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Her Inverted Intimacy Challenge: Part 3
Monday, 2 March, 2026
Porn, masterbation, confessions, and demonstrations.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 close. Have you?”Jake shook his head. “No, me neither.”They sat together in silence, the picture of the nude model on the computer forgotten.Anna took a breath and asked, “What does it feel like to… have an orgasm?”Part of him was expecting this question. He thought about the countless times he’d masturbated. What was it like to not know?“It’s okay,” Anna said with disappointment. “I didn’t mean to pry.”“You’re not prying!” Jake said quickly. “Sorry, I’ve never talked about this with anyone. I’m not sure how to describe it. I’m happy to share it with you, but please be patient with me.”Anna’s face relaxed. She waited patiently while Jake thought.“I think it’s kind of like sneezing,” he said.Anna looked confused. “What?”Jake smiled. “Well, kind of. You know that tickle in your nose before a sneeze? It’s annoying, and not a strong sensation, but you know unmistakably a sneeze is coming. The feeling builds, and builds, and then suddenly there’s this out of control explosion that somehow your whole body is involved in. The explosion is related to the tickle, it comes from it, but is orders of magnitude more powerful. More intense. And then afterwards it feels like relief, like all this tension was suddenly released.”Anna looked doubtful. “You’re not really selling it.”Jake laughed. “Well the difference is, unlike a sneeze, it’s all pleasure. It starts as mild pleasure. It feels good, and it builds. It can continue building, and just feels amazing. Sometimes it’s nice to take it slow and enjoy that feeling. When the orgasm hits it feels like the pleasure-o-meter goes off the scale.”Anna laughed. “If it’s that great, why aren’t you masturbating, like, every day?”Jake’s cheeks turned red. “It’s not necessarily every day.”Anna’s eyes widened. “Oh.” She giggled nervously.Jake nodded. Anna sat in quiet thought.“What I’m wondering is,” Anna finally said softly, haltingly, “for me, would it be different if I was… masturbating… with a… friend?”Jake could only see one interpretation for what she just said to him, and yet it seemed impossible.“What do you mean?” Jake asked, studying her face for any sign of joking.“Would you be willing to… masturbate with me?”Jake stared at her stupidly.Anna turned away and moved to stand up. “Sorry, I know that was weird. Please forget I asked.”Jake held tight to her hand. “YES!” he blurted out.Anna turned back toward him.“I mean, no that’s not weird,” Jake continued. “Yes, I will do that with you. Masturbate.” Anna smiled. “After all, that’s an extremely normal thing for friends to do together.”They both laughed. “What’s your vision?” Jake asked. “How will this work?”Anna gestured at the computer in Jake’s lap. “Do you think you could find a movie of something we could both, um, enjoy?”Jake laughed. “Can you be more specific?”“A man and a woman having sex?”“Okay. Any turn offs?”“What do you mean?”“You haven’t watched much porn, have you?”“No,” Anna answered.“That’s okay. Let me sketch a typical ‘plot’ for you. Couple kisses. Couple undresses. Couple takes turns performing oral sex on each other. Man puts penis in woman’s vagina. Lots of thrusting and then, usually, pulling out and ejaculating on the woman.”Anna made a face of disgust. “ON her? Why do they pull out like that?”Jake laughed. “Okay noted, what penises do is disgusting. This brings up another issue we should discuss. If we do this together, I feel I must point out to you I have a penis, and when I orgasm my penis ejaculates semen. If that is gross to you, maybe this isn’t a great idea?”Jake felt a little bad confronting her so directly on this. He thought it was disgusting too, but she hurt his feelings.“I’m sorry, you’re right. But I am curious–why is it normal for the man to pull out?”“I don’t know, I think just so the camera can see the climax? Anyway, I’ll find one where the penis stays inside. Any other concerns?”“Do they always do oral sex? It seems gross to put your mouth where someone pees.”