Lady Chartlees’ Lovers Transgender & Crossdressers


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Lady Chartlees’ Lovers

Note. This is a longer version of the original to get to the second part find *2* in the test. I’ve included everything as it has been so long since the first part was published.

Lord Conrad of Chartlees was a slight and unassuming man who dressed extremely flamboyantly and tended to keep out of the public eye as much as he could. He was the complete opposite of his much younger wife who adored the money, fame and power that she had achieved through her unexpected marriage into the landed gentry.

Conrad, or Connie to his friends, loved his dog, a King Charles Spaniel called Molly, and would take her for long early morning walks through the woodland of their stately home. He preferred to be home before the grounds opened to the public and the hoi polloi surged through the ornate wrought iron gates to rampage through his house and estate with ice cream and picnic hampers. He was very much looking forward to the house closing for the day, more so than usual, as there was a party that evening to celebrate his fifth wedding anniversary. He was a little nervous about how it would turn out as he would be presenting himself rather differently and was not sure how people would react.

***

Conrad did not sleep with his wife, something they agreed upon early in their relationship. He slept in the old stables which was a much better deal than it sounded as they were beautifully converted and had a wonderful view across the lake. He had decorated them to his taste: quaint, quirky and old fashioned with walls full of ancient family portraits which comfortingly reminded him of his status and past.

His wife spent most of her time in what had been the servants quarters on the top floor of his ‘ancestral pile’ and which had been extensively refurbished and was now a large well equipped and spacious luxury apartment with a private lift. It was modern, designer and her bedroom was a boudoir full of silk, velvet and frippery. Both places had been converted when Conrad had realised that the only way he could afford to keep the house meant that he regrettably had to turn it into a tourist attraction.

That is how he had met his wife Elena. Apart from being tall, elegant and beautiful, she was well educated with a doctorate in hi. She was also extremely smart, ambitious and self assured. Her parents had been famous hedonistic musicians who had done far too much, much too young and were now largely a forgotten force residing in a sort of hippy rehabilitation home near Los Angeles. She kept in touch, but it always felt like she was entering another world whenever she spoke to them.

She had no admiration for their rather flakey careers and this had spurred her on to make her life a more stable, memorable and conventional one. Her natural abilities and hard work had meant that she had risen rapidly to the position of a house manager at a prime property of a major conservation organisation. She had taken advantage of the contacts from her parents to get started, but at the end of the day she was successful because she worked hard and was damned good at what she did. When the head hunting agency appointed by Conrad approached her about Chartlees Hall she seized the opportunity, seeing how it could easily be a successful and premium business. But there was another incentive too.

Within a year of her starting she had married Conrad and become Lady Chartlees, having seduced him with considerably more difficulty than she had ever had with a man before. She also conceived his heir with somewhat miraculous haste and had paternity tests done in case he doubted her. This had all proved unnecessary since, for Conrad, it was just what he needed to fulfil the dying wish of his mother. At last he was to be married to a beautiful and charming wife with a son and heir.

The marriage was a hasty, but nonetheless impressive affair, to which she used her parents’ contacts to invite as many celebrities as she could. In fact it became the event to be seen at that year which was quite an achievement and her organisational problem turned from making it a success to not upsetting important people. The marriage was all about marketing more than matrimony and creating strong headlines rather than heartfelt emotions.

Indeed, love, romance and matrimony were the last thing on Elena’s mind. She did genuinely like Conrad, but he was too passive and uninterested in for her and she needed men who wanted her and could fuck all night. He had at least surprised her with one gift he had and she would still occasionally take advantage of it. Conrad’s problem was that he was plagued by insecurities and his mind preloaded with a catalogue of family horror stories that meant he feared . This fear was something that had been reinforced on the two occasions he had found himself alone and naked with a woman, both of which he had found humiliating and just reinforced his negative body image.

