Kaitlyn and Cheryl Ch. 02

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John and Cheryl visit Kaitlyn in Boston.
11.1k words
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Part 2 of the 3 part series

Updated 11/01/2022
Created 12/07/2010
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WhatIKnow
WhatIKnow
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When my alarm went off it was still dark outside. Cheryl was curled up in front of me and was sound asleep. We had about thirty minutes before we had to leave my place, but I wanted to get moving. My dick was hard so I rubbed it on her ass. Cheryl stirred and she pushed her ass against me. After rubbing for a few minutes she finally opened her eyes, but by now I was ready to go and it seemed that she was as well. I looked at the clock and saw we only had about twenty minutes, but my little brain took over and I pressed it against her ass.

Cheryl moaned as she felt my hard cock press against her and she pressed against me, but just as the head was about to squeeze into her, she looked at the clock.

"Fuck John, we don't have enough time, but you feel so good." She let the head press against her a little more but then let out a huge groan and pulled away from me. "You should have woken up sooner. Now you're going to make me wait all day."

"You're not the only one stuck waiting." I followed her into the bathroom to grab my toothbrush, my boner bouncing as I walked. I grabbed my toothbrush and paste and left the bathroom so she could take care of what she needed.

She came out of the bathroom brushing her teeth and looked at the clock, then at me. My cock was still standing at attention and seeing Cheryl naked in front of me didn't help very much. I started calculating whether we had enough time and decided what the hell.

I finished brushing and spit and Cheryl did the same. Now with my mouth clean and fresh, I grabbed Cheryl by the waist and pulled her tight, trapping my cock between our bodies. She didn't resist as I lifted her up and she helped by wrapping her legs around my waist. Then she pulled herself up, adjusted my cock and sank down. Her pussy was soaking wet and it felt incredible sliding into her.

"I was hoping for some anal action, but this will have to suffice. We don't have much time, so you better get moving."

I walked over to the bed and laid her down. I pulled her legs from around me and spread them wide apart. I started to thrust hard and she grunted each time. Then she reached between her legs and rubbed her clit.

"I'm not going to have a chance to shower before we get to Boston. I'm going to smell like a cheap hooker by the time we get there."

"I could stop if you want."

"No you couldn't, so don't even try that. Besides, I'm so close right now that I don't care." Then her orgasm hit her and she was reduced to grunts and groan. Her pussy tightened around my cock and just a few more strokes had me unloading into her waiting cunt. I didn't want to pull out, but reluctantly I did. My cum immediately started to leak out of her and she lay on the bed for a few minutes catching her breath. I got a towel and cleaned her up gently. Then we got dressed and I grabbed my bag. Cheryl followed me down the stairs. It was just starting to get light out and Cheryl looked out the window. "I was really looking forward to lying in bed and looking out that big window this morning."

"Maybe another time."

"Maybe, if you're lucky."

I locked the door behind us and we went down the steps to the car. The drive to her house took ten minutes and I followed her in. "Stay here. I don't want to wake Krista." Almost thirty minutes later she came downstairs. She had changed into something a bit more appropriate and was carrying a different bag with her. She had also grabbed a quick shower it seemed from her damp hair.

"How about I fix us some coffee? We've got some time according to my estimate."

"Why don't we just grab something at the airport. I know there is a Starbucks and probably a place to eat.

Parking and getting through the airport was a breeze so early on a Saturday and we found ourselves with more than enough time before our flight.

"Damn, almost forty minutes before our flight. I bet we could have enjoyed ourselves some more," I complained.

Cheryl just chuckled at me and continued to read her magazine. Time seemed to drag, but we finally boarded and were in the air. The flight was just over two hours and Cheryl had leaned her seat back and was immediately asleep. Everything went smoothly and we soon found ourselves driving to Kaitlyn's sister's house, just outside of Boston. I had the address and rented a car with GPS, so I trusted the device to get us there. It was almost noon when we pulled up to a middle class, suburban neighborhood. A couple more turns and we pulled up to the house that matched the address.

Cheryl and I had decided she would go to the door, just in case her sister answered and she got nervous about me. "I hope she's home."

"She should be. She said she was going to be home studying all weekend," Cheryl said.

