Playing with the Principal

Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me. Your opinions are welcome but your attacks are not.

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Over the years that my son had been in high school, I'd attended many events where his principal, Dr. Oaks, at the very least made some opening remarks, but I wasn't sure that she knew me more than to wave hello if she noticed me. I was pretty surprised at this particular event when she sat down beside me in the auditorium before things got started. Not only that, but she mentioned something that she and my son had had a conversation about, which meant that she not only knew him but also knew that he was my son. While I was pleased that she was acknowledging my kid, I was also pleased that she was acknowledging me. Although Dr. Oaks was not necessarily a stunner, she was not a bad looking woman and she had a nice figure. I didn't know what her situation was but, since I was unattached, I was interested in finding out, especially as the conversation continued and we got mildly flirtatious.

"So what's the career path to becoming a principal?" I asked her at one point, "Is that in the back of your mind when you start teaching or do you take a class on 'The Principles of becoming a Principal' somewhere along the line?"

She laughed hard enough to attract some attention, though I thought it was mildly amusing at best.

"That's funny," she said, "Can I use that? If you're really interested and not just making polite conversation, maybe we can talk about it over coffee sometime."

"I would really like that," I replied, "though I suppose you wouldn't want to hit one of the coffee shops frequented by your students."

"Well, I am single, so I am allowed to have coffee with a man," she stated, "but, since you are a parent, we don't want to put anyone in an awkward spot."

"I work downtown," I told her, "so there are plenty of places we can meet near my office if you'd prefer."

"That sounds like a good idea," she said so I gave her my business card and told her to just give me a call when she had the time. I didn't get another opportunity to talk to her after she took to the stage and made her remarks but I had a good feeling about the way things had gone.

It wasn't very long before I heard from her, which pleased me. She was okay with driving downtown to meet so I suggested someplace to park and said that I'd meet her at the coffee shop across the street. It didn't really feel like a date but it seemed like it could potentially lead to one, depending on how it went. We got our coffee and sat and talked...and talked...and talked. The conversation really flowed and we both probably would have been content to stay there for the entire afternoon, but neither of us had planned for that. It felt like too soon that we both had to get back to work. We agreed that we'd figure out when we could see each other again then I offered to walk her to her car.

We crossed to the parking garage and, once we reached her car, we had a limited degree of privacy compared to a parking spot on the street. I took advantage of the opportunity to slip my arms around her and planted my lips on hers as her arms went around my neck. A potentially quick kiss goodbye quickly evolved into making out while holding each other tightly. I was resisting the urge to slip my hands down to her ass but I couldn't prevent my cock from growing so I was sure she must have felt it between us. Maybe that was what motivated her to suggest we sit in her car.

With my slacks tented out, I moved around to the passenger side while she slipped into the driver's seat. As we leaned toward each other and went back to making out, her hand found my hard cock and started to massage it.

"It's been a long time since I've been with somebody who I've wanted to do this to," she stated after pulling her lips away from mine, "but would you mind if I sucked your cock?"

"Of course not," I replied with a smile, even more pleased with how this was going.

As she went to work opening my slacks, I reclined my seat so that I could comfortably watch. She extracted my cock and pumped it in her fist as I slipped my slacks and underwear down just a bit further. I savored the feeling and let out a moan as she wrapped her lips around my tool and engulfed it in her hot mouth. I certainly hadn't been expecting a blowjob when we'd made our plans for coffee but I assumed that, being single, maybe she just hadn't had an opportunity to enjoy some cock in a while. I was certainly more than okay with being the cock to end a drought. I was glad that her shoulder-length blonde hair was pulled back so I could watch as my cock disappeared repeatedly into her mouth.

She definitely had some skills when it came to cocksucking, which I bet her students would never have imagined, but I didn't get the sense that she was trying to draw out my pleasure. We both had to get back to work, so that was fine with me, but as I thought about how wet her pussy probably was, I had no intention of letting her leave without giving me the opportunity to confirm it. The combination of the visual and the feel of her hot mouth on my cock had an orgasm building pretty quickly, which I think we were both fine with. I suspected that there would be more opportunity to indulge ourselves at some point in the future based on the way this day was going. When I exploded into her mouth with a moan, her reaction was barely noticeable as she continued sucking me off while swallowing my load. She didn't let my cock fall from her mouth until I was completely spent, then she sat up, wiping her mouth.

"Thank you," she said with a smile.

"Oh, no," I replied, "thank you. And don't think I'm going to let you get away without returning the favor."

"You don't need to," she started.

"Actually, I think I do need to," I told her, "and not just from the standpoint of proper etiquette. If I let you run off without tasting your pussy first, I will be dogged by what I missed until I get another opportunity."

