onto her back, massaging small circles at the base of her spine, then finally centering on her buttocks. By the time his fingers first approached her pussy, she was a glassy pool, so relaxed she was half asleep.
That changed when he brushed over her anus the first time. She was so anxious for this, so excited for the penetration. She wished he’d get on with it, to satisfy both her curiosity and her appetite.
He silently proceeded just as she wished, slipping a generously oiled finger into her hole. The electric sensation was pleasurable, but she felt her muscles involuntarily tense against the intrusion, and knew he would go no further until she relaxed once more. And she tried. It required more concentration than she expected to relax those muscles, especially when the sensation of pleasure was so strong it was an effort to breathe, let alone concentrate.
Finally she managed not to clench at his finger, breathing deeply.
“Nice, nice,” he murmured quietly.
He pressed harder, and though she had to concentrate still, the sensation remained constant, unchanged, even when he pushed his finger in all the way. He left it there for a time until he was sure she could remain relaxed.
“Okay. On to the next step.”
He showed her a glass dildo much smaller and longer than the type she would choose for vaginal play.
“This will hurt a bit. There’s no avoiding it, no matter what anyone might have told you. Just tell me to stop if it’s too much, and don’t worry. I won’t push if you tense up.”
She nodded, impatient to feel more, and very, very glad he was experienced at this. She wasn’t sure she could have trusted anyone else with so delicate a process. And he was right. When first the glass dildo slipped inside her anus, the sensation was not immediately pleasant. It was relentlessly intense, and complex. It stung and it burned but it also felt good, illustrating for her what others meant by painful pleasure.
This time it took many deep breaths before she could relax against the pressure, but Josh was endlessly gentle and patient, massaging her back when she needed to breathe, sometimes rubbing her clit when he thought it might help. It did help. The more she wanted him, the faster she was to relax, the more eager to feel him deeper inside.
All the while, she was aware of having a very narrow focus, of being almost overwhelmed with the sensations inside her anus. It was almost like being hypnotized, crystallized to pure, decadent sexual delight.
The thought occurred to her that she might be asked to do this with clients she didn’t know. She immediately tensed up.
“Hey, whoa,” Josh said. “What’s wrong? Does it hurt?”
She whimpered, unable to relax again. “No, it feels great. I love what you’re doing, it’s just... I don’t think I could do this with clients. It’s too...”
“Don’t worry.” He rubbed the small of her back. “It’s easier for some people than others, and we don’t have to go any further if you don’t want.”
“No, I want to keep going. I want you to take me all the way.”
He went quiet again and continued to massage patiently while she breathed through the tension. Once she’d relaxed, he removed the small dildo and moved up to a medium-sized version, warming and lubricating before teasing it against her sphincter a moment, melting her all over again, then pushing it in.
This time, the pleasure-pain was even greater. She was getting better at breathing and relaxing now, even when saturated with sensation. They cycled up through two more gauges. With the largest, Josh gave her a few soft, experimental thrusts to test whether she could remain relaxed.
She did it, and begged him to fuck her. Everything inside was liquid and quivering and demanding satisfaction.
Josh did not immediately give in to her pleas. When he finally did take the ultimate step, the feel of his cock, the tip superheated and softer than the glass dildos, was glorious. He was built more