It Doesn't Hurt to Ask
Chapter 1

Copyright© 2008 by Westside24

Romantic Sex Story: Chapter 1 - 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  

The flight from Chicago to Tampa so far had been relatively smooth and Mark Scales hoped it would last but doubted that it would. He had checked the radar before leaving for the airport and noticed a rather severe storm entering Georgia that could cause some turbulence which could make for a bumpy flight.

What was outstanding about the flight so far was the flight attendant in the first class section. She was beautiful and just watching her was making the flight very enjoyable. Mark thought that flight attendants that looked as good as she did were just a man’s fantasy. She was about thirty years of age, five feet six inches tall with short blond hair and was immaculately groomed. She was wearing a knee-length skirt with a white blouse that showed a pair of fine legs, thin ankles and a cute little butt. Her breasts weren’t overly large but were in proportion to her body. Just watching her move around was a treat. She was definitely eye-candy.

Mark’s thoughts about the calmness of the flight not lasting were proven to be correct. The pilot announced to the passengers that they were going to be going into some rough weather for a while and asked everyone to take a seat including the flight attendants. The fasten-seatbelt sign was illuminated. The good looking flight attendant sat in a jump seat kiddy corner across the aisle from Mark who was sitting in the first row of first class seating. He was staring at her when she looked up and caught his gaze. Since the window seat next to Mark was unoccupied he asked, “Would you be more comfortable sitting here if I moved over to the window seat?”

She smiled at him and responded, “Thanks, that would be nice,” and she moved to sit next to Mark.

“It was very nice of you to offer your seat to me.”

“Well it’s every man’s fantasy to have a beautiful flight attendant sitting next to him.”

“I thought Pam Anderson was every man’s fantasy?”

“I would have to agree that she certainly is in the top ten. Every man has his own list of women that are his fantasy. Changing the subject where are you going next after the plane lands in Tampa?”

“Oh that’s it for me, it’s my home. I started out from there today and went to Kansas City, to Chicago and now back to Tampa. Normally I fly Tampa to Atlanta to Europe and after a layover then fly back. This month I just wanted to break the routine so I selected a route that was more of an 8 to 5 job. In a few days I will go back to my normal hop.”

“As a world traveler it must be interesting to be seeing the world and the many different countries.”

“It is, but we don’t get that much time between flights so it’s a lot of airports and hotels I only get to see. The advantage of these long flights is that my flight hours add up quickly which gives me some time off between flights.”

“Is Tampa your home town?”

“No, St. Pete is. I was born in Ocala and raised in St. Pete and its right next door on the other side of Tampa Bay.”

“I was wondering that if you aren’t doing anything tomorrow, if would you like to be my tour guide? This is my first time in the area and I do have some free time as this trip is a combination of business and pleasure. I would like to see the area and it would be nice to be shown the area by someone who is familiar with it.”

“Are you asking me out?”

“I guess in a roundabout way I am. But like I said, I would like to see the area.”

“How do you know I’m not married?”

“Well, I don’t see a ring on your finger. As attractive as you are I don’t doubt that you get asked out a lot. I am hoping that there currently is no significant other. You seem to enjoy helping people and I can only hope you would take pity on me and help me see the interesting places. By the way, my name is Mark Scales. I know I have a choice of tour guides when I tour and I can only thank you if you will be my tour guide.”

His remark brought a little smile to her face.

The pilot came on the speaker just then and announced that we were through the rough weather and the flight attendants could resume their duties but advised everyone to keep their seatbelts fastened when seated.

“Let me think about it,” she said as she got up to check on the other passengers.

When it was announced to fasten the seatbelts for landing, she sat in the seat next to Mark. She handed him a card that had her name and address and other contact information on it. The name on the card was Trish Stevens.

“You can pick me up at ten and I will give you a tour. There are places I haven’t seen in a while myself, so it should be interesting to see if they have changed.”

The landing was smooth and Mark received a nice smile from Trish as he exited the plane.

