It was Friday morning early. Ian woke and got out of bed with a slight groan. It wasn't that the thought of the day because this was a day off, it was the pain under his arm that hurt.
It was clear that there was no way that he could play golf today.
He got on the phone to Ray.
"Ray sorry mate but I'm going to have to cry off our golf match this morning."
Ian could sense Ray's disappointment.
"Look why don't you come round about half ten and we'll have a coffee together?"
It was definitely second best for Ray but he agreed.
By nine Ian had the house to himself. He went on line and into the nifty website to see if there were any new stories. He liked the TV teen section best, having written a few stories himself, but any new TV stories he would welcome.
He read a few and they stirred him to want to dress.
So he went upstairs and got some of his clothes out of the loft where he hid them.
He stripped naked and began to dress. He put on a black bra. As he clipped it behind him he marvelled that so many stories spoke of TV's having to clip the bra at the front and turn it round. Next was his black suspender belt. He reached into his case and pulled out a black stocking, which he rolled expertly up his leg but then struggled to fasten to the suspender belt because he was so excited. But he managed and repeated the process with the other stocking. He stood up and looked down at his legs and his flaccid prick hanging between the suspenders. He pulled a cream pair of panties up his legs and tucked his prick up between his legs to give a better shape to his front. He bent down and let his hands run up his legs enjoying the sensual feel of his stockings. Finally he slid a short black slip down over his head. Its hem only just came below his stocking tops but the material and its feel was out of this world.
Ian stood there for a while and luxuriated in the femininity of it all. But he knew he had things to do. So he put on his blue jumper and jeans, picked up a pair of socks and his trainers and went downstairs. Now as he sat at his desk he looked his normal male self but his feet would give the game away if any one other than himself were to see them.
He toyed with the idea of not wearing socks when Ray came round, half wanting to be discovered but he dare not. There was too much to lose.
So, as he saw Ray's car come into the drive, Ian dived down below his desk and quickly slid his socks and shoes and was standing at the door by the time Ray got there.
As Ian made the coffee he explained the situation regarding the pain under his arm.
"I used to be a paramedic," said Ray, "why don't you let me have a look at it?"
"No it's all right," Ian blustered, "I'll probably go to the doctor's tomorrow."
As he spoke he turned away from Ray to look for the biscuit tin.
"But it may not be possible to get to see a doctor. Come on let's have your top off."
Without Ian realising it Ray had come right up behind him and in a flash pulled his jumper up.
Ian stood there with the jumper over his head and his bra and slip on view.
"Oh crumbs," said Ray.
Ian pulled the jumper down.
"Sorry about that," Ray muttered.
"Yeah well...." But words seemed to fail Ian.
"You want to talk about it? Or do you just want me to forget what I've just seen?" Ray asked.
"Could you forget?" Ian asked.
The question was rhetorical. It was obvious Ray could not forget.
But anyway hadn't Ian half wanted Ray to find out? Well yes half had, but the other half had most firmly wanted this delicate secret kept firmly in the closet.
However now it was, in part at least, out of the closet.
As Ian made the coffee and showed Ray through into the lounge his brain was working overtime. Many times in the past he'd been almost found out by his wife and had learnt to be nimble on his feet. Now he was working out how much he needed to tell Ray, or, on the other hand, how much he wanted to tell him.
This was either a big opportunity or could be a disaster.
The first question was important.
"Look Ray if I talk about myself does it stay with you?"
Ray said "yes!"
"Are you sure? If not then I'd rather you went away with what little you know and no more."
"Look Ian we've been friends for ages. I don't want that to change. So whatever you say will stay with me."
That was what Ian wanted to hear and it made him more than relaxed, it excited him. He had wondered earlier about letting his secret slip to Ray and now he had the freedom and the security, he hoped, to tell Ray everything and who knew what might happen as a result. Ian had clearly in mind what he wanted to happen. He most certainly wanted Ray to see him fully dressed as Lucy and then see where that led.
"It is a long story," Ian began as the two of them sipped their coffee. "I started dressing in women's clothes when I was small. I would put on a pair of my Mum's panties and stand in front of the mirror. I can't remember what else I did. The next memory I have is when I was about 14 or so and I really date my transvestism from then. I was in the scouts and we were doing a 'Gang Show', a kind of variety show. Because it was all boys I was chosen to take part in the can-can. I can remember the costume as if it were yesterday. I had blue satin dress with black lace and blue satin panties with similar lace. (see the Making of Lucy for more details) We were allowed to take the costumes home for a few days before the dress rehearsal and performances. At home I took every opportunity to wear the costume and especially the panties. If I wasn't hooked before I was now. More and more I took to sneaking into my parents bedroom and putting on my Mum's panties. If I went to my Grandma's I would make an excuse to go upstairs on go into my Aunt's bedroom, who was living there, and touch her undies. One summer I even had the run of the house for a week. Each day I would leave my girlfriend, such was the pull, and go to my Gran's house and put on some panties and either a beige slip or a yellow nightie. I would lay on the bed with the gorgeous material draped over my body and masturbate.
