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SataiRolePlayingGuy

Cantina x Logan - Losing Virginity in the Whorehouse

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SataiRolePlayingGuy

Logan had wrestled with the decision for a few weeks.  But now he found himself, wearing a hooded-sweatshirt to hide his face, standing outside the doors to the building unofficially known as ‘The House of Sin’.  He felt kind of embarrassed, visiting a whorehouse like this, but he accepted reality that he might not ever touch a woman without this and that was even worse.  With a sigh, he pushed the door open and walked in.

 

There were not many windows in the building.  None in this part, so he pulled the hood down.  There was just a hallway in front of him, dim lights on the wall, faded carpet.  Reminders that this was a partially converted office building, not something designed for this, or for people to live in general.

 

A rope blocked him going way.  A note with ‘employees only’ written on it taped to it.  Going the other there was a stairway with another rope but no note.  He guessed he would be going that way later, after the appointment was made and it was time to visit the girl he chose.  Continuing down the hall, he found a door that opened into an office.  The lights were brighter, but it still had much of the same look.  Directly in front of him was a desk, with a single girl behind it.  One he guessed was only a little older than him.  She looked up at him with a smile.  “Welcome, I don’t believe I have seen you before.  Are you here to set up an appointment?”  He only nodded.

 

She stood up and walked towards a side room.  “Excellent, follow me.”  He walked into the room and sat at one end of the table and she sat at the other.  She passed him a sheet with various options and prices on it.  “How long of an appointment were you looking to make?”  He looked at the various options.  He did not want to be rushed, but did not want to overdo it either.  “A few hours.”  The girl and passed him a large book next.  He paged through it.  It had profiles for all of the girls currently working there.  Pictures, both clothed and nude, as well as some of the things they liked and disliked.

 

“Take your time.  We have A LOT to choose from.  Many ages, many tastes, and some who fall into rather niche categories.”  She was not in there he noted, though he would not have guessed the reason why.  That she was not available to male customers and would not made it obvious to female customers either most of the time.

 

She had seen a lot of customers come and go.  She was pretty good at guessing what people were after and why they were here.  “You haven’t done this before, done it before, am I right?”  His silence and refusal to look up from the book answered her.  “There is no shame.  People come here for many reasons and it would be hypocritical of any of us working here to judge you for it.  We are here to help.”  She got up and paged through the book, finally stopping on a specific one.  “You ultimately get to choose who you want, but I think you will like this one.  She is very open minded.  If you come back, you could try a whole lot with her.”

 

Logan looked at the girl in the book, Catina Ericson, certainly a beautiful girl.  He was fairly inclined to trust this girl’s judgement.  “Yeah, I think I will choose her.”  The girl nodded and gave him a new sheet.  This time a checklist of what he wanted to do and the prices for each.  Rather quickly he chose the ‘standard package’.  Allowed for most of the basic stuff, oral, vaginal, anal, foreplay, kissing all that sort of stuff.  He was allowed to finish however he wanted, inside or outside.  The only note being that the girl was very likely to be on birth control unless he paid extra to get her off it temporarily.  A choice he did not make.  Nor did he choose anything else of the long list of fetishes, which almost all had to be paid for individually.  The girl took it back and nodded “Perhaps a good idea for the first time.  Now for the last step.”  She pulled out a tablet and began looking though the various girls calendars for setting up a specific time.  “I suspect you don’t want to do it right now, did you have any time preferences?”

 

Logan considered it for a moment.  “Probably a weekend evening.”  The girl nodded and scrolled through the calendar.  “Would Friday night, 7:00-10:00 pm be good?  You of course don’t have to use the whole time, but you will have that available to you.”  Logan nodded again.  “That’s fine.”

 

“What should I put down for the name on the calendar?  It does not have to be your real name if you don’t want to use it.  We like to be discreet.”  Logan thought about it for a moment and decided to go with the initial.  “Just put L.”  The girl nodded again.  “We will see you then.  We will take your payment when you come back, before going up to see her.  We have everything set up.  We look forward to seeing you then.”  Logan nodded, stood up and made his way out the building, looking forward to how it might go.

