For A Dollar More Pt 05

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Disclaimer:

All characters are consenting adults (over 18). This story is loosely based on

my actual experiences; however the names are fictional.

Story background:

Mike is a 45-year-old married (to a woman) man who has secret desires to explore his sexuality with other men. Mike is athletic and fit and generally alpha in his daily life. But for some reason, Mike has secret thoughts about being a bottom for other masculine men.

During the day, while is wife is at work, Mike sometimes visits gay cruising sights to explore his fantasy and consider potential hookups. Mike works from home and works for himself as a tech business consultant. Since he is self-employed, he can set his own schedule.

Earlier this week, Mike met a guy online named Gus. Gus is five feet five inches tall, he's from Nicaragua and he has a thick, six-and-a-half-inch uncut cock. Gus invited Mike over to engage in some role play. In the role play, Gus is a paying customer, and Mike is a cheap street whore that is willing to do things for Gus for a certain price.

Gus has been using his "For a dollar more..." fetish to take control of Mike's mind. Mike is now doing things that are slightly outside his comfort zone. Gus keeps taking him deeper and deeper into his perverted world.

Gus has convinced Mike to wear a wig, lipstick and let himself be called Mary. Mike does not think of himself as a crossdresser, but Gus has used his fetish to bend Mike into submitting. He used a photo he took of Mary to drum up "customers" using the same online service that Mike used to meet Gus.

We catch up with Mike as he plans to meet Gus a fourth time. He knows that Gus has invited three other men to the meeting today, so he is nervous and excited at the same time.

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It was a little after 10 a.m. when I signed out of my computer and went upstairs to prepare myself for the meeting with Gus and the new "customers" he had lined up for me. I knew that my old friend, Ned, was planning on being there. Gus had also mentioned to other men in their sixties who agreed to attend, bringing my total customers to four.

I was excited by the idea that I would be entertaining four men at the same time; but I was a little concerned that two of the men were in their sixties. I was also hoping that none of them were perverts like Billy. I was excited to find out what it was like to service four hung men at the same time. But I was little concerned that I was letting myself fall too deeply into my secret world.

While I was upstairs showering, my cock wouldn't settle down. I guess my thoughts about today's events were registering in my subconscious, causing me to have a permanent erection. As I walked into the closet to find the shorts I wore yesterday, It occurred to me it didn't matter what I wore during the two mile drive to Gus's place, since he made me strip in the garage anyway.

I recalled how I stripped just outside his garage door yesterday, just to add some extra excitement. I started to consider the fact that my alter ego, Mary, was a slut, maybe I should act more like one. So, I decided to wear the minimum clothes I could for the drive over and then leave them by the garage door before I entered. I threw on the tiny running shorts I wore yesterday. My cock imprint was obvious through the thin material, and the back went right into my ass crack. I decided I could make the two-mile drive with no shirt, and I also left my sandals in the closet. I was going to leave the house wearing just a single item of clothing.

I headed downstairs, grabbed my keys and stepped into my garage to hop in my car. Once inside, I started the ignition and then opened the garage door using the remote.

"I can't believe you're going out of the house dressed like this," the voice in my head screamed, "What if you get pulled over, you're only wearing a tiny pair of running shorts; your cock is practically poking out."

I didn't listen to the inner voice; I was too horny to stop the momentum created by my lust. When I went to Gus's house, Mike left the picture and Mary emerged. Mary was a prostitute who fucked men for a dollar. Mary didn't wear clothes into Gus's house. Mary wears no more clothes than she needs to while in-transit to serve customers.

Mary Meets Customers for a Dollar More

I was so excited on my drive to Gus's that I let my cock poke out of my shorts through the leg opening. I gave myself a few strokes every once and I while as I navigated the treelined neighborhood streets just before 11 a.m. Fortunately, most people were at work and the kids were in school, so I wasn't worried about being discovered.

After a few minutes, I pulled onto Langdon Street and pulled into the driveway of the fourth house on the left. Today, I noticed more cars parked in the street near Gus's house than I noticed days prior. As usual, I pulled into the driveway on the far-right side and turned off the ignition. I was instructed to enter the garage via the side door of the garage which was located on the right side. I looked around to ensure there were no neighbors out and about, then I started to open my car door to make the short walk to the garage.

