It had been about a month since the night that Randy had forced his way into my life. Since his office was upstairs from my business we saw a lot of each other, but he never mentioned that night until today.

Unbeknownst to him, I had thought of that night fairly regularly even though Al and I were still going at it pretty often. He was after all well hung and quite good at manipulating his tool.

I was closing up for the evening and he wandered in to say goodnight like we were friends. Friends we were not. We were simply two business owners that occupied the same small house.

I found it odd that he wasn’t any more chummy since that night but maybe he took it for what it was, just sex. As he started his normal weather and traffic babble I simply ignored him and continued my nightly closing ritual.

Normally when he noticed that I was ignoring him he would simply say goodnight and leave. Tonight was different though and I was about to find that out. Mid-sentence, Randy stopped talking and cleared his throat as if to command my attention. Thoroughly annoyed with his demanding behavior, I quickly spun in my chair to find five one hundred dollar bills lying on my desk.

Now anyone that really knows me knows that money is not a motivator for me, at all. Before I could speak, Randy offered the following deal. He wanted to fuck me at least once a week and would pay me five hundred dollars each time.

He would like me to dress in one of my outfits and would even buy me a new one for each meeting. He would like to make it a regular night and would let me decide which night would work best for my schedule.

When he finished talking I simply sat silently for a minute imagining all the new outfits that I could accumulate in just a couple of months. It seemed that while I was thinking of my new wardrobe Randy thought I was looking for more money and he quickly dropped two more hundred dollar bills onto the stack. I didn’t really stir at that, he said that he would let me film all of our sessions as insurance.

Picking up the money, I turned to face him and asked him why he wanted me so badly. I knew that he had had a regular thing with a woman on Friday nights and thought that that was still going. As he collapsed on the chair across from my desk he simply told me that I was the best piece of ass that he’d had in a very long time. He couldn’t get that night out of his head and that is why he initially tried to blackmail me when we were done fucking.

Handing him back the money, I countered with the following deal. I told him to keep his money as he would need it to buy me two complete head to toe outfits for each time we fucked. That meant lingerie, stockings, shoes, wigs, makeup and even some sexy dresses all on his tab, and by my counting, he already owed me two full sets. The frown that had covered his face when I gave him back the money suddenly turned into a huge grin.

Randy scampered around my desk as if to give me a hug but I quickly stopped him by extending my hand in the form of a handshake. He gave me kind of a queer look and I told him that this was simply a business transaction and nothing more, he would get to fuck me and I would get material gain.

Continuing to look at me oddly, he said that it was obvious that I enjoyed our time together as much as he did, so why was I being so standoffish. I replied that while I did enjoy it too, it was nothing more than a simple transaction and did nothing to change the status of our relationship as co-workers. As all of that seemed to sink into his head he grabbed my hand and we shook on the deal.

We sat for another twenty minutes going over the details and decided that he would open a simple checking account for my purchases. I told him that once I received my first order we could set up a weekly rendezvous after closing time on Tuesdays, if that worked for him. He readily agreed to everything and said that he would set up the account tonight online and give the information tomorrow so that I could order my things right away.

After Randy left the office I watched to make sure he had driven off before I did my happy dance. I had played my disinterest well, and had scored not only a source of high-dollar lingerie, but also a willing and talented sex partner.

I honestly had no interest in him other than for sex and knew that I would have to continuously remind him of that. But that aside, it was a great deal for me and I spent the evening browsing online for my first order.

The following morning there was an envelope on my desk that had the words our deal written in black. Opening the envelope I found the account info and a simple request for something in red. Fortunately for Randy, I already had an entire outfit in red in one of my many carts, so I ordered that and a pink set first. Since it was already Friday, I opted for the Saturday delivery at my home so we could get started the following Tuesday.

Later that evening as I was closing for the day Randy appeared and asked if I had received everything that I needed. I replied that I had and that the items had been ordered and that I expected that we could begin our contract on the upcoming Tuesday. A huge grin crossed his face that bordered on psychotic looking, as he brought his right hand to his crotch and began to rub himself.

As his cock swelled rapidly Randy asked if we might have a quickie right now and I told him that Tuesday was his night and no other. The quick turn down did nothing to wipe that sickening smile from his face but he did turn and go out the door. I briefly wondered whether I would regret this deal, but decided that I could stop any time since I did have the original recording of our first time.

Saturday came and so did my packages so I spent the afternoon trying on my new treasures and taking lots of pics. For the red ensemble, I got a short red wig to go along with the lingerie which included a red lace corset, red lace g-string panties, red thigh-high stockings and red five-inch pumps.

Randy wanted red and red is what he’ll get. I spent Sunday practicing my make-up by reviewing online videos and trying to get it right, repeatedly. I wasn’t going to wear make-up for Randy but I was interested in going out fully dressed at some point and make-up was key to accomplishing that.

