This happened last night, and I hope it happens again soon
Feeling very horny one night, I logged into my 'alternate' IM account. You see, the reason I call this my 'alternate' account is because of the 20 male contacts whom I cam with when I get this horny. As a bisexual male, seeing other guys jack off whilst they see me jack off was a fantasy which I have now turned into reality.
I had been stroking for 30 minutes before I logged on, and I only wanted a quick cam show just to finish off. It was very early in the morning, but luckily I had one friend on, who we shall call Tim. I was desperate to cum and get off, but he seemed interested in talking more, so politely I followed suit.
I know Tim through a website where I post videos of myself masturbating (another fantasy and turn on for me!), and whilst we were chatting he was watching one of my videos, where I'm dressed up in school uniform and getting myself off. He tells me he loves the video, so I ask whether he wants a live stream...
A few minutes later, and my school uniform is on, as our respective webcams cast upon ourselves before the roleplay - me as a cheating student, Tim as headmaster ready to unload my punishment.
On his orders, I bend over my chair, my hairy ass up in the air, in full view of the webcam. I use my hands to spread my butt cheeks, as I glance at the webcam to see him moving his hands down south, and taking off his clothes. He instructs me to put something in my ass. I grab for the nearest biro, and never having done this before, I plunge it deep down and nearly buckle at the sensation. I thrust it in and out, secretly enjoying these new feelings as my anus relaxes. The anal stimulation alone nearly sends me over the edge.
Next I turn around, and remove all my clothes - tie, shirt, trousers and pants. I begin wanking my aching throbbing cock, until Tim orders me to stop. I show my body off to him fully at his request, desperate to clutch my penis again. Eventually, he allows me to sit down and begin furiously wanking. I hoist my legs up onto my desk and around my laptop, with my webcam facing my aching cock. 3 more minutes of double handed pumping, and my throbbing 9inch cock shoots hot cum all over my chest.
I see Tim spray his load before I log out, hoping my punishment has been fulfilled, until next time......