As I was pulling the handle, I wondered if I had the nerve to leave my shorts in the car and make the walk to the garage naked. My cock was already rock hard, so the shorts weren't hiding much anyway, my perverted mind reasoned. Without much consideration, I slide my shorts down and pulled them over my feet. Then I placed them on the passenger seat next to me.

"Don't do it!" the voice in my head screamed, "there are consequences to this kind of crazy behavior! You could get arrested! What happens when you leave? You're not thinking this through!"

My heart was racing considering the sheer lewdness of what I was about to do. It was daring and exciting. Besides, nothing says dollar store whore like walking the streets totally naked.

Before I could reconsider the move, I opened the door and stepped out into the world. I closed my door calmly and walked to the door on the side of the garage. My erect cock slapping back and forth between my thighs as I made the short jaunt. Once in the garage, I made my way to the steps in front of the steel door to the house. As usual, there were my wig, my lipstick, and a bag for my clothes.

"No need for the bag," I laughed to myself, "I didn't bring any clothes today!"

I felt extra slutty putting on my wig and lipstick before I entered Gus's place. I expected to find four men inside waiting for me. As I opened the door from the garage into the house, I heard music playing and a bunch of voices coming from the living room.

Mary's Customer Base Expands

I walked through Gus's kitchen and rounded the corner into the living room. When I did, I was surprised by the crowd waiting for me. Gus rushed toward me, naked as usual, with a big smile.

"Mary, look at all the customers I've lined up for you!" Gus beamed, clearly proud of the bounty his efforts produced.

"It's quite a group," I replied looking at the six men in the room that were all smiling back at me while they devoured my body with their eyes.

Gus, my Nicaraguan host with the fat, seven-inch uncut cock had become my makeshift pimp. Ned, my favorite customer, was a handsome black man with almost eight inches of cock that he used like an artist. Then there were four new men.

"Gus, please introduce me to my new customers," I said, politely, choking back the excitement and concern at the same time.

"This is Morrie," Gus said, pushing a tall seventy-year-old man forward, gently, by the shoulders, "He's a retired married guy who is anxious to find some regular relief since his wife has lost interest in sex."

It was clear that Morrie was an attractive man in his earlier years. He was still somewhat fit and had a full head of hair. He was well over six feet tall and looked well groomed. But it was what was between his legs that really stood out. Morrie was packing an eight-and-a-half-inch monster with big low hanging balls. He was also sporting an old-school bush to top his look off.

"Nice to meet you Morrie," I said, trying to keep my focus above his waist when I addressed him.

"You are very pretty, Mary," Morrie replied, "Gus has told us all about you and we're all glad we can help."

"What the fuck did that mean?" I wondered to myself, I assumed that Gus had told all of them that I was a starving dollar store whore who needed more customers.

Next Gus walked another Latin man forward, "Mary, meet Eduardo," Gus said, "He and I were friends in our old neighborhood. He is also from Nicaragua."

I smiled at Eduardo and nodded. He was about a half inch shorter than Gus, and looked to be about the same age, in his fifties. He was also sporting a very thick, uncut cock that looked like he had just shaved. I appreciated his hygiene, and I wondered why these little Nicaraguan guys were hung so thick and always uncut. It must be something in the water, I presumed.

"And this is Sam," Gus said, as he again pushed one of the men forward by the shoulders.

"Pleasure to meet you Mary," Sam said, as he stroked his meat with no regard for anyone's presence, "You are much prettier than your profile picture."

From that instant, I suspected that Sam might be trouble. He was the youngest of the group, maybe late thirties. He was about five-ten, but very physically fit. His entire body was tan and shaved of all body hair like he was a body builder but without the muscles. He had dark hair and overly whitened teeth. This dude should have no problem getting laid; why was he here for a dollar store whore who is a very non-passable crossdresser. The cock he couldn't keep his hands off was about seven inches. I needed to watch out for this guy.

"Last but not least, this is Hank," Gus introduced the final man in the six-man group.

"Maybe last should go first," I joked, "Nice to meet you Hank," I smiled.

Of all the men, Hank looked out of place with the rest of the group. He was early forties, and he looked like a suburban, corporate, family man. He was clean cut and the only one still wearing boxers. He wouldn't look me in the eye when he greeted me, it was clear he was uncomfortable with the situation, but his lust had caused him to step outside his comfort zone. It wouldn't surprise me if Hank snuck out once things got real.

