Meeting The Hooker

This story could have gone to the transsexual, BDSM, and anal categories. It starts with fetish so I choose that one.

If you have read my stories you might know my style to write. My style and things I am interested in are not the mainstream so if you are looking for something like that the story may not be the choice for you. If you read it and liked it I am glad if you share it with me.

This time I had also help with editing. Thank you, editor!

Chapter 1

I am fit, but not a big guy in my forties. I have had some relationships with women but am currently single. I am a bit shy and not very confident with women. Every relationship has involved lots of time, effort, and pure luck that they have happened at all. I still haven't found the right one.

Being shy, I am a person that has one-night stands. If I want to relieve my sexual needs without masturbation I have chosen to use prostitutes and other sex workers. It is easy. You just make the appointment and give the amount of cash they want and they do the rest. I have always been strict that I would not get involved with pimping or other ugly things that can be happening in commercial sex.

After a long dry season, I have started to look at the internet sites with ads for hookers. I also look at sex forums to try to see if there are any hookers that catch my eye.

There are two options. My home town is not that big and has few hookers advertising. Some of them are local and some of them are passing through as they tour between cities and countries. If I travel a few hours to the bigger cities I have commonly more and better options to choose from.

Local would be the best. Those touring girls are more likely under some pimp and if you really enjoy her it can be disappointing to never be able to see her. Traveling to another city takes always time and money.

I wrote in an online forum that I was looking for interesting hookers and asked if anyone knows about interesting touring girls coming to town. I have the typical answers. No good ones come to this town and so on. Maybe so. In a big city, there are better chances to and more expensive ones. The cheaper girls often visit smaller towns because there is less competition.

A few days later I had a private message in my inbox of the forum. "Rose" messaged me saying that she read my message in the forum. She thought I seem trustworthy and might make a good client so she decided to write to me.

She tells me that she is local in my hometown but keeps her advertising low. She wants to choose her clients and have just a few regular clients. She has a regular job and only sees one client per day. She has a client scheduled today, but said she could meet me the following day. Her price seemed reasonable so I agreed to meet the next day.

Chapter 2

As always, I get quite nervous about meeting some new person for sex. The time before the meeting seems to pass very slowly.

The next afternoon I have a shower and put on clean clothes. I want to make a good impression.

She told me to send her a Whatsapp message two hours before our meeting. When I confirm that I am coming and she will tell me the address where to meet her.

Being anxious I send the message early. I only have to wait a few minutes for her response. She gives me the street address and reminds me what time to arrive, but she doesn't give me an apartment number. She tells me to message from outside her building and she will give tell me how to find her apartment. I look up the address and Google Maps and wait anxiously.

I go to the address a little before to be sure that I find that place. The place is easy to find. It is in a midtown apartment building. I walk a little nearby the address to pass the time. When the meeting time arrives I send her a new message that I am on the street and she sends me the information about the right floor and apartment number.

At the building door, I ring the doorbell of her apartment and she answers by opening the electric lock. I go to the elevator and choose the right floor.

When I am on that floor. I see her apartment door and it is slightly open. Many sex workers do that because so clients don't have to knock or ring a doorbell. They want to keep a low profile because of neighbors.

I go to the door and open it slowly and step in.

She is behind that door and quickly shuts the door.

We look at each other.

She is a little older than me. Maybe in her fifties but she is in perfect shape. Her pelvis is wide and her breasts are something like a D-cup. Her waist is narrow and her legs are almost endless. She is taller than me and a little bit amazon. She has high heels that even make her taller.

She has skin-tight leather-like leggings and a shirt that is open so that I can see between her breasts.

"Hi, nice to meet you and welcome! I am glad you came even though I did not give you any photos of myself. So, this is like a blind date," she says smiling at me.

"I did not send any pics of myself either, so I think we are even," I say trying to hide my nervousness with humor.

