to be great being fucked by you in your women's clothes.' They lay on the big bed and drew each other close, hands groping up each other's skirt: he seeking the deep, hot slit between her widespread, stockinged legs, she skipping her fingers over his garters and stocking tops, feeling the lace of his new panties and then stroking the bulge under the satin. Finally she freed his cock, grasping it tight as he slid three fingers into her. 'I'm going to make you cum in your clothes,' she whispered. 'I want to cum in you,' he said, kissing her. 'Later,' she smiled and slowly teased his stiff cock, drawing her fingers down the shaft, her fingernails almost scraping his skin. He gave a moan and she let the panties slide back over the erection, continuing to rub it through the thin, delicate fabric, letting the sensation of her touch and the caress of the satin panties arouse his deepest desires. He came with a cry, pumping out his semen into the white lace and yellow satin. 'Now lick me,' demanded Sandra, extracting his hand from inside her and climbing over his face, hitching her skirt up round her hips. 'Make me cum through my panties.' He looked up, saw her smiling down at him and extended his tongue, pressing it against the taut, sopping wet crotch of her black panties, the musky smell of her aroused sex filling his senses. Jon licked, slowly, intensely, his tongue straining hard to push up into her vagina through the fine layer of her underwear, stretched over her wet cunt. 'More,' she gasped. 'Do it harder.' He licked harder, her juices soaking through the fabric and burning his tongue, until she came with a shout, pressing herself down on to his face and almost smothering him. 'Don't stop,' she shrieked, and he didn't even though his jaws ached and he was fighting for breath. Eventually, she slid off him. 'You've passed,' she grinned. He looked at her, puzzled. 'You made love like a woman makes love to another woman. With your tongue.' She grabbed his head and kissed his mouth, her tongue reaching into him, seeking out any taste of herself. 'I still want to fuck you,' he said, as they broke the long, deep kiss. 'You will. In your new clothes - whatever it is you bought.' Jon climbed out of the bed and rooted in a drawer, pulling out something red. 'It's a basque,' he said, holding it up. 'You bought that? Good choice.' 'I'll need help putting it on. There's a lot of hooks at the back.' 'And six garters. You must have looked around for that - you don't get those in the mall.' 'I had it mailed,' he confided, beginning to strip off his clothes. 'It's great what you can find on the net.' Sandra smiled and waited for him to get naked and then she carefully hooked the basque round his waist, insisting on fastening his garters for him. She paused only to tease his hardening cock, bending to lick the head of it to ensure it was fully erect. Then she made him wait while she inserted the breast forms into the basque's lace cups and adjusted the straps. 'You look fantastic,' she purred finally, lying back and spreading her legs wide. Jon mounted her, feeling his stockinged legs rasp against hers as he drove his cock deep into her. It felt wonderful as he came: the only disappointment was that the dildo up his ass didn't kick in at all. And he had no idea it was the last time he would ever screw the woman he loved. --- The cab door opened and Jon climbed out gingerly, testing his heels before he put his weight on them. Sandra climbed out after him, paying the driver. 'Just relax,' she whispered to the man in the dark red dress and black high heeled shoes, taking his arm. 'Remember everything we practiced in the apartment, all the things I told you.' 'Shit, Sandra. I feel everyone's looking at me.' 'Maybe, but has it occurred to you that you look exactly what you are: an attractive woman with style. That always draws a look or two wherever you are.' 'Maybe they recognize I'm a man in a skirt! Why did you bring me out here? It was okay in the apartment.' 'We agreed that you have to be seen in public. So, just walk, nice and easy. We're two women out shopping. Friends going round the stores.' 'My slip feels like its gonna come down.' 'No, it's just you're not used to the breeze on your legs, under your skirt.' Sandra smiled. 'Actually, you're doing well - if you can stop staring ahead like that. Relax and look around at the store windows.' 'What am I supposed to be looking at?' 'Women's clothes, obviously.' 'Robert could have us followed.' 'If there's a tail it's me that gets followed. Anyway, so what? I'm out with a girlfriend, shopping.' She laughed, steering him towards a window display of evening gowns. 'We look good, you look natural.' Jon blushed slightly as they stood, Sandra pointing out the price of an electric blue gown. 