by Kaci Rose
I smile thinking of her calling me on the food on Monday and picking her own place. I really enjoyed the restaurant more than I have a place in a long time.
"Who is she?" my mom asks.
"What do you mean?"
"You have been spacey and smiling all evening, it has to be a girl."
I frown. My mom knows everything, even that my last 'girlfriend' was a sugar baby. While my mom hated the idea, she was supportive. Just happy I was slowing down and getting out.
I tell her about Ellie starting with the mixer and up to clothes shopping on Monday, the texts, how she calls me on my bullshit, all of it.
"You like her." My mom says.
"Yeah, she's different. She doesn't seem to be after my money, but I know she's spending time with me because she needs it, she's a single mom to two girls." I tell my mom about her ex and what happened, and my mom nods.
"Have you met her kids?"
"No, I saw them in the car when I talked to her Monday, but that's it."
"Sounds like she needed some breathing room, and you came into her life at a good time."
"Thing is, if I wasn't paying her, I don't think she would have gone out with me much less taken money to help with her kids. So, I'm glad it happened like this, I like knowing she is taken care of and I'm helping the kids too."
"Would you go out with her without this arrangement knowing what you know now?"
This is the test from my mom, and I’m aware of it. I know what she is fishing for and I could lie to her, but this woman gave her all for me growing up.
Sometimes she worked three jobs and would protect me from my dad on his worst nights. It's my turn to take care of her now and I have paid her bills, bought her this house, her car, and given her money each month so she can do what she wants.
Mom has a good heart. She volunteers at the women's shelter that took us in, and at a kid’s activity center downtown. She is involved in several charities for single moms and survivors of domestic violence.
My mom is a huge influence of the charities myself and my company support and the events we attend.
I think of all this while I look into her eyes and I know I can't lie to her. Not now, not ever.
"Yeah, I would date her without the arrangement."
My mom smiles and sits back in her chair. "I knew you would say yes, that's why you’ve been texting all week. You like her."
I can't help looking at my phone again. Still nothing from Ellie.
"What's she doing tonight?"
"Her friend came over for a girl’s night."
"Ahh, they’re talking about you."
"Yeah," I mumble.
My mom laughs. "When do you see her again?"
"Tomorrow and again on Saturday, then not again until the following Friday."
"So, if things go good Saturday, ask her to meet up on Tuesday night."
"I have a meeting with Jeff and his wife that night."
Jeff is my company’s CFO, but also a friend. His wife and he invite me over once a month for a company meeting at their house, but I think it's mostly to make sure I have a home-cooked meal. They always send me home with food for my freezer and whatever leftovers there are from that night.
"Perfect excuse for a date, isn't it?" My mom smiles at me then changes the subject.
She talks about the girls at the women's shelter and the gala Saturday night and what they plan to do with the money from the event.
This event is for my mom, but she never feels comfortable at the galas. After a few times of watching her suffer through them, I told her she doesn't have to go. Instead, she can help plan and she agreed.
She helps me with my speech for the event as well.
As I'm getting into my car to head home, my phone pings with a text.
Ellie: What time tomorrow and what should I wear?
Me: 4 pm and casual jeans and that cute purple top you got Monday.
I smile thinking of her in it. It was one of my favorites from the shopping trip besides those jeans she got. Oh man, I got hard just seeing her in them. They hugged every curve of her ass in just the right spot and made her legs look long and amazing.
I wonder what it would be like to have my hands on her ass and all over those curves. My cock wanted her so bad all week, and he hasn't been happy with my hand.
I'm pulled from my thoughts with another ping from my phone.
Ellie: Can't do 4. My daughter has a field trip I'm chaperoning that day, can we do 6 just to be safe?
Me: 5?
I know I'm pushing my luck, but I'm itching to see her again, especially in those jeans. I know the entire night will be sweet torture.
There is a pause between messages.
Ellie: You can be here at 5, but I might not be ready. This is the first field trip I've been able to chaperone and I don't know what to expect.
I smile. I love knowing that she was able to do this because of our arrangement. I like I could help her with that.
The other arrangements I've had like this I didn't care what they did with the money and I never thought about it. Always assumed it went to name brand clothes and things they wore.
Honestly, we never talked about things on a personal level, so I had no idea.
But with Ellie, I know the money is going to help her girls and I have this male pride that I'm providing for them. While I'm happy, I'm not sure what to make of it either.
Me: I don't mind waiting.
Ellie: Okay, see you tomorrow.
Me: See you later. I can't wait to hear about the field trip.
Ellie: If I survive. I'm actually nervous.
Me: You’ll do great and I bet your daughter is excited
Ellie: She is, she's been talking about it all week.
Me: I'm glad you get to go. Get your rest you’ll need it.
Ellie: Good night.
∞∞∞
Friday at five I pull into the parking lot at Ellie's building and debate going and knocking on her door, but I know she wouldn't want that so call her and let her know I'm downstairs.
