I sat behind my desk, concealing the predatory smile that had been welling up ever since the young man had stepped into my office. His name was Calvin Gray, he was twenty, and he potentially faced a sex offender registry sentence. My job as the court-appointed social worker was to evaluate him and make a recommendation to the judge as to the proper punishment.

“Cal,” as he asked to be called, was potentially handsome in a nerdy, andro kind of way. He wasn’t a “Chad” as incels termed a regulation stud-muffin—honestly, I preferred the more intellectual types over the frat-boy cavemen—but like many incels, Calvin’s grooming and social comportment were definitely lacking. Staring at my breasts from almost the moment we met—they aren’t overly large, nor was much cleavage on display—it was clearly a habit for him—was a big tip-off.

“So you know why you’re here, right, Cal?”

“Uh, yeah Miss—er, Ms. Masters, ‘cause of the deepfake.”

He’d taken video of a young woman in one of his classes and used an app to marry it to hardcore porn footage of a cheerleader getting double and triple penetrated, then getting facials from all three. Then he’d posted it online. He’d been sloppy and the campus police traced it right back to him. He was looking at a felony charge.

“We’re just talking socially here. Call me, ‘Kathy’ if you like.”

“Okay, Kathy. I know I shouldn’t have, but she made me so mad.”

“Must have been pretty bad, what she did.”

“She humiliated me. She fu—she teased me and lured me and…”

“A lot of young women do dress provocatively, don’t they?”

I purposefully put a note of disapproval in my voice to get him to drop his guard. He wouldn’t speak his mind unless he thought he had a trustworthy, sympathetic ear. In my opinion, women have the right to dress within the limits of indecent exposure laws as long as they were willing to get hit on—but not to be stalked, assaulted or turned into deepfake porno versions of themselves.

“Hell, yes! It’s like they’re cockteasing on purpose.”

“It seems like every year girls have less respect.”

In reality it had been only six years since I’d earned my MSW, and young women really weren’t that much more exhibitionist than when I’d been a UCLA freshman twelve years ago. What was different was guys spent more time watching their phones and game stations and porn than talking to actual women. They thought the girls getting DP’ed and faces full of semen represented most young women.

Calvin took the bait. “Exactly! They act like sluts and then give us blueballs and laugh right in front of us. Practically.”

I took a thoughtful tone. “I suppose… a girl gives you a boner on purpose, it’s kind of… her duty to do something about it.”

“I know! Right?!”

“You must have felt so humiliated.”

“Finally somebody understands!”

“So that’s why you deepfaked her—to teach her a lesson.”

“I just wish I could have seen that cunt’s face when she saw what I did,” he smirked. He looked for my reaction. His smile died. “What?”

“Just supposing, Cal. What if a gay dude got a boner looking at you? Wouldn’t it be your duty to, say, blow him?”

“That’s fucking gross. And it’s not the same thing at all. I’m not into dudes, so his boner is his own problem.”

“And if a woman isn’t into you? Still her duty?”

“It’s still not the same thing. Faggies are, like, gross!”

“You’ve missed the point of the question. Just because a woman turns you on, why does that mean she must be attracted to you?”

He got the point and then got huffy. “Why wouldn’t she?”

I laughed so loudly, he actually blushed. “Are you kidding? You’re like the poster boy for desperate incel fashion, even without the creepy Columbine trenchcoat and that gamer T-shirt.” I wrinkled my nose. “How long since you washed that thing? It smells almost as bad as your breath. That’s just style and grooming, Calvin. Want to know why girls avoid you like a steaming pile of shit?”

Tears stung his outraged eyes as his mouth worked desperately to get a word out. Finally he managed, “You! You have no right. I don’t have to sit here and take this!” He stood.

“Sit down, little boy,” I snapped.

“No. And you can’t make me!” He started toward the door.

“That’s true. But I can make sure you go to prison and get stuck on the sex offender registry.”

His hand froze on the doorknob. “You… you can’t do that.”

“Turn and look at me, Cal,” I said gently. I loved how he so slowly, grudgingly complied. “My report to the judge will determine how you will be punished. If you don’t do everything I say, you can go to jail for a year and the registry will ruin the rest of your life. The probation officer told you everything that entails. Your parents live near a school, so you would have to move out, probably to a halfway house with other sex offenders. And everywhere where you move, for the rest of your life…” I trailed off as he started crying. Perfect.

“I’m sorry, Ms. Masters. I’ll be good. I promise!”

