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Mother and Son Peta Wilson The boy and his mother were working alongside one another as they often did. When it came to housework they thought of themselves as a team. She had encouraged their special relationship over the years. When he was younger he had been "Mommy's Little Helper" but at twelve he had grown into the second team member. And there were just the two of them. She had divorced the boy's father many years ago and once she had recovered from the shock and hurt his mother lavished her love and affection on the boy at the expense of any other potential suitors. There were some who, if they knew of it, said that the relationship was not healthy, that the boy should spend more time with other males, boys his own age and older men as well. But the boy and his mother did not miss older males and so far as other boys were concerned, the contact he had at school was sufficient to put him off. He unashamedly preferred the company of his mother. This afternoon, a Sunday, they were sorting items from the laundry hamper for washing. The boy passed a pretty white slip to his mother who placed it with the pile of whites already sitting in the washing machine. He followed with three pairs of panties. "These are pretty," he commented, unselfconsciously. "Aren't they? They're new." "Didn't think I'd seen them before." His mother's undergarments were not foreign to him. He had handled them in this fashion many times but he often saw his mother wearing them as well. Their special relationship was such that the mother had never had any qualms about her son, from a very early age, seeing her in a state of semi-undress. There was nothing to be ashamed of in the human body, she always said. In truth, in the past year or so, the boy was quite keen to see his mother in her underwear or, better still, if he could arrange it, nude. He made a habit of entering her bedroom in the mornings particualrly when he knew she would be dressing and his timing was usually pretty right. As boys often are he was interested and fascinated by the female form but in his case not just because it was sexy to see his mother this way but also because, well, there was an element of envy in his voyeurism. In fact, he often thought he would quite like to look like his mother. And it is true that, at thirty two, she was youthful and pretty. Much prettier than the mothers of other boys at his school whom he did not envy one bit. He didn't make it too obvious but he was quite often "around" when she was dressing or undressing. He had not felt inclined to say so but, something he could not explain, he was also interested in her clothes; that is to say to say he had a yen to wear these pretty things himself. And so, one could say, he was about to test the water. "Mom," he ventured at this point, "why is it that girls can wear soft, pretty things and boys get to wear boring old cotton and stuff?" "Actually I don't know honey. It's just some silly tradition I guess. But personally I don't see any reason why boys shouldn't wear such things if they want to." So encouraged, he pressed the point. "You never buy anything like this for me." He passed across a satin chemise top. "No you're right I don't. I guess I just buy the run of the mill conventional stuff. I'd never thought about it, tell you the truth." "They certainly feel nice. Nicer than my stuff." "I think you're hinting at something. Are you telling me you'd like to wear things like that?" "Hmmmm, maybe." "You don't mind the idea of wearing things that were meant for girls?" "Hmmm, no not really. It's not like someone else is going to see them." "Well then, if you're serious, maybe I'll get you some Boo-Boo." She placed the last of the whites into the washer and added laundry powder and switched it on. When the boy arrived home from school the next afternoon he went to the kitchen for milk and cookies as usual and took the glass and plate to his room to attack his brief homework. He had just about completed his work when his mother arrived home an hour later. He finished off and went down to greet her with the usual hug and kiss. "I have something for you," she said. "As promised." She passed him a small shopping carry bag and he delved into it and came up with three pairs of very feminine panties in white, pink and blue and three chemise tops in matching colours. "Oh wow," he exclaimed. "They're super." "I'm glad you like them," she said, with an amused voice. "Why don't you go and try them on for me?" He went off to his bedroom and stripped and chose to pull on the pink panties and chemise. Their softness against his skin was delicious and he immediately preferred them to his own underwear. His mother entered the room and he turned to show her. "They look nice," she said. "In fact you're very cute in them." "They're so soft and smooth feeling. I love them." "So you really don't mind wearing girly things?" "No one can see them except you and me." "No I know. They're the same size as mine. You're only an inch or two shorter. I thought they'd fit. Put the others in your drawer. I'll replace your other stuff for you over time if you prefer." He put the two sets into his underwear drawer and crossed the room and gave his mother and hug and kiss. "Thank you Mommy. I like them." "That's my pleasure darling. Now just put your dressing gown and slippers over the top and we'll go and make dinner." She left the room and he put on his woollen chequered pattern dressing gown and slippers and followed her down to the kitchen. The new underwear was so...so...wonderful. He liked it. He thought he might be brave enough to try a further suggestion. "This is what I mean see! This is the same," he said, displaying the dressing gown. "It's boring compared with yours." "Yes it is a bit drab looking isn't it? Is this another hint?" "Not...necessarily." "But you feel you would rather wear something like mine?" "Well it's much nicer than this isn't it?" "Undeniably. Would you like to borrow it then?" He looked at her beneath silken lashes. "Can I? Just for tonight?" She smiled, more to herself that to him. "If you want to. Sure. You know where it is." He went off to his mother's room where her white satin peignoir hung from the back of her door. He removed his own dressing gown and put on the other. He looked down at his feet in the ugly woollen slippers and kicked them off and replaced them with his mother's satin mules. They had a little heel. Then he returned to the kitchen. "Better?" she enquired. "Oh much. This is dreamy." "I see you're wearing the mules too?" He looked down at his feet. "Yes." She was, again, amused by his reaction and by the expression 'dreamy'. What's this all about? She wondered "Aren't you a little old to be playing dress-ups?" He colored a little. He felt she was trying to tease him. "I don't know," he said. He was examining the floor at his feet. "Would you wear it if I buy you one like it?" she said. Determinedly he looked her in the eye. "Yes." The next day he wore the pink set of underwear to school beneath his school clothes and when he arrived home his mother was already there and waiting with a very pale pink, satiny peignoir. It was knee length and very youthful and feminine. She had also bought a pair of pink satin mules not unlike her own and with a tiny heel. Showing absolutely no embarrassment, excitedly he raced off to his bedroom to try them on and returned to show them off. "Do you like them?" she asked. "Oh yes. It's sort of warm and cool at the same time. I love the way it swirls around my legs and it feels so nice to wear." "You know you look exactly like a girl