Chapter 17: Hobart Explored

The next morning Frank woke up feeling refreshed and invigorated. He was pleased that he had resisted making love to her last night, which he probable could have at a pinch, although it would have been quite an effort. But now he was definitely eager and ready to do so.

He turned to her, looking at her beautiful body as she lay on her back, sleeping, her breathing heavy; almost, but not quite, snoring. After gazing at her for several minutes, he traced gentle kisses on her breasts and tummy and finally went down to her nether regions. As his tongue slid along the lips of her sex she woke, feeling lovely, wonderful sensations, but quickly realised what Frank was doing to her and slipped her hands to the back of his head, pulling him hard against her, as she told him how good it felt.

Frank continued with his oral and digital stimulation until she experienced her first orgasm of the morning. Once her moans of pleasure ceased, he knelt between her legs and guided his erect penis into her as she let out a sigh of contentment. It wasn't long before Frank had her legs doubled back over his shoulders as he drove into her.

By the time he exploded inside her she had already reached another massive climax.

As they were laying there recovering, the door bell rang and a voice called out "room service." Last night Frank had ordered breakfast for 8am so that they would be ready for their day out.

"Are you going to get up and let him in?" he asked.

"Oh Frank, I can't. I'm still wet from what you just did to me" she said embarrassedly, so Frank got up, pulled his shorts on and walked out of the bedroom, leaving the door wide open as he walked into the lounge room and let the waiter in. As he put the tray on the table, the waiter could see into the bedroom and could not help but notice the young girl lying on her back, her legs wide apart, looking as if she had just had sex.

When the young waiter had closed the door behind him, Frank went back into the bedroom and told her with a big smile "that was a wonderful view you gave the young man. He seemed to really appreciate looking at you, if the bulge in his pants was any indication."

"Oh Frank, should I have closed my legs or covered myself?" she asked with concern, worried that she had done the wrong thing, as she had deliberately lain like that thinking that was what Frank wanted her to do.

"No darling, you looked beautiful and I'm sure that he could tell you had just made love too, as I could see evidence on the lips of your sex" he replied.

This caused Helen blush profusely and undergo a wave of mixed emotions, pleasure from the compliment that Frank had given her, embarrassment from deliberately exposing herself and shame that the young waiter knew that she had just made love to Frank. But she realised that secretly she was excited as well and had actually enjoyed the experience.

But, Frank insisted, it was time to get up, have breakfast and get ready for the day's adventure.

Their drive along the Derwent River, west to New Norfolk was very pretty and Helen loved looking around the historic town, especially at some of the old buildings.

After a substantial morning tea there, they drove back on the other side of the river, stopping at Pulpit Rock Lookout to enjoy the views and then driving through Bridgetown. Here they went north to Brighton then east through Tea Tree before continuing down to Richmond, another historic town.

Here they had a late lunch, before looking around the old buildings and the goal. Helen chattered excitedly about what they had seen as they drove back to their hotel, getting there just after 5pm.

When they were back in their room, Helen was hoping that he was going to make love to her again, but he told her to shower and change and they were going back out for drinks in an old hotel then dinner at a posh restaurant.

It was 9pm when they got back in their suite and Helen realised that she was just a little tipsy. Frank had encouraged her to have two pre-dinner cocktails and then she enjoyed a couple of glasses of champagne with her dinner and even had a Tia Maria and cream with her coffee.

She went straight to the bathroom, cleaned her teeth, then showered and got into bed, anxiously awaiting Frank, as she realised that it had been over 13 hours since he had last made love to her and she was more than ready for him again.

Frank decided it was time to take her sexual experiences to a new level, so once he was in bed with her, he started kissing her several times before suckling on her breasts, taking her hard, long nipples firmly between his teeth and gently biting them. She groaned from that mixture of pleasure and pain that she was starting to enjoy.

Next, he moved his attentions to her sex, licking, sucking and fingering her, until she was extremely aroused and wanted him inside her. But he had other ideas. He rolled her over onto her tummy and started kissing and fondling her bottom. He ran his hand under her, his fingers moving along the lips of her sex and then into her vagina, while the fingers of his other hand were sliding along her cleft teasing the entrance to her anus.

After getting her further aroused, he reached for the tube of lubricant and put some on his middle finger and gently inserted that into her anus. She enjoyed having fingers inside both orifices, which he had done before, but soon there was a second finger in her anus and that felt just a little bit more uncomfortable, especially as he was thrusting them in and out. But he continued to massage her clitoris with his other hand.

