The Winthrop Foundation and Winthrop Institutes Explained

Priscilla Gay Bouffant

Explanations, Descriptions, and a Brief History from the Mysterious World of the Cassandra Sisterhood

    On occasion, in a number of my stories where the Cassandra Sisterhood is present, both the Winthrop Foundation and the Winthrop Institutes are alluded to.

    As you may know, The Cassandra Sisterhood, which was the forerunner of all of this, was founded by Ms. Cassandra Winthrop in the late 19th century, in England, during the Victorian age.

    At that time, Cassandra Winthrop had recently graduated from Lady Margaret Hall College in Oxford England. Lady Margaret’s was one of the first two, All-Female colleges in England.

    Cassandra Winthrop had just taken a job as an Associate Headmistress at the college. She was seeing a young man, and madly in love. She became pregnant. She and the boy agreed to be married. However, at the last moment, upon the day of the wedding, the young man left her pregnant, at the altar.

"Easter Couple" by Joseph Christian Leyendecker

    She was devastated but not defeated. She would of course have the child, Lucinda, and raise her. She would also exact revenge on the young cad in the most unusual manner. She knew of an aggressive, very early stage, feminist Barrister. Cassandra’s Barrister knew of a like-minded female Justice.

    A law suit for “Breach of Contract” as well as criminal charges for Fraud, were brought against the young scoundrel. The lady judge found 100% in Cassandra’s favor. In Lieu of a substantial sentence for fraud, along with the appropriate fine, as well as a hefty settlement for the Breach of Contract suit, the Judge offered the young man a unique form of probation.

    “For two years probation, you will be under the personal Wardship of Ms. Winthrop and whomever she assigns to supervise you. During that time you will be dressed, coiffured and be made to look and act as a female maidservant. Otherwise you may spend two years in confinement with the considerable fine and financial compensation for Ms. Winthrop,” The judge said.

    The frightened young man took the probation. He was enrolled in charm, hairdressing and cosmetics classes at the Lady Margaret’s Annex and given the feminine name of Minerva. Then he was assigned to the most demanding Sorority as a Ladies’ Maid. With Cassandra having the child she could hardly be expected to do more than check up on “Minerva” from time to time.

    But once Lucinda Winthrop was born and Cassandra was resettled in her quarters as Associate Headmistress at Lady Margaret Hall College, “Minerva” the sissy maid moved in with her new Mistress, Cassandra Winthrop. 

    For the next 18 months, Minerva served as housekeeper to Ms. Casandra, and Wet-Nurse, baby sitter and Nanny to Lucinda. In fact, when Minerva the Sissy Maid was told she was free to go, she cried her eyes out, begging to stay with her Mistress and the young Lucinda.

    It seems that “Minnie” had fallen in love with her Mistress Cassandra, in a nearly worshipful way. And she adored Lucinda as if she were Lucinda’s Aunt or Mother. “Aunt Minnie” wanted to help rear the child. Cassandra thought things over. 

    She took counsel with the female judge, the college headmistress, the lady barrister, and several other ladies that had already begun to form the nucleus of what would become the Cassandra Sisterhood. “Minnie” was no longer the only Sissy Maid present at Lady Margaret Hall College, either. 

Victorian Era ladies "enjoying" the company

of each other after the men in their lives left 

them at the alter.  

    These Victorian Ladies now had a number of Sissies flouncing around waiting hand and foot on them. Cassandra Winthrop made a decision. She would marry Sissy Minerva in a secret Lesbian Ceremony, conducted by Judge Angela Collins, who would become the very First High Priestess in the Cassandra Sisterhood. 

    Cassandra knew she would soon be a busy women. She wanted to bear no more children. She was more than satisfied with Lucinda. If anything did happen she would simply adopt. Minerva the Sissy Maid was gelded, just as any pony might be. When Lucinda was sixteen she was told just who “Auntie Minnie” was. She shrugged her shoulders and helped her mother and the other Cassandra Ladies with their work. 

    By the time Lucinda graduated from College, there were numerous Chapters of the Sisterhood throughout England and the “Movement” had reached France. It would soon be spreading throughout Europe. Lucinda said, “Mother, we need to start a school for Sissy Maids here in Oxford.”

    As Cassandra Winthrop was now Headmistress of Lady Margaret Hall College she took a portion of the endowment and opened the first “Winthrop Institute,” and began training Sissy Maids. Lucinda decided she wanted to have two daughters. She appropriated one of the newest and prettiest sissy maids, “Dolly”  from the school.