in it. You don't mind that?" "Not just with you. Who cares? These things are much nicer to wear." She grinned. "Maybe I should be calling you Gail instead of Gary," she teased. He blushed furiously and she half expected him to object but instead he said: "If you want to. I don't mind." "You're quite pretty actually. If we did your hair differently..." She stopped herself. "I suppose now you've discovered girl's things you'd rather be sleeping in a nightie?" "I hadn't thought about it but if they feel like this, yes I would." Where is this going? she thought. She kept expecting him to rebel, to admit this was a whim, a joke, something. But in fact she could see no harm in it. He was not, she knew, you're average boy and probably that came from being entirely under feminine influence with only a female role model. But she was a liberal minded woman and, in truth, she thought she preferred him cast in her mould rather than in the prototype macho, masculine image she personally disliked. This attitude stemmed from her experiences with a super macho, hard drinking, occasionally violent domineering father whom she loathed and, later, from a not too dissimilar experience with the boy's father, whom she married young in order to escape her father, only to walk into an almost identical situation with her husband whom she had mis-read totally. When she caught him with another woman after only two years of marriage she divorced him and vowed it would have to be a very special man, indeed, before she took up with another. Another had not yet come into her life. So the "man" in her life was her son and if her son was growing up with a feminine streak, so be it. So given the circumstances she said: "I'll lend you one of mine tonight and you can see if you prefer it." She loaned him an ankle length pale pink satin nightgown and he far preferred it to his conventional pyjamas. So his mother bought him a range of nightgowns just like hers. When he came home from school he changed out of his school clothes, leaving just the panties on, and dressed in a nightie and his peignoir and satin slippers for the rest of the evening. Sitting at the meal table, or in front of the television doing his homework he was clearly not uncomfortable wearing these feminine things. And he looked so damn feminine she thought. His slim, straight body, nice legs, clear, soft skin, high cheekbones, fullish lips. He completely gave up wearing his regular clothes in the evenings after this and sat, sometimes, at the dressing table mirror in his room dressed this way and with his longish blonde hair falling to the nape of his neck he thought he did, perhaps, look quite like a girl and he found, increasingly, that he actually rather liked looking this way. Like a younger replica of his mother. Certainly he really did like what he was wearing. He also sat, quite often and dressed this way, on the floor in front of the television set, his mother alongside and when she wore short skirts which she often did, he allowed his fingers, apparently absent-mindedly, to gently caress the inner edge of her legs. For his part he wanted to be as close to her as possible; to smell her, feel her, to be a part of her. For her part she not mind this intimate proximity although at times his gently roving fingers distracted her and, in bed at nights, she had to relieve the sexual tension which clearly existed between them He raised the subject of his likeness to her once over dinner. "Mother do you think I look like you?" "Yes you do a bit. You have my features and hair colour." She smiled. "And specially when you're wearing your girly things. I must admit I sometimes have visions of you as my daughter. I would have enjoyed having a girl as well as you. I hope you're not offended by that." "No," he said, dreamily, "I'm glad I look like you. I think you're pretty." "Well thank you darling. I don't think most boys would like to look too much like their Mommies. But then you're not like most boys are you?" "I hope not. I'm not interested in what other boys are interested in." "What are you interested in by the way?" "I'm not sure really. I know I'm not much keen on sport and stuff. I like girls better than boys. I like reading and drama. And writing stories." She laughed lightly at this. "And you like girly clothes?" He blushed a pretty pink. "I like the things you've bought me to wear." "You're quite a pretty boy I must admit. Does this mean that you like to look pretty?" "Yes I think I do." "I thought we might be heading that way. I've been wondering since you started wearing girl's things, would you be interested in a little experiment?" "What sort of an experiment?" "Do you think you might like to wear other girly things?" "What sort of other girly things?" She was trying to sound casual but she was quite interested to see how he would react. "Oh a dress maybe, skirt and top, pantyhose, lipstick?" He laughed what sounded like a nervous little laugh. "I'd look like you then wouldn't I?" "A lot more like me I should think." "Would I look like a real girl?" "Oh yes I'm sure you would. I imagine you'd be very pretty as a girl." "A dress? And pantyhose like yours? And make-up?" She knew he was going to say yes. She knew he was just being coy. But he was clearly uncertain. "Would it...be alright?" Her asked. "I mean, you wouldn't mind?" "Darling you've been wearing girl's things for weeks. Why would I mind? I bought them for you." "You won't tell anyone?" "Of course not." "All girl's things? Your things?" "High heels even. A bra. We could do your hair. Just to see just how pretty you could be? We could have a whole dress-up day. Sunday if you like You could be my daughter for the day." "You're teasing me." "No I'm not. Really be Gail for the day. It would be fun." He blushed to his roots. "Yes I think I'd like that." For his part, he could hardly wait. She wondered for a while why she had made this suggestion. She thought, perhaps, that he would go this way anyway and she might as well be a party to it rather than take a pointless negative approach. Time, and circumstances, would tell, of course. And she really was interested to see how he would look. He was at breakfast on Sunday wearing his nightie and gown. She thought, again, he already looked very much like a girl. It wouldn't take much. She chose to try him out. "How's my girl this morning?" He blushed deeply but also smiled from beneath silken lashes. "I'm fine Mommy." "Looking forward to your first bra and heels?" "Yes I am," he replied, softly. "What a grown up young lady you'll be. After breakfast you go and take a nice hot shower and when you're dry sprinkle some of my talc over your body. Make you feel nice. And then put on your undies and come to my room." He padded down the hall in his satin slippers smelling vaguely of roses, wearing his pink panties and chemise. His mother was waiting. "Come and sit here at the dressing table. Back to the mirror." He did so and she went to work on his face. He had watched her doing it often enough so he knew what she was doing. Light foundation, blusher, eye shadow, mascara and, finally, lipstick. He felt kind of dreamy, like he was giving himself over to another person who resided within him. "Okay up you get," she said eventually. "Now we need to give you some boobies. Take off your chemise a moment." She fitted him with a pretty, lace lavished bra which seemed to have a shape all it's own. He did not know, yet, that she had bought it for him, the classic teenage training bra with it's own padding. "Put your chemise back on." He did so and she showed him how to roll a pair of sheer, flesh-toned pantyhose up his legs. He