Lip and Annie - Cover

Lip and Annie

Copyright© 2010 by jake60

Chapter 6

Drama Sex Story: Chapter 6 - 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  

After stopping at the condo for enough time to freshen up and change their clothes, Robert and Annie timed their arrival perfectly, and met Fred and Sherry at the entrance to the restaurant. They were soon seated at a table where formal introductions were made.

From the first few minutes of their time together it was obvious that Annie fit in with Fred and Sherry as easily as Robert did. The two women could have been cousins, as at least in height and hair color they were very similar. Sherry had short hair, which was a major difference between them.

Eventually they finished their meals and while they sat waiting for the arrival of dessert menus they got into a conversation about music. Fred announced that he was a big fan of Bob Dylan, among others, and Annie surprised him by letting him know that she lived about a block from his first home in Duluth. She was quite knowledgeable about his Minnesota roots and had a spirited conversation with Fred about him and his music.

Once their desserts were ordered, the two women decided to make the obligatory joint trip to the ladies room. They had barely left the table when Fred said, "I really like your girlfriend, Robert. Maybe I could ask her to get me a photo of Dylan's first home. I'd really like that: do you think she'd mind?"

Robert was a little embarrassed as he said, "She's not my girlfriend. We are friends, for sure, and no, I don't really think she'd mind your request at all."

Fred looked a little puzzled as he said, "Well, you may not think she's your girlfriend, but from the looks I see her giving you, she hasn't got the memo yet. She's one heck of a good looking woman, and it's obvious that she really likes you. She's constantly smiling as she looks your way, and she does that a lot. You had better get off the fence, or someone is going to beat you to her."

Robert was obviously flustered now and said, "I ... I guess I didn't notice that. I'm not used to the idea of having a girlfriend, but Annie would certainly be better than I probably deserve." He saw that the two girls were on their way back to the table, and didn't say any more than that. Fred noticed that Robert did look at Annie closely as she came back to the table, and it was obvious that she had a big smile on her face, and that it was directed towards Robert.


It was almost 10 o'clock when they left the restaurant, and everyone was in agreement that they'd had a great meal. Rather than call an end to the night they decided to visit a nearby bar that advertised a band and dance floor. As they entered, Robert and Fred told the girls that they would limit themselves to one drink so that they could drive safely, but the girls could enjoy more than one if they wanted to.

Since it was a weeknight, there were several tables and booths available, and the two couples were soon seated in a booth enjoying their first beverage. The two men chose light beer, while their companions decided to try something fancier.

It wasn't long before both couples were on the dance floor, enjoying themselves. For Robert it was especially enjoyable, as he normally didn't get a chance to dance unless his sister was in attendance. Annie seemed to be quite comfortable with the idea of sharing a slow dance with him, although he noticed a couple of times that she stiffened up when he moved such that their bodies made full contact.

He was trying to keep that from happening though, as he knew that he'd likely respond in a way that might cause a bigger reaction in Annie. That had almost happened the last time they had been this close together, the night that they held a lengthy embrace in his room in Hinckley.

The two couples were on and off the dance floor often over the course of the next hour, and at one point Fred suggested that they switch partners for a dance. Robert could see that Annie was momentarily flustered, but she soon smiled and said, "That would be fine, Fred." The two couples changed partners and carried on with the next dance, another slow one.

Robert and Sherry were only dancing for about half a minute before Sherry said, "I really like your girlfriend, Robert. She's really nice, and you two seem to get along very well."

After a few seconds Robert answered, "I was telling Fred that Annie and I weren't really a couple, that way. We are good friends, though, and I guess I wouldn't mind at all if she was my girlfriend. We haven't really ever talked about anything like that."

"Well, I can safely say that she seems to like you a lot. She told me that she came here to Thunder Bay because she was afraid you were trying to discourage her from getting to know you better. She said that the two of you straightened that out, and she certainly seemed happy about that." Sherry chuckled at the look of confusion on Robert's face and continued, "Oh come on, Robert! Surely you realize that she would be more than happy to be your regular girlfriend."

