tagGroup SexUndercover Agent To Mole Ch. 01

Undercover Agent To Mole Ch. 01


READERS NOTE: This story could have been listed under a number of different literotica categories but I chose to list it under group sex since there is much of that is the story. The story contains group sex, anal sex, oral sex, vaginal sex and lesbian sex. There are also accounts of reluctance and non consent. I had planned that it only be one chapter but as it got longer I decided to break it up into three chapters. All characters are at least 18 years of age.


Callie Sanders had been with the FBI for ten years and she had been one of the most effective agents in the district. She knew that she had to keep up with male agents so she worked extra hard and took on dangerous assignments. She had earned many citations and awards, enough to irritate her male colleagues. But today she was sitting in the Director's office for a different reason.

"Callie," Director Barnes began, "We have been watching you for the past two years now and we know that you are the mole in the department."

Callie cringed as she always knew that this day would come. As she sat in the chair she reflected on when and why she went to the other side. Her thoughts took her back to three years ago when she was undercover and had penetrated the Donatello family.


Callie Sanders had volunteered for the undercover role to penetrate the Donatello family and gather incriminating evidence against them. Callie was a pretty blonde at the age of 29 and she kept herself in fabulous shape. She worked out everyday and she had attained a black belt in karate. Callie was 5'7" and weighed about 120 to 125 pounds. She normally kept her hair short but she had let it grow longer for the assignment. Callie had a cute figure with small firm breasts, shapely lags and a very delectable ass. She almost hated her ass because it always drew a wandering hand from men in a crowded area. She often heard her male colleagues comment about her killer ass. Callie was no virgin as she had lost that in college but she was very selective about whom she slept with. She did not date anyone from the Bureau and she did not engage in any kinky sex, particularly anal sex. On occasion guys would try to get into her ass but she put them off and it was the last time that she dated them.

Callie had been accepted as a potential buyer when she penetrated the family. She had been to several meetings and had earned their trust to date. She usually met with Frankie, Joey and Sal three of the soldiers for the family. She had hoped to get closer to the head of the family Tony Donatello but that was going to take a lot longer. Sal was still a little suspicious of her particularly when she asked about meeting Tony; she was a little too persistent for Sal. The night that the buy was to take place Callie was wearing a wire.

Callie entered the warehouse to meet with Sal, Joey and Frankie while the building was staked out by bureau agents. As soon as the buy went down the building would be rushed and arrests would be made. Callie walked in and as always Sal patted her down. Callie despised his touch but she knew she had to endure it. Sal smiled as he felt her up and he always patted her ass several times. Joey and Frankie laughed as they knew that Sal was feeling her up.

"Hey Sal, lighten up. You know she's not packing," Joey said with a laugh.

"Yeah, yeah but the first time I don't check you know what happens. She'll drop all three of us," Sal replied also laughing.

"Come on doll we are going in the other room," Frankie told her.

The three of them walked in another room and Joey held the door for all of them. Callie never saw it coming as Joey moved quickly behind her and covered her mouth with a chloroform soaked rag. Callie was out cold in seconds. The three guys carefully lowered her to the floor and then Frankie turned on a compressor to fill the room with sound. Outside the agent listening could only hear the compressor as he tried to pick up voices in the warehouse. Frankie, Joey and Sal did not talk however and they carefully removed the wire from Callie's body. Sal got a hard on just from looking at her bare skin when they opened her blouse. The three of them set the wire down on a table and then they carried Callie out back to a car parked behind the warehouse.

By the time the agent in charge of the stake-out decided that Callie might be in danger and ordered the bust, Callie was already on her way to another location with the three family soldiers. The agents rushed the warehouse and found the wire on the table. They then realized that the bust went bad and that Callie was in big trouble. They left the scene and reported the outcome to the Bureau Chief. The FBI then obtained a search warrant and headed to Tony Donatello's mansion on Long Island.

Tony did not resist the search of his property and he denied any knowledge of Callie's abduction. When questioned about the whereabouts of his three soldiers, Tony laughed and replied that they were probably out with their girlfriends and getting laid. The FBI was frustrated with Tony but they knew that they could not prove that he was involved. They left Tony's house and returned to Manhattan frustrated with the events of the evening.