'Of course,' said Sandra, 'The real test is getting you into that dress. Trying it on.' 'No,' Jon gave a strangled cry. 'I can't!' 'Why not? It's your size. It would suit you.' 'Sandra, I can't go into a woman's changing room.' The man looked around anxiously. 'Someone might see.' 'Here they have individual cubicles, not a shared room,' Sandra calmed him. 'It would be totally private. You try the gown on and come out, show me, if we agree it's not right and you go and take it off. If you like it - we like it - we buy it. We resume our trip.' 'The sales clerk will know.' Jon said, jaw set hard. 'How? You think the women who work in here are closet lesbians and voyeurs who want to look up your skirt?' 'No, but...' 'There is no but about it. Let's go.' Sandra commenced walking, arm threaded through Jon's arm, towards the doors. A man, aged fifty or so, held the door open for the two of them, giving Jon a smile. 'You see that?' gasped Jon. 'An admirer,' grinned Sandra. 'Maybe he'd like a date. Or is he too old for you?' 'For fuck's sake Sandra, this isn't a game!' 'No, but it should be fun.' She sighed. 'We agreed being convincing is what will make the difference, okay? Then we can be together.' 'Sandra, look I rea -' Jon stopped, his face flushing slightly. Sandra guessed. 'The vibrator's kicked in? Great. Just stand here by this rack of blouses, make like we're choosing one.' 'Yeah,' Jon managed weakly as Sandra picked out a cream and brown patterned blouse and held it up against her boyfriend. He didn't resist, even when she told him to hold his arm out so she could measure it against him better. To Jon's horror, Sandra called out to a sales clerk nearby. 'Hi, have you got this in the next size up for my friend?' 'Of course,' said the girl, stepping over. She looked about eighteen, blonde with a cute nose. Attractive. The name on her badge said 'Kirsty'. Under other circumstances Jon might have thought about trying to get a date. He blushed and Sandra noticed, giving him a curious smile. 'Yes, here,' said the young woman, pulling a blouse out from near the end of the rack. 'It's a really popular line and we don't have many left - I'm glad we found one.' She held it out, not towards Sandra but towards Jon. 'The changing rooms are behind you,' she said, pleasantly. 'Oh, and we have the perfect skirt to go with it. Over here.' To his horror, the young woman led the way towards the changing area, towards a rack of skirts. Sandra followed the sales clerk while Jon, clutching the blouse, followed nervously. He wanted to say: 'I can't do this, Sandra,' but his girlfriend was deep in conversation about skirt lengths for the coming season. 'Madam will find this perfect,' said the girl, picking out a dark brown skirt, showing it to Jon. 'Button fronted, but it's very popular with that style blouse. You should try it on with the blouse.' Jon glanced at Sandra and saw she was standing back. He was alone, and said 'Yes, thanks,' faintly, at a high a pitch as he could. He took the skirt and set off for the changing rooms. 'I'll wait here,' said Sandra. 'Come out and show me.' The two females watched Jon disappear, hesitantly, into a cubicle. 'What do you think, Kirsty' said Sandra. 'Good enough?' 'Very good,' said the girl. 'Better than you said. He just needs to relax.' 'I should wait here, but...' Sandra looked at the girl. 'We could go over to the coats, behind them.' Kirsty's perfect eyes twinkled. 'He'll be a good few minutes with all those buttons.' Sandra smiled and nodded. The coats made a good screen, and nobody else was there. Kirsty glanced round, satisfied they were alone and leaned forward to plant a soft kiss on Sandra's lips. Sandra's hands were up, fumbling at the buttons on the girl's blouse before they broke the kiss. 'Quick,' breathed the girl as her white bra covered breasts were exposed, Sandra's hands on them. The small fastening in the valley of the girl's breasts came undone, the smooth skinned breasts tumbled free. Sandra had her lips on one of the girl's large, hard nipples. 'Sandra,' moaned the girl, barely above a whisper. 'Please...' Sandra had her hand up the girl's skirt, groping eagerly, fingers sliding into the wet, open sex of the teenager. In an instant she was working her hand in and out, savage and swift. 'Fuck,' whispered the girl as stood, swept up in this rampant lesbian sex. presently she came, Sandra's teeth biting down hard into the tender flesh of Kirsty's engorged nipple, making the girl whimper in pain and pleasure. Sandra stood, calmly wiping her wet fingers on the lining of a coat and slid out from behind the rail of clothes, idly examining one of the price tags as she did so. She could hear the merest sounds from the drained teenager sorting out her clothes, and with a smile moved easily back towards where Jon was standing, dressed in the blouse and skirt. He had a look of panic on his face. It dissolved as he saw Sandra approaching. 