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Chapter 6

“I want you to feminize my boyfriend,” she said to me with a blunt face.

“I don’t know what you’re talking about,” I said, looking around the room. A few students were still filtering out.

“You feminized my friend,” she said. “He told me that he’d never had a single girly thought before he met you. And it’s no secret that you have your little study. Just make my boyfriend your next subject; I already convinced him to sign up for the class.”

“Are you in my class?” I asked, feeling my skin turning pale. I tried to keep my body calm, not wanting to expose myself through my body language. It was possible that she was a senior psych student who knew more than I would have liked.

“No,” she said. “But he is. So please, do your thing to him.”

“I’m sorry, but I really don’t know what you’re talking about,” I said. If caught, deny, deny, deny. I’d spent a lot of time around lawyers when I was working for the government. I overheard them talking to clients often.

“Okay,” she said. “Well, then maybe I’ll go to the dean and tell him what I’ve heard.” She had a big childish smirk on her face. She was a real brat.

“Who’s your boyfriend?” I asked, biting my tongue. “And why do you want him… to be girly?”

“His name is Christopher. He’s the guy with the messy red hair and the freckles. I’m going to break up with him because he cheated on me, but first I want to embarrass him.”

“This doesn’t sound ethical,” I said.

“Nothing you do is ethical,” she said to me, letting her smile grow bigger. “Look: here’s the deal: feminize him and I keep my mouth shut. I just want to catch him trying on my clothes. I want to post a picture online for all of his friends to see. And then I’ll break up with him. It’s just revenge.”

I tried to talk some sense into her. I tried to calm her down; she was angry, with fire in her eyes. But there was no sense in trying to cool her hot head; she wanted her boyfriend to be humiliated.

And I didn’t want to lose my career. I didn’t need the school launching an investigation; I was already on thin ice after the Tucker incident; his father had lawyers looking into a lawsuit, because he was convinced that the ‘liberal institution of post-secondary education’ was determined to destroy masculinity. If that lawsuit went ahead, and the lawyers were actually allowed access to transcripts, they would see that Tucker stayed in my class until the end of the semester, and they would see that he even earned extra credits; then, they would come to me and ask what the credits were for, and they may even question my past students; if I really did have this new reputation, then I could end up in a lot of heat.

So I promised myself that Christopher would be my final subject.

“Why do you want to talk to me?” he asked as he stepped into my office.

“Just put your bag down, Christopher,” I said. “I want to talk to you about a few things.”

He was a tense person, keeping his arms crossed, avoiding eye-contact. Breaking through to him was difficult. “I want to get a reading,” I said to him after a fifteen minute questionnaire. “But I need you to take off your pants.”

“Not doing it,” he said bluntly.

“It’s just for a reading. It’s for a study.”

“Still not doing it,” he said.

“Christopher…” I said, thinking. “If you participate, I can have two additional credits added to your transcript.”

“Don’t want them,” he said.

I was going to need a new strategy. He really wasn’t going to budge, and I didn’t want to dangle his class grade over his head, because I didn’t want him ratting me out.

So the next day, I decided to wear something a bit more enticing to class. It was a bralette top, tight and almost see-thru. I wore a short skirt. The men in the room noticed; their faces turned red when I looked at them. I made sure to throw glances towards Christopher constantly, grinning when I called on him. I did the same thing the next day: a tiny black mini-dress with heeled leather boots. Then, I wore a tight romper with no bra underneath the day after that. Finally, I called Christopher back into my office. He obliged.

“I really want to get that reading, Chris,” I said.

“I’m not taking my pants off,” he said.

“Please,” I said. I bit down on my lip. “Do it for me.”

“No.”

“I’ll make it worth a your while,” I said softly, glaring into his eyes. I watched as his heart skipped a beat. I watched as he tried to swallow a big lump in his throat.

“What do you mean?” he asked, his voice cracking slightly.

“Just do it and find out,” I said. I didn’t mind using myself as bait. Sex, for me, was a means to an end.

Well, he did it. His cock was half erect when I took the reading. His number was low though: 110. “Do you jerk off a lot, Chris?”

He shook his head. “Never.”

“So you fuck a lot then?” I asked, trying to put on my best seductive voice.

He shrugged his shoulders. “I do alright,” he grinned.

I stared into his eyes for a long, long moment. “Do you want to fuck me?” I sat up on my desk and spread my legs wide, so he could see up the short legs of my romper, to see that I wasn’t wearing panties. His gaze found my pussy. His face darkened and he cleared his throat. “Is that an offer?” he asked.

“It could be.”

“I have a girlfriend.”

“She doesn’t have to know anything. Besides, Chris—it’s just for science. I just want to get some… readings.”

