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Kaitlyn and Cheryl Ch. 01

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This is the continuation of Back in the Saddle. I got several requests to continue the story and felt like it was time to describe what happens once everyone is back from the festival. For those just joining the story line, you can start here without losing much or read Back in the Saddle to catch up with the characters.


“What do you mean she broke up with you?” Dan asked.

“Exactly what I said. We were talking Monday night and the next thing I knew, she was dumping me.”

“Did you even suspect there was a problem?”

“Nothing more then long boring talks on the phone at night. I agree with her that long distance relationships suck, but it was only for a couple more weeks.”

“Well, don’t let it get you down. You only knew her briefly anyway,” Brad said.

“Yeah, I know. I was looking forward to seeing her in a couple of weeks though.”

“What about Cheryl? Have you spoken to her at all?” Brad asked.

“Not very much. We spoke once last week, but I haven’t heard from her since.”

“Well, that sucks. Maybe when she comes back she’ll change her mind,” Dan said. “Do you have the kids this weekend?”

“No, I don’t pick them up till Monday.”

After talking about Kaitlyn and the kids, the conversations turned to more fun things and about midnight I headed home. Every other Wednesday, the guys and I got together for drinks at the Sports Bar. It was a pretty cool place to hang out and watch whatever game happened to be on. It was also trivia night and Brad loved going for that reason alone. The guy’s head was completely full of useless information, but every other Wednesday, he became King of Trivia.

After opening the door to my quiet condo, the first thing I did was check messages. There were none. I still found it strange that Kaitlyn had dumped me, claiming she couldn’t deal with long distance relationships and that it was probably for the best. I didn’t even try and fight her about it, but still held hope that she’d change her mind.

I was still a bit wound up and decided to check my email before heading to bed. The last email of the night happened to be from Cheryl, which is something that I hadn’t thought to see. It was timestamped only twenty minutes earlier and asked if I was still awake. It was only about just after midnight, so I sent her a quick email to see if she was still awake and told her to call me if she was. Not even a minute later my phone rang.

“Hey sexy, what are you doing up so late?”

“I was out with some of my girlfriends and thought I’d see if you were around. What about you?”

“I was out with the guys and just got home. I’m a little wound up so I was checking emails before heading bed.”

“So, how have you been? I’m sorry I haven’t spoken to you in a while, but things got real busy on a project and I haven’t had much free time.”

“Things are good. Work’s been busy and I had the kids all last week, so I haven’t had much time for excitement.”

“How often do your kids stay with you?”

“Every other week. I pick them up from school Monday afternoon and I have them till I drop them off the following Monday.”

“That must suck for the week you don’t have them.”

“It does, but unfortunately, that’s what happens when you can’t live with the other person. The kids are doing pretty well with it though.”

“That’s good. I’m sure it’s not easy for any of you.”

“No, not really.” I sighed as I thought about how hard it has been. “But in all honesty, it’s been better for all of us that we are separated. I’ve had more fun with the kids than when we were together and I’m a lot happier with myself.”

“That’s good.” She paused briefly as if thinking about something. “So, does this mean that you are free this weekend?”

“Yeah. I thought about a short trip to the mountains, but it’s not really anything urgent. Do you want to get together?”

“Actually, I have this dinner on Friday night. It’s kind of formal and I’d like to see if you’d be interested in coming as my date. I know you and Kaitlyn are still together and you probably need to ask her…”

“We’re not together. She actually dumped me a couple of nights ago. The usual long distance thing.”

“Oh, I’m sorry John. That sucks. I wonder why she did that?”

“Who knows. But she’s not in the picture anymore.”

“So then you can come Friday?”

“Definitely. Give me the details.”

After telling me all about the dinner, we agreed that I’d pick her up and have some cocktails with some of her coworkers before the dinner. We spoke for a few more minutes before I heard her yawning and decided to head for bed.

The next couple of days flew by and I found myself pulling up to Cheryl’s apartment about five minutes early. After knocking, I heard someone on the other side say “Just a minute. I’ll be right there.” When the door opened, it wasn’t Cheryl on the other side.

“Hi, you must be John. Come on in. I’m Cheryl’s roommate Krista.”

“Thank you. Nice to meet you Krista. I’m John.”

“Cheryl said she’d be down Beylikdüzü escort in a few minutes. Just a few finishing touches. Can I get you a drink?”

