L'il Sis Ch. 08

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Ryan takes his sister on a date and more.
10.3k words
4.56
77.6k
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Part 8 of the 12 part series

Updated 11/02/2022
Created 10/04/2012
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TomWine
TomWine
935 Followers

I can't believe Ally's been out with Hunter all morning. They were only supposed to drive into town and pick up some things from the music store, but they've been gone all morning. As they walk into the band room, they discover we're all eating lunch. Ally looks surprised, so I suppose some "distraction" lasted longer than she thought, causing her and Hunter to run late. Ally looks over at me as they enter the room. At least she's smiling, I think to myself. At least she's OK.

Ally leaves Hunter and walks over, sitting next to me at the table.

"Did you get me any lunch?" she asks.

"Yeah, but I almost ate it," I say handing her Hardee's bag to her. I got her a sandwich, fries and a coke.

"Thanks, bro," she says, giving me a kiss on the cheek. "You're an awesome brother," she says while she tears apart her lunch and begins eating like she's starved to death.

"Work up an appetite while you were out with Hunter?"

"Yeah, really. I'm really hungry," she replies while eating.

"You better chow down, we only have about ten minutes left."

"OK. Just let me eat."

She really appears to be hungry, but otherwise, seems to be fine. I can smell sex on her though, so she and Hunter found someplace to do it. She continues to gulp down her lunch without saying anything about her morning.

"So, are you going to tell me what happened?"

"I will, but it's a long story and will have to wait until the ride home. I have to help Hunter with the shit we got at the store, and then practice. Thanks for the lunch, bro, you're terrific," Ally replies, grabbing her coke and what's left of her sandwich and heads to the back room to help Hunter. There are several people going in and out of the storage room, so nothing's going to happen in there. After a couple of minutes we all get up and head back to the practice field, with Hunter and Ally walking behind us.

"So, did you two have a good time?" I ask Hunter as he walks past me.

"You wouldn't believe it, Ry. That sister of yours is something else, believe me. I'm sure she'll tell you all about it. She says she tells you everything. See you later."

Practice goes well for the afternoon, and after breaking a couple times for water, it's time to head home. Mr. Wilkins gathers us up for our usual parting words, and then we head out to the car. It's been a long day, and I'm dying to hear what went on with Hunter and my sis.

I see Hunter and Ally heading to my car, talking. He gives her a little kiss at the door and then heads over to his car, gets in and drives off.

"Everything go OK with Hunter?"

"I'll say, it was awesome, Ry. You wont believe what happened."

"Try me," I say.

"Are you sure you want to hear this? I was pretty slutty. I mean REALLY slutty."

"Yeah, I think. Tell me about it."

I start up the car and head toward the main road. When I get to the intersection, Ally tells me to turn left, rather than right, which is the way home. While turning left I ask her, "What's this way?"

"You'll see. Just keep driving until I tell you to turn. It isn't far."

She was right, I don't drive a mile when she tells me to turn left into an apartment complex. I know the place. There are some kids from school who live in here, but mostly it's made up of college students in town, and others who moved out from home and attend the community college.

As I pull in I ask, "So, did Hunter take you to someone's apartment this morning?"

"Not exactly. Keep driving to the back and take the last left."

I follow her directions, and then she tells me to turn into the parking garage. I figure we are going to park and go to someone's apartment.

"Drive up to level C, turn left, and go back to space 54," Ally instructs. One thing this girl has is a memory.

I do as she says, and in a couple minutes I am parked in space 54.

"Is this where you parked?"

"Yes, and this is where we fucked, too."

"You guys fucked in the parking garage? Are you crazy or something? What if someone came out and saw you?"

"Well, we did fuck in the parking garage, right here; and, someone did come out and see us, and he fucked me too," Ally replied.

"You fucked two guys in the parking garage? Who the fuck was the other guy?"

"I don't know his name. He was watching from over there," Ally offered, pointing to a row of parking spaces. "He watched us fuck, then came over and fucked me too."

"Christ, did that really happen or you just telling me this shit?"

"Believe me, Ry, it really happened. I still have cum inside me to prove it, I'm sure. Let's head home, and I'll tell you the whole story."

I pull out of the parking garage and head home. On the way, Ally tells me the whole story, not leaving out any details. Christ, I know she's telling me the truth; you can't make this shit up. She doesn't finish her story until we are just about five minutes from home. My mind's swimming with the details and thinking about Ally spread out on the hood of Hunter's car fucking Hunter and some guy she doesn't even know.

