It's a Beautiful DaybyBabyPink©
The weekend started off the same as any other for Simon. He threw off his drab male work clothes with alacrity and stepped into the shower. He shaved his face, legs and pubic area as was his custom, then, after turning off the tap, moisturised his legs, stepped into a pair of lacy pink panties and hooked on a matching bra.
The feel of the light, soft, feminine fabric had always been a thrill to Simon, ever since that fateful day when, aged fourteen, he found himself alone in the house all day. He put on ladies clothes for the first time -- his older sister's panties and slip -- and had felt so aroused he had masturbated almost continuously until he went to bed.
He then inserted into his bra a pair of expensive breast forms that gave him that reassuring weight on his chest and made him feel so much more feminine. Next on was a pair of sheer black hold-up stockings. The nylon felt wonderful against his freshly shaven legs.
Walking into his bedroom, he opened his wardrobe, which was filled with an array of skirts, dresses and tops, but very few masculine clothes. They were all bought by mail order, since he didn't have the nerve to go shopping for ladies' clothes. He unhooked a pretty blue and green floral jersey dress from off its hanger. Pulling it over his head and smoothing it down, he felt immeasurably better and began to put the tensions of the day behind him. He strapped on a pair of black Mary Jane shoes and sat at his dressing table to put on his make-up.
He was always very meticulous with his cosmetics, taking his time so as to do a good job. First he put moisturiser on his face, then foundation cream, blending it into the neckline. He then put blusher on his cheeks and several layers of cherry-red lipstick on his fleshy lips. Afterwards, he carefully applied black eye-liner and pencilled in his finely plucked eyebrows. He then brushed on blue eye shadow, applying a lighter shade on the area below the eyebrows and a darker one to his eyelids. After about fifteen minutes he looked in the mirror and decided it was good enough. He then clipped on a pair of large hoop earrings through his pierced ears, and then put on two rings, a bracelet and a nice gold necklace. He sprayed his neck liberally with his favourite eau de parfum and finished by painting his nails with a bright pink varnish. He was done. His transformation was complete. He was no longer Simon, but Simone, as he liked to think.
As ever when he was dressed up, Simon felt a tremendous rush of sexual energy and his thoughts immediately turned to men.
But Simon's clothes, make-up and jewellery were cloaking a secret sadness. He knew it even though he tried to deny it to himself. It was a sadness he was increasingly trying to drown in alcohol, which was becoming a worry to him. He desperately needed a boyfriend, but he was too shy, too frightened of people, to go out and find one. He looked back with horror to his early teens, when he had to endure a great deal of nasty name calling and bullying at school because of his delicate, feminine ways. That had made him turn in on himself and become very isolated. To Simon's credit, however, he had fought back through sheer hard work and his sharp intelligence. He became one of the best students at his school and had gone on to university, where he studied computer science and gained a first with a distinction. He had then obtained a good job as a software engineer with a large plastics company, where he earned enough money to satisfy his craving for all things pertaining to the opposite sex. He moved into a flat in the town where he had studied, where he could indulge his passion in perfect anonymity.
Not only did Simon spend large sums of money in acquiring a wardrobe and range of cosmetics any shopaholic, fashion conscious girl would have been proud of, but he had even started using hormone creams on his chest, bottom and thighs. The results were disappointing for the first three months or so, then one day he noticed a puffy swelling around his nipples in the bathroom mirror, signalling the beginning of breasts. His thighs and bottom also began to fill out, his skin becoming softer. He had no idea where all this was going, but he felt compelled to follow the path of increasing femininity. Simon wanted desperately to look, dress, think, walk and even sound like a girl. He had developed a passable female voice by following a feminisation cd he had found on the internet.
Still, he felt a horror of being discovered as a cross-dresser and feared being taken advantage of by more cynical people, being so timid. So he comforted himself with his fantasies.
Indeed, Simon's masturbatory fantasies were extremely lurid. He would insert an anal vibrator inside himself, imagine being taken vigorously from behind, and ejaculate copiously. This evening, as usual, Simon reached for his bottle of gin, logged on to his favourite porn site, and watched a succession of gorgeous ladyboys being pleasured by handsome men, wishing with all his heart he could be like them. For him, they were the ideal to aspire to; they were so slim, sexy and had lovely small breasts.
