The Many Loves of Anna Marie Pt. 02

Stephanie shook her head as if trying to shake something off it and frowned severely at me as she said, "Miss O'Reilly, I want you to see me after class."

"Yes, Mrs. Grierson," I replied meekly before flashing a big smile that only she could see.

Stephanie composed herself and started her lecture for the day. Today, she studiously tried to ignore me, but the first time her eyes landed on me, I spread my knees apart, my short skirt not hiding the blue and white shorts I was wearing under it, before snapping them back together. Stephanie stopped dead, her mouth hanging open. She quickly recovered, cleared her throat, and continued with her lecture after throwing me a fleeting scowl. I sat there with an innocent look on my face, beatifically smiling as I took notes in my notebook.

I behaved myself during the rest of the lecture, taking copious notes and trying not to ogle Stephanie's ass when she'd stop in front of me and turn from side to side as she lectured to different sides of the classroom. I could tell she was putting on a show for me, and I loved how her skirt cupped her ass. When she walked away from me, I could tell she was putting a little extra in it, making her ass move in a way that made me wet and needy.

Finally, Stephanie brought the lecture to an end. She reminded everyone about the quiz at the start of Monday's class before wishing everyone a fun weekend. While everyone was filing out, I stepped up to Stephanie.

"You wanted to see me, Mrs. Grierson?" I asked loudly so the other students would know I was acting appropriately with Stephanie.

Stephanie looked at me severely and asked loudly, "Miss O'Reilly, do you think that's an appropriate outfit to wear to class?"

I fought hard not to smile or give away the fact that my nipples were tenting my sweater as I stood there. "No, Mrs. Grierson. I'm sorry." I said contritely, just as the last student left the room.

Suddenly, Stephanie smiled and softly said, "I love your outfit."

I smiled and stepped up to her, our bodies nearly touching. In her heels, Stephanie towered nine inches over me, and the swell of her breasts was right below my eyes. I wished she wasn't wearing the jacket so I could see if her nipples were as hard and extended as mine. I tilted my head back so I could look up into her eyes. I put my best sweet innocent look on my face and said, "I love your outfit, too." After a beat, I asked, "So what did you want to see me about, Steph?"

Stephanie asked, a shy smile on her face, "I was just wondering if you were ever going to schedule an appointment?"

I smiled widely and said, "Actually, I do have a problem I want to see you about."

"Is it class related?" Stephanie asked, her eyes going wide and nearly black.

"No, it isn't," I nearly moaned, losing myself in those wells. I licked my lips and finished, "That's why I think I'll need an appointment."

"Well, I'll be otherwise occupied most of the day," Stephanie said, licking her luscious lips. "Would seven o'clock in my office work for you?" she asked hopefully.

"It will," I replied, my whole body pulsing at the thought of seeing Stephanie tonight. My nipples threatened to rip through my sweater, and Stephanie's eyes locked on them. She was licking her lips, so I knew she wanted to suck on them. I wanted that, too, so I smiled and said, "See you at seven." I spun around so quickly that my braid swiped across Stephanie's breasts. I heard a moan behind me as I bounced away, toe-walking to the door, making sure to sway my hips and ass as much as possible.

Seven o'clock couldn't come fast enough, but eventually, I found myself outside the door to Stephanie's office. I was still wearing my cheerleader outfit but had stopped at the bathroom down the hall from her office, removed my shorts and panties, and walked up to her office door commando. I had also taken a couple of items out of my 'toy box' and stuck them in my purse before leaving my room.

Right at seven o'clock, I knocked on the door. Almost immediately, Stephanie called out, "Come in, Anna."

I opened the door and walked in, noting the scholarly clutter on the shelves surrounding three sides of the office. The office was dimly lit by a single desk lamp, and there was a small alcove behind the desk and a partitioned-off area that I assumed was a bathroom. Stephanie was sitting at her desk, facing me. I noticed that she had taken her jacket off, which was now lying on the arm of the couch in the alcove behind the desk. There were two straight-back chairs in front of the desk for visitors.

