Me on CD in Havana



Hi, my name is Vanessa. I was born in December 1975 and now have a 34AA–24–35 95-pound figure with blondish hair. In 1998 I quit my boring existence in a little town in North Wales and went to work as a Housekeeper for a middle-aged man in the East Midlands of England. It was a brave decision to make as I’d applied for the job after seeing the job advert in a BDSM magazine that someone had left in the hairdressers where I worked. I didn’t really know what I was letting myself in for, but I really did need to do something because my life was so drab and boring. Even the interview for the job was unbelievable, but I was so desperate to change my life that I did everything that was asked of me, and I was finally offered the job.
Shortly after starting the job my employer (Jon) told me to write a Journal of my new life, and he has since created a web site that it is published on.

http://www. asstr. org/~Vanessa/

If you care to read my Journal you will discover that my relationship with Jon is rather different to that of most employee and employer, but I have easily come to realise that I have a life that just could not be more satisfying or pleasurable. I love my life and all the little adventures that Jon and I get up to.

Apart from a little bit of hair that grows on my legs, I have no body hair below my neck. It’s all been removed with electrolysis. I’m slim with small(ish), pert breasts that have small aureoles and giant nipples. When they’re hard Jon says they’re like chapel hat pegs. I have a nice firm, flat stomach with a pubic bone that does stick out a bit.

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   In my pussy lips I have 2 little gold rings that Jon put in me. My clit is very prominent and is usually sticking out between my lips. It’s about an inch long with a little round head. Jon sometimes calls it my little dick. I don’t own any bras, knickers, trousers, leggings or shorts; and 90% of my skirts and dresses can be described as mini or micro. I used to be a very shy girl, but I’ve now gone completely the other way, and get a great thrill from letting other people see my body.
I hope that’s enough to satisfy the people who asked. If it isn’t, perhaps they would like to e-mail me with specific questions.

vanessaevans69@hotmail. com

Jon told me to stop writing my Journal in the summer of 1999, but has recently asked me to document, some of the more interesting experiences that we have had since then.

Both Jon and myself have been scouring the Internet looking for ideas for little adventures or incidents that we could manufacture to have some fun. We’ve found one or two stories that appear to be slightly rewritten copies of some of the text in my Journal, and one or two that are very similar to some of the adventures that we’ve had and that I’ve written about in my Journal. At first I was a bit annoyed about this, but Jon said that I should be honoured that someone thought our adventures were good enough to copy. I’ve started thinking that way as well.

Me on CD in Havana

Right, Jon had to go to Miami on business (computer software).

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   It was a bit of a rush job but he told me that I was going to go with him because he wanted me to get some sun on my 27th birthday.

As usual Jon had more clothes with him than I did (well he was going to business meetings and I was expecting to spend most of the time by hotel pools or on a beach). Jon decided that I would wear just a coat and shoes until we got onto the plane so off we set with Jon driving down to Heathrow. Once the car got warm I had to unfasten my coat and keep it wide open. No excitement on the journey (it was dark), but Jon did get me to give him a blowjob half way down the M40.

No problems going through the airport either, Jon got me to remove my pussy rings a few months ago so the metal detectors didn’t have anything to bleep at.

After we’d taken off Jon opened his briefcase and gave me a little package. He told me to take it to the toilet and put it on. It contained one of my thin cotton mini-dresses and one of my remote controlled vibes. As I put that in I got a bit wet with the anticipation of what I was expecting Jon to do to me without actually touching me. As I got back to my seat Jon told me to take the coat off before I sat down. As I climbed over Jon to get to my seat (middle one of three) the woman on the other side of my seat looked at me and I saw her eyebrows rise as I leaned over Jon. I guess that she’d noticed that the top of my dress was hanging down (it’s a bit baggy, especially as I never fasten the top two buttons) and she must have seen my breasts. As I sat down I made sure that my dress wasn’t between my pussy and the seat. I didn’t want to get off the plane with a big wet patch on the back of my dress.

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The woman smiled at me and said, “I expect that it will be quite warm when we land. ” I said that I hoped so, and got myself comfortable for the long flight.

