My Days At St Mary

This story was somewhat difficult to classify, but I do believe that it fits best with the Mature (May/December) section, particularly the third, final and major part of the story, but also earlier parts as well. However, please be warned that it also does briefly contain other themes and components (e.g., fetish, submission, spanking).

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Victor Wilson had become so terribly frustrated. He had worked quite hard in graduate school. He had studied hard. He got A's in most every class. He had garnered a considerable amount of teaching experience, serving as an Assistant Professor for Introductory Counseling, Research Design, and High School Literature. He had even been given the honor of conducting his own independent course: Psychology in the Classroom. He was going to publish his dissertation in a scholarly journal: American Journal of Educational Psychology. Mind you, it wasn't going to be published within the very best journal of the field. But, still, it was a top-rated journal and the paper was surely to be received as a very well regarded pedagogical treatise on the costs and benefits of the New School method of classroom corporal punishment. It was an innovative perspective that was garnering considerable interest within the field. Victor had even completed an internship with the renowned Mr. Peters at Templeton College, who was perhaps the most visible expert on the New School.

Yet, his attempts to gain an instructorship at a well-regarded, four-year, liberal arts college went for naught. He did get one interview, at Templeton. He was understandably hopeful, given the connections he had established during his internship there. Nevertheless, even Templeton turned him down. He tried for three straight years, which was unheard of for a graduate of Livingston, and rather distressing, if not humiliating. He couldn't figure it out.

His mentor, Professor Henry Desmond, suggested that it was just unfortunate timing. The science of discipline was in its early stages. Only three colleges were even known to be applying the principles to the classroom: Templeton, Abberville (where Victor had completed his undergraduate education), and Livingston, where he was receiving his graduate education. Livingston University was in fact the only graduate level college in which disciplinary studies were being offered. It was a difficult area of research in part because it was at times rather problematic to get the studies approved by the respective college's internal review board. This was why Victor had traveled to Templeton for his internship.

After three years of repeated failure, he considered starting over. Well, not really starting over, not all the way back to the first year of graduate school. But, he could perhaps just alter his field of investigation to something more socially acceptable, more politically correct, more pedestrian. His mentor, however, had another thought, a quite radical thought, and one that just might work.

"Victor, I want you to take a look at this add."

"Oh, Professor Desmond, not another one. I don't think I can handle another rejection." He didn't even like looking at the adds anymore, let alone getting his hopes raised once again, only to be dashed and shattered. It was like being a pauper outside a department store window during Christmas. All that one saw were wonderful things that you could not have.

In some respects, the position sounded perfect. The add read: "Seeking applicants for undergraduate instructor at St. Mary. We are particularly interested in applicants with a specialty in pedagogical principles, notably the science of discipline." My goodness, it would seem to be a perfect match! Drs. Desmond, Mr. Peters, and only a few others were the leaders of the New School. Victor was even publishing in the area. How could they possibly choose anyone else?

But, Victor then read further: "Applicants must be female, as St. Mary is a private college for young ladies."

"Dr. Desmond, this one is ruling me out even before I apply!"

"Victor, you would be a perfect fit for this position and you know it. In fact, they forwarded me this advertisement personally prior to its appearance in The Chronicles, inquiring if I might have someone to send them. You are the one for this job."

"Yea, well, unless you're suggesting a sex change operation, I don't think it's a good fit at all."

He just looked at me, expressionless.

"Dr. Desmond, I'm not going to get a sex change operation."

"I wasn't thinking of that, Victor. I was thinking of something a little less radical."

I had no idea what he was thinking. I just shook my head and shrugged.

"I was thinking, perhaps, that you could pretend you're a woman."

"What?!"

"Sure, why not?"

Dr. Desmond was a pretty radical thinker. I had read his works as an undergraduate and was terribly impressed by his willingness to defy conventional wisdom, to push the outer bounds of social mores, to explore alternative lifestyles, themes, and theories. But, this seemed a bit absurd, if not crazy. "Why not? You ask why not?"

"I think you could very easily pass yourself off as a woman."

"Well, thanks!"

