My neighbor Karen lost her husband some time ago and for a long time afterward withdrew into her own private world.

It was hard for her friends and neighbors to get her out of her shell, despite the fact that she was still a very attractive woman, still only in her 30s.

When I was 18, Karen asked me if I could help her around her house. She was in her late 30s then, and still really attractive, so I didn’t hesitate. The first thing she asked me to do was help her straighten out and organize one of her closets. In that small space we kept bumping into each other. At last I realized she was backing her very fine rear end into me on purpose. Suddenly she asked, “Do you have a girlfriend, Mark? Have you ever had sex with a girl?”

“Um, well, no,” I said. I’d just fooled around with a few girls and jerked off a lot daydreaming about having sex.

“Put your arms around me,” she said. “Hold me.”

Karen was a little shorter than me, and it thrilled me to feel her generous breasts pressed to my chest. “It’s so long since a man has held me,” she said. “And it feels so good. Would you like me to show you what a woman’s body is about? You mustn’t tell anyone about it, though. Do you understand?”

I said I did, and she put my hand on her breast, and even through her blouse and bra I thrilled to the softness of her. Then we kissed. I half expected to hear lush music like you do in the movies. That didn’t happen, but even so, I never forgot that first kiss.

Karen undid her blouse so I could play with her tits, still in her bra. While I was enjoying myself, she opened the bra and let her glorious globes fall free. My brain was spinning. She said to lick and suck on her nipples, because she loved that. I found it totally wonderful, and would have been content to do that indefinitely — my pecker was hard as a rock in my jeans. But she took my hand and led me to her bedroom, where she lay on the bed and said, “Suck on my tits some more,”

I went back to work on those luscious nipples. As I played with them, she drew her knees up, with her feet flat on the bed. Her skirt slid down over her thighs until I could see a bit of her pubic hair and realized she didn’t have panties on. I knew that in a minute I was going to see my first real pussy!

“Mark,” she said, “I want to show you something.” She pulled her skirt out of the way, and there it was!

While I stared, she spread the lips of her vagina a little with her hands. “This little knob at the top of my slit is called the clitoris,” she said. “If you play with it very gently, it’ll send me into orbit.” So play with it I did, gazing in fascination. As she arched her body I could also see her puckered asshole. A bit hesitantly, I slid a finger in that wet-lipped pussy and probed as far as I could. It was fascinating to me, and my groping seemed to send her into ecstasy.

After a while she said, “Okay, I’m going to take off my clothes, and you take yours off too. I want to see your young manhood.”

In seconds we were both naked. Karen held my cock for a while, looking it over and playing with it. Then she lay back, spread her legs and said, “Fuck me!”

Hoping like hell I would know what to do, I climbed on the bed, my cock swinging freely, ready to enter that warm, hair-covered hole. Karen drew her knees way up and spread them wide, causing her crack to open a little. I was so excited, I could hardly stand it. It felt awesome, jamming my shaft for the first time inside a real woman. I started pumping, and Karen wrapped her legs around my back. Of course I didn’t last long. In minutes I was shooting deep inside her, and she was whimpering. Then it was over.

As I left Karen’s house, she said, “Can you come back tomorrow to finish that closet? I’ll show you more about sex too. Just remember, you mustn’t tell anyone.”

Of course I went back, and the fucking, in several positions, lasted longer and was even more fun. After that we settled into fucking two or three times a week. Karen taught me about oral sex. I learned how to eat her cunt, and she really loved to suck on me.

The first time I came in her mouth, I thought I was in heaven! There I was with my cock sliding in and out between her soft warm lips, and I could feel my balls getting ready to blow. While I was wondering if it would be all right to shoot in her mouth, all of a sudden it was too late. While I shot off helplessly, Karen just kept sucking and swallowing, with her lips tight around my shaft. I couldn’t believe how good it felt, coming in her mouth, with her pretty eyes watching me while her fingers played with her clit. When I’d finished shooting my wad, she licked off all the remaining jism that was dripping from my dick.

One day while Karen was sucking me off, she said, “God, I want to feel that cock in me! But I’m having my period, so you’re going to have to stick it up my butt.” She got a tube of something called K-Y jelly, smeared it all over my erection and on her anus, then got on all fours and waited for me to enter her. From behind her I could see the string of her tampon hanging out of her pussy. Above it was her tight-looking anus. I probed it with a finger, then two. It started to open up.

“Come on,” Karen whimpered, “let’s do it!”

As I positioned my cock at her little brown hole and began to push, my foreskin started to pull back. Suddenly my cockhead popped in past her tight sphincter, leaving my foreskin retracted. The feel of that tight muscle around my cock as it slid in was fantastic. I eased the rest of the way in, then started a slow, short back-and-forth stroke that brought moans from Karen.

The thought of my cock deep in her fabulous rear end, and the knowledge that I was soon going to shoot my load deep in her rectum, soon brought me to the brink. I knew I better slow down or this wasn’t going to last long!

Meanwhile Karen was fingering her clit. I felt her shudder in orgasm, that little brown hole squeezing my cock with hard pulses. She begged me not to stop, and I kept right on fucking her as she started the process all over, building her way to another climax.

