Charley and Trish Pt. 01

Trish and I have spent a lifetime together. When we met, she was 15; I was 16. We weren't exclusive in high school, and we had our ups and downs. We have managed to make our marriage work longer than most.

One day last year we were talking about friends we had in high school. One stood out to us both. I had met Charley thru his dad's friendship with my dad. She met Charley when she moved to some new apartments with her mother in the next town over. This put her in a different high school, and along with a new home and a new school, she made new friends. Charley was two grades behind her in school and lived in one of the homes across the parking lot from her apartment. They quickly became friends. He didn't have a car. He would call Trish to set a "date" with her, and then when the time came, he would walk to her apartment, "pick her up", and they would walk to wherever they were going. Both their fathers were construction workers, and because they came from similar blue-collar backgrounds, they talked about things they had in common. As Trish describes it, they became close friends.

Trish tells me they did nothing beyond kissing and occasional feel up sessions. It might have mattered to me back then if they had gone further, but it doesn't now. Trish says she wouldn't do anything more because he was two years younger than her, and she didn't do "those things" anyway. She freely admits that Charley, being a hormone-driven teenage boy certainly tried to do more, and she, being a hormone-driven teenage girl wanted to do more. He worked her trying to talk her into doing more. I told her If she admitted today that she had done more, it wouldn't matter, because that was before we were married, and what was between friends stayed between friends.

As we discussed Charley and other friends, I asked Trish if she might like to see him again. She thought for a moment and said, "Yes, I think I would. It would be nice to visit with him again." I was comfortable with that, and my sexually imaginative mind kicked into gear. I began thinking of them being together. The picture in my mind was one of them walking down the front sidewalk of our house, hand-in-hand, to Charley's car for their first date as adults, with both of them knowing that I approved of whatever they would choose to do. With my agreement, they would mutually decide how far they wanted to take their renewed friendship.

Trish loves for me to tell her naughty stories when we are making love. I introduced Charley into our next session, telling Trish how she had "unfinished business" to bring to closure with Charley. As I looked into her eyes, I asked her if she had my permission, would she go for it. She simply said, "Mmmmm". I told her that wasn't an answer. She kept quiet for a few seconds as I turned up the Rabbit Vibrator I was using on her. She jumped. I firmly said, "Give me a real answer! Will you go out with Charley if I say it's okay?"

"Yes! God yes! I will!" She answered.

I pushed the toy deeply into her and watched as her eyes rolled back. "Will you take your friendship where you wanted it to go back then?"

She whispered passionately, "Yes!"

I pumped the toy as it vibrated at its highest speed. "Will you suck him to get him as hard as he can be for you? Will you lick his pre-cum from the tip of his cock? Will you look him in the eyes as you do that and tell him how good he tastes?"

She began pumping the toy while screaming, "Yes, yes, YES! Oh, gawd yes!" And she climaxed, thinking of sucking and fucking Charley. She went limp, exhausted in the act of being the woman she is.

The next morning, Saturday, we were in the kitchen getting coffee and breakfast. We have vastly different tastes in food, so breakfast usually is made by each of us separately. We were each occupied with our own thoughts, when Trish said, "You know, fantasy is one thing. Real life is completely another."

I paused for a moment. Her comment was a line she had used many times. I responded with one of my favorites. "While that's true, it only goes so far. If you don't do what you can and want to do while you can, you'll later find yourself wishing you had, because now you cannot."

She looked at me quietly with a thoughtful look on her face. Then she calmly turned back to fixing her breakfast. After eating, we went about our normal Saturday chores, errands, and runs. That evening we settled in with a drink. Trish watched some television shows, while I engaged on the computer. I went to a people search engine and put in Charley's name. I got a few hits and, lucky for me, the third item on the list included Charley. I ran a more in-depth search and picked up his address and phone number, along with that of his oldest son carrying the same name. After paying for and running the law enforcement check and finding him clean, I made note of the information and put it away for the time being.

I joined Trish in watching television. It had been a good, busy day. We were comfortably tired and went to bed early.

Sunday morning, we woke up and cuddled for a while. One thing led to another, and we made slow, sensual love.

