Perplexed Pt. 01

“Hello?”

“Greg? Oh, thank goodness you’re there,” Dana said between tears.

“Dana? What’s wrong?”

“The train was full. I couldn’t get a ticket. I am at the train station, and I don’t know what to do. Greg, please help me.”

“I’ll figure something out. Call me back in five minutes.”

“Okay. I will talk to you soon.”

“Bye.”

“Bye,” Greg said. He hung up the phone. He looked at his map of Chicago. There was a circle on the map. Greg looked closer, and the circle was at the intersection of State Street and Harrison Street. The word “Travelodge” was written next to the circle.

Greg picked up the phone and dialed information.

“Information, what city please?” the voice in the phone answered.

“Chicago, Illinois,” Greg responded.

“What listing?”

“The Travelodge on Harrison Street.”

“Thank you.”

The line clicked, and a pre-recorded voice was heard.

“The number is 800-578-7878. This call can be completed for no charge if you press one.”

Greg pressed the one key on the handset.

“Thank you for calling Travelodge reservations. This is Andre. How may I help you?”

“Hi. Do you have any vacancies for tonight?”

“Yes, sir. We do have a few rooms left.”

“What is the rate?”

“We have a non-smoking room with a king-size bed for $96.”

“That will be fine.”

“Name?”

“Greg Simmons.”

“I will need a credit card number to hold the room.”

Greg gave Andre the number from his Visa card, and the expiration date.

“Thank you, sir. Is there anything else I can help you with?”

“Yes, there is. I will not be coming in until late tonight. But, a young woman named Dana Nelson will be coming in shortly to check in. Will that be a problem?”

“No, that will not be a problem. I will add her name to the reservation.”

“Thank you.”

“Okay, I have you down for a king-sized bed, non-smoking, for one night at the Travelodge at 65 East Harrison Street in Chicago. You or Dana Nelson will be checking in tonight. Your confirmation number is 897456.”

“That is correct.”

“Thank you for choosing Travelodge.”

Greg hung up the phone. A few minutes later, it rang.

“Hello?”

“Hi, Greg,” said the voice, timidly.

“Hi, Dana. I have a plan. Are you ready for it?”

“I guess so. Greg, I am so scared.”

“It’s okay, Dana. I promise you it will be all right. Are you ready to take some more notes?”

“Yes. Where am I going?”

“I booked a room for you at a hotel.”

“Greg, I don’t want to spend the night alone in the city. Please, there must be another way,” Dana sniffled as she fought back the tears.

“Dana, you won’t be spending the night alone. I am coming to get you.”

“Really?”

“Yes, I am. But, we will need to spend the night in Chicago. Is that okay with you?”

“Are you serious? You are too nice to me. Greg, I don’t know what to say.”

“You can think about it while I am driving to Chicago. Are you ready to take some notes?”

Dana took the cap off her pen.

“Yes, I am ready.”

“Go out of the train station, and get back on Adams Street. Cross the river, and walk towards the Sears Tower. Walk for about six blocks down Adams Street, until you come to State Street. Make a right on State Street, and walk for three blocks to Harrison Street. Make a left on Harrison, and there will be a Travelodge there. There is a room in our name, the confirmation number is 897456.”

“Okay, I think I have it.”

“It is six o’clock now. If I leave right away, I can be there by eleven.”

“Please hurry, Greg.”

“I will go as fast as I can.”

“Thanks. You are too sweet to me.”

“You deserve it, Dana. I will see you soon.”

“Goodbye.”

“Bye, and take care,” said Greg, right before he hung up the phone.

Chapter 22

Kristy had spent two hours looking for Shane at the party. She would walk from the kitchen, where she could fix herself a gin and tonic, to the family room, out to the deck, into the laundry room, and down into the recreation room in the basement. There was no sign of him. Shane had told Kristy that he would be there, but it looks like she had been stood up.

After four laps through the house of a well-to-do classmate, and four gin and tonics, Kristy went upstairs, and pouted in a bedroom, working on her fifth mixed drink. Wendy, wearing a pink sleeveless top, white ruffled skirt, and flip-flops sat next to her on the bed. She drank a rum and Kool-Aid on the rocks.

