They laid together, gently fondling eachother’s skin, and underwear, and hair……. Heaven!

Neither said a word, for a while. Each was conscious of the other’s breathing.

Their thoughts were similar, coming from different angles.

Jenny thought…….. How has this delightful man kept his secret so long… and not shared it the way he can obviously do so, so generously. He had given everything to her in their love-making. Asking nothing in return. She had willingly given him what he clearly wanted deep down…. But his was the giving side……… What a wonderful fuck……….

Andy’s thoughts ran in parallel……. “How lucky I am to have found a lover for Karen…… Just by little encouragements, she’s set me free of all the inhibitions that I’ve carried for years… and kept secret for years……. She’s so good at sex it’s incredible….. and she let me act the girl inside me….

“Martini?” said Jenny, indicating that the love-making wasn’t over, merely paused…….

“Shaken, not stirred….please!” replied Karen in her increasingly sexy voice.

Jenny stepped out to the kitchen and found the fridge, cupping a handful of ice for each glass and pouring a generous measure into each of two glasses. Then she had another thought….

She took another handful of ice cubes with her as she left for the bedroom.

“Close your eyes……… Your beautiful blue eyes…” she said to Karen.

Andy obediently closed his eyes.

The shock of the ice cubes that were suddenly upon her inside legs, between panties and stocking tops, was high voltage. Her suspenders quivered as she convulsed, first in shock, secondly in laughter……. “You minx!!!” Andy shouted, very much in his boy’s voice…….

Jenny was quick enough to move the ice into his groin where his bollocks hung behind his half-hard cock. More shock treatment! The effect was excruciating… but irresistible……..
He wanted more of the same! Jenny had judged him well…….. His cock hardened. He grabbed the Martini and drunk it back in one swallow, the lipstick now missing from his lips, leaving the empty glass unmarked.

Jenny sipped her Martini with a coy, flirtatious smile…… And waited.

Andy, dressed in heels, stockings, suspenders, panties and bra, with a bodyshaper underneath looked incredibly sexy.

His cock betrayed his gender and his intentions. — to fuck another time, this time even more playfully. He pulled Jenny up from the bed so suddenly, that her hair flew in his face and their mouths joined instantly.

“Mmmmmmmmmmmm………………!!!” they gurgled in unison.

Her wet hands grasped the nape of his neck, her cold palms sending further shivers down Andy’s spine. That ice!! he thought……. I’ll get my own back for that!

There was no Karen about him for more than a few moments. Now, he was a guy with his cock ready for fucking…….. And his lover was all ready! That he wore gorgeous feminine clothes served to heighten his excitement.

“Stop!” Jenny said, breaking loose…… “You have no lipstick left!”

“See if I care…..” said Andy.

“Well, I do care…. Go and get some…. Andy put loads of it on, yourself! Do it now!”

Jenny resumed commanding form…… but not for long. Andy did as he was bidden, and returned with fully laden lips in a beautiful plumy-red — no gloss, just wonderful colour.

“There, satisfied?......” he asked.

“Not yet, and no chance of being so…. Yet………. I want you… NOW!” Jenny growled.

“Then you have to do the same… NOW.” Andy commanded…… Or was it Karen?

Jenny did the same and hurried back into the bedroom. Their lips met and their hands clawed at eachothers’ undies……. Andy placed lipsticky kisses on both Jenny’s nipples and squeezed her tits so hard she squealed. In return, she grabbed his bollocks and held them ……. Gently at first, but threateningly……. She could squeeze much harder if she wanted…….

But she didn’t. The threat was enough. For her to feel in control.

“Now, fuck me…….” Jenny implored him/her.

Andy pushed his cock between his own legs — to hide it briefly — and slowly forced Jenny back onto the bed. He splayed her legs apart and sunk his lipstick-laden mouth onto her pussy, to make sure she would be wet ….. wet enough for a full entry when the time came. But the time wasn’t then…. Before that, inside his head, he became Karen again and rose up to kiss Jenny fully on the lips, allowing her body to connect directly, pussy-to-pussy.

Their pelvic movements soon felt into a glorious rhythm and Jenny’s clitoris proved to be the fulcrum on which the rhythm rested.

