Bill and Trudi Go Undercover

Double Penetration

Bill and Trudi had been undercover, internal investigators for the state Highway Patrol for almost five years. They liked to work together. Bill accepted Trudi’s attraction to other women, despite the fact he thought she was wasting her beauty on them. Many times he tried to sway her back into the heterosexual world, and each time she refused, although Bill was one guy that might make her think twice. He was cute, if not quite a hunk. They were both single and in their thirties.

Their assignments normally involved theft of equipment by Highway Patrol officers or employees, or the occasional attempt at bribery. This one was different and they were both more than a little excited about it. They had been assigned to confirm a suspected improper relationship between a post commander and one of his subordinates.

It would be a piece of cake to accomplish the task and the possibilities of what they might see in the process had them both tingling with anticipation. The commander was a forty year old man and the female officer in question was an adorable, petite thing ten years younger than him.

Bill and Trudi had the commander’s office bugged, with a wireless camera installed in a corner of the ceiling. They would be stationed in an abandoned farm house across the street from the rural Patrol post ready to monitor the audio and video feeds.

Results were immediate.

Bill and Trudi were halfway through their KFC meals when Bill mumbled something, used his extra crispy wing to point to the monitor, and looked over at his partner. Trudi nodded in acknowledgement of the female officer’s entrance into the commander’s office a few minutes before 7 PM.

Officer Jill Brown struck a stunning pose in her Patrol uniform. She had short, light brown hair and dramatic facial features. The uniform did a good job of understating her chest, but hints of very full breasts still existed. There was no denying her tiny waist and tight, round ass packed inside the standard issue pants.

“God,” Bill uttered between bites. “She is SO sexy. Would you do her?”

Trudi grinned. “I’d rather have HER breast than this one.”

She erotically licked the chicken she was eating and Bill smiled from ear to ear.

Post Commander Ed Smith had Highway Patrol written all over him. Tall and burly, he was an imposing figure next to the diminutive female officer. He was not the type a speeding offender would question. And, as was suspected now, young female officers might be inclined to submit to any order he gave.

Bill, Trudi, nor anybody else in the Highway Patrol cared what was going on inside Jill’s mind as Ed approached her behind closed doors. They cared about the fact he was now holding her in his arms, kissing her passionately.

Soon, one of Ed’s hands moved up to the top button of Jill’s shirt.

“Here we go,” Bill said. “Show time.”

Without ever breaking off the kiss, Ed had the shirt unbuttoned down to Jill’s belt. Finally, they separated just enough to allow Ed to pull the rest of the shirt out of her pants. Two more buttons were undone and the shirt lay open, revealing bare skin and part of a white bra.

Ed’s hands slithered inside the shirt as the couple kissed some more. His body concealed a sufficient amount of the action from the camera to cause Bill to state, “Fuck. Move over, damn it.”

“Be patient,” Trudi urged. She took a bite of biscuit. “I’m thinking you’ll see plenty here in just a minute.”

It didn’t take that long. Ed yanked off the shirt almost immediately and began kissing the newly exposed skin. The bra Jill wore was silky white and barely covered her full, firm breasts. Ed skimmed across the top of it with his lips, dove into her cleavage for a second, and then covered her stomach with licks and more kisses. The smile on Jill’s face turned into a sensuous grin when Ed’s hands enveloped both breasts and massaged them through the tiny bra.

“Ohhhh, Ed. Take it off, please,” Jill could be heard begging.

Silently, Ed moved around to her back. The bra was unhooked and he playfully allowed it to slip off her tits and down her arms.

“It’s about fucking time,” Bill declared.

“Christ, Bill. Aren’t you the greedy one.”

Bill looked at Trudi and said, “Are you wet yet?”

“Hell yes. Are you hard?”

“Why don’t you find out?” Bill replied.

“No thanks. Talk to Ms. Brown, here,” Trudi answered, returning her gaze to the monitor.

Ms. Brown was now topless and was having her tits worked over from behind by her boss. Ed had the young woman moaning out loud when he reached down for the silver handcuffs dangling from her belt.

“I’m glad you remembered,” he told her.

“Please don’t hurt me, Mr. Patrolman,” Jill squealed in a clearly false plea for leniency.

Ed pulled on the cuffs, stretching them out in front of Jill’s face.

“But you’ve been bad. You were fifteen minutes late getting here tonight and I’m horny. What should we do about that?” he asked.

“Don’t cuff me, please.”

