Mike the Gang Bang Bitch

Mike tried to repeat the name back to Mr. Thomas but with a thumb in his mouth he did little more than mumble. Mr. Thomas smiled, "Never heard of it. Let me explain. You will be arrested crossing the border with a ridiculous amount of cocaine. You will have a trial, but it will be a shame. By Tuesday you will be processed and in a cell in Centro de Ejecucion de Sanciones, that is where they send all the drug runners. As a gift to them I am going to dress you in the little girl outfit I offered you for the back alley."

Using his thumb to guide Mike to a chair Mr. Thomas sat the captive sissy down. "Now I give it an hour before you officially go missing. The paperwork will say you escaped. But that is just so no one comes looking for you. The last 24 hours will be a cake walk compared to the rest of your life. So can you be honest with us?"

"Yes Sir." Mike muttered as he looked down at himself. His penis was rock hard and tenting out the front of his satin g-string.

"When did you realize you were a sissy whore." Mr. Thomas asked pulling his thumb from Mikes mouth and stepping back No camera was visible but Mike was sure they were recording this somehow.

He was asking about the dream the dream Mike had had every night since his wife left. Gerald's, his mother's boyfriend, voice was garbled in the dream the words always illegible. But Mike knew what they were "You little freak. What kind of perv wacks it to his mommy's panties."

The dream was always the same forced to strip Mike was only allowed to wear the panties he had just came in for the next week. It was summer so Mike had no were to go. Every morning Gerald would fuck Mikes mom and then have Mike give him a blow job. Even after just fucking Gerald could always fill Mikes mouth with a heavy load of cum. Every night before bed Mike was forced to beg Gerald to fuck him in the ass, and every night Mike would cum in unison with Gerald. His mother didn't speak to him the entire all week; and when the week was over Mike left home and never returned.

"Interesting story, We will expand on that later." Mr. Thomas said as he handed Mike a large Dildo. "Why don't you fuck yourself while we talk."

Mike turned around in the chair and pulling his panties aside slid the plastic cock inside his body. The base was a suction cup that secured the cock firmly to his chair. Mikes legs were sore but he did his best to bounce up and down on the dildo while Mr. Thomas talked and talked. Mike couldn't remember all the questions he was asked but he did know he answered them truthfully. Terrified of living a life as a Mexican prison whore.

A hard knock on the door ended the questions. Mr. Thomas stood up and motioned for Mike to answer the door. Standing up the dildo made an audible pop as it slipped free from Mike's ass. Walking to the door Mike took a hold of the door and looked to Mr. Thomas, hoping for a miracle reprieve from what ever was to come.

"When you open the door have a big smile on your face and yell, as loud as your little whore throat will allow - I need cock and I need it now."

Opening the door Mike froze. Mr. Thomas wasn't lying there were easily a hundred guys lined up outside the door. Mike tried to call out but his voice trembled and his lips wouldn't part. Leaning in as he give him a hard slap on the ass Mr. Thomas whispered into his ear, "Talk now or we drag you to the parking lot and fuck you out in the open."

"I NEED COCK AND I NEED IT NOW." Mike screamed. His voice more terrified then erotic the assembled crowd of men went wild. Mr. Thomas smiled and stepped back.

The first man entered and bent Mike over the bed not even bothering to unzip his pants he just pulled them down and slammed his cock deep into Mike. Letting out a moan Mike braced himself against the bed as the man pounded into his backside. Taking a hold of Mikes shoulders the man rammed himself fully into Mike 5 times before he pulled out and shot his load all over Mikes back.

Shaking the last drops of cum from his cock the man snorts and says, "I have had better."

Standing up Mike returns to the door for another man. The sun is setting as the tenth man walked out. His legs ready to give up Mike stumbled to the door. Looking over at Mr. Thomas who was bored while looking through his phone. "You know Mike, your going to run out of time."

"What are you talking about." Mike asked waved the next man in.

"Did I forget to tell you. You don't finish fucking these one hundred johns, well you are off to Mexico." Mr. Thomas said, an evil smile spreading across his face.

Mike looked from Mr. Thomas to the door. Walking back to the door. Mike pulled the next three guys in. Jumping on the bed. Mike directed two men to his holes and grabbed the other two cocks in his hand. Within Minutes the two in his holes shot their loads, both pulling out and spraying all over Mikes body. The two in his hands moved quickly to his holes, barely giving Mike enough time to call out, "Next two come on in."