Yet Simon wasn't as far behind them as he thought. He was only 5 feet 6, of a very slender build, and had a nice shock of blonde hair that almost reached his shoulders. He had tried experimenting with wigs but decided his own natural hair looked best.
That night he staggered drunkenly into bed and had the worst nightmare of his life. It was a recurring nightmare but this time it felt particularly menacing. He was walking on a path through a dark forest, dressed only in his lingerie and high heels. Every now and then he would come across gay couples having sex. When they saw him they laughed scornfully at his inability to be his true self. It carried on like this until he left the forest, a storm of derisory laughter sending him on his way. He walked on until he came to another forest, where the same humiliation was repeated, then another forest, again and again.
Simon woke up in a cold sweat, terrified and very upset. He put his head in his hands and cried for several minutes, which made him feel a little better. Then he felt a determination that he had not experienced since school, when he resolved that the bullies would not drive him to suicide. He must break out of his isolation and meet a man, someone who would really care for him. Anything would be better than this gradual descent into alcohol dependency and depression.
So Simon decided to place an advert in the personals column of a very respectable newspaper. The ad went something like this: Intelligent 21 year old, lover of animals and literature would like to meet older man 25-30 for friendship, perhaps more. Simon sent the ad off, already feeling better that he was doing something positive to improve his situation.
The ad appeared in the paper over a couple of weekends. The first week, nothing happened, but on the Monday of the second week, Simon received three calls, all from guys who wanted to meet him. Simon arranged to meet them all over the course of the week for a drink. Simon honoured the dates but nothing came of them. He was so shy he couldn't give the best of himself and didn't know how to start or maintain a conversation. Anyway, he wasn't impressed with his dates. They all seemed to want someone more outgoing and fun-loving, whereas Simon was very reserved.
Simon was beginning to feel it had all been a waste of time. He received no more calls for two weeks. Then, out of the blue, on a Saturday, he received a call from a man, obviously American, who wanted to see him. Could Simon meet him that very night? Why not, thought Simon. They arranged to meet outside a pub called 'The Peach' in an area of town where there were a large number of gay bars. Simon made the ten minute walk and waited nervously, his newspaper tucked under his arm; the old tried and tested method of being identified on blind dates. Simon felt a mixture of apprehension and anticipation. He had been in very few pubs full stop, let alone gay bars.
The arranged meeting time of 8 o'clock passed. At ten minutes past, Simon thought sadly there was no point in waiting any longer when a tall, nice-looking black man approached Simon and asked in a polite voice if he was the guy had had rung earlier.
Simon immediately recognised him to be a lecturer from the university, from the modern languages department to be precise. He was openly gay, but that wasn't usually a disadvantage in academia. "Hi, I'm Greg," he said, holding out his hand.
"I'm Simon." They shook hands warmly, and then Greg motioned Simon inside the pub.
"Don't I know you from somewhere?" asked Greg.
"You might have seen me at the university where you teach. I left there just a few months ago."
Greg's eyes reflected pleasure that Simon knew who he was. At least they had something in common. Greg asked Simon what he studied and what he was doing now. Simon felt at ease with him, and spoke openly without nervousness. They moved on to talk about relationships, Simon not being ashamed to admit he hadn't really had any. It turned out that Greg had just broken up with his ex-boyfriend rather acrimoniously and wanted to find someone else.
The wine flowed and the evening flew by. They talked more freely with one another. Simon had never spoken so openly about his thoughts and feelings and found Greg to be utterly refreshing as a person as well as easy on the eye. However, Simon didn't mention his cross-dressing. At a certain point in the evening, Greg decided to take a chance and stroked Simon's wrist under the table. The effect on Simon was dramatic. It was as if sparks were shooting up his arm. He didn't pull his hand away, much to Greg's relief. Indeed, he squeezed Greg's hand tightly and smiled at him, as if to assure him his touch was very welcome.
Eleven o'clock arrived and Greg announced he had to go home. "Do you live very far away, Simon?"
"It's just a ten minute walk."
"I'll walk with you then, if I may."
"Of course you can!" Simon felt so comfortable with this man. He particularly liked the way he called him "honey" and "baby" in that charming American way.
