A Courtesan and an Assassin

"Feel it" she said "see how you have to ensure the dick is lubricated all over and pay particular attention to the head. As the head enters first you need to ensure that it has a thin layer of lubrication. A sensitive lover will also make sure that he has put lubrication in your arse as well, but you can always do that yourself if necessary. Now stand-up, and take of your clothes."

"Sorry." said a flustered Alysha "you want me to take off my clothes."

"Yes. Take off your clothes. I am going to take mine off as well. But this lesson needs to combine theory and practice to make sure you are ready for your practical with one of the stallions in 40 minutes."

Alysha stood up, turned away and took her clothes off, and folded them onto a chair next to her. She turned around and saw that Miss Rim was naked as well.

Miss Rim looked at her and said "You certainly have a great body, Alysha, and an arse that many men will want. Mmm. Even I wouldn't mind a bit myself, but that's for another lesson."

Alysha didn't know what to say but felt a tingling excited feeling in her chest.

Miss Rim took out another smaller dildo from her bag and gave it to Alysha. She then took out some anal beads and a small butt plug. She handed these over to Alysha as well.

"You can keep all of these. You can use them to practice with. Right now we are going to focus on the dildo -- the replica of the man's dick. Now you need to make sure that you cover it well with lubrication -- and also put some lubrication at the entrance to your arse."

"Good. Now there are as many ways to have anal sex as there are vaginal sex. The most common is from behind, doggy style, where the man is in control and you have to communicate with him on how fast and deep he can go. The other method which is good for beginners puts you in total control is for you to ride the man's dick, where you control how fast and deep it enters your arse. Which one you prefer depends on how you feel -- some women prefer the feeling of giving themselves up to the man, and prefer the comfort of being fucked from behind. Others need to feel they can stop if they want. What do you think you would prefer?"

"I'm not sure" replied Alysha. "I do like being fucked from behind, but with this I think I might prefer to be the one in control."

"OK. Well just watch me. And I'll talk you through it. So you know what to expect when you we go next door."

Miss Rim stood up and went over to the sofa in the corner of the room, carrying the larger of the two dildos. Her body Alysha noticed was very well toned and her breasts were still firm. She had long legs that seemed to go on forever and she walked in a confident athletic way.

"Come over here and watch".

Alysha moved closer to the sofa and watched

Miss Rim turned around and faced Alysha. Closed her eyes for a few seconds then opened them again. She had a smile on her lips and a glazed look on her face. She had conjured up some erotic memory to get her in the mood. She asked Alysha to come over and sit in front of her. She passed her the dildo saying "I'll tell you what to do with it when I am ready", she then put her fingers in her mouth and then to her pussy and started playing gently with herself. Slowly circling her clitoris, and then dipping slowly one finger into her pussy, then another.

Miss Rim began to talk again…"Anal sex is part of sex and a courtesan's love-making repertoire. It's not a stand-alone position or act that is independent of everything else; kissing, stroking, foreplay, vaginal sex and the rest. If it's done properly the intensity it can bring to you and your partners orgasms will be out of this world, but like a good dessert you don't need it at every meal, unless you are like some girls who actually prefer it in their arse."

Alysha looked at her in disbelief " Yes. Surprising as it may seem some girls do prefer it their arse. I am one of those girls -- I love a large hard cock in my arse - which explains why I teach this class I suppose"

Miss Rim began to take shorter breaths and her face was becoming more flushed as she became more excited, and her clitoris became aroused.

"Oh yes. I think I am ready now. Just hold the dildo firmly on the sofa."

Alysha took the lubricated dildo and held it firmly with one hand, resting the base on the sofa.

Miss Rim slowly lowered herself onto it. She paused as tip of the dildo touched are arse-hole.