Just as she was reaching an orgasm, he stopped, withdrew his hands and placed them on her hips lifting them into the air, while at the same time, he was spreading her knees further apart. He then quickly applied more lubricant to his erect penis and guided it to the puckered entrance of her anus. This hand then went around her and grasped a breast, teasing her nipple and fondling her.

Helen couldn't believe what was happening. He was actually pushing his penis into her bottom. Her initial reaction was one of revulsion and she was about to tell him no, you can't do that to me, but then remembered her promise. She grit her teeth, and tried not to resist as he pushed slowly into her anus. But it hurt and she tensed as she cried out. He stopped and she thought that he was going to withdraw, but no, it was merely a pause as, after she had relaxed, he slowly started to go deeper into her.

Again she cried out "it hurts, Frank, you're too big for me there."

Frank stopped, holding still inside her as he thought how nice it was to hear a young girl tell him he was too big, but he knew what she meant. He knew, though, that he just had to persevere, a little like when he took her virginity.

Helen had started to relax, thinking that this time he was going to listen to her and stop, but then she felt him move very slowly. His penis was sliding deeper into her, gaining a little ground with each movement before pausing again. Finally, she felt his body against her bottom and knew that he was all the way inside her.

Frank lay there motionless, except for his hands, which continued to manipulate her clitoris and breast until the pleasure she was receiving from this attention overcame any discomfort she felt from the invasion of her bottom. She realised after a while, that it was now only discomfort, and that the pain had disappeared.

As she relaxed and enjoyed his attentions to her clitoris and the way he was manipulating her nipple, Frank started to slowly pull his penis out a little bit but then he pushed it quickly back in. This hurt and she grimaced, but realised that it hadn't hurt as much as the first time. Again he paused for several moments, but he did not pause in his manipulation of her with his hands. Then he repeated his slow withdrawal and quick re-entry.

Frank repeated this time and time again, until she found that it wasn't hurting at all and she was actually thrusting back to receive him. Suddenly a wave of pleasure swept over her and she experienced her first anal orgasm, although, she thought, it was probably more from his stimulation of her clitoris.

Nevertheless, she was now enjoying what he was doing to her and the resultant relaxation of her muscles allowed Frank easier access. Now he was able to increase the depth and frequency of his thrusts and she experienced increased pleasure.

Finally Frank was able to enjoy the exquisite pleasure of sliding in and out of her tight bottom, especially when her muscles clenched him as she experienced another orgasm. But he didn't relinquish the attention to her clitoris and breast, knowing that at this stage, most of the pleasure she was getting was from this.

As his pleasure increased, Frank squeezed her breast tightly and he started to pound into her bottom, which hurt a little but Helen was feeling more pain from his treatment of her breast. This, however, was a pain that she had felt before and actually enjoyed, so ignored both pains and cried out for more.

He couldn't keep this up, he knew, but just as he exploded inside her anus, and she felt him throbbing in that secret place, she felt yet another climax wash over her.

Frank lay still for what seemed like ages, taking his weight on his elbows and knees, but some was on her bottom as he pushed hard into her still. He started to kiss the back of her neck, telling her how good she was and how much pleasure she had given him again.

Helen felt on top of the world. Her lover, an older experienced man, was telling her how good she was and how much pleasure she was giving him and this made her feel fantastic. That and what he had just done to her, she realised, made her want him to stay there for ever.

Eventually, Frank rolled onto his side, pulling her with him so that he could stay behind her, cuddling her and fondling her breast. He withdrew his hand from her sex and his penis from her bottom as he lay there, at first just kissing her cheek but then her lips as she turned her head towards him. Finally, he was able to slide his tongue into her mouth kissing her deeply.

Frank was soon asleep, still holding her, but Helen lay awake for ages, remembering each of the experiences she had enjoyed since arriving here with him. And enjoy them she had, realising just how much he had taught her. She had even enjoyed the shame and embarrassment of being seen by the waiter and knew that this would not be the last time she had anal sex.

Finally, she too drifted off to sleep.

This was to be their last day in Hobart and Helen wished she had been able to persuade her mother to take at least one more day off school. She had woken up first and had turned onto her side so that she could look at Frank, sleeping peacefully beside her. She wondered what experiences she was in for today, but didn't care. She would do whatever he wanted. So far she had enjoyed everything he had done to her.