"Clients mostly send me pictures of their cocks so it is nice that you did not send me one. I am not interested in some wankers cocks and true clients show them in here," she says with a chuckle.

I take my jacket and shoes off and she offers me some coffee she has just made. I accept and we go to her kitchen.

In the kitchen, I give her the money.

"There doesn't need to be any hurry with that. I trust you would not leave without paying and if you would try I have my ways to get what was agreed," she says and looks at me confidently.

It seems that she has the experience and can read her clients well.

We sit at the table to drink our coffees. She sits at the end of the table and I sit at the side.

"Well, I am anything like you were expecting?" She asks.

"So far everything has been better than I dared think," is my polite answer and it is also true. I had almost no knowledge of her or her place so this trip was quite risky. There could have been almost anything waiting for me but this far everything seems to be great and I'm starting to relax.

"That is great to hear. I am also happy with what I see. As I said, I try to have only a few regular clients. Ones that interest me and are trustworthy. You are cute and I think you are at least a little submissive. I think we get along very well. I want to take some things a little deeper with clients I like, so some chemistry is needed between us. I feel that we can have that connection. You are looking at me in a certain way and I wanted to grope your ass in the entry," she says and looks at me with a very sexy smile.

"Grope my ass" and she seems to like me seeming submissive. I'm trying to figure out what she meant by that. I did not ask for any special services from her when we were exchanging messages. We did not discuss anything about what would be involved sexually. In my experience that usually means regular vanilla sex.

"I am trying to find clients that inspire me in different ways. Like I said I like to take things a little or a lot deeper with clients. So often there are some elements that are not just vanilla. I try to keep things interesting for both of us. Usually, I find things that clients have secretly fantasized about or have not even known that would like to experience," she says and looks at me with curiosity.

"For example, I found some notice in a sex dating site where a young girl was trying to find someone to teach her about sex. At first, I thought that it was written some guy but then I read it again and it looked very sincere. I thought that some old pervert can ruin her life if I do not contact her. She was a little surprised about having an answer from a woman but when I explained to her that it would be very safe for her to learn and practice some skills with me. I would not have any other goals than to have a good client that keeps going back if she wants. Professionals never trick you or try to do something that you do not like. I also know things from a woman's point of view and as a pro I also know things and can do things for her that normal guys do not," she tells me.

I just listen to what she has to say to me and this sounds very interesting. Many hookers can be talkative but it is often a waste of time. They try to spend the agreed time talking, leaving less time for sex. With Rose, we have not even agreed on how long our meeting will last.

"I have met her twice. I was a little surprised that she messaged me quite soon after our first meeting. Women are more complex, so I did not know for sure what she was thinking after our first meeting. She wanted to meet me again. She is quite a special girl. Young but not underaged. She was a virgin in every way. She is very shy and did not have the courage to meet any boys. She is cute like you and is quite petite. Under that shyness, she has very strong sexual needs. I had thought that I would have to go slow with her, but I ended up fucking her face with my cunt and ass. She did not even know the term rimming, but when I put my ass to her mouth and told her to lick my anus she did it long and deep. I took her virginity with my strap-on. First in her pussy and then I fucked her ass so long that I had so many orgasms that my legs went numb. I thought she would have quite a lot to think about when she left, but in two days she was wanting to visit again." She tells me this like it was a normal conversation about a regular day at work.

I feel my face getting red. I'm getting excited by what she is saying. The story makes my cock stiffen and my mouth goes dry.

"So, have you any virginities left that we could deal with?" she asks with a sexy voice and curious look.

"I think my virginity is long gone," I say nervously.

"Really? Most men that come here have never been penetrated themselves. Have you done it to yourself or someone else with a toy, or have you had a real one in your ass?" she asks with curiosity.

Oh God, did I say more than I was supposed to do? What I meant was that I have had sex with a woman. Vanilla sex. But I didn't mean to say I had done those the things she just described. I wondered what I should say next -- should I just lie to her and tell her that I meant just vanilla sex? Or tell her that I once tried finger in my ass. Or do I tell her the whole truth?