'Now this is the most delicate part. You have to make sure the man's dick is well and truly hard before he fucks you in the arse. A limp dick just won't do. Now when you feel it come into contact with your arse-hole you need to wait a few seconds, take a deep breath and breathe out very slowly, concentrating on relaxing your sphincter muscles. At the same time lower yourself down ever so slowly, letting the dick slip its way in, not forcing it." Miss Rim moved slowly down onto the dick, a few millimeters at a time. She stopped once a few centimeters of the dick was inside her. "Now this is when your sphincter muscles could clamp onto the dick, which if does happen can cause the man some discomfort and can take a while to undo as the muscles will only relax when the dick goes limp. But don't worry about that. Once the dick is a few centimeters in, it should go past the sphincter and the muscles are relaxed, it should slip in smoothly like so, especially if it's well lubricated."

Alysha's eyes grew wider as she saw the dick disappear in one thrust up Miss Rims arse.

"But, but how did you do that…it doesn't seem possible that something so large can go in something so small."

"Fuck that feels good." gasped Miss Rim as she resumed circling her clitoris with her fingers as she sat on the dildo.

"Now once it's in, you can do one of several things. As you get more experienced and your muscle gets used to a dick up your arse, the man can fuck you as hard as he would if he was in your pussy. But I don't recommend you do that at first. Your muscles aren't ready for it and it will probably leave a burning sensation. I suggest that you take the approach I am taking. Just let the man move with it in deeply, not pulling it out and thrusting it back in. That way you can concentrate on yourself as well and getting used to the sensation of a dick in your arse."

Miss Rim started to put two fingers into her pussy and then stroking them up to her clitoris. She was closing her eyes now. Her fingers were moving faster. More urgently.

Alysha was watching Miss Rim strumming faster and faster on her pussy and the big dildo thrust into her arse and before she knew what she was doing she had put three of her fingers deep into Miss Rims pussy which was so wet that they just slipped in all the way.

"Yes. Shove them in and out. Yes do it Alysha. The feeling of both my holes filled is just too much. Christ. I'm going to come."

Miss Rim, started to move up and down on the dick, taking it right to the end, then driving hard back down on it. It Alysha, could feel the dick moving up and down through the membrane separating the pussy and the dick. She was wondering what that would feel like, but right now the feeling of Miss Rim's pussy that was starting to twitch made her feel incredibly horny, and she was getting wetter by the minute.

Miss Rim poised at the top of the dick for a few seconds then pounded down, crying out as she came in wave after wave of ecstasy. Alysha felt her pussy convulse around her fingers, before she slowly opened her eyes and smiled down at her.

"Now that was good. Not as good as live one, but still good" as she took the dildo out her arse.

" Now I want you lie down on the sofa as I'm going to prepare you for your practical."

"Do you have any questions so far?"

"I don't think so. I just think it's something that either works or it doesn't."

"Sometimes, yes. But if you are well prepared, and sexually excited the adrenaline numbs any slight pain and makes it that much more arousing .And the feeling of owning that dick. Taking it all in, gives me a great sense of power. And no man, no man, can resist a lady who has a beautiful arse and knows what to do with it. You will have them forever…Now will you please lie down on the sofa as we only have a few minutes before I hand you over to a stallion."

Alysha sat down on the sofa, and Miss Rim came in front of her. She deliberately put some Astroglide on her fingers, and opened Alysha's legs and started licking her wet pussy. Alysha murmured as she felt her tongue touch her clitoris, and begin to dart across it. Then the tongue moved lower, down to her pussy lips then in her pussy, now moving lower, finding her arse hole where it circled the whole tempting threatening to go in. it jumped across her hole, flirting with the entrance. Miss Rims left hand was playing with her pussy and she could feel her clit beginning to throb. This was too god she thought. The tongue entered in, shallowly at first, then deeper. She could feel it was tight, resisting the intrusion, and then it started relaxing as the tongue went deeper and a finger, and then two entered in her arse as well. fuck this was good… but it still wasn't a dick.

Miss Rim stood up and Alysha opened her eyes. "What? she said.

"It's time for you to go next door."

"Already. But..."

"You are ready. And sometimes you just have to jump in. And theory is just theory."

Miss Rim pulled Alysha of the sofa and took her to a door at the side of the classroom. She opened the door and led her in. Inside was a brightly decorated room with various beds and other bits of furniture placed around the room, chairs and sofas but of a design she had never seen before. Two men stood up. They were naked, young, no more than 25 years old and had great muscled bodies which were tanned to a deep copper. Their eyes looked at her greedily, as they looked her up and down. Their dicks were flaccid, and one of them was noticeably bigger than the other.

