Anal Stories: Dr. Ana

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Dr. Ana Von Gaarten read all responses she had received so far and sighed. So many wonderful stories of people who enjoyed anal sex, people who had worked past the pain and perhaps the taboo associated with the practice and found enjoyment. Dr. Ana trembled. She had always enjoyed anal sex, probably more than most, but she’d never been able to find a man who would bypass her pussy to indulge in her asshole on every encounter. Many who had serviced her had grown tired of her request. They saw her ripe pussy, flush with juices and wanted to bury themselves in it. She didn’t want her pussy filled; she wanted her ass filled.

All this reading had made her horny and with haste, she stripped off her hose and skirt, got down on all fours and slid her favorite dildo up her ass, sitting down and grinding against it in ecstasy. Oh, it was so good! This was all she had to do. She rose up, pinched her butt cheeks together a bit, and frigged her clit, rocking back and forth and driving the plastic toy deeper. “Oh God! Yeah! Yeah! Fuck!”

She came hard and fast, gasping for breath at the sensations that rocketed through her body, her ass muscles clasping and her pussy pulsing in response.

Then, she suddenly felt her eyes sting and she fought back the tears as she shakily arose and sit at her desk, the dildo forgotten on the floor.

Her eyes fell on the letters and she could do nothing but cry.

Matt Houseton heard Dr. Ana’s crying but didn’t enter the office. He knew she needed to be alone and his heart cried out to her. He had been Dr. Ana’s assistant for six years and knew her like the back of his hand. He’d listened to her take lovers in her office providing a shoulder to cry on. However, those relationships always went wrong.

He knew why they went wrong but he never told her why. He’d heard a couple of the guys complaining about “not getting the pussy” and saying that she was sick because she only wanted to be ass fucked. He didn’t know why she was like that but he knew that he was the man for her.

If she’d only give him a chance.

The intercom machine at his elbow buzzed and he answered it quickly. “Yes, Dr. Ana?”

Her voice was thin and filled with unshed tears. “I’m going to go home early, Matt.”

“Are you okay?”

“Yes. I just need some time off.”

“Wait. Let me come in.”


Matt heard her cry once again but chose to ignore it, sensing that there was something else wrong with his employer. He opened the door and walked into the room, astonished at the sight he saw. A shit-stained dildo sat on the floor. Her hose were half on her body and her lovely face averted in shame. He knew what had happened and he knew, deep in his heart, that he was the only person that could make it right and make Dr. Ana whole. Tears left wet tracks down her face as she sat silently, sobbing.

“Get your things. I’ll take you home,” he said.

But Dr. Ana just sat quietly, not canlı bahis wanting to move. She heard Matt’s words but she couldn’t move. He had seen her in her worst moment and she was so embarrassed that she couldn’t move.

“Dr. Ana …”

“Matt, just go home. I’ll be fine.”

“No, you won’t.” He hissed angrily. He was tired of seeing her like this. It was time that someone took control, if she wouldn’t. “Now, get your purse and whatever else you need to take.”

“I need my laptop.”

“I’ll take care of that. Go into the bathroom and fix your clothes.”

Dr. Ana lifted herself from the chair and drifted toward her private bathroom door. She turned to look at Matt before going through and her brow furrowed. Why was he doing this? Matt had been her confidant for six long years and he had never once acted like this towards her. In fact, she thought he was a gay bottom. Now …

“Matt, I need to take the letters,” she said.

“No work. You’re taking vacation tomorrow.”

“Matt, I … “

“No. You haven’t taken a vacation in the time I’ve been here. When was your last vacation?”

She couldn’t answer. Oh yes how long had it been? Ten years? Fifteen?

“That’s what I thought. Fix yourself up and let’s get going,” said Matt, shaking his head.

He watched her as she disappeared into the bathroom, then turned to gather her purse and pack her laptop away, as he had on several occasions. Taking the items, he went back into his outer office and turned his computer off. And then, he grabbed his knapsack, making sure he had everything he needed.

She appeared a few minutes later, her hose replaced and her hair pulled back into her characteristic ponytail.

“Are you okay?” he asked. When she nodded silently, he added, “All right. Let’s go.”

Outside, he hailed a cab and helped Dr. Ana inside, keeping her tight against him. She tried to rebel a bit against his arm but relented when it became clear that he wasn’t planning to release her any time soon. He took her keys when they reached the brownstone and let them into her house, closing the door behind them with a ringing note.

“You may go home now, Matt.” She said hoping to dismiss him. When he didn’t all she could do was watched helplessly when Matt stride towards her, grasp her arm tightly and wrench her around to face him.

“I may go home? Is that what I may do? All these years of watching you suffer and taking care of you and I may go home?” His handsome face moved closer to hers. “Screw you!”

“Matt …”

“What?” he asked.

Dr. Ana gazed into his deep eyes, quivering over the control that he was exercising over her.

“Don’t you dare ask me to leave! You need me!”

She couldn’t deny his words but she didn’t want him, of all people, to be here for her. Why? Her heart asked the question even though she knew the answer. Because it was Matt. Because he knew all of her secrets. Because he was the bahis siteleri person who could hurt her the most.

“I know,” she whispered.