“No, I’m good, thanks. I didn’t realize Cheryl had a roommate.”

“Kind of a long story, but I was married till about two months ago. We’re separated and Cheryl is letting me stay here for a while till I’m back on my feet.”

“That sucks. I’m sorry to hear that. How long were you married?”

“Just under ten years. Luckily we don’t have any kids to worry about, but it’s still hard.”

“I know what you mean.”

“Oh, that’s right. You’re separated too. Do you have kids?”

“Yeah, three boys. They’ve handled it pretty well so far.”

“That’s good to hear.” We both turned when we heard Cheryl come down the stairs. My eyes popped as she descended the stairs and more of her came into view. She was wearing a little black dress that showed off her shapely legs and hugged her hips and ass nicely. She must have been wearing a push-up bra because her small tits were jutting out nicely. As she reached the bottom of the stairs and turned to us, I could see a nice amount of cleavage. Her hair hung loosely past her shoulders and her blue eyes sparkled.

“Wow, you look amazing,” I told her.

“Thank you. You look pretty incredible too.” Cheryl was close to my own forty years, but looked much younger. I was feeling very lucky to be there with her right then. “So, you’ve met my friend slash roommate Krista. She’s living here till she gets settled.”

“That’s what she said. Shall we go?”

“I just need to do one more thing and I’ll be ready.”


She went into the kitchen and I heard a door open. A few minutes later she came back with a small black purse and a cover. “Just in case it gets cold later. I’m ready now.” I realized I felt extremely awkward suddenly. The last time I’d seen her, we had just finished having crazy sex up at the music festival and we hadn’t spoken since then. She must have felt it too, because she suddenly took my hand and pulled me upstairs to her room.

She still held my hand as she turned to me and stared into my eyes. “I don’t know about you, but I’m feeling kind of weird right now.”

“Me too. Everything ended kind of suddenly and now here we are.”

“I don’t want to feel weird. And I don’t want you feeling weird. What happened at the festival happened and I’m glad it did. I’m a little sad you never called me after we got back to at least say hi, but at the same time, I could have called you.”

“I did try to call, but never left a message. Then things got crazy that last morning and I guess I didn’t know how to handle it. But I’m glad you called and I’m happy to be here tonight.”

“Good, because I’m glad you’re here too.” Then we were kissing and all those memories of the weekend came back. We kissed for a long time and I started to let my hands wander. She stopped me quickly though. “Not now. I don’t want to have to clean myself up before dinner again.” She backed away, checked herself in the mirror to fix her lipstick and came back to me. She looked at me for a few minutes and seemed to come to some decision. She then walked over to her closet and pulled an overnight bag out. “OK, I”m ready now.”

I looked at the bag and smiled. “Planning on staying out late?”

“Don’t be a jerk or I’ll put it back. I’ve been going back and forth for the last two days on whether I should pack some stuff and initially decided not to bring it. I’m still not sure about it, but I’ll bring it just in case. So don’t ruin it.”

“You got it boss.”

She slapped my arm, but was laughing. “Let’s go before I do something really stupid.”

“Sounds like a good reason to delay.” She gave me a dirty look, but laughed when she saw my smile. “I promise, I’ll behave myself.”

“You better.”

On the ride to the dinner we made idle chit chat to get to know each other better. It felt odd, considering what we’d done the weekend of the festival. But I realized I really didn’t know much about her. When we arrived, I felt a lot more comfortable and she seemed to feel the same way as she took my hand. My nervousness had completely disappeared and I felt like we were going to have a very good night.

We entered and Cheryl gave our names to the people at the registration desk. We got our name tags and table assignment and went into the dining room. I was a bit shocked to see it decked out so nicely, with a large dance floor and a three-person band playing. We found our table and Cheryl put her purse in her chair. Then we made our way to the bar. On the walk over, we heard someone whistle and Cheryl turned to see one of her co-workers. They said a few words, she introduced me and then we continued to the bar.

Suddenly I heard, “Yo John. What are you doing here?”

I turned to see my buddy Sean walking over. “Hey man. I came with Cheryl.”

“Cool deal. Get yourself a drink. I’ll be right over there.”

“OK, give us a few minutes.” I found Cheryl at the bar and stepped up next to her. “I just ran into Beylikdüzü escort Sean. I forgot you guys worked together.”

