Erotic Massage

With this story, I had good help from Jack Bucky in editing.

Sam is a man in his twenties. Kind of a smaller-sized male with a kinky little mind. He is also a bit of a shy guy with very few intimate female contacts. He uses a lot of the internet to browse porn sites and any sites that are about sex. He has a big sexual drive, but sadly his hand, is the only thing that gives him release.

One day he found a site that is more like a bulletin board. There he finds a lot of conversations about using professional sex services. There are main topics to all bigger cities and also a lot about different services. The people on the site are telling about their experiences with professionals. Some professionals have great reviews and some don't.

This site quickly sucks Sam in. There is so much interesting to read about. They also tell that there are those professionals who are advertising about what they are reviewing. It's so true because he finds a lot of new sites that are full of advertising for sexual services.

He comes back to the site for many days and finds many very interesting professionals that are recommended on that bulletin board. Sadly, most of them are not near him or not even in the country right now.

One day, one of the quite old topics pops up when someone is adding writing under it. It is so old that Sam hasn't read it. The person doing the writing tells that there is big news for massage enthusiast males -- Anna is coming to town in near future.

He starts to read the whole topic from the start. There are a lot of reviews about that woman and that she is the best masseuse that many of them have known. They make it quite clear that the woman called Anna gives only outstanding massages with the happiest endings but doesn't do any other sexual services.

The city that she is visiting soon is about an hour and a half drive away from Sam's hometown. So she is not coming to his town but will not be that far away either. He finds her ad and there is something that also makes it easier for a shy guy to approach her. She has added an email address to it.

Sam decides to write to her from his anonymous email address. He is asking if he can schedule an appointment and what would an hour of massage cost. He gets her answer back quite quickly and she tells him what it would cost and also the dates when she will be in that city.

The dates are suitable for Sam and the cost is also reasonable. Now Sam has to only make his fantasies turn into reality and that is not easy. He decides to just agree on an appointment with her through email and that's it. There's no thinking -- just doing. He quickly has an appointment that she agrees to. Now, there is one very long week to wait.

The long week of waiting eventually passes and the day comes when he will travel in his car to that bigger city. He knows the hotel where she is staying and he is told to send a message when he is at that hotel's door at the time agreed upon. She will send the code for the door and the room number then. The hotel has no staff, and that is good.

He leaves his car in a parking garage near the hotel and walks the rest of the way. It is is not yet the time to meet but he wants to be sure about the hotel location and finding the right door. He finds both easily, so he has time to walk around the block slowly killing time. At the point that there are 15 minutes until his appointment, he sends a message that he is nearby and ready when she is.

About 5 minutes pass and he has a message: "Okay, the door code is 4387. Fifth-floor, room number 523.

He walks quickly to that door and uses that code. He takes an elevator to the 5th floor. When the elevator doors open he looks at the room numbers and which way he should go.

He heads to the left and finds the door that has sign 523. He knocks silently the door. He sees that a shadow comes into the peephole. It is there a few seconds and then it is off and someone is opening the door.

Sam goes in quickly through that slightly opened door, and she pulls the door shut behind him.

Now he can see her. She is a blond, Slavic-looking woman in her forties or maybe fifties. She is more like an Amazon. She is standing in her bare feet and still, Sam's head is barely at the same level as her tits. She looks strong and looks at him like she's rating him on what kind of a customer walked in.

He smiles at her shyly and manages to say hello. She says hello back and looks at Sam, taking his jacket and shoes. She seems not to be a big talker either, but not in a shy way.

Sam offers her the money agreed upon and she informs him where Sam can leave his clothes.

He starts to take his clothes off and puts them on the chair she had pointed to him. She goes to take something from the fridge at that time. When Sam is bending over and taking his underwear off he notices that she is right behind him. Her hand comes and takes hold of his shoulder making him stay in that position. Her other hand goes right between his buttocks and presses something hard and cold but slippery through his anus to his rectum with one smooth movement. The object is not big so it went in easily, but it is big enough that he feels a little pressure in his rectum.

"Do you want to take a shower before the massage?" she asks as if nothing has happened.

Sam knows that he is a little sweaty after the nervous trip to the city and agrees to go to the shower first. In the shower, he has time to think about everything that has happened in that hotel room.

