A Holiday Worse Than Hell

Kate put the bra on me and as I was obviously without breasts, the bra had molded padding. The knickers, thankfully were just normal and again I stuffed my cock back between my legs. The dress slipped on quite easily. It had thin shoulder straps, a long back zip and was quite short. The material had quite a bit of stretch to it. So when the zip was done up the material tightened around my whole body, from my bum to the chest. Thanks to the padding in the bra, it actually looked like I had a couple of sweet little boobies. As the shoulder straps of the dress were thin, it was easy to see the soft pink bra straps as well.

Kate handed me a pair of strappy shoes with small heels. Once on Kate looked at me, laughed at my stupid hair that hadn't seen a barber in years. She brushed my hair and a couple of times she used a pair of scissors. Once she was happy, she passed me a pair of big sunglasses. Once those were on I actually looked like a lady.

Without a minute to loose, Kate had us walking very fast down the road to catch a coach for a day trip. I asked where we were going and Kate replied Simi. At the bus stop we met up with Zoe and Megan who were very interested in my dress and heels. Megan took out some lipstick from her bag and motioned to put some on me. I moved back, but Kate said let her. Soon I sported some pink lipstick to go with the dress and underwear.

Sitting down on the coach and I then realised how short the dress was. I uncomfortably pulled at the hem in the vain hope it would go down an inch or two, but it just wouldn't. An hour later we were boarding a ferry from Rhodes harbour to Simi harbour.

Kate insisted on sitting on deck rather than inside. That was fine for the girls as they all wore jeans and had cardigans and jackets. It was bloody cold out in the open waters for me though. I had goose bumps on goose bumps. I just looked like a lady incorrectly dressed for the occasion.

Simi was a beautiful island and the town was all lovely pastel shades. We had a wonderful time and I completely forgot about what I was wearing. I think it was starting to annoy Kate, me doing these things and carrying on. It gave me fresh energy to keep doing the dares and tasks, and maybe she would give up, in the knowledge that I was the prank master.

That evening we eventually got back to our resort and we fell into our restaurant. Nicos was so surprised by what I was wearing. He was really impressed with my figure. Soon Kate was taking more photos of the two of us. We enjoyed yet another lovely meal and I went to pay with my card and it was declined. Kate verbally laid into me, telling me how pathetic I was, spending my money on a silly hire car. She pulled out her credit card and paid. Nicos spoke to Kate in Greek and they sniggered and laughed. Later I caught Kate joking with Zoe and Megan but I was out of ear shot.

The next day was a quiet one by the pool. I couldn't possibly wear any of the bikini bottoms Kate offered me, so wore a pair of linen shorts and just stayed on the side.

As five pm came along, Kate insisted I get ready for the evening. It was really early, but did what she asked.

Soon after a shower I was wearing white bra and knickers, a short denim skirt and a t-shirt and heels. Kate rushed me down into town and we were back at the fish restaurant, almost an hour before opening. Nicos was there and greeted us. I was whisked to the back after Kate said goodbye. I didn't have a clue what was going on until Nicos insisted I change into a bodycon black mini skirt and a sheer white blouse. Nicos explained that because I couldn't pay for the meal the previous evening, Kate decided I needed to do some waitress work.

Once dressed, my white bra was in full view and the skirt hardy covered anything. Nicos then showed me where the kitckens were, the menu, how to take orders and where to take them.

Halfway through the evening, Kate, Zoe and Megan turned up and I was tasked with showing them to a table. I could hear Zoe saying, the way I looked was a vast improvement and Megan even said she could fancy someone like me. Later I over heard Kate say, I think we can do better, whatever that meant.

That evening I ended up serving all the noisy and loud groups of men and regularly had my bum grabbed and felt. A couple of times, my blouse was almost ripped open. I realised it was quite a meat market. Later on, one of the noisy men grabbed my waist, and In full view of Kate and her table, the man plonked me on his lap and proceeded to snog me. I tried hard to get away from him, but he was massively stronger and I couldn't get away for a good five minutes. His hands went almost everywhere. It was awful and he stank of body odour and lager.

The only other table to give me trouble was Kate and Zoe. Megan was as nice as pie, but the other two kept pulling me up or getting me close enough so they could pinch my bum. That night, once back at the apartment, Kate laid into me again for being a complete tart with that bloke. She saw me kissing him and sitting on his knee. Once things had calmed down I slept so silently as I was utterly exhausted.

In the morning, I was allowed a little lay in, but before long Kate was chivvying me to get up and get dressed. Kate was going all out today to embarrass me I thought.

After the shower, Kate gave me a thong and a matching lacey bra. Once those were on, she gave me a tiny skater dress in a bright orange colour. The top half was skin tight and then at the waist it flared out and the hem was literally only an inch or two below the base of my knickers. Having been given a pair of shoes with a two or three inch heel, Kate took me into town. As we walked the skirt swung from side to side.

