Rachael Ch. 07: The Lesson

The Lesson: Jenny's first anal

Jenny returned at 9:00 AM and smelled very good. Whatever she used preceded her into the room. "Phew" I said, "what is that perfume?"

"Something new I just tried, you don't like it?"

"It's a little flowery for me I think, do you like it?"

"It's ok, not going to be my favorite."

"Tell me what you want to be able to do and what you know about anal sex."

"That's easy, I don't know much of anything beyond putting his dick in my asshole and I want to do it with this client without getting hurt. That's what scares me the most, internal damage."

"Here are the basic rules and we will look at each one of them individually as the lesson goes on."

"Number one, there is no such thing as too clean. Your rectum must be spotless, no crap of any kind. First off, if it gets on his dick it will irritate your anus and you won't like it, second he will be pissed if he pulls out a painted dick."

"Number two is never put an uncovered dick in you, anywhere. That's pretty normal here at Madame's."

"Number three is always maintaining control. Never let the guy plow you up like a farm animal. I will show you ways to do that but if you let him hurt you it's your fault, got it?"

"Yes," she replied.

"Let's get started. The douche is where you start your preparation. Warm water and if you need to go, put a little of the Fleet preparation in the mix to help you. Did you bring your douche bag?"

"Yes, I have it here."

I showed her the bottle of fleet preparation and told her I hated the small bottle with a tip but in a pinch, it worked pretty well. Putting the bottle of Fleet in the douche bag I then filled it up with warm water. This would give her several fill ups for her first douche, and everything should come out fine.

"Sit on the toilet please and go if you have anything to eliminate. When you are ready, just insert the tube in your anus and open the flow valve just like you do for a pussy douche. You need to get a second tip for the hose. You shouldn't use the same tip for pussy and asshole."

"Is it going to hurt?" she said.

"Only if you do it wrong. You must learn the proper angle of insertion. If it's not straight, then it will hurt some. Here use a little of this lotion on your hole and just experiment with putting it in. Take note the angles and how some are harder than others to make penetration. Remember that when you take a dick in there that's when it really counts. A crooked angle with a big dick can really hurt."

She lubed her asshole and played with the douche wand for a bit and finally got it inside her. I like to use the pussy wand tip because it sprays from all sides and does a better job. I showed her the difference and told her again not to use the same one in both holes. We released the water and I told her to shut if off when she felt full.

"Gee that actually feels good," she said.

"I know, I love the feeling myself and I do it a lot, sometimes just to feel better."

She shut the water flow off and pulled the wand out.

"Hold the water in as long as you can. The chemical in the Fleet solution will make you want to eliminate but resist it."

She let it go in about three minutes and after she wiped, I told her to look in the toilet and see what she deposited there.

"Now do it again. We will use the whole bag or more until the water that comes out is clear."

"Ok."

I left her alone for a bit and let her figure out how to do the douche. She was used to douching her pussy, but this was new, and I wanted her to experiment with it.

I went and got a cup of coffee and returned.

"All done? I asked.

She showed me a clear toilet and said, "yes and I feel terrific."

I handed her a tampon and said, "Put this in the hole."

"What for?" She retorted.

"To dry things out, it will feel good too"

She put it in and made sure that it didn't get lost. I told her to leave it in for about fifteen minutes and then she could take it out.

"Ok, you are now ready to be fucked."

"I don't need to teach you about condoms but make sure that you don't forget."

"I won't, I learned that lesson a long time ago."

"Lubrication is next, and the golden rule is that if you think it's enough, use more. He won't be able to tell if it hurts you, only you can tell that and, in most cases, he won't care. Butt sex never seems to last as long as the porn films show it, but it can be a painful few minutes if you're not lubed enough. There is no natural lubrication like the pussy, it's dry and will irritate very quickly. Whatever you use for body lotion will help keep it moist too. I use it every day after I shower, just put a little on my finger and rub it into the hole. Here try some."

I gave her some lotion and she pulled the string and got the plug out. She felt around some and I could see her putting her finger in the hole, she made a bit of a face as I watched.

"Talk to me," I said.

"Well, it hurts a little"

"Does it actually hurt, or is it just uncomfortable?" I queried

"I don't know."

"Turn around, bend over and let me see what is going on."

"Ok"

I spread her cheeks with my thumbs and looked up into her anal area. "Holy crap Jenny, this is dirtier than a dump. You're cleaner inside than you are outside. Don't you wash this place?"

"No, I guess I don't very often."

"Well you better start. Some guy is going to want to rim that thing before he fucks it and he won't stay long if it's like this."

"Okay, sorry."

I got a washrag and soaped it up for her, instructed her on how to use it and she cleaned herself up. Then I had her do it again with more soap, she is a girl, this should be second nature.

When she finished the second time I said, "Turn it up for inspection."