I have no time to say anything before she looks knowingly at me and I know that she knows. She sees the true me.

"You do not look or act like a gay. I think I have quite a good radar about that. But you have had a real cock in your ass! That is interesting. I know a few heterosexual men that are meet transsexual hookers. They are interested in women but also like to have a cock in their asses. I think you are like that. I am not judging you at all. It makes you more interesting. You are open to finding new pleasures and are open to using every spot in your body to have great feelings. And you guys have quite a spot in your ass," she says and looks at my humiliation with laughter.

"I bet you have even shaved your ass so that is nice to use when someone gets behind you? How have you done that?" she asks.

I just say the truth because she is gonna find that out eventually: "I have regular appointments with a cosmetologist."

"Wow, you have put some effort into it! That is great! I often see bad results when someone has tried to do it themselves. Does she wax you?" she asks.

"No, she does it by sugaring," I answer.

"How did you make your first appointment? What did you say to explain why you wanted your hair off down there?" she asks with curiosity in her voice.

"I said that I am so hairy in my ass crack that it is more hygienic to lose the hair from there," I answer.

"I bet you have no hair on your balls either. Did you just say the same hygienic reason for losing that too?"

Shit, she knows everything! I am an open book to her. I'm just sitting here and letting her interrogate me when I just came here to have sex.

"I just said to her that I want my ass crack hair removed but every time I visited her she took some more off and now I have only one little spot left above my penis."

"So, she saw through you too. Interesting. Have you done anything sexual with her?"

"No, never. We just talk about casual things as she does her job and then I am gone."

"Have you finished your coffee? Do you want some more?" she asks.

"Thank you, I am fine," I answer.

"That is, good because now I want to see what I am dealing with. You can take your clothes off and put them on that chair side of you," she says pointing to the chair beside me.

I rise and start to take my clothes off. She watches me intently.

"You should put your clothes on the chair neatly. I do not want to see any mess." She speaks in a normal tone, but I feel that it is a command that I am supposed to obey.

After I am naked she tells me to stand in the middle of the kitchen and starts to walk around me, looking at me from head to toes. She sees my half-hard penis dripping pre-cum.

"Someone is enjoying it already. Was that the story of that girl or did you wet yourself when I was asking about your habits? I think both of them excited you. I am right again?" she asks and I just nod.

She takes a disposable glove from the drawer.

"These are handy in the kitchen for when you touch meat," she says with a grind when she snaps it on loudly.

"Open your mouth! I want to see what I might be kissing or what might be eating my body parts." She takes hold of my jaw and gloved fingers go in my mouth.

"Seems that you have had some cavities but they are all fixed. Quite a clean mouth so there is going to be quite a lot of oral between us," she announces.

Then she takes hold of my penis and balls.

"Your package is not that big, but big enough. I think I'll take you some time with me to fuck that girl I told you about. She has to learn about double penetration too," she says and sticks her gloved finger under my foreskin and rotates it around my penis's head.

"I am very ecologic. Everything your penis drips here is recirculated to your system. Normally I would feed it to you by putting my fingers in your mouth but this time I want to stick it in your ass," she says and goes behind me.

"Lean yourself over the table and arch your back!"

I do what I'm told.

"Good! Seems like you are a trained bitch because you immediately take just the right pose."

Her fingers spread my asscheeks.

"Well, well! Very nice job done in here. Your ass crack is so smooth. We have a clear way to your ass," she says and I feel her finger enter me with just my precum as lube.

Her finger inspects my anal canal - every spot.

"The insides are as smooth or even smoother than the outside. That is great! You are quite tight so your ass has not been used much. That is great too. I like to work with tight asses." she says and takes her finger out.

"My finger is clean too. Did you have an enema before leaving home?" she asks.

"Why would I have an enema at home if I came here to have just regular sex?" I think.