Once in town, Kate looked at a scrap of paper and soon we were walking up a small side alley and Kate knocked on a door. The door was a simple and boring back street door painted white. But once inside, there was a counter and the room was well lit. I didn't have a clue what this place was until we were directed into a room that had what looked like a weird lady beautician come doctor. I found out later that Greece has a subculture of unofficial doctors doing abortions and other things. This doctor had been struck off year before, so work hidden from the authorities. Kate demanded I sign a form that had been thrust before me and then to strip off behind the curtain. I wasn't going to argue as still I believed I should follow through with whatever Kate chucked at me.

Soon I was laying on a gurney with the medical person looking me over. Kate chatted to her in Greek. Before long a sort of screen was put up at my neck height, so I couldn't see the rest of my body. I could feel the lady give me a couple of injections. Soon I felt my groin go numb as well as my chest, but wasn't alarmed as Kate was there watching. I must have been laying there an hour, with assistants coming and going. All I could feel was being prodded and poked a great deal, but eventually the beautician/doctor said in perfect English "All done."

The screen was removed and the first thing to take my eye was that I had two large breasts. Seriously, I had boobs. Kate saw my face and said not to worry as they are just saline injections and would go down in a week or two. The biggest shock though was to follow. Between my legs my cock was gone, completely gone. All that was left, for want of a better word, was a ladies gash. I panicked but Kate assured me my dick was ok, just under the surface of the skin and when I pee, it will come out of the gash. Kate went on to say that the medical stitches will come out in a few weeks and everything will be back to normal.

I asked Kate why she had done this and she said "You WONT be playing with that old lady again will you! Your life revolves around your dick so I thought, lets see what your like without it for a couple of weeks!" She then gave me the skater dress to put back on. I waited for the underwear, but Kate said "Don't you remember. You said to me many times that women don't need underwear."

Carefully I put the dress back on and the boobs stuck out alarmingly from the dresses cleavage. And when I looked down it only just covered my private area, but now without any knickers, any breeze would show everything!!

The rest of the day was spent around town going from shop to shop. Kate bought me a denim mini skirt and a tiny bikini. It was Karma.

The next morning, I wasn't given any chance of a lay in as Kate demanded I get up and we go to the pool, with me wearing the new tiny bikini. I put the bikini on and it really was a joke. The bikini bottoms tied at the sides and at the back was just a string in my bum crack. the front was tiny, but as I had no hair, thanks to Zoe, it fitted fine. The bikini top, also tied, had tiny triangle and only really covered my nipples.

Setting up on loungers by the pool, I seemed to attract every male pair of eyes in a one hundred yard radius. Some simply stared while others looked like spies, peeking over their newspapers or round the side of their books. My every move seemed to be important news to every man.

Kate was smirking at my situation, but I could tell she was really getting cross as I just played along and didn't get upset at what she was doing to me. At one point, Kate had me laying there topless and I was just waiting for the moment when a guy fully clothed would fall into the pool. Kate now wondered how far she could push me being topless. First she got me to go for a swim. The tiny thong really covered very little and in the water at any moment could slip off.

After the sun had dried me off, Kate instructed me to go to the bar and get a couple of drinks. The bar was next to the main road and so I would be standing topless only a few feet from lots of people. As in reality I was a guy, I wasn't embarrassed about showing my boobs, so I just got up and went for it.

For the rest of the holiday, I was made to wear mini dresses, mini skirts and sheer tops, with absolutely no underwear! You cannot imagine how many times I was propositioned by men and boys. They literally just treated me like a sex object. Kate, Zoe and Megan loved it. Thankfully though Kate made sure I didn't get into any trouble.

We woke on our final day and started to pack. Kate demanded I wear a bikini and short sarong for the return trip home. I closed my eyes and was about to say "please no!" when I saw her face with a gleam of victory in it. So I agreed and her face fell.

Standing waiting for the coach in a white string bikini and a flowery short sarong, this holiday had been very weird. I wont forget this holiday in a rush. The coach arrived and we were off to Rhodes airport.

The flight was the usual end of holiday quiet trip with everyone thinking of the return to home and work. Kate and I were the last to get off the plane as we were at the back. As I got up Kate undid the side of my bikini bottoms and pocketed them. I was now just standing there in the bikini top and a short sarong tied at the side. Before I could say anything, Kate was pushing me down the aisle. Walking through Gatwick almost naked was a very strange experience.

I was expecting all sorts of problems at passport control, but when we got there, Kate showed me the new automated system. When getting our passports a photo of our retina had been taken and fingerprints. So at the automated system, it read our eye and index finger and we were through.

We got the case and nipped to the lost luggage to see if my case had returned from its trip to Nepal, but it had not. They assured us they had our details and when the case came back, we would be informed.

I was expecting us to head for a taxi home, but Kate told me we were catching the train!! For this holiday, Kate really made me suffer and I needed another holiday to get over it.