Her Inverted Intimacy Challenge: Part 4

Anna almost loses Jake, then beds him.

By darrenr - Listen to the ► Podcast at Steamy Stories.

Wordlessly they lay there, Anna clutching his hand as he held her. Eventually her breathing returned to normal, and her grip softened. Jake realized he had his dick pressed against her bottom in their hug, but it had softened during the past few minutes. He felt proud of himself and his soft dick. Anna was the epitome of his sexual desires, but in this moment even his perpetually rude cock recognized this was not the time to make selfish demands. It felt nice snuggled up against her soft bottom.

His face resting on Anna’s back, he couldn’t help smiling. He had done it! He had most definitely given her something she’d never felt before.

A small movement from Anna brought him out of his reverie, and he realized she was crying. In a single second his heart fell from impossible heights of blissful pride and satisfaction down into despair.

“Anna, are you okay?” Jake asked, his voice small. “Did I hurt you?” For what felt like an eternity, there was no response at all. Then Anna’s grip on his hand tightened, and she pulled it against her chest.

“Thank you,” she said, her voice cracking. Holding his hand tight, she moved to sit up and he pulled back to give her space. She looked at him with cheeks wet with tears. “I have no idea why I’m crying. No, you didn’t hurt me. You made me feel more pleasure than I ever thought possible. I don’t know where all this emotion is coming from.” She leaned her head against his shoulder, and he put his free arm around her again. They sat in silence for a few minutes more. Jake’s heart gradually recovered from its moment of terror, and he breathed easy again, the sweet scent of her hair in his nose.

With a deep breath Anna lifted her head and looked at Jake. Still feeling elated from his success, he started to grin. This in turn made Anna smile.

Making a goofy face, he said, “Well?”

They both burst out laughing. Jake felt elated at what he had accomplished, giddy with delight at what they had shared, at how close he felt to Anna.

When the laughter died down, Anna’s face grew thoughtful. “What I just experienced, was that normal? Is that what everyone feels when they orgasm? Is that what you feel?”

“I doubt I’ve ever experienced anything even a tenth as good as that,” Jake said. “That seemed to be in the earth-shattering category.

“It really was. My legs feel weak. I can’t get over how good that felt. I honestly didn’t know anything like that was possible. How did you know how to do that?”

He thought about all the ‘how to’ videos about sex he had watched, all the guides to please a woman he had read, how he poured all his love and focus into doing the best he could for her. “I think I just got lucky.”

Anna laughed. “No, I’m the one who got lucky.” She sat in silence for another moment looking at her toes.

“Jake?”

“Yes?”

“You kissed my pussy.” It still caught him off guard when she used that word, but he liked it.

“Yes. I hope you don’t mind. I knew you needed more and that was my only idea,” Jake said.

“Was it, was it gross?” Anna asked.

“Quite the opposite,” Jake said. Of course, the truth was he was overflowing with affection for her. Confessing all that now seemed too much. He kept silent.

“Anna,” Jake said quietly, “Did I hurt you?”

“What on earth are you talking about?” she said.

“You know, when I, when I put my finger inside.”

“Oh!” she giggled. “No, it didn’t hurt at all. Quite the opposite. Completely different from the doctor.”

“Oh good,” Jake said, his finger remembering. Warm, snug, delicate. He felt his arousal start to grow and tried to think about something else instead.

After a few minutes, Anna asked, “How tired are you?”

“Oh, I’m fine.”

“But it took me ages to reach the climax. You must have been getting a little tired?”

“A little,” Jake admitted. “But I’m fine now.”

“All recovered?”

“Yes, all recovered!” Jake said, laughing at the interrogation.

“Good!” Anna said, distractedly stroking the top of her thigh. “Good, I’m glad. That was an incredible thing you did for me, just an incredible thing.”

“Anna, please,” Jake protested, turning his head to meet her eyes. “I enjoyed it too, you know.”