Soon, she was losing control and, with two previous orgasms to drive her higher, Jenny went into what she called “another place”… a place where ecstasy is universal. She shook her head from side to side, her curly hair flying in all directions.

Karen’s cock soon emerged. The time was right and there would be no going back……. She knew.

She now knew as much as she needed to about her own sexuality.. and about Jenny’s too. Jenny wanted to be fucked by a woman. Karen’s cock fitted easily into Jenny’s clutching hands and, as she guided it into her pussy, Jenny said, “Darling, just don’t stop.. don’t ever stop….!”

The two women fucked for it seemed like ages. First, Karen was on top. Before long, Jenny swung a leg sideways and over Karen’s thigh, twisting sufficiently quickly to over-turn her lover onto the bed. His cock was hard enough to climb onto — and to ride with passion.

Karen laid back with his cock nearing exhaustion but loving every minute. Jenny grabbed her hands and forced them to the pillows, where Karen’s hair now lay in a mass of tangled curls and extensions. All dark auburn and blonde. Jenny kissed her again, deeply this time.

Andy was overcome with heat. He wanted out of that bodyshaper ……now… it had served its purpose. To do that, his bra, slip and panties had to go…… He could keep on the stockings, suspenders and heels.

This required getting up from the bed. It didn’t take long. So there he was, soon after, not having cum again yet, but dressed only in stockings, suspenders and heels.

I’m getting the hang of these now — he thought of how difficult the heels had been to wear at first. Not now — they’re deliciously female and sexy, especially with the stockings so sheer and clingy….

Jenny looked up at him and realised that there was a time for everything — and a time to pause was now….. Their dress, hair and make-up was all now in total disarray…….

“Another Martini?” she said, as provocatively as she knew how.

************

The dawn was breaking as Andy woke, finding Jenny nestled in his arms.

He lay there on the bed, pulling the duvet up around his chest.

He was naked.

Ah! He remembered. Jenny had finally undressed him, removing his stockings and suspenders. His bra had long since disappeared and Jenny had reached out for the lipstick that was on the little table beside the bed.

She had carefully traced circles of deep red colour around his nipples.

Then she had chewed then for what had seemed like ages.

He felt his cock stirring again at the thought. It never did that, just on a thought,

……… never once in the previous ten years. Sex had become so repetitive, what passed for sex between him and his wife, that was. Never…… But he had never dressed as a woman in bed before. Never shard his love of dressing….. Jenny had set him free. He thought…. Never to be locked away again.

“Jenny……. Jenny………. Mmmmmmmmmmm……” he whisperered to himself.

She stirred, but didn’t wake.

He put his free hand on his nipple and squeezed. His tits had never been sensitive like this before.

In fact, they had been almost painful. Never before had they played a part in foreplay.

Elation. Pure elation!

Karen was nowhere to be seen at that moment. He was Andy. He was a guy cradling his lover in his arms. This beautiful woman. How good could it get — not much better than this, that’s for sure!

************

Jenny’s slumbers were disturbed by movement in the bedroom…..

Andy had returned having showered and made breakfast of what he could find in her kitchen…. Oh-Jay, toast and honey, coffee — decaff and black…….

She opened her eyes and saw him, standing over the bed. This complicated and vulnerable man… He had unpinned the hairpiece and so was short-haired for a change, his dark red hair glinting in the sun that shone through the window. He was naked apart from her satin dressing gown.

“Nothing else to wear!” he smiled.

Come here and let me feel……..” Jenny reached for him, her hand slipping between the soft folds of the gown. “I’m pleased to feel it!”, she said. Her hand took his cock gently into her grasp, tugging slightly…. To which there was an obvious and immediate response.

“Thank you for all of that!”, she whispered…… “All of that wonderful fucking…”

“It’s me who can’t say thank you enough, you wonderful, wonderful woman.” Andy replied.

She wanked him slowly and seductively, her eyes never leaving his.

“You do realize that you’re not finished, don’t you…. I mean, we have a week together……” Jenny meant business. A plan was evolving in her mind…… “A week here with me in my home, you’ll never forget……. I have to go to work during the daytimes….. But you don’t. You have to stay here………” She paused to let his imagination catch up with what she was saying…….

