A Holiday Worse Than Hell

Hi, my name is Maxwell, but everyone calls me Max. At twenty six years old, ladies tell me I am fit! Unfortunately its because I do lots of marathons and distance runs rather than the way I look. My hair though is pretty long and all females seemed to like it. Kate, my amazing girlfriend of five years says I am sexy, but then she spends half her time taking the mickey and I never know when she is serious or not. In fact we really rib and prank each other as often as possible. Kates only weakness is jealousy. She seems to think, just by me talking to other women, I am trying to get them into bed. So she can be a bit possessive. I do though have to say that the erm, physical side of things is fantastic as we try most things. Plus she liked that I had quite long hair. She said it made me look a bit "Jesus".

Anyway, we had a holiday arranged. It was going to be late in the year (October) as work had been crazy in the summer. At least it would be two weeks on the Greek island of Rhodes. Temperatures would still be pretty good and the resort was quite a chilled out place. The apartments we booked had their own bar, restaurant and pool, and wasn't far from the beach. Plus there wouldn't be any kids about as it wasn't a school holiday.

We packed our two silver matching cases. I offered to pack for Kates and put in just a few tiny bikinis, but she said no. I did have a big bag of rice handy, if I had the chance to pour it in her case for a laugh, but nothing doing. Once all packed we had an early night, ready for the taxi to Gatwick early in the morning.

All bleary eyed we showered and breakfasted. When I was about to dress, Kate suggested I go commando in my black linen trousers. She had a wicked grin on her face which made my dick jump to attention. So without any thought I did as she asked. Walking out to the taxi in just linen trousers, shirt and flip flops, October was damned cold in Britain.

Gatwick was nice and quiet as we waited to board our plane. Kate was her usual mischievous self and in a café she was rubbing my cock through the thin linen material. As our plane was called, I had a very difficult walk to the gate.

The flight was three and a half hours and in Kates mind, to stop me talking to the stewardesses, she insisted on keeping one of her hands warm in my trouser pocket almost the whole way. She worked my cock through the thin pocket material. If there had been a chance for some action there and then, my cock would have exploded almost straight away.

At Rhodes airport we waited with all the other passengers for the luggage to come out. The first of our silver cases came out and it had my red label on it, so that was mine. Then we waited and waited and waited. Kates case didn't come out and we were still there when the next plane arrived. Dejectedly we headed to the lost luggage. I had to act sad as inside I was laughing my head off. The only clothes you can buy in these resorts is either grossly over priced designer stuff or tiny bikinis, mini skirts and sarongs. I carried on acting sad though in support of Kate who looked pretty down. As we spoke to the lost baggage office, Kate said all her expensive makeup and creams were in that case and as it had been a last minute trip, we hadn't got travel insurance.

After giving the people our contact details and where we were staying, we headed to the coach that would take us to our resort, down on the south east side of the island.

While sitting at the back of the coach in a corner on the journey, Kates hand wandered again. I had received five hours of this treatment now and my penis needed no encouragement. She didn't do anything crazy, just kept giving my manhood lots of attention. When the coach stopped at our resort, I again had to walk down the coach carefully or I could have poked someone's eye, I was so stiff. Kate was smiling and I was glad she had perked up from the disappointment of her lost case. We got our one case and headed in to the apartments reception.

The room was fine, after all it wasn't five star but it was clean and it was tucked away in the corner of the apartments. The pool looked really inviting and after the flight, a refreshing swim before unpacking would have done me good, but Kate had other ideas. After locking the door and pulling the curtains, she came over to me and pushed me towards the bed. I could see aggression in her eyes and I had no intention of stopping her. From experience Kate knew I got excited if she started ripping clothes off.

She grabbed the front of my shirt and pulled all the buttons off in one go. Turning me around, there was a small pleat at the bottom of the shirt at the back and from there she ripped it off me. "Bloody Hell!" I thought, but she wasn't done with that. I know linen isn't the strongest of materials, she literally tore the trousers off me, leaving them in tatters on the floor. My cock was so hard it was almost painful. I was then pushed onto the bed, next to the towels made into a swan. She knew I wouldn't last long so she prolonged things by yanking off her knickers and moving her body to my face. There hidden by her denim skirt was a beautiful sight and soon she had me eating and licking. Kates hands moved to my nipples and she tortured them with several pinches and twists. She liked me groaning with pain while my mouth was engaged down there. All too soon Kate flinched once, twice, then came. That signalled her to now see to my rock solid cock. With deft hands and tongue, I all too soon had shot an almighty load.

