At 18, I was the frustrated second-string catcher on my high school baseball team, sitting in the dugout, getting little playing time, feeling underrated.
Coach had a young wife I’ll call Cynthia. The first things I noticed about her were her bronze tan and her dark rock-’n’-roll-styled hair. I was infatuated, but I didn’t dream that she would be the one who gave me my pussy baptism, as my pals and I called it back in the day when we were fumbling in the dark in search of elusive manhood.
Cynthia often accompanied Coach to games. She sat in the stands in either a light summer dress or shorts and a sleeveless blouse. She became the object of dirty jokes by all of us. Our preoccupation with the female anatomy had us all boasting of what we would do with her if we ever got the chance.
Coach had the team over to his house for a barbecue. Cynthia was in the back yard sunning in a two-piece swimsuit. Of course she knew the team was coming, but I was too green to put two and two together. From the kitchen I saw her reach for one of Coach’s T-shirts and pull it on over her head. She slid the glass patio door open and passed by us on her way to the bedroom without saying a word. A teammate said, “Coach’s wife is a stuck-up bitch.” I nodded agreement.
One evening at practice while I was kneeling retying the shoestrings of my cleats, I turned and saw Cynthia standing a few feet behind me. I was shy and polite to a fault, and utterly terrified of this dangerous woman I’d seen in a bikini a few days earlier. “Hi there,” she said in a friendly tone.
“Hello,” I said. She smiled and walked off. Those were the first words we spoke. In the following weeks when she saw me she made a point of saying hi and asking how I was doing — first formal and proper, then friendlier, until her face lit up when she saw me. When Coach’s attention was elsewhere, she fawned over me like a big sister.
Cynthia was fun to talk to, and I started to like her. Then a teammate noticed. “You and Coach’s wife have the hots for each other,” he said.
“She’s just being friendly.”
“Yeah, sure,” he said. “You should drill her little cunt. I would if I were you.”
“Your mind’s in the gutter, asshole,” I said. “Cynthia is a really nice person, so just shut your filthy mouth.”
“Fuck you too,” he said. “You got no sense of humor.”
I wasn’t about to let him make Cynthia and me a locker-room joke. But he’d got me between the eyes. I was in love with Cynthia, and was trying to keep it from showing, especially around the guys.
One day after I got home from practice there was a knock at the door. I found Cynthia standing on the porch wearing two pairs of sunglasses — hers pushed up on her forehead, and mine covering her eyes.
“Guess what you forgot, young man,” she said, smiling. She came in, took her sunglasses off her forehead and slipped them on me.
“These are yours,” I said.
“I know,” she said. “I’m just being silly.” She lifted my glasses off her nose, letting her eyes show. “Peekaboo!”
I laughed uneasily. She’d been acting goofy around me, as if trying to sound like a teenager herself. She took my sunglasses off and exchanged them for hers.
“Thanks for bringing these to me,” I said.
“I was in the neighborhood,” she said. “Are your parents home?”
“They’re at work,” I said.
“Do you expect them soon?” she asked.
“They get home at six.”
“Are you here alone?”
“Yeah,” I said.
Cynthia startled me by leaning forward and kissing me on the mouth. Goose bumps raced up my spine.
“You’re blushing,” she said. “Let’s try that again, shall we? You kiss me this time. A friendly little kiss.”
I leaned forward nervously and pecked her lips.
“You’re a really handsome young stud,” she said. “Why doesn’t your girlfriend come to the games anymore?”
“We just broke up.”
“May I ask a personal question?” She didn’t wait for an answer. “Have you ever been with a woman?”
“What do you mean?”
She smirked. “You really don’t know what I mean?”
“Oh, that,” I said.
“Yeah, that,” she said.
“Not exactly,” I said.
“May I show you something?” she said. Again she didn’t wait for an answer. She unbuttoned her blouse and undid her bra. I gaped at her stunning breasts.
“Well, say something,” she said. “What do you think of my boobs?”