It was about 30 minutes before Jon gave me the first blast from the vibe. He’d waited until a few minutes after the woman next to me started talking to me again. She was a bit of a stuck-up bitch who fancied herself. She started telling me about herself and her servants, how it was nice to get them to run around after her. When Jon switched the vibe on it caught me by surprise a bit and I gasped and grabbed the seat arms. Both Jon and the woman asked me if I was all right at the same time. Jon went on to ask me if he could get anything for me. Not thinking too well I said, “No, I’m fine than you Master. ”

After a few seconds the woman said, “Your husband seems to care for you a lot. ” Oh, he’s not my husband, he’s my Master, and yes, he does care for me a lot. ” I replied. “You mean …. .

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  ” she started to say, but I interrupted her saying, “Yes, he is my Master, and I am his slave. I am his, I am devoted to him, and I obey his every command, without hesitation. ” “Blimey!” she retorted. “That’s freaky. Really freaky, I thought I was the lucky one with servants, but to have someone who’s a, a submissive, your err. Master is a very lucky man. Do you do everything that everyone tells you?” “I obey only him. ” I said. “Pity,” she said, looking at me with a funny but naughty expression on her face. She was staring at my legs and short dress. “So if I were to ask you to do something for me, your Master wouldn’t allow it?” she said. “I obey only my Master,” I repeated, “I’m forbidden, to touch anyone else, or have anyone touch me unless my Master tells me to it. ”

Just then Jon interrupted and asked me if I wanted a drink. I said, “Yes please, I’m starting to get a bit warm. ” With that he switched the vibe off.

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   I guessed that he’d realised that the vibe was starting to do its job. Jon got me a glass of wine and it wasn’t long before I was feeling sleepy. I dozed off and when I woke up the next top two and the bottom two buttons of my dress weren’t fastened, Jon had undone them while I was dreaming about him fucking me on a gorgeous beach with about half a dozen people watching us. There was then only four buttons left fastened. If it hadn’t been for the seat in front of me and the fact that I was in the middle seat of three, I would have had a minor problem of people being able to see my bald pubes.

“I see that your Master likes to keep you ready for anything,” the woman next to me said. I looked at her in a puzzled way and she continued. “The lack of underwear, I couldn’t help but notice when you were sleeping and leaning on your ‘Master’. It must have been a nice dream, you were obviously enjoying it. ”

My pussy was quite wet, and Jon must have heard the woman because he switched the vibe on again.

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).

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   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.

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.

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.

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   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.

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.

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   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.

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.

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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.

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   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, “There’s laws about pornography in this country, and you have just broken them. ” I hadn’t a clue what he was talking about until he turned the monitor round so that I could see what he was looking at.

It was a video of me on our ‘fucking machine’. For any readers that haven’t read part 6 of my journal, the ‘fucking machine’ is a machine that Jon got someone to build in the back bedroom, or ‘punishment’ room at home. My hands are tied above my head and the machine raises then lowers me onto a dildo over and over again.

About 8 months ago Jon bought a video camera and taped me on all the machines in the punishment room, and being punished in various ways. I knew that Jon had loaded them onto his PC but I didn’t know that he was giving copies to people.

As I watched, the video ended and with a click another video started. This one was of me spread on the whipping-T with Jon administering a well deserved, and gratefully received whipping. We watched Jon whipping my backside and pussy as I counted the strokes out loud. At 30 I could clearly hear myself moaning with pleasure as I had a fantastic orgasm.

When that video ended the sergeant looked up at me and said, “Maybe I’d better search you a bit more thoroughly, take your top off,” he said. I didn’t respond quick enough and he shouted, “Now. ” He sounded angry and I wasn’t about to get him more upset so I took my hands off my head, un-tied and removed my top.

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   My nipples were really hard and tingling.

The sergeant stared at me for a while then got up and walked round the desk to me. He stood in front of me then started mauling my breasts. He kept pulling and rolling my nipples between his thumb and finger. I had a real problem keeping from moaning with pleasure.

