Lip and Annie - Cover

Lip and Annie

Copyright© 2010 by jake60

Chapter 5

Drama Sex Story: Chapter 5 - 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  

Over the course of the next two weeks they exchanged emails on an almost daily basis. Robert could tell that Annie seemed to be much more open as she corresponded with him. On several occasions, late in the evening, he found an excuse to phone and speak to her directly. They had pleasant conversations for over an hour each time.

Neither of them was quite ready to plan their next poker trip. Robert had lots of work with his business, and she was working extended hours due to injuries three nurses had suffered in a traffic accident on the icy streets.

The third week of January proved to be of great consequence to both of them as individuals, and ultimately to their budding relationship.

It started when Annie wrote an email that excitedly informed Robert that she had been invited by one of the male nurses to accompany him to a retirement party for one of their supervisors. She had agreed, and was positively excited about having had the confidence to agree to attend the party with him.

This information caught Robert very much by surprise, and upset him much more than he would have thought it would. This message had the effect of making him believe that he had helped Annie to get over some of her fears, only to let one of her coworkers be the beneficiary of her new-found confidence and courage.

There wasn't much time for him to mull over this news, as the very next day his sister phoned him in a panic, wanting him to arrange to come immediately to Toronto to do some work on a computer network that her company's lawyers used.

The firm that normally did the work had suddenly declared bankruptcy, and it seemed that the other firms that should've been able to take on the job were already backlogged with new clients that had resulted from the bankruptcy. The legal office was having trouble with their server, and were unable to generate billings.

Patty sounded desperate on the phone, "Please say you can catch the first flight for Toronto. I know you can help us out much better than the smaller companies here could. We're sort of desperate. You can stay with Mike and me, in our guest bedroom, and the company will be happy to pay your other expenses as well as your hourly rate."

By the time he got off the phone, Robert had agreed to take the next flight to Toronto to help his sister's firm out. He knew that he could do his normal work from virtually anywhere, including Patty's condo. By the next morning he had arranged an early flight, packed his suitcase and laptop, and was standing on the concourse of the Thunder Bay Airport waiting to check in.

Two hours later he was in Toronto taking a cab to his sister's office. She quickly introduced him to the office manager, and he wasted no time in getting to work.

That night, at his sister's condo, he was finally able to thank her for getting him the job, and settled into the guest room in her condo. Patty was a willowy 5 foot eight, just a bit shorter than her brother. Her shoulder length hair was lighter than her brother's, approaching dark blonde. Mike, her boyfriend, was just slightly taller than her, and sported a shock of red hair.

Robert had met him on an earlier occasion and found him to be fun to be around, as his sense of humor was infectious. He also noticed that the two of them had settled into a very comfortable living arrangement together, and he decided that they were as good as married by their actions.


The next few days were very busy for him, but by the end of the second day everything was under control with the balky server, and he was spending his time auditing the hardware and software that had been in use at the firm. He had already advised his sister that there were improvements that they could make to prevent a similar outage in the future.

Within half a day the firm's senior partners and their accountant gave Robert the go ahead to prepare a proposal for them. As a result of his long and busy days at the law offices, he was forced to skip over Annie's emails so that he would be able to have enough time to maintain his own business in the evenings.

Finally, with some time to sit back and relax, Robert brought up the various emails that he had set aside for lack of time. Besides several from Annie, other friends had also been in touch with him, and he began reading and replying to them in order.

When he finally reached the first of Annie's emails, he discovered that it was a long and very cheerful description of how much fun she had had at the retirement party.

As he read, and then reread her message, Robert felt himself slowly but surely becoming deflated. This description of how Annie, and her date Sid, had enjoyed dancing at the club that the majority of the guests had attended after the retirement party was over, got to him.

He couldn't help but feel that he had given Annie the confidence she needed to carry on with her life. She even told him how in the low light of the dance club she had been able to remove the sweater she wore over her short sleeved blouse. She was ecstatic that none of their party had commented about the scars on her arms, assuming they had noticed them at all. She thanked Robert profusely for helping her to see herself in a new light.

