Pam and Rich were relaxing after Christmas, it had been a quiet affair, the kids had left years ago just returning for family gathering as they lived so far away, but most telling was the absence of Pam’s parents who had died during the year. So with the house back to its normal quiet state, they sat enjoying a mid morning break from the housework that follows a big visit.

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Pam looked at Rich with a different expression on her face to usual, ‘Fancy the sales this afternoon?’

‘Anything you have in mind’

‘No just go and have a look, thought you might like some new clothes, maybe try something different while it doesn’t cost full price’

They finished up and set off for town, it was while they sat having a snack before hitting the shops, Pam drifted off thinking if what she had in mind would work and whether it was a really good idea. Rich had told her before they married that he was a cross dresser, he enjoyed the feel of women’s clothes and borrowed his mother’s at times even sleeping in her nightie, she felt sure he was still interested in the feel of fabrics, but trusted him not to have been wearing her things, mostly because she was size 10 and he would be a 12. Losing her parents had made her realise how brief life is and why should Rich not explore things he wanted, also like with kids who want to do something you don’t approve off, once you encourage it the interest dies. She looked at him and looked at his smooth pink face, cute, she thought, even at 50.

‘Penny for your thoughts’

‘Just thinking where we should start’ Pam replied

‘So where?’

‘The Next store’

‘So we can spend more time in the women’s than the men’s’ Rich just gave her a smile

‘Well maybe, let’s see what they have in the men’s first’

After the short walk to the first shop they looked around the men’s floor, Rich looked at his usual jeans and shirts; Pam was looking for something more adventurous she first picked out cream linen trousers, she could see him feel the linen.

‘Feel nice don’t they, like mine,’ she gave him a sly wink ‘Try them on, see what you think?’

While he went to change she continued to look and found another pair in the ladies racks, he came out to say they were too long, and she passed him the new pair, these he came out wearing to see what she thought. They were tight around the hips but flowed loosely down the legs.

‘Do you like them? She asked

‘Bit tight here’ Rich said running his hands over his bum.

‘Yeh, but it makes them look good’

Rich was obviously feeling out of his depth and suggested looking around some more.

Next they had a look through the ladies, Pam not particularly looking for herself, but was looking at things that might look ok on Rich, plain blouses, plain jumpers and trousers.

Three stores later Pam has tried nothing on, but Rich has been striped at least five times, leather pants, cashmere jumpers and a shirt with sparkly silver thread running down it.

They ended back up at the first shop, he had a brown cashmere polo neck top and Pam wanted him to get the linen pants, so he agreed and tried them again. Luckily the assistant had not put them back in the ladies, so he changed into the size 12 cream trousers with his new top. The top was not his normal long baggy fit and with the tight hipped trousers he came out feeling self-conscious.

‘Gorgeous, I think we have found you a new look’

Rich leant close to Pam, ‘they are ladies pants, I’m not so sure’

‘I know and they fit you so well I don’t care, just let me go and pay for them’

While Rich dressed himself, Pam quickly went and paid for them. Rich rejoined her and walked back to the car quiet in his own thoughts trying to work out what Pam was thinking, she had never encouraged his earlier cross dressing and now she had bought him a ladies outfit, or near enough as made no difference if you knew and she most certainly did.

‘This is a different style, are you sure about it’ he asked once in the privacy of the car.

‘Yes, it suits you and I thought you might like the feel of them’

‘Well yes, they feel nice, but you are confusing me, I have tried hard get over my early interest in clothes, and now you buy me these’

‘Maybe I am having a change of view, and after seeing you in the outfit I can’t see anything wrong’ she then leant over and kissed his cheek and slid a hand down his leg.

He turned and smiled, then disappeared into his thoughts. When they got home, Pam asked him to change while she started the meal. He obliged and came down after a longer time than expected. Not just changed but washed and smelling of a sweet cologne, on closer examination she noticed there were no lines under the tight trousers. A hand over his arse confirmed this.

‘My underpants show’ Rich informed her as he blushed

‘Commando then?’

He blushed even deeper ‘borrowed one of you thongs, hope you don’t mind’

‘Very nice aren’t they, bit tight I guess’

‘Yes’ was all Rich could manage.

