/******************************************************************************
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.
*******************************************************************************/
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"