“Not always,” Jake said, “though it’s very common.”“Why is gross stuff common in porn? That doesn’t seem sexy.”Jake thought about how much he’d like to put his mouth on her. “I think it depends on the relationship. A stranger, or someone you’re not attracted to, then I agree it’s a big yuck. Someone you are attracted to, someone you care for deeply and find beautiful and appealing, well, maybe it’s a special intimacy? I’d also guess it feels good in a unique way. I have no personal experience, though. Just speculating.”“Hmmm.” Anna seemed doubtful.“You’d prefer something without oral sex?” Jake asked.“At least to start, please.”Jake found a suitably tasteful example of the genre, put the laptop on the coffee table in front of them, and started the video. Sitting beside Anna, Jake became very conscious of his shrunken dick. He was too embarrassed to be aroused or to touch himself, and his hands rested on his thighs. Anna sat in about the same position, hands on her thighs.The woman in the video took her bra off. She had small breasts with big nipples.“I like her breasts,” Anna said. “She has great nipples. Do you like them?”“Yes, they’re nice.” Jake would have preferred to be looking at Anna’s, though.The woman in the video pulled down the man’s pants and stroked his dick with her hands. “What a beautiful cock,” the woman said in a sultry voice.Anna giggled. “Do people really talk that way?”Jake shrugged. “They do in porn, at least.”“Cock is such a funny word,” Anna said. “Is that what you call your penis?”Jake let out a short laugh. “Believe it or not, I don’t talk to my penis that often.”“I think you mean you don’t talk to your COCK,” Anna said. She nodded toward the screen. “His cock seems to like her,” she said, clearly enjoying the word. She looked over at Jake’s shrunken dick, stark evidence of how uncomfortable he was in this unusual situation. “But yours doesn’t seem so interested. Do you want to try a different video?”“Sorry,” Jake said. “It’s not the video. This just feels weird. I feel a bit paralyzed.”“It is awkward, but we can overcome it,” Anna said. “How do you, normally, how do you touch yourself?”Jake spoke slowly, feeling nervous. “I hold my… penis…”“Cock,” Anna corrected with a smile.“Okay, I hold my cock, and I squeeze until it is hard. Once hard I… I stroke up and down the length of it.”Anna nodded, staring at his limp dick.“How about…” Jake swallowed. “How about you?”Anna laughed. “Well as I explained I don’t really know what I’m doing.”“Okay, I know, but what have you tried? What is your… plan for this attempt?”Anna frowned. “Just general rubbing around my vulva, I suppose.”“Any particular places?”“I’ve read I should focus on my clitoris, but that’s way too sensitive so I kind of rub around it.”“Do you put your finger… inside?” Jake asked.“Oh no,” Anna said, shaking her head. Then, quietly, “I’ve never put anything inside.” She turned to face him. “My gynecologist has, of course, but it was uncomfortable, and I’ve always been a little afraid of doing it on my own. I suppose that sounds stupid.”Jake shook his head. “Not at all. There’s nothing stupid about listening to your feelings. The whole point of masturbating is to feel good.”For a moment they sat in silence watching the video. Finally, Anna put her hand between her legs.“Come on, slow poke,” she said with a smile. “Catch up!”Jake took hold of his shrunken dick.“This isn’t so bad,” Anna said. “How are you doing?”“Doing okay,” Jake said.“Then let’s start stroking.”Jake started rolling his limp dick between his fingers while, out of the corner of his eye, he saw Anna rubbing between her legs. He wanted to watch Anna instead of the video, but he kept his eyes on the screen. The man in the video was now stroking the woman’s pussy. Jake thought about when he had stroked Anna during shaving and moisturizing, which he found deeply erotic but wasn’t supposed to be about sexual pleasure. He wondered what it would be like to stroke her to make her feel good. Sharing his first explicitly sexual moment with her was powerfully arousing and soon he was fully erect.