Educating Pam

Writers note: This is the fifth chapter of my story about an affair I had 8 years ago. All the events here actually happened. Things did get a little more interesting in this chapter. And as with the other chapters, there is some bathroom play in here as well. But that was part of our fun. I do appreciate all the comments received.

T

*

It was the morning after I had introduced Pam to the pleasures of anal sex and I had this feeling that talking with her on ICQ was going to be very entertaining that morning. Was I ever right!

She came on-line, but instead of her usual long kiss, "My heiny is sore!"

"Poor baby," I replied, "what happened to it?"

"Some man stuck his dicky in there!" she wrote back.

"Twice if I remember correctly," I said.

"One and a half times," came flying right back, followed by, "my poops are sliding out real easy too!"

I laughed so hard that people a block away could probably heard me.

I said, "it will be all better by tomorrow," and sent a smiley.

She replied, "you should come over and kiss it to make sure!" and sent a smiley back.

"I guess this means you will let me do it again," I wrote.

"ONLY if you ask very nicely," was her reply and followed another smiley.

Before I could say something back, she wrote, "maybe I should get one of those strap-on dildo's and do yours sometime. What do you think about that? Huh?"

I had told her about a one previous encounter I had with woman and a strap-on dildo. But having gotten to know Pam pretty well over the past month and a half, I decided that wasn't a really bright thing to do. She didn't have a lot of knowledge about such things and I could see her showing up with one so big that it would scare the crap out of a female horse. Nope.

"Cat got your tongue?" she asked before I could reply.

"I'll have to think about that one," I said and changing the subject quickly, "how was the chat with Kathy last night?"

"We were really busy last night and we didn't a lot of time to talk. I told her I enjoyed it, of course I lied!" was her next line and finished with, "she's not working tonight. But we are going out for drinks tomorrow night so I guess I will have to bare my soul."

"More like your ass!!" I wrote.

"Ha! Ha! Ha!" she sent back, and then wrote, "You are making me so damn naughty!" and again with a smiley.

I said, "I've only just started. And if you are feeling too much like a naughty girl, I do have a cure for that."

A couple of seconds passed before she asked, "and what might that be?"

"What happened when you were naughty as a kid?" I asked back.

Again a pause and then, "you wouldn't dare spank me like that!"

"You wanna bet?" I said.

It got quiet at her end.

I waited almost a minute and asked, "remembering something?"

"Yes!" she wrote, "when I was 12, I got into a fight with a girl at school and of course the school told my parents. My dad hadn't spanked me in a few years. But that night he did!"

"Bare ass?" I inquired.

"Bare ass!" she sent back, "first with his hand. Then with his hairbrush. I could hardly sit down the next day!"

I smiled and wrote, "I bet you didn't get into any more fights!" and sent a smiley.

"Shit no," she said, "and before I went out on my first date when I was 16, he stood there holding that hairbrush and said, "you are never too old for a spanking." I was a very good girl that night and for many more after that."

I started laughing so hard again I could barely breathe.

I said, "I wouldn't spank you that hard."

Taking one of my previous lines, she said, "I will have to THINK about that one."

But I had gotten to know her well enough that little seeds like this, once planted, could turn into a whole new level of fun with here. How soon it would happen, I couldn't say but, at least she had something to think about.

I was thinking of a new subject when she wrote, "yesterday was so nice. Thank you for being gentle."

"My pleasure," I replied.

"Mine too!" she answered with a smiley at the end. "Do all the women you screw in the ass have an orgasm?" she then asked.

I said, "Nosy. Some do, some I have help along by rubbing their clit."

She responded, "it did feel different, not bad, but different."

I answered, "pure anal orgasms tend to be a lot stronger. It has a lot to do with the nerves in the ass."

"You are a fucking expert or should I say an expert on fucking," she wrote.

"You should know," I answered, then "kissssssssssssssssss."

"Kisssssssssssssssss," she replied, then added, "I need to get a few things some stuff done here before I go to work. Plus I have to go poopie again."

I laughed and said, "that enema is still working?"

"All 3 of them!" she wrote back. She had given herself an enema before coming over to meet me yesterday, plus the two loads of sperm that I had shot in her ass. I had also to get going for the day. We exchanged long kisses again. As was her practice of late, her last message was some sort of smart-ass remark and today was no exception. It read, "off to poop, I go, I go!"