I wanted to shoot so bad, I wasn’t sure I could wait for Karen to come again. But her passion was building with more even more urgency than before, and soon she was making noises like a bear growling as she went over the edge. Her asshole spasmed away on my cock as I blew my load deep in her clenching butt.

Before I left that afternoon Karen told me that a very nice gentleman was taking her to dinner that evening. She thanked me for taking the edge off her sex drive so she would be able to stay cool.

Walking home, I felt a little jealous. But after all, I knew that my affair with Karen would end sooner or later. She’d taught me all about sex, and I’d helped her get over a rough spot.

In my mind what followed is all part of my “first time” story. In school now I felt like a different person. I watched the girls in an -entirely new way as they moved around in the halls and sat in class. I saw them as women, imagining them naked, with the anatomy I’d gotten to know so well thanks to Karen.

Which didn’t mean I had any better idea how to get into their pants!

There was a cute blonde girl in my class I liked very much named Louise. One day I got up the courage to ask her out. We went to the movies and afterwards for a snack. At the end of the evening I kissed her good night and she melted into me, saying, “Mark, I like you very much. I always hoped you would ask me out.”

I said, “Would you like to go out again next Friday?”

“That’d be wonderful.”

That night I masturbated thinking about Louise, trying to imagine her secret parts. I wanted her so bad, I began to think I was in love with her. I wondered how long it would be before she’d let me have sex with her.

That Friday night after the movie I slid my arm around her waist while we walked, and she snuggled into me. “Mark, I have something to tell you,” she said. “As soon as I knew we were going to be together, I got on the Pill. After all, all of our friends are doing it.”

My heart was pounding! “That’s great,” I intoned as steadily as I could. “When can we, uh”

“How about next Friday?” she said, smiling sweetly.

That week I jacked off every night except for one, when I went to Karen’s. We had a nice slow fuck, and then I told her about Louise and she told me about her gentleman friend.

I was glad that Karen was still letting me fuck her, but all I could think about was Louise. Friday night finally came, and Louise and I went to the park, to a thickly wooded spot known as a trysting place for lovers. We found a place in a grove of trees where we were hidden by bushes. Soon I was kissing “my girl” passionately, feeling that I was really in love with her and hoping our sex would turn out well.

Louise broke off the kiss, saying she had to tell me something, but she didn’t stop me as I unbuttoned her blouse, then reached around to open her bra, and there were her breasts! As sweet and round as I had imagined them, with stiff pink nipples. I had to kiss them and lick them, which made her sigh. I took off my shirt and pressed that wonderful chest to mine.

“Listen,” she said, panting, “I, I’m sorry, but I started my period this morning.”

Naturally I was thunderstruck. But immediately she said, “But you can, we can do other things.” She looked in my eyes. “We can do anything you want.”

I couldn’t believe how sweet she was, and how willing. I lifted her skirt and looked down at her white panties. I pulled them down over her hips, with her help, and there found a shaved-hairless pussy, with nothing covering the sweetest cunt in the world.

Drawing her to me, I again pressed her hard-nippled breasts to my bare chest. She raised a leg and swung it over me, straddling me with her knees against my hips. This left her groin wide open. My hand went right to her beautiful crack, and I ran it over her slit to her anus, then back to her clitoris. I began to stroke it, and her pelvis moved slightly but rhythmically back and forth.

“Mark, I’m going to come,” she gasped, and she did!

I slid my fingers back to her anus and probed it gently while she rode out her orgasm. She clung to me and whispered in my ear: “Mark, I have something to confess to you. I like to play with myself, doing what you just did. I play with my clit and sometimes stick a finger in my butt to get myself off. Is that awful?”

“Oh Louise,” I said, “anything you do would be okay to me. Even if you had sex with another girl.”

I don’t know why I said it, but I was only joking. I nearly fell over when she giggled and said, “I did that too.”

“Really?” I said, amazed. “Was it any good?”

“We got pretty good at it.”

Armed with this intriguing new information, I suggested she play with her clit, and for the next half-hour I helped her play with herself! It was so erotic, I was almost sorry when her dam finally burst and she exploded.

Afterward she asked what she could do to get me off, and I said, “You don’t have to do anything. I loved helping you enjoy yourself.”

“But I want to see you come,” she said breathily. “To see what it looks like.”

She unzipped my fly and pulled my very hard cock out, then began to play with it, pumping it up and down. After she’d done that for a while — to excellent effect, I should say — she asked if I’d like her to suck me. “I’d love that,” I said, “but only if you think you would like it.”

She kissed the tip of my hard-on and licked off the precome, then slid my cock in her mouth. As my breathing grew more labored, she paused to say, “Listen, if you’re going to shoot, don’t shoot it in my mouth, okay? I want to see what it looks like when it comes out.”

I nodded weakly, and she returned to sucking my cock. She soon had me gasping, “Look out! Here it comes!” She pulled my rod out of her mouth and held it with one hand while she cupped her other hand to catch my jism. When I was spent, she stuck her tongue in the puddle on her hand. Then she licked her hand clean! “Next time,” she said, “you can shoot in my mouth if you want.”

That was just the start of my adventures with Louise. And none of it would have happened if not for Karen.