Once we had come down from that high, Kate suggested I unpack while she throws my torn clothes in the big rubbish bin we passed as we came in, and I agreed.

I was just thinking about going for a swim as I unlocked the case. Also knowing we would need to go shopping for some fresh clothes for Kate. Swinging the case open, I was in shock. Kate came back into the room and asked me if everything was ok? I blurted out "Its your case not mine! Its your case!" Kate burst out laughing, a real loud belly laugh. I looked at her, but she couldn't stop laughing.

Eventually she admitted she had planned everything and switched the labels on the cases as I slept. I asked where my case was and she said "Rhodes airport is RHO and I changed it to RHP. So your bag is on its way to Nepal!" I sat there on the side of the bed, totally naked with just my flipflops of my own.

As Kate unpacked her things, I had to ask "But if you planned this, what am I going to wear for these two weeks?" She replied "Oh, don't worry. We are about the same size, you can wear some of my stuff as I have brought plenty." I asked "Are you kidding me?" but she wasn't. Kate went on to say "This makes up for that time you stole all my underwear while on that holiday to Spain! And that time to Cyprus you replaced all my clothes with mini skirts and tiny bikinis! And that time in France where I had to fly home in a bikini!" She reeled off another half a dozen instances of me pranking her. Then she said "This is the first holiday in years, I can be comfortable with what I am wearing. So suck it up buttercup!" And she burst out laughing again. "Maybe this time you WONT be chatting up all the other women we meet!" she said.

I asked where my clothes were that had been torn off me. Kate replied "In that big bin we passed on the way in. I wouldn't go near as when I threw your rags in, they landed in some rancid yoghurt and coleslaw." She carried on unpacking.

Thinking about the situation and all the years of pranks I had done on Kate, I was amazed she was still with me. So I determined there and then to follow this through and do what she asked...whatever! But did I have the guts to go through with it?

As it was still only mid morning, being naked I obviously stayed around the apartment as Kate made us both a coffee and then once changed she was going to head out to the pool. Before she left, I asked what about me. She sniggered and then said that she had packed stuff for me as well. She explained "On the right in the wardrobe are a few pairs of ladies linen trousers, shorts and a few nice blouses for you to wear. Also in that drawer are some knickers that should fit you. And in the drawer down are a few bikini bottoms that you should be able to get away with wearing."

When she was ready to go she looked at me and said "Are you coming?" I went to the drawer that she had pointed out and inside were some bikini bottoms. One pair had a black and white pattern on them. The second were a bright metallic blue pair, so I kept looking. Third was a pair that were a deep red that was almost a deep pink. This was followed by a blue and white gingham check pair and finally was a plain black.

I grabbed the black pair and slipped them on. At the front there was less material than a mans trunks, but as the material was more stretchy it seemed to cover what was needed. BUT, something I wasn't aware of was than women's costumes have just a single layer of material. My cock and balls could be seen clear as day pushing out of the stretchy material. Kate had a good snigger as we left the apartment and stroked my cock through the smooth material.

We set up camp on a couple of loungers by the pool. The bar was on the other side. We rested there, covered ourselves in sun cream and soaked up the October sun. I looked round the pool to see who was there. Next to the bar were three mature ladies who were a bit loud and dare I say getting tipsy this early in the day. Other than that there were a few couples who were either deep in a book or fast asleep.

When I got too hot, I went for a swim. Thankfully the water helped me cool down on this first day. After swimming about for a good ten minutes, I rested by hooking my arms on one of the sides of the pool.

I must have actually fallen asleep in that position as I was rudely awoken by a hand cupping my dick and balls through the thin material. I looked round expecting to see Kate but it was one of the mature ladies. Before I could say anything, her hand went inside my trunks and in an everyday voice said "Hi, my name is Rose."