Anna smiled but quickly looked away in embarrassment. “Of course, now, now it’s your turn.” Anna was clearly getting nervous. “I owe you some–”

“No,” Jake said a little too firmly, sitting up. “No, listen. There’s nothing owed. Nothing transactional here. If some day in the future you find yourself needing to touch me, truly deeply needing it, then nothing would be more welcome. Nothing. But I’ve been slapping this salami and having orgasms for years. I’m fine. What’s important now is you’ve taken a huge risk with this first step, and it was a good experience. I think you should load up on good experiences before taking more risks.”

“'Good experience’ rather understates things,” Anna said with a laugh.

“Here’s what I think,” Jake said. “No offense, but you look a bit worn out. How about I get us a snack and we watch a movie to relax?”

Anna smiled. “I do feel a bit drained. That would be nice.”

Jake returned with some apple slices, cheese, and crackers. Anna cued up a movie and he realized he was feeling pretty drained himself.

Sometime later he awoke to find Anna still sitting with him. The movie was over. It took him a moment to notice she was looking down at his crotch.

Jake must have moved a little because Anna startled, looked away, and began to get up.

“What’s the matter?” he asked.

“Sorry, I shouldn’t have been staring while you were asleep.”

Jake laughed. “Are you joking? We’ve been naked with each other for weeks now. Why would I mind if you looked at my ugly wiener?”

“I don’t know,” Anna said, settling back down on the couch beside him and leaning against him. “It just felt like peeping or something.” She smiled. “I guess I was being silly.” Jake nodded and put his arm around her again, feeling her shoulders rise and fall as she breathed, enjoying how her breasts moved.

“I don’t think it’s ugly,” Anna said after a few minutes.

“Huh?”

“Your penis. Your cock,” she added with a smile. “I don’t think it’s ugly. It got super small while you slept. I thought it was cute.”

Jake felt the topic of discussion begin to swell. He whispered, “Uh oh, it knows you’re talking about it.”

Anna bent down close to his dick and whispered to it, “I think you’re cute when you’re all shrunk up small!” Then she sat back up, giggling.

His dick jumped a little in response, and Anna laughed more.

“Can I tell you something stupid?” Anna asked.

“Of course.”

“This is embarrassing, but, when your cock gets really big…” Anna looked down. In a quiet voice, she said, “I feel a little bit scared of it.”

Jake immediately began to shrink. He frightened her? He moved to cover himself with his hands.

“No wait,” Anna said, grabbing his arm and pulling him back down. “That’s not what I meant. You didn’t do anything wrong.” She pulled his hands up so his crotch was exposed again. “All I meant was it’s intimidating when it gets big.”

Jake thought for a moment. “I have to be honest. It’s hard to not be aroused when I’m with you. But I will try!”

“No,” Anna said. “No, I don’t want that. This doesn’t make sense, but I also like when it gets big. I feel both excited and a little afraid.” She looked down and then back into his eyes. “I guess what I mean is I appreciate how patient you’re being with me. I intend to return the generosity you’ve shown me, but, but I’m just not ready yet.”

Jake let out the breath he didn’t realize he was holding. “Oh, well that’s no problem. I thought we already settled this? You don't 'owe' me anything."

"I know," Anna said, "I just--"

"Listen," Jake interrupted. "Believe me. I'm having a... profoundly good time. All I can think about is hoping you'll invite me back for another round."

"What does your schedule look like tomorrow evening?" she asked.

Jake chuckled, and he felt his dick jump at the thought. "I think I can fit you in," he said.

Anna smiled, and leaned her head against his shoulder again.

Unexpressed Desires.

Anna didn't like to directly ask for Jake to work his magic on her. Her face would occasionally get this hungry look that was extremely obvious, and Jake made sure to offer. As he practiced on her more and more, he became immensely proud of his growing expertise. He had learned to read her feelings, her body's reactions, and her needs. Sometimes it was clear she needed immediate relief, and he would give it to her. Other times, his favorite times, she enjoyed dragging it out. He would bring her right to the edge, and then back away, teasing her over and over until she couldn't stand it even one more second. When she reached that point, he would take her over the edge into an incredibly powerful orgasm that left both of them exhausted afterwards.

She wasn't ready to return the attention. Occasionally she would offer, though it clearly came from a sense of obligation. J