"C'mon Victor, be honest."

There was a bit of truth to that, perhaps even considerably more than just a bit. I had to admit that I was a rather feminine appearing male. Well, maybe even more than that. I was only 5'4'', with quite soft facial features. My voice was even naturally high. I used to be tremendously annoyed with charity cold callers that responded to my "Hello, can I help you?" with "Hello, Mrs. Wilson." My voice was high for a man, but was it really that high? Apparently it was. I had at first corrected them, with evident annoyance added to my inflection, but I eventually just gave up and played along. I would sometimes even suggest that I really couldn't make any donations until I spoke to "my husband."

Dr. Desmond pushed his argument. "I suppose you're too young to remember 'Bosom Buddies'?"

"Bosom Buddies" was indeed well before my time, but I had seen it in syndication. I thought it was pretty funny, particularly as one recognized how far Tom Hanks had come since the days of impersonating a woman.

Peter Scolari though was much more convincing as a woman than Tom Hanks. Actually, my friends had often said that I reminded them of Peter Scolari or, when they wanted to tease me, that I would be even more attractive than Peter Scolari. "You want me to be another Hildegarde, Dr. Desmond?"

"Sure, why not?"

"Dr. Desmond, that was a television show. It was fiction. This is real life!"

"Son, have you forgotten your abnormal psychology studies? Are you not aware of the transvestites that spend much of their time dressed as women out there in the general public, fooling everyone around them? And, what about the transsexuals? Many of them will spend years cross-dressing before they obtain an operation. I realize that some of them are rather obviously men, but many, and I do mean many, are really very convincing."

He had a point there, but it still seemed awfully absurd.

"What do you think of Miss Lumet?"

"What has this got to do with Miss Lumet?"

Dr. Desmond just smiled, and I quickly got his meaning.

"My goodness, Sonney Lumet is a man?!"

"I tell this to you in complete confidence, Victor, only to help convince you of the actual possibility of pulling this off. She, or I guess I should say he, is a transvestite. He only let me know about it one night when a few drinks released his tongue."

"But, sir, won't they figure it out, through other means? What about the name on my paycheck, my social security number?"

"Sonny has it in his real name, Samuel. Payroll at St. Mary, as it is here, is handled by a private firm, separated entirely from the university. There won't be any chance of cross-communication."

"Health insurance?"

"Handled through payroll, and so again separate."

"ID?"

"That's handled through personnel, along with the registrar office, and other university administrative matters. For that, you can use your 'maiden' name."

"This would really work?"

"Absolutely. Seriously, talk to Sonny if you have concerns. I asked him if it would be alright to inform you of his real identity and he agreed, as long as it is quite clear to you that this is to remain in the very strictest of confidence. He would obviously lose his job if he was discovered."

Victor did speak to Miss Lumet, and was reassured, much to his surprise. With considerable trepidation, and out of sheer desperation for his academic future, he decided to go through with it. Sonny though proved to be extremely helpful in working on Victor's outward appearance, dress, make-up, and mannerisms. "She" also had a number of transvestite friends who chipped in, finding the "extreme makeover, gender edition," to be a fun challenge.

The physical transformation wasn't so difficult, much to the disappointment of Victor. His skin tone was already rather soft. He didn't have much body hair. He didn't even have much of any appearance of an Adam's apple. And, as noted by Dr. Desmond, Victor's voice didn't need any real work. What was most difficult was trying to behave in a feminine manner without acting like a caricature of a woman. Miss Lumet's friends were particularly helpful with that.

Renting the entire series of Bosom Buddies helped with confidence and morale, as well as providing some relaxing levity. Deportment was the most difficult part. It was quite hard to learn to walk in a more feminine manner. Sonny suggested imagining that he was wearing a rucksack that was pulling him back and throwing his chest forward, but not too much to make it obvious. Sitting was easier. "She" suggested that he feel the chair with the backs of his legs, always holding the skirt in position, sitting on the front of the chair and pushing back into the seat with shoulders straight. It was fine to sit against the backrest, as long as both legs were slanting to one side and feet were pointing the same way, with one foot slightly in front of the other. He certainly could never slouch, which was his natural inclination. What to do with his hands was often a concern. Miss Lumet encouraged him to clasp his hands lightly together, at the hem of his skirt. How to walk in heels was the worst. That took considerable practice. He wondered if his ankles would survive.

