For A Dollar More Pt 03

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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.

We catch up with Mike on his third day with Gus. He has committed to meet Gus at 11 a.m. again today. It is starting to look like Mike will be visiting Gus daily now.

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Mid-Morning, Mike's Wife is Gone at Work

It was 10 a.m. and I was again home alone while my wife was at work. I had done a little work in the morning, but I was taking a coffee break and I was back on the cruising site and I was already receiving messages from Gus.

Him: "I expect you at 11 again today, Mary"

Me: "I'll be there as we agreed"

Him: "Strip in the garage, clothes in the bag"

Me: "Just like yesterday?"

Him: "Yes, you will also find your wig there and your lipstick"

Suddenly, the wig and lipstick were mine. I never really agreed to wear them, but he was also calling me Mary and I was allowing it.

Me: "Any other instructions?"

Him: "No need to knock anymore, I know when you'll be here, just come in"

Me: "OK, see you soon"

Him: "Good girl'

I had an hour to get ready and get my mind together. I couldn't understand why I was allowing Gus to call me "Mary" and dress me as a woman. Crossdressing isn't something I like; it does nothing for me, sexually. In fact, it kind of turns me off. Yet, Gus had me dressing up for him again today, and I had agreed.

"You should stop now," my inner voice screamed, "This has gotten away from you. You're losing control!"

My curiosity over-ran my inner voice. As if in a trance, I walked upstairs to get prepared for my meeting with Gus. My body seemed to be on auto-pilot as I showered and prepared myself. I found myself in my closet again, picking out a shirt and then pulling on my jeans. For three days now, I had skipped wearing underwear so I could strip faster in Gus's garage. I wore only three articles of clothing, a shirt, jeans and sandals.

Today, the spring weather had warmed up, the high temperatures were expected to be in the mid-seventies. I wondered if I should dress a little less conservatively. Gus wanted a hooker, maybe I should dress more like a hooker. My cock started to swell as I considered the concept. In the back of my closet, I had a very short, tight pair of running shorts that I stopped wearing years ago. I dug them out and pulled them over my naked body.

I stepped out of the closet and looked at myself in the mirror. I looked like an X-rated Richard Simons with an erection. I turned around and noticed how far the shorts went up my ass. I imagined that a male prostitute would parade around in shorts like this. The shorts sat so low on my hips that if my erection pointed upward, it would protrude over the top of the shorts. The things were obscene, and I decided I was going to wear them. I threw on a tight, short t-shirt to complete the ensemble and headed downstairs.

I stopped to look at myself again in the main floor powder room. I couldn't believe I was leaving the house dressed like this. My partially erect cock was clearly visible in the shorts and the crack of my ass was on full display as well.

"Your such a cum slut," I told myself as I looked in the mirror, "You love taking Gus's thick, Latin cock, don't you, Mary."

"Jeezus, what's wrong with you!" my inner voice screamed, "Do you hear yourself?"

I ignored the voice and headed toward my garage. I grabbed my keys and headed out to my car. Soon, I was rolling through my neighborhood, dressed like a prostitute, on the way to visit Gus for another role-playing session. My mind had fully accepted the terms of the arrangement. Gus was paying me a dollar to perform lurid sex acts for him; and I liked it.

I turned on to Langdon Street and made my way to the fourth house on the left and turned into the driveway. As usual, the neighborhood was quiet, so I climbed out of my car and walked to the side garage door. My erect cock was tenting my tiny shorts, it made me even more horny. Once I was alongside the house, I looked around one last time and did something I've never done before; I stripped right there in public and left my clothes in a pile on the ground in front of the door. I stood there for a second to take it in. My cock was rock hard, I felt like a total slut.

Mike Embraces His Inner Mary

I entered the garage, naked and walked over to the steel door that provided access to the house. On the step, I found the grocery bag in which I was supposed to leave my clothes.

"No need for that!" I said to myself, "I left my clothes outside, like a good slut."

