Mrs. O'grady's Boarding House

Mrs O'Grady's Boarding House for Young Women

A boarding house where the female residents pay their rent by services rendered to male clientele.

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Author's notes:

1. This is a work of fiction. The activities and practices described in this story are not necessarily either condoned or recommended. If you choose to do anything described in real life with real people you do so at your own risk.

2. All characters are fictional and any likeness to any living person is purely coincidental. The story is purely imaginary and, to the author's knowledge, bears no relationship to any factual occurrence. To the author's knowledge, institutions such as the one described in this story do not exist and are completely fabrications of the author's imagination.

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"Geez, I'm totally skint," complained Jessie.

"Well, you're in luck. I just happen to have some cash so I'll buy lunch for us. Sound good?" replied Melissa, a friend she'd met when she first arrived in the city.

Over lunch in an average café, Jessie, who had recently arrived from the country where she'd been working on a ranch, told her friend that work was just impossible to find unless you had experience.

"And how am I going to get experience without having work? It's a catch 22 situation. I don't want to have to go home again to be told 'I told you so' by my know-it-all parents, but I simply cannot afford to stay here. The rent I'm paying for a run-down room is exorbitant. Food's expensive and I have only a few dollars left before I have nothing. Please, Melissa, as the only person in this god-forsaken city who even gives a damn, what do you advise?"

Melissa stared into her eyes for a long moment. "Well," she began at length, "There are several options. Firstly you could simply go home, but I know you don't want to do that. Secondly you could keep searching for a job, but you've been doing that for, how long now?"

"Four weeks," muttered Jessie.

"Yeah, well if you've found nothing in the last four weeks you'll be unlikely to find anything in the next four. Or you could change your accommodation to a less expensive option like I did when I was in your predicament a year or so ago."

"But the room I have now is a slum, anything cheaper is bound to be worse," reasoned Jessie.

"Not necessarily so. My room is wonderful; it has a pleasant view, is quite large, has a very comfortable king size bed, has an ensuite and a small kitchen. Everything I could want actually."

"And just how much does this palace cost you?" sneered Jessie.

"Well, actually, nothing; not a cent. But I do have to do some work providing services for people in return, and then not only do I receive free accommodation, but also free food and even a small cash allowance."

"That sounds almost too good to be true," replied Jessie, "Are there any vacancies? It sounds just perfect."

"Well, actually one of the other girls left last week, no need to go into the reasons for that, so there is a vacancy at present. You interested?"

"Absolutely. Can we check it out now? Hey, and we'd be living in the same accommodation. That'd be cool. What's this place called?"

"Yes, we can check it out this afternoon, and yes that'd be cool and the name of the place is Mrs O'Grady's Boarding House for Young Women."

"Hmmm, that sounds a little pedantic and old fashioned. We don't need to wear ball gowns when we eat or anything like that do we?"

Melissa laughed. "No, of course not, this is the 21st century. There are some dress standards but they are very informal and never strict, in fact, if the truth be known, they are often extremely casual. You'll see when you get there. Hurry and finish your lunch then we'll go."

They finished their lunch and quickly walked the three blocks to the boarding house, where Melissa let them in a side door with her key. The first thing Jessie noticed was that it was very tastefully decorated with discreet lighting, thick carpets and drapes and wall hangings in profusion. It gave the air of being opulent without being flashy.

Melissa led Jessie through several corridors until she finally came to a large entrance foyer opening onto the main street with a wide, grandiose stairway leading upstairs. To one side was an office with a large dark-stained wooden door on which Melissa knocked and waited. The door was opened by a young woman, well dressed in an almost transparent top and short tight skirt.

"Melissa," she greeted, "How may I help you?"

"This is my friend Jessie and she's really short of money and I told her a little about this place and she thinks she'd like to live here."

"Well, I guess she'd better have a chat with Mrs O'Grady then. Come on through. By the way, Jessie, my name's Trish."

Trish led them across her outer office and knocked on an inner office door which was opened by an elegantly dressed older woman. She smiled at Melissa and then flicked her eyes over Jessie as Trish explained the situation.

"So you think you might like to stay here for a while," she said.