Mike spent the next eight hours with cocks constantly spewing cum across his body. When the last man filed out. Mike turned his head towards the door and smiled when he realized the line was now gone. Exhausted and for the first time sure that he wouldn't end up in a Mexican prison he passed out. All night he dreamed of cocks and dancing around in skimpy panties while being showered in Cum. The showers of cum began fill the room more and more until Mike was wading knee deep in cum. His lust over came him and he dropped down gulping handfuls of it. The more he drank the more it rained down on him. Soon it was up to his stomach, and then his chest. Panic started to rise in Mike. He was going to drown he was going into drown in cum. Just as the cum was about to cover his eyes Mike felt a splash of warm piss hit his face and he was awake.

Stepping from the shower exhausted after service all the men that were still in the hotel room Mike looked to the bag Mr. Thomas had left with his clothes. Pulling the garments from the plastic bag Mike wasn't surprised to find out the deal wasn't what he thought it had been. The flower bra and panties from yesterday were in the bag someone had stripped them off of him during the gangbang. There was also a very tiny pair of denim shorts and a pink spandex tube top. The clothes were clean but the bra and panties were stiff with dried cum. Mike dressed quickly taking a moment to look at himself in the mirror the bra straps looked ridiculous and the waist band of his panties was visible. After pushing the panties down into his shorts Mike put on his heels and exited the bathroom.

Mike was desperate to go home and wasn't happy when he found twelve men as well as Mr. Thomas waiting for him. "I thought it was over and I could go home."

"You will, very soon. Just a couple of parting gifts." Mr. Thomas said as he walked Mike to a small table and bent him over. With a rough tug he pulled Mike's shorts and his panties down to mid-thigh. Placing a cold metallic object against mikes sore sissy cunt he pushed it deep inside him. Thankfully Mr. Thomas had lubed it before inserting it. Grabbing a pinch of Mike's hair Mr. Thomas pulled him to a standing position. Mr. Thomas pulled Mike's shorts and panties up making sure the panties were sitting a good inch above the waistband of the shorts. But he didn't button the shorts up. Instead he walked Mike to the rooms door, which stood wide open, and stood him so that he was visible to anyone in the parking lot. "Everyone here was so happy with you this weekend that they wanted to offer you one last cum shot."

Mike started to get down on his knees but Mr. Thomas stopped him. "Oh no slut, Not your face."

Pulling mike back up Mr. Thomas pulled the front of his panties away from his body. "OK gentlemen, time to give your thanks."

All twelve men lined up with their cocks out and ready to explode. Each man in turn stood in front of Mike and masturbated until they shot a load into the front of Mikes panties. AS the last men left Mike looked down and the thick pool that was already soaking through the denim shorts he was wearing. Letting go of his panties, Mike zipped the shorts up and looked at Mr. Thomas. "Can I go now."

"Would you like bus fare?" Mr. Thomas asked a wicked grin on his face.

"I drove." Mike responded looking out to the parking lot.

"Oh they were threatening to tow that so I had it driven to your apartment, and dropped off. I figured it was the least I could do." Mr. Thomas said as he slipped a phone from his pocket and started dial, "That isn't true at all, you made me negotiate too much this weekend Mike. I started to feel like I wasn't going to come out ahead."

Looking up with a grim smile, Mr. Thomas reached up and took a hold of Mike's nose, "I always come out ahead."

Making his call Mr. Thomas held the phone up to his head. AS he started his conversation he fished two more crumpled dollars from his pocket and stuffed them down the front of Mike's panties.

Mike closed his eyes and waited for Mr. Thomas to leave. Once everyone was gone Mike looked around the room desperately hoping they had just hidden his clothes. Not finding anything Mike reluctantly left the motel. The bus ride home was surprisingly easy, turns out no one wanted to sit next to the sissy that was dressed like a slut and smelled like cum.

Stepping off his bus Mike was happy to find that his car had been returned it was backed into a spot three doors down from his apartment. Slamming his door shut Mike kicked off the heels and tore of the thank top and shorts. He paused at the panties, they were still wet and cold against his skin. Slowly pulling them off Mike made sure to his best not to lose any of the cum that clung to the delicate fabric. Carefully he scooped the cum that clung to his body free before stuffing the panties in his mouth. Closing his eyes Mike moaned and reached down tugging gently on his sore penis.

