Lip and Annie - Cover

Lip and Annie

Copyright© 2010 by jake60

Chapter 3

Drama Sex Story: Chapter 3 - 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  

The month of December always passes quickly, and it was that way for Robert and Annie. They were in the habit now of trading almost daily emails, discussing minor events in their lives, and often trading simple messages and jokes. Robert was still playing online poker, and managed to win a very welcome $1500 in an online tournament. Annie was still not a fan of the online game, much preferring to play live in a casino.

About a week after their return from Hinckley, Annie described how she had made an appointment with her psychiatrist and they had attempted to address her lingering fears. After describing what had happened in Hinckley to her Doctor, the psychiatrist asked a lot of questions about Robert and what had happened.

According to Annie, in a message that was one of the longest that she had sent to Robert, the Doctor felt that it would be good for Annie to continue interacting with Robert, as he seemed to be a very safe male figure for her to be with.

When he received that message, Robert wasn't quite sure what he should think of it. It seemed to suggest that Annie would be pleased to continue their friendship, because her doctor thought it would be good for her. Considering that he enjoyed her company, he decided that he would accept being Annie's "safe" friend.

It seemed very much to him that continuing their friendship would be beneficial for both of them. He would have a woman he could enjoy corresponding with, someone who shared his love of poker, and she could have a non-threatening male friend.

On December 15th Robert received another package of coupons from the Grand Casino Hinckley, another attempt to entice him to visit their poker room. The coupons were good for the next six weeks, and it immediately got Robert thinking about making another trip for a weekend of poker.

He decided to ask Annie if she had received the same coupons, and whether she would be interested in accompanying him to Hinckley. He was already considering the last weekend of December because New Year's Day fell on the Monday following it.

New Year's Eve parties were never something that Robert worried about attending, because he made a point of avoiding events that would require him to have a date. As a result, it was the perfect weekend for him to consider a trip to the casino. Once he had made up his mind that it would be a natural weekend for the trip, he wrote Annie asking her if she'd be interested in going on the same weekend. While he was hopeful that it would be a good weekend for her to get away, he also assumed that she could have other plans.

Both of them had Christmas plans that had been in the works for quite some time. Robert was going to be traveling to Toronto to spend Christmas with his only sibling, his sister Patty. Patty was a year older than Robert, had a long-term relationship with her boyfriend, and worked in Toronto as a Corporate Lawyer. Their parents had died in an auto accident while he and his sister were both in university, and they had only each other now.

Christmas with Patty was becoming a tradition for the two of them, and Robert was looking forward to seeing her and her boyfriend, Mike. Annie's Christmas would be spent with her parents, who lived in Minneapolis.

Three days later Robert received an email message from Annie in which she accepted his suggestion to share a getaway to Hinckley on the last weekend of the month. She was off work already, having booked her last week of vacation for that week, and had been wondering what she would do with the time off.

He was reading her message, pleased that she had agreed to make the trip at the same time as he was going to be there, when another message arrived in his Inbox. It too was from Annie, a simple one sentence message asking if his previous offer of a ride to and from the casino still stood, because she was willing to accept it now.

Rather than reply by email, Robert immediately picked up the telephone and called Annie. He emphatically confirmed his willingness to pick her up on his way to Hinckley, and also offered to make the reservations for their rooms. His offer was quickly accepted, and very shortly after he got off the phone with Annie, he called the casino to make the reservations for two rooms, one in each of their names.


Robert's Christmas visit with his sister Patty went very well. Mike and Patty had apparently moved their relationship to the next level, as they were now sharing the condo that had previously been Patty's alone. Robert was tempted to ask them if they intended to someday be married, but decided against delving into her relationship with Mike, knowing that his sister would once again ask him what he was doing about finding himself a girlfriend.

He knew he could have stretched the truth a bit about his friendship with Annie, especially since they had what seemed to be an ongoing relationship, but he wouldn't have wanted to be forced to admit that it seemed that Annie's interest in him was that he was a safe male figure. He was comfortable with the way that he and Annie related to each other and didn't see a need to bring his sister up to speed on that aspect of his life. Hell, for all he knew Annie could decide at any time to move on with her life and leave him behind.