Over the next few years I bought the occasional pair of panties and some tights to wear when I could. I couldn't see a girl without wanting to know what she was wearing under her clothes. With my girlfriends I paid as much attention to their undies as I did to their bodies.
When I went away to college I got together a little stash of undies. Sometimes I would steal a pair of panties or bra from the laundry room. But it was only when I got my first job and lived in a bed sit that I bought outer clothes. Then finally, not long after I got married, I made my first trip out dressed. Just a quick walk one night."
"Weren't you afraid of being caught?" Ray asked.
"Oh yes but the desire to be seen as a woman and the thrill of being out with the wind up my skirt and round my stocking tops was too great to stop me. I nearly did get caught one night driving out of the drive but it was dark and I got away with it. I remember that night very clearly. It was the first night I went to a TV group in Islington. I had prepared very carefully. I wore a white bra, which I padded out, a whites suspender belt with black stockings. I can still recall the sweet pair of little pink panties I had at the time. I put on a light green half slip with lots of lace at the edge. The fashion at the time was for the lace to show below the hem of the skirt. I had on a black skirt with pink and green flowers and a cream blouse with elasticated waist and a pair of black shoes with low heels. I borrowed my wife's wig, did my make up as best I could, put on one of her coats and drove down to Islington.
The whole thing was quite scary but I had to be seen and I wanted to meet other TV's. I was made quite welcome but the thing that stays in my mind was a straight man asked me to dance. So suddenly there I was with this guy with his arms round me dancing. He even asked if he could take me home. I wouldn't let him and he had to be satisfied with a kiss on the dance floor.
From there the desire to dress has just grown along with my own wardrobe, which obviously I keep well out of sight. Now, many years later, I dress when I can, often, as you have seen, just wearing undies but sometimes getting fully dressed and even going out.
So in a rather large nutshell that's me."
Ian waited to see what Ray would say and to answer the questions. Over the next twenty minutes or so they did come but not the one question Ian wanted. After a while he realised he would have to engineer the situation a bit.
So when Ray asked "Do you think you are convincing as a woman when dressed?", Ian pounced.
"I think so but I have to let others be the judge of that. Why don't you judge for yourself?"
"What do you mean," Ray asked, "me see you fully dressed?"
"I think it would be only fair to both of us. You have seen me partially dressed and might want to see the real thing, and for me I wouldn't want you to go away thinking I bet he looks like a dog's breakfast when he's dressed."
Ray agreed that it made sense.
"Right I'll wait here while you get dressed then" he said.
"I have a better idea," Ian replied. "Why don't you go off for a couple of hours and give me chance to get properly ready and then come back?"
So that was what happened. Ray left and Ian set about getting ready.
Ian rushed upstairs stripped off and jumped into the shower. There he removed as much hair as he could or dare to.
Stepping out of the shower he dabbed himself dry. Now what to wear? It wasn't really a question because he'd spent most of the time in the shower working it out.
He put on a white bra, into which he placed his breast forms. He clipped the white suspender belt round his waist. It was tight and deep, which meant it stayed in place better than some of the other belts he had. He opened a new packet of black stockings and slid them up his legs. With the addition of some white panties and a white cami-top he was ready underneath. He loved the virginal white, though he knew it wasn't completely appropriate.
Ian sat in front of his dressing table and did his make up then brushed out his wig and put it on. He looked into the mirror, not bad he thought and hoped that Ray would think the same.
He sprayed himself with deodorant and walked over to the bed where his dress was lying. The dress was a rich blue. It was quite figure hugging until mid-thigh where it flared out in pleats. He stepped into the dress and pulled it up, managing to zip it up behind.
He stepped into his black court shoes with 2 1/2 inch heels.
Back at the dressing table he put on his earrings, necklace, rings, watch and bracelets.
Finally he was ready to paint his nails with the bright red varnish he so loved.
He stood up and moved towards the long mirror and there was Lucy looking back at him.
Lucy looked at her watch it would be half an hour before Ray arrived.
She went downstairs and did a little tidying up, got things ready to make some tea and every few minutes looked at her watch, which seemed to move so slowly. To say she was on tenterhooks was a huge understatement.
At last the doorbell went.
Lucy peeked through the curtains to check it wasn't some unwanted visitor and there stood Ray.
Lucy flew to the door and let him in.
Ray's face on seeing Lucy said it all but the words helped. "You look amazing Ian. I would never have believed you could look so good."
"Thank you kind Sir," she said, "and the name's Lucy."
Lucy led Ray into the lounge, hoping his eyes were on her bottom and legs. She left him there for a moment while she made the tea and brought it in.
