Lip and Annie - Cover

Lip and Annie

Copyright© 2010 by jake60

Chapter 2

Drama Sex Story: Chapter 2 - Can Texas Holdem bring two lonely souls together? Or will they lose on life's river card. You've got to know when to hold them....[Sorry, I had to go with the poker flow, but it's not 'the' story.] Note the CAUTION category. It is explained before the story starts.

Caution: This Drama Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Reluctant   Heterosexual   Safe Sex   Oral Sex   Masturbation   Petting   Slow   Caution  

Two days after returning to Thunder Bay, Robert sent Annie an email, asking how she had done at the tables on Sunday night. He let her know that he had managed to come out ahead by $150, which when added to his previous day's winnings meant that he had had a very successful weekend.

About three hours after he had sent her the message, he heard his laptop announce that an email had been received. When the TV show that he was watching had ended, he went to check his messages and discovered that Annie had replied to his earlier message.

She let him know that she had broken even that last night, but was quite satisfied considering her large win on Sunday afternoon. Throughout the evening she had been working on making sure that she developed a standard routine when checking her chips, and felt that she had been able to eliminate the tell that Robert had taken advantage of. She thanked him for agreeing to share his knowledge of the habit that had cost her his participation in the hand that had won her so much money.

It was mid-November, and Robert's business was getting busier day by day. A lot of his clients sold their products on the Internet, and the Christmas rush was already well under way. When he wasn't busy on their behalf, he found time to play poker online. Even though he couldn't pick up clues from the physical appearance of the other players, he was able to make some observations of their online habits that allowed him to come away with a profit most days. He missed the opportunity for human contact though, and was already looking forward to his next trip to the Grand Casino Hinckley.

At the end of his first week back he received a mailing from the casino that included coupons for a free stay over the last weekend of the month. There were also coupons for $40 worth of free chips, and he immediately decided that he wanted to make the trip to Hinckley that weekend. Once he had made that decision, he wondered if Annie would also receive similar coupons. He had enjoyed her company at supper that night, and while he knew that she doubted he was telling the truth about never having been on a date, it was true. While he entertained no thoughts about anything developing between the two of them, he wouldn't mind talking with her again.

With those thoughts in mind he sent her an email that night, letting her know that he had received some coupons for the casino, and that he intended to go down for the last weekend of November. Shortly after he had sent her the message, he made a phone call to the casino to book his room.


That weekend Robert took Fred and Sherry out for supper, and did manage to slip in a couple of mild stories about Fred's years in high school. It was nice for him to spend some time with the couple, and he soon decided that he really liked Sherry, while Fred had been a good friend for what seemed like forever. Later, after enjoying a good meal with them, Robert begged off when they suggested he join them for drinks and dancing in the attached bar.

He had been in that situation a few times in the past; the unattached guy with a couple who wanted to go out and party. It always ended up with him feeling embarrassed at being turned down by an unattached female after he had asked her to dance. It seemed that in every case the couple he was with would feel obligated to find him a dancing partner, and the night would always end on a sour note when they couldn't convince a female friend to join their group. He couldn't help but know that his scar and the nasal sound of his voice were the largest contributors to the problem.

The weekend ended on a good note though, when he found a new message from Annie in his mailbox on Sunday night. She told him that she had received a similar coupon package from Grand Casino Hinckley, and would probably be using her coupons as well. She had already verified that her shifts at work wouldn't conflict with the plan, and all she had to do was reserve her room. Robert was feeling surprisingly happy about the news, and sent her a quick reply saying that he looked forward to seeing her there. Even though his trip to Hinckley wasn't scheduled for almost 2 weeks, he was already planning for it.


Robert was kept very busy over the course of the next seven days and didn't have much time to think about his upcoming trip. With some free time on Sunday afternoon he began to think about preparing for the drive to Hinckley, wondering what the chances for early winter weather were going to be. It occurred to him that since he was going to be passing right through Duluth, he could offer Annie a ride to and from the casino. With that in mind he wrote her another message, this time offering to pick her up and asking for her address in Duluth. He was looking forward to hearing back from her.

As each day of the following week went by, he anxiously awaited Annie's reply, and was rather surprised that he hadn't heard from her. Finally on Thursday night, just before he was going to retire for the night, he found her reply in his Inbox.

He was rather surprised by the curt nature of her message. She simply said that she appreciated the offer, but she would be taking her own car to Hinckley. There was no explanation as to why she wanted to take her own car as opposed to accepting a ride from him, and he was surprised at how much the tone of her short message bothered him. For someone who was quite used to getting negative responses from the opposite sex, he hadn't anticipated this reaction from Annie. He finally decided that perhaps he was simply reading too much into her email or how she perceived him.


The next morning he packed his suitcase, gathered his toiletries and laptop, and was on the road by 9 a.m. He was looking forward to a couple of days of relaxation, good poker and good meals. He had been looking forward to Annie's company as well, but her reaction to his offer of a ride to the casino had more than dampened his enthusiasm. Most men would simply plan on moving on to the next available woman, but that wasn't an option for Robert. He had few female friends, and none who were interested at all in playing poker.

The trip was made without incident, and he arrived at the casino at 3 p.m., which was the normal check-in time. He quickly made his way through the check-in process and was soon on his way to his room where he quickly had his clothing unpacked and his toiletries set up in the bathroom. He had made enough of these trips to be able to take care of these normal activities quickly.