"Now Alysha these are stallions John and Wayne pointing to each one in turn. You have to choose which one you want to be your partner for the next hour. They're both very experienced and will go gently with you as it's your first time."

Alysha looked at them and they smiled back. Christ how was she going to choose. The smaller dicked one. That was it. Smaller meant easier…

"I'll take Wayne." She said. John looked disappointed and left the room.

"Mmm. I thought you would. Wayne you are a naughty boy aren't you. You've put your dick in ice before coming in here?"

"Would I ever descend to such a low trick, Miss Rim" he said smiling.

Alysha realizing what had happened went quiet. Fuck it she thought. Let's get this over with.

"Alysha, you are on your own. Wayne will report back to us at the end of the practical. You have one hour."

The next hour passed in a dream-like state for Alysha. She could remember every detail. Every movement. But if felt like she was there, but not there, at the same time. She was herself, but she had become this other person that she found within her -- Alysha the Elite Courtesan- not Alysha the student.

Wayne was a true gentleman. He gave her a glass of wine which helped relax her. Then told her that he was in his last year as a stallion as he would reach the upper age limit of 26 next year. And then he was going into service in a rich nobleman's family where he would keep the nobleman's wives satisfied when the nobleman was on his travels.

Alysha didn't know when they started kissing, but they did and then she moved down his hard, toned body to his dick which was still flaccid, but now noticeably larger than before. She took it in her mouth and started to suck it gently paying particular attention to making sure that it was good and wet. It grew rapidly in her mouth, so much so that she realized that this was not a small dick, this was one hell of a large one, and it was as hard as rock. They moved to the bed where she continued licking his balls, taking them one-by-one in her mouth. He groaned with pleasure. He took hold of her hips pulling her gently towards him, where he took over from where Miss Rim had been only minutes before. God he was good. His tongue was circling her pussy then disappearing into her arse. It was still relatively loose but her muscles tightened on his tongue a little. Relax she thought -- relax.

Alysha moved up to the head of his dick taking as much as she could into her mouth. God, if only she could get it all in. But she would have to wait and learn such advanced techniques so she remained content with getting it half-way in, where she started taking it in and out of her mouth, whilst firmly holding the base of his penis. She felt a finger go in her arse. Slowly at first, then faster. He had bigger fingers than Miss Rim she thought as another finger went in covered in lube. She could feel his tongue against her clitoris while she was doing this. God it felt weird but good at the same time. It was now or never she thought. She stopped sucking his dick, and got up.

"I'm as ready as I'll ever be' she said.

"Yep. I think you are." Wayne replied.

"I want to be in charge' she said,

"No problem. I love reverse riding as I get to watch your beautiful arse swallowing my dick"

Wayne lay down on the bed with his hard dick sticking up straight in the air. Alysha took the Astroglide and squeezed a healthy amount into her palm and rubbed it all over his dick. She then squatted over him, grasped the dick by the base and placed it at the entrance to her arse.

"Christ that's big" she gasped

"Just go slow. It'll fit easy."

Alysha lowered herself slowly onto the rock hard dick playing with her pussy whilst it entered.

"Christ that's tight' exclaimed Wayne. "It's fucking great, keep going."

Miliimeter by millimeter Alysha lowered herself onto the dick until she felt her sphincter muscles stretching so much that she thought they were bound to tear, when suddenly she felt a small pop and the head of the dick had squeezed passed the now relaxed muscles and slipped all the way in.

"I feel completely full. Christ it' weird, but great at the same time."

Wayne started to tense his dick inside her. And Alysha began playing with her pussy and her clit focusing on keeping her arse open and not clenching or trying to push it out.

"That's it" said Wayne "Just relax and clench at the same time. Now put your fingers in your pussy and feel my dick through the membrane."