"Well, Gus, it's your party, how do you want to start?" I said, smiling around the room at my six soon to be customers.

Gus Sets the Ground Rules

"Alright guys, first off, thanks for coming today, I'm glad to help Mary find new customers so she can make ends meet. The ground rules are simple; Mary doesn't bareback but she does swallow. If you need to feel yourself unloading inside without a condom, her mouth is the place for that. As we discussed, Mary's price for any activity is just a dollar. Please use the phrase, 'For a dollar more' when you make your request and then place your dollar in the box on the coffee table. Tips at the end are always welcome. Mary must leave here by 2 p.m., so pace yourselves accordingly. I've donated plenty of condoms and lube on the coffee table here, so feel free to use them as needed."

I barely heard Gus explain the ground rules, the voice in my head was screaming too loudly, "You're naked, except for that stupid wig and lipstick, letting a Nicaraguan guy sell your body to a group of six strange men for a dollar! Are you fucking crazy?"

I had to admit, when my voice put it that way, it did seem like I was kind of far out over my skis. What started as an impulsive meeting with Gus had quickly escalated to something I could have never imagined; in just four days. Gus was either a crazy pervert, or a genius with fetishes. He had gotten into my head and turned me into Mary. Now I was about to let six men use me for just a dollar a time.

"Why don't we show them how this works, Mary," Gus's voice interrupted my thoughts, "For a dollar more, would you please get on your knees and suck my cock."

As the five other men watched, I dropped to my knees in the center of the living room and took Gus's uncut cock into my mouth. I heard the other men whispering among themselves as they watched me get to work on Gus. I wondered how this was going to work; since I only had two holes and there were six men to pleasure. I wondered what they would do while they waited for a spot to "open" for them.

I was so turned on having a group of naked men watch me suck Gus's thick cock. I loved having an audience watching me morph into a total slut. My cock was rock hard with excitement and lust. Mike disappeared and Mary was fully engaged. She started putting on a show for the waiting men. I took Gus's thick cock balls deep and held my nose in his pubes. Holding him there for as long as I could.

"Oh Fuck, Baby," Gus moaned, "Show them your deepthroat skills. I can't wait to see how you handle Morrie's big cock."

"Mary, for a dollar more, can I fuck your ass?" I heard Ned say in his low voice.

I saw him drop the dollar in the box on the coffee table, then take a condom out of the pile and work to put it on his hard cock. Ned had a big cock, and he used it like an artist. Every time he fucked me; it ended in a very satisfying orgasm. It was just 11:30 a.m. and I was already being spit roasted.

I heard the other men whispering among themselves while they watched Gus and Ned share my body for pleasure. I was on all fours letting my customers fuck me at both ends. I felt my right arm being pulled off the ground. Then I felt someone putting their hard cock in my right hand.

"Sam, remember the rules," Gus scolded in his Spanish accent, "Please use the phrase and put a dollar I the box."

"For a dollar more, Mary, will you stroke my cock?" Sam said, his voice shaking with excitement, as he put a dollar in the box.

This was a first for me. At first, I had a hard time keeping my mind on stoking Sam's cock while I had Gus's cock in my mouth and Ned's cock in my ass. I realized that I needed to let Gus and Ned do the work so I could focus on Sam's cock in my hand.

"For a dollar more, will you stroke my cock too?" I head Eduardo say in his thick Spanish accent.

Another dollar went into my box and was quickly in an awkward position trying to balance myself with a cock in each hand while getting spit roasted. I had seen something like this in porn movies, but I never thought it would be happening to me. I felt bad for Hank and Morrie who were patiently waiting for my availability. My mind was buzzing as I thought about bringing each of these men to orgasm eventually. If I was expected to swallow them all, I'd be going home with a very full stomach.

Meanwhile, Ned was working his usual artistry. His big cock seemed to be everywhere inside me all at once. Gus had his hands on both side of my head, holding me in place while he took full strokes into my throat. Sam grabbed my hand and started pumping his cock faster; clearly, he wanted more attention than I was giving him. Of all the men, I was worried that he might become more like Billy, the weirdo we threw out last time.