Getting a rental car with GPS made the drive to the condo worry-free. When Jim Stanford the father of Brad, a life long friend of Mark’s, heard that Mark was going to Tampa he insisted that Mark stay at his condo. The condo was in St. Pete. Jim and his wife had gone back to Chicago for the Christmas Holidays and wouldn’t be going back to the condo till mid-January so it was available. Jim insisted Mark stay there saying it would be nicer than staying in a hotel. Mark had to agree with Jim that staying in a three-bedroom condo on the top floor of a fourteen story building overlooking the gulf was a very nice accommodation.

After a short drive along Gulf Boulevard, Mark stopped at one of the many restaurants located there and had dinner and an adult beverage. He went back to the condo and watched a little TV before calling it an early night.

Since the rental car came with GPS there was no problem in finding Trish’s condo next morning. Mark pressed the doorbell and he heard her say on the speaker that she would be right down. A minute later she opened the door and looked as beautiful as he remembered her. She had on a white blouse with khaki shorts that came down to just above her knees. The shorts weren’t overly tight but they did show a nice jiggle to her butt when she walked.

“Well, are you ready to start your tour?”

“Who wouldn’t be with a beautiful tour guide such as yourself?”

That brought a little blush to her face but Trish was serious about the tour. She started off by showing him downtown St. Petersburg, its pier which was slated to be torn down and the Baywalk. She pointed out the route of the formula one road race that runs through downtown St. Pete and into the small airport that would be staged there in about three months. They went past Tropicana Field where the Rays played baseball and drove out to Fort Desoto. There they visited the fort which was in a little disrepair, gazed at the Sunshine Bridge, and walked on the famous and highly rated north beach. It was back up from the fort and over to Gulf Boulevard to head north and up the coast to St. John’s Pass. They stopped for a late lunch overlooking the water and took a walk around the many shops that were there. Their tour finished up with a quick drive farther north into Clearwater and its downtown.

While Trish was nice and personable, Mark sensed something was going on with her that he couldn’t quite put his finger on what it was. He felt that she was being defensive with him and that she had put up a shield for some unexplained reason. Mark assumed that she must get hit on quite a bit and maybe this was her normal reaction to men. He hoped he could get through this barrier he sensed that she had erected. A second thought he had was that he hoped she did like men and that she didn’t bat from the other side of the plate.

Back at her condo Mark said, “Seeing the area with you was very informative and enjoyable. In view of you hard work today how about you letting me take you out to dinner? That way you can continue your tour and show me some of the nightlife the area has to offer.”

“I enjoyed seeing those places again and the drive as well. I hadn’t been to some of those places in a long time. It is a pretty city and an interesting area. You have been a perfect gentlemen and dinner would be nice. Where do you want to go to dinner?”

“You pick the place. Somewhere with good food and atmosphere and if it has music, that would be a plus.”

“One of the ex-Tampa Bay pro football players has a restaurant in Clearwater that meets those requirements. If you want, I can call and make a reservation.”

“That would be great. How about I come back and pick you up a seven?”

“I’ll be ready.”

Driving back to the condo and getting ready for dinner Mark couldn’t help but think about Trish. She was a walking wet dream and while she had a nice personality and was intelligent, he sensed that she was holding something back. Maybe she just didn’t know Mark that well yet and that was the problem. He again hoped that he could overcome her hesitancy if that was what it was.

Wearing an open collared button-down blue shirt and a tan sport coat with dark slacks he pressed the doorbell on Trish’s condo precisely at seven. She answered that she would be right down. When she opened the door Mark thought it couldn’t get any better that this. She was wearing a dark green straight cut knee-length dress with a square neckline that just showed the tops of her breasts. The dress was made of some sort of shiny material and while it wasn’t overly tight, it did highlight the enticing curves of her body.

“Wow, you look absolutely beautiful but I bet you hear that all the time.”

“It’s nice to hear those remarks anytime.”

Mark helped Trish into the car. He had a hard time driving because his eyes wanted to stay on her instead of the road. He could tell she knew she had this effect on men. He thought that maybe she wanted to be appreciated for something other than her good looks and he thought he would take that approach with her.

At the restaurant her entrance confirmed what Mark already knew. She was a head-turner. All of the men and most of the women watched Trish as she was escorted to their table. This gave Mark a sense of pride as he knew all the men would be envious of him.

