Lip and Annie - Cover

Lip and Annie

Copyright© 2010 by jake60

Chapter 10

Drama Sex Story: Chapter 10 - 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  

Late Wednesday afternoon Robert made a phone call to Dr. Maier from his home in Thunder Bay. Although he was sure that Annie was completely past her emotional problems, he decided to seek confirmation from her doctor.

"This is Dr. Maier."

"Hello, this is Robert Porter calling. I know that Annie had an appointment earlier this afternoon, and I'm wondering if I could speak to you about her."

He could hear a sharp intake of breath, even over the phone. "What is this about? Has this to do with what we discussed a while ago? Surely you aren't..."

Robert interrupted with, "Oh, no! I'm not thinking of breaking it off with Annie; I'm even more in love with her! I just wanted to know, if you can tell me, what you think about her ... her mental state ... now that we've been active sexually. I just wanted to know if you think we've gone too far, too fast."

Dr. Maier quickly answered, "Absolutely not! I'm so glad that Annie gave me permission to speak with you. I can assure you that she is doing fine, even better than I could have ever hoped. She is the happiest I've seen her in all the time that she has been my patient."

Dr. Maier had given Robert exactly what he was hoping to hear; complete reassurance. The two of them spoke for a couple of minutes before ending their call. It was Robert's turn to smile broadly after a telephone conversation with the doctor.


A few minutes later Robert was on the phone to his friend Fred. Annie had told him the night before during their longest telephone conversation ever that she was planning on coming up to spend the weekend with him in 10 days. She had suggested that perhaps Fred and Sherry might like to get together for supper again.

After they had exchanged greetings Robert said, "Hey, Fred. Annie is coming up the weekend after next. We wondered whether you and Sherry might like to join us for supper, I'm thinking Saturday night here at my condo."

His invitation was accepted, and when Robert suggested that maybe he should phone and talk to Sherry first, Fred just laughed, saying that she was right there beside him; she had moved in with him two weeks before.


It was Friday and Robert was nervously waiting for Annie's arrival, anxious to be with her in the flesh, rather than by phone. When his intercom finally buzzed, announcing that someone was trying to contact him from the building entrance he was very quick to get to the speaker. The moment he heard Annie's voice he quickly pressed the door release to let her enter the building.

Annie must have hurried, because she was at his door in what seemed like just a few seconds. Robert managed to say, "Hi Annie," before she was in his arms and her lips were on his.

When their kiss ended, and they had exchanged more traditional verbal greetings, Robert picked up her suitcase and started carrying it down the hall towards the bedrooms.

He didn't want to appear that he was taking Annie for granted, and when he got to his bedroom door he stopped. "Did you..."

That was as far as he got before Annie said, "Of course, silly. You don't want to have to wash two sets of sheets, do you?"

They had set their course now, as in no time they had Annie's suitcase empty, her clothing in his closet and a couple of the dresser drawers, mixed together with his.

Robert had made a simple casserole for supper, something that he was able to leave heating in the oven while he waited for Annie to arrive. After their simple meal, followed by dessert and a leisurely half-hour spent in the living room enjoying an after dinner liqueur, Annie excused herself to have a shower and freshen up.

Half an hour later she called him to his bedroom where she met him dressed only in the lingerie that he had bought for her. She had dimmed the lights, and except for that one concession to her demons, she was as relaxed and open as she had been on their last day together in Duluth.

An hour later Robert emerged naked from the bedroom and quickly made the rounds of his condo to shut off the lights. He seemed to be in a hurry to get back to his bedroom.

The next day they emerged late from the bedroom and spent the first part of the day relaxing around the condominium. Later in the day they started preparing the meal they intended to share with Fred and Sherry that evening. Annie would make lasagna, and Robert would handle the Caesar salad, garlic bread and dessert.

Their tasks kept them occupied for several hours after which they changed for supper and then spent a pleasant half-hour with a glass of wine each while they waited for their company.

Their shared supper with Fred and Sherry had been enjoyable, and Robert sent the two ladies to the living room with a glass of wine each while he cleared the table under the watchful supervision of Fred. He had convinced the two women that since it was his condo, he knew where everything had to go. It hadn't taken too much convincing to get them to go and relax with their drinks in hand.

Robert was busy loading the dishwasher when Fred said, "I guess you're not going to argue about Annie being your girlfriend, now are you? While I was telling you about how Sherry and I had decided to move in together, I heard her whispering to Sherry that the two of you were practicing being a ... couple."

Robert looked up sharply when he heard Fred's words, because he had missed the conversation that Fred was referring to. "Annie said that, did she? I wasn't sure if I should mention she and I were getting that close. Obviously I didn't need to worry about what she would think if I said something."

He laughed and glanced towards the living room before continuing, "You probably realize I've never had a girlfriend before; that's pretty common knowledge, I think. I can't tell you how much it means to me that Annie and I have hit it off so well."

Fred smiled back and replied, "All I can say is that we are blessed with two very good looking women, Lip." He smiled conspiratorially and quietly added, "I'm seriously thinking of popping the question to Sherry very soon. I've never met anyone else that I've felt this way about."

Robert smiled and said, "I know what you mean Fred, I know what you mean."

The rest of the weekend was as pleasurable for Robert and Annie as Friday night had been, however their parting on Monday morning wasn't easy for either of them.


