by WannabeGinger

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Chapter 11

When they returned from the restaurant, the previous night, Karen again slipped into a nightie of Jenny’s and they folded into eachothers’ arms and, after cuddling and some deeply satisfying kissing, slept immediately. Neither woman could face removing all their make-up, or rolling their hair for the morning. The result shocked Jenny when she awoke.

Looking at Karen, sleeping, and looking at herself in the mirror, Karen thought she’d been in an orgy of some kind. Hair everywhere, styles ruined. Make-up totally spoilt. They had to start from scratch.

Jenny decided not to wake Karen but to leave her a message.

She scrupulously cleansed her face and washed her hair — no time for a shower. The salon wouldn’t be busy as it was a Monday, so she would do her hair and make-up there.

Karen’s were a different matter; but she would have to try for herself. Jenny was already late to leave. She closed the door having left a message on the table:
 
 
Dearest Karen,

I hope you slept well! I certainly did. Thank you for a wonderful “yesterday”, I enjoyed every minute and finished totally breathless! You are one hell of a lover! Thank you! How DID I ever find you???!!!

Please, when you wake, use the whole morning to cleanse your skin and look after yourself. Have a shower and use any of the creams and lotions on my vanity unit that you need. After that, try to roll your own hair up in a pretty curly style. See how you do!

Then, while I go shopping - I took the cash from your wallet, by the way… Good that you carry quite enough! I’ve taken it all.. You won’t be needing it!

Yes, while I go shopping, you can have fun trying on some of the clothes in my wardrobe. Treat them with respect, but try on anything that you like the look of. Meanwhile, I’ll be buying you some lovely things to keep for yourself! Use your own underwear, but do expect me to come home with some unusual items in that department. I do so love nice undies on my lovers!

Lots of love and hugs,

Jenny xxx
 
 
Jenny thought about her new lover as she drove to work.

How could she make this relationship develop , and grow,… and last??? How could she liberate this man from a marriage that some would say had failed, some would say his dressing had ruined, and some would say could have lasted better if his wife had accepted his dressing as part of Andy? …. And loved him just the same as before she knew?

What Jenny didn’t know was what Andy was thinking, now he had woken up to find her gone. He lay in bed, still wearing one of her nighties. Still trying to feel girly, but really not succeeding. His thoughts rambled…….

Because of her relative lack of experience with cross-dressing among her clients at the salon, Jenny wasn’t aware that many marriages do survive and flourish where women accept that a husband’s dressing isn’t a criticism or a lack of love for her………

Quite the reverse, in many cases, Andy thought, it’s a mark of adoration from husband to wife that’s so strong, He wants to be She… like her……

There is a saying that most married cross-dressers frequently choose to look like their “other halves”……

They surreptitiously wear their wives’ clothes. Like I did……

They read their magazines, avidly. Like I do……

They wear their hair in similar styles, and often colours… Like I dreamt of……

They almost succeed in their efforts to be “their other halves” in more ways than one.

Some even choose their wives’ names for their own “femme” names.

Jenny didn’t know these things, but she did know that Andy’s marriage had been ‘on hold’ for a long time. He was embarrassed by his wife’s reaction to his dressing long ago. He felt he could never mention it, or broach the subject at all…. He had no way to prove to her that it was just another facet of his life, part of him…… that he hoped she could love him for…..

So, their thoughts were entwined, even though he was still in bed, and She was at work.

Andy realized that he had to get up, and get dressed….. and get cleaned up. He looked in the mirror and saw a tart that had been pulled through a hedge… backwards! A shower! He needed a shower! He slipped out of the nightie and stepped into the jet of water and felt better.
 

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Jenny had endured and endless morning — of boredom. He had dealt with a couple of “walk-in” clients whose needs were very ordinary and provided little satisfaction. Her one definite appointment had called to cancel with less than an hour’s notice, and so she was left with nothing to do. An ideal “closed until 2pm” opportunity for her to go shopping. She put just such a notice in the front window of the salon and locked the door.

Near enough to the salon, just three or four miles away, there had been a new out-of-town shopping area created, offering a large new Marks & Spencer’s and a Next store, alongside a Boots Pharmacy & Beauty store — which would be handy to buy the cosmetics Andy would need when transformed into Karen over the coming week, Karen thought to herself as she drove away from the pretty little salon.

Her journey took only a few minutes and she decided to choose the clothes for Karen “from the inside out”. She would buy some underwear and night clothes first, then choose between M&S and Next for the outerwear.

The underwear was easy to choose. The M&S selection was as good as ever — every conceivable size and colour. He would be a 38B in British sizing for the bras, of which she picked out two absolutely gorgeous ones; the first with burgundy satin and white lace, and the second with soft peach cotton. Both were ‘uplift’ styles with a slight padding and under-wiring, that would give Andy the tits her alter ego wanted. There were also pairs of clever little inserts made of silicone; not breast-forms but just enough to give tit-shaped outlines to whatever Karen would be wearing. Very pretty! Jenny chose matching knickers, three pairs to go with each bra.