Alysha willingly obliged slipping two fingers into her pussy which was now really tight due the dick taking up a lot of the space inside her. Christ that felt good. She could feel the dick inside her and how tight and full and perfect it all felt. She began to move up and down on his dick, she couldn't help it -- it felt too good, slowly and just a little at first, then faster and more deeply as she began to feel the waves of ecstasy pass through her convulsing body as she began to come.

"Christ I'm coming' she said as she felt Wayne's dick get even harder than it already was, as he began to thrust back in time with her downward motion.

"I'm coming too" he replied "Fuck' "Christ' . "Yes" Yes"

Alysha felt the warm cum shooting up her arse and loved every bit of it as she rocked back and forth on his dick as the last of the spasms came over her.

They stayed like that exhausted for a few minutes holding each other Then Alysha slowly stood up as the dick now going limp slipped out She had done it. She was no longer an anal virgin. And it wasn't half as bad as she thought it was going to be. In fact it was bad at all. She felt a tingly feeling in her arse. Maybe she had been a bit ambitious for the first time, but hey nothing training and practice wouldn't solve. And she was certain she had a cream that could counteract the burning somewhere in her stuff.

"Well Lady if it wasn't for how tight you were at the beginning, I would say that you were a highly experienced chick at anal sex. But as you aren't I can only think you must be a natural."

Alysha opened her eyes and smiled, but then realized that she wasn't at the School for Elite Courtesans.

The cell door was opening. Someone was coming in.

"Get up. Prior Zephid will see you. I hope for your sake that you aren't wasting his time"

Chapter 15: A courtesan and an Assassin -- The Rescue

We were entering the atmosphere of the planet Rasburg. Araka-san had coaxed every last parsec out of the ships engines so we must only be a day behind Alysha, if she was still alive.

"I have picked up her signal" said Araka-san "She is alive and as I thought in the mountain fortress of The Providence."

"Yes! I knew she would still be alive." Andrew shouted and then looked around in embarrassment at this emotional outburst. But Araka-san was ignoring him.

On the displays in front of him an aerial photo of the Fortress popped up and started rotating. Arakasan commented "The fortress is virtually impregnable. Half-way up a mountain, covered in treacherous ice, access is only possible by The Providence hover copters that are all digitally synched with the defense systems in the fortress." The fortress dissolved into a 3 D schematic and then zoomed down to the bottom of the cliff face, and then along the valley that led up into mountain range.

"Well Tin Can how the hell are we going to get in?"

"I have a way, but we are going to need some luck."

Alysha was led into the office of Prior Zephid, which was at the end of a long dark corridor, the same corridor that led to the chapel she was in last night. She shivered as the brutal image of what they had done to Cerise flashed into her mind. She had to escape. She had to find a way. Prior Zephid was sitting behind his desk in a well furnished dark wooden room with a large window behind him overlooking the frozen valley below.

"Leave us". He said to the guard.

"You wanted to see me, whore?"

"Yes I did, Jason. I have a proposition for you. You don't want to kill me tonight. That's too quick and tomorrow you'll be regretting it. Why don't you keep me for yourself as your slave where you can have what you want when you want it? I saw they way you looked at me yesterday."

Jason looked at her silently, a maniacal smile coming to his lips, then a laugh that wasn't a laugh. It was pure evil.

"Do you think I honestly want to keep you, a used whore just for me? You are dirty and must be purified and the only way is by holy oil, holy semen and fire as you saw last night. But now you are here I feel obliged to give you a taste of what you will feel tonight."

He went to the door and opened it.

"Guard, see that no one disturbs me for one hour."

He came back and grabbed Alysha by the hair and flung her on the desk. She couldn't resist as she was handcuffed and weak from lack of sleep.

"Don't do this Jason. This is …"

There was a crash of exploding glass as Alysha saw three shapes or was it one shape fly through the window in front of her. They appeared to be hovering above the ground. "What the fuck" said Jason letting go of Alysha's hair. One of the shapes dropped to the ground and kicked low into Jason's groin then kneed him in the head as he doubled over. He was knocked out in a flash and went sprawling across the floor.

Alysha looked up and brushed the tears from her eyes which had formed when her hair had been pulled.