“You have no clothes with you — apart from those you arrived at the salon wearing….. and very girly you looked too…… But you have no other clothes……. How lucky!”

Andy could hold himself back no longer. Quietly and with total abandon, he felt himself cum in Jenny’s hand. His breathing was shallow, as she spread his cum all over his face and kissed him.
She ruined what make-up there was left o his face…. But he didn’t care!

************

“Nothing to wear……. Yes, you did come to the salon dressed, didn’t you? That was quite a step I should think….. Did it feel good?” Jenny probed his feelings as they sat together over a coffee in the kitchen, an hour or so later.

“Not really…… It was knowing I was coming to see you that made me feel good…..”

“Oh, come on, you’re not serious…. Dressed as a girl…. Walking to your car…. Driving there….
Sitting in the car, getting out of the car in full view of anybody…. Coming into the salon, just like any female client I have…….. And it didn’t feel good???!!”

Andy paused and thought…… Perhaps now was the time to explain……

“No, no, you misunderstand…… It felt good, because I was coming to your salon — and to see you…. Not because I was going out dressed……… That’s not where the buzz comes from… for me…. Not being out there, trying to pass myself off as a woman….. It’s the getting dressed and the having my hair done, and doing the make-up……. And it’s sharing al that with someone who’s kind enough to indulge me….”

“You’re kidding me….. You mean you don’t get kicks from looking like a girl for other people to see you…..? You must want to be accepted as a woman, surely?” Jenny was puzzled.

“Well, I’m realistic enough to know that I’m not pretty enough….. I’ll always look like a bloke in a dress, but that doesn’t stop me loving the doing of it — the dressing, the make-up and the hair-styling I love cross-dressing…… I don’t want to attract men and get fucked…… I want to love and be loved by a woman — a woman like you, Jenny — like you!” Andy’s heart was pouring out.

“Hey, take a deep breath…… It’s all ok… really it is……. You seem worried now… when you weren’t just a few minutes ago…… Just take it easy…… I wasn’t putting pressure on you about passing as a woman….. It’s right it should be how you want it to be….” Jenny was back-tracking.

Just a bit

She went on: “…….tell me how you started. How it came to you that you’d feel this way…”

Andy was thoughtful for a moment, regaining composure a little……. He did feel able to talk out loud with Jenny about these things — like he couldn’t with any other human being. He looked into her eyes, beneath the tumble of curls and the quizzical brows.

“It’s….. almost….. like it’s always been so…. I guess…….. When I was in my teens, I was shy with girls but, somehow, I enjoyed being with them… maybe not like every guy did — I wasn’t wanting to have sex or anything…. I’d been told about that rather later than other boys in my class. I just enjoyed being with them…. I was always quiet and maybe that made me different from the other guys they knew… so most girls I knew would be happy to have me around….”

Andy stopped and thought how true that was…. It hadn’t been long before the girls found ways to involve him in their conversations…… Never about boys thank God, but about almost everything else that girls talk about……

“I’ve read so many stories about how boys of that age get sisters or other relatives to treat them as girls…. This was different……. I found myself wanting to be in their circle… wanting to be one of them…… But always as a boy…. A girly boy… but a boy. I never found them wanting, like you read in some stories - or perhaps you don’t - wanting to practice make-up on me, or hairstyling…… Much, now, I know, I’d have loved it if they had done…” Andy paused again.

“So, it was when you were at college that you dressed for the first time… Am I right?” Jenny had picked up on the early exchanges they had had during his first visit to her salon. “You told me about a Turnabout Ball……”

“Yes, but that did come later…. Long before that, I had collected - or begun to collect — some nice pretty things……” Andy confessed. That was the time…… “I was about seventeen….”

“How did you feel, when you were buying them? …When you wore them?” Jenny was intrigued.

“I felt at ease…… Maybe worried I’d get discovered… but at ease otherwise…. I loved the soft and gentle feel of them next to my skin…… I slept in a nightie and I wore panties and a slip in the daytime. I wished I had tits but had nothing to put in a bra, so didn’t bother….. at first.”