“They’re really pretty” was all that I could come up with!
“Would you like to touch them?” she said. “Go on. Don’t be shy.”
I put my hand on her tit, then let go. “I barely felt that,” she said. “Go on and give it a squeeze. I’ll let you know if you’re hurting me.”
I gave a light squeeze, not much stronger than before.
“Don’t you find me attractive?” she said.
“Ohmygod,” I said, “You look like a movie star.”
“Well, you don’t act like it. Look, I have something to ask. Would you like me to be your first girl?”
My mouth went dry.
“And don’t act like you don’t know what I mean.”
I turned in an effort to avoid eye contact.
“Don’t look away,” she said testily. “Look at me!”
I glanced back fretfully.
“What I’m saying is, if you want me, I’d like to be your first. I promise, nobody will know. Would you like that?”
I was tongue-tied. Cynthia laid her hand on my arm and brought her face near mine. “Nod for yes,” she said softly. “This will be our little secret.”
I gave a slight nod, then said, “When exactly do you want to do it?”
“What’s wrong with right now?” she said. “Why not take me up to your room?”
“Not there,” I begged. “My room is gross.”
“I’ll take my chances.”
My pulse raced as Cynthia followed me upstairs. My yearning to have sex had consumed endless daydreams that gave way by night to wet dreams and incessant jerking off. Now that it was about to happen, it terrified me. Though I’d fantasized often about Cynthia, I had never imagined anything actually happening.
We stepped in my room, and she closed the door. “Would you like to undress me?” she said. When I didn’t answer, she smiled and said, “Let’s just get out of our clothes. Maybe it’ll be easier if we undress at the same time. Shall we?”
She removed her blouse and bra, kicked off her sandals, took off her skirt, then slid her panties down and tossed them on a chair. I undressed, feeling increasingly self-conscious of my nakedness and hers.
When her gaze fixed on my groin, I felt mortified. “You are very well-hung, hot stuff,” she said. Really? I didn’t think I was all that big.
I gawked at the triangle of frizzled hair in the vee of her thighs. She moved to within inches of me and said, “May I touch you down there?” I was unable to utter more than a garbled sound.
She slid her fingers under my sac and lifted my balls, then with the fingertips of her other hand stroked my cock. The nerve endings in my glans went wild.
“Feel good?” she said.
I said, “Yes, it does.”
“I could put my mouth down there,” she said. “Shall I do that for you?”
The mere suggestion was all it took to trigger orgasm. My cock convulsed and shot a jet that splashed her belly, followed by another.
“Oops,” she gasped, stepping back.
“Oh jeez,” I yelped, “I didn’t mean to do that.”
“Shhh, it’s all right,” she said. “Don’t worry about it.”
Red-faced, I handed her a whole fistful of tissues. She daubed the rivulet of come streaming down her leg, then dropped the wad in the wastebasket.
“I’m really sorry, Cynthia. I feel like such a dork.”
“Just a little mishap,” she said, smiling. “It’s my fault for rushing you. I’m not upset, so don’t feel bad. Okay, baby?”
“Okay,” I said.
“Lie down on the bed. We’ll do this differently.”
I climbed on my bed and stretched out on my back, sure I’d die of embarrassment. Cynthia kissed my midriff. She sat nestling her thigh against mine and laid her hand on my belly.
“Nice, isn’t it?” she said. “Our bare thighs touching like this.” I nodded. “Sex isn’t just getting off, you know. It’s savoring the texture of your lover’s skin, the softness of her hair. All the little things make sex wonderful.”
Her soothing voice was finally putting me at ease.
“This is a first for me too,” she said. “I’ve never deflowered a virgin before, so I’m kind of nervous too. Would you like to see my pussy?”
She raised her leg and swung it over me, planting her foot on the bed. Her thighs spread as she scooted up close, giving me a bird’s-eye view of her naked crotch. I stared at the slit between folds of pink flesh nestled in a patch of ebony-colored hair.
