It Doesn't Hurt to Ask - Cover

It Doesn't Hurt to Ask

Copyright© 2008 by Westside24

Chapter 3

Romantic Sex Story: Chapter 3 - Story about a man who goes to Florida for business and pleasure and meets some interesting women.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic  

Mark had visions of Nancy as he drove back to his condo. She was something else he thought and he would definitely follow up to see her again. Maybe he would fly out to New York and spend some time with her. It’s not that often you meet a woman who is intelligent, athletic, beautiful, and has a great personality. She is the whole package, he thought. He chuckled to himself as he thought that her having a fine butt doesn’t hurt either. She was something and he was glad that he had met her.

He parked his rental car in one of the guest’s designated parking spots and proceeded to the elevator with his sport coat and tie in one hand. Standing at the elevator was a woman who seemed to be struggling because she was holding a large number of shopping bags in her arms and hands.

“Here, let me help you with those,” and he took three of the plastic bags from her hands.

“Thanks, I should have taken my shopping cart but I thought I wouldn’t need it. I didn’t plan on buying so much.”

The lady appeared to him to be just a few years older than himself. Height was just an inch or two over five feet and she had short very dark hair. Because of the dark color of the hair he thought that it probably had received some assistance. Her breasts seemed to be too large for her small frame. A pleasant smile and Mark got a first impression from looking at her eyes that she was a fun person to be with.

The elevator arrived and she pressed the button for the seventh floor.

“I haven’t seen you in the building before. Did you just move in?”

“Oh no, I am just visiting the area for business and also taking advantage of what the area has to offer. I am staying in Jim Stanford’s condo. He insisted I do so and treats me like his second son. My name is Mark Scales.”

“I know Jim and his wife. We play bridge together when they are here. They are good people.”

“Yes they are.”

The elevator came to a stop on the seventh floor and they walked to her condo with her leading. This woman had interesting figure thought Mark. What is going on here, he wondered. It seems that every woman he sees in Florida has an interesting figure or good looking butt.

Entering her condo, Mark placed the bags he was carrying on her kitchen counter.

“I’m sorry but I forgot to introduce myself. My name is Connie Durbin and I want to thank you for giving me a helping hand. Can I get you something to drink?”

“If you have a cold diet soda, it would hit the spot.”

Mark sat on a kitchen chair and watched Connie go to the refrigerator and bend at the waist to the bottom shelf to look for the soda. Her slacks tightened as she bent down and Mark again was treated to a nice butt shot. Not a great butt he thought, but a nice butt.

“How is your visit to Florida going so far?”

“Oh, it’s been very enjoyable. I am hoping the enjoyment will continue. My only problem is finding the nice places to go since I am unfamiliar with the area.”

“What are you looking for?”

“Restaurants with good food and lounges that cater to an older crowd rather than the college crowd would be nice. I would think that based on the demographics of the population here there must be some places like that, but I have no idea on how one can find those places.”

“There are a number of those places. Charlie O’s in Treasure Island is one of those places. It has good food, an easy-listening three piece band and draws a good older crowd. I don’t think it has changed since I last was there but that’s a guess on my part.”

“Would you like to go there tonight? Before you say anything, let me explain. While I enjoy going to a singles bar, I hate going to a restaurant and sitting alone at a table. I just feel embarrassed. If you can’t go and have other plans, I can understand that. I will still go to Charlie O’s, but my dinner will be some carryout at a fast-food greasy spoon.”

“Well I wouldn’t want you to do that. Thanks for asking me and ordinarily I would turn your invitation down since I have a steady boyfriend. His name is Gordon. We have been sort of a couple for about a year now. Unfortunately, he had to go back to Columbus for some family function and isn’t due back till tomorrow afternoon. I have nothing going on for tonight and it would be interesting to see if there have been any changes at Charlie’s. If you are serious about wanting to take me, I will go.”

“What time should I knock on your door and do I need to make a dinner reservation?”

“I’ll take care of the reservation and instead of coming back here, are you parked in the guest’s spots? You are, well let me meet you there. The reason I say that is Ben, who lives down the hall is an old biddy and if he sees us together his tongue will start wagging. Yes, it’s best for me to meet you at your car. Seven should be the right time.”