I turned and closed the door, making sure to lock it so that if things went well, we wouldn't be disturbed by the maintenance man. I turned back to Stephanie, walked up to one of the chairs, and stopped. Stephanie stood up and leaned over the desk, extending a hand for me to shake. Her blouse had the top three buttons undone, and it billowed open. I couldn't help but notice that she wasn't wearing a bra as I admired her impressive cleavage. I didn't hide the fact that I was looking, either.

When our hands touched, it felt like a bolt of lightning had flashed through my body. I moaned, and my nipples immediately tented my sweater, the ache hurting so much it felt good. I saw that Stephanie's nipples had done the same, and I gasped at seeing how far they poked out. My mouth watered at the thought of sucking on them, and I hoped she wouldn't mind my biting them.

Stephanie's eyes were locked on my nipples, and I hoped she wouldn't mind sucking on them and biting them. She gripped my hand as though she feared I'd disappear in a puff of smoke if she let it go. I was mentally undressing Stephanie, wondering what the color of her nipples was and if her carpet was the same color as the drapes.

Finally, she let go of my hand and straightened up before indicating that I should sit. We sat down together, and Stephanie steepled her fingers and asked, "So, Anna, what sort of problem did you want to see me about?"

"Well, Steph," I started, putting an embarrassed look on my face as I reached into my purse and pulled out a flesh-colored 8" silicone dildo with a bulbous head and ridges all the way down the shaft, "I got this the other day. However, it didn't come with any instructions." I set it down on the desk between us, standing it on end to proudly point to the ceiling as Stephanie's eyes grew wide, and she pulled in a sharp breath.

After several false starts, Stephanie found her voice, leaned in, and asked, "And how can I help you with that?" Her eyes were locked on the dildo, and her tongue peeked out and licked her lips.

I leaned forward, licked my lips, and said, "I was hoping you could teach me how to use it."

Stephanie started, gasped again, and asked, "Teach you?"

I picked up the dildo, brought it up to my mouth, and began licking the end of the dildo. Stephanie's eyes were focused on my mouth as I explained, "You know, tell me how to use it." I locked eyes with her, smiled, and with my best bedroom voice, said, "Or, you could show me how to use it?"

Again, Stephanie started and gasped. Before she could get over the shock, I stood up, walked around the desk, and held the dildo out to her. Her gaze kept switching between the dildo and up to my face as I held an innocent look on my face. After a beat, she reached out and took it from me. Once Stephanie had the dildo, I flipped up my skirt and hopped up onto her desk. I spread my legs, resting my sneaker-clad feet on the arms of her office chair as I leaned back, holding myself up with my hands behind me.

Stephanie's eyes snapped to my hot and wet pussy and got so big that I was momentarily concerned they would pop out of her head. She gasped and moaned, "Oh, my, Anna."

In my sexist voice, I asked, "Do you think you can help me, Steph?"

Stephanie's eyes came up to meet mine, and the smoldering desire I saw in them made me moan. She licked her lips and said, "Yes, Anna. I believe I may be able to help you with your problem."

I smiled and said, "That's great, Steph. I knew I could count on you to help me."

Stephanie got an introspective look on her face while tapping her chin with the tip of the dildo. I wondered if she realized how sexy that looked. She started, "Now, we just need to decide what approach we're going to take to solve the problem." She leaned forward and said, "First, I'll need to examine every aspect of the problem." She focused on my pussy, which was so wet I could feel my juices dripping down over my perineum and onto my anus. I hoped I wouldn't mess up Stephanie's blotter.

I watched intently, my whole body on fire, as Stephanie leaned in and took a deep breath. Watching her breasts rise, and her nipples trying to burst through her blouse made me moan. I pulled my right hand from the desk, holding myself up with only my left hand, and began massaging my aching nipples. It felt so good to pinch and pull them, although I really wanted Stephanie to be the one to do it. A look of appreciation came over Stephanie's face, and she went, "Ahhhh," before she husked, "Oh, God, Anna. You smell so good!"

I moaned, "So, that's not a problem?" while rolling my hips.

"Oh, God, no!" Stephanie said as she took another deep breath. Her eyes snapped to my hand, which was busily massaging my nipples, and she licked her lips again at the sight of my nipples tenting my sweater. She smiled and said, "However," drawing out the last syllable before continuing, "I think your sweater may be interfering with my investigation."

