The Wingman - Part 3 - Sex Stories

The Wingman - Part 3

... moment. Maybe Alan was the sort of guy she hoped he wouldn't be. "So I know it's a really, really dumb move to talk about past relationships in a moment like this or even on first meetings, but can I just let you in on a little bit about me?" Alan asked. Cassie nodded. Taking a deep breath in, Alan began to explain the last year of his life. Not in so much detail to make Cassie fall asleep trying to keep up, but just enough to let her in on how he got to this very moment with her. He admitted how the break up with his ex, while mutual, was partially his own fault. He admitted that he couldn't bring himself to meeting new women, how the closest he got was online things that had less than a chance of becoming reality. And then after throwing all of that out there to this gorgeous amazon sharing his bed, Alan simply sat there for a moment in silence thinking that he probably just showed how much of a loser he truly was. Still he couldn't take it back. And in more ways that not, he wasn't upset about that anymore. "I know I probably shared too much, Cassie, but I just wanted you to understand me. Honestly, during the time I was with my ex we only had sex for a certain period of time until she felt guilty over it. She asked that we do anything but have sex from that point on and we amazingly still made things work for 2 years after that. It was actually even more intimate to just do what we did that way because it made us learn what we both enjoyed more than just jumping ahead to ...

... the sex, if that made any sense." Alan suddenly found himself on autopilot as he talked, telling her things that, in the moment, probably shouldn't have been said. Things that he shouldn't have admitted so readily, like the way he enjoyed fingering his ex to help her orgasm over and over before she even had to touch him and how giving to someone he was attracted to was so exciting compared to his own pleasure sometimes. The little voice in his head kept telling him to shut up but his heart just kept letting him say everything on his mind, opening up to Cassie in such a way that it was all or nothing. Finally Alan found himself quiet, sitting in the striped darkness of his room. Cassie touched his hand and Alan took hers in his as he looked over at her. She sat up next to him and pressed her lips against his once more. The kiss was gentle and loving, as if without saying a word she was simply telling him she understood him. For all the worry of him saying too much and opening up to her so fast, the kiss was making Alan's walls crumble to the ground even faster. "So I didn't scare you off?" Alan panted between kisses. "Not at all," Cassie said, pulling him down to the bed with her. "You're sure if we do some things tonight that if we don't have sex you won't be upset?" Cassie asked quietly. "As cliche as this sounds, doing anything at all with you would be an honor. Why would I want to be upset and ruin anything that could happen?" Cassie took Alan's hand in hers and brought it ...