knew how to do it. He'd watched her often enough and wondered, more that once, how they would feel on his legs. When he had fitted them she said: "Lovely legs, Don't they feel nice?" He could only nod his agreement. She took out a pink, short skirted micro-fibre dress, with short sleeves and a scooped neckline and helped him into it. "Nice fit. Now sit down again a moment." She placed a pair of white high heels at his feet and he slipped his feet into them. She took up a brush and comb and teased his hair and brushed it. She placed a pair of small gold clip earrings onto his lobes and a single strand gold chain around his neck. "Just stand up a moment, honey." He stood, a little unsteadily in the heels. She stood back and appraised him. "My, my," she said. "I'm impressed. You are so lovely. And now you certainly look like my almost grown up girl. Take a look." He crossed the floor to the long mirror and stood before it. He took some deep breaths to stop his heart from beating so strongly. He allowed his eyes to roam over his body from ankles to head. "Oh Mommy," he breathed. "What do you think?" "You've made me so pretty." "I must admit I'd be proud to have you as my daughter. I'd love to be able to show you off." He stood there almost disbelieving. In his panties his twelve year old penis began to stiffen. It had happened before once or twice. He knew what it meant. They'd talked about sex. He was pleased it remained constrained by the firm fitting panties. For quite a few moments he just stood staring. "Turn around. Let's look at you again," she said, taking his hands and holding them out wide. "My word being a girl agrees with you I think. You're positively glowing." "Do I look like you now?" "Yes you do. Very much I think. I thought you'd be pretty but you're better than I had expected." "Do I..." he lowered his head coyly, "do I look like a real girl?" Pushing it she said: "Is that what you want to look like?" He hesitated a long moment. She said again: "Is that how you want to look?" "Yes," he said, very softly. "Like you." She put her arms around him. In the high heels he was only a little shorter. He leaned against her. "Yes you look exactly like a real girl. No one would ever know." They stood for a moment holding each other. She said: "I think I'm going to have trouble keeping you out of my wardrobe after this experience aren't I?" He moved back from her slightly. He has such pretty eyes, she thought. "Does that mean...I mean...is it alright if I...if I wear your clothes sometimes?" "It's important to you isn't it?" "Oh Mommy, I love what I look like, how I feel." "I think you'd just go behind my back if I said no. But I'm not going to. Yes you can wear my clothes sometimes" I wonder how often, she thought. "I kind of thought this might be coming when you started wearing panties and nighties." "Can I wear this dress all day?" "Sure if you want to." She figured this as confirmation of a suspicion. Maybe he was not yet a confirmed cross-dresser but, she surmised, he was well on the way. During the day she noted the number of times he sought a mirror, not obviously, but he could not pass one without taking at least a glance at himself. It was clear enough he was fascinated by his own feminine image. And he was clearly relaxed and happy. Almost without thinking she made some suggestions about walking in high heels, about movement generally and she realised she was actually encouraging him. In bed with her thoughts that night, with her son in the next room sleeping in a feminine nightgown and with the image of him in a dress and make-up still vivid in her mind, she resolved to help him, to be a part of his fantasy world, to see where it would lead. But at the same time she decided to let him take the initiative. He was, at first, a little reticent about asking if he could wear her clothes and satisfied himself with his own items of female attire. It was two weeks before he could bring himself to ask again "Mommy," he said over breakfast, looking very bashful, "can I wear your clothes again?" "Darling I said you could. You don't really have to ask. Just get yourself something to wear." "I don't know what to wear." "Well then I'll teach you." She helped him into one of her prettiest day dresses and heels and did his face and hair for him. The bashfullness disappeared as soon as he was completely dressed and he spent the day in a state of obvious blissful contentment. A week later, the same thing. Free Sundays became his days to be Gail, the name they just adopted without further discussion. Except for those Sundays when they had commitments - not very often - he would ask her permission to dress and she would assist him in his change of gender. Six weeks or so of such Sundays and he asked if she would teach him to do his own make-up and she spent a couple of hours instructing him on the basics. She also showed him how to do something a little more feminine with his hair but it was becoming clear he was never entirely happy with it. She thought about the idea of suggesting he try dressing a little more casually but it was apparent, with such relatively limited opportunities, he wanted to dress "up". He became quite proficient with high heels; he moved like a girl, used his hands expressively, and even began to sound like a girl in the way he spoke. When he was dressed, at least, it was like he became a different person. She commented about this once. "You're quite different when you're being Gail," she said. "Am I?" "Yes. More outgoing I think. It seems to make you happy." He stopped seeking permission to dress after about two months or so and just assumed his Gail role. It could not have been clearer that he enjoyed this activity and she pondered the situation from time to time, wondering where he was in his head, considering the possibilities and ramifications and wondering whether the influences were environmental or genetic or perhaps both. She thought she might be personally responsible for her son's feminine streak but she suffered no guilt. So be it, she thought. She was a pragmatic women. . When she woke up one morning to find him already in panties, bra, a garter belt and stockings and high heels and rummaging through her closet to find something to wear she resolved to take steps. On the following Monday evening when he arrived home from school she casually mentioned there was something up on his bed he might enjoy. He raced up to his room to find a dress, a pair of pantyhose, a pair of white high heeled shoes and a new bra lying there waiting for him. All new. Still with the tags on them. He stripped off and put on these delightful items which he had already assumed were for him to keep. He had just finished dressing when his mother entered the room. "Did you look on the dressing table?" she asked. He went to the dressing table and found a small lidded box which he opened to reveal a full make-up kit. "Save you using mine," she said. He immediately gave her a huge hug and a kiss and sat down to apply his new make-up. She stood watching and was aware he had already achieved quite a degree of expertise with things which should be unfamiliar to him. As he completed the task and began to brush up his hair she stood up and went to the wardrobe and took out a box. "Close your eyes," she said. He felt her fitting something to his head and when she finally allowed him to look he was wearing new hair, much longer than his own, below his shoulders in fact and styled in a completely feminine fashion. "It's a wig." She said. "Save you having to do your hair each time you change." He was a little breathless. "Oh Mommy it's beautiful." "Do you like