Selecting the Right Girl
Chapter 12: Two Second Dates

Copyright© 2010 by Pappyok

Romantic Sex Story: Chapter 12: Two Second Dates - Frank is a 45 year old recent divorcee, but now a multimillionaire. He decides to engage a young lady to accompany him on a first class around the world tour. See how he selects his travelling companion - the interviews, follow-up dates with some and then brief holidays with a selected few. Each of these girls tells her story and why she applied. Follow Frank on his gourmet dates, sexual adventures and travel until he choses his right girl.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Mult   Consensual   Romantic   NonConsensual   BDSM   Spanking   Oral Sex   Anal Sex   Sex Toys   Food  

WHEN FRANK WOKE up he was amazed to find that it was 10am already and today he was to have a second date with Helen. He decided to go down and use the hotel's excellent gym and get some much needed exercise, especially to offset the excessive intake of rich food that he was experiencing.

Once he was back to his room, he had a long, hot shower, shaved and dressed and went out to have brunch in a café. After last night's dinner and knowing that he was going out to dinner again tonight, he figured that this would be the only other meal he would have today. Not that he was hungry.

But he actually enjoyed the scrambled eggs and bacon on toast and washed down with a glass of orange juice and then a double short black coffee.

He read the paper as he ate while he reflected on lasts night's date and how much he had enjoyed Sharon's company.

After he had finished, he went to a travel agency as he thought it was time to start making some tentative plans. Once he had outlined the big picture for next year, he suddenly had a very attentive and super helpful travel agent. There was potential for a lot of commission and a lot of work out of this customer, the agent could see.

He also made preliminary bookings for Norfolk Island, as that was only a month off.

He came away with a fist full of brochures and timetables and a promise to develop a few suggested outline plans for him to consider. After all, potentially he was leaving on this holiday in about three months.

It was mid afternoon by the time he returned to the hotel, deciding that this would be a good opportunity for another short workout and then a long swim in the indoor pool.

Two hours later, he was sitting in the upstairs cocktail lounge waiting for Helen. He was only drinking water at this stage replacing some of the fluids he had lost during his exercise.

Right on time, Helen came in, spied him sitting at the same table they had shared last week and came over to him. He stood up to greet her, enjoying looking at her slim body, wearing a dress that showed plenty of very attractive flesh and wearing her hair in away that made her look older than last time. She could easily be 19 or 20 the way she looked.

She came right up close to him, gave him a small kiss on the lips and whispered her greeting.

"What would you like to drink, Helen, a different cocktail or the same as last time?" he asked her after telling her he was glad she made it OK.

"Surprise me" was her response. Then a little later she added "Mmm, this tastes yummy. What is it?"

"Tequila Sunrise. Glad you like it" he replied.

They sat there enjoying their drinks, Frank settling for another Dry Martini, gazing at the fantastic view of the harbour. It had been a beautiful sunny day, but now the sun was setting, the reflections on the water absolutely beautiful.

The hour rushed by, Frank enjoying her bubbly, excited persona. He had had a second drink, a small single malt with a splash of water, while she had sipped slowly on her cocktail. At 7pm he stood up and invited her to come to dinner. He held her hand as they walked to the lift and waited for it to take them to the floor that the restaurant was on. Once in the lift, with no one else inside, she snuggled close to him and gave him another small kiss, telling him how much she had been looking forward to tonight.

They shared a bottle of white wine and an entrée plus a main course, but when he offered dessert, she declined.

"Do you mind if we go to your room for small night cap, I'd like to discuss a few things with you in private and it is a bit difficult to talk about the things we need to discuss here, with the waiters walking by" she said softly.

What she said made sense, although as they walked out and caught the lift to his suite, he started to have second thoughts about taking her back there. Still, she was old enough and it was her idea, so there shouldn't be any problem, his mental process told him, but he had no intentions of having sex with her tonight.

Once they were in his room, she sat on the lounge while Frank poured them both a small drink. He gave one to her, a Tia Maria and milk, while he had a cognac, and then sat down next to her.

"Frank, please be honest, are you seriously thinking about taking me as you travelling companion next year or do you think I am too young for you?"

He hesitated for a moment before telling her "I guess I am worried that you might be a bit too young and that you would get bored with me after a few weeks, even though I really like you and enjoy your company. What's more, you certainly make a very beautiful companion."