As I was saying this, I was sliding her skirt up her long, thin legs until her panties were exposed. She didn't resist when I started to slide them down, raising her ass off the seat to allow me to reveal her trim, blonde bush. I could feel the blood already trying to return to my spent cock as I admired it and, once I'd set her panties aside, I moved in for a closer look. I ran my fingers through the short blonde fur then stuck my tongue out and ran it up her slit, tasting her pungent juices. She made a sound that I don't know if I could describe, but seemed to embody desire, arousal, relief, frustration and pure lust all at once. I wouldn't say it was exactly what motivated me but it didn't hurt. I went from licking her slit, lapping up her nectar, to licking and sucking her clit while sliding a couple of fingers in and out of her juicy pussy. She was holding my head, humping her pussy against my face while sounding as though she was trying to refrain from moaning extremely loudly.

I didn't think it was going to take much to get her to cum and was certainly hoping for another opportunity to spend more time devouring her pussy, but I figured a quick, intense orgasm would improve the odds of that happening. Her pussy was so wet and getting more engorged with every passing second. I knew I wouldn't be able to fuck her then, but I'd certainly be thinking about how incredible it was going to feel when I finally did. I could tell she was getting close to cumming not only by how wet and engorged her pussy was, but also by how she was tensing up and arching her back. When she did start cumming, the first thing that happened was she suddenly went limp, then her body started shaking as she gasped. I continued eating her as she rode out a long and apparently quite intense orgasm. When she finally went still and let out a sigh, I raised my head, though my attention initially was still on her blonde bush.

"Oh, that was a long time coming," she finally said and I raised my gaze to her face, "Thank you so much."

"It was my pleasure," I replied, "though I expect to be invited back."

"Absolutely and without a doubt," she assured me, "but for the moment, I think we've probably already got people wondering where the hell we are."

She slipped back into her panties as I got myself tucked away and my pants closed up. Once we were presentable, I gave her my personal contact information and we kissed, briefly but passionately, before I slipped out of her car and headed back to work.

Over the next few days, we couldn't find a time to get together for a more extended and less public encounter, but we texted and emailed and finally got desperate enough that Dr. Oaks suggested something really naughty. We scheduled an appointment for me to come see her in her office at the high school. I made sure that it was during a time when I was not likely to run into my son and she made sure that she was not likely to be interrupted. I came directly from work so I looked very professional and, when she came to greet me and escort me into her office, we acted as though we were just acquaintances and nothing more. Once the office door was locked behind us, however, it was an entirely different story.

We were immediately in each other's arms, making out passionately as my hands dropped down to her ass so I could pull her against the growing bulge in my slacks. I detected something else as my hands explored her ass and decided that I needed to confirm what I thought it was. She had wisely chosen to wear a dress that buttoned all the way up the front, so I moved my hands between us, first fondling her substantial tits, then starting to unbutton her dress from the top down. We ended up separating as I continued down, in part, I think, because she wanted to see my reaction to what I discovered. Once I reached the last button, she held her dress open for me and my eyes went wide. Her bra was low cut enough to show her succulent cleavage but, in addition to bikini panties that matched the bra, she was also wearing a garter belt to hold up her black stockings. I thought my cock was going to burst out of my Dockers.

"I had a feeling you'd like this," she said, "but I don't want you staring all afternoon. I'd rather you fuck me right here in my office."

That got me moving so I opened my slacks and let them drop then had my underwear follow as my rigid tool sprung out. As she reached out to pump it, I started to slide her panties down over the garters and stockings until they were headed for her ankles. She kicked them away then hopped up onto her desk and lay back. I guided my cock toward her blonde bush and slipped easily into her hot, wet pussy, both of us biting back a moan. I hooked her legs over my arms and leaned forward as I started to slowly slide the full length of my cock in and out of her. Her pussy felt absolutely amazing, just as I'd expected, and her tits were soon bouncing with my thrusting so I knew I'd have to free them from their confinement to enjoy them a bit, too.

I'd never fantasized about fucking a principal, mainly because mine had all been old men while growing up, but Dr. Oaks, with her blonde hair, substantial tits and garter belt, would have made an ideal fantasy. If only the hormone-laden teenage boys all over campus could see what she was up to at that moment. I fully appreciated how fortunate I was to be experiencing what she had to offer and was savoring the feel of her hot pussy as my cock slid in and out of it. The harder I was fucking her, though, the more she was starting to slide across her desk. Even as I held her legs and she reached down to hold onto the edge of her desk, because she was lying on her blotter, she was moving around a bit. Reality is always a little bit different from the fantasy. Finally, I suggested we reposition.

She slipped out of her dress as she got up, laying it across her chair, then turned around and leaned on her desk as I moved up behind her. I guided my cock back into her hot pussy from behind and took her by her narrow hips as I eased all the way into her. Again I was appreciative of how awesome her pussy felt as I slid my cock in and out of it. Once I had a good rhythm going, I slipped my hands up to cup her tits as one of her hands dropped down between her legs to stroke her clit. I caressed her tits, still encased in her sexy, low-cut bra, feeling her hard nipples pressing outward, before reaching for the clasp and unfastening it. As she slipped out of her bra, my hands were on the soft, smooth flesh of her swinging tits.