While sipping on their cocktails and during the meal Mark avoided any talk about her physical beauty but instead asked her about her work and the places she visited. He asked her about her insights as to those places and she seemed to enjoy relating her thoughts on the various locations. He complimented her about her comments on these various cities although he thought they really weren’t that insightful. She seemed to enjoy these compliments. What she thought the historical significance of certain places were and the shopping that was available at those places seemed to be her two favorite subjects. She seemed to warm to Mark as she talked of these locations and what to her were the attractions.

Sipping on an after-dinner drink, Mark noticed that a band in the lounge had started playing. He asked Trish if she wanted to go into the lounge to listen to the music and maybe dance. She said she wasn’t much of a dancer.

“Let’s go in there for a while. I too am not much of dancer but I do a mean two-step.”

This brought a smile to her face with her saying, “Okay.”

In the lounge they found a table where they placed their drinks and proceeded to the dance floor to join the other couples. Trish fit nicely in his arms. His arm was around her with his hand on the small of her back. She wasn’t plastered up against him but she was quite close. The scent of her perfume and the cleanliness of her hair were two things that Mark noticed while they danced. They had danced to a few songs when the band decided to take a break. They went to the table and finished their drinks. Because of the hour, Mark asked her if she wanted to leave. She nodded in agreement.

The ride back to Trish’s condo was somewhat subdued with just a little small talk. Mark parked the car and turned to Trish.

Before he could say anything she smiled at him and said, “Do you want to come in for a drink?”

“Yes, that would be nice.”

Watching her walk up the steps in front of him, Mark thought her hips moved like a well-oiled machine. There was such a nice sway to them in that dress that gave Mark some carnal thoughts of what he would like to do with this very beautiful woman.

Once in the condo, Trish put her purse down on a table. She was taking off her ear rings and while doing this turned to Mark and said, “What can I get you?”

He walked up to her, placed his hands on her waist and gazing into her eyes said, “I was hoping to hear, coffee, tea or me.”

Nothing more was said and there was a quietness in the room as they gazed into each other eyes. Mark very slowly bent to kiss her and while Trish did not move to meet him, she didn’t move away from him either. Her hands had dropped to her sides as he was bending to kiss her. His lips touched her lips but there was no response from her. He continued to kiss her and then maybe after thirty seconds it was like a dam had burst. Her arms went around him while her lips opened and her tongue became active and dueled with Mark’s. Trish’s body was up against Mark and it surprised him as she was rubbing up against him like a bitch in heat. His hands dropped down to her buttocks and caressed her bottom. The shiny material of her dress slid smoothly over her panty-covered ass.

One of his hands rose to her breast and it fit very nicely into his cupped hand. After some fondling of her breast, Trish broke apart from the kiss and the look in her eyes was one of pure lust. Her breathing was deep and pronounced. She took one of Mark’s hands and led him to her bedroom saying, “My roommate is in Paris tonight and not due back till tomorrow afternoon. We won’t be disturbed.”

In the bedroom she gave him another toe-curling kiss and then turned her back to him. He took the hint and pulled the zipper on her dress down. While he was at it, his also opened the clasp on her bra. She just let the dress and bra fall to the floor. Trish turned toward him wearing a single string of pearls, bikini-cut green panties and thigh-high nylons. Mark thought that she put any Playmate he had ever seen to shame.

Mark was just staring at her when she stepped forward toward him, gave him a little kiss and said, “Let me help you with that.” Her hands went to his belt buckle and then pulled down his zipper while he was working on the buttons of his shirt.

Stepping out of his pants he noticed her hands dropping to the top of her panties. “Oh no, please don’t! Let me do that.”

Mark dropped to his knees as he lowered her panties down her legs to the floor. He looked at her most private part which was shaved except for a little tuff of blond hair above it. She was a true blond he thought. He bent to kiss it and she opened her legs to give him access. The scent of her arousal was evident. The kiss turned into licks and her hands dropped to his head to guide him. His hands were on her buttocks pulling her into him as much as he could.

They were next to the bed and one of Mark’s hands pressed on her stomach. She understood what he wanted. Trish first sat down and then lay down on the bed with her legs drawn up and opened wide. She was giving him unlimited access to her most private part. Her hands continued to guide his head as he was worshipping her.

