Jon had woken me up because it was time to eat and just then the 'cabin attendant' asked me what I'd like to drink with my meal.
The rest of the flight was quite uneventful – unless you call 2 orgasms as I pretended to watch the film eventful as Jon brought me slowly to, and over the brink twice. I'm sure that the woman knew what was going on, she kept giving me these strange, knowing smiles.
It was fantastic getting off the plane into a very warm, gentle breeze.
When we arrived at the Hotel it was great, very big and posh, our room was on the 15th floor and had a great view out to the sea (looking sideways). It was late at night so we went straight to bed. Jon let me ride him to my 3rd orgasm in the last 24 hours.
Sunday Next morning, my birthday, Jon woke me up by playing with my pussy for a while then lifting my legs over his shoulders and ramming his dick hard into me. I'd woken-up while he'd been fingering me (fantastic way to wake-up), but I pretended to be asleep right until he rammed into me. There's no way I could sleep through that, and Jon knows that.
It was just a light, thin cotton skirt and tight tube top for me to breakfast, and Jon's juices running down my legs and onto the restaurant seat. The skirt is very short and low slung, if I pull it down as far as it will go you can see the top of my pubes – not that it's easy to tell cos I don't have any hair there.
After breakfast we went for a long walk, it was great feeling the warmth of the sun. Jon had to go and meet a business client in the afternoon so I spent it by the hotel pool. I wore a Wicked Weasel bikini that Jon got over the internet from Australia that's so small that a Band Aid would cover more. The material is so thin that you can see the different colour of my nipples and it hugs every contour of my crack and protruding clit. The atmosphere round the pool was a bit formal and I didn't feel like going topless, but I did get quite a few looks in that bikini.
That evening Jon took me to a posh restaurant for a big birthday dinner. Candles, wine, the lot. I was wearing nothing but a very small, white backless dress and shoes, the back of the dress is so low cut that you can see the top of the crack of my ass so it was obvious that I had nothing on underneath. I was half expecting Jon to tell me to wear a vibe or Ben Wa or something, but he didn't. Instead he got me drunk and had to half carry me back to the hotel.
Monday Jon was gone when I woke-up and I grabbed a bottle of water and went out onto the balcony in my usual sleep attire – nothing. I sat there for about an hour soaking-up the sun not caring who – if anyone could see me. Later I put on a bikini skirt and top (no bottoms) and went to a fast food place next door for some breakfast before going for a swim in the hotel pool. I'd only gone back to the room to collect a towel, not to put anything else on, so I had the pleasure of swimming virtually bottomless. The place seemed more relaxed and I flashed a couple of the waiters by lifting my knees up on the sun lounger as they walked towards me. One waiter even went round the pool and came back for a second look. He adjusted the chairs and loungers near my feet so that he could get a longer look. To reward him I opened my legs a bit. I smiled at him as well, but he only saw my lower lips smiling at him.
That afternoon I decided to go to the hotel gym. I needed to get some exercise, and besides, I'd seen a nice 6 pack go in there and I wanted to tease him a bit. I took a pair of Jon's unlined running shorts and a crop top with me to wear. The shorts are way too big for me, so they leave my pussy well exposed when I open my legs. I managed to have a bit of fun and left the place with a couple of men with bulges in their shorts.
That evening we had dinner in the hotel and then stayed in the hotel bar. We sat on this large very soft sofa that we almost disappeared into. My bum was lower than my knees and as I never cross my legs, just about everyone who walked passed and looked could see my pussy. We got amazing service from the same waiter who stared at me by the pool. Poor bloke, his trousers must have been real uncomfortable that night.
Tuesday Jon arranged for me to go on one of those sightseeing tours. I suppose it was interesting, but a bit boring at times. By the end of it I was getting a bit fed-up with an old man who kept trying to get near me and touch my leg. I know it was my fault for letting him look up my skirt, I suppose I should have scared him off by saying,
"come on then, get it out and fuck me right here, you've been trying to for long enough,"
loud enough for the others to hear, but I didn't.
