A Little bit of a pain in the ass, and not so humiliating.

You're not extremely sure that your alright with having sex with Faith anal or otherwise but she does look like she will enjoy it, as well as the fact that Cora and Dzaya who have been with you pretty much since this strange school day started seem to oddly approve as well as Kaylee the school nurse. You look from one to the next, and realize your teacher Faith has the largest breasts of the group but you are not sure if it is because of the breast feeding or not, you are almost embarrassed at the idea of asking her if it is, considering that she is mostly preparing to take your huge dick in her ass it would be silly since they have been topless for so long to bother asking now about something so pointless. So you just move your gaze from one to the next, really looking at them. You notice that your guess at Dzaya's breast size was mostly wrong and even seeing them lose they must surely be a solid C Cup, as you rotate to look at Cora's your pretty sure they are bigger then Dzaya and you wonder if that is one of the reasons Dzaya was so defensive in her pursuit of you simply because Cora's breast are bigger. Your gaze shifts to the nurse and you notice she might have the smallest tits in the room but you also realize they seem the most perky even in comparison to Cora's and Dzaya's breasts. She also has the second largest nipples after Faith's, thou you think Faith's might be larger because of her breast feeding as well.

You are pulled back from your thoughts as you follow Kaylee's movements even thou your looking at her breasts, you look up to see her grinning and reaching into her bag. It seems she pulls out two bottles of lube and tosses one to the girls, along with a small sex toy. She had pulled out, just before you noticed she had moved to the bag. Faith smiles at Dzaya and starts to give her instructions and all though they are close to you can't quite make it out, and since Cora is still between your legs. Kaylee tosses her the other bottle of lube and comes back over to sit down and starts to give Cora instructions, on how to lube up your dick properly.

You hear Kaylee say things like " Safety first and make sure to get it on all of it." You look beside you as Faith gets up to go get something only to come back with a piece of string and a ruler. You look at her funny, and Dzaya are still holding the lube and the sex toy as if she is expecting to have to carry out the task that the teacher had given her. But your not sure if or when that might happen and Dzaya looks on expectantly.

Faith asks you " Please stand up John, I think for practical reasons we should measure your penis before we move on."

You decided if they wish to measure you, its as good a time as any to ask about her breasts, " I was wondering before that, I will stand just give me a second even if I am not sure why. Your breasts, are they bigger from breast feeding? Or the area around the nipple or the rest?"

Faith looks down and adds " A little more weight maybe as they fill yeah, if I need a milking so to speak they are bigger. And as for the nipples and Areola around them, they in deed got darker and a bit bigger. But my breasts have always been a back killer more or less. So large hey tend to be in the way, and well not needed because I can find bras the right size. I often go to get them custom made, because like feet both breasts are not always the same."

Consider this a moment and then add " So one is bigger then the other?"

Faith laughs a bit, as she adds " Only a little, even Kaylee and these two are likely to find one is a little bigger then the other. Or how the breast sits on the chest as they grow or had grown older is off to the side a bit, which is in fact the reason why I get custom bras, because helps to hug the breasts, without pulling and pinching if it was made to fit it the way it has grown."

She raises her arms and turns and puts her arms behind her back and lefts and shifts them a bit and adds " I will let you focus and play with them another time if you like."

You look at her as if she is crazy but you get up anyway, but this forces Cora to move as well, and she did not even get to start putting lube on you but she does not seem to upset. As you stand the teacher reaches down and jerks your cock a few times before getting down and sucking you a bit more to make sure your as long as you can get and as hard as you can get and then brings the string to the base of your dick, and run it up to the tip. She then brings the string next to the ruler she is holding and gasps, but before she has a chance to tell anyone the results she puts the string in a circle around the base of your cock and measure it and then half way up it and does the same and then the head. She has a huge smile on her face after she takes all the measurements.

Kaylee then turns to her friend and says " I was not expecting us to measure it til I gave the first lesson, you little cheat. I was expecting you to ride it without measurements."

Faith nods wickedly to her friend and says " The measurement from the base to the head of his penis, is 11 and half inches give or take. I think if we could get him any more excited then he is already he might gain another 1/4th to a 1/2 an inch. Thou I am unsure if we can manage that. The measurements for his girth was 8 and half inches around, 8 inches at the mid point and 7 and half at the tip. Circumference of about 8 inches around, which means his penis has a diameter of 4 inches. I think that would make for a good dildo anyway we cut it. It also means he is quite a bit bigger then average. So good on you John." Your not sure but after she said it would make a good dildo, the look in both Kaylee and her eyes seem to have shifted a bit not in a bad way just a bit softer then you expected.