As we lay there, basking in the afterglow, Trish raised up on her elbows, looked me in the eyes, and asked, "Do you want me to fuck someone else? Do you want me to fuck Charley?" When she asked that, I knew we were on our way, and the thought of it turned me on tremendously!

I looked her in the eyes and calmly stated, "I want you to enjoy yourself. I want you to do what you want to do. I don't want you to hold back because you THINK I don't want something. We've built a life together. A home, great kids, and now grandkids. We should enjoy ourselves. I don't want you to go off permanently with Charley or any other man, but I want you to have fun in life. If that means you get yourself fucked silly, then that's what I want."

She looked at me lovingly. It was one of those moments. She simply said, "I love you." She kissed me, and then hopped out of bed to begin the rest of our day.

As we were in the kitchen for breakfast, I asked her if she would like to reach out to Charley. She responded by wondering how we would do that. I told her I found his contact information online, and if that didn't work, I had his oldest son's information also. I had also run a records check and Charley wasn't an ax murderer. Her eyes lit up as she looked at me and gave me one of the biggest, brightest smiles ever.

"You're amazing! You know that? You're absolutely amazing!"

"Thanks, sweety," I answered. "I feel the same about you."

"Are you sure you would like me to go through with this?" she asked.

"I'm as sure as I can be." I responded. "It's been a long time since we've done anything like this. The jealousy isn't there at all, but there is some concern because Charley was a particularly good friend of yours back then. We haven't seen him since we left our childhood home area. If I thought about it too much, it could bother me, but I trust you. As we've talked about before, we've built a good life, and I want you to want to come back to it when you are done playing."

"Rick!" she said emphatically. "There is nothing that would make me want to leave what we have! I am yours! Always have been! Always will be! I hope you know that. We did things you wanted to do earlier in our marriage. I did them because you wanted to at first. Then I did them because they were fun for me also. But nothing, nobody, ever made me think twice about us. I love you and only you! You got that?" She slapped me on my shoulder.

"Yes! Yes! I get that. I wanted it stated and out in the open because this is a little closer than the other times and other people. You've always had a fondness for Charley. I've known it. Deep down, you know it. And like all our other adventures, I want transparency. Believe me, I know! I got it! And I love you for it. I'll reach out to Charley today. Is that okay?"

In a quiet, subdued manner Trish responded with a simple nod of her head and a straightforward, "Yes." I could tell she was thinking. She was thinking about Charley. She was thinking about me, the love of her life, setting her up to be fucked by her good friend from years ago. She was excited because she was thinking of all that could happen -- that would happen because she would be sure it would happen.

Later, after a day of finishing up a few odd jobs around the house, we sat in the family room. Vickie was reading a book as I picked up my phone and dialed the number I had for Charley.

Three rings and I heard, "Hello."

"This is Rick, Charley. Rick from a long time ago."

"You're kidding! Rick? I'd recognize that Texas accent anywhere. How the hell are you, man?"

"Haha! I'm doing fine Charley. How are you?"

"I'm doing great for an older guy. Are you and Trish still together?"

Wow! I know where his thoughts are right away with that question, I thought to myself.

"Yes, still together. Who did you marry, and how's that going, Charley?"

"I married a little gal from Washington Missouri. That was my Margie. She passed from cancer almost six years ago now", responded Charley sadly.

"I'm sorry to hear that, Charley."

"Thanks, Rick. She was the love of my life. We had a good life together. She gave me our son, and he's grown into a fine young man with a family of his own."

"That doesn't surprise me, Charley. You were always a good guy. You even took care of Trish when I wasn't around. I appreciated that. I would expect your son would be the same way", I told him.

Trish was listening as we spoke. She watched me carefully as Charley and I chatted. We talked about his brother, Jay, who was a good friend of mine back in our youth. I told him about my military career and where we had settled and our family. I stopped him for a moment and asked if he would like to talk to Trish. He said he would. I noticed a note of excitement in his voice as he responded to the question.

I took the phone over to Trish, muted it briefly, and said, "Ask him to come see you." I unmuted the phone and handed it to her.

She quietly, almost shyly said, "Hi Charley."

They began talking and I left the room to give Trish privacy for her conversation.