the dress? "Oh yes." "I'll buy you some more as I can afford it. But darling there's a condition to all this." "What's that?" "We're not going to have you hiding away at home. I want to show off my pretty daughter. We going to start going out places." She had been thinking about this for some time. She was bored with spending Sundays at home just to satisfy his need to be a girl. She was also now convinced he would pass easily as a girl. Anywhere. There were things they could do together, places they could go. And when she was completely honest with herself she quickly came to terms with the fact that she actually did want to show off her "daughter". She liked Gail. She liked Gary too but as Gail, Gary was a very relaxed young individual, full of laughter and life whereas Gary was inclined to be tense and less spontaneous. She had, understandably, been observing her son very closely these past weeks. There was no doubting he preferred dressing as a girl. He had been most conscientious about learning make-up techniques and about selecting outfits to wear. He read fashion magazines. He cared for his nails which were longer than any boy had any right to wear them. He had tried really hard to find a way to wear his own hair which worked and although it was pretty hair she could not let him grow it, set it or wear in too girly a fashion because of school. But she watched his frustration with it with some pity. Which was what prompted the purchase of the wig. She did not know whether he wanted to be ae girl, which of course was impossible in the real sense, or just to look like one. But she felt it was becoming imperative that she knew. Or knew as much as she could. "Going out? As a girl?" "That's right." "Oh Mommy I'd love that. Can we really?" "We can and we will. Starting next weekend." This decision marked another turning point in their lives. This was a Monday night. He went down to assist his mother with the preparation of dinner dressed in his own female clothes with a new and very feminine long wig which had added a further dimension of realism to his appearance and wearing make-up applied by his own hand from a kit which resided on his own dressing table. And she had offered to take him out as a girl. Not too surprisingly he took this as an indication of approval, support and even encouragement. He could only assume - and he was right - that his mother liked him as a girl. "Poo to Sundays," he thought. When he arrived home from school the next day and immediately after greeting his mother, he went directly to his room and shed his male clothes and dressed in his outfit of female attire. She made no comment; threw up no barriers. He did the same on Wednesday night. She did not object. Thursday night. Friday night. First thing Saturday morning. At breakfast, she announced: "It's market day. We're going shopping. You're overdressed, honey." His heart raced. "What should I be wearing?" "We'll fix it after breakfast." Following the morning meal she offered him a pair of her jeans, white flats and a crisp white sleeveless blouse. "Put these on," she said. "It's what a girl would wear shopping with her Mom. You don't need the chemise." He dressed in these new items and appraised himself and knew immediately it was okay to dress like this. There was no doubt he still looked entirely like a girl. He liked the fact you could see his bra straps through the thin material of the blouse. It was soooo girlish. His mother came in with a small handbag he would wear from a long shoulder strap. "Put a lipstick and powder in here. It's enough. You're wearing a little too much make-up but it's okay this time." They left the house and strolled to the bus stop. His heart was racing and he couldn't figure out whether he was nervous or excited. Or both. Most probably. It was very clear almost immediately he was getting away with it. He hadn't really thought it would be a problem but here was the confirmation. No one looked twice. Just a pretty girl out with her pretty mother. They did the marketing and, the essentials done, she bought him a few things. Just trinkets really but the sort of things a twelve year old - almost thirteen year old - girl would have. A set of six thin gold plated bracelets which he chose to wear immediately. A little dress ring. A couple of pairs of inexpensive earrings. Two necklaces. Girly stuff. He loved it. Even more he loved the two casual tops and a cream skirt, two pairs of pantyhose and three additional padded bras. It was like collecting treasures. "Let's have lunch while we're out," she suggested. They retired to a small cafe and he ordered a ham and cheese sandwich in his own voice, without hesitation. It was an androgynous voice, his mother realised. But it will break soon enough. What will we do then? At home they unpacked their foodstuffs and he took his new goodies to his room and put them away. Back in the living room his mother said: "We have to talk." He sat opposite her in the wing chair. She picked up a booklet from the drawer in the dresser. "I want you to read this," she said. "It will only take about fifteen minutes. There's much more to it but it's a start." She handed him the booklet and he read the title. "A SHORT GUIDE TO CROSS-DRESSING, TRANSVESTISM AND TRANSSEXUALITY" by Amy Brennan. "Read. I'll make us some coffee." He read. And he learned he was not alone and that there was a name for what he was doing. One of them. His mother returned with two cups of steaming coffee. She sat opposite him again. "I'd like to ask you some questions, hon. And I'd like completely honest answers." "Okay," he nodded. "You're at the age of puberty, sweetheart. Are you getting erections...masturbating?" He looked shocked and blushed beneath the make-up and the long dark eye- lashes. "Mother!" "Come on. We can't have any secrets." He squirmed in the chair, lowered his eyes. "Yes." "Does dressing up turn you on?" "Yes." "Do you know if you are interested in girls or boys?" "I don't like boys much." "I mean sexually?" "Girls." "You know that for sure?" "Yes. I ....look at girls sometimes...you even... and....yes girls." "Me? I'm flattered." It was her turn to squirm for a moment. Her son looked at her sexually? My God! "New subject. Do you identify yourself in any of the descriptions in the book? He paused. "All of them to some extent." "Okay I think that's fair at your age. It's confusing I know. We'll have to wait. But you don't necessarily think you're transsexual?" "If that means...what it says here. No. I mean I don't what my...my..." "Penis?" "That....cut off." "I'd like us to meet with Amy Brennan." "Who's Amy Brennan? I mean I know she wrote the book but..." "Well for a start, despite her name she's not a woman. She's a male. A cross-dresser. In her middle forties." "How do you know her?" "I don't actually. Except for a brief conversation on the phone. She's a counsellor with an organisation called Chameleon. It's a self-help group for men who like to dress as women. I asked her is she would visit if we asked her and she said yes. That's her job." "You call her 'she'?" She laughed. "I call you 'she' don't I?" "I guess so. Gail mostly." "I think of you as 'she' then ?" "Do you?" "Yes mostly. I see enough of you as a 'she'. Specially this past week. More 'she' than 'he' ". "Sure I'd like to meet her." "Okay I'll ask her for dinner one evening. Want to go to a movie tonight?" "Sure." "Wear your pretty dress. We'll go into the city." Amy Brennan came to dinner the following Friday night. When his mother opened the door to her she was, for a moment, sure she - they - had made a mistake. Amy Brennan was about five feet eight, slim, immaculately