Five Dates Ch. 01

I settled into a chair in the lawyer's office next to my sister-in-law Trish. Maybe I should say sister of my late wife, since we weren't technically in-law's any longer since my wife had passed. It had been exactly one-hundred and eighty days since the funeral. I really didn't know what this was all about. Trish was as surprised as I was to get the call from the lawyer two weeks ago, setting up the meeting for today. Exactly today.

"Any idea what this is about?" Trish asked as she settled into the seat next to me.

"Not a clue," I answered. "The only hint that I got was that this was part of Nancy's will."

"So," the lawyer said as he sat down on the other side of the desk, "I know this is unusual, but Michael, your wife was a very determined if not unusual woman. She left very specific final instructions, of which this is part. She recorded a video to explain this all. She asked that the two of you watch this together." He reached to his computer and started a video, which played on a large-screen tv next to his desk.

"Hello Michael, Trish. I know this is coming as a surprise." My late wife said as she sprang to life on the screen. She looked weak, her head covered in the bright-pink flowered cloth that she liked best. I could tell that this was recorded very late in the process. She might have had on a normal top, but I could still tell she was sitting in the hospital bed, the muted tones of the machines she spent so much time wired to in the background.

"I've kept a secret from you Michael. I know you'll forgive me, you always do, but believe that I had my reasons. By now it's been six months. Hopefully by now you've gotten used to me not walking down the hallway, not sitting down next to you, not coming home from work. You've had to get used to sleeping alone and eating alone and being alone. You've probably already figured out that I put my sister on the spot. I tasked her with helping you out, trying to get you organized and living life. I know it was hard on you, I never planned on ending this way or this fast." She paused and took a drink, her face clearly screwing up in pain for a moment. A view of her that I saw too many times in the few short months that we had together once her body started being ravaged by the cancer.

"You know those silly lottery tickets that I bought every week? Yeah I know in ten years I won a few dollars here and there. You always said it was a waste of money. Well, the ticket that I bought the day before I was diagnosed with this turned out to be a big winner. Kind of ironic. I won big on one lottery and lost big on the even more important one. Yes, I know. I didn't tell you it won. You see, when I got diagnosed, I learned the hard lesson that if I managed to beat this, and yes I knew day one that it was a long shot, that my years would be numbered. It was rare for anyone to survive this more than a dozen years. What I thought I'd do is hold it as a surprise. When I beat this we could use the money to both retire early and spend our years doing all those things we planned for retirement. We'd have to do them soon though, because I wouldn't be growing old and gray with you. I knew that. I accepted that," she said, reaching up to wipe her eyes with a cloth.

"But I know that there's no happy ending to this fight. I'm down to days left, and each one gets harder. I've done my best to prepare you for the change this will be in your life. We've talked about your life moving on. You of course promised that you'd find a way to be happy and live, but I know you. You're a horrible liar," she said, wiping her eyes again.

"We both know that you're going to turn into a old broken-down hermit. We've been so much each other's lives for so long. But I don't want you to do that. I refuse to let you waste away. You have so much more life and love to give to someone. The problem is, you wont go looking. You wont even try, no matter how much you promise me. I can see it in your eyes and hear it in your voice. You think love is gone from your life forever when I leave. You're wrong, but the only way you'll ever believe that is for you to see first hand that you can still have fun and enjoy life. Once you can do that again, you'll know you can love again."

"Sis. You've said for so many years how jealous you are of me, of how perfect Michael has been for me and how you wished you could meet a man that was like him. You've said that you wished you could just date a guy that was half as perfect as Michael. Well, I have a job for you to do. I want you to convince Michael that he can indeed still live life and be happy." She paused to take another drink, a fleeting expression of pain once again coming to her face.

"How the hell am I supposed to do that sis?" I heard Trish quietly ask her sister on the screen.