I explained that I another option for my report. Instead of the terrible things I mentioned, he could be referred to eight weeks of counseling to help channel his urges into healthier things. Once he had completed the sixteen sessions—twice a week—he’d get off with a simple malicious mischief charge and a year of probation.

“Does that sound better to you?”

“Oh hell yeah! Sign me up!”

“It’s not quite that easy. I still need to evaluate you. I can’t refer a client who isn’t willing to comply with treatment. If you’re inclined to be rebellious or anything other than a hundred percent cooperative…”

“I will do anything you say,” he blurted.

“Good. Go lock my office door.”

“What did you say, Kathy?” His tone was as shocked as his look.

I stood and leaned over my desk, looking down into his eyes. “You will now call me Ma’am until I order otherwise. Understand?”

“Order?” he asked with a note of outrage.

“I see you’re having trouble with rebelliousness. Lack of ability to cooperate. Do you know what happens to boys like you in jail?”

He practically knocked his chair over on his run to the door. He was so haunted that when I ordered him to strip fully naked, he hesitated but a single second before shucking off everything but his boxers. I quickly saw why. They were tented with a smallish boner.

“Those too. I know you have a stiffie. Don’t worry about it.”

He pulled off the striped shorts and tried to stand to one side until I motioned him to face me. His cock was so hard it pointed right at the ceiling. It was just about average length: a little less than five inches. He blushed bright red as he tried to conceal it with his hands.

“Now the little dick jokes start. Right?” he said sullenly.

“You think you have women all figured out, don’t you?” I said coolly. “We’re all Staceys or Beckies, interested only in a guy’s looks and stud status. The ‘manosphere’ mentality has you all turned inside out. Well, I’m going to cure you of it.”

“You? … Ma’am?”

“That’s right. I do counseling too. And a few other things on the side as well. Lucky for you. Now stand in front of my desk.”

I retrieved a big, cafeteria-style plastic tray from a cabinet and put it on the desk just in front of him. I told him lean over my desk with his hands spread on the sides of the tray, so that his dick was pointed at it. Finally, I had him spread his feet wide apart, cracking his buttcheeks and exposing his tight little asshole.

“I’m afraid, Ma’am.”

I favored him with a small, cordial smile as I removed a box of pink latex gloves and a bottle of sex lube from my desk. “There’s no need to be, Cal. You’re about to learn something about yourself that… I just know you’re going to like.”

I circled around to the front of my desk and paused to admire his ass, so smooth, plump and girlish. If he ever was sent to jail, he would get turned out as a sissy on the first day. I fondly patted his butt, earning a whine and a shudder.

His breath picked up as I pulled rubber gloves on both hands and squeezed several ounces of slick, silky lube all over his shapely butt. With both hands I thoroughly rubbed it all over both of them, coating them and the crack of his ass so thoroughly.

“Hold on tight, Callie,” I coaxed.

“What for?” He whimpered.

“I’m going to use a bit of force here.”

Thinking I meant to invade his butthole, he immediately tensed up. Deeply I massaged his sweet, young ass, from the small of her back to the bottom of those jiggly globes, always gliding a hand between those cheeks and pushing firmly against his tightly puckered asshole. Within a minute his tension bled away as he relaxed into my hands.

I concentrated more on his asshole, swiping one hand then another past it as I kept up my wider sweeps, slowly narrowing them until only the cleft and his anus got massaged. Tiny whimpers and the feel of his anal sphincter yielding said it was time.

With the pad of my index finger I circled his butthole with mounting pressure while still doing lazy sweeps of his buns with my free hand. The pucker got more and more loose until my fingertip started to slip past the ring of muscle, while his whimpers became tiny moans.

Subtly, slowly I eased my finger into his asshole: first knuckle, second knuckle… his sounds of pleasure increased, the further I went in until my finger was well into his rectum.

“Do you like my finger in your boy-cunt?”

And just like that his finger clamped down. Hard. “No, Ma’am! That… it’s weird. It’s totally fucking gay! Please take it out!”

“I’m a woman. How can it be gay? Besides, you’ve been loving it.”

“I… I haven’t.”

“Oh, no?”

I slowly slid my finger out, which caused him to relax. I slipped it right back in, angling it to graze his prostate. This time he moaned. The effect of him was huge, especially when I locked my eyes with his. His gaze had a pleading look to it. He wanted me to continue.

I slid in a second finger, which he immediately accommodated like he was used to it. I made it a point to keep teasing his prostate.

“Tell me, Callie, honestly. It feels good, doesn’t it?”