"No, I did not," I answer.

"That is good. Seems like your system keeps you clean and I will be giving you an enema anyway. I like to see liquid going into you and watch you whimper," she says.

"Let's take this to the bathroom," she says and taps my ass.

Chapter 3

She guides me to her bathroom.

"On the floor on your hands and knees. Put your chest to the floor", she commands and I obey.

She takes something from the cabinet and comes behind me between my legs. I feel something hard and slim go straight into my anus. I feel liquid rushing in my colon with a spurt. She has some kind of a syringe or pump.

She moves beside my head and sits on the floor. She has taken her pants off and moved her pussy towards my head.

"We have time to kill when we wait for that enema doing its job so you can lick my pussy, since you are in a perfect position. The faster you can make me orgasm the faster you get rid of that enema," she says with laughter.

Her pussy is hairless and already moist. Those lips are very inviting. The liquid in my ass is already making me uncomfortable.

I start with kissing her lower lips and licking them with my tongue. She tastes good and clean.

She starts moving her hips and I hear soft moaning. Then she takes hold of the back of my head and presses my mouth firmly against her pussy.

I start licking between her pussy lips and penetrate her with my tongue. Occasionally I lick around her clitoris and press it with my tongue.

Giving the oral has given me something to think about besides the enema, but the pressure is growing. I start thinking that I won't be able to handle it much longer.

I start to focus on her clitoris more. She takes hold of the sides of my head and presses my mouth strongly against her clit. I am licking and sucking. She moans and moves her pelvis. She is approaching orgasm.

Then it comes. It starts like electric shocks through her body. She arches her back and holds my head with a strong grip. Then her pussy starts to pulse and some liquid squirts to my face and mouth.

"She is a squirter!" I think. I've never experienced this, but heard it was possible. Now my face and mouth are full of it!

"Oh God, that was an orgasm!" she says.

"Now lick my cunt and your face clean and then you are free to release that enema!" she commands.

The urge to release the enema is great. I lick her pussy quickly. With my finger, I try to wipe her cum from my face into my mouth. The cum tastes very odd but not bad. I have no time to think about the taste.

"Now you can go to the toilet and release yourself. After that clean yourself well and come to the playing room," she says and leaves me alone in the bathroom.

Chapter 4

When I have released and cleaned myself I leave the bathroom and look around. "Where is that playing room?" I think in my head.

One door is a little bit open and I hear her heels clicking to the floor. I walk to the room and when I open the door I see a bench in the middle of the room. It is covered with black leather and is shaped so that you can be tied up on your hands and knees or on your back with your legs raised up.

"I want you on your stomach at first, but when I fuck you I want to see your face," she says and points to the bench.

I walk into the room and notice that it has cabinets and shelves on the sides. She has placed a tray near the bench that has a packet of black gloves, a big bottle of lube, condoms, different sizes of dildos, and buttplugs. There is also a little bottle that I think contains poppers. I've never tried that.

When I have positioned myself on the bench she secures my arms and legs with straps. A big belt goes also over my lower back. I cannot move.

"Do not be scared. This will be pure pleasure for both of us and that is why I do not give you a safe word," she says. I hear the snap as she puts gloves on her hands.

Next, I feel something similar to an enema. Some narrow nozzle goes in my ass and with a long spurt of liquid into me, she draws it out.

"Now your ass is full of very good lube and we can start. You can make as much noise as you like. It will turn me on. But if you get too loud I will have to put a gag on your mouth," she says and I feel her finger on my anus.

She pushes the finger in and it goes easily now. She adds fingers one at a time and when she is putting in fourth in I tense and she stops.

"There is the first limit?" she asks. "I think the first limit is a soft limit and we get past it fast. Just relax your buttocks and I'll warm you up with three fingers a little more. Then you'll be able to take it when I ease the fourth in. Just keep breathing slowly and keep yourself calm," she says. When I feel those three fingers go in again I feel so full.