“Strip!” barked the guard.
“All right! I heard you the first time,” Heather
Stanton replied. As an FBI agent, Stanton made
countless trips to prisons around the United States,
but she was accustomed to more preferential treatment
under the aegis of her gold badge. Today she signed
into the prison visitors’ area as Shelby Taylor, and
she had a role to play.
Stanton normally wore business suits and subtle
cosmetics. In the guise of Shelby Taylor, she wore
platform shoes, bell bottom dungarees, a baby doll t-
shirt, bright lipstick, heavy dark liner around her
blue eyes, and reddish-brown fingernail polish, a
color named “Morrocco” that deserved a less exotic
label like “Mud”. Shelby Taylor would have been the
finest example of trailer trash womanhood imaginable,
if not for the corrections officer in the room with
The CO’s dark hair was combed down flat against her
head. A severe part ran down the middle exposing a
strip of her white scalp like the center line of a
divided highway. Her jowls sagged, but looked almost
high and firm compared to her double chin. She had the
body of someone who had super-sized her McDonald’s
lunch a hundred times in the past year, and a vacant
look in her eyes that indicated despite her
familiarity with the Big Mac, she still had no idea
what the sum of $3.79 and 39 cents was. The strip of
bakelite pinned to her uniform had the name “Drury”
etched into it.
Stanton made a mental note of Drury’s name, and
started to take off her shoes. She looked away from CO
Drury as she unlaced and kicked off the platforms, and
then wiggled out of her blue jeans. Drury glanced at
Stanton’s legs, and her eyes narrowed. Normally Drury
liked to rush this along and make things as unpleasant
as possible on visitors, as she had when she called
this one out of line and into the room for a spot
search, yelling orders in a clipped voice. Now,
though, she thought it might be nice to slow this
sweet thing down, get her to take her time getting
“Wait a second,” Drury said. She pointed to a shiny
band around Stanton’s ankle. “What’s that?”
“Ankle bracelet,” Stanton replied.
“I know that, missy!” Drury snapped. “What’s hangin’
from it? Some kinda contraband?” There was no ‘r’ or
‘d’ in the way Drury pronounced the word, and somehow
an extra syllable slipped in. It sounded like
Stanton mimicked the pronunciation. “It’s not
‘conchabayin’. It’s just a charm.”
“Let me see it,” Drury said, licking her lips. “Put
your foot up on that chair there.”
As Stanton obeyed, Drury moved closer, took hold of
Stanton’s ankle with one pudgy hand, and examined the
heart-shaped charm. Her face stood inches away from
Stanton’s bare knee. Drury looked up from the cheap
piece of jewelry. White cotton panties covered
Stanton’s crotch, and Drury looked them over far
longer than she had examined the charm. She knew she
was going to see it all soon enough, and the sight of
the flimsy underwear and the contours of the mound
underneath only increased her anticipation.
“I guess that’s okay,” Drury relented, not bothering
to look back at the anklet.
A cold shiver went through Stanton’s body. She took
her leg off the chair and pulled her shirt over her
head. The dark hair that hung in her face obscured her
vision, and Stanton was glad that she didn’t have to
see Drury’s reaction. She stood still.
“What’s your name again, missy?”
“Shelby Taylor,” Stanton answered. Who the hell came
up with that name?, Stanton wondered. But she was
relieved to concentrate on her figurative cover rather
than her uncovered figure.
“And where’r you from, Shelby?”
“Springfield,” Stanton answered.
“Well, Shelby, I don’t know what they teach you in
Springfield, but when I say ‘Strip’, I mean it down to
the bone. Now keep on goin’.”
Stanton quickly unhooked her bra and rolled her
panties off her legs. The skin itched where the
underwire of her bra had pressed against the soft
flesh of her breasts, but she didn’t want to draw any
more attention to herself by scratching them. The
irritation simply added to her discomfort. “Sit down.”
Drury said tonelessly.
Thankful that the seat was wooden and not metal,
Stanton sat down. It was still cold, however, and heat
seemed to rush out of her body through her back and
backside. Drury watched as Stanton’s nipples hardened
in a purely involuntary response. Drury approached the
chair and took Stanton’s head in her hands.