A month later Robert and Annie were entering their room at Bally's Hotel and Casino. It seemed to be at the heart of the Las Vegas strip and wasn't very far from where the tournament he was entered in would be held.

"Well, what do you think of it Annie? Is this room going to be okay for the next 14 days?"

Annie had quickly checked over the amenities and soon replied, "This room is great! Lots of space and the bathroom is just fantastic." She gave him a wicked grin and added, "I hope you don't get too tired out at the poker tables, because it has a lovely shower that will hold two very comfortably."

He took her in his arms and they were soon well on their way to losing track of time. He finally broke their kiss and said, "We need to get unpacked and put everything away. I have to go over and see which day I play in the first round. No matter how it works out we'll have the other three days of first-round play open to do whatever we want."

"I hope I can get into tomorrow's session. At least we'll know quickly whether I have to worry about being around for the rest of the tournament. Not that I'm expecting to get knocked out in the first round. I mean, I hope that doesn't happen." His nerves were a little frayed, and he noticed that his speech was being affected.


Robert had managed to get into the Saturday session, and he was somewhat glad that Annie had insisted he get a good nights rest. He could see that several of the other players at his first table seemed to have spent the night partying, at least judging by their bloodshot eyes.

The day progressed better than he had hoped, and he managed to end the day without being knocked out. In fact he had a respectable number of chips to carry forward to the next level the following Wednesday. The winners from the Saturday and Sunday sessions would be playing together to weed out more of the players prior to a further consolidation on Friday.

By prior arrangement he phoned Annie, and they decided to meet back at their room. She was waiting there for him when he walked in.

"Robert, you made it! I'm so glad that you survived the first round. How did it go?"

Robert had been sitting for most of the day, and he was quite happy to remain standing for a while, so he simply removed his shoes before replying, "I think it went great, Annie. I've got almost four times the 30,000 in tournament chips that I started with, and I know that there were people at my last table who had very few left. I managed to avoid any bad beats, anyway."

Annie was very interested and quickly asked, "What was your best hand? Did you have any really good hands where you really cleaned up?"

Robert laughed and answered, "I had a couple of really good hands today. I got pocket aces twice, and both times an ace was turned on the flop. Both hands did very well for me. I knocked two people out of the tournament the first time. A small pair flopped with the ace, and my Full House was golden."

"The second time my set of aces didn't do as well for me, as I think most people figured me for only a pair of aces, and nobody else had a good hand. One guy didn't believe I had trip Aces and stayed with two pair, aces and threes. I got quite a bit of his stack."

Annie knew that Robert was quite tired, worn out from his stressful day, so she didn't argue when after dinner he had a shower and went to bed. She joined him, both of them naked, and when she could see that he was wiped out, was content to cuddle and then spoon up to him when he drifted off to sleep.

The next morning Robert woke up refreshed and horny, spooned up behind Annie. When he began playing with her breasts she woke up too, and they soon decided to share the shower. They had already been together for a shower in Robert's condo ensuite bathroom, and knew what they both liked when it came to sharing a shower.

The only thing that was still off limits for Annie was anything that suggested anal sex to her; this meant that they were a little limited in what they could do in the shower as approaching her from behind was off the menu. Being inventive, though, they both managed a climax under the spray of warm water.

Robert and Annie spent Sunday touring the nearby casinos, even spending half an hour in one of their poker rooms playing their usual Limit Holdem game. Between them they broke even, as Annie was ahead by the $30 that Robert was short.

They had supper at a dinner theater that featured a topless review. By the end of the show their meals were finished and they had come to agreement that one of the hiring requirements for the dancers was a minimum D sized chest. They couldn't agree on how many of the ladies were sporting silicone enhancements.

Robert did manage to gain a few points when he told Annie that he wouldn't trade hers for any of the ones on display. She flushed a pleasant shade of pink when his comment was obviously overheard by the couple at the next table, but she calmed down when he reminded her that What Happens in Vegas...

Later, after enjoying a glass of wine and a beer in the piano bar of their hotel, they returned to their room. It was obvious that Robert was nervous about something once they entered the room, and Annie gave him a couple of worried looks before he took her hand and seated her on the bed beside him.

Robert swallowed twice as he worked to get his speech under control. Finally he took both of Annie's hands. There was still a look of concern on her face, but he didn't really notice that.

"Annie, I'm not sure how to go about this, but I need to know something." He swallowed again before he continued, ignoring the look he was getting from her, "I love you very much, Annie, and I believe you love me too. I ... I would like ... Annie, would you marry me?"

Robert felt like his heart had stopped as he waited for an answer from Annie. She had listened to his question, but it almost seemed that she didn't understand it. The look on her face had quickly changed from concern, to shock, and then to the most wonderful smile that seemed to take over her entire face.

After what seemed like forever to Robert, but really was probably no more than a handful of seconds Annie answered, "Oh, Robert! I will!" Her face seemed to cloud over and she continued, "Are you sure? Are you sure you really want to marry me?" Concern quickly washed over her face as she waited for him to answer.

Robert instantly answered, "I've never been so sure of anything in my life, Annie. I know we haven't known each other for even close to a year yet, but I know you're the one for me." As he held her hands he leaned forward to gently brush his lips across hers.

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