dressed and groomed, younger looking than mid-forties and damned attractive. "Hello I'm Amy Brennan," the person at the door said, with a pleasant smile. The voice was husky but not deep, not necessarily masculine. For just an embarrassing moment she was speechless. "Oh...oh...sorry. I'm Linda Grant. Please come in." Amy Brennan followed her into the living room where her son stood up to greet the visitor. "This is....Gail," Linda Grant said. Gail was dressed in a short skirted pale blue sheath dress - one of Linda's - with almost white panty-hose and white one inch heels. Jewellery, make- up, hair, perfect for a thirteen year which he was about to be. Nails shaped and a pretty pale pink. Lips full in a shade darker. Eye lashes long and silky in dark mascara. Beneath the sheer pantyhose, legs smoothly shaved of fuzz for the first time. He was so authentically feminine Amy Brennan stopped in her tracks for a moment. "Hello," Gail said in a soft voice and caught Amy Brennan's eyes for the first time and, in their secret way, they knew each other. Amy Brennan was wearing a classic black dress, with a scoop neckline, short capped sleeves and a shortish skirt which showed off perfect legs in sheer black, feet in high heeled black pumps. Her light brown hair featured reddish highlights, and framed her face in a halo. Her face was made up in subdued, yet sexy manner and Linda thought, a little enviously, that she looked only a few years older than herself. "My gosh what a pretty girl Linda," Amy Brennan said, still smiling graciously. "You look lovely Gail." "Thank you," Gail said in his soft voice. Do I look lovely? Linda wondered, feeling somehow frumpy. She wasn't. She was wearing a green Thai silk dress, also with black hose and heels, her own blonde hair a natural version of Gail's wig. She was beautiful and Gail knew it and Amy Brennan knew it even if Linda didn't. She felt flustered. "Please...sit down. Can I get you something to drink?" "I'd love a gin and tonic." "Be right back," Linda said and left the room. Amy Brennan sat, smoothing the fitted skirt beneath her, sitting slightly forward in the wing chair. Gail sat opposite. "How's school Gail?" Amy Brennan enquired. "It's...okay." "Boys give you a hard time?" Gail stared at the visitor for a long moment. How did she know? "A bit. I don't....wear girl's clothes to school." "Oh I realise that. But they know something don't they those little thugs?" Gail lowered his eyes. "I guess so." "You're not like them. But that's okay. They won't be around to annoy you forever." "Did you have trouble at school?" Amy Brennan laughed softly. "Oh I've had trouble with everything. Until a few years back anyway. I think you are most fortunate Gail, with a Mom like yours." "I guess so." "Believe me." Linda returned to the room with three glasses and passed them around. "I was just saying Gail is very fortunate to have a mom like you." For reasons which made her feel very disconcerted, Linda averted her eyes. "Thank you," she said. She sipped her drink. "Dinner will be ready very soon," she remarked, realising immediately the pointlessness of the remark. "Sounds wonderful," Amy Brennan said. "In the meantime is there anything in particular you'd like to discuss?" "I think there are many things," Linda said. "But I'm not sure I know where to begin." "Shall I start the ball rolling?" "Please." "Well I think I should say to Gail that she's far from being alone. It is estimated there are well over a couple of million cross-dressers around the western world alone. It's not uncommon. But it's still a little difficult to deal with for some. In the first place working out who you is a bit of a challenge. And I mean who you are, not what you are. So at some time and as soon as possible you have to believe you are a human being with all the rights of any other human being in the world and that how you dress and how you feel and behave in terms of both your gender and your sexuality is no body's business but yours and, in due course, those who chose to be close to you." Linda realised Amy Brennan was addressing Gail but she thought Gail would be unlikely to contribute more than his ears at this time. "Is that difficult? Knowing who you are I mean?" "It can be. It is for most of us but I can assure you Gail has a huge advantage over about ninety nine per cent of us in having you." "So it was difficult for you?" "Very much so. I was closetted for years and hiding away then then I had to go through a divorce with a woman I once loved very much in order to find myself." "How long ago?" "Eight years." Linda wanted to stare and had to force herself to behave normally. She was trying to find signs of masculinity, manhood even , in this person sitting so comfortably in her living room, looking so much like a woman. An attractive, intelligent, vibrant woman. She glanced from time to time at her son, seeing a fellow traveller, wondering if he - she? - would look the same at forty plus. Amy went on to describe how she had been a childhood cross-dresser, sneaking her mother's and sister's clothes at every opportunity. And how she married with the honest thought it would all go away. And of purging expensive collections of clothes. And of a totally unaccepting wife. Gail and Linda listened, saying nothing. Linda found her heart going out to this fascinating creature, wondering why? Why a thousand things? A bell sounded from the kitchen. "Oh dinner," she said. "Gail would you take..." she hesitated. "Amy please." "...Amy through to the dining room?" "You look wonderful," Gail said when she had shown Amy to her seat at the table. "Thank you. Gosh though I wish I were your age and looking like you do." "Do you like girls or boys?" Amy smiled at the innocent frankness, knowing it was a valid question and probably one Gail was asking himself. "Girls. Women. I'm not gay in the sense that I am sexually interested in men. I am a lover of women and all things feminine." "I think that's me as well." "Very likely. But there's yet no need for you to be certain of that yet. There's plenty of time." Linda brought a white covered dish to the table and lifted the lid to reveal a steaming lasagne. "Oh gorgeous," Amy said. "I adore lasagne." There was much small talk throughout the meal with Amy leading mostly, putting mother and son at ease, being thoroughly charming. She ate artfully, like a woman, Linda observed, sipping the wine she served almost daintily. It came as something of a surprise to Linda to learn she lived as a woman. Fulltime. Name change and all. She was a computer programmer who worked from a home office but otherwise there were no constraints on her going wherever she pleased, being who she wanted to be. She had larger than average hands, Linda realised, but they were beautifully groomed, as was the rest of her. Her nails were lacquered in a color which matched her lipstick. An odd thing was that she made Linda feel competitive. When asked Linda offered that she worked in a small real estate office, as administrative manager. She gave some background to her unsuccessful marriage without going into detail. "Do you blame yourself for Gail?" Amy asked. Linda shrugged. "Not exactly blame. I don't see it as any kind of crime. But I suspect my influence has something to do with it. A feminine role model I suppose." "Yes I'd say you're right. Partly anyway. Environment is a contributor in many ways but there has to be a genetic factor as well. Gail may well have chosen this path with other environmental factors. She is I'm sure, if you'll excuse the bluntness, a feminine boy." Yes, Linda thought. Thank you. I've always known that. "I