    Lucinda and “Dolly” were married in the same sort of Lesbian union that Cassandra and Minerva were joined in. After two children were born, Dolly was not neutered, just yet. One of the children was a boy. “She” was to be raised as a girl named Kendra. “Her” older Sister Dahlia was to be groomed to run the Sisterhood along with the third child, Brittany. 

    It would be Dahlia and Brittany along with their loyal sister and social secretary, “Kendra” that would be the impetus behind the forming of the “Winthrop Foundation.” The Winthrop Foundation was to be the Charitable, Political and Business arm of the Cassandra Sisterhood. 

    Lucinda had informed Dolly, “Whether or not our third child is a girl or boy, I’m having your little nuts clipped anyway darling. If the third child is a boy, “She” will also be raised as a girl. I’ll simply adopt a second daughter.” 

    By the time Dahlia and Brittany had the Winthrop Foundation in full operational order, there were Winthrop Institutes throughout both England and Europe. These wonderful academies now, not only trained Sissy Maids, but were also branching out into the tutelage of “Trophy Brides” and “Trophy Sissies” for wealthy females.

    It would be Dahlia and Brittany’s daughters that would finally bring the Cassandra Sisterhood and the Winthrop Institutes to the America’s. Today, the Sisterhood, the Foundation and the Institutes are all in good hands. Two cousins, Winifred and Miranda Winthrop, the Great-Great-Great-Granddaughters of Cassandra Winthrop are now steering the ship of ardent feminism.

    “Winnie” and “Randi” as they like to be called, carry on the traditions of all of the Winthrop females of the past. The ladies have even expanded the reach of the Sisterhood into India and the Far East. Globally they have set up Beauty Spa’s, Vacation Resorts as well as Clinics for the relaxation, pleasure and use of the Sisterhood membership.

    “Winnie” tells the story; “We want our members to look, feel and know they are female and beautiful. And if they want their Lesbian lovers or their Sissies to look and feel the same way, then great. That’s the purpose of our specially designed Beauty Spas.”

    “If they want their Sissy to have bigger breasts, then the clinics are available. Maybe they want their Sissy to get fixed? Well you know how that goes. Mistress always knows what is best. What if the Cassandra Sister and her Lesbian girlfriend want to be off by themselves?” Winifred asks.

    “Then they book a vacation at one of our resorts and leave the Sissy Maid at home to keep the house spotless and make herself pretty for their return. And why not? We have plenty of Sissies to wait on them hand and foot at the resorts. We even have a combo Resort/BeautySpa and Clinic on the Costa Del Sol in Malaga we are testing out,” Winnie added.

    “Randi” (Miranda) continues; “The place in Malaga is just perfect. The ladies can vacation. If the Mistress or the Sissy need their boobs done, they can. And they they can have a hairdresser from the salon doing their hair a few days later while they are convalescing. Maybe the Sissy has agreed she needs to get completely fixed and become a girl. No problem there, either. Done right in Malaga at he clinic.”

    “We really think these Combination Resort/Spa/Clinics are our future. Right Winnie? Oh I did forget to tell you something. Neither Winnie or I really ever cared for men. But neither of us had really found the perfect Lesbian lover. So we stayed single until last year,” Miranda smiles and looks at Winifred.

    “That’s correct. Then we decided to find the right Sissy for a submissive Lesbian Bride. That was easy. We found a couple of really dumb, doe-eyed beauties, that we knew we could turn into fashion models if we cared to. We had a double wedding and honeymoon. We slept with our bimbos the first night. Of course we were on top,” Winnie said.

    “Then we banged them both silly, in their sissy-ass-pussies, until they fainted. Finally by the end of the honeymoon we knew how to make our perfect world. We found a couple of Lesbian girlfriends to keep on the side. We hired a governess for each of our sissy bimbos. We told each Governess to milk her sissy dry. We had the sperm stored up in a sperm bank,” Winnie explained.

    “Then we had each sissy gelded. Eventually they both begged to have a sex change because they got so jealous of our Lesbian girlfriends. Now the two bimbos still wait on us and all they want, is to get banged with a dildo and eat our pussies. And if either of us or our Lesbian girlfriends want to have a baby, well, we just cash a check at the sperm bank,” Miranda laughs. 

    “You have to wonder if our great-great-great-grandmother ever thought it would get this good?” Winnie asks.

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Thanks for reading, Priscilla Gay Buffont. 

priscillagaybouffant@gmail.com