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.
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 and regular shaving. I’m slim with small, 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. 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’ve asked. If it isn’t, perhaps they would like to e-mail me with specific questions.
Jon told me to stop writing my Journal in the summer of 1999, but has asked me to document, some of the more interesting experiences that we have had since then.
Update September 2011
Sorry that this update has taken so long. I have been helping Jon with some of the work for his business as well as looking after Hannah and Sam. I know that it’s not a good excuse, but that’s all I’ve got. Any suggestions for a suitable punishment? Email me at firstname.lastname@example.org
The last winter was long and cold. Down to minus 14 at one point. Okay I know that minus 14 is nothing to people in Scotland or Alaska or a few other countries, but it’s bloody cold for this part of the world. Jon bought me a couple of knee length warm coats and a couple of pairs of warm knee length boots and I was going out wearing just one of the coats and a pair of the boots. We went to one restaurant, with me dressed like this that was very hot inside. The staff kept asking me if they could hang-up my coat. After about the third time I decided to shut them up. I stood up in front of this waitress, opened my coat wide and said, “What do you think?” She looked me up and down, went bright red, apologised and walked away. We got a few sly looks from the rest of the staff after that.
Another effect of the cold weather was that I wasn’t been able to go out jogging so the exercise bike with the dildo that goes up and down in the saddle has done a lot of miles without even moving. The girls were queuing to use it as well.
Thankfully, the really cold weather finally went and we got back to the usual mediocre weather that is so common in England these days and I was able to get out jogging again. I’ve bought a new tennis dress that I now wear while jogging. It’s just as short as the old one and motorists still honk their horns at me sometimes.
Jon read a story about rigged Sharking (The New Me by JustJessica) a while back and decided that we would have a go at it. At that time the weather was still quite cold so I had plenty of time to modify a summer dress so that it was strapless, wouldn’t fall down on its own, and would easily come off completely with one tug in the right place. I also had to buy a thong (yuk!) and change it so that it was held on with tiny bits of Velcro on each side. I also had to buy a hoodie top for Jon so that he could keep his head covered.
I chose a thin cotton mini dress that buttons all the way down the front. I elongated the button holes so that they would pop easily. I had big problems getting it so that it didn’t fall down on its own, and finally decided that I could do that by keeping my arms close to my sides. After all, I would only be wearing it for a few minutes at a time.
When the weather finally got better (not exactly hot, but warm enough for women to be wearing summer dresses), we set off for a big city about 20 miles away.
The plan was that we would drive round multi-story car parks looking for one that had no ccvtv cameras.
It took hours to find a suitable car park but eventually we found one and set about practicing Jon’s plan.
I had to wait in the stair well with a big shopping bag in each hand, and keep peeking out until I saw a middle-aged man, on his own, getting out of his car and walking towards the stairwell. I was then to walk towards him and as I got close to him, Jon was to run from behind the man, rip my dress and thong off, then run off with them, down the stairs to the floor below where he had hidden a shopping bag behind a car. He was then to put my clothes and his hoodie in the bag and come back up the stairs as if he was following me back to our car.
The first attempt failed miserably, my dress just wouldn’t come off. I think that it was my fault for holding my arms too tight to my sides. Anyway, Jon ran off leaving two buttons on my dress still fastened. I cut those two off for the next attempt.
The second attempt was even worse, just as Jon was running up to me a family with about three young kids appeared out of the stair well a bit behind me. Jon ignored me and kept running.
We had to wait about 20 minutes for the next ‘victim’, an unfit looking guy who was carrying a large box.
It worked a dream. The man and me were about 5 metres apart when Jon appeared from behind him, grabbed my dress (which came off easily), then my thong (it rubbed hard against my wet clit as it came through my legs); then he was gone. It all happened in seconds. Even though I knew it was going to happen I was still a bit shocked. I managed to scream then just stood there, naked with my mouth wide open, pretending to be shocked and still holding the heavy bags. After a couple of seconds I tried to cover my pussy and breasts but it was impossible with the bags still in my hands.
The man walked up to me, trying to say something but I couldn’t understand what. I think that he was as shocked as I was pretending to be, but his eyes were still looking me up and down.
After what seemed likes minutes (probably only seconds) of us both looking at each other, and towards the way Jon had run off, the man asked me if I was alright. I certainly was, I was excited and very wet, but I wasn’t going to say so.