I let out a long sigh and had another good laugh. She never ceased to amaze me. Then it was off to take care of the business of the day. Friday I also had a lot to get done, so I didn't have much time for chatting.

After she came on-line and we exchanged long kisses, I asked, "all better now?"

She replied, "yes, much better. Thank you.

Then she sent, "well I got asked the question today."

"What question is that?" I replied.

"When was my thing going to be done?" she sent back.

This was how her husband would ask if her period was done, so he knew it was safe to have sex.

"I guess you will get lucky this weekend," knowing that her period had started last Sunday.

"It stopped yesterday, but I told him it was today," she wrote and added, "I can hardly wait."

I laughed and typed, "it will be over before you know it and who knows, he might surprise you?"

She sent back, "you mean fall asleep and forget about it? That would be great!"

I laughed again. I kinda felt sorry for the guy, knowing just know how much her sexuality had awakened. But on the other hand, he had free and easy access to it, but only took minimal advantage of that wonderful sexy woman laying next to him and only for his own pleasure. "What a fool!" I thought. I wrote, "I do have to get going soon dear. It's going to be a busy day. I just wanted to talk to you a little."

"Love me and leave me!" she answered.

"Now, now," I sent back.

She said, "I know. I guess I will talk to you on Monday with the score and all the boring details."

She was referring to the fact that she would count the number stokes of her husband's cock as he screwed her. Needless to say his average was pretty damn low.

"Have fun with Kathy tonight!" I replied.

"Oops, I almost for got about that. Kisssssssssssssssssssss", she typed.

"Kissssssssssssssss," I sent back.

Her final comment which was usually a wisecrack of some kind, but today it was, "I'll close my eyes and imagine it is you." Then she disconnected.

I knew this was getting intense and I was feeling it as much as she was. She hadn't come out and said that she loved me yet, but I knew she came close to it on Wednesday. I wasn't going to be the first to go there, but if she did, well I would respond. But it wasn't like she didn't have plenty of other ways of showing it. The weekend came and went pretty much like any other. Monday morning, her name lit up on ICQ as she signed on.

I was expected a long kiss, but what I got was, "11 1/2. He went soft so quick that I wasn't real sure about the last one." I laughed hard, then she sent, "yes and yes."

Which was her way of telling me that she had masturbated and then tasted a finger full of her husband's sperm after she did.

"The second yes is getting to be a habit?" I wrote.

She said, "I need to do something to make it interesting. I went to the bathroom and took take care of business, then I came out and got back into bed. He was still awake, which is unusual. So I leaned over and gave him a nice kiss."

"With tongue?" I asked.

She sent a smiley and replied, "yes! He had no idea!" I roared with laughter, as she sent, "He is away on a business trip this week. He left on Sunday and won't be back until Friday night. My mom is going to come over and keep an eye on the kids when I am at work."

"Nice little marital vacation this week," I wrote and sent a smiley. I then asked, "how was the date with Kathy?"

She wrote, "she is nosier than you! She wanted to know everything. Not just about Wednesday, but everything! How big you are, how much sperm you shoot, did we do anything kinky?"

"Did you tell her?", I asked.

"A little," was her answer and I am sure she was blushing as she sent it. "She did say that you sound like a great guy and she wouldn't having you for a morning herself."

"Oh boy," I thought as I asked, "and?"

She sent a smiley and typed, "I said I could probably arrange it. We had a good laugh after that so I don't know if she was serious or not."

"That could be interesting," I thought.

Then she wrote, "Now I have a VERY serious question for you!"

All of a sudden I had this weird feeling that was going to be trouble. Knowing women as well I have gotten to know women over the years, I was pretty sure their conversation was about more than just sex. I was sure the subject of how she felt and how deep the relationship was had been discussed between them.

"Yes?" I sent back.

"I want a complete and honest answer," was her next one.

I wrote, "okay, I'm waiting for it."

"None of this beating around the bush nonsense and I'm not talking about mine either!" she sent.

I had never grabbed or hit a woman in anger in my entire life. But at that point in time, if I could have, I would have reached into the PC, through the telephone lines, grabbed her and screamed "TELL ME WHAT YOU WANT!"