She turned and bent over in front of me and I said, "spread-em." She pulled her cheeks apart for me. I saw all pink inside now and I gently pulled her ass toward me and took a long lick. She jumped, and I pulled her hard into my face, forcing my tongue up against her button and felt her relax a bit.

"That's pretty good now, tasty."

"Did you really do that, it must be disgusting," she said.

"If you think your asshole is disgusting, what do you believe your big tipper is going to think? You need to learn to love that hole if you are going to use it to earn a living."

"I guess you're right, I just never thought about it."

"You keep your pussy spotless, don't you?"

"Yea, of course."

"Well this is the same thing."

"Your right, sorry again."

"Maybe you need to appreciate an asshole a little this morning."

"What do you mean?"

"Come to the bed with me, you will get to examine mine for a bit, so you can see close up how it works."

I took off my robe and kneeled on the bed, pulling my cheeks apart so she could see my pink pucker spot.

"Look at mine and imagine yours looks the same. Now put your finger in there and feel it. It won't bite you. You need to know what it's like and how you will feel to your partner.

"Ok, I can do this."

"I sure hope so or this is going to be a short lesson."

She felt around for a little bit and after a few passes she began to really feel how soft the outer tissue is. I moaned a bit to indicate I liked what she was doing, and it encouraged her.

"Put some spit on your finger sweetie and rub it onto the pucker."

She did and studied it some more.

"Now push your finger thru the middle"

"It's so soft," she exclaimed.

"Yes, it is, yes, it is"

"Should I kiss it like you did?"

"Absolutely," I responded.

I could feel her cheeks press against the inside of my butt cheeks and then the hard reality of her tongue on me. She licked it one time, tasted it and seemed pleased because she went back for more.

"Oh honey, that is really good," I told her.

She liked the encouragement and dove in, pressing hard against me and pushing her tongue hard up into my hole. Now I seemed to be getting a little worked up and needed to either get fucked or start fucking.

"Oh Rachael, that is really good, it even tastes good, I could never imagine doing that. Are all assholes like that?"

"No baby, they aren't, only clean assholes are like that and very few are that clean. Did that turn you on a little?"

"Yes, it did, my pussy is actually getting a little wet and my nipples hard, wow this is great."

"Then we should move on," I said.

My dick was hard by now and I wanted some relief but knew I needed to give her a little more training before I fucked her. She was really getting wet, so I told her to bend over for me and I slipped on a condom and then inserted my penis into her hot wet pussy. She was surprised but seemed pleased.

"Do you get a lot of guys who want to do it doggie style?" I queried.

"Yes, it seems to be a favorite position for married men, they don't want to look at your face," she chuckled.

I just left it in her for a bit so we both could relax in the position and get a good feeling for each other.

"Do you want to cum?" I asked.

"I already did twice."

"Then you should be relaxed enough for us to proceed."

"What's next," she asked.

"I think we should use a trainer, so you can warm up to the insertion of things in your butt."

I went to my special drawer and got out a small butt plug. I used these a lot with guys who wanted to be fucked. I never liked using them on multiple partners, so I keep a supply of new ones.

"This is for you, you may keep it, and you must keep it clean. Use it when you feel like, and never let anyone else use it."

"Okay," she replied.

I showed it to her and explained how the steep slope on the sides allowed it to open her up slowly and make expanding the hole much more comfortable. I moved her to her back, had her put her legs up high and lubed her anus. I put more lube on the plug and then put the point on her hole.

"OK, here we go. Relax and let it happen, your natural tendency is to clamp down and resist. You must fight that off, it's kind of like the throat when giving good head. Relax now and let me push."

I moved the plug in and out for a few minutes, getting about half of it in. She seemed to relax a bit and the smooth penetration along with my rhythm was helping her along.

"Now I want you to do it to yourself," I said.

She reached down between her legs and took hold of the base of the plug and began to push it in and out the same way I had been doing.

"Harder now and push it deeper. Do it at your own pace," I said.

Without telling her, I gave the plug a final push. I knew it would pain her a bit but the next thing she knew it was in and seated.

"That plug is half the size of a cock, so don't think you are ready yet."

"It's ok, it only hurt when you pushed it the last little bit. It feels ok now."

"Get up and walk around, keep it in, don't let it fall out."

She did as I instructed and a couple of times she had to reach back and push it back in place as she felt it coming out. She was doing fine.

"This is your exercise, put it in and walk around with it, do it as often as you like but at least twice a day. Sometimes I like to use it and wear heals, it feels dainty for some reason," I laughed.

"Ok, I can do this," she replied.

"Go to the bathroom sink, take it out and wash it with warm soapy water, always keep it clean. Since you just douched it should be clean but that won't always be the case, you need to keep it clean."

She did as I asked and then returned to the bed where I was waiting, hard and lubed up just for her.

"You are as ready as you are going to get Jenny, so now you need to learn how to keep control. Come over here on the bed with me and straddle me like you are going to fuck a guy cowboy style."