Ed roughly görükle escort pulled one arm behind Jill’s back and slapped on the cuffs. The other arm was yanked behind her and a second later she was a defenseless prisoner to the commander’s desires. The smirk on her face and the erect nipples on her tits belied any words of fear.

Ed pulled on her hair, jerking her head back and jutting out her tits even more.

“It’s time to atone, officer,” Ed said. “Be good and you’ll keep your job. Be VERY good and I’ll invite you back.”

Jill’s heart pounded, knowing what was coming. Each time they met, Ed tried something different; something better. Never had she been handcuffed, and the excitement inside her was unbearable. Her pussy dripped with juices in anticipation of the long, thick cock she knew would soon penetrate her. But how, and where?

“God damn,” Bill sighed. “We get to watch the whole thing, don’t we?”

“Yes. Can you make it that long?” Trudi said.

“You’ll be the first to know.”

Ed pushed Jill towards his huge, wooden desk. The surface was purposely cleared of all papers. Jill stumbled against it, her stomach taking the brunt of the contact with the edge of the desk. Ed was quickly behind her again, pressing his cock against her ass.

“Are you ready?” he said in a deep, dangerous voice.

“Yes,” Jill whimpered.

“Spread your legs.”

Jill obeyed and Ed slapped his hand up against her pussy, followed by a few seconds of swipes with his fingers.

“You’re hot, Jill. I can feel it,” Ed said.

Jill bit her lip and just nodded.

“Do you want me to fuck you?”

She nodded harder.

“Tell me.”

“I need to cum, Ed. Fuck me, please!”

Ed undid her belt, unbuttoned her pants, and pulled down the zipper. His hand slid inside, the outline of his fingers plainly visible as they worked their way down to Jill’s pussy. He lingered there for a moment.

“Yep. You’re soaked,” Ed said. “I think you’re liking this a bit too much.”

The handcuffed, topless officer didn’t reply as Ed lowered her pants and took them off. On his way back up, he grazed his fingers along the insides of her thighs and across the back of her small, white panties. Jill’s body stiffened at his touch, especially when he put his hands inside the back of her panties and clutched at her ass.

Bill snuck a peek over at Trudi and saw her running her tongue across her slightly parted lips. His cock hardened even more than it already was, knowing that both of them were enjoying this immensely.

Ed had his ‘victim’ naked by the time Bill looked back at the monitor. Jill looked extremely vulnerable and tempting with her hands cuffed behind her and her body somewhat bent over the desk. Ed slapped her ass one time and said, “OK, babe. It’s time to get serious. Turn around.”

Jill twisted her body around, a look of desire and anxiety on her pretty face. Ed wasted no time in leaning down to take one of her tits into his mouth. The sounds of his licking and sucking were heard by Bill and Trudi, who stared at the screen as if missing one second of it would blow the case. Jill moaned her approval as her nipples were pulled by Ed’s lips and lightly bit by this teeth.

Then Ed stepped back and opened the fly of his pants. His hand disappeared for a second, only to reappear with a sizeable erection in his palm. Jill watched it point straight at her when Ed let go.

“Get down and take it,” he ordered her. “Just like you did in the cruiser the other day. Only this time you don’t get to taste me. I have other plans.”

Jill uneasily lowered herself until her lips could kiss the swollen dick. Then she licked the tip and the entire length of both sides. The cock twitched and began to point more at the ceiling that at Jill.

Bill frantically wanted to rub his own cock. He looked at Trudi and froze at the sight. She was openly rubbing her crotch, slouching in her chair and spreading her legs a little wider with each couple of strokes. Their eyes met.

“Well,” Trudi exclaimed. “I can see how hard you are. Are you going to do anything about it?”

“Not if I’m the only one,” he answered.

Trudi responded by opening her jeans and placing her hand directly on top of her panties. Bill unzipped his pants and rubbed his cock.

“That’s not fair,” Trudi said.

“What?! It’s not like you care what it looks like anyway.”

“Get it out. I want to watch,” Trudi pleaded.


But it only took a second for Bill to expose his rock hard cock and stroke it while watching Jill begin a long, lustful blowjob of her boss. In return, Trudi’s hand moved inside her partially pulled down panties.

Ed let the officer service him for a short time, then he drew her up by one arm and shoved her backwards against the desk. Jill nearly fell on her own, but Ed lifted her and slid her back until only her legs hung over the side. Leering down at her, looking at her chest as it protruded up because of the hands underneath eskort bayan her and the bare pussy awaiting his cock, Ed smiled with disgusting satisfaction.