“Hey, Kristy, what’s wrong?”

“It’s Shane. He said he would be here tonight, we were supposed to talk.”

“Were you going to get back together with him?”

“Wendy, I love him so much. I hope that I haven’t lost him.”

“After what he said to you at the prom, are you sure you want him back?”

“That’s just his sense of humor. I overreacted,” Kristy starting to gently sob, as the alcohol toyed with her emotions.

“It’s okay, Kristy. Everything will work out,” Wendy said, softly holding her best friend’s hand.

“He always made me feel wanted. I hope I haven’t screwed it up.”

Wendy set her drink on the nightstand, and hugged Kristy.

“Oh Kristy, it will be all right.”

Kristy started to cry more.

“I feel so alone. Something’s missing without Shane.”

“I’m here for you, girlfriend.”

Wendy released her hug. She ran her hand through Kristy’s hair.

“Thanks, Wendy. You’re a great friend.” Kristy hugged Wendy again. Wendy held her tight.

“Shh, you’ll be okay, Kristy,” Wendy whispered. Wendy leaned back, so that the girls’ noses were almost touching. Kristy’s hands were behind her neck. “You’ll always have me.”

Kristy kissed Wendy on the lips.

“Kristy, what are you doing?”

“I don’t want to feel lonely. You’re so pretty, and I just love you so much.”

Kristy kissed her again. Wendy felt a tongue against her lips. She had never been with another girl before. Wendy opened her mouth and her tongue met Kristy’s. Wendy gave in to Kristy, and shed her inhibitions.

Wendy pushed her weight forward, causing Kristy to collapse on the bed. Their chests were pressed together, and Wendy’s hand started to feel Kristy’s inner thigh. Wendy’s gentle fingertips grazed Kristy’s soft skin. The girls’ tongues rolled over one another. Kristy felt warmth in her mouth, and heat on her body. Wendy’s hand moved further up Kristy’s dress, rubbing a wet spot in Kristy’s thong. Kristy’s nerves were on pins and needles. She couldn’t take the teasing, but she didn’t want Wendy to stop.

“Stay right there,” Wendy said after she broke the kiss.

Wendy got up, and closed the bedroom door. Kristy was too shocked to move. Wendy turned off the light, and kneeled on the bed near Kristy’s waist. She pulled the hem of the black cocktail dress up to Kristy’s navel. She started to tug the black thong down Kristy’s legs.

“Wendy, I’ve never done this before.”

“Neither have I. You’re so hot, and it feels so good. I want to make you happy.”

Wendy put the thong on the bed. She pulled her pink shirt over her head, while moving between Kristy’s legs. To Kristy, it looked like she was wearing a purple bra. Kristy and Wendy had shopped for lingerie together, so she knew that Wendy was a size 36C. Kristy had always been a little jealous of Wendy’s bust. Wendy’s figure in the moonlight made Kristy realize how sexy Wendy’s breasts were. Wendy pulled off her bra, and bent between Kristy’s thighs.

“Hand me a pillow.”

Kristy dutifully gave Wendy a pillow from the queen-size bed. Wendy pushed upward on the side of Kristy’s buttock. Getting the hint, Kristy raised her hips, and Wendy put the pillow beneath her. Wendy put her shoulders on the back of Kristy’s thighs, feeling her calves on her bare back. Wendy started to feel Wendy’s flat stomach, and lowered herself to taste her best friend’s pussy.

Wendy did her best to not bury her teeth into Kristy’s pubic flesh. The pungent taste of Kristy’s juices disgusted her at first, but she had come too far to stop now. Wendy’s tongue started to tingle as it got used to the flavor and smell. Wendy tried to push her tongue deeper into Kristy. She flittered her tongue, as if she were a cat lapping up milk. Wendy wanted to pleasure Kristy, wondering if her tongue was satisfying Kristy’s pent up frustrations.

Kristy’s body started to go numb. She stopped caring that there was a party with over a hundred guests downstairs. She stopped thinking about Greg and Shane. All she wanted was for the magical work on her clitoris to continue. Her arms were pulling her dress further up her body, touching her sides and her chest, occasionally encountering Wendy’s fingers. Kristy started to moan as she felt the tension rise in her body.