The man was still muttering something and looking all around as Jon appeared out of the stairwell. He ran up to me and asked me if I was alright, then what had happened. Then before I could answer he asked in the man had done anything to me. The man looked even more shocked than before.
Jon put his arm round me and pulled me towards where our car was. I looked back to see the man staring at my naked backside as we walked away.
Our car was just round a corner and as soon as we got in, Jon pushed his seat back and told me to climb on him.
Our next victim was a couple of teenage lads who were busy talking as Jon appeared behind them. Jon timed it perfect and I was naked in front of them in seconds, trying to look shocked and embarrassed. The lads stopped and stared at me for ages before one of them came over to me and asked if I was okay. All the time both of them were staring at my little tits and bald pussy. The second lad just started to say something when Jon appeared behind me shouting for them to leave me alone. The first lad started to say something but the second lad grabbed his arm and they both ran off with Jon shouting at them.
We’d both just got in Jon’s car when a police car drove slowly passed. We took that as a queue to get out of there.
This summer was another big disappointment. It was slightly warmer than the last few summers we’ve had, but with only a handful of days that were quite pleasant, but there is no way that they could be called hot.
Over the school holidays I’ve been exchanging emails a couple of teenagers in Canada who are both into dares and flashing. They’ve had an ‘interesting’ summer where one of them got caught by the police while out walking, naked early one morning. She managed to talk her way out of any serious trouble and bounced back quite quickly. She also did a dare in a sex shop where she ended up naked with the shop assistant (a woman). Unfortunately a male ‘plant’ in there took loads of photographs on his phone and later tried to blackmail her into a gangbang. Fortunately her friends rallied round and showed this young man the errors of his ways. I still think that he got off too lightly.
The other girl got tricked by her friend into stripping in public places and ended up having to get home, on her own, wrapped in newspaper once and a plastic rubbish bag another time. She also got tricked into going into a sex shop naked to collect some clothes and the money for a taxi ride home that had previously been left with the shop manager. Unfortunately the manager broke his promise and he and a couple of his mates used her in a way that was totally wrong.
Fortunately both these girls are tough and they both survived to do another dare. If either of them read this, both Jon and me wish them all the best for future ‘adventures’ and for the rest of their lives. One suggestion to them both – make sure that whatever you get up to is safe and that someone is watching your back.
I just wish that there were more people around the world like these two.
One thing that I did learn from these two amazing young ladies, was the art of ‘dipping’. What they do is to purchase a hot dog in a fast food outlet then ‘dip’ the sausage in their pussies. Either they or their friend would then take a bite.
They also do this with their fries. All this is done in the open restaurant. Obviously they would be wearing a short skirt and no knickers. They told me that ‘dipping’ is also sometimes done at parties with everyone watching.
Amazingly, neither Jon nor I had thought of doing this and since then we have been looking for a fast food restaurant round here that sells hot dogs that have sausages hard enough. They’re usually soft and wouldn’t survive being pushed up my pussy. Perhaps I’ll start looking for some that I could take with me and swap when no one is looking. I’m sure that Jon will want to do some of the ‘dipping’ while my legs are wide open and the odd man or two is watching.
These 2 young ladies got me thinking about dares and about the fun adventures that Jon and I have had. I’ve turned a number of our adventures into dares and listed them below. How many of these do you think you can do?
Go on, have ago – I DARE YOU.
1. Find a clothes shop where they have curtains on the changing cubicles, and where these cubicles face the main store. Strip naked then put your shoes and some knickers on. Pull your knickers down to your knees and then stumble trying to take 1 foot out of the knickers. Stumble against the curtain and fall out into the open.
2. If you can get someone to help you, go to a clothes shop and both go into separate changing cubicles. Strip naked whilst both of you count to 60. Leaving your clothes where they are, both of you open the curtains and walk into the others cubicle. Get dressed in the others clothes and leave.
3. Wearing only a dress and shoes, go to another clothes shop. Find a summer dress and try it on out in the store (not the changing rooms). Do this by taking your own dress off then put the stores dress on. Change back in a similar place and way.
