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My Teaching Days, Part 1

My first intimate encounter with a student included some basic lessons
Almost nineteen years ago – imagine that! – I started as a combination English and physical education teacher at a high school in eastern Pennsylvania. I was still single, although I wouldn’t be for a whole lot longer. Perhaps most amazing of all, and I don’t expect you to believe this, I was still a virgin at the age of twenty-one.

My virginity got in the way of real relationships. My intention, based on some combination of conservative schools and conservative parents, was to “save myself” for marriage. Fear of pregnancy factored in a little, but I had enough faith in science that it didn’t weigh me down. Do you know how many fingers you need to count the number of guys that age who accepted my common sense premise and would take the time needed to build a real relationship? No fingers at all. You can, and should, use them on yourself instead.

I believe I was as horny as any woman my age. In fact, back then, I thought I was more sex-crazed than anyone else, because I never found the relief I thought that fucking provided. Later, I learned that fucking pushes the craziness to background noise for a while, but it doesn’t take long for it to crawl forward and squeal loudly again.

Everything except intercourse was inbounds. This included hand jobs, blow jobs (although I didn’t yet swallow on purpose), a very few college encounters with women, and plenty of masturbation. While a virgin by any standard definition, I’d lost my cherry years ago. I’d even had my first cock, made of blue silicone, not all that different from one I now kept in a drawer. I suppose anal sex should have been OK in principle, but it wasn’t.

Making matters even worse, if “worse” was the word, part of my physical education duties included managing the cheerleading squad. Unlike some schools, our squad consisted entirely of girls. While I loved them all, their constant jabbering about boys and sex sounded all too much like the voices in my own head.

I’m sure you’d like to read about a shower room full of naked cheerleaders and maybe I’ll get around to that, but not right now. The school had four thousand students in grades nine through twelve, so I expect it’s obvious I taught at a public school. I had only eleventh and twelfth grade English, with an emphasis on the above average students, which suited me perfectly. I liked boys and girls who could think for themselves and who could express what they think. I liked my adults that way, too, and still do.

In April of my first year teaching, with the big cheerleading sports of football and basketball behind me and school beginning to slow toward its inevitable conclusion, one of my most promising juniors remained behind after class, the last of the day. Chad had straight A’s in everything, I think, but I doubt he’d mastered anything as well as writing. His paper on existentialism blew me away. His poetry included metaphors that weren’t ridiculous. He was only sixteen, while many of his peers had already turned seventeen. He had some nerdish qualities, and he played no sports, but he had a quick sense of humor and a bright smile.

“Miss Taylor,” Chad began, “I’d like to interview you for the school paper. Do you have any time today?”

“We can do it now,” I said, “if you want to walk me home. I’m only fifteen minutes from here.”

There was no urgent need to go home. I liked the idea of company instead of walking alone. Taylor, of course, was my maiden name, and I still miss it sometimes. You might think that I was nuts for letting a student know where I lived, but all my cheerleaders had been over to my place and it was no big secret. Perhaps times were less scary then, or maybe I was naïve, I don’t really know.

We walked and talked. Chad wrote for the sports page and his only interest was in the cheerleading part of my job (and looking at my boobs, presumably not part of the article). It wasn’t so much an interview as it was a conversation. When we reached my apartment, he’d taken very few notes.

“Sorry, Miss Taylor, there’s a lot more I should ask. Can we do this again? Soon? Deadline is Thursday at six.”

“We can do it now if you want to come in.”

“I’m supposed to be home soon,” he said, frowning with concentration. “But this is more important. Thanks!”

My apartment wasn’t much, a small one bedroom with a small living room and a galley kitchen. There was nothing out of place. If you looked in the drawers you’d see everything folded neatly. Only the bathroom had a few items not put away, and while that bothered me, storing them somewhere would be too inconvenient. The kitchen counter space was limited and free of clutter except for a coffee maker, a thing that heated water and a toaster. I’d made a tiny office out of a closet by sticking a desk in it; when I sat there, the chair took up half the hallway. In the living room, we both sat on the second hand red leather sofa. There was nowhere else to sit.

In this more formal setting, Chad asked questions and I answered them. When he paused to think of the next one, I looked him over. While I usually fantasized more about the big football and basketball players (or, less often, certain of my cheerleaders), Chad’s lean Jimmy Stewart build appealed in a different way. He had a quick smile to go with his quick mind. His hazel eyes sparkled when he enthused about something.