After a few minutes of this he stood back and said, “Now the skirt!” What choice did I have? My only real concern was that he might fuck me and give me some horrible disease. Jon doesn’t get too upset if men (or women) force me to do things just so long as I don’t let them fuck me. Not that I would have had much choice this time, I was on my own with a man that had a gun strapped to his waist.

Anyway, I unfastened my skirt and stepped out of it. I was totally naked. The sergeant told me to put my hands back on my head and spread my legs again. Of course I did. He then started to slide his hands all over my backside and pussy. He spent a lot of time feeling my bald pubic mound, I guess that he’d never come across one before. Eventually he pushed a finger into me and quickly pulled it out when he felt my Ben Wa Balls.

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   “What’s that in your cunt?” he said.

I said, “Ben Wa Balls,” but he just looked blankly at me as told me to take them out. I squatted down and squeezed them out onto the floor before standing up again. He picked them up, smelt them then squeezed them. He then threw one of them back onto the floor. When it didn’t break he looked at me so I said, “solid steel. ” He picked it up and had both of them in one hand. He was rattling them about in his hand and obviously trying to work out what they were for. They were knocking into each other and after about a minute or so a smile came on his face and he pushed them back into my pussy.

He turned to me and grabbed my pubic bone again. This time when his finger went into me there was no resistance, it went straight in. He moved it all around inside me. I couldn’t help it, I let out a moan and shuddered as I orgasmed. After he’d had enough with his finger he pulled it out and stood back. “Bend over the desk,” he said.

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Oh no! I thought, he’s going to fuck me. I was getting scared. I could hear him doing something and it sounded like he was undoing his trousers. I thought ‘brace yourself girl’.

The next thing I felt was a finger going into my ass. It waggled round and pushed quite hard into me. Then it came out. A few seconds later I felt a thumb going into my ass and a finger going into my pussy. I was then lifted up by that hand. That hurt.

He moved me about a bit then pulled his hand out and told me to stand up and turn and face him. I then had to spread my legs again and put my hands on my head. He then went round to the desk and got out this lump of plastic with 2 metal bars coming out of one end about 2 inches apart. At first I didn’t realise what it was, but I soon found out.

He kept me standing there for a couple of minutes before coming up to me and rubbing the device up and down my front.

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   He was saying something about not wanting women like me in the country, but I wasn’t really listening to him. Every time the device went over my breasts or lower stomach I got a tingling in my nipples and pussy. It wasn’t from the device, it was just where it was being rubbed. I could feel my juices starting to run down the insides of my legs.

Then it happened, the device was on my right nipple when I got this incredibly strong pain all over. I’ve had the odd 240-volt shock by accident at home before, but this was like hundreds of times stronger. My knees buckled and I screamed out in pain. Somehow I managed to stay on my feet, but I’m not sure how. After the initial pain my nipple was rock hard and hurting like hell. My pussy was responding too, I could feel an orgasm coming on.

Readers of my journal will know that pain is something that gives me pleasure, the more the pain, the more the pleasure.

I looked at the sergeant and saw the smile on his face, and the bulge in his trousers.

The stun gun moved to my left nipple and I watched and waited. I think I saw his finger move a bit, then I saw the blue arc of electricity as it jumped from one prong, through my nipple then to the other prong. This time I did collapse to the floor.

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   The incredible pain took me over the edge and I moaned and shook as I had one of the best orgasms that I’d had for weeks.

The man just watched me, and when I stopped shaking he told me to stand up again. While I was standing there he cleared just about everything off the top of the desk then told me not to move. He disappeared for a couple of minutes then came back with another guard.

The new guard had a good look at me then explored my breasts and pussy with his hands. When he touched my nipples and clit I just about came again. My nips were harder than they’ve ever been before.

The sergeant told me to lay on my back on the desk. When I was there he told me to put my hands on my head, and to open my legs again. By that time my pussy was gaping open and I could feel their breath inside my hole as they bent down for a close look.

