48 Hours Ch. 14

Chapter 14 -- Matchmaker

After their successful evening together Lynn, Chris and Alan had come to an agreement whereby Alan would visit them at home once a week for his "exercise class" and get a psychiatric nurse to look after his wife for the evening and see if she could elicit any improvement.

Thursdays with Lynn and Chrissy were not just about sex, it was a chance to talk and enjoy each others company, and one evening they ended up having so much fun just being together that by the time Alan had to leave the most they had done was have a mutual cuddle.

They had not heard much from Graham and Sara, but realised that the new lovers would naturally be very much discovering each other and not have much time on their hands for other people.

Things were going well for Chris and he was really enjoying his Wednesday night stint in Belinda's club, Transcentral. The working from home on Thursday and Friday was perfect as he could be Chrissy all day and then greet Alan and Lynn when they showed up in the evening. The combination of the club evening and the following day meant that midweek he was beginning to really feel like a woman rather than an actress and his mannerisms were now becoming completely natural rather than forced. They were even sometimes straying into the more frequent times that he presented himself as male.

Chrissy was becoming quite an institution at Transcentral and was taking the whole thing very seriously. She had bought a new and expensive bob style wig that Lynn has trimmed and styled for her and had now perfected her whole club make-up routine, especially her eyes, where she was keeping her eyebrows tidy and shaped and had standardised on a specific set of fake lashes that really suited her, appearing both natural and full. She had also mastered a smoky shadowing technique that gave her eyes depth, size and extra height in a look which, although hardly light, was not so extreme that it would not be suitable for the day.

She had also changed her diet so that she had lost some weight and the daily regime of moisturisers and lotions was making her face and skin smoother and softer. The result was that she really did appear to be an extremely attractive woman for a middle-aged man and was absolutely loving the attention she was getting!

She had also been building up a collection of rather flattering clothes which had proved to be a very economical experience as one of the punters called Jason had taken a shine to her and was apparently the manager of a branch of a high-end fashion retailer in town called Sonja's. He was forever bringing in new outfits for her to try on and keep if she liked it. The great thing was that this guy really knew about clothes, so the outfits were always classy and sexy. He, himself, was extremely slim and had a very healthy tan, but was also short and balding, so not what you would call good-looking.

However, what, he lacked in looks he made up for in intelligence and humour, and he was also a closet bisexual and wore women's lingerie all the time under his fairly outrageous colourful clothing simply because he loved how it felt. Chrissy had asked him why he didn't dress outwardly feminine, and his answer was a bit sad. He just didn't feel he could carry it off, so was grateful that a lot of men's fashions were quite androgynous these days. He was always saying how much he loved Chrissy's 'three time a lady look,' a reference to his view that Chrissy was so convincing that it was only on your third good look that you began to suspect that she was not entirely the hot woman she appeared to be. So impressed was he, that he had even invited Chrissy to pose for the company's internal magazine and was keen try and push this as a complete advertising spread about Chrissy in a magazine.

Chrissy was not quite ready for all that exposure though and saw it as some lovely flattery, but she did appreciate what this guy was doing for her and had shown her gratitude when the opportunity arose one evening at the shop. They had spent an evening trying on various sexy outfits and inevitably ended up getting aroused and in need of some relief. Chrissy was wearing a beautiful bright scarlet A-line dress in a shiny satin that had an integral underskirt made from several layers of ruffled white satin that pushed out the skirt and created the most amazing 1950's hour glass shape. With nearly-nude hold-ups, matching red court shoes, and an oversize pearl necklace that went three times round Chrissy's neck, it really was quite a spectacular look and Chrissy found it hard to pull herself away from the mirror.

Jason had put on some black lace-top stockings held in place by a six strap silk suspender belt and matching camisole top. This lingerie was also unbelievably beautiful, finished in ivory and pink shades which flowed from bottom to top underneath black branching detailing. The variation in sheen under the light made it seem like a winters sunset seen through the branches of a tree. However, it was the four inch heel patent leather boots which were the piece-de-resistance. They really were over the top as well as over the knee and fitted Jason's legs like a glove (Chrissy was super envious of Jason's size 7 feet!). Once adorned, he had then bent over a chair in front of a full length mirror, pushing out his plump tanned ass making it very clear what he was after, because, although he was bisexual, he was not really into topping as he had so much trouble getting an erection these days and had a phobia of drugs of any type.