Carefully the CO ran her heavy hands through Stanton’s
long dark hair. She pulled out a hairpin and continued
the search, looking down at the brunette’s bare
shoulders, her breasts, and the nipples that stood out
proudly. Drury wanted to stop for a moment and feel
the hard curve of her shoulders, and the soft curve of
“Stand up,” Drury ordered. “Grab the table.”
Clenching her teeth with anger, Stanton followed the
She bent slightly at the waist and rested her weight
against the edge of the table. Staring at a chip in
the paint on the wall, Stanton braced herself for the
body cavity search. Momentarily, she was jarred from
her quiet resolve by the snap of latex gloves being
put on behind her. Wrapped in latex, Drury’s plump
fingers looked like small sausages.
She squeezed a dollop of lubricating jelly on to her
right hand and smeared it around her fingers. She took
a moment to admire the smooth firm haunches in front
of her, the muscular back and the furrow that reached
to her waist and ended at the tailbone, flanked on
either side by a little dimple. Drury could just see a
tuft of dark hair at the juncture between her legs.
“Spread ’em,” Drury ordered unceremoniously. Stanton
moved her feet apart as far as she could and held her
breath. She felt the cool, slippery gloved hand
between her legs, spreading, stretching, poking.
Despite the lube, some of Stanton’s pubic hairs were
caught in the glove. She winced once, slightly.
“If you shaved that it wouldn’t hurt,” Drury said
knowingly. In one rough thrust there were two fingers
inside her, probing the smooth walls of her sex.
Stanton allowed herself to exhale when Drury removed
them, seemingly hours later.
“Bend over more,” Drury commanded. Again Stanton
complied. Drury spread some jelly around the winking
hole of Stanton’s ass and then worked a gloved finger
inside. She used her middle finger, and placed the
butt of her palm against one of the smooth strong
cheeks of Stanton’s ass. Awkward as that was, it left
Drury an open view of the woman’s pussy flushed red
and wet with lube.
Drury pushed in until her knuckles rested along the
crack of Stanton’s ass. She heard the naked woman gasp
for air. The CO smiled and took her time removing her
chubby finger. Drury stepped back and took a moment to
admire the fine form in front of her before ripping
her gloves off.
“OK, get dressed,” Drury said. Then she mumbled to
herself, “Did that little girl a favor. Now her con
boyfriend can take her any way he wants her.”
Stanton rushed back into her clothes. She avoided
looking at Drury and followed her out of the room.
Outside the door stood a tall male CO with a toothpick
jutting from between his lips. He wore sunglasses,
tinted dark brown, but tilted his head up and down to
let her know he was looking her over. He shifted the
toothpick from one side of his mouth to the other and
“Oh, Jesus,” Stanton thought, “He saw that, didn’t he?
Through a window? Maybe even a camera. They probably
have that on tape. They’ll be taking bribes from
convicts to show it on television.” That kind of
corruption was the reason she was there. The Bureau
had an agent inside the prison to investigate
allegations from former inmates. The undercover
operation was running smoothly until one inmate made a
big stink one night. He had noticed that although the
agent wrote and received plenty of letters, he never
had a visitor. Enter Shelby Taylor, as portrayed by
Special Agent Stanton.
The tall CO stepped out of Stanton’s way when the
magnetic lock released. A loud buzz sounded, a green
light flashed, and the barred door to the visitors’
area slid open. Stanton was one of the last in, having
been delayed by the strip search. Drury hadn’t offered
her anything to clean herself with, and as she walked
through the tables, she felt the lube squish between
her legs. Almost as cloying, she felt the eyes of
guards and prisoners on her as she looked for the
Stanton was given his assumed name, Leo Calderone.
Without knowing his real name, it was impossible to
slip up. She had seen his picture, and he had the dark
Latin features to match his surname. Stanton scanned
the room, looking for him. She spotted one inmate with
a woman’s head bobbing up and down between his legs,
and another with a blonde straddling his lap, a short
skirt hiding their copulation from view. What a
welcome, Stanton thought. She spotted Leo. “Leo,
“Oh, Shelby, you look good, baby!”