Things moved slowly after the big starting day. Rich would wear the polo neck, but the trousers he felt conspicuous wearing. Pam persuaded him to wear them both and go out with her, this felt easier and he was able to relax and enjoy the clothes. As they got ready for bed she asked if he would be wearing them more often, he had to accept he would have to if he was going to enjoy them. So by Easter he was wearing them as his preferred casual outfit. Pam had bought him a pair of control thong pants that left no lines and pushed his man bits out of sight.

Clearly he was comfortable, so when they were shopping for Pam he found himself looking out for items that might suit his style as well as Pam’s more girlie statement. It was when they were home he found they had bought some size 12 knickers.

‘We got the wrong size’

‘No we didn’t’ Pam said as she gave him a big grin, which made Rich blush.

They were a lovely silky fabric, and if he had been slow to take to the linen pants the knickers were an instant success, as they became regular underwear for him. Not confident to buy some more he asked Pam too, who took it one further and bought him cami tops as well to wear under his shirts. Which he unsurprisingly did.

‘I think we could go shopping again’ Pam suggested one weekend morning

‘Anything in mind?’

‘Well you need some more clothes, and I fancy a new skirt’

Rich thought about going in jeans and rugby shirt, but it did not last long and was soon in his ladies outfit and waiting for Pam.

Shopping can be hard work, especially when you are not sure what you are looking for. Pam found her white gypsy skirt, Rich found a pair of black trousers he liked the feel of, and Pam found him a soft cotton blouse they thought would look good under a jumper so the buttons were hidden. He also bought a pair of androgynous sandals, which meant when they got home and she suggested going out to eat, he could dress totally in women’s clothes.

Rich’s office job changed and he could work form home sometimes but when at work he was in a private cubicle, which meant he only really met the people he wanted too. This lead to his wearing the black trousers to work, which meant Pam, urged him to get another pair.

Still changes happened slowly, in the summer Pam was filing her nails and suggested Rich should take more care of his, and gave him a manicure, finishing him off with a matt coat of polish, she said to protect them.

The next big event in the coming out of Rich was his hair, it was never short, but would grow till it’s length annoyed him, and at the time it was the fringe but Pam kept asking him not to cut it and soon he could hold it behind his ears.

Talking of ears, he surprised her one day coming home with small gold studs in his lobes, and to his surprise, no one at work commented which made him bolder in his cross dressing, eventually wearing all his clothes to work.

Soon it was coming up to Christmas again and she wanted Rich to embrace far more of the dressing, not only did she like the new look, but it made Rich happier. So she suggested that after the kids had gone back to their homes she treat him to a few special treats.

But first they had Christmas to enjoy. Their daughter was curious about the uncut hair and studs, but she only saw the black trousers and never guessed their true gender. The son never noticed a thing.

As soon as they were gone Pam got out her extra presents, gold hoops and a satin blouse. He eagerly slipped them on, and then Pam came out with the first of her big surprises. The blouse did not fit well as the darts made it look odd without a womanly chest and presented him with her next gift, a padded bra. This he needed help with, not only being persuaded it was the right thing to do, but also with the fastener. Now back in his better fitting fitted blouse she dropped her biggest shock. After all those months of persuading him not to get his haircut, now she wanted him to have a trim.

‘Where on earth could I possibly get a cut at this time of year, and dressed like this?’

‘Oh that one is easy, you know Denise who does my hair, well I was telling her how long yours was and she offered to sort you out’

Rich had a worried look ‘You have made me an appointment, haven’t you’

‘Yes’

‘When?’

‘This morning’ Pam said with a smile, ‘You have the salon to yourself, she is supposed to be shut’

‘Well OK, just let me change’

‘No you look great, white shirt, black trousers, slip a coat on and I shall drive you there’ Pam could see he looked nervous, so with a gentle kiss as she swept her hand through his hair, she weakened his resistance. ‘Come on and enjoy yourself’

Rich surprised himself as he got up and meekly followed her.

Denise turned out to be Denis a stereotypical camp hairdresser which put Rich of his stride at first, but after he had talked about this and that to Pam for 5 minutes Rich was feeling a little more relaxed as Denis was running his comb around the hair.

‘So what do you fancy’

‘I have no idea really, usually it just gets trimmed when it annoys me, what do you suggest’

‘Well if it is up to me. Let me ask you, would you be up to using a gel or moose if I cut a style that needed a little help staying in place’

‘I guess not, is it hard to do?’