Getting himself together but not removing the panties Mike hurried into the bathroom and turned the shower on reaching back for the first time. Mike tried to remove the plug Mr. Thomas had inserted before sending Mike home. The harder he pulled on it the larger it seemed to get but once he stopped pulling it would return to its original size.

An alarm made Mike jump, it was Monday morning and his alarm was going off that meant he had to leave in 15 minutes. Rushing through the closet connecting his bathroom and bedroom Mike didn't notice that his clothes were different. In his darkened room he didn't notice the giant wall mural that covered the wall opposite the door. HE turned off the alarm and rushed back to the shower. Pulling the curtain open Mike noticed the first change since getting home. Mounted across from each other were two large dildos. They were bolted to the wall and while Mike didn't have a lot of time to try and remove them they didn't budge when he pulled on them. Mike washed up and dried off as quick as he could.

Pulling the now cumless panties from his mouth Mike walked into his closet and flipped the light on. Once again he froze. Almost all of his clothes were gone, replaced with woman's clothing. All that was left was one pair of men's slacks and one dress shirt. Even his undershirts were gone, replaced with camisoles. The one dress shirt he had was very thin and it would be noticeable if he didn't wear an undershirt. Looking through all the camisoles in the drawer mike found the least feminine one and pulled it on before selecting a pair of panties. Without putting too much thought into it Mike searched through the entire drawer until he found a pair that matched the camisole. They were cotton, but a thong so maybe a little less sexy but still a little slutty.

Once his pants and shirt where on Mike went hunting for socks. Only he didn't have any his sock drawer was now filled with nylons and pantyhose. Slamming the door shut Mike decided to skip socks and grabbed shoes heading into his room. Flipping the light on Mike froze, dropping his shoes. Opposite of the door to the living room was a giant photograph. Wall to wall and floor to ceiling of Mike wearing just a pair of bright pink panties and covered in cum while surrounded by cocks.

Mike kept his feet under him, but started to cry. Sucking the inside of his cheek between his teeth Mike bit down hard enough to draw blood. The lack of pain was supposed to wake him up but it didn't there was pain and this was all real. Steading himself Mike turned the light off and went back out to the living room, moving through the bathroom.

The drive to work was quickier then Mike wanted, no traffic meant no time to contemplate the situation he had gotten into. Pulling into the parking lot Mike's heart sank his boss was standing outside the office talking into his phone. Mike pulled into a spot and started to climb from his car. His feet slipped around in his shoes and Mike was regretting not stopping and buying a pair for today.

"Mike, good you're hear the client moved the meeting up to first thing. We are already late. I tried to call but... whatever let's go. This is a big contract." Mike climbed into the passenger seat of his bosses oversized German car and slipped into the seat. Mike's boss Jack had never had his Fathers eye for accounting, but he worked hard to keep the company afloat. "This guy's third wife is leaving him, and is demanding a full audit of the company. I talked to him last week, said he has had his eye on our firm for a while and is interested in keeping this relationship going past the one month for the audit. I doubt this guy is hiding anything the wife sounds like a real bitch."

The conversation was one sided and Mike ignored his boss talking. All he could think about was the panties he was wearing and the plug in his backside. Pulling into the parking lot Mike instantly recognized the building. The Anderson building was an art deco masterpiece that had gone to ruin before it was bought by hedge fund a few years ago. The owner was supposed to be a reclusive old school tech billionaire that got tired of silicone valley and moved to the mid-west.

A secretary met them in the lobby and escorted the two men to the top floor. She kept eyeing Mike out of the corner of her eye looking up and down. Normally he would have been excited, but right then he was terrified that she realized he was wearing lingerie under his clothes. The elevator finally chimed for the penthouse and the two were escorted to a glass encased conference room. One man was seated with his back to the window and the other was looking out. The man seated looked familiar but Mike couldn't tell from where.

Opening the door, the secretary called out, "Mr. McCormic, Mr. Winslow your eight AM has arrived."