Monday flew by without any contact from Randy until the end of the night goodbyes. He did ask what time he should come down to the back room since he knew that I would need some time past closing to get ready. I told him that five thirty would be okay since I close up at five and that he should just knock on the backroom door around then.

He did have a little grin as he turned to leave and that’s when I told him not to forget to bring that big hard cock of his too. His grin turned maniacal again as he starting strutting to the back door.

Tuesday morning came and I got up a little early to spend some extra time getting an all-over shave to give Randy his money’s worth. I always love the compliments I get for being so smooth and clean no matter who my partner is and whether it’s just sex or making love. 

Once all of my preparations were complete I gathered all of my items in an overnight bag and headed off to work. Pulling into my parking space I noticed that Randy was still in his car and must have just gotten there himself. As I got out of my car I made a bit of a show by bending over at the waist as if I’d dropped something on the ground.

After I pretended to find that which I dropped, I slowly rose to see Randy staring blatantly at my ass. I thought I would give him a little bit of tease since I did spend nearly six hundred dollars of his money in lingerie and accessories.

Noticing that it was working and seeing no one else around, I intentionally dropped my keys and bent over to pick them up. With Randy only a few feet behind me I pretended to lose my balance and backed right up against him, still bent over. He instinctively grabbed my waist to break my fall and ended up pulling me tighter against his swollen cock.

As I went to stand, I purposely rubbed the crack of my ass against his cock. Then pretending to fumble with my keys, I got a few more rubs in before it was too obvious what I was doing.

Once I finally stood up, I was the one grinning like the Cheshire Cat. Walking towards the door I turned and said that I couldn’t wait until five thirty. Randy just stood there dumbfounded as I headed to my desk.

The day went by rather quickly as most of them do and I didn’t really have much time to think about our upcoming coupling. Randy did stop by momentarily to see if I wanted anything for lunch but I had already brought mine with me so he headed off.

I didn’t see him again the rest of the day. When five o’clock came I quickly locked up and headed to the back room for a quick cleaning and lubrication. Now it was time to get dressed and I lotioned up one more time before donning my lingerie.

I had the redhead wig and all the lingerie on with the exception of the heels when there was a knock at the door. I quickly slid them on my feet and strutted to the door. Opening the door slowly with my back to it I asked who it was. Randy didn’t utter a word but slid his hand across my ass and gave it a light smack. Pulling the door open with my back still to him I slowly bent over as I had in the parking lot earlier that day.

Randy quickly took the hint and moved forward until his hard cock, still in his pants, made contact with my ass. As I started to rub up and down on him he told me that he definitely enjoyed all the red I was displaying. After a minute of rubbing against his pants, I reached between my legs and unzipped his fly and was pleasantly surprised that he wasn’t wearing underwear. With his cock free, I once again started rubbing against his cock while I fondled his balls.

Placing his hands on my ass, Randy squeezed my cheeks in rhythm to my stroking and soon we were both moaning and getting hot. I had no intention of sliding his cock into me, as far as I was concerned he would decide when he needed to be inside of me. I just wanted to get him so worked up that he couldn’t resist sliding that magnificent tool into my ass.

Apparently Randy had other plans as he quickly knelt down and started flicking his tongue across my hole. Now I was really moaning and it slowly dawned on me that with both of us teasing the hell out of each other we were going to be here for a while.

His plan did seem to be working as I was close to begging him for his cock. Still bent over I opened my eyes long enough to see that his cock was pulsing, covered in pre-cum and just within reach if I really stretched.

I started fondling just the tip but that was enough to get his attention. He quickly raised up and pushed me towards the desk with his cock in hot pursuit of my needy ass. When I bumped into the desk his cock slid smoothly inside as if it was meant to be there. There was no slow easy pumping now, this was a jack-hammer fuck that would end quickly and with glorious orgasms for both of us.

My prediction came about within two minutes as the fever pace that Randy had set got the better of both of us. I started cumming first and my contractions undoubtedly set of his. He continued pumping into me as he squirted what felt like a gallon of cum into my ass. When he finally quit he laid down on top of me with his softening cock still buried deep into me.

I really enjoy the aftermath, especially when a guy stays on top as he did until his cock slipped out. When he finally did stand, I asked him if he could go another round after a little rest. He said that while he appreciated the offer, there was no way he could go again tonight after that pounding. I replied that I was just trying to make sure he got his money’s worth.

Grinning his sly little grin he replied that he definitely got what he paid for and he was looking forward to next week and the outfit I would be wearing.

This story is a bit of a continuation of ‘It Wasn’t Love But It Sure Felt Good!’ but was written to stand on its own. If you want a little more background for this one then I would suggest reading the above.