We thought we were so clever. Jerry won two tickets to a remote Caribbean Island couples resort. The type that guaranteed to reconcile a floundering relationship. The type that only accepted couples. When Jerry’s ex-girlfriend Hannah declined to go we figured we could have a little fun with it. I’d dressed up as a cheerleader for Halloween and had been told that I was actually passable. I still had the makeup, wig, and body shaping undergarments and a simple purchase of some regular women’s clothes finished up the look. It took all our willpower to not break out into laughter anytime someone called me ‘miss’ on the plane ride down.
The sign in process was simple… we were shown the contract and had to sign it. There was a lot of legal mumbo jumbo but at its heart we were agreeing to any method they saw fit to reconcile our relationship. Most of the details were already filled in with Jerry’s previous attempt to get back together with Hannah. He had to learn how to accept her life choices and she had to learn how to be more pleasing and sexually open. I Imagined sitting in some sort of group therapy with a bunch of girls talking about sex and I thanked God for that gaffe holding back my cock as it tried to raise up into an erection. This was going to be SO hot!
After that Jerry and I parted ways. They told us we’d see each other in two weeks. That’s when the nightmare began. My first stop was their beauty salon. I guess my masquerade wasn’t good enough to fool these professionals as they kept telling me through their work that there was nothing wrong with a man wanting to be pretty and feminine for his boyfriend. When they put me into the chair they actually strapped me down. The team came in and I must have had eight people working on me. Washing, styling, and weaving extensions into my hair. Cleaning up my fingernails then attacking long blue fake nails. Cleaning up then painting my toenails in a matching blue. Exfoliating and softening my face. Massaging and rubbing down my entire body. When it was all said and done I looked far more feminine than I had when I walked in. I had no clothes nor makeup on to fool the eye… but I looked like a girl.
I broke down and tried to tell them that this was a mistake. That this was already going to far. That I didn’t want to be made feminine and pretty. But they just chuckled and reminded me of the contract I had signed while they wheeled me to my next stop. A doctor gave me a thorough examination and then injected me with what he called a special blend of high powered hormones. As I cried he told me that I should have budding breasts in just a week. He guessed that in a month I’d end up somewhere between a B and a C cup.
After the long day I was finally guided to my room… but there was no rest for me there. I was strapped down into some kind of machine and a VR visor was placed over my pretty face. My protests were silenced when what I could only imagine was a dildo was pushed into my mouth… although my muffled scream of surprise was still loud when they pushed another well lubricated dildo into my ass. All night the VR visor and dildos forced me to experience sex with men, all from the woman’s perspective. I kneeled before them and took them in my mouth. I laid down on my back and took them missionary style. I went on my hands and knees and took them from behind. Each time they came I was fed a chemical flavored ‘cum’. By the time the sun came up I must have swallowed a gallon of the stuff and had so much injected into my rear that it was leaking out and dripping down my thighs. Through the entire night I also heard a voice. She told me that it was ok to be pretty. That I wanted to be pretty for my man. That I wanted to be sexy for Jerry. That I loved Jerry. That I loved sex. That I loved pleasing my man orally. That I loved my man fucking me. Over and over and over, all night long I was fucked while a woman told me that I loved it.
The entire week went like that. Beauty enhancements and body modifications all day, VR sex all night. It seems all of my nutritional needs were being met by my ‘lovers’ at night as they never once fed me. And when I did drift off into sleep my dreams were filled with men making sweet love to me.
After a week of treatments, I was told that I’d be meeting Jerry. I held on to the smallest hope that Jerry could break me out of this horror show and that we could escape this nightmare island. I was placed out on a lovely balcony and saw the results of their week of beauty treatments. With my little clitty pulled up between my legs there was no telling that I wasn’t a woman. The injections had indeed given me small perky breasts with oh so sensitive nipples, but it hadn’t stopped there… my waist was pulled in while my hips flared out. My ass was cute, pert and jiggled perfectly as I walked. You couldn’t see where my hair ended and my extensions began. And with only some lipstick and a little eye shadow my face was more feminine that most women I’d ever met in my life.
When Jerry was guided in they told us we had the afternoon together. When Jerry looked at me I could see his erection grow, but the same time he started to cry. He came to me and pulled me close in a hug and started to blubber out an apology. Before I could scream or cry or accept his apology he guided me over to the couch. In horror, I watch him strip off his clothes and lay out on his back. I tried to struggle against the instincts they’d placed in me, but I still found myself kneeling between his legs… a beautiful smile on my face. As I grabbed his cock and started stroking it up and down it felt so familiar. The familiarity came from doing this same thing in VR several times each night. My stomach churned as I realized what would come next if I couldn’t break free…. We’d chat a bit, laugh, cry, profess our love for each other, then I’d lean forward and take him in my mouth. But this wasn’t VR. This wasn’t a dream. This was Jerry’s hard, hot, amazing cock in my hand.
When I finally got up the strength to tell Jerry that we had to get out of here, the last bit of my hope died. The look in his eyes told me there’d be no leaving or escaping. His words confirmed that he had gone through similar training. “Leave? But Hannah the program is working so well. I promise I won’t make a fuss anymore about your life choices… I’ll support you being as feminine and lovely as you can be. And if you want I’ll pay the extra money so that they’ll make you all woman before we leave. No more embarrassment over your little clitty, I promise!”