I felt the stun gun prongs on my clit and got scared. I know that my pussy can take being whipped, but I didn’t think that it could take the stun gun. I tensed-up in anticipation and my face showed that I was scared.

It hit me. I’ve never screamed so loud and cum so hard.


   My clit felt like it was a burning lead football. I’m sure that I was squirting cum out over the desk. I was shaking and sweating for what seemed like hours. I vaguely remember seeing the big grin on the two men’s faces.

Then it happened again. I thought that Jon’s whippings had taken me to the limits, but I was wrong. I came over and over again. I was shattered.

The third time it happened I just felt a bit of pain then the next thing I knew I was waking-up in a heap on the floor. The two men were still there, but there was a middle-aged woman there as well. I guess that she was their superior as they jumped when she shouted something at them.

The men grabbed my arms and dragged me out of the room and out into the open air. My wrists were tied together and the rope was slung over a beam at the side of the building. I was pulled-up until my feet just touched the ground. Ropes were tied to my ankles and my legs were pulled apart.

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I’ve spent many hours restrained in that position so I didn’t need to try to support my weight on my feet. I was too knackered anyway. You get used to being having little blood going to your hands, and your shoulders get used to the pain.

One of the men got a bucket of water and threw it over me. It felt nice, and it woke me up. The man who spoke English then told me that they didn’t have a prison cell there and that I’d have to stay there until my flight out of the country.

Little did he know that I like being naked out in public, especially when I have no control over it. Even if I had just about been killed with the pain and pleasure.

After a minute or so I started to take in where I was. I was at the side of some sort of service road to the airport. There were what looked like airport workers walking up and down the road and the odd lorry going passed. The road was about 3 metres from where I was and most of the passing people were looking over towards me. Most just looked and kept walking, but a few stopped for a while and had a good look.

After about an hour or so some teenagers (boys and girls) saw me and came over to me. They were talking to each other, but I couldn’t understand what they were saying.

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   Eventually one of the boys put a hand on my left tit. When he touched the nipple I winced, it was VERY tender and still rock hard. His hand pulled back for a second but soon came back, and had a good grope. The hand then went down to my pubes and he gave a slight smile as he held my bald pubes. Only for a second though because it soon went in between my legs and into my pussy. When he touched my clit I really winced and tried to pull back. My clit still felt like a burning football.

They all had a grope of me, even the girls who seemed very interested in my lack of pubic hair and large clit.

Eventually they left and I was left to soak up the sun. My pussy was leaking juices all the time, but the sun was drying them before they dripped off my feet.

A couple of hours later a dirty, scruffy man came up to me. He looked like a vagrant, and a slightly retarded one at that. He had a good grope as well, and even got his dick out and tried to get it to reach my pussy. He didn’t appear to have the sense (fortunately) to realise that he’d have to have something to stand on to get high enough.

After a few minutes he gave up and wandered off, much to the amusement of one of the guards who came out to check on me.

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It was a guard that I hadn’t seen before and he wasn’t going to miss the opportunity to have a good grope. He was a bit surprised too when he pushed a finger into me and found Ben, but that didn’t stop him bringing me close to cumming them then leaving me frustrated.

By the time the guards finally untied me I was getting a little sun-burned. They gave me my clothes and told me to put them on. It was a bit difficult because my arms and hands were numb from having hung by my wrists for hours.

Eventually I managed it and they ‘escorted’ me to the international airport and to the check-in. Walking was painful as my clit was still very swollen and sore. After I’d checked-in they saw me through passport control then left me. I checked my handbag, everything was there except for the CD with the videos on. I guess that it (and copies of it) will be doing the rounds in Cuba now.

The flight back to Miami was uneventful, albeit a bit painful, and it didn’t really help wearing Ben, they only seemed to make my clit swell more. I was very thirsty and drank quite a lot of water and beer on the flight.

When I got back to the hotel Jon was waiting in reception for me. He knew something was wrong because he’d had a phone call from his client. When he’d been unable to find me he’d asked around and heard that a blonde, white girl had been arrested.


   He’d decided to get out of there as soon as he could.

