Encounters
Chapter 4

Copyright© 2012 by Westside24

Erotic Sex Story: Chapter 4 - A widower makes a decision if he should become involved with attractive women, some of which are married

Caution: This Erotic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Cheating  

Dan Casey’s time in Florida was coming to an end. He had a very enjoyable time not only because of his golfing and fishing activities but because of his intimate involvement with his lady friends.

He knew that everything wasn’t peaches and cream in his relationships with all of his women friends. The biggest blow to these relationships concerned Linda. She phoned him to tell him her husband had been promoted to a position at the company’s Los Angeles office. She was moving as soon as she could put her home on the market. The drug store chain where she worked had told her that they had positions opened for pharmacists at stores in the LA area. That would enable her to continue working which is what she wanted to do. Linda told Dan to look her up if he was ever in the area and that she would do the same if she was back north or in Florida.

Dan was going to miss Linda for a few reasons, not all of which were because of her large breasts. She was a genuinely nice person. She was also a good lover and made an effort that was similar to Dan’s in wanting her partner to be satisfied when she made love.

After thinking about her and the memories he had of her, Dan drove down to the adult store and purchased a ‘2-for.’ He mailed it as a present to her along with a note that said, “Use it in good health and think of me when you do.”

Kerrie had difficulty arranging her flight schedule for her to have periodic layovers in Tampa. She was only able to arrange two layovers during this winter period. She was a great love partner and while Dan was hoping for more, he was happy that there were these two layovers.

During one layover she said that her husband Ralph was starting to question why she was continuing to have layovers when because of her seniority level she shouldn’t be having any. Because of the long international flights, it was easier to justify layovers in Chicago as opposed to Tampa which was more of a feeder airport for her airline.

Dee was a bright spot in his relationship with women. She would send him an e-mail every three weeks telling him when she was going to be at the Seminole Hard Rock Casino. Dan would be in his room when she phoned to ask him for his room number.

Once inside his room, she was all over him with very few preliminaries. They were both naked and in bed in a few minutes. Dan was not capable of making love for the three and half hours they had together, but he was able to give her a lot of the loving and the satisfaction she craved with the ‘2-fer’, which he had introduced to Dee. If her reaction to his travel vibrator was good, her reaction to the ‘2-fer’ was off the charts. Just seeing her having the many orgasms she experienced gave him tremendous satisfaction. He loved seeing her reaction during the large and long orgasms she had.

The time flew by and Dan was on a flight heading north for the summer. Linda not being there put a big hole in his social life but Kerrie added some joy to it when she could do a layover.

He had the usual household chores at his townhome and visiting his ever-growing grandchildren helped fill some of the voids in his social life. It was amazing how fast the grandkids grew up. Their schoolwork reflected a high intelligence level which he thought should translate into academic success and meaningful careers.

His phone rang late one morning and in answering it he recognized the voice of his ex-secretary, Carol Papas.

“It’s so nice to hear your voice, Carol. How are you doing and when are you going to retire? I’m enjoying myself and I haven’t yet met anyone who has retired that isn’t enjoying retirement.”

“I have three more years and then Stan and I will retire together. We’re thinking about moving to Texas to be closer to our daughter who now lives there.”

“Enjoy life and your grandkids, it’s amazing how fast they grow up.”

“Oh, that I know. The reason that I’m calling is that I don’t know if you’re aware that Bill Grennen is retiring and that there’s a retirement party for him this Friday.’

When Dan was still working, Bill was one of the two other high school principals in the school district and an overall nice guy. Bill and Dan had friendly competitions on how their students would test out. Unfortunately for Bill, Dan was usually the winner in this competition.

“When and where is the party and put me in. I’ll reimburse you when I see you.

Carol said she would do that and gave Dan the information about the party.

“Have they announced whose Bill’s replacement is?”

“Yes, it’s Dana Carson who was Bill’s assistant for the past six years.”

“A good choice from what I know of her and I think she’ll do fine.”

There was a little more conversation before the call ended. That call brightened his day and he was starting to look forward to going to the retirement party. It would be a nice change from what he normally would be doing in the evening and maybe he would see some old friends.

Based on the number of cars in the parking lot Dan thought it looked like there was a large turnout for the retirement party. That was good since Bill had over thirty years of service in the district and was a nice guy whose career had touched many lives.

Dan saw a large number of people as he entered the hall. He only recognized a few people that were there and he assumed that most of them were from Bill’s school. Spotting Bill he walked over and congratulated him on his retirement.

“Thanks for coming and I’m glad that you did. It’s nice to see you,” said Bill.

“I had to come and wish you well. You had a fine career and your retirement will be a loss to the district.”

“Thanks for saying that as it means a lot to me hearing you say that.”

A voice behind him said, “Who is this retired high school principal that I hear spends all his time in Florida?”

That remark caused Dan to turn around and he saw Dana Carson standing there smiling at him. He had long admired Dana for several reasons when he had seen her at various district meetings. One reason was that she always dressed as if she had just stepped out of a fashion magazine. Another reason was that she was a tall, attractive lady with a very nice body. Lastly, she was an intelligent lady who was very professional in how she conducted herself.

“For your information pretty lady, I don’t spend all my time in Florida. It’s nice to see you Dana as you always look like you stepped out of a fashion magazine. Congratulations are in order on your promotion and I know you’ll do a fine job.”

“Well I hope so but I’m a little nervous about being the principal and these new responsibilities.”