So needless to say, Chrissy had fucked him. She fucked him really deep and hard at first because Jason's ass was one of the sweetest she had ever seen and the submissive way he presented it made her want to use it, teach the slut a lesson! But after the first few angry thrusts, she began to savour every moment of the tightness, the heat and the feeling of his soft white skin when she bottomed out. But that was not what made this special, it was the way Jason wiggled and jerked like he was desperate to get Chrissy as deep as he could. It was the way he used his internal muscles to push and squeeze. But most of all it was the way he did all these things at precisely the right moment.

As the sensations became stronger Chrissy had to speed up, the ass she thought she owned, now owned her. Her balls and thighs slapped against the soft white orbs that pushed out towards her meeting every thrust, pushing and pulling, faster and faster, deeper and deeper, slap, slap, slap, slap, slaaaaaap! Chrissy jerked and twitched, pouring out her cum while Jason shook uncontrollably as he also came to a quivering orgasm, an orgasm so strong there were tears in his eyes.

It was actually all a bit too intense for Chrissy too and although she had enjoyed the sense of power at the start she knew she couldn't adequately reciprocate the lust and desire that Jason obviously felt for her. She felt a little trapped, a bit like this was the start of something she didn't actually want. Jason was such a nice guy she was actually really happy to have brought him so much pleasure and wished she could do more for him, but she just didn't fancy him at all, well, just his ass. Chrissy needn't have worried. Jason was not looking for love.

"Wow, who would have thought I'd get my best fuck ever from a chick with a dick." He laughed turning and smiling at Chrissy and even now Chrissy couldn't believe it, they had high-fived. It was such a relief, that Chrissy just burst out laughing. Jason was as straight in his actions as he was queer in his desires. There was no love, it was just sex, and Chrissy could relax again. She had already told Jason about Lynn, and Jason had been quite surprised to find out that hhe was married and in an open relationship. What really made him up though was when Chrissy invited him round for Dinner on Saturday. They were now clearly friends, and for Jason that was everything.

Another younger nerdy guy called Aaron had also taken a shine to Chrissy. He happened to be an aspiring digital artist who had only recently graduated and was struggling to find a job. He fantasized about cross-dressing, but because he lived at home with his father did not dare. He had taken to Chrissy as a bit of a mother figure, someone living out his fantasies, and with her consent was working on a secret project, a graphic novel called Transcender in which Chrissy was the model for his main character. It wasn't brilliant, but it was fun and very well executed.

Chrissy was on the one hand very flattered that she was now this young man's muse, but she did also sometimes find the adoration just a bit creepy. Aaron had mentioned some trouble he was having with picturing specific idea for a scene he had in mind where the heroine was being held against her will by an evil computer expert who was making sure that women were not welcome in the Gogglebook Corporation by exploiting their sensitive nature and making the recruitment tests biased.

After he had described the scene Chrissy offered to pose it for him, but with some conditions that she was sure would be enough to put him off. In reality Chrissy could see beyond this lads clinical shyness and appalling lack of style and knew that all Aaron needed was some guidance on achieving a look that gave him the confidence he needed to get to know people and come out. Once he felt comfortable with someone and crept out of his cage of shyness, like he did with Chrissy, he was both interesting and engaging. So although Chrissy said that she would help him out, she did so on three conditions. Firstly he would approve the final drawings; secondly, that Aaron would get his medium length dirty blond hair restyled into something a bit less nerdy; and thirdly, that he would get some new designer glasses. Chrissy had shown him exactly what he should get in both cases and although he was really not comfortable with it he agreed. Chrissy was pretty sure that he would not go through with it though!