“What did you say?” I asked.

“I want to make sure I’ve got all the names right for the cheerleaders,” he said, pointing at a list in his notepad. “Especially on a school paper, names are critical.”

I scooted over to check the list and my leg pressed against his. I think he would have moved away, but he was already at the end of the sofa. I took my time with the names and realized I enjoyed the contact. As though I were thinking absently, I scratched at the top of his thigh with my fingernails. I swear that’s all I did, but it must have been enough to cause an erection. He tried to be subtle, standing and turning away to adjust his cock in his jeans, but it was obvious.

Intimacy with a student entailed risks, but also offered the possibility of an orgasm from someone who would respond to me as a teacher instead of guy realizing he wasn’t going to get as lucky as he wanted. Before Chad could bolt out the door, I stood alongside and put a hand on his trapezius, massaging it with my fingers. Not for nothing was I a phys ed teacher.

“You seem a little tense,” I said, even though he wasn’t, and got behind him to use both hands. After probing quickly, I rolled my thumb over his lower TrP3 trigger point - that often tense spot right next to his shoulder blade - so he’d be aware of the small knot there, and used the fingers of the other hand to stroke his neck more erotically. If it was an erogenous zone for me, why shouldn't it be one for him, after all? These were skills I’d developed to make up for not putting out. “Why don’t you lie down and I’ll massage that knot out.”

I all but pushed him into the bedroom, just a few feet away. He probably should have objected, but a sixteen year old boy turning down a massage? And, back in the day, I looked pretty good. My job kept me fit, my boobs matched my size, which was tallish, and I wore my hair a lot longer. I wasn’t beautiful, and I didn’t like to be called cute, but I believed lots of men my age found me attractive, never mind a boy who’d lust after a watermelon with a hole in it.

Chad started to lie down, but I pressed my advantage, saying, “Take off your shirt, please, we don’t want to crumple it.” Good, eh?

I massaged his shoulders with some intensity before switching to slower, lighter strokes the length of his back. I caressed his entire arm, using a little extra pressure when moving towards his shoulder. I grasped his right hand with both of mine and “milked” each finger. He smiled when I pressed the ball of his thumb, so I spent some extra time there, too. I had no plan, but I was thoroughly enjoying the contact, and yipping in the back of my mind was the notion that it would be both fun and easy to make him come. Oil would have helped a lot, but I didn’t want to lose the momentum.

“Roll over, Chad, and I’ll balance your chakras.” I’d read about chakras in a novel. I didn’t really know what they were. I thought it sounded good.

After a half minute of proper chest massage, I returned to the light erotic touch that everyone, including me, enjoys and finds arousing. I teased his nipples as though they were mine. I reached across him to do his other arm, making sure my boobs pressed against his skin. A minute later, his hips were squirming. His jeans hid his erection well, but I knew it was there. My fingers glided over his skin, with leisurely attention to his nipples, and across his stomach. I put my hand where the end of his cock had to be and pressed lightly, in circles.

“Does this feel good, Chad?” I asked, figuring I was either done or just beginning.

“Yes, Miss Taylor, it really does.”

Wasting no time, I unbuckled his belt and stuck my hand in. I rubbed the wet spot on his jockeys and the magic sensitive spot near the top of his cock that still seems to me to be like a man’s version of a clitoris. Like every cock I’ve ever known, blue silicone included, Chad had been circumcised, so I don’t know if that makes a difference.

“That’s so good, Miss Taylor,” he said.

I pulled off everything else he was wearing. Chad lay outstretched on his back, his hard cock pointed at his ear and trembling slightly. With long strokes, I traced his skin from his neck to his knees, careful not to touch his cock. On the way back up, my fingers grazed the insides of this thighs, close enough to brush the thin hair near his balls before continuing up his hips to his nipples. A drop of pre-cum formed at the end of his cock. I knew I was doing well.

“Now that I have your attention,” I said, “I think I’ll get comfortable, too.”

While Chad watched with wide eyes and an open mouth, I unbuttoned my blouse and added it to his pile of clothes on the floor. I slipped out of my bra and my skirt, but after hesitating, I left on my plain cotton panties. My hand rubbed his tummy and almost grazed the end of his cock. I pulled his hand to my boob and held it there.

“Do you like how that feels, Chad?” I asked.

