Disclaimer -- Everyone involved in sex is of a legal age, this story contains, blackmail and coercion if you do not like these scenarios this story is probably not for you.
Reginald or Reggie to his friends and family is a forty-seven-year-old widow, he kept himself in shape going for early morning runs and the gym a few times a week. Gradually turning grey but otherwise could easily pass for being late thirties.
His wife passed away just over four years ago. It was unexpected and sudden due to a ride malfunction at a major park. He went into a world of his own after distancing himself from everyone.
He never thought he would find love again so instead of moving on, he ventured online. He started to talk with strangers on chat sites, sometimes these would be innocent, with some he would exchange fantasies.
One night he was talking to a woman in a different country. He referred to what he would like to do with his big dick to her after she sent him a raunchy censored photo. She asked how big he was. When he replied nine inches she asked for proof.
He sent her a picture just of his cock. She instantly replied asking if it really was his and not just a random internet picture. He then sent her another one with a message on paper next to it, for you cherrylips99 it said which was her username.
She then messaged him saying you should use that thing for cash. He replied with a lol emoji. I'm being serious, I'd pay to watch you jack that beast off she replied. A little back and forth went on and she sent him a link to a couple of web sites with live chat and donation or payments options.
He agreed to investigate it as was intrigued. He was ok for money as he received a payout following his wife's passing, mentally he wasn't ready for work. The payout wouldn't last forever though so a little bit here and there might help.
The following night he signed up to one of these sites, when he logged on to the chat site cherrylips99 was online so he dropped her a message saying he had signed up.
They started a private chat, he explained he wanted to stay private so she talked him through going live and making sure not to show his face. Once he was set up and ready he pulled his cock out. Wow she messaged him in awe at its size and girth.
He then noticed a payment hit his account and a message telling him to start wanking. He did as was asked, once it was fully erect another deposit was made with a message that said cum for me. He started to wank faster.
He was getting turned on knowing he was being watched, it didn't take him long before jets of cum shot out, he moaned out loud as he squeezed every last drop out.
Another deposit hit his account, that wasn't so hard now was it, I came also was the message attached. She then talked him through coming off live stream and back to chat.
They talked for a while and Reggie was shocked that there were lots of women willing to pay to watch men jack off. Cherrylips99 even said she would recommend him to a few other members.
Over the next month whenever he logged on, he would be inundated with requests for private shows, he ended up doing group rooms with some of them. He would get requests to masturbate in different places. He couldn't do these as was worried about live streaming outside of his home. Besides the money was good but more than that he was actually enjoying it.
It was suggested he set up an account on a porn site or even his own site where he could film himself wanking off in different places when he felt he could safely then share them. He joined a site that lets you take a subscription from members for videos you upload for them, he also set up on a few porn sites where people could pay per video.
He didn't expect to get much from this, but the ladies on his original chat all signed up and made requests. He would refuse some but others he thought about. Wanking on a bus came up a couple of times, in the woods and in a pool were also popular requests.
In just a couple of months he had gone from a no one on a chat site, to being an online porn creator. His main income now was the subscription site he charged at £20 per month and with over 300 regular subscribers, and the payments from chat and porn sites he was doing quite well.
He started to buy better equipment, going on short holidays and making more videos. He was then approached by Liam; Liam had been in a chat with Cherrylips99. She had mentioned how he was similar in size to Reggie and how successful he had been so suggested the same to him.
Liam wasn't interested in running a site and the pressure of making lots of material. So contacted Reggie to see if he'd be interested in taking him on as a content maker for him. It turned out Reggie was also based in England but a different city but meant they could meet up easy enough if needed.
Reggie was relieved as he could now reduce the amount, he made but still meet his subscriber's quota. Having two stars kept his mostly female members happy. Liam was also a bit more daring to make videos, so this helped. He almost doubled his subscribers over the next few months.
With less pressure on Reggie, he decided to take up an offer from his younger brother Kevin to visit him at his new country family home. It had been over five years since he last saw him.
Reggie and Kevin's wife Lucia didn't get on, Reggie had caught her cheating on Kevin, Lucia was thirty-eight and Spanish, five foot two, light tanned skin, long black curly hair. Pair shaped figure, small breasts and waist but great rounded hips and bottom. She turned heads everywhere she went.
Reggie was adamant he had seen her out with another man years ago, but at the time his brother didn't believe him and called him a liar, which had caused a rift between them. He accused Reggie of being jealous of his sexy Latino wife. It was because of her, he never reached out after Reggie's wife passed away either.
Kevin was very successful, he worked as a football agent for a large company. Lucia was able to be a stay home mum but with their kids being fifteen and thirteen she was basically a lady of leisure now and spent most of her time socialising these days.
Reggie knew he was mainly being invited out so his brother could show off his new house under the guise of making up, he had always liked being the most successful brother. At this stage though Reggie was actually earning more than Kevin.
As Kevin's new house was in the countryside Reggie knew it would present new filming opportunities. His nearest neighbour was over two miles away. The property was a seven-bedroom house on 180 acres of land, the stables had been converted to a pool with jacuzzi and sauna. It also had a gym and wine cellar amongst its potential filming sets. There was also lots of woodlands.
When Reggie arrived, it was early afternoon. He was surprised at the length of the driveway from road to house, this was really secluded away. As he drove round a fountain to park, he thought to himself he needs somewhere like this.
He had a little look around before he was greeted by Lucia who looked amazing, she must have just been in the gym as she had on a very tight set of light blue leggings and matching crop top. In a not so friendly tone she said, "oh so you have still actually decided to come visit us!"
"Kevin did invite me so here I am," he replied nonchalantly.
She then directed him into the house and upstairs, he followed her watching her ass sway as she went up the stairs. His dick was throbbing as he watched her.
She explained to him that Kevin had urgently had to go into work as some big transfer deal was happening, he would probably be away a couple of days as the player was moving to an Italian club. She then told him the kids were still at a camp for the next week.
Reggie looked at his phone and noticed the missed calls and message from Kevin to make him aware in case he wanted to reschedule. "I don't pay much attention to my phone when I'm out, so I didn't realise. Is it still ok if I stay?"
She replied in an uninterested tone "up to you, I'm going out shortly do you need me to show you around or are you happy to find your own way?"
"I'll be fine," he replied. His room was huge, it was like he'd checked into a hotel. It had a king size bed, flat screen TV on the wall, en-suite plenty of storage space. He made a second journey back to his car to grab his travel recording bag. He noticed Lucia getting into her car and leaving.
He decided to take himself for a wander around the house. That's when he stumbled into the master bedroom which was bigger than some one-bedroom flats. It had everything you could imagine. Reggie liked the TV that popped out of the footboard in the bed.
Still feeling a little turned on by Lucia he decided to have a little rummage through her draws. He was surprised to find a seven-inch dildo tucked away in her knickers draw. She had some very sexy underwear in there also.
After his find he felt like he needed to whack off so headed back to his room. Not one to miss an opportunity he set up two cameras. These were disguised in bags to make outdoor filming easier.