'Sorry,' smiled Sandra. 'I was distracted by an offer in the coats.' She looked her boyfriend up and down. 'You look great in that. Just walk up and down for me.' Jon, an imploring look on his face, begged her to let him go back and change. She shook her head and insisted he paraded a little in the clothes. The young sales clerk, face a little flushed, arrived at Sandra's side. 'Perfect,' said Kirsty, standing a shade too close to Sandra. 'Would madam be taking them?' Sandra, enjoying all this, looked at Jon. He gulped and nodded. --- 'I can't believe you made me buy these things,' Jon said as they walked away from the store. 'That sales clerk - she looked as if she knew I wasn't a woman.' 'Nonsense,' purred Sandra, taking Jon's arm and steering him this time towards a shoe store. 'That's your imagination. She was completely fooled. I spoke to her and she made no mention of anything odd. Now you need some shoes to go with that. Black shoes are no good with a brown skirt.' 'Please, Sandra, do we have to?' 'Yes,' smiled Sandra. 'We have to. No arguments.' She was firm, her eyes sparkling. 'But don't worry if they haven't got anything here. There's a better place further down.' Jon endured three shoe stores before he was fitted with what Sandra decreed as proper shoes. Then it was on to another clothes store, trying on a black dress this time. That was added to the collection. 'This has cost me three hundred dollars,' the man groaned as Sandra hailed a cab. 'Yes, but wasn't it great? Women always enjoy spending on clothes and shoes.' 'I'm not a woman,' complained Jon. 'Soon will be,' winked Sandra. The man thought about objecting but the cab pulling up made him postpone his comments. --- If one thing pleased Jon it was that Sandra was turning up more and more at his apartment. What displeased him was the length of visits: short, urgent calls often with no notice. He knew they were to check what he was wearing, ensuring he had the right underwear, the right shoes and even the right makeup on for his outfit. But seeing her was everything. 'When are we going to have sex?' he would ask as Sandra inspected him, making him turn to show how he looked all round. 'Soon enough,' she would reply, but the nearest he came to it was on two occasions when Sandra lifted his skirt and performed oral sex on him. Hurried, but at least some satisfaction. But she didn't swallow the second time. 'I'm in a hurry, honey. Be an angel and finish yourself off for me,' she said. Jon thought it odd that she didn't leave until he came on the carpet while she watched. He wondered if he should ask why if she had not time to blow him did she stay around to watch what he did. But she was gone the moment his semen splattered on the floor. On the phone later she told him to be patient as it would be better, and he had no option but to believe it. Then Sandra began to issue lists of things he had to do: instructing him to wear a dress for so long and then change into something different. Sometimes she insisted they went to the mall and browsed clothes and shoes and lingerie endlessly. He now had six pairs of shoes and had got so used to wearing heels about his apartment he had difficulty adjusting to ordinary men's shoes when he went to the office. And the anal vibrator buzzed at all sorts of unexpected moments. It was eight weeks after their first public show as she called it that Sandra said everything was in place. Jon would accompany her to Northwood and be introduced to Robert. The rest of the family would no doubt be there - maybe even Robert's daughter from his first marriage. All Jon had to do was act like he had so far, dress modestly and smile. 'You need a name,' said Sandra, watching Jon as he did yet another twirl - this time in a pencil skirt and tight knitted top that emphasized his artificial breasts. 'Joanne,' she said immediately as if it was settled. 'Joanne Revalt. Robert will never guess you were ever a man called Jon.' She smiled. 'Then I will introduce to him the idea you should have a place at Northwood as my companion.' 'Companion? Isn't that old-fashioned?' 'That's Robert for you. He'll like that idea: very European.' --- Northwood was European in style - or at least how someone had imagined European architecture should be: obvious gables and turrets, white shuttered windows, Greek columns at the front, medieval stone statues flanking the steps. Jon had only heard about it from Sandra's descriptions, and he was slightly overawed as he got out of the cab. He was nervous, as he expected, but Sandra said not to be. Someone was calling from the steps: Robert, calling to his wife, coming to greet her. 