The man seated stood and smiled, he really looked familiar to Mike, then the man at the window turned. It was Mr. Thomas. The man seated stood and smiled broadly, extending a hand to Jack, "Gentlemen sorry to have to reschedule, Mr. McCormic was in negotiations all weekend on a new acquisition and is flying out in a few minutes to take a much needed vacation."

"Mr. Winslow, nice to meet you finally after all of our phone calls and the negotiations it is nice to put a name to a face." Jack said as he shook Winslow's hand. Mike never noticed that Winslow didn't offer to shake his hand as they were directed to take a seat.

Folders were slid across the table to Mike and Jack, Mike picked his up and immediately jumped into his spiel about how they wanted an independent audit, and would be fare but honest and transparent. Mike picked up his packet and opened it just enough to see that it didn't contain any financial paperwork. It was full of pictures of him, posing, fucking dressing, getting pissed on ever act from the weekend was represented.

Finally, Mr. McCormic spoke for the first time. "I expect you to be independent and transparent. I am not hiding anything. The myth of my wealth can be very troubling at times like this."

Jack had a terrible poker face and was not hiding his star struck gaze. "I have gotten this far by knowing a mans character at a glance. I tell ya Jack I have a good feeling about your company. Listen Jack, I want... I'm sorry what was your name again?"

Mike mumbled his name. "Mike that is right. Listen I want Mike to get started right away, and I have a flight to catch. If it is ok with you I am going to have you and Frank finalize all the details and I am going to walk Mike over to our accountants and get him introduced."

Jack shook his head and patted Mike on the shoulder. Mike felt the strap of his camisole laying between two fingers as Jack talked he couldn't hear what was side he was too distracted, convincing himself that Jack knew what he was wearing under his shirt.

Standing Mike shuffled out of the room and into an elevator with Mr. Thomas, no Mr. McCormic he corrected himself. As the doors closed McCormic reached up and smacked Mike in the back of the head. "Get those boy clothes off. In this building you will dress like the sissy tramp you are."

Without out arguing Mike pulled his shirt off and dropped his pants to his ankles. He let the shirt fall to his feet as he stepped out of the pants. "Shoes too."

Mike kicked his shoes off and pushed the pile away just as the doors opened. McCormic stepped out waving Mike on. As he stepped from the elevator Mike was greeted by a stern woman in a perfectly tailored outfit. She was holding a pair of acrylic platform heels - they obviously weren't for her. Mike put a hand on her shoulder as he slipped the shoes on one foot at a time. As he was slipping the second heel on she finally spoke, "I wouldn't take too long, he likes to send Sissy's down to the mail room to be broken in."

The heels clicked furiously as Mike crossed the room wearing nothing but a white cotton camisole and thong panties. As he crossed into McCormics office the woman closed the door behind him. "How long have you been planning this?"

"Mike you get one question before I explain things to you, is that what you want it to be?"

"When will this be over?" Mike asked as squirming just inside the door.

"Now that is a better question." McCormic said as he waved Mike closer, "Decent question, officially this ends in one month."

Once Mike was close to the table McCormic grabbed him by his hair and forcefully bent him across the table. "Unoffically, it ends when your ass bores me. The better question is how this ends."

"How does it end?" Mike asked just before a thick leather belt slammed into his backside.

"Very good, you can be taught." McCormic said as he slammed the belt into Mike's backside once more. "I want you to count now."

WHIP

"ONE" Mike called out tears streaming down her face.

"Terrible outcome, I sell you to a brothel down in southern mexico.'

WHIP

"TWO"

"Bad outcome, I sell you to an acquaintance who has a dungeon full of sissy slaves." McCormic said as he reached down and pinched Mike's ass.

WHIP

"THREE" Mike whispered as he tried to catch his breath.

"Good outcome, I turn over all the video and photographic evidence to you and you walk out of this building a well-trained sex doll."

WHIP

"FOUR." Mike said through clinched teeth. "What about my job."

"That is a second question...

WHIP

"FIVE"

"I will answer it anyways. This is your last job as an accountant. You will sign anything and everything I put in front of you. The only counting you will be doing is how many cocks you sucked that day. Now you are really going to regret asking that question."

WHIP

"SIX"

"You know Mike, when you walk out of here big fake tits and plump cock sucking lips you are going to thank me for opening your eyes to just how much of a sissy slut you really are."

WHIP

"Seven"