"I'm sure that you're wondering how you're supposed to keep this request. First, let me tell you that it won't be easy. I know Michael, he can be very stubborn. Don't think I don't know that you've wanted into Michael's pants over the years. Well, you're going to get your chance, and not behind my back, but with my blessing. Your job will be to tease him, flirt with him, entice him, even cajole him into having fun and sex. Yes, I know what you're thinking, but I have faith that you can. Michael, here is your task. You are to go on five dates. No! Don't protest. I won't accept any arguments. You will go on five dates, with my sister, or with someone else you find interesting. Each date to be a week or more apart, but all five dates to be with a four month period. Here are the rules. You both listening? Good. Each date should start at or before five PM, sooner if you want. Each date has to be different. No duplicates. Go dancing, fishing, camping, hiking, whatever sounds fun. But each date has to last at least until the next morning. Yes, you heard that right sis. On the first date, which will be yours, I expect you two to spend the night together, in the same bed, and yes that means naked. I want Michael to wake up in the morning with his arms around a woman. So yes, sis, I expect you to wake up in his bed. What you do there is up to you,but I know you sis. You've hinted more than once that you wished Michael would make love to you the way he does to me. You have my blessing. Tease him, seduce him. If you can coax him to make love to you, not just have sex, but make love to you, then I know that when the time comes he will be able to open his heart again. For that matter Michael, you have my blessing to be with anyone you want, any time you want and any way you want. No, having sex with someone other than me isn't cheating. I'm gone. I had you and now it's time for someone else to enjoy all the things that you brought to me," she said, pausing for another drink, the pain on her face lasting longer this time. I watched her sit and catch her breath for long seconds before she looked up at the camera again.

"Just so you don't think that I think this is going to be easy, for either of you, there is a reward at the end of the tunnel. Sis, you have to certify to the lawyer after each date that Michael goes on, he did his best to have fun. If he didn't, the date doesn't count. Michael, I know you will try and fake it just to get this over with, but please, for me, don't. Do your best to have fun and enjoy these dates. The whole idea is to teach you to date again and to be able to open your heart again. I know that you're terrified of trying to do that. I know you'll want to not do it because you don't want to hurt like I know you are now. But please, for me, don't hide from it. You can't feel love if you don't risk putting it out there."

I wiped my hands across my eyes, unable to hold back the tears any longer. Trish reached over with one hand and rubbed my back, her other hand rubbing her own eyes.

"Now, the reward. Remember that lottery ticket? After taxes the lump sum payment was a little over three million. Yep, that's right, three million dollars. Sis, at the end of five dates, good or bad. If he just kind of does them and doesn't try to enjoy them, you get a hundred grand. If he jumps in and tries hard, you get to have fun with him and still get the hundred grand. Do with it what you want. I know I'm asking a lot of you, so the reward should be equally large. It's not every day that a woman asks her sister to seduce her husband, but that's pretty much what I've asked. Twenty grand a date is pretty good, isn't it? Michael, you get ten grand per date to spend. If you want to fly off to the Caribbean with someone, Trish or someone else, you have the money to do it. The rest of the money is sitting in a special account. You get the money if and when Trish tells the lawyer that you completed five dates. You don't see any of the money until you convince Trish that you've had five dates that you truly enjoyed. In the surprising event that you find someone else besides Trish that you want to take out, feel free to. All you have to do is convince Trish that you had fun. Expect her to ask pointed questions about what you did and how you did it. You're a terrible liar, and I have no doubt that she'll be able to tell if you're not being honest. Trish, if he didn't get laid, I wouldn't consider it a fun date! Not for Michael. I know how sexual he can be and how visual he is. Make sure he really enjoys himself. How you get him to prove he had a good time is up to you," my wife said with a crooked little smile on her face. "I know how I'd do it. I'll just leave that thought with you. Well. I think that's it. Michael, know that I am doing this because I love you. I have loved you more than life itself. I wish we could have grown old together, but I guess the Lord has other plans for me. I will miss you. Be safe and be happy!" she said before motioning to someone off screen. The screen flashed dark as I sat there, staring, tears streaming down my face.

