Vacation of a Lifetime

I should tell you something about myself. I’m kind of a loser. I have a good job but all I do is work. I don’t go out with friends or women or do much of anything outside work. The other thing is I’m approaching fifty and still a virgin. I know, what the hell?! You’re probably wondering how that is even possible. My only outlet is online porn.

I think my problem is I’ve wanted to be a girl as long as I can remember. I remember having dreams when I was younger of being a lesbian before I even knew what that really meant. They weren’t so much sex dreams but being turned into a woman by some magical means. I never pursued these dreams. It was to much work or I was scared or who knows. I just kept those thoughts secret. Over the years as more and more opportunities were made available online through chat and games I explored these desires. As the years passed I tried more and more kinky things. My desire for being with another woman evolved into wanting to be with men too. In the abstract at least. I didn’t find men sexy in real life or did I want to be with them as a man. If I was woman though that would be okay.

This past summer I had a chance to go the vacation of a lifetime. I was going to a tropical island that had a reputation for strange things happening. When we got there we were divided into two groups. Not men and women but a mix of both in each group. There were more men in my group but a few women as well. I also noticed that all us men were rather small compared to the men in the other group. We were taken to a building and left in separate rooms. A voice of a woman keep over a speaker and asked me to get undressed. I was hesitant but then it was like she was in the room talking to me. She was saying “you want to be a woman”. “Don’t deny it, I can see your thoughts”. This should’ve freaked me out but it didn’t. I undressed and waited for what came next. Suddenly the room was filled with pink light and it bathed my body. I could feel myself changing. It was slow but I was getting shorter. My skin was getting smoother. I looked at my hands and they were softer and my nails were growing. Next my new breasts developed. They weren’t big but they felt nice. I could feel my face reforming into something very cute. I don’t know how I knew that but I just did. My hair got longer and turned brown. Suddenly I stood there as a transgender woman. I still had my penis. This didn’t disturb me because I had fetishes of being a woman like this too. If this is were how I ended up I would be fine. Then the final changes took place. I felt it and looked down to see my penis shrink down to nothing and then go inside as my new vagina formed. The other change that happened that I wasn’t aware of was that I got much younger. I was now in my early twenties. The first sign of this was that I felt so good. No chronic pain in my body anymore. I was alive and young and all woman. The light went off and a woman came to lead me out of the room. I joined the rest of the young women in the hallway and followed them to a dormitory.

My vacation was over but my new life was just starting. Over the next weeks and months we learned how to be women. The women who started out with us at the beginning were our teachers. I took to the training right away and excelled. I had pretended to to be a girl so often that besides actually putting on makeup and wearing dresses I already knew how to act like a woman. At least this kind of woman. We were being trained to be trophy wives. I couldn’t wait to meet my man and please him in every way. Finally the day came. We would meet our new husbands and start our new lives for real. I nervously walked to the bungalow where he was waiting. I got undressed outside and put my hair up in cute loops and then I walked up to the open door and walked in doing a sexy twirl. There he was lying on the bed. He was naked and stroking his cock. I crawled onto the bed to join him. I felt his muscled legs. So firm and manly. From his broad shoulders to his six pack abs he was every girls dream and now he was mine. I lowered my head to his cock and licked it. We had not been taught about how to do this it just seemed to come natural. I gave it a few licks and then opened my mouth taking him in. I slowly lower my head onto him taking more and more of that delicious cock down my throat and swirling my tongue around it. From his moans I could tell I was doing it right. I loved it, I couldn’t believe it had taken so long in my life to come to this point. I was meant to be this woman. I licked and sucked and played with his balls until he came in my hungry mouth. I took all his cum and licked him clean. Then I opened my mouth to show him all his cum before I swallowed it. I then crawled up next to him and he put his strong arms around me and I felt safe and wanted for the first time in my life.


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