Strap-On in St. Tropez: How I Took His Anal Virginity

Every once in a while, when I am feeling particularly generous, I will share stories of my exploits, both professional and personal… this took place a few years ago, when I was on vacation in St. Tropez. At the time, I was living in Paris, and decided to spend a week at a luxury hotel along the French Riviera. I planned it to be a cute, relaxing seven days by myself, but I also decided to pack some gear, just in case I came across someone I wanted to use. As it happens, that occurred on the very first evening.

After a long day at the beach, I was having a cocktail—a crisp, dry martini, if I remember correctly—in the hotel lobby. I was dressed to kill and felt sexy as hell: black Louboutins, tight leather dress (also black), and my favorite piece of jewelry, a simple, elegant silver necklace. As I relaxed with a book, I felt someone looking at me and glanced around. It was a man, probably in his mid-40s, well-dressed and in decent shape. He was cute, in a way. When I looked up at him, he quickly averted his eyes, and went back to playing with his phone. I returned to my book. A few minutes later, I looked up again and his eyes quickly darted elsewhere. This time, I stared at him—and kept staring. I could tell he knew, and he began to fidget anxiously. That kind of nervousness turns me on so much. Spotting the waiter, I instructed him to bring the man another drink and tell him to come to my table. He did that quickly (good boy), and the man immediately walked over to me. He looked a bit unsure as to whether he should apologize to me, thank me, or hit on me. I told him to sit down. We introduced ourselves, made small talk for a bit, and flirted. Then I explained that it was rude to ogle a woman, and he said he was sorry. I went silent, letting him get a bit uncomfortable.

“Why were you staring?” I asked. He stammered. “You… are so beautiful,” he finally managed to say. “I am obsessed with you after only knowing you for a few minutes.” All I could do was laugh. He was putty in my hands at this point. I explained that it was his lucky day. He was going to have the chance to show me just how much he adored me. No, he would not be fucking me. No chance. But he would get to come to my room and please me. “Have you ever been fucked in the ass by a woman before?” I asked. “No…no, I haven’t,” he said. He sounded scared, but I could tell he was getting excited. And I was exquisitely excited, too, because I love taking a man’s anal virginity. I told him he had 30 minutes to go to his room, shower, and present himself at my door, kneeling. He was to knock, lower his eyes to the floor, and follow my instructions. Precisely half an hour later, he did just that. He kissed my feet at my room’s entrance, crawled inside, took off his clothes, and bent over the bed. I slipped a tiny plug—liberally covered with lube—inside him, and he moaned wildly. Clearly this was a man who had been waiting his whole life for a beautiful black dominant woman to train him properly. I worked the plug deeper and deeper inside him as tears grew in his eyes. “No crying and no cumming, baby,” I told him. He nodded. I was so proud of him.

I pulled that plug out and inserted a much larger one. It was a good six inches, and I could tell it hurt him, but that he was adjusting to it. I’m always amazed by how smoothly a man’s boy pussy can be stretched when he is in the proper mindset. He then massaged my feet, my calves, and my back, as I ordered. He was shaking a bit from that anal stretching, but he did a good job. Next I cuffed his hands and feet with handcuffs and told him that the big moment had arrived: I’d be popping his cherry. Could he be quiet like a good girl? “Yes, Ms. Tasha,” he said.

He looked super hot while immobilized and deep in subspace, and I came three or four times while taking him in the ass. He was giving his whole body to me, feeling waves of pleasure, and was so clearly satisfied. (Though not as satisfied as me, I am certain.) I then unlocked his cuffs, and revealed that I was going to give him a special and very rare privilege: he could suck my cum off of my fingers. I still remember the intensity of his reply. “Thank you, Ma’am,” he said, sounding as grateful as someone who has just won the lottery.

He was headed back to New York the next morning, so that was the only time he got to take my dick, but we have kept in touch since then. He has bought every single one of my clips, sends occasional lingerie boxes, (and gets teasing photos from me), and sometimes calls my Niteflirt. Best of all, he’s told me that he has craved girl cock ever since our meeting, which makes me very, very happy.