He did not speak as he used his hands to further spread her legs and step between them. The tip of his cock rested at the entrance to her cunt. Ed grabbed Jill by the hips and spread his own legs to give himself a more stable stance. Then he made the final adjustments to put his cock exactly where he wanted it.

In a sudden, near-violent thrust, Ed drove his dick forward.

“Fuck,” Bill said loud enough to drown out Jill’s wailing. “I didn’t think that would fit.”

“Neither did she,” Trudi said, never slowing down the finger rubbing her clit. “But I guess she’s probably felt that before now.”

Their mutual masturbation continued while Ed started to fuck Jill in earnest. He didn’t have to lift her much because of the handcuffed hands under her back. Jill made things easier by wrapping her legs around his waist and Ed leaned over far enough to suck on her tits, soliciting more moans of joy from Jill.

Soon, it was difficult to determine if the commander’s office or the abandoned house was seeing more action. Bill and Trudi were aroused not only by the video, but by each other. They were sprawled out in their respective chairs stroking as fast and hard as they could. Ed and Jill were doing the real thing, and the sounds of their sex was growing louder and louder with each passing minute.

For the moment, Bill and Trudi could forget about their primary task. It was essentially over. But Bill could fantasize about fucking either Jill or Trudi and Trudi could fantasize about having the lovely Jill all to herself. Ed didn’t need to fantasize about anything. He had what he wanted.

Jill won the race to an orgasm. She cried out with pleasure as her body exploded in a climax that started over and over again each time Ed sucked on her tit or his huge cock hit a new spot in her throbbing cunt. She thrashed on the desk, rolling back and forth as much as Ed would let her.

Trudi quickly followed. She wasn’t nearly as loud as Jill, but there was no doubt in Bill’s mind that she was cumming…more than once. Finally, she convinced him by shrieking, “Ohhhh my God! Yes! Yesssss!”

That was all Bill needed to hear. Just in time, he pushed his cock inside his shorts and rubbed it while long, warm shots of cum poured onto his body, leaving a huge, wet stain of cum at the top of his shorts.

Ed concluded the foursome by groaning hoarsely, pulling his cock out of Jill, and depositing large pools of cum on her chest and stomach. Jill looked on with gratification, suspecting that her long-term tenure with the Patrol was even more secure than the day before.


“What’s it worth to you if I said I could hook you up with Jill?” Bill asked his partner the next day.

Trudi looked at him with suspicion. “I might even start to like you.”

Bill grinned. “Nobody at headquarters has seen the video from yesterday or heard anything from us. I was thinking last night that we are in a very favorable position to demand things from Jill that might otherwise be out of reach.”

Trudi understood. “Tell me more.”

“Here’s the plan…”


The following day, Jill’s personal e-mail contained the following message from an address she’d never seen before: “Officer Brown, I had the rare opportunity to observe you and the commander the other night in his office. You looked SO sexy in those cuffs. I’ve watched the video a half dozen times since then and, well, I’ll let you guess what happened each time. Anyway, since I doubt that you want the chief to see this, I have a favor to ask of you. Today, during your routine patrol of the interstate, you will come across a small blue and white motor home along the side of the road with its emergency lights flashing. Pull in behind it and go around to the side door on the right side. Knock once and enter the motor home. The rest will be self-explanatory.”

Jill’s stomach tightened as she read the message a second time.

“God damn it. I knew somebody would find out,” she said to herself. “Fuck.”

She realized she had no recourse except to follow the instructions of the anonymous sender. It was blackmail, for sure, but the alternatives were far worse. Bill took the chance that Jill would even check her e-mail before work, but was prepared to repeat the process until Jill complied. Her hours were 10 AM to 6 PM and every mile she drove caused her to get more nervous. Bill easily found out what segment of road she was assigned and had Trudi park his motor home in the most secluded area around 11 AM.

They didn’t have to wait long.

Jill’s heart stopped at the sight of the seemingly disabled motor home with the flashers on when she came over the top of a small rise. She pulled in behind it, took several deep breaths to compose herself, and got out of the cruiser.

Only the sound of a single passing car on the opposite side altıparmak escort of the median, and a few birds, disturbed the rural tranquility. The stones under the soles of her work shoes crunched as she approached the side door. She hesitated, and then knocked.

After a brief pause, she opened the door and stepped in.