Victor though did eventually appear to get the hang of it. They ran Victor through a series of exercises and trials, eventually leading to some practice runs at the mall of a neighboring town: shopping for dresses, make-up, and even lingerie. He passed with flying colors. Actually, that wasn't true. There were a few glitches, particularly within the lingerie department, his eyes naturally wandering to the other ladies within the dressing room. But, when it was done it was clear that he could do it.

After one particularly successful sojourn through the mall, Victor was feeling proud of himself. When he returned home to his apartment he paused to admire himself within his bedroom mirror. "Man!" he said, but revised that to "Girl, you are really quite stunning!"

He really was that evening. His lashes were quite appealing, his eyes were large and sparkly, his cheeks were full and flushed, and he had the most engaging, fetching, smile. "You know, I wouldn't mind going on a date with myself," and with that he could feel a bit of swelling within his panties. He was told to always wear panties. There might be occasions, although rare, when his underwear might be revealed, at least for a brief moment, and all might be lost if he was wearing masculine boxers or briefs. If he was going to do this, he should go all the way.

He didn't mind. In fact, on the contrary, it was one of the aspects of cross-dressing that he enjoyed, from the very beginning. It was difficult not to enjoy the feel of the smooth silk or soft cotton of the various panties he had purchased at Victoria's Secret. It brought back memories of when he was an adolescent and he explored the panty drawer of his older sister. Just the thought of seeing girls wearing those sexy, flimsy, little garments brought on an erection, and then actually exploring, feeling and fondling the panties of his sister, knowing where they would eventually be worn, and knowing how upset she would be if she knew what he was doing, well, on occasion he would just have to take a pair back to his own bedroom.

He had never put on any of his sister's panties. At the time he would have thought that to be too girly, too gay. However, now he found it to be rather titillating. And, seeing himself looking so incredibly sexy within the mirror of his bedroom, his face so pretty, his figure so attractive, well, he couldn't help himself. He turned to the side to admire his profile; actually, the profile of his perky breasts. They were not particularly big, but they were very well shaped. Two nice bubbly round boobs. Of course, they were just falsies that he had purchased at an adult shop, but they did look quite real, and quite nice.

He recalled the fantasy he had as a child of waking up one day and discovering that his brain had been transplanted into a woman's body; how much fun it would be to have free, private, and total access to the body of a woman all day long. He could feel "her" boobs as long as and in any fashion he wanted. And, of course, he could explore and finger her pussy hours on end, if he wanted. He could even stick his finger up her butt, and she would have to let him do it.

He had imagined playing with his boobies during classes at school, and perhaps even fingering himself during a class. How many guys wouldn't want to fondle boobs or finger a girl during class? In his fantasy he would return to a male the next morning, but every once in awhile, if he said the correct magic words, he could, once again, transform his own body into that of a lovely woman that would, once again, be all for his own amusement over the next 24 hours.

Well, this was now a pretty good facsimile of his fantasy. As he stood before the mirror, he lightly ran his hand along the curve of his breasts. They were particularly sweet this evening as he was wearing his little hard nipple attachments. Apparently some actresses wear these when the director feels they need to have a good or sustained nipple effect. In any case, they certainly did feel real. His cock swelled within his tight panties as he circled his finger around his taut, perky nipples, his gleeful, naughty feminine grin smiling back at him from the reflection in the mirror, watching the tips of his fingers circling around and around his pointy little nipples.

He grasped his left breast with his hand and squeezed. He felt the soft pliancy of the falsie with his hand, and that was really quite pleasing, but, regrettably, his breast was, of course, essentially numb. He could feel the breast, but not his hand. Still, what he felt with his hand was nice, and the picture of him doing it in the mirror was terribly erotic: his masculine hand grasping, squeezing, the soft breast of the lovely girl in the mirror, who seemed to enjoy any and every thing he did.

