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Prep School Teacher and Lactating MILF

"My husband and I teach at a prep school and I end up being a whore for the students."

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Famous Story

The job market was very tight for teachers when my husband and I got out of college. Ed has an undergraduate degree in history and my undergrad is in biology. We met in a New England college when working on our master's degrees in teaching. We got married right after graduation and were anxious to find teaching jobs to help pay back our substantial student loans after six years of school.

It took us a year to finally find a teaching opportunity at an exclusive prep school in a rural area in Connecticut. The beginning pay was low, but they provided living quarters, and it gave us a chance to earn some income to start our new life and to gain valuable experience. The school also had no problem that I need some accommodation since I am nursing our three-month-old daughter. My name is Lena, and Ed and I are twenty-five years old.

The timing and specifics of that opportunity were astonishing. The school just happened to need both history and biology teachers, because another teaching couple left due to a scandal. I did a little research and found out that it was some kind of sexual scandal, but the details weren’t available. One of the wealthy parents apparently paid everyone off to make the issue go away and keep the details confidential. The head master would not provide any details during our interview, except to say that it was a contractual disagreement. We took the jobs anyway because of our dire financial situation.

The school is isolated on fifty acres of lush forest land and fields. Because of the remote location, part of our compensation includes a small apartment a short walk from the school. The all-boy student body resides in dorms, and most of the teachers and the administrators live on the property as well.

Silas is the head master, and he is a stern and imposing man. He’s sixty years old, thin and has craggy facial features, with a full head of gray hair. His appearance is sinister when you consider that he's six feet and two inches tall and always wears either black, charcoal gray or navy blue, three-piece suits. He has piercing blue eyes that see right through you. He has a great deal of confidence and is commanding in his dealings with subordinates and students, and I was intimidated by him.

The rules of behavior and our classroom responsibilities are clearly stipulated in our contracts, as well as the consequences for any breaches. However, there is one obscure requirement that says we may be asked to perform special assignments for additional pay, that would be contracted separately, and we are expected to cooperate for the advancement of learning at the school. We signed our contracts, not having much concern about that last requirement.

Our teaching assignments were going very well, and we liked the school, but we soon realized that we weren’t making enough salary. It was costly to purchase and maintain the wardrobes that are expected of us, and our expenses for normal living and the baby were higher than expected and becoming onerous. We were falling behind on our student loan payments and keeping our eyes open for other teaching jobs that would pay more.

We spoke confidentially with a couple of other teachers about our situation to see if they could refer us to other opportunities. When school resumed after Christmas break, Silas called Ed and me into his office after class to discuss a special assignment.

Silas said, “Please come in Lena and Ed. I have been receiving very good reports on both of you. The other teachers and students like your pleasant personalities and professionalism, and the testing on your subject areas has shown that you are very effective teachers. And Lena, they said that you also handled that tricky sex education class with minimum discomfort for everyone. That’s why I am sad to learn from talking with a couple of the other teachers that you are thinking about leaving us. I know that the beginning salary levels are not as high as we’d like, but there is a way for you to make much more if both of you are agreeable to a special assignment.”

He paused for a moment and Ed said, “It’s disappointing that those two teachers betrayed our trust to you, but Lena and I like teaching here, and will welcome a chance to make more money.”

Silas smiled and continued, “Don’t be too hard on those who confided in me. We consider ourselves to be a family here, and they're only looking out for you. This opportunity will seem highly unusual to you at first, but please hear me out. For the past two years we have offered an advanced sex education class to juniors and seniors in the spring before the summer break. This class is only available to those students who are at least sixteen years old, and their parents must pay a very substantial, special fee.

The fee allows us to pay the teacher an additional amount. Their payment to us and our payment to you will all be in cash, with no tax consequences, since we don’t want an official record of the class. This class was initiated when several of the wealthy fathers wanted their sons to have some real-world sexual instruction before heading off to college. There were only six boys in the class the first year, ten last year, and nine have signed up so far for this year.”

Ed and I sat there speechless as Silas paused to gauge our reactions, and then he continued, “I want to offer the assignment to you this year Lena, since you are so young and beautiful, and you are also breast feeding your daughter, which will add a new element to the course. If you accept, you will be required to teach the most intimate details about the genitals of men and women, with graphic written descriptions and photos that leave nothing to the imagination.”

