We first meet Dr. Sheila Shepherd in Welcome to College IV. At that time she was a freshman at DuPont named Sheila Summers. She was introduced to the story as Stephanie's freshman roommate who immediately hit it off with the girls:
Sheri had moved into the Delta Theta sorority house her sophomore year. That left Stephanie without a roommate and the university had assigned her Sheila Summers, a freshman volleyball player who grew up dangerously close to my parents' house. Sheila was a very tall and athletic girl. She stood 5 foot, 10 inches tall and she had legs that were at once long and beautiful and capable of exerting tremendous power. To call her an Amazon would be a cliche, but she looked like I imagine Wonder Woman would have looked had she gone to college. Sheila was also very intelligent with an SAT score that cleared 1250 and she was also quite easy going and likeable. She immediately fit in with the girls and with her acceptance into the group; Stephanie started hanging around a lot more too.
Sheila really put an end to physical rebellion on my part. She was strong and although she wasn't particularly mean, she had the physical power to throw me around like a rag doll. The one time, I tried her out I quickly found myself over her knees getting the spanking of a lifetime. By the end, I was blubbering like a baby and kicking my legs with each powerful smack. Trying to fight when you're wearing heels and a dress and your opponent isn't, probably isn't a great idea anyway.
Sheila became an integral part of the Welcome to College crew and even gave Kylie his first dildo, which she regifted from a gag gift she had received from her sorority sisters. She seemed to relish putting Kylie in his place:
"Merry Christmas, Kylie!" cheered Sheila, "I got this as a gag gift at the sorority Christmas party. I hate regifting, but it just seemed so perfect for our sissy."
"Thank you, Sheila," I said with tears beginning to form, "It's just such a shock. Even a fake cock, it's just so degrading."
"And you're going to become so good at it," laughed Karen.
When we next meet her, it's in Calendar Girl. She is now presumably married as her surname is Shepherd rather than Summers. She is now a full time professor in DuPont's English department. Brandi mentions her when he apologizes to Jen for being late meeting her at the sorority house:
"I know I'm late," he apologized, "I got held up by Professor Shepherd."
Doctor Sheila Shepherd was a Delta Theta alumnus from the class of 2006. It wasn't much of a secret as she was in old yearbooks and such. She was one of the better volleyball players that DuPont ever had and was all over the volleyball record book and athletics guide. Sheila was also a college friend of Linda's aunt Amanda; that's right, the one who once feminized a sissy maid of her own. Between her experience with a pinup girl of her own from her Delta Theta days and Linda's aunt's maid, she was well versed with feminizing guys. This had to be a very interesting chat.
As a former Delta Theta sister herself, she didn't have much sympanthy for Brandi's tale of being feminized by the sisters:
"What did she say?"
"She told me that I shouldn't try blaming you for something I clearly was enjoying. She accused me of choosing to wear the hair clips to her class to be a clown since there were no Delta Theta sisters there to force me," he recalled clearly upset.
"She makes a lot of sense."
"I don't want to do this."
"Don't argue; just tell me what she said next."
Brandi took a deep sigh afraid to continue, but unable to do anything else with me staring him down, "She said that before I brought any complaints to Dean Morris, I better have my facts in order because she would tell him about my hair clips."
"Well, you should remember that. Now, let's get working on your makeup," I commanded.
Sheila is a very important part of the DuPont community. She is a respected professor who will be featured in several future stories. She can be very tough, as the character of Luke will find out in the story French Exchange. She is his faculty adviser and is not thrilled when he comes to her complaining about his class schedule: