My Sister Set Me Up on a Blind Date

"Yes."

She went back to staring at the glove box. "About a week ago, I was with a bunch of my friends and somehow kissing your brother came up. All of my friends were grossed out at the idea. I didn't say anything, but I thought, 'Hey, my brother is a good-looking hunk. What would be so bad about kissing him?' So I took it as a challenge to test if kissing my brother on a date would be yucky or fun. I felt entitled to lie to you, to pull a big switcheroo when you got here. I didn't care if you wanted to go on a date with me or not. And of course, I got my way. But only for a little while because it was a stupid idea." Ashlynne turned to me. "Would you have kissed me at the end of the date?"

"No." I quickly amended. "Probably not. At most, a quick kiss on the lips."

She went back to staring at the glove box. "I was wanting a lot more kissing than that. That wouldn't have proved if kissing your brother is fun or yucky. Like I said, the whole thing was a stupid idea."

I hated seeing Ashlynne looking so miserable. I had grown over the summer to like her a lot. I wanted to end the evening on a positive note.

"Ashlynne, I give you permission to act entitled to me."

"What?"

"You can act entitled around me. Just make it fun."

"What are you talking about? You hate it when I act entitled. And rightfully so."

I stopped and pulled my thoughts together. "When Mandy first brought up the idea of us going out, she had a big list of Do's and Don'ts that I would have to follow on the date. My gut response was to say, 'No way.' But Mandy was a wonderful person that I really enjoyed being with, so I said I'd give it a try. It was rocky at first, but we eventually developed a strong relationship. You're a wonderful person that I really enjoy being with. If acting entitled is a part of you, then I'm willing to accept that as long you try to make it fun for me."

"I don't believe you."

"Look, Ashlynne. Tonight was fun until I lost my temper. If I hadn't gone along with your idea, I would have had another boring, sucky Friday night. So even though you acted entitled, I gave you the benefit of the doubt, and everything turned out okay."

"Until we had the fight."

"Which was a good fight to have. We needed to discuss those issues. I was never fully comfortable around you because I knew that eventually one of those issues would blow up."

"I've felt the same way."

"But I think we can move on from them now. And I think I can handle you acting entitled if you make it fun for me. Any other issues we should address?"

"I'm a perfectionist."

"That's not an issue."

"It is. It makes me miserable all the time."

I didn't see how being a perfectionist could make Ashlynne miserable. I decided to leave that alone.

"Wrapping up - I'm suggesting we wipe the slate clean, we act toward each other as we act toward our friends, and I'll let you act entitled around me as long as you make it fun. Think it over and we'll talk about it Monday at breakfast."

"Okay." She sounded agreeable to the idea. Ashlynne took the hint and gathered her stuff to go. "Thanks, Todd."

I watched her walk down the driveway. A fence ran along the driveway, and Ashlynne went through a gate in it. I then drove home.

* * * *

Monday morning, Ashlynne came in wearing a nightshirt and carrying two books.

"Good morning, Todd."

"Good morning, Ashlynne."

"So how is this going to work?"

"I don't know. Act like you want to act, and we'll talk things through."

"Okay." Ashlynne handed me a book. "I want you to read this." It was a young adult book with a female protagonist. Not my type of book. "It's my favorite book. I've always wanted to have a serious discussion of it, but none of my friends are interested in that type of thing." Ashlynne seemed uneasy, like she half expected me to flat out reject the idea.

I took the book, looked at the cover, and read the back. "Does it have any explosions?"

"No."

"Hot sex scenes?"

"No, you silly."

I sighed in fake exasperation. "I guess I can read it anyway."

Ashlynne gave me a big smile, set her book down on the dining table, and went to get her yogurt and cereal. "How was your date with Grace?"

I thought it a very odd question. "It was good until we had a fight."

"She told me that she had a good time up until the fight, and she was sorry for starting it. I had a good date with a guy named Oliver, but it got interrupted."

Ashlynne sounded psycho to me, but I played along. "Sorry to hear that."

Ashlynne sat down and told me about some show she had seen at her friend's house.

* * * *

The next morning I came down carrying Ashlynne's book. A bookmark was inserted about a quarter way down.

"How do you like the book?"

"I'm enjoying it."