For Elena, uninhibited was something she had always enjoyed and never worried about. was fun, something she had discovered during the wild parties of her youth where she could forget about the crazy, confused and troubled world of her family life and find joy by escaping into the arms of a lover, preferably two, and sometimes more. Such activities were secretly welcomed by her parents who knew nothing other than the freelove ethic of the seventies.

It was this liberated past that had taught her many things of which one was that a large and perfectly formed cock was a rare thing. Such a cock possessed great beauty and was capable of delivering the most amazing pleasure, especially to a woman who knew how to use it and was prepared to endure the initial pain and worship it. She had been educated into this secret by a porn star on her 21st birthday, a man who met the criteria and what a woman needed. She, therefore, knew how fabulous it felt, but also that it was something that should be an occasional treat.

For regular satisfaction, experience had taught her that the best thing was young men, preferably inexperienced and straight out of college. She could teach these young stallions the art of making love to her satisfaction and have fun with them at the same time. They were so easy to seduce, so hard and horny, and so willing to please, that she could mould them into her perfect lovers. She had enjoyed a number of men when she worked for the conservation organisation and had already ually devoured three fresh faced and handsome interns that she had brought into Chartlees Hall. She had even managed to arrange a menageatrois with two of them and was particularly satisfied that her gentle, but forceful, persuasion had brought out their biual side.

They were both so cute that she felt it would be a great shame if they went through life and never explored all the arts and forms of love making, so she had let them fuck her in the ass several times until they began to adore it, even more when she got them to plug themselves. She successfully pleaded with them that she desperately wanted to experience sucking while being fucked, or be spitroasted as one of the young men called it, a ruse because she had done it many times, but a ruse that worked.

Once they had agreed to this and she had let them take her, swapping over positions several times, she dared them to see how it felt to have a cock in their ass, a dare she knew they would not refuse as they were besotted with her. It was so hot watching them fuck each other, but even hotter later when each young man took it in turns to lay on his back and let her and the other straddle his naked body. She ground her pussy into the recumbent’s face and trembled as his tongue tortured her clitoris just how she had taught him while his hands softly caressed her nipples. Meanwhile, her mouth hungrily sought the lips of the other as he rode the hard cock beneath him, arms wrapped around her neck, groaning and squealing in delight. She absolutely adored the total, intense, and all encompassing body tingling sensations that only two mouths and two sets of arms could give her, and so did they.

***

These transient lovers had adequately satisfied her libido, but there was a shallowness that she missed brought about by a lack of any real connection to them, a problem that she felt was solved by the arrival of Maria at Chartlees. Maria had come to work as the stable girl, a sweet and innocent young thing that Elena had instantly fallen for and had proven to be a much harder task to win over. Men were just so easy!

She had obsessed about Maria ever since she arrived at Chartlees and began riding every day just to be near her. Her beautiful face and long blonde hair always tied in a ponytail, reminded her of the girl that had first brought her to a blissful but violent orgasm during summer camp and with whom she had fallen in love, only to be brutally cast aside when some meaty hunk had decided to date her. Maria reminded her of how special that Sapphic love had been and how much she missed it.

Elena would insist that Maria rode with her through the estate, sometimes side by side, but preferably following her, lusting after her straw coloured pony tail which flowed from under her helmet and pointed down to her gorgeous ass in ultra tight beige jodhpurs which rose up and down so seductively on her saddle. Her body would quiver with excitement, the whole experience of being with her, on a horse, legs wide apart, her own hard saddle rhythmically rubbing on her as they gently trotted amongst the trees would leave her in a blissful semiorgasmic state and she would have to relieve herself emotionally the moment she got back to her apartment.

Eventually she managed to lure her into her boudoir and, with the help of soft music, a y romantic movie and copious volumes of champagne, she eventually received the kiss she had been craving. For her previously straight lover it was a difficult boundary to cross and it was a hesitant and uncertain kiss at first, but one that was full of pentup emotion and a latent desire to let heart rule head. As she threw aside the shackles of her ual norms their passion grew like the torrent from an overflowing dam. A gentle trickle at first, tender and electric touches, lips, tongues and moans. Then mouths pressed hard against mouths, hands exploring bodies, as the inhibitions were washed away and, finally, clothes were urgently shed as their bodies burnt with desire and they were carried away in a powerful cascade of lust.