“The first phase is three weeks of formal course work in the classroom. During the second phase of the course and beyond, you will strip naked in front of the boys, so they can see your body up close. The plan is to have only two or three boys at a time in the apartment, allowing for more individualized instruction. That will take place in an empty apartment next to yours, since we can’t risk having that activity in the school building.”

His proposal was upsetting enough for me to momentarily overcome my fear of him and I said, “You must be kidding Silas. Do you really expect me to strip naked in front of a bunch of horny teenage boys? I’m not a prude or anything, but that is really asking for trouble. And by talking about the second phase and beyond, that implies there are other phases? What else is there to this, and just how much extra would we make anyway?”

Silas smiled his sinister smile and said, “The amount of extra pay depends on the number of students. The parents of each student are required to pay a fee of ten thousand dollars for the ten-week course. The school will keep one fourth of that amount, and you will receive the rest. So, at this point, with nine boys signed up, you will be making an extra sixty-seven thousand and five hundred dollars.”

Then Ed said, “Damn Silas, that's a lot of money for just posing nude. So please answer Lena’s question. What else is involved in this?”

Silas continued, “That is a lot of money, and you will earn every penny of it. Those fathers want their sons to be able to see, touch, taste and smell all aspects of an adult woman. They are paying an extra two thousand dollars each this year since Lena is lactating, and they want the boys to feed from your breasts. They also want you to fondle and masturbate the boys. A highlight of the class will be you two having sexual intercourse in front of them, so they can see how to treat a woman properly. If anything else happens, that's between you two and the boys.”

“The only requirement is that everyone involved has to get a clean bill of health from our school doctor, since we don’t want any chance of spreading diseases, and all must sign a confidentiality agreement. So please consider my offer and come back here tomorrow after classes to give me your decision. If you decline, I need to make other arrangements.”

Silas likes my teaching skills, but I’m not kidding myself about why I was chosen for this assignment. I am pretty, five feet and six inches tall and weigh one hundred and twenty-five pounds, with straight, light-brown hair and large, jade green eyes. My breasts are normally a firm, round D-cup, but now that I am breast feeding our daughter, they are full E-cups with less than the expected sag for tits that big. My ass is large and a perfect heart shape, but still firm.

We went back to our apartment to discuss Silas’ offer. The idea of doing the assignment was upsetting to me, and although Ed seemed upset too, he was basically supportive of whatever decision I made. He’s never been jealous of me around other men, even when we were just dating, and he has always encouraged me to dress in tight and skimpy clothes, and I don’t think he would have minded seeing me with other men. His dick is a smaller-than-average four and a half inches long and thin, and he's always trying to convince me to fantasize about other men when we're having sex, but I’ve never given in to that. He usually has to suck me after we fuck to give me an orgasm, eating his own cum from my pussy. So, it was hard for me to trust Ed’s input on this decision.

After a long and sleepless night, we decided that I would take the assignment, mainly since the extra money would go a long way to paying off our student loans and making us more financially secure. We discussed that being paid to give those boys access to my body makes me little more than a whore but determined that it wouldn’t be so bad if they just looked at me, touched me, and suckled my breasts, with no sexual intercourse.

Silas was very pleased the next day when we told him that we would do the sexual training for the boys. I was given the course materials to prepare for the first phase and was surprised at how graphic the written material and photos are. The photos showed close-up shots of sexually aroused and wet vulvas, parted labia, lactating breasts, and even internal views of women’s pussies. The male shots showed equally close-up views of men’s soft and hard cocks and various sizes and shapes of hairy, hanging balls. The most titillating shots were of men and women in the sex act, with those penises inserted into the women’s vaginas.

By the time we started the class on the following Monday, there were eleven students, six of whom were sixteen years old, and the other five were seventeen. I have to admit that it was a big turn on for me seeing the looks on those boys faces as we read aloud and studied the text, and then especially when they saw the photos. They were all excited by the depictions of oozing, precum covered cocks, and then the pussies leaking semen and sperm after the women in the photos had been fucked. My pussy was wet the whole time as they stared at me, trying to compare my body to the women in the photos. Most the boys were openly rubbing their cocks through their pants, as if they were daring me to say something about it. I didn’t say anything about it and let them have their fun.

