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.