How wrong she was! The following Wednesday a rather exotic and sophisticated young man turned up at Transcentral who turned quite a few heads as he walked upstairs seemingly in a trance and completely unaware of the effect he was having around him. One guy actually tripped up the stairs behind him as he was so distracted! Aaron's hair was styled in a sort-of pageboy look with a sweeping fringe across his forehead. The salon had added black streaks to emphasise his natural straw colour and whatever conditioner they had used had given it a beautiful sheen. He was wearing a pair of tight black trousers and a black open necked shirt with a deep red jacket.

He found his usual stool at the end of the bar and sat down, looking up slowly at Chrissy who was standing behind the bar staring at him. He waited for the judgement. Not only had Aaron followed the instructions to the letter, he had obviously studied and embellished the look in the photos Chrissy had sent to him and had a small silver chain earring in his left ear connecting the lobe to the side. He could see that he had shaved very close and was even heavily scented with what he thought he recognised as CK One. He also had applied some concealer and foundation to his face to hide the few spots that he had. The look was definitely male, but beautiful man rather than the traditional rugged look that most guys strive for. The transformation was quite unbelievable.

Chrissy had heaped praise on him, but could see him tearing-up. She took his to a quiet corner and gave him a big hug and a kiss on his forehead. Aaron opened up to her. To cut a long story short, he had had one hell of a week. He had woken up one morning to an email which was the breakthrough he had hoped for. An American Sci-Fi magazine wanted to serialise Transcender and had requested he sign a contract with them. As an incentive were going to give him an advance of three thousand dollars! With true US efficiency, the money was wired to his bank account the next day.

He had blown a lot of that on getting the new outfit and hair style which he saw as an investment as his desire to perfect the new scenes was now even more pressing and he desperately wanted Chrissy's help! On the down side, his father had been less than impressed when he had returned home that afternoon sporting his new look and in the ensuing row a lot of very hurtful things had been said, especially by his father. When Aaron had angrily stormed off, slamming the door, his father had shouted after him that he shouldn't bother coming back until he had sorted himself out.

Chrissy was concerned that he was in a deeply emotional state and called the club owner Belinda down, who was equally taken aback by how amazing Aaron looked. When she heard what had happened, she was equally worried about what she had been told and so whisked him upstairs to her flat to talk things over. Chrissy was pleased. Although she loved looking like a woman, she knew she simply would never possess that completely selfless caring and comforting ability that all women seemed to be born with and was confident that Belinda would have all the right words and appropriate hugs to sort him out.

Chrissy left the confines of the bar to check if any of the newly arrived customers wanted a drink and was waylayed by Jason who was intrigued by the goings on at the bar and asked who the new kid was. When Chrissy returned with a tray holding various drinks, she left Jason's Gin and Lime to last and sat down briefly to explain about Aaron and the "dare." When Jason realised who Aaron was, his jaw almost hit the floor and he repeated "amazing, absolutely amazing!" several times while he slowly shook his head from side to side. He then began entreating Chrissy to introduce Aaron to him.

Chrissy promised she would and had returned to bar duty when Belinda brought Aaron back, giving him a quick peck on the cheek while smiling at Chrissy to say all was sorted. Aaron was going to stay in her flat tonight, and for a several days if that is what was required to let the situation cool down. He would collect a few things like his laptop and some clothes from his father's tomorrow while he was at work and then confront him in the evening knowing that he could stay at Belinda's if he needed to. He was also going to talk to his mother, but she had moved to Manchester with her boyfriend since the rather messy divorce and had not really taken much interest in him so he was not sure about her situation or whether he would be welcome there.

Chrissy was true to her word and introduced Aaron to Jason and, to her surprise they got on really well, so well in fact that Chrissy felt that she wanted to be a match-maker, and extended the Saturday dinner invitation to Aaron who was delighted to accept. At the end of the evening, once the club had closed in the early hours, Belinda invited Chrissy up to the flat with Aaron and they had a bit of a chat about everything. Belinda chastised Chrissy for the "dare," but only jokingly as she did point out to Aaron how much better he looked and he should really be thanking Chrissy for that.

