The prolog:

This is a story is about transsexualism, leather, Fetish, Anal, and the BDSM. The story is about transsexualism, Anal, and BDSM. If you like that genre I hope that you enjoy reading this story.

The story:

Sam is a guy that is 35 years old and has a nice job and apartment. Nothingtightening he is managing quite well. He does not spend a lot of money traveling or anything else that takes lots of money. He is living in a smallish town and he spends his time after work mostly bicycling or training in the local Crossfit box.

The Crossfit box is training a great variety of people. Men and women from different ages and backgrounds. The heavy training together has created the people bond as a strong society. So the people that have trained there longer also meet each other outside the box too.

Sam has been invited to a party at one of the training friends’ house. The friend is a woman in her fifties. She is inviting her friends from different places. Of course from the box but also her work and other hobbies like horse-riding people are invited.

Sam is waiting for this party a lot. He likes that woman. She is very nice and funny and has a humor that involves a little kinky humor too. She is married so there is not anything else involved in their friendship than typical friends have together. He knows that at her parties the people are nice and funny and easy to be with. There is also at all times good food and maybe a sauna and Hot tub in their backyard are also in use.

She lives only a few kilometers away so Sam decides to ride his bicycle there because there is also alcohol involved. Sam could not drive back home in his car but on a bicycle, he can. He takes some own drinks with him and a towel and swimming pants if there is the Hot tub in use.

When he gets to the party place he notices that there is already quite a many people but many of whom he knows that is coming has not come yet. He is welcomed to the party and leaves his bag in the backyard where the parties are starting. There are tables with name tags and he finds his place on one of the tables. She has mixed her friends so that at the same table are sitting people from different friend groups she has.

When the parties are officially starting they have champagne glasses and they lift a toast to the evening. After that, they go to sit in their places.

Sam notices that at his table are sitting some people from the box but also people he doesn’t know. They are of different ages and genders. They begin to explore where they have met the party host during eating the fine food. Alcohol is involved so the people are soon as they have known each other a long time. Sam is a shy guy so a little bit of alcohol makes him open and soon he is the humor guy at that table that is telling stories and others are laughing.

They are very nice people and he is talking with every one of them. At some point, he notices that a woman from the other table is observing him. She is in her fifties, tall and gorgeous. She looks very self-confident and looks with her intelligent eyes through her eyeglasses. She smiles at Sam when she notices Sam looking at her. Sam thinks that maybe he could drink a few glasses of water next. Maybe he is too much drunk and because of that too noisy so that they are starting to stare at him from the other tables.

After the dessert, they begin to leave the tables and associated less formally. Sam goes into the house to discover a toilet because he thinks that the bubble in his head starts to show. After finding and using that he sees that same woman standing in the corridor. She smiles at him again and looks at him like she would like to talk with him.

“I hope that I wasn’t too loud when we were eating,” Sam says to her and smiles back.

“No way you were. It was nice to listen to your talking, You have your way express things so that you make people laugh and happy around you. That is a nice gift that everybody doesn’t have and your smile is so cute. Your eyes sparkle like stars when you smile. I bet you have heard a lot about your eyes,” the woman says smiling but Sam notices that her intelligent eyes are piercing him when she is talking like she is investigating his mind and body.

“Yes, on a few occasions,” Sam says humbly. His eyes have been something he has heard about a lot from childhood to this day.

“My name is Rita and I am a colleague with our hostess and we also ride horses together,” she introduces herself giving her hand for a handshake.

“I am Sam and I am from the Crossfit box she trains,” Sam says and shakes her hand. Her handshake is firm but not too strong and she holds his hand a little longer than people usually do.

“It is very nice to meet you, Sam. This party is a great opportunity to meet people you would not meet otherwise. Like the hostess, her friends seem to be all so nice or even more,” Rita says leaving open what she means by that more.

“Yes, it is very nice to meet new people on such a friendly ground like here. I would never talk with strange people out there,” Sam confirms her saying.

