Diana sat back and let Jake begin to recover from the powerful sensations she’d showered on him. “It’s time to finish taking care of you.” She picked up the bottle of oil that Vanessa had given Jake and drizzled a small amount over Jake’s cock and balls. The cool fluid hitting his hot skin felt amazing and he began reascending the mountain of bliss she’d started him on. Diana smoothed the lotion over his skin. “Vanessa said that for now I need to be gentle here.” She withdrew her fingers from his rod. “I’ll be gentle here too,” she said trickling the slippery liquid onto Jake’s perineum so that it flowed down to his opening where it puddled. It felt phenomenal and he moaned. “You like that?” It wasn’t really a question, but Jake nodded yes, too overwhelmed to form words. Diana ran her fingers through the slick fluid, tenderly rubbing it into his skin. Jake moaned his pleasure louder. “More?’ Jake shook his head yes as he abandoned himself to a rising tide of carnal pleasure. “Nothing is forbidden. I want everything for you,” Diana purred and massaged around Jake’s sphincter. “Absolutely everything… unless you tell me otherwise.” She pressed more firmly against the muscular band at his entrance, studying him carefully for any sign that he wanted her to stop. Instead, Jake rocked his hip upward, forcing himself into her touch. Diana smiled and pushed harder until the tip of her finger slipped just inside of him.
Jake felt like his head was about to explode. He’d never imagined that what Diana was doing could feel so good. A part of him thought that he shouldn’t enjoy it. Like she’d said, he’d thought that it was wrong, indecent, and maybe meant he was secretly gay. But a deeper part of him had heard Diana and agreed with her; nothing that feels good should be forbidden, and what she was doing felt incredible.
“Oh, that feel good,” Diana breathed. She twisted her finger and pressed in a little farther. “So hot and so tight. I know that I’m your first, so I’ll be extra gentle.” She dribbled more of the slick oil onto him. “Relax and let me in so that I can make you feel amazing.”
Jake struggled to relax like Diana said. Even though the sensations emanating from his hole felt amazing, his body didn’t want to cooperate, and his sphincter clamped hard onto her finger. He focused on the pleasure and fought to loosen his muscles.
“That’s it,” Diana purred. “Let yourself go. Give yourself over to it…over to me. Let me take you to paradise.” Her voice was like a drug and enticed Jake to do exactly what she asked; he gave himself over to her completely. As Diana drove her finger past his relaxed sphincter and buried it all the way into him, Jake cried out, “Oooh god!”
Diana answered his wail with an exclamation of her own, “Oooh yesss!” She pressed in even deeper, then slid back out. “And now I’m going to fly you past the moon.” She pushed back into the tight confines of Jake’s rectum, found his prostate and pressed firmly. Jake spasmed hard as crushing waves of pure sexual pleasure coursed through him. Diana massaged his prostate and then pulled her finger all the way out. Just as she expected, Jake pushed his hip upwards desperately trying to force her back inside of him. Diana smiled, “You want more, don’t you?” Jake whipped his head back and forth and continued to push his hips up answering with his body. “You will get everything you want.” Diana re-entered him and began spearing the full length of her finger deep in and out, massaging his prostate with each stroke. Every thrust drove him toward what they both knew would be an epic orgasm. It wasn’t long before Jake was writhing on the bed, clutching the sheets in his fists, and calling out, “Oh god! Oh god! Make me cum! Please make me cum!”
Diana knew that p-spot stimulation was intense, and that she could keep a man teetering on the edge of climax for long minutes. She’d done this with lovers before and witnessed their ecstasy, but she was taken aback by how unreservedly Jake was displaying his sexual pleasure. “Anything for you,” she said continuing to drive in and out of him. With her free hand, Diana swirled one finger over the highly sensitive, tiny ridge of tissue just below the crown of Jake’s rigid cock. At the same moment she increased the pressure on his prostate. Jake exploded. With a loud moan he arched high in the air and released a torrent of cum. “Yesss!” Diana exclaimed as if announcing a victory. “Cum for me!” She kept rubbing his dick and stroking his prostate as jet after powerful jet of warm, white goo shot from him. His orgasm was everything that Diana had hoped for, and he unleashed more semen than she’d ever seen. She kept pumping into him until the fountain tailed off to a dribble and Jake collapsed back onto the bed. As Diana withdrew her finger and sat back, Jake shuddered hard one final time and a last pulse of cum escaped his wilting cock. She wiped her hands on the towel and stood beside the bed. “That was amazing,” she said looking down as Jake caught his breath. She ran an index finger through the lake of cum coating his stomach and lower chest. “You are one very sexy man.” Diana raised her slick finger to his lips and pushed it inside. When he’d cleaned her, she dipped it back into the puddle and sucked a large dollop into her own mouth. “Very, very sexy.” She stepped to the bathroom and returned a minute later with a warm, wet cloth and a towel. Jake laid still, drained as she cleaned the mess off of him, then laid down beside him. “That was incredible. Thank you,” Diana said softly as she put her head on his shoulder and pulled the sheet over them. “Thank you,” Jake mumbled. They both fell fast asleep.
Jake opened his eyes. It hadn’t been long that they’d slept, but he felt fully recovered from the powerful experience. Diana was gazing up at him smiling. “How do you feel?” Before Jake could answer, she added, “And I don’t mean physically.”
“Wow, is the only word I can come up with.”
Diana punched him in the arm. “Do better.”
“I’ve never felt anything like that before. I had no idea that it could feel so good. First just you touching on the outside, and then when you started pushing in, it was so intense.” Jake took a deep breath and trembled as if reliving the experience. “When you said ‘let go’ it was like a kind of flood gate opened up. Or maybe a better analogy is that it was like flinging myself off a cliff without a parachute. I had no idea where I was going, or how I’d land, but I knew that it was going to be incredible. Trusting you like that felt as good as your finger did.”
Diana beamed and hugged him. “I like the trust part. Thank you for giving me your virginity. I truly feel honored that you trusted my with that.”
“You kept me on the edge of orgasm for so long. I thought I was going to explode.”
“You did. And it was beautiful. I could watch you cum all day.”
“I wish that I could do that for you, but I’m not a teenager anymore.”
Diana sat up in bed. “Do you mean that, the part about wishing you could climax more for me?”