Elena was so on edge when Maria slowly ran her tongue down her tummy and kissed her inner thighs she was trembling uncontrollably. When Maria’s tongue finally gently lapped at her throbbing clitoris she came almost instantly, arching her back and pushing herself against that pleasure giving mouth, wanting more. Maria did not disappoint, making love to her tenderly yet firmly, riding the waves of ecstasy that were making her belle writhe beneath her until she could take no more and had to gently push her away.

That was the night that both Elena and Maria became confirmed s, albeit biual ones. Waking up with Maria holding her tight, silk drapes around their soft smooth skin and sweet scents everywhere, evoked a feeling of togetherness that Elena had never felt before and, a week later, Maria had become Conrad’s maid and Elena’s companion. In reality she was Elena’s lover, her closeness to Conrad the perfect cover for their illicit and permanent affair, although, to be fair, it was not a difficult job as Conrad was a dreamer who rarely saw beyond what he expected to see and wanted to see. He was happy to have an attentive and attractive maid who looked after him and even prepared him for the occasional night that Elena would come to his bed.

***

Maria was quite understanding of this arrangement, after all, Elena was married to Conrad, but being part of these preparations meant that Conrad became part of their relationship, even though he did not know it. Elena had told Maria all about how she had seduced him, a that Maria found quite amusing but also intriguing.

Elena told Maria how her normal subtle seduction techniques had gone nowhere and that Conrad was even harder to win over than her. She had therefore decided that a more direct approach was her only chance of becoming Lady Chartlees. After a long meeting about a new venture she excused herself and had then reappeared in the room wearing the most erotic lingerie she owned, complete with fully fashioned stockings, high heels and a chiffon gown. Conrad was frozen to the spot, his sense of fear more than overpowering the excitement he so wanted to feel. Elena kissed him and was completely surprised when she felt the front of his trousers and found that there was no sign of any hardness at all. She could sense how uncomfortable he was and so took control, crouching down, unclasping his belt and gently pulling down his trousers, kissing him through his tight white underpants, finally satisfied that there was some reaction as she felt him twitch. She eased down the last barrier and took his small soft cock in her hand and began to gently kiss it, pleased that it began to swell enough to take into her mouth, which she did. She looked up at him with her infamous puppy eyes as she rested the tip on her tongue, sure he would explode any moment. He didn’t. His cock just kept getting bigger until Elena was forced to push him out of her mouth and gasp at the gorgeous sight that filled her vision.

Conrad had no idea that he was endowed with such a monumental phallus, but at eight inches long and with a girth of six inches, a very slight upward curve and a glorious uncircumcised purple head, it was simply magnificent. The two girls who had seen it before had simply been shocked and not allowed him to come near them with it, which he had concluded meant he was in some way deformed in that department. For Elena it was a delight and with her experience she was not reticent in showing him how she could take advantage of it and get him to use it to the best effect. She always insisted he take sildenafil so it was the very best slick, silky and steely tool it could be for as long as possible. It was no wonder she had conceived so quickly.

***

One thing Elena had done from the outset of their marriage was to encourage Conrad to adopt a more dandyish persona, in fact these days he had a decidedly cavalier look with long flowing hair and colourful clothes of the best fabrics, especially silk. She felt this suited his character much more than the boring formal suits he used to wear. For his part he loved this transformation, relishing the unconventional style and playing up to its eccentricity. He even got so used to being referred to as Connie by his wife that he began using the short form himself as it felt more appropriate. He found himself happier than he had ever been and his clothing and mannerisms began to be more outrageously feminine as he relaxed into a persona that felt completely natural.