think I've just been letting her be, if you know what I mean?" "Yes I think I do. I think mother's identify things in their kids very early but some fight against it. Against nature even. It's not right, they think but they mean it's not socially acceptable." Gail said. "I like being a girl." "You're not really a girl darling," Linda said. "You know what I mean. Like a girl." They discussed their outings, Gail's comfort and pleasure at being able to pass so easily. Gail said: "I prefer girl's clothes. I'd like to be able to dress this way forever. Like you." "And you may well be able to do that with a Mom like yours. But there are hurdles to cross yet and in the meantime you will have to be content to live a dual life for a while yet." "I can do that I think," Gail said. More small talk while Linda cleared away. She came out with a bottle of dessert wine and a pot of coffee. "Honey," she addressed Gail. "I need to spend some time talking with Amy. Take yourself off to bed. Come and say goodnight when you're ready." Gail was obviously reluctant but left the table. Linda poured the wine and the coffee. She was silent for along moment. "Cat got your tongue?" Amy asked. "Not exactly. I must admit that despite my relationship with Gail I feel strangely disquieted by you." "In what way?" She hesitated, took a long sip of coffee. "I don't actually know. Not wary or anything. Not uncomfortable even." She paused. "I must beg you to forgive my forwardness but, well, I think I'm attracted to you." Now the silence was reversed. Amy Brennan stared at her coffee cup for some moments. "My God," she said, eventually. "What?" "If you knew how long I've waited, how I've longed for a woman like you to say that to me..." "A woman like me?" "A beautiful, intelligent, broad-minded, accepting woman like you." "Am I all of those things?" "Yes. Undeniably. Gail alone is proof of that." "She's...he's my son." "Yes and your daughter." "That too I guess." "I don't exactly know where Gail is heading Linda but if you can keep a tight rein on her for a while I have the feeling she is going to be a very happy young lady. There will be some difficult times but I'm sure you will work it out." They both sipped at their drinks, and their eyes met over the rim of the glasses. Gail came back into the room. He was wearing his peignoir and had removed his make-up but not the wig. Linda noticed he was also, apparently, still wearing his bra. He came to Linda's side of the table and leaned across and kissed her. "Goodnight Mommy," he said. "Goodnight darling." He went around to Amy's side and repeated the ritual, kissing her on the cheek. "Goodnight Amy. Thanks for telling me...stuff." "Goodnight Gail. It was lovely meeting you." When he had left the room Amy said: "She's beautiful." "Yes," Linda said and for a moment pondered the pronoun. "She is." There was another brief silence. Linda's heart was racing. "Would you like another drink?" "I'd love one thank you." Linda poured. For the second time their eyes met as they raised their glasses. Linda reached out her hand and placed it over Amy Brennan's. It was a compulsive gesture. She had not even thought abut doing it. "You're beautiful too." "Thank you," Amy said simply. "And I don't just mean the way you look." "Thank you again." There was another lengthy silence between them. "Amy?" Linda could hardly believe that she was about to do something she had never done before; never, ever dreamed of doing before. She stood up from the table and moved around to where Amy sat in anticipation. Linda leaned down and kissed her on the cheek, just as Gail had done. She reached down and took her hand. "I want to take you to bed," she whispered in Amy Brennan's ear. Amy slowly pushed away from the table and stood up. Linda led her from the room and along the hall and into the spare bedroom on the lower floor, furthest away from Gail's room. She closed the door behind them and moved in the dark to the bedside table and switched on the lamp and the room was suffused in a soft glow. She turned back to Amy and they embraced and kissed so gently it was little more than a brush of lips and then a little more firmly. Linda reached up behind Amy and slowly unzipped her dress. Amy allowed the dress to fall to the floor and Linda felt her step out of the shoes. Amy's arms were under Linda's, around her, holding her close. Linda could feel her...breasts...pressing against hers. She undid Amy's bra and let it come away and let out a tiny audible gasp as she realised Amy's breasts were not padding. Linda kicked off her shoes and now she was the shorter. She felt Amy's fingers undoing the buttons on the back of her dress and suddenly it was gone and she kicked it aside. Linda could feel Amy's breasts pressing against her bra. But breasts were not all she had. She could also feel Amy's male part, urgently hard, pressing against her. She reached down and placed her hands on Amy's firm bottom. She was wearing wide- legged panties and a garter belt and stockings and Linda was briefly and irrationally angry that she had worn pantyhose. At this point and rather suddenly Amy took the initiative. She eased Linda down onto the bed and lay alongside her and for the next...hours it seemed...she explored with her lips and her tongue and her finger tips, every inch, every nook and cranny, very crevice, every mound of her body. Linda felt as though she was on fire. She had never, never been so aroused. She felt Amy ease off the pantyhose, was aware of her positioning between her legs, felt her...penis...my God...at her entrance. She gasped as Amy entered her. Later they lay quietly. Linda was resting her head on Amy's shoulder, her fingers gently playing with a nipple. Amy's breasts, Linda realised, were larger then her own. Her clitoris, she giggled quietly at the thought, certainly was. She leaned down and flicked her tongue over the erect nipple. Amy stirred in response. "Amy?" she said, quietly. "Yes." "This is my moment of complete insanity. Please forgive me. I think I've fallen in love with you." "Yes," Amy said in her husky, throaty voice. "Me too." ***************** Three months after their first meeting Linda and Amy were married in a ceremony many would have thought bizarre. The celebrant was a senior member of Chameleon appropriately dressed in a navy suit, the skirt knee length, the calf heels high. Amy's attendant was a drop-dead gorgeous twenty two year old transitioning transsexual named Sally,a protege of Amy's whom she had also met at Chameleon. Sally was wearing a very pale pink Chanel style short skirted suit, with white stockings and white high heeled pumps. Identically dressed, alongside Linda and looking every day of five years older than her real age, as pretty a young woman as one could wish to see, was Linda's "daughter", Gail. The brides wore identical , ankle length white satin, deep fronted dresses, with balloon sleeves in the finest chiffon and caught at the sleeves and underneath, the sexiest basques one could imagine with six garters and white opera length sheer hose and pearlescent white heels. In the interim period since they had met Amy and Linda had done nothing other than confirm the love-at-first-sight scenario, because that, in fact, is what it was. It was as though they had been waiting for each other all their lives; for Linda a male who was elementally female, caring, sensitive, gentle with a love of the feminine and with an approach to sex which was, for her, as she herself put it when she finally had to admit to Gail what was going on, 'heaven on a stick'; for Amy, a woman who understood her, who appreciated and enjoyed her femininity, a