“Can I cum inside of you?”

He was a vulgar young man with a dirty mind. “Maybe,” I said.

“I’ve never fucked a milf before,” he grinned.

I walked up to him and reached down, grabbing his cock. I gently massaged it until it was rock-hard. “If you want to fuck me,” I said, looking down at his reddened tip; it already looked like he was on the verge of ejaculating. “I need you to get your reading higher.”

“What? What does that mean?”

I explained to him how my little machine worked. He was curious but frustrated as I stroked him until he was on the verge of ejaculating. He clenched hard and groaned, and then I let go. “No!” he cried. “One more second. I’m coming!”

“No coming,” I said. “Not until you can get those numbers higher.”

“How long will that take?” he asked with a sigh of frustration.

“A week,” I said. “If you can stop yourself from ejaculating until then.”

“But then I won’t last more than thirty seconds with you,” he said. “That wouldn’t be much fun.”

“If you’d like, we can also address your premature ejaculation problem. That was my specialty for a long time.”

“I’m not a premature ejaculator!” he cried, jumping back from me and stuffing his cock away. “I’m just saying… a week is a long time.”

“A normal man should be able to go a week without ejaculating and still last at least five minutes, Christopher.”

Now, he was getting frustrated. I had to be careful not to upset him. “The offer is on the table: one week of no coming, and you can fuck me however you want to fuck me.”

His eyes lit up. “What about the ass?” he asked with a beaming face.

“Even the ass,” I said.

I was a woman of my word. He managed to get his numbers higher (not quite Absorption levels, but I had to make some progress with him), so I put out when he came back. I let him put his cock into my ass—and he had a very large cock… but he really didn’t last very long. It was a sore next day, but I was getting somewhere with him. “I’ll blow you if you can do another week without coming,” I told him.

And he did it. When he came back, he was in that Absorption Zone, so I took out an old schoolgirl outfit. “Put this on.”

“Hell no,” he said, crossing his arms.

“I’ll suck the cum straight from your cock if you wear it for me,” I said. “It will feel amazing, unlike any blowjob you’ve gotten before.” Then, I flipped down the top of my blouse, exposing my breasts. “C’mon, Chris. Let me suck your big-boy cock.” I pinched my nipples and pulled, and that was enough for him.

He put on the outfit, laughing and scoffing as he did so. I put up my end of the bargain, with my PMR in my hand, taking readings constantly. I kept his numbers high, and even got him to look at himself in the mirror while he was coming. It was more progress, but there was still more progress to make.

It took six long weeks, letting him fuck me, sucking his cock—and each time was hard to get him to get dolled up in various outfits. Finally, I had him steal some clothes from his girlfriend’s closet to wear. I did some hypnosis tricks, complimenting him on how cute he was while I rubbed his cock, programming him to feel immense pleasure from the idea of being dolled up. “You’re so fucking sexy, Chrissy. You look so fucking sexy in that little skirt.”

He groaned and came on my face, ruining my makeup, but we were one step closer.

Finally, near Christmas, he was caught. The video was posted online and I saw it: phone footage taken by his girlfriend. The video started with her creeping down the hall and then throwing open the door.

And there was Christopher, on their bed, on his knees, in a purple nightie and makeup—and with a very large dildo eight inches deep in his asshole. He gasped and expelled the toy from his body. He tried to run at his girlfriend to apprehend the phone, but she managed to shut the door and rush away before the video ended.

The video had lovely quality: good resolution and crisp detail; it was unmistakably Christopher, and he didn’t look half-bad the way he’d done his makeup (I never did his makeup with him, so that was a skill he learned on his own). Christopher never came back to class; he transferred schools after his girlfriend dumped him: his way of escaping the humiliating, knowing everyone in school had seen that video.

And I wasn’t sure how to feel; I’d helped to embarrass a cheater, but the revenge was worse than the crime as far as I was concerned. Enjoying some femininity shouldn’t be something to be humiliated about, and now Christopher was going to live with a lifetime of sexual trauma and dysfunction—and he would probably never truly embrace his feminine side; that had never been my goal as a sexual educator. I believed in the freedom of sexual expression without judgement, be it from right-wing puritans or left-wing neo-puritans—or just the jocks and Stacys in the middle who liked a good laugh.

I felt bad about what I was doing, even if some good had come from it. Lots of bad had come from it; Tucker was disowned by his family and Christopher was chased off to another state.

So I told myself that I would stop… but I didn’t stop. The very next semester, I saw a young man who was the perfect candidate, who, like my first subject, suffered from serious sexual confidence issues. I thought I could help him with his issues while also satisfying that little craving that I had: that desire to turn normal men into sissies.