When Callie came to she was naked and bound. She was tied up with her hands behind her back that were held by an overhead rope. Her arms were pulled up tight causing her head to rest on a mat on the floor. She was on her knees unable to move and her killer ass was pointed in the air. She knew she was very vulnerable and she was fearful of what they would do to her. The she realized that her abductors were naked also.

Sal walked over to her with his hard cock bobbing in front of him and spoke, "The boss said we could have some fun with you before we bring you to see him," he said as she ran his hand over her shapely ass.

"Keep your hands off of me you pig," Callie snapped.

The three of them laughed and Sal said, "Now I don't think that you are in any position to be giving orders."

"Fuck you!" Callie snapped again.

"No see you got it wrong again. We are going to fuck you," Sal snapped back and added, "In fact we are going to fuck you in your hot tight ass."

Callie realized her fate and then she changed her tune, "No please not in my ass I have never done that. You'll hurt me bad."

"Nonsense once we break you in, you'll be begging to get an Italian sausage up your poop chute," Sal replied.

Joey moved over and began to lubricate Callie's asshole. He stuck his oily finger in her ass and applied the lube liberally. "She's really tight," he announced.

Callie screamed for him to stop as she tried to move away from him. But she was unable to move and Joey continued to finger her ass. He tried to add a second finger and Callie screamed again.

Sal scolded her and said, "Stop screaming and let Joey get you ready. If you keep yelling I am going to dry fuck your ass and then you will feel unimaginable pain. Behave yourself and we will break you in and fuck you with the smallest cock first. It's your choice."

Callie knew it was going to happen and she resolved to suffer the least pain possible. Joey was smaller than Sal and Frankie but even then he had an impressive cock. Joey liberally lubed his cock and then he placed it at the entrance to her ass. He pushed against her sphincter and the head began to open her up. Callie screamed again in pain this time as the head pushed its way into her ass.

He was gigantic, long and wide and Callie screamed as he began to work his way into her poor tight ass. Callie could actually feel her stomach cramping around him as he stirred her insides and it burned when she clenched her ass muscles around his thickness. Shaking and sobbing with painful ecstasy, Callie fell forward on her head with Joey's hands keeping her ass high in the air for him to plunder. Callie screamed as it felt like a hot thick poker had just been rammed into her ass. Tears filled her eyes as her violated asshole spread to accommodate Joey's thick cock. Callie thought back to when she first lost her virginity and remembered the pain was just as intense.

Callie cried out loud only to have the sound ignored as Joey's complete length filled her. She felt him flex his cock deep within her bowels as the searing pain continued. Joey reached one hand under Callie and teased a nipple. Then he moved his other hand down and rubbed softly against her clit. Callie's body responded to his stimulus and her stomach convulsed with mixed signals.

The intrusion in Callie's ass didn't feel quite as bad now as Joey's fingers continued to tease her clit. She felt him move inside her ass now and she tried to relax her ass muscles. Callie's body was working back and forth on Joey's cock now and she was amazed at the feeling of the cock in her ass. Callie's clit was buzzing and the fullness in her ass just seemed to excite her pussy even more.

Joey started hammering into her ass now. His fingers were still busy on her clit but now he had two fingers drilling in her pussy as the others fluttered around her clit. Callie's whole body was aflame as she could feel his fingers pressing against the thin membrane separating her ass from her pussy. She could feel his hard cock sliding in her and the pressure of the fingers on his cock through the membrane.

Frankie yelled out, "Oh yeah, fuck her, fuck her ass, fuck it good!"

Callie didn't need Joey to force her on his cock anymore. Callie's entire body was fucking back at him of its own accord. She could feel an enormous orgasm building with in her. Her pussy was swollen to new proportions.

"Oh God," Callie thought to myself, "I'm going to cum again, Oh God!"

