Helping the Widow

By the middle '70's my life was good. I had a great job with a Fortune 500 company and a promising future. I was able to purchase a townhouse in an upscale part of San Antonio. While most guys my age were running around in sporty cars I chose a Town Car to better handle my 6'3", 240 pound body.

I had dated several young ladies even enjoying a few "sleepovers". But I really wasn't looking for anything long term because, frankly, I enjoyed the freedom I had.

One of my neighbors in the complex was Elizabeth Hughes, better known as Liz. She was a fifty something widow who had downsized to her townhouse when her husband, Dale Hughes passed away four years previously. Mr. Hughes had owned a car dealership for many years and had left Liz well off.

Liz was 5'6" tall and weighed a well proportioned 130 pounds. Courtesy of her hairdresser, she had short blond curly hair, was always immaculately made up and dressed very expensively. I imagine Liz was a knockout as a young woman and had aged well. She visited the gym at the complex three or four times a week and maintained her shape very nicely.

Liz and I had developed a bit of a friendship while at the gym and in conversations in the complex court yard.

When I was out of town Liz would collect my mail and hold it for me until I came home.

Returning home from a trip one evening I went to Liz's house for my mail. When she came to the door it was obvious she had been crying. I said "Liz, my goodness, what's wrong?".

She shook her head and said "It's nothing.".

I said "Well it's something, what is going on?".

Liz slumped onto her couch and began crying. On the coffee table were bills, notices and receipts all jumbled together. She said "I don't know what has happened. I know I have plenty of money but I keep getting late notices and phone calls. I even got a call from Nieman's threatening to close my account.".

I asked Liz if she would like for me to take a look and see if I could help.

She said "I don't want to bother you with this, I know you are a busy man.".

I told Liz if she didn't mind my looking at her personal information I would help. I told her to get her checkbook and bank statements. When she gave me what I asked for I went to work.

After a couple of hours I had her checkbook balanced and checks written for her signature that would get her caught up with everyone. It was obvious that Liz was running through her money at a dangerous rate. Shopping sprees, expensive meals and frequent trips were draining her accounts. I told her she needed to slow that down.

She said "I know but Dale always took care of the money and he didn't seem to care how much I spent so I have developed some bad habits.".

As I was leaving Liz patted my shoulder and thanked me for helping. I said "You're welcome just watch your money a little closer.".

Three weeks later Liz and I were at the gym and I asked her how her money management was going.

She said "Not great, I got two late notices on bills I didn't know I had.".

I told her I would drop by that evening to take a look. She said "I would appreciate it.".

After a few minutes of looking at her records I leaned back with an exasperated look on my face. Liz asked "Is it bad?'.

I said "Yes, you have checks missing but not recorded, you have bills that are late again and I see receipts for some serious shopping. This just must stop, you are going to go broke.".

As I was leaving I saw one more receipt sticking out from under a magazine on the coffee table. I picked it up and saw it was for 2100.00 to a furrier in Dallas. Not believing what I was seeing, I said "Liz, a 2100.00 fur cape? In San Antonio?".

Liz could see I was angry and said "I told you I had some bad habits.".

I said "Well we're going to start breaking them right now, I grabbed Liz, tucked her under my left arm and swatted her bottom about fifteen times.".

Indignant, Liz said "Why did you do that?".

"Because that's what happens to spoiled brats."

Liz yelled at me to get out, so I did.

A few days later at the gym, Liz came to me and asked if I would come by for coffee that evening. She said "I owe you an apology and would like to talk.".

Assuming I would again be balancing a checkbook, I told her I would come over after work.

When I went to her house Liz and I sat at her dining table. She said "I was wrong to yell at you. You took me by complete surprise by spanking me and I didn't know how to react. I need your help until I can get the hang of managing my bills. If you agree to help me I will agree to getting spanked when I go off track. I have been spoiled all my life and I need to change that.".

Wanting to help my friend and not just a little excited about having her over my knee, I agreed.

The next two times I went over her expenses, there was very little wrong. Certainly nothing that was a spankable offense. I praised her and she seemed to bask in the compliments.

After a month I checked on her and was confronted with a disaster. Not only did she not record her expenses, she had several unpaid bills and I discovered she had treated five of her friends to a very expensive night out.

"God damn it Liz", I yelled "Did you just forget everything we talked about?".

She played with her hands and said "I got behind and couldn't figure out how to catch up.".

I crossed my arms and stared at her.

Liz said "I'm going to get a spanking aren't I?".

"Unless you would rather I leave, yes"

"Don't leave."

I pulled out a dining chair and told Liz to come . I said "Liz you are going to be spanked for not keeping up with your money and for not telling me when you got behind. Do you understand?".

She slumped her shoulders and nodded her head.

I guided her over my lap and scolded her for her behavior. I began smacking the seat of her designer pants hard enough that she kicked her legs and cried. After a good ten minutes I told her to stand up. When she started to move away I said "No, we aren't finished.".

With that I unbuttoned her slacks and let them fall to the floor. Liz turned beet red and said "Oh God" as I put her back over my lap..

I spanked her very expensive panties for another ten minutes, When I finally let her up she reached to pull up her slacks. I pointed to her panties and said "If I have to do this again, these are coming down.".

Mortified, Liz ran from the room.

When she came back, she had a different attitude. She asked me if I would really spank her bare bottom. I assured her I would.

She leaned into me and said "If I asked you to do it now would you?'

"You want me to spank you again?"

Liz became like a coy teenager and said "When I thought about your hand on my bare behind I actually became aroused. I don't understand it, the spanking hurts, but I was excited for the first time in a long time.".

I hugged Liz close to me and said "If that's what you want, ask me.".

She snuggled close and whispered "Please spank my bare bottom.".

I sat down on her couch and said "Liz, remove your slacks.".

With trembling hands Liz unbuttoned and unzipped her slacks and stepped out of them. Then I said "Liz, remove your blouse.".

Liz was not expecting this and hesitated before following my direction. She was actually shivering and it wasn't cold.

Maintaining control I said "Now your bra."

She said "Why?".

I simply said "Because I told you to."

She reached behind her and unfastened her bra holding it over her breasts a moment before dropping it to the floor. She had an amazing body for an over fifty woman.

I patted my lap and Liz crawled over it with her face buried in a sofa pillow.

I put my hand on her butt and said "Are you sure this is what you want?".

She nodded her head yes.

I took my time taking her panties down and then rubbed her bottom before spanking her fairly gently for several minutes.

While massaging her ass, I said "Enough?".

She shook her head no so I swatted each cheek six times hard. Her cries were muffled by the pillow.

Liz was very wet between her legs. I took the panties completely off and told Liz to spread her legs.

I rubbed around her pussy and worked a finger in and out to the motion of Liz's hips rising and falling. Finding a firm nub I rubbed it and pinch it until Liz's legs went stiff and her hips jerked as she screamed into the pillow.

When she had regained some composure Liz cuddled up next to me still naked. She kissed me and at the same time unzipped my slacks and extracted my dick.

She took me in her mouth and squeezed my balls until I shot my load in her mouth. Not knowing quite what to do, she swallowed it.

Liz gathered up her clothes and went to her bedroom. When she was dressed she shyly sat down next to me.

She said "My ass hurts. But I hadn't had an orgasm in ten years so I guess it was worth it. We must do this again sometime.".

Over the coming months Liz got her financial act together but would "mess up" just enough to get a spanking and sex. She said I made her feel 20 again.

Then, a transfer to LA. I introduced Liz to my financial adviser. I was sure he could keep her solvent. I didn't think he would spank her.