Next to the bag was the same wig from yesterday. Right beside the wig, was the red lipstick and a small handheld mirror. I assumed that Gus wanted me to gussy up a bit before I walked in. I pulled on the wig and looked in the mirror to ensure it was on correctly. Then, I used the mirror to apply the bright red lipstick. I looked like a perverted crossdresser, but I didn't care. My mind had become malleable to Gus's weird mantra. Every time he said, "For a dollar more..."; I seemed to be willing to do whatever he asked me to do next.

With my wig on and my lipstick applied, I pushed the door open and entered Gus's house. Once inside, I instantly knew that something was different. I heard voices laughing and talking from further inside the house. I was suddenly terrified I was in the wrong house. I checked my surroundings and they looked familiar, I was clearly in Gus's house. I walked toward the living room, toward the talking and laughter.

Mary's World Is About to be Rocked

As I entered the living room, I saw Gus sitting behind a wheeled desk, peering into his computer screen. He was naked as usual, but this time his cock was in one hand and his phone was in the other.

"She just showed up!" Gus laughed, turning to look at me, "She looks just like the picture but she is naked, no thong today."

"Who the fuck was he talking to?" I wondered, "...and why was he so focused on the computer when he had a willing, naked, slut waiting to service him?"

"Yeah, she's fuckin tight," Gus continued, "Bring a stack of one's, she'll do almost anything for a dollar."

"You've got the address, right?" Gus asked the person on the phone, "That's it, see you soon."

I approached Gus, my blonde wig causing my shoulders to itch. I recognized the site Gus was watching; it was the gay hookup site that I used to find him. As I looked more closely, I saw that he had multiple chat sessions open, and he had one of the user's profiles open on which he was particularly focused. When I recognized the profile photo, my heart stopped.

The profile pic was the photo he took of me yesterday. I was wearing the wig and my wife's thong. The profile caption read: "Cheap whore does it all for a dollar..."

"Gus, what the fuck!" I shouted, "What the hell are you doing? That's my picture!"

"Mary, I'm trying to help," Gus laughed, "I can't possibly fund you by myself, you'll starve on just ten dollars a day, I want to help grow your business."

"This is role play you dumb fuck!" I shouted, "I'm not a street whore, this isn't my business!"

"Mary, you need to calm down, nobody knows who you are," Gus assured, "You should see the hot comments you're getting. I'll pay you a dollar just to look," he continued, turning the monitor slightly my way; then he handed me a dollar bill.

I was suddenly calm, and I was curious about the comments. Gus had converted my rage to curiosity, I couldn't help but start to read what people were saying about "Mary". There were almost a dozen men talking about how they wanted to fuck my face, or my ass, or both. Everyone thought I was a hot piece of ass. They were shocked that I was willing to do almost anything for a dollar.

I looked at some of the pics. There were guys of all shapes and sizes. Some of them were very hung. My cock was getting hard thinking about taking some of the big dicks who were expressing interest. Mary was getting way more interest than Mike ever did. It seemed like everyone on the site wanted to fuck my tight ass.

"Mary is getting a lot of interest," I mumbled out loud.

"She certainly is," Gus agreed, "For a dollar more, would you consider sitting down and engaging with some of these men?"

"You want me to chat with them as Mary?" I asked, my voice trembling as I considered impersonating a woman and soliciting men on a gay hookup site.

"Yes," Gus said, handing me another dollar, "Take a seat, let's get you some customers."

I sat down at the rolling desk and grabbed the mouse. There were seven or eight open chat windows. I started to browse through each of them. Most of the profiles were men in their mid-40's and mid-50's. As I reviewed each of them, I was pleased to see that all of them were tops. One of them had an impressive cock he claimed was nine inches. He was a black guy who showed nine miles away on the map.

If I were on with my own profile, I'd be very pleased with the activity. I had never had this kind of action on the site. I picked a guy whose location showed he was less than a mile away. It was obvious that Gus had been whipping interest in "Mary" into a small frenzy.

I engaged the guy who was close by. His profile stats were: 51, 6'2", 220#, Athletic build, 8" cut, thick, Top, need to travel:

Me: "Hi baby, it's me Mary"

Him: "Is it really you? Gus has been telling me you need new customers."

Me: "Are you interested, baby?"

Him: "Yes! Can I really fuck that tight pussy for a dollar?"