woman who had a son who was treading the same path. Gail had no real idea of the sexual possibilites of the relationship but he knew that his mother was undeniably happier than he had ever seen her And he had no complaints. Amy was someone who knew where he was coming from and, very probably, where he was going. In a different way he loved her too. There was a bonus as well. In the time that Amy had been Alan and struggling his struggle had made him rich and although he had shared generously with his ex-wife, there was plenty left over and Linda and Gail suddenly had access to money they had never dreamed of. Gail's wardrobe increased seven fold in less that two months. Amy lavished gifts on him, a compensation, she readily admitted, for the deprivation she suffered as a child and specially as a teenager, which she agreed was the most important period in a girl's life. In this way, except for the difficult school period, Gail became a virtual girl. When the ceremony was over a strange but perhaps predestined situation occurred. Amy and Linda as wife and wife, although to all intents and purposes they were simply lesbian lovers, took off for Hawaii for a two week honeymoon. They left Gail who still had schooling to complete in the hands of Sally who moved into the house as a nanny. Sally, who was more promiscuous and adventuresome than Amy had imagined, introduced Gail to sex. Inevitably Gail was inquisitive about Sally. He knew she was "on hormones" but didn't understand what that meant. Sally explained. On their first night alone, while preparing for bed and dressed in nothing more than panties and bras, Gail was keen to see Sally's developing breasts and Sally was proud to show him her budding "bumps". Gail wanted to touch them and Sally let him. Her breasts were an erogenous zone and Gail handling them playfully turned Sally on. Although she was keen to be rid of it, her penis was still reactive and Gail could not avoid noticing the burgeoning erection in Sally's panties. Gail's penis was up too. He reached down and touched Sally's penis. Held it. Sally's eyes glazed and closed. She, in turn, closed her hand around Gail's penis and lightly stroked it. "Want me to do you?" Sally asked, breathlessly. "Wha...what do you mean?" "I'll show you." Sally dropped to her knees and took his cock from under his panties and put it in her mouth. Gail had never felt anything so heavenly in his life. Sally placed her hands around his buns and pulled him onto her and sucked and the inexperienced Gail exploded in seconds and was shocked that Sally did not pull away but swallowed him.. She let him go then and stood up and kissed him and he could taste his own salty sweet cum. "Do me," she said. An uncertain Gail went down on his knees and took Sally's erection into his mouth.. He sucked gently at first but Sally thrust at him and he worked more vigorously. She took a lot longer to come than he had and when she did he thought at first he was going to gag but the ejaculation didn't taste bad and he found he could swallow. "Nice," was all she said with a grin, when he stood up again. Gail was too overwhelmed to say anything. He turned aside and continued dressing for bed. "Let's sleep in your Mom's bed," Sally suggested. She had dressed in a short, white baby doll nightgown. Gail was unsure again but agreed and they went to his mother's room and turned down the bed and climbed in. Gail switched off the light. Sally snuggled against him. "Ever fucked a girl?" she asked. "No," he said. "You could start with me. Can you get it up again?" Gail was already "up again". He felt Sally reach for him and hold him. "You're cute," Sally said. "I can take you easily." She rolled onto her stomach and moved into a kneeling position. "Kneel up behind me," she instructed. Gail positioned himself. "Put it in me," Sally said. Trance like, Gail maneouvred his cock at the entrance to her body. She pushed back against him but he jammed there. "You're a bit dry. Wait." He felt Sally's hand on his cock and it was wet with...something. She moistened the tip and positioned him and pushed back against him and suddenly he was inside her. "Oh yes," he heard her say. "Nice. Fuck me, baby." Instinct took over then. He pushed deep inside her and it was...it was...magical. His whole body glowed with pleasure. He withdrew a little and thrust again and began immediately to develop a rhythm. He was lasting longer this time. In and out. In and out. She was helping him, pushing back against him. And moaning and sighing. "Oh that's so good," she said. "Oh yes," he heard himself say and then he knew he was close. Harder and deeper, as deep as he could go. He was coming. His eyes were closed, his head back and he was coming. And coming. When he was done he slowly withdrew and Sally collapsed flat on the bed. Gail lay beside her on his back. "Oh that was heaven," Sally said. Gail said nothing but lay staring into the darkness. After a few minutes something occurred to him and he slipped out of bed and padded into the en suite and washed his penis. He returned to be bed and Sally wrapped herself around him and he slept. It was light when he woke and he realised it was Sunday morning and that his mother and Amy were in Hawaii and that he was in his mother's bed and that...he was not alone. He reached out his hand and felt soft, warm skin and remembering what they had done just before sleep his became hard. He moved across the bed and snuggled against Sally and pressed into her back. She stirred and moved back against him. After a moment she said: "You're little tiger aren't you? You can do it from there if you want to. Just move down the bed a little." Still on his side he moved down and sought her entrance with his finger and positioned his cock. "Wet the tip with your spit, honey," she said. He did so and pressed hard against her and he felt himself slip easily inside. He heard a long, low moan. "Oh yes. Do it again." He fucked her again, thinking how perfectly he fit into her and how his body was glowing with heat and the tingle in his loins became a mountain of pleasure, no a volcano and he emptied into her in a spasm which rocked his whole being. He withdrew after a time and she rolled onto her back. "Honey you've made me hard. Could you do me please?" He knew what she meant this time and he slid down under covers and took her in his mouth and sucked her to vigorous orgasm. "Oh you're good," she said after a time. "Just think, we've got two whole weeks of this." He was indeed thinking exactly that. They went to a movie that afternoon. He dressed in a short skirt and high heels and overdid his make-up a little wanting to look older, sexier, like Sally did. In the theatre foyer boys ogled them and, for the first time, he wondered what it would be like to... That night he asked Sally. "You have to relax totally," she said. "Don't clam up on me or I can't get in there. Hmmm, that's it. Easy does it. Let me in, baby." He was trying to relax, trying to give her access but it was hurting. She was only about an inch in and he didn't think he could take it. "It hurts," he cried. "Wait." She dismounted and he watched her go to the en suite and open the cabinet over the vanity. "Ah ha," he heard her say. She came back to bed. "KY Jelly," she said. But he was none the wiser. But when she tried again she was much slipperier and she slid into him easily. It still hurt but not nearly so much. But it was not what he expected it to be based on her reaction. He preferred it the other way. When she had finished he told her so. "That's fine baby. We don't have to do it that way. I'm a girl/boy and you're boy/girl." "What