“Not so much together, but we do have some projects our companies pair up on. What do you want to drink?”

“How about a Manhattan straight up?”

“One Manhattan coming up.” She turned to the bartender and placed our order. I was happy to see it was an open bar, but made the decision to take it easy.

We got our drinks and led Cheryl to where Sean said he’d be. It took a few minutes, but I heard his booming voice and finally found him.

“John, good to see you man. Hey Cheryl, how’s it going?” He gave her a hug.

“It’s good to see you Sean. I had forgotten you’d be here. Luckily it didn’t take much to convince him to come tonight.”

“Knowing Johnny, you probably just had to take a picture in that dress and he was eager to go. You look fantastic.”

Cheryl blushed and muttered “Thanks. So where’s your wife?”

“Our sitter backed out at the last minute, so she had to stay with the kids. Maybe we’ll have you guys over some time.”

Cheryl and I looked at each other but didn’t say anything. As far as I could tell, this was only a first date, so, for me, getting together with another couple was down the road a ways. “We’ll have to see how things go,” I said to Sean.

I could tell he wanted to say something else, but kept it to himself. “Hey, sorry I missed you guys Wednesday, but I had to finish up a presentation for today. Hopefully next time.”

“Every other Wednesday, same time, same place. Have you heard anything from Jack?”

Jack had gotten himself arrested at the festival and we never heard from him after that. Through the wives, we heard that his wife had picked him up, brought him home and then kicked him out. He almost got into a fight with me while he was trying to pick up Cheryl. Other then that, we have no idea what happened to him.

“Nothing more then what you guys know. I think he’s staying at his brother’s for now, but I’m pretty sure their marriage is over.”

“That’s what Dan said the other night.” Cheryl was squeezing my hand and her look said she wanted to talk about something else.

“I have to find some of my coworkers. Do you want to come?” Cheryl asked.

“Sure. I’ll catch up with you later Sean.”


After we walked away I asked, “You OK?”

“Yeah. I just didn’t want to talk about Jack. But I can give you some more info. His wife is suing him for divorce and I’m being asked to speak about what he up at the festival.”

“I’m sorry. I had no idea. I kind of miss info not being married. My ex doesn’t always share with me.”

“No, that’s OK. It doesn’t seem that anyone else knows about it either. From what I gather, she actually filed about three months ago.”

“What? Are you sure?”

“Yeah. Apparently, I’m not the only girl he’s tried to hit on. She’s found messages from other girls on his email account and phone. It’s been going on for a long time and she finally had enough.”

“What a shit head. I knew about that, but thought it was all in the past. I didn’t know about them getting separated, especially since he was still living there.”

“Don’t tell Sean. I’m not even sure I should have told you.”

“OK.” We found our table again and there were several other people sitting. Cheryl introduced me and they quickly got into work talk, which meant I was left out. I had finished my drink and asked Cheryl if she would like another. Instead of giving me her order, she came with me.

“I’m sorry about that. That was really rude of me. I shouldn’t have let the talk center on work. We’re here to have fun.”

“That’s OK. I know how it is.”

“It’s not even like I hang out with any of them, which is probably why we only talk about work. I promise, we’ll leave early if you start to get bored.”

“Don’t worry about it. I can tough it out. Especially if I get to stare at you in that dress.” Cheryl blushed and I placed our drink order, tipped the bartender and we made our way back to the table. The talk immediately turned to work again, but Cheryl tried to steer the conversation away. She wasn’t very successful, but we were saved when the food was served. The food was good and once we were done, Cheryl and I excused ourselves.

Since the weather was so nice, we took a walk in the gardens outside of the hall. Cheryl took my hand as we walked. I was having a really nice time and we got to know each other some more. I was glad to hear she loved the outdoors, and I asked if she’d like to go hiking tomorrow. I got a big smile as she accepted and I took a chance by pulling her close to kiss. She didn’t resist and the kiss went on till we heard an announcement that awards were going to start in five minutes. She kissed me again just before we went inside. But rather then returning to our table, we stayed at the bar.

We were talking quietly when suddenly Cheryl’s name was announced and she turned to the stage. She’d won an award for a project she had completed to help a local community, Escort Beylikdüzü but she didn’t go to the stage right away. Sean actually came over and pulled her up to the stage to receive her award. I could tell she was really nervous as she accepted her plaque and gave a really short speech, thanking her team for all of their support. When she was done, she came over to me and I could see the excitement in her face.