"That's it," the lawyer said quietly. He passed a little slip of paper across the desk to Trish. "Here's my private cell number. You can call me or text me anything you think is appropriate as these dates progress. Michael, I can tell you that your wife wanted for you to be happy. She set this up to help you. I didn't know her long, but I know you were a very lucky man," he said before holding out an envelope for me. "Here is the money for the first date. You can spend as much of it as you want," he said before standing up. "Thank you both for coming in. I'll expect to hear from you soon, Trish."

Trish and I stood up and I walked from the room almost in a daze. I didn't care about the money. I'd have traded every penny of it just to have her back again. But that wasn't going to happen. Trish drove us home in silence, pulling into the driveway and then helping me into the house.

"You going to be okay?" she asked quietly, her hand rubbing gently across my shoulders while she stood next to where I sat on the sofa.

"I think so," I finally answered, wiping my eyes once again, the memory of seeing her on the screen making the feeling of loss so real again.

"If she wasn't already dead, I think I'd kill her," she said with a chuckle.

"I'm sorry you're stuck with this. I don't know what she was thinking."

"I do. I know exactly what she was thinking," she said as she moved to sit next to me. "She was thinking that she loves you so much she doesn't want you to fade away and lose what life you have left. Just because she can't be here to share it, doesn't mean she doesn't want you to enjoy life."

"Yeah, that kind of does sound like her." I nodded, wiping my eyes again. "She didn't give me, us much time, did she? Twelve weeks."

"She knew that if she did, you'd just procrastinate. No, she wanted you to start now. She told me you'd be difficult after she was gone. She asked me to spend as much time with you as I could make. Now I know why."

"So what do I do?" I asked, feeling a bit lost.

"Well, what YOU do is find something you enjoy. Find something you would like to share with someone, maybe even something you would have shared with her. Then you invite me. If I like the idea, I say yes and we go on a date," she said with a shrug. "I can't do it for you. This is on you. You have to decide what and where and when. Then you can ask me out." Then she whispered, "But trust me. I probably won't say no. And it's not because of the money. I'd have done this for her without the money."

I looked at her feeling slightly confused. "You would?"

"Sure. How could I not?"

"I don't get it," I whispered, shaking my head, still not understanding.

She chuckled, a soft feminine laugh. "Oh, Michael. I've listened to my sister brag for years about how wonderful you are, how happy you can make her, how... how wonderful you can make her feel, just by touching and holding her. Two failed marriages have taught me an important lesson. Not all men are Michaels. Some are just selfish, self-absorbed assholes that think of women as just someplace to stick their dick. Not once in all the years of dating and marriage has anyone made me feel like you made her feel. Even if it's only five dates, why would I ever pass up the chance to see if I can feel that?"

"But you're my sister-in-law," I said with a frown. "She wants me to date you, but I've spent the last thirty years trying NOT to look at you that way."

"That way? What way is that?"

"Come on. You don't remember last June? When we went camping at the lake for the weekend and Nancy invited you along? What did you wear the whole weekend?"

"Oh, that. Yeah. That little yellow bikini. That was after Marco broke it off. I was feeling a little...."

"Yeah, less than desirable. I know. She told me to just be me."

"Just be you?"

"Yeah, you know. Just be a guy and enjoy the view?" I said, thinking back to how good she actually had looked in that bikini and how hard I spent almost the whole weekend. If Nancy hadn't agreed to have sex with me, quietly of course, in the night, I doubted that I'd have made it through the weekend, not with both of them showing so much cleavage and butt.

"You did seem to have a pretty big hardon in your shorts every time I looked at you. I don't know how you managed to not have one when we went swimming."

"That's easy, someone jacked me off under the water before I got out of the lake," I said with a chuckle, remembering how Nancy had teased my dick out of my suit and played with me while we floated in the warm water until I couldn't help but unload.

"That explains it." She nodded, looking at my lap. I looked down and couldn't help but notice how much of a bulge even our short discussion had caused. "Maybe that should be our first date? Going to the lake?"

I thought about it a few moment. "Maybe. It's hard for me NOT to have a good time at the lake."

"Have you even gotten the boat out this year?"

"No," I admitted, which was unusual for me. It was almost August and the boat was still winterized.

