Alana loved making me do things that I knew I shouldn't do but couldn't resist doing for her. I went into work one Saturday afternoon to try and catch up on some paper work, but as I sat at my desk and fumbled through file folders, I couldn't stop thinking about her, so decided to give her a quick call.
"It's so nice to hear your voice, Daniel,” she said when she realized it was me.
"I hope I'm not interrupting anything,” I said quickly.
"No, not at all, just doing a bit of house cleaning and laundry. What are you up to today?"
"I came in to work to do some paper work,” I told her, “but I can't seem to concentrate on it."
"Why is that?” she asked.
I blushed. I knew there was almost 20 years between us but she was the most beautiful older woman I had ever known.
"Because I was thinking about you."
"And what happens when you think of me?” she asked.
The blush on my face got a deeper red.
"I get hard."
She chuckled to herself.
"Are you touching yourself, Daniel?"
I loved the way she called me by real name instead of the stupid nicknames my immature friends made out of it.
"Yes ma'am. A little. Just through my shorts."
"I want you to do something for me."
"Okay. Anything."
"Unfasten your shorts and pull them down to your knees."
A short gasp escaped my throat.
"Right here? Right now? In my office?"
"Yes. Right there. Right now. In your office."
"What if someone comes in?"
"Then you should get up and lock your door, shouldn't you?"
"Yes ma'am."
I quickly got up to lock the door and then returned to my chair and my phone call with her.
"It's locked."
"Then do as I asked you to do."
I blushed again.
"Yes ma'am."
I unfastened, unzipped, and pulled the shorts to my knees.
"They're down."
"And what are you wearing under them?” she asked.
"Boxers."
"I want you to pull the boxers down."
I gasped again.
"But ma'am,” I said, lowering my voice as if someone else could hear me,” then I'll be bare from the waist down."
"Yes, I know that, Daniel. Now do as you were told."
"Yes ma'am."
I quickly looked around to make sure no one could see me, then put my thumbs in my waistband and slid the boxers down to meet the shorts. The leather of the chair was cold on my bare skin.
"They're down."
I could feel her smile through the telephone line.
"Do you feel like a naughty boy when you do things like this for me?” she asked.
"Yes ma'am, very naughty."
"Do you know what happens to naughty boys?” she asked.
I could feel the muscles in my body tense up. I knew exactly what she was about to say.
"No ma'am."
"Naughty boys get their bare bottoms spanked,” she said as-a-matter-of-factly.
"They do?"
"Yes, they do."
"But ma'am, I'm a grown man. I'm twenty-five years old. I'm too old for a spanking."
"No, you are not too old,” she clarified.
"May I ask how you would spank me if you were here right now?” I asked.
"If I was there right now,” she said, “I would make you stand up from your seat, I would sit down, I would put you over my knee, and I would give you a long, hard bare bottom spanking just like I did to my sons when they would misbehave."
I felt a tingle go through my body and I swear I could feel her breath on the back of my neck.
"Would you stop if I started to cry?” I asked.
"No, I would not. I wouldn't stop until your bottom was the shade of red that I wanted it to be."
I couldn't resist. I couldn't hold back. I wrapped my fingers around my naked cock. A moan escaped my lips.
"What are you doing there, Daniel?” she asked.
"Please don't be mad,” I whimpered, “but I had to touch myself."
I heard her sigh.
"What am I going to do with you?"
I chuckled.
"Blister my bottom?"
She laughed.
"Among other things."
I stroked as she told me how, after catching one of her sons smoking when he was a young teen, she had made him come to her bedroom and lectured him on the evils of cigarettes. She said it wouldn't have been so bad until he started back talking to her and she began to get madder and madder.
"What did you do then?” I urged as I continued to caress.
"Well,” she said, “he had on a pair of elastic waist sweat pants, so I jerked them down, whirled him around so that he was bending over the end of my bed, and I began swatting the daylights out of him.” She stopped and giggled. “He never expected that, so I had gotten several good swats in before he even realized what happened. I think being bare bottom in front of his mother at that age was better discipline than the spanking. Much more embarrassing."
The story was too much for me and my orgasm erupted, the cum flowing out of the head of my cock and over my hand. As much as I tried, I couldn't keep the moan from coming out and being overheard by Alana.
"Daniel?"
"Yes … yes ma'am?"
"What just happened there?"
"I … um … I came. I'm sorry. I couldn't help it."
She chuckled.
"I know."
I was taken by surprise.
"You're not mad?"
"No, I'm not mad. I know young men get aroused easily."
"Thank you, ma'am,” I sighed my relief.
* * * *
As Alana and I got closer, our desire to meet increased. I felt like I knew every thing there was to know about her; from the color of her eyes to the first pet she had as a child. I told her everything about myself, not wanting to keep any thing from her. I had never wanted to be this close to anyone, not even girls my own age, and actually meeting in the flesh was the next step.
We decided to get together at a public shopping center at a popular coffee shop. I got there an hour ahead of time and made several trips to the men's room to check my hair and pop a breath mint, and was never really satisfied with a stray lock that kept falling down on my forehead.
I recognized her when she walked in the door. She was beautiful … poised … graceful … every thing a young man would want in an older woman. She had fluid curves, softened and rounded by time, and not sickeningly stick thin like most of the girls that I knew tried to be. She was dressed in a silk blouse, black skirt, high heels and stockings as if she were going to work, so I assumed our meeting was going to be a short one. I stood up and when she saw me, she smiled and walked straight to my table.
"Good morning, Daniel,” she said.
"Good morning, ma'am,” I replied, my heart beating so fast that I was sure that she could hear the thumping.
"I hope you didn't have to wait long."
"No ma'am, not long at all. May I get you some coffee?"
"Yes, please. Just a small decaf with one sweetener."
"I'll be right back with it."
I ordered myself a hot chocolate and came back to the table with the two cups.
"You're even prettier in person than you are in your pictures,” I told her.
She smiled.
"Thank you, sweetheart, that's very kind of you to say."
We chatted over our drinks for a while and then I asked her if she was going to work afterwards.
"No, I took the whole day off."
I was surprised.
"Oh, okay. You looked as if you were going to work."
She smiled.
"Well, if you will remember back a few weeks, you asked me to wear what I wear to work if we ever met. So now we are meeting and this is what I wear to work."
I chuckled. It was coming back to me then.
"I had a brain flicker, I guess."
"Or a testosterone surge,” she giggled.