The Jewish Princess

by Jacqueline Jillinghoff

Copyright© 2011 by Jacqueline Jillinghoff

Sex Story: Winter. The second of my Newsboy stories, described by one reader as “femme-domme with a vengeance.” Finding safety in numbers, a trio of young girls decide to see just how hot they can get the boy they call Kid. But he braves it out, and they wind up just as turned on as he is. Based on a true story.

Caution: This Sex Story contains strong sexual content, including mt/ft   Mult   Oral Sex   Masturbation   Exhibitionism   .

In an odd way, my nude encounter with Mindy made us buddies. We never played I'll-show-you-mine-if-you-show-me-yours again. We never even mentioned it, but in the weeks and months that followed, we talked about everything else, and I'm sure it was no coincidence. She became my booster. I became her confidant. I heard all about the boyfriend, the deflowering, the inevitable breakup, and the boyfriends — lovers, really — who came later. Her sex life became an open secret.

But Risa, the girl who lived next door to her, became my nemesis. We paid no attention to each other my first year or so as a paperboy, but when we finally did, we fell into one of those mutually insulting relationships that sitcom writers think are so hilarious. We constantly tried to top each other with put-downs, and once teenagers start cutting, retreat and reconciliation are impossible. I don't recall a pleasant word ever passing between us.

I did get her good once, I remember, baiting the hook by asking her if she was a very happy person.

"I'm happier than you'll ever be," she said automatically. I had expected a reaction like that. I'd prepared for it all day.

"Well, that proves it," I said. "Ignorance is bliss."

Yuk, yuk, yuk. But her dad, who was standing between us, laughed.

"Touché," he said as he handed me the week's money for the paper.

She could have topped it simply by calling me a faggot, but not with her dad there, and besides, that level of sophistication was beyond her.

Another time, I challenged her to name five presidents from the first half of the 20th century. She did it, barely, with some help from her mother, who was one of the loveliest women I've ever met. I never understood how she managed to raise such a bitch of a daughter.

My few little victories meant nothing, of course. No matter what insults I could think of, or steal from All in the Family or a Marx Brothers movie, I never got the better of her. In the first place, she was dense. Words bounced off her. And in the second place, I was in love with her. She was slimmer than Mindy, with tits just big enough to fit under my hand and a beautiful, compact ass. Like the knight in Camelot (told you I was a faggot), I loved the sight of her in summer in a clingy tube top and denim cutoffs, or in winter in a mini-skirt with white stockings and thick-soled pumps.

Once I nearly asked her out. Seriously. A real date. All down the block on collection night I imagined myself confessing my feelings and apologizing for all the insults and telling her that all I wanted in the world was for her to come with me to the mall. But when I got to her house, there was another boy sitting in her living room, a wiry jock with curly black hair and a well-muscled chest, and I lost my nerve, which, I'm sure, saved me from a taunting rejection.

So the Dozens went on — pointlessly, because Risa had already won. She didn't know it, but I would gladly have crawled naked across her living room just to kiss her feet. At a word, she could have peed all over me and made me lick it off the floor.

And of course, the one thing I wanted was the one thing I never got. When Risa finally decided it was time to establish her dominance over me once and for all, she didn't deign to do it herself. She sent a ringer.

It must have been sophomore year. I would have been fifteen. I was collecting again, this time in the frigid dark during Christmas vacation. Strings of hell-red, ghost-blue, and goblin-green lights outlined the windows of the few gentile homes on the block. My tribe, the papists, was easy to identify this time of year.

I was wearing my blue cloth coat, with the hood down, and no gloves, since I needed my fingers to make change and check off payments in my book. My money apron hung around my waist, heavy with coins.

Risa's home had no festive lights. A single lamp shone in the living room window, as it might if no one were home, but I heard girls' laughter as I passed beneath the front window. The bullies at school hadn't beaten God out of me quite yet, and I prayed her parents were there. I did not want to face her and a pack of her friends without a buffer of adults. In numbers greater than two, girls that age will eat a boy alive.

But, business being business, I knocked. At once a tumult arose inside, and one high voice pierced the general confusion with the words, "That's him!"

I heard the inside vestibule door open and the bolt in the front door shoot back. The door opened just enough to let me slip through, and, stepping inside, I found myself cornered by three girls. One of them was Risa. I didn't know the other two, but they were as beautiful as she was, in their adolescent way, and just as aggressive.

Risa closed the front door and furtively locked it again.

"How much is it?" she said. She had a talent for making the simplest question sound like a sneer.

"A dollar ten," I said. (Unlike Mindy's parents, Risa's also took the Sunday edition.) Risa walked back into the house, leaving me with her two friends in the four-by-four vestibule.

"Risa tells me you do really good in school," said the one in front of me.

