A Lesson

I matured kind of late physically, and was very shy, so even toward the end of high school with my 18th birthday behind me I had not yet managed to lose my virginity. I had gone out with girls a few times, and even had a couple of girlfriends that I had made out with, and felt up (as much as they would let me), but had never even gotten to touch a bare pussy much less get to penetrate one.

I got a really unexpected lesson one summer day. My best friend, Doug - who I had known since the very beginning of school - and I spent a lots of time at each other's house. Doug had a sister, Linda, who was much older (maybe by 10 years). In spite of the age difference she and Doug were very close, and from things Doug said she liked to teach him the ways of the world. When we were little I remember seeing her sometimes since we spent a lot of time at each other's house. There wasn't too much interaction with her, but she was always friendly. By the time we were out of elementary school she had gone off to college, then got a job in another city so didn't see her as often. This particular summer her job had her in a temporary assignment back in the city where we lived, and so she was living an empty bedroom in her parent's home. I had seen and talked to her briefly a couple of times when I had gone over to Doug's.

That particular day I had gone to Doug's house in the morning, and we had started playing a military battle board game (which often took all day to complete). He had told me he had a doctor's checkup at 11, then he and his mother were going to get lunch with his father downtown. Not surprisingly we were still mid-game when his mother came in and said it was time to go. We carefully set aside the game pieces, and agreed to meet later to finish. Doug and his mother were a little late, and in a rush to get out of the house.

I wanted to get a drink of water before biking home, and headed toward the kitchen. Doug's mother called out as she went out the door, "Linda's home today, so don't worry about locking the door when you leave." pulling the door closed behind her.

As I finished my glass of water Linda wandered into the kitchen, grabbed a coffee cup and filled it from a thermos on the counter. She added milk and sipped, letting out a soft "Ahhhh" as she did. "I really need coffee to get going in the morning." she sighed.

I stood looking at her, probably eyes wide and chin dropped. She was wearing a very short silky robe that ended just a little way down her thighs. The material conformed to her body and it was pretty obvious that she didn't have a bra on underneath it, I could clearly see her nipples protruding and could see nothing but skin in the V where it opened at the top.

She gave me a funny smile, and said "You and Dougie have grown up so much." Then motioned, and added "Come over to my room for a minute, I need a smoke and I can't do it out here."

I knew she smoked cigarettes, but that her parents were against her smoking. I followed her toward her room, my eyes fastened on her lovely ass moving under the robe which barely covered it. As I went into the room she closed the door behind me, and leaned over to reach into her bag on the floor with her back to me and as she did the robe slid up until it was very clear that she did not have even panties on under the robe. There was an immediate swelling in my groin in response, causing a bulge in my shorts. Linda had taken out her cigarette, lit it and took a deep drag. I remember Doug saying she had 'taught' him to smoke, and after taking another drag held the cigarette out to me. I accepted it and also took a deep drag, then blew out a stream of smoke. She smiled at me as I held it out to return it to her. She sat down on a chair next to her unmade bed and finished the cigarette before crushing the butt out and leaving it in the ashtray.

She looked over at me again. "Do you have a girlfriend now?" she asked out of the blue, then took another swallow of coffee.

I stammered a bit before answering "Not right now, but I have had a couple."

Doug and I talked about girls pretty often, and I knew he was way more experienced than me, or at least he claimed to be. My shyness held me back from asking girls to go out.

"Dougie thinks you're still a virgin, is that true?" Linda asked.

I'm sure I blushed furiously, and sort of hung my head down as I answered "Yeah, it's true. I've gone out with a couple girls but they haven't wanted to go all the way."

"I guess you aren't choosing the right ones then" Linda replied. "You DO like girls don't you?"

"Yeah, I like girls but I get really shy about asking them out. And when I touch them they seem to like it but stop me before we get very far."

"Maybe you just need more confidence." she said. She gave me a long look up and down, then added "I think you just need some lessons." As she said this she parted her legs slightly, and sitting on the bed as she was, exposed her pussy to me.

The swelling and bulge that had started from looking at her body through the robe was by then a full-blown erection and she could probably tell that she was having the effect on me she probably intended.

"Are you up for a lesson now?" she asked.

I just nodded my head.

