My Sister Set Me Up on a Blind Date

"Oooh! I like that! Take a picture of me and my big chest!"

I did and then leaned forward again. "All the interiors make your chest look big."

"I like that even better!" Ashlynne smiled and then winked at me.

After that, I did my best to play along by constantly complimenting her looks, showering her with attention, and taking her picture whenever she seemed close to striking a pose. I let her be the star of our date.

"Which one are you going to buy me, Oliver?"

"That one," I said as I pointed to a massive four-by-four truck.

Ashlynne laughed. "That's for guys with small dicks."

"No, it's not. It's the vehicle of choice for someone living a lifestyle that you don't understand. That doesn't mean that it's wrong, it's just different. You'll learn to respect alternative lifestyles at college."

Ashlynne snorted. "I'm too familiar with that lifestyle. And I still think it's for guys with small dicks."

"Don't take human sexuality at college. It sounds cool, but it's actually boring. The only thing I found interesting was the discussion of dick size. Most guys think their dicks are too small, even if they're of average size."

"And you don't think your dick is too small?"

"No. It's about average, and I've never gotten any complaints. It's not that important to girls."

"What makes you think that?" she said as she batted her eyes at me.

"I'll believe it's important to girls when they come out with the boxer's equivalent of a push-up bra." Ashlynne laughed. "And what do you think of dick size?" Ashlynne blushed and said nothing. "I think it's become a new curse. Before people would say," I raised my fist and shook it, 'May the fleas of a thousand camels invade your armpits!' Now, people say, 'May you have a microdick!'"

I said the last line too loudly and several people turned and stared. Ashlynne giggled while holding tight to my arm.

"My, my, Oliver," Ashlynne said in a pompous voice. "You must learn to watch your language."

"You're acting crazy."

"Go ahead. Get in my face and tell me I'm acting like a crazy, entitled princess."

I scrunched down so that I was at her eye level with my nose an inch away from hers. "You're acting like a crazy, entitled princess."

Ashlynne kissed me.

I felt like I was stuck by lightning. I heard Ashlynne giggling as she danced around me. I stood there like a statue. I finally gathered my wits and moved on to the next Chevy. Ashlynne moved next to me and gave me the 'I want to hold your hand' signal. I didn't and instead said, "That was very bad of you."

Ashlynne snorted and giggled, then danced away from me.

I couldn't believe how my sister was acting. She had always been so serious. One of my favorite ways to annoy her had been to tell her to lighten up or to smile. Both of course had the opposite effect every time.

Ashlynne asked, "What do you think of this paint job?"

I looked at Ashlynne, and she was bent way forward over the hood of a small car. I could see all the way down her tank top. She was wearing a lacy red bra that was dangling down enticingly.

"Eye-catching."

Ashlynne cracked up and danced away again. Then she came up to me and said, "This is so different from my other dates." She held up her hand next to her head and made circles with her finger. "I've got these thoughts running through my head..."

"You know, you're giving the universal crazy, entitled princess signal."

Ashlynne exploded in laughter. "That was very bad of you."

I shrugged.

Ashlynne held out her arm, wriggled her fingers, and said, "I know you'll forgive a hot girl who knows how to turn you on." I shook my head and then took her hand.

We finished the Chevrolet display and started wandering through the other car brands. Ashlynne said, "I've never really flirted before."

"How come?"

"Mom would punish me if she thought I was flirting. It wasn't what good girls did."

"Mom wasn't around you all the time."

"Yes, but guys who I didn't want to encourage were."

"And you want to encourage me?"

"Of course! As I was saying before you rudely interrupted, I'm constantly thinking of ideas of how to encourage you. That's never happened to me before. When you're on a date with a girl, are you constantly thinking of ideas to encourage her?"

"No. I'm trying to figure out if she has any padding in her bra."

Ashlynne snorted. "Are you familiar with positive consent, Oliver?"

"I've had the term explained to me."

"You keep your hands to yourself unless I give you permission beforehand. And it doesn't apply to me."

Ashlynne gave my ass a squeeze, then exploded in giggles and danced away. I shook my head in mock disapproval, which made her giggle more.

"So what are you encouraging me to do?" I asked.

"I should be clear on that. When we leave here, we're going to go to my friend's house and park in the driveway. It's a very private spot, and she's told her dad to not bother us. We're going to make out there for a while. Then I'm going to go into her house, and I'll never see you again. Is that okay with you?"

