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.
He smiled, nodded, closed his eyes and kissed her gently on the lips. He pulled away from her still smiling, and as he turned to go and pay for their meal she noticed a bulge in the front of his pants.
Clearly, they were ready for each other.
Chapter 3: The Night Begins
The taxi ride to her place was short, but long enough to arouse her. With every bump in the road, her plug moved inside her. She could feel her dress sliding underneath her naked and exposed vulva. Her labia swelled with each uncontrolled and sinful thought of the night ahead. Even her breasts felt sensitive as her dress rubbed over her cold and erect nipples every time she squirmed at the intensity that was building inside her. His intoxicating scent drove her wild to the point that she thought she might cum right there in the back seat of the taxi. She never felt anything quite like it before.
Arriving home, she invited him to sit on the couch while she got a bottle of wine. He took off his jacket, sitting in the middle of the couch, and arms spread wide over the back of the seat cushions. She had no choice but to get close to him now. She sat on the couch next to him, feet up behind her, and nestled into his waiting left shoulder. He wrapped his arm around her, resting his hand on her stomach. She loved feeling his warmth around her, and the naughty feeling knowing that he could see down the top of her dress.
"It must be obvious to him I have nothing underneath" she thought to herself.
As they drank they talked, and she asked him to tell her what happens next. "Tell me what you want to do to me" she said.
"I'm going to lay you naked on the bed and drive my tongue deep inside of you" he said.
She moaned at the thought and closed her eyes in anticipation of the story to come.