 

The girl, Aileen, made a copy of the paperwork.  With a few notes about the boy, his appearance, and why he was here and took it upstairs.  She stopped at the door to Catina’s room slid it under and knocked.  “You have a new appointment Catina!  A first time customer.”  She walked back towards the front desk before the other girl could open the door.  She was only there to let Catina know about the appointment and was expected to stay at the desk during office hours.

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IsabellaRose

Catina picked up the copy of the paperwork that had been slid under her door. She sat on the edge of her bed and read over it. A basic three-hour sex package, nothing special. She was insatiably curious about all of these fetishes and specialties that she heard about, but hadn't been hired for any of those yet, despite being willing to perform any and all acts. She had been here exactly two weeks, and in that  time had only had a handful of customers. She had hoped for more work. At least she had a roof over her head, regular meals and baths, beautiful clothing. It could definitely be worse. It had been worse.

When Friday arrived, Catina spent the afternoon bathing, shaving, moisturizing, and generally pampering herself. This was her favorite part of living and working here; the self care in which she was able to indulge. She had reviewed the paperwork for tonight again, and found that there was no requirement for a particular outfit, no specification for a certain hairstyle, no details at all really, just sex. She was okay with that. She combed her hair until it was silky smooth and then put on a set of black lingerie - matching panties, corset, garter belt, and stockings. She slipped on the 5 inch platform heels and inspected herself in the mirror. She was beautiful. Touching up her lipstick, she pursed her lips and then smiled at her reflection. She shrugged on her sheer black robe and lounged back in a chair, awaiting the arrival of her client for tonight.

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SataiRolePlayingGuy

Logan returned on Friday night.  Again he stood outside the door, hood up.  He was both nervous and excited.  Right now of course he just wanted sex.  That was the priority for one who had never had it.  Yes the list was rather impressively long, and maybe he would want to try more later.  But it was best not to get in over your head.  Start wit hthe basics, Catina did not yet know the potential she was about to meet, someone who just needed an introduction to the world of sex before indulging more unusual or extreme things.

 

He waited until it was around 10 minutes before the scheduled start time, not sure how long it would take to set up, he then went in.  He found Aileen at the desk again.  This was off hours for her, but she needed to return to work briefly to accept the payment and get him where he needed to be.  She looked up when she saw him come in and nodded.  “Good.  We do occasionally get people who have cold feet.  But I thought you would not miss this chance.  First there is the matter of payment.”  She put an invoice on the desk.  Logan looked at it and reached into his pocket.  He pulled out the necessary cash and put it on the desk.  Other payment methods were accepted, of course.  But due to a desire for discreteness, people paid in cash the vast majority of the time.  Aileen put the money away and stood up.

 

“I will now show you to Catina’s room.  This is my last part in the process.  Once the door to her room is closed it will just be the two of you.  I won’t be at the desk if you want to schedule a new appointment, but feel free to back another time if you enjoy the experience.”  The two silently walked up the stairs and down the halls.  Occasionally Logan thought he heard noises from rooms they passed, other women with their own customers, most likely.

 

They then stopped at their destination.  Aileen gave one last piece of advice, considering his circumstances.  “She knows what you are here for.  She is being paid to do this with you.  You can be as assertive as you like, as much or little foreplay or discussion beforehand as you like or during it or afterwards if you have time.  Some customers keep this purely business, some like to get to know the girls, especially if they come back, still business but with a more…personal or affectionate relationship.  You can also let her take the initiative if you want.  As long as you don’t start getting into fetishes you did not pay for or go longer than you payed for, you have control over how this goes.”

 

Logan just nodded.  Aileen then knocked on the door.  “I’m dropping off you customer!  Have fun!”  She then opened the door, Logan stepped in and heard it close behind him.  He took a moment to study the room and look for the girl, Catina.  He had not yet decided what sort of approach he wanted to take with her, though he had to decide soon.

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IsabellaRose

Catina was brushing her hair in a chair before a vanity with an oval mirror mounted above it. She turned and looked up as Logan entered the room, setting her brush on the top of the vanity beside a matching comb. 

