Discovering Amber

"I see a guy in lingerie." I replied sheepishly.

"Now what do you see when you look at me?" She asked.

"I see a gorgeous woman in lingerie Ms. Allison." I replied drinking in her reflection.

"We will fix that soon enough you realize don't you muffin?" She smirked.

"Yes Ms. Allison." I replied wondering exactly what that meant.

"Now I asked you earlier what comes next in your little cross dressing night of fun," she started, "now answer my question and tell me what comes next."

This wasn't a question it was a demand and I knew if I did not answer that she would move out in the morning. Allison is a wonderfully loving and amazing woman with a stubborn streak true of her Irish heritage, if she left she'd leave for good.

"Ummmm ..." I stammered trying to find my words, "usually I ummm ... jerk off."

"Jerk off?" Allison taunted. "No muffin, real guys jerk off. They take out their big manly cocks and stroke them they don't dress up like slutty women and shove a cock in their ass before they do it." I went to protest but Allison saw it coming. "Are you going to try to tell me that's not a cock in your ass?" She asked taunting me more and walking towards me. "Tell me then what do you call something that's long and hard and put into a willing orifice like that?" As she asked Allison pushed on the base of the plug and wiggled it making it dance in my ass, the feeling was so intoxicating I couldn't answer. "That's right it's a phallus and something that trains your ass for what is to come." Her hand never left the plug as she spoke. "Now pull that dripping shaft of yours out of your panties and stroke it for me." I complied quickly and began to stroke furiously while Allison played with the plug base.

My mind was in overdrive and I didn't know what would happen next but what I really needed was to cum. I had never masturbated in front of anyone before so this was all so new but so incredible as well. I would pop in no time, then Allison turned up the heat and I was done for.