Kaylee looks at the two slightly scared 18 year old girls and says " Don't worry girls, the vagina is an amazing organ it can stretch to fit anything with proper stimulation same with the anus. Which is why Dzaya is holding a sex toy and lube and why Cora is holding lube. So if you would sit back down John, we can move on with the lesson before the period of class ends and the students of the second period start to knock on the door expecting to get in." But before she does anything else she looks down into the baby carrier to check on the baby, you notice Faith does the same. You once again are reminded of the school rule that all females must wear a skirt to school staff and students as you sit down and watch as Faith lean forward in front of Dzaya and flips her skirt up as Dzaya pulls down her panties, as your pretty sure she had been instructed prior to the measurement. Cora seems to get upset with you just staring at your teaches ass instead of sitting down, so she pushes you into your seat. And starts to lube up your dick, you feel her hand glide over the tip, and down the back side. One hand on the top one hand on the bottom it feels amazing the lubrication of your prick compared to how there hands felt on your dick earlier without it.

But you watch as Dzaya squirts lube onto the toy, and a bit on her finger and she slowly works a finger in to Faith's ass. Faith lets out a small gasp as the pressure of the finger passes her asshole and enters, you can see her visibly relaxing to allow it. You see Dzaya put a little more lube on her finger and lubing the teachers anus before she starts in with the toy. You notice the toy seems pretty standard like a small purple and white candy stripe vibe, and then you realize it is ironic because Kaylee the school nurse had been carrying it around in a bag.

Kaylee waves Cora up to her lap, for which Cora seems hesitant but because she had finished her lubing of your dick. She complies to the request. Then Kaylee says " Ok, so now that you all have seen that it is important to use safety. It is important to decided how you wish to watch Faith take it. What I mean is she can face, toward John or she can face away from. And the fact is if she faces him he will not be able to watch it enter and exit, only feel it. And it also means that we would have to get off the couch to watch it our selves. Or we can just let her get on his lap pretty much the way she seems to be for Dzaya but replace the sex toy with his dick, and she would end up more on his lap then she is on Dzaya."

Cora nods and looks down as she notices that Kaylee is playing with one of her tits but shrugs and starts to play with one of the nurses tits in response, Kaylee is of course smiling as she has been since you all entered. Which is kinda strange considering her normal school nurse style behavior outside of class. Dzaya on the other hand, starts to feel adventurous and starts to run a hand softly over Faiths, crotch for which she is reward with a light moan. But this scares Dzaya and she stops what she is doing. But Faith looks back over her shoulder and smiles at Dzaya, but you take this more as an offer for you to do something if Dzaya is going to not do it, so you reach over and start to prob at the teacher's crotch with your hand til you find her vaginal opening and insert a finger. You do this slowly, but quickly bottom out. Your teacher lets out a moan and looks over her shoulder at Dzaya who shrugs so she looks over the other one and smiles at you.

Faith finally says " I think I am as ready as I will get, and I will do it this way I think it will be the most entertaining for most of us but me. The only way I can watch his dick enter and exit me is if it is in my cunt and I clearly think the group decided other wise til the next lesson at least."

Kaylee grins at her friend and says " Sorry Hun, your going to have to wait."

Faith sticks out her tongue and says " Bitch." But then smiles at her friend as if to say whatever.

Faith stands up and Dzaya removes the toy from her ass, you spread your legs in a y shape and have her come sit on your lap. Your dick is pressing against her ass, you can feel the heat of her body against your dick. The image of how deep your dick is going to go into her from the back before penetration is a bit of a shock to you and to the two 18 year old girls.

Faith then adds " Don't worry girls, things stretch to fit. And the fact is I feel little or no pain from anal, I just normally don't feel much pleasure when I am with my husband."

Kaylee looks at Faith strangely and says " Your husband never had a chance to come to feeling anything like what your about to experience dear, dear Faith and I hope you will understand the difference for yourself by the end of this."

Faith lefts herself up and pushes your dick down and sits, it pushes out between her legs and she giggles and starts to play with it a bit, she has Cora hand her the bottle of lube and she makes sure there is enough lube on it for her taste even thou it is lubed pretty well. You can feel your dick, rubbing up against the warmth coming from between her legs. It is by far one of the most powerful feelings you have ever felt before, and like so many sensations like feeling her jack your dick genitally with her pussy pressed against it. You just feel you have trouble doing it true justice.

Cora looks down to see, that Kaylee is playing with both of her breasts. And she is starting to feel heated herself, by closer to how she felt when she was sucking on your dick. Thou she is having trouble over the feelings coming from a female, she had always considered herself straight and she is pretty sure she still is but she does not find the touching or kissing of a female unpleasant. Or at least well in the presents of a male, thou this something she is feeling deep down.

