Educating Pam Ch. 01

Writers note: This is a real story. Of course, the names are changed. It is about a woman that I met and had an affair with. This first half of this chapter is a little heavy on the dialogue, but I feel it is important to set the stage for what happens later in this and the other chapters. There is little bit of very tame bathroom play as well in here. On a scale of 1 to 10, for that kind of play, at best it ranks 1 and probably is closer to a .5. It does get a little more involved as the story progresses through the other chapters. If you don't like reading about that sort of play, well don't read this. Otherwise, enjoy!

T

Chapter 1.

Eight years ago, I met Pam on-line. She had posted a fairly tame ad on one of the adult personal sites, but like most women, she soon got overwhelmed with responses. Most of which being the, "how soon do you want to get together and fuck?" variety. I sent her an email through the site and said that I just wanted to talk and to get to know her a little better. It took about a week but she finally emailed me back. A couple of emails passed between us over the next few days. She seemed comfortable with the fact that I wasn't trying to drag her into bed right away. I got her on ICQ, which was the instant messaging program, that was popular back then.

For the first week, we just talked about anything and everything, except for sex. She was married, I was married, but you know how the story goes. She told me that she worked afternoon shift as a medical secretary at one of the local hospitals. That left her mornings free to chat. She had three kids, 14, 16, and 18, all still in school. I told her about mine as well. She couldn't get on-line on the weekends, because of husband and kids being around.

The next Monday, I saw her come on line and sent my usual "good morning" message.

She typed back "Good morning to you".

We chatted for a little while about what went on over the weekend, then she typed, "I have a question for you?"

I sent back, "sure, what?"

"How come you haven't asked how big my boobs are yet? That seemed to be the first thing that everyone else was interested in?" was the reply.

I typed, "well, I didn't want to be too pushy and I figured we would get around to that, sooner or later."

She sent back, "oh, okay."

Then another one came, before I could reply, "38D."

I said "nice and thank you."

"You are welcome," she replied and then "and no, I'm not shaved either".

I sent back, "LOL, I guess you got asked that a lot, as well."

She replied, "yes. Does that bother you?"

I said "I prefer shaved or well trimmed, but to be perfectly honest, it isn't a big deal with me."

She sent back, "that's good."

And another "anything else you want to know?"

I shot back "really bushy?" with a smiley at the end.

"Really bushy!" was the reply with a smiley in return.

"Sounds real nice to me!" was my answer.

And on it went. That day and for the rest of the week. Each day, the conversation got a little more intimate. She told me about her husband and how sex with him, which was never great to begin with, had gotten pretty mundane.

"Once or twice a month for a couple of minutes and that is it," she wrote.

I asked back, "do you climax?"

After a little hesitation, she replied, "yes, after he falls asleep."

I wrote back, "well that seems to happen with a lot of the women I have talked to."

"Are you seeing any now?" was her next question.

"No," I said, "it's been about 6 months."

"And your wife?" she asked.

"I said if I'm lucky if I get it once a month and it's more like every other month. It is a battle to get there and then I have to listen to her bitch about afterwards," was my reply.

"I'm sorry," she wrote.

I sent back, "we both have our problems."

She said, "yes we do."

We exchanged non-nude pictures that week as well. She was your average mom type, 40 years old, about 160 lbs. but from what I could see in the photo, nicely distributed. She was a brunette with shoulder length hair. Average looks, but I wasn't going to win any best of show awards in that department, either.

On Friday, while looking for something new to talk about, I asked, "how did you loose your virginity?"

She replied that, "that is an very personal question!"

I was thinking of something to reply, when she sent, "in the back of a car, with my husband before we were married."

"Okay," I replied.

She continued, "I didn't know much about sex. We had fooled around a lot, but one night I was feeling a little braver than usual and let it go past the fooling around stage."

"He got on top of me, and before I knew it, he pushed it in me. It hurt like all hell, and then he came right away", was the next line.

"I spent the next 2 weeks praying I wasn't pregnant, which I wasn't," with a smiley at the end.

I said, "yeah, that could have been a problem."

She wrote back, "so I got some rubbers and made sure he used one after that."

"Did the sex ever get better?" I asked.

