Her Inverted Intimacy Challenge: part 4 - Anna almost loses Jake, then beds him. (first time) 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 interro