Girls’ Vacation
By Maryanne Peters

I just thought that pushing him all the way would finally put an end to this whole crossdressing thing. I had tolerated his crossdressing for our entire marriage but with the kids having left the family home it was as if he had a license to wear women’s underwear constantly, and to act like a woman in the kitchen. It seemed that he had only been constrained by the thought of our children learning of his perversion. My opinion did not matter.

It seemed to me that I needed to push him a little. If you want to be a woman, then maybe you need to try some cock? I just assumed that he would be horrified by the thought.

I mean I have read up on this stuff. Heterosexual transvestites just get a thrill from dressing as a woman. It doesn’t make them gay or trans or anything like that. It is a fetish like some people are into leather, or rubber or raincoats. It does not even make him less of a man. It is just a weakness. But I disliked it … intensely. I wanted it to end. Weakness can be overcome with resolve – that is what I thought.

I formulated a plan to have him go even further, but it could not happen at home. We needed to get away and away by a good distance.

We had two weeks in Cabo scheduled as I read somewhere that there is a place where plenty of men are looking for older women to bed. It was my idea that we should go as two cougars on the prowl. Me and him as her – this alter ego of his that had taken up mincing around our kitchen for his pleasure and my annoyance.

The idea was that we would leave home for the drive into the city as man and woman and then there I had booked him into a transformation boutique to get a full man to woman makeover just before we went to the airport. He would have to explain when he presented his passport while I stood aside.

I have to say that I was shocked by what the beauty team was able to achieve. First, when he explained that he was going to be two weeks as a woman they sold him into a package that included hair extensions and a Brazilian wax, plus breast forms stuck on his chest and a rubber panty thing that could give him a smooth crotch. But the thing that surprised me most was the makeup job – he really did look like a woman!

“Everything is tucked away so well that they tell me that if I take my medication, I will be able to wear a bikini!” he said, almost giddy with excitement

“What medication?” I asked.

“Just something to make me feel girly and to stop my cock from growing into something embarrassing,” he said.

I didn’t want to believe what he was saying. I preferred to think of him as responding to my actions in the same fashion. If you want to push me into being a woman, then I can pretend to welcome it. He was giving it back too, or so I thought. There would be no “medication”.

We took a cab to the airport and the whole way he was making stupid noises with his throat.

“I have received a little instruction on lifting my voice up a little,” he squeaked. “It is all not putting on a falsetto. You have to lift it up just a notch or two and keep it there.”

He had paid the bill and received a bag of stuff from the boutique. He said that it was mainly makeup which came with instructions on the crucial looks that he would need for daytime, evening and at the beach or the pool. He said that it was “worth every cent I paid”. I had no idea how much that was, but I was not happy.

What is in the box?” I asked him, pointing to a package inside the bag.

“It is a little gift of ‘something extra’,” he said. “Have a look.”

But we had arrived and needed to check in so I said I would look at it later.

As I followed him into the terminal, I was surprised that his exaggerated walking style seemed to have been replaced by a more restrained gait. Clearly the boutique must have to him that real women don’t walk like drag queens. Still, there was a confident swing of the hips right up to the counter and the presentation of his passport - Sex: M.

The lady behind the counter just smiled as she held up the passport photo. She was only concerned to see that this document related to this person. It seemed that if he had been painted green, she wouldn’t have shown a flicker of surprise.

On the flight it started. He was shamelessly flirting with all the men he ran into. It was going to get much, much worse.

The flight was over 6 hours but by the time we arrived he was ready to just briefly freshen up and go out for drinks and dinner.

“That’s what we do down here,” he said. “Food and drink are cheap and everybody is out for a good time. I have packed something sexy, and now that I have realistic looking breasts, I will be able to wear it. I hope that you have something along the same lines.”

I had indeed chosen some items that could show off my assets, just to remind my husband that I was still a very attractive woman in good shape, and worth keeping and keeping happy. But what he had looked to me to be just plain slutty.

He set to work applying his evening makeup as he had been instructed. That too, was too much for me. The false eyelashes were massive and totally age inappropriate as far as I was concerned. But what surprised me most was the ease with which he went about his work, and how he arranged his hair just as if he had worn locks this long his entire life.

“I don’t want you making a fool of yourself, and not just for my sake,” I told him.

“Darling, you said that we are here as two cougars on the prowl,” he said. “This was your idea not mine. Now just relax into it. We can have a safe word if you like. Let’s make it “London”. Either of us says the word and we head back here.”

I have to say that I didn’t even know what a safe word was, but the worrying thing was that he seemed to be enjoying all of this far more than I had hoped. I had to believe that he was just having me on, but I was starting to doubt that.