Mark went up to the condo and took a two hour nap. He thought there was something about these Florida women that they could wear a fellow out. Then again, what a way to go! Since Connie has a steady, there shouldn’t be any extra-curricular activities tonight. Those were his last thoughts as he fell asleep.

He was sitting in his car at seven and about five minutes later, the passenger door open and Connie slid into the seat. She looked good in a black silk blouse, tan skirt and nylons. Her make up was done nicely and her perfume was evident.

“You look very nice.”

“Thanks, I am looking forward to tonight.”

Connie directed Mark to Charlie’s. There was a decent crowd already but it still was early. More men than women were there now but he thought women usually came in later when the band was already playing. Their reservation was confirmed and they were shown to a table that was next to the dance floor.

Mark was able to get Connie to talk about herself. She had been married twice before. Her first husband died in a truck accident while her second husband was killed at work in a construction accident. While she had received two nice settlements, she loved her husbands and the cash couldn’t cure the hurt. She had been going with Gordon for over a year and he has treated her very nicely with trips and cruises and some nightlife. She has two daughters from her first marriage and she has four grandchildren. Connie was most proud of her first grandchild who was finishing her first year in medical school.

That last comment cause Mark to do a quick calculation in his head and he concluded that Connie was somewhere in the vicinity of sixty five years of age. That was older than his mother. He gave her a close a look as he could with the light being what is was. Maybe her makeup was good but her face was not the face of a sixty five year old woman even if she was as they say ‘well preserved.’ In looking at her hands, they did indicate that maybe she was that old but he wasn’t sure. Connie must have had some surgical enhancements on her face for her to look as young as she did. The facial skin was awfully tight. He also noticed in doing his appraisal that a few of the buttons on her blouse were undone and there was some cleavage showing. She had a very a nice set of large breasts and he wondered what size her nipples were. Mark had never been with a lady this old and maybe nothing would happen but it would be interesting if something did. He thought she was sending out some signals but he wasn’t sure what these signals were saying. Mark was a little confused by how Connie looked at him and acted.

They had a drink and gave the waitress their selections for dinner. When the food was brought to the table, they ordered a refill on the drinks. Those Grey Goose martinis tasted good. In spite of her age, Mark had to admit Connie was a desirable woman. She did have a nice personality and had a way of looking at you when she talked that made you feel you were the only one in the room. Her breasts were becoming more impressive and he had a hard time of looking her in the eyes when he spoke to her. The more he talked with her the less her age became a factor.

The band had been playing for a while and when they finished their meal, he asked Connie to dance.

“I haven’t danced in I don’t know how long. I may have forgotten.”

“It’s like riding a bike, once you learn, you never forget.”

The music was fast and once Connie adapted to Mark’s dance style as she followed his lead easily. She was light on her feet and quick to react to Mark’s dance moves. The second dance was a slow one and Connie positioned herself so that Mark’s right foot would go between her thighs when he stepped forward. Mark figured this out quickly and moving forward was his favorite dance step. This movement in which Mark’s leg would rub against her inside thighs was causing her to moisten. Connie’s breasts were touching Mark’s chest. Since she appeared to enjoy contact with Mark’s body he brought her closer to him so he could press his partially aroused love tool against her stomach. He though he heard an intake of her breath and an “Oh” when he did this. Connie wasn’t resisting any of this body contact.

Sitting out some fast dances, they had their drinks refilled. Mark thought the top three buttons of Connie’s blouse had been unbuttoned but now he saw there were four buttons unbuttoned. The view of her cleavage became more pronounced.

Connie bent toward Mark and said, “Can we dance some more? I am really enjoying myself.”

Mark rose and led her back on the dance floor. The lights had been dimmed considerably. The dance tempo was slow. Both of Connie’s hands where on the back of Mark’s neck with her fingers playing with the hair on the back of his head. Her body was up against Mark’s in full contact. He thought that she had to be aware of his arousal the way she was pressing against it.

Connie moved back in his arms and looked up at Mark and said, “Thanks for the compliment,” and without waiting for a response, moved right back up against him. Mark’s hands had slipped lower and were pressing the tops of her buttocks. There was no objection and in fact she seemed to be rubbing against him a little more.

When the band announced that they had finished playing for the evening, Mark looked at his watch and suggested to Connie that they should leave. The time had just flown by and she reluctantly agreed. Walking to the car she wrapped her arm around Mark’s arm with the end result being his arm was being pressed against the side of her large breast.

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