Her Inverted Intimacy Challenge: part 3 -  Porn & masterbation confessions and demonstrations. (mutual stimulation) By darrenr.  Listen to the Podcast at Steamy Stories. One evening, Anna sat beside him on the couch with a serious look on her face. “Jake, listen, I know I’ve already put a lot of burden on our friendship these past weeks. There’s something else I want to ask you about. I don’t want to do a cycle of agonizing self-doubt this time, so I’m just going to go out on a limb and ask you. Do you promise to tell me if my question makes you uncomfortable?” “Of course I’ll tell you,” Jake said. “You know that model you showed me earlier, the one with the inverted nipples?” “Yes,” Jake laughed. “Yes, I remember.” “You found those pictures pretty quickly. Have you looked at pictures of her before?” “Well, yes,” Jake admitted. “And when you looked, it made you feel, aroused?” Jake felt his face turn red. There didn’t seem to be any point in denying the obvious. “Yes.” “Even though she has weird nipples?” “Anna, look. I don’t see her nipples as a negative. It just made her more enticingly unique and fascinating.” Anna nodded. “And when you felt aroused, looking at her pictures, did you, well did it make you want to, touch, yourself?” “Anna, are you asking if I masturbate when I look at porn?” Anna nodded. “The answer is yes, of course I do. I’m not proud of it, and I’ve never talked with anyone about it before. But you seem to sincerely want to know. I’m, I’m not really interested in being teased about this.” “Why would I tease you? I wouldn’t do that.” Jake gave her a doubtful look but saw only sincerity in her expression. “Do you mind if I ask you more questions?” Jake laughed. This woman bared her beautiful body to him every day. How could he say no? With a sigh, he said, “Go for it.” “How did it start? Wasn’t it weird?” “It started quite innocently. I somehow noticed it felt good to touch myself there, and it seemed like all positives and no negatives.” “Were you looking at porn then?” “Oh no, not at first. I’m not even sure I thought about girls at first. That connection came later.” “Did you hide it?” “Well, yes. I clearly sensed this was a private thing.” “And that’s it? All positives, no negatives from the start? No shame involved?” “Oh, I didn’t mean to suggest that. I said it started quite innocently.” Jake paused briefly, and then continued very quietly. “Eventually I got the message it was something to be ashamed of, and I associated profound guilt with it.” “Then you stopped?” Jake shook his head. “Of course not. It felt so good! I simply internalized the shame and self-loathing.” Anna squeezed his hands in hers. “Do you still feel shame?” Jake took a deep breath. “Not the same way. Eventually I realized I wasn’t hurting anyone, and while it isn’t the most productive use of time it’s not worth beating myself up over. The only thing I struggle with anymore is keeping my fantasies respectful.” “What do you mean?” “Well, like, I used to try to imagine what every girl in my school looked like naked. But it didn’t seem right to fantasize about someone who hasn’t, invited me to. I can’t help what images pop into my head and try to ignore the inappropriate ones. That’s why I feel okay about looking at porn. Those people have given permission to be fantasized about.” Anna squeezed his hand and was silent for a while in thought. “For me, I also got the message, as you said, that I shouldn’t touch myself that way. And I didn’t. I’ve since accepted, intellectually, there is nothing wrong with it. But I can’t seem to shake this latent shame. I’ve tried, and it just doesn’t work for me.” “What doesn’t work?” Jake asked. “Touching myself. Masturbating. Every time I try it, I can’t overcome the feelings of shame.” “You’ve never masturbated?” Jake tried to not sound incredulous. “Not really, no.” Jake hesitated a moment, and then asked, “Is it different when you, have sex?” “Oh, I’ve never had sex,” Anna said. “Never really been