Jon took me up to our room then inspected the ‘damage’. He assured me that my nipples were all right, just swollen. When he touched them I nearly came because they were still tingling and very sensitive. I did cum when Jon inspected my clit and then retrieved Ben. After that he told me to take a ‘cool’ bath – which didn’t help – apart from feeling clean again.

It was late(ish) that night when Jon took me to a restaurant with me wearing just my red mesh dress and high heels. It was a good job that I don’t wear underwear as they would have been quite obvious. Wearing nothing under it looks a lot more obvious. We got lots of attention from the waiters but I was too tired to enjoy it.

Jon let me sleep until 8:00 am. When I woke up the sun was shining, the curtains were wide open and Jon had taken the covers off me. I turned my head and looked out of the window to see a man on a balcony in the hotel opposite. He was staring straight at me.

There was a knock on the door and I heard Jon shout from the bathroom.

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   “Get that please V. ” I quickly looked for a robe or something but everything was put away. ‘What the hell!’ I thought and opened the door in the nude. The look on the waiter’s face was priceless. Jon had ordered breakfast and the waiter wheeled it in and set it up on the table. All the time he kept looking over to me. I just stood and watched, still holding the door wide open.

A young couple walked by and the man got quite a surprise when he saw me, but it was the woman who stared at me until they were passed me.

The waiter ran out of things to do to prolong his stay and walked up to me and held his hand out. When I realised what he wanted I walked over to where my bag was. It was on the floor so I bent at the waist and gave him a great view of my pussy as I slowly got some money out. When I stood up I saw Jon standing in the bathroom door watching with a big grin on his face. The waiter hadn’t even seen him.

After breakfast Jon told me that he’d just got one more day’s work before we’d have to go home. I didn’t want to be out in the sun all day because I was still a little red from ‘hanging around’ the previous day, so Jon told me I could go shopping.

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Before he left me for the day, Jon inspected my nipples and clit again. They were still swollen and tingling. He told me to wear something soft over my nipples and keep walking to a minimum so I put on a silky back-less mini-dress with an ‘A’ skirt that’s quite low at the back.

I went for a taxi and asked to be taken to the nearest mall that had lots of clothes shops. It didn’t take long and I was soon slowly walking through the mall getting a measure for what was there. Wow, Miami has some great shops, and just about everything I saw was cheaper than in the UK.

I started in a lingerie shop and bought a slip that I’ll be able to wear as a dress, Ultra short and slightly see-through.

Next I went into a boutique and selected three skirts to try on. All three were low-slung, the type that you can easily adjust the ‘waist’ so that they feel as if they are about to fall down any second. Of course I had to take my dress off to try the skirts on and the changing cubicle didn’t have a mirror in it. It looked as if it did at one time because there were screws that looked as if they’d held a mirror in place once. So, to see what the skirts looked like on I had to go out into the main boutique are. The young girl did a double take when she saw me, but carried no serving someone else.

When she’d finished serving that woman she came over to me and asked if I wanted any help. I asked her if she though the skirt looked good on me and watched her eyes as she said it looked great.

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   Her eyes never even looked at the skirt, they were glued to my swollen nipples. I have to admit, my nipples are big (not like the rest of my tits) at the best of times, but they were like Jon’s thumb ends after the stun gun.

I turned away from her and she stopped daydreaming. She started to say something about me not being out in the main shop area topless, but I ignored her and I told her that I’d go and try one of the other skirts on. She asked if I’d like any help. After a quick thought I said, “Yes” and she followed me into the cubicle. Before she’s closed the curtain I dropped the skirt I was wearing, much to the pleasure of a man that had come over to see if he’d actually seen a topless woman.

The girl stared at me again, this time down at my bald pussy. I let her for a few seconds before asking her to pass me one of the other skirts. She woke-up again, said sorry, and got one for me. To break the silence I told her that I never wear underwear and hoped that she didn’t mind. She said no, and told me that she didn’t either. And just to prove it, she lifted her skirt at the front to reveal a nicely trimmed bush. “Much nicer being free, isn’t it?” she said. “Absolutely” I replied.