It wasn’t long before her legs closed and her thighs were squeezing Mark’s head and pressing on his ears. He knew she was having an orgasm. He increased his efforts of sucking and licking her clit. She seemed to be having continuous orgasms and was twisting her hips from side to side. Finally she released the pressure on his head and Mark was thankful as his breathing became easier.

“That’s enough... , enough. I can’t take any more. Please come up here. Make love to me.”

Mark thought he was already making love to her but he stood and dropped his shorts. She was moving back on the bed and he crawled towards her.

She saw his enlarged love tool as it bobbed up and down. “Oh that’s a nice one, nice and big and ready. I have just the place for you to put it to good use. Come here,” and she raised her arms toward him.

He mounted her easily. Her hand grasped and guided him into her. In a few thrusts he was completely seated. Mark waited just for a little while for her to adjust to him while he kissed her. His hips went into the age-old motion of making love. Trish’s arms where around him and his hips were in a slow motion of his shaft penetrating her. He was alternating nibbling on her ear lobe and putting his tongue into her ear.

While doing this he whispered, “Earlier we talked about a man’s fantasy. My number one fantasy is happening now. Making love to an intelligent, beautiful, sexy, passionate, flight attendant has always been my number one fantasy. This is a fantasy come through. You are one super woman.” He then thrust his tongue further into her ear and wiggled it around.

Trish squealed as he did this and then broke free. She then did to Mark’s ear what he had been doing to hers. Her legs rose to where her heels were resting on his buttocks so she could get more leverage. “Do it, do it, do it. Love me, love me, love me. Oh God, love me,” she said.

She stopped her movements and shuddered as she climaxed. He could feel her internal muscles squeezing his shaft. When the moment passed, her legs dropped to the bed and she gave him another long and loving kiss. He continued to thrust into her until he felt his moment approaching. He asked her if he could cum in her and she told him she was safe.

As he was pumping his sperm into her he heard, “I can feel you cumming. You are filling me up. This is so good, so damn good. I love making love. My heart is beating so fast.”

When he was spent, Mark dismounted from Trish and lay down next to her. They were each having their own thoughts about what had just occurred. She cuddled up to him and her hand was lightly caressing him by going up and down on his chest and periodically checking if he was ready for another go-round. His arm which was around her was also caressing her and periodically giving her buttocks a squeeze.

“That was awesome. I am glad I agreed to be your tour guide. I didn’t know they had such fringe benefits,” and she chuckled in saying this.

“I am glad you were my guide as well. Being with a beautiful and intelligent woman who gives completely of herself is something we red blooded males can only dream about. You my lady, are a dream come true.”

“It’s nice for you to say that. Are you ready to go again?” She grasped him and realized that in another minute or two he would be.

He was and this time it was much slower and longer lasting. Afterwards they whispered sweet nothings to each other and fell asleep in each other arms.

Mark awoke with the morning light filtering into the bedroom. Trish was still sleeping and the cover was down to her waist. He studied her and was mesmerized by her physical beauty. Her lips, her breasts, her nipples were all works of art. She must have felt his eyes on her because she awoke and he watched her breasts do wonderful things as she stretched while she yawned.

“Can I get you something for breakfast?”

“Yes you can... , you.” He reached for her and she felt his morning woody pressed against her.

“We aim to please.” Trish put her arms around Mark and twisted so she was atop him. She reached down and lined him up so that he could insert him into her. They fell into a now familiar rhythm with her reaching a climax before him.

He didn’t want to leave but she had to get to the airport by noon for the first leg of a flight that would eventually take her to Paris. Mark did have an appointment for lunch with the CEO of a small company that Mark was considering purchasing some stock in for his mutual fund. Mark thought it was best to give Trish time to get organized and ready for her flight which had him shower and dress.

“Do you ever have any layovers in Chicago? If you do, you could give me a call and I could show you Chicago. Maybe we could put some real meaning into the word, layover.”

She laughed at his statement and said, “That is a major hub for our international flights. I think something like that could be arranged. It would be nice to relax after coming back from a long flight.

Trish gave him a long-lasting scorching kiss at the door.

She surprised him when as he was walking out of her condo. She patted him on his butt and said, “We know you have a choice of flight attendants when you tour and I thank you for choosing this one.”

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