Inverted Intimacy

"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 the stream. After a few minutes she started to moan, and finally her body jerked as she orgasmed.

Anna contemplated for a moment and nodded. "Okay, sure, that seems worth a try. Why not? Come on." She got up and walked to the bathroom. Jake followed eagerly, his erection bouncing crazily as he watched her cute bottom lead the way.

Anna turned on the tub faucet about halfway, just to a gentle stream, and sat on the edge waiting for the water to warm up. Satisfied with the temperature, she stepped into the tub and sat down. Lying on her back, she spread her legs and scooted her bottom down toward the tub spout's stream of water, stopping with her thigh in the stream with her knees bent sharply.

"Like this?" Anna asked. Jake nodded. "Oh, it's just a bit too hot. Can you please make it just a tiny bit cooler?"

Jake gave the knob a small adjustment.

"Hmmm. Now just a little warmer?"

Jake put two hands on the knob and twisted it the smallest possible amount in the other direction.

Anna let out a sigh. "Okay, that's perfect." She rested her head against the bottom of the tub and closed her eyes. "I feel stupid, though. This is embarrassing."

Jake took her hand from the rim of the tub and held it. "It's not stupid to work toward understanding yourself and your body better. You've nothing to be embarrassed about as far as I'm concerned. I don't know if, when you find something that feels good to you, it will be like it is for me. But if it's similar, I think it will have been worth the effort. Maybe this suggestion of mine is stupid, but if it doesn't work we'll just try something else. Yeah?"

Anna smiled. "Yeah, okay." She looked down at the stream of water. "Okay." She slowly moved her hips until the stream hit the target. Jake felt her fingers tighten on his hand. "Oh! That is... that is interesting."

"Interesting in a good way?" Jake asked.

"It's definitely not bad," Anna said, resting her head back against the bottom of the tub as she closed her eyes again and slowly moved her hips to try different targets for the stream.

Jake looked over Anna's naked body. The drain was open, so the tub wasn't filling, but the flow was strong enough water was pooling in the bottom and it wet her hair. Her breasts were somewhat flattened against her chest, but he couldn't tell by looking if her inverted nipples were at all hardening. Jake looked down her belly to her bare vulva. Pussy. He loved saying 'pussy' with her. Her pussy spread open wide, her inner lips fluttering in the random turbulence.

"Oh!" Anna said, grimacing slightly with her eyes squeezed tight. "Ohhhh, something is happening."

"Is it a good 'something'?" Jake asked.

"Mmmmmmm... yes," Anna replied. "It is good."

Jake watched her shift her hips a bit more, and it looked like the stream was focused directly on her pink clitoris. Her hand gripped his tighter. Anna smiled and Jake couldn't help smiling in return, even though her eyes were still closed. It was intensely arousing to see her enjoying herself. He gently squeezed her hand in return, savoring the beautiful sight.

For several minutes Anna lay there, often making small adjustments to her position as the warm water tumbled over her pussy. Finally, she let out a big sigh--frustration or disappointment he couldn't tell--and sat up, releasing his hand and pushing herself away from the tub spout as she stretched her legs out straight on the bottom of the tub.

"Oh, that's much better. I couldn't stand having my knees bent for even one more minute." She leaned forward in a stretch, rubbing her leg muscles.

"Another failure then?" Jake asked.

"Definitely not!" Anna said, turning off the water. The tub drain gurgled noisily. "I've never felt anything like that. It was nice. But the good feelings plateaued, and my legs started to cramp, so I don't know how close I got to having an orgasm."

"I see," Jake said, disappointed. "Sorry."

"Sorry? That was a great suggestion. Now I know I can feel these kinds of feelings. It just wasn't enough for taking me all the way to orgasm town, wherever that is."

Jake felt his heart warm with pride. She liked it! She was smiling at him. He smiled back.

"So, what other ideas do you have?" Anna asked as she stood up in the tub and dried herself. "I feel like we're on the right track, we just need to keep searching."

Jake's smile faltered when he realized he didn't know what to suggest next. He supposed a vibrator would do the trick, but they had none. Anna was vigorously toweling herself when she saw his face and paused.

"Only if you feel like it, of course," she said, a bit quietly. "It's no big deal."

Upon hearing this horrifying misunderstanding, Jake panicked. He couldn't ruin this!

"I could touch you," Jake blurted.

"What?" Anna said.

Jake felt himself turning bright red. Had he really just said that? He hoped he hadn't ruined everything. He looked down at his feet.

"Sorry, that was a bad suggestion." Jake was speaking quickly in desperation. "Please forget I said it. The truth is I'm happy you enjoyed the tub faucet, and I'm having a lot of fun joining you on this journey. I'm sorry."

"Whoa, slow down," Anna said. "You would touch me, that way?"

Jake looked her in the eyes, his face contorted in anguish. "I'm so sorry. That was inappropriate of me. I'm having the best time with you, and I didn't mean to ruin it." Jake looked back at his feet. His ashamed dick had shrunk to a tiny nub.

Anna held her eyes on his. "You're serious. You're not joking." It was a statement, not a question. Jake nodded.

"I can't promise it would work, of course. I've never done this before. It was just a stupid suggestion." Jake looked away again.