Cora refocuses her eyes on the ass in front of you and watches as the teacher pulls off your crotch a bit, and asks " Kaylee, hold his dick still for me, just for a moment?" Kaylee reaches down and grabs a hold of the base of your dick, and with her other hand she aligns it with Faith's asshole. Faith pushes down, slowly and her asshole gives way pretty easy. Your pretty sure it had to do with the prep work with the finger and the toy, but Faith slowly sinks down. She shifts a little from side to side trying to take it all into her ass. You smile to yourself, around the time she is about half way down. You reach out and slap her on the ass, the shock of this event as she was focused on lowering herself makes her slip all the way down the rest of the length of your dick, as she bottoms out on your dick you both grunt out in a bit of pain. You almost feel her weep a bit, from the shock or maybe gasp from having all the air from her lungs your not quite sure.

Kaylee is shocked at this but is still smiling and reaches out to touch her friends shoulder in support, Faith does not take as long as you thought to recover. Faith as soon as she can says " Well, that was a bit of a shock. But other then that, it does feel different. I feel full, I mean I almost feel like I am full in both holes."

Kaylee smirks and says " See, Told you so."

But with Faith bottomed out on your dick, you reach down and pull her skirt off her. You figure it is better then getting it dirty and toss it aside. You then pull her so she is sitting with her back against your chest, and you grab onto her chest and cross your hands across them like an x and kiss the back of her neck. You figure if she is going to let you fuck her in the ass the least you can do is be kind about it, you really did not mean to spook her and her to take the rest of you so quickly. Faith relaxes against your chest, as you play with her tits. And nuzzle your face and lips against her neck and shoulder, and kiss here and there. Faith starts to moan and you really have not started to fuck her yet or her fuck you so to speak since she is in control of the real action. You reach one hand down from her breast down her pretty fit stomach considering she had a baby, you rub your hand in a circular movement. And stop at her belly button, and then move to her waist, as you trace a line from one side to the other with your finger. You then trace your fingers down to her crotch, you run it over the sides and the top. You realize she has a nicely trimmed mound of pubic hair right over her clit, so you work your middle finger between her lips and rub her clit. You are pretty absorbed by your own actions as you feel the others move around on the couch just a bit.

It seems Cora and Dzaya have taken to sucking on Faiths breasts again, and Kaylee got bored and dropped to her knees to eat out her friend. You of course can't see much of any of the actions the girls are doing because your teachers body is in the way, but it becomes clear very quickly that she is enjoying. Her hips start to buck and your dick starts to move in and out of her ass, as her body responds to the being done by the other three women. You grab a hold of her hips, and slowly try to help her raiser her up and down your dick. But as you place you hands on your teachers hips, it becomes clear that your friends Cora and Dzaya, are pressing there face into your teachers tit well wrapping there arms around her. As best as you can tell the two, are holding one and others arms and are mostly going to start lifting the teacher for you. But you can't be sure, As Kaylee licks out her friends very so often she licks your balls as well. The Flesh Pressed to Flesh on all sides of your teacher is becoming a bit much for her and she arches her back to a great that she is resting her head on your shoulder again, in doing this the teacher removes your dick almost completely form her ass only to drop back down it in one swift movement. She starts to thrush about in your lap.

You notice Kaylee take, your teachers hands and place them on her shoulders as she stands up from Faith's Pussy. And has her hug her close. You also notice her give a couple of signals to Cora, or Dzaya. And they begin to lift Faith as you had suspected. Your Faith's arms are around Kaylees neck, and Faith is just making the strangest sounds. You have a hard time making sense of it as a whole, thou you do know she is mostly at least enjoying it. You can feel her anus tightening and then relaxing over and over again as the girls lift Faith up and down your dick. As a little while of this you start to meet the movement with your own thrust, and Faith's body seems to heat up. You can tell the sensation of it even in her ass on your dick. The tightness and the heat and wet and general over all contacted is starting to become to much, and as much as you would love to make this last. You know you can't.

Kaylee seems to notice something in your eyes from over Faith's shoulder and starts to smile to herself, she waves her hands one last time and the girls bring the Faith's asshole so that your dick is just barely in her ass, just the tip. They hold her there, and your starting to go a little crazy with want or need. And start to buck your hips up into Faith's ass as high as you can get it from were you are, this does not work so well so you brace yourself a bit and try that. To find it also does not work, so you put your arms out and touch Cora and Dzaya on the shoulders. As you pull yourself to your feet and drive the cock as hard as you can into Faith's ass, it was not entirely intended. But her ass clamps down on your cock and starts to contract and spasm, your not entirely sure what is going on but it feels amazing. And it is not long before the girls let go of Faith and let Kaylee hold her between her and you. This brings your cock to settle just a little bit deeper then before, and the extra little sensation of the heat and contacted. Pushes you over and her spasming ass milks your balls of all the pent up cum, you have left after the shared blowjob you had earlier.