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I gave her the skirt back and asked her to put in on me for me, she seemed a little surprised, but unfastened it and bent down holding it open for me to step into it. As I did she saw my swollen clit and said, “that looks painful. ” “It is” I said, “it needs some TLC” wondering if she’d volunteer. She didn’t and when both legs were in she slit the skirt up to my hips. The skirt fastened at the front and her soft gentle hands felt good on my stomach as she slowly fastened it. I slid it down onto my hips and said, “Lets go and see what it looks like. ” She started to say something, but I eased passed her and out to where the nearest mirror was. The man was still there, pretending to be looking at tops on a rack.

The girl followed me and watched as I smoothed the material down. I told her that I wanted to see if I could get it any lower so I adjusted the fastener and pulled it down on my hips again. “Oops!” I said as the skirt slid too far down my hips and down to the floor. Needless to say I didn’t rush after it, in fact I looked over at the man and the girl to make sure that they were looking before I stepped out of it and bent (at the waist) to pick it up. The man got a great view of my pussy and I felt a bit of a rush of juice as I looked between my legs to watch him watching me.

I picked the skirt up and walked back into the cubicle, and turned to watch the girl following me, and the man staring at me.

I tried-on the third skirt with the girl fiddling round the top of the crack of my ass to fasten it.

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   I didn’t like that one so I took it off and I put my dress back on. The man looked a bit disappointed when I appeared with my dress on.

I bought the first skirt that I tried-on, it felt good, looked good, could easily blow up in the wind, and could easily be adjusted so that it wouldn’t take much for it to fall down.

From there I went for a coffee at a café in open area of mall. I sat there right next to where lots of people were walking towards me. I never cross my legs, but with my painful swollen clit I needed to give it plenty of room so that it didn’t hurt more. I noticed one old man go round three times to get to see more. When I saw him coming the third time I deliberately opened my legs wider so that he really could see everything. I think I made that old man’s day. I had three cups of coffee before I finally moved on.

Next I decided to go up and down the escalator a few times. I wanted to make a few men’s balls ache and maybe get a few wet patched on the front of their trousers.

I know, I’m a real tease.

I spotted one man following me up a couple of times, he had this bag that had long handles so the bag was nearly on the floor. I thought I saw a video camera pointing up out of it so I thought I’d make his efforts worthwhile.

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   I timed it so that I was right in front of him as we got onto the escalator then stood with my feet about a foot apart. Half way up I lifted my left foot up a step and leaned forward to rub my foot. I looked back down my side and saw the bag virtually in between my legs. I saw a red light in the bag as well.

When I walked off the top of the escalator I went to a shop window and stood looking in, with my feet well apart. I felt the bag brush against my feet but didn’t move. Eventually I saw him walk away, I guess he was pleased with his efforts.

Next it was the obligatory shoe shop. There’s no way I can go shopping without flashing my pussy to some lucky male shoe shop assistant, and by that time it was a very damp pussy. I waited around just looking until this young man was free. As he walked over to me I could see him looking me up and down. I didn’t disappoint him and by the time I left he was as close to cumming as I was.

I was dying for a good fuck so I got a taxi back to the hotel and went up to our room to wait for Jon. Fortunately I didn’t have to wait long and Jon was just as keen to have me on the balcony as I was to have him. It still hurt when Jon caressed my nipples and clit.



We had a quiet night in the hotel restaurant and bar that night.

Jon inspected my nipples and clit again. They were still swollen and throbbing. Jon then took me out onto the balcony and had me as I looked down onto the swimming pool area. After he shot his load into me and gone soft, he pulled out and slapped my backside.

We went down for breakfast with me in a little halter-top and short skirt with our juices running down the insides of my legs.

After breakfast Jon told me we were going for a walk. I had to go and change into what is basically 3 rectangles of material. The one that goes over my breasts is held with 2 cords, one round my neck and the other round my body, a bit like a bikini top, but totally unfitted. The other 2 rectangles cover my bum and pussy. A cord goes round my hips to hold them in place. When Jon got me to make it he got me to include a detachable cord that goes in between my legs to the bottom of the rectangles. It’s to stop the front or back blowing right up. As it turned out that cord stopped a few people seeing my bum and pussy because it was quite windy that day. Jon also got me to take a couple of small towels – just in case.