Joey continued plowing into her. The hot dry depths of her ass were so tight around his cock she knew that he was going to cum hard too. He worked his fingers faster inside her as he rammed his cock hard into her ass. Callie started sucking air like a mad woman. Joey's groin made hard contact with Callie's ass. Callie felt her pussy spasm suddenly and then her whole body went rigid. She felt Joey's cock swell in her rectum and then hot spurts of liquid lava hit her deep in her bowels, giving her a cum enema. Both of them shuddered hard as every muscle tensed and then relaxed. Callie felt a hot explosion as her body was overcome with the most violent orgasm she had had in awhile. Callie could still feel Joey's cock throbbing and spurting deep within her. She felt Joey's cock shrink in her ass and then slowly back out making an audible popping sound. Callie's ass was still high in the air and her thighs were aching. Joey lovingly caressed Callie's shapely ass cheeks.

"Well done Joey, well done Callie," Sal congratulated them both.

"God I feel like 2x4 was shoved up my ass. I have never had a cock that size in there before today," Callie gasped.

"You did well you were able to take it all. It was exciting to see your ass full of cock," Sal added and then said, "The others will be easier to take now."

The rope holding her arms was loosened but her hands were still tied behind her back. Callie knew that she was in for another sound fucking. Sal wasted no time in getting to her pussy. He rolled Callie over onto her back and massaged her firm tits with his oily hands. Then he slid his hands down her body and massaged her legs and thighs before finally moving to her pubes. Sal rubbed Callie's vulva with his oil soaked hands and then he began to finger her pussy. Sal pushed two fingers into Callie's pussy and then another finger into her asshole. Callie moaned with the double intrusion but she did not object. Sal then pushed his middle finger into Callie's ass and his thumb into her pussy as he lowered his mouth to her cunt. He then drove his big thick cock all the way into her sopping wet pussy with one thrust. Sal fucked Callie hard and fast causing her to cry out in ecstasy.

Sal rolled over pulling Callie with him and all the while he kept his cock buried in her pussy. Callie was now on top of Sal and he reached up and fondled and squeezed her tits. He rolled her nipples in his fingers as he drove his cock up into her pussy. Callie was out of control as she rode his cock. Just then a familiar figure moved in front of Callie.

Callie recognized Joey and instinctively taking his cock in her mouth. Sal continued to fuck her from below and fondle her tits as she sucked on Joey's cock. Then Frankie moved behind Callie. He was already erect and he thoroughly oiled his cock before getting behind Callie. Sal held Callie tightly pulling her down to his body and causing her ass to rise slightly. Joey held her head firmly between his hands as he fucked her face.

The young man aimed his cock at Callie asshole and began to push in. Even though Callie had her asshole stretched by Joey and Frankie had lubed his cock, the fit in her ass was still incredibly tight. Callie realized what was happening to her again and she once again tried to break free but Sal and Joey held her securely in place. Callie tried to protest verbally but her yells and screams were lost on Joey's cock and her actions almost caused her to gag. Frankie had about half of his cock in her when Callie tried to scream in protest and tossed her head from side to side.

The pain was excruciating as it was before as Frankie's cock worked its way deeper and deeper into Callie's ass. Her eyes welled up with tears and she felt her anal channel being stretched to new dimensions. Everyone had remained still until her ass was penetrated and now the three men picked up the pace again fucking Callie in all three of her orifices. Callie could only go with the flow and let her self be used as they had intended. The pain had subsided somewhat and now she felt more of a bloating and cramping sensation. The three men had established a rhythm and their cocks were now gliding easily in and out of Callie's holes. The cramping had stopped and now Callie only felt somewhat constipated with the cock in her ass. The young man in her ass suddenly stiffened and fired a barrage of spunk into her ass. She had never felt that full as her asshole was flooded with his seed. The warm liquid did feel somewhat soothing in her recently ravaged asshole.

Frankie pulled his semi-hard cock from Callie's ass and she could feel the cool air of the room touch her anus. She also felt his cum trickle out of her ass and run down between her thighs onto Sal's big balls. Callie had just started to relax and focus on the two cocks in her pussy and mouth when she felt another cock at her asshole. Frankie had remained hard and decided to fuck her ass again.

"Not again," she thought to herself.

