Hi Webmaster,
Part 3
We had seen Doug a couple of more times but only as casual meetings which made everything better. There was always a few flirts both ways but nothing serious. It built a relationship between us over the months and I was getting anxious and frustrated. I wasn't sure where it was going and Doug played it smooth. He and I would talk often from work and we both agreed to take it easy in order for it to work best. I told him about our experience with the other guy and he loved it and was sure it would happen.
Finally one day I confessed my real fantasies which involved her being involved with another guy without me knowing or planning it. I can't explain it but the thought of her having sexual experiences on the taboo are really exciting.
Jane lives about 1:30 hours north of me so we usually end up spending the entire weekend at each other's place. This led me to my suggestion with Doug. He lives just 20 minutes north of her so he is much closer than me. I told him if there was anything we could do with that. My suggestions were a little over the top but after a few days he came up with the perfect idea.
Ok, so now we've hung out with Doug for 5 months almost every weekend for one thing or another. Meeting for happy hour on Friday, hanging out at his place with his 'party' friends, etc. She got to know most people and I was finding it so strange that someone who I never knew was actually becoming a friend. Two weeks ago he was having an early xmas party at his condo. Three days prior I mentioned that to Jane that my boss needed my team to work over the weekend prior to the end of year …. Perfect excuse since I work at an accounting firm.
Nothing was said about the party. On Thursday Doug called with the excuse he couldn't get ahold of me to confirm about the party and she told him the bad news. This is where he worked his magic and mentioned how some of the girls were asking and hoping she would come since they always had a great time talking the night away. She ended up calling me and telling me what he said and I could tell she was waiting to see if I said anything. I casually told her that she should go since I would be stuck at the office Friday and Saturday and wouldn't see her until Sunday. Done!!! She said she wanted to and hang out with the girls.
Doug and I talked about many scenarios and as usual, the reality was none of them. This is what Doug told me happened since Jane didn't say anything for over a week … but that is another story.
Jane drove up to his place on Friday night around 8pm, a while into the party. She wore a sexy black party dress since everyone was dressing up. Most of the night she was talking to everyone and Doug made sure to make his presence known. He would get her drinks and check up on her. There was one point where they were on the balcony and ended up alone for a good 30 minutes talking about anything. Doug brought up the beach, bathing suits, and then brought up a few stories of his sexual experiences in the water, getting caught, etc. She didn't say much but he could tell she was listening and blushing.
He constantly touched her back and rubbed her legs, complimented her, and would brush up against her. She would also flirt with him and put her arm around him, lean on him, and things like that.
He tried to get a game of TOD going but it never took off. Most people were more interested in drinking and ended up smoking some pot. Needless to say Jane did both. By the end of the party the two of them were on the couch and she had her head on his lap as a few of the people left just talked and got high. He stroked her hair for a while until the rest of the people left. He wasn't sure how to take it to the next level and asked her if she wanted to stay since she was pretty buzzed and not in the best condition to drive home. She kept insisting that she couldn't and it was better if she got home. He ended up saying she was in no condition to drive and offered to either call a taxi or drive her himself.
She took him up on the offer to drive her home and he did. On the drive over he kept his hand on her leg and rubbed slowly up and down her thigh. At some point he took out a digital camera he kept in the glove compartment and took a few pictures of her telling her he was going to make sure I knew how drunk she really was. She just laughed and posed. Then he took a couple of close up shots of her breasts and she got a little embarrassed but didn't stop him. He said he wanted to show a coworker of his what a perfect pair she had. She asked why and if he spoke about her at work and he told her he always does.
She loved it and he told her all the sexy things he would tell his coworkers (which was really me … lol). Her outfits, her body, the game of TOD.
This is where he pushed higher on her thigh and pushed her dress up a little and she parted her legs exposing her pussy. She was wearing no panties. She took the camera and took a picture of him fingering her and told him to show his friend that shot.
When he got her house, he walked her in and as she was turning off the alarm, he pulled up her dress and began to finger her from behind. He said she just kept breathing really heavy. She realized the front door was she was moving towards it to close it and he wrapped his arm around her and squeezed her breast and pulled her against the wall next the door. He turned her around, door still open, and got on his knees to eat her out.
There she was, dress pulled up, a guy between her legs, and both exposed if anyone drove by.
I was really hoping for a lot more build up but he said he was so horny and she was about to orgasm. He took her to a chair in the kitchen and he sat on it quickly putting on a condom. While he did this, she took off her dress and bra and then sat on top of him, facing him … riding him. Turns out he is a very thick guy … about 6 inches long, but very very thick and took her a little time to have him inside.
This was the first time Jane had a man nearly twice her age.
They finished quite quickly and he took her the bedroom. This is where I got a call from her to let me know she got home and that she was exhausted and going to bed. She didn't talk very long and hung up. At this time I had no clue and found out later that night when Doug called me. While she was on the phone with me he was going down on her.
After she hung up he popped up on the bed, lifted her legs and went at it again. He didn't last long again. He talked to her while they were going at it and brought up how he wanted to fuck her since the first night and how he knows 'I' can't fuck her like he can. These are things I wanted him to say. She just kept saying yes, yes, yes … this is your pussy, fuck it.
He left not long after and called me on the way home to give me all the details. We were on the phone for over 2 hours and I was dying.
The next day Jane had a friend drop her off at his place so she could pick up her car. Because it was a private condo with gate she had to go upstairs and get the gate key from him to leave the underground garage.
Doug says she didn't say anything but was courteous and thanked him for the party. She was wearing a pair of PJ like shorts and a plain t-shirt saying she didn't think she was going to see him and only jumping out of one car and into the other. He offered her to hang out and enjoy the beach but she was pretty short and just wanting to leave.
He tried to kiss her a few times at the door and she stopped halfway through the 2nd kiss saying it wasn't a good idea. Doug was only wearing a robe since he had slept in and took her hand and as soon as it touched the outer part she pulled back. He kissed her again and grabbed her hand again … pulling it firmly until it slipped it inside and on his cock. She didn't pull away.
I called her a couple of times with no response. She finally called me and said she had slept in late and was going to go shopping with her girl friend. I didn't get another call from her until 4pm when she got home from his place but told me her friend just dropped her off.
Turns out she was with him all morning and afternoon. According to Doug, they had sex at least 5 times throughout the day. They went to the beach, had sex in the water, in the shower, in the kitchen, and in the bedroom. Needless to say this is an amazing fantasy come true. He took a few more pics with her … one he had her take off her top while at the pool and had her finger herself. The other was in his bedroom as he had her try out some lingerie he had (not really sure why she did that but he says it turned her on to try them on for him).
To this day she was not said anything to me and we have seen him together twice but nothing else between them. I can tell she wants to tell me but isn't sure how to. I'm sure the time and place will come but until them I will plan some more things with Doug.
Jack - JackFrostDare @ gmail.com
PARTS 1 & 2 ARE BELOW.