She replied, "a little, but not much."

I said, "okay. And are you baby proof now?"

She sent back "LOL, yes! I had my tubes tied after my daughter was born."

"That's good," I said, "cause I'm not much for wearing rubbers any more. Besides I can think of much better places for my come to go, other than a trash can."

"You are so naughty!" was her reply.

It was time for her to get ready for work and I had work to do as well. I was self-employed, so I had a bit of screw off time, but still needed to get things done.

I said "I'll talk to you on Monday, have a great weekend."

She replied back, "yes, you too"

Then came in, "Kisssssssssssssssssssss."

That was a first, so I sent one back as well.

Next Monday rolled around and when she came online, I wrote "Good morning dear. Kisssssssssssssss."

She sent back "Good morning to you dear. Kisssssssssssssss."

"How was your weekend?" she then asked.

"Nothing out of the ordinary here. Yours?" I replied.

"Pretty much the same here," she said.

Feeling a little bit of the devil, I asked, "get lucky?"

A little hesitation and then, "Saturday night."

"Oh," I said, "short and sweet?"

"Short" was the reply.

Then she asked, "Are you doing anything this morning?"

"Not really," I said.

"I was wondering if you wanted to meet for breakfast someplace?" she replied.

Usually, I was the one to suggest a face to face meeting, in a neutral place, so this was a bit of a surprise.

I said, "that would be nice."

I knew we were about 40 miles away from each other, so I suggested a diner that was about half way between where we lived. I was also thinking that there would be less chance of either of us, bumping into anyone else that we knew. She knew where the place was, so we agreed to meet there in 45 minutes. I told her I what I was driving and she did the same.

I signed off with a "kisssssssssssssssss."

She did the same, "kisssssssssssssssss."

I did a few quick things around the office, then I got on the road. I got there with 5 minutes to spare, but she wasn't there yet. The time came and went, then 5 minutes late, then 10 minutes late. I was just about to leave, when I saw a vehicle pull in the lot, like the one she said she was driving. The window rolled down and it was her. She saw me and waved. She pulled into the parking space next to me.

We both got out at the same time and she said "I'm sorry, it took longer than I thought."

"No problem," I said.

We went into the diner and got seated at a booth in the back, away from anyone else. She was wearing a ribbed turtleneck shirt that showed off her breast's nicely. I took a few discrete looks to get the lay of the land. The waitress came over and we ordered our meals.

I said, "I was really surprised that you suggested this."

She shrugged her shoulders and replied, "I just wanted to meet you in person."

"Oh, to see if I am real?" I asked with a smile.

She laughed and said, "yes, that was the reason."

I said, "you are a lot prettier than our picture."

"Thank you. You are a lot more handsome as well," she said back.

"I'm sorry again about being late, it just took longer to get ready than I had planned on," was her next comment.

"You didn't have to get all fancied up for me," I said.

"It's a girl thing, you know, first date and all that" she said with a smile.

I said, "I guess this is a first date. I hope I at least get a kiss," and winked.

She said, "you never know till it happens," and winked back.

Then our food came and we started eating. The conversation was pretty much about work, life, and kids. Nothing, that if overheard, could be taken for anything other than a couple of old friends catching up.

Then she said quietly, "did you check me out yet?"

I said back, "I've taken a few looks but I wanted to be discrete."

She replied, "I thought you were, but I wasn't sure."

I looked her in the eyes, and then lowered my gaze to give her breasts the official inspection. They were nicely rounded. I had hoped for a glimpse of nipple poking through her bra, but there was none to be seen.

When I looked back up, she was blushing a little, asked softly, "get a good look?"

I laughed a little and said, "very lovely."

"Thank you," she said back in almost a whisper.

We were finished eating. The waitress came over, cleared the table and left the check.

She went to reach for it and I said, "don't even think about it."

"Okay, but at least let me leave the tip," she replied.

We got up to leave. I let her get out of the booth first, being the gentleman that I am, but I also wanted to catch a good glimpse of her ass, before she put her coat back on. She had on dress slacks and I was pretty sure she had pantyhose on underneath with no panties, because I didn't see a panty line. I figured I ask about that later. We walked out of the diner and over to her car.