Ashlynne and I spent breakfast and a good deal longer discussing the book. The book was so-so, but discussing it with Ashlynne was a lot of fun.

* * * *

When I got home that night, I found a note in my room from Ashlynne. "I'd like a big favor tomorrow morning. Please be ready to go out by 8"

When I came down to breakfast, I asked Ashlynne, "So what's the big favor?"

"Mrs. Armstrong was my favorite teacher, and she has to go to school today for a half-day. I volunteered to watch her two boys, and I'd like you to help me."

"You want me to babysit?"

"I want you to have fun playing with the boys. They're four and six, and I think they'd enjoy playing with a big guy."

"And you'll..."

"I'll do the little things to make sure everyone has a great time. I have lunches and snacks packed."

"And I get half the pay?"

"I'll give you three-quarters. You can split zero any way you want to. I'm doing it because I like Mrs. Armstrong, and I know you liked her, too."

I drove us over to Mrs. Armstrong's house, and we took the boys to a park. I played tag, hide-and-seek, run-from-the-scary-monster, and a few other games that Ashlynne thought up. I pushed the boys on the swings. I gave piggyback rides. I raced the boys and always lost. Ashlynne took the mommy role, and I took the big kid role. Ashlynne made sure we were all hydrated and had sunblock on. When one of the kids acted up, I would do the same and then Ashlynne would sternly scold me. The boys found that hilarious. Once Mrs. Armstrong was back, we took the boys home. They gave me big hugs and told me I was the best babysitter they had ever had.

Back at our house, I said, "I've had my workout for the day. I'm going to take a nap."

"Before you go, would you please tell me something?"

"Sure."

"You said Mandy was big into positive consent and that it was rough initially. What did you mean?"

"Positive consent means that both of us had to consent to every step in the making out process every time."

"Every step every time?"

"Yes."

"Didn't that feel stupid, particularly after a while?"

"It felt very stupid at first. On our first date, we went to dinner and a movie. At the movie, I asked if I could hold her hand and she agreed. Then she asked if she could kiss me and I agreed. Once the movie was over, we got in the car, and once I was out of the parking spot, I reached over and grabbed her hand. She yanked it out of my hand and told me that I needed to ask permission before I did something."

"And what did you think of that?"

"I thought this was going to be our only date."

"But you went out again?"

"I changed my mind when later, back in her room, she asked if she could give me head." Ashlynne chuckled. "We quickly dropped verbally asking permission and went to using hand and body gestures."

"Like what?"

"If I wanted to hold Mandy's hand, I'd stick my hand out like this." I held my hand down at 45 degrees from my body with my fingers spread wide. "If she wanted to hold my hand, she'd grab it. But she wasn't obligated to do so."

I discussed the other gestures we used to ask and give permission. There were a lot of them. I finished with, "If I wanted to touch her pussy, I'd put my palm on her belly button with my fingers pointed down. She would spread her legs to give me permission. Same for her if she wanted to touch my dick. We'd always ask verbal permission for oral sex and for intercourse."

"Wow. That sounds so crazy."

"It was, but I got used to it. Positive consent was how Mandy wanted foreplay. And as sex with her was frequent and good, I was willing to do it. Any more questions?"

"Was Grace's date with you like your dates with Mandy?"

"Not really. It was somewhat like my first dates with Mandy in that I was trying to treat Grace with respect. To not be in charge and to not say 'We're going to eat here' and 'We're going to do this after dinner.' Instead, I suggested dinner and went along with her suggestion of mini-golf. My later dates with Mandy were much, much different."

"How so?"

"They were. Trust me."

"Tell me how. You brought it up. It's not fair to dangle clues then not tell me."

She had a point. "Okay. You have to understand that Mandy and I saw each other every day in the dorms. We did lots of things together, either by ourselves or with friends. Dates were a special time that happened only occasionally. After we had been together for a while, we decided that dates would be a safe space where we could act differently than we normally did. Dates for us were all about sex. Positive consent went out the window. We'd grope each other, and Mandy would flash me. I'd talk dirty to her and tell her in graphic detail what I was going to do when I got her back to the room. It was all about building up a sexual frenzy. Then once we got back to the room, we were like animals. We were all over each other and anything went. Once we were satiated, we'd cuddle and have long, serious talks. We'd talk about how much we loved each other and our plans for the future. During those cuddle sessions, I could see us getting married and living the rest of our lives together." I missed those dates. "Do you know what's ironic about our dates? It's the university's policy that every couple do positive consent every time for every step. Mandy is the biggest advocate of positive consent I know, and even she couldn't handle it all the time. I've come to understand that positive consent is a good thing because it makes the guy pay attention to what the girl wants, but the university's policy needs to be something mere mortals can follow."

