Resort Fling
A Vignette
By Maryanne Peters

Him

She was not classically pretty but I thought that she was as sexy as hell. Some men might say that she looked “striking” but I am not sure what that means. She might have been a young 50 or an older 40 but she was younger than my 60. She had broad shoulders an narrow hips but a tight butt, and she had the tits of a teenager – the kind that sit up even when she was not wearing a bra under one of those robes women wear to the spa. She was hot.

Her

I was recovering from bottom surgery in Thailand. For the first time in my life, I could wear the bathing suit I had always wanted to wear – something that could show off my new camel toe. That was something that I had recently paid good money to replace the junk that was now junked in some Thai private hospital furnace. It had taken years, but I was now complete.

I could have gone for some facial surgery too, but I was happy to look at myself in the mirror and see a real face looking back, not some plastic version of pretty. The truth is that I never had much of a chin and I did have good cheekbones. I had been living a woman for many years and I had become comfortable with the way I looked. Plus, my hair was my own and after wearing it long when I first transitioned, I had found a practical length that looked feminine.

I felt that I looked good in my swimsuit too. I was trim and working on a tan after weeks in a bed, and now I felt right. I had a woman’s body at last. I could not help myself running a hand across my crotch regularly just to check that it was flush down there, and almost giggling with joy each time.

I was not looking for sex that afternoon. I was months away from that. There was healing to be done. I was doing my regular dilation, and it was still painful, but it was a pain mixed with sheer delight. To see that significantly sizeable dildo disappear inside me was wonderful confirmation of my new capacity. I could take a man, and while I was still interested in women, I was keen to feel a hot piece of man fill up my new cavity

Him

It seemed to me that her tan was about the same state as mine – more pink – but she was lying in the sun. I asked her if she minded me taking the sun lounger next to hers, as the one I had been using was now in the shade. She said yes in a sexy husky voice that seemed to match her look perfectly. I made a little conversation and then offered to fetch her a bottle of water.

Opening with an apology for being over familiar I asked if she would mind putting some tanning oil on my back and I would return the favor. She seemed happy about the idea. Her hands were strong and they moved across my back with skill and purpose.

When my turn came I was amazed at how smooth and soft her body was, as if every hair had been removed and as if every muscle had been softened. I seemed as if I could feel a slight shudder from my contact, like stroking a captured bird. I found it unexpectedly exciting, and when I backed away that fact would have been visible through my speedos.

Her

He asked me politely, so I applied suncream to his back. I think that it was the first time I had ever run my hands over a man’s body, or rather a man’s body other than mine, when I had one. Somehow the hardness and the hairiness was now exciting, where it used to repel me. The male body was now attractive to me in a way that perhaps I more hoped than expected.

Then when he took turn to apply suncream on me, the touch of his hands thrilled me to bits. The thing is that the extent of my delight was no longer visible, but his was. He was developing an erection, and as he stepped back it was almost in my face. I smiled and thanked him. He lay down on his stomach perhaps as decorum required, given that there were others around the pool.

I felt very pleased with myself. I was a full woman and I had officially turned a man on. I could not help but smile.

We spoke a little about the resort and the country. He seemed an interesting man, but I was only thinking about his cock.

Him

After a while we decided to take a dip in the pool. We were both hot and it seemed that if the oil washed away, or sunning would be over. The day was drawing to a close and I was ready to offer to buy her a drink. We just sank into the pool up to our necks and looked at one another, and we drew closer.

She said that she found me attractive, and that I didn’t have to say what I thought, because she had seen it. We drew closer and our lips touched. There was no mistaking what it was – we had chemistry, as the film directors like to say.

I asked whether she had dinner plans, and suggested that we dine together in the hotel restaurant. She happily agreed. Even in the cooler waters of the pool my cocked swelled a little in anticipation. I had been alone for a while, and here was a definite vote in favor.

Her

I had dated plenty of men, but I always believed in telling them early that consummation was not possible unless they were happy with hand or blow job, or they enjoyed the prospect of giving anal sex, because while I considered myself a woman, in one critical respect I was not one. The thing is that now that was no longer true. I was now confirmed female in body. Now what was I supposed to say?

The fact is that my vagina was still a wound. To use it for sex would not only be painful but injurious. But at the same time, I had one. I hoped he had noticed.

I decided to wince a little and then explain that I had recently had surgery “down there”. I said that I would love to join him for dinner, and would even see matters progressing quickly from that, but that some things we “off the table for now”.

He said that the only thing that would be on the table that night was the meat and some cocktails. He was clearly a gentleman.

Him

It was not until we parted so that we could go to our respective rooms that I started to wonder about the surgery she might have had. I told myself that it did not matter what it might be – I know nothing about a woman’s internal organs. But I had a sudden thought about all of those ladyboys in Thailand, and some I knew had chosen to have sex change operations. Could this sexy goddess I had just met be transgender and in Thailand as a “medical tourist”?

I went to the hotel restaurant and I waited for her for only a little while, but I spent that time wondering how I could ask a question to find out whether I was right or wrong.

When she walked in, I decided that it didn’t matter. She looked fantastic in the gossamer kaftan that she wore with a glimpse of sexy underwear beneath,

She actually apologized for dressing in such a sexy way and said that she hadn’t intended to frustrate me.

I simply asked how long it would be before her new vagina could be put to use. I must have immediately blushed when I said it. It just slipped out. I had not intended.

She gave me an exact date, and 10 weeks following.

I suggested that whatever happened that night we should definitely make that date another date night for the both of us – no matter where she was I would go there and taker her out to dinner again.

She smiled and agreed.

The End
1408

© Maryanne Peters 2025

Author's Note:
This is another one of several “Sissy” images by lindasummers214 on Deviant Art that sparked a story.
Could I please just ask readers to post a comment on this and other stories. Reader participation seems to have dropped away lately, and it is an important of the creative process - for me, anyway.