She said, "I had a really great time today."

I said, "so did I."

She then said, "I have some errands to run, so I won't be back online till tomorrow."

"I understand", was my reply.

She opened her car door and got in.

She said, "you still want that kiss?"

I leaned in, as best as I could, and she put her arms around me. The kiss started off softly. Her lips started moving, and I moved mine back. Then I felt her tongue probing my lips. I parted mine and sent mine out to meet hers. It was a really great kiss. I thought seriously about reaching out and feeling one of her breasts, but I decided not to.

After a few way too short minutes, we ended it and I said "drive safe dear."

She said back, "you too, dear."

The wait until the next morning seemed like years. Finally she showed up on line. We traded good morning's and kisses.

She asked, "so what did you think?"

"About what?" I asked.

"Yesterday and me, silly!" was the reply.

I said, "yesterday was great and you are one very beautiful lady."

"You tell that to all the women, I bet!" she sent back.

"Darling, you were the only one I was with yesterday, so that eliminates the rest of the world," I answered.

"And the kiss?" was her next question.

I said, "that was very nice!"

Then I sent, "I have to say, I came very close to putting my hand on one of your breasts."

She said back, "that would have been okay."

I said, "Damn, I will remember that for the next time", and added a smiley.

She sent a smiley back.

Her next message was, "so where would you like to meet the next time?"

I thought about for a minute or so, then another message comes in, "still there?"

"Yes," I said, "I'm still here."

"If I had my say in the matter, there is a motel about 4 miles north of the diner," I typed.

Now the silence was at her end. I thought that maybe it was too soon to hope for that.

I just starting to type something, when she replied, "that sounds good to me."

I was so stunned that she had said yes, that the slightest gust of wind could have knocked me off my chair at that point. My cock got instantly hard.

"When?" was her next message.

"Tomorrow?" I wrote.

Silence, then "okay, what time?"

I wrote, "when can you get there?"

"9:30," she wrote back.

"I'm not sure where this place is," was her next message.

I said, "just meet me at the diner and you can follow me there."

"Okay. Do you want me to wear anything special?" she wrote and sent a smiley.

I thought about for a little bit and said, "a blouse with buttons down the front, that can be easily removed, and a skirt."

She said, "I have a long jeans skirt that buttons down the front as well, is that okay?

I wrote back, "Perfect. Underwear is optional," with another smiley at the end.

Little bit of silence at her end, then "I will have to think about that."

"It is up to you," I replied and added, "Whatever you feel comfortable in doing is fine with me."

"The blouse I am thinking about wearing is kind of sheer. I might have to wear a camisole," she wrote.

"That sounds nice," I said.

"I also have a full slip," she wrote.

"Now that sounds sexy," I replied with another smiley.

"Not really," she sent back, "and I'm going to have to really think about going out with no underwear on."

I said, "you weren't wearing panties yesterday."

She sent back, "You really checked me out, didn't you! I was wearing pantyhose."

"Yeah," I wrote, "that's what I figured."

"My ass is too big," she said with a smiley at the end.

I replied, "looked like two really nice handfuls, just like those great breasts."

Double smiley from me.

"I do have one thing to ask," she said.

I said "sure, what is it?"

"Nothing kinky?" was her reply.

"Naw," I said, "at least not on a first date."

"This will be our second," she reminded me.

"Not this kind of date it isn't," I wrote back

"If you say so," she replied.

I looked at the clock and remembered that I had an appointment to get to.

I wrote, "I hate to do this dear, but I have something to do this morning."

"Okay" she wrote.

I replied, "I will be here till 8:45 tomorrow morning so if anything changes, let me know, okay?"

"Okay", again was the answer.

"Kisssssssssssssss,", I sent.

"Kisssssssssssssss," was the reply.

I went out on my appointment, which went longer than planned. I got back to the office and looked at ICQ. She was offline and there were no messages from her. Good I thought, she hasn't backed out yet. Having been doing this for a while now, cold feet at the other end was always a possibility on a first time motel date.