The two embraced. Stanton closed her eyes as they
kissed, and felt his hands reach for her ass and give
her a playful slap. Had to play the part. At least
Calderone was easier on the eyes than Drury.
Her brief was thorough, her job minimal. All she was
supposed to do was get inside and give Shelby Taylor a
face. She was to hold hands with Leo, complain about
her boss and her job at his little accounting firm,
and ask when Leo was going to get out of jail. It was
a simple performance, pure fluff, but Stanton decided
at that moment to ad lib a bit. She started to cry.
Agent Stanton buried her head in Leo’s chest and
sobbed, heaving her chest as if she’d lost control
over her ability to breathe properly.
“Hey, hey, Shelby, what’s wrong?”
“Oh, Leo,” she said between sobs, “When are you
getting out of here?”
“Soon, baby, soon,” he answered, wrapping his arms
around her shoulders and holding her tight. Stanton
returned the embrace, and buried her head in his chest
for a moment. When she looked up again, she saw a
guard walking by escorting a prisoner through the
visitors’ area. It was time.
“Oh, Leo, I don’t think I can do this again, baby. I
can’t come back here again!”
“Shelby, don’t get upset,” he said. “I’ll be out soon.
You don’t have to come again.”
That was all Stanton needed to hear. She hoped the
guard and the inmate also heard the exchange. Shelby
had a face, and now a damn good reason not to have to
show it at this prison again. Stanton was satisfied
with her performance, glad that she was through being
humiliated, and looking forward to coasting through
the rest of the visit. The pair of agents quickly
moved through the litany of Shelby’s frustrations at
work. Stanton rattled off her complaints and Calderone
dutifully nodded his head and sympathized. Calderone
mentioned possible dates of release, and it was
Stanton’s turn to nod in ascension. After that she
figured it was high time to leave the place behind. It
was at that moment that she saw Curly Williams.
The nightmare of any agent working undercover is to be
recognized for what they really are, to be ‘blown’ as
the saying goes. As a Special Agent, Heather Stanton
had investigated and arrested Curly Williams for
running a prostitution ring out of a set of dry
cleaners and tailors. The press labeled Curly the
‘while-u-wait’ pimp and jokes about ‘sew-jobs’ filled
the late night talk show monologues. Having your cover
blown was no laughing matter, though, even if it was
the while-u-wait pimp who did it. There was nowhere to
run. Curly might see her, he might not, but he was
certainly headed her way. Stanton’s mind raced to find
a means of disguise. She hadn’t realized she’d stopped
speaking in mid-sentence.
“What’s the matter, Shelby?”
Blown. It was the only word that came to mind.
Stanton snapped back to her surroundings. Wondering
where Curly was, she took a quick look around. To the
left was a woman resting on a prisoner’s lap. They
must have finished. She wondered if the other one was
done giving head to her…
“C’mon, Shelby,” Leo pleaded, “What is it?”
No sooner had he finished asking the question than
Stanton’s head was buried in his lap, and her fingers
were working the button fly of his prison coveralls.
The undercover agent was so surprised when she took
hold of his floppy dick that it actually shrunk back a
bit. “What the…?”
The man gasped when Stanton took his limp organ in her
mouth and swirled her tongue around its soft crown.
Whatever surprise and nervousness he felt dwindled
rapidly, and in equal measure his cock swelled in
size. “Oh, fuck!” he stammered. This was the first
time he’d ever met the brunette agent and her pretty
blue eyes; now she was kneeling between his legs and
sucking on his prick as if a snake had bit him and she
needed to extract the venom.
“Damn, Shelby,” he said in utter amazement. This agent
sure as hell knew how to get into the act. Quite a
finale considering a few minutes ago she was signaling
that under no circumstances was she making a repeat
performance. His cock had stiffened and lengthened,
but she continued to work over its full length, with
her hands resting on his thighs, and her dark hair
falling near his navel.