"Yes please. I'm used to hard work and can do just about anything," replied Jessie.

Mrs O'Grady chuckled. "Well, the work's not really hard, is it Melissa?"

"No, Ma'am," replied Melissa.

"And being willing to do almost anything would certainly be a distinct advantage. We do have a vacancy so I am very willing to give you a room for a trial period, say one week. Would that suit you? It would give you time to work out whether you wanted to remain and it would give us time to see how well you were suited to the tasks expected of you."

"Oh thank you Mrs O'Grady, thank you so very much. You don't know how much this means to me," gushed Jessie.

"Yes, well, we'll see. You may change your mind after a few days but till then you can have room 17; first floor, next to Melissa's. She'll show you where it is. Melissa, can you please also explain the basics of what Jessie needs to know. Oh and by the way, just call me Ma'am, please."

"Yes, Ma'am, thank you Ma'am, I assure you that you'll not be disappointed."

Melissa escorted Jessie to her new room 17, next to Melissa's room 16, and showed Jessie in. Jessie was dumbfounded when she saw what, to her, was unaccustomed luxury. She spent a few minutes exploring the room and fittings while Melissa showed her how things worked. Once she had finished exploring, Melissa sat her on the bed and began to tell her what was expected.

"This is not your usual boarding house," she began, "It does serve another purpose. It is a well-known entertainment establishment for men."

"Oh, you mean like a gambling den or something like that," interrupted Jessie.

"Yes, something like that. Men may just call in for a while or may often stay the night."

"So what has that to do with us?"

"God, you are so naïve!" exclaimed Melissa. "When men stay here the night, they stay with the young women who live here, in the same rooms, in the same beds, and I hope I don't have to explain what happens between the sheets."

Jessie was silent for a few minutes, then hung her head in embarrassment. "No, you don't," she muttered, then raised her eyes to meet Melissa's. "So what you're telling me is that I now live in a brothel."

"Well, you put it so crudely, so I'll be blunt; yes. But don't ever let Mrs O'Grady hear you use the 'b' word. She considers this establishment to be a far higher standard than a common old brothel. So let's get to the nitty gritty. You're not a virgin are you?"

"No. One of the ranch hands saw to that last year."

"A pity as you would have received a large bonus. But it can't be helped and it's probably best for you. Are you on the pill and do you have any sexually transmitted diseases?"

"Yes and no. I went on the pill just in case I met some lothario who fancied me in this big city, but no such luck."

"Right, so you're ready to start work straight off. I'll let Mrs O'G know. The going rate for us is 10% of what the client pays plus free board and meals, so long as you service at least four clients per week. Less than that and you receive less cash, more than that and you'll get a bonus. Mrs O'G is quite generous to those who work hard but just try not to get on the wrong side of her. I'll go now. I have a booking in a short time. Trish will be up to measure you for some sexy clothing. See you later and good luck."

"Thank you again, I think," replied a distinctly less enthusiastic and more nervous Jessie as Melissa closed the door behind her.

Jessie lay on the bed and thought. So she suddenly lived in a brothel and was about to begin work as a prostitute. Oh well, at least she couldn't complain that life was boring.

During that afternoon Trish took Jessie under her wing, explaining the rules, sorting out some elegantly sexy clothing for her to wear when meeting clients, organizing an STD test for her, buying some cosmetics that suited her skin color, introducing her to many of the other residents and eventually gave her an appointment with her first client the following day. Jessie had a moment of panic.

"What do I do when I meet him?" she asked, "I mean, it's not as though I can just say 'I know you're here to fuck me so fuck away'."

"Just talk with him as though he was any guy with whom you wanted to be friends," advised Trish. "Many of these guys are here because they're lonely and want company, not just sex. It's not like we can do a dry run; every time's for real. Just remember he's not here for you to fall in love with, just to provide a service to, and the golden rule, always use a condom."

"Yeah, I guess it will be OK. He'll probably be as nervous as me anyway."

The appointment time the following day came around too fast; time dragged then suddenly it was there. A lunch date with a guy who gave his name as Jake; probably not his real name and Jessie noticed he wore a wedding ring. The date went well, Jessie thought, and she told Melissa about it that evening as they sat together on her bed.