"For a dollar more, Mary, can I put my cock in your mouth along with Gus's?" Sam asked in his nervous voice, while he inserted another dollar into my box on the coffee table.

Mary Starts to Multi-task

I'd never had two cocks in my mouth at the same time, but I guess I was about to find out what it was like. Gus rotated a bit to my left, making room for Sam to slid in next to him. I held my mouth open as the two men forced the heads of their cocks into my mouth. My lips stretched to accommodate the large cock heads of both men. Gus and Sam took turns shoving their cocks into my open mouth. I was amazed that I was able to get half of both men's cocks into my mouth at the same time.

"I've never seen anything like this," Hank said, in his quiet, reserved voice.

I felt a calloused hand grab my right hand and place it on a giant cock, without looking I new it was Morrie.

"For a dollar more, Mary, will you stroke my cock?" I head Morrie ask, in his firm, low voice.

As another dollar went in the box, I struggled to juggle all five cocks I was supposed to be pleasuring. I was surrounded by men who were told that they could do almost anything they wanted to me for just a dollar more. I wondered how I let myself fall this far down the sexual rabbit hole.

"Let me have her mouth for myself for a minute, Sam," Gus moaned, "I'm getting close here.

"Fuckin' hot, man," Sam chuckled in a creepy way, "I can't wait to see you blow your load down her throat."

Gus grabbed my head with both hands and started to focus on his own pleasure. Meanwhile Ned was driving me within a few inches of my own orgasm. I had Eduardo's cock in one hand and Morrie's big snake in the other.

"Mary, for a dollar more, can I slide my cock in your ass next to Ned's?" Sam asked, in his excited, creepy voice.

"I'm not gay," Ned said in disgust, "I don't want my cock touching yours. Besides, I'm getting close, why don't you just wait your turn."

"No worries, big man," Sam acquiesced, "I'll just make our little bitch cum while you fuck her."

I felt Sam place his arm around my waist as he reached for cock and started stroking me.

"Shit, she's too dry," Sam noted, as he reached for the lube, "Let's get you nice and slippery, he said as he poured a pool of lube into his palm and then spread it all over my throbbing cock.

Ned had already pushed me very close to orgasm. Sam didn't know that he was holding a loaded gun. Meanwhile, I saw Hank out of the corner of my eye. He put a dollar in my box and then slipped out of his boxers, exposing a hard, handsome, totally shaved, seven-inch cock. He was sitting on the couch, stroking his cock as he watched the live sex show unfold in front of him. I thought it was nice that he put a dollar in the box just to watch.

Morrie's cock was not at full staff. It was the biggest cock I had ever seen in person. It was a throbbing and thick, with a giant purple head. It looked almost as long as my forearm from elbow to wrist. Even though I was so close to orgasming, his massive phallus struck fear as I wondered how I would accommodate his old monster.

"Are you ready for Papi's first load?" Gus growled, as his thighs shook involuntarily.

Gus's words, along with Sam's stroking and Ned's fucking pushed me over the edge and I started to spray cum everywhere.

"Oomphf, Mmphf" I snorted as my cock blasted most of the contents of my balls all over Gus's living room floor.

"Fuck, yeah," Ned purred, "I love how her ass spasms when she cums."

"I'll keep her going for you Ned," Sam laughed like a little boy as he continued to stroke my cock while I orgasmed hard.

"Swallow for me, Mary!" Gus howled as his knees bent and he held his cock deep in my throat with his big balls resting against and under my chin.

I could feel Gus fill my stomach with his hot semen as I writhed under my own orgasm. Eduardo and Morrie seemed to understand it was hard for me to keep stroking while my body was spasming as hard as it was. I was a little annoyed that Sam continued to stroke me aggressively even thought my orgasm was trying to subside. My spasming ass was driving Ned very close to orgasm as well, I could feel him slowing his stokes in order to keep fucking me longer.

My orgasm was subsiding, but Sam was still stroking me like a fiend. I used one of my hands to try to swat his hand away, but he just kept stroking me. It was becoming more than a little uncomfortable. Gus's orgasm had completed, and he expected me to clean his cock just the way I always did. He pushed out the final drops in his shaft using his thumb and forefinger. I held my mouth open to take it in and then sucked his shaft clean.