What I (Really) Did on My New Year’s Vacation

Paul curtsied as Gloria entered her private quarters. He was, of course, standing ready and awaiting her return . . . as a lady’s maid should.

“Fetch me a Campari and Soda, Pauline,” ordered Gloria crisply.

“Yes, Ma’am . . . at once,” said Paul. This was his new form of address to his mistress.

He wiggled his way across the room on his high heels. He was quite used to them by now. Quite used to walking like a woman, too. It had become second nature. The daily hormone injections had smoothed his skin so that it was just like a woman’s . . . and his breasts had developed so much that he no longer needed to wear the false plastic ones which Delia had put on him. Although removing them had been a painful process even with the solvent.

It was now only necessary to wear the false ‘vagina’ underneath which his genitalia were permanently crushed. Paul felt the tightness of his cincher belt. Felt the stretch of the suspenders to his stocking tops. Felt the cling of the pretty little panties he wore. Gloria had forbidden him to wear a brassiere as a general rule, saying she didn’t consider him sufficiently developed. Even so, his breasts had become as fulsome as many a young girl of sixteen and he was constantly aware of the bounce and quiver of them as he moved about.

“I’m thinking of letting a man have you” said Gloria out of the blue.

Paul shuddered. It was the one thing that he had always secretly dreaded. “Yes, Ma’am,” he said weakly.

“You like the idea, of course?” she said.

Paul was on a cleft stick, as so often with Gloria. Was the right answer ‘Yes’ or ‘No’?

“I am your slave, Ma’am,” he said, “it is not for me to have likes or dislikes . . .”

“True . . . true . . . Pauline . . . but I guess you would like it all the same. That’s why I might keep you waiting a little longer.”

“When I do give you to someone,” Gloria was saying, “I shall make sure it is a man who actually thinks you are a girl. But a man who doesn’t like sex with women in the normal way. A man who likes to bugger women. Because I suspect that may be the only avenue of pleasure left to you. I find that idea rather amusing.”

Paul said nothing. What was there for him to say? Anything would be dangerous.

“Why so quiet Pauline,” Gloria taunted, “perhaps you would like me to strap on a dildo and make love to you as we women do?”

Paul blushed deeply at the suggestion which seemed to touch a cord deep within him. Did he really want that, or was it just the suggestion that his mistress would make love to him? He lowered his head shamefully unsure of what he truly felt.

Gloria stood up, smiling knowingly. “Undress me, girl,” she ordered.

Paul moved forward and began a most familiar – yet ever nerve-racking task. It occurred to him briefly that he should be glad his mistress had suppressed his manhood, for at least he could not offend her in that way.

As item by item was removed with infinite care, the splendours of his mistress’s body were revealed. Always it gave Paul a sense of awe. No matter what she had done to him, he idolized this woman. To have been given an order just to kiss the tip of one toe would have delighted him.

Naked, Gloria moved slowly and gracefully to her dressing table. There, while she removed her make-up, he brushed her rich dark hair. Long and lustrous. This was another delight for Paul. It is a long time he thought since she beat me. Indeed, the new smoothness of his bottom was unmarked. Perhaps there is no longer any need . . . because I am now the perfect slave who satisfies all her wants. It was, indeed, Delia who had made him writhe in torment under the rod and lash. He was glad indeed to have escaped from that vicious, buxom blonde . . . to the haven of a mistress who punished – but who punished with justice and not simply for her own amusement and sadistic gratification.

For, whenever my mistress has made me suffer, he reflected, it was to further my training or because I have truly deserved it. I have failed her, or disobeyed her, and that is not permitted to a slave. It merits punishment. Paul felt an almost irresistible desire to bend and kiss the smooth, creamy-white back so near him. It would have been an act of reverent gratitude for Gloria’s principles. He resisted the temptation.

Such an action, he was well aware, would rightly have earned him a most memorable ‘good hiding’.

“Pauline,” said Gloria, stretching her arms high and wide, uplifting her voluptuous breasts, “your mistress is feeling a little perverted tonight.”

Paul’s nerves tingled. “Yes . . . Ma’am?” he said.

Gloria smiled into the mirror, lowered her arms and firmed her breasts upwards. “Yes . . .” she said, “sometimes your mistress likes to have a girl to please her. Her maid, for instance. You, I mean. They call it lesbianism, I believe!”

“Yes, Ma’am,” said Paul, his pulses now pounding.

So I am now going to bed,” said Gloria. “You girl, will go to your room and get undressed. Everything but your corset and stockings, that is. Then you will come to my room and, on your knees, ask if I am still in the mood for your services.”

“Yes, Ma’am,” said Paul. There was now true adoration in his voice.

Of course, he had often enough served Gloria in this way in former days. As a male slave. He was also aware of the regular attendance of slave-girls to his mistress’s bedroom at night; he had little doubt as to the service they performed. But he had not done that for a long while. Now however, he was not really serving her as before. He was also serving her in a female capacity . . . and that was different. He remembered vividly how often Gloria had taken ecstatic pleasure in having her maid ‘please her’ in England. It had always seemed to Paul that his services were second best. For Gloria was indeed a true lesbian. Now though, he would be pleasing her as she basically wanted to be pleased. Because, to all intents and purposes, he was now a woman!

He curtsied and left the room as she moved towards her bed.

* * *

Paul knelt naked by the bed, feeling the hair of his blonde wig brushing his shoulders. He was glad his skin was now so hairlessly smooth. Proud of his swelling breasts, now fast getting beyond the girlish stage.

“Your slave is here, Ma’am,” he said, “ready to serve you as you wish.”

Gloria was sprawled elegantly on the top of the black satin covers of the bed. Her eyes swivelled slowly to him. They were half-closed, cat-like, slanting. They had a liquid look about them. Paul got the impression she may have taken some drug, possibly to heighten her pleasures. His blood was racing at the thought of being able to please her so intimately. There was painful pressure on his genital-restraint, of course, but he had become quite accustomed to that. It was now part of everyday life. Just as was the impossibility of ever getting any release. Fortunately, the desire for that seemed very gradually to be lessening. Probably something to do with the female hormone injections.

Languidly Gloria stretched out a hand and lightly fingered one of Paul’s breasts. He could not control a shudder. A shudder of delight.

“You’re getting quite pretty, Pauline,” she said “you are growing up . . . .”

Paul’s head reeled. His mistress had paid him a compliment! Had she ever done that before? No . . never . . . never! It was an almost ecstatic moment for him. He bowed his head.

“All I wish is to please you, Ma’am,” he said. “In any and every way . . . .” He meant it. Absolutely.

“You’d better,” said Gloria reverting to her usual manner. “You may come on to the bed, girl.”

Heart hammering, Paul insinuated himself into the world of soft-scented, womanly luxury.

“You will begin with my breasts, using both your mouth and your hands, ” said Gloria.

“Yes, Ma’am,” whispered Paul. These moments of supreme delight seemed, at the time, to compensate for all his sufferings. He bowed his head into the lush warmness of the resilient flesh and went about his exquisite task. Gloria’s reactions, he noted, were more pronounced than usual. No doubt because, looking at his blonde head and feeling the new softness of his hands and his body, she was actually thinking of him as a woman.

Ten minutes later he was ordered down between the long, luscious thighs . . . down to the liquid-warm delta of silk in the valley of bliss. He was not only at the centre of all his desire, but at the fountain-head of all the female power over him.

Paul could not possibly have been more content.

And, something like half an hour later, one could have said the same of Gloria. Having ordered her servant from her bed, she slipped down into a deep, contented sleep . . . while, Paul went away to dream again of the services he had been permitted to render.