"Thanks, Frank, but I don't mind and you probably are a little bit right. Although I can assure you that if I did go with you, you wouldn't be sorry and I would make sure you enjoyed our nights together, if you know what I mean" she said in a soft, sexy voice, before adding after a slight pause "but I do have a very big favour to ask you."

"What's that, Helen?" he asked.

"I really, really want you to take me away for a short holiday. I'm happy for it to be for at least five days, in fact I'd like it to be, and then I won't be unhappy if you tell me you don't want me next year. But before you say anything" she quickly added "let me first tell you that I promise you won't be sorry and I will do everything and anything to make sure you enjoy our time together."

"But why? It seems you actually don't want to go with me next year, do you? Is it just so you can get the $5,000 your mum made me offer?" Frank asked a little disappointed, but not totally surprised.

"No, not entirely, although, being honest, that obviously is one reason as I'm sure you know how much I need the money. But, in fact I can assure you that if at the end of our holiday you wanted to take me with you next year I would more than happily go. I still quite like the idea of the year long holiday you are offering. I just think that you will probably realise that the age gap may be too much for us to be together for a whole year.

"No, let me tell you the whole truth. I met someone a few months ago and, although mum doesn't know, we spent a fair bit of time together over the school holidays while she was at work. Last Sunday I met him again and he is still keen on me. I put him off, saying that I would contact him on Sunday and possibly see him in the second week of the next school holidays.

"I know what you must be thinking, but you're wrong. I am still a virgin and, in fact, that's one of the reasons I want to spend the time with you. I would really like my first lover to be someone like you, older, sophisticated, nice, caring, experienced, someone who will teach me to not only how to make love but also how to enjoy doing it.

"One of the reasons I am putting off meeting him again until after we have our holiday together, which I do hope eventuates, is just in case you also want me next year. If you do, then I won't see him again. At the moment he is just a potential boyfriend, but I know if I start seeing him I'll want more from him.

"That leads me to another reason I want to spend the time with you. Mum knows that I have gone on the Pill. She took me to the doctor as soon as we knew I was getting an interview and I have been taking it for three weeks, so in another couple of weeks, I will be able to sleep with you safely.

"I hope to be able to persuade mum that once I have lost my virginity with effectively her blessing, if you then don't want me anymore, I should still continue taking the Pill. That will allow me to enjoy a relationship that would probably develop soon after you reject me, assuming that is what you end up doing" she finished, almost exhausted from the strain of telling him all this, but then, sensing Frank was still a little undecided she added "but before you make your final decision, let me try and influence you a little."

With that, she leaned towards him and kissed him, not a little peck on the lips, but a full blown, passionate, tongue and all kiss, that left him tingling with excitement. Her hands were cupping his face, playing with his ears, as she drew him in for a second, even more passionate kiss. His arms involuntarily went around her, drawing her close to him as he returned her kiss with enthusiasm.

As the kiss ended, she moved back a little and reached behind her, pulling the zip on the back of her dress down, allowing the front to fall below her waist. This revealed the most perfect pair of breasts Frank had ever seen; small, firm, round, milky white breasts topped with beautiful, surprisingly long nipples. She grasped his right hand and placed it on her left breast as she gave him yet another delightfully passionate kiss.

As soon as her lips left his, she drew his head down to her breast, holding his mouth to her so that he could suckle on that long nipple making it hard, his teeth gently scrapping back and forth along its entire length. His other hand came around and started fondling her other breast as he opened his mouth and sucked as much as he could of her breast into his mouth.

Frank was squirming with desire, knowing he couldn't consummate their relationship, at least not until he took her away for a holiday, but suddenly he felt her hand opening his fly and reaching in to fondle his engorged penis. She pulled away from him momentarily, using both hands to undo his belt and then his trousers, pulling them and his underpants right down to his ankles. He let her take them off completely, before she knelt between his legs, fondling and kissing his now very erect penis, while using one hand to gently fondle his testicles.

"Are you sure you want to do this?" Frank moaned, hoping she would say yes. But she didn't. She simply took as much of his penis as she could into her mouth, sucking it, making him slide in and out as her lips closed tightly on his flesh.

His hands came down and gently held her head, but his hips started thrusting up as his penis throbbed inside her mouth. She continued to hold and stroke the base of his penis with one hand while caressing his testicles with the other. Her mouth didn't stop moving up and down along his throbbing shaft, her tongue licking and teasing the end of his penis every time her movements brought them in contact.

