Back when I was 20 and money was tight, gas prices were through the roof and I had a minimum wage job at Home Depot working as a cashier. I had a client that used to come through my line fairly often, probably a couple times a week. Very nice guy probably mid 40’s at the time, and super easy to talk to.

At some point we were talking and he asked if I knew any young men that could help him with spreading mulch in his backyard. My broke ass piped up and said well shoot, how much does it pay? He told me $200 bucks, doesn’t matter how long it takes, I’ll pay you when it’s done.

As some one whose two week take home check was less then $600, I was in. He gave me his number, I told him which day I could do it and we went on with our day.

A few days later I was finally off and ready to go make that big money. I got over to his house early, and he answered the door in a silky Hefner style robe. Didn’t think much about it, just assumed that he hadn’t gotten ready for the day yet. He took me to the backyard pointed out the massive pile of mulch and the planters that it would need to go in, and I quickly got to work.

I busted my ass on this pile of mulch for hours and was getting no where. After probably ten hours of trying to get this spread out I finally gave up and told him that I would have to come back. He was totally fine with it, and being his kind self, he invited me in to get a drink and pay me out a portion of what he was paying for the job. We had a nice conversation about life and what my plans were along with pretty much all the small talk stuff, nothing too out of the ordinary. The only thing I remember being slightly strange was when he got me a refill on my drink, we had been sitting across from each other but when he returned he sat down next to me. But nothing happened, we simply finished up our conversation and I went home, $100 richer than I was before.

After a few days of working my retail job, I finally had a day to go back to his house and get more of the work done. I knocked on the door to let him know I was there and once again he answer with the Hugh Hefner robe. I walked through the house and into the backyard. This day was fairly hot and I was dying trying to get this done, and he could tell. Sometime mid day, he popped out the back door and told to come inside, cool off and get some lunch and a drink. I set my tools down headed for the door, just excited to get a piece of that air conditioning.

When I got in the house there was pizza sitting on the counter and an ice cold coke poured in a glass for me. He told me to go a head and just take it over to the couch, and eat there so I grabbed my plate and headed over. As I set my plate and cup down I glanced at the magazines sitting on the table and on the very top was a cover showing a probably early twenties guy in only a jog strap that instantly took my breathe away; only for a moment but I was in pure shock. He saw and ran over, grabbed it and tucked it to the bottom of the pile of magazines, apologizing for having left it out. I remember reassuring him that it’s fine, don’t worry about it but it definitely got quiet and awkward for a bit while we ate lunch.

After a few failed attempts of starting small talk, he finally looks at me and goes, well I guess you know now but I’m not exactly straight. I reassured him that it was fine and I didn’t care what he was into. We played it off in a kind of joking manner, with him cracking the joke “well now that you know, maybe I can pay you a little more to work with your shirt off.” And my smart ass piped off with something along the lines of “I’ve got bills, if you pay me enough I’ll work in whatever you want me too.” He laughed and through in his last jab saying “you do that, just watch how big the payment gets!” As I walked out the door still laughing about the exchange I took my shirt off and said “well let’s see how much it’s worth to you then.”

With as hot as it was I was actually totally ok to play that off as an excuse to not wear a shirt. I finished off the last few hours of the day sweating my ass off again before going back in to collect my money and head home. He pulled out his wallet grabbing 2 hundred dollar bills, setting them down individually saying this is for the work and this one… this one’s for the uniform choice. We laughed, and told him it was joke so don’t feel like you have to, to which he told me “nah, a deals a deal.” We laughed and parted ways.

This went on for the two remaining days it took me to complete the mulch pile. I would get there and I would quickly take that shirt off and without fail I had an extra hundred bucks. Once I finished I thanked him, and let him know because of the generosity I was able to almost catch my car payment up, also mentioning that if there was anything else he ever needed to just give me a call.

A few weeks went by, just seeing this guy on occasion as he made his way through my line at Home Depot with whatever the week’s project was. Finally one day he came through my line and tells me that he doesn’t have a bunch of work but if I want to make a few bucks I could come over and cleanup his house a bit. I agreed told him what day I could do it and I continued on with my retail duties.

