An Aunt’s Life

Double Penetration

Jeffrey and his aunt were driving in silence. The engine soothing in the background. They were headed to LA. There was a therapists’ convention she had to go to. He was her secretary.

They had gotten up at around four in the morning, and driven for six or so hours. They were supposed to be there by three in the afternoon. They had a few hours to just sleep and check in. They were all supposed to go to dinner around seven. Tomorrow was the start of their conferences. She had a lot of work to do in the meantime. Jeff would be taking care of all of it. Or most of it, anyway.

“You know, I could have driven some of the way here.” She said smiling at him. “Thank you, Jeff.”

“You’re welcome aunt Tory. I love driving.”

They got there four hours later. It was around two. They checked in, and went upstairs to go to sleep for a little while.

“Looks like they only gave us one bed.” She said as she put her stuff in an armchair. “Oh well. It’s not like we’re strangers.”

“I haven’t shared a bed with a woman before.” He said making her laugh.

“And it’s been quite a while since I’ve shared my bed with a man.” She said as she went into the bathroom to get ready for bed.

“I’ll take the inside.” She said as she finished brushing her teeth. “You’re the man. I want protection.” Both of them started to laugh.

“You need anything before we hit the hay?” she asked.

“Nope.” He said as he stripped down to his boxers. He noticed she was wearing a see-through night gown. He was careful not to stare.

“Well, let’s go to bed then.” She said grinning inwardly as she said that.

Victoria had been crushing on her nephew for quite a long time now. He’d been her secretary since she opened her practice two or so years ago. She’d never looked at him in a sexual way before. Until she overheard someone at her building saying something about therapists sleeping with their clients or secretaries.

It had lit some kind of fire under her. She wanted to get him into bed so badly. He was her nephew and she was also his boss. That made her so wet. That made her pussy throb and ache.

She got her opportunity a month later. This therapist’s convention was the perfect opportunity. No one knew him here, hardly anyone knew her. They were away from his mom. This was the night.

Jeff felt so stiff after the ride here. He was about to go to bed, when he changed his mind. He stripped all the way, and went to the bathroom. So what if his aunt saw him naked. She changed his diapers when he was little for crying out loud.

“See you in bed.” She said with another inward grin.

Jeff loved the smells of the shampoos. He loved the jets in the water. He loved the warmth. He almost wanted to sleep here instead. The bathroom full of steam, the tub so soothing. He had to get out of here, though. His water would get cold soon.

He got out of the shower, and got into clean boxers. He made sure he was dry, and headed to bed. His aunt was breathing softly on her side of the bed already. He pulled back the sheets, and got gently in. She let out a soft sigh, and shifted. He settled himself beside her, and was out in no time.

He awoke to find she was gone. He heard her taking a shower. He stretched. He wondered if she’d already eaten. All he could smell was coffee.

He got out of bed and headed for the bathroom. He had a very big very hard erection. He always got these in the morning, without fail. Most of them were harmless. Like this one. Some of them were arousing. He waited patiently as this one faded. Then he went.

“I see you there, Jeffrey.” Tory said with a smile in her voice.

“Yeah. I see some of you, too.” He said smiling as he saw the shadow in the steam.

“I hope you’re not uncomfortable. I don’t mind if you see me.”

“Well, then,” he said with another goofy grin. “I guess I don’t mind if you see me either.”

“I suppose I can ask for another room.” She suggested.

“Aunt Tory, just relax. I don’t mind. It’s just me. It’s just you. We’re comfortable with the other. Or no?” he asked.

So he got dressed as she showered. It was about six in the evening. They were supposed to be at the dinner in an hour and a half.

“You look good.” He said as she came out to meet him.

She huffed at him. He looked at her curiously. She huffed again.

“What?” he asked.

“I look good? That’s all you can say?” she asked. She huffed again.

“Uh, you look very good?” he tried again. “Very, very good?”

“You’re such a man. Never notice the things around you.” She muttered.

“Aunt Tory, what am I supposed to say?” he asked laughing.

“How about, hey aunt Tory. You look very sexy tonight.”

“I don’t see it. You’re my aunt. I don’t notice those things about you.”

“Just shut up and let’s go before you say more asinine things to get yourself in trouble. Let me take your arm.”

They had such a wonderful dinner. He met some of the other people she worked with. He met some other secretaries and assistants too. They all had the pinbahis yeni giriş same topic on their minds. This convention was just a bunch of uptight work-a-holics.