‘Oh no, you just rub it in as you are drying usually. So let’s get started, over here to wash your beautiful locks first’

As Denis worked they chatted, Denis about his clothes and where Rich could find some more, Rich talked about his clothes and Pam’s encouragement. Denis knew all about this and more it seemed, a stylist seems to be a confessor as well Rich commented, to which Denis gave a big gesture expressing how many tales he had heard from his ladies. Denis then let on that he had been unsure if Rich would turn up, and if he did what would he wear, Pam had said that the clothes Rich turned up in should determine the style. Rich suddenly realised that wearing a fitted satin blouse with a bra underneath, would mean only one thing; Denis would have cut his hair in a feminine style. As this fact sank in Denis unveiled the new Rich. His once shaggy hair was gone, a straighter style that curled under just off his shoulders and flicked across his forehead was most definitely not a man’s first choice, but it had been Denis’s. As Rich looked in the mirror thinking how he was going to face Pam and the world looking like this Denis broke in,

‘You are a cross dresser? Right, well make the most of it; get some heels and something nice to go with that divine blouse and I shall show you around the places you and I can be accepted’

Rich could hardly string words together.

‘I have to see a man about a dog in fifteen minutes, so I need to lock up, here’s my number if you fancy a night out give me a call’

With that Rich found himself outside feeling very conspicuous and strangely elated to be out dressed so femininely. Pam turned up as the door was being locked.

‘Look at you, Denis you are wonderful, how can I repay you?’

‘Just make sure he treats it right and comes back to me for a trim every now and then’ he said as he cheek kissed them both.

Pam turned to Rich as Denis walked away, ‘Now how does that feel, because it looks fantastic’

‘Not sure yet, Denis suggested I get some heels and something to go with the blouse’ Rich ventured

‘How about some make up as well, do the whole trip’ Pam looked at him for the unspoken hints, she could see he was unsure but had not dismissed it, otherwise why was he wearing such a neat bob and not freaking out.

Within an hour they had been to a shop Denis had suggested and come away with a cream vest top, a brown shrug, brown trousers with enormous bottoms and a pair of gold sandals with 2” heels which was just enough to lift the hem of the floor. Next Pam insisted he get some make up, nothing to brazen, he did not shave so light foundation, gold and browns for the eyes, and pink for his lips. Then it was home to check out what the bags contained. Soon Rich was washed and changed into his new outfit, with Pam giving him a quick make up lesson.

‘Ever thought of doing this as a kid?’ she asked

‘No, but I would be lying if I said the idea had not crossed my mind since’

As she moved away after doing the last stroke with the lip wand she opened her mouth but nothing came out. Eventually managing ‘Take a walk over there so I can get a full view’ he moved away ‘Stunning, you are not male you know, we have created a beautiful woman’ She left Rich looking in the mirror trying to work out where his masculinity had gone because all he could see was a well dressed female.

‘Denis says he will meet us at eight in town and show us around’

‘Why have you done that, I cant go out, people will laugh, I only want to feel the clothes’ he rambled on with excuses till Pam stopped him.

‘Shut up and listen. This has taken both of us a lot of effort, you look great, let’s not waste it sitting indoors, Denis knows some great places, how about we drop all our inhibitions and just go and doing something totally out of character’

‘And me dressed like this is normal?’ Rich tried to come back with.

‘Besides I fancy a night out, and I like Denis. Now find that gold clutch bag, there is a pashmina in my drawer you can borrow, then go and call Denis to tell him you are coming as well’

The evening went well, Denis had his partner a well dressed man called John, Denis was even camper than before and wearing a pink shirt with white trousers stood out more than Rich who was looking like a woman through and through.

John and Denis showed them around the bars they used, meeting other friends with kisses sometimes more intimate than one would expect from hetero friends. Denis was a perfect girl for John’s man, but when Denis went off chatting with a friend and Pam was chatting to a newfound friend, John leant over to Rich and confided that he wished Denis would dress like him. Rich had never thought of himself as attractive before, but John was obviously flirting with him, and to Rich it felt great. As the night wore on, Denis suggested a club, as he wanted to dance, John didn’t but smiled and led the way. Another gin and Rich was finding heels were not so bad to dance in, and as men came to ask Pam for a dance which she accepted, Rich would find himself dancing with John or Denis, sometimes even a stranger. In the early hours the DJ finished with some slow songs, John and Denis found each other, Pam had been dancing with particularly well-toned man who just continued to dance with her getting closer with each move. Rich was about to leave and get a drink when a man caught his arm and asked for a dance, the grip made Rich think it would be easier to say yes, so he did, the partner soon had his hands around the waist and pulling them together, the man’s erection easily felt on his hips, then he found his lips being kissed and a tongue finding it’s way in. it was a most wonderful dance and his first as a woman, well sort of.