First, he had expected to find some nice little lady in this room, but then there was an Amazon who is still quite attractive although she is older than he would expect. Second, what was the object she just pressed into his ass? It went all the way in so he hopes that it wasn't any toy because now it is hard to get out. The pressure and coldness it gave him are going away. So did she give him some suppository from the fridge that melts in the ass? If so, what was in that suppository she gave to him? Is it some drug and soon he will be senseless and she can rob him or something? He thinks that she doesn't have to get him drugged to rob him. He felt that she was so strong when she took hold of him that she can do whatever she wants with him. However he feel okay that's not the case.

He showers quickly and when drying he notices that something slick is dripping from his anus and sliding down his leg. In his finger, it feels like lube. Did she lube his ass with that suppository? Why? What kind of massage this is? No one wrote on that bulletin board about anything than an awesome massage with a great happy ending.

After drying he goes out of the bathroom and she points to him lying in the middle of the bed where she has put a towel.

"On your stomach," she says and he obeys.

She starts from his back. She uses some oil and her firm hands slide nicely over him. Her touch is firm but also very sensitive. This massage is not just petting. It is also very skillful and he feels his tense muscles relax in her hands. He learns to trust her when she is doing so great a job, and that makes him even more relaxed.

It feels so great when her hands come to his shoulders and neck. She knows just how to use the right amount of force that it feels strong but doesn't hurt too much. His scalp and hands also get a massage and that brings him heavenly feelings. She also massages his ears and she finds erotic spots as she also found on his neck that give him shivers.

Her massages move down his back and onto his buttocks. She gives his buttocks a very strong pressure that even hurts a bit. She massages the top of his buttocks and then the sides of his buttocks. She uses her strong hands almost to a point when he can't stand it any more.

Suddenly, her grip changes, becomes more sensual, and she goes between his buttocks sliding her fingers on the sides. This change gives him another shiver and she can sense that. When her hands slide on the sides, some of her fingers accidentally touch his anus when passing by.

Then she moves to the perineum. She massages it very sensually sliding her oily fingers on it. That gives him shivers again.

After a while, she starts to massage his legs and uses again more force. She massages them completely from up to down and then starts to go up again, but this time, more sensitively sliding her fingers on his inner tights.

He is in heaven again. It feels so nice and relaxing but he's also shivering. He feels the tension growing in his body when her hands are again near his perineum. This time the tension is not normal muscle tension. He feels a sexual need to be touched from there. Her hands have made the work so that his body gravitates to the touch in certain parts.

When she touches his perineum even more sensually than before, he feels that his inner pressure is going up and she follows that by putting her fingers on his anus and moving her other hand to his balls massaging them at the same time that her thumb rubs his perineum.

The fingers on his anus make a slow circular movement. His anus feels very slick. The suppository that has now melted completely has spread slick lube all over his anus and part of it has come out to his anus. He knows what will happen. He is afraid because the suppository was the first invasion of his rectum. He has never had anything pressed in there before. Soon there will be something else and he knows it but he also wants it. With her moves, she has made him want it and he will peg it soon if she doesn't do it.

Her hands are so amazing that he feels that he is near orgasm but yet so far from it. Her fingers put more and more pressure on his anus and soon he feels one sliding slowly in. He has seen on the internet prostate massages done but they have used gloves. She goes in with a bare finger.

Soon the finger goes slowly out and the other finger replaces it slowly. She uses her fingers one by one as she goes in there slowly. The last one is her thumb he thinks it feels wider than the others. Then in goes two of her fingers, again slowly, and they stop at his prostate, pressing and massaging it slowly. His penis drools fluid out to the towel on the bed.

Then she slowly stops and withdraws her fingers.

"Turn around," she simply says and he turns to his back, hoping for more ass play.

She starts from his legs massaging them from down to up. When up her fingers slightly touch his perineum and balls again and even his penis that has been limb and drooling this far. Now it is quickly at attention.

She massages his stomach area and chest. She also massages the cervix area and face. That feels very nice and he wonders how her fingers are so clean although she has just penetrated him with them.

Then she goes slowly down back to his penis and starts to massage it slowly. It feels wonderful but she keeps doing it slowly so that he doesn't orgasm. Her other hand goes under him to the balls and perineum and finally in his ass. Her slow movements keep him on the edge.