It took Robert a few minutes to work up the desire to even answer her message. When he did write, his reply to her was a terse three lines congratulating her on finally getting out, and letting her know that he was working in Toronto for the next week or so.

His interest in replying to any of his remaining messages had evaporated in tandem with his growing belief that Annie would be moving ahead without him, and he soon shut down the laptop before heading for the shower and his borrowed bed.


Robert managed to keep very busy the next week as he inspected the network, decided on a course of action to recommend, and then implemented the changes that were agreed to almost immediately after he had made them. Finally, he created documentation that would allow any future firm contracted to work on the system to fully understand the system and what he had done with it.

He had spent most of his evenings at the law firm, leaving himself hardly any free time to keep up to date with his own clients, and virtually no time to spend with his sister and Mike. His personal email accumulated in his inbox, as he continued to skip over it so that he could select only messages that were necessary to maintain his business clientele.

On Friday afternoon Robert was finally finished at the legal firm, and he insisted that Patty and Mike accompany him for a nice supper and night out. When they finished their Irish coffee after the meal, they moved to the nearby lounge with its dance floor. Patty and Mike soon spent a lot of their time dancing to the quartet that was performing.

As he watched them dance, Robert immediately pictured Annie and her faceless date Sid in their place, and the image quickly depleted the enjoyment he had been having. He did manage to enjoy a couple of dances with his sister, but when she suggested that it was time for them to leave, he quickly agreed. For some reason he simply wasn't in a dancing mood any more.

The next day he was determined to get caught up on his email messages, as well as finishing up a few of the jobs for his own clients that he had set aside. As he worked his way through the emails, he came to several from Annie, wondering why he hadn't been in touch with her.

Rather than answer them all, he deleted them after he read each one, having decided to send her one email when he finished the last one in his inbox. Eventually he was caught up, and he quickly wrote a message to Annie that summarized in two paragraphs what he'd been doing in Toronto.

His third paragraph told her he'd be returning to Thunder Bay the next day, Sunday, and that he hoped they'd run into each other in Hinckley. Where his emails used to be friendly and folksy, the last two messages to Annie had been cool and business-like, a change that fit with his new assessment of their relationship.

Deep down he now believed that he had to insulate himself from Annie. He knew that as her confidence grew she'd be less and less inclined to want to spend time with him; after all, it was the way his life had been ordained to be.


Early Sunday evening, after Robert had unpacked and thrown his laundry into the washing machine, he finally got a chance to sit down and put his feet up, a cold beer in his hand. He had just picked up the remote to see what was available on cable, when he heard a light tapping at his door.

He was a little surprised by that as his was a security controlled building, and no one had buzzed for admittance. Likewise, his neighbors were mostly retirees, and he didn't know very many of them well. He set his beer on the coffee table and went to the door.

When he opened the door, he was shocked to see Annie standing there. "Annie! Where did you come from?"

She gave him a small, nervous smile and said, "I just drove up from Duluth. I got off work at four o'clock, and I have a few days off, so I came to find out why you're avoiding me all of a sudden. I was just going to buzz your condo when a nice older lady let me in." He could see that she was a bit skittish, and he immediately wondered if he was making her nervous again, or if it was something else.

He quickly got over his surprise, and his curiosity about her nervousness and said, "Come on in, Annie. I'm just surprised to see you." He stepped back and ushered her into his condo, his confusion plain on his face.

She walked past him, turned, and once he had the door closed she began to speak immediately. He could see the look of determination on her face as she spoke.

"You've really got me upset, Robert. I thought we were really getting to be good friends, and all of a sudden you're emails were so distant I didn't know what to think. Dr. Maier suggested I should phone you, as she says that she's really noticed how it has affected me, but I decided to come and see you in person. I have a few days off now, and I want to get some answers from you before I go back home."

Her words had come out in a rush, and now that she had finished speaking she was standing there looking at him, her face flushed, and her hands clasped together in front of her.