After all, he’ll be wearing these for the future, I’m sure. Jenny thought to herself.

To these, she added a suspender belt for each, followed by a visit to the stockings display. Here, she found two pairs each of black sheer support stockings — to go with burgundy — and two pairs each of sheer ‘natural’ support stockings, to go with the peach coloured set.

He needs the shaping provided by the support stockings, sheer as they are….. and very sexy! Jenny smiled a long smile to herself. She was enjoying this!
Moving on quickly, as time wasn’t unlimited, Jenny found the nightwear and lingerie section of the store and chose a heavy-weight satin nightie and dressing gown set, not unlike her own, but in a distinctly pretty rose pink, The edges of the fabric were rolled in a darker pink shade. He’ll look good in these! Jenny thought II really think I could get used to shopping for him/her!

And so on to the Next store “next door”!
 

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Meanwhile, Karen was dressed at Jenny’s home. He had washed his hair in the shower and sat at the vanity mirror in Jenny’s bedroom, struggling with the rollers she had suggested he use to make a curly style…… It was no use. He failed miserably. The rollers wouldn’t stay in. The hair section he marked out weren’t straight. The back of his head he couldn’t see….. Disaster!

Andy gave up. His ‘Karen’ could do it, but he couldn’t…… His Jenny could do it… but he couldn’t…….. Better to dry it straight and have Jenny work her magic when she got home!

Let’s get on with the make-up! He was thinking like Karen again. She had removed his false eyelashes and chose to wear quite under-stated make-up after he had showered that morning. A little foundation. Lipstick, of course, but he found a “nearly naked” shade that looked good and tasted wonderful on Karen’s luscious lips. She admired her handiwork in the mirror..

He struggled with the mascara — he always did! — but avoided poking his eyes out. The look was just right…… He didn’t intend to open the door if visitors called, so it was for himself that Karen was dressed and made-up.

Karen now delved into Jenny’s underwear drawer, having first stepped into the bodyshaper that she had worn the previous day. The crotch was refastened, hiding her little cock once again. She wore again the bra and panties that had served so well yesterday. They might have been in place for some of the sex, but it wasn’t a problem to wear them again, as nothing was stained! Likewise, with the suspenders and stockings.

Having made her face up, Karen took for ages to choose between the dresses, skirts and blouses in Jenny’s wardrobe. She chose a very plain stay-at-home outfit which brought it home to her that girls do have to live without glamour some of the time. It was right. She would change again, this evening, to welcome Jenny home. But for now, it was ‘everyday’ gear. Andy’s mind was focused… on being Karen in mind as well as dress…….

She wore a beautiful sheer white cotton blouse that had embroidered flowers and scalloped sleeves. This went well with a tight pencil-line skirt in a shocking pink colour - shocking maybe, but it was a bright sunny day and Karen felt like “living just a little”! Her stockings were flesh toned and Andy found a pair of low-heeled slipped in leather that matched the skirt.

He stood and admired his choice of dress in Jenny’s full-length mirror in the bedroom. It all looked wonderful, except…..

Except, there are no tits! I want tits! There was nothing in the bra, so the blouse just seemed touching to Karen’s chest. The outline of the bra could be seen through the fabric… but there were no tits! No shape. He still felt, because of this, that he was looking at a bloke in a dress!

He stepped back to Jenny’s underwear drawer……. Nothing but rolled-up stockings would come close…….. and there were only new nylons in fresh undisturbed packaging there…….

“I must phone her……. “ Andy said out loud…..

But he didn’t know her mobile number……. He only had her number at the salon….. And she wouldn’t be there! “Bugger!” he said out loud, to whoever would listen.

It will have to be a handkerchief…… One for each tit……

Karen sat down with a coffee in the little lounge of Jenny’s cottage and thought back over the previous few hours and also over the salon visits that had led up to this weekend’s delights. How great it was that I had the courage to ask her to do my hair that first time….
 

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Back in the shopping precinct, Jenny decided to investigate what was on offer in the Next store, next door! There were some of the right things and a few purchases were easily made to get her started. A delightful floral print dress with an extremely tight, and hopefully flattering, waist Girly! Jenny giggled to herself as she moved on.

To this, she added several other items that would see Karen though her week’s confinement in Jenny’s home……. And on one or two ventures out! Jenny mused with herself.