“I cannot get my aunt to put down her books at times. Then I get dragged into conventions, and workshops, and employee dinners. I thought she was self-employed.”

“Well, if we pretend to like it, we get sex.” One of the men said smiling.

“No. Jeff here doesn’t get sex.” Another woman beside him said. “That’s his auntie.”

“No. I don’t get sex.” He said with an even bigger grin. “I get a car.”

Tory heard a sudden loud cheer from the next table. Then there was laughter. She looked over, and saw it was Jeff who’d started the cheer. She wondered what they were talking about.

“Remember all.” Said one of the leaders. “Don’t get too drunk if you’re drinking. We have an early morning tomorrow.”

Jeff looked over, and saw that of course, his aunt was drinking. He wondered how much she’d drank so far. At least they were still in the hotel.

“And then, at least where we live,” Jeff was saying angry as he vented about working for his aunt. “The insurance companies take too long to pay the clients’ fees. We don’t even have an automated appointment reminder system. I have to send all the reminders all by myself.”

“I hate working for people that work too much.” One of the ladies said sadly. “We get paid well, though. Not just with gifts or sex.”

“So are most of you husbands or wives?” Jeff asked laughing. “Am I the single twenty-seven-year-old?” he asked.

“You’re not the youngest.” Said a man across from him. “You’re just the only single guy.”

Soon, the dinner was over. Everyone got some food to take with them. Jeff made sure he helped his aunt to their room. She was slightly drunk.

Tory didn’t know how to make the next move. She had only ever had two boyfriends. The rest all one-night stands. What should she do? Should she go to sleep and sleep off her buzz? Yeah. Maybe that’s it. She didn’t like drunk sex, anyway.

“Let’s play a game.” She suddenly said as they got under the covers. “Have you ever played, would you rather?” she asked.

“No. But I get the gist of it.”

“Would you rather have gone on this trip with me, or stayed home to get girls?”

“I’m not dating.” Jeff said smiling shyly. “So, the first thing.”

“Would you rather, eat one live snake, or a teaspoon of turpentine?” he asked.

“Turpentine.” She didn’t hesitate. “It’s said it’s a good home remedy for colds.”

“On what planet?” Jeff asked starting to laugh. “What do you do? Drink it with a little orange juice and a rolled-up spider’s web?”

“Hey!” she said as they kept laughing. “It’s an essential oil! It’s in the books.”

“Would you rather, stick your hand in a hole and not know what’s on the other side? Or, get bitten by a lab monkey?” she asked.

“The monkey.” He answered. “Have sex like cats do, or eat blended beetles?”

“Beetles. With nose plugged.” She said as she turned to face away from him. She was going to pop the question. “Would you rather, have one night of passionate sex with your boss, or a trip to the happiest place on earth, with a free pass to get to the front of all lines?” she asked. She didn’t want to look at his face.

“That’s easy. I’d have the sex. Orgasms feel way better than rides, fried food or sculpting out the Disney characters. At least with my boss, I have a chance. Who knows who’s behind that mask.”

“Would you rather, have sex with a woman, or go to Jury duty that lasts a whole year?”

“I’d pick the jury. I’m too afraid of lesbian sex. I mean, it sounds messy and unpleasant. I hate sex toys.”

“Would you–“

“It’s my turn!” she said nudging him. “Let’s play truth or dare?”

“Nah. That’s too immature. And we don’t really have any dares. That’s more for parties.”

“Fine.” She said as she tried to direct the conversation another way. “Would you rather, have an incestuous relationship, or join the mafia and burn off your fingertips?”

“Hmm. I go to jail for both.” He sighed as he tried to weigh out the pros and cons. “Of course, for incest, I could probably get house arrest. So incest.”

“On that note, good night.” He said grinning. “Have a good sleep.”

Tory felt awful as he lay there, drifting off. She had wanted things to move fast. She wanted a night with him. They didn’t live together, so she couldn’t just get him alone. She was losing time as the night drifted on. She didn’t know what to do. Should she wake him up? She sighed sadly a while after. She had to just resign herself to the fact that she may never have sex with him.

Her alarm rang in what seemed like no time at all. She was groggy and tired from her drinks last night. She had some trouble getting up.

“So, I’ll be gone from noon to five. Then dinner. Then I’ll be gone from seven to ten. While I’m gone, you’ll call the list of clients I gave you, and try and see if you can fill next month’s calendar for me. You have access to pinbahis giriş my calendars.

