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As the evening began, a nervous excitement filled the room. They had both been willing to explore anal play, but this was a new experience for both of them.

They had prepared for the night with plenty of lube, a anal plug, and lots of communication. They set up soft lighting and laid out towels for easy clean up.

As they undressed, their eyes danced with anticipation and eagerness. She led him to the bed and instructed him to lie on his stomach, and she began to massage his backs and legs. Her touch was gentle and calming, but the anticipation they both felt was anything but.

As she felt him relax beneath her fingers, she gently inserted a probe, feeling him tense slightly before calming once again. He was surprised at the sensation; it felt almost like a gentle nudge against his prostate.

As he began to relax more fully, she slowly increased the size of the probe until she was able to insert the anal plug. With a deep, controlled breath, he let himself be filled. The sensation was overwhelming, but in the most pleasurable way.

As she stroked his cock, she could feel him getting harder by the second. She whispered in his ear, “Are you ready for more?” He nodded, and she slowly began to insert her finger into his ass. As she moved in deeper, he let out a deep moan. She continued to move around inside of him, feeling the muscles tighten and loosen with each movement.

With one hand still stroking his cock, she reached for the vibrator and gently placed it against his anus. The vibrations mixed with the movements of her hand on his cock, giving him a sensation he had never experienced before. The intensity of it all made him feel like he was on the verge of orgasm the entire time.

As she increased the speed and intensity of the vibrator, he began to lose himself in the pleasure. Suddenly, he let out a deep moan as he came harder than he ever had before.

As she pulled the plug out, she moved up close to kiss him passionately, both of them still trembling from an intense orgasm. They had both crossed a line and experienced something new and exciting together – something that they would explore again soon.
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