"Then let's make that date one. This weekend. Do you want to play for the day and them come home, or camp overnight?"

"Oh hell. I don't know," I muttered, trying not to think about going with Nancy and having a horrible time not thinking about it.

"If we camp, we'll have to get more stuff ready. Saturday isn't that far away," she said quietly, lifting her hand to my back again to rub across my shoulders. "Want a hand?"

I turned my head to look at her for long seconds. "You don't have to do this. I mean, all you have to do is say you enjoyed the date and you'll get the money Nancy promised," I said quietly.

"I could. But that wouldn't be fair. Besides, Nancy knew exactly what she was asking, of both of us. I'm not about to dishonor her attempt to help you by cheating on this. Hell, it isn't the money. It would be nice, but I'd do this just because she asked me, and of course to get into your pants." Then she whispered, "Now, what do we have to do first?"

"I guess see if the boat will run," I said with a shrug. "We still have a few hours of daylight."

"Good. Take me home and show me what to do."

"Well, first thing when we get home is to get changed. I don't think we want to go work on the boat dressed like this."

"No probably not," she said, looking down at her own dress. "I Don't think I have anything here to wear though."

"I'm sure I can find something for you at the house," I said, as we walked out to the car. We got to the house and she followed me inside.

"Why don't you find something for me to wear. Maybe something old that Nancy didn't wear any longer? I'm going to go to the bathroom. If you hand it in, I can change in there."

"Sure," I answered as she headed to the bathroom, leaving me to stare at my wife's dresser. I hadn't opened these drawers since I had to find clothes for her burial. I pulled open the drawer that I knew had t-shirts and shorts in it. I dug down, not wanting to use anything Nancy had worn recently, and found a few shirts in the bottom that looked like they'd work, shirts with no real logos or anything that might remind me of her. Shorts were easier. I found a pair of nylon running shorts I bought for her for Christmas years before, shorts that she simply refused to wear because she said she didn't want to feel exposed while she was running, she wanted to feel comfortable. Admittedly, I bought them specifically because I thought she'd look sexy running in them. I pulled them out along with the plain gray t-shirt and knocked on the bathroom door.

The door opened part way and Trish held a hand out. I couldn't help but notice that I could see her in the mirror, her entire back bare except for a small amount of white underwear covering her butt. I didn't have much time to enjoy the view before the door closed again. I walked to my dresser and pulled out a pair of shorts and t-shirt for myself. It only took a few moments for me to undressed stripping everything off except for the spandex briefs that my wife loved me wearing. I workd quickly, somehow nervous about her seeing me mostly naked. Nancy always enjoyed both how the briefs made me look while I was undressing, and also how they felt when she got playful. As a result, that was pretty much the only thing I had for underwear in my dresser. I turned around to where I'd set the shorts and shirt on the bed and looked up when I saw movement.

"Don't let me stop you," Trish said as she leaned against the frame of the now open bathroom door, her arms crossed over her chest, her legs bare below the very short nylon shorts. She stepped away from the doorway into the bedroom. "After putting these on and realizing just how much they show, I didn't figure you'd mind giving me equal billing."

"Equal billing? " I asked as I quickly picked up the shorts off the bed and held them in front of my crotch, which gave every indication of starting to suddenly harden and bulge out the front of the snug-fitting underwear.

"Uh huh," she said, looking down at the shorts and gently swiping her hands back and forth across the legs of the shorts, which clearly exposed the crotch of the small white panties she wore under them. "Good thing I was wearing underwear today, or you'd be seeing a whole lot more of me."

"Wearing underwear today?" I said quickly, before I even realized what I was asking.

"Sure. I don't always wear underwear. Sometimes I go without, just to feel sexy. Something I picked up from Nancy years ago. She used to go without all day when she was planning on teasing you later in the day. She said going without made her horny and less inhibited. That way she could flash you without being too nervous. How else do you think she got up the nerve to expose herself to you in the movies or in the car?"

I looked at her in surprise. "I just always thought she took them off when she got home from work."