“Then, I need to have you go down the list of clients, and see if their insurance is all caught up. If not, make a note, and we’ll get in touch with the company later. That should take most of your day.” She sighed. “I’m so sorry, Jeff. I feel bad. I’m going to my conference, and leaving you here.”

“Are you getting paid?” he asked.

“Yes.” She said sadly. She really wanted to be having fun with him. Even if they didn’t have sex, he was a great kid to hang around.

“Are you going to pay me for coming with you?” he asked.

“Yes, of course.” She said catching his eye. She slowly winked at him.

“Am I working?” he asked.

“I sure hope so.”

“Then, don’t feel bad. If I want to, I’ll take breaks, or something. But I’ll be fine.”

“Don’t forget to check my emails, and flag the important ones. I’ll text you if I need you to come down and take notes.”

“Got it. Have a good meeting.” He said as she got ready to go. “Oh, and aunt Tory,” he said as she backed out the door. “You look sexy.” She was on cloud nine.

Both of them loved working. She loved being a therapist. She loved being able to help people. She loved being self-employed.

He loved working for his aunt. She left him alone for most of the day in her office. Left him with a fridge full of drinks and snacks. He had his music, and her Netflix, Hulu and prime. Soon, he was plugging away, making appointments and checking emails. When Tory would come and check on him, he was usually spread out all over the desk.

“How do you find anything in here?” she had asked one day as she came in to grab another pad. “Nothing is in its place. There’s garbage everywhere.”

“Nuh uh.” He said as he grabbed a handful of garbage and tossed it into the trash.

“How do you know that was all trash?” she asked.

“It just is.”

“Okay.” She said testing him. “Where are the cheat sheets for the insurance papers you’re supposed to be working on?” She tested him every once in a while. He never failed to find what she was after.

“You amaze me all the time, Jeffrey.” She said as she looked over his desk. “I think you have ADD.”

He received a text four hours later. She wondered if he was done. She needed help taking notes. The speakers were going too fast, and all she could do was pay attention to the power points. He made it to the conference room twenty minutes later. He couldn’t find her, but let her know he was there. He got out his notebook, and started taking notes. Jeff was amazing at this.

Jeff was the glue to her practice. He had set up her website. He had helped her get her calendars synched with her phone and her laptops. He did all her paperwork. He was such a great person to have. Crossed her T’s and dotted her I’s.

They met up for dinner that night. He gave her a shaft of papers with a lot of notes. She thanked him and slipped them into her brief case. They all sat down and settled to eat.

“So?” he asked. He was sitting next to her this time. They had decided to pick their own seats, instead of having groups. “You learning anything?”

“Not much. You? Get any girls while I was gone?”

“No.” he laughed. “You know you’re the only girl in my life.” Yep. Still cloud nine.

She sat in silence eating with him for a while. She didn’t know exactly what to say. She wanted to play another game of would-you-rather. She wondered if it was safe in public though.

“You all right?” he asked squeezing her knee.

“Yes.” She said as she felt a chill down her back. She hoped tonight was the night. They had to go back Monday. So they still had some time to have a great couple nights together.

He gave her the run-down of all the things he’d done. Some clients weren’t able to be fit into the calendar. As usual. So he’d made up the cancelation list. He had made up a list of all the clients who’s insurance hadn’t yet paid them. Including how many sessions they’d missed out on.

“So you going back to the meeting?” he asked as they finished their food.

“Yes. I don’t need you though. I think we’re past the frenzy of note taking.”

He was tired after that long day. He settled down in bed, and put the TV on. He was sleeping before he knew it. Safe and sound in his hotel room.

When he woke up, it was dark. He was lying on his side, his arms wrapped warmly around something. He waited to see if his mind came back to him. He realized his aunt was sleeping beside him. Her breasts were in his hands. He had a very hard penis. He had to find a way out of this grip. If he moved, he’d wake her up. Oh well.

He gently moved his left arm from around her. He wiggled his right arm from under her. She opened her eyes, and jerked awake.

“When did you get back?” he asked looking at the clock. It was two in the morning.

“Eleven.” She said softly. “You were asleep so I didn’t want to wake you.”

“How was the rest of the conference?” he asked.

“Fine.” She sighed. pinbahis güvenilirmi She really wanted him.

“What do you all talk about anyway?” he asked curious.

“We talk about the DSM. About what kind of techniques work to help certain clients. We divide into groups and talk with people specializing in the things we specialize in. It’s a big networking conference. The goal is to make contacts.”

