Teaching Carol, Ch. 1

It was dusk, nearly dark. A warm, late-September evening. Carol and I were sitting on top of a picnic table near the reservoir, she in the center, her feet on the bench, and I behind her with my legs on either side of her as I massaged her shoulders. 

We didn’t know each other that well, but there had been a slow flirtation going on and we had somehow decided to take a walk together and wound up here. She was small and dark—her last name was Spanish-sounding—and her petite figure looked very girlish in what seemed almost like a pre-teen’s white party dress, plus clunky sneakers and knee socks. She certainly didn’t appear to be a particularly sexual person; in fact she seemed rather shy and virginal, in manner as well as dress, and I believe she was, basically. When I made a slightly off-color joke she smiled and blushed, looked down, and said, “Jeez.” And yet there must have been some quality about her, some hint of submissiveness, because I just knew somehow she would let me do whatever I wanted.

As I massaged her shoulders I was telling her how much I liked touching her, and apologizing with humorous insincerity for my inability to keep my hands to myself. She accepted my apologies with laughing graciousness and did nothing to discourage me.

Even though it was fairly dark, there were other people not too far off so I pointed at the silhouette of some trees near the shore and said I wanted to go over there. She agreed and laughed a little nervously when I picked her up in my arms and began to carry her over to them. The back of her dress was hanging down where her knees were hooked over my arm, and I think we were both aware that the backs of her thighs were pressing against me there.

I’m sure she hadn’t been planning to get sexually involved with me. When I put her on her feet in the shelter of the trees and pulled her to me, she put her hands against my shoulders as if to push me away, and said, “Jonathan!” in a way that made me think her next word would be either “No!” or Stop!”

But when I kissed her, she offered no resistance, opening her mouth to my insistent tongue, her hands now holding tightly to my shoulders. This was even more of a turn-on for me: ‘I shouldn’t do this, but I can’t resist’.

I wanted to see if it was true. I pressed her back against a tree and, without removing my mouth from hers, began fondling her left breast through the stiff, ruffled fabric of her dress. Again, no sound of protest, no hand plucking at my own.

I decided to push my luck, and put both my arms around her waist again before easing my hands down onto her behind, then bending my knees just enough—and she bent with me—to slip my hands under her dress, up the backs of her thighs and onto her behind again, now caressing it through the fabric of her cotton panties.

I couldn’t believe it. I knew she thought she shouldn’t be letting me do any of these things, and yet she was doing nothing to stop me. And I certainly wasn’t planning to stop unless she did.

Still probing her mouth with my tongue, I brought one hand around and slid it between her legs, fondling her there. We were both breathing heavily by then, but she made no sound, beyond the occasional small whimper.

Even when I pulled my mouth away from hers and dropped to my knees in front of her and lifted her dress, she said nothing, did nothing.

When I began to kiss and nuzzle the mound between her legs.

When I reached up, letting her dress fall over my head, and pulled her panties down to her ankles.

When I lifted first one foot, then the other, to remove her panties completely, and spread her legs apart so that I could lick her there.

Her pussy was moist, and became more moist as I licked, but still she made no sound, either of enjoyment or of protest, until finally I stopped and stood up, picking up her panties as I did. I tucked them partly into my pocket before putting my arms around her waist.

By now it was so dark that I could barely make out her face. She let me take her into an embrace, putting her arms around me and resting her head on my shoulder. Then, finally, she spoke. Her voice contained both surprise and relief as she said, “You know when to stop.”

She’d apparently been expecting me to pull her to the ground and have my way with her—and, just as apparently, she would have let me. But intercourse, especially unprotected intercourse, without some kind of understanding beforehand, was beyond my moral limits. Instead, I cheerfully replied, “Do I?”, then took her right hand and pressed it against the front of my jeans. She gave me two or three half-hearted rubs there, looking down as if surprised to see what her hand was doing, then tried to take it away, saying, “It’s getting cold,” as if it were time to start home.

It was starting to get a little cold, especially for her, in that dress with no sweater or jacket. But I was feeling powerful, and I placed her hand firmly back on my zipper, saying, “Keep going,” as if I were gently correcting an unintentional display of bad manners. As I expected, she complied, one arm still around my waist, running her fingers and palm nervously up and down the length of my erection and peering up at my face through the darkness as if waiting to be told what to do next.

Again the sense she gave of being in my power was irresistible; I had to see how far I could take it. I let her stroke me for a while in silence, then said, “I can’t feel it. Unzip me.”

I actually expected some resistance at this, and in fact for a moment it seemed as if she were going to speak. But after a slight hesitation she began to fumble at my zipper, at first trying to open it one-handed, then bringing the other forward to hold it straight while she worked it with the other. She unzipped it with a slowness that suggested reluctance more than sensuality (which of course made it even more sensual for me) and her expression, what I could see of it, seemed a little fearful. But she nevertheless undid my belt and unbuttoned the top of my pants without further prompting and placing her hand back on my erection, now straining outward against the fabric of my underwear, began again to stroke it.

I took her face between my hands and kissed her, saying, “That feels nice.” I wanted to ask her if she liked what she was doing, but I was afraid of breaking the spell. Besides, I wanted more.

After a while I took her hand away from me. She must have thought we were done, but I quickly disabused her of the notion by pulling my pants, and then my underwear, down to my thighs, so that my erect cock was bobbing in the dim light. Carol backed away slightly, thinking perhaps that I was going to take her after all, but I caught her arm, then pulled her panties free of my pocket, and pressed them into her hand, saying “Use these.”

She stared with some dismay, first at me, then at my cock, then at the white, crumpled panties in her hand. Hesitantly, she unfolded them, looked at me again, then, stepping closer, wrapped her panties loosely around my cock, and began rubbing them up and down the length of the shaft, looking at me all the while as if to say, ‘Is this right?’

It certainly was. The smooth fabric, combined with the warmth and motion of her hand, were beginning to stir something deep within my scrotum, and I knew I’d be coming soon.

One thing more.

I placed my hands on her shoulders, and began to press her gently downwards. She knew what I wanted immediately, and her eyes went wide, but she allowed me to guide her down onto her knees without missing a stroke.

At first she simply continued to stroke me with her panties, but she stared fixedly at the head of my cock as if gathering her courage. Then slowly she leaned forward, continuing to stroke as she brought her lips to the very tip of my cock, kissing it lightly. She started to move away, thought better of it, and returned to kiss it again. She held the kiss for a little while, as if unsure what to do next, then opened her mouth slightly, taking the head of my cock a little way in. Finally, with a sigh, she open her mouth wider and took the head all the way in.

The touch of her tongue was all it took. I immediately grabbed the back of her head as I began to come. When she felt my semen squirting into her mouth she tried to pull her mouth away, making little panicked choking sounds, but I held her there until I was done.

When I allowed her to pull her head up she looked at me in distress. It took me a moment to realize that she didn’t know what to with what she had in her mouth. I knelt down to face her and said, “You can spit it out if you don’t want to swallow it.”

Swallow it? She looked at me as if I were crazy, then turned and spat what she could into the grass. Then she turned back to look at me as if wondering what happened next.

I quickly tidied my self up. Then I helped her to stand and, taking the panties from her hand—fortunately they were unstained—I knelt again and helped her to put them on. Then I rose to my feet and removed my jacket, then placed it around her shoulders as we started to walk home.