“I think you are talkative on familiar ground but quite shy when you are not feeling that you are on your ground. Maybe the alcohol makes you a little bit more open with strangers like me,” Rita says and watches with her piercing eyes still smiling at Sam.

Sam notices that she knows exactly how he is.

“Yes, that is me. You went straight in my head,” Sam says and smiles back at Rita.

“I observe people that I think are interesting and I think that you are very interesting so I have observed you a lot. From the minute when you came here on your bicycle,” she says looking directly into his eyes.

Her straightness makes him a little uncomfortable and his face goes a little red. He feels like he is a schoolboy and she is his teacher making notes from him or a psychiatrist investigating his behavior and telling the results to him.

“Don’t take it bad. All I have seen is something I like. Maybe you don’t always see all of your good sides yourself,” she says and walks outside,

Sam stays standing there for a little time. He is thinking about what just happened. Why did she tell her all those things? What does she is wanting from him? That didn’t sound like typical small talk.

He goes out too and sees his friends there and drinks some beer with them. When it is getting a little dark the hostess tells everyone that the sauna is warm and the Hot tub in the backyard is for everyone’s use.

Sam likes to sit in the sauna a lot so he goes in there immediately with a few of his male friends. They sit there and talk and take some more beer. At some point, they decide to go to the tub. They Shower first and wear the swimming pants and go out to the tub.

It is a little cold already outside and people have their jackets on. The tub is nicely warm to sit in. The size of a tub like that fits easily eight people. Sam notices that Rita was again watching him when they were walking from inside to that tub. Some women also join them in their bikinis. The tub is full of people and they are sitting shoulder to shoulder. People are getting loud and more drunken. There are also lots of people standing around the tub and talking.

Suddenly Sam feels a hand on his shoulder. He looks up and Rita is standing behind him outside the tub. How long has she stood there he doesn’t know. She just looks at him and turns and goes inside the house.

Sam thinks that she wanted him to go after her. He rises from the tub and goes inside to the bathroom where his towel is so he can dry himself. Rita is in the bathroom holding his towel.

“Maybe you should have a Shower first and we must dry your well. There is quite cold outside already,” she says and stands there watching him.

Noticing that she not gonna go away Sam goes to Shower. He thinks about what to do with his swimming pants and concludes that he has to take them away in the Shower.

Rita looks directly at him. As a Finnish man and trained quite a lot Sam is comfortable being nude in front of people. But is a little bit different when someone is fully clothed and observing you. Sam is also getting more aware of the woman’s sexuality. Although her look is very professional and discreet he notices her strong legs and buttocks. She has a rider’s body. Her tits are not massive but good B-cups. Sam is more the Ass man so she is in his eyes very attractive. His penis swells a little but he can maintain his calmness and showers quickly.

When he shuts off the Shower and reaches for his towel in her hands, she doesn’t give it to him. She starts to dry him with it. She rubs his head first dry with her strong fingers and then goes lower and lower drying also his penis and balls and from behind his Ass and also between his buttocks. He lifts his legs a little so that she doesn’t have to squat.

“Then to the changing room to dress your clothes on,” she says and slaps his buttocks.

When he is dressed she gives him the towel so that he can put it in his bag.

“I think there is some evening snack served. Let’s go to have some,” she says and guides him out of the dressing room.

They have some snacks and sit together on one of the tables inside. Sam has time to look at her more. Her Ass looked amazing in her tight leather pants when he walked behind her.

They eat in silence. The silence is not uncomfortable. Sam feels oddly natural to sit with that woman in silence and eat. The hostess looks at them and Sam sees a knowing smirk on her face. He is himself a little confused. Why did she want him out of the tub and eat with her in silence? Did she only want to see him naked and touch him through that towel?

After they have eaten Rita wants that they go outside. Most people have come inside because it is getting dark and cold outside. She takes her leather jacket with her and Sam helps her put it on.

“You are a gentleman also,” she says.

Sam just smiles at him and walks behind her out. She walks around the corner of the house where no one is seeing them. When she stops she turns to Sam and asks: “Would you be comfortable answering some intimate questions?”