I felt slightly disappointed for some reason. "Yes."

"And I can trust you to do only what I give you permission to do?"

"Yes."

"Great!" And she bent forward to give me another look down her shirt.

After she had giggled some more, she sidled up to me and took my outstretched hand. "I feel so wicked. And I'm having so much fun. I can't imagine acting this way all the time, but it's a lot of fun acting this way in a safe space." Ashlynne hugged me. "Thanks for playing along and giving me the safe space." She released the hug and went back to holding my hand. "Maybe I should go into the bathroom and take off my bra?" She flashed me a wicked smile and then laughed some more.

I couldn't believe how my sister was acting. The girl who spent years not letting me see her in a nightshirt was talking about flashing me her tits? "Aren't you worried that you'll give me the wrong impression?"

"No." Her voice was serious for once. "I've realized that I can't worry about giving the wrong impression. After my date with Jeffrey, I beat myself up over and over for having led him on more than I intended. I thought it was my fault that I ended up having to lock myself in the bathroom. But I've done a lot of reading since you talked to me about Mandy, and I've realized that I did nothing wrong. A woman cannot act or dress in such a way that some man doesn't get the wrong impression. My mistake was going on a date with someone I couldn't trust." Ashlynne stopped me and gave me a hug. "Thanks for letting me go out on a date with someone who's worthy of my trust." She went up on tiptoes and gave me a kiss. It wasn't a long kiss, but it definitely wasn't a sisterly kiss. She moved back to my side and took my hand. "Ready to go?"

"Yes."

As we walked toward the exit, Ashlynne swung our hands way high. I laughed at her childishness.

"By the way," said Ashlynne. "I've already resolved my challenge. Kissing my brother is fun."

* * * *

This story was written by 8letters and published on Literotica

When I got into the car, Ashlynne said, "My crazy, entitled princess phase is over."

"You're now merely an entitled princess."

"Yes. And a very happy one. What's the gesture for you want to hold hands in the car?"

I held my hand outstretched a foot above the console. Ashlynne laced her fingers in mine.

I felt that we were both nervous on the drive to her friend's house. I responded to my nerves by being quiet, and Ashlynne responded by talking more, so the drive consisted of Ashlynne prattling on with me occasionally saying something in response.

On the drive, I thought back to something Ashlynne had said about her date with Jeffry - because it had gone well, she was going to let him do anything he wanted as long as the clothes stayed on. I felt like our date had gone great so far. Would she let me do anything I wanted as long as our clothes stayed on? No, that was crazy. I was her brother, and she wouldn't let me go too far. But I could probably stroke a lot of her body and that'd be okay. But not her tits. I definitely wasn't going to touch her tits.

I parked in the driveway in front of the garage at Ashlynne's friend's house. We were well away from what looked like a quiet street. Her friend's house and the house next to it were both one-story, so no one could look down on us. It was a very private place to park.

"Let's get in the back, Oliver."

We got out of the minivan and opened the side doors. I could hear the faint sound of a movie or TV show from her friend's house. The neighbor's house was dark. As we got back into the minivan, Ashlynne slipped her fingers in mine. I felt so nervous - I hadn't felt so nervous since my first few dates. I tried to think of some line of conversation to discuss, but my mind was mush. I thought briefly about sitting in one of the middle seats but Ashlynne pulled me toward the back.

When we were seated on the back bench facing each other, I said, "Grace, thanks for the-"

Ashlynne kissed me. Then she broke quickly broke it off.

"I'm sorry," she said. "I should have asked permission."

She seemed defensive.

"It's okay. Do what you want. Don't worry about positive consent. You're not going to overpower me and make me do something I don't want to. I'll do positive consent so you'll be in charge. Can I hold your hand?"

"Yes." She laughed nervously.

I took her hand. "Are you okay?"

"Yes." She seemed anxious.

"We don't have to do anything else. I've had a great date, and I don't mind ending it here."

Ashlynne seemed to be getting pissed. "I want to kiss. I want to make out. Let's not talk about it anymore."

"Okay." I leaned forward to kiss her, giving her plenty of chance to stop me. Instead, she leaned into my kiss. It was a short, soft kiss that was followed by another one, then a longer one. I slipped my hand across her flat stomach and pulled her closer to me. It was like a switch turned off in my brain, and I no longer thought of Ashlynne as my sister. She was a woman who wanted to be kissed, and I wanted to kiss her.

