Her Inverted Intimacy Challenge: Part 3

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."

"Hmm." 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