Tim Ch. 02

Jessica was enjoying this. She forgot how much knowledge about whoring she had accumulated since coming to the island and Holly seemed a very willing pupil. Eventually the inevitable call came from Miss Christensen. They were told to put their uniforms on and go to suite 652, they were to attend 'Seb Prasca'.

When Seb answered the door, the girls curtseyed and asked if he wanted some company. They looked almost painfully attractive and Seb was grateful that he didn't have to go out and try to pick up such a girl. He knew they were there for his pleasure but he still somehow felt shy about approaching a prostitute.

Seb had made a mint in the internet boom and unlike many of his peers had managed to get out before the dotcom crash. He was innocent of the real world and fantastically wealthy. He had been recommended Cartwright & Palmer by one of his partners who had been impressed that although the prices were high neither the girls or the management had tried to rip him off.

Jessica led Holly to the centre of Seb's huge suite. She loosened Holly's tie, she then began to unbutton her shirt. Holly was quick on the uptake and started to reciprocate. They stood in the middle of the room and shed their shirts, then bras. Jessica reached around and unzipped Holly's skirt. As she lent over she kissed Holly, tentatively at first then as Holly responded with ever greater passion. When they had struggled out of their skirts and stockings and were left in their panties, they knelt before Seb.

"Can we go sunbathing together, Master?"

Seb thought this was a great idea, but was still too shy to change in front of them. He briefly left the room and returned in some shorts. Seb lay on the central longer. As it had been designed for two, Jessica and Holly found it easy to curl up on either side of him.

Jessica leaned over and smiled at Seb, as they chatted she began play with his nipples. Holly started to massage Seb's inner thighs, she snuggled up close and let Seb feel the heat of her pussy.

"Seb, it's hot. Would you like something to drink?"

"Yeah, can I have a beer please? There are some in the fridge by the bed." Jessica got up leaving Holly entertain their client.

When she returned with three beers, she put them down on the table and said, "Seb, is it OK if I strip off. I hate tan lines." As Seb did not immediately object she quickly stepped out of her panties and lay down beside him. Holly immediately got up and teased Seb as she slowly removed her panties.

"Jessica, you know I have sensitive skin, can you help me with some sun tan lotion." Jessica got up and crouched over Holly's calves and massaged the cream into Holly's back. Holly turned over and Jessica did her front. She started with Holly's lower legs, moving upwards, being a friend she took a long time to ensure that there was ample cream rubbed in the sensitive area between Holly's legs. She then moved on doing Holly's tits, then neck and shoulders. As she did this her tits rubbed against Holly's. Holly looked serene as Jessica worked, but as Jessica moved upwards she opened her mouth and was rewarded when Jessica gave her a romantic kiss. Seb watched amazed at the performance. When Jessica had finished Holly returned the favour.

The girls returned to Seb's side and Jessica continued to play with his nipples. Holly started rubbing his thigh, but gradually her hands eased upwards to begin with massaging the area each side of his penis but when she got no resistance went on to the penis itself. Her touch was light and she was massaging through the material but Seb quickly became erect, as her massage continued he became painfully erect straining at the shorts' material. As Holly continued, Jessica leant over and started to kiss Seb.

Nothing was said but Jessica and Holly started to ease Seb's shorts down his thighs until her was completely exposed. When he was naked Jessica rolled him over and then began to massage the sun cream into his back. Jessica leant so close that Seb felt her tits rubbing the cream into his back. Holly concentrated on his legs or rather his buttocks and the area between them. At Jessica's signal they rolled Seb over and massaged cream into his front.

Seb had never felt bliss like this before, this was no quick professional service he had received from other whores. He felt desire from every pore of his body, Jessica and Holly were so gentle but it was so erotic. He had a huge erection. Holly knew her duty and straddled him and eased his prick into her pussy. She slowly rose, then fell, once, twice then with increasing the pace. Jessica eased away as Holly got into her rhythm. Seb reacted reaching for Holly's tits. Holly clasped Seb's cock in her pussy and rode him without mercy. He did not last long but Seb felt it was one of the finest orgasms he had ever experienced. Jessica and Holly both snuggled up to him and they dozed in perfect contentment. They woke in time for lunch that they took in Seb's suite. The girls remained naked throughout as they ate their salads, Seb struggled into his shorts.