"Do you still love Mandy?"

"No. She had me believing that I was the most important thing in the world to her, and then I discovered I wasn't. Love is all about commitment, and I'll never believe again that she's fully committed to me."

"Thanks for telling me all this." Ashlynne gave me a firm hug. Once the hug was over, I turned to go up for a nap. Ashlynne added, "Grace wants to go out Friday."

"What!"

"She wants to go out with you Friday. You pick the place to eat; she'll pick what you'll do afterward."

"Ashlynne...I thought the date with Grace was a one-time thing."

"It was. But it got interrupted. And she said she has a challenge she wants to finish with you."

I shook my head. "No, Ashlynne."

"She'll make it fun."

"No, Ashlynne."

* * * *

Thursday morning, Ashlynne came down in a nightshirt I hadn't seen before. It was a light blue that nicely complimented her blue eyes and blond hair.

"Is that new?" I asked.

"I was getting bored with my old nightshirts, so I traded with a friend. Do you like this?"

"It looks great on you."

Ashlynne smiled.

The nightshirt was also very clingy and thin. I could see her tits quite well. I could easily discern the dark ring of her areola. Ashlynne's nipples tented the fabric. Ashlynne was well-endowed and the nightshirt clung tightly to every curve of her tits as they stood up proudly on her chest.

I realized that I was staring at Ashlynne's chest. When I looked back up to Ashlynne's face, she smiled.

"I got a game for us to play," she said as she handed me a video game. It was a dancing game.

"I'll suck at this."

"Doesn't matter. You'll have fun anyway."

I hemmed and hawed, but finally agreed. I got the feeling that my fighting her suggestions made my final submission even sweeter for her.

We played for over an hour, and I did suck at the game. Ashlynne got near-perfect scores, particularly after she had done a dance once. But it was fun. Ashlynne played braless and watching her big tits bounce up and down as she danced had me hard the whole time.

When we were sitting on the couch after playing, Ashlynne said, "If you went out with Grace on Friday..."

"I'm not going out with Grace on Friday."

"If hypothetically you went out with Grace on Friday, it could be a safe space, couldn't it? You could let Grace act as she wants, and you'd go along, even if that's not how you would want to act on a day-to-day basis?"

"I'm not going out with Grace on Friday."

"But if you did, would you go along with what she wanted? And not hold how she acted against her?"

I knew what Ashlynne was doing - I'd seen her do it a million times with our parents. Whenever she decided to do something that they didn't agree to, she'd push and push and push. Most of the pushes were subtle so our parents hadn't been able to say to stop bringing up the subject. Ashlynne would turn almost every topic into how great it would be if she had her way. Eventually, she would wear them down, and they'd agree. I wasn't going to wear down.

"If I were to go on a hypothetical date with the hypothetical Grace who I would hypothetically never see after the date, then I wouldn't hold any of her actions against her when I didn't see her again."

Ashlynne smiled, apparently accepting my statement as agreement. "I really like the idea of a date as a safe space where I could act how I want to act, not how I feel I should act."

I was very distracted at work that night. When I got home, I was eager to jerk off but I couldn't find any porn that was satisfying. I eventually closed my eyes and came while envisioning Ashlynne's naked tits bouncing in front of me.

* * * *

Friday morning, Ashlynne came down in the light blue nightshirt again.

"What are your plans for your day off?"

"Work out, take the minivan to the dealer, and then play Xbox at the house of a a friend from work." Mom's minivan needed some routine service, and Dad had volunteered me to take it the dealership while Mom drove my car.

"I'm going to spend the weekend at my out-of-town friend's house again. You could play with your friend on Saturday and go out with Grace tonight. She's picked something to do that I think you'll really enjoy."

"No, Ashlynne. I have other plans."

"If you change your mind, let me know. She'll be waiting for you."

