I tried working on her renter’s quote several times but ,every time I started, it would lead to my cock getting ridiculously hard. The only way I could get relief was to jerk off again. I knew that I needed to move on to something else or I would rub my cock raw. I decided to read up on how to direct her to achieve her needs without putting her in dangerous situations.
After about three hours of clinical definitions and suggestions on how to cure or curb exhibitionism I certainly wasn’t hard anymore. I was also no closer to deciding how to aid her in safely exposing herself without being harassed. After much back and forth in my mind, I figured the easiest approach would be to take it slowly. I would set up safe situations where no-one was very close or, if they were, that it would be someone I knew.
As different scenarios started flooding my brain, I attempted to write down as many as possible. I also decided that Anne could never know that I was controlling the risk factor. I’m sure that that would remove some of her excitement in exposing herself. Since she had only shown herself to me so far I thought that bringing in a second customer would up the ante a little.
It was Friday afternoon when I finally finished Anne’s quote. I gave her a call to give her the price and after modifying a few coverages over the phone, we were all set. As we were finishing up, I suggested that she wear a short summer dress and opened toed sandals for our Tuesday appointment.
Anne asked what time she should come by and I told her about four. She inquired why four since our other appointments had been earlier in the day. I said that I had another appointment at three and I probably wouldn’t be finished until about four. As we said our goodbyes, I knew that she understood that now she had a chance to show off in front of somebody new, in the safety of my office.
In the days leading up to our appointment I envisioned several more scenarios for Anne and continued to write them down. Tuesday arrived and my three o’clock appointment was my buddy Ted. He wasn’t here for insurance and he knew exactly what the deal was. I told him that, while he couldn’t touch Anne, he could show his appreciation in other ways.
Ted got to the office at two thirty and we decided to pretend to be writing his home insurance, even though I already had his home insured. I did tell him that there was a possibility that she wouldn’t show until her appointment time. I ran through the whole process as if we were actually writing it so that Anne wouldn’t know that it was a setup.
Just as I suspected Anne showed up early, at three thirty and feigned stupidity for having written the wrong appointment time. She asked if she should come back later and I told her that she could wait if she wanted since we were almost finished. Wearing a yellow and white polka dot sundress that came to mid-thigh and simple white flip flops, she was stunning.
As Anne sat in the chair that I positioned perfectly for her earlier, Ted and I attempted to continue. The dress was perfect: buttoned in the front for easy opening, it rode up to the top of her thighs when she sat. All Ted had to do was glance to his right, and I to my left, to get a great view of Anne.
While Ted and I continued, Anne busied herself with sending text messages while crossing and uncrossing her superb legs. To say that Ted and I were having a hard time, was the understatement of the year. As I babbled away about cost estimator’s and liability limits, Ted was openly staring between Anne’s legs. I’m sure he was trying to determine if she was wearing panties.
Easily noticing the dramatic effect that she was having on us, Anne decided to change things up a little. She bent over to pick up her purse and uncrossed her legs to lay it on her lap. She left her thighs spread just enough for us to see that she was wearing white cotton panties. With her purse on her lap and pretending to rummage for paperwork, she discreetly unbuttoned several buttons on her dress.
When Anne finally found the papers that she was looking for, she bent to put her purse back on the floor. I knew this meant that if she was braless, her beautiful breasts would be nicely exposed, and they were. Even though I had seen those perfectly shaped breasts with their perky nipples before, it was still a cock stirring sight.
Ted had glanced back at me just as she bent down so I quickly pointed out what he was missing. Just as Ted’s gaze turned to Anne she raised up so that he had only a passing glance of those sweet orbs. When she was upright again, Anne went back to texting but left her legs slightly apart. It was at this moment that I turned to her, with an obvious hard-on, to tell her that we would be done in about ten minutes.
While I printed off some papers, pretending that they were an application, Anne asked where the restroom was located. She obviously knew where it was but I pointed her down the hall directly behind Ted.
There is something to be said for a confident, in-shape, fifty something woman, showing off her assets. Anne must have practiced bending over in that dress a hundred times, because what we witnessed was perfection. She didn’t bend her knees to retrieve her phone and her dress quickly rose to the edge of her ass cheeks.