“Then just do me a favor and shut the fuck up, will you?” He gave her a stern but gentle smile. “For once, I’m running the show. Now go upstairs and take a bath. I’ll fix dinner.”

Dr. Ana thought of a sharp retort but shrugged her shoulders, giving herself up to Matt. She trudged up the stairs, ran a bath and spent nearly an hour soaking. She cried, she worried, and fumed. In the end, she relented, promising herself to allow Matt to help her climb out of the hole she’d so deftly dug. She got out of the tub, dried and dressed in a thick, cotton robe and headed downstairs.

The most wonderful smell met her nostrils as she came around the corner and she stood stock-still, observing Matt in the kitchen. He had two pans on the top of the stove, one with chicken breasts, searing in olive oil and the other filled with chopped mushrooms, garlic and butter. He completely cut the heat under the mushrooms and covered it. Then, he turned the heat down under the chicken.

He grabbed a pair of mitts, pulled a golden brown pie shell out of the oven and set it out to cool. He was taking a second wine glass down from the cabinet when he noticed her standing in the shadows.

“Want a glass of wine, Dr. Ana?”

“Sure.” She felt so shy. He poured a glass and placed the glass in her hand, wrapping his warm hands around hers. His smile warmed her deeply. “Thanks.”

He served dinner and the entire time, Matt watched Dr. Ana’s face. At first, she picked at the food, then once she’d tasted it, she had ravenously devoured the entire chicken breast Matt had prepared for her. She praised the garlic/mushroom coating and ate a couple extra bites, washing it down with wine. He sent her to the couch and after cleaning the kitchen, he joined her there, placing an arm around her back.

“Now, tell me.” He spoke to her heart. “Tell me what you want.”

“I … “ Dr. Ana was haunted by the sincerity in Matt’s eyes and the confession that she was ready to give got stuck in her throat. “Matt, I…”

“Just tell me. You like it in the ass.”

Dr. Ana stared at him wide-eyed. How could he know what she liked? The dildo…she closed her eyes, hoping to erase the extreme embarrassment that she felt.

“Come on, Dr. Ana. Tell me,” he goaded.

Dr. Ana Von Gaarten swallowed a huge lump of pride, looked into the dark eyes of her best friend and spoke.

“It was my father. We first had sex when I was fourteen and several times a year after that. He never touched my pussy. I think he truly believed that it wasn’t sex if he didn’t cum in my pussy.”

“So he came in your ass instead?”

Dr. Ana nodded. She felt strange: confused, humiliated and uplifted all at once. “Yes.” She closed her eyes, the remembrance of the heat of her father’s first cum scalding her ass insides. “And bahis şirketleri I’ve enjoyed anal sex ever since.”

“Do you ever let anyone cum in your pussy?”

Matt saw tears gather in her eyes. “No.”

“You don’t know how to enjoy it, do you?” His voice was soft and again, a shake of her head. Matt laid the trump card on the table and took a deep breath. “Would you let me show you?”

Dr. Ana thought she was dreaming. “As long as you fuck my ass raw.”

Matt didn’t wait. He turned her in his arms and matched his mouth with hers. Her mouth was needy under his, desperate to feel his taking of her, his complete and utter domination of her senses.

His large hand swept over her body, across her pebbled nipples and into the juncture of her legs, searching for and finding her wet core. She moaned against his mouth as he took no time to push past the folds of her robe and sank one long finger into her pussy. The welcome intrusion seemed to set her aflame and he began to move slowly inside her.

The first orgasm caught her completely off-guard. She had always only orgasmed from assplay and now … she could barely think as her overheated pussy spilled its juices onto his fingers. His finger stroked again and again, bringing her to the brink and crashing her into the rolling surf as his heel mashed against her clit. She had never felt anything so wonderful.

He released her mouth and stripped off her robe, moving behind her and pushing her onto all fours. His thick prick slowly pushed into her dripping pussy, stretching the little-used muscle as he gritted his teeth, willing himself not to cum.

She was so tight. He pumped into her quim until he heard her breath catch and knew she was cumming again, her muscles rippling against his hardness. Now nicely lubed, he removed his cock and entered her ass hole.

Dr. Ana groaned. Every nerve ending of her body was tingling and she thought she was going to go crazy. Matt was relentless, slamming his cock into her asshole and his fingers pumped into her pussy hole, wringing two orgasms from her pussy before taking her to the most intense orgasm she’d ever felt. His cock swelled and loaded her ass with his steaming cream just as her pussy exploded onto his fingers, ass muscles milking him dry. When he was finally able to stand on his feet, he took her upstairs and laid her on the bed, then quietly, reverently wiped her clean.

She watched him as he returned from the bathroom, his clean body wet against hers. She closed her eyes against unexpected tears as he put his arms around her. “I never knew it could be like that.”

Matt pressed a kiss to her ear. “Isn’t that why you wanted to do the study? To explore anal sex and the pleasures that could be derived from it?”

“Yes, but I didn’t expect it for myself.”

“You should, Dr. Ana. If anyone deserves happiness, it’s you.” Matt turned her so that he could see her eyes. “And I’ll be right here giving it to you if you let me.”

Dr. Ana smiled and accepted his kiss, whimpering as his thumb slid into her ass and fingers into her pussy.

No need to do any more research, she thought. She had found all the answers.

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