Jane's Adventures - by Boyfriend Jack - Part 2

Hi Webmaster,

Part 2

About 6 weeks later ( and all that time planning) I made reservations to a bed and breakfast about 5 hours drive from home. I had already contacted about 4 guys in the area and narrowed it down to 2 guys through conversations and emails. They were interested in experimenting with me on this and see where it led. The first guy bumped into us on our second night there at a local restaurant/bar. He was friendly but never closed the deal or even flirted with her. He seemed more nervous than anything and I had to call it a night before he said something to get me in trouble. It was awkward and didn't seem natural. Jane never said anything but I was glad it ended.

The next night we went to a pub on the same street as our B&B. David (alias) was already there and played it cool. We had a few drinks and then played some pool games where David came into the picture and asked to play winners. It was his suggestion to go there and it was perfect. We ended up taking turns and he told us his 'story' which was all bullshit but built the momentum. He was here doing reviews on local hotels and B&Bs. He mentioned he was staying at the at the same one as ours. That got him asking Jane a bunch of questions and her opinion on it and they talked for ever.

We ended up hitting another bar after this one closed and continued having some drinks. He made himself seem like the world traveler and Mr. moneybags and all the time I knew he had never left the State. She was eating it up.

This bar closed an hour later and it was 3 am by now and we started our way back. Although he really didn't have a place at the hotel, we figured we would try and see if we could work something out before we got there. We had come up with a plan where he would offer a bottle of amaretto he had in his room and I would gallantly suggest bringing it to our room since ours was a suite with a couch.

It worked and Jane was all into it. We got there and waited for him (to go to his car and get the bottle). She changed out of her clothes and into her comfy jogging pants and oversized shirt. David came in and we all got comfortable on the couch and Jane on the bed.

After a while he turned on the TV and started to change channels to see if anything good was on and ended up on Cinemax (more like skinemax). It was a soft port movie but it got us talking about how fake it all was and Jane started to ask a bunch of questions about if they were really having sex, etc.

I jumped on the bed and David soon followed. Jane stayed laying down on her stomach with her head at the foot of the bed watching TV. David and I sat on either side of her with our back on the headrest. We kept looking at each other and I wasn't sure what to do.

After a minute or two I left to the bathroom expecting to come out into a moment, but that was just wishful thinking. Instead as I came out, David had laid down next to her in the same position. I turned off the lights to help watch TV J .. and sat next to her the way I was before. I could see both of them and kept rubbing my pants imagining what might happen but trying to convince myself it might not happen.

David poured us all drinks again and dared her to gulp it down with us. She did and just about coughed a lung. He kept rubbing her back and was basically pressing his body to hers while he did. I was rubbing her leg and making sure she was OK but wanted him to do the work.

By the way, David was almost 6ft tall, bald as can be, and had a couple of tattoos. Definitely could be a one of those biker guys you see on the weekends.

David started to ask her questions as they watched the porn about her own sex life and if she had ever done (a list of things). That is when he got her to talk about the truth or dare game we played and the thing s that happened. He ended up asking me infront of her if it didn't bother me that another guy had touched her or that they were looking at her. Here is where I got gutsy and said 'not at all … to tell the truth it was sort of a turn on'. He asked how she felt about that and if she felt weird having me watch her do those dares. She said she didn't even think about it but it was fun.

This is where David took control. He started to ask me if it would bother me if he … and as he asked he placed his hand on her ass. Jane kept her eyes on the TV without ever looking back and my dick got hard as a rock. I told him no, it didn't bother me. Then asked the same question and this time he began to kiss her neck. All I saw was Jane tilt her head a bit and I gave the same answer.

He asked the same question again and pushed her on her side as he squeezed her breasts. Her eyes were closed and I gave the same answer. He never looked at her as he talked to me which made it weird and exciting … as if she had no say in it.

For most of the night he would ask a question every time he did something to her. He put her on her back, pushed up her shirt, sucked her tits, took off his clothes, laid down next to her and made out for a while.

I could see him put her hand on his cock and she would play with it for a while. Then he asked again and had her give him a blow job. She looked at me the entire time making sure I was ok with it and I was sitting there stroking myself.

David took her over the bed and pulled down her loose pants, leaned over, and started to eat her out. There was Jane with a shirt half off, jogging pants around her ankles, and a stranger in her ass licking away. Just so you know, I already came once and was going for two.

The last question he asked is if I minded him fucking her. This is where she voiced her disapproval and said she didn't want to go all the way. She knelt over and kept sucking him off.

I was a little disappointed but couldn't complain. The rest of the night was great. He left not long after and her and I talked about it all night long and the next day. Then we didn't bring it up for 2 weeks. I think she was nervous about it or something.

Needless to say we did talk about it and that led to another gathering with Doug (truth or dare guy) and his friends.

Jack - JackFrostDare @ gmail.com

PART 3 IS BELOW.