She climbed up on the bed and sat on my groin with my hard cock in front of her. She reached down and felt its size and slipperiness with her hand and smiled at me.

"I want you to turn around and squat over top of my dick. Hold it with your hand between your legs and ease yourself down over it. This is not unlike cowboy and you can control the rate of penetration. Squatting allows you to open yourself up like you do on the toilet. It's much easier."

She did what I told her, and I could feel her sitting down on me, I could also see what she was doing from my vantage point. She managed to balance herself and as I held my erection in my hand, she slid down right over it.

"Slowly, don't hurt yourself, if it hurts stop"

"Oh Rachael, it actually feels good, no pain and it seems to go in so easily."

"Let yourself down all the way and rest your weight on me, then you can come out of the squat and down onto your knees."

She sat down on me, rolled to her knees and began to pump me in and out of her new ass pussy.

"Jenny, lift off now and turn around to face me"

"Ok"

She lifted off and I looked to make sure there were no surprises like shit or blood on my dick. She turned and squatted again and this time it wouldn't go in.

"Rachael, it won't go in like it did before."

"I told you that angles were important, if you try to push the dick thru the tunnel and it's not straight it won't go in and can be painful if forced. That's why you must control the initial penetration. Adjust your body now to align yourself so it will go in. The approximate angle is a direct line extension from your back bone."

She moved around, lifted up and down, and worked to find the right angle. I just lay there holding my dick trying to give her a good target. She finally leaned back far enough, with her hands on the bed behind her and her feet forward of my hips and I slid into her easily. She was doing very well for the first time.

"Good girl, now you can sit up, get back to your knees and lean forward. Once it's in it's much easier to move and get comfortable."

She sat upright and cupped her breasts in a typical cowgirl position only the cock was in her ass not her pussy. Now, she was all smiles.

"This actually feels really good," she said as she moved around on top of me, pushing up and down to stimulate both of us.

She leaned forward too far, and I popped out of her and she frowned and proceeded to put it back in. It was much easier now since I had penetrated her three different times. Her anus had relaxed a bit and was allowing entrance.

"Are you ready to fuck now?" I asked her.

"I thought we were fucking," she said.

"No baby, this is practice."

"Oh, you say the nicest things."

I flipped her off me and put her face down in the bedcovers, rolled up on top of her and attacked her very round bottom.

"Lift your hips up off the bed."

I straddled her as she lifted, and I slid right in her now soft anal opening.

"OOOOO, that's good," she exclaimed.

I slapped her ass cheek and started to fuck her really hard and fast, "you like that bitch?" I said. "You want some more of big daddy?"

I was ramming her hard for a minute or so and she was doing well for the first time. I had to slow down, or I was going to cum, so I eased up and just stayed inside her for a bit.

"Are you ok," I asked, breathing very hard.

"Oh yes, it's wonderful, I never knew it was going to be so good."

"We need to look at some other positions before we quit so be still while I pull out and roll off."

I pulled back and stood at the edge of the bed, checked my dick and everything looked pretty good. I leaned over and spread her cheeks with my thumbs and looked to see if she was ok and she was. No blood or mud.

"Jenny, the classic butt fuck position is doggie style. I don't think it's the most comfortable for the bottom but it's easy for the top to control things and it's more comfortable for him. Don't let a stranger start you this way, you must remember if it's wrong it will hurt. Move to the edge of the bed and be on your knees."

She did that and I adjusted her height so that I was in the right position to continue the fuck. Once again, I slipped in easily because everything was lubed and relaxed with her.

"Feel good?"

"Oh yea, really good."

She pushed back against me and we began a fucking rhythm with hard slams. She was getting into it now and I was having a hard time not exploding.

"Jenny, I either have to stop or finish," I said.

"Give it to me, give it to me, I want to feel you cum inside me."

With that little encouragement I started pounding her hard and soon we both had what we wanted.

"Don't pull out, please keep it in there for a bit," she whimpered.

"Okay," and I pressed into her keeping things in place.

Soon I fell out and went to the bathroom, disposed of the condom and took a wet cloth back to her in the bed. I cleaned her bottom for her, and then she sat up looking at me.

"Do you fuck like that all the time?"

"What do you mean?"

"In the ass."

"That's all I have Jenny, no other way for me to fuck."

"I know but that was really different."

"Did you have an orgasm?" I asked her.

"No, but I was getting excited, and I think maybe I could."

"That's good, maybe with a better lover you will. I have had female type orgasms on occasion but it's not easy and I have to be in a certain position and relaxed more than normal. It's pretty amazing when it happens."

"So, you think I will be able to have orgasms while being ass fucked?"

"It's possible, you just need practice and experimentation. It's not the same for everybody."

"Are you hungry?"

"Starved."

"Let's go get some waffles," she said.

"You're on."

We both got dressed and went out to the local Waffle House and pigged out. This was not good for our girlie figures, but we were young and had burned a lot of calories that morning.