"Shit, Ally, Hunter had a friend of his watch the two of you fuck, and then you fucked him too and sucked them both off after that?"

"Yep, that's about it, Ry."

"Holy Christ. I can't believe all this. Was he a good friend of Hunter's? Maybe I know him."

"By the way they acted, I think they are REALLY good friends, Ry; but I didn't recognize him; maybe he went to the county school. I know he didn't go to ours."

Ally pulls out her phone and sends a text. She sends and receives a couple more before she says anything else.

"His name's Damon, and he went to county. Hunter met him in one of his DC classes at the community college last semester. Hunter also asked if I'm telling you all this. I told him, "Of course."

"You told him you are telling me? Does he think that's odd?"

"He thinks our relationship is odd, but what the fuck. I don't care what anyone thinks."

'So, what was Damon like?"

"Well, he's taller than Hunter, sort of thin, long hair, cute, nice circumcised cock, and smokes weed."

"How do you know that?"

"Oh, I left that part out. We smoked a couple of joints too, that's what loosened me up enough to fuck Damon too."

"Christ, Ally," I reply.

"There'll be plenty of weed tomorrow night."

"You didn't invite Damon to the party did you?"

"No, but only because I didn't think of it. Christ, I would like to, I could fuck him again. Probably will, too. I told him and Hunter we could do it again, only inside the next time."

By this time I'm pulling in the driveway. I look at my watch and see that it's almost 5:00.

"We only have an hour before we need to leave, maybe a few minutes more, but we really need to head out around six."

"You seem upset, Ry, does this bother you?"

"I don't want to talk about it now, I want this to be our evening."

"Are you going to tell me where we're going?

"Nope, just put on your short black dress."

"Anything else you want me to wear?"

"Not really. The less you wear the less I'll have to take off you when we get home."

"I like the way you think, bro. I need to take a quick shower. It wont take me long to get dressed," Ally says as she jumps out of the car and heads inside.


I pick up our things from the car and head inside. I drop some shit on the kitchen counter and walk over to dad's liquor cabinet. I take out his flask and fill it with some Jack. Thinking of what Ally told me on the drive home, I feel I need a drink to keep my cool, so I down some Jack straight from the bottle. I feel anger welling up inside of me, and take another drink. I take the flask up to my room and set it on my desk, before going to Ally's room to check on her. As I walk into her room, she is pulling her shorts off.

"Christ, I love watching you undress," I say to her.

"I like you watching me undress," she replies, stepping out of her shorts and pulling her top off. She walks over to me and wraps her arms around me, bringing her lips to mine.

I kiss Ally on the lips and drop my hands to her sweet ass. Fondling her, I say, "I love you sis. I want you all to myself this evening. Nobody but the two of us."

"Ummm, I like that. Let's head to the shower," Ally replies, pulling me along with her. While she turns on and adjusts the water, I shed my clothes, and we get in the shower together.

Ally kisses me again.

"I'm sorry it bothers you so much what I did today. Christ, I'm such a slut. Once I saw Damon's cock, I knew I wanted him to fuck me. Why do I do that?"

"I don't know, Ally. Because you like it, I guess. Just don't get tired of fucking me."

"I'll never get tired of fucking you, Ry," Ally replies, giving me another kiss.

We thoroughly wash each other. She has me pay special attention to her pussy, to get it clean from her double fuck this afternoon. I clean it good, and feel her up some while we are in the shower, but we don't have time for much more. After we finish washing, we get out of the shower and dry off. We head to our own bedrooms to get ready for dinner.

I comb my hair, put on deodorant, and start getting dressed. I put on a pair of dress kakis, a light blue shirt, and my navy sport jacket. Looking in the mirror I think I look pretty good. After putting on my socks and shoes, I take the flask and put it in the inside pocket of my jacket. I leave my room and head downstairs. As I walk past Ally's room, I notice the light is on inside and I can hear her getting ready.

I walk out to the car and make sure it is cleaned out. I want everything to be perfect for our date.