"M, M, Max!" I tried to reply. "Well hello M, M, Max, and may I say, its a lovely item in my hand." Rose looked a charming lady of about 65. She cared about how she looked and her makeup and hair were just so. My cock went rock solid. Roses eyes lit up feeling my penis harden. My brain was trying to think how to get out of this situation, but my cock definitely wanted to stay there.

Just then Kate shouted to me did I fancy some lunch. Kate was giving me the evil eye and also shot a nasty glance at Rose. Roses hand was gone in a shot and she swam as if we had not spoken. I got out and we sat in the bar eating baguettes with cheese, meat and salads. The rest of the day was pretty quiet as we were tired from the travel. I did suggest we go to Rhodes town to get some "man" clothes, but the look on Kates face answered that. We stayed around the pool that afternoon and had an early night as we were exhausted.

On our second night we decided to go out for a nice evening meal at a fish restaurant. Before I could investigate my clothing options, Kate insisted I take a shower and she would choose my outfit.

In the shower I had to use Kates shower gel, so I came out smelling heavily of lavender. My skin felt nice and smooth though. On the bed Kate had left my clothes for the evening.

A pair of lace white knickers laid on top of some white linen full length trousers. Next to it a brown/grey shirt. Kate said "Come on, I am ready, Buttercup!" I grabbed the knickers and pulled them up in a way that I hoped would rip them. But they fitted fine apart from going into my bum crack as I pulled them up too hard. The linen trousers were next and they also fitted, in a manner. There was plenty of room in the legs but they cut between my legs really tightly and pushed the knickers all the way into my bum crack.

Both Kate and I looked at them and Kate told me to push my dick down between my legs. The knickers seemed to hold my bits in place and the trousers fitted quite a bit better, although now with a flat front and still cutting my bum cheeks apart. Finally the shirt, well blouse as the buttons were on the wrong side. As I picked it up I could tell it was made of silk. As I buttoned it up Kate said it was a mushroom colour. Brown/grey to me, but hey. The blouse had plenty of room and to be fair was perfect for a warm evening. I put MY flipflops on and we headed to the restaurant.

Luckily at this time of year, as well as no kids about, there were very few groups of lads or lasses out getting drunk. We enjoyed a lovely meal in a fish restaurant with a couple of bottles of wine and found a bar to "people watch" the evening away. It was only as I sat in the bar that I realised I was wearing purely ladies clothes and no one had said anything or given me funny looks. I definitely relaxed a bit after that.

On the next night, we decided to go again to that fish restaurant. Like the previous day I showered in lavender. When dry, on the bed was my outfit for the evening. Another pair of white linen trousers, some white knickers and, "Oh god!" I said to myself, a bright red semi sheer chiffon blouse. I looked at Kate and all I got was "Come on Buttercup, I am ready! You shouldn't play with women in the pool!"

First trouble was the white knickers as they were a thong. I did the trick from the previous night of pushing my dick and balls between my legs and there was just enough gusset in the knickers to hold my bits there. I picked up the trouser and then spotted an issue. Kate was stifling a laugh, as she admitted that the zip was on the side. I had no choice and put them on. As I pulled up the zip, around my hips and crotch, these trousers became really quite tight. Again, between my two bum cheeks, I could feel the material from the trousers cutting in. This was made worse by the white thong. My heart was pounding as I picked up what was clearly a blouse and not a shirt. I did up the buttons and it was pretty loose on me. I made the mistake of going over to the mirror to have a look. The red, was really bright and I could see my nipples through the material. That wasn't the worst of it though. I looked at the linen trousers and they were see through. The white thong could easily be seen and when I looked at my backside, it didn't look like I was wearing any underwear. As I stood there, Kate reminded me of a time in Italy when I got her to go out in just a see through dress. I was determined to follow this holiday through and so we left the apartment.

The air was definitely colder and the chiffon and linen materials were not going to keep me warm. I looked at Kate who had chosen to wear a pair of jeans and a jacket. I thought her jeans must fit me if this other stuff does, so I thought about ways of obtaining them.