'Robert, darling. I'd like you to meet Joanne - Joanne Revalt. I told you about her.' Sandra stood aside, Joanne stepped forward, praying not to turn his ankle in these heels. 'Pleased to meet you,' said Robert, reaching for Joanne's hand. The nail polish looked bright in the late afternoon sunlight as he reached out towards Sandra's husband, remembering to grip softly, not as a man would. Robert was older than Joanne expected: Sandra had said her husband was older than her and Joanne had guessed that meant 45, but he was clearly nearer sixty. With his mane of white hair and a distinguished features he wasn't bad looking for an older man. Joanne thought: but I can see why Sandra would still prefer a younger man like me. 'Hello,' said Joanne, softly - the only way he could realistically simulate a woman's voice. Sandra had told him the pitch and level worked, and sales clerks like that teenage Kirsty had bought it. Robert smiled and turned back to his wife as if nothing was wrong. I've passed the test, Joanne thought with a gulp. For now. The man and wife began walking towards the house, clearly expecting Joanne to follow. For a moment Joanne felt an urge to jump back in the cab, but it moved off. Joanne had no choice but to follow the couple, walking as best he could in his unfamiliar heels on the gravel. Robert suddenly turned with an apologetic look on his face. 'Forgive me for not telling you of the terms of service - you must think me very careless.' Joanne, confused, could only mumble 'Of course not.' You'll have your own room, of course,' he said. 'And a uniform.' 'Uniform?' Joanne hesitated. 'I hope you don't mind, but my husband is quite romantic.' Sandra clutched her husband's arm affectionately. 'He likes the maid to be a proper maid. In uniform.' 'I can't... I mean, I didn't...' Joanne stared and then blushed, feeling helpless. This wasn't what he thought would happen. 'Oh I should have explained to you, darling.' Sandra smiled at her husband. 'Joanne's last employer allowed her to wear everyday clothes for her duties.' 'Really? How unusual. Well, I believe maids should look the part, don't you agree, Joanne?' Mutely, the cross-dressed male nodded as panic swirled in him. He tried to catch Sandra's eye but she was avoiding his, looking at her husband, saying: 'I'll show her to her room, darling - and make sure her uniform fits.' 'Good,' smiled the man, as if everything was settled. 'I look forward to seeing her at dinner.' --- 'What do you mean, maid?' Joanne was near to tears as Sandra closed the door to the small room at the top of the house. 'It was the only way I could truly get you into the house,' said the woman. 'I persuaded Robert to allow me to have a companion, but he suddenly decided against it. He said we should have a maid again - the last one left several months ago. So in desperation I told him I knew someone who was available.' 'But you didn't tell me!' Joanne sat heavily on the edge of the hard single bed. 'I didn't want to be a servant. If I'd known I wouldn't have done all this.' Sandra sat next to her lover, taking his well manicured hand in hers. 'There wasn't time to tell you. It was a very late decision. It was either this or drop the whole plan, and we'd gone too far to turn back.' She leant forward and kissed Joanne's full red lips gently. 'I knew you'd be shocked but I thought it would give us even more chance to be together.' 'How could it? I'll be... I'll be in some stupid maid's outfit up here on my own!' 'No, you'll be around the house all the time. Robert will be so used to seeing you and me together he won't question anything. He's a traditionalist anyway: he wouldn't dream of finding out about your background or never discusses womanly things with a maid. He'll ignore you more this way.' 'But, you said we'd be companions. We'd go shopping, have dinner, take in a show or two. Have a good time - that's what you said!' Sandra sighed. 'Be patient. I got you in here without him objecting, right? We can build on this. You'll prove yourself to be a good maid and Robert will trust you. I know he will. Then, after a few months we can -' 'Months? I have to stay like this for months?' Sandra continued as if there hadn't been an interruption from the cross-dressed man. '...He will be so used to you being here that when I suggest it would be great if the maid and I went out maybe to the mall, perhaps took in a show he won't say anything but sure, have a great time.' She paused. 'Plus, he will like the idea even more when I tell him he suggested it would be safer for me to be out with a woman. He'll believe that - thinking he thought of me having a chaperone.' 