Conquering Anneliese Pt. 03

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.

"You may swallow, but do not wipe you mouth until get to you desk. Also, you better takes great pains to make sure no one sees that jizz on your face while you walk across the office. Stand up."

Anneliese rose and I reached under her dress. I felt her thighs, which were clean, and slipped two fingers into her pussy. Anneliese squealed. "Still wet, I see" I teased, leaving my fingers. I started to pump her thinking I'd reward her with a quick orgasm, but then realized my door was still open. I pulled my fingers out and smelled them, taking in her scent. "Come back once everyone is gone." The thought of Anneliese having to turn away from colleagues to hide the cum on her face as she walked back to her cubicle made me smile.

Having blown my load in Anneliese's mouth, I fell back into productivity for the next two hours, barely checking the clock. At 6:30, Anneliese appeared in my doorway, her chestnut hair perfectly framing her beautiful dark blue eyes as she held three shopping bags. "Everyone has left the office, sir." she said. I could see her eyes darting around my office, her nervousness evident.

"Come in Anneliese, and close and lock the door. You may place the shopping bags on the desk. In the bureau across the room you will find a wine opener and glasses. Please pour me a glass of wine." I watched the erotic swishing of her dress as she walked across the room and retrieved the items as instructed.

As she poured the wine, I continued "Anneliese, you disappointed me this morning by not following our rules regarding your panties."

"I'm sorry sir, I promise it won't happen again" She quickly interrupted. I held my hand up, signaling her to be quiet.

"I understand, and I believe you, my gorgeous creature. But, I cannot have you disobeying me. Take off your dress please." Biting her lower lip, Anneliese slid the straps of her dress off of her shoulders and allowed her dress to fall to the ground. Seeing her naked before me, I said "I am glad you had the common sense to not wear a bra in here this evening."

"I removed it this morning as soon as I got back to my cube. I wanted to be sure you could access my breasts easily if you wanted. I was actually a little disappointed you did not check when you let me suck you this afternoon."

Anneliese was being exceptionally deferential; she knew she was in trouble. "Anneliese, climb up on my desk and lay down on your stomach with your head hanging over the edge. You may look ahead or down, but do not look behind you." As she moved to comply, I drank some of the wine and began to take the items out of the bag behind her. I gently folded her left leg up, bending it naturally at the knee and I began to suck each of her toes, something I had never done to her before. She cooed in enjoyment as I finished her pinky toe and then slipped a sock on her foot. I repeated the same treatment on her right foot. I then gripped her ankles, and widely spread her legs. She squealed as I forced them wider than she was comfortable with. I slid the the PVC pipe between her ankles and began to duct tape one side of the pipe to each ankle.

Anneliese's head came up from the desk and she began to protest "What are you doing! I didn't..." In a flash I came around to the other side of the desk and grabbed her head by a fist full of hair, bringing her eyes to mine. "You will be silent unless I ask you to speak, or your punishment will get worse." I yelled. With a whimper, Anneliese let her head down, resting her chin over the edge of the desk.

Sipping more wine, I took the sections of rope Anneliese had purchased earlier in the day. I carefully looped a section around each ankle and tied it to a leg of the desk. I walked around to the other side and placed her arms at comfortable (relatively) diagonals and secured each hand to another leg of the desk.

I poured more wine and circled desk admiring my handiwork. Anneliese was tied in an "X" on top of my desk with the PVC pipe and duct tape serving as a makeshift spreader bar, the socks making sure I did not harm her beautiful alabaster skin. From the rear, her ass and pussy were exposed. To the front, her head hand below the edge and she had to lift it to look forward. I stood in front of her head now. "Anneliese, how do you feel?"

"Sir, I'm sorry. I've learned my lesson. You don't need to tie me up. I will always do whatever you want."

"Yes, I know, sweetheart, but what I want right now is to tie you up and punish you for your earlier fuck up. Do you understand that?"

"Yes sir" She replied. I could see that her eyes were teary and that she was scared.

"Anneliese, you know how much I enjoy our arrangement, don't you? Do you trust that I never want to hurt you? However, in this case, I feel you need some discipline. You trust me, right?"

"Yes sir" Anneliese sobbed.

"Excellent, I think we should continue then." I checked the ropes and saw she was secure. From behind, I began to probe her pussy with my index finger. She was moist, but not wet. I went to work, but only used the one finger, penetrating her and rubbing her clit. Soon, her body responded and pussy was wet. Anneliese even let out a little moan as a rubbed her little bean more aggressively and added a second finger.

I reached back into the Target bag and retrieved the rolling pin. "My pet, do remember when you gave me attitude and I put that stapler into your pussy?"

"Yes sir, please don't do that again."

"Well Anneliese, today's infraction was more severe. I don't think that the stapler will quite cut it." I lined up the rolling pin with her tight pussy and for a moment doubted it would fit. Then I used both of my hands and pull open her pussy and pulled it in opposing directions. I was gentle but firm. I lined up the left side of her opening and began pulling her pussy around the right side of rolling pin. At that moment, I am sure Anneliese cursed herself for buying such a large one. It had to be two and a half inches in diameter and 14 inches long.

"Please sir, that will never fit inside me. You will kill me!" Anneliese screamed.

