Anna’s Tales: Catering to the Unconventional
After two years of being an erotic masseuse, I have learned that some men like to be fucked in the ass. By a women. You might wonder how a woman can really fuck a man. I wondered too. And perhaps my choice of words isn’t really appropriate because women don’t have dicks, but that’s just a technicality. I use the word “fucking” because that’s what my clients call it. They scream out, “Fuck me in the ass,” as they buck on my table, eyes squinted shut with their head thrown back.
Jamming a finger or two up the ass is a way to satisfy the desire, but I have those clients who like to take it a step further, if you will. Robert was one such client.
After responding to my Backpage ad, Robert booked a lunchtime appointment. He looked like every other well-dressed, neatly groomed business man. He just happened to have an unconventional desire. After I led him from the waiting room to the inside of my massage studio, he quickly and unabashedly disrobed. The non-shy clients are always more fun.
“Are there any areas you’d like me to focus on?” I asked, as I began massaging his muscular and tanned back.
“I like my ass played with,” he said, lifting his butt as I pressed hard into his ass, allowing my hands to slide down his inner thigh and gently brush his hairless hole. Robert groaned in pleasure and I could tell he was the kind of guy who liked full insertion. With a gloved hand, I gently inserted one finger, then two, pressing on his prostate as I entered.
“That was amazing,” Robert said afterwards. After our session, Robert sent playful texts and let me know he had a special request: He wanted me to fuck him in the ass with a strap-on, specifically one with a very large dick. And with that request, he assured me generous compensation. Robert had a juicy ass; one that was molded through perfection from hours of bicycling the foothills of the Rocky Mountains. Being pressed up against his luscious rear was titillating and so I obliged.
The deal was that Robert would bring his own strap-on, that way he could pick the size dick he wanted. He presented it to me with a smirk at our next session. Robert was Caucasian and preferred a black one up the ass. At first it seemed a bit odd to attach a cock, one that would be more fitting for a 6’6” black porn star, to my genitalia but once I saw the look of glee on Robert’s face I got into my role.
Robert and I started as we always did — him face down on the massage table as I kneaded his muscles and I slithered on top of him. This time I had both tits and a dick to rub against his back; he loved both my female and fake male parts. After thirty minutes of teasing, Robert begged me to stick it in, to “fuck him in ass.” I generously lubed up my enormous dildo and slowly entered Robert — just a tiny bit at first, and quickly pulled out.
“Go deeper,” he said.
I squirted more lube on both of us. “Are you ready?” I asked as I plunged deeper. It was a curiously empowering maneuver—one in which I was taking the more aggressive stance in sex. Deeper and deeper I pumped away inside him until Robert couldn’t stand it any longer. I withdrew, flipped him over and used both hands to stroke his rock-hard cock, causing him to spurt in an arc. His body shook a bit afterwards like the after shocks from an earthquake and then he sunk back into the massage table.
“I’ll be back,” he said. Yet another satisfied customer. And another service to add to my menu.