'I don't like it,' grumbled Jon. 'I thought I'd get here and we'd get straight on with sex.' Sandra looked cross. 'Do you really want to spoil it within ten minutes of arriving?' 'But it's been weeks since we had a good fuck,' objected the man. 'Don't you miss it?' 'Of course I do honey,' soothed the woman. She stood and straightened her skirt. 'But I'd miss it more if we ruined our chance. Trust me. We just have to bide our time, Joanne.' The woman's eyes twinkled as she said his female name and he felt himself color up. 'I don't like you calling me that,' he frowned. 'Can't you call me by my proper name while we are up here?' 'First of all,' said Sandra as she moved to the door, 'we can't afford a mistake. I have to force myself to call you Joanne all the time, so I don't slip up and second, I won't be coming up here again. This is your room. The lady of the house doesn't go to the servant's quarters. Your uniform is in the closet. Please present yourself in your maid's attire in one hour.' Before Jon could object, his lover was gone, leaving the man frustrated and angry. For ten minutes he sat in silence, fuming, wondering if this was the time to get out. The Jon in her decided she had to make a move. He got up and marched across the room and took out the black skirt and blouse hanging in the closet. For a split second he wanted to tear it up, throw it on the floor. But he didn't. It looked as if it would fit, he decided. --- The maid's uniform had a surprisingly long skirt. For some reason, Jon had expected one of those brief french Maid type outfits with a short flared skirt showing off a froth of white petticoat lace and, if he wasn't careful, his stocking tops. But this skirt was between knee and ankles and heavy, so it hung straight. The blouse - black like the skirt but in a satin fabric - buttoned up to his neck with a small, starched collar. There was no mop cap like the type of thing he'd seen in porno movies but there was a plain white, starched white apron tied at the waist and buttoned to the front of his blouse, just below his artificial bust. There was no high heels either as he had imagined. Just a pair of plain black women's shoes with a strap across the front a two inch block heel. He was however thankful as heels that were too high would have been impossible to work in. Work? Jon checked himself. Where the hell did that idea come from? He felt another wave of anger in him. This was, he concluded, ridiculous. For weeks - months - he had been dressing as a female in a bid to stay close to Sandra. Now he had the prospect of months dressed as a maid and worse still, having to work as one in sight of Sandra and knowing she wouldn't encourage him to even think they could have sex, let alone allow it. There wasn't much furniture in his room but they had provided him with a reasonable sized mirror that allowed him a limited view of himself. The cross-dressed man turned on his heels a couple of times and tugged the apron and blouse into place. He resigned himself to the idea that he would have to endure this unless (and a slow smile spread over his face as he thought it) he could persuade Sandra to at least lift his skirt and suck his cock. Yes, he was sure he could manage to get her to do that. Perhaps straight after dinner, when the old man was relaxing with a brandy elsewhere. Jon looked, as he expected, completely different to what he had worn coming over to Northwood. The uniform wasn't particularly flattering and if anything made him look like a middle-aged woman. There again, that probably was part of Sandra's plan: a plain, average looking woman was no threat at all to the Carter household. The sound of the large clock in the hall reminded him he was supposed to present himself downstairs and he hurried from his room, hastily pushing his hair into place with his fingers as he moved quickly down the stairs. --- The family had gathered in the living room and Jon knocked before opening the door. The family was there - or at least the man of the house, Sandra and a young woman barely out of her teens. 'You were told to be down in one hour,' said Sandra, a little icily. 'You are three minutes late. Please do not let it happen again.' 'Never mind,' said Robert, briskly. 'First day. We should make an allowance this time.' He paused and gestured to the young woman sat near him. 'The rest of my family will no doubt be stopping by but for now I'd like you to introduce you to my daughter, Kirsty.' Jon looked at the teenage girl for the first time since he entered the room and couldn't help but give a small gasp; it was the sales clerk from the mall, from when he and Sandra went shopping and he bought a blouse and skirt. Whether she recognized him however was unclear. She smiled in a friendly way but gave no sign she had seen the man before. 