For an answer, he squeezed my boob. I took his hand and showed him how he could do better.

“Cup your hand like this,” I said, molding his hand to my boob. “Now, notice how lightly I’m touching you now. Move your hand around, but keep your hand light, like that, especially around my nipple. That’s nice! OK, now do it with just your fingers.”

Once he’d mastered that, using my hands over his, I showed him how to squeeze my boobs. I had him rub a nipple while I rubbed the other and he copied everything I did.

“You’re doing great, Chad. Now one hand on each boob.”

While he massaged my chest, I quite openly rubbed my pussy through the fabric. I wondered if he’d ever seen a woman masturbate. Probably not.

I had been thinking I’d try to make him come without touching his cock, but now that seemed too cruel. Surrounding the length of his cock with my fingers so his damp tip didn’t quite touch my palm, I drew my fingers along his shaft, repeating the stroke many times over the last three hard inches.

“Play with my nipples,” I ordered.

More pre-cum oozed from his cock. It dripped so slowly it almost defied gravity, like poured honey, leaving a thread between his cock and his tummy. My fingers smeared the slippery goo into his skin. His hips jerked when the back of my hand inadvertently grazed the head of his cock. I traced a line down the center of his dick and held his balls gently. Manipulating these twin plums carefully, my fingertips kneaded the area underneath and he sucked in a deep breath. I swear that a whole quarter teaspoon of his honey leaked from his cock, a slow dribble of anticipation.

Holding the base of his shaft, I massaged the pre-cum into the end of his dick, that sensitive “clitoris” area I mentioned and the smooth head. I had only meant to excite him more, but he said, “Uh, oh” and blasted a stream of come into my hand. With his cream sliding down my wrist, I masturbated him so he spattered all over his chest. The last large drops pooled on his tummy.

“OK,” I said, “now you’re really relaxed.”

With his cock disarmed so he wouldn’t be tempted to have it go off inside me, I lay down beside him, the length of my body in contact with his. My boobs pushed into his chest, still wet with come. I kissed him lightly on the lips. I was more concerned I’d spook him with a kiss than I had been jacking him off.

“Did you like rubbing my boob, Chad?”

“Totally. You are so . . . soft.”

“Would you like to rub my pussy? Maybe pay me back a little?”

His hand dove for my pussy and I grabbed his arm.

“Slow down there, partner. While I’m sure I’m pretty wet down there, you don’t want to rush a woman. Here,” I said, taking his hand in mine and leading it slowly into my panties, “just feel my cunt gently, how smooth it is. Yes, like that. Feel the slit, but don’t go looking for the hole yet. Here, let me take these off so you can see what you’re doing.”

Now we were both completely naked. I spread my legs and put his hand back on my pussy. I showed him where to rub, putting pressure on my clitty without actually touching it.

“OK, push a finger in slowly. A little lower. Oh, yes, farther in. Now wiggle it slowly and suck on my boob.”

Chad performed as well here as he did in English class. Soon, there were two fingers sliding in and out of my cunt. His lips were clamped to my nipple and I encouraged him to lick it broadly, then with the tip of his tongue. I asked him to lick underneath and near my ribs. I spread my legs a little more, completely comfortable and completely aroused. I longed for an orgasm.

“Would you like to eat my pussy?”

“I don’t know . . . sure, I guess, if that’s what you want.”

He slid down the bed and he began to lick the insides of my thighs, working his way up, probably orienting himself to the reality of a woman’s cunt. He seemed surprised at everything. He licked alongside my pussy and kissed my tummy, as though he couldn’t commit to my cunt. After much licking, his tongue centered on my slit.

“Lick me slowly. Use your whole tongue.”

I spread my legs even wider and his tongue gained enthusiasm. Soon it was finding its way partway into my hole and, by licking wildly up and down, he occasionally jolted my clitty. The next time he got it, I told him to suck me right there. A little more guidance and we had perfection. Without being asked, while he was licking and sucking my swollen nub, he pushed first one, then two fingers inside me.

“Oh, Chad, that’s so good. Fuck me with your fingers. Fuck my cunt. Do you like me talking dirty to you? Eat my cunt. OH, yes! Suck me right there, lick me, lick my clitty harder, harder . . . harder!”

My orgasm came from a long way off. A faint pulse in my middle grew stronger, warmer, becoming a tension between my clit and my gut that wound tighter, and tighter, and then it snapped.

