Chapter 8: Expectations

It was Friday night and Roger was dropping off his date for the night. Jill Abrahms was the last woman Roger would ask out from the single parent groups. He had already asked out all the rest of the women that interested him. And one date with Jill was enough. Roger felt like he spent half the night just trying to get her to pay attention to him.

With The Plan, or what was left of it, running out of steam, Roger wasn’t quite sure what to do next. Well, he still had a couple of women with long term potential. Jessica was certainly promising.

It was six o’clock on Saturday when Roger arrived at Jessica’s house, wine bottle in hand. He handed it to Jessica with a gentle welcoming kiss. Jessica asked, “Would you like something to drink, Roger?”

“Why don’t you open the wine I brought,” Roger suggested. Jessica turned and left the room.

A couple of minutes later, Jessica returned with two glasses of red wine. After she handed Roger his glass, but before she could sit down, Roger asked, “Do you have any family photo albums we can look at?”

Jessica’s face reflected her puzzlement at the request. She quickly recovered and answered, “Sure, just give me a minute to go find them.”

She went to a trunk in the corner of the living room and pulled out two albums. Jessica returned to the couch and sat down next to Roger while she placed the albums on the glass coffee table in front of them. Jessica opened the first album and started a running commentary about the pictures inside. Roger looked at the pictures, including the kids playing on the beach, or Sadie’s (the oldest) 8^th birthday party. Roger asked about some of the other people in the pictures. Jessica spent about ten minutes going through the photos with Roger.

When Jessica went into the kitchen to start dinner, Roger spent a few more minutes looking at the pictures. As he looked at the album, Roger couldn’t help but think about Jessica. She was an attractive woman with a very pleasant disposition and a sharp mind. She was also very attentive to Roger. She had two daughters and a son. He hadn’t heard much about Blake, yet, so he wasn’t sure how he fit into Jessica’s life. All this left Roger unsure how he wanted to proceed with Jessica. Then he remembered Dr. Franke’s advice – “relax” and “have fun”. Having tensed up while thinking about all this, Roger took a deep breath and let it out. His shoulders relaxed, and he slumped back into the couch.

Roger sat down for a nice dinner of tender, juicy ribeye steak, buttered green beans and mashed potatoes.

As they ate, Roger said, “Jessica, this may be the best meal I’ve ever had.”

Jessica blushed and smiled, saying, “Thank you. I’m glad you like it.”

After dinner, Roger sat with Jessica on the couch and watched Death Becomes Her while they drank wine. When the movie ended, Roger suggested, “Shall we go to bed?” Without waiting for an answer, Roger grabbed Jessica’s hand and led her to the bedroom.

When they got to the bedroom, Roger turned and pulled Jessica in for a passionate kiss. His mouth was on hers before she could even take a breath. Roger’s hands wrapped around Jessica’s body and slowly started caressing her back with one hand while he squeezed her butt cheek with the other. He broke their lip lock and immediately started to kiss and suck on her neck. Jessica was still recovering from the sudden attack and embrace. She grabbed his waist and just tried to hold on as Roger passionately sucked on her neck and shoulders.

With her temperature raised, Jessica moved with Roger over to the bed. He laid her down and started to undo the buttons on the pale blue silk blouse that Jessica had worn that evening. With her soft breasts exposed, Roger went to suckle on Jessica’s large, pink areola. He started on the left breast and lightly sucked the nipple into his mouth and then nipped at it with his teeth. This brought a moan from Jessica as she brought her hands up to hold Roger’s head to her chest.

While Roger worked on Jessica’s breasts with his mouth, he eased his hand up Jessica’s leg, using his finger nails to lightly scratch up the inside of her thigh. His hand worked higher under the black, knee-length floral print skirt that Jessica wore. Roger was surprised to find that not only had Jessica not worn a bra this evening, she had also gone sans-panties.

Roger lightly touched Jessica’s slit with his index finger. As her pussy grew wetter, Roger started to worm his middle finger inside while lightly rubbing her clit with his thumb. After a couple minutes with Roger working on Jessica’s breasts and pussy, she pushed him up and removed his pants. Freed of his pants, Roger guided Jessica back down to the bed and moved between her legs. She placed his cock at her wet opening. Jessica was so worked up that Roger pushed forward and drove home in one stroke.

In her highly aroused state, it only took a few strokes for Jessica to reach orgasm and scream out in pleasure. Once Jessica came down from her first orgasm, Roger helped to reposition her so she was on her side and he straddled her right leg. In this position, Jessica quickly built up to another orgasm and started grabbing the comforter as she tensed and screamed out her second orgasm. Straining to hold back, Roger took Jessica’s second orgasm as permission for his own release. He pulled out of Jessica and came on her thigh.

Roger laid down behind Jessica and wrapped his right arm around her. Both lovers lay on the bed catching their breath. After a few minutes, Jessica got up and used a moist wash cloth to remove the cum from her leg. While she did this, both she and Roger finished removing their clothes.

Once clean, they pulled back the covers and climbed into the bed. They kissed on the lips and teased each other’s tongues. After a few minutes of kissing, Jessica’s head disappeared under the covers. She found Roger’s shrunken member and started to lick and suck on it. After a few minutes of Jessica’s attention, Roger’s cock started to grow. She started to increase the intensity of her efforts and took the first several inches of Roger’s cock into her mouth.