“That’s more like it,” Anna said, nodding at his erection. “Look at that beautiful cock! Feeling better?”Jake took this opportunity to look over at Anna, her friendly face and her bare breasts making his heart long with desire as he stroked himself.“Much,” he answered. “How are you doing? Is it working better having company?”“I think so. It’s still weird, isn’t it?”“Pretty weird!” Jake agreed.In the video, the man was now fingering the woman. She was shaved except for a small patch.“Wow,” Anna said.Eager for any opportunity to turn his head in her direction, Jake asked, “What?”“That woman’s labia are enormous!”“Hmmm, I suppose they’re reasonably prominent,” Jake replied.“Reasonably prominent? They don’t even fit in her vulva, they’re just hanging outside like, 'Hey, what’s up?’”Jake laughed. “Okay, yes. But based on my, uh, experience examining imagery of such things, they’re not unusually large.”Anna sat up a little and leaned down to look between her legs. Jake followed her gaze and was amazed to see she had pulled her outer lips apart, spreading open the petals of her labia.“But look, they’re so much bigger than mine!”Jake took in the sight of her inner pinkness glistening with moisture. Spread open like this, Jake was pretty sure her clitoris wasn’t erect, but his heart thrilled to be seeing in there. His hungry cock throbbed.“You’re so beautiful,” Jake blurted out.Anna laughed. “Right,” she said with sarcasm.“Beautiful,” Jake repeated, looking her in the eye to make his point.Anna looked away in embarrassment and leaned back on the couch, resuming her gentle rubbing while watching the video.“She seems to like that,” Anna said. The woman in the video moaned with pleasure as the man pushed two fingers into her. “She sure talks about her 'pussy’ a lot. Pussy, pussy, pussy! It feels naughty. Say it!”Jake giggled.“Come on, Jake!”“Pussy,” Jake said, quietly.“Pussy!” Anna said, louder.“Pussy!” Jake matched her.“PUSSY!!” Anna nearly yelled. The woman in the video orgasmed loudly while they giggled. “Well she either really enjoyed that or did a good job acting like she did,” Anna said. “I wonder if an orgasm really feels that good.”“It totally does,” Jake said. “Or it can. Speaking of, how are things going in your quest?”Anna sighed. “I don’t know. It feels nice touching myself. I don’t hate the video. I like doing this together, with you, but I don’t feel like the physical sensations are building toward anything.”In the video the man pulled his dick up to the woman’s opening, and then slowly pushed it inside.“That’s kind of beautiful,” Anna said.“It is,” Jake agreed, thinking about Anna.They watched together while the couple in the video had sex, the man thrusting faster and faster while the woman moaned in pleasure. Finally, he grunted, and his body jerked as he ejaculated inside of her, and the video ended.“Oh,” Anna said as she looked over at Jake. “What about your orgasm? Did that video not do it for you?”“It’s not that, exactly,” Jake said while idly gripping his shaft. “It’s more that I wanted to go there with you.”“That is sweet of you, but I’m afraid my equipment might not really work. Honestly, I’m not feeling anything building. But it was very helpful for you to do this with me, because I didn’t feel the shame this way.”“Are you sure you want to give up right away?” Jake asked.Anna’s face looked determined. She shook her head.“No, I’m not giving up,” Anna said. “But, well… do you have another suggestion?”“Have you ever tried, um,” Jake regretted his idea but didn’t know how to back out now. “Water? Like, the tub faucet or shower head?”Anna laughed. “You mean, like, shoot a stream of water into my vagina?”“Well, not so much 'into’ as 'at.’ I don’t know, it was just a thought. I’ve heard some women enjoy it.”“Heard? From who?”“I guess what I should say is I’ve seen videos of women pleasuring themselves with the stream from tub faucets. It could be fake, I certainly don’t know.”“Show me,” she said, nodding toward the computer. Jake found an example. In the video a woman climbed into a bathtub, adjusted the water temperature, and arranged her body so her vulva was in t
