This is a story about romance but includes themes of grief, dogging, men pissing videos and a bisexual incident. The story includes descriptions of an actual video. All the references to Sandbanks, Studland, Swanage, Old Harry Rocks, Brownsea Island, Gerry's Point and the ferry are authentic.
Poole harbour really is the second largest natural harbour in the world.
The Story Starts
Brad asked his best male friend John "Would you go on a date with my lady boss while I'm away on my next business trip? You can use my master bedroom, if you strike lucky."
John rented a single bedroom from Brad. A single bed would not be very sexy if he was trying to impress a woman. This applied even more if that woman had a middle management position. Brad's en-suite double bedroom would be much more suitable for seduction.
Brad said "Fiona is about 10 years older than you, respectable and business-like. She has average sized breasts. She keeps herself in good shape, she used to exercise in a local gym.
At the office Christmas party she made us look twice. She wore a Christmas outfit that showed us most of her breasts. She was dressed as Santa's helper. Most of the men wanted to be Santa."
John said "She sounds impressive."
Brad continued "Fiona's husband, Tom, was dressed as an elf. I thought that he was lucky to get Fiona as his wife. But I knew that they were very much in love.
We little realised that Tom would be dead before the next Christmas party. She lost Tom due to a heart attack. Fiona went through a 2 year period of depression. She was often caught crying in the ladies loo. She only survived mentally because of her work.
Gradually she got over her bereavement. She had 2 dates but they never lasted. I have been Fiona's best friend and soulmate, other than her husband. for the last decade. I know her hopes for the future. They are a perfect fit with yours."
I could see that both men were unsuitable. They aren't as nice as you are."
John said "Thanks for the compliment."
Porn Videos
Brad continued 'Basically Fiona wants someone to be like Tom, but to be a bit more open to the sexual world.
Over the decade Fiona and I shared our sexual experiences and fantasies. She knows things about me that no one else does. I know that Fiona's husband followed you on your porn website. He liked the dogging videos you posted and left you comments.
John said "So Tom was "Scot_sex69". He was one of the few who posted comments. He also liked my "women sucking dicks" videos."
Brad replied "Technical that was Tom and Fiona. So she kind of knows you. If you look at "Scot_sex69" you will see something of Fiona's sexual tastes."
Dogging
Brad had introduced John to the world of dogging. At the dogging sessions Brad was active sexually whereas John liked to watch. Like lots of the male voyeurs he played with his prick while watching. There were few female voyeurs.
Brad continued "Fiona often asked me about my sexual adventures. She liked hearing about me cuckolding men. It turned her on but she would never want to cuckold Tom. Anyway she asked me about my dogging experiences. In answering her question I revealed to her that you are a voyeur. I gave her your porn address and that's why "Scot_sex69" sent you a friend request.
Fiona The Porn Director
Fiona's fantasy is to actually make a porn video. She says she would like to recreate some of my cuckolding and dogging adventures, but with her and Tom's slant of sexuality."
John said "So I am going to date a porn auteur?"
Brad replied "That oughta make it good."
John didn't laugh at Brad's bad pun.
Brad continued "Anyway, when Fiona had a man in her life she was happy. When she was happy, so were we underlings. A happy boss means a happy underling".
John said "So if I go out with your boss you get an easy time at work?"
Brad said "And a happy friend. She earns a lot of dosh, she has her own home since the insurance money paid off the mortgage. She is a good catch. You are a good catch. You would make a great couple."
John liked that Brad, who was a babe magnet, thought that he was a good catch. He agreed to go on the date.
John's Prepares For His Date.
John was excited at the prospect of a dinner date. He wanted to make the best impression. Brad loaned him some money and John bought a new suit.
Fiona chose an upper class restaurant for lunch in a place John had never heard of John knew he would be nervous and didn't want to wait around all day so having lunch suited him.
Brad helped John to buy a new suit, 2 new shirts and 3 ties. John bought new shoes and socks. He bought some designer underwear.
When he got home John got dressed in his new glad rags. He looked in the mirror and felt like a new man. He had never looked better. John considered shaving off all his pubic hair but in the end just trimmed it. The trimmed pubes made his cock look a bit bigger.
John felt that his hair let him down. He decided to book an appointment at a pricey hairdresser. This was the first time he had booked an appointment at a barbers. The haircut cost him £70, which was more than 3 times what he usually paid.
The haircut took twice as long as his normal appointment. John felt that this was a "rip off". His hair looked no better than his usual barber. The one consolation was that there was a woman cutting his hair and she displayed a large percentage of her breasts. He liked seeing the hairdresser's barely covered breasts as she washed his hair.
Scot_sex69's Favourites
John investigated Fiona and Tom's favourite porn videos. They had lover 60 videos ranging from soft core excerpts through to cuckolding and bondage films. It didn't really give him much of a clue what Fiona liked. They had lots of friends who had lots of fetishes. Tom's profile said he was male, with interested in dating no-one. His fetishes were not shown.
John watched some of their favourite videos. But there were too many to watch them all.
The First Date
Brad was away on a business trip. Fiona picked John up in her BMW. The restaurant was 3 hours drive away at upmarket Sandbanks.
Fiona explained "Sandbanks is THE most expensive real estate in Britain. it is even more expensive than London. The local estate agent has nothing on his books cheaper than £1 million. One of the celebs who lived there recently got permission to knock down his £7 million house so he could build something even larger and more expensive."
They chatted about inconsequential things as they sped towards Sandbanks.
At the posh Sandbanks restaurant Fiona said to the waiter "Give us lots of time between the courses, please."
The waiter brought Fiona chilled water with a twist of lime in it and a glass of white wine for John.
John asked "Why have we come so far from our Midlands homes?"
Fiona explained "I grew up in Swanage. I had always dreamed of having a swish meal at Sandbanks but my family was too poor. Tom, my deceased husband, thought that "paying for a name" was a waste of money. Now I have money and someone to share this much delayed treat.