After about twenty minutes, at ten past six, Ally comes down the stairs, looking like a dream date. Her hair is combed and hanging down on her shoulders. She has on a beautiful pearl necklace, that hangs down onto her chest. The black dress looks awesome on her, and the neckline shows lots of cleavage. Almost too much. The dress fits her snugly, clinging to her hips as she walks, It hits about mid to quarter thigh, showing off plenty of skin. Christ, I don't know if I can make it through the night with her looking like this. She is fucking beautiful, and I know whats under that dress -- the most wonderful body in the world, and its all for me after we get home. Christ, I start throwing a boner looking at her.

"I see you like this dress, Ry," Ally says, looking at my crotch.

"Yeah, I do. I hope I don't cum in my shorts looking at you, sis."

Ally sways over to me, walking very seductively, reaches up and plants a hard kiss on my lips. I drop my hands to her waist and let them fall to her ass. Reaching under her dress, I cup both cheeks, noticing that she's not wearing any panties.

"Christ, Ally, you're not wearing panties?"

"Nope, I thought it might be more interesting if I didn't, and I'm not wearing any bra either. I want this to be a fun date."

"Oh, it will be, believe me."

"Are you going to tell me where we're going?"

"Nope, you'll find out as we drive. You might guess where we are going, you've been there at least once before."

"OK. Let's get started before I tear your shirt off and fuck you in the living room," Ally teases.

"We'll save that for later."

We walk out to the car, and I open the door for Ally. She slides down into the seat, spreading her legs a little, giving me a shot of her pussy.

"Christ, I don't know if I can last the evening without jumping you, sis."

"I think you'll manage, but I'm going to make it as difficult as I can."

I shut the door, walk around to my side of the car, get in, start the car, and head out of the driveway.

We drive for about thirty minutes, heading out of town and into the country.

"I think I know where we're going, Ry. Are you taking me to the Vineyard, to that Italian restaurant? Christ, you are! I love that place! That's the perfect place for us to go on our date! Ally leans over and kisses my cheek. "I'm so excited now! I can't believe you're taking me there!" After kissing me, Ally takes a Kleenex out of her purse and wipes my cheek. "Got a little lipstick on you, bro."

"That's OK. I want a more of it on me later on. Christ, I love you Ally."

"I love you, too, Ry."

Ally really seems excited to be going to the winery. I thought she would like this.

We finally pull into the driveway, at 7:00 on the dot. They have Valet parking, so I pull to the front door. An attendant opens Ally's door for her, and as she exits the car, I see her give him an eye full, spreading her legs a little as she gets out. With that short dress, there is no graceful way for her to get out of this car. I get out of the car, hand the attendant the keys, and he gives me a claim ticket. Ally and I walk toward the restaurant while he parks the car.

It's a beautiful night, and the view from the winery is awesome. The mountains surround us, the sky is clear, and I have the most beautiful woman on my arm, who also happens to be my sister.

Ally leans in a kisses me hard on the lips. I put my arm around her waist and pull her in for another kiss, dropping my hand to her ass and giving her a little squeeze through her dress.

"This is so awesome, Ry. Thank you."

"You're welcome, Ally. You look so great tonight. I have the prettiest date in the place, I'm sure."

We walk inside and up to the maître d' and give him our name.

"Reservation for two at seven o'clock. Nice, quiet table in the corner, I believe. Yes, follow me please."

We follow close behind him, and he takes us to our table. He pulls a chair out for Ally, and she sits down, very gracefully, holding her knees together as tightly as she can, not wanting to give this elderly gentleman a heart attack.

The table's set beautifully. There's a candle in the middle, a small vase of fresh flowers, and more silverware that I've ever used at one time. Christ, this is a fancy place. The lights are dim, and Ally looks beautiful as the flame casts a slight glimmer over the side of her face.

"What are you staring at?" Ally asks.

"Just you. You are so beautiful in the candle light. I know I may sound stupid, Ally, but you really are beautiful, and especially beautiful tonight."

"Thank you, Ry. That's very nice of you to say. You look quite handsome as well, all dressed up. I love my date!"

"I love mine too."

The waiter comes over and hands us a menu.

"Would you like to order your drinks?"

"Yes, please. Two cokes and two glasses of water."

"I'll be right back with your order, sir," he says walking briskly away.

"No wine?" Ally asks.

"No ID," I reply.

"Oh, yeah, I forgot about that! I wish we were in France. It wouldn't matter. Oh well."

"But I have something else," I tell her. "Just wait until the cokes come and I'll show you what I mean."

We look over the menu for a few minutes trying to decide what to order.

"Will you order for me? I have no idea what to order," Ally asks.