4. Yet another clothes shop dare. Select 2 sets of skimpy see-through underwear and a micro skirt. Strip naked apart from shoes and put the most modest set of underwear on. Stick your head round the corner and wait for a single man coming close. When in ear-shot, ask him if he could help you. If he agrees (he must be gay if he says no), tell him that you’re shopping for some clothes that your boyfriend will like. Tell him that your boyfriend has never seen you in your underwear and you are worried and want to look your best for him. Assuming that he says okay, open the curtains and give him a full frontal. After a few seconds do a 360 then ask him what he thinks. Pretend that you are not sure and ask him if he could wait while you change into another set. At this point you can either close the curtain to change, or do it while he watches. Repeat the full frontal, 360 and asking him what he thinks. When done ask him which set he thinks your boyfriend will like the most, offering to show him the first set again.
If he’s still with you and hasn’t had a heart attack, ask him if he could give you his opinion on a skirt that you are thinking of wearing on your next date with your boyfriend. Change into just the skirt and show him. Bend over at the waist (back to him) and ask him if he thinks it’s too short. Ask him if too much is showing.
At the end, remember to thank him for his help.
All this can be done without you even leaving the cubicle.
5. And yet one more clothes shop dare. You need to find a friendly clothes shop owner and arrange to be a mannequin for a few hours. Of course, you have to stand in the shop window, and the shop owner has to change your clothes.
In the Street in town
1. With another female, both of you wear just a dress and shoes. Find a quiet (but open) corner in town and swap dresses in the middle of the road.
2. Go out on the street in just a dress and shoes and ask random men to take a photo of you. At the last minute take dress off saying that the photo is for your boyfriend who is working away. Another female could help you with this one, and perhaps join in.
3. Sharking - Wear shoes and a summer dress with no sleeves or straps; and an elasticated bodice. Nothing else. Carry a heavy looking shopping bag in each hand. Get a friend wearing a hoody to run up to you and pull your dress down to the floor leaving you with your dress round your ankles. The friend runs off leaving you standing there pretending to be embarrassed and still holding the 2 shopping bags. Ask the man who was walking towards you to pull your dress back up.
4. Wearing a short skirt and no knickers, walk around town until a man walks towards you. When he is about 8 or 10 metres from you drop your purse (or something similar). Squat down with your knees wide open and take your time picking up your purse which needs to be to one side of your legs, not in between them.
1. Sit at an outside table and push 2 Ice cubes in to your pussy and squeeze your legs together.
2. Get a carrot and put it right inside your pussy at home. Sit at an outside table and slowly expose your pussy to at least five men. When flashing the fifth man, squeeze the carrot out so that he sees it come out. Lick it, then put it back in.
3. Sit at a table on the street side and face the way that most people appear to be approaching from. Wear sunglasses and pretend to be reading a book. Uncross your legs and open them wide enough for people approaching to be able to see up your skirt to your pussy. Extra points if you are knickerless. Watch approaching people but don’t be disappointed if people don’t appear to notice. 95% of people just don’t look at what is going on around them.
1. The old pizza dare – order one by phone for home delivery and answer the door naked.
2. If your PC has a microphone find a web site that will record the sound and create an mp3 that you can download. Record yourself having a genuine orgasm and email the mp3 to 3 of your friends.
3. Arrange for a friend to restrain and blindfold you naked. That friend is then to get an un-named man to spank you, then disappear without you finding out who it was.
4. Arrange for a friend to restrain and blindfold you naked in your bath tub (no water). That friend is then to get 4 un-named men to quietly sneak in and give you a Golden Shower.
5. Same as the dare above but the men are to masturbate and shoot their load over your upper body.
Do you own (or can borrow) a bicycle
1. Set the saddle on your bike so that when you peddle along you slide from side to side on the saddle. With no knickers and a short skirt on, go for a ride with you skirt over the back of the saddle and your bare pussy sliding from side to side on the saddle.
2. Ride the bike whilst naked through a public park in broad daylight when there are lots of people about.
1. Pull your dress or skirt up and squat down and have a pee in the open in a public park when there are lots of people about.
2. Get a friend to ‘lead’ you through the park with you wearing only shoes, microskirt, skimpy top, dog collar, dog lead and handcuffs (fastened behind your back).