She was in black lacy underthings, a bra, panties, a garter belt and stockings under a sheer black robe that hung open down the front. Her shoes were strappy five inch heels, and she stood easily in them, leg long legs seeming to go on forever, the straps of her garter belt enhancing the illusion. A black ribbon was tied around her neck like a choker. She smiled at Logan and took one step away from the vanity before stopping and letting her eyes drop demurely to the floor before her.

"You must be the mysterious 'L'," she said, her voice soft and melodic. She looked up at met his eyes. "I am Catina. Thank you for choosing me." 

She curtsied, using the bottom edges of the robe instead of the hem of a dress, and when she straightened, she tried to gauge the young man before her.

She waved one arm around the room, as if to show everything to him. There was the vanity with her comb, brush, and makeup. A dresser stood against another wall, a silver tray atop it with several decanters of alcohol, an ice bucket, and several styles of glasses at the ready. A tall, narrow lingerie dressed was in the corner, and against the far wall was the bed. It was a four post bed with a canopy, billowy fabric decorating the top. The comforter sported a floral pattern and the sheets were white.

"Please, make yourself comfortable," she said. "Would you care for a drink before we begin?"

Her eyes traveled up and down his body, to his face, looked at his hands, his style of clothing, trying to get a feel for him. 

 

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SataiRolePlayingGuy

Logan was sure she understood why he had not given his proper name.  Both customers and employees had reasons to be discreet about this, though he did not have as many reasons to be discreet as some customers.  There was no girlfriend or wife he was hiding this from.  For now he would not say more about that, if he came back, maybe she would get his name later but not this time.  "Yeah, that's me."  He looked around briefly and considered the offer.  Maybe if it had been an all nighter he would have accepted, but he thought he would be better off not doing it this time.

"No, that's fine."  He walked over to the bed, still standing next to it.  He supposed its size was chosen intentionally.  Two people could fit on it, but there was not going to be much personal space.  Fine for the choice he had made, but it seemed a little cramped for two to sleep together.  He decided to be upfront as he turned back to face her.  "I'm not sure how much the girl at the desk told you.  I am here because I have no experience with women, have not been very good with interacting with them and I want to change that before I get much older.  I have a basic idea of how all this works, but no experience with it."  If he needed to use a whore to do that he would, though he left that part unsaid.  He walked back towards her, slowly circling her body and looking her up and down.  He wanted it to be clear he might be a little clumsy due to lack of experience, but he wanted to be the taking at least most of the initiative and lead, though he was willing to consider her advice.  Seeing her up close, she was certainly attractive, he had known that from the pictures, but it was a little different in person.  He was still considering what he wanted to do start, so she had a moment to consider and respond to what he had said.

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IsabellaRose

Catina felt his eyes devour her frame, felt the appraisal in his gaze as he circled her. She knew he had selected her from photographs and a description, so he must already find her attractive; she hoped her reality matched up to his expectations from the photographs. She hadn't pegged him as the dominant type when he came in, but it looked like he might try to assert himself based on his posture and attitude.

She smiled demurely as he explained his reasons for being here. She turned to face him, her eyes filled with the promise of an adventurous evening.

"Where would you like to begin?" She asked the question simply, without pretense or any sort of dominance in her voice. She was his to use as he saw fit for the next three hours. She hoped he could please her as well as she knew she could please him, but after his explanation about his lack of skill or experience, she didn't have high hopes. It looked like this might be another night of a man taking his pleasure from her body, then trying to find her own pleasure with the toys in her nightstand drawer after he left.

Catina trailed her fingertips down the side of her neck and onto her chest, then down between her cleavage as her eyes held his gaze. 

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SataiRolePlayingGuy

That did unfortunately come with the job.  Customers were primarily looking for their own pleasure, and considering they were paying for it, it was not entirely surprising they would feel that way.  Of course some got satisfaction from being able to please the women, and some just did it naturally by their style and technique.  Things were sometimes different too with longer term customers, especially those who tried to make a degree of connection rather than keep it purely business.  All of this was still too far off for Logan to think about though.  Losing his virginity came first, after that he could decide what came next.