The sexual tension was high as the course work ended, and the boys knew that they would begin coming to the apartment next door to ours, for the nude and hands on portions of their training. During that phase, Ed planned on being in the room with us as much as he could, leaving only periodically through the connecting door to check on our baby. The first two boys, who were both sixteen, came to the apartment on the following Monday after school. We had agreed that the boys could call me by my first name during those sessions.

I was very nervous when the first two boys arrived. It was one thing to teach the boys from books and pictures, but it was another to expose my naked body to them. It also felt funny doing it in front of my husband. I stood in front of Larry and Michael as they sat on the couch, and I slowly stripped in front of them. When my round, full, lactating breasts swung and jiggled less than a foot from their faces, they didn’t hesitate to weigh and fondle them in their hands. Then as both boys leaned in to suckle my nipples and areolas, I continued removing my skirt and underwear.

Ed watched intently and was rubbing his crotch as the boys fed on my breasts and I dropped my skirt and panties to the floor. My pussy was wet and swollen with lust from the reality that I was standing nude in front of two teenaged boys as they fed on my milk. Ed had never sucked milk from my breasts before, and I had no idea how erotic it would be. I nuzzled them with my arms holding their mouths to my nipples, as the smell of my pussy permeated the room. After draining my tits for about ten minutes, the boys pulled back and looked at my totally naked body.

They looked at and sniffed my wet, hairy and puffy labia as I stood before them with my leg spread slightly. Both boys slid their fingers into my wetness and began finger-fucking me. It was such a turn on looking down at those sixteen-year-old boys as they got their first feel of a woman’s pussy. Then the boys started rubbing all over my body, starting with my breasts and even reaching around and squeezing and massaging my ass. They took turns fingering my pussy, using two or three fingers, until I had a mind-blowing orgasm right in front of them.

They were so happy with themselves for giving me and orgasm, and I said, “Thank you, boys, that was wonderful. Now you two stand in front of me while I return the favor.”

Ed moved around to a better vantage point as I sat on the couch nude, and the boys stood in front of me. I alternately unfastened their belts and pants buttons, and lowered their zippers, allowing their pants to drop to the floor. Then I was staring at the almost hard lumps of their cocks and balls in their tight, white underwear. I was pleasantly surprised when I pulled down their underwear, and those big, teen cocks sprung out in front of me. Both boys’ cocks are almost twice as long and thick as Ed’s dick, and I was guessing that both boys' cocks are almost eight inches long, and with big, low-hanging balls.

I took one of their cocks in each hand as Ed pulled his dick out of his zipper and began stroking it. I wasn’t sure whether he was just excited about me holding them, or if he was excited at the size of their young cocks. They were already oozing precum as I began stroking their cocks, and it felt so good to have such large cocks in my hands, after being used to Ed’s little dick. I was so tempted to take their cocks into my mouth, but I wasn’t sure how Ed would react to that, and the boys weren’t expecting that as part of the class.

Being teenagers, and with the excitement of fondling me and having suckled my breasts, they only lasted about three minutes. Both boys began spewing their thick and voluminous teen cum all over my face and breasts. At the same time, I saw that Ed shot his smaller load on the floor.

They were in rapture as Larry said, “Ahhhh, ooooh, oh shit, that feels so damn good. Look at our cum spraying all over Lena’s face and huge fucking tits, while her little-dicked husband shoots his load onto the floor.”

I surprised the boys and Ed when I licked the boy’s cum from my breasts and scooped it from my face and into my mouth, as they got dressed to leave. When we were alone, Ed and I talked about everything that had happened.

I asked him, “So how did you feel about seeing me with those boys like that? Did that feed your fantasies about seeing me with other men? And what did you think about the size of those boy’s cocks? Their big cocks felt so good in my hands, and their big cum loads were very tasty. My goodness, honey, their cocks make yours look tiny by comparison.”

Ed looked a little embarrassed as he responded, “I did enjoy seeing you with those boys, and my goodness, honey, their cocks are so big and meaty. I envied watching you stroke them that way. Tell me more about how their cum tasted.”

I thought that Ed was maybe just a little too interested in the boy’s cocks and cum, but I replied, “Their cum is much thicker and creamier than yours, and it tasted salty and maybe just a little bitter. Those boys were happy being with a woman for the first time, but I can hardly get over the fact that I was able to jack off and eat the cum from boys their age. I was afraid to do this at first, but now I realize what a thrill it is to play sexually with those boys.”

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