Rather than immediately heading for the tables, he decided to check his email account and take care of any of the required website changes he would find there. There were three requests for information and modifications, so he spent the next hour dealing with those. By the time he was finished, a fourth request had also arrived, so he spent another half hour performing the work that it demanded. With all that time spent playing catch-up, he decided that it was late enough in the afternoon that he may as well go down and have supper before heading for the poker room.

By the time he was seated in the restaurant, he realized he had been watching for Annie on his way through the casino, and even in the restaurant as they took him to his seat. Later, as he was enjoying his meal of prime rib of beef, he thought of her again, and how much he had enjoyed her company the last time he had eaten a meal like this. It was obvious that she had had an effect upon him, something that he thought he had hardened himself against. He decided that he would just have to work harder at protecting himself from disappointment at the hands of the opposite sex.

By seven o'clock he was seated at a poker table, and the only thing on his mind was developing a read for the other players around the green felt. He was in his element now; it was Robert against the world. Over the course of the next six hours he did make a lot of headway against the other players that came and then went as their chip stacks dwindled away. Robert had a very productive evening, and a lot of the chips that the other players lost ended up in front of him. By 1: 30 in the morning he was seated at the bar enjoying a beer, with almost $600 in profits safely in his pocket.

It was five minutes after 2 a.m. when he entered his room. He immediately went to his laptop to check the status of his email account. There were two new messages from clients requesting work on their sites, and when he checked them, he saw that one of the jobs would only require about five minutes of work. Believing that there was no time like the present, he called up the required files and had the job done quickly. The other job could wait until the morning.

As he undressed for bed he happened to notice that there was a flashing 'message' light on his telephone, so he called the front desk for the message. There were very few people who knew he was in Hinckley, so he was a bit curious as to what the message was about. He was surprised to learn that the message was from Annie, and had been left there for him early in the evening. Considering the time, he decided against calling her room, and instead planned to do that in the morning.

The news that she had tried to reach him cheered him up as he lay in his bed, and his last thought before drifting off into sleep was to wonder what it was that she had called for. He had already managed to start relegating his thoughts of her to the back of his mind, and he hoped they weren't going to be dragged back out to hurt him. That had happened to him too many times in the past for him to want to go through the 'same old same old' once more.


Robert was sound asleep at 8:30 the next morning when the ringing of his phone woke him up. Normally he would be up by this time, but because of the late night spent at a poker table, he hadn't set his alarm clock. He was still getting his bearings as he picked up the telephone and answered with a curt, "Hello."

After a couple of seconds a woman's voice, a voice that he quickly realized was Annie's, said, "Robert? Is that you, Robert?"

He was completely awake now and answered, "Yes, it's me. Good morning, Annie. I was going to call you this morning. I got your message last night, but it was pretty late. What can I do for you?"

Annie could sense the detachment in his voice, and quickly replied, "Oh, I wasn't needing anything done; I was hoping to join you for supper last night." She hesitated before continuing, "I guess we could have breakfast together instead, if you like."

Robert was momentarily at a loss for words, but finally said, "Sure, if you'd like to go for breakfast, that would be great. It will take me about half an hour to get ready, as I need to take a shower and shave." He reached over for the note that he had made the night before, looked at it and said, "You're in room 418, aren't you? How about I meet you there as soon as I get ready?"

Annie seemed unsure as she answered, "Ah ... okay; that would be fine, I guess. I'll be waiting for you."

After saying their goodbyes, Robert bounced out of bed and headed for the shower. He wasn't sure what he had expected Annie to say, but being invited to join her for breakfast hadn't made the list. He was soon whistling under the spray of hot water.


Right on time, Robert knocked on the door of room 418. It was opened almost immediately, and Annie stepped out quickly into the hallway. She smiled at him and said, "I'm sorry I woke you up. I didn't want to wait too long in case I missed you; I was afraid you'd be down in the poker room."

Annie was smartly dressed in a pair of dark slacks and a figure hugging green sweater. It seemed that she had changed her hairstyle a bit, although Robert couldn't be certain of that. He just knew it suited her.

He smiled at her and lied a bit as he said, "I shouldn't have been sleeping so late. I don't mind having you wake me up; I'm quite ready for breakfast."

The two of them walked the familiar route through the casino to the restaurant, and were soon seated in the same booth that they had occupied almost a month earlier. After they placed their order Robert said, "I'm sort of surprised that I heard from you. When you said you didn't want a ride down here, I sort of assumed you weren't interested in hearing from me."

There was obvious discomfort on her face as she said, "Oh, Robert. I'm sorry if I gave you that impression. I ... I just didn't want to agree to travel with you until I got to know you better. I should have explained myself."

Annie's revelation that she was hesitant to join him for the 1 1/2 hour drive from Duluth to Hinckley surprised Robert. He had never before had anyone express hesitation about being alone with him, and he found it hard to understand. He began wondering if he had given off some form of signal that caused her concern. "I'm sorry if I gave you cause to wonder if you were going to be safe with me. I can assure you that I have nothing but respect for you."

Annie was clearly embarrassed, and seemed at a loss for words. Before she could say anything else Robert added, "I never considered that you would be nervous around me." He laughed before he continued, "Believe me; I am the most trustworthy person I know."

She was still clearly embarrassed, but his comment drew a smile, and she said, "I really am sorry, Robert. Someday maybe I'll explain to you why I have this problem. Please don't be upset with me."

Robert smiled broadly at her and said, "How could I be upset with you. You're my only poker playing female friend, and I enjoy your company. I just sort of thought that you were pushing me back a bit. I have sort of come to expect that type of treatment, and maybe I overreacted."

Annie looked at him questioningly and finally said, "I'm not sure what you mean by 'that type of treatment'."

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