Since my last story went over pretty well, this is the one that gets me most worked up. I hope you like it too.
Working in a restaurant, I meet lots of young and cute women. Alexis was only 19, but she always wanted to hang out and talk, sometimes about sex and relationships. I wanted to be helpful, also couldn’t pass up a thin adorable redhead talking about her sex life.
Alexis had a bunch of rough relationships, bad guys who didn’t treat her well or listen to her needs. She felt like she was just trying to please other people, and I wanted her to know that the only person she really needed to please was herself. I guess she took that kind of literally, because one night after closing, we were having drinks and talking about being single. I said that sometimes to just have to make love with the person you care most about: yourself. She confessed she’d never masturbated – never with a toy, or fingers, or a pillow or anything else around her house. I casually said that it was worth it, and she should just take an evening to think of hot and sexy situations, and let her hands do the rest.
We left work, and a few days later, Alexis came up to me on her break and admitted she tried and couldn’t do it. She felt weird, and couldn’t get aroused. And then, she asked me the single hottest thing I’ve ever heard: she wanted me to help her learn how to cum on her own.
I was very surprised, never been asked that before by anyone, let alone a smoking hot young redhead. Of course I said I would help, but it would be mostly up to her. She laughed, saying she didn’t want sex, I shouldn’t get the wrong idea, but having a little encouragement and some tips would be nice. Alexis was a bit sheltered, obviously didn’t get the sex talk from her parents, and didn’t see any problem with asking a friend for some personal help. So we made plans to hang out at her place that night.
I was very nervous and also kind of in a horny trance when I got to her place. Was she just going to masturbate for me? Or just ask questions? Or maybe she’d chicken out, realizing this was an awkward ask. But I got up to her door, and she was wearing her normal sweats and a t-shirt, offered me some tea, like it was no big deal.
We sat down in the living room, and she admitted that one of the reasons she asked me to help her is because she heard me talking about some casual sex encounters I’ve had, and had never considered sex to be like that. So we talked about teasing and foreplay, all the time I’m getting hard and imagining her wet pussy getting stuffed as she makes cute little whimpers. At some point, we start looking at pictures, and she says that what turns her on most is hearing another person be turned on. And this is where I almost blew my load in my pants… she wanted me to find some porn I liked, and masturbate to it with her.
The rest in part 2…
Source: reddit.com/r/gonewildstories/comments/105fo19/m_teaching_my_friend_how_to_get_herself_off_pt_1