Frank woke up and opened his eyes. He was looking straight at a beautiful young face that was staring adoringly at him, so he couldn't resist taking her into his arms and gently making love to her.

They went through the same routine as yesterday getting their breakfast, but this time Helen spread both knees wide apart, flat on the bed and pretended to sleep as Frank let the waiter in and asked him to put it on the bedside table. She hadn't realised that he was going to do that and as she half opened an eye, she could see the poor young man staring at her exposed sex, stammering as he put the tray down, asking "is this where you want it, sir?"

As Frank slowly signed the bill, the waiter took it without looking at him and backed out of the room.

As soon as the door closed, Frank laughed and said "you should have seen that. It was priceless."

"Oh Frank, I'm so embarrassed and feel so ashamed. I didn't realise you were going to bring him in here; I thought he would just catch as glimpse from the other room as he did yesterday. Did you really want me to show myself off like that?" she asked, mortified by what had happened, but secretly thrilled too.

"That's why I brought him in here. I knew how you were lying and I wanted him to see you close up. It gave me a buzz and you have nothing to be ashamed about. Your body is beautiful. In fact, when we go shopping this morning, I want you to wear something revealing and no underwear. I might buy you a pair of shoes, but you'll have to try several pairs on and get the salesman to help you, of course" he told her.

Helen felt a delicious shiver of forbidden excitement run through her as she thought what the salesman would see and how embarrassed she would be. She knew that she would be looking at Frank's face to see his pleasure from her exposure and ensure she had his approval. She hoped that this would make her feel good about exposing herself to a total stranger.

After they had eaten their breakfast, Helen showered and put on the dress she had worn on the first day, but this time without any underwear.

"Is this all right, it's the best I've got?" she asked.

Frank looked carefully at it, asking her to turn around and bend down, then sit on the chair and lift her leg. While she looked lovely, not a lot of secret flesh was exposed.

"I think our first stop will be a dress stop for something a little more revealing" he stated.

Again Helen felt herself shiver at the thought of wearing something even more revealing, especially with no underwear. She believed that the way she was dressed was rather daring.

Fortunately it was a fairly warm day, which for this time of the year was not always the case here in Tasmania, so she was not cold, but nevertheless, she felt strange walking down the street with no panties. She was used to going braless, as her breasts didn't need support, but the fresh air around her groin felt somewhat erotic.

Sure enough, their first stop was a dress shop, but Frank couldn't find what he was after there. In the second shop he found a lovely soft dress with tiny thin spaghetti shoulder straps that went all the way down her back to join the dress on her waist while at the front the straps widened out to barely cover her breasts, again joining the skirt of the dress at her waist. The dress was tight around her waist, but the short skirt flared, so that the slightest movement made it twirl around her. The material was gossamer thin, and looking in the mirror she could see her nipples almost poking through the material.

"I can't wear this Frank, surely you can see too much?" she exclaimed.

"You look absolutely beautiful. We'll take it" he said to the salesgirl, asking her to wrap her old dress.

"She does look lovely in it. Why not take these too. I'm sure that they will enhance her appeal" she replied as she passed Frank a g-string made of sheer material.

"Good idea. Put them on, darling" he told Helen, adding as she seemed as if she was going back to the change room to do it, "you can put them on here. There's no one else in the shop."

She did what he wanted, putting them on in front of the saleswoman, knowing that each time she lifted her leg to step into the g-string, the woman could see her sex.

"Let's see what they look like" Frank said, lifting her skirt up and revealing the transparent g-string that seemed to highlight her nudity rather than conceal anything.

She felt even more ashamed and embarrassed as the woman said "she is a real beauty. You must be proud of her."

"I am" he replied and Helen felt a warm glow all over.

As they stepped out onto the street, Frank carrying her old dress in a bag, Helen told him how embarrassed she had been, and how naked she felt now, but he reassured her telling her that he was really looking forward to her flashing some young guys now.

First, though, they wandered through several arcades browsing in shops. Frank insisted that they go up and down a number of escalators, knowing the view anyone below her would see if they cared to look up at Helen.

She wanted to find a present for her mum, so Frank not only helped her find something, but also insisted on paying, not only for the present she chose, but for a second item that she had considered as well, which made her feel really good. Frank was just happy to be able to give Dawn something.

"Here's the Cat and Fiddle Arcade" he told her, having arrived just two minutes before 11am, which he had been endeavouring to do.

