But yeah, I dig her.”“You always use protection with her?”“Yup”“Condoms or…”“Saran wrap.”She looked up from her computer. She was ...issed. I chuckled.“Yeah, condoms,” I said.“Dennis, please understand that these are serious questions. I know you might be nervous or uncomfortable with discussing this aspect of your private life, but it won’t be shared with anybody and I’m only trying to help.”“Yeah, I know. Sorry.”“Okay.”After that conversation, a whole lot of things happened. I went in to a. Problem was, he was close to cumming and was worried he wont have time to break her in properly so that she would be a willing slave. But his worries werent founded. Her pain slowly turned to pleasure and the remaining pain added to the pleasure. He was moving constantly in a slow rhythm going deep every time, her face which was contorted with pain at the beginning was slowly turning to that of ecstasy. He moved one hand and wiped off the remaining tears off of her face and cupped her face. I fucking loved it!! Then I feel the head of his cock against my ass and it was unreal!! I couldn't believe it was happening. He's rubbing the head of his cock around my ass then gets to my asshole and presses against it. Then reality hit....it fucking hurt!!! We didn't have any lube and I had never taken a dick before. I got a little scared because just the pressure of him pressing into me hurt, I thought the pain of his dick spreading my hole open was gonna kill me.I tried to stay calm and. I felt myself limping. I did not hear his steps leaving the booth or something but I was pretty upset. Most glory hole users know, it is the word of mouth play there. Anyway, I pulled my cock back, rolled it into my jeans but decided to see, if possible, what the game was. I came out and it was easy to get into the next booth because it was not bolted from inside for a good reason. In the light of the TV screen, I could see as he raised his head and smiled at me. He must be a college aged boy,.
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