After a few seconds Robert responded with, "Thanks for the information, Sherry. I guess I'll have to do something about that, but I'm not really experienced with girlfriends, or even dealing with the whole subject." She had given him a lot more to think about, and his mind was now on Annie, and whether his friends were right about her feelings.

The subject ended when Sherry said, "Just be yourself, Robert. I don't know you well, but what I've seen of you makes me realize that you should be any woman's idea of a good boyfriend."

Robert wondered briefly if Sherry was serious with her comment or not, but realized he already had enough to think about. As they continued their dance he looked over and noticed that Annie looked very good in the skirt she had chosen to buy. Her legs were slender and flawless below her skirt, and he was happy that he had convinced her to switch from her normal attire.

Sherry had added a lot more information for Robert to consider, and for the rest of the time that they were in the bar, his mind was partially occupied with the here and now, while the rest of the time he was considering what his friends had said.


At slightly after midnight Robert and Annie returned to his condo. She was feeling the effects of the two mixed drinks that she had enjoyed in the bar, and thanked Robert for a wonderful night out. "I haven't had this much fun in a long, long time. I really like your friends, and maybe someday the three of you can come down to Duluth and I'll take you out on the town there."

"Be careful what you suggest, Annie, as we may take you up on that. I know that Fred would probably go down there tomorrow if you could point out the house that Bob Dylan first lived in. I knew he had grown up in Hibbing, but I didn't know about the Duluth connection."

They continued their conversation as they sat in the living room, with Robert pointing out that over the course of the evening Annie didn't seem to even notice the fact that her scarred arms were visible. She had to acknowledge that neither Fred nor Sherry seemed to take note of them. Eventually, though, they agreed that it was time to call an end to the night. As the two of them walked into the hallway leading to the bedrooms, Annie turned and then took Robert into her arms.

"Maybe it's the two drinks I've had, or maybe it's just time, but I'd like to have a kiss from you."

Robert could tell that she was a bit tense as she leaned forward so that their lips could meet. They started out very tentatively, but it wasn't more than a few seconds before it became a little more heated, and Robert felt her lips open slightly. Their kiss lasted almost another minute, with each of them letting their tongues join the activity.

When the kiss ended Annie said, "That was nice Robert. I didn't think it would ever be possible for me to share a kiss with a man again." She suddenly burst out laughing and continued, "Don't even think that I meant I contemplated sharing a kiss with a woman. That's not my thing."

After they exchanged goodnight wishes they each headed for their separate bedrooms, although both of them were thinking about what might have been. Robert had just taken off his clothes and crawled between the sheets when there was a light knocking on his door.

"Yes, Annie. What is it?"

"Could I come in Robert?"

"Sure! I'm already in bed so it's no problem." The door opened and Annie, dressed in her pajamas, walked in tentatively and stopped when she got to the end of the bed.

"What I'm going to ask you probably is very, very unfair to you. I'd like to expand my progress with my ... problems by getting into your bed with you ... just to see if I can handle it."

Robert didn't need to think about his answer and quickly said, "Certainly, Annie." He smiled and continued, "I promise to be on my best behavior, but I have to warn you that I don't wear anything in bed." He thought about that statement for a couple of seconds, and then gave a nervous laugh and added, "I suppose that's more information than you needed to know."

Annie was noticeably nervous now and slowly worked her way to the far side of the bed, opposite to the side that Robert occupied. "That's okay. I just want to see if I could push my boundaries a little."

She lifted the blanket and sheet and quickly climbed into bed, facing away from Robert, and as close to the edge as she could get. It was obvious to him that she was very anxious, and that her body looked very tense.

The two of them lay there for a couple of minutes without saying a word. Eventually Annie turned enough to look over her shoulder and see how far she was from Robert. Slowly she slid herself over so that she was about a third of the way across the large, king-sized bed. She stopped while there were still over a couple of feet between them.

Since this was Annie's decision, Robert stayed where he was and didn't say anything. He was watching Annie, and the image of having her there beside him in his bed on a permanent basis flashed through his mind. He knew, though, that he couldn't be that lucky.