I looked out the window at the parking lot, making sure there were no other cars and therefore no one could hear her. I began to push on the rolling pin, and Anneliese screamed louder. Slowly, her vagina stretched to accommodate its latest intruder. As I pushed, I stroked her clit. I was in no rush. Once it was in a half-inch, I paused, both to refill my wine and give her a break. Little by little, the rolling pin disappeared into that tight, pink, pussy. After 10 minutes, it was inserted 4 inches. I walked to Anneliese's head.

"How do you feel?"

"It hurts sir. I have never had anything so big inside me. I feel stretched. Please take it out."

"Oh Anneliese, we are not close to done, I am simply giving you a break." I replied. With that I took of my shirt and dropped my pants. Would you like to have your break last a little longer, or should I continue?" I asked.

Anneliese lifted her head and immediately opened her mouth. After playfully slapping her face with my limp cock, I placed it in her mouth. This was different than earlier in the day when Anneliese quickly worked her mouth on my cock. Now she focused on sucking. It was clear that she had no intention of me cumming quickly. Having already cum twice earlier the day, that was likely a foregone conclusion anyway, so I let her suck me for around five minutes. I withdrew from her mouth hard as a rock and walked back towards her ass. The rolling pin had been pushed out of her pussy and inch or so from where I had previously inserted it. I could tell because of the wet mark Anneliese's pussy left on it. I slowly rotated it around while stroking her clit and pushed it back to where it had been.

I kept at her clit and kept pushing the rolling pin. Now the question entered my mind, "how far can I push this before I actually injure her." My intent was control and to make her uncomfortable, not harm my plaything. I figured that my cock was about 6 and a half inches long, and in certain positions I could bottom out Anneliese's pussy, bumping her cervix. I figured she should be able to take another 2 to 3 inches of the rolling pin and I kept pushing. Two things happened. As I rubbed her clit, Anneliese came. When she came, I slid the rolling pin deeper until I felt the resistance of her cervix and she screamed in pain. I pulled the rolling pin out a quarter inch and poured more wine, marveling at what I saw before me. This gorgeous woman tied and helpless across my desk with 7 inches of rolling pin sticking out of her twat.

I walked to her head again and grabbed her by the hair. She opened her mouth and I fucked it vigorously for about a minute. I pulled out and walked back towards her rear.

"Anneliese, it is now time to punish you and then show forgiveness."

"WHAT?!?!" Anneliese exclaimed, shocked. "I thought the punishment was you fucking me with that huge rolling pin."

"No, my pet, you will now be spanked like a disobedient child. Spankings will be how you are disciplined from now on. I will spank one of your ass cheeks 10 times and you will count. When I reach 10, I will switch cheeks. This will go on until I am satisfied. Let's begin." By swat # 8, Anneliese was in tears. I finished her right cheek and increased my tempo, slapping her left cheek 10 times in quick succession. I paused to look at my handiwork. Anneliese's ass was bright red, with numerous hand prints visible. She was sobbing uncontrollably.

"Anneliese, before we continue, would you like to cum?" I asked her.

"I don't know if I can!" Anneliese sobbed

"Would you like to try, or should I continue with your spanking?"

"Yes sir, I'll try" said Anneliese, willing to try anything to give her tender backside a break.

I rotated the rolling pin inside her slowly and reached under begin massaging her clit gently with my fingers. I went slowly, allowing her to catch her breath and stop her sobs. When she had calmed, I withdrew the rolling pin three inches and slowly pushed it back, establishing a steady rhythm of fucking her with her Target purchase and rubbing her clit. She began to rock, wordlessly telling me she was moving towards an orgasm. I stopped fucking her, leaving the pin inside her, and continued on her clit. I licked my index finger and gently placed it on her asshole. I caressed her tiniest hole with my finger tip, all the while keeping steady on her clit.

"What are you doing, sir?" Anneliese asked.

I knew Anneliese had never had anything in her ass, and that her anal virginity was intact. She had professed to never, ever, want anal sex and it was a boundary I had respected.

"Relax Anneliese. Enjoy the feelings my hands are giving your body." I responded as I applied the slightest pressure to her asshole. She obeyed, and my fingertip penetrated her tight virgin ass. I had achieved one of my objectives and now wanted to reinforce her good behavior. I withdrew my fingertip and used my right hand to spread her ass cheeks and leaned down to tongue her asshole. I pushed my tongue into her ass and increased the rate and pressure at which I rubbed her clit. In less than a minute, Anneliese climaxed. Hard. Her limbs pulled at the ropes restraining her to the desk. I kept rubbing her clit and tonguing her ass, allowing her to cum and cum until she begged me to stop.

"How was that Anneliese?"

"Oh my God sir, I don't think I have her ever cum that hard." she gasped, still out of breath.

"Did you like me touching and licking your asshole"

"I, I'm not sure. I never wanted to be touched there, but when you did it while playing with my pussy, I... I came so hard."

"This was another lesson, my sexy girl. You must allow me to use you completely. I will always make sure you are rewarded. Now, let us finish with your punishment so we may put this unpleasantness behind us. Are you ready?"

"Yes sir, please finish."

My cock had been at full mast for a while now and my interest was shifting from her punishment to my pleasure and how Anneliese would again drain my balls. Each of her cheeks received another 10 slaps, plus 1 for good luck. Anneliese sobbed, but was much more contained than after the first round of spankings. I walked around the desk to her head. She lifted her head and I saw her beautiful face covered with streaks of tears. Before I said anything, she opened her mouth.