Continued from Part 2: https://www.reddit.com/r/gonewildstories/comments/71o6we/mf_i_28m_let_my_fiancée_26f_dress_me_up_in_a/
I had never sucked her strapon before. I was taken aback and buzzing with anticipation. “Hop on the bed and get on all fours,” she said. I quickly obliged. I heard her picking up the lube and putting on a latex glove. I knew what that meant. “Hike your dress up, *Princess*.” After hearing that nickname, with it’s simultaneous endearment and degradation,
She had gloved just the hand she intended to use and started caressing my butt cheeks with the other. She made downward strokes as if she were gauging how well a particular horse had been broken in. She began talking me through it. “We might as well make use of this time by getting your ass ready.” She gingerly inserted one lubed, latex-clad finger into my ass, moving it back and forth. When I had relaxed she stuck in a second and repeated the process. Once she felt no resistance against both of her fingers, she pulled them both out and readied the plug. Nothing special, just a medium, black latex piece that she used to dilate me. She began caressing my ass again as she pushed it in. There wasn’t much resistance by that point. “Good job,” she remarked. “Now get down and drop to your knees.”