"I think this might be a good time for it." Linda said softly. Then "This is just a lesson about sex, ok? This does not mean I love you, or that there will ever be another session between us. And I will tell you now sex with someone you love is even better, but "just sex" can be very good."

I lamely nodded again.

"When I ask you questions you have to answer me completely and honestly. If you don't I will be able to tell, and the lesson will end right then."

Another nod.

"Ok, first I need to know what you know. You have kissed girls, right? French kissing?"

"Yes" I replied, "I did that a lot with two girlfriends, Marilyn and Janet."

"How about touching them?" was the next question.

"Marilyn let me feel her boobs, but only through her shirt. They were medium size and really soft." I began. "She let me do it a few times after we had been kissing for awhile, but she wouldn't let me get my hand under her shirt or bra. We didn't go out that many times, she was kind of religious and got a bit weird about it."

"Ok, that's good. What about Janet?"

"Well, she let me feel her breasts too. Hers were quite small, but a different shape. They pointed out more, and her nipples would get really hard. I could feel them even through her shirt, and she usually didn't wear a bra. Once when we were out hiking she let me pull up her sweater and touch them bare. That was really nice."

"Did you touch her anywhere else?" Linda asked.

"I rubbed her pussy sometimes but only through her pantyhose or pants" I replied. "I wanted to get my hand inside but she wouldn't let me. We went out for a few months, but then she decided there was someone else she liked better than me."

"Did either of them touch you?"

"Marilyn didn't, but Janet rubbed me through my pants. It wasn't enough for me to finish" I replied.

"No handjobs, no blowjobs?" Linda asked, following with "Poor boy, I bet you had blue balls a few times. You DO jack off don't you?"

I nodded, ashamed to admit that I usually masturbated as soon as I got home from those dates, and yes, sometimes with very achy balls.

"How often do you do it?" was the next question.

"Almost every day" I answered honestly.

"Ok, come over here." Linda said, patting the bed next to her. As I sat down she leaned over and kissed me. It was a slow, sensual lingering kiss, with tongues playing toward the end. We continued for several minutes. I wanted to touch her, but wasn't sure if I should since she seemed to want to be in control.

"That was nice, you're good at that part." she said as we broke the kiss. "To be sure you're ready for what's next I think we need a little anatomy lesson. Most boys don't actually know what's what on a woman's body."

With that she stood up and took off the robe, standing completely naked in front of me. I had seen pictures of lots of breasts in Playboy, but was surprised by how much light brown bushy hair there was over her pussy (this was the days before girls commonly shaved down there). Her breasts were really nice, medium size hanging down a little, with prominent nipples.

"Most women have sensitive breasts" she began. "Be gentle, especially at first. As a woman gets excited the nipples usually get hard. You can see that mine are already erect, is kind of like you getting a boner but also happens when it's cold so don't assume hard nipples are necessarily sexual excitement."

She ran her hands up over her breasts from below, then moved them up and down, and used her fingers to pull gently on her nipples, which were definitely erect.

"You should start with gentle stroking. Then as things progress you can do more, like pulling or pinching softly. For many women the nipples are connected to the pussy and as she gets excited her pussy will start lubricating. For some women kissing, licking and sucking on the nipples is the best."

"Try it" she said, reaching over and pulling my head down to her breasts. I licked and sucked on her hard nipple very softly.

"You don't have to be that gentle" Linda said after a minute, and I started to suck a bit more on it. I really got into it, sucking the nipple into my mouth and releasing it, and running my tongue in circles around it when it was in my mouth.

I put my hand on the other one and played with that nipple too, pulling gently on it. Then I switched and sucked on the other one, and used my fingers on the first one that was slick because of my saliva. Her nipples were very hard by then, and when I sucked firmly and used my teeth just a little as I pulled back and let go of them Linda let out a distinct moan.

"I think you have that part" she said, "let's move on." She leaned back and spread her legs. "This is the center of most of the action" she said as she used her fingers to spread herself. "The vagina, but that sounds awfully clinical. I like pussy better, or cunt but that seems kind of crude."

"Move over in front of me so you can see" she said, spreading herself even more. Then with a finger she pointed and said "These outer parts are the labia majora, with the public hair." Then spreading more "These inner lips are the labia minora, the size and what they look like varies quite a bit among women, just like penises vary. The hole down there is the actual vagina