 

With several hours he could afford to take his time a little bit.  It was hard to guess exactly how long the actual sex would last, but if he rushed into it too quickly they might have too much time left over either sitting around awkwardly or with him leaving early.  So he decided to start simple and delay that a bit.

 

Aileen had told him there was no judgment here.  The girls got all sorts of customers and as whores themselves, it would be fairly hypocritical for them to judge their customers, but he did not know for sure how true that was yet and he was not sure how she would take his starting approach.   “I’m going to start simple.”

 

He walked behind her, wrapping one arm around her waist.  The other hand groped her breast for a moment, wandered over to her ass and then back to her breast, cupping it, gripping it, just getting a sense of how it felt.  As a man with no experience, he had curiosities about a woman’s body he wanted to indulge a bit before getting more serious.  Partially to prepare himself, partially to make it slightly less ‘innocent’, he also ground his crotch against her ass.  While he did not think he was going to start with anal, was not sure if he would not try it tonight, he slight pressed his cock inside and out to the extent their clothes made it possible, not nearly far enough in to properly penetrate but teasing it to a degree.  “There are a few simple things I need to experience before we really start going at it.”

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IsabellaRose

Catina smiled as his hands moved over her body. He seemed so tentative, but still aggressive enough to excite her. She got the impression that this wasn't a man who wanted her to do all the work. He seemed like he wanted to take charge. That worked out well for Catina; she hadn't realized how much she loved being told what to do until she started working here. It was a major turn-on for her to be at the mercy of a strong man or woman, to be subject to their wishes and orders. Still, it couldn't hurt to try to help him decide where to start.

"Shall I disrobe for you, L?" He was still behind her, pressing himself hard against her ass. "I can take the lead, if you like, or you can." 

She presses her ass back against him, grinding hard until she feels his bulge pressing between her ass cheeks. 

"We can go as fast or slow as you like," she says, her voice almost a purr of erotic enticement. "Lots of guys like me to start with my hands, then my mouth, before we go further. Would you like that?" She presses back against him again. He's larger than she would have guessed, she can feel him through the layers of fabric of their clothes. 

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SataiRolePlayingGuy

Logan was not sure how genuine she was being and how much was an act yet.  Maybe her reactions were genuine and was getting aroused but perhaps she was just doing it for his benefit and to encourage him.  He would not be surprised if they were encouraged to do stuff like that, either way he figured he would get a better idea of it as they went along.  He was also perhaps more inclined to take control, he was just not sure yet what he wanted to do with that control, but intentionally or not, the first seeds had been placed and it still needed a lot more development but she was already encouraging him to think of her and to a lesser extent all women in certain ways.  "I'll let you know if I feel like doing any of that a little later."  He was already starting to more strongly assert himself.  They were perhaps good ideas, he thought he would like to get a blowjob as part of the experience, but they would happen if and when he wanted them to.

"Let me tell you what to do unless I say otherwise."  He did want to be careful about how strongly he asserted himself.  Partially because he was new at this and partially because the extreme varieties of dominance and submission, enough to make feel like he had truly complete control required spending extra which he had not spent.  The customer/client relationship gave him a lot of control but she was still far from a sex slave.  The control was limited to what he had paid for, making her provide the basics services and companionship he asked for the scheduled time.  Outside of those circumstances she was still free.

"As far as what I want now.  I am going to let my whims control it for a moment and this is actually pretty interesting."  He had not planed on it initially, but he decided to take what they were already doing one step further.  Though not yet to its natural conclusion.  He reached down, unfastened his belt and pushed down his pants and underwear.  He left her clothes in place but his now exposed cock now had more reach.  He pushed it deep between her cheeks but stopped the tip just before proper penetration.  He did a few semi-thrusts, sliding the cock almost out and then back in but still not penetrating.  He was going to leave her guessing on whether or not he would actually penetrate yet.  He had not actually decided yet.  For the moment he liked just doing this, and was curious to see how she reacted.  Was this something she wanted, or at least had an interest in beyond just being his customer?  He had a vague awareness that a number of women might have preferred more foreplay first, but a woman working here was probably more used to things more faster and might even prefer it in at least some cases.

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