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After walking a mile or so Jon saw a shop selling things for the beach. He went in and got us some flippers, masks and snorkels. He’d decided that we were going swimming.

There was no way that I could strip naked and go swimming, not there, so I had to swim wearing what I had on. The water was cold at first, but I soon got used to it, especially with Jon messing about. With only those 3 rectangles on it felt as if I was naked. Swimming naked is a feeling that I really enjoy.

As I said, Jon was messing about a lot, and it was only when a man, who was also wearing a mask, spent quite a long time getting close to me and swimming round and under me that I decided to look to see what he could see. Imagine my surprise when I realised that all 3 rectangles had gone. Apart from the mask and flippers I was naked. I swam over to Jon and asked him if he knew. He told me that I’d been like that for ages, but he wasn’t going to tell me.

We carried on swimming and messing about for a while longer until the man got bored and left. Then Jon took me to a shallower bit and fucked me.

After that there was the problem of getting out of the water and back to the hotel.

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   I asked Jon if I could borrow his shorts and shirt but he said “no. ”

Jon got out of the water and was getting dry while I stayed in waiting for things to get a bit quieter. Eventually I decided that I’d have to make a move. There was this nice hunk walking down the waters edge on his own. I stood up and walked straight passed him to Jon. His face was a picture. Jon was just amused by it.

I dried myself and wrapped one of the towels round myself. It was way too small and wouldn’t tie properly. It only just covered my bum and pussy. Anyone walking passed me on my left would be able to see that I was naked under it. And with me not being able to tie it there was a great danger that it would fall down anyway.

Jon decided to get a taxi back to the hotel and the driver had a good look as I got in. At the hotel the doorman got a real eyeful when he opened my door. In the lift Jon took the towel off me and gave me the flipper to carry.

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   I had to walk all along the corridor to our room totally naked except for 2 pairs of flipper. A middle-aged couple looked really surprised when they came out of their room right in front of me.

We were on an evening flight back to the UK so after a shower Jon told me to get us packed. Jon left me in reception while he went and bought something. When he came back with nothing I asked him what he’d bought. It was a stun gun and he’d posted it to himself. He reckoned that it stood a better chance of getting though in the post rather than us carrying it. He said that they’re illegal in the UK.

There was no problem in the airport because Jon told be to carry Ben in my bag. No metal detector problems. Once we cleared security I had to put them in. I was pleased because the low vibrations of the flight keep me excited.

The flight was nearly empty and we settled in a window seat. After some food and drink I leaned over and dozed off with my head on Jon’s lap. When I woke-up I had a blanket over me, Jon told me that he’d got a stewardess, sorry cabin crew person, to get one for me.


   It was so quiet, and Ben had been at work, so I got Jon’s dick out and filled my mouth.

After a couple of minutes Jon decided that we should renew our membership of the mile high club. I don’t think that anyone saw us go into the toilet but as we were walking back to our seats a stewardess walked passed us and gave me that ‘knowing smile’. In the toilet Jon lifted me up straight away and opened my legs. Before I knew it he was pushing his dick into me. Problem was he’d forgotten that I was wearing Ben. He didn’t hurt himself and quickly put his finger in and got them out. The surprise hadn’t cooled him down and he came quite quickly.

The seat was quite wet by the time we landed at Heathrow.

It was the Sunday before my nips and clit were back down to their normal size and the
stun gun arrived the following Wednesday. Jon keeps it on display in the punishment room. He hasn’t used it on me yet, he’s teasing me because he knows that I’ll enjoy it. Each time he mentions it he checks my pussy and finds that I’ve got a bit wetter.

That was my first experience of America (and Cuba); I hope Jon takes me back there soon. I also hope that Jon gets me to write about more of our adventure soon, it’s nice remembering them and getting excited as I write all the details.

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