Robert was very surprised by Annie's statements, but he immediately realized that she had a point, as he had intended to dial down his relationship with her. He had assumed that she was getting on with her life and was leaving him behind. He was now both embarrassed and flustered, and finally said, "I am sorry, Annie! I ... I didn't intend to upset you."

He suddenly realized that she was wearing her winter jacket and boots, and quickly added, "Please, let me take your jacket. You can put your boots over here, and we can sit and talk when you're comfortable." He escorted her to the closet where he hung up her jacket, and she placed her snowy boots on a plastic tray where they could dry.

Annie hadn't said anything more beyond a polite, "Okay," when he asked her about taking off her winter wear. When that was done, the two of them went into his living room, where Robert resumed his seat on the sofa, and Annie took the offered seat in a comfortable armchair adjacent to the sofa.

"Would you like a beer or something to drink, Annie? I can offer coffee or tea, or a glass of juice if you prefer that."

Annie appeared to be a bit more relaxed, and replied, "I wouldn't mind some orange juice, if you have it. I drove straight through from Duluth, and I didn't realize I was thirsty until you mentioned it."

Robert immediately left to get her a glass of cold orange juice, and when he returned with it she gratefully took it from him. After taking a large drink, she said, "Thank you, Robert. I needed that."

She shifted in her seat, and began speaking again, "I'm sorry if I've caught you when you have other plans, but I just had to talk to you. Your friendship has meant so much to me. I don't know if you intended to back away from our ... relationship or not. I just had to find out. If me and my problems have been more than you want to be involved in, just say so."

Robert was a little bit embarrassed as he thought about his rationale for stepping back from Annie. He wasn't sure if he should tell her what had really been behind his decision, but finally decided that he had to be up front with her, especially since it had meant enough to her that she drove almost 200 miles from Duluth to see him.

"Well, ah ... I wasn't sure ... I didn't know if you were going to still want to be as close with me, now that you have started to get out on your own, ... and have a more normal life." He was finding it hard to put his feelings into words, as he realized that his reasoning was pretty selfish.

"When you told me how much fun you had with Sid at the nightclub, ... and how much you enjoyed getting out, I just sort of ... I assumed you and he would be going out again. I thought I would give you the chance ... to get back to your life, on your own."

A look of surprise crossed Annie's face, and she blurted out, "I think you're jealous that I was out with Sid! Sid is ... here, wait a minute while I get my camera out of my purse. I have a photo here of Sid."

She fumbled in her purse until she withdrew her digital camera and then spent a few seconds scrolling through her stored pictures. Finally she found the one that she wanted, and held up the camera so that Robert could see the display.

"Here's a picture of Sid, and it is obvious that he's a little too old for me. I think he's 62, and that's not all. He's gay! His partner was away on a training course, so that's why he asked me to go with him. It's why I felt comfortable going with him." She was clearly amused now that she realized the cause of Robert's decision to cool down their relationship.

Robert was obviously embarrassed now, as it was plain to see that Sid was old enough to be Annie's father, and if he was gay, that made Robert's actions all the more off-base. He wasn't sure what to say, but sheepishly came out with, "I guess I just made a lot of bad assumptions, didn't I?" He was red in the face, and didn't continue speaking because he really didn't have much else he could say.

Annie decided to let him off easy, as she could see how embarrassed he was. She reached over and patted his hand before saying, "I'm flattered that you would be affected that way: it made my drive worthwhile! And here I was thinking you didn't want to get mixed up with a messed up person like me."

Robert decided that the best way out of the situation was to change the subject completely, and asked her, "If you didn't stop for anything to drink along the way, I guess you're probably hungry too. I had a very late lunch, and sort of planned on ordering a pizza this evening. Can I interest you in joining me for a late supper?"

He couldn't believe how happy he felt, now that he had learned Annie and Sid weren't a potential couple, and that she valued his friendship enough to drive for four hours to confront him about his rather cold replies to her messages.

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