Melissa's New Position Ch. 12

She went to her bedroom and found Sandi asleep. Instead of trying to find her her own bed, she just got in with her. She got behind and spooned her, her arm reaching around and touching her small breast, carefully avoiding the sore nipple. It actually felt very nice to have someone to hug. Sandi pushed back, snuggling her butt up agains Melissa and they both fell asleep. Their nude bodies touched most of the night, a comfort to Melissa as much as it was to Sandi.

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The next morning Melissa felt great, but Sandi seemed sore and walked gingerly as they went down to the kitchen for breakfast. Sandi was still naked, and it did not seem like she would be getting dressed anytime soon. They both padded slowly down the corridor.

Breakfast was good. There was fruit, eggs, bacon, and toast. Melissa was hungry. Sandi seemed less so, but she did eat. Melissa wanted to make her feel better somehow, but didn't know how to do that.

"By the way, Sandi, I'm Ron. I sort of run the place. Chief cook and bottle washer, really. I know Mr Hartford wants you trained and Melissa will do most of that. I'll do some as well. We'll see if we can help you get to where Mr Hartford wants you to be, okay?"

Sandi glanced at Ron, but did not look at him as she responded "Okay." Her voice was not very loud and she seemed much more nervous than she had when she got there yesterday.

"I suppose we can start with my morning blowjob. Melissa usually helps me out with that, but I thought this morning you could do it. It will give us some idea what your baseline is."

Sandi looked even more nervous, and looked to Melissa for reassurance. Melissa smiled encouragingly. Sandi paused a moment, then got up and walked over to Ron. She got down on her knees in front of him, but did not look up at him. She gingerly took hold of the elastic waistband of his shorts and slowly moved them down from his hips, exposing his penis, which bounced up, partly erect, as soon as the material set it free. Sandi pulled back as though she had seen a jack-in-the-box. Her eyes were wide when she saw the thing.

Melissa watched as Sandi reached up and touched his cock, putting her hand around it like she was trying to hold it still. Her hand was small and his penis was not, and the contrast was impressive. She moved her hand back and forth a little, and saw his cock start to swell to its full size as a result of her efforts. If she looked apprehensive when she first saw it, she looked almost scared as it grew.

She leaned her head forward and stuck her tongue out and touched the little clear drop that had formed at the tip. She then licked the end several times before she put the very tip into her mouth. It was like it was a sucker or an ice cream cone that she was licking. She still grasped it hard in her hand, as though she was afraid it would either get a way or attack her somehow. She didn't seem to trust it, in any case.

She moved her head slightly, taking the head into her mouth and then pulling back. She did not get very much of him in her mouth at first, but gradually she made more of a stroking motion with her head, taking in several inches of him. She started to move her hand up and down his shaft, almost abruptly as though she just remembered that part. Her tight grip and rough movements could not have been all that enjoyable for Ron, but he did not say anything. He did reach down and take her hand and gently loosen it, taking it off his member. He put it on his hip, and she kept it there, using only her mouth. She seldom did get any more than a few inches of him in her mouth at a time, and when she did Melissa could see her stomach tighten in that jerky way that meant she was trying not to lose its contents. But, she did get a rhythm going and after a long while, Ron began to show signs her efforts were about to bear fruit.

It looked like he wanted to grab her head and take control, but he never did. Instead he finally leaned back, thrust his pelvis out, groaned loudly, and discharged in her mouth.

When he did, it was clear that Sandi was not prepared. Mellissa knew that when Ron climaxed he was pretty prolific and it seemed that Sandi found the copious semen he gave he more than she knew what to do with. Her eyes popped open in obvious surprise. She did not swallow any of what he gave her, and in a moment her cheeks bulged and some of it came out of her nose. She looked horrified, and had no idea what to do next. Melissa could see she was not going to swallow, so she reached over and took a kitchen towel and handed it to Sandi. When she did, Sandi then pulled back and put her face in the towel, spitting out the contents of her mouth. She still had semen dripping from her nose and she looked miserable. Ron did not say anything, but just pulled his shorts up and went about cleaning up from breakfast.