He walked well in heels. I had disliked him wearing them around the house for the sake of the flooring, but he had obviously acquired the skills. I have to say that his legs looked good – shapely rather than muscular. Many women would kill to have legs like that.

We arrived at a place I had booked for dinner. I had heard that this was popular for what I had planned and there were certainly several tables with women only but with four or more seated. Some already had men hovering around, and some had invited men to sit with them.

He asked for a larger table, so we took one with four chairs, and we ordered some drinks and mixed dips as an appetizer. It was not long before a couple of men turned up.

They would have been younger than us, but not by much. They made the usual small talk about what we should chose for a main course and how well we knew Cabo. It turned out that they were American, but they had been to Mexico many times and knew all the best food to eat.

When they asked for our names, I gave them mine and then introduced my fellow diner as “my husband” giving his male name. I guess I did it because he just looked so comfortable and feminine playing at being a woman, and it was beginning to get on my nerves. I wanted these men to know the truth, and to remind my man that what he was, was my man.

He could have been enraged by what I did, but after the two men had walked away, he just smiled and reached out and held my hand. I thought that it was some kind of expression of spousal love, which would have been perfect if it was, but it looked more like pity. If eyes speak they would have said – “You sad, insecure woman. I feel sorry for you”.

But I felt that my words had done their job. I saw the two jilted men in conversation with others and glances our way. My husband’s secret was out, and I was glad of it. But we were not really talking between us by that point.

We took the advice of the men and ordered the barbacoa lamb, but we had barely started to eat when an expensive bottle of wine arrived on our table and the waiter pointed out the two men who had bought it.

“This time let’s just accept the offer of some company,” my husband said. “Everybody in the restaurant will know what I am by now, so let’s just enjoy some meaningless conversation with a couple of strangers.”

I shrugged my shoulders and when they came over I did not object to them being invited to sit with us.

I was glad that they did. The more refined looking one complemented me on my dress and then proceeded to give me some very useful information about local boutiques. You rarely meet a man who likes to shop, but it turned out that this man was in the garment trade. He was very interesting. I hardly gave much attention to his colleague, who was soon in deep discussion with my husband.

The other man was not refined looking. He was powerfully built and had a shaved head, but he was well dressed and apparently quite intelligent. I was aware that he was discussing social problems with my husband, who always likes to talk about such things which usually bore me to bits.

We must have talked for hours. The men bought another bottle of wine and a dessert for all of us. It was like we were two couples, but my husband and I were not one of them. As if to confirm it the man talking with me took my hand.

I would normally have pushed it away – I assume. Such a thing had never happened to me before. I suppose for reassurance I looked across the table to look at my husband. Imagine my shock when I saw my husband kissing the shaven-headed man!

“Actually, we need to go,” I announced loudly. “I am expecting a call from London on the hour, and I need to take it in private. London, darling.” I just needed to make sure that he heard it.

“Oh, that’s right,” said my husband.

We all rose, and the men went to pay our check as well as their own. I protested, but I suddenly needed to go to the restroom. I just whispered to my husband that we needed to pay our share, and then I excused myself.

When I got back both of the strangers had gone, and my husband was standing by a mirror near the door freshening his lipstick.

We walked back to the hotel arm in arm, as a couple might, or two women who are close. We talked about the evening and our conversations. It seemed to me that I should be positive. I had enjoyed talking to the man I sat with, and I had averted disaster by using the safe work in the nick of time.

“Thanks for calling “London” on me Darling, although as it was pointed out to me it is 5:00 am in Britain at the moment,” he said as we walked into our room. “Anyway, I needed to get back here because I have to grab something from the bag I got from the boutique and put it to use. Can you get that box for me while I take a pee?”

I went to the bag and pulled out the box and opened it. To my disgust and horror inside was a kit for preparation to receive anal sex – materials for an enema and a selection of butt plugs in expanding sizes, with instructions and lubricant.

“He has given me a duplicate key to his room which is on the penthouse floor,” my husband called out from the bathroom. He was sitting down and pissing like a girl.

As I stood in the toilet doorway I was going to give him a blast, but I looked at him sitting there, his eyes full of excitement, and I just started to cry.

I had got this all so wrong. I thought that I would be able to end his crossdressing, but all that happened was to end his life as a man.

The End
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© Maryanne Peters 2024

Author's Note: This is a story from my latest anthology of short stories on Amazon - 19 stories set in Vacation or holiday scenes. I will post a blog with links. If you do pick up this book be sure to leave a review on Amazon