Twenty minutes later she comes out wearing the purple top and the jeans so tight they look like they were painted on her. She looks beautiful. So much so I'm starting to get hard and don’t want to scare her off, so I step behind the car door and help her in and sit down.
When she is looking out the window, I adjust myself and ask about the field trip. Ellie laughs and says she survived.
I like hearing her laughter. It washes over my body and relaxes me and makes me smile too. I enjoy the way her face lights up when she talks about only needing to use one band-aid when her daughter's friend skinned her knee.
She tells me it was a trip to the zoo, and they had all these fun little things planned for the kids and the zookeepers set up lunch picnic style in the gorilla exhibit.
Ellie tells me they sat in the viewing area which was a big circle and had several different enclosures for the gorillas. There were floor to ceiling glass windows to see them.
Her laughter is contagious when she starts telling me about the gorillas that started pacing in front of the window watching the kids eat and finally got mad that they weren't sharing and jumped at the glass window scaring everyone.
I could tell she had enjoyed this time with her daughter by the way she was telling the stories and how her face lit up.
She got a text message from Mia, something about where something was. I took that time to message my assistant to set up a donation to the zoo. I want to make sure those smiles stay on Ellie's sweet face.
She is an amazing mother and reminds me a lot of my mother growing up. I love how much she loves those girls and I know right then I wanted to do this longer than just a month.
I want to know I’m helping her take care of the girls, giving her time like this with them. I want to give her the freedom to write her book and have breathing room.
Of course, I enjoy her company and want many more dates like Monday and this one. She’s fun t
o talk to, even about the personal stuff, and I enjoy learning about her.
Thinking back to the conversation I had with my mom last night, I ask Ellie about Tuesday, deciding like always, my mom was right.
"Can you come with me Tuesday? I have dinner with Jeff, my CFO, and his wife. It's a work dinner but will be at their house and his wife is a fabulous cook."
"Yeah, I can do that," she says.
"It shouldn't take long, but I’d like you to come back to my house afterward. There’s something I want to talk to you about." She doesn't say anything at first.
"I promise to have chocolate cake and I promise no funny business, no expectations, just conversation."
"Okay," She agrees, but is still hesitant.
I try not to think about how excited I am to have her in my space and show her my house. I wonder if she’ll like it. I hope she will.
I pull my phone back out and text my lawyer about the contract. He’s also a good friend of mine and we went to high school together, so I trust him. I let him know of a few changes I want to make and that I want the contract ready by Monday so I can look over it.
He says he’ll have it ready and asks about the changes. I just say he’ll have to make time for a beer with me and I'll tell him everything. He agrees.
We pull up to the restaurant and I help her out of the car. She sees where we are and laughs.
"Cracker Barrel?"
"Yeah, you mentioned it on Monday, so I thought you’d enjoy it."
She smiles and leans up to kiss me on the cheek. Her lips are soft and warm, and her breasts push up against me as she places her hand on my arm.
"Thank you," she whispers before pulling away.
The kiss goes straight to my dick, and he springs right to life. It sends sparks down my body making my heart race. This is a feeling I haven't felt before and it's just from a kiss on the cheek. A simple touch, a simple kiss, and I can’t remember the last time I’ve been so turned on.
As we walk in, she lets me hold her hand. We are slightly overdressed, but she doesn't seem to care. We check in with the hostess and are told it will be a twenty-minute wait. I pull out my wallet ready to buy us the next table when Ellie stops me with her hand on my arm.
"The wait here is part of the fun, come on."
I start to protest, but she stops me. "Trust me?"
I take a breath and nod. She takes my hand again, which gives me a weird sense of male pride. She’s reaching for me on her own. I wonder if she realizes she is doing it. Does she notice this shift between us? Or is it all in my head.
We walk around the small store and Ellie gushes over some of the decor items, but when I try to buy them for her, she stops me saying she is just window shopping.
This woman is so different than the other girls I've met. They want me to spend my money on them, buy stuff, and take them to fancy restaurants where the dinner is expensive. They’re always hinting at gifts and things they want.
Not Ellie. She likes window shopping and likes her meals to fill her up. She likes to actually eat. She enjoys things that don't cost money like a walk near the water. I also suspect any money that is spent she'd rather it be on her girls than her.
Once we walk around the store, she takes me outside. The front of the restaurant is set up like a large country porch with rocking chairs and checkers tables. We sit down in two rocking chairs.
Ellie tells me about people watching and we just enjoy the night air.
"Have you ever been to a Cracker Barrel before?" She asks me.
"No, we didn't eat out when I was a kid and when I started working, I was a workaholic, only eating out on business meetings until a little over a year ago."
The weather is nice tonight and I have to admit it is relaxing to sit here and rock with Ellie.
When our name is called out over the speaker we are shown to our table. I take in the menu and it's all very much southern cooking.
"What would you recommend?" I ask her.
