The Lost Bet
Introduction:
Did I deliberately lose the bet
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. 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. 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.
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 I 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.
The Lost Bet
One Sunday last summer Jon was watching a F1 Grand Prix. Trying to show some interest I asked Jon who was winning. His reply didn’t make much sense to me, but just for a bit of a laugh I said, “I bet the red car wins.” Jon took me up on the bet, which I eventually lost. Jon was happy when he told me that I had lost and told me that as the forfeit, I would have to do something special for him. Nothing really different there, as I always do what Jon tells me, whatever he asks.
Jon kept me waiting for about a month before I had to pay my forfeit. Whenever I asked him he said that there was a lot of organising to do.
Eventually, one Friday afternoon Vicky and Bridie arrived at our house at 8 o’clock. We all piled into Jon’s car and he drove us to somewhere in West Yorkshire. It was a rugby club, but I’ve no idea where. We 3 girls were to provide waitress service for the drinks whilst a comedian did his show. We were the only women there. The comedian was real down-to-earth and quite disgusting really. Quite funny as well. Oh, we had to wear just ultra-short skirts and shoes – nothing else.
I’m sure that Vicky and Bridie got groped as much as I did; by the time the show ended I was soaking.
As the comedian was coming to the end of his show he asked me to go to a room at the side of the stage. Jon was waiting for me and he gave me a schoolgirl’s uniform (complete with bra and horrible schoolgirl knickers) to put on, and then a pack of cigarettes to put down my blouse. He then told me that we were going to give a show similar to the one that we’d put on in the Canaries a few years ago.
Jon put on one of those teachers’ flat hat things and a gown, and we went out. On the stage Jon pretended to be the teacher who had stopped a girl who he suspected had some cigarettes. He asked me for them and I said I didn’t have any. He said that he didn’t believe me and that he’d have to search me.
He told me to take my blouse off. I did, tucking the cigarettes into the band of my skirt as I did so. Next it was the bra, then the skirt. Finally it was the navy blue knickers. As they came off the cigarettes fell onto the floor.
Jon then told me that schoolgirls who smoked and lied got punished. A cane then appeared and I had to bend over, with my backside facing the audience. Jon gave me 5 strokes in quick succession. As always, after each one I thanked him.
I then had to spread my legs as wide as I could, giving the audience an even better view of my dripping pussy. As I did so I saw Vicky and Bridie through my open legs, each of them was sitting on a man’s knee with the man’s hand on their bald pussies.
Jon then gave me 10 more strokes harder than before. Some of them were getting just one cheek as the end of the cane whipped round onto my pussy.
I came during the next and last 5. I needed to put one hand down on the floor to stop myself falling over. I was still shaking when Jon told me to stand up and face the audience. As I calmed down I could hear all sorts of comments from the crowd.
Next Jon asked if it was anyone’s birthday. When he got no reply he asked if it was a stag night. The whole crowd pointed at one young man and called out the name Martin. Jon then asked Bridie and Vicky to bring Martin up onto the stage.
Poor Martin, he was so embarrassed, even though he was a bit drunk.
Jon then asked the audience if Martin should help to punish the naughty schoolgirl. Guess what everyone said?
I then had to bend over again while Martin first stuck a couple of fingers in my pussy, and then hit my backside with the cane. He wasn’t very good at co-ordinating his movements so Jon told him to lie down on the floor. When he was down, Jon told Vicky and Birdie to strip him. Vicky and Bridie were on him in a flash, and got his clothes off, even though he was struggling a bit. He had a semi that he was trying to cover-up. Pointing at Martin’s semi, Jon told Vicky and Bridie to do something about that. While Vicky and Bride played with and sucked Martin’s dick, Jon told me to squat down on Martins face.
Poor Martin, he was in heaven and hell. After a couple of minutes, Jon got a condom out of his pocket and gave it to Bridie. She didn’t need telling what to do. When it was on Vicky and Bridie stood up and Jon told me to impale myself on Martin’s dick.
That was the first time that Jon has told me to fuck another man. I was a bit surprised at first, and as I was standing up I looked at Jon who gave a little nod.
I lowered myself down and then started going up and down on my knees. While I was doing this Jon told Vicky and Bridie to do a 69 with each other. They didn’t need to be told twice.
It wasn’t long before I could feel Martin cum so I went down as hard as I could and then lay back. As his dick went soft I could feel it sliding out of me.
When Martin finally flopped right out, Jon told me to get Martin’s clothes, take him into the changing room then come back.
When I got back, Vicky and Bridie were still at each other.
I thought that the show would have been over then, but Jon had one more thing that I had to do. He told the audience that I would be walking round the room, and if anyone wanted to put me over their knee and spank me, they could, but for no longer than 20 seconds each. He asked everyone to play fairly so that everyone who wanted to could have a go.
I looked round and there must have been 50 or 60 men in there. I was a bit scared, but I knew that Jon would make sure that I was okay.
I looked at Jon then went over to the corner of the room and asked the young man if he wanted to spank me.
In the next 30 or 40 minutes my backside got redder and redder and more painful. My pussy got more and sorer as it got finger fucked by about 50 young men. My nipples got twisted, pulled and pinched until they were very tender. I even got a couple of fingers pushed into my backside.
After about the 15th knee it all got to be a bit of a sexual high haze. I came 2 or 3 times and the men had to lift me from knee to knee. I remember slipping out of the hands and falling onto the floor once. It wasn’t the men’s fault; I was covered in sweat and pussy juice.
To be fair to the men, not one of them tried to take advantage of me, they all (I think) took no more than the 20 seconds that Jon had told them.
When I finally got back to where I started I was absolutely shattered, I could hardly stand up. Vicky and Bridie had to hold me up.
The fun was over and with Jon thanking everyone for helping to punish me we all went to the changing room and into the showers. The four of us in the big shower area. Jon had missed out on having the fun so Vicky and Bridie were taking care of his hard-on while I just stood under the warm water soothing my painful backside.
I was just starting to feel something like normal when Martin came in with a tray of drinks. Jon invited him to join us but he declined.
On the way home Bridie and Vicky both told me that they’d been very nervous before it all started, but that had all disappeared once they’d had the odd finger or two in their pussies.
Altogether, a most unexpected by pleasurable forfeit. I think I will have to have a few more bets with Jon.
Love,
V