Ray sat on one of the two two-seater sofas while Lucy sat in a chair.
The dynamic and the chat were different from what it had been earlier. This was no longer two mates passing the time of day. Now there was Definitely a sense of sexual frison in the air.
Lucy knew that she could sit demurely with her legs tucked backwards and ankles crossed but she wanted to attract Ray and so she teased him by regularly crossing her legs, which of course brought her pleasure as well as she felt the rub of nylon on nylon.
She was well aware that Ray was staring at her legs.
After a while when things didn't seem to be getting anywhere Lucy asked, "Ray you've been here with me some time now let me ask how do you see me? Do you see a man dressed up or do you see a woman?"
Ray pondered for a moment. "It is hard to forget that you are a man but if I didn't know that and just saw you I'd see a woman and a very attractive woman."
"Perhaps you'd like to see some photos of me in different things," Lucy suggested.
She went across to where Ray was sitting and sat next to him and showed him some carefully selected photos.
Lucy was very aware of the man sitting so close to her and it was clear that Ray was aware of her as a woman because firstly she felt his leg push up against hers and then his hand brushed against her leg.
Lucy wanted to encourage him and so she edged closer to him so that their legs were fully touching and she gently slid her arm under his arm as she pointed out something on one of the photos. In so doing of course she got even closer to Ray.
It was the clearest signal she dared to give him.
Ray did respond, "Your legs look really nice in this photo," he said as he put his hand on her leg.
He paused waiting to see how Lucy responded.
"Yes I love the way stockings make my legs look....... And the way they feel."
His hand ran up her leg a little.
"They do feel nice Lucy," Ray said.
Lucy turned to face him and because she had got up so close her face was very close to his and it took just a small incline of his head for their lips to touch.
It was just the briefest of pecks but when neither moved away it was clear to each that the other was happy with this.
Ray leaned forward again and this time it was a proper kiss he planted on Lucy's red lipsticked lips.
Lucy opened her lips a fraction and Ray's tongue pushed into her warm mouth.
She felt one of his arms go round behind her as the other hand rested on her knee.
Her head was swimming and her heart pounding.
As they pulled apart Lucy looked at him, "wow Ray," she gasped, "you do see me as a woman don't you?"
His answer was simply to kiss her again. Lucy sucked his tongue deep into her mouth and played with it with her own tongue. She felt his hand go up to her breast and, while she could not feel his touch as a normal woman would, the very fact that he was squeezing her there spoke of how he saw her as a woman.
Then his hand went down to her leg. She could feel it warm through her stockings.
Lucy reached out a hand and touched Ray's crotch. Yes she had had the desired effect, his prick felt hard to her touch.
Their kissing became more passionate and Lucy felt herself being forced back on the settee. Ray's hand was moving inexorably up her leg. She felt on fire. Every nerve ending was tingling. She had never realised she could want someone so much.
Ray's hand had now reached the top of her stocking and landed on the soft flesh of her thigh. Lucy gave a little moan of pleasure as Ray stroked her skin. In response she squeezed the growing lump in his trousers.
Ray moved his body so that he was almost lying on top of Lucy. She could feel his prick pushing at her tummy and his hands all over her body. There was no doubt where this was leading and the thought made Lucy's own little prick stiffen in her panties.
Eventually she forced herself to push Ray off her.
"Why don't we go upstairs?" she suggested.
Ray was more that willing.
As Lucy led the way up the stairs she felt Ray's hand go up under her skirt. There was no doubt that this man was hot for her. Now she was very glad that she had lubed her cunt earlier on.
Once in the bedroom Lucy closed the door and turned to Ray flinging her arms round his neck and kissing him.
He responded by pulling up her skirt allowing his hands free access to her pantied bottom. Lucy squirmed with pleasure and pushed her hips towards him.
For a fleeting moment Ray let go of her bottom, but only so that he could slide down the zip on her dress.
Lucy wiggled her shoulders and then her hips and the dress slid down her slender body and ended up in a heap at her feet.
Ray's hands roamed sensuously over her nylon clad body as their kisses grew even more passionate.
Lucy's hands were at work first undoing and removing Ray's shirt and, while she would have loved to spend time running her fingers through the hair on his chest, there were more pressing things to do and very soon she had his trousers undone and them and his pants down round his ankles.
At last she had his prick in her hand. She gently held it. It was so hard, about 7 inches long and quite thick. She was really going to enjoy this invading her girly body.
Lucy opened her legs and pulled the prick between her thighs, which she quickly closed to keep it there.
Now as they kissed she moved backwards and forwards stimulating Ray with her fleshy thighs.
Lucy felt so feminine standing there in just her undies with a prick stuffed between her legs. But there was so much more and such better things yet to come and Lucy was determined to enjoy every delight she could while she had this man with her.