An hour later Pam and Rich are home and cleaning off their make up. Pam has one last gift, a silk nightie for Rich to sleep in. It was not until the morning that they have slept and got over the alcohol, and are able to consider what happened the night before.

Rich spends ages trying to work out how to get his hair looking good as he happily sits in a bra knickers and cami. Pam eventually wakes and comes to his rescue showing him how to use the moose, dryer and brush. Then she helps him redo his make up, gets him to wear the satin blouse outfit before asking how he felt about the evening. Rich said he was not happy with her being so intimate with other men, but her come back was the observations of Rich’s slow dance and how he was fighting the man off. They finished saying they would definitely be out again, neither sure how to say, as soon as possible please.

The next couple of days are spent immersing Rich in femininity, Pam shows him how to pluck his eyebrows, do his own make up and after all that time keeping his nails neat she buys a set of false nails which she insists must be a deep pink, Rich does not object as he is enjoying his Christmas break too much.

Rich knew it would come, two days after going to the salon he is fully dressed and Pam suggests shopping. Rich knew it would be for him, what he did not know was what they would be shopping for. After a long shop they arrived home with plenty of bags and even more clothes. He now had a day outfit of wrap over top, double layer skirt and boots, a figure hugging short dress Pam said would be great for going out at night in with stiletto sandals. Along with several pieces of jewellery, make up and what he considered sexy underwear. Rich was not aware but Denis and Pam were setting him up, each for their own reasons.

So when he got a call from Denis asking him out he suspected nothing. Pam suggested the dress, so he dressed in his new stockings, dress and best jewellery, then having practised in the high heels took them for their maiden outing.

John and Denis were waiting at a table in a smart bar for Pam and Rich with a bottle of ‘champagne’ which slipped down far to easily, then as they moved onto another bar Rich stumbled and was caught by John who offered his arm just in case it happened again. The evening went well, Pam and Denis kept on disappearing, then when they got to a club with a dance floor, Pam was of with the first man that looked at her and John asked Rich for a dance which he accepted. Rich noticed that Denis and Pam though around were not sitting with them, and as another bottle of wine emptied he realised he was alone with John, who finished the evening with a few slow dances which included intimated touching and kissing. John only lived close and as Pam had gone of with Denis, the offer of his flat seemed very attractive.

Once behind closed doors, John repeated how much he liked Rich and the fact he was a man who looked like a beautiful woman turned him on. Rich was unaware of where this was going but was certainly enjoying the way he was being treated. When John slid the zip down the back of the dress revealing Rich’s lacy black bra, thong and suspenders, still on his heels John pointed out how sexy he was, Rich was now completely spell bound. John explained how he knew it was his first time and he would be gentle with him.

And so Rich lost his virginity, to his complete surprise when he got up in the morning he found a bag with his other skirt and all the make up he would need in it. There being no alternative he dressed, John told him how much he had enjoyed the night and would be happy to repeat it anytime he wanted. But Rich was interested in why the bag was there and what had Pam been up to.

He turned up at his own front door looking very attractive, Pam was sitting reading and obviously waiting for him.

‘So, how the bag get there, I am guessing you had some hand in this’

‘Sit down and calm down’ Pam started ‘Did you enjoy yourself? Was it terrible? Would you fancy doing it again?’

‘What?’ Rich was confused.

Pam explained how since Rich had not been able to get a proper erection for ages she thought about the alternatives, and this was one of them, he could have sex without the need for an erection, he would just enjoy the pleasure.

‘It is painful you know’

‘But did you come?’

‘Well yes’ he admitted

‘So there you are, you can enjoy your cross dressing and a bit more’ Pam said with a smile.

‘But what about you?’

‘Don’t worry about me, if you can play away to get what I can’t provide, then so shall I.’ she said with a cheeky grin spreading across her face, adding ‘I still love you, that is why I have been prepared to do this for you’