The door opened, and light from the hallway flooded the room.

Chapter 23

Greg had dressed and packed quickly. A backpack with toiletries and a change of clothes was all he needed. A note was left for his parents to explain the situation. Another note with the same contents was taped to the door of Dana’s apartment for her mother to read.

Greg ran down to his Chevy Cavalier and drove under the gateway, and out of Thomas Mill. His head was clouded with thought. He had sex with his sister twice today. That is the same number of times that he had met Dana. Yet, he was driving three hundred miles to see her.

He tried to rationalize the situation. Technically, they weren’t in a relationship. There was no verbal commitment between the two of them. He had never said he would not see other people.

His feelings for Dana were suddenly not as overwhelming. He had doubts if they could have a lasting relationship. Kristy was much prettier than Dana, and Greg estimated that Kristy was better in bed than Dana. Dana’s inexperience had the potential to be frustrating, and he didn’t want to teach her everything about sex.

Maybe Kristy wouldn’t get back together with Shane. Greg could try and talk her into going to Central Iowa State. Perhaps she could be persuaded to share an apartment with him. Greg explored the possibility of dating his sister. Children and marriage would not be an option. It would be difficult to keep such a close relationship a secret. If they had a falling out, it could destroy the Simmons family.

Greg’s thoughts were racing through his head, like the dotted white lane lines were dashing past his car. The solution could be to date Dana, and keep Kristy on the side. If he tired of Dana, he would still have Kristy. He and Kristy could have a no strings attached relationship. His whole relationship with Dana would be based on lies. Greg wrestled with the thought of living dishonestly.

Dana had done nothing to deserve that treatment. She had been warm, caring, and trustworthy of Greg. Greg didn’t know if he could continue breaking that trust. The girl who had just walked out on her father had asked Greg for help. Greg responded by screwing his sister. A pain from guilt hit Greg in the stomach.

Greg saw the sign for Interstate 55. He took the northbound entrance ramp. He would have three hundred miles to sort out these feelings.

Chapter 24

All Kristy could focus on was the intense feeling of pleasure that was overtaking her body. Wendy popped her head up to see who had entered the room, but Kristy forced her head back into her crotch.

“Don’t stop now! Please don’t stop!”

The door closed, and again the room was dark. Wendy resumed her tongue play on Kristy, but she was aware that someone had entered the room. She heard Kristy moan, but she also heard a zipper. She tried again to see who was there, but Kristy stopped her. She felt a weight behind her on the bed. Her skirt was being lifted up. Wendy licked recklessly, trying to bring Kristy to orgasm, so her head could be released. Wendy’s panties were pulled down to her knees, and her bare bottom was in the air. She felt a pair of strong hands grip her waist. She couldn’t move, as she felt something rubbing against her vagina. Wendy realized that it was a penis, and the stranger was about to penetrate her.

Kristy’s body burst with a powerful orgasm. She clenched Wendy’s hair as her body went stiff. Energy radiated out of her body and she tried not to scream. Her legs, arms, back, and neck seemed to clutch, and then release as she started to come down. She had trouble catching her breath, and she was shaking.

At that moment, the stranger thrust his penis deep inside Wendy. It was bigger than anything Wendy had ever felt before. She felt his balls against the back of her thighs and Wendy dug her fingernails into Kristy’s thighs. The man bent over so his chest was against Wendy’s back. He reached around and started to play with Wendy’s hard nipples. At that angle, the man’s penis massaged her clitoris as he started to slowly move in and out of her. Wendy relaxed as she fell into her own state of sexual bliss.

Kristy was too exhausted to move, she saw the scene before her. The man’s curly, raggedy hair on the top of his head, and his big arms as he held Wendy was all that was visible. He was strong with Wendy, but careful. He didn’t impose his will onto Wendy, instead she looked secure. She looked safe, as the man gracefully fucked her.

Kristy saw the man slowly thrusting in and out of her best friend. He released Wendy’s breasts, and straightened his back. Wendy had a look of pained pleasure on her face as she continued to be filled by the unknown man. She was too drunk to be scared, and too aroused to tell the man to stop.