Melissa helped Sandi to her feet and walked her down the hall to the bathroom. Sandi blew her nose over and over, crying as she went. Melissa hugged her as they walked. When they got to the bathroom, Melissa helped her into the shower and waited until she was done. As Sandi toweled off, Melissa said to her "I think you are going to have to learn to swallow."

"I know I should have, but it came so fast and so much and it caught me off guard. I did that horribly. Ron must think I'm a piece of shit."

"I doubt he thinks that. He knows you are here to learn. He said he would help, and I will, too. You'll get good."

"I don't know. Do you think I can? That was the worst I've ever done. I'm glad Mr. Hartford did not see that. You won't tell him, will you?"

"Of course not. Why would I?"

"Do you think Ron will?"

"I don't think he would. I don't know why he would do that. Let's just help you get better so it does not happen again, okay?"

"OK. I really do want to be good. I don't want Mr. Hartford to get rid of me."

"Get rid of you?"

"If I can't get good at all this, I'm afraid he won't be happy with me. I know he won't. You'll help me, right?"

"Of course I will. Let's just go to the beach for a little while, and then we can work on helping you practice."

"We can do that?"

"Sure. We don't even have to change!"

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For the better part of the next hour, Melissa listened while Sandi talked. It turns out that she was only recently 21 years old, and that it was on her 21st birthday that her friends took her out to an exclusive club one of them had enough of a connection to get them into. They all lived in a small town about an hour and a half from the city, so this was quite out of the ordinary and over-the-top exciting. They arrived and went to the hotel room the four of them were sharing and got dolled up for a night on the town. Dressed as hot as they knew how, she and her friends were pretty uninhibited. They encountered some folks who offered some cocaine to go with their alcohol and one blazing good time ensued. Sandi, celebrating her birthday, was particularly enthusiastic on the dance floor, and caught the eye of an older man who chatted her up. Instead of hitting on her directly, he asked about her interest in sex and her sexual prowess. She was not lying when she enthusiastically endorsed sex, though she did exaggerate some about her level of experience. Given her level of intoxication, she could not be blamed, perhaps, but when he started asking if she might be interested in working on an island at a retreat where she would be, in part, entertaining men, she (coyly, to her mind) suggested that she might be.

"I really had no idea what he was talking about. I was pretty wasted. But when he said I could earn as much as $100,000 a year, I was pretty interested. I did not get a lot of details. He said I was guaranteed $1000 a week. He gave me what he called a 'sign on bonus' of $10,000 and told me to have a good time celebrating my birthday. He gave me an address to meet him at in a couple of days and told me that I did not have to give back the money unless I changed my mind."

The money fueled a hell of a party for that day and the next two. She used a lot on coke, on fancy meals, on shopping, and on more clubbing. She also recalled going to a casino, though she could not remember much about it. She and her friends had a weekend of a lifetime, but when it was over, little of the ten grand was left.

Sandi did show up to Mr. Hartford's office when she was supposed to, but she looked like she had been through the wringer and felt like it as well. Mr. Hartford was not as impressed with her as he seemed the other night, and she felt bad that he seemed disappointed. She tried to get her head clear and make herself presentable while he explained what his plans for his resort were. He was going to have a getaway that high-achieving executives could enjoy if their performance warranted it. He wanted it to be for motivation, and one of the things the getaway would offer was her services.

At this point, mostly sober and without the rush of her Girls Gone Wild weekend, his offer did not sound nearly as enticing as it had three days ago. On the other hand, she could not produce nearly any of the $10,000 she had been given and had no way to pay it back. Her friends had gone home and she had expected to go on to her new job, and it seemed like there was not another direction for her to go, so she decided to go along with it. If she did not like it, she could just quit. At least after ten weeks.

It was still a surprise to her when he stood up and said "Suck my cock."

"I was shocked a little, though I don't know why I was. I felt like hell and did not want to do it, but I did. I thought I had to if I was going to do this."

