The next months proceeded wonderfully. Anneliese dutifully returned to me after a day off (and every 3 weeks thereafter) and presented her freshly waxed vagina for my inspection, and often tasting, fucking and/or probing with whatever object happened to be within reach on my desk. One of my fonder memories was in the first or second month of our arrangement, Anneliese had responded to me quite snarkily, so I decided to stretch her little pussy with my stapler. She squealed and squealed, but ultimately, took it all. I told her she had to keep it inserted until she made me cum. Try as I might, when she was focused on sucking my cock, it was hard to last more than 2 or 3 minutes. Even now, sometimes the simple act of using that stapler gives me a semi that Anneliese then needs to take care of. I have threatened her with the stapler or other larger objects, but had not needed to use them. Plus, I really have no intention of permanently stretching the tiny, tight, bald pussy that brings me so much pleasure. However, I am definitely open to stretching it a little from time to time as needed for my enjoyment or to ensure her obedience.
Anneliese and I settled into a nice routine. Once a day, around lunchtime, she would ask how things were going. This was how she offered her services. We developed a nice little code. I would smile and nod my head when I wanted her to close my office door and enter for a service, I would give her the "come hither" sign with one finger when I wanted her to leave the door open and crawl under my desk, or I could shake my head "no" when work was too pressing for even a quicky. In addition, Anneliese could stand in my doorway and flash me her pussy if she was feeling particularly needy and I could consider her request. If I need to empty my balls before she appeared in my doorway, or later in the day, I would simply sent a "!" on her instant messenger and she would come running.
Throughout it all, I continued training Anneliese and making rules that governed our arrangement. This was completed either directly by laying down rules which then had consequences if broken, or subtly, by reinforcing positive behavior and expressing my displeasure at poor behavior. During the first weeks, I established my expectation regarding her panties. To start, they had to always be sexy to the point of garish sluttiness. Her panties were worn, or not worn, for my pleasure. We established that Anneliese could wear underwear each morning, but once at the office, whether they stayed on was up to my whims. On days where I would summon Anneliese for use, she was to remove her panties in her cubicle, then carry them in her hand and place them on my desk. This obviously led to the necessity of Anneliese wearing a dress or skirt, so the panties could be removed discreetly around her coworkers. I conceded that she was allowed to wear pants twice a week, but only if they appropriately highlighted her magnificent ass. In those cases, she could keep her panties on until she reached my office. Generally on pants days, I would simply have Anneliese crawl under my desk and suck my cock while I worked, or I would bend her over the desk and yank down both the pants and panties together before taking her from behind.
Early on, Anneliese once forgot our rules and she came into my office with her panties on. "Anneliese, why aren't your panties on my desk. You know the rule."
"I'm sorry sir, I forgot. I tried to get here as soon as I saw your message and I forgot. It'll only take a second." She said as she reached under her dress and dropped her undies.
"Unacceptable. I see you need consequences in order to remember anything. Tonight, you and I will remain in the office until no one else is here and I will demonstrate the consequences. In the meantime, over the desk." Anneliese complied without another word. I walked behind her and lifted her dark green dress. Her legs, already spread shoulder width, did not hide her beautiful pink pussy hanging just below her ass cheeks. I inserted one finger in her, enjoying the feeling of how tight she felt around just one digit. The anticipation of knowing she would soon take my cock into her tight slit never failed to give me a thrill and make me rock hard. I noted she was already moist and withdrew my finger while lining up my cock with her opening. "What do you want most of all Anneliese?" I asked.
"To feel you inside me, sir."
I immediately pushed into her, balls deep, and enjoyed what must be the best pussy the world could offer. All I could do is let out a sigh. I paused to fully enjoy the sensation, then pumped her little pussy for all I was worth. "Don't move." I said after filling Anneliese and withdrawing from her now sopping vagina. I stepped back and sat in my chair and enjoyed the view of he pussy, slightly agape, but slowly closing while my cum dripped out and began to run down her legs. I waited there until the first drops had made it to her feet.
"Anneliese, you will now run an errand for me at Home Depot and Target."
"Of course sir, what do you need?" She replied standing and beginning to smooth out her dress. It intrigued me that Anneliese paid no attention to the cum running down both of her legs, but I let the thought pass.
"At Home Depot, buy four sections of 1/2-inch diameter nylon cord, one roll of duct tape, and one 54-inch length of PVC. At Target, buy yourself a pair of socks and one of those rolling pins without handles. I'd also like to you stop by a grocery store and buy a bottle of Caymus Cabernet Sauvignon. Unless I summon you for a blow job between now and then, I I do not expect to see you until after everyone else is gone."
"Yes sir, I'll leave right now." Anneliese said, and with a swish of dress, and a shake of her ass, she left my office.
I began to plan Anneliese's punishment in my mind, but otherwise went back to work. I found that as the day went on, it was harder and harder to focus on my work. By 4 pm, I was fully distracted and knew I had another 2 hours before the office would be empty. I opened a chat on instant messenger and sent Anneliese a "!".
Thirty seconds later, Anneliese dutifully arrived at my office door. I asked her how her shopping went. "I got everything you asked for, but, umm..."
"Yes, Anneliese?"
"That was a pretty strange list, can I ask what they are for?"
"Anneliese, I don't have to justify every purchase I make, do I? I have some plans and I have not had time to shopping."
"Of course, sir." She responded, but I could tell her mind was trying to figure out if any of the items were related to her earlier infraction.
I beckoned her to come into my office and get under my desk. "Put that mouth to work like you did in college. I want to see how fast you can make me cum, and do not swallow until I say." Without a word, she walked around my desk, checked the door to make sure no one was in the hallway, and dropped underneath. She unzipped my pants and in under a minute my semi-hard cock was in her mouth. She was bringing her "A" game, I immediately noticed as I felt her tongue swirling all over the underside of the purple head of my manhood. Quickly hard, I then felt tongue licks up and down its length before I was quickly back in her mouth. What could I say? The girl was talented (and as discussed in Chapter 1, well-practiced). Using only her mouth, she went up and down faster than I could have imagined. As usual, I gave her no warning before I came, filling her mouth. Still sitting, she scooted from beneath the desk and looked up at me.
"Show me." I ordered.
Anneliese opened her mouth to show me the cum she was holding.
"Thank me."
Anneliese mumbled a "thank you" that caused some of my sperm to trickle down her face.