Once again Sal and Joey held her securely as Frankie's cock was pushed into her ass. Once again her rectum was stretched to accommodate to the new intrusion and once again Callie experienced the same feelings, initial pain transitioning to bloating and cramping and then the feeling of fullness. The three men again established their rhythm and worked Callie's body. This time she felt Sal stiffen and shoot his load into her pussy and right after him Frankie in her ass ejaculated. Her holes were flooded and drenched with male seed and as she felt the hot spunk flowing into her holes Joey caught her off guard and came in her mouth.

Callie couldn't believe all the sperm that filled her holes she seemed to be swimming in it. As the bodies untangled a different cock entered Callie's pussy and soon another entered her mouth. Then a third cock entered her asshole. Callie's body was consumed with lust and she just allowed her self to be manhandled and used for pleasure. Sal was the last one to fuck Callie's ass. Callie was lying face down with cum still oozing out of her ass and pussy. Sal lifted the almost lifeless body of Callie up by her hips until her asshole was level with his hard cock. Callie kept her face down on the mat and turned to one side to watch Bridget. Sal slowly slid his thick cock into Callie's well used asshole. Callie just emitted a low moan as she felt Sal's thick cock enter her ass. Callie had lost track of how many times the cocks had fucked her that day but she knew that all three had been in her ass. All she knew was that she had been repeatedly stretched more and more each time she was butt fucked. Now she felt Sal stretch her even further as he sank his cock all the way into her ass. He then began to fuck her slowly watching his cock chamber and re-chamber in and out of her shapely ass. Sal stroked a few more times before he felt his orgasm build in his balls. One deep thrust and then he flooded Callie's ass with another huge load of cum that mingled with the numerous loads that previously filled her ass. Callie looked as if she was in a trance as the big cock filled her ass. Sal pulled his softening cock from Callie's ass and he watched as his seed ran out of her enlarged anus. Callie squeezed her muscles as if she were trying to poop and forced more cum out of her anal channel.

"Okay let's get her cleaned up and dressed. We don't want to keep the boss waiting," Sal directed.

Callie was wiped with wet towels and then dried off. Her wrists were untied so that she could get dressed and then they were retied. Callie was led out to the car and placed in the back seat between Sal and Frankie as Joey drove the car to the Donatello mansion. Callie had no idea what was in store for her when she finally met Tony Donatello.


Callie was ushered into a huge room in the Donatello mansion where she was told to sit a chair facing and impressive desk. Shortly afterward, Tony made his appearance and smiled at her as he sat down behind the desk.

"So my dear how are you feeling? I hope the boys weren't too rough with you? You don't look so bad. Can I offer you a drink?" Tony began.

"Some water would be great," Callie said timidly.

"Joey, bring the lady some water and bring a bottle of wine too," Tony ordered.

"So Callie, I have learned that you are an FBI agent and a very good one at that. Also we knew that you were wearing a wire tonight. We were a little suspicious of you so we had the scanner set up in the room," Tony told her.

"What's going to happen to me now?" a frightened Callie asked.

"Well that's up to you. You have some options. The first option is to cooperate with the family and be a mole for us in the FBI office," Tony explained.

"And the second option," Callie asked.

"That one's not so good. We would have to kill you but before we did you would be turned over to my 25 soldiers and they would have their way with you first," Tony said firmly almost annoyed that she asked.

Callie knew her life was over if she refused to cooperate and just the thought of 25 men having their way with her was worse than the threat of death. She knew she really didn't have a choice. She was a clever agent and she was convinced she could pull it off as a mole in the Bureau.

"All right, I accept your offer. How does it work?" Callie replied with more confidence in her tone.

"That's a good girl," Tony said and poured a glass of wine for both of them.

He held the glass up and said, "Salute," in a toast to the arrangement.

"Oh there are some more details. You will receive compensation for your cooperation. Also if Sal, Frankie and Joey want to spend some time with you, you will accommodate them. They will be discreet and your cover will never be blown," Tony promised.

Callie looked at the three soldiers in the room and they were smiling at her. She knew that they were anxious to get back at her hot ass and there was nothing she would be able to do to deter them. She decided that it was still better than death so she nodded in agreement.

"Good, then it is done," Tony said and then concluded the meeting by saying, "I will leave you four lovebirds alone then."

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