I must not have replied back fast enough because she asked, "still there?"

"Yes," I said, "I still am dear."

"Totally honest because I hold you to it!" was her next one.

I started a slow ten count because I was going to write something nasty, but then she sent, "when and if this happens and I am not going to say that it will happen." Then followed with, "how are you going to spank me?"

I let out a big sigh of relief and laughed again. I thought about it for a couple of seconds. I didn't want to scare her off about this but, on the other hand, I wanted to make sure I got to do it right.

"First you get over my knee," I wrote.

"I think I knew that already," she answered back.

I said, "The first ten are administered slowly. Not too hard, but still hard enough. In between each spank, I'll be playing with your cunt and clit."

"No asshole?" she sent back with a smiley.

Ignoring that, I continued, "I will time it so you reach an orgasm around the eighth slap, then I add the last two as you are climaxing."

"That doesn't sound too bad," she said.

I typed, "The next 20," and hit the send button

"20?" she wrote.

"Are given in groups of 10. Not as slowly as the first set, but not too quickly either. And of course they will be progressively harder," was my next line of the conversation.

There was silence at her end.

I wrote, "the last 20," and again hit the send.

"20 more?" came flying back.

I said, "are usually administered with something that the woman was spanked with as a child. I have done paddles, wooden spoons, leather belts, and of course, hairbrushes."

It was a good 30 seconds before she typed, "and do they cry?"

"Most don't," I wrote, "if does happens, it is usually towards the end of the last 20."

After another long pause, just an "I," came from her.

"Yes?" I asked.

A few more seconds passed, then, "I still have my father's hairbrush. Mom gave it to me after he passed away." Then she added, "I was looking in one of my drawers for something a few weeks ago and found it. That thing still scares the shit of me!" I was going to reply back, but then she asked, "I guess my ass will be really red?"

"Yes," I answered, then said, "I try to be careful and not leave marks or bruises but sometimes it does happen."

Another pause at her end, then she wrote, "so I guess if I was going to try this, this would be a good week, since he is not around."

"Probably," I answered.

"Oh," she then said, "I forgot I have to go someplace this morning. I'll talk to you tomorrow. Kissssssssssssssss," and disconnected, without one of her usual ending comments.

"Very interesting," I said out loud, "very VERY interesting."

The next morning she was a little late getting on-line. We exchanged long kisses.

She said, "sorry I'm late. I decided to take my shower early today, instead of before I went to work."

"That's okay," I answered.

She wrote back, "I was very naughty," and sent a smiley.

"Oh?" I asked.

After a few seconds of silence she wrote, "I shouldn't tell you this. But I will. You had me thinking about this for a while!"

I wasn't sure what she was talking about so I sent a "?"

"I put on the pair of my panties that I had worn yesterday. I got in the shower and aimed the head down so I wouldn't get wet. Then I got the water running." I was pretty sure that I knew where this was leading but before I could respond, she typed, "I pee'd my panties," and sent a smiley.

We had talked about this once before. She had accidentally done this as young child. I had told her that some women enjoyed doing it as adults, but I never thought that she would try it.

Then she surprised me even further when she wrote, "then I touched myself."

"Good touching?" I asked with a smiley.

"Very good touching," came back with another smiley, then she added, "I got under the water and then washed up."

"Did you take the panties off?" I asked back.

"Eventually I did," she wrote, "and I now have very wet pair of panties, drying over the shower curtain bar."

I laughed and said, "you are wild! That was very very naughty!"

"But nice," she answered.

My office phone rang, so I typed and sent, "phone call."

She said, "okay."

When it was finished, I let her know.

She typed, "so tomorrow, since I was very naughty today, I guess you will have to spank me." I got a huge smile and my cock got hard at the same time. Then she wrote, "and I am only doing this for one reason."

I asked, "and that is?"

There was a little silence, then "because I was very very naughty today," and sent a smiley.

"Kisssssssssssssssss," I sent.

"Kisssssssssssssssss," was her reply, then she said, "since he isn't around this week, I can get there a little earlier, like around 8:30?"

"That would be fine with me," I typed, "but will you be okay? After working tonight and then going back in tomorrow afternoon?"

Another smiley from her came in, and then, "I have a bunch of personal days to use up before the end of the year. I took tomorrow off."