It had been a couple of months, since I had last had sex and my balls were ready to burst. I thought, with this gal the last thing I need, is to have an short fuse in the orgasm department. So I headed for the bathroom, sat down on the toilet and pumped my cock to the point of cumming, all the while thinking of her. I turned around and unloaded a big load into the toilet. I washed my hands and cock off, then got the clothes back in order. I then worked away the rest of the day, thinking about the day to come.

I was back at my office early the next day. I worked alone, except for a very part time secretary who came in twice a week to help with the paperwork. I fired up ICQ. Around 8:30 she came online. Oh shit, I thought, she's going to back out.

"Kisssssssssssss dear, are we still on?" she wrote.

"Kisssssssssssss dear, yes we are," I wrote back.

"Okay, I promise not to be late," she replied.

"Great," I answered.

"See you at 9:30," she wrote and then disconnected.

I let out the deep breath I had drawn in when she first came on line. I counted the minutes till it was time to leave, and then I hit the road. Got to the diner where we were supposed to meet, early again. 9:30 came and went. Finally around 9:40, she pulls in, rolls down the window and yells out "sorry."

I just smiled. I started my truck and we drove off. The place we were heading to was a very cheap if paid in cash, no-tell motel. While along a main highway, it was far enough away from the surrounding towns, that most of it's business was of the day time variety. I had been there before during a previous affair and when I called on Tuesday to reserve a room with a king sized bed, the owner still remembered me. The place had five different buildings with rooms. I pulled in by the office and she pulled in behind me. I went in, paid for the room, came out and showed her which building to head over to. We drove up, parked and got out of our vehicles. There was nobody else at that part of the motel that day. It was a cool autumn day and she was wearing a long coat, not quite as long as her skirt. I opened the door and we went inside. The lights were off but the curtains were open.

She looked around and said, "it's not the Ritz, but I guess it will do. I do have to leave by 12:30 though."

I said, "that is fine".

The lights in the room were all table lamps. I turned on one and closed the curtains. There was enough light to see, but it was still a little dark in the room. She took off her coat and laid it on a chair. I looked at her. Her blouse was very sheer. I could see the outline of the slip very clearly. I could also easily see that she wasn't wearing a bra. Poking through the thin fabric were two nice big nipples. I could even make out a little bit of her areola though the fabric.

I said, "you look stunning."

"Thank you," she said, blushing a little.

I walked over to her and put my arms around her kissed her. Her arms came up around me and before long, our tongues were a dancing like a couple of teenagers in heat. I started moving my hands up and down her back, bringing my fingers up to stroke her neck and into her hair. She really liked this, because she started moaning as we were kissing. I brought both of my hands around, and cupped a breast in each hand. I played with them for a bit, taking in their softness and fullness. Her hand slid down to the front of my pants where she started stroking my already erect cock through the front. I then zeroed in on her nipples with my thumb and forefinger.

"Oh my God," she moaned, as I kept kissing and squeezing.

I let go of one nipple, and started to unbutton her blouse with that hand. She brought her arms up around my neck and I could feel her unbuttoning the cuffs. I pulled the blouse tails out of her skirt, then I pulled the blouse off of her and dropped in onto a nearby chair. She reached over and unbuttoned my shirt as we continued to nibble and kiss. I brought my hands around and unbuttoned my cuffs. Her hands came up and stroked up and down the hair on my chest. Then she reached up, and pulled my shirt off. Drawing her close again and holding her tightly, I turned up the intensity of the kiss. I slid my hands down her back to her ass. I grabbed a cheek in each hand and started playing and squeezing them together. I traced my fingers down to where the panty elastic should have been and there was none.

I whispered in her ear, "you naughty girl, you forgot your panties."

She whispered back, "this is the first time I have ever went anywhere, without panties or pantyhose."

I said, "I'm glad it was for me".

Moving back a little, I reached around and slowly opened the buttons on her skirt. She reached down and pulled on my belt to open it. Then she opened the top of my pants. I kicked my shoes off, and when enough buttons were open, I slid down her skirt, which she stepped out of. Off on the chair that went. A quick pull on my zipper and my pants were added to the pile. I stood back a little and looked at her standing there. The slip wasn't fancy, but at that point in time, it was damn sexy looking. Even with the dim light in the room, I thought I saw the outline of her pubes through the slip.

I said, "damn, you look so hot".