Two days after Christmas Robert was on a plane back to Thunder Bay, with one day to catch up on his business and get ready for his trip. He was looking forward to seeing Annie again, and wondered if she had managed to conquer some of her residual fears.

Robert had thought about his interactions with her a lot, and he realized that there were a lot of signs that she had been uncomfortable around him at times. He simply hadn't picked up on them, but now that he was aware of her story, he knew he would be able to catch most of the signals that had so easily gone over his head before. So much for his ability to read people's 'tells', he thought wryly.


At 11 a.m. on Friday, Robert pulled up at the address that Annie had given him. It was a modest home on a quiet street in the East End of Duluth, and once he was parked he got out and started up the walk way to the front door. She must have been watching for him, because as he reached the foot of the front steps, she came out of the door carrying her suitcase. They exchanged belated Christmas greetings before Robert took the suitcase from her hand and led the way down to his three-quarter ton pickup that was parked in front of her home.

"I didn't realize you drove a truck, Robert." It was a large model, and was tall enough that a running board was a major convenience for anyone getting into the truck. It was one of the extended cab models, and Robert opened the passenger-side rear door in order to place Annie's suitcase on the rear seat.

"I have a car as well, but this truck has four-wheel drive, and if the road conditions aren't great that feature will come in handy. I use the truck for fishing and hunting in the summer and fall more than anything. It's a diesel, so I hope you don't mind the fact it's a little bit noisier than normal vehicles." He proceeded to open the passenger door and assisted Annie as she got into the passenger seat.

As they pulled away from the curb in front of Annie's home, Robert asked, "Have you eaten lately? I skipped breakfast this morning, so I'm wondering if you'd be interested in stopping at the Perkins Restaurant on the way out of town for brunch."

Annie was in complete agreement with this suggestion because she hadn't had very much for breakfast either. Just a couple of minutes later they were pulling into a Perkins that overlooks the Duluth harbor, and is just off of the beginning of I35. As they were placing their orders they were also taking their first sips of the ubiquitous cups of Perkins coffee.

Robert could already sense that Annie was a little more relaxed around him, smiling and laughing much more freely than he had ever noticed before. They engaged in polite conversation about how they had spent their Christmas day, and it seemed that both of them had had an enjoyable holiday. By the time their meals arrived, they had pretty much covered the subject of Christmas.

Neither of them had ordered anything that was very fancy or time-consuming to eat, so it wasn't long before they both finished their meal and were back at their bottomless cups of coffee. After he set his cup back down Robert said, "I'm really looking forward to this trip. Christmas is always so hectic, and I find sitting at a poker table to be pretty laid back most of the time."

After Annie voiced her agreement with his sentiments, he continued, "That afternoon that you showed me your Taser, you mentioned that there was more to your story. Maybe you could explain what you meant on our drive to Hinckley. We'll have about an hour and a half on the Interstate."

"Oh, I hadn't considered that. I've seen my psychiatrist a couple of times, and she suggested that I do precisely as you ask, but I'm not really sure if I'm quite ready for that right now. Maybe instead of me telling you all about what happened to me, you could tell me how you came to have never had a date, and yet you claim that you are not a 30 year old virgin." She sort of grinned at him after saying that, and then added, "I'm still not sure you have me convinced that you're telling me the whole truth about that."

The smile quickly faded from Robert's face with her suggestion that he be the one to provide the details of his experiences before she completed her story, but realized there was really no reason that he could use to refuse her request.

In a moment he answered, "I guess there's no good reason for me to insist that you make your explanation first. I'll explain how what I said is true when we get on the highway. I don't really want to get into that while we're here, in the restaurant." He was blushing a little as he finished his statement, and the return of his Hypernasality signaled he was more than a little affected by his decision.

"I'm going to hold you to that, Robert." Annie could sense that he was both embarrassed and hesitant to get onto the subject, so she didn't push against his request to wait until they were driving.

There hadn't been a whole lot of conversation as they drove through the maze of overpasses and on and off ramps that skirted West Duluth. When they finally climbed the long hill that ended with the turnoff to the small town of Proctor, Annie finally turned to Robert and said, "Spill it, Robert. Explain how you can say things about yourself that seem to be pretty well mutually exclusive." She grinned at him as though she had already won the minor contest over whether his statements had been entirely truthful.