Aaron was obviously grateful, but his lack of self-confidence meant he much preferred blending in to the crowd rather than standing out, and now his light was shining so brightly he knew that he needed to adjust his mental state to be the same. The fact that he was finally going to be published had really helped him feel better about himself, and there was one other interesting development that Belinda managed to extract during the conversation which was that Jason had not only talked to him about a position at his boutique on condition that he kept the whole knew look, but also that he could live in one of the two flats above the shop for a nominal rent. This was really like having all his Christmases as once, but although Aaron was obviously very grateful for this opportunity, he was also rather nervous as to why a stranger should make him such an offer. Belinda and Chrissy reassured him that Jason was a very decent guy and although he was bisexual was not at all predatory and not to be feared. He was, they both echoed, a little bit lonely and just loved good company.

Despite a later than usual night, Chris had woken early with a surprising amount of energy. He saw that it was not long before Lynn needed to get up for work and gently parting her legs he set his tongue to work gently on her clitoris, enjoying the sound of her quiet moans as she reached orgasm. She lifted the sheets and Chris smiled at her.

"Well that was a lovely way to start the day, to what do I owe the pleasure?" She asked jokingly, running her fingers though Chris's hair, but before he could answer her hands pushed him down on her again!

After her second orgasm, Chris slid himself up the bed between her legs and his cock slipped easily into the wetness of her waiting pussy. Raised on his arms and the front of his toes he performed sexual press-ups on his sexy wife, just the way she liked. He was so turned on by her taste in his mouth that it took all his will power to hold back, but when he felt her arch her back and come, he exploded inside her, both of them grunting loudly.

As they lay side by side, he told her that he had invited Jason and Aaron round on Saturday for Dinner. His exertions had clearly been worth it as she didn't complain at all, but began to discuss what they might like to eat. She was certainly aware of Jason and knew Chrissy had spent some time with him and fucked him, but was more interested in his shop as she had already pinched some of Chrissy's clothes and really liked them.

The tale about Aaron brought out the mother in her and she had a little rant about people who had kids should look after them properly and be more supportive. Chris was relieved! He even explained about Sunday morning and Lynn was keen to come too and catch up with Belinda who she hadn't seen for quite a while, as well as see what Aaron was actually up to with this graphic novel of his.

Saturday arrived and the dinner was a great success with them all getting on really well, especially Jason and Aaron. Chris was Chrissy in a sleeveless knee length fitted dress that consisted of a purple top that gradually merged into a yellow lower with a sort of falling rain pattern made of small irregular rain drop shapes. It was one of her favourites from Jason but since it was quite restricting was not ideal for the club so this was the perfect opportunity to wear it. The clinging nature of the material meant stockings were out of the question as every bump would show, so she had shaved closely and applied some fake tan so she could be bare legged in some black Roman sandals.

Aaron was in tight jeans, black converse and a tight white top that he had borrowed from Belinda and was initially a bit down since his father was having nothing to do with him. It seemed he was a complete homophobe and simply could not get his head round his son looking like a "raving poofter." His mother had made a load of excuses as to why he could not go and stay with her, which were so pathetic, that he realised it had been a mistake to even contact her. So he had stayed with Belinda, and had, over dinner, made his mind up and agreed to work for Jason and take up his offer of one of the flats above the shop. With such a weight lifted, and a few glasses of wine behind him, he had cheered up completely. Similarly, Jason, who was in a plain black suit, couldn't stop smiling!

The after dinner conversation was free flowing, as was the wine, and it changed direction all the time. At one point Lynn mentioned how much she loved some lingerie that Chrissy had given her from Jason's shop as it had not been a good fit for her. It was a dark green lace teddy and she rather manipulative dropped into the conversation that she had it on tonight in Jason's honour, so to speak! They all laughed, but the talk about lingerie and everyone's favourites continued as Jason was keen to talk about the very latest item he had just got in which was a Basque and thong set in rich brown nylon mesh with gold lurex detailing. Lynn said it sounded heavenly and Jason, with a smirk, let out he was wearing it and offered to show her it, but, rather cheekily, was keen to see what the teddy looked like on someone with as good a body as hers.