Lucy, like every TV, knew that you had to make the most of every encounter with a man because there could be plenty of periods where there was no such contact.
Lucy felt Ray's hand go inside her panties and begin its search for her pussy. She allowed him access and he slid a lovely finger up inside her. Now she really was squirming and little mews were coming from her painted lips.
What could a TV enjoy more than to be in her delicate underwear with a man's arms round her, his prick pushing at the thin gusset of her panties and his finger deeply embedded in her cunt?
Well Lucy knew there were a few better things and so with some reluctance she pulled away from Ray's hand and slid to her knees.
Now she was at eye level with his prick. The foreskin was covering the head. Her hand with its bright red nails held the prick and slid the foreskin back to reveal the lovely purple head.
Lucy leant slightly forward and licked the purple head. She let her tongue lovingly lap round and round it before licking down the stem and then over his balls.
Now she was ready and opened her lips again and let the head slide into her warm wet mouth. Oh it felt so good to suck on Ray's prick!!!
She began to bob her head up and down on the member. She had never managed to deep throat but she had had no complaints with what she was able to do and from the sounds Ray was making it was clear he was enjoying Lucy's ministrations.
Lucy would have loved to have sucked Ray to completion but that was not what she wanted, so after about 10 minutes of this pleasure she felt that she and he were ready for the final phase.
Lucy stood up and walked towards the bed and lay down. Her legs were wide open.
"Why don't you come and join me?" she said to Ray. Then she watched tantalised as he walked towards her with his hard prick bobbing up and down.
Ray stopped by the bed and, possibly for the first time since he removed Lucy's dress from her, took a good long look at this unusual woman.
He saw a vision in white lingerie and the hardness of his prick showed that he liked what he saw.
"Oh Lucy you make a wonderful woman," he sighed as he lay down on the bed beside her.
Their legs intertwined as their lips met and hands touched each other's intimate parts.
"I want you to make love to me Ray," Lucy said. " I want you have me as a man has a woman, to fill my cunt with that lovely big prick of yours."
Ray knelt up on the bed between Lucy's legs as Lucy slid a pillow under her hips.
She lifted her legs onto Ray's shoulders while Ray pulled her panties to one side.
Edging forward Ray located her little rosebud with the head of his eager prick.
Ray gave a slight push and it was in.
Lucy gasped with the initial pain.
"Just stay there a moment," she urged him.
Lucy kissed Ray as she got used to the feel of his prick stretching her tight pussy.
"O.K. Ray," she said, "now start to fuck me but go slowly to begin with."
Ray did as he was asked and eased his prick deeper inside her. It felt much longer than it had looked and Lucy loved that wonderful full feeling.
Then Ray pulled back and the empty feeling followed.
When he'd done it two or three times Lucy felt much more relaxed and began to move her pelvis to match Ray's thrusts.
Ray got the message and began to speed up a bit.
Lucy allowed her legs to slide off Ray's shoulders and round his waist.
Now they were totally joined to each other and began to enjoy the fullness of their sexual linking.
Lucy marvelled at the incredible feeling of femininity that flowed over her as she took Ray's manhood deep into her willing and effeminate body.
"I love being a woman," she cried into Ray's ear. "Fuck me Ray, fuck me and make me your woman. Fill me with your cum."
That was the course that Ray had inevitably embarked on from the moment he entered the bedroom with this sexy woman.
Lucy's words spurred him on and she could feel him thrusting faster and his balls slapping against her thighs as he pushed right up inside her.
If ever she wanted a moment to last for ever it was now.
But the excitement was too much for Ray and suddenly Lucy felt his body judder in that very familiar action as he shot his sperm up into her tummy.
Squirt after squirt of the creamy goo was shot into her insides before Ray collapsed on her.
"Oh Lucy," he sighed, "that was the best sex ever. I can't remember when I last came as hard as that."
"Well now you know all about me, you know where I am and we can always do it again sometime," said Lucy, hoping that this could happen many times in the future.
Ray lay on top of her for a while until his prick shrank and slid out of Lucy's wet hole.
Lucy pulled her panties across her pussy but she could feel the gentle seep of Ray's cum out of her cunt.
She lay back on the bed and luxuriated in the wonderful feeling of having been made love to.
She watched as Ray got up off the bed fascinated by his now floppy prick as he stuffed it in his pants.
Lucy stood up as well and now the seep became a sexy flow as the semen dripped into her panties. She knew she'd keep them as a souvenir. She wrapped her arms round Ray and exacted one last kiss and cuddle from him.
"You will cum back and see me again soon won't you?" she asked.
"Oh yes it certainly beats golf. I definitely want to see more of Lucy and especially to fuck you more."
With that Ray left the room.
Lucy sat in front of her dressing table, feeling the lovely squishy mess in her panties and brushed out her hair glad to be a woman and feeling that wonderful post-sex glow.
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