However, most of Sandi's sexual experience had been letting boys screw her. She did not really do a lot more than that, and everyone was happy. She liked guys fucking her. They liked it, too. She had not done much that was more active, however. She had sucked on guys a little sometimes, but had never actually given a blowjob that involved his climaxing in her mouth. This was going to be different. And it was. She had little skill, and her clumsy efforts were not all that pleasant for Mr. Hartford. He finally pushed her away and zipped up.

He was pissed at her, and accused her of misrepresenting herself. She was upset, saying that she would do better. He said she had to give back his money. She said she did not have it. He said she would have to come up with it. She said she did not have a job, but she would do whatever she had to to be good at the one he had offered her. He glared. After a long moment, he walked over to his desk and called someone.

He had called Mr Dorn, and in front of Sandi, described what had happened and how it was he was now stuck with some dumb bitch who said she wanted to work at his resort but could not even suck a cock. Sandi was in tears at this point. She could only hear one half of the conversation, but it was clear enough after a few minutes of Mr Hartford's ranting that Dr Dorn had offered some kind of solution, because Mr Hartford started nodding his head.

"I appreciate it. I think that would work. All right, let me get over there and we'll do that. Yes, I appreciate it. Okay. All right. You, too."

And he hung up.

"Okay, I have a friend how has a setup like the one I want to have and we're going to take you there and have his girl teach you some of what you need to be able to do. I'm not going to pay you any more until your training is over, but if you can get up to where you need to be, I'll put you on the payroll. If you can't, I'll sell your services to someone who is less exacting and let you pay it off that way."

Sandi could tell he was still mad, but she was sure that he meant what he said. She definitely wanted to please him. She understood clearly that if she had to work off her debt, it would most certainly involve her being used sexually anyway, and probably not at very high wages. She imagined having to serve men, not at a resort, but in a brothel or something like that. And probably not at $100,000 a year but at $20 an hour. It would take a lot of hours to pay off $10,000.

"I'll learn everything you want me to. I'll do this right. Honest."

Mr Hartford seemed to be placated some. "OK. See that you do. I want you to be a star at my resort. I want you to shine."

This was much more like what Sandi needed to hear. She was relieved and resolute. "I will."

Melissa listened while Sandi told her all of this. She wondered how Sandi must feel. She figured she was every bit as much out of her league as Melissa had been when she got here, in a way, but Melissa had much more experience with sex because Roger was so demanding. Still, she could feel some empathy for Sandi and did want to help her succeed.

"He told me that if I get really good, he'll buy me some boobs, too" Sandi said with a little excitement. She had been kind of down while she told her story but was bouncing back quickly.

"You have such pretty boobs. I'd love to have boobs like yours. I don't know if they can do that but I'd like it. Did you have your boobs done?"

"No, this is just the way I am."

"Well, you're lucky. You're really pretty too, not just nice boobs. I don't think I'm that pretty. Boys always liked me, but I wanted to have bigger boobs. I hope Mr Hartford is happy with me and he buys me some. Boobs are expensive, you know?"

Melissa had no idea how to talk to this woman. She found herself protective of her, in a way, and she liked her and all, but she seemed to have some weird ideas about things. At least weird to Melissa.

"Well, I'll help you as best I can.

"I really appreciate it. I do. I have to learn to do what you do and learn to do it like you do. I want to be good. What should I do to start?"

"Well, I suppose you will have to have practice with sucking. We have some dildos that you can practice on. Let's go down to the playroom."

As they walked, Melissa said "You will also probably need to get used to stuff in your ass. Guys are really interested in anal sex. I think they do not have a lot of opportunity with their wives or girlfriends or whatever. Most guys want to stick it in my ass."

"I don't like it in my butt at all. I had a boyfriend try that once and it really hurt. I would not let him do it. I made him stop."

"It hurts, but you can get to where it does not hurt too much. Actually, once you get going, it can feel pretty good. When I first started, when I guy put it up there, I could hardly breathe. It's much better now."

"How do you get to where it doesn't hurt?"

"I had to start with butt plugs. I think we will have to do that with you. You start out with a small one, and then after a while, go with larger ones. You get used to it."

