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He came back with a few items.?And now for your punishment.? Wait, the ball crusher wasn?t the punishment? I became extremely nervous for what was next. He put a gag in my mouth and secured it tightly around my head. He showed me a countdown timer set at five minutes. He reached up and showed me a handful of clothespins.?Oh Fuck.? I mumbled through the gag.?I told you to be careful what you wish for. You wanted punishment. I expect you to make it. No safe word unless you absolutely need it.? He began placing them across my cockhead like before. They dug in and I knew I was in trouble. He started the timer in front of my eyes and left it there. I stared into the mirror, looking at my cock and balls wondering how I was going to survive ten minutes. I started struggling after only a minute and pulled back too hard and the nipple clamp on my right nipple disconnected. He immediately returned and reset the clamp in the other direction on both nipples, increasing the pain. Jessie bit into the pillow howling!“Take it out” she muffled through clenched teeth...and repeated it over and over again.Jessie’s teeth were gritted into the pillow and tears were flowing down her cheeks.“It’s okay....it’s okay....it’s done now...I’m in...just relax and let yourself get used to it!” said Leon soothingly, and he rubbed Jessie’s bum and lower back to comfort her.Jessie stopped complaining and began to breathe deeply....it looked like she was in labor, the way she was positioned and breathing , trying to get used to Leon inside her.Eventually Jessie quietened down and her body relaxed.“That pain... you felt, was me breaking your Hymen, you’re now open for business” laughed Leon.Jessie looked down between her legs and saw spots of blood had formed on the bed sheet, She knew that was normal for her first time and she smiled, her virginity was gone.“Now I must make a path in you princess...not just for me, but for every man who will be lucky enough to find you on the end.
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