I slipped my tongue inside her mouth, and she greedily sucked it in. I explored her mouth while my hands roamed across the top of her collarbones, across her shoulders, down her arms, and along her long smooth legs. Ashlynne kept her hands pressed against my chest, holding me in the same relative position as her. I withdrew my tongue, and Ashlynne's followed mine into my mouth.

We Frenched like that for a long time. Ashlynne wanted to kiss on her blind date, and I was happy to go along. It had been a long time since Mandy left, I enjoyed kissing, and it felt good to use my lips and tongue so intimately again.

My hands kept roaming and in each circuit, they moved a little bit closer to Ashlynne's tits. I kept the presence of mind to not grope my sister. I pulled back and kissed her on the lips. That triggered a series of hot, sloppy kisses where we kissed each other all around our mouths. As we kissed, I kept thinking about her tits. How they looked when the last time I saw her in a bikini. How they looked in various nightshirts. I tried to not think about them, but the harder I tried not to, the more images of them leapt unrequested to my mind. I had never dated anyone with tits as large as Ashlynne's. And they called to me like sirens.

I decided to do something different. I broke off our kisses, dropped my head down, and nibbled lightly on Ashlynne's neck.

"Do you like that, Grace?"

"Oh yes, Oliver."

Ashlynne ran her fingers through my hair as I continued lightly nibbling on her neck. I nibbled upwards until I reached her right ear. I whispered in, "You're so wonderful, Grace." I nibbled her earlobe. "Do you like that?"

"God yes, Oliver."

Ashlynne was panting. I nibbled her ear a few more times before swinging my face around for a kiss. As I did, Ashlynne grabbed my head and rammed her tongue into my mouth while pulling me upwards so we were somewhat standing with one bent knee on the bench seat and one angled leg on the floor. Our tongues dueled frantically in my mouth as we ground our bodies together. Any thought of asking permission was gone. Besides, Ashlynne was initiating as much as I was. I realized I was cupping Ashlynne's ass with my right hand to balance myself. When I moved my hand away, she grabbed it and pulled it back. I began running my hand up from above the back of her knee up to her ass and then back down as we continued to frantically kiss. On each trip up, I gave her ass a strong rub and a squeeze.

I broke off the kiss and switched to nibbling on her neck. At the same time, I grabbed Ashlynne's ass with both hands and pulled her against me.

"Do you want this?" I asked.

"Do it!"

I rubbed her shorts-covered pussy up and down on my cock. My brain was filled with animal lust, a lust that didn't care that this woman I was madly groping was my sister. I continued dry-humping Ashlynne while squeezing her perfect ass. We were moving too much for me to nibble on her neck so I concentrated on grinding my crotch against hers. It felt so damn good that I was completely lost in the pleasure. The only things that existed in the world were Ashlynne's ass, my dick, and her crotch.

Suddenly, something else existed - sperm. Lots and lots of sperm. They were fleeing my balls in a quest for freedom. My cock exploded with a massive cum inside my underwear. Each spurt felt huge. My knees almost buckled from the strength of the explosion.

What the hell was I doing? Dry humping my sister? This was not what I intended. This was crazy. And sick. And crazy sick.

"Let's stop, Grace," I said.

"Did I do something wrong?" Ashlynne sounded scared.

"You did nothing wrong."

I put my hands on her hips and guided her so that I had one leg down the bench seat and one leg on the floor and Ashlynne in front of me with her back pressed against my chest.

"If I did nothing wrong, then why are we stopping?" The pitch of her voice was rising.

I wrapped my arms around her.

"I got carried away and should have checked in more. Were you okay with what we were doing?"

"Yes. Are you sure that I didn't mess up?" Ashlynne sounded close to tears.

"You were great! You were too good. I wanted you to be in control, but once I started kissing you, I lost control. I'm sorry. You were a great kisser."

"Really?"

"Yes, really. It was crazy hot kissing you. I did things that I didn't intend to do, so I stopped to make sure that you weren't upset that I had gone too far."

"No. I wasn't upset at all. When you stopped, I thought it was because of me."

"Would you like to kiss some more?"

"Yes."

Ashlynne twisted in the seat, and we kissed. With a big load blown, I didn't feel nearly as frantic. The kisses were softer and more caressing. I slipped my tongue into her mouth again, but slowly this time. I was in no hurry and broke off kissing to talk.

"You're wonderful to kiss," I said.