Faith is just wrathing between you and Kaylee, Cora and Dzaya after letting go of there teacher had moved behind you and pressed themselves into you to make sure you don't fall over. If you had no idea what love felt like before today, you at least got some idea what it might feel like after it. Your also amazed at how long you were able to fuck your teachers ass before you had to cum, even thou you had the blow job. You also realize that if Faith had been facing you instead of away from you this might have been a bit more personal for her and you. And this pains you a little to realize it only after the fact.

Faith stops shaking, and finally lowers her legs from around Kaylee, you figure maybe Kaylee had been fingering her well you were standing up it is hard to know. But Faith finally manages to shake off the shakes from sex in her ass and she turns her head as best as she can over her shoulder and says " You know, as much as I like the feel of your dick in my ass. We might want to clean up soon." As she turns her head to the clock to check the time and says " we only got 10 minutes or so" she then adds " we might want to open a window or get an air freshener in here. Plus you three might want to return to math class before the period is over to get your homework if there is any."

Faith makes a move to try and pull your dick out of her ass, but your still rock hard and straight up. She has trouble getting the extra foot on her tippy toes to get off it, also Kaylee is still in her way. She tries to wave her hand off and get her out of the way but Kaylee grins at her and says " The Anal Sex was not humiliating enough, it pains me to have to tell you this Faith. And I do so in good faith. Your going to have to blow the boy clean, I mean the girls are going to have learn about it sooner or later and I know you most likely feel strongly enough for him to go ass to mouth with him. More so after the reaction he just had to what, your 20 minute climax? I think it is only fair don't you?"

Faith looks at her friend a little upset with the suggestion but faintly smiles and leans forward to push her friend out of the way so she can get your dick out of her ass, as she leans forward you watch as your dick exits her ass and a lot of cum starts to leak from it. She looks to the ground in shock, you can tell the other girls are pretty shocked to considering you had cum just 20 to 25 minutes ago in Cora's mouth. Faith turns around sore in the ass, and looks at your cock. It is covered in cum, and lube and as best as she can tell pretty clean. So she nods her head and waddles forward a bit because of the sore ass, it is clear she never had anything as big as you in her ass before. She drops to her knees and starts to the amazement of Cora and Dzaya to lick and suck your dick clean as her ass leaks more cum under her.

Kaylee on the other hand quickly gets a towel from the bag she has, and you start to wonder the reason she carries this stuff around with her everywhere but shrug it off. And watch as she starts to clean up the mess, you also see Kaylee take out an some kind of ointment. And she bends down puts some on her finger and starts to push it into Faith's ass, Faith groans a bit as Kaylee does this. But Kaylee finishes as fast as she can, and stands up and says " Well, that should heal fast. And you should suffer no pain or any kind of side affects." Faith quickly finishes cleaning your dick, and then towels it off just to make sure and stands up. She turns around to say something to Kaylee and you notice her asshole is not gaping or leaking any more.

Faith says " good thing you brought the pain stuff, and tightener with you. I would hate to be leaking into my panties all day, in less it was from my cunt. Then again we can't have others seeing semen running down my leg either. At least for a few days if not a week." She says it with a wink that you and Cora and Dzaya don't see, to Kaylee.

Kaylee smiles and starts to put on her shirt, and says to the Cora, Dzaya and yourself " Get dressed you three, get to your math class before the bell rings I will send some passes to you in the next class, I will need your help to get set up.The rest of the time you three can do whatever you want. Thou I suspect you might want to do your home work, from the class before it before you start to screw around or screw off or whatever the three of you do with your time before the fun starts. Before you leave the class you will need to get your homework assignments, you will still be responsible for them as you would be any other time. Thou I think Faith is not going to give you three any homework. So her class will be the first real break you guys get more or less, thou you will be present for the whole thing. Then tomorrow you guys will show up for the testing that has to be done, in the gym for which we set up for today. And the rest of the time tomorrow you will be aiding me in making sure others keep in order, or giving support to students who have trouble with the tests that they have to under go. You three will be first, and you will be doing it early tomorrow morning before the others have to do it. So you can tell the other students what to expect. I hope that is suitable. The rest will be explained next period as you help me set it up, all gym activities for the most apart will be done outside. In less they are helping set up, which I have not checked."