Stephanie laid the dildo down in her lap, reached, and started working the bottom of my sweater up over my core. When she saw my abs, she stopped, her eyes going wide. She gasped and then moaned, "Oh, God!"

I loved it whenever I got that reaction. I worked out hard, making sure my core was cut, and I was proud of how it looked. Stephanie's response was typical for someone who saw it for the first time. She looked up with wonder and said, "My God, Anna. Your core is incredible!"

I moaned, "So, that's not a problem, either?" flexing my abs and making my little six-pack more distinct.

"Oh, my God, no!" Stephanie moaned fervently, letting go of my sweater and running her fingertips down my core. The sensations made my muscles spasm as her fingertips left trails of fire behind them. She was fascinated with my abs, and I was willing to let her spend some time examining them. I loved how she traced the ridges of my six-pack with her fingertips.

While she was examining my core, I was still busily pinching, pulling, and rolling my nipples, enjoying how intently Stephanie was investigating my problem. Finally, I decided to help move her investigation along. I sat up straight and pulled my sweater up over my breasts, loving how the cool air felt on my nipples.

Stephanie's eyes snapped to my breasts, and another moan left her lips. I watched her lick her lips as she slid her hands up over my ribs and captured my breasts, cupping them and ensuring my long hard nipples were between her thumbs and forefingers. "God, Anna, your breasts are wonderful!"

Stephanie started massaging my breasts, her fingers digging deep into my flesh, pinching my nipples while doing so. The look on her face made my body thrill even more, adding to the pleasure of her manipulation of my breasts. I moaned, "Oh, God, Steph, I think you need to investigate them closer to see if they're the problem!"

To further aid her investigation, I leaned forward. I watched Stephanie as she leaned in and captured my right nipple in her mouth. The heat of her mouth on my nipple was divine as her tongue circled my nipple, licking my areola. When Stephanie finished that, she started lashing my nipple, sending spikes of pleasure to my clit. While she continued her investigation, I pulled my sweater off over my head, pulling my braid through it before tossing it over onto Stephanie's blazer.

I moaned loudly and put my hands behind my neck, interlacing my fingers and spreading my elbows wide, arching my back and thrusting my breast harder into her mouth. Our eyes were locked, and I could see the lust in Stephanie's eyes as she captured my nipple between her teeth and bit down on it. The pain/pleasure was exquisite, and I nearly elevated my ass off the desk as I wailed, "Oh, God, Steph!"

Stephanie quickly switched to my other nipple and did the same thing, eliciting another "Oh, God, Steph!" from my mouth as the impulses made my pussy flood. With a satisfied look, Stephanie backed away and shakily said, "I don't think there's a problem there."

My saliva-covered nipples rapidly cooled, and they hardened even more. I moaned with desire and reached out and started unbuttoning Stephanie's blouse. I said, "I think this may be getting in the way of your investigation." Her eyes watched my fingers working on her buttons, and as soon as the last one was undone, she practically tore her blouse off in her haste to remove it. She moaned, "You're right. We can't have anything interfering with finding the solution."

I loved what I saw. The first thing I noted was the tan lines that showed Stephanie had worn the skimpiest bikini possible with only small triangular patches of lighter skin around her areolas. The second thing I noted was that her areolas were relatively small, barely visible as a ring around the quarter-sized base of her cone-shaped nipples. They were darker than mine, and my mouth watered at the thought of sucking them into my mouth and thrashing them with my tongue before biting them.

"In that case," I said, reaching down to unbutton my skirt, "you should probably make sure this doesn't get in the way, either." As the last button came undone, I grabbed the edge of the desk with my hands and lifted my ass off it. Stephanie quickly worked my skirt down over my hips and off my ass. I sat back down, took my feet off the arms of her chair, and held them straight up in the air, pointing my sneaker-clad toes to the ceiling.

As Stephanie got my skirt past my knees, she went to stand up, and the dildo that had been forgotten began to fall off her lap to the floor. She grabbed it and stuck the bulbous end in her mouth so she could finish removing my skirt. I gasped at the sight of Stephanie's lips wrapped around the shaft of the dildo, making me moan. She quickly pulled my skirt off my feet and tossed it over on my sweater. I began to lower my legs, spreading them wide, coming down parallel to the edge of the desk until I was in a split, and the heels of my sneakers were resting on the edge of the desk.