I heard an occasional giggle and an outright laugh during the conversation. It started getting a little quiet, so I wandered back into the room and settled into my chair. Trish looked at me, smiled, gave me a wink, and then said, "Charley, come see me. Come visit me." There was a pause, and then "He's okay with it, Charley. Rick is the one that suggested I ask you. When can you make it?"

I was proud of her. She was pushing him to commit. She was making this happen. He was responding to her, so I didn't hear that part of the conversation. Then I heard Trish say, "Hold on, Charley. Let's get Rick in the conversation, so we can be sure our dates line up. I'm going to fill him in what you just said." Trish turned on the speaker phone setting, and Charley listened as she explained that he suggested one week from this coming Saturday -- less than two weeks away! I countered the suggestion. I said he should extend the weekend, flying in Friday morning or early afternoon and staying until Monday morning. I would plan to be off work, and we would be able to make a complete weekend of it. He responded positively to the suggestion.

He said, "I'll make flight arrangements and hotel arrangements and will let you know when I have them locked in."

I told him to make the flight arrangements, that he would stay at our place through the weekend, and that we would take care of food and fine adult beverages. He paused for a moment and then agreed. I gave him Trish's phone number and told him to call her with the details when he had them. We would pick him up at the airport and the weekend would begin. I mentioned that he would want to bring along one nice set of clothes -- slacks, a front button shirt, and probably a blazer -- as we would go to at least one nicer restaurant over the weekend. He agreed to that. Trish was listening intently. I told Charley that I was switching off speaker phone and giving the phone back to Trish so they could wrap up their conversation.

Trish took the phone, and smiled at me as she said, "Hi again!" to Charley.

She didn't leave the room; nor did I. They talked for just a couple of minutes and I heard Trish say, "Okay. That sounds so good. I love you, too!"

I smiled at that. When she hung up the phone and handed it back to me, I asked, "I love you, too?"

"Oh, uh, well, he said..."

I cut her off. "I'm only teasing my dear. It's perfectly okay with me if you love him, as long as you stay in love with me. You've given me everything I could hope for in our marriage, putting up with my military deployments, my hours, days, and weeks at school, both military and college. It's okay if you love a guy that was a confidant, friend, and near lover earlier in your life. I love that tenderness you have."

She kissed me. I noticed she had tears in her eyes. I was touched even more.

I jumped up and said, "So! We have getting ready to do during the next couple of weeks. The weekends will be especially busy."

"Why?" she asked.

"You need new clothes for being with Charley. We'll spend next Saturday and, if needed, next Sunday shopping for them. You get to provide input. I get final say in what is purchased and what you will wear when." I responded.

"But I have nice clothes!" Trish said.

I answered her objection, "I have something in mind, and I think you'll like the idea when you see what I'm thinking. I'm not telling you anything right now, but it won't be slutty or outrageous. Just bear with me until Saturday morning and our shopping trip."

Throughout that week, Trish commented about how nervous she was, how excited she was, and how much anxiety this whole thing was causing her. She would text me at work three, four, five times a day letting me know. When I could, I would call her to help her calm down, and we managed to get through the week.

Trish had let me know each time Charley had called. We had his travel details, so we knew what that Friday would look like. I didn't ask what the conversations were about, but I had an idea. I mean, Charley could have passed along the travel details and then not needed to call again, but they were reestablishing their friendship and having fun on each call. I was fine with that no matter how far they took their conversations.

Saturday was upon us and we woke up early, showered, went out to an early breakfast, and sat and talked about the event while waiting for the stores to open. Trish was less nervous than she had been during the week. Time helps, and the frequent phone conversations didn't hurt at all. We skirted the thoughts of how far she and Charley could or should go. We never went directly at that topic, but it would come up soon. I would be sure to address it with her, so I could be sure she was settled on the idea of "being with" Charley.

I had done my homework and had taken some time off during the week to look through three of her favorite stores and establish a connection with a salesperson who would be on-duty Saturday morning at each of the stores. I had explained what I was looking for and asked each of them to have something in mind when we came in.