Me: "Why don't you come over with a stack of one's and find out?"

Him: "Are you serious?"

I turned to Gus and asked, "I've got a customer who wants to come over now, do you want me to keep going?"

"Absolutely," Gus replied, "I'd love to watch you sell yourself all day long."

Me: "Sure, as long as you can be here in the next 30 minutes"

Him: "Give me the address, baby"

Me: "(address given), please use the door on the side of the garage."

Him: "See you in fifteen minutes"

"See, we found you a new customer!" Gus exclaimed, "I knew that you'd attract a lot of action, Mary."

I couldn't believe what I was doing. I was soliciting strange men on a gay website for sex. I was sitting in a stranger's house wearing only a wig and lipstick prowling the internet for people who were willing to pay a dollar to fuck me. Gus's role play fetish was becoming more real each time we met. I was letting him call me Mary, I was dressed as a street whore and now I was soliciting strange men. Even so, my cock was rock hard.

"As your pimp, I take seventy-five percent of everything you make," Gus laughed, "Just remember that when you're selling your ass for a dollar."

"C'mon!" I whined, "I'm never going to make any money if you take that much."

"Jeezus, you're acting like this guy is actually your pimp," my inner voice barked, "Get a hold of yourself, you're doing this because you like it."

"Why don't you suck my cock while we wait for our visitors," Gus proposed, "The first one should be here any minute."

"What are you talking about?" I asked, "The guy I just invited over won't be here for almost a half hour."

"Oh, I invited a guy over as you were walking in," Gus confessed, "He said he'd be here in twenty minutes, and that was at least fifteen minutes ago."

"Who is the guy?" I asked, shocked but somewhat excited.

"He's a guy in his sixties, he's retired, and he gets horny during the day," Gus answered, "He's an ex-jock, bigger guy, with almost eight inches uncut. Oh, and he's black."

"So, there are two hung guys coming here?" I asked, "I'm not sure I'm ready for this."

"Yes, Mary, you will have three customers today," Gus clarified, "I am going to pay you for pleasure as well. My hope is that you leave today with a few new regular customers who can help you make ends meet."

Just then, there was a knock on the steel door that led to the garage. Gus left me in the living room and went to see who had arrived. I went to the couch and sat down; I was getting a little lightheaded with everything that was happening. I wasn't sure if Gus was a madman who actually believed I was a dollar store street whore. Or was he a phycological magician who had taken control of my mind. Either way, I was about to entertain three men at the same time as a prostitute named "Mary".

Mary Gets Down to Business

I heard Gus and the new man talking and laughing in the kitchen. Then Gus emerged with a tall black man in tow.

"Mary, this is Ned. He's very anxious to be your new customer," Gus said, looking toward the tall man who was wearing only a pair of boxers.

"Hi Mary," Ned said, "I found these clothes by the door, are they yours?"

"Hi Ned," I replied, my face flushed with embarrassment, "Oh yes, I left my clothes outside because Gus won't let me in his house unless I'm naked."

"I like that rule," Ned laughed, "I guess I should take mine off too then."

Ned put his thumbs under the waistband of his boxers and pulled them down revealing his thick, black cock. He was unshaved and his cock had a nice afro covering his pubic area. Like Gus, he was also uncut. He also had very large low hanging balls. I could feel my mouth hanging open as I stared at his manhood. He was all of seven and a half inches.

"Mary, why don't you get on your knees and show Ned how you like to suck my cock." Gus proposed, he held up a dollar bill to make his point, "I think Ned needs to see what you're willing to do for just one dollar."

I got off the couch and crawled over to Gus while Ned watched. I took on of his big balls into my mouth and let his erect cock rest on my face. When I let his ball pop out of my mouth, I saw the ruby red lipstick line I left behind.

"Would you be more comfortable sitting down in your chair, Papi?" I asked, looking up at him from my knees.

"How considerate of you, Mary," Gus answered, as he walked over to his chair, "Why don't you crawl over and continue your display for Ned."

I could feel Ned's eyes watching my every move as I crawled between Gus's open thighs and took his cock into my mouth.

"Mary gives the best dollar blow jobs in town," Gus moaned, "and she swallows every time."