They started off together towards Simon's flat, continuing their conversation. When they drew close to Simon's flat, Greg persuaded him to make a little detour behind a wall which hid them from the main street. "Listen, Simon. I've had a great evening. You're really sweet and I'd like to see you again."
"I've really enjoyed it too, Greg. Of course I'll see you again."
Greg held Simon around the waist and asked if he could kiss him. Simon nodded and put his arms around Greg's neck. There followed the most delicious moment of Simon's sad young life as Greg's mouth met his in a very short but oh so sweet kiss. Simon's heart was thumping. He couldn't believe this turnaround in his fortunes. They walked the remaining distance to Simon's flat together. Greg promised to ring the next day.
Only the call didn't come. Simon's heart sank. Just when he felt his life was on the up, his hopes had been dashed once again. The next day was the same. Simon reflected sadly that Greg was just too good for the likes of him. It was Friday when his phone rang. Simon replied in a tone filled with hopelessness. It was Greg.
"Listen, Simon. I'm so sorry. I had to go away for a few days in a hurry and stupidly I forgot to take your number. If you'll forgive me I'd like to take you out this evening. That is, if you're not doing anything else."
Simon knew from his tone that his apologies were genuine. His heart leapt at hearing Greg's voice again, and his spirits were given an immense boost. "No I'm not doing anything else, Greg. Just give me half an hour to get ready!"
"OK. I'll call for you!"
Simon hastily pulled on his jeans, t-shirt and a thick black sweater as the early spring weather was still quite cold. His doorbell rang. Opening the door, Simon could see that Greg's face was full of regret. "Hi babe," said Greg kissing Simon tenderly on the cheek. "I feel really guilty about not ringing you the other day. Let me make it up to you. We'll go for a drink then a meal. It's all on me."
"Sounds good to me," replied Simon. "You had me really worried, I must admit. But I'm sure you had good reasons for having to go away. Please let's not mention it anymore."
They spent a delicious evening together, drinking several glasses of wine in one of the smarter bars in town, and then heading off to a pizza restaurant. Greg was very frank with Simon about the series of disastrous relationships he had had. His personal life was almost at the opposite extreme to his professional life, which was very successful. At the age of 29, he was already regarded nationally as an expert in his field. Simon suddenly felt that, in return, he had to be honest with Greg.
"Listen, Greg I have something to tell you," Simon said in a nervous voice. "I've been really worried about this and I hope you don't think me strange or anything, but...at home I dress as a lady. I've been doing it for years."
"Well, so what?" said Greg, astonished that he'd even raised the issue. He grasped Simon's hand to reassure him. "After all, it's a free country! I know a lot of cross-dressers but I know you'd look better than the lot of them! How far do you go with your dressing up?"
"The works: clothes, make-up, accessories, jewellery, the lot. I've even managed to develop a girl's voice."
"That's cool." Greg felt himself grow hard in his shorts. He had always been secretly turned on by the thought of boys wanting to appear more like girls.
As for Simon, it was as if a huge weight had been lifted from his shoulders. They proceeded to talk freely about Simon's fashion preferences and how he began cross-dressing. Simon felt enormously liberated. He had never talked like this so frankly with anyone.
"Listen, Simon. Why can't I take you out all dressed up?"
The very thought made Simon shudder. "I couldn't Greg. I just wouldn't have the courage."
"Go on! You'd look great!"
"I'm sorry Greg. Please don't make it a bone of contention!"
Greg admitted defeat, albeit temporary. "OK then. We'll compromise. Put your best dress and heels on and come over for dinner to my place tomorrow. I could pick you up. You wouldn't have to walk very far in the open."
Simon was very reluctant but his reticence began to fade as the level of the bottle of wine in front of him gradually emptied. He agreed, on condition that it was pitch dark when Greg picked him up and Greg parked his car as close to Simon's flat as possible.
Greg walked Simon home. Again they stopped at the high wall near where Simon lived. This time Greg didn't need to ask. He held Simon tightly around his slim waist, pulled him toward him and kissed him deeply, his tongue entering Simon's mouth. Simon felt dizzy, not only with the drink but with the intensity of Greg's passion. "I've never met anyone like you, Simon honey. I feel so good when I'm with you. You're so sweet."
