Undercover Holly

by T.S.Severe

Rachael Ross 1982 - 2012

Romantic Sex Story: Jack has been working vice for nearly a year as a prostitute named "Holly", much to the amusement of the other cops. When things unexpectedly heat up with a rookie, however, it begs the question...Who's really undercover?

Caution: This Romantic Sex Story contains strong sexual content, including Consensual   Romantic   CrossDressing   First   Oral Sex   Anal Sex   Masturbation   Petting   .

"Hey sugar!" A black Lincoln pulled up, riding slow under the neon and I kept walking, my heels click-clicking on the sidewalk. "You need a ride home?"

"You know where I live?" I asked him without looking, swinging my purse and putting one foot directly in front of the other so my narrow hips turned nicely in that short leather skirt. My ass was high and round, rolling sweetly and I was giving him a lot of long toned leg too.

"Why don't you get in?" the guy suggested with a grin. "You can show me the way."

"Oh, I don't ride with strangers." I stopped, bending over to look inside open passenger window of the car. My top was tight around my tits, but he could see how full they were, how firm and heavy as I gave my bare shoulders a little shimmy like I was cold.

"Come on, sugar." He smiled at my beautiful face, perfectly made up beneath my wavy auburn hair. "We won't be strangers for long, I promise."

"Nah thanks," I wrinkled my pert little nose at him and rolled my big green eyes. "You look like a cop."

"A cop?" He laughed at me. "I'll give you a hundred bucks, come on. I got a room at the Roosevelt."

"A hundred huh?" I pursed my soft red lips and looked around for a second. "What do you want? I don't do any weird stuff."

"I just wanna fuck your brains out, sugar," he promised. "That too weird for you?"

"Nope," I smiled and Peter was already flashing his badge, appearing as if by magic at the driver's door.

"Hands on the glass, now!" Pete had his gun out too and so did I, because you never know about some of these guys.

"Vice, sugar." I looked down the barrel of my little BDA .380 and smiled. "You're under arrest.

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"God. My feet are killing me," I said, sitting in a booth at Murphy's, a little bar not too far from where we working.

"Twenty-two tonight. Not bad at all." Detective Pete Robbins was putting a rum and coke in front of me and I needed it. "Day off tomorrow, then we'll do the airport for awhile."

"Yeah," I grinned, picking up my drink. "Paperwork and night court, some day off."

"Ah, couple more months and you'll be done," he grinned and we'd been partners for awhile now, almost a year, and we were both looking at transfers soon. "You'll get a good look at the board."

"Nobody makes detective first time up," I shrugged. "It would be nice though."

"If anybody's got a shot at history, Holly..." Pete held up his beer in a little toast, " ... You could be the first."

"Yeah, right." I licked my lips, looking around, but that was just habit. "How many beers you drink?"

"Just the one, Jack," he laughed lightly. "Gonna be tough calling you that again."

"Heh!" I grinned at him and let it slide. Pete hadn't said it very loudly and we'd been talking a lot of shop. Murphy's was a cop bar anyway, so it was cool, but anywhere else...

We had a rule though, a serious one, that if I was dressed, I was Holly. It saved a lot of confusion and out on the streets like this you never knew who might be listening, and like it or not, Holly was on duty everytime she put on her shoes. Pete knew it as well as I did and he was good about it, as he should be after some ten months of working together. The man hardly recognized me when I wasn't dressed up and every now and then I'd be in my blues at the precinct, looking like Officer Jack Turner, and Pete would have to take two or three hard looks before he'd believe it.

"Hey, Pete ... Holly! Lookin' good, baby!"..."She comin' on or goin' off?" A couple uniforms from the precinct walked by, grinning at me.

"Hey fellas," I gave them a sexy smile. "Gettin' off, I hope."

"Shit." One of them, the blond shook his head and gave his crotch a little rub.

"We sit with you guys?" the other asked and I'd seen him around.

"Yeah. Pull up a chair, Barney," Pete nodded. "They got you guys walkin' now?"

"Fuck. Mayor's new policy. Gotta have a presence," the darker one, a guy named Barnes grimaced. "Whatever the fuck that means. You know my partner? This is Mitchell."