Stephanie must have figured that, as long as she was standing up, she'd shed her skirt, too. I watched her hands as she undid the button and unzipped the skirt until she could work her thumbs under the waist and work it down over her wide hips. I gasped when I saw that she wasn't wearing panties, and her neatly trimmed and bikini-waxed pussy appeared over the top of her skirt. Her carpet was as blonde as her drapes, and it didn't hide her inflamed and red lips shiny from her excitement, her juices seeping out from between them.

As Stephanie sat down and scooted her chair closer to the desk, I asked innocently, "Is that how you use it, Steph?" indicating the dildo in her mouth.

Stephanie took the dildo out of her mouth. The head glistened from her saliva coating it. Stephanie used her lecturing voice as she said, "It's important to make sure that the dildo is well lubricated. Saliva works well for that if you don't have any other water-based lubricant handy. You need to ensure that the entire length is properly covered with enough saliva to ensure there is no resistance when using it."

I watched Stephanie intently, hanging on to every word and nodding my head. Stephanie continued, "There are several ways to do it. You can simply lick it all over with your tongue like this." Stephanie demonstrated the technique, carefully running her tongue up and down the shaft. I was fascinated by how long her tongue was as it deftly worked her saliva into every crook and crevice.

When she was done, she showed it to me and said, "As you can see, it is now properly lubricated and is ready for use." I leaned forward and looked closely at it, loving how it glistened in the dim light of the desk lamp.

Stephanie pulled it back and started lecturing again, "While effective, using just your tongue can take more time than you may be willing to spend. A second technique, which can speed up the application of the saliva, is to use your throat in combination with your tongue, like this." Stephanie tilted her head back and put the bulbous head of the dildo in her mouth, put her fingers on the end of the dildo, and pushed the entire length of the dildo into her mouth. I watched in fascination and moaned my appreciation as I saw the head distend her throat as it moved through it. Stephanie held it there for a beat as I watched her tongue move before she pulled it out of her mouth, a string of saliva hanging between the tip of her tongue and the head of the dildo.

Without missing a beat, Stephanie continued, "Of course, this technique requires you to control your gagging reflex as the tip of the dildo enters your throat. Note that the time required was significantly less for this technique." Once again, she held out the dildo for my inspection.

I leaned in, stuck out my tongue, and licked some of Stephanie's saliva off. Stephanie gasped before pulling the dildo back.

I asked, "Once the dildo is properly lubricated, what do you do next?"

Stephanie's eyes lit up with delight. "Allow me to demonstrate," she said. Stephanie thrust her hips forward and lifted and separated her legs, draping them over the arms of her chair, displaying her inflamed and wet pussy and making it accessible. She moved the dildo down and placed the head against her clit. She then worked it down her wet glistening slit, getting her juices on it along with her saliva. When the tip reached the bottom of her slit, and at the entrance to her hole, Stephanie stopped and said, "Once the head of the dildo is positioned correctly, you can then start the insertion process."

Again I leaned forward to get a better view, my tongue wetting my lips. I watched in fascination as Stephanie began lecturing again, "At this point, you need to decide how you want to insert it. I'd suggest you ease it in slowly for the first few times to ensure everything is properly lubricated. You wouldn't want to cause any damage from insufficient lubrication." With that, I watched as the head of the dildo slowly entered her hole, the walls of her vagina stretching around the bulbous head. I heard a low moan escape Stephanie's throat as her vagina closed around the shaft of the dildo once the head was entirely in.

"At this point," Stephanie continued, "your vagina is sufficiently stretched so the rest of the shaft should easily enter. Now, it's up to you to decide how far you want to insert the head. Some women are satisfied with short strokes with the head inserted just far enough to stimulate the g-spot." She demonstrated, moving the dildo in and out about an inch or so, slowly speeding up the stroking. I watched in fascination, pulling and pinching my nipples as I heard Stephanie's breathing increase as she started moaning. I joined her, our moans making beautiful music.

I cleared my throat and asked, "Why is the dildo so long if only the first three inches are necessary?"