The day came and I headed over to his house. When I got there he answered the door the same way he did everytime. I walked in and he started escorting me through the house showing me all the house hold tasks he needed done, eventually ending up in the hallway just outside his bedroom. He paused here for a moment, then looked me in the before saying in a strikingly matter of fact tone, “and if you want a little bonus I have an offer for you.” I chuckled asked “what’s that.” He guided me into the room and on the bed lay a French maid uniform. He glanced at me and said, “you don’t have to but… if you wear this while you clean my house, I will pay $300 on top of the $200 I’ve already been paying you.

I don’t know if he knew, but I was already a bit late on rent, I still hadn’t gotten my car payment completely caught up, and my account balance was barely hanging on. I sat there for a while not sure what to do when he told me no pressure just think about it, and we walked back out.

I started the list of chores he had given me with vacuuming. I made my way all the way through the house thinking about the offer. I knew I needed the money but the thoughts rushed through of all the things he would be doing with the mental image of me, and trying decide if I cared.

Well I finally vacuumed my way all the way to his room, and there it was, still laid neatly over the foot of his bed. I took one last second to think about it and decided. I needed that money, so I closed the door and began removing my clothes, folding them before placing them on the bed. I picked up the first piece, a skinny lacy top with a bra sewn in and began sliding it on. To my surprise the silky texture felt wonderful against my skin as it stretched to fit around my male form. But now came the nerve racking part for me. A lacy thong with the skirt sewn in. If I wanted that extra money there was going to be no way around this. I stood up, lift one foot, and placed it in the appropriate side followed by the other foot. I slowly pulled them up to there final location. The string split my cheeks and disappeared while my manhood had a bit of a hard time hiding itself behind the small piece of fabric that made up the front. Then came the stockings, I pulled them over my manly feet and watch my legs immediately appear soft a delicate. Again the feeling of this silky smooth fabric was a sensation that I was not prepared for, but admittedly enjoyed. I finally finished the uniform with the heels he had placed on the floor below the bed, and grabbed the blonde wig he left with the uniform.

This being my first time in heels It felt like learning to walk again, but I made my way to the long mirror attached to his door to try and place the wig neatly on my head. I felt sort of sexy for doing this as I made my way across the room, but then I saw myself in the mirror. I looked like a man stuffed into lingerie. I had never shaved around my balls before so the fabric covered bulge was surrounded by outstretched pubic hair, and my happy trail could be clearly seen through the lace top. It shot my confidence, but I figured this wasn’t for me and I would still at least try and make that money. I got the wig placed over my hair, took one last look at my self and walked the vacuum back out the door.

I was so nervous about what he would think of me, I was doing this for the money but I still wanted to do a good job for him, which meant looking half way descent. I walked down the hall way and back out of the living room where the tile floor started. As the heels began hitting the tile it felt like it echoed through the whole house. I kept me head down slowly making my way to the closet were he kept his cleaning materials, placing the vacuum back in its location and closing the door. I turned around and there he was leaning over the kitchen counter, one hand holding his chin, the other hidden behind the counter, but I could assume where it was, biting his bottom lip, staring at my barely clothed body.

He gave a long drawn out “Oh… My… God…” as I gave a shy smile. I could tell he was adjusting himself behind the counter before walking straight towards me. He placed his hands on my shoulders and looked me up and down. “You look incredible” he said before walking towards the couch. As he turned around I could see the imprint of his cock against the silky robe. I was definitely still a straight man doing this for money but the idea that my body had gotten this man so excited in such a short amount of time began to turn me on. I could feel my dick starting to stiffen beneath the fabric from the this thought alone. I began to turn around and headed back to the closet to pick up supplies for my next project. All the while I could feel him staring at my nearly completely exposed ass.

I spent the rest of the day walking back and forth across the house, accomplishing every task he had set aside for me. I became more and more comfortable with the idea that I was turning him on with every step I made, and came to enjoy the feeling of being sexualized. I decided to finish the day by getting on my hands and knees to mop the tile floors in the kitchen and living room, paying special mind to the direction I presented my self. As I came to the last section of the floor, he heard him get up from his seat, walk towards me, and stop. I continued wiping the floor when I felt his finger pull the elastic waist of the miniskirt/thong combo and the feeling of cold, hard cash being slide into it.

I glanced up at him and simply said “Thank you sir, same time next week”

“Absolutely” he responded