“Y-yes, Ma’am.”

“And you want more, don’t you?”

“Ohmigod! Yes, Ma’am.”

Prostate fluid dripped from his rigid cock onto the plastic tray. That tray would be splattered by the time I was done with him. I pulled my fingers from his asshole and stripped off the gloves.

His eyes followed me to the far side of the desk. He gaped in surprise as I unzipped and stepped out of my knee-length office desk. Now I wore only upscale bra and panties, and he was mesmerized by the sight. His eyes filled with hope that perhaps he’d get lucky.

The look on his face changed after I unlocked my bottom desk drawer and pulled out a nine-inch dildo and a harness. I could see he was dying to protest, but the fierce look on my face told him not to protest. However, his boner hadn’t gone down at all.

“This is the final test to see if I will take you on as my therapy patient. If you please me, you have a good shot at misdemeanor: no registry and no jail time. Okay, Callie?”

“Yes, Ma’am.” His voice was sullen, resigned.

I was tempted to make him suck the dildo to lube it, but it was too soon for that. I coated it with lube, got behind him, and gently eased it all the way into his asshole. His satisfied groan lit me up inside. Slowly, I slid in and out of him, cupping his girly ass as I did so. I was getting hornier by the minute.

So was Calvin. Perhaps unconsciously, he pushed his ass back to meet my dildo thrusts, which became less gentle each minute. I angled the toy to directly stimulate his P-spot. If I could give him a prostate orgasm, he’d become helpless, bisexual jelly in my hands.

* * *

I can’t fucking believe this is happening to me!

From the moment I walked in here it was like one shaky minute to the next. All I knew was I’m meeting some kind of counselor the judge sent me to and that deep shit—sex registry bullshit—could happen, so of course I’m nervous. Then it turns out it’s this Stacy with a smokin’ body under that office dress, who first seems all understanding. And now I’m bent over her fucking desk!

I was so confused! My balls ached so good when she took off her dress—total porn-star body—so I know I’m not gay. But why did her fingers feel so good up my ass? And now this! I’ve heard of this. She’s pegging me! This hot almost-MILF is fucking my ass with a strap-on dildo and my dick and balls feel like they’re going to explode!

“Please don’t do this to me!”

“You said you like how it feels. That you want more of it.”

“Just because it feels good… I don’t see how it isn’t gay!”

She slowed her strokes but kept the depth, making the knot in my groin get even bigger. “My last boyfriend in college was varsity sports, and he loved to have his asshole played with. He ended up leaving me for what you’d call a ‘super-Stacy.’ They have two kids now.”

My head spun. I said, “No fucking way,” even though I knew she was definitely telling the truth.

“Yes, way,” she grinned at me. “And you. Know. It!”

She jabbed me hard with each word, causing my nuts to swell. I knew I was about to cum and no hands had touched my cock at all. Fuck—I was about to cum really hard!

I tried not to think about how good it felt: that rubber dick that looks just like a real one, sliding deep up into my asshole. The hot and dirty feeling of it pushing through my rectal meat, sending a thousand tingles through me—especially into the whole pit of my groin, my nuts and my cock. And now it was like my balls really were exploding!

“Oh my god, god, oh my god!” I cried out as it all clenched as I shot my load into the tray on her desk. The ripples of pleasure ran through my whole body and almost caused me to fall face forward on her desk.

I had cum harder than I even had in my whole life.

“Feel good, baby?” she purred.

I was so dizzy I could only groan for an answer. I looked back into her eyes, which blazed with joy, lust and dominance. I only then just realized I’d lost my virginity… but I was the one who got fucked. My eyes filled with tears that I couldn’t help.

“What’s the matter, baby?”

“What you just did.” I couldn’t admit what I just thought.

“You mean, me taking your virginity like you were a girl?”

I felt sick. “You don’t need to rub it in.”

“Why should you feel bad? That’s how male sexuality is wired. Your orgasm was natural and you’re still recovering from it. Even Chads enjoy this.” She patted my shoulder.

I moaned loudly when she slowly eased her dildo out of my ass. My dick was still rigid and the anal stimulation sent electricity through it. Only because she was a MILF, and because she was being sweet, this situation didn’t freak me out as much as it should have.

“I’m taking you on for counseling,” she said. “Put your clothes on and we’ll talk a little more.”

“Thank you, Ma’am,” I sighed.

Only when I straightened up did I see how much cum I’d shot into the tray. There was enough to fill one of those big shotglasses. I was oddly proud at how much I spurted. It was the most jizz ever. My balls ached so intensely good. And my dick was still rock hard.