She kissed me, got out of the car and walked to the front door. She rang the bell and waited. A minute later the door opened and Kaitlyn was staring out the door at Cheryl with a look of complete disbelief on her face. Then they were hugging and Cheryl pointed to the street. I had gotten out of the car and was leaning against the front panel. When Kaitlyn saw me she let out a huge screech and raced to the street, jumping into my arms and squeezing my mouth against hers.

"What the hell are you doing here?" she asked after she let go.

"You sounded so sad last night and we both wanted to see you. So, here we are."

"Holy shit, you're the best, do you know that?" Then she was kissing me again. "So explain to me what you're doing here."

"We're giving you a day off. Go pack some stuff and get back here quick."

"I can't go with you guys. I told you last night, I have to study."

"No, you need a break. You're going to burn yourself out. Give yourself some time to relax and unwind."

She got tears in her eyes, but wouldn't budge. "John, as much as I want to go with you guys, I need to get my studying done. I've got two more exams and then I'll be home."

"Look, I understand how much you want to do well, but you're going to burn yourself out if you don't take a break. Come with us and we'll have you back here before lunch tomorrow.

"I can't. You have no idea how hard this stuff is."

"Listen to him sis," another voice said. Kaitlyn spun around and I looked up to see a slightly older version of Kaitlyn. "You've been working too hard. Whoever this is is right."

"But I..."

"No buts. You know he's right. Besides, I've been telling you the same thing for a week now. All you've done is study and mope around the house. You're room is starting to smell and when was the last time you showered."

Kaitlyn's face turned a deep red, but she didn't back down. "I just have a few more days..."

"And you already know the stuff. Every time I quiz you, you get it all right. And mom agrees with me."

"You told mom on me?"

"Yes."

Kaitlyn stood staring at her sister and I saw her shoulders slump. "Sis, this is John, the guy I've been telling you about and that is Cheryl, another one of my friends. John, Cheryl, this is my older sister Tammy."

I held out my hand and Tammy shook it. "Nice to meet you Tammy. Sorry for dropping in like this, but I got the sense she needed some time off."

"You have no idea how right you are. She's spoken a lot about you and I can see why she likes you so much. Not too many guys would fly to Boston just for a girl they barely know."

"Well, she's a great girl, if not a bit stubborn." Kaitlyn didn't even smile or look at me. "Can I speak to her alone for a minute please?"

"Sure," Tammy said. "Can I get either of you a drink?"

Cheryl said, "Sure, I'd love something."

Tammy led Cheryl into the house and when the door shut Kaitlyn said, "You shouldn't have come."

"Well I'm here and there's nothing you can do about it. If I have to, I'll drag you into the car and take you back to the hotel suite by force if I have to."

"Please, don't do this."

"Then I'll strip you down and tie you to the bed so that Cheryl and I can take advantage of you."

"Please John, not now. Just a few more days."

I grabbed her arm and turned her to face me. "No. Tonight you are with me. We'll drop you off tomorrow and you can go back to your little world of studying, but for tonight you're with me and Cheryl."

Her eyes filled with tears and she slowly sunk to the ground in a sitting position and cried. I was concerned and sat down with her. "What's wrong?"

"I don't deserve you."

"Stop being stupid, would you? I'm here and we're going to have a great day together. Just go get dressed, pack some clothes and come with us."

Finally she relented and nodded her head. "OK, you win. I'll come with you. But I have to be home early tomorrow."

"No later then lunch." Suddenly she launched herself at me and tackled me to the ground, kissing my face like a crazy woman. It didn't last very long, but when she was done, she had a smile on her face and was laughing.

"I don't deserve you. You're too good for me."

"You're just tired. Now go get ready."

"It's going to take some time. I need to shower and get myself presentable."

"You look great, if not a bit musty smelling. Go pack your stuff and you can shower at the hotel. I've got some other stuff planned before dinner."

"I'm sure you do. And I'm pretty sure the shower is an excuse to see me naked and take advantage of my weakened state."

"Weakened state my ass. You're body is just as hard as I remember it." I gave her ass a spank and she stood up with a yelp. She reached down, helped me up and pulled me in for another kiss. This one had a lot more passion to it and we had to step back before we went too far in front of her sister's house.

We were holding hands as we entered the house and Kaitlyn was smiling the whole time. She didn't pause as she took me upstairs to her room and as soon as the door was closed she was back in my arms. I started to pull her shirt off, but she stopped me.

