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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.
