Chapter 2: Transforming Her Tutor

Chapter 2: Transforming Her Tutor


Fiction by Miss Ivy Omigosh


As I started out to say—you’ll forgive me if I digress sometimes, because since I’ve been living two identities, it’s been happening more often with my confused mind—if you saw me last Thursday night as I walked toward Olivia’s apartment, you wouldn’t have blinked an eye. I wore my usual nondescript male clothes. But as I walked my mind was in total turmoil. I thought about how wearing panties and stockings and bras and heels and slips and wigs and makeup had made me feel so different in my body, and I wondered if anybody on the street could detect, looking at me now in my plaid sport shirt and blue jeans, that my body felt unmoored from reality, that I felt alien in what had been my normal clothes for twenty-two years, and that every inch of me was aching to get to Olivia’s to put on something feminine…so that I could walk and move like the female she had decided I really was. 

I was a psychological and emotional mess. I wanted to cry, really, but I held it in, not wanting to reveal my girlish self on the street. Even bookworms can aspire to a certain machismo…

I got to Olivia’s and went up the steps of the brownstone. She lived on the second floor in the back, facing the yard. She once said when the weather got really warm she was going to make me lay out there in a bikini and get a tan…she wanted to see my slender male body with feminine tan lines. The idea horrified but excited me. I knew that when I did that, I would finally be exposed to the world as the girl I wanted to be. There would be no hiding or pretending then.

I rang the bell in the vestibule and Olivia buzzed me in. When I got upstairs, she was waiting in the doorway, stunning as always in just the perfect skirt and top and heels, with her long hair cascading down to her shoulders and her polished crimson fingernails gleaming as she grabbed me by the face, squeezed my cheeks, and planted a big lipstick kiss on my forehead, like an aunt would do with a silly child, instead of what a girlfriend would do with her guy. The kiss was humiliating but it made my penis leak. 

“Why the long face, Joanie?” she said, as that was my “girl” name. “Don’t you like it when Auntie Olivia kisses you?”

“You’re not my aunt,” I said, pouting, my voice already high and girlish even before the door was closed behind me. I could see her boyfriend Brick standing in the kitchen having a beer.

“I’m better than an aunt,” she said, “I’m your mentor. I’m saving you from the boring self you could have been. Instead I’m bringing out the girl you always kept hidden inside. I found her and I pulled her out for your own good. And you were the one who thought you’d be doing the tutoring, haha!” She laughed and, with a twirl of her forefinger, told me to strip.

“What do I have to wear today?” I said nervously. 

“You’ll see, sweetie.” While I took off my clothes—every stitch—she went into the kitchen and kissed Brick. She ran her hand over the front of his jeans, clearly enjoying the bulge of his huge cock. He was one of the school’s star football players—I don’t know what position, I never follow that stuff—and I knew that Olivia had a passionate relationship with him. Several times, they’d had me sit on a stool and watch them have sex in Olivia’s bed, an event which they called “Sissy’s Sex School” because Olivia would usually dress me then like a schoolgirl in a white blouse, red plaid skirt, white knee socks, penny loafers, and a blond wig. Olivia painted freckles on my face so I felt like I was Raggedy Ann or something, and then she and Brick ordered me to take detailed notes on a pad about how men and women like to fuck each other. A subject about which, in fact, I had no experience. My penis had never been inside a vagina.

I expected Olivia to say something when I was completely naked, but she simply continued kissing Brick, so I stood there with my hands in front of my peenie, which was leaky but shriveled in humiliation. At least I didn’t have to take notes and could just watch. I have to admit, it excited me to see her with him. Of course, I had once fantasized having her myself, but when she made me realize how unlikely that was given my girlish nature, I adjusted my expectations and became grateful to be their voyeur.

Olivia was so pretty even though she was so mean to me. Maybe her meanness made her even prettier, I don’t know. That siren thing again, luring me to my doom…I watched her tongue probe Brick’s mouth, and then she slid down his body until she was crouched, fully dressed and perfectly balanced on her strappy heels, as she kneeled in front of his crotch and took out his ridiculously thick and long penis. She wolfed it into her mouth so deeply, and every time she did so I understood how lost a cause it was that she could ever get any kind of thrill taking an acorn like mine into her rich red lips.

“Come here, Joanie, come here,” she said, taking her mouth off his meat for a moment, then leaning down to suck on his balls which hung over the zipper of his jeans.  “Walk over here like the girl you are, and take his cock in your lips. No reason why you have to be dressed first. After all, in your case, clothes don’t make the girl. You already are a girl—that silly dangling thing doesn’t fool me—and you’ll be a girl if you’re sucking him while you’re nude.”

