Gently Pleasing knew he wanted to try anal sex but he was a bit apprehensive, not sure exactly how it would feel or even how to go about it. He had talked to his friends and read a few articles online but was still not sure if it was something he was ready to try.
One night he had made plans with an escort and told her that he wanted to try something new. She had smiled knowingly and said that she knew just the thing. She had promised it would be gentle and that she would give him all the time he needed to get used to it and adjust to the sensation.
Gently Pleasing stepped into the boudoir and was immediately greeted by the smell of incense and the sound of soft music playing in the background. He was immediately put at ease and felt a wave of anticipation tingle through his body.
The escort directed him to the bed where she had laid out blankets, pillows, and other items he would need to make this experience pleasurable. She had also lubed up a special, curved vibrator with a thick, silicone coating to make insertion smoother.
Gently Pleasing lay down on the bed and the escort straddled him and started to massage his inner thighs and buttocks, working her way up until her fingers grazed his anus. He had to admit that it felt good, and after a few moments of gently caressing and teasing, she pressed the tip of the vibrator against his anus and worked it in slowly, inch by inch.
At first, he was a little uncomfortable and tensed up, but the escort worked her way in slowly and paused whenever he needed a break. Eventually, he got used to the sensation and started to become aroused. The escort then cranked up the vibrations and Gently Pleasing felt himself getting close to orgasm until suddenly, a wave of pleasure and relief engulfed his body.
Gently Pleasing was filled with an intense pleasure and was so thankful that his escort had led him through the experience. The sensations had been unlike anything he had ever felt before and he thanked her for her patience and her skill.
Afterward, the escort gave him a gentle hug and a tender kiss before leading him back into the living room where he thanked her for the experience and left feeling completely satisfied.
Gently Pleasing had been hesitant at first to try anal sex, but now that he had experienced it, he found himself looking forward to it and was eager to try it again. He had discovered a new level of pleasure that day, and it was one he would never forget.