I want to describe my first anal sex. It happened pretty late by Catholic standards. I was a prudish and clean girl, while many of my girlfriends had all the fun in the world exploring the "God's Loophole". Of course, they told me all the details. I was intrigued.

When I was 21, I found myself in between relationships and had a fling with a 38-year-old French expat. He was an engineer who came to Poland on a 6-month contract with one of our telecom companies. His name was Hugo.

I joked, "Hugo - does this mean huge?" He was moderately endowed but skillful and attentive. Also, he was tall, lean, and had a toned body from all the hiking he did in his free time. His hair was brown and curly, and he had a well-groomed beard. He had a sexy accent and was very charming. I liked him.

We had something between a relationship and a series of one-night stands. We talked a lot, and I was fascinated with him, and I think he was interested in me. Or at least he faked it convincingly. We were not exclusive. He had other flings simultaneously, and I was seeing other men occasionally. We both were open about it.

Hugo was not the jealous type. He had no problem with me seeing other people, and I enjoyed being free to explore my sexuality. I would tell him all about my adventures, and he was always eager to hear.

One night, we were at his apartment, drinking wine. It was a warm spring evening in Krakow. We were kissing, and I was aroused. I looked at him and said, "You know, I've never had anal sex before."

He raised his eyebrows and laughed in a friendly way, "I can help with that, Annette," he said, "Go refresh your makeup for me." I was surprised but did not ask any questions. I always had my toiletry bag with me when I was visiting his apartment, so I went to the bathroom and put on some fresh makeup and lipstick.

When I got back, Hugo was in his bed, naked. He was stroking his cock. "Come here, ma cherie," he said, "Let me show you how it's done." I was curious and horny. I crawled onto the bed, naked. He leaned over and kissed me on the lips. "I'm going to make you feel so good," he whispered.

"Lie down on your stomach," he instructed. I obeyed. He started massaging my ass, gently caressing my butt cheeks with his hands. Then he spread them apart and blew gently on my anus. It was a new sensation, and I giggled.

Hugo grabbed a bottle of lube and coated his fingers. He rubbed it around my anus and inserted one finger inside. I moaned. His touch felt so good. He added another finger and scissored them inside. It hurt a little, but the pain was mixed with pleasure. I had never experienced anything like it before.

Then he got on top of me and rubbed his hard cock against my asshole. He pushed in slowly. It was painful. He started thrusting inside me. He grabbed my hips and pounded into me harder. I was moaning and begging him to "stop", but in a playful way. I did not want him to stop.

The pain was intense, however. Hugo was relentless. He thrust his cock deeper and deeper inside me. He grabbed my hair and pulled back. I could feel his hot breath on my neck. I was screaming. My anus felt stretched to the limit. It was a deep ache that spread through my entire body. I could feel his cock pushing against my internal walls.

I was moaning and sweating. I could hear the wet sounds of our bodies slapping against each other. Hugo was grunting. He was fucking me so hard that I thought he would rip me apart. But then, as he was fucking me, the pain started to fade. My anus suddenly felt relaxed and open. That was another new sensation for me. I had never felt so full and open before.

He pulled out and flipped me over. He wanted to see my face while he fucked me. He looked at me, grinned, and smeared the remains of my makeup with his hand.

I felt dirty.

I felt slutty.

I felt ugly.

I felt happy and liberated.

He flipped me over again, inserted his cock, and continued pounding. He grunted and moaned as he thrust deep into my ass. He was sweating. I could feel his cock throbbing inside me. He was close.

And then, without warning, he exploded inside me. I felt his hot cum fill up my anus. It was a strange and unfamiliar sensation.

Hugo pulled out and collapsed on the bed beside me. We were both sweaty and exhausted. We lay there in silence for a moment. Then I said, "Wow, that was amazing."

He smiled and said, "I knew you would love it, Annette." He was right.

Later I learned that he was gentle to me by the anal sex standards. He took me in the lying doggy position, so the penetration was shallow. It felt so overwhelming to me, a beginner, nonetheless!

We continued having anal sex regularly, with deeper penetration, until his contract in Poland ended and he got back to France.