"How ya doin'? Mitch," the blond boy held out his hand.

"Pete. You're that rookie Barney's always bitchin' about, huh?" Pete grinned as they shook hands.

"Yeah, he's gotta have somethin', right?" Mitch gave his partner a grin and the boy could have been about twenty minutes out of the academy. He looked at me. "Hi. Holly is it? I'm Officer Mitchell."

The way he said it left little doubt that Mitch had no idea who I was and that was cute. He thought I was just a whore taking a load off her feet, maybe giving a little info to Detective Robbins, cause the working girls were always a good source. Could be I was giving the Detective a little something else too, Mitch thought, judging from that little smile playing at his lips. Rookies believe everything they hear and they get their chains yanked mercilessly.

"Hmmm ... I can see that, Officer," I smiled, letting him hold my fingertips for a second while Pete and Barney exchanged amused looks. "Are you here to protect ... or service me?"

"Can't I do both?" he grinned and it was a good one. I bet Mitch had broken a lot of hearts growing up.

"You be nice to Holly," Barnes told his partner. "She's got a thing for cops."

"A real thing," I giggled and gave Barney a little wink.

"Is that right?" Mitch chuckled. "And me sitting here with a thing for red heads."

"Oh, now you're teasing me," I pouted.

"He's just new," Pete laughed, reaching for his beer. "You be nice too, baby."

"I'm always nice." I put my hand on Pete's thigh, giving him a little rub and he almost choked on his drink. "You know that, Petey."

"Maybe we're interrupting something here," Barnes grinned at Pete.

"Hey, you wanna dance?" I asked Mitch and Pete gave me a look. "Come on. They got a juke box!"

"Uh, no ... I don't..." Mitch was shaking his head.

"Yeah, you do!" I giggled and I was already standing, tugging at the policeman's hand while he smiled self-consciously.

"I thought your feet hurt?" Pete chuckled as he watched me pull the blond man to his feet.

"Not anymore," I smiled at my partner. "Officer Mitchell's gonna hold me up anyway, aren't you?"

"Uhhh..." Mitch grinned at me.

"Go on, rook. You better dance with her or we'll never hear the end of it," Barney waved the boy away. "Only one though!"

"That's all we're gonna need!" I giggled, pulling the reluctant young officer towards the jukebox.

"I'm, uh, not supposed to be dancing in uniform, I don't think," he cleared his throat. "Holly."

"Oh, I like the way you say that!" I smiled over my shoulder at him as I pushed buttons, rocking my pert round ass back and forth in that short skirt. "Say it again."

"What?" Mitch smiled. "Holly?"

"Yeah..." I sighed, turning around as the music started. "I definitely like it."

I'd picked some slow songs, this being one of those nights where it felt like everything was running down. I held out my arms for the man, smiling at Mitch and for just a second I didn't think he was going to do it. Being on duty and in uniform like that, he could get in a little trouble for fooling around, but who was gonna know? Barney would cover for him and he did like the looks of me.

I liked him too. Officer Mitchell was all kinds of manly. Over six feet and solidly built, rugged handsome like a cowboy. He just needed some seasoning, some years under his belt because he had one of those faces that looked real good when they hit thirty-five or forty maybe. Mitch didn't belong in the city, he belonged outside someplace, riding a horse, I thought, with his blond hair and blue eyes and gentle hands on my waist all of a sudden.

"Like this?" he asked, looking down at me because even in those three inch spikes I was easily half a foot shorter.

"Uh-huh," I nodded, reaching up so I could put my hands on his broad shoulders. "See? You know how to do it."

"I guess I do," Mitch smiled and I stepped a little closer, just because he wasn't ready to pull me close yet.

"You're a good looking man," I breathed, moving my long red nails so I could tickle the back of his neck. "You have a girlfriend?"

"Uh, no," he shook his head. "I mean, I had one, she went to college out in California, so..."

"Awww..." I pouted. "I don't have a boyfriend either."

"Well..." Mitch chuckled softly and I felt his hands tighten a little around my narrow waist. "You have a different boyfriend every night, right?"

"What?" I giggled. "No! Be nice. Business is business, but when I go home ... I just want to curl up, you know?"