"Yeah," I replied. Not knowing what was coming, I just wanted to get my money and get out of there. The girl looked directly at me with bright eyes and a strange smile. Just to fill the silence, I said, "I made first in my class this semester."

"Oh, Kid, that is so good," she said. Her feet were bare, one crossed over the other. She wore bell-bottomed jeans that hung low on her hips and a black, long-sleeved leotard top with a low scoop neck, the kind ballet students wear to rehearsal. It molded itself to her breasts and tummy and the inward curve of her waist. Her hair was sandy brown, cut short, with a sweep across her forehead.

This was the Chosen One.

Risa came back with a pair of dollar bills and held them out to me. My fingers were just grazing the rough paper when Leotard-Top snatched them away.

"Uh uh. You can't have it," she said. "Not till you feel down my bra to get it."

President Washington disappeared down the scoop neck.

"Go ahead, Kid," Risa said. "Be a man."

To this day I don't know if Risa ever learned my name. To her I was always Kid. While I dithered, staring at the shadowy dimple between the girl's boobs, Risa and the second friend — whom I'll call Number Three — backed into the living room and shut the vestibule door. I heard the key turn in the lock, and suddenly I noticed the key to the front-door bolt was gone. Risa took it with her as part of the plan. I was caged in a four-by-four room with a strange girl who was having the time of her life embarrassing the hell out of me.

"Now you'll be in there together forever and ever," Risa called from the living room. The inside door was glazed with fifteen little windows, five rows of three, leaving me and Leotard-Top open to inspection like a pair of lizards in a terrarium. Risa and Number Three huddled together, shoulder to shoulder against the glass.

"Whatchya waitin' for, Kid?" Leotard-Top said. The folded bills made an oblong bas-relief in the black cloth below her left nipple.

"What would you do if I actually took you up on that?" I said, trying to sound brave.

"Try it and find out."

"Oh my God, he's gonna do it!" yelled Number Three.

Leotard-Top fixed her eyes on mine as I twisted my left arm so the palm of my hand faced her chest and my long fingers broke the border of the scoop neck. The soft globes closed in on them from each side. There was a film of slippery sweat in her cleavage, despite the chill I had brought inside with me.

My fingers snaked along the crease below her breast and covered the crisp bills.

"Jesus Christ, his fingers are fucking freezing!" she yelled. The girls in the living room squealed.

The nipple under my hand grew solid. The other one stood up in sympathy, poking up beneath her bra. Leotard-Top tried to stay in control, her eyes unwavering, staring me down, but her breathing had changed, subtly. She exhaled with just a little too much force.

"Go ahead and take it," she said.

"What, the money?"

"Yeah, the money. What are you, an idiot?"

"Well, we are dealing with two competing desires here."

"God, Risa said you were weird."

The moment passed. I closed my hand, careful to flick her nipple with every frostbitten fingertip, and extracted the bills.

"How'd it feel, Kid?" Risa called. "Or don't faggots like boobs?"

"As a matter of fact, I did like it," I said.

I took a fistful of icy coins from my apron, picked out a dime, a nickel and three quarters, and dropped them into the left front pocket of my jeans.

"Now, if you really want the change..." I said.

With a smirk, she dipped down into the pocket and felt around, pretending the coins were eluding her.

"Kind of stuck way down there," she said, sliding her hand across my penis, which had grown erect at an awkward angle.

I, too, exhaled with a little too much force.

"Is his thing all hard?" Number Three called out.

"Oh, God, yes," my Mistress said.

"Let's see it!" Risa said.

"You heard her. Do it," said the Mistress in the black top. She gave my pole a squeeze through the pocket and called out, "It's not a bad one."

I wondered about her range of comparison.

"Come on, Kid, let's see it," Risa said.

"Take this off," my Mistress said, pulling at the zipper of my coat with her free hand. I helped her, and the stiff, heavy shell slid to the floor, leaving me in my soft black sweater. I was bare-chested underneath it.

"Now this," she said. She pulled the coins from my pocket and jingled my change apron. I reached behind and undid the strings, and the bulging pockets dropped to my knees. Nervous as I was, I took care to fold the apron into quarters and wrap the strings around it, tight, like I was squeezing out a teabag. I dropped it in the corner behind me.

The two girls chanted through the door, "Do it! Do it! Do it!"

I knew they were laughing at me, like it was some display of weakness to show them my dick, but the lure of exposing myself was too strong. Even humiliation would be a pleasure. I opened my zipper and pushed down my jeans and underwear together. My dick dropped like a drawbridge.

"Whoa!" the girls yelled through the glass. Number Three was cupping one of her tits through her clothes. She was dressed like Santa's preppiest elf: a red corduroy skirt, forest green panty hose with no shoes, and a green crocheted vest over a pink Oxford shirt.

"Say, 'Kiss me, you fool, '" Risa commanded.

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