“Yes! Yes! Don’t stop! Yes!”

Whether he knew what was happening or not, Chad kept his tongue where it belonged and his fingers moving. I fell back, muscles slack, legs spread wide.

“OH! Stop, Chad, stop! Oh my God, that was awesome.”

Chad started to crawl back up my body. He kissed my tummy. He kissed my boob. Just as he was about to kiss me on the lips with his pussy-wet lips, I felt his hard cock poking near my hole.

“No!” I shouted, and my ass slid three feet up the bed before I knew what I was doing.

“What?” he asked, concerned and maybe frightened. “What did I do?”

I was breathing hard. I tried to calm myself.

“Sorry. You didn’t do anything wrong. I just got too relaxed. I’d rather you didn’t fuck me. We can still have plenty of fun. But no intercourse. I should have told you.”

He looked dejected, but he’d already had a pretty good day. He said, “Maybe that’s what Camus meant by ‘find excess within moderation’.”

He didn’t sound convinced and his cock pointed at me like an accusation. His brain had processed what I said, but his dick didn’t know when to quit. This was, I supposed, my fault.

“Lie back down, Chad.”

He complied easily enough. I spread his legs apart with my knees and lowered my mouth over his cock. My hand stroked him while I sucked, both because I thought men liked it better that way and to make sure he wouldn’t ram it down my throat. I expected he’d come quickly and I’d let the white guck stream out of my mouth. While they were coming, guys didn’t even notice I wasn’t swallowing as long as I didn’t take my mouth away.

After a few minutes, though, my post-orgasm reserves of energy were fading. I changed position to lie beside him, my pussy touching his knee, and continued stroking him. His cock remained completely hard, but I couldn’t make him come.

“Maybe it’s not going to happen,” I said after several minutes and a tiring arm. I’ve always believed that orgasms have a mind of their own, but until then I’d assumed that a hard cock always implied an eventual ejaculation.

“I’m pretty sure it will,” he said.

“You do it for a minute,” I said. “Maybe I’m doing something wrong.”

When Chad hesitated, I pulled his hand to his cock. To ease his obvious embarrassment, I put my lips around the end of his dick as though it were a straw.

“It’s OK, just masturbate into my mouth,” I said.

I’d never done this before, but it seemed like a good idea, with no risk of getting rammed and flooded. My mouth sucked and my tongue licked at the last inch or two of his cock while he stroked. His hand touched my lips several times before I realized he wanted to stroke himself nearer the end – wanted to get at that “clitoris” part. I wished he would talk more. With my lips barely touching the tip of his cock, he pumped his cock faster and faster. I cupped his balls and massaged the area just below his plums as though I could push the come out.

“Do it, Chad, masturbate for me. Come in my mouth! Seeing you jack your cock like that is so hot! Do you like being watched? Are you going to come soon?”

I guess I expected him to say something when he was going to come, but without warning a burst of jizz splashed my face. I jerked away, but I’d already been blasted by almost all he had. The rest trickled over his hand. That well was completely dry.

“Sorry,” he gasped, “I didn’t mean to. Your face, you know.”

I wasn’t pleased. No one had ever come on my face before. But assuming it didn’t mess up my skin, it didn’t seem so awful, either. I was still learning that good sex is messy sex. One of my cheerleaders told me later that come is supposed to be good for the complexion and that she loved having a guy masturbate on her face!

Leaning close, I said, “It’s OK, you just surprised me.”

I kissed him on the lips and we shared the taste of his come, which wasn’t as icky as I remembered. He grimaced, though, and I suspected it grossed him out a little. Nowadays, of course, I sometimes like come on my face and I’m eager to swallow when I give a blow job. My husband loves the taste of his own come.

I let him use my shower to clean up before he went home. He was going to be really late, he said, but it was totally worth it.

“Miss Taylor,” he asked, suddenly coy, “if I think of more questions can I stop by? Maybe ‘still have plenty of fun?’”

“Chad,” I said, “I am sure your story is going to require some follow-up. I’m looking forward to it.”

I trusted him to keep quiet and as it turned out, I never had any problems from any of the students I interacted with intimately. Maybe my luck wouldn’t have held forever, but less than two years later I was married and pregnant. Now, so many years later, sometimes when I see my son’s friends who are exactly the same age that Chad had been, my tummy flutters a little and I remember that distant afternoon when I received that first splash of come in my face.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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