"My sister was right. It's been a few days since my last shower. Believe me, I want to right now more then you can imagine, but I'll be a lot more fun after a shower." We kissed for a while longer and then she pulled away and went to her closet. I sat on her bed and watched her pack a bunch of clothes. "What do I need for tonight? You mentioned dinner."

"Pack something nice. I know a really good seafood place near the hotel."

I looked around the room and saw that it was a complete disaster. Tissues were all over her floor and were overflowing from her trash can. The desk was covered with books and papers and the floor around her chair had more stuff piled up high. There were fast food bags thrown in the corner and coffee mugs all over the dresser. The closet was a complete mess with dirty clothes all over the floor around a small hamper.

Kaitlyn had pulled some clothes and was holding up a nice little dress when she noticed me looking around the room. "I'm sorry, I wasn't expecting company." Her face had turned red with embarrassment. "I'm not usually like this. It's been a tough week."

"Have you been sick?" I said pointing out the tissues.

Her eyes turned down when she said, "No. I've done a lot of crying this week."

"Because you broke up with me?"

"Yes. I was afraid you'd never want to see me again."

"I didn't."

She dropped the dress onto her bag and came over to me. "I'm so sorry I did that. I spent so much time thinking about you that I felt like I was neglecting my studies. It was completely selfish, but I also knew that you'd be able to hook up with Cheryl. I had convinced myself it was the right thing to do. Obviously I was wrong, even if it did turn out for the best in the long run."

"You're an idiot, you know that?" Her eyes opened wide, but I pulled her tight and kissed her. This time the kiss turned hot and she didn't resist when I pulled her shirt off. Her body was just as amazing as I'd remembered, if not better. Her breasts were large and firm, her stomach was flat and toned. I held her tight and tried to pull her onto the bed, but she resisted.

"Not yet. I really do need to shower and take care of a few things before I let you go further. But when I'm ready, you better watch out. Last night made me hornier than I've ever been."

I laughed at her and gave her another kiss. "Go finish getting ready." I glanced at her clock and added, "We have someplace to be in about an hour, so hurry up."

"What do you have planned and should I be nervous?"

"Just pack and get ready to have some fun." She grabbed a few things from a drawer, but kept them hidden from me. Ten minutes later we were heading back downstairs and found Cheryl and Tammy talking.

"I was beginning to think you weren't coming back down," Cheryl said.

"Sorry, we had to have a little talk. I'm ready now though."

Tammy said, "I'm glad you guys are finally getting her out of the house. She's been driving everyone crazy for the last week. Maybe I can get into her room and clean it out."

"Don't you dare go in there. It's disgusting and I don't want to put you through that."

"Well, did you at least open a window? It needs to be aired out."

"I'll go do that, but you are not allowed inside. Promise me."

"OK, OK, I'll stay out. But you will clean up when you get home tomorrow."

"Yes ma'am." Kaitlyn gave Tammy a big hug and said, "Thanks sis. I'll be back to normal tomorrow."

"Geez, I hope not. Any chance you can fix her?"

"I'll see what I can do," I answered. Kaitlyn punched me. "She's a pretty touch cookie though, so I don't make any promises." She punched me again.

"I'm going to the car, are you guys coming?" Kaitlyn headed to the door, leaving her bag at my feet.

"It was nice meeting you Tammy. I'll have her home safely." Cheryl was already outside by now and I tried to catch up to her, but Tammy grabbed my arm.

"I'm not sure what she did this week, but I can tell you, whatever it was, she regretted it. She likes you a lot, and I'm not talking about some silliness. When she got back here, she was floating on cloud nine and couldn't stop talking about you."

"Why are you telling me this?"

"Because she has a history of sabotaging relationships for stupid little things. Most guys deserved it, but I get the sense you're a good guy. Stand up to her and don't let her do something stupid."

"Again, no promises, but I'll do my best." Tammy surprised me by giving me a big hug.

"Thanks for coming. She really needs this."

"Your welcome. Hopefully I'll see you tomorrow."

"Probably, I'm usually around here."

"OK, bye." Then I left. The girls were standing against the car waiting for me.

"Ignore everything my sister said. She doesn't know what she's talking about."

"She told my that you are an over sexed little slut and that I should make sure I keep myself safe."

"Yeah, right, because I've been out every night hooking up with strange guys all week."

The girls stepped back from the car and waited. "What?"