Without knowing what she will ask Sam just says: “Sure.”

She looks smiling a sexy smile at him and asks: “How do you find a little older woman than you?”

Sam thinks about what he should answer to that but he thinks that she means what he thinks about her? Is she interested in her?

“They can be very attractive if you meant that kind of thing?” Sam answers.

She nods and asks again: “Are you seeing anyone just now?”

“No, am not,” Sam says.

“Have you ever been with someone?” she asks.

“I have had one short relationship if you were asking that?” Sam says.

Rita smiles and says: “Yes, I was asking that. I didn’t ask if you have had Sex with someone because I think you have.”

Sam sees a smirk on her face.

“Was she older than you?” she asks.

“She was older. About five years.” Sam says.

“Are you about 35?” Rita asks.

“Yes, you are guessing right.” Sam answers.

“Do you consider yourself as a straight, bi, or homosexual? That last one you can forget. I have seen from your eyes that you are not gay.” Rita says.

“I am straight,” he says.

“But you like to take it in the Ass?” Rita says and looks directly at Sam.

How does she know that? He likes to take strapon in his Ass but knows no one that would use it on him. He has only had a few random experiences with professionals.

Rita sees from Sam’s face that she was right! She had tested him when drying him with that towel. First, he was submissive when he let her dry him like that and took those swimming pants before her off. He doesn’t also put any effort against her when she dried his Ass also between his buttocks.

“I don’t like men like that at all,” Sam just tries to say.

“But you didn’t deny that you do like to take it in the Ass,” Rita says with a grin.

How this has happened to him Sam thinks? At a nice party, he is at some point talking with an older woman he likes to take in the Ass.

“What you like to take in there then? You play with plugs and dildos and fantasy that someone would take you with a strapon?” she asks.

Sam cannot say anything. He just looks away.

“If I would be you and would like to have something happen I would go inside and thank the hostess for a very nice evening and then I would take my bike and ride on it to this address,” she says and gives him a card.

Sam looks at the card and it is a company card with her name and phone number and also the address.

“Before you leave, turn around and lean with your hands to that wall!” she commands.

Sam obeys and turns. Next, his pants are drawn down. She takes something from her bag and comes behind Sam. Her other hand covers Sam’s mouth and another presses something straight to his Ass. He would yell, but the hand muffles his sounds. When the pain is his Ass is almost bearable, his Ass sucks the object in and its base stops it from going further and leaves outside. It is a buttplug that is pressed in his tight Ass.

“If I would be you I would be going already,” she says like commanding.

Sam wakes up and lifts his pants up and almost runs in. He finds the hostess and thanks to her for the evening. Then something happens. The plug comes to alive. It vibrates and rotates in his Ass. He tries to keep his calm when talking to the hostess. She wonders why he is leaving so early. Sam explains something about the early begin to the day and tomorrow the same thing. She wants to hug him goodbye and Sam tries to keep his hips far from her because he is having a little bulge in his pants and she might notice that if he would press it against him and the plug is vibrating and giving him little electric shocks.

He leaves and takes his bike. When outside the yard he stops and takes the card and looks at the address and puts it in the phone’s GPS. The plug is now doing nothing but causing pressure to his Ass.

That is only a few kilometers ride. He would be there in a few minutes.

When he arrives at the location everything is there silent and dark. The whole neighborhood is sleeping already. He looks at the card and looks at the house in front of him. He thinks that he is in the right place. The house is big and looks expensive. It is also in an expensive area.

Looks like she is not here yet so he is on the road and waits. He hopes that no one sees him. Someone would think that he is some stalker or robber or something.

Minutes passes. He starts to think that was some sort of a joke to send him here. Then the plug comes alive again and he almost jumps into the yard.

Then after 15 minutes of waiting a car’s headlights are showing in that street. A two-seated Mercedes-Benz curves into the yard and drives directly into the garage. Sam sees Rita driving that car so he drives also in the yard and leaves his bike in the garage ceiling.

Rita comes out of the garage and guides Sam inside the house.

