second chances (closed)

I swear, I did everything I was supposed to do.

I was second runner up for Miss Teen Alabama, and that spring, I met Ray. He was old as dirt, but he had a brand new BMW and he wanted to take me down to the shore. He promised he just wanted my company, and it wasn't anything to be ashamed of. So I went, and I played it right. I didn't put out for him. I kept him drooling after me the whole week.

By the time I graduated High School, I had a 2k diamond ring on my finger, and we were married in July. We spent our honeymoon in Cancun and, thanks to a big bottle of little blue pills, we fucked like rabbits every chance we got.

In ten years we had our ups and downs, but that's normal, right? I didn't do what some girls do, I never let myself go, and I kept him satisfied. He said college was a waste of time, so I stayed home, went shopping, wrote checks to animal shelters and generally lived a nice, comfortable life. So maybe I wasn't quite in love with him. We had a good thing.

It really broke my heart when he died. It was a stroke, he was driving, and by the time they got him out of the car, he was a vegetable. A week later, he passed. That was when I found out we were broke. He had borrowed for everything, and had been running scams that made my head spin to keep it all from falling apart. The banks were taking the house, the cars, the money, everything. I had to hock jewelry for a fraction of its worth just to put a deposit on this crappy little apartment.

I'm not out, though. 28 isn't 18, but it's not 30 either, and I know I still look good, and that's got to be worth something. The thing is that guys have changed in ten years. I'm not a cute teenager anymore. I can't hold out for the ring. So I put myself out there on a few dating sites, hoping something good will happen. I didn't know what to say, really, so I hoped my pics would speak for me.

"28f seeking single man for committed relationship. I'm in great shape, and I love to dance, have fun and try new things. No druggies or drunks. Steady job a must.

Heya. My name is Buddy Orr, and I have spent the last six years building an insurance business along the Alabama / Georgia border. The first two years right after college (Roll Tide!) were tough. Shit that first month I had a bring home pay of $27.64. Between building a business and trying to meet my financial obligations wore on me and I ended up working 70 hours a week, if not more. Depending if I worked both Saturday and Sunday instead of one or the other.

Then one day I looked around and had a staff of three working full time for me and I no longer had to work weekends.

Heck I even take Friday afternoons off now.

It was one of these Friday afternoons when I saw the ad on a popular dating site. Yes I use a couple. It made things easier when I was working. He'll I am only 28 after all; and, every guy my age has needs that need to he addressed, and for the most part porn and masturbatory acts only take the edge off. It doesn't bring real satisfaction.

Staring at the close up, I could not believe it was her: Alison.

As I read the ad I laughed. The bitch was flat out looking for a sugar daddy. I muttered, "I got your Daddy right here," and decided to answer the ad.

I have a good business and know how to take care of my lady. I have more time and money than I have hobbies can you fill that void?

​

I hit send not knowing if she would respond or not.

She had run out on me 10 years ago during our last year of high school with some old dude. Maybe he divorced her? Who knows, all I was sure of was that the intervening decade had not been unkind to Alison.

I have a good business and know how to take care of my lady. I have more time and money than I have hobbies can you fill that void?

Well, so far he sounded perfect. The profile didn't give much information, and didn't have a pic, which was a little disappointing, but to be fair, I wasn't going to be picky. By the time I met John he was pudgey and bald, and you had to really look to see the good looks he'd had as a younger man. I hadn't married him for his looks, and if sometimes I fantasized about a different man taking me, I had been happy with my situation. I even joked with my friends that I was pretty enough for both of us.

In a better world, I'd have taken some time to get used to the whole concept of internet dating. Everyone said you had to be careful, there were predators out there. Maybe he was one of them. Maybe he wasn't, and I didn't really know how to check him out. I'd only ever dated a couple of guys that I went to school with before I met John, so I'd never had to do that kind of thing.

Now my back was against the wall. If I sold off the jewelry and clothes I had managed to get away with, carefully, I had enough to stay in this shithole and live like a peasant for maybe a year. Maybe I could find a job in that time, but after a few weeks of looking, I wasn't hopeful. Im 28, no college, no experience, and I was too pretty. Every woman I talked to about a job hated me, and every man wanted to fuck me. I wasn't going to spread my legs to get a job. At least, not the jobs they were offering.

It left me in a tight spot, and maybe this guy was the way out. The only way I could think of to decide was to meet him, get a feel for him. Maybe he was my white knight.

"I'm Alison," I typed. I thought. I wanted to find out if this guy was for real. I was getting a lot of messages, though most of them were pretty vile suggestions for a first date. This was the only guy who seemed to have any possibility, and I wanted to see if there was any hope at all. "I'd love to meet you and see if we hit it off. Do you know Bahama Billy's down in Gulf Shores?"