They had arrived in the playroom. Melissa when to the cabinet with the butt plugs, picked one about the size of her first one, and grabbed some lube to go with it. Getting the thing in Sandi's ass was another thing entirely, however. She had her bend over and tried to insert the lubed up plug, but Sandi was as tight as she could be, and Melissa was not getting very far.

"Owww! Stop! I don't think I can do this."

Melissa said "I can stop if you want, but if you don't stretch out some, it's going to hurt a lot more than that when someone puts a cock up there. And, it looks like whether you do it at Mr Hartford's resort or whoever he sells your debt to, you are going to have someone putting a cock up there. Trust me, guys really like that."

The reminder that it was not if, but where, she was sodomized seemed to have a sobering effect on Sandi.

"OK, you're right. I know. I have to do this. Just go easy, okay?"

Melissa had been going pretty easy, but instead of the plug, she inserted one finger into Sandi's anus. She then moved it in and out some, and pulled out enough to rub her slick finger on Sandi's tight butthole before penetrating it again. She did this, knowing it would feel good, and sure enough, after a while, Sandi started to relax. With her other hand, Melissa stroked Sandi's little nub while still moving her finger in and out of her behind, and that really started to loosen her up. Melissa added another finger, and moved them both in and out of her ass, still fingering the swollen little clit with her other hand. Sandi started to have trouble standing up. Melissa was starting to get into this, and actively worked to get Sandi aroused.

It was working. Soon she had two fingers deep inside Sandi and was pulling up on her, almost like she was trying to lift her up by her anus. This stretched her a little more, and when Melissa tried to insert the plug this time, it slipped right in. All Sandi said was "Oooh!"

Melissa went over to the sink and cleaned her hands, and Sandi tried to straighten up and walk with a plug in her ass. She looked a bit comical and Melissa reflected on what she must have looked like when she had her own first time with one. She still smiled. Sandi was still obviously aroused and could probably have used a nice orgasm at that point. Melissa thought she might do better if she were turned on, so she made no effort to relieve her. There would be time for that later, perhaps.

Instead, she went to the cabinet with the dildos and retrieved one that was not anywhere as large as Ron and gave it to Sandi.

She showed her how to suck on it. She gave her instructions to start by licking the tip, working around the head, licking the length, and eventually moving it into her mouth. She was patient, explaining the finer points of cock sucking, and Sandi practiced over and over sucking on this modest phallus.

She got to where she could get it all the way into her mouth, and to the back of her throat, with Melissa's encouragement. She still gaged easily, and it was easy to see her stomach lurch as she tried to keep the contents of her stomach in her stomach. Still, she persevered.

For her part, Melissa found she kind of liked being in the role of instructor here. She surprised herself at how much she actually knew about penises and what people who owned them liked. She was a cock coach. That made her smile.

Over the course of the rest of the morning, Sandi sucked on dildos while Melissa offered tips and encouragement. The small dildo was exchanged for progressively larger ones, and by lunch Sandi was much more confident and competent in the cock sucking department. She hadn't tackled a particularly large one, but she seemed more comfortable with the whole business. It seemed to lighten her mood, perhaps because she really did see herself being able to do this well at some point.

Melissa was encouraged as well, getting into her role as instructor. Deciding to press the anal issue, she told Sandi to lay down on the bed in the adjoining room, and to put her legs back as far as she could. Sandi was pretty flexible, and put her legs back so that her ankles were on either side of her head, so Melissa had her put her arms on the back side of her legs, keeping her folded in half like that. This exposed her sex and anus about as much as possible. Melissa took the plug and began working it around, moving it in and out a little, stretching the little pucker holding on so tight. At the same time, she rubbed the little clit that popped up so pronounced in this position, drawing moans from Sandi. She then removed the plug entirely, and replaced it with one of the dildos. It was larger than the plug, but it was not that big. She moved it in and out, however, like she was fucking Sandi with it, all the while continuing to work on the swollen clitoris.

Her efforts with the dildo and her fingers worked together to build Sandi's arousal to a peak, and then brought her over the edge in a dramatic orgasm.

All Sandi said was "Wow!" as she unfolded herself. "That was pretty intense. This butt stuff is not so bad as I thought. Thanks!"