Small Dick Encouragement Role Play

"I'll take another, bartender." Yes, Ma'am." I answered meekly.Kim reached over and grabbed my scrotum. "Do you have any more nuts?" she asked with a playful grin on her face."I'll check, Ma'am." I grunted as she gave them a tug before letting me return to the bar to fetch the drinks.As I was returning with the drinks, Lori and Kristen returned with the presents. The girls were still commenting about the dancing when Anna commented, "It's a good size, but too damn hairy!" So shave him!" Kim suggested. I stopped in my tracks and looked around at them, some nodded while others asked Lori, "Oh, can we?"Lori took one look at my hard cock, maybe she thought I was enjoying myself too much, maybe she just enjoys toying with me, but she quickly grinned and said, "I'll be right back with the razor." She quickly returned with a razor, shaving cream and a towel. She looked me right in the eye as she said, "You volunteered to help make this an unforgettable night for Stacy, and since the the. Hold on I said. I stuck 3 fingers of my gloved and greased hand into her ass crack and probed for her anus. The minute I found it, I stuck 3 fingers in and felt the end of the cucumber right away. Erica yelped in pain as I intruded into her tightest orifice. She had felt my penis before on many occasions and fingers and toys of every description and now a cucumber. But the shock of the rapid entry of my hand into her bottom was too much. I had no choice but to stick my thumb into her butt as well. I couldnt get any kind of a grip without it and my hand isnt nimble enough to use only a finger and thumb. I had four fingers up her tender little-lady bottom. She tried to get away from me and I had to hold her hips to keep her from sliding away. She was panicked by the pain of my retrieval. I had to put my body weight on her to steady her as I burrowed my hand deeper into her ass. I could grab the cucumber, but with the lube and all, it would slide this way or that and I couldnt pull.
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