After their coffee, Jessica took Seb's hand and led him to the bedroom. She lay down on the bed, spread her legs and beckoned Seb over. Jessica guided him to another passionate climax. Seb thought she was a genius, so tender, so sensual and the body of goddess. He had never been so tired or so absolutely sexually satisfied in his life. He was beyond bliss. It was with huge reluctance that he allowed Holly and Jessica to put on their schoolgirl uniforms and leave. They were all content, Holly was pleased with her performance and Jessica was proud of her charge. The girl was a natural, but was disciplined and had faithfully followed all Jessica's instructions.

Jessica and Holly's second date was with a young and by reputation hugely successful trader called Greg. Greg went for the preppy look but Miss Christensen had warned Jessica he liked to punish his girls. This would be Holly's first big test. Greg ushered them into a school room where he told them to bend-over one of the desks, drop their knickers and raise their skirts. They did as they were told, Jessica thought Holly looked fantastic with her long legs perfectly straight, bending over pushing out her luscious bottom. Greg agreed as he caned them hard. He started with Jessica, his strokes were hard rather than erotic. Jessica knew he enjoyed hurting girls rather than merely play-acting. She bit her lips trying to avoiding screaming, but this only seemed to encourage Greg who struck her harder and harder until she cried out in pain. She cried and pleaded as he whacked her again and again. Eventually Greg seemed satisfied. He then went to work on Holly's virgin bottom. Jessica was hugely impressed that Holly also tried to restrain her cries. But Greg showed no mercy, he beat her until her bottom glowed. Holly quietly sobbed, but made no attempt to move or protect her bare bottom. She took her punishment like a professional.

"Good, my little ones. Jessica kneel. Holly spread your legs."

Holly felt Greg's hands on her now very sensitive bottom. God it hurt. She then felt his penis inch between her buttocks. Holly knew she was about to lose her anal virginity. She tried to relax as Jessica has trained her. Greg eased himself in. He then started to thrust, gently at first but with increasing vigour until he was close to climax when he was pounding away with all his might. Jessica saw Holly was in huge pain, but still tried to cry out in 'ecstasy' telling Greg how much she was enjoying it. Eventually Greg came.

As soon as Jessica saw this, she approached and led Greg over to the bed and started to suck his now soft penis. She hoped this would give Holly time to recover from her first anal experience. Jessica was now quite expert at blowing men and could resuscitate even the most spent member. Greg was no exception and she quickly got him erect again. As she looked up she was surprised to see Holly now just dressed in her stockings and suspenders coming over. She looked sensational, she leaned over Greg and started to nibble his ears and then to kiss him. Jessica had never seen anyone give such an erotic kiss. Holly seemed to putting her heart into it straining to get her tongue as far down Greg's throat as possible. Tenderly embracing him. Jessica now redoubled her efforts and was quickly rewarded as Greg ejaculated again. This time the poor boy was truly exhausted. Holly and Jessica dressed in their uniforms, curtseyed and left. It was only now that Holly complained at how much her whipping and fucking had hurt.

With Miss Christensen's permission Jessica allowed Holly to go on her first solo date the next morning. Jessica watched her performance via CCTV ready to step in if there was a problem, but Holly handled things well and she had her first client of her own. When their time was up, Holly thanked Jessica profusely for her guidance. She said she would still like to have a go at being a model but was confident if this didn't work out she would be very happy applying for a job on the island. Even if the modelling went well Holly said she might ask Miss Christensen if she could work on a part time basis.

The first guests started to leave the island on Sunday afternoon. Whores were expected to go down to the marina, in uniform, to wave goodbye. Tim knew Christin was leaving on the 4pm shuttle so was keen to see her one last time. He eventually caught her eye and knelt as she approached. Christin gave ruffled Tim's hair and ordering him to stand gave him an affectionate hug, whispering that she hoped to be back soon to continue his education.

Personal goodbyes finished, Tim joined the rest of the whores. Everyone was smiling and waving, it was a happy scene. They really had recruited some very beautiful boys and girls. He looked around, struck by how flattering the uniforms were. He saw Claudia enthusiastically waving to an ex-client. As she did, her satin skirt rose up, revealing her bottom. This was criss-crossed with vivid red lines, the poor girl had clearly taken a harsh beating, but one would never guess this from her happy demeanour.

The weekend had been a lot of fun, tough at times, but Tim enjoyed playing the school boy. He just wished he could wear his uniform more frequently. He loved the feel of the satin, and knew the tight shorts showed his legs off to the great advantage. He would look forward to the next school party.