"Thanks. You're great kisser, too. I'm sorry that I panicked there."

"It was okay. You had nothing to be concerned about it."

"It's just that..." Ashlynne sighed. "I'm a perfectionist. I hate doing anything wrong. On dates, I worry constantly that I'm screwing up; that I'm kissing wrong; or I'm kissing when I should be doing something else; that I'm too aggressive or I'm too passive."

"You were wonderful. Relax and enjoy."

I moved Ashlynne so we could kiss again, and she rose to meet me. We kissed awhile, some Frenching and some on the lips. I stopped us once more.

"So good," I told Ashlynne. "You're great to be with."

"I know this is probably going to sound awful, but I was really enjoying it when we were out of control."

"And I was enjoying it too." My nasty underwear was a testimonial to that. "But we were doing things that you enjoyed. It could have gone on to something that you weren't ready for. It's a lot better to go slow." Ashlynne pouted slightly. "You're not trying to set a speed record. You're trying to build a strong relationship. A strong relationship takes trust. And building trust takes time. So go slow."

She seemed more satisfied with that. She leaned back into me and sighed.

"I never thought I'd say this," I said as I wrapped her in my arms. "I like being the protective big brother."

Ashlynne laughed. "You do a great job of it. I feel safe with you." She put her arms on my arms and squeezed, effectively giving herself a hug. "I don't mean just physically safe. I feel emotionally safe with you. I had that panic, and I was afraid that I was going to ruin the date again, but you calmed me down and made me feel good about myself."

I gave her a hug. "You have a lot to feel good about."

"I know. It's that..." Ashlynne sighed. "Mom and Dad have always been DON'T DO ANYTHING. And I've always been a good girl. But I feel like I should have moved beyond that long ago. I should have spread my wings and explored. I feel like when I go out now that guys expect me to have a certain level of experience that I don't have. I'm afraid that I'll do something super stupid, then my date will laugh at me and tell everyone at school that I'm such a noob. When something happens that I'm not expecting, I panic."

"Be upfront about your inexperience to your date. I'm sure that he'll understand. He'll probably find it exciting that he gets to teach you. I'd find it exciting."

"You would?"

"Yes."

"There you go, making me feel good about myself."

"We've done everything you wanted to do. Are you ready to go in?"

"Not yet. Can we kiss some more?"

"Sure. I'll kiss you as long as you want to kiss."

We kissed some more. As we kissed, our kisses got steamier. Soon, we were Frenching vigorously. I was sorely tempted to slide my hands up and cup her big tits. I was getting too excited, and I stopped.

"How do you feel?" I asked.

"Happy. Sexy. A little out of control, and I like that. Ready to do some exploring."

I didn't know what to make of Ashlynne's last comment. She didn't give me any time to think about it - she resumed vigorously kissing me. As she kissed me, she put her arms over mine and pressed her fingers inside of mine. As we continued to tongue wrestle, she slowly lifted my right hand up until it cupped her tit. I stopped kissing.

"Ashlynne, we shouldn't do that."

"I'm an entitled princess - we'll do what I want."

"Ashlynne, I don't think-"

She cut me off with a kiss, sliding her tongue into my mouth. I lost my train of thought and was soon ardently kissing her back. I noticed that we had dropped the "Grace" and "Oliver". It was now Todd and Ashlynne who were making out. She raised both of my hands and put them on her tits. Fuck it - if she wanted me to grope her tits, I wasn't going to fight it.

I broke off the kiss and then repositioned Ashlynne so that I could kiss on the right side of her neck while she leaned against me. I cupped her tits in both of my hands and gently massaged them.

"Do you like this?" I asked.

"Very much."

I went back to kissing Ashlynne's neck while she gently moaned. I loved the feeling of her tits in my hands. It would have been even better if she hadn't been wearing a bra. Still, it was far, far more than I had expected being able to do when she first suggested that we go on a blind date together.

"You're so wonderful," I said between kisses. "And beautiful. You have such a great body." Ashlynne made a kind of purring sound as she pressed her body against mine. "You've been great to be with tonight. You're such a fun person. I've loved talking with you."

As I continued complimenting Ashlynne, she started arching her back to rub her ass against my now hard dick; essentially dry humping with her ass. Damn - we should talk through that escalation of physical intimacy, but I was enjoying it too much to stop it. The more I said sweet nothings while rubbing her breasts, the more she undulated against me. I was losing control again.