My pride, my head was telling me this was the most awful thing in the world. I should hate her for doing this to me. But as I watched her step that juicy ass of hers into the dress and saw those epic tits in that wispy-thin bra—and knowing she was going to help me get out of really bad trouble—I could only be in awe of her.

Besides, you didn’t have a choice, right? She was just trying to make some point with you. She thinks she’s trying to help you. She—

“Come have a seat here with me, Cal.”

She was on a small sofa, patting the cushion behind her. She hadn’t buttoned up her blouse fully and was showing max cleavage. I nearly tripped going to the sofa, my eyes were so locked on those glorious boobs of hers. Only when I sat down did I tear my eyes away.

“Woman Lesson Number One, Cal. When a woman purposefully displays her body sexually, then it’s okay to stare. It’s nice if you’re speaking with said woman that you look into her eyes like she’s an actual person. In other words, even if a woman dresses like a sex object, it’s still a good idea not to treat her like that’s all she is.”

I held her eyes and nodded. “Yeah. I get you.”

“Remember when I asked if you want to know why girls aren’t into you? It’s the same reason they’re turned off by most guys with an incel mentality. Any guy who thinks they’re owed sex, who only see women as tits, pussy, mouth and asshole—most women can sense that. They’re not porn stars, they don’t want to be looked at like they are.”

 “I guess.”

She handed me a business card. “Here’s my private office. Be there at four tomorrow. Be prepared to stay for two hours. Bring $160, cash, check or credit card.” She held up a hand to cut off my protest. “You’re getting a discount, Callie. My private clients pay $100 an hour.”

“Thanks, I guess.”

“I promise you’ll be thanking me a lot more. See you tomorrow.”

My dick stayed hard in my pants all the way to my car.

The next day I showed up at a medical professional building, the kind that has doctors, dentists and shrinks all under one roof. Kathy’s office was big, with a large wooden desk, a long leather sofa, three big, sturdy armless chairs, and a strange piece of furniture that looked like a cross between a gymnastics horse and a sawhorse.

No sooner had I taken a seat on the sofa than she locked the door and stepped out of her dress. I gasped at the sight: she was dressed like a dominatrix with the garterbelt and stockings and high heels. Her bra had the cups cut out so they propped up and display those luscious tits and hard nipples. And she wore no panties: her pussy was nude and she was standing in such a way the glistening labia were split open.

“What… what is this?”

“It’s the start of your training. You’d like to jerk off, wouldn’t you?”

“I want to do a lot more than that!”

“No matter what you do, you’ll need to take your clothes off, won’t you? It’s only fair since I’m naked here.”

Thirty seconds later I stood there, bare-assed, my wang throbbing. “So now we’re both naked. What’s next?” I grinned.

“I think you best sit down for the next part. You’re in for many surprises today, Callie, as you’re already seeing.”

“I can’t wait!”

She turned on a big flat-screen TV on her wall and plugged in a thumb drive. A few remote clicks later and I was seeing the desk in her court building office. Then I saw a nude body from waist-down walk up to the desk and the plastic tray slide in front of the guy’s hard dick, and I knew it would be my face when I bent over.

“You taped it?” I gasped.

“Keep watching.”

Somehow she had the camera angled just perfectly to capture all that happened to me and showed nothing of her face. I felt sick as I watched my ass get finger-fucked, then dildoed and that massive cum. As awful as it was to see, there was a tingle in my cock and balls.

“Imagine that on Reddit in all those manosphere groups. And all the amateur porn sites. Do you want to imagine that?”

“I’ll tell. I’ll tell on you.”

“No you won’t. Because the only way they might even slightly have a chance of believing you is if I do post this wide. And you’d never let that happen, would you?” She giggled. “Oh my goodness. You’ve got a boner, don’t you, Callie? Being powerless to a woman excites you!”

“Why do you keep calling me that?”

She sashayed to her desk, grinding her sweet ass to tease me, and bent over to reach into a drawer. Her legs were spread wide enough to reveal her pussy and her asshole. My cock started doing push-ups. Then she pulled a lacy, pink bra and panties out of the desk and tossed them to me, ordering me to put them on.

“Right fucking now! Or I put in my report to the judge you were belligerent and hostile and should be sentenced for the sex-offender charge. It’ll be with you the rest of your life.”

“No! No, please!”

“C’mon Callie, put them on. You’ll love how they feel on you.”