does that mean?" "I'm a receiver and your a giver. You're more of a boy and I'm more of a girl." He was a little disappointed in this notion because he wanted to be a girl/girl; no boy at all. But he figured he might still learn. But in the meantime he would be happy just fucking Sally. And sucking her for that matter. So that's what he did. At least twice a day for the whole two weeks. As usual he was a girl all the time except for when he was at his hated school. He envied Sally that she could dress as a girl every day. In the mornings she went off to her job as a sales person in a dress shop and he went off to school. When he came home he rushed to get into a dress before she arrived home so she wouldn't see him as a boy. They went out a few times. Just to the movies or to MacDonalds or somewhere like that. He learned a lot from her. He dressed older and sexier while he was with her, knowing his mother would not approve. He learned to flirt with his eyes and body language. He copied her, worked at being just a girly as he could be. But in bed he remained the boy/girl and she remained the girl/boy. "Six more months and it will be off," she told him when he enquired about her little operation. "Then I'll have a cunt and maybe I'll let your fuck me there." He winced sometimes at her language. He wondered what it would be like to cut off his cock and couldn't imagine being without it. Specially now he'd learned to use it so well. "I don't know if I want to do that," he said. "Oh no, baby. Don't. You're a boy/girl like I said. Like Amy. Your mom wouldn't have married her if she was a girl/boy." He tried to imagine his mother and Amy fucking but couldn't get his head around it. And yet it would not be so different from him and Sally. "Your mom might have another baby," Sally said. He thought about this too. A baby with two mothers. He giggled about it. What if it was another boy who wanted to wear dresses. Maybe it was catching. He could certainly imagine why it might be. He thought about a household full of women. Sally could live with them. Amy, his mom, him and a little boy sister. How weird, he thought. He wondered it he wanted to marry a boy or a girl. A girl, he thought. They could have a baby too. A little boy daughter. He laughed out loud. "What's funny? Sally asked. He told her what he had been thinking and she laughed with him Then she took him to bed, wanting him inside her again. What if they had a baby, he thought, as he came deep inside her body. Amy and Linda returned looking tanned and fresh and happy. Sally stayed with them for another month while Amy arranged to sell her apartment and buy a new house so they could move out of Linda's rented apartment. Gail snuck into the spare room to sleep with Sally at every opportunity. To fuck with her anyway. Gail was conscious of the fact that Amy and his mother were very affectionate with each other. The touched often, kissed and fondled. Not trying to be obvious but not as subtle as they hoped. Once he padded along the hall late at night and stood at his mother's bedroom door. Listening he could hear soft noises which sounded like Sally. And himself for that matter. He eased the door open and in the half-light he could see them intertwined. Accustoming to the dim light he saw a body move into an upright position and saw the breasts, firm and jiggling. For a moment he thought it was his mother until he realised the hair color was wrong. Amy! He was immediately deeply envious. He realised his cock was hard and he was playing with it. He closed the door and went to the spare room and climbed in alongside Sally. Amy's breasts became a minor obsession. He wanted to see them up close and found ways of spying. When there was just his mother and himself he had seen hers often and not been discouraged. But Amy was different. For a start her breasts did not just grow there like Sally's. Amy wasn't "on hormones". There must be another way Gail decided. But he was hesitant to ask. Inevitably he was caught in his spying. He had been standing at the door which was ajar for only a few seconds, looking at the mirror which imaged the whole room when Linda saw him from the corner of her eye. "Come in, honey," she called. "You want something?" He pushed the door open and entered the room. His mother was dressed in a nightgown. Amy was sitting on the edge of the bed, in panties with a nighgown in her hands. She was bare topped. Gail goggled for a moment. "I...I was just coming to say goodnight." "That's sweet. But you don't normally do that. Why tonight?" He stumbled. "I....I was just..." "Wait," Amy interupted. "You just wanted to see what I look like didn't you? It's okay. That's understandable." "Well...I...." "Oh Gail stop it. It's okay. They're just like mine and you've seen them," Linda said. "I know...but...how..." "Come over here Gail." He crossed the room for a 'close up'. Amy cupped them in her hands and then went on to explain saline inserts and how they were implanted and she showed him the tiny scars in the folds beneath. "Did it hurt?" "No not at all." "They're beautiful." "Is it...is it possible...?" "In time honey," Linda said. "Wait. You're not old enough yet. I...we...were waiting to see if...well, I guess we know don't we. You want to live as a girl?" "Yes." "A few more years is all. As soon as we can. Now off you go to bed." When they moved house Sally moved into an apartment of her own. Gail visited with her sometimes. At the beginning of winter that year Sally had her operation. Three weeks later Gail was given his first opportunity see her new "equipment", as she described it. He decided immediately he was not having that done to him. But he was happy enough to make use of it when she offered. Not long after that Sally acquired a new boy-friend and Gail was not so welcome there anymore. He missed her. After he turned fourteen, Linda and Amy sought and received permission to take him out of his hated school on the grounds that he was going to a special school to learn computer sciences. Gail gave away his boy's school clothes with relish and was enrolled at the academy as a girl. By now he had a new role model. He would follow the lead of Amy and be, as Sally has so descriptively put it, a boy/girl. Linda and Amy did not have another baby. By the time she was sixteen Gail was five feet eight, willowy, her own hair a flowing golden mane. Her voice did break but she sounded no more like a man than Amy did, with a sort of rich, sexy huskiness. And all the girl inflections were there, of course. But she was still flat-chested. During her seventeenth year Amy made the arrangements for her and her padded A cup became an almost overflowing B cup. Boys were interested in her but she was not interested in boys. Unless they were boys like her, or like Amy or like Sally. She joined Chameleon and took a job as a programmer in Amy's small but flourishing company. She met and had sexual adventures with a number of the cross-gendered boys and men she met at Chameleon. When he was twenty four Gail met another "Sally" at Chameleon and they fell in love. Tracy was nineteen, small, rather delicate and with a mother like Linda, who had encouraged her in her gender preference from an early age. A very early age in fact. Tracy had an even greater advantage than Gail. She had been living as a girl since she was ten and had attended an all girl's school for five years. She had started on a hormone program when she was fifteen but no doctor would operate until she turned eighteen. Soon after her twentieth birthday Gail and Tracy were "married". Like Linda and Amy before them, they made a beautiful bridal pair. THE END