"I love their meatloaf and their fried chicken and can never decide which one to get."
"How about you get the chicken and I'll get the meatloaf and we can share?"
The smile that lights up her face warms my heart. It's the little things with Ellie that make her happy and that makes me want to keep doing them.
Dinner was really good, but I enjoyed talking to Ellie more. She surprised me by asking questions about the women's shelter, saying she looked it up so she could talk about it if needed.
I was completely shocked. I've never taken a date to a gala that even cared what it was for, much less looked any of it up.
With this being such a personal charity to my mom and me, it means a lot to me that she did.
Ellie was right, both the meatloaf and fried chicken were amazing, but I didn't like the fried okra she made me try. I noticed on the menu they have a Coca Cola Chocolate cake, so I ask if Ellie wants to split it with me and of course, she does.
After dessert, I head back to the gift shop to pay the bill and Ellie goes to use the restroom. I take this chance and grab a few of the items Ellie liked earlier and buy them when I pay the bill.
As we head out to the car, she eyes the bag, but doesn't ask. We get in and I hand her the bag with a sheepish smile.
"Oh, Owen, I love them, but I told you I was just looking."
"I know and the fact that you didn't want me to buy them for you made me want to buy them even more."
She smiles and leans in to kiss me on the cheek again.
"Thank You."
"Would you like to go see a movie with me?" I ask.
"Let me call Mia and see if she’s okay staying with the girls.”
She calls and I can hear the girls laughing in the background, and it makes me smile. Mia agrees she can stay.
I pull up the movies playing on my phone and we decide what to watch.
"Nothing horror, please. I will be the first to admit I'm a big wuss and don't like scary things. I won’t be able to sleep for a week."
"I'm not a fan of horror movies either," I say, and she looks relieved.
I offer to go watch a new romance movie, but she surprises me and says she'd rather see the new action comedy movie.
When we get to the theater, I purchase our tickets. I get some soda and popcorn because no matter how full you are, you can't go to a movie theater without having popcorn.
We head in and I let her pick the seats, but I have to say the view of her ass walking up the steps has me getting hard and very different ideas of what we could be doing in the dark back row. This girl is curvy in all the right places, and I can't help but notice.
We sit down and watch the previews and whisper about what we would like to see and find we have a lot of the same tastes in movies. Once the movie starts, we are laughing at the same parts.
I look over at her watching the movie, the light bouncing off her face and how she smiles at different parts.
I put the popcorn down and lean into her ear to whisper.
"Can I cuddle with you?"
She hesitates for only a minute and then nods.
I move my drink and lift the armrest, put my arm around her and pull her close. I take in her citrus and floral scent. It’s Ellie. She rests her head on my shoulder.
"Are you comfortable?" I ask.
She wiggles again and shifts a little before saying she is.
We watch the rest of the movie like this with me lightly rubbing her arm. At one point in the movie, she laughs, and her hand lands on my abs and I don't know if she realizes it, but she doesn't move it.
I let my mind wander, what if we could be a normal couple on a date. Would she still want to cuddle with me? Would she even want to date me?
Keeping the money between us is supposed to uncomplicate things. But I'm starting to realize Ellie is real, she isn't like the girls at the mixer. I knew that when I went up to talk to her, but I don't think I knew just how much she wasn't like them. With Ellie, the money only complicates thing
s more.
After the movie, I drop her off at her house and she lets me walk her up to her door. I remind her I have someone coming to do her hair and makeup tomorrow and they’ll bring a few dresses for her to choose from.
She looks a little nervous so before I can think too much about it, I put my hand on her waist and pull her towards me.
"Hey, you are going to do great tomorrow. I promise I won’t leave your side. I'm not throwing you to the wolves I'll be right by you the whole time."
She looks at me but doesn't say anything and I notice her eyes drop to my lips. Shit, does she want me to kiss her? Because I'd love nothing more than to feel her soft lips on mine.
The thought has me getting hard, and I take a deep breath to calm myself. I kiss her forehead, wish her good night and she goes in.
I head home and once I walk inside; I shoot her a text.
Me: Good Night Ellie.
Ellie: Good Night Owen.
It's silly, but that good night text has become part of my routine and I can't sleep until I get a response from her.
I try to sleep but all I can think about is Ellie's kiss on my cheek and watching her shift from date mode to mom mode before walking into the door and I'm rock hard.
I take my cock out and start stroking it, thinking of Ellie in those jeans and the view of her ass I got at the movie theater. I think about what if we had gotten a seat in the back row. The theater wasn't full, we'd have had some privacy.
What if when she was cuddled to me, I had brushed against her breast? Would she have let me take it further? Slipping my hand down her pants and rubbing her clit, I'd tell her to keep her eyes on the movie, but I'd have my eyes on her.
I'd make sure she was nice and wet. Of course, she'd be sopping wet for me. Fuck her being turned on has me nearly coming. I slow down, take a breath and picture it.