When he thinks he can't take any more and that he will come, she suddenly stops and says: "Turn around!"

"What now?! Turn around now?" he thinks but obeys.

When he turns she takes hold of his hips and lifts him so that he knows that she wants him on his hands and knees.

She presses also his upper back down so that his chest is against the bed.

"Do you want that I carry on like I did before or is it okay if I do something special that I don't do with customers?" She asks sitting on her knees behind his ass.

Part of him wants to just have the orgasm quickly with those methods she used before, but the other part is thinking otherwise. She has made him curious. What special thing would be that customers usually don't have?

"What is that special thing?" he asks.

"I can't say it. You have to promise that you don't tell about this to anyone. Especially on any bulletin boards and so on," she answers.

"Okay, I promise!" he says and thinks that because everything in this session has felt more and more good, the surprise treatment will too. Well, all of this has been one big surprise to him but everything so far has probably been from her normal package.

"Look!" she says and when he turns his face she takes a picture of him.

"This will be my insurance that you don't share our secret. If you don't share then I don't share. Understood?" she says with a stern voice.

"Understood," he says with an afraid voice.

"This is turning maybe in a bad direction," he thinks.

"Turn your face back against the bed," she commands.

When he obeys, he hears some rustling noises and ripping sounds when something has torn to parts.

From the movement and rustling, he guesses that she had taken some of her clothes off and when he feels her breast on her back he knows that it is true.

Her other hand comes to his shoulder but her other hand goes further and takes hold of his mouth.

At the same time, he feels something stiff sliding between his buttocks. Like an ice-breaker, it splits his buttocks wide.

"Now, just let it happen and be calm. Soon it will feel nice. Now it's not possible to go back." she says with a husky and stern voice.

He mumbles something to her hand but can't talk because of her powerful grip. Tears come from his eyes because he is so afraid. The thing between his buttocks feels huge and the thing must be a penis! She is a trans!

She slides back and forth her penis between his buttocks and then changes the angle so that the head of it is pushing into his rectum. He yells at her hand but can't make any sound. Slowly but steadily she presses her huge penis into his ass.

He feels that she will split him in a half. When he is almost passing out from pain she stops and he feels her hips against his buttocks. She stays there for a moment and then goes just a little back and slowly, fully in again. She keeps her strong hold on her victim and he just can be there on his hands and knees. Ass up for his fucker.

He doesn't know how long that takes but it feels like a very long time when she slowly increases her movement bit by bit. At some point, it doesn't even hurt like hell anymore. The pain is something he thinks he can take.

"Yes, relax and this will be sooner over. I don't promise that soon but sooner if I can fuck you properly," she says and takes longer strokes.

He tries to relax and it is hard but at some point, the pain is away and her penis goes in and out using the whole length.

"Now I could take my hand away from your mouth but in this hotel room, you can't shout. At the start, you would shout from pain and soon you would be shouting from pleasure. I bet that you were a virgin. So tight you are. I have never managed to give any virgin an anal orgasm but I want to try it with you because you were so near it when I fingered you. Many of the men are such a sluts. They cry in pleasure when I finger their rectums. I make you even a bigger slut when I teach you that the biggest orgasm you can get is from taking a big cock in your ass. That is what you will want the rest of your life. I happily give you the pleasure and I know that you will come for more!" she says and starts to fucking him.

First, he is in pain again, and then comes the painless situation. After that, comes something he doesn't have experienced yet. It feels like her fingers were in his ass but much more and much deeper.

She was right. Soon he is in a state where he would shout if he could. The pleasure is so powerful that he feels that he will pass out. Then it comes. Huge orgasm. It starts from somewhere deep and goes on and on, and at some point, he feels that the cock in his ass starts to pulsate in the same rhythm as his ass.

Their orgasm is long and he feels her grip so tight on him when she presses herself as deep as possible and draws him against her hips.

After orgasm, she draws her penis out and goes to clean herself in the bathroom. When she comes back she just says: "Your turn."

He walks slowly to the bathroom and tries to wash. When he comes out she is already fully dressed. He dresses also and starts to leave.

"I will be here again next month. You are very welcome again," she says and taps his ass when he walks out.