With all this dirty talk, my penis did harden. “Come on, sway your hips, Joanie,” she said as I approached. “Keep your thighs close and put one foot in front of the other. That’s the girl, now walk in a circle, let me see how you’re doing before you take this meat in your mouth. Come on, come on. Good girl, keep walking in a circle. Get on tiptoe too. Say, you polished your toenails better this week! Oh, you’re getting more feminine by the minute. And your tushy looks so sweet! It might be real competition for mine, so I better keep it away from Brick’s boner, haha!”

My mind was like a broken kaleidoscope. I didn’t know what I was: girl, boy, sissy, gay, bi? Sometimes Olivia got nasty with uglier terms, because she knew how much I could leak at cruelty and humiliation; said I would never be more than a “ridiculous little sissy cocksucker who’d do anything to lick balls and drink cum!” But overall she didn’t want to brutalize me and hurt my feelings and tell me that kind of thing too often, so she usually just said I was on my way to becoming a real girl. She said it would be better for me if I believed that too. Ohmigosh, what was I??

Finally she said I could stop walking naked and tiptoe in a circle on the carpet, and scoot over and start sucking Brick.

At first when I sucked Brick, several weeks earlier, I had felt very ashamed, but after more feminizing treatment by Olivia—shaving me completely, giving me bubble baths, perfuming me, making up my face, putting me panties and bras and nylons—I started to see myself as a female, and the shame got smaller. If I was a girl, I could suck a penis and it was right. So yes I was a girl. Yes.

Olivia trained me to suck her boyfriend's huge cock

Olivia trained me to suck her boyfriend’s huge cock

On the other hand, as I took his inches into my mouth now, sliding the satiny veiny thickness through my lips and onto my tongue, sometimes I wanted to feel ashamed because it made my peenie even harder. Wanted to hear the bad words…wanted Olivia to press my mouth on his dick and whisper into my ear, “Yes, dear, this is the proof, so always remember you’re a dirty nasty sissy boy who will do anything for cock and cream!”

“Look at Joanie suck!” said Olivia, standing up. She pointed her manicured finger in my face and directed me to take over Brick’s orgasm tonight. “I was only warming him up for you, Joanie. Make him cum and then we can get you dressed for my tutoring.”

So I moved my mouth back and forth over Brick’s cock, grabbing him by the back of his butt through his jeans and moving my face faster and faster and deeper and deeper on it. I couldn’t suck as deeply as Olivia yet, but I was getting better. Brick told me to suck his balls a little more like Olivia did, and it seemed to make him even thicker and harder. By the time he slid his prick back into my mouth, he was leaking furiously and was on the verge of cumming.

“Look at you, girl,” said Olivia. “Your clitty is a little rocket. You just can’t help the boy inside you.”

She was confusing me again.

“I want you to cum when Brick does, then I have a nice surprise for you to wear,” she said. “Come on, sweetie, you know you want his sperm.”

“Oh baby!” cried Brick, jamming his cock into my mouth so deep. Suddenly I could feel his cream jetting out but I kept my mouth closed like a good girl even though my eyes were tearing and I was almost gagging.

“What’s wrong with you?” snapped Olivia. “Didn’t you cum when Brick did, like I told you to?”

Brick slid his penis out of my lips and told me to lick up any last drops of sperm. I wanted to answer Olivia but my mouth was still busy. 

“I asked you a question, girl,” said Olivia, coming closer with her hands on her hips.

I swallowed the spunk, licked the rest off my lips, and then looked up and said, “When Brick jammed his cock in my mouth so fast, I gagged and lost my stiffie.” Olivia told me to call it my “stiffie” because that sounded more feminine to her.

“Are you blaming Brick for your not following my order?” Olivia said. 

“No, just explaining—”

“Brick, Joanie needs a spanking for disobeying. You give it to her while I get his outfit for tonight.”

Brick looked down at me. “It’ll be my pleasure to spank this bad, bad girl.”

“Good,” said Olivia. “I’ll be back very shortly.” And she went into her bedroom.

Kneeling, naked in front of Brick but feeling literally as if I had the body of a female (my cock was certainly small enough to almost qualify for a clit), I felt myself tearing up as he pulled me over to a chair on which he sat down. Then he tugged me over his lap, securing one of my legs under his, and began smacking my bottom. “You’re naughty, not following Aunt Olivia’s instructions!” he said. “I’ll stop when this cute girlie ass is red!”

And of course, with nasty words like that, even though he was sending fire through my cheeks, my cock began to harden against his jean-clad lap.

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Read the whole story in Forced Womanhood 73

Forced Womanhood 73

Forced Womanhood 73