I watched as she put it against Tim’s anus and pushed gently. “Relax Tim. It won’t hurt as much if you don’t fight it.”“That’s easy fo... you to say.” He winced as Jess applied a little more pressure.“Maybe not. Just relax, you’ve seen it work for Jess.” He must have relaxed a bit because the plug started to slip inside him. Jess kept up a firm but gentle pressure and I watched as Tim’s asshole expanded to let the plug inside. His eyes widened as the widest part of the plug stretched him. I learned that from experience, I realized he was not new to seducing sissy boys like me. He did mention he had a few one-night stands but he stopped for a year.He slapped my ass and turned me around. He said that he saw almond oil in the shower and asked me to to bring it to him. I obeyed him and he resumed his activity, now with the oil. I was having a really hard time standing and bending over for him. He noticed that told me to kneel down if it was uncomfortable. I told him we could go. More

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