Sometime ago, I stumbled upon a nice gif of a breathtaking woman extracting a buttplug, accompanied by the tantalizing caption, 'I think it's time for a bigger one.' Driven by an impulsive flirtation, I replied, 'I dare you -X-'. To my surprise, a direct message arrived the following day, simply stating, 'I saw your comment, are you up for a challenge?' Excitement coursed through me as I eagerly agreed, my curiosity piqued by the implications of her words."

This time, the DM contained more details. She wrote, 'I'm looking for someone to do an online challenge with. Based on your profile, you seem like the perfect candidate. If you're up for the challenge, purchase the toys listed in the link below. Once they arrive, send me a photo, and the challenge will begin. No further questions or contact, or the challenge ends.'

I clicked the link and was presented with a set of buttplugs of varying sizes: a small one at 3 centimeters, a medium at 4, and a large at 5. Having recently experimented with anal toys with someone I'd met on Reddit, I was eager to take on this challenge. I immediately bought the set, telling my wife I wanted to train for when she was ready to peg me – my number one sex bucket list item. I then waited for the package to arrive.

Once the package finally arrived – deliveries in the Netherlands had been significantly delayed due to extra packages related to Christmas – I took a photo and sent it to her. Shortly after, I received a message with her Snapchat username and a request to add her. I added her, and almost immediately, I received my first task. The message read, 'Step one of the challenge: create a tribute video for me. Insert the buttplug (and film it). Penetrate yourself a few times with the buttplug and then masturbate to the photo below. Display the photo on your laptop and ensure your semen covers the photo. You have 48 hours to complete the first step of your challenge.' Below the message was a photo of her, also with a buttplug inserted – I guess it was the one with the diameter of 3 centimeters – and her stunning, large breasts. I took a closer look and guessed they were at least a cup F.

I didn't need the full 48 hours. I quickly found myself alone. I undressed, set up the photo on my laptop, and lubricated both my anus and the plug. The plug slide in smoothly, and I penetrated myself a few times. This action, combined with the arousing photo, had me hard. I began to masturbate and realized this was going to be a quick one. A minute and a half later, a large spurt of semen sprayed across my laptop screen. I slowly filmed the semen dripping down, hoping she would appreciate it. I quickly sent her the first video with the message that I had completed step one. Shortly after, I received a message saying I was a good boy and had advanced to round two.

A few days later, a second message arrived, outlining a new challenge. The instructions were similar to the first, but this time, I was to use the 4-centimeter buttplug. The accompanying photo was even more explicit, revealing her intimate parts in a state of arousal. The time limit was now reduced to 24 hours.

This was a daunting task, as I was about to engage in intimate activities with my wife. Juggling these desires proved challenging, a stark contrast to my youthful vigor. After a tense wait, I finally managed to complete the challenge just before the deadline. The forceful ejaculation missed the screen, so I smeared my semen over the photo, hoping it would be arousing. To my relief, I received a message filled with enthusiastic emojis, indicating that she was pleased. I advanced to the final round. For nearly 24 hours, I anxiously awaited her next message. Finally, the third and final challenge arrived. I was instructed to lie naked on my bed at a specific time, with the 5-centimeter buttplug and lubricant within reach. She would video call me through Snapchat.

As the appointed time drew near, I lay naked, my anticipation building. My member was already hard, and precum was beginning to form. When she called, I eagerly accepted. The sight that greeted me was breathtaking. She was clad in a revealing red lingerie set, her beauty captivating.

Without hesitation, she outlined the final challenge: I was to insert the 5-centimeter plug and penetrate myself. Then, she would do the same and pleasure herself with a dildo. I was to masturbate while watching her, but I could only climax after she did. If I failed to complete the task or climax too early, the call would end. I nodded, understanding the rules. The plug was wider than anything I'd used before, but with careful lubrication and deep breaths, I managed to insert it. The sensation was intense, and my initial arousal waned. I could see her smirking, enjoying my struggle. Eventually, I overcame the discomfort and began to pump the plug.

She, on the other hand, effortlessly inserted the plug and dildo. Her movements were fluid and confident, and her moans grew louder as she reached her climax. My desire reignited, and I focused on masturbating without crossing the finish line.

Finally, she declared it was my turn. As I neared my climax, she instructed me to remove the plug, revealing my gaping anus. With a final, explosive release, I coated the screen with my semen. She responded with a virtual kiss and ended the call, leaving me breathless and satisfied.