“Well, sorry if I get too cuddly in my sleep. I never even felt you come in.”

“Would you rather, go back to sleep, or go to a twenty-four hour movie theater?”

“Yeah. Sleep.” He said bitterly. “Nothing matters but sleep.”

She inwardly groaned with exasperation. The time was slipping away from them. She had to throw caution to the winds and just go for it.

“Jeff?” she asked a few minutes later. “Are you really that tired?”

“Meh. I’m not too tired. I just don’t want to leave the room. I’m pretty comfortable here.”

“Have you ever wondered,” Tory said slowly. “What sex is like with an older woman?”

“You know, aunt Tory, you’ve been talking a lot about sex. Thinking I don’t notice. Are you trying to tell me something?” he asked.

“Well, yeah.” She said. As if he should already know. “You’ve got that kind of personality and physique I have a desire for. I had crushes on guys like you when I was young.”

“So are you asking me for sex?” he asked as he propped himself on his elbow to look at her in the moon light.

“Maybe. Does that freak you out?” she asked. “You’re not going to tell your mom.”

“No, actually. It’s kind of flattering. And no, I won’t tell my mom.”

“So, what do you say?” she asked. “Have you ever had a crush on me?”

“Well, no. I never stared at my family members or felt any kind of pull towards them. But now that I get a good look….”

“What do you think about it?” she asked.

“The sex? I don’t know, aunt Victoria. One moment, I’m your nephew. Your assistant. Now you want to have sex? I mean, it’s weird. You’re my boss, you’re my aunt. I think we should consider those two angles before we do anything stupid.”

“I truly want this, Jeffrey.” She said softly as she leaned in. “And we don’t have much time left.”

She leaned in before Jeff could stop her. Her lips pressing against his. Both of them moaned softly. Jeff’s body awakening with sensation.

“I’ve already considered you from all angles.”

“But you’re my boss.” He moaned as she pushed him onto his back. “You can’t do this. You’re my aunt.” He had the most amazing smile on his face.

“Oh Jeffrey.” She moaned as she ground against his pelvis with hers. “I really want you. I want to know what that nice wood between your legs feels like inside me.”

Wow, that got him really hot. Jeff pushed her off him and they switched positions. He gently laid her back, and started grinding his package against her. He looked into her eyes as they moved. He felt so good. He swore he was leaking.

“How long have you fantasized about me for?” he asked.

“I don’t know.” She moaned. “Since you turned twenty-two.”

“What is it about me?” he asked as he got off her and took off his boxers.

“I love your voice. I love your hard body. I just love how sweet you are with the ladies. You’re such a gentleman. I want to be treated like that at least once.”

“Aunt Victoria, do you go out with men that aren’t gentlemen?” he asked sadly. “Like, do you get treated like a queen on dates?”

“Not really.” She said just as sad. “I seem to attract guys that don’t really pay attention to treating girls nice like that. Holding doors open or pulling out chairs. You’re a different kind of guy, Jeffrey.” She smiled. “Please have sex with your boss.” She said with command in her voice.

“Will I get fired if I don’t comply?” he asked as he leaned down and gently bit at her neck.

“Mmm. Yes.” She teased. “You’re fired if you don’t put out.”

“Well…, Hmm. I wouldn’t want to get fired.” He said with a grin. He leaned down and gave her another kiss.

“How do you want me to do this?” he asked as he sat up to look at her.

“I don’t know. Rip my clothes off with your teeth or something. Just have your way with me, baby.” She let out a moan akin to a porn star. He smiled.

He grabbed the neck of her nightie and pulled. He heard the rip of the threads as he yanked some more. She moaned sexily as he worked.

“Next time, do it faster.” She advised. “Slow kills the mood sometimes.”

He started kissing her all over. Her neck, her chest. He kissed her shoulders and face. She was moaning as he did this. He could feel her jerking and squirming under him.

“Tell me what you like.” He said between kisses. “I want to make you feel so good.”

“Oh Jeffrey. It sounds like you’re just as dedicated to sex as you are to your work.” She cried out as he started kissing her breasts. “Yes. Oh Jeffrey.” She moaned. “Suck them. Please suck them.”

She loved this. He spent so much time on her. Just licking and sucking her boobs, kissing and leaving marks on her thighs and rib cage. Coming back to her neck once in a while and leaving marks there too. He loved sucking her nipples. They were hidden most of the time. With stimulation, they got longer and longer. She had awesome breastfeeding nipples.

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