She returned to the car with the dress, a neat dark blue A-line skirt with a wide belt that would help with training Karen’s waist, a blouse to match the skirt — in a pale, pale blue, with a high collar that would hide his Adam’s Apple……. (Yes, I had noticed!) she thought to herself….. And finally, a little frivolity… a chiffon blouse that was see-through and would look good on any tart! That would be for early evening s and would be followed by sex once it was removed! Jenny had plans in that direction! This is going to be one sexy week, for sure!

She stopped for a moment and again thought of the last few hours.

“I’ve fucked him, and he enjoyed that.” Jenny said under her breath, just to herself. “He’s fucked me, and I certainly enjoyed that!” Her thoughts ran away with her….. I’m going to seduce him, tease him and make him so excited that he’ll cum without control, just from what I say to him and what I make him do… to become her, Karen, my lover, again.

I’ll make her wait. Until, as they say, she’s gagging for it……. I’ll sit on her face and make her eat my pussy. I’ll stroke her panties but keep her locked inside the lace of these panties…… She will never want to leave me!

Jenny returned to the hair salon and spent the afternoon dreaming of what was to come. Time passes very slowly. The few clients she had were all uninteresting……. Nothing to imagine would suit her Karen. Not soon enough, five-thirty came around and it was time to close the salon. Jeny imagined Karen waiting for her, hopefully with make-up done, hair all set nice and curly, and dressed in something of hers… something sexy…..
 

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Karen was indeed waiting, but with her hair simply dried straight, awaiting Jenny’s touch…… She heard the car door slam when Jenny arrived. She went to the hallway and smoothed her clothes, pleased she had found shoes to match the pink skirt that she had chosen to go with the beautiful sheer white cotton blouse that had embroidered flowers and scalloped sleeves.

She looked at herself sideways in the hall mirror. Couldn’t be much better! Karen thought as the key entered the lock and the door opened. Pity the hair’s losing its colour….

“Oh, Wow!!” Jenny exclaimed as soon as she entered……. “You look stunning!.....”

“I wanted to look my best for you, honey!” he replied, trying his best to feminize his voice again.

“Well, you have succeeded, One Hundred Per Cent! I love the outfit you’ve chosen….. Just right to welcome someone home that you love and who loves you……
“I’m really sorry that my hair is such a mess…. I tried, I really did, but I made a real mess of the rollers and it didn’t seem worth it to carry on when you can do so much better….. So, please will you?.... Later? Or in the morning……?” Andy was gabbling now, his Karen voice lost for a moment.

“Hey, hey… don’t worry — that’s easy to put right…. I’ll give you the benefit of my curling tons before dinner….. How about that? Now twirly-whirl for me. I want to see how the skirt flares when you move!” Jenny said admiringly.

“Not until you kiss me hello!” Karen retorted. A beautiful, long, lingering kiss followed which made both of them fell quite light-headed. Andy was pleased that he hadn’t been excessive in his use of make-up. The resulting damage was limited and would be easily repaired while Jenny showered before dinner.

“You go change and I’ll make the Martinis.” Karen said, pushing Jenny towards the bedroom.

“You might have tidied up the clothes you didn’t choose!” called Jenny, thinking “Men!! You can’t get them to leave the bedroom tidy!” Some things never change and leopards don’t change their spots. Jenny was a little disappointed that the feminine time Karen had spent on her own hadn’t made him feel just a bit more girly in that sense. She would have to make him change his ways!, she thought.

The shower was wonderful on Jenny’s skin. The luxury bath crá¨me made her feel good and the water cascading through her hair equally so. She felt like a new woman….. And, luckily, I have one in the kitchen!, she thought, and laughed out loud.

“What’s so funny?” Karen shouted, hearing her laughs. Jenny smiled to herself again and said…. “I just thought I feel like a new woman…. And then I thought… You’ll do! You’re my new woman! You are!”, she said as she stepped out of the shower and surrounded herself with the biggest possible bath sheet, its toweling all soft and tumble dried, still warm from the rail.

“Cheeky!!” Karen replied, as she entered the bathroom and sat on the bath-side, watching Jenny dry herself. “Here, have a drink — you must be needing one.”

“Too right…” Jenny replied, taking the glass and at the same time, allowing her towel to fall to the floor, leaving herself naked. Inviting an approach.

“You do look fabulous, you really do….” said Jenny’s fully clothed lover. They both took deep swallows of their martinis and Karen felt an immediate warmth in her cheeks…. And also between her thighs. There was no bodyshaper there now. Just stockings and panties.

“There’s wine in the kitchen. Let’s order a pizza for delivery.” Jenny said with a glint in her eyes. “That way, we get to stay in and wait for it…….”
“Nice idea….” was Andy’s response to the idea. It will give us time for some fore-play.

“There’s still much more I want to know about you and your girly side…… So we can talk while the pizza’s coming and the wine’s going down…….. I’m not going to get dressed again — apart from some nice pretty undies and my dressing gown. Ok with you?” “And Ok for you to open the door to the pizza boy too”, she thought.