Like a dork, I gaped. “It’s pretty.” God! Everything I said sounded utterly stupid!
“See these lips?” she said while fingering herself. “This is my labia. Now I expect you’ve heard about the clitoris. Let me show you how to find it. See that bit of tissue? Just pull it back, and there it is. See it? Go on and touch it.”
I couldn’t budge.
“Let me help,” she said, taking my hand. She wet my finger with her tongue, then guided it to her clitoris. “Now rub gently. That’s it! Umm, that feels good.” Timidly, I withdrew my hand. “Little rogue,” she said, raking her fingers through my hair and laughing. “Think you’re ready to fuck me?”
“I guess,” I said.
I know now that what Cynthia did next was a coy pretense that she wanted me to do her a big favor, when in truth she was letting me off the hook. She bent forward and said, “I know men like being on top, but I’d love it if you’d let me be on top for your first time. Is that okay?”
I said, “Sure,” relieved at not being expected to lead.
“Just lie still. You be the saddle. I’ll be the rider.”
She rose up, positioning herself for penetration. She gripped my penis and guided it in. As it squeezed in her, she sank down, and I had my first experience of vaginal walls spreading at the invasion of my cock. She sank down until it was fully embedded in her.
“Put your hands on me if you like, on my legs, my ass, my tits, wherever you feel like while I’m riding you.”
My hands groped her tits clumsily. As I lay inert, she rocked slowly back and forth. She lifted herself till my cock was nearly extracted, then sank all the way back down. She leaned forward till our noses touched.
As she moved up and down, I felt her breath on my face. “We’re doing it,” she cooed. “We’re fucking. You’re fucking me.”
It didn’t take long for me to climax. As my torrent began unloosing, my pelvic frame instinctively thrust up in her. I clutched her waist as my body went stiff. When my body relaxed, she lowered her face to mine.
“You’re not a virgin anymore,” she said. “You just fucked me. How’s it feel?”
“I don’t think that I did so good,” I gasped.
“Why, you did great,” she said. “I loved it.”
“Thanks, but I know you’re just saying that to be nice.”
“Oh, am I?” she said. “So how come I can’t wait until we do it again?”
“Like when?” I said.
“Whenever we can set something up,” she said. “That is, if you feel like doing it with me again.”
“Sure I do! Absolutely!”
“Why not come to my house tomorrow afternoon before my husband gets home? We’ll fuck again, and maybe try something new.”
“I’ll be there,” I said.
“You do know what this means, don’t you, guy?” she said. “You just scored.”
“I did, didn’t I?” I said. “I actually got laid.”
“Yes, you did,” she giggled delightedly. “You and I both just got laid.”
“This is awesome,” I said. “My first time ever getting laid and it’s with a total fox.”
“Young man,” she said, “that’s about the nicest thing anyone’s ever said to me.”
She laid her cheek on my collarbone. Her hair tickled my chin. We cuddled, stroking each other and kissing. That night I tossed, embarrassed over my ineptitude of that afternoon. Cynthia was my first woman, and it had been up to her to do everything. Ejaculating all over her was the worst humiliation of my life. I mustn’t let that ever happen again.
The following afternoon when I went to see her, she popped a cassette in the VCR and I saw my first porn film. When it was over, she introduced me to the pleasures of oral sex, both giving and receiving. And as we continued our trysts, I grew steadily less awkward.
From the time I awoke each morning, all I could think about was seeing Cynthia. It didn’t bother me that she was married. I couldn’t get enough of her. She was so patient helping me learn how and where a woman likes to be touched.
My secret visits came to an end that fall when I went off to college. I saw Cynthia one last time when I came home for Christmas break. I was getting into my car as she drove past. We waved.
I’ve been married twice now and have had several relationships — some good, some disappointing. But if I live to be a hundred, Cynthia is the one I’ll always remember. And now that I’m older, I can see how I might be the one she’ll remember. At least I like to think so!