He loved the stylish and comfortable clothes his wife ordered for him and was naive enough to not worry that they were mainly for women. Blouses, slacks and kitten block heeled shoes graced his exterior while against his skin he wore delicate camisoles and pantaloons. She eventually had him wearing opaque tights, silk stockings, corsets and even introduced him to subtle make up. On the third anniversary of their wedding she bought him Molly, his beloved spaniel and commissioned a local artist to paint a large ostentatious family portrait with Christopher and Molly. She hung it in pride of place over the fireplace in the ballroom. Their relationship was unconventional but it was strong, built with genuine affection and respect.

***

The business was booming and with Elena’s influence their lives were becoming ever more ones of lord and lady of the manor, although many of the now substantial staff quietly joked that it was more like “lady and lady of the manor.” Maria, his maid, who would help him dress and do things like lace up his corset and slide silk stockings up his smooth legs would encourage him to wear new things. When she bathed him she would remove all his unsightly body hair and loved to give him a full massage which her gentle touch was always successful in making him grow. He was so embarrassed at first, but Maria was as fascinated and in awe of his impressive tool as Elena and insisted on washing it thoroughly, a job she enjoyed as much as Conrad. As it became more and more routine she began to take him in her mouth, something that they both enjoyed. Conrad was both impressed that she seemed to have a much bigger mouth than Elena and that she had the most amazing technique.

Maria became his confidant which meant Elena got to know every thought he had and was able to direct Maria to gradually push his boundaries. At first Maria introduced him to the idea that anal cleanliness was vital for good health and a thorough douching became a feature of his bathroom routine. She then brought him some anal plugs explaining that they would enhance the blow jobs she gave him. As she sucked him she would ease one in and out and Conrad could not believe how amazing it felt. He was delighted that the pleasure increased as she gradually upped their size. Eventually Maria produced a lifesize dildo which he was a little reluctant to try, but Maria was insistent and he was not capable of resisting, not in small part because of the thought of coming in her mouth as she massaged his prostate. He was so glad he had succumbed as the feeling was the most intense ever and he literally exploded in Maria’s mouth making her choke and gag, something she hardly ever did. He loved bath time and he loved his ass being filled, so much so that he often kept a plug up his ass all day, a special one with a red jewel at the end.

Elena and Maria did not just influence his ual leanings, they also encouraged him to gradually dress even more effeminately. He soon found that wearing long jacket dresses with piped seams and big metal buttons that went all the way up the front were fabulously comfortable and made him feel so good. He matched the dress with tight white lacy panties under opaque white tights, a combination that Maria had chosen for him. He loved how they hugged his bottom and prevented his bulge from spoiling the line of his clothes, the tighter the panties the better!

He had always been a frugal eater and he remained slim as Maria had put him on a fibre diet that was rich in natural oestrogen and low in calories. He had developed small breasts and larger hips which were suitably exaggerated by the cut of his clothes.

When he accidentally overheard a comment about ‘the two ladies of the manor’ he raised a concern with Elena that his clothing was perhaps becoming far too feminine and she explained that he had his own style and that some were simply unable to handle such individuality. She showed him several historical images of men from the seventeenth century and he was immediately convinced that his was the most modern interpretation of the style of that era.

She also added quite pointedly that he was lord of the manor and could wear exactly what he wanted. To make a point she bought him some beautiful tartan pleated skirts and wide white belts that she said were the perfect reinvention of the rather old fashioned kilt and sporran. He loved them, especially one that was really short and looked amazing with a white blouse, dark tan tights and white ankle boots. She made a reference to the term used at a staff meeting and it stopped being used.

The person he had overheard was Oliver Mountjoy who had joined the staff as estate manager and was someone that Elena had worked with in her previous job. He was a burly man who was well over six feet tall with a physique to match, in short, the very epitome of masculinity. Naturally he had been through Elena’s ual finishing school and had been a perfect student. She had included him in one of her threesomes with an intern and as a result he had discovered that he particularly enjoyed anal with men, a discovery that gave Elena some satisfaction from the point of tutor, but disappointment from the fact that he no longer had as much interest in her as he used to, preferring to be the dominant one.

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