Who was this woman? He wanted to get another look at
her. As he tried to brush her hair out of the way, one
of her hands leapt off his lap and slapped him sharply
on the wrist. For the first time since she’d suddenly
dropped to her knees, Stanton released her mouth from
his shaft. “Leave the hair alone,” she said quickly,
before going back to work.
“Whatever you say, baby.” He was as confused as when
she started, but aroused enough not to care anymore.
Rock hard, his cock pulsed in her mouth. Stanton
thought Curly had to have passed by now. She pulled
off again, taking the wet sticky shaft in her hand.
“Can you see Curly?”
“Curly?” he said in surprise. It just so happened the
man was walking by at the time.
“Yeah, what you want, man?” Curly asked loudly.
Stanton’s heart leaped into her throat. It was a good
thing that she no longer had a cock there; the
collision could have been rough. She had to get rid of
Curly. She squeezed Leo’s cock. “Ahhh,” he exclaimed.
“Nothing, man. I’m busy.”
“Shit, I can see that. Izzat yo woman?”
“Yeah,” Leo answered.
“Well, when she’s done there, send her my way.”
“Fuck you, Curly.”
Curly laughed and walked away. “See ya back at the
Now Leo could guess why the agent had buried her face
in his lap. That was a pretty smart move. He was about
to tell her that the coast was clear when he
remembered that he was sporting a monster hard-on,
there was a blue-eyed girl with her head between his
legs, and he was in prison, undercover or not. “Keep
going,” he whispered. “Curly’s a few feet behind you.”
She worked slowly and methodically. Leo helped by
guiding her head with his hand, but he was careful to
let her hair cover her face. Her mouth was warm and
wet sliding along his rigid prick. “Keep going,” he
said. “That’s so good.”
Stanton heard the last bit of what he said, and it was
her turn to realize what was going on. But she was a
bit too late. Leo erupted in orgasm and two months of
frustration burst from his balls and into the roof of
her mouth. If she pulled off at that point, she risked
a shot in her face or hair, so Stanton let him blast
away. Two, three, four warm streams filled her cheeks.
When the spasms stopped, Stanton opened her mouth. The
goo trickled along his shaft and down onto his balls
in his coveralls. Most of it, anyway. She wanted to
smack him, but instead she kept to their cover. She
“You’re the best, Shelby.” he said, and meant it.
“I can’t wait until I get you outside this prison,”
She meant it, too.
Stanton let him peck her on the cheek, and then she
turned to leave. Naturally, Curly was nowhere to be
seen. As she walked, she felt the lube again between
her legs. She wanted a shower. She wanted a breath
mint. She needed to get the hell out of there. What
she got was a guard stopping her on the way out.
“That was a helluva show you put on there.” Drury said
“Fuck off,” Stanton replied.
“Hold on there, bitch,” the guard said, catching her
by the arm.
Instinctively, Stanton thought of flipping the CO over
her hip. Instead she stopped and stayed in character.
Drury went on talking. “We have rules here, and that
little indecent act is against ’em.” Stanton met her
with a blank stare. “The fine is fifty bucks,” she
A bribe, Stanton thought. On top of all that, she
expects a bribe. Stanton pulled three twenties from
her jeans and thrust them at the CO. “Happy now?”
“Not really. But now that you know the rules I guess
you can go.”
Not really happy, Stanton thought. She wasn’t the only
one. She made her way back to the beat-up CRX the
bureau procured for Shelby Taylor and headed back to
the field office. During the debriefing, she simply
mentioned a ‘distraction’ that she arranged with Leo
when she saw Curly. She filled out the bureau’s
copious forms, and a local field agent gave her a lift
to her hotel. After a long hot shower, she met her
partner Maytag at the hotel bar.
“How did it go?” he asked.
“I don’t want to talk about it.” Stanton took a long
swallow from her gin and tonic, then looked over at
her partner. “Hey,” she said. “What happened to that
orange tie you had on this morning?”
“I don’t want to talk about it,” Maytag answered. It
was a story for another time. They finished their
drinks in silence.