He used his right hand to slowly lift up the girl's pretty, feminine, summer skirt; slowly working his way up her thighs, bit by bit revealing the full length of her brown sheer nylons, past the garter belt holding them up, until finally exposing the front of her tight, silk, pink, bikini panties.

He found it to be a very sexy sight, his skirt raised up high, his panties fully exposed, wrapped tightly around an obviously full erection that was so clearly straining against the feminine silk. His dick was clearly much too big for his panties, and the very tip of the soft, purple bulb of his erection was just peeking out over the lacy frill of the panties' waistband. He couldn't understand why he found this to be so sexy, so arousing, but it was clearly a fact and no explanation was really needed. It just felt and looked so hot.

He let go of his tit and used his left hand to hold up his skirt as he lightly caressed and stroked his hard cock through the sheer silk panties.

His dick bulged even further with the touch of his hand, and the full head of his cock forced its way over the top of his panties. He smiled at its boldness, at the contrast of his manly, hard, tough cock thrusting up and out of the panties. No girly panties could apparently hold his hard dick inside. He never felt so manly as he did now, wearing the girlish panties.

He lightly slid his fingers up and down his shaft, admiring how pretty "she" looked: "her" sweet delicate, flowing hairdo, "her" soft fluttering eyelashes, "her" rosy round cheeks, "her" feminine flowered blouse that so nicely wrapped around "her" soft perky breasts, "her" matching skirt raised high to show off "her" pretty pink panties from which thrust his hard, rigid, masculine tool.

He wanted to just strip down his panties and grasp hold firmly on his cock, to beat himself off with the intense urgency that so clearly wanted to overwhelm him.

But, instead, he just lightly caressed the tip of his swollen dick with his fingers, massaging into the smooth, purplish bulb the wet sticky precum that had leaked from his cock slit. He sighed and groaned with pleasure as he watched himself circle his finger around and around the tip of his dick, poking out over the feminine silk and beneath the upraised skirt. He would never consider himself to be a transvestite, but he felt that he now knew the intense pleasure, the luxury, of being so bathed within feminine attire and yet still so boldly masculine.

He groaned and then grunted as he felt the surge in his loins of his orgasm bursting up from his balls. He ripped down his panties with one hand and grasped his shaft firmly with the other, just as his cum shot out from the engorged head of his cock. The cum spurted with considerable force and splatted hard against the mirror, staining the reflection of his panties and dripping down onto his nylons, at least visually. He jerked himself off through the rest of his orgasm, his knees buckling, his head feeling faint as he continued to squirt his load onto the mirror.

As his knees buckled his skirt fell back over his cock. He had tucked it under his elbow when he thrust down his panties but he was so overwhelmed by the orgasmic waves sweeping through him that he could not fully control his body or his clothes. He twitched as he felt the soft fabric gently fall against the sensitive skin on the tip of his swollen bulb and his last few spurts splashed against the delicate thin fabric of the sweet summer skirt, staining the feminine cloth with his hot sticky thick cum. Rather than try to avoid any further stain, he wrapped the fabric tightly around the bulb of his cock with left hand as he continued to jerk his cock underneath with his right, tightly wrapping his cock within the feminine folds of his girlish attire, continuing to spray, gush, and stain the pretty cloth with his manliness.

When he was done he fell to his knees, so weak and exhausted from such an intense orgasm. He was gasping for breath as he lifted up his skirt to inspect its state, and it was indeed a mess, as the front of the skirt was now thoroughly spoiled with a big sloppy, sticky, wet mess, as was his mirror, the splats of cum now slowly dripping down to the floor. He wondered whether he would be a bit self-conscious about bringing the skirt to a dry cleaner. Perhaps he should consult with Miss Lumet about how to best wash such stains out.

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The interview with the Dean of Undergraduate Education at St. Mary, Ms. Lilly Sinclair, went surprisingly smooth. Victor really shouldn't have been surprised, as his credentials were indeed impeccable. "She" was precisely the professor St. Mary was seeking, and they couldn't be happier that she had applied.