It was a little 50's style seafood shack, where you order from a window and sit at a picnic table under an awning by the beach. It had survived when the big resorts sprouted up around it by giving people good food at good prices, and it kept the big hotels from blocking the way to the beach. John and I had eaten there a couple of times when we spent that week there when I was still in high school, and I had good memories.

It was also a couple of hour's drive, which meant it would be unlikely he would want to meet there unless he was serious.

I had to smile. How desperate was Alison if she wanted to meet so fast, without so much of 'What is your name?' Was the poor thing really in such dire straits?

"Guess it is time to find out." My heart started to race a little. The feelings of when I was a teenager came back in full force. Alison was about the only girl I had ever wanted and she had run off on me.

I replied:

Yes I know it pretty well. Tomorrow night at 6:00PM for dinner?

I will flag you down when you arrive.

Unless you would rather meet tonight someplace a little closer. In which case how about at the Casino at 7:00? My treat to a buffet.

​

I hit send on the reply and brought up one of the popular online booking agencies and looked for a hotel room for tomorrow night. I found one a couple blocks away from Bahama Billy's with a Gulf view. I thought what the hell, even if I didn't score Alison, I would at least get a good night of sleep near the water.

I also checked the Casino to see if they had any rooms available, just in case, and it appeared they were booked completely full. Shrugging it off, I figured if I got that lucky tonight, I could always bring her home, or to a motel not far from the Casino, of which there were several.

I went to my work out room and hit the stationary bike for about an hour while waiting on a reply.

I came back from run, missing the private gym and pool I'd had at John's house, and found my mystery man had replied already. He hadn't told me his name, which was cause for a little concern, but I shrugged it off. The other messages I'd received were a pic of a sad little cock and a simple question: "u like 2 party?????? 3::::::::~~~ O-:" I blocked both accounts and thought about the reply. Gulf Shores tomorrow or the casino tonight?

If we went down to Gulf Shores for dinner, he'd probably expect me to spend the night with him. After all, it was a long way, and a long way back. Just because I had time to kill, didn't mean he did. He'd think it was a big waste of time if he didn't get something out of it. Specifically, a nut. I didn't want him annoyed, but I didn't want him thinking I was so easy a fried seafood plate was all it took to get me into bed.

"Yeah. Casino's probably a better idea. See you at 7. You think you might send me a pic or tell me your name, or you want to stay all mysterious?"

I had a little time, but I had a lot to do. Shower, hair, nails, make up, etc etc etc. Then I had to figure out what to wear. It was all part of the bargain. It was a buffet, not exactly fine dining, so I didn't need to dress up too much. After several changes, I settled on my good jeans, that rode low on my hips and hugged my ass without carving too deep between my cheeks. High heeled sandals, to show off my pretty pink toenails. A white silk t shirt with a deep v neck showed a nice amount of cleavage, without flashing my bra. I looked in the mirror.

I looked good. I looked right. It was time to go.

My F-type had been repo-ed, so I had bought a reliable, used car. There's a special horror that I felt every time I got in, like someone might see me. When the best thing you can say about your car is that it's reliable, you don't want anyone to see it. I hated it, but it fit my new life perfectly.

I started my pop playlist as I drove towards the casino. Hopefully, Pharrell would convince me I was Happy by the time I got there.

After the hour ride, I checked my emails and saw her response about the casino and wanting a photo. I looked at the clock and had plenty of time to do it, but why should I? Giving up the photo now might spoil the surprise, and I wanted to know if she would remember me.

Which I doubted.

I replied:

And give up the surprise? A guy has to keep his secrets doesn't he? See you at 7:00

​

I shaved, showered and dressed in a pair of slacks and a polo shirt. I left the house around 6:00 to ensure I was there on time and lounged out front by the doors waiting. When I saw her, I couldn't wait any longer and walked up to her, "Hi Alison, remember me?"

I parked a short hike from the front doors, because I didn't want him to see me getting out of the car, and I was just about to go in when someone called me by name.

"Hi Alison, remember me?"

I turned to see a guy in a polo shirt smiling at me. He was roughly my age, a little thick at the middle, but not in bad shape. I shook my head slowly. He looked kind of familiar, like when you know you've seen an actor in a different movie but you can't think what it was.

"Not exactly," I said. I glanced at my watch. Quarter past seven. My guy was probably inside. "I'm meeting someone, actually, so...." I look at him again. "Unless you're mysteryman00766?"

I gave her a half smile and replied, "At 7:00 I was yes. At 7:15, I am not so sure."

I stood there and crossed my arms, asking, "Are you always late? Hasn't anyone take the time to teach you that punctuality is important?"

Not nice to see you. Not you look good. Not sorry about the mystery, my name's <whatever>. None of that.

Instead, he was getting an attitude about fifteen minutes? As if they were going to give away our table or something, at the buffet.