She started pushing back against my incoming thrusts the longer we fucked and an occasional soft moan would slip out. I could also feel her pussy becoming even wetter and more engorged as we continued fucking, which had my orgasm slowly beginning to build. I was really enjoying playing with her tits but, as she pushed back against me harder, I had to take her by the hips again to keep us in synch. I imagined that her tits were swinging like crazy but I wasn't necessarily disappointed to no longer be fondling them as I relished the feel of her hot pussy on my cock. When she pushed back hard against me and I felt her body trembling, I just held her so that my cock remained fully embedded inside her as she came.

Her orgasm appeared to be long and intense and, when she finally relaxed, I slipped my cock out of her because I'd been thinking about how her pussy had been flooded with additional lubrication. One thing this meant was that it'd likely make me cum faster, which I wasn't ready for yet. It also made think about getting my tongue down there and lapping up some of that pungent nectar. I also wanted to make her cum again since she'd quite obviously gone for a while without someone else making her cum based on our first encounter.

She straightened up and turned toward me so we made out briefly while I fondled her unencumbered tits before I lowered my head to lick and suck her hard nipples. I continued fondling the soft, smooth flesh then also caressed her ass and brought a hand around to her pussy, finding it still overflowing with juices. This motivated me to have her sit up on her desk again as I sat in her desk chair. She spread her legs, not needing convincing this time to let me do this, and I kissed her inner thighs before running my tongue up her slit. She gasped as I lapped at her slit, slurping up her copious juices, before slipping a couple of fingers into her. As I pumped them slowly in and out, I was licking and sucking her clit while she held my head and humped her pussy toward my face.

This still wasn't the time and place to indulge myself and eat her through multiple orgasms, so my goal was to make her cum so that I could then cum myself. As such, my focus was on giving her intense pleasure rather than drawing out her pleasure. Her reaction was giving me a pretty good indication that I was achieving exactly that. I glanced up as I continued to chow down, admiring the substantial swell of her tits and, beyond them, the ecstatic look on her face. Her pussy was becoming even wetter and more engorged the longer I ate her, so I knew it wouldn't take very long before she came, but I was hoping she'd be able to contain any expressions of pleasure that tried to slip out. I couldn't imagine the repercussions if she let out a loud, passionate moan that could be heard outside her office, especially by students.

When she did start cumming, a gasp was the only thing that slipped out and even that was very reserved. I continued eating her as her body trembled, not wanting to miss any of the additional juices that were flowing as she came. Her orgasm proved to be long and apparently as intensely pleasurable as I'd hoped it would be. When she finally let out a shaky sigh and went still, I reluctantly raised my head, my attention still on her trim, blonde bush until she spoke.

"My God, that was amazing," she exclaimed as she tried to catch her breath.

I looked up, my gaze locking on her tits momentarily before we made eye contact. She smiled at me and started to sit up as I straightened up in her desk chair.

"Let's switch places," she suggested and I immediately had a good idea of where things were going. I stood, my rigid cock sticking out before me and immediately catching her attention. She reached for it as she hopped of her desk, her tits bouncing and catching my attention. As I reached for them and caressed the soft, smooth flesh, she took my cock in her hand and stroked it as we traded places. She took my place seated in her desk chair, taking her boobs out of my reach, so I hopped up onto her desk and watched as her head moved toward my cock. While she continued to stroke my cock, she ran her tongue over my balls then up along the underside of the shaft before wrapping her lips around the head. As she pumped the base of my cock, she slid her lips up and down, once again demonstrating her undeniable skill as a cocksucker.

I would have been perfectly content to just watch her suck my cock until I blasted a load down her throat, but she had something else in mind which I had no issue with. She raised her head and moved her chair under her desk more, then hefted her tits in her hands and squeezed them around my cock. I had to bite back a moan as she slid the soft, smooth flesh up and down my throbbing tool and immediately felt my orgasm beginning to quickly build again. Leaning back on my elbows, I watched her sumptuous globes engulfing my cock as her attention was on my cockhead disappearing and reappearing. The building level of pleasure was incredible and I was definitely savoring it as my cock swelled even more in anticipation of cumming. I figured I'd be spewing on her cleavage but, when I was right on the verge, she released her tits and engulfed my cock in her hot mouth again.

Pumping the base, she slid her lips up and down as I tried to bite back the moans of pleasure that were trying to escape. I know she glanced up at me a couple of times but I was beyond offering any reassurance other than the look on my face that I'm sure must have reflected the pleasure that I was feeling. When I finally exploded into her mouth, it took everything in me not to let out a loud moan. She continued to suck me off while swallowing my load, which seemed to spurt endlessly into her mouth. When I was finally spent, she nursed my softening cock a bit longer before letting it fall from her mouth and smiling at me.

"That was fun," she purred.

"You're not kidding," I replied, "We really need to plan some quality time alone."

"I totally agree," she said, "and the sooner, the better."

Unfortunately, at that moment we really needed to make ourselves presentable again, but we did make it a high priority to plan some time together, just the two of us, as soon as possible. When we finally got the logistics all worked out, it ended up being completely mind blowing.