'Kirsty works in a store,' sighed Robert disapprovingly. 'Normally I would expect my children to enter the family business but I understand she wants for now to make her own way in the world.' 'Honey, it's good for her,' smiled Sandra before turning her attention back to Jon. 'Now, Joanne, please go and lay the table for dinner. There will be five of us dining - we three and Robert's son Stuart and his wife Marlena - and you may serve us when they arrive.' She waved her hand as if they no longer required the maid in the room. As Jon turned to go, he thought he saw Kirsty smirk at him. --- 'You didn't tell me,' Jon growled under his breath when for a few moments he managed to be alone with Sandra after the family had finished their meal and he had cleared the dining table. 'Tell you what? There is nothing to tell.' Sandra sounded imperious, even irritated that the maid should speak to her like that. Jon gripped the woman's arm but she shook it free. 'About her... Kirsty!' the man hissed. 'You didn't tell me who she was when we went to that clothes store!' Sandra waved the argument away. 'Oh that... Relax, she didn't recognize you.' 'How do you know? I think she did. She gave me these funny looks, while I was serving the food.' 'Hmm, perhaps. But she hasn't said anything and certainly won't to her father. In case you hadn't noticed they don't really like each other much.' Sandra turned to go. 'And if that's all, please go and get on with the dishes.' Jon glowered but said nothing. He was trapped and he knew it. 'Oh and one more thing,' said Sandra stiffly as she stood at the door. 'Try to remember Joanne that when you serve, you serve from the left hand side. It looks more professional.' 'Sandra...' began the man but she had gone. --- 'You think he knows?' Kirsty giggled as Sandra's hand slid between her legs. 'Course he does. And he's petrified, but frankly I don't care too much right now about the fucking maid,' grinned Sandra. 'Non-fucking maid,' chuckled Kirtsy. 'Dead right.' Sandra bent to the teenager and their lips met, a gentle kiss dissolving into full, tongue-in-mouth passion. When they broke, Sandra said: 'Just for the record, I've told him you and your father don't get on too well.' 'True. We don't... aaah!' gasped Kirsty as the older woman's fingers found her clit and pinched it. 'You like that, slut?' Sandra liked calling her step-daughter names - and Kirsty liked it too. 'You know I do,' whispered the girl. 'Are you gonna fuck me, mommy?' she added in her special mock-baby voice. 'Too right, cuntpiece, but first you have to lick my pussy and tell me how much you want to be fucked.' 'Yes, mommy dearest... aah!' --- Jon was surprised how easily he slotted into the maid routine. There was no doubt he looked the part and he had no doubt no one suspected underneath all this old fashioned maid's uniform he was anything but female. He was troubled by his submission, of course, and in some ways far more humiliated than he thought possible. But he did his duties as well as he could and even drew praise from Robert for all his efforts. Jon blushed - not at being praised, but at how he liked the old man praising him. There was even praise from Sandra at times, though she had turned out to be a hard task-master. If anything Robert was much kinder, more considerate, than his wife. The man seemed far more interested in Joanne that Sandra - or for that matter Kirsty - did. In some ways he enjoyed serving Robert. So much so, Jon had difficulty remembering he was doing this to be close to Sandra, especially as the woman appeared to have forgotten entirely they were ever lovers, that this was all her idea. Sometimes Joanne tried to catch Sandra's eye as the maid served meals but she rarely had her eyes on him. But at least the old man made the right appreciative noises and even grinned at the maid at times if she did something really well. He always saw Kirsty and Sandra together. They seemed close, sharing jokes and confidences, even in front of Robert, who ignored them as if he was glad his troublesome daughter had a friend he didn't have to worry about. But there were moments when Jon wondered: moments when he saw they seemed to be touching, or almost kissing as they whispered. On the few occasions Jon managed to speak to Sandra alone she was curt, even dismissive. If he mentioned that she had promised they would get an opportunity to be together she made some excuse about not arousing her husband's interest and suspicions, that so far they were managing to fool him but it still required constant application. They couldn't slacken, either of them. Jon didn't slacken. If