I smiled and said, "you really planned all this out didn't you? The latest I can stay is around 3:30."

"That's good for me as well," she replied, "I figured we could get some lunch in there. We will probably need it!"

"You are probably right there," I answered

I made a mental note to call the motel and change our schedule for tomorrow. The place catered to the daytime trade so I didn't want to run into any problems. It was probably going to cost me a few extra dollars but it was going to be worth it.

"I guess, I will see you tomorrow then," she wrote.

"I can't wait!" I wrote back.

We exchanged long kisses and her final comment was "neither can I, my dearest, neither can I."

I made the call to the motel and then did some schedule shuffling so that my day would be free. Then I started counting the minutes. It was getting later in the fall. It hadn't snowed yet, but that was coming soon. Wednesday was cold and it was drizzling as I drove over to the motel. He charged me an extra $10 for the extra time in the room, but that was nothing. I had gotten there around 8:15 so I had time to turn up the heat in the room before she got there. She was a little late in arriving. I heard the car pull up and I had the door opened for her as she got out of her car. She smiled when she saw me waiting there. She walked into the room.

"It's nasty out there today," I said as I closed the door.

"I'm sure it will be nice in here," she said with a smile.

I was going to say something else, but she walked up to me, and pressed her finger against my lips, which is the signal to be quiet. She smiled again, turned around, and walked over to the table where she always set her purse on. Her purse was a large one, more like a small travel bag. I knew it was big enough to hold the panties and bra she always brought to put when we finished for the day. She never wore them when driving over to meet me here. She opened her purse, reached in and pulled out a folded up pair of her white cotton panties. Which was a little unusual, since she never got them out until we were getting dressed to leave. Sticking her hand back in the purse, she slowly pulled out a hairbrush. I could see it was an older one made out of wood. She set it down very carefully the table, like it was going to explode. The last thing to come out of her purse was a handful of small packs of K-Y jelly.

"She was ready for anything today," I thought to myself.

Then while still facing away from me, she slid off her coat, dropped it on the chair that was next to the table, and slowly turned around. I noticed two things right away. She always wore the same outfit, which consisted of a sheer blouse, a denim skirt that had buttons down the front, and a full slip underneath. But today, she wasn't wearing the slip. Her breasts were clearly visible through the fabric. She could have just as well had not been wearing the blouse, it was that sheer. Looking downward, I saw that her skirt, which she always had buttoned down to the last button, was opened to the one that was right in front of her pubes.

Breaking the silence, I said, "you look stunning today."

She smiled and said, "I felt like being really naughty today."

She walked over to me, put her arms around my neck, and kissed me slowly at first. But as such things go, it got hotter and hotter. It easily lasted 5 minutes. We pulled our lips away for a little while. She was already breathing heavily. We then kissed again for another 5 minutes.

This time when it ended, she looked at me with a little smile and said, "I want to undress you first."

Being one to never refuse such an offer, I said, "I would like that very much."

She moved her arms down and unbuttoned my shirt. She pulled the front tails out of my pants and opened the last button. Sliding her hands back up my chest, she pushed the shirt aside and placed her hands on both of my breasts. She placed them on my nipples and started gently playing with them. This was something she had never really done in the past. After a few minutes of this, she leaned forward and kissed me gently on the lips. Then removing one hand, she bent down and sucked my nipple. I'm not overly sensitive there, but it still was damn sexy. This was also something new from her. After a minute or so, she replaced that hand and moved to my other nipple with her lips and tongue. When she was finished there, she reached behind me, pulled the back tail out, slid the shirt off my shoulders, and walked it over to the chair.

Returning over to where I stood, she knelt down, untied my shoelaces, and slid my shoes off my feet. She then slowly slid down my socks and pulled them off as I lifted each foot. Moving those off to the side, she slid her hands slowly up my legs to the front of my pants where my rock hard cock was straining to burst free of my underwear. After a few eternally long seconds of stroking it through the front of my pants, she reached up, opened my belt, and then the top of my pants. After slowly sliding the zipper down, she rubbed the front of my underwear for a little while, then worked my pants down my legs. I stepped out of them and I as did, she got off her knees, took them from my hand, and picking up my socks and shoes, she turned and everything over to the chair. She placed my shoes neatly underneath it.