1. Go to a co-ed students dorm at a time when you think some boys will be showering. Go into the boys shower room, strip off and take a shower. Leave your dress (and knickers and a bra that you have brought in a bag) visible so that if a boy comes in he will see your clothes and realise that there is a girl (or a tranny) in the shower. Leave the cubicle door/curtain open whilst showering. Stay there until at least one boy has seen you naked. If anyone says anything tell them that all the girls showers were all in use. When you think you should leave, streak out of the place naked and get dressed (not the bra or knickers) outside.
10 Pin Bowling
1. Go bowling wearing an ultra-short skirt with no knickers on, and play at least 2 full games.
1. Find an Art school and become a nude model.
1. Go shopping wearing a miniskirt (no knickers) that is pulled so far down that the top of your crack (front and back) is just showing.
2. Wear a miniskirt, shoes, see-through top (no bra) and a jacket; the go for a walk round a shopping centre. As you enter the building, take your jacket off and carry it over your arm.
1. Drive to a local wooded area that has a path through it. In the car park strip off everything except shoes. Get out of your car, lock the doors and hide the key close to the car. Walk along the path for at least a mile before turning round and walking back to your car.
2. With a friend, drive to a wooded area that has a path through it. Walk about one mile along the path. At a suitable tree alongside the path, strip completely, Get the friend to tie your wrists together and tie the rope over a branch so that your hands are high in the air. Tie your angles to a long thick stick so that your ankles are wider than your shoulders. The friend then leaves you there all alone for at least an hour. They must be out of sight and within shouting distance in case of an emergency. If anyone else appears tell them that you are doing it for a dare. After the hour, the friend rescues you, but you have to walk back to your car naked (shoes permitted).
How many of these can you do or have you done?
Remember, when doing all these dares you should take a friend with you so that they can look after your safety and make sure that you don’t get arrested.
Sam still hasn’t started developing a teenage girl’s body and still looks like a 12 year old boy, although her nipples are now on top of little mounds. There are a lot of young boys these days with bigger breasts than Sam, and me for that matter. BTW for those readers who haven’t read about my previous adventures, Sam is now 17.
Jon has been taking Sam to sports centres with her dressed as a boy, and both of them using the men’s changing rooms. After whatever they’ve been playing, they’d then go and use the men’s communal showers. Sam usually wants to wait until other men used the showers so that she could look at their cocks. She’d face the wall so that they couldn’t tell that she is a girl and look over her shoulder. After a while she’d turn round and face them. Sometimes it took ages before they notice that Sam doesn’t have anything between her legs. Some got embarrassed and turn away, a couple actually watched her and got a hard-on, much to Sam’s delight. Only one man started telling Jon that he shouldn’t take a young girl into the men’s showers. Jon told him that Sam was only a little kid that was too young to be upset by it and too young to use the Ladies room on her own. Just to get the man more annoyed (or happy), as soon as he went to get dressed Sam went to get dressed and sat on the bench opposite the man towelling herself dry, with her legs wide open. In the end the man left with a red face.
On one of the warm days, Jon took us all to a country pub for lunch. All us girls were wearing just short summer dresses and shoes. This pub had a kids playground with a swing and slide and other such things. While we were eating some lads in their early teens arrived and were hanging around the playground. When San had finished eating Jon told her to go and play. She was on the climbing frame at the back, away from the adults and I could see her hanging upside down. Her dress was up/down round her neck leaving her little crack and chest showing. I smiled to myself and a minute later one of the lads saw her, nudged his mates and they went over to the climbing frame. Sam let them watch her for a short while then climbed down and went over to the swing. She started swinging back and forward. Each time she came forward her dress was up round her waist and her legs wide apart.
Needless to say the lads had followed her and were enjoying the view.
This went on for ages and a little girl went over to her, waited for a bit then asked Sam if she could have a go. Sam shouted at her and she ran off crying.
Jon saw (and heard) that and called her over. Sam stood in front of him looking down at the floor. Jon was telling her off just like any parent would discipline a young kid when he saw that he had an audience of the lads and a couple of men drinking at a nearby table. Thinking quick, Jon told Sam that she needed a spanking to make her remember to be good. Jon swung round and slapped his thigh.
Sam knew what to do. She moved round so that her back was to the men and lads and lay over Jon’s lap. Jon lifted her dress over her butt and pushed her kegs apart. He then proceeded to give her 10 hard slaps with his hand. All this was done in silence, Sam and the audience.