At the gym, a guy kept trying to talk to Ashlynne after she had put on her earbuds and started running on the treadmill. I had to come over and explain to him that my sister wasn't interested. He gave me an ugly look but finally moved on. Ashlynne gave me a big smile while she kept running.

After lunch, I took the minivan to the dealership. While I was chilling in the waiting area, my friend from work called. "Hey, Todd. Courtney called in sick, and I'm going to work her shift. I need the hours. Sorry about canceling on you."

"It's okay."

"Get together tomorrow?"

"Sure." We set a time, and I hung up.

Another Friday night and nothing to do in our podunk little town. Of course, I had another option. I could go out on a date with 'Grace'. I'd almost certainly have fun. Lots of fun. Maybe too much fun.

If I went out with Ashlynne, I could show her how a guy should treat her. I knew from training people at work that you could tell people how to do something over and over again, but it never sank in until they actually did it. After the date, we'd hopefully go back to being brother and sister. When Ashlynne went out on a date at the university, she'd know how to steer the relationship in the right direction, and she'd never have to call me to come rescue her. Mission accomplished by the protective big brother.

The problem was that Ashlynne and I weren't acting like a brother and sister anymore. As stupid as our fights over her nightshirts had been, they had made sense in terms of a normal brother-sister relationship. We were acting more like Mandy and I had acted before our first date. That made me feel queasy about going out on a date with Ashlynne.

The other choice was to stay home, lock myself in my bedroom and beat my meat while watching some babe with fake tits that I cared nothing about get fucked by some dude that I'd never seen before.

Having fun won.

"Hey, Ashlynne." I said when she answered her phone. "My friend canceled, and I'm available for a date with Grace."

"Great!"

"I'll text you where to meet. It's someplace close to the Chipotle we ate at last time. I'll see her at 5:30."

* * * *

Ashlynne was waiting outside when I arrived. She was wearing a tank top that had a unicorn on it which showed off her nice shoulders.

"Hello, Grace. Good to see you again."

"Good to see you, Oliver."

"Is that a new shirt?"

"How would you know if it is a new shirt if you've only met me once before?"

Duh. I rolled my eyes, and we went inside.

One problem with the blind date charade was that I couldn't remember what we had told each other. Ashlynne was prepared, and she spent most of the meal recapping what we had told each other before. After that, we talked about the novel she had given me and that I had finished at the dealership.

After dinner, Ashlynne wouldn't tell me where we were going, but only that it was about a half hour away. She had the address plugged into her phone, and I followed the directions. While we drove, we talked more about the novel, compared the movie to the novel and discussed similar movies.

Our destination was a convention center not that far from the university. They were having a car show.

"Is this okay?" asked Ashlynne.

"Should be interesting."

In the parking lot, I got out and opened the door for Ashlynne. When she stood up, she stuck out her hand and wiggled her fingers. It was the gesture Mandy and I had used to request to hold hands. It was decision time - was this going to be a show date like our first date or a real date?

I took Ashlynne's hand in mine.

Ashlynne said, "Let's go see what the cousins have been up to."

'The cousins' was the term in our family for the Chevrolet division of General Motors. As they had been nice enough to name a car brand after us, we had always felt obliged to support them. Dad drove a Chevy, as did Ashlynne and I. It irked Dad to no end that Mom had insisted on driving a non-Chevy minivan. My dream job was to work for Chevrolet, preferably designing cars. I thought it would be great to freak people out. Some vendor giving our department problems? "We'll have Mr. Chevrolet speak with you."

Inside the show, we made a beeline for the Chevrolet display, where we lovingly checked out each car they had on display. Ashlynne started acting differently - sillier and more demanding.

"Open the door for me, Oliver." "Now take my picture." She batted her lashes at me. "How do you think I look in this car?" as she posed with one arm raised behind her head. "Does this interior color go with my lipstick?" "Did you bring any reflective sunglasses? I need to see how I look in this car with reflective sunglasses on."

I didn't know what Ashlynne was doing. She had never been this vain and shallow. I took lots of pictures of her because she wanted me to take lots of pictures of her.

As she was getting into a Silverado with a black interior, she stopped and thrust her ass at me. "Does this interior make my butt look big?"

I rolled my eyes. I had no clue how to answer that. She got the rest of the way in, sat up in the seat, and closed the door. I leaned through the window and said, "The interior makes your chest look big."