Another couple of minutes passed before Annie said, "Robert, could you move over this way a bit, and give me your hand."

He didn't reply, but his movements showed that he was acquiescing to her request. She had extended her right arm and hand behind her, and when Robert felt it with his hand he moved forward far enough that he could stop a few inches from her back. He was very nervous that if he moved any closer to her she would feel the erection he was now unable to control.

Annie was now holding his right hand, and after squeezing it several times she pulled it up onto her waist to a point about where her pajama top ended. Another delay ensued before she slowly brought his right hand under the top of her pajamas, stopping when it was near her navel.

She shifted her grip on his hand and then took his index finger and moved it to an area of the skin that felt a bit uneven. She slowly began to move his hand upward, tracing the uneven skin with his index finger. He realized immediately that his finger was tracing one of Annie's scars.

She continued to move his hand upward, and he realized that she was going almost to her neck, as he noticed his free fingers dragged along the side of her left breast. He could feel her body get tense when that happened, but she didn't stop moving his finger along the scar. When the scar ended she hesitated a few moments before moving his hand down and over to a position below her right breast where she traced another scar with his finger.

This one wasn't as long, perhaps all of four or five inches. When that one had been traced there wasn't a delay before she moved to the other side of her chest and traced the scar below her left breast. To Robert it seemed very much like the one on the right side.

Annie seemed to be thinking about something and the two of them lay like that for almost a minute before she slowly brought his hand up onto her left breast and traced a 1 inch scar. He thought it felt like it must be high enough up on her breast that it would have come close to the areola around the nipple.

Another long pause was accompanied by more squeezing of his hand after she moved it so that it lay back near the center of her stomach. This was Annie's time, and he let her have full control of it, not moving or saying anything throughout the time that they lay there together.

It seemed as though Annie was trying to make up her mind about something, as finally she began to move his hand lower, below the waistband of her pajama pants. Robert was now very unsure about what she had intentions of doing, and decided to just let her continue to control the situation. He was beginning to think she was moving his hand to her pussy when she moved his finger slightly to the right, and he could feel another scar, this one horizontal.

She slowly traced this scar, by far the most uneven of the ones she had traced to this point. It extended across her lower stomach, at about the same level that the top of a small bikini would cover, and ended just before they started tracing around to the side of her hip.

When Annie finished that scar she pulled his hand back up to her stomach and they lay there quietly while she was squeezing his fingers again. Another minute passed before Annie said, "They feel obvious, but they look even worse."

Robert wasn't sure quite what to say at first, but he finally replied, "I don't care what they look like; they don't define who you are, so don't let them control your life." He knew how difficult this was for her, as he had felt her alternately tensing up and then relaxing as she took his finger on the extended tour of her scars.

Another delay ensued before Annie made what turned out to be the most important move of their time together in his bed. She turned to her right, let go of his hand, and used her free hand to pull him closer to her so that she could give him a kiss. Their lips had barely touched when she turned her hip far enough that his erection slid up onto her upper thigh.

She immediately tensed up completely, let out a small cry, and quickly got up from the bed and ran out the bedroom door towards the guest bedroom.

Robert was shocked, and he didn't react until after she had gone out through the bedroom door. He suddenly moved into action, quickly getting up and slipping on his bathrobe and then heading out the door towards Annie's room.

He could hear her sobbing in the bedroom as he stood at the closed door. "Annie, are you okay? I'm sorry I ... upset you. It wasn't intentional."

He was really worried, because he realized that she had been doing extremely well until his erection touched her unexpectedly. He could imagine that that must have brought strong memories back to her. His despair at having caused her such alarm had brought back his Hypernasality more severely than had happened in years, and his words had actually been difficult to understand.

"It's not your fault, Robert! I'm so sorry that I reacted like that; you didn't do anything wrong. It's me! I'm the one that's screwed up!" She cried for a short while, and Robert was just about to say something, anything, in the hope that he could help make her feel better when she continued, "Things were going so well, and I'm so sorry."

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