You shake your head confused of course and look right at the nurse and say " Ok, so I go to my normal classes as I normally would?" Kaylee nods and you ask " And I still have to do my homework? Even thou I get good grades? and doing extra credit by helping out?"

The Kaylee nods again and says " The extra credit, for each of you should end up bumping your grades a bit. So if you had a B+ you now mostly will end up with an A."

You then look at Kaylee and say " All that being lazy to not show up the students is going to go down the drain, what is it with all you teacher trying to me look good? And draw attention to me?"

Kaylee smirks and says " Maybe we saw something, maybe we did not. But you Sir, need to get back to class." You look down and see your still naked, and Cora throws you your shirt and boxers, as Dzaya throws you your pants. And it seems they had gotten dressed well you were making trouble for Kaylee who just took it in stride, you shrug to yourself as you finished getting dressed.

Kaylee looks at Faith as she is about to put her thong back on, a semi-transparent black thong. And says " I think John, Earned this don't you agree?"

Faith looks from Kaylee to her thong, and then at you and smiles and says " If he wants them he can have them."

You shrug, being as you had been raised outside the united states you did not know the custom but surely it seems these two know the score. Cora and Dzaya also look at the teacher funny as she says this but shrug.

Kaylee says " A trophy, it is very common for soldiers or guys in the United States to take a trophy from there conquest. Also in some regards, you might even be able to consider this part of her submission or letter of intent."

Faith looks at Kaylee and says " John, try not to read to deep into it. Kaylee is a little strange, I bet she is not even likely to tell you three one of the most private things about herself even if you asked her."

You smirk at Faith and say " Oh? and what is that? You mean the fact she is a Virgin even thou she looks that hot? Or should I say Technical virgin because she has taken it in the ass a few times?"

Kaylee's face goes pale as Faith smiles and says " Oh, so you figured it out?"

Cora and Dzaya are just looking at Kaylee and wondering how she could still be a virgin, and then you say " Well, the fact she was first to accept the suggestion that I fuck her in the ass, she almost squealed in delight. And then the fact she offered herself to me, in the way she had. Would suggest that she was trying to over come some form of fright she was even being bashful about it. If I am able to recall the interaction as well as I can. The fact she does not want to get close to Mr. Jackson as another give away, it was not just her father who has the issue its her. Also the fact she had the lube and all the other stuff pointed to the fact that for some reason she had her over night bag with her. Or the two of you often mess around in the morning. Which also suggests that you knew this would mostly happen once you asked us up here Faith."

Faith looks at you seriously for a second and then nods but says " I did not really so much expect things to go as far as they had, thou I knew Kaylee mostly wanted milk for her tea. Or at least that is what we have been calling it." As she looks down to check on the baby again, and you realize her daughter has got to be one of the most quite children ever.

Kaylee looks at you and nods and says " I guess we will talk about this later, finished getting dressed." she looks down, so you walk over and kiss her on the cheek.

You then add " The good news is, I got just about the experience you have with this. But it leaves Cora and Dzaya behind me."

Kaylee shakes her head and says " Your experience was there experience more or less, they took part. They understand whats going on , and they even seem to enjoy it."

Cora nods and says " It was interesting to watch what it looked like, I can clearly tell you that it did look fun. And Faith sure looked like she enjoyed it." Faith once again notices that Cora must agree that whatever happen between them left her using her middle name as she had asked.

Dzaya then grins and says " It does look a little scary and there is the fact she has at least experienced before as you had Kaylee." Kaylee nods but just smiles.

Faith then says " Alright, all is in order. Here take this." She runs the thong across your nose to show you it smells like her arousal before stuffing it into your backpack for you. She smiles to herself and says " You hold on to that alright? Maybe I will bring my perfume bottle tomorrow so I can scent it properly for you."

You shrug and return to math in the last few minutes of the period with Cora and Dzaya following behind you, the three of you get your home work assignments and Toshi stops you after class to talk to you, as Cora and Dzaya leave the room as it seems Toshi dismissed the class a few minutes early.

Toshi smiles at you and says " John, did you find the many paths? That one action can result in? Did you go with it or did you resist it?" He looks at you a few moments and then smiles and says " The river pushes but you move like water, you flow with it. But wish to control it." He looks over you one more time and smiles again and says " Very good, you learned the lesson. Don't worry about the homework, I know you have the ability for what the homework covers so don't worry about it, same for Cora and Dzaya. You three learned the lesson that was needed, now you will bare witness to the future as I said." You look at him funny but he bows and says " If only I had learned to do the same so long ago, pity the things I missed things by not noticing them sooner."