Karl Baxter was an unmarried man aged forty who spent a lot of his time as attractive thirty-something Carla Baker. Throughout his twenties and early thirties, Karl had had sexual liaisons with both females and males but if he were to express a preference at that time it would have been for cock rather than cunt. At about the age of thirty-five, Karl had started to dress, from time to time, as a female although in the early weeks and months of doing it he never ventured outside.
As confidence and techniques improved, Karl found that when he looked into a mirror a rather attractive female would be looking back at him and confidence grew to such an extent that one night, late, Carla was born and she nervously at first walked around the neighbourhood. Confidence continued to expand and sometimes Carla would smile and attractively blush at wolf whistles that she would attract from passing motorists.
Her first face-to-face encounter was with a man who was probably slightly older than she and Carla found herself sucking his erection to ejaculation as he stroked her hair. As Karl, she had given many a blowjob but this was a first as Carla. The man's request to meet her again was met with a, "Perhaps one day honey," and a light kiss on the lips.
Karl had had many a cock in his arse in homosexual fucking but now Carla wanted a penis in her arse hole whilst dressed. She decided that despite the fact she looked very feminine she would not be able to get as far as baring her arse without her male companion becoming aware of her cock and balls so the predicament was how and at what point to let a prospective 'fucker' know that she was a he.
By now, Carla was attending local bars in which attractive 'ladies' of both sexes would go to meet men who were perhaps looking for some sex outside of their own marriages or maybe just on the lookout for some no strings attached sex. She had wanked a few cocks and given a few blowjobs without yet identifying herself as a male although undoubtedly some of the owners of the said penises were fully aware that 'she' was a he.
The first time that Carla went all the way was with a man named John Richards, at least that was what he said his name was, and he was aged twenty-four. The two of them had been kissing and petting heavily and things looked like going further so Carla decided that, for better or for worse, she had better make sure that 'John' knew just what he was about to take on. As Carla gently stroked 'John's' rather large penis she said, "You are expecting to fuck me with this thing aren't you, darling?"
John, not surprisingly, confirmed that, so Carla said, "That is fine, sweetie, but you will need to put it in my arse because I um do not have anywhere else for you to put it."
Now that could have produced all sorts of reactions from John but, to Carla's delight and relief, he replied, "I wasn't sure but I was hoping that you had got a cock."
With that settled, they went back to John's flat and he had Carla bent over, knickers off and skirt raised and he gave her a good fucking in the arse during which Carla's own penis spurted semen onto the floor. After that night, John fucked Carla a few more times and so did various other men from the local bars.
Carla Baker had now got herself a reputation as not only looking gorgeously attractive but also being a great screw and men of a bit more wealth than her earlier conquests were starting to show an interest.
One such man was Simon Morrison who was a handsome man of fifty-six who had a liking for males, particularly those that looked effeminate and especially one that had a backside like Carla's. Carla became his number one gurl and often accompanied Simon to party's where the guests were exclusively male even if about fifty percent of them were dressed as females. Carla was a huge hit here too and Simon, whilst liking to show her off, sometimes became jealous if another man paid her too much attention.
Carla would sometimes flirt with other men, she was confident of her position with Simon, and occasionally her flirting went too far. After one party, Carla was over Simon's knee for a very long and very hard bare arsed spanking although the lovemaking that followed was sensational for both of them.
Just occasionally Simon would allow a special friend of his get close to Carla, usually if some sort of business deal useful to Simon resulted from Carla's dalliance with the said friend.
One night at a party, Simon introduced Carla to an old school friend of his, Reginald Theobald and it so happened that Simon was trying very hard to get Reginald to sell him some property. Reginald was actually the headmaster at an all-boys school and had to keep his homosexuality in check for the sake of his job. He, like most men at these party's, was extremely impressed with Carla who found herself being treated as a bit of a bargaining tool in the prospective property deal.
Carla did not find Reginald to be unattractive but she was a little bit put out that her lover was seemingly happy for another man to have her for the sake of a building or two.
Eventually, Simon got Carla to agree to spend a night at Reginald's house just outside the school grounds with the promise of yet more clothes. A further chat between Simon and Reginald revealed that it would be nice if Carla could dress as a schoolgirl for the night at Reginald's and that she might be expected to bend over to receive a caning.
Simon then had to tell Carla about the possibility of getting a caning and she was very reluctant to agree to that. When Karl was still at school the use of corporal punishment was still permissible in private schools although it had been banned in state schools in the UK in the previous decade. Karl attended a private school and had actually once received four strokes of the cane across his seventeen-year-old backside but the memory of that did not make the prospect of a caning for Carla any more appealing.
In due course, the date for Carla's visit to Reginal Theobald's house, along with everything that was likely to go with it, was agreed and on the arranged day Carla arrived dressed very sexily and with her school uniform to change into.
Reginald gave Carla a long kiss and his erect cock made him consider fucking her there and then but she was there to help achieve one of his long-held fantasies although he had once before caned a male dressed as a schoolgirl.
He took Carla to a room in which she was to change and instructed her to knock on the door further down the corridor once she was in her schoolgirl attire. In the early days of dressing, Carla frequently got an erection whilst in the process of dressing but now such an occurrence was rare but as she looked at herself in the full-length mirror in her blouse and tie, indecently short gymslip, green knickers and stockings her penis was rock-hard. She would have loved to relieve the erection with a wank but knew that Mister Theobald would be getting impatient so she headed for the door that had been indicated with the knickers stretched at the front despite, or perhaps because of, the upcoming caning.
Carla tapped lightly on the door, "Enter!" boomed a voice from inside. Carla entered a room that was to all and intents and purposes a headmaster's study with a large desk, a couple of armchairs, and a large cabinet. Behind the desk was seated Reginald Theobald with a headmaster's gown over his suit, shirt, and tie.
There was a moment's silence whilst the two of them appraised each other's appearance until Reginald said, "Do you know why you are here, Miss Baker?"
"No, not really," replied Carla.
"You will address me as sir, you insolent brat," said Reginald as he slammed his hand down on the desk making Carla a little bit frightened.
"Sorry sir, not really sir," she stammered.
"Well, young lady, you are here because your behaviour warrants punishment and you are going to get a dose of the cane," said Mister Theobald who was close to cumming in his underpants.
Carla's erection had started to diminish slightly but these words brought it back to full size and the short skirt was being pushed forwards noticeably.
Carla did not know if she was supposed to speak or not but she did know that she was feeling a mixture of trepidation and sexual arousal at the prospect of what was about to happen.
Reginald Theobald stood from behind his desk and his own erection became obvious before he turned to the cabinet and extracted a whippy looking cane. He bent the cane and then slashed it through the air a few times as Carla watched open-mouthed. He put the cane down on the desk and moved behind Carla and grabbed the top of her knickers at the back but his initial attempt to pull them down was blocked by Carla's rigid penis. The headmaster manoeuvered the clothing clear of the obstruction and pulled the knickers all the way down before instructing Carla to step out of them.
He then picked up the cane and ordered, "Bend over the desk and grip the far edge, you will not stand until I tell you."
Carla bent as instructed and gripped the far edge, her short skirt rose to almost completely bare her buttocks but Mister Theobald folded it halfway up her back leaving her glorious arse completely exposed. Carla was positioned so that her erect penis was trapped between her stomach and the desk. Again, Reginald was very close to cumming as he slashed the cane through the air twice more before lining it up across the target that he was about to lash.