All too soon he was warning her that his conclusion was about to happen, expecting her to withdraw and finish him just with her hand. But she ignored his warning and just continued sucking him, harder and faster until he could hold back no longer and fired his culmination deep down into her throat as he groaned with pleasure.

Helen stayed with him, gently sucking and stroking until he had completely stopped his spasms, finally sliding her lips along the entire length of his slowly subsiding erection, kissing the head of his penis and licking the last drops of moisture from him before she totally withdrew.

Frank pulled her up to him and kissed her deeply, tasting himself in her mouth, although she had swallowed what he had given her.

"Now where are we going for our time away Frank?" she asked in a seductive voice, much older than her years.

When Frank had calmed down and recovered his equilibrium, he merely said "where would you like to go, Helen?"

"How about Hobart? I'd like to look at some of the old buildings there and in the surrounding towns. I'm told there are some great examples of architecture that I would benefit from seeing" she replied, having thought about alternatives during the past week.

"That's fine, so when would you like to go?"

"Friday the 2nd of October would be good for me. That's in two weeks and I can get off at lunchtime and be back at school on the Wednesday. Oh Frank, thanks, I promise you that you won't regret it. I'll do everything I can to make you enjoy it too" she gushed.

Frank dressed, finished his drink and told her that he better take her home. He rang for the limousine that he had on stand by and took her downstairs.

She sat in the back cuddling him, excited and pleased that she had convinced him to take her away. She was really looking forward to being able to spend the time away with Frank and what he would do to her. She just hoped the next two weeks would fly by quickly.

Frank gazed down at her, having difficulty reconciling this excited young girl with the one who had made love to him so passionately and given him so much pleasure just a few minutes ago.

He hoped he wouldn't regret his decision, but he was convinced he was doing the right thing by her, anyway. He was almost certain that she would be relieved, however, when he told her that he wouldn't be asking her to be his travelling companion next year. He felt rather certain about this now.

Just before they got to her place, she pulled his head to hers and kissed him deeply, whispering to him how happy she was and promising to make him happy too, for at least the five days anyway.

As she went to get out of the car, Frank told her he would ring her in about a week to finalise the arrangements for their time together in Hobart, adding that if she or her mother changed their minds to let him know, preferably before he had booked the flights and accommodation and before the legal papers were drawn up.

Frank assured her that these legal papers were only to satisfy her mother, but she insisted that there was no possibility of either her mum or her changing their minds. It just was not an option and she would definitely be going with him.

As the chauffeur drove him back to his hotel, Frank mulled over everything that had been said and done during the evening. He still couldn't believe how much pleasure she had given him in his suite and just how nice she was.

He also realised that she was putting a big load on his shoulders by expecting him to be a super lover and teach her all about sex. It was a prospect that was both exciting and daunting.

That night he fell asleep dreaming of his forthcoming week in a luxury hotel on the waterfront at Hobart and the experiences he was going to have with an incredibly beautiful, albeit far too young, girl.


Frank enjoyed another sleep in, although not as late as yesterday. After he had showered and dressed, he ordered room service, deciding to sit out on his balcony and enjoy the sun while he read the Saturday papers.

He had to leave at 10:30am if he was to pick up Sandy at 11 as arranged.

Right on 11am the chauffeur pulled the limousine up outside Sandy's place. Frank got out and rang her bell. She quickly answered the door, with her things ready to go. Frank picked up a rather heavy briefcase commenting that there must be enough material to study for the week. She also had an overnight bag, but she insisted on carrying that herself.

When she saw the chauffeur, standing next to the limousine, waiting to take her bag, she nearly flipped "I thought you must have hired a car and were going to drive me. I never expected this. Wow, it's great" she bubbled.

They enjoyed the drive, chatting away like old friends. He found he was very comfortable with her and she seemed equally relaxed. She told him about the two nights she had danced last weekend after she had left him, but that she was pleased to be having this enforced break.

"Not that you are forcing me, I mean my period is" she said with a lovely laugh, and Frank joined her in laughing at what she had said. She added "hopefully it will finish tomorrow and I'll start on the Pill, so that I should be ready to go to Norfolk Island with you if that's what you still want. You suggested about the 21st of October I think, is that still when you want to go?"

 
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