Anna’s Tales: Massaging the Prostate

As an erotic masseuse, I get a lot of unusual requests. I do the things that wives won’t do. And I’ve come to learn that many significant others are unwilling to fondle their lover’s prostate. Sure, it’s like a lover black hole, but for those willing to go where others won’t, you’ll be a sexual superstar and for the erotic masseuse, you’ll make bank.

Reese was the first client I had who showed me how prostate massage could drive a guy crazy. I had a boyfriend once who liked a finger in the ass when he came during a blow job, but a digit way up there during a hand job was a new area for me.

During our first session, my client twisted around, grabbed my finger, and then inserted it. I was hesitant at first, thinking perhaps he just wanted me to tickle the outside, but oh no, he confided later FULL insertion was his thing. He was a big tipper and promised more if I was willing to accommodate him.

The next time Reese booked, I was prepared, with latex glove in hand and a full Internet search of the best prostate massage techniques. While Reese lay face down, I began my massage, digging deeply into his muscles and sliding my hands between his legs, while letting my fingertips press into the space between the ass and balls. He lifted his butt and groaned in pleasure. With a fully lubricated glove, I inserted my middle finger fully into his ass, finding the walnut-sized prostate behind the penis. Reese bucked and groaned on the table as I moved my finger gently around, continuing to massage his thighs with my free hand.

I withdrew my finger and asked Reese if he was ready to flip. He did and as I began to stroke his cock with one oiled hand while re-inserting my finger back into his anus. I have read that the massaging of the prostate can feel like a constant orgasm and the look of intense pleasure—to the point of intolerance—on Reese’s face indicated this was true. I was completely in control of him.

“I’m going to come,” he said breathlessly as I increased my stroking, which concluded with a heavy exhale from Reese. After his body stopped convulsing, he opened his eyes, and looked around almost as if he had been in another place and he was surprised to find himself in my massage studio. “That was fucking amazing,” he said.

Another satisfied customer. And a well-compensated masseuse.