"We met in the foyer and he seemed nice enough. It felt strange to be hugged and pecked on the cheek by a total stranger but then he held my hand and we stepped out onto the street. I felt like everyone was staring at us, as if they all knew who we were and what we were going to be doing.

"He took me to a very nice restaurant where we had a light lunch. I had a glass of wine and he had a beer, and we chatted a bit about ourselves, revealing little but filling in the space so we sort of got to know each other. I guess he was my type, at least superficially, and I found him easy to talk with. Lunch went well, then it was my turn to lead.

"We headed back here and I led him to my room, closing the door behind us. I then approached him and embraced him, reaching my lips up for him to kiss, which he did. Soon we were open-mouthed kissing and I felt myself starting to become aroused. Slowly and sensuously we undressed each other until we were both fully naked. His cock seemed enormous and I wondered if it would all fit inside me, but I needn't have been concerned. He began stroking me all over and led me to the bed so we could be more comfortable, as he said.

"He asked me to suck him so I did. I'd never sucked a man's cock so had no idea what to do, but he seemed to like it just fine and very soon he told me he was nearly ready to cum so I'd better stop if I didn't want that. Well, I'd never had a man cum in my mouth and was curious about how it felt and what his juice tasted like, so I just kept on going. A few seconds later I felt my mouth filling with liquid and I had to swallow or drown. It tasted sort of salty but certainly not unpleasant. Jake had tensed right up and then relaxed after he squirted and we rested for a while as I explored his balls and he caressed my nipples and my pussy, inserting first one then two fingers into my hole. It felt really good, especially when he found my button and rubbed that.

"About twenty minutes later he rolled me onto my back and positioned himself over me. I had the presence of mind to tell him he needed a condom and rolled one onto his hard cock. It was very similar to what I did in practice with Trish using a carrot. He then pulled my legs wide apart and entered me slowly. I felt every inch of his wonderful hard cock move into me, stimulating the nerves in my pussy walls as it first pressed them gently then spread them wide to effect its passage. It felt much nicer and I was much wetter than when I'd had sex with the farm hand on the ranch. His cock filled me so wonderfully that I really enjoyed making love with him. He massaged my breasts and nipples and kept on fucking me for ages, probably because he'd already cum, until I felt that I was going to cum. I told him this and he thrust harder and faster into me and suddenly I was there.

"It was my first orgasm with a man and it felt wonderful. I held him tightly, pressed myself against him and really let myself go, so much so that he came again too. I'd have loved to feel his cum flood my pussy but I guess the condom prevented that, but I did feel a warm fullness inside me. Then we lay together, panting and kissing until his cock shrank. He then held the condom as he withdrew carefully. I felt so empty and would have loved to have his hard cock in me again, but I guess that all good things have to end sometime. We then lay on the bed for a while, kissing and fondling each other, then dressed and kissed and I escorted him to the lobby and he left."

"Wow, that was awesome," replied Melissa. "It sure sounds like you had a good time too. What a way to start life as a pro."

"Well, I certainly hope they're all like that."

"Be great if they were but they're not. Many are uncaring and simply use you as a receptacle. Often they don't see you or treat you as a human being but simply take their pleasure and leave. However, Trish does try to arrange someone pretty good for the first time so looks like she succeeded this time."

"Yes. I'm really looking forward to my next appointment. It's really strange, for weeks I've been slogging my guts out looking for work and now I have all this time with little to do. I'll have to find a hobby or something."

Melissa looked at Jessie in a calculating way for a few seconds, then took the bull by the horns.

"Well, many of the girls feel the same way and most of us have found ways to deal with it in a very pleasant manner," began Melissa hesitantly. "Have you ever made love with a woman?"

"No, never. Never even thought about it. Is that what girls here do to occupy themselves and keep themselves amused?"

"Yes, most girls, almost all of them, are bisexual, which means they are as happy making love with a woman as with a man. They're not strictly lesbians because lesbos don't usually like being fucked by a cock, so that makes them bi. Have you thought of it at all?"