"For a dollar more, Mary, would you let me watch you suck Ned's big cock?" Gus asked, "I'd like to see if you can deepthroat his big cock."

"Yes, Gus," I replied, turning to look at Ned.

Ned walked over and sat on the couch. I decided to crawl the two feet over and get between his muscular thighs as well. As I approached, Ned's aroma was intoxicating. I had never seen a black cock in person, and now I was about to suck the biggest cock I've ever had. I remembered that in a few minutes a guy with an even bigger cock was going to show up at Gus's door.

I started by taking one of Ned's big balls in my mouth. The earthy smell of his cock caused my cock to become rock hard. I loved Ned's aroma, it was intoxicating. His balls were hairy, warm and huge. I alternated between them listening to Ned moan and sigh as a did. I felt Ned set a dollar bill on my back as I released his balls and licked my way up his thick, black shaft. I worked my way to the head of his cock and took him into my mouth. I worked on his shrouded cock head for a while, listening to him moan. Then, I forced myself down on his cock, working to deepthroat his big black cock. I wanted to bury my nose in the thick afro at the base of his dick. It took me at least a half dozen attempts before I made it all the way to the base.

"Fuhk, Mary," Ned moaned, as he placed his giant hands on my head, "Take that cock, baby."

Mike Becomes Mary the Dollar Store Whore

I couldn't believe what I was doing. I was wearing only a wig and lipstick, and I was pleasuring two strange men with my mouth at nearly the same time. I couldn't believe how aroused I was. My body was literally vibrating with lust and excitement.

"For a dollar more, Mary, can I fuck your ass while you suck Ned's cock?" Gus asked.

I pulled off Ned's cock and looked over my shoulder to see Gus standing behind me holding up another dollar bill.

I answered, "Go ahead, Gus, that's my going rate."

"No shit," Ned blurted, "She'll let you fuck her for a buck?"

"She'll do almost anything for a buck, Ned," Gus replied, "Just say 'For a dollar more' when you ask."

I turned back to suck Ned's big cock, and I heard Gus ripping open a condom. I knew it wouldn't be long, and I'd have both men using my holes at the same time. Ned grabbed my head and was helping me find the correct rhythm with which to fellate him. I was amazed at how quickly I had learned to throat his nearly eight-inch cock. I was certain that his balls would create an impressive load when I finally made him cum. I was only twenty minutes into my visit with Gus and I was about to endure my first real spit-roast.

I felt Gus applying cool lube to my anus and ass crack. I knew that I was about to get fucked by the little man for the third time in as many days. I was so ready for his cock this time. Especially with Ned's big cock buried in my throat. Gus entered my ass in a single thrust.

"Hmmphg" I sputtered as Gus entered my ass.

"Yeah, take those cocks, bitch," Ned moaned as he watched Gus fuck me while I sucked his cock on all fours.

"How many singles did you bring, Ned," Gus asked, as sawed his cock in and out of my ass, "Mary will likely sell you a limb for ten bucks."

"I've never met a whore I could fuck for a dollar," Ned laughed, "Where did you find this dollar store cunt?"

"Same place we found you," Gus panted, as he plowed my ass, "and we're just getting started."

"Leave some of that tight ass for me, Man," Ned moaned, "I plan on cumming at least twice, maybe more today."

I was lost in stimulation. For the first time in my life, I had two strange men using my holes at the same time. Every nerve in my body seemed to tingle with lust and arousal. I couldn't get enough. I realized that the moaning sound I heard wasn't Gus or Ned; it was me. I was moaning like a cheap whore taking both the men's cock's balls deep. Anyone who arrived on this scene would see a blonde slut getting gang banged by two men. I was getting fucked so well, I even started to think of myself as Mary, the dollar store cunt.

The contrast between Ned and Gus was almost humorous. Ned was taller than I was, and Gus was almost a foot shorter than I was. I was sandwiched between David and Goliath; taking a beating at both ends. My cock was rock hard, and I was leaking pre-cum all over Gus's hardwood floors. I knew that I wasn't going to last much longer with both men using me hard. It was just a matter of seconds before I blew my load all over Gus's living room floor.