anything he was working harder at being a maid than anything he'd ever done before. Away from the myriad of household chores Jon looked forward to the nights alone in his room at the top of the house when he could get out of the black maid's clothes and slip on something of his own - a bright blouse and a light skirt. He had, in the time he'd been at Northwood, forgotten what it was like to wear male clothes. Sandra had assured him his old things were safe in his apartment and one day she would bring something of his old clothes to wear in the privacy of his room, but she seemed to always forget or say she was too busy. Or that it would be terrible if Robert found them. Jon had long given up trying to argue with his former lover. He was faintly surprised he regarded her as that now but that was how it was. All he seemed to be living for was working as a maid in a large house, looking forward to dressing in his own, pretty female clothes when he finished at the end of each long, hard day. There was also the occasional bursts of pleasure from the anal dildo he still wore, and that made things worthwhile. That and being praised by Robert. In fact, it slowly dawned on Jon that the kindest person in the house wasn't Sandra (and certainly not Kirsty, who almost sneered at him when she saw the maid) but the man. Jon as Joanne began to work harder, be more attentive to Robert's orders, aim to try and please him and thus bask in any praise that he earned. Then, one evening, came a knock at the door of room. Jon had slipped, as he usually did after work, into his leisure clothes as he called them. This time a white lace bra and panty set and a light, satin skirt in red and brown and a soft, yellow flower patterned blouse. For a moment he wondered if Sandra had finally come to provide the sexual contact he longed for and he opened the door without asking who it was. After all, no one else had ever been up to his room. It wasn't Sandra. It was Robert. 'S... Sir,' stammered Jon, blushing at the sight of the man standing in the doorway. The old man had a bottle of wine in one hand and two glasses in the other. 'May I come in?' asked Robert. 'Why... yes, of course. I wasn't expecting anyone and I just got changed...' 'I can see that,' smiled Robert as he stepped into the room. 'Do you need me for any duties, Sir? I can get changed and be down in ten minutes.' 'Oh no,' said the man, setting down the glasses and the bottle on the small table. 'Nothing like that. This is a social visit.' 'Sir?' 'Relax, Joanne. There's no problem. I was hoping to have a little chat with you, make sure you're happy working at Northwood. I thought a little wine - nothing too expensive, alas - would help us forget our normal selves.' Jon blushed. May I say, Joanne, those colors really suit you.' The man gestured at Jon's outfit, making the cross-dressed man blush more. 'So much better than the black you have to wear each day.' 'But it's traditional, my maid's uniform. You like the uniform,' said Jon as he blushed at the praise. 'Indeed I do. A maid should be a maid. But when a maid is off duty, I am glad to see she has taste.' Robert winked at Jon as he uncorked the wine and started pouring. 'I also think a young lady should sit back and allow her boss to pamper her.' 'Pamper?' A sense of panic was filling Jon. 'Have someone else do something for you. Make you feel special.' Robert offered Jon a glass of wine. Hesitantly, he took it. 'Let us drink a toast,' said Robert, lifting his glass. 'To better understanding.' 'Understanding,' echoed Jon as he took a sip, puzzled what that meant. He felt foolish but for some reason wished he'd freshened his makeup. 'Now,' said the man, draining his glass and helping himself to another glass - and having encouraged Jon to do the same. 'Why don't we sit down and discuss what it is that makes us so attractive to each other.' Jon felt a wave of both revulsion and pleasure at the idea the man - a sixty year old man at that - should be drawn to him. But then, Jon was so convincing as a woman that the man no doubt thought that was what he was. 'Sir... Mr Carter, I like working here and I appreciate your kindnesses but I don't think we should be... well, doing this.' 'Why not?' laughed the older man. 'We both know what life's about, don't we?' Jon blushed, knowing what he was getting at. 'But you're married. Your wife is downstairs.' 'Sandra is out with Kirsty. Again,' said the man without rancor. 'They spend a lot of time together as you will have noticed.' 'Mother and daughter - well, step-mother and step-daughter,' began Jon, feeling the wine get to him. It might not have been the best vintage but it was certainly strong. 'Nonsense!' roared the man with a huge grin. 'They may be