Chapter 1: First Date
She met him on line. He was twice her age, but that's okay by her because she likes older men. In fact, it's her fantasy.
For some time now she had been exploring herself, intimately. Exploring places in her own body she never knew could be explored in such an erotic way. At night, alone in her bed, her fingers wandered down her body exploring between her legs. Lately though, her fingers have been going further and further. At first it was just light touches around her little rosebud. She liked the way she could make herself reflexively clench at the lightest touch.
Before long, she was exploring deeper and deeper. A little bit of rubbing, a little more pressure, and soon the tip of her finger was inside her ass. The first time she did it she was taken aback. She always thought it was wrong, it was dirty. It felt so good and she was conflicted, but went with it anyhow.
The first night, she didn't go too far. She inserted about half of her finger until she felt as if she needed to go to the toilet. Her mind knew it was her finger, but her body wanted it out. Quickly she pulled out leaving her rosebud tingling, and her chest heaving with excitement at what she had just done.
She snapped out of it, realising she had been daydreaming about her first time. She had come so far since then. Fingers, toys, vegetables, you name it she has probably tried it. Tried everything but the real thing.
Tonight was the night she was to properly lose her anal virginity.
Fresh out of the shower, makeup on, she stood at her dresser looking in her drawers. She had three butt plugs to choose from. Small, medium, and large. Knowing what was to come tonight she wanted to be prepared, and at first chose the large.
She knew she must have been nervous for her date, because the large wouldn't go in easily like it usually does. Instead of fighting it, she went back to the small one, relaxed on to it and suddenly felt the enticing feeling of fullness inside of her. She slipped her dress over her otherwise naked body, turned out the lights and left for her date.
Chapter 2: The Restaurant
They met at the Treehouse and shared a wood fired pizza with a salad on the side. They drank hot chilli margaritas that quickly loosened their lips and the conversations flowed throughout the meal.
It was a cool winters night, and a lazy breeze came over the restaurant. She shivered slightly, and he politely asked her if she was cold.
"Yes, I picked the wrong night to wear this dress" she replied.
"I'm glad you did, you look stunning."
"Any suggestions on how to get warm?" she asked with a sly grin, smiling with her eyes.
"I'm told that sharing body heat is always the best."
He moved over to her side of the table, stretched out his hands inviting her to stand and held her in a long warm embrace.
She rested her head against his chest and drew a deep breath of his intoxicating cologne. She felt a rush of warmth through her body, a shudder, and then the sweet moisture between her legs. She knew he was going to be the one tonight.
She gazed up at him, her eyes smiling with drunken lust. "How about we go back to my place and get warm?" She spoke softly, and welcoming almost in a whisper.