“And you said your hair has always been important…. Did you grow it longer from that time too?” Jenny asked, getting closer to her own area of expertise……. “I dated lots of guys with long hair when I was your age then…..”

“Well, it was easy… of course… it was the time… in my case the late Sixties and early Seventies. I always took care of my hair and gave it a lot of conditioning. I did go to a salon, well away from where I was living, and had my hair set…….. You know… I asked for rollers….. Nooooo questions were asked, so I told them no lies……!”

“And you sat there, in the salon, at the mirror, with rollers being put in your hair, with everyone watching……. Or probably ignoring you!?”

“That’s right…” Andy was telling the truth now… “I told the receptionist what I wanted — a set in a female style……. I said there had been a stand-off with my parents over the length of my hair and they said if I wanted it that long, I should have it set like a girl…. So I did!”

“So you walked out in the street with you hair set? Didn’t that feel incredible??....”

“Well, not really…. Not the walking out bit……. Inside, yes….. The whole thing in the salon was like a dream.. I just sat watching after I’d had a back-wash for the first time…. Watching, like I did with you, watching the rollers go in one-by-one, all tight to my head….. I found I loved every minute of it…. The girl who did my hair.. I can remember her even now… she was only a Junior really, not much older than me, and a redhead. I told her my story — about my parents — and she said what a cool thing to do — face them off with it!”

“Did she do your comb-out after being under the dryer?” Jenny could picture the scene.

“Sure, she did…. I told her to comb it out as full as she could — I really got to know the meaning of back-combing that day! And clouds of lacquer…. It was stiff as a board!”

“And then you paid and left?”

“Too right! I just walked out the door with my hair combed high! Then, I rushed to the car and escaped!” Andy laughed as he admitted losing the plot at that critical moment.

“You see I’d dressed in jeans and a tee-shirt…. Light stuff… nice underwear underneath….. Oh, and by this time, I was wearing suspenders and stockings… but still no bra……… I thought then, if only I had tits….!”

Jenny put her head on one side and asked, gently, “Well, sounds like wanting to pass as a girl to me….. But then, I’m no expert!”

“No, honest, not that time……….. I was just loving the experience, not really how I looked….. When I got home, I must admit, I had gone via Marks & Spencer’s and bought a bra — still nothing to put in it — but I had got one! I got one to match the panties and slip that I already was wearing. Stupid really, I bought a 34D when I needed a 36B.. but they say most women are wearing the wrong sized bra, don’t they?!”

Jenny affirmed that, indeed, they do.

“Everything you tell me about that salon visit sounds like the day you came into my place- apart from the Mum and Dad things…….. Thank you for trusting me that day….” Jenny was truly grateful. “Did you go back? Ever? To that same salon?”

Andy saw how Jenny was almost ahead of him in the story of the beginnings of his cross-dressing. How could she do that??!! It was true. He HAD gone back — to the same salon — before going to University. He had had his hair set again……… He had had rollers and a ’proper’ set and comb-out. That time he had asked, on the strength of a continuing argument with his parents, for a bouffant top surrounded with a wonderful roll of flipped-up curls around the neckline.

He went on: “Indeed, I did……. And I came away with a style like the little girl in the movie ‘Hairspray’… you know the one with the bouffant….. and the highlights… I didn’t get colour or highlights because I didn’t have enough money but I’d have been tempted…. But wow, did I get a bouffant!?!.....

Andy was fully carried away with the reminiscences…. “……The same girl did my hair and she thought she was really going to offend my “parents” by doing so much. For me, it was only a question of getting home and making it last without discovery for as long as I could!”

“You brave boy!” said Jenny admiringly towards this now sixty-year-old sitting in her kitchen who was wearing her satin dressing gown…….. “So when you were challenged with a Turnabout ball at Uni, am I right in thinking you protested that you couldn’t possibly…….!!!?”

“Well,….. yes! But I did… and maybe, that’s how I come to be here now. With you.” Andy’s hand reached across the kitchen table and grasped Jenny’s. “Thank you, again, from the bottom of my heart.”

CHAPTER 10 FOLLOWS.........