"Well, I've heard of it but never thought to try it. Of course I've masturbated myself to some wonderful orgasms, but I've never done it with another woman. It sounds like fun though; do you have time to teach me now please? Could we make love together now, do you think?"

"Sure, honey, why not," replied Melissa moving herself closer to Jessie. She then leant forward and kissed her full on the lips, a long, lingering, tongue-filled kiss that left them both panting afterwards.

"Oooh, that felt wonderful," said Jessie breathlessly after they had broken the kiss, "Can we do that again please?"

"Of course, as many times as you like," replied Melissa once again initiating a sexy kiss and this time toppling them sideways so they lay face to face on the bed, still kissing as their free upper hands roamed over their bodies. They broke the kiss briefly.

"Follow with your hand what I do with my hand," instructed Melissa.

They resumed kissing and Melissa began introducing her hand under Jessie's top, cupping then kneading her breasts, feeling her own breasts being cupped and kneaded in turn by Jessie. She reached around and unclipped her bra, feeling he breasts hang free once Jessie followed suit, then began gently caressing, squeezing, and twisting her nipples.

Melissa had done all this to herself but never to someone else and had never had it done to her by someone else. The effect was extremely arousing, not only from the sensations felt by her own nipples, but also by the knowledge that what she was doing to Melissa was causing her to feel the same way. It also seemed to flow through her hand and arm and the sensations of Melissa's breasts in her hands seemed to arouse her also. She became aware that she was very wet between her legs.

Melissa must have been the same way because in a few minutes she lowered her hand to Jessie's legs and ran them up her thighs under her short skirt, then moved from the outside to the inside of her thigh. Jessie moaned as she felt Melissa's hand so close to her sopping mound and repeated the movements on Melissa, eliciting a moan in response. Both women continued caressing the pubic area, avoiding the more sensitive labia and clitoris for the time being, focusing on pure sensual enjoyment of each other's body.

After a long few minutes, by which time each woman was humping her pussy against the other's hand trying to gain more stimulation, Melissa eased Jessie's panties down her legs then began caressing her shaven lips, before beginning to gently rub her clit and introduce her fingers into her opening. Again both women moaned with pleasure.

After another ten minutes or so of this stimulation, by which time both women had achieved a rhythm that was rapidly taking them towards their orgasms, Melissa abruptly stopped.

"Time to get naked," she said huskily.

They wasted no time in sitting up and quickly removing their tops, skirts, loose bras and pushing their panties the remainder of the way down their legs. Then they hugged each other, front to front, breasts and pussies pressing each other's breasts and pussies and they ground their pubic bones against each other.

"I guess you've got no toys," said Melissa.

"No, none at all."

"Pity, I'll introduce you to mine some time. Right now it'll have to be manual or oral. Which do you want?"

"Well, I've done manual on me, so let's do oral."

Melissa lay on her side and instructed Jessie to lay on her side so her mouth was level with Melissa's pussy. Once they were positioned, Melissa again instructed Jessie to follow her lead. She began by tonguing Jessie's lips and clit, pushing her tongue between her lips, drawing it the full length of her gaping slip, sucking gently on her clit, then nibbling it with her lips then lightly with her teeth. While doing all this, Melissa was pushing one, two then three fingers into Jessie's vagina, moving them in and out and stimulating the passage walls with each thrust. Needless to say, Jessie was doing exactly the same on Melissa, as any conscientious student would.

Together they climbed hills of arousal, then progressed to the mountains. Each was pressing her pussy against the other, seeking greater stimulation until after what seemed like forever in this growing blissful nirvana, Melissa gave an almighty thrust inside Jessie as she came hard on Jessie's fingers and tongue. The sensation of having Melissa cum on her mouth and fingers was too much for Jessie, who also pressed into Melissa as she achieved a mind-blowing orgasm.

They lay together, unmoving, allowing the sensations to die gradually as their bodies slowly relaxed into that post-orgasmic bliss that is so relaxing, so restorative, so peaceful. After a while they stirred and parted reluctantly, kissed deeply and sat up facing each other.

"And that," said Melissa, "Is one way women make love together. Like it?"

"Oh did I ever," enthused Jessie, "It was wonderful. Better than either of the men I've had."