"I feel the same about you, Greg. Simon rested his head on Greg's shoulder, sorry that their evening together was at an end. They parted. Simon felt on cloud nine. Never had he known happiness in his life. Now that he was experiencing this emotion, he didn't really know what to do with it.
When he awoke the next morning -- it was Saturday -- Simon immediately regretted allowing Greg to persuade him. A knot of fear began to develop in his stomach at the idea of stepping out into the open air dressed as a lady. But he had agreed to and he wasn't one to go back on his word. Anyway, it would be dark; maybe no-one would even see him, let alone recognise him.
Simon fussed and fretted about what to wear on his first outing as a lady but eventually settled on an elegant black dress, with a hemline just above the knee. He also put on some fancy lingerie, black stockings, and a pair of black stilettos. He rounded off his look with a nice chain necklace with large links. He decided to pull out all the stops, and even put on some false nails and eyelashes, which he felt made such a difference.
After Simon had put on his make-up, he sat on the settee and downed a few glasses of wine for some Dutch courage. Eight o'clock came and the agreed-upon pattern of knocks was heard at his door. Simon was so paranoid he was frightened someone other than Greg would coincidentally call and catch him in his preferred clothing. But thankfully it was Greg. He looked Simon up and down and said nothing for what seemed a long time. Simon took this as a sign of disapproval and his face became downcast. "You think I look ridiculous, don't you?" Simon said sadly. But he needn't have worried.
"Honey, you look gorgeous. No, you do really. A lot of the cross-dressers I've known just look like guys in drag, but you are the real deal baby. The only problem is...I probably won't be able to keep my hands off you!" Simon smiled, took him by the hand and kissed him tenderly on the cheek. Simon breathed a huge sigh of relief. He had been intensely worried about how Greg was going to take him dressed up.
Simon picked up his clutch bag, filled with cosmetics and other girly things. They walked down the one flight of stairs, Greg's arm tightly around Simon's waist. Greg opened the main door to the block of flats and they emerged into the open. Simon felt as if he were crossing a kind of Rubicon -- no going back. The cool night breeze blew deliciously between his legs and up his dress, filling him with a sense of freedom and making him feel wonderfully feminine. He relaxed a little. Greg didn't let him go, knowing how worried he was. It felt slightly surreal, Simon's stiletto heels click-clacking sexily against the pavement. Several people passed them but they didn't blink an eye at the couple. Finally, after about two hundred yards, they reached Greg's car. He opened the passenger door for Simon in a gentlemanly manner and he stepped inside, smoothing his dress under him before he sat down. He had made it!
On the short journey Greg felt the need to give Simon further reassurance. "Really, baby, you have a fantastic dress sense. I can't wait to see you in your other outfits."
"Well I try to keep abreast of the fashions and what girls like to wear nowadays. I normally prefer mini-skirts and skimpy tops, but I thought seeing it was my first trip out I'd be a little more conservative."
"Well you look like a very seductive lady. If I didn't know better, I wouldn't be able to tell the difference." Greg placed his hand on Simon's leg momentarily.
Greg only lived ten minutes away. The pulled up outside quite an old but elegant block of flats. Greg opened the door for Simon and the pair walked hand in hand to Greg's ground floor home. Simon had grown in confidence and didn't flinch when a resident came out of the main entrance right in front of them and greeted Greg. He obviously knew him.
The entered Greg's flat. It was neat and tidy with a nice feel to it. Everything was in its place and there was no clutter. "I've cooked you vegetable lasagne. I hope that's OK honey." Greg knew Simon was a vegetarian.
"I'm sure it'll be fine darling." The use of the term of affection was not lost on Greg. Simon was becoming more relaxed and this was reflected in his speech.
"Pour yourself a glass of wine while I get everything ready." Simon did so while Greg put some nice ambient music on his cd player.
Simon settled down on Greg's sofa, crossed his legs and lay back. He hardly believed this was happening to him, the born loser, Simon. He had found a man he fancied like mad and his feelings seemed to be reciprocated. Even better, he appeared to accept his cross-dressing without qualm.
They had a lovely meal while they chatted without reserve about their likes and dislikes, hopes and fears. Simon smiled freely in a way he had not done since early childhood. When the meal was finished they sat together on the sofa, holding hands, while Simon continued to down Greg's delicious white wine. Greg abstained, knowing he had to drive Simon back home.