The Challenge

Recently, my wife Lisa, her friend Dani, and I were all drinking as we sat in our hot tub. My wife and I have been together for 6 years, I’m 30 and she’s 27, and her friend Dani is 25. Dani also has a younger brother who just turned 19 and is currently living with her. We’d been drinking quite a while when her brother, Keith, called Dani on the phone. She hung up then began sharing her concern that he’d never get married or have a girlfriend. Lisa said he’s not really a ‘bad looking guy’ and asked why she felt that way. Dani explained because he’s very awkward and has another ‘physical deformity’ that she feels will prevent it. Lisa was unaware of this and asked what she meant, so she explained.

She had accidentally walked in on Keith about 2 weeks earlier. He was sitting on the bed naked with his iPad watching porn. She said she was shocked, not because he was watching porn, but because he was stroking the “damn biggest cock I’ve ever seen!” The problem was, it wasn’t even hard. They were both embarrassed about her seeing him, he actually started crying, but she didn’t want to just ignore it so she told him to get dressed and come to the living room to talk to her. She explained what he did was normal, he knew that and that wasn’t what upset him. He told her he simply couldn’t get an erection like “normal” people. He’d never been with a woman before, partially because he is socially awkward, but also because he’s embarrassed by the size of his cock.

She didn’t know what to do, she certainly couldn’t help him, so suggested he see the doctor. They ended the conversation with him still very upset. I could tell by Lisa’ s reaction she didn’t quite believe this story, she even stated she’s never seen a dick so big it couldn’t get hard. As the drinking and discussion continued, she finally said “As long as Rick (me) doesn’t care, I’ll get his fucking dick hard and I’ll help him get over that fear of women too.” I laughed and said that was up to her, Dani and Keith but I didn’t mind her trying. Dani laughed and told her it wasn’t going to work, but told her to go ahead and try. They devised a plan to have Keith help her with some stuff around the house the following weekend when I was going to be ‘out of town’.

That Saturday afternoon he arrived around 3:00, Dani and I were hanging out at her place drinking and waiting on the update. This is what she told us happened. She had several minor things for him to do, hanging a few pictures, cleaning out a portion of the garage, and moving several plants outside that were too heavy for her. She had promised him dinner and drinks when they were done. When he finished, she told him to go ahead and shower while she finished dinner. She’d laid out some swim trunks on the bed that he could wear, and they’d be perfect in case they wanted to get in the spa afterwards. They had dinner, then she went to shower as well.

When she came out of the shower she was wearing just a short bathrobe. He was still sitting at the table and she started doing the dishes and cleaning up. Keith got up to help her and as they worked, she let her robe fall open 2 or 3 times, which seemed to get his attention, she was naked underneath after all. When they were pretty much finished, he sat down as she put the dishes away. The last few she grabbed a chair and stood on it to put them on the top shelf by the sink. She knew her ass and pussy were visible to him and saw him staring as she turned to get down. She asked if he was embarrassed and wanted her to put on some clothes, he just stared and shook his head.

She then grabbed him by the hands and led him to the bedroom telling him, “I want to be your first woman.” She said she took off her robe and lay down on the bed and instructed him on how to eat her pussy. He caught on quickly and she soon came then had him stand in front of her as she sat on the bed. She slid his shorts down and was shocked at the size of his cock. It was several inches long, not hard, and very thick. She began giving him a BJ and found his dick getting firmer, but not really hard. She eventually gave up on the BJ and spread her legs and guided his semi-hard dick inside her. She said she doubted she could have taken it all had it been erect. She did manage to get it inside her pussy, but he couldn’t really fuck her because it would fall out. Eventually, she just held him tight against her as she ground her pussy into him. She actually came again and asked him how he was doing. His eyes were closed tight and he just nodded his head. He finally came inside her, even though he wasn’t hard.

Afterwards, they showered together, she tried again to get him hard, but failed. He left a bit later, still unable to get an erection, but at least he was happy. Lisa was disappointed for failing him but refuses to call it quits and wants another chance soon.