"Aren't you going to be a gentleman and open the door for us?" Cheryl asked.

"Mi'ladies," I said as I opened the door and stood aside. They both climbed into the back seat, I shut the door and got into the driver's seat. I set the address for the hotel into the GPS and started on our way. The girls were chatting, so I took the opportunity to look at Kaitlyn in the mirror. I was shocked to realize how terrible she looked. Her eyes were red and she had huge bags beneath them. Her hair was slightly oily and didn't look very good and her face seemed drawn. She looked at me through the mirror and smiled, but turned back to Cheryl to keep talking. Hopefully this night would get her feeling better.

Thirty minutes later we pulled up to the hotel and I helped the girls get their bags. I checked in and was glad to hear that our room was ready. The hotel clerk looked at me and then over to the girls and gave me a big smile. "I hope you enjoy your stay sir. If there's anything you need, please feel free to call the front desk."

"Thank you. I would like to confirm our appointment at the spa for three o'clock."

"Yes sir, I have three reservations for massages as well as two for pedi/mani."

"Thats right. Thank you."

I took the keys and we made our way up to the room. The girls followed behind as we got off the elevator. I pushed the door open so the girls could enter first. I had ordered us a huge suite so that we would all be comfortable and they both were impressed.

"Wow, Johnnie, this must have cost a fortune."

"Not at all. I got a good deal on the room. Kaitlyn, if you want to shower, you need to do it now. We have an appointment in about an hour."

"An appointment? Is that what you're calling it today?" Cheryl laughed.

"OK, give me a little while. I'll be out soon." Kaitlyn grabbed some stuff from her bag and headed through the master bedroom into the bath. "Holy cow," we heard her say. Cheryl ran to see what she was so excited about and I followed.

Both girls were standing to the entrance to the bathroom and were staring. I had stayed here before on business a few years ago and knew what to expect. The bathroom was huge with a large spa/tub and big shower stall with a bench. "You guys like?" I asked them.

"Hell yes. I may not want to leave," Cheryl said. "This bathroom is bigger then my whole master room at home." I chuckled at that and watched Kaitlyn walk over to the shower to turn the water on.

"This shower is just as big as the bathroom I have at my sister's house," she said.

Cheryl turned to leave and said, "I'm going to check out the rest of the place."

I turned to leave, but Kaitlyn said, "Can you stay for a minute?"

"Sure." Cheryl looked at Kaitlyn with a smile and then left, shutting the door behind her.

"So, why did you come?"

"I'm not sure. I probably shouldn't have, considering you broke up with me."

"I'm so sorry I did that. I was wrong and I hope you can forgive me."

"I'm here, aren't I?"

"Yes you are. And I still can't believe that you are." She was standing directly in front of me. "I must look like hell. I haven't gotten much sleep this week."

"Maybe you should take it easy and not kill yourself studying."

"It had nothing to do with studying. I was beating myself up over breaking up with you."

"Then you should have done something about it."

The bathroom was getting steamy and Kaitlyn turned back to the shower. "Can you turn around please?"

"I've seen you naked you know."

"Please. I've kind of neglected a couple of things and want to clean myself up before you see me naked again."

"Sure," I said as I turned around.

I heard the shower door close, turned around and saw her silhouette through the door. I took a seat on the commode so that we could continue to talk.

"Tell me why you really broke up with me."

"Because I wanted you to go out with Cheryl and we thought you weren't talking to her because of me."

"You're both idiots. I tried to call her, but she had my number wrong on her phone. I just didn't leave a message and when she didn't call me back, I gave up."

"So she said."

"You shouldn't have done that. You could have told me that she wanted to ask me out."

"She was afraid you would only have gone because I said it was OK. She wanted to know you wanted to be with her." She stressed the word wanted.

"I guess we need to discuss what's going on here? Am I dating both of you or is she just around when you're not."

"We'll talk after my shower."

I looked at my watch. "We probably won't have time, but we can talk over dinner."

"What's so important that our talk has to wait?"

"It's a surprise. Even Cheryl doesn't know about it."

"Can I get a hint?"

"Sure, it involves all three of us being naked."

"And you need an appointment for that? All you have to do is ask nice."

"Funny girl. You asked for a hint and I gave it to you."

"That's mean. Can you do me a favor?"

WhatIKnow
WhatIKnow
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