Bill had turned to talk to some other well-wishers which left Dan alone to talk to Dana.

“Don’t be, you’ve learned and seen a lot as an Assistant Principal and all of that will serve you well. Have they announced your replacement yet?

“No, they asked me for my suggestions and I gave them a few names but nothing yet. Talking business for a minute if I may, your students tested out better than our students did when you were a principal. I know that was a thorn on Bill’s side. Can you tell me what your secret was?”

“No secret really, it was just that I got the parents involved in their children’s education. How I did it was too invite all of the incoming freshmen’ parents in for a meeting at the beginning of the school year. I also had a follow-up meeting with them when their children became sophomores. I spelled out what we as teachers were going to do in teaching their children at these meetings but for us to do that we needed the parents’ help if they cared about their child and their education. I pointed out why they needed to become involved if their child was going to be a success in this competitive world and why their child’s grades mattered when they applied for work or went to college. Study habits, homework, and use of the internet to see what homework was assigned, all were subjects that I covered with them. I asked for their help in this partnership that I wanted to establish with them to provide their children the best education we could give and the importance of it.”

“We don’t have those meetings now but I will see to it that we do this fall. That’s a great idea and something I’ll work on.”

“I think I have an outline of the speeches I gave at home. I can drop a copy off to you if you’d like.”

“That would be great and I’m at school during most of the summer. I am already getting ready for the new school year.”

“You should also know that I gave each class a fire and brimstone speech at the beginning of the year telling them what they could expect, why they needed to apply themselves to their studies to the fullest, and what it could mean to them in later life. I will say that not all the students took what I said to heart but I think the great majority did.”

The announcement was made asking everyone to take their seats as the meal was ready to be served. Carol sought Dan out and said that they had put an extra setting at their table for him. At the table was Gordon Daniels, who had replaced Dan along with some of his staff and a few teachers that Dan knew.

One of the teachers sitting at the table was an attractive lady named Emma Baker. Dan remembered her well because of some of the carnal thoughts he had when he would see her. She had a nice figure and wore tight skirts that showed off her very fine derriere. He thought that she had caught him admiring her butt a few times but she never said anything if she did. Dan knew that she was divorced and had heard she dated some of the male teachers but that’s about all he knew about her. Seeing her caused him to quickly wonder how she would react to the ‘2-fer.’ He thought it’d be very interesting if he was lucky enough to find out.

The table conversation initially centered on Dan and his retirement. He told them about spending the winter months in Florida and what he did while he was there. He extended an invitation offered to all of them to come and visit him and said that the second bedroom in his condo was always available for visitors. He teasingly said that since the school year was going on, the standing rule about no vacations during the school year applied which meant that he probably wouldn’t see any of them.

Emma looked at him a little challenged and said, “Don’t forget that we have clean-up week and I may take you up on your offer.”

That response caught Dan by surprise but he said he’d be happy to have her visit.

Dan had a good feeling when he left the party. He thought a little about Emma’s response and wondered if he should try and follow up with her in any way. He would put money on that she would be one exciting woman in bed.

Dan perused his files the following week and found the outline of the speeches he gave that he mentioned to Dana. He stopped by Dana’s school to drop the outlines off and was fortunate to find her in her office.

“Here are the outlines of the speeches we talked about. There are also some CDs that Tim Stuart made of me giving speeches. I made you a copy of the CDs since they may contain some comments I made that aren’t in the outlines.”

“Thanks for coming in and giving me all this information. I will listen to the CDs for sure. Since it’s past noon why don’t you let me buy you lunch if you haven’t eaten yet as I can pick your brain some more.”

“That’s the best offer I’ve had all day.”

Dan had an enjoyable conversation with Dana at lunch. Sure she was good-looking and dressed nicely but they also had a lot in common because of their profession. While Dana knew about Dan and the tragedy of Jenny’s accident, Dan didn’t know that much about Dana. He took the opportunity to ask her about herself.

Dana told him that she had now been divorced for twelve years, after eleven years of marriage. She had no children and while that was good because of the divorce, it was also one of her regrets. Her brother had three children that she spoiled rotten when she visited them in Indiana. Other than playing a little golf, her activities were limited to working out and reading. The summer evenings were a little boring but she knew she would be quite busy once school started.

Dan agreed with her on the evenings being boring and said, “I enjoyed talking to you and I’d like to do something like this again. Maybe we could go out to dinner, but there is one rule I would impose on both of us if we did.”

“Yes, I would like to go out to dinner with you but what’s the rule?”

“No shop talk, let’s leave work at work and just enjoy ourselves.”

“You sir have a deal. Here’s my card and give me a call when you want to go out.”

He thought Dana had a fine backside as he watched her walk back to her car. He also thought this summer as some have said, “Could be v-e-r-y interesting.”

Kerrie phoned him to tell him that she had been able to change her flight schedule. She would have a Tuesday night layover at O’Hare every other week for the next two months. Dan told her that was great news and checked that she still had his cell phone number to call him when she was ready to be picked up. She said that her first layover would be a week from this coming Tuesday.

While he anticipated Kerrie coming in next week, Dan also wanted to do something this weekend. He phoned Dana at the school and made arrangements to take her out to dinner.

Dana looked good in the dark green dress she was wearing. He told her that she did saying she looked like she just stepped out of Vogue magazine. She thanked him for the compliment and he could see that she appreciated hearing him say that.

 
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