“Leave your clothes here,” she says and Sam is quickly naked.

She amuses herself by giving electric shocks with the plug to Sam.

Sam is guided to the basement. There is an open space and a few doors around it. She takes the door that is locked and opens it staying standing at that door and pointing with her hand that Sam should go in.

In that room is a bleak light shining in the space. In the sailings are hanging shackles, whips, hoods, and other BDSM objects like gags and so on.

Then there is a bench in the middle of the room. That sort of where one can be bounded in the bend-over position.

On the bench is laying a belt made of leather. It is wide from the backside and it has a strap that goes between the legs from the backside to the front side. On the front side, it has a metal ring.

She sees him looking at it.

” I didn’t attach the dildo to it yet because I didn’t know what is the size of the anus I will penetrate this evening,” she says with a grin.

She takes the belt and says: “I think you know your position.”

Sam bends over the bench and Rita ties him to it with leather straps that are attached to the bench. His face is the O shape ring that the bench has as a headrest so he sees only the floor beneath it.

He hears the sound of the surgical gloves put on and then the plug is forced out of his Ass. He yells when the widest point of it stretches his Anal opening.

“Here you can yell as much as you like. This space is soundproofed,” she says and pets his buttocks with her gloved hands.

“Let’s see how big strapon you can take,” she says and he feels the cold lube on his anus. Then he feels some harder object pushed with a finger in his Ass.

“That was a suppository that melts and lubricates your anus very well so no need to be afraid that I will break you,” she says and laughs.

Then he feels her fingers on his anus. She sticks two of them right away in and he gets thrills.

She massages his anus and prostate with her fingers and then adds a third in and after that the fourth. Then she takes them out.

He hears a sound that comes when the gloves are taken off and something is taken out of the cabinet. Then he hears that she lifts her legs first one and then the other and something is lifted that rubs her leather pants making the familiar sound that leather makes. Then comes the sound of belt-tightening and steps walking between his legs.

He knows what is coming. She has dressed the strapon and installed a dildo to it. Now she is standing right behind him and he feels her hands petting his buttocks.

“From petting to pegging,” she says and he feels the dildo head on his anus and going slowly but firmly in.

The dildo is not thin. It is quite large but not too large. Just so large that he barely can take it.

She goes with one slow firm movement so deep that he can feel her hips against his buttocks.

“Feeling full?” she asks.

“Very,” he cries.

“A little bit of pain at this point is good. Then you know that it wasn’t too thin. In the end, it will feel so nice in your Ass and I have good pressure against my clit and that is very important for you because I will fuck you until a come and I don’t come easily,” she informs.

Slowly she starts the fucking. At first, he feels the pain but after a moment the pain is away and it starts even feel good. She pushes longer strokes and faster strokes. After a while, he is feeling an odd feeling that comes somewhere deep, and then it strikes him. A big Anal Orgasm that he has never experienced. His Ass pumps and his half erected penis jets sperm to the floor.

“I knew you will come before me. Someone could be angry but not me. You can come as soon as you like and as many times you like but this will not be over before I come,” she says and starts to fuck him even faster.

That feels at first quite bad because he has just orgasmed but then it starts to feel nice again. The second time takes a long time for him to reach the Orgasm again but it comes and his Ass pumps again. After his even bigger Orgasm than the first one he hears her breathing that is now fast and her grip on his hips is very strong that she is near Orgasm too.

When she comes she pushes the dildo to the hilt and presses her pelvis strongly against his buttocks. She moans when she comes and her hips have thrills.

She takes her dildo out of him.

“You have to wait here a moment alone but I will be soon back,” she says and he hears the heels clicking to the hard floor when she goes away.

There is absolute silence and he can only hear his breathing. He feels the lube and his juices running on his legs.

Then he hears something like talking and steps taken with two pairs of high-heels.

“Here he is. Isn’t he cute with his Ass up and the anus still a little open after fucking?” Rita says to the other person.

“Yes, and those juices running on his legs,” says the other person with a deep female voice.