As we shopped in each store, we took our time and found four outfits for Trish that I particularly liked. I tipped each of my special "helpers" for being ready for us with ideas. The outfits consisted of skirts with hems enough above the knee for her beautiful legs to be noticeable and matching front button blouses. One in each color -- black, navy, turquoise, and red. That took a little over four hours of shopping, so we stopped in at a small sandwich shop which we both liked and had lunch. I asked Trish to tell me what she thought of the outfits. She was pleased with them, and as I expected expressed a little concern over the shortness of the skirts. She had not worn anything that length in at least a couple of years and was worried about how she would look. Trish has some of the finest legs around, and I reassured her that she would look perfectly fine. She looks 12 or 15 years younger than she is anyway so she will be fine in the skirts we picked out.

I then suggested we look at shoes. I thought a new pair for each outfit would be nice. That surprised her and she readily agreed. Trish loves shoes. Most women do, right? We finished up our sandwiches and headed off to the shoe store. We had to visit five shoe stores to acquire four pairs of shoes for the outfits. At the very first one, we selected a cute pair from the window display. I asked the shoe salesman if he had a place Trish could change into one of the outfits and see how the shoes paired up with it. He showed her to the employee restroom which had just enough space for her to get out of her slacks and pullover top and into one of the outfits.

When she came out into the store, the salesman stared. He stared a little too long, and had to recover quickly, asking Trish to have a seat again. As she went to the chair in front of him, she looked at me with a questioning look on her face. I nodded and winked. She broke into a smile and sat down to be waited on by the salesman.

When he brought the left shoe up to put on her foot, she shifted in the chair to the right and then opened her legs to bring the left foot up for the shoe fitting. The salesman almost dropped the shoe. Trish had opened just enough to give him a nice leg and panty shot. He hesitated a moment and looked Trish is the eyes. With a twinkle in those eyes, she gave him a big smile. He understood then that she meant to do it. He carefully looked over at me. I grinned and nodded. He knew then that he could look all he wanted as far as his eyes could see.

The process was the same for each of the stores, and while it took a little longer than I expected, we came out with a pair of shoes perfectly matched to each outfit. Trish was flush with satisfaction and smiling her biggest smile. She had new shoes, and she had completely enjoyed flirting with her beautiful legs with each of the salesmen.

I had one more surprise for my loving wife. As we walked out of the store, I steered her towards the left. I knew where we were going. She didn't. We arrived in front of the lingerie store. She was still in the red outfit we had matched to the shoes. As we entered the store, a middle-aged lady asked if she could help us find anything.

Trish started to say, "Well, I, uh...."

"We have four new outfits. Skirts and tops with matching shoes. We need lingerie sets, panties, bra, thigh highs to match. We want to look at a couple of matching garter belt and stocking sets for each of the sets. Can you do that?" I said as I stepped into the conversation.

"I'm sure I can do that. What colors do you have to work with?" she asked.

I opened the bags and showed her the skirts and tops. Since Trish had on the red skirt, blouse, and the matching shoes, and I said, "Let's start with red."

"That outfit is so cute! I'm sure we can find a match. Let's start with matched panties and bra, and then we can move to the garter belt and stocking sets" She exclaimed.

"That sounds good. We'll try on each outfit with whatever lingerie you bring us. We'll need you to check each set to ensure it fits Trish properly, so feel free to come and go in the fitting room as we work on this."

Trish gasped. I looked at her with a questioning look, raised an eyebrow, and asked, "Is that okay with you, dear?"

"Umm...can we talk?" She asked.

"Sure, babe. Pardon us a minute, uh, Sherri." I said as I checked her store badge.

I walked with Trish a few feet away. She turned, looking at me, and asked urgently, "What are you doing?"

I responded. "You are getting ready to go on one of the biggest adventures of your life. This is something you've wanted to do since high school. Fucking Charley is something you wanted to do. As long as you don't say no, it will happen. You will fuck Charley, and Charley will fuck you. I want the entire adventure to be remembered as something special for you. I want you to remember everything we did to make it as thrilling as it could be. Relax while Sherri helps us, helps you, to find just the right lingerie to wear with the outfits you have for the weekend with Charlie. I guarantee that every time you see him looking at you in your new lingerie, you'll remember picking it out. You'll remember Sherri pushing, pulling, and tugging to get the right fit, and you'll get excited. And you'll be more excited about Charley looking at you hungrily."