Fumbling to pick up her phone with her left hand, she must have pulled down on the front of her dress with her right hand. That quick jerk of her dress was enough to show us her cotton covered mound and the fact that she was wearing a g-string. Anne quickly stood up after that and entered the bathroom where she stayed for the next couple of minutes.
Ted turned back to me and asked me how I was keeping from fucking this super sexy woman. I told him that I probably wouldn’t be able to resist much longer, but it was so hot watching her expose herself. I then told him that we would be pretending to finish up when she came out, but to keep an eye on her crotch. I told him that the last time she went in to the bathroom, she removed her panties.
Just as Ted started shaking his head in disbelief, Anne came out of the bathroom and headed our way. With Ted facing me while we pretended to sign papers, Anne took the opportunity to quickly raise the front of her dress and show me her gorgeous flower. Stuttering for a moment, I finally told Ted where to sign as Anne sat back in her chair.
It is a good thing that I was sitting behind a desk, because at this point there was an obvious wet spot on my pants. Printing off a couple of pages to complete Ted’s fraudulent transaction, I turned towards Anne to retrieve the pages from the printer behind me. In that brief moment Anne noticed my pulsing hard-on, as well as the wet spot and flashed me a knowing grin.
Not quite ready to leave, Ted asked me a couple of questions. While continually looking back and forth from Anne’s legs to me, I know he was hoping for one last flash. Picking up on his desires, Anne spread her legs wide just before bending over to pick up her purse again. In that all too brief couple of seconds, Ted and I saw all of Anne’s beautiful assets.
Standing to leave, Ted seemed extremely proud that his cock seemed ready to burst forth from his jeans. It also seemed to have an intoxicating effect on Anne as she momentarily slipped a finger inside herself after he passed by. After coming down from her high, she moved to the chair in front of my desk and unbuttoned the rest of her dress.
As I admired her near perfect body, Anne seemed to be feeding off of my obvious desire. Leaning her head back, she slipped the middle finger of her right hand into herself. As she slowly started pumping it in and out, her left hand reached for a nipple and began gently twisting and pulling. Now I am not one to take advantage of someone, but I certainly could take care of myself and did just that.
When Anne heard my zipper go down, she looked at me through lust-filled eyes and asked if she could watch me. I stood at my desk, letting my pants fall to the floor and started stroking myself. With her eyes fixed on my cock, Anne added two more fingers to her pussy and began pumping in earnest. The sight before me was one of such lustful abandon, that I don’t think it was more than sixty seconds before I was shooting ropes of cum across the desk.
Seeing my cum exploding towards her, Anne put her bare feet up against the side of my desk in what seemed like an attempt to spread herself wider and get her fingers deeper. Whether or not she got any deeper, the effect was explosive. With an ever louder series of “Oh God” she reached a massive orgasm that left her hand, thighs and my chair soaked with her cum.
After pulling up my pants, I made sure to lock the doors and then came back to clean up my mess. Anne was still lying back in the chair with her feet on the desk and a wicked grin on her face. When she finally started to come around I handed her some paper towels but she grabbed her panties instead. When she finished wiping herself and the chair with her panties she told me to keep them as a souvenir.
Anne got up and headed to the bathroom with her dress still wide open, but when she returned a few minutes later it was as if nothing had ever happened. Approaching my desk, she said that she didn’t have time to complete the paperwork for the renter’s policy today. Then she asked if we could set another appointment for Friday at around the same time.
I told her that Fridays were generally quite busy, with a lot of customers coming to make payments. But if she didn’t mind the interruptions, I was sure we could get it done. Leaning in close enough to kiss me, Anne whispered, “Thank you, I had a wonderful time.”
Then she asked if I had any more ideas for our little joint venture.
Producing a notebook from my desk drawer with a list of numbered lines ending at thirty eight, I said I have a few. With her eyes wide from excitement she said, “We’re going to have a lot of fun.”
Then she walked away, pausing to raise the back of her dress to show me that superb ass one more time.