Again, Kate decided we sit outside when most of the customers were inside due to the drop in temperature. The meal was just as good as the previous night and we got chatting to the waiter Nicos. As we had our after dinner coffees, Nicos came and asked if my name was Max, Max Dawson? I said, yes in an apprehensive manner. Nicos face lit up and said he had seen my photos in a magazine!! I was so embarrassed.

I need to give a bit of detail here. A couple of years ago, as a prank, my dear Kate had entered me in a male model competition. When I got the news I had won and would be sent a cheque for £500, I was gloating like crazy. After the photo shoot though, I was all sheepish. The photo shoot was for a male magazine. Many of the shots were of me in skimpy swimming trunks and a number were of me naked. It was the most embarrassing thing I have ever done. I am not anti LGBT or anything, just that it wasn't me, or was it?

In front of Nicos, I went nearly as red at the blouse I was wearing. He wanted to shake my hand and asked to have photos with me. As many of the customers had departed as it was late, Nicos then got the chef who also knew me from my photos. I spent ages having Kate take photo after photo with Nicos and the chef. Nicos liked my shirt and then Kate suggested, I take off the shirt for more photos. The two Greek men were well up for that and Nicos almost took the blouse from my back.

Kate was really getting into her stride for wickedness, when after another dozen photos she looked round and the place was deserted so suggested I take off my trousers. I was in shock, but Nicos and the chef were like giggling children. So I didn't get a say at all and soon it was photos of me in a white thong. We stood on the balcony overlooking the town. The side wall was just a fraction higher than my waist, so all the people in the streets down below, just saw me without a shirt on.

As more photos were taken, Kate was suggesting poses and some included Nicos and the chef holding my bum cheeks. Another had both Nicos and chef on their knees with their faces near my groin. I wanted to curl up and disappear.

Kate went in for the kill. Why don't you take off the thong. Nicos and the chef were whooping with joy. She was rubbing in the embarrassment as she now had ALL my clothes on the table and I was in various poses with Nicos and Chef. Kate must have taken a hundred photos of us on Nicos phone.

Eventually after insisting on paying the bill that Nicos wanted to refuse, Kate passed me my clothes so we could leave. What she hadn't passed me was the thong. I looked at her questioningly, but she just waived for me to get dressed. Once the trousers were on, I looked down and the sheer material hid nothing. My cock was like a beacon of silliness and the blouse wasn't long enough to cover it. It made my cock jump into action and I soon sported a massive hard on that anyone could see.

Kate insisted on us walking slowly back towards our apartments and even entered a couple of tourist shops on the way. She got chatting to one old lady that ran a shop. Seems the old lady hated what I was wearing and Kate had explained something to her in Greek which made the lady nod and sit back down behind the counter. Kate picked up a tiny pink bikini, the sort I would have her wear and held them up to my body. The old lady laughed and they chatted some more in Greek. That was the last of that eventful day and we got back to our apartment and headed to bed.

A couple of days later, Kate insisted we head to the local beach. She pulled out the black and white patterned bikini bottoms for me and we headed down to the beach. Down the narrow path we went past a bar/restaurant hidden away overlooking the beach.

After paying ten euros for a couple of loungers, we settled down for the day after covering ourselves in sun cream. At lunchtime we enjoyed a snack and cold drinks from a hut nearby, I was getting hot. So I told Kate I was going for a swim.

The water was crystal clear and lovely. I had been swimming for ages, when Kate came and joined me in the water. We stood up next to each other, the water was above my waist. I could see an idea on Kates mind and she started to stroke my cock through the thin material of the bikini bottoms. She looked back to the beach that was half empty and then started to slip the bikini bottoms off me. I immediately panicked but she said it would make things easier for her.

Once the bottoms were off me, she stuffed them down the side of her bikini bottoms so she could use both hands on my cock. I was in heaven and her hands were everywhere, twitching my nipples, grazing my bum cheeks with her nails and pumping my now rock hard penis. She kissed me intently and being all dominant, she pushed her tongue into my mouth and got more aggressive. I was getting so close to cumming when she let go and told me to finish myself. My cock was aching to cum and my hand finished it off in literally a minute. When I came, I looked up and Kate was back walking up the beach. I was in the water completely naked. When she noticed, I heard her shout "Have a good swim!"