When it was over Jon told her to stand up and sit down next to me. Sam didn’t cry and as she sat down she smiled at me. She’d enjoyed it.
We finished our drinks and went to the car. Hannah got in the front and I got in the back with Sam. I did a quick pleasure check. Her puss was dripping. She really had enjoyed it.
Jon has been very busy at work these past few months. The continuing recession is affecting his business the same as most other businesses. He’s even had me there helping at times, and he’s brought lots of work home for me to do. None of the technical stuff, just the admin type work. Because of this we haven’t had a holiday this summer. I’ve really missed the sun and sand, and the other fun that we’ve had at his villa. But he has promised that we can go there during the October school holidays.
Shortly before the school holidays he told me that there would be no holiday and as a way of making it up to me he took me away for a few days to this hotel and spa somewhere near Birmingham. Clothing was optional and it was common for naked people (including Jon and me) to be seen walking around the place. The most notable part of those few days was the massage that I had there. It was given by a young man who had a little chat with Jon before he started. Jon stayed to watch and learn.
He started on my back and I have to say that I was VERY relaxed when he told me to turn over. My head was next, then my legs that were over his shoulder as he did my upper thighs, getting very close to (but not touching) my pussy.
By this time I was dripping but my nipples and pussy hadn’t even been touched.
Then the really good bits started. My little breasts got a treatment that I have never had before. They were squeezed, pummelled, pulled, tickled, stroked, and just about anything else you can think of, all by these oily hands.
My stomach was next, but that wasn’t long before he started on my pussy. He was prodding and squeezing bits all around my pussy that I didn’t know I had. I had my first orgasm the second he touched my clit. The second one came shortly after as my clit was ‘massaged’.
I looked over to Jon and saw a big grin on his face and a big tent in his robe.
A couple of minutes later the middle two fingers of his hand went inside me and started probing all over inside me. At the same time his other hand was pressing down on different areas just above my pubic bone. Then all of a sudden he gripped my pubic bone with the palm of his hand that still had the middle two fingers in me, and he started lifting me up off the table and putting me back down, over and over again.
The next thing that I knew, I was giggling and jerking all over. He had removed his hand but I was still bouncing all over the table with a bloody big grin on my face. It was one orgasm after another, orgasms like never before. And he wasn’t even touching me. It went on for what seemed like 10 minutes.
When I started calming down his hand went in me again and I was bouncing up and down again. He’d ‘topped-up’ my orgasms and I was back in heaven again.
This time when I stopped giggling and jumping about so much, Jon did what the masseur had done and I was back up there having more orgasms.
After what seemed like another hour Jon let me come back down to earth. The masseur had left us. I was totally exhausted. I have NEVER had so many absolutely knackering, fantastic orgasms.
Jon had to help me back to our room and put me in the shower where I slumped to the floor and fell asleep. When I woke up the shower was still running and I felt happier than ever before.
Jon got his relief shortly afterwards.
One Saturday during the school holidays Jon took me shopping in a big city not that far from us. In one of the thousands of clothes shops I found a couple of dresses that I liked. When I got to the changing rooms I saw that there was a long queue. Jon told me to follow him and we went to a corner at the back of the store. Now this store was quite big and there wasn’t much space between the racks. The owner obviously wanted to get as much stock out on the shop floor as possible.
Anyway, in this corner Jon told me to try the dresses on there. As you will know by now, I don’t wear underwear so when I took my own dress off I was naked apart from my shoes.
No one saw me as I put the first dress on, but as I took it off two teenage girls appeared from behind a rack. One of them looked shocked but the other grinned and said, “Cool.”
After I took off the second dress Jon told me to look through a couple of racks where we were before I put my own dress back on. In that time a young woman, with her man in tow, started browsing a rack nearby. The woman didn’t notice me, but the man certainly did. By the time he stopped staring his girlfriend was half way across the store.
I didn’t buy either of the dresses.
One thing that Jon bought me a few months ago is a butt plug. Not for me to wear in my butt, but in my puss. It has a cone shaped bulb about 3 inches in diameter, a 2.5 inch stalk and a diamond (not real) in the bit that is visible. Jon has had me wearing it quite a bit, but it’s not as much fun as my Ben Wa balls.
Well, I’m sure that I’ve done other things that I should be including in this update, but that’s all that I can remember at the moment. Hopefully it won’t take me so long to write the next update.