"Sure. Yeah," he nodded sympathetically. "What, uh ... How old are you?"

"How old do you think I am, Officer?" I arched my thin eyebrows playfully.

"Um, I don't know," he shrugged. "Nineteen?"

"Oh, you are sweet!" I sighed. "I'm going to be twenty-three next month."

"Really?" Mitchell nodded. "I'm twenty-one myself."

"Maybe you'd like to take me out on my birthday?" I pulled him by the neck and he didn't mind taking me a little tighter.

My tits rubbed against his uniform and my flat little tummy was touching his crotch, feeling the unmistakable bulge beneath his dark blue trousers. His belt too, that big leather utility belt stuffed full of guns and flashlights and handcuffs. That was a little annoying.

"Oh, birthday?" He sucked his top lip. "What's, uh ... What's a date with you go for?"

"Go for?" I giggled. "Is that a proposition, Officer Mitchell?"

"Huh? No!" He blinked at me and his face turned a little pink.

"Just professional curiosity, huh?" I licked my lips slowly. "Too much of that makes my pussy nervous."

"Excuse me? Oh. I was just ... Wondering, yeah." He was a bit flustered which was amazingly cute, and I felt warm all over.

"Oh, about a hundred dollars an hour," I shrugged. "All night gets a discount though."

"A discount?" Mitch swallowed hard, his hands moving towards the small of my back, and the man was doing a little grind against my tummy while we hardly danced at all.

"Five hundred for you," I whispered, looking up into his big blue eyes. "I take traveler's checks and all major credit cards."

"Oh." He looked so serious I almost blew it with a real laugh, but I was pretty good at this stuff by now. Real good at it and I wondered how long our partners were gonna let the rookie dangle before they let him in on the joke. I was enjoying myself a lot.

"No personal checks though," I sighed, putting my cheek against his chest. "Sorry."

"Yeah. well, a girl has to be careful, right?" Mitch cleared his throat. "Do you like it?"

"The work?" I asked softly. "Yeah, I love it. It's a real public service."

"Heh!" Mitchell laughed at that and his fingertips were at the top of my ass, looking for a feel through the thin leather of my skirt.

"Like you." I looked up suddenly. "You work long hours, right? Come home tired and beat. You just want a girl to make you feel like a man, get you all relaxed and comfortable, work all that stress out of your body."


"You don't wanna go out and hit some bars. Hit on some girls who just want to know what kind of car you drive," I spoke gently, stroking Mitchell's neck. "You want a girl who's going to love you for a little while. No strings attached, right?"

"Maybe..." He was holding my ass now for real, giving me a nice squeeze and I wriggled a bit, giving myself to his hands. It was a funny how good that felt, how his fingers fit my curves so perfectly and I hitched a little breath.

"A girl who doesn't mind if you want a little something..." I shrugged with an inquisitive smile, " ... special? A little different maybe? A girl who won't say no to anything you want to do?"

"Yeah," he sighed with a small grin. "That would be nice."

"Yeah," I agreed softly. "See? That's what I'm providing. A service for men like you, Officer. Something you need."

"I see." He kept his right hand on my ass while the left moved up and down my spine slowly, giving me little chills.

"But even a girl like me wants a man to come home to," I whispered, looking up and playing my tongue between my lips. He had some serious blue eyes. "I could make the right man feel more than just special."

"Jesus, you're beautiful." Mitchell was hardly breathing and his cock was hard as steel, jutting against me through his trousers like a railroad spike.

"Do you like me, Officer Mitchell?" I stared into his eyes. "Do you want to take me home? Handcuff me to your bed maybe?"

"I wish..." He was bending his head and I felt it, like electricity between us.

He was going to kiss me and I'd never done that. I wasn't gay, I was just undercover and I blinked hard, wondering what the hell I was doing. Why was I attracted to him? Because that's what it was, undeniably. This man was sexy and holding me right. The way I wanted him to, and he was hot and hard and I was melting for him. My heart was going fast and it had been, without me even knowing it. My skin was tingling and he was going to kiss me and...

"All right, break it up, you two." Pete was there to save me and Barney was sitting at the table laughing.

"Come on, Rook..." Barnes called his partner, " ... Let's take it for a walk."

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