"I apologize for wasting your time, whoever you are," I said, all hint of warmth gone from my voice. I turned and started to walk back to my car.

I called out, "Alison, wait!"

I walked up and said, "Listen, I have waited ten years to see you again, and I was miffed you didn't remember me."

Catching up, "I had chased you around high school for three years, asking you out almost every week, and the week you seemed to be most inclined to say yes, you went off with your husband."

Not knowing if I was understood fully, "I am Buddy Orr. Let's go eat, talk, and reminisce. See what happens "

I don't stop, but I slow down. Then he says he's been waiting ten years, and I turn to look at him again. My annoyance is still burning hot, but I do want to know what he's talking about. Why would I remember him. I study his face, thinking as he's talking to me. High school? Asking me out? A lot of guys asked me out in high school, but only a couple with any kind of persistence. This guy wasn't black, so that meant he could only be....

"Buddy Orr?" I say it at the same time he does. Suddenly I see it. He was one of those guys whose body didn't do them any favors as a teen. He was a shrimp, until junior year he shot up, and spent months looking like a scarecrow as his weight caught up to his height. It wasn't until senior year that he really looked like a person, and by then I wasn't really looking at high school guys anymore.

I walk back to the doors, shaking my head.

"Did you know it was me when you replied to the ad?" I ask, smiling.

I nodded while saying, "Yeah, that is the only reason I responded."

I held the door open while Alison walked in giving me a perfect view of her tush, which seemed to have only gotten better over the years. To be honest if anything she looked better over all. She was still tight but now womanly instead of girlish. Time had been very good to and for Alison, at least physically.

The casino was smokey and full of people from blue hairs to twenty somethings like Alison and I. For a second I thought that maybe this wasn't the best first date of all time at least as far as location went. The exception to that would be the buffet which was as good or better than most sit down restaurants.

We got into the line for the buffet and I asked, "How have things been? Did you and your husband have kids?"

As we stood in line for the buffet, he started with small talk. It was only fair, I supposed. He had been a good guy all through high school, and I had never really given him a chance. I had never been bitchy about it, but I'd never really thought of him as a potential boyfriend. More like a lost puppy. I tried not to think about my situation, and how I was the lost one now.

"Yeah, no," I said. "He had a couple of kids from his previous marriage, so...." I didn't need to tell them that his kids were all older than me. That they hated me. I gave him a smile.

"So what about you? I haven't really stayed in touch with anyone from home. What have you been doing with your life? Did you ever settle down?" Now that we were here, now that I knew who the mystery man was, it was actually nice to see him.

I shook my head, "No, I have been too busy to bother with a family. After attending Alabama I started an insurance business which is doing well now."

I shuffled from foot to foot for a second then continued, "Most of my dates come from one online service or another. Sometimes they work out for a while, mostly though they are one and done."

I glanced around a moment then asked, "What made you post online? "

I looked at him and took a deep breath. I could have given him a bullshit answer and seen how things go for a while, or I could just be straight with him. I let out a sigh. I'd never been a very good liar, and there was something about the idea of Buddy Orr coming to my rescue that just struck me. I couldn't say why, unless it was just that he'd been waiting twelve years to date me.

"I was married for ten years," I said. "He passed a few months ago. He never wanted me to work or go to college, and I thought he was going to take care of me for the rest of my life. But there was nothing. Everything we had got taken by the banks."

I knew how it made me sound, but I also knew that for some men, this would seem like a golden opportunity. I was still beautiful. I felt my eyes tearing up at the thought of what I was about to suggest.

"I'm lonely and I'm in a bad spot," I said, my voice a little choked. "I really need some help. I was always a really good wife." I look up at him, hoping he understands.

Looking at her I could tell that Alison was in a bad way, worse she appeared lost and scared. A bad combination for anyone our age. By now we should have our shit together a little better than Alison did.

But then, she had been a kept woman for all her life. First her parents then Ray, she never had to live alone until lately.

I reached across and placed a hand over hers, giving what comfort I could to her. "Damn Alison, how can I help?"

I shook my head and sighed. This was happening way too fast. He was being sweet about it, but I wasn't kidding myself into thinking that he actually wanted to take care of me. I'd hoped I'd have a little more time to get his interest, but maybe I had lucked out. Maybe Barry was still a little obsessed.

"I don't know," I say, a little breathless, looking across the table at him, hoping he would be my white knight. "I'm stuck in this tiny little apartment, and I can't even afford that. I'm selling off jewelry to pay the bills, because nobody wants to hire a 28 year old woman with no education and no experience. I just need someone who can help out while I figure something out."

I sat there kind of dumb struck. Was Alison asking me to be her sugar daddy? The more I thought about it the more it had a certain ... appeal.

What was I thinking? She looked good that is God's truth. But could she fuck? Could she hold a conversation? Did it matter to me?