I don’t know why, but they were exciting to wear, especially the panties. My hard cock stood out in the satiny fabric and precum soaked through. When she stroked my ass through the panties, my dick and balls ached so much more.

“I knew you’d love them, Callie. Time for your next surprise! The amazing Esmerelda. Wait until you see!”

She knocked on a door on the far wall. In came a total Stacy of a tall woman: perfect tits and ass in a miniskirt and bare-midriff top. Kathy had me kneel on the floor, my boner tenting the panties. I felt ashamed to have such a hot chick see me like this, but then I saw that it excited Kathy somehow. And it clearly excited this Esmerelda.

“Go feed her, Esmee.”

This puzzled me for a moment until the tall, blonde babe stepped up in front of me and stripped off her miniskirt. There was a huge bulge in her panties. She flopped out seven flaccid inches. It quickly grew to ten, when she began stroking it.

She?! He?! … She?

I was in shock. Sure, I’d seen enough glimpses of trans porn—I never jacked off to it—but to see a total Stacy with a huge dick right in front of me freaked me out and fascinated me at the same time. It was hypnotic, right up to when she-he smeared precum on my lips.

I started to get up, to get away, but Kathy was standing behind me, ready for this. She held down my shoulders, keeping me on my knees. She hissed that all of my worst nightmares would come true if I didn’t open my mouth and start sucking.

“Please, Kathy,” I cried. “Please don’t make me suck his dick. I’ll let you fuck me all you want! Lick your asshole, even!”

“First—you will call her ‘she’ and ‘her’ and you’ll think that so you don’t let a male pronoun slip out. If you do, I’ll punish you bad for it. Second, you’ll do everything I tell you to do. Without hesitation!”

“Don’t worry baby,” the tranny said in a sweet, girlish voice. “I’ll be so gentle with you. I know just what you’re going through, and you’re going to love this. I swear.”

“That’s what I’m afraid of.”

“Suck. Her. Cock. Final warning.”

I opened wide and took her cockhead in my mouth. It was so soft and warm. It pulsed on my tongue, exciting me in a way I didn’t fully understand. The taste of her precum turned me on. Soon I was sucking her dick with abandon. After two minutes I didn’t want to stop!

 Kathy had us change positions so I was on all fours, sucking dick, and she was behind me, pulling down my panties and lubing up my asshole. For the next half-hour I sucked cock while Kathy worked on my asshole: one finger then two then three. At fifteen minutes she had her whole fist deep up my asshole when I kept sucking trans cock.

“Mmmmm,” Esmee muttered. “I could cum any time. Would you like me to cum in your mouth, Callie?”

I was in rapture from being fisted and from tasting and loving her cock all this time. There was no way could avoid the truth I was one of those bisexuals, and it turned me on. What a perfect way to prove to myself what I really was.

“Oh, please yes, Esmerelda! I want to drink your cum!”

I opened wide and looked on with desire as she beat that cock hard and pointed it at my lips. I whimpered with pleasure as hot, thick spurts of tranny jizz shot all of over my lips and tongue. Kathy chose this moment to batter my prostate with her knuckles, giving me a P-gasm!

She gently pulled out of my asshole while I sucked the rest of the jizz out of her cock. I lay there on the rug and looked up at both of them with such desire. I asked what was next. It turned out that Esmee was a porn performer and could always do a second load.

“She’s going to fuck me?” I asked hopefully.

Kathy took a knee beside me as I knelt there in her bra and panties. “Yes, she is. And… I’m really into you, Callie. More than any other guy I’ve had in here like this. I want to do something special while she takes your true virginity.” She kissed my lips. “How would you like to lick my pussy while she fucks you?”

I don’t know what excited me more: the sweet taste of her vaginal juices or being fucked by a chick with a dick. I just know it was the best half-hour of my life up to that point.

The second hour brought in guys, some real Chads, whom I gladly sucked off and took up my sissy ass. All in, five guys had my hips and lips during those glorious sixty minutes. In the space of two hours I had abandoned everything I thought I knew about sex or labels or anything else like that.

My hots for Kathy proved I wasn’t quite gay, and over the next two months I worked as her receptionist. We talked a lot about male-female relations and she helped me work on interactions with women. The last thing I didn’t need as much help with any more. Now that I knew what it was like being a sex object, I could relate.

I have to admit, sometimes I look at transgirls like Esmee and I get envious. Sometime I look in the mirror and see if maybe I could maybe be pretty enough to be a girl like that someday.

One thing’s for sure: if I became one—I’d put out for all the boys!