my first anal play experience header image showing a woman in lingerie posing in front of a webcam

My First Anal Play Experience

When live cams changed from a curiosity to a lifestyle.

my first anal play experience header image showing a woman in lingerie posing in front of a webcam
Image: Shutterstock

I’ve always been one for sex positivity and maintaining a healthy relationship with all my sexual encounters, no matter how intimate, or how foreign. As part of my job selling high-end cosmetics, I have the luxury of traveling non-stop and always meeting new people, exploring new places that became my favorites, mostly because of the lovers I “acquired” when I visited these exotic locals. From Paris to Rome, Russia to Spain, I’ve been all over, so my sex stories may be kinkier than most, and experimental. Yet, throughout my many adventures, I never allowed myself to consider what, for some reason, is still very much a taboo – Anal.

When I was younger, I loved letting my partners explore their sexuality just as I was exploring mine, but somehow for the men that I was with, getting fingered by me was completely normal. Fucking me in the ass, however, was not, I didn’t even consider it and I believe they didn’t either, as in the States, anal is almost considered “dirty”, something people do in porn but not in real life.

And then, something completely shifted my way of thinking, involving an accidentally turned-on camera, an oblivious bystander (Me), and a scorching hot model called Izabelle. I found her review on This woman taught me everything I now know about anal, and many other sexual fetishes that became normalized following our sessions. Though I consider myself a straight woman attracted to men, this live cam hottie blew my mind, perhaps because I met her so unexpectedly. I was in Venice at the time, attending a huge conference and met a charming Italian man that I knew was going to get to know my bedroom well during that week. I wasn’t wrong, and he was an incredible lover.

One day I came to meet him at his hotel, and we had one of our classic Italian romps involving pasta and handcuffs, his weapon of choice to completely dominate me, which was a welcome change from my norm. On our fourth day together, I arrived at his room when he was in the shower. I let myself in with the room key he had given me, and did some fun snooping, the kind that isn’t intrusive, just curious. I looked around to see what he brought with him in his suitcase, not moving anything out of place, and enjoyed discovering he had a couple more toys in his possession we had yet to try. As I was walking around, my thigh brushed against his laptop, which made the screen turn on, and I suddenly heard a surprised greeting spoken in a sensual female voice behind me. “Buongiorno!”

I almost jumped out of my skin, as I was wearing nothing under my oversized sweater and high thighed boots, and got very self-conscious, very fast. I returned the greeting and replied “Buongiorno?” in an unsteady voice. When she started speaking Italian, I finally directed my gaze to the laptop and saw the most beautiful woman I had ever seen, with the kind of body I’m sure many Italian poets had written about, in great detail. And, she was completely naked. I started laughing and then suddenly stopped, and placed my hand on my mouth, because it dawned on me there was a naked woman on my guy’s computer. Was I supposed to be jealous? Worried? Angry? … Turned on? 

I sat in front of the screen and apologized, I didn’t know her language. She quickly switched to the most adorable broken English and asked for my name. I hesitated, but gave her my real name, and blushed. She giggled and told me hers. She asked if I was Marco’s girlfriend, and I said he was just a friend. “Sex friend, yes?” she replied. I got more comfortable and laughed, nodding. We went on to speak a few more minutes, and she told me she works on several cam sites as a model, mostly with men who love anal. That took me by surprise, that such a thing existed. How naïve!  

My Italian lover walked in on our conversation, and surprisingly, was not surprised and happily joined in. Izabelle wanted to know what anal play we were enjoying, which was the first time in a long while I felt almost apologetic, when I replied that we weren’t even attempting it. “Why?” asked the live porn pro, and I had no logical reply, which I usually have an overabundance of. Nothing came, I was mute. She smiled wide and exchanged a knowing nod to Marco, that casually asked “Wanna try?” 

I did. Anything that involved this natural beauty with the long black hair, curls enveloping her tiny waist and huge breasts, I was game for. She got up and started bringing in her toys, which didn’t seem to end, displaying them all on her bed and asking me to pick. So, I chose the cute, pink, small dildo that bounced around like jelly and seemed harmless. “Good choice!” She exclaimed happily.

What transpired in those few hours between the three of us can only be described as a cornucopia of firsts. First threesome, first anal play, first sex webcam sites experience, first time with a woman, first… anal climax. It’s funny thinking of it now, because it has become such an integral part of my sex life, I wonder what I did before, and why the hell I didn’t try it earlier. These days, it’s rare for me to have any sexual session with a semi-stranger without exploring this fetish. I haven’t been in a threesome since, but I have had frequent chats with Izabelle, just her, and her toys. She’s taught me so much about real sex-positivity, which I used to think was about being comfortable with my sexuality and body. It is, of course, but it’s also more. It’s about taking a chance, trusting yourself and your instincts, being as open as you can be to new kinds of sex, and people. Izabelle was my first anal play experience, but she was also my first real foray into true sex positivity.   

My First Anal Play Experience: When live cams changed from curiosity to a lifestyle is a sponsored guest post written by Best Cam Sites.


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