When Jon came back to the hotel he told me that he'd got a bit of a problem, the job there was going to take a lot longer than he'd expected and he was supposed to be flying over to Havana the next day, but he wouldn't be finished Miami. He had to get some software to a client there and they were having problems with their internet connection and they weren't convinced that they'd manage to download it on time. He'd arranged for me to take a copy over there just in case. I was a little nervous as I'd never flown on my own, nor been to a foreign country on my own. Jon told me that I didn't have to do much, just fly in, go over the road to the domestic airport and wait until about 2 pm when the Santiago flight got in. The client would find me. I'd give him a CD and then catch the 3:40 pm flight back. When I asked Jon how the man would know which woman to approach he laughed and told me that there wouldn't be many slim, blond white girls there showing lots of flesh.
We had a quiet night in the hotel bar.
Wednesday Next morning we were up early. Jon told me to wear one of my light, short cotton 'A' skirt and thin white halter-top. The skirt is a low slung one that relies on the size of my hips and stomach to stay up. I did manage to lose it once when I really held my stomach in when I was in a dress shop. No one was around so the effort was wasted – except for knowing that I could do it if I wanted to. I also wore sensible shoes, sunglasses and my Ben Wa Balls (Jon's orders).
After breakfast Jon gave me my tickets, the CD, some money, and put me in a taxi to the airport. Before he shut the taxi door he gave both my nipples a tweak and said,
"don't get your white top dirty playing with them too much."
I smiled at him and we drove off with 2 bullets pushing out my top and a little tingle between my legs.
No problems at Miami airport except that Ben set off the security alarms. This security man moved this wand thing close to me all over, smiled at me then let me go.
The short flight was uneventful except for the vibrations of the airplane bouncing Ben about a bit. It was a good job that I'd made sure that my skirt wasn't between my pussy and the seat.
It was still early when I got to Havana so I went to a snack bar and had a coffee before walking over to the domestic airport. The main airport was quite nice, but the domestic airport is a bit of a run-down dump. I wasn't looking forward to the long wait.
I was wandering around looking for somewhere to sit down and wait when I was approached by a security man. He asked me for my passport and travel documents. After he'd looked at them he pointed his gun at me and directed me to an office that had a man, who looked as if he could be a sergeant, working on a PC. The guard who took me there said some thing to the sergeant then left.
The sergeant kept me waiting for ages before finally looking up at me. His English wasn't as good as the guard who had taken me there. He told me that there was a problem with drug smuggling and that they'd had a tip-off that some drugs would be coming into the country that day. He apologised for interrupting my journey and told me that I must understand that he had to check-out everything unusual and that a beautiful blonde girl, on her own, coming into the country was unusual. He said that he would have to satisfy himself that I had no drugs on me.
He told me to put my bag on the desk and then told me that he was sorry, but he'd have to search me. After being scared a bit by the guard pointing his gun at me I was a bit more relaxed with the nice sounding, apologetic sergeant. When he said that he'd have to search me I have to admit that I got a little excited and my nipples went hard. I could feel them pushing my top forward. He got up and walked round to me and told me to put my hands on my head and spread my legs. He then ran his fingers through my hair and then ran his hands all over the rest of me, and I mean all over me. My nipples tingled as he lingered on my breasts, and when he ran his hands up my left leg he stopped dead when he realised that I wasn't wearing any knickers. He brought his hand up to his face and looked at my pussy juices on the side of his hand for a minute before running his hand up my other leg. This time he lingered at my pussy before putting the palm of his hand on my pubic bone and putting a finger slightly inside me. I shuddered and nearly came but he removed his hand before I did.
Next he went to my bag and tipped it out onto the desk. He looked at my passport and then counted the money. Next he picked up the CD and asked me what it was. I told him but he opened it and 2 CDs fell out onto the desk. One has Jon's company logo on it but the other only had the letter 'V' written on it.
"What's on this?" the sergeant asked.
I told him that I didn't know (which was true), and after a few seconds staring at it, he put it in his PC and worked on the keyboard. All of a sudden his eyes opened wider and then he said,