"Why do they call it that?" she asked him.

"Ah, that would be telling" he said, trying to make another few moments go by as he pretended to ignore her, before he pointed up high on one wall and added "look up there."

Where he pointed there was not only a replica of a cat with a fiddle, but also a moon with a cow below it and right on 11am, the cow jumped over the moon. Helen laughed, enjoying the significance of the arcade now.

"We have to find a shoe shop with a young salesman" he told her.

After looking at several, they found one that sold sports shoes. At Frank's request, Helen went in by herself, so that he could come in separately. She started to look at a pair of cross-trainers and a pair of runners, when a young salesman came up to her and offered to help. She said she didn't know which type she needed so wanted to try both on. He, of course, offered to help, which she readily accepted.

Soon she was seated at a bench, noticing Frank examining some shoes a couple of metres away where he could see the young man's face and still see her. Meanwhile, the young salesman had laced up the first pair she had looked at and started to help her put them on. She lifted her leg up to assist him, knowing that her skirt would fall back and her sex would be visible through the transparent g-string. She looked at Frank who smiled at her and she could see the beginning of arousal on his face, as he wet his lips with his tongue.

She stood up, swung around on the shoes, her skirt flying up so that her almost naked bottom was visible briefly, then bent down to adjust the laces. She knew the view from behind would have shown virtually everything, but she was also trying to let the young man catch a glimpse of her breasts and saw Frank's approval as he nodded. But she hadn't counted on the slippery material of her dress sliding off her shoulder and suddenly one breast was completely exposed. For a moment she tried to pretend she didn't notice, then blushed as she saw the man staring at her, stood up and adjusted her dress.

Helen sat back down and asked to try the other pair on, allowing the salesman to undo her laces, lift her ankle and take the shoes off her feet. She could see him staring into her crotch and felt herself getting wet, then realised how visible that would be as there was only the thin layer of material barely covering her sex. Once it was damp, it may as well not be there, she thought.

But for Frank's benefit, she went through the motions of trying on the other pair, this time bending right down as she sat there, allowing her breasts to be seen again as the dress fell forward.

"Sorry, but they just don't seem right. Sorry to have bothered you" she smiled sweetly at the young man who was helping her remove the shoes, while staring between her legs. He quickly reassured her that it had been no bother, as he tried to hide his groin by holding a box of shoes in front of him. Helen had already seen the telltale bulge, however, before she stood up and walked out the door.

Frank meanwhile had refused the offer of service from another salesman, saying he was just browsing and soon followed her outside and joined her several doors down.

"Did you see the look on his face?" she asked excitedly, adding with concern "you did enjoy it though didn't you? It was what you wanted?"

"Of course I enjoyed it, especially when your dress slipped and your breast fell out. You sure had an affect on him though. You should have seen the bulge in his pants" he assured her.

"I did. I still find it hard to believe that I can make a man become that aroused so easily. Must be because you have turned me into a woman" she murmured. Then she added "I'll have to go back to our room and take this g-string off, though, it is sopping wet."

"So you did enjoy it then, because I assume it's wet from your arousal, right?"

"Yes" she admitted, hoping that he would take her back and make love to her.

And he did, but he too was extremely aroused from their morning's fun and was rougher than he had been before, squeezing her breasts hard, biting her then rolling her over and taking her from behind so that he had the freedom of access to cruelly pull at the lips of her sex and pinch them, scrape his fingernails roughly on her clitoris and bite her earlobes.

Helen didn't quite know how to react. She was extremely aroused from the shame and embarrassment of her flashing adventures and from Frank's pleasure, but she was experiencing more pain than she expected or even wanted. But Frank seemed so aroused and to be enjoying what he was doing to her that this in itself caused her pleasure.

Suddenly she felt him withdraw from her and his hand smack her hard on her bottom.

"Ouch, what did you do that for?" she cried out.

"Be quiet and lift your bottom higher" was all he said so she complied. Almost immediately, she felt his hand smack her hard again, causing her to grunt from the brief sting, but she did what he wanted, kept quiet with her bottom in the air.

Smack, smack, smack, his hand went, but she didn't lower her bottom or complain. Frank had his hand cupped so that in fact it made a lot of noise rather than actually hurt much.

She was grateful when she felt his penis again thrusting in her vagina as he pounded her, because at least he wasn't smacking her. She realised though, she was actually enjoying what he was doing to her, despite the fact that it hurt a tiny bit.