Honestly it did. What was the point of being with someone if there was nothing to spend time on? Yeah maybe we could screw our brains out day and night but a guy has to recharge.

I could though give her something. ..

"Tell you what, for the time being if you want to earn some cash, you can work for me."

I could discern exactly what went across her face, but, I said, "It is a temporary thing. Until you find what you are looking for. In the meantime I can help with the rent and whatnot. "

It wasn't what I had been expecting, exactly. Then again, I hadn't really expected Buddy Orr to show up, either. I'd expected to go out with someone on a few dates before having this conversation, though. They'd see me and want me, and when they saw how I was forced to live, they'd want to be the white knight. Instead of that, I had Buddy offering me help, and work.

Maybe that was better. It was what there was, though.

"That's really sweet of you," I said. "I don't know what to say except thank you." I smiled at him, and then I gave a little giggle. "And yes. I accept, gratefully."

Then I looked down at my plate. I'd hardly touched my food, though it was good. I took a bite of the salad I had made for myself and as I chewed, I thought. I thought Buddy and I probably needed to put the past to rest.

"I know it was a long time ago," I said. I tried to keep it light. "But I feel like I owe you an apology. I know you had a crush, and I think you asked me out about a hundred times, and you were always nice about it. I never appreciated that. I was in high school. I was shallow. If I knew then what I know now...." I shrugged. Who knows what would have happened, but that kind of devotion is almost unheard of. For a moment, I wondered if he still had those feelings for me, but I shook my head. Even I can only be so full of myself.

I sat there a moment and then said, "Yeah, it was a long time ago. I am not the puppy dog I once was. I discovered somethings about me along the way which changed how I view a lot of my life, especially relationships."

I looked down at my food and took a bite and mulled things over while chewing. "One thing I have learned is to take things as slow as possible, but not artificially so."

I shrugged, "It is a fine balance one has to strike."

I grinned at her and mused, "But you are still pretty enough to make a man puff up in pride."

I blushed. It was a sweet thing to say and more to the point, it was what I needed to hear. A man who wanted to show me off would want to show off for me, and that would mean making sure I was taken care of. I hoped.

"I didn't mean to say you were a puppy...." I shrugged. Of course, that was exactly how I'd thought of him back then. I thought about what he said, and wondered who had hurt him. Someone had. Men didn't want to take things slow unless they were afraid of something.

I reached across the table and put my hand over his.

"Buddy," I said. "We can take it any way you want it. We're both different people than we were back then and I'd like to get to know this you." I smile. "And if I can make you proud along the way, it's my pleasure."

What the fuck? Am I 18 years old again? One simple touch from her and my cock rises to the occasion like it was a once in a lifetime occasion. But the warmth of her hand seeped into mine and up my arm down my torso, feeding the already ravenous cock that was throbbing in my pants.

Something about the way she said 'it's my pleasure' resonated deep inside me and I wanted to hear it again.

I said, "I am positive you will."

Looking at her, her pale eyes seemingly drawing me in, I asked, "Tell me about the time you have been away. Were they good years?"

I nodded, a lump forming in my throat. They had been good years, but the man my life had revolved was gone. It wasn't love, I guess, but it had been comfortable and safe.

"The best," I said, hoarsely. I bit my lip and looked down at his hand. Would he take care of me the way John had? Could he become the center of my world? I looked into his eyes and gave the slightest shrug. "Sorry. I'm still getting used to, you know, being a widow."

I gave his hand a gentle squeeze. He wanted to know what had happened.

"We got married about a month after graduation, and then I was his wife. It was amazing. Like being a princess." I shook my head. "But somewhere along the line, things got fucked up. He knew his way around finance, so he was able to keep up appearances, but as soon as he died, it all fell apart."

"It was good while it lasted." I smiled. I didn't want to scare him off, and who knows how he might react to my story?

I nodded sympathetically as she told the story; I had heard a variation of it maybe fifty times in the last few years. A good life policy would have prevented Alison's pain, or at least the monetary part after his death.

I looked up and said, "Well that did bring you back to me after a decade, which, sadly and happily, is good in my estimation. " I knew there was no real easy way to say that, and a smarter guy probably would not have, but then, who ever said I was smart?

I looked across at the casino and asked, "A game of chance or two? "

The last thing I needed was to throw money away gambling. I had some jewelry and some couture left, but I was only getting a tiny fraction of what it was worth selling it online. It wasn't going to last me for long, and when it was gone, I'd be up against the wall. Still, Buddy seemed like he wanted to help. The more fun we had together, the more likely he'd be to want more. The more he wanted, the better my chances. So it wasn't gambling so much as investing.

"Sure," I said, giving him a shy smile. I probably should have agreed sooner, but it wouldn't hurt for him to see that I needed it.

I walked close beside him as we went to the tables.