“I can’t believe I won. I knew I was nominated, but didn’t think I’d have a chance.”

“Congratulations. Obviously you did an amazing job. You’ll have to tell me about it.”

“It’ll bore you, but thanks for asking. This is so amazing. I’m actually shaking.”

I pulled her close and gave her a big hug. She looked up at me and kissed me briefly before turning back to the ceremony. Instead of standing next to me, she stood in front of me, so I wrapped my arms around her and she leaned back against my body. The ceremony finally ended and everyone settled down. Sean found us again and congratulated Cheryl for her win.

Cheryl excused herself to use the restroom and when she was gone Sean asked, “What happened with Kaitlyn? I thought Cheryl was off limits.”

“Kaitlyn dumped me on Monday because she didn’t want a long distance relationship.”

“And you immediately hook up with Cheryl. Niiice.”

“Nothing like that. She actually called me Wednesday night to invite me here. How could I decline?”

“No kidding. I never knew what a hottie she was. Whenever I see her she’s either in work attire or ready to get down and dirty in some screwed up river. But I always did thought she was pretty cool and cute.”

“I agree. When she first came down in the outfit, my eyes bugged out. I’d only seen her camping and thought she was pretty cute there. And we know how bad most people look after a few days of camping.”

“No shit. Well, good luck with her. She’s a great girl.”


“Agreed about what?” Cheryl asked as she came back.

“That you’re a great girl,” Sean answered with a smile towards me.

“Nice try Bozo.”

“Really, that’s what we were talking about.”

“Yeah right. I’m ready to leave if you are.”

“Oh, sure. I’m ready to go. Talk to you later Sean.”

“Later.” He had a sly smile on his face but didn’t say anything else.

We grabbed Cheryl’s stuff and went back to my car. She was very quiet on the ride. “So, your place or mine?” She didn’t look up and didn’t say anything.

“You OK Cheryl?”

“Yeah. Can you just take me home?”

“Sure.” I was completely deflated. I thought for sure she’d come back to my place. She didn’t say another word the entire ride back, even after I tried to start several conversations. I had no idea what had happened, but decided to just let it go. I pulled up to her house and she got out of the car before I could turn off the engine. I got out quickly and followed her to the door.

“Hey, what’s the deal? I thought we had a pretty good night and now you’re giving me the cold shoulder?”

She stopped with her hand on the door knob, but finally turned around. She actually had tears in her eyes. “What were you really saying to Sean?”

“What do you mean? I told you exactly what we were saying.”

“Give me a break. You didn’t say anything about getting lucky tonight?”

“No. Not a word. He was telling me that he thought you were a great girl and thought how amazing you looked tonight. I agreed with him and that was it.”

“Why didn’t you call me when we got back here?”

“I did. Twice.”

“I never saw any messages or calls from you. And I checked. Every night for a week. Krista talked me into emailing you, but I had given up. I finally emailed only because Krista wouldn’t leave me alone about it.”

I pulled out my phone and pulled up my call history. I quickly found the two calls I’d placed and showed them to her. “I didn’t leave a message because I thought it was a work number, but you never called me back.”

She looked at my phone and then looked at hers. “I thought those were wrong numbers. That’s not the number you gave me.” She pulled up her contacts and showed me the number she had for me. It was off by one number. “Damn John, I had the wrong number in my phone. That’s why.”

I was angry now. “You know what, just forget it.” I turned and walked back to my car. I saw her overnight bag in the back seat and pulled it out. When I turned to give it to her, she flung herself at me, pushing me against the car.

“I’m sorry. I thought you were blowing me off. Please forgive me. It’s just been a terrible year and I thought you were just another typical guy getting his jollies. Please.”

Her eyes were filled with tears, but I was still angry. “Look, maybe we should just call it a night and try this another time.”

I handed her bag to her and got into the car. She was still standing next to my car as I started to back away. I looked at her and she was crying now, but I still started to pull away. Just as I put the car into drive, I started to feel like a real ass. I didn’t move for several minutes and finally looked over at Cheryl. She still looked incredible, even while she was crying. Besides, I had a really amazing night with her. I put the car into park and got out. I took a deep breath and walked over to her.

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