Now that they were past the section of I35 that required constant vigilance, Robert had relaxed a bit and turned to look at Annie, as she sat beside him in the passenger seat. The truck sported high backed bucket seats, and she had reclined hers just enough to be very comfortable. He noticed that she was wearing another of her apparently endless selection of long sleeved turtleneck sweaters under her winter jacket.

The heater in his truck was quite good, and she had fully unzipped her outerwear so that she could be a little more comfortable. It was impossible not to notice that she appeared to be very fit, and was in possession of very elegant curves beneath her sweater.

Robert didn't consider himself an expert in the matter, but he certainly felt that she was more than amply endowed. After having dealt with her reluctance to be alone with him for this drive a month earlier, he was actually quite impressed with the change in her overall attitude. The counseling she was receiving from her doctor seemed to be doing some concrete good.

The night of their first supper together Robert had found it quite easy to suggest that at some future time he would explain to her how he could truthfully say that he had never been on a date, while maintaining that he was also not a virgin. Now that that time had arrived he was finding himself at a bit of a loss for words.

Most of what he would have to tell her was not the type of thing that he had discussed with others in the past. He finally decided to honor his promise, as there didn't really seem to be a reason to expect she would be able to talk about him to anyone else he knew. Mind you, he didn't really think she was the type of person who would do that anyway.

After clearing his throat he began, "Well, I guess I can start back when I was in my second year of high school. I must've been 15 at the time. I was going through the awkward years where I had begun to notice girls, but besides the normal shyness of a 15-year-old boy, I also had the added burden of the appearance of my face, ... my lip. Teenagers of both sexes can be pretty cruel at times, and I got more of that than most of them."

"There was a girl in my class named Brenda. She wasn't one of the ones that were involved in sports or cheerleading or got on the honor roll for her academics. She was a decently pretty girl, and for the most part she just did her best to get along with everyone. Anyway, one of the cheerleaders, Amanda, whose boyfriend was a running back on the football team, got into some kind of a disagreement with Brenda. She and her boyfriend hatched a plot to get back at Brenda, and they used me to do it."

He glanced over at Annie for a moment, and could see that she was following along very seriously with his words. He continued, "What they did, was the boyfriend, Adam, told me that he and Amanda had arranged a blind date for me with a friend of theirs. I was pretty excited, since I wasn't one to normally even think about going out on a date. Being on a double date with Adam and Amanda made it seem all the better, because they were quite popular."

"I found out much later that Amanda gave pretty much the same story to Brenda, except they told her that her date was with one of the football players. I remember being so excited that I even told my parents and sister that I was going on a double date with one of the most popular couples in the school. They were so happy for me, because usually I was picked on pretty badly." He stopped speaking for over a minute as he relived the events in his mind. Annie was about to ask him if he wanted to forget about telling his story when he started speaking again.

"The big date was set for Saturday night, and at seven o'clock Adam and Amanda picked me up at my house. I can still remember looking back and seeing my parents standing off to the side in the living room watching me leave." There was another hesitation now, but this time he carried on without waiting for more than a handful of seconds. "Mom and Dad had been so excited for me; they had me in a really good mood as we went to pick up my date."

"Eventually Adam pulled up in front of a house and they said that I should just walk to the door and surprise my date. Well, I guess it was quite a surprise for her, because the moment that she saw it was me she let out a yell. I was just registering the fact that the girl I was going to be taking out was Brenda, when she burst into tears and I heard the laughter coming from Andy and Amanda as they stood there by his car." Robert stopped then for another long delay, and Annie could see that he was beginning to get upset as he remembered the incident.

"It seemed like only an instant before Brenda had run back into her house after slamming the door, and Andy and Amanda had got back into his car and left. There I was, standing by myself in front of a closed door, while the people who had brought me there drove off."

After another short hesitation so that he could regain control of his voice, Robert continued. "I was so upset and hurt, that I didn't know what to do. It was obviously a big joke, and Brenda and I were the victims of it. It was a nice spring evening, and there were people outside their houses along that street. Some of them were standing there watching me."

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