'Sure, I can do that. Do you trust me?"

"If I didn't trust you, I wouldn't have asked you to order for me, Ally says laughing.

The waiter returns with our drinks, and asks if we are ready to order. He tells us the specials for the evening, and honestly, I don't understand a word he says.

For appetizer, we'll share the Frittelle di Aragosta, and the Piatto di Salumi Nostrani, please.

"Excellent selection, sir. Obviously you have dined here before. Those are the best of the house. I'll place your order."

"Sir," I call out as he turns to leave.

"Yes," he replies, walking back to hour table.

"There's no rush. This is our first anniversary, and we want to enjoy or evening. What time do you close?"

"We don't close until eleven, sir, and we never rush our diners. Enjoy your evening, and if you need anything, anything at all, all you need to do is ask."

"They're really nice here, Ry. I love this place."

"Yes, they are," I say while pulling my coke in close. I take the flask out of my jacket, open it, and pour a shot into the glass. I place the glass in front of Ally, and she watches closely as I take her glass and do the same, then setting it down in front of me.

"Just a little Jack for the coke, that's all. Dad said we had to stay out of the wine cabinet, but he didn't say anything about his liquor cabinet. He'll never miss it."

"This is great, Ry. I LOVE Jack and coke," Ally says as she takes a sip. "This is good, Ry."

"I'm glad you like it."

They bring our appetizers shortly, and we begin eating our lobster salad and salami. They split the salad in the kitchen, so they bring it on two separate plates.

"This place is so romantic, Ry. Do you think I can slide my seat closer to you, I hate being this far away, and I don't like the flower in the middle of the table."

"Hey, whatever you want, sis," I say as I begin to move her plate to the side of the table. The waiter notices what we are going, and walks briskly over to our table.

"Allow me to assist you, sir," he says as he moves everything for us. He turns to Ally and says, "Allow me, Signora," as he takes her hand helping her stand, moves her chair, and then assists her back in her chair. I keep a close watch on the bottom of her dress, fearful that she might accidentally flash the waiter. She handles it perfectly.

"Shall I get you a refill?" he asks, referring to our cokes, which are already empty.

"Sure, two please," I reply.

"Certainly."

He leaves to get our cokes.

"This place is so nice, Ry. Thank you. This is so sweet of you."

"Anything for you, Ally."

"You really are nice to me, Ry."

When he brings our cokes, he asks us if we would like to order our first course.

I reply, "I will have the Zuppa di Gamberi e Ceci, and Ally will have the Tagliolini al Ragù di Carne."

"Excellent selections, sir."

As he walks away, Ally asks, "What are we getting?"

"I'm not sure, but I looked over the menu online and selected some things I thought we'd like. I think they'll be good."

"I'm sure they will, and you speak Italian beautifully!"

I pull my coke in close and pour another shot of Jack, set it in front of Ally, and to the same to hers.

"Are you trying to get me drunk so you can have your way with me, Ry?"

"Do I need to get you drunk to have my way with you?"

"Nope, but it sure as fuck is going to help!" she says quietly, giggling. Maybe I need to cut back on the Jack a little.

We have a pleasant conversation during dinner, talking about mom and dad and what they might be doing, what they would think if they knew we were out on a date, and here of all places. We talk about tomorrow night and what might happen at the party, but nothing is said about the events earlier today. I think Ally knows I really don't want to talk about that tonight. All in all, we're having a very nice evening.

The waiter brings our first course, and we dig in. Ally tries a little of my soup, and I try her dish. Both are very good, and there's so much food.

"I read online that we don't have to order all the courses in an Italian restaurant, but I thought, 'what the hell, why not.'"

"It is all good. Thank you again for doing this, Ry. I wont be able to eat anything else for the rest of the week after this."

"You're welcome, Ally, and we wont have any money left after tonight, either, so you wont be able to eat anything else the rest of the week," I saying only half way kidding.

The waiter brings us another round of cokes, as we have now emptied two each. I do the same thing with the Jack, so we're both on our third mixed drink for the evening.

"This coke and Jack is starting to get to me, Ry. Maybe I better stop for a while."

"No problem. Just take it easy, you don't have to drink anymore if you don't want to."

"Oh I want to, but I better not, for a little while, anyway."

We finish our first course, and the waiter clears out dishes and returns and asks what we would like for our main course.

TomWine
TomWine
935 Followers