“Good morning, Officer Brown. Please close the door.”

Jill followed Bill’s orders and then turned to face him. Bill was in a plush seat near the front of the motor home. He was dressed in jeans and a t-shirt. Jill’s attention then shifted to the woman on the couch across from the door. She wore a short, white bathrobe that seemingly covered nothing but skin.

“Don’t be alarmed,” Bill said. “We’re officers, too.” He showed Jill his badge and then flipped his wallet closed and stuck it in his pocket.

“What is this?” Jill asked.

“It’s your opportunity to keep your job, Officer Brown. Or can we call you Jill?” Bill asked. “Is that what the commander calls you, or does he have a nickname that he uses?”

Jill scowled and said, “Give me some proof you have the video you say you have.”

Bill scoffed at her. “C’mon, Jill. What more proof do you need? We saw the cuffs, the blowjob, the fucking on his desk…”

“OK,” Jill interrupted. “What do you want?”

“It’s not what I want, Jill. It’s my partner Trudi,” Bill said.

The women exchanged glances. Trudi smiled wickedly.

Bill said, “She thinks you’re awful cute and wanted a close up view. It would be in your best interest to follow her instructions. I’ll just kind of watch…for now.”

With a nod of the head, he handed off to Trudi.

She crossed her legs in the opposite direction, exposing substantial skin in the process. “You can’t believe how hard I came watching you and the commander, Jill. Watching you strip out of that uniform and taking him in your mouth. Then I saw your beautiful pussy and I just wanted to dive in and eat you so bad.”

Bill felt his cock begin to harden as Trudi spoke, knowing that Trudi herself must be getting wetter and wetter. And the look on Jill’s face was priceless.

“Those uniforms are SO unflattering, don’t you think? I mean, who knew you had such a great body,” Trudi said. “Why don’t you take it off now, Jill, and let us see you in person.”

“You will both pay for this if it’s the last thing I do,” Jill said with contempt.

She removed her holster first. Then she started on her shirt buttons. Trudi and Bill watched every action of her hands as she slowly unbuttoned the shirt down to her belt. Early indications told them the bra she wore today was not nearly as skimpy and sexy as the one she wore for the commander. But as she untucked the shirt and let it hang farther open, the beauty of her tits made them forget about the quality of the bra.

Jill had no previous lesbian experiences. The concept of undressing, and more, for the pleasure of another woman was not something she’d spent much time thinking about. Even now her mind was on Bill. But it was the lovely woman under the bathrobe that she should have been concerned with.

When Jill hesitated, Trudi ordered her to continue. The shirt came off and all eyes focused on the full breasts supported by the black bra. Bill surreptitiously moved his rigid cock to relieve the pressure inside his pants. He fought the temptation to rub it, knowing they were in for a long session and he’d have plenty of chances.

“The pants next,” Trudi said.

Jill removed her shoes, socks and pants with Trudi and Bill both getting excellent views of her body as she bent down to pull the pants off her legs. A matching pair of black panties hugged her ass and pussy. Trudi felt her nipples harden and extend against the soft fabric of her robe.

“Now get naked,” she demanded.

Jill forced herself to think about Bill and the ever-growing lump in his jeans. Anything to not take into account the real reason she was stripping…Trudi. She reached behind her to unhook her bra and consciously turned slightly to face Bill, not Trudi. Jill let the bra slip down her body until she stood with it in her hand, topless for the other officers to see. Then she tossed the bra on top of her pants.

“Face me,” Trudi told her.

When Jill was squarely facing her, Trudi said, “Touch your nipples. Squeeze them. Play with them.”

As Jill obeyed, Trudi reached inside her loosely tied robe and began massaging her own tits and nipples. Her lips parted just a crack in response. She uncrossed her legs and let them spread a little.

Bill couldn’t resist any longer, He rubbed his cock through his jeans and leaned back in his chair to take it all in.

Once Jill’s nipples were sufficiently erect, Trudi said, “Now the panties.”

Trudi and Bill stared intently as Jill pulled off the underwear and uncomfortably stood naked in the center of the motor home.

“Touch yourself, Jill.”

Jill wanted to protest. She wanted to cry out, ‘Enough is enough.’ But her career, what might be left of it, flashed through her mind. She thought about the video, and a hand unconsciously sank between her legs. Next thing she knew, Jill was swiping her fingers over her moist cunt and up to her clit. She separated her feet a few more inches and started to masturbate.