Once he reached full hardness, Roger turned Jessica over and eased her back down on the bed. He then lowered his head to her pubic mound where he admired her well-trimmed bush that had been shaved into a narrow triangle above her slit. He started by nipping at her inner thighs, moving from side to side as he moved closer to her pussy lips. Jessica started to gasp as he moved closer to her moist opening. As the pitch of Jessica’s squeals rose, Roger grabbed her lips between his thumb and index finger and squeezed the two sides together. At the same time, Roger licked Jessica’s clit and she screamed and tensed as the overwhelming intensity of the pleasure surged through her muscles. Roger kept licking her clit for a few more seconds as Jessica rode out the orgasm.

Once Jessica hit that first orgasm, she was off to the races. For the next ten minutes, Roger kept pinching Jessica’s vulva and licking and nibbling at her clit and licking her pussy lips. While he did this Jessica experienced four more strong orgasms.

Finally, she grabbed his head and begged, “Stop ... Stop...”.

Roger stopped, but only momentarily. He moved up the bed over Jessica and didn’t pause as he quickly slid his phallus into her soaking box. After a few minutes, he erupted inside her and collapsed in exhaustion.

Once he caught his breath, Roger went to the bathroom. He cleaned up and got a clean wash cloth with warm water and came back to bed to clean Jessica. After his task was completed Roger spooned in behind Jessica and the pair was soon asleep.

Roger awoke to a warm moist sensation on his groin. In his dazed state, he reached down to find Jessica’s head. Roger maintained contact with Jessica’s head as she brought him to another climax. Jessica swallowed what Roger gave her and continued to suckle and swallow for a couple more minutes as Roger started to shrink in her mouth. He got out of bed, glanced at the clock, which said 3:12, and he headed to the bathroom to relieve himself.

The next morning Roger lay in bed thinking. ‘Is she the right woman for me? How does she feel about submissiveness or Polyamory?’ He needed time to sort things out in his head.

About fifteen minutes after Roger woke up, Jessica rolled over and placed her arm across his chest. Roger gently started scratching her back.

“Good morning,” Roger said softly.

“Morning,” she croaked back.

They rested, holding each other for a few minutes.

“Look, Jessica, I hate to kiss and run, but I need some time to think about us, before we go any further. I’m going to head home. I’ll call you later in the week.”

Suddenly more alert, Jessica responded, “Umm, okay. You’ll call me?”

“Yes, just give me a few days to sort some things out,” Roger said.

Roger dressed and left a rather stunned Jessica.

Jessica called Roger’s cell phone on Monday, but Roger was at dinner with a client in Georgia. She left a message on his voicemail.

“Hi, Roger, it’s Jessica. After the way you left yesterday, I’m a little worried. I hope everything is okay. I really want to see you again. Give me a call so we can talk.”

Roger called Jessica back later that evening, but only to tell her he needed more time to think.

By Thursday, Roger was ready to talk to Jessica.

“Hi Jessica,” Roger said into the phone, with a sigh.

“Roger,” Jessica replied, cautiously.

Quietly, Roger continued, “I’ve had some time to think and figure out what I want to say to you, but I don’t think this is a phone conversation.” He paused. “Can we meet for coffee on Saturday, or would that ruin your Valentine’s day?” Roger asked.

“I don’t mind meeting on Valentine’s day,” she said, firmly.

“Great. What about the kids, will they be okay?” Roger asked with a touch of concern.

“No ... no problem with the kids. They’ll be with their father this weekend,” she said.

“Okay. Can you make it at ten o’clock?”

“Yeah, I can make it at ten,” Jessica answered.

“All right, I’ll see you at ten this Saturday at Starbucks on Peachtree,” Roger concluded.

“See you then, Roger.” Jessica said, ending the call.

Friday night, Roger picked up Cathy for dinner and dancing.

During the drive over to the restaurant, Cathy asked, “Do you think we can go out on Saturday night next time?”

Roger sighed.

“Look, Cathy, so far I’ve been free on Friday nights. If we want to go out again and I’m free on Saturday, we’ll go out on Saturday. Putting unreasonable demands on me is a good way to bring this relationship to a quick end,” he answered as his face slowly turned to a frown.

“Sorry, Roger. I’m just a bit frustrated. Each of our dates has been on a Friday night so far. I just don’t feel like I get to spend enough time with you,” she pleaded.

Roger’s expression softened. “I’m sorry, too. I have a very busy schedule and I’m pretty sensitive to having someone tell me how to run my life.”

Cathy was pleasant for the rest of the evening. She even matched Roger step for step when they tangoed.

As agreed, Roger met Jessica at Starbucks. Once Roger and Jessica both sat down with their drinks, Roger started, “Jessica, you look lovely, as usual.”

“Thank you, Roger,” Jessica replied flatly, without any emotion.

“I’m sorry I’ve been so aloof this last week. You’re the first person I’ve started to get serious with since Stacy died. I’m trying to make sure we both know what we’re getting in to. I’ve been thinking about what I want my life to look like going forward and how you fit in. So, I’m going to tell you some things now that may be difficult to hear.” Roger took a deep breath and paused for a minute, giving Jessica time to process what he had said so far.