"Well, if you're sure you're willing to, we could try it. But only on one condition: When it's too boring or tedious, you must promise to stop and tell me. No hard feelings! Okay?"

Jake couldn't help but smile. "Deal! And you have to be patient with me. I have no idea what I'm doing."

Anna resumed drying herself. "I have to admit I'm pretty excited. If you can make me feel even better than what I just experienced in the tub it will be... well, it will be wonderful." She thought for a moment. "But am I being unfair to you, though? I still don't want to have sex."

Jake laughed. "As long as you don't mind how much I may enjoy this."

Anna hugged him, pressing her naked body against his. "You're my best friend," she said. She took Jake's hand and led the way back to the couch. She sat in her usual spot, on her towel, and spread her legs apart. Jake knelt between her knees, looked at her pussy, and froze. She looked so lovely before him, the smooth outer lips framing inner lips extra pink, still gleaming, and a bit swollen from their treatment in the bathtub. More than anything he wanted to bring her ecstasy with his love. Instead he found himself paralyzed with fear of failure.

"It's okay if it's too weird! As I said, no hard feelings," Anna said, trying a little too hard to sound casual.

"It's not that. I'm just... intimidated." Jake closed his eyes and then looked at her again. "It feels like a lot of responsibility, and I don't want to mess it up."

"Listen, Jake, take it easy. I appreciate you doing this for me. If it doesn't work, that just means we learned a bit more about how my body works. Either way it will all be okay. It's just me. Your friend, Anna," she said with a smile. "Now I don't mean to be demanding, but right now I'm feeling rather impatient and I want to be touched on my PUSSY." With a laugh, she grabbed Jake's hand and pressed it flat against her. Jake felt the warmth emanating from her cleft and almost swooned.

Jake started slowly moving his palm in small circles. He was used to touching her when he shaved her, or simply to comfort her. The closest he came to stroking her before this is when he would apply moisturizer after shaving. While he knew she enjoyed that, probably more than she'd admit, this was completely different. This was not about intimacy or comfort. She was asking him to stimulate her sexually.

Jake knew he was in over his head. His knowledge about pleasing women sexually all came from porn, and he knew how unreliable that was. His only hope was paying close attention to her reactions like a game of "hotter or colder" where the hidden prize was his best friend's first orgasm.

Keeping the gentle pressure on her pussy, Jake drew his other hand up her belly, dragging his fingers between her breasts, around them, and up over her flushed areolas. He was encouraged to feel some firmness beneath his fingers where her nipples hid. He spent a moment gently caressing her before dragging his hand down to join his other between her legs.

Remembering something he saw in a video, he gently pinched her outer lips together so her clitoris was trapped within and then pulled them up and down to stroke it.

Anna moaned softly.

Bringing his hands together, he ran his thumbs down and up her smoothly-shaved outer lips. The down strokes pulled against her clitoris, the up strokes spread her open revealing the pink entrance to her vagina and the delicate petals of her inner lips. Down and up his thumbs stroked her, each time moving his thumbs inside a bit more and picking up her growing slickness. When they were wet enough he gently pinched each outer lip between a thumb and forefinger and pulled them apart a bit. Pulling down and then pushing up, in this way his fingers stroked every part of her outer lips and gently tugged against her clitoris without direct contact.

"Ohhhhh that's good," Anna breathed.

After several full strokes up and down her cleft, he felt his thumbs were wet enough to try touching her clitoris. He pushed them up against and over her bump, feeling its firmness. Anna gasped, and he looked up to her face. Her eyes were wide.

"Wow," she said quietly.

Encouraged, Jake spent some time pushing his thumbs up and down over her clitoris, feeling it get even more erect under his touch. Anna's breathing got faster.

"Put a finger inside," she said.

"Are you sure?"

She nodded decisively, but her face showed nervousness. "I'm sure. I trust you. But just one finger, okay?"

Jake nodded and turned his attention back between her legs. Keeping one thumb stroking her clitoris, he tenderly explored her opening with the forefinger of his other hand. Circling and teasing until he was sure his finger was lubricated enough, Jake watched her face as he pressed against her opening and his finger penetrated to the first knuckle. Anna's mouth jerked open in surprise.

"Are you okay?" Jake asked.

She nodded again, biting her lip. Jake slowly pulled his finger out part way, and then pushed in a little deeper. While his other hand kept slowly stroking her clitoris, he worked his finger in, out a little, in deeper, out a little, until finally his finger was fully buried in her. Anna breaths became slightly ragged with excitement.

"How are you doing?" Jake asked.

"Good," Anna said. "Really good. Something is definitely building."

Jake smiled. He was doing it! Matching the rhythm of his thumb on her clitoris, he kept his finger straight and moved it out and in, out and in, out and in. The air was perfumed by the delicious scent of her arousal. Anna grabbed her breasts and squeezed them. Jake's erection throbbed to see her so excited.

Trying to remember what he'd read about stimulating a woman's g-spot, he curved his finger up to stroke where he hoped it was.

Anna gasped. "Oh god. Oh fuck. Don't stop!" Jake's hands were starting to tire, but he was determined to get her there. He increased the pace of the strokes on her clitoris. Anna's hips were moving in response to his touch.

"I think... I'm... close," Anna said in between breaths. "Please... I need... just... something more."