Jenny’s hands wrapped themselves around Karen’s waist as she drew herself closer to her. She offered her lips up to initiate a kiss she hoped would lead to more…. And sure enough, it did. Karen responded to the taste of Jenny’s lipstick and probed her mouth with her tongue. Soon enough, their embrace became quite ardent.

Incongruous though it was, Karen felt it was almost sexier with Jenny naked and she herself still fully clothed.
 

*          *          *
 
The sex they enjoyed for the next hour was “everything to everyone”. He was he, for once, she was she. Then he became she, and they were both ‘she’, Then she — the real she — became he. They role-played to extremes. He came on strong to her. Then she flirted with her, finally seducing her deliciously. Then, she remembered her toys, and took over control. By the time they paused for rest, Jenny had been tongue-fucked, fanny-fucked and allowed to give her lover a blow-job. Andy had fucked her missionary-style, then been treated like a girl and arse-fucked with Jenny’s dildo. Finally, Karen had been touching Jenny’s velvet and tasting the juices as she felt her lover cum while Jenny sat on her face.

The ice in the second Martinis had melted..

Karen had allowed Jenny to remove her ‘everyday’ clothes piece-by-piece, ending with her too being naked. With that, they decided to massage eachother with fragrant oils to rejuvenate their lust. It didn’t take long, but the night was yet young.

Jenny rose from the bed and said “We still have so much to talk about, my lover. Let’s have a break, another Martini and just lounge around for a while.”

Andy knew he needed a break and, in his Karen voice, seductively said “Whatever you choose my darling. I’m in your hands.”
 

*          *          *
 
As the Martinis continued to flow, Jenny thought it was time to find out some more about Karen’s history. I know about his early twenties, but not much more……

“You have to tell me about your life after Uni. I’m intrigued - you’re married, with a family and you got here somehow — tell me what led you to my door.”

Andy was thoughtful. As Karen, he was in this woman’s hands completely. Nothing he could do for her, he wouldn’t. She was in control. So, he was bound to answer….. but as Andy? Or as Karen?

“It depends who you’re asking…….. me, as Karen….???” Giving himself time to think. How far should the details go, if she presses for them?
“Oh, just for now, you’re Andy…” Jenny said, studying the face of this man laying naked beside her. She would dress him later in the clothes she had chosen for him….. for him to become “her” again. She wanted first to find out how his dressing had been submerged in everyday manhood… before it had emerged again in her salon, that day he came in……

Andy laid back and reflected. How had it been… before? He found it hard to recall….

And then there was the question of how much to reveal………… May as well be ALL!

“How far did we get? I guess towards the end of my Twenties…. And I was working as a Lecturer. And everyone seemed to accept me the way I was…….. I dressed for special occasions, for fun, and there were two very special ladies I loved very much at those times, who liked me to do that. So everything was easy. It was easy to get a liking for dressing. So, I carefully collected a wardrobe of clothes that were just right for different moods. I probably ended up with a better girly wardrobe than a male one. After all, what do College staff wear? Jeans, tee-shirts, sweat shirts and old jumpers. So what if your hair’s very long? Nobody seemed to care. So what if it was blonde sometimes, and red another? Nobody cared. In fact, it was my trademark and I enjoyed having the distinction……”

Andy paused. He recalled some of the instances where that was especially true.

There were the college ball events — at which he had routinely appeared in more and more exaggerated Diva costumes.

There were the private times when he had dressed for his own pleasure.

There were occasional forays into the night, when, in the days it was afe to do so, he could feel like a young woman with all the joys that brought.

There were times that female friends had suggested, in the days when “being gay” was almost becoming mandatory, that he might attract men when dressed the way he did. And certainly times when they were flabbergasted, and then intrigued, when he had made it very clear that he had no homosexual leanings at al…… he cross-dressed, for pleasure. That confused them...... “Aren’t you all gay?”, they had asked.

Over the next hour or so, Andy confided many of these things to Jenny, thereby helping her to understand more than she ever realized she didn’t know about cross-dressing and the men who do it. She was delighted that Andy felt able, seemingly, to let down all his defences.

She recognized that there was an inner softness and beauty in this man……. A man who, when dressed as a woman was evidently “different”…… but who was at ease with his “difference”.

Jenny herself chose the moment to break the conversation. She had spent the day thinking about these things and it was time for Karen to re-appear and for Jenny to indulge in trying on all the lovely clothes she had bought for her lover.

“I’m going to want you to keep these things here at my home, you know. I’m not going to let you go and they’ll help keep you coming back.”
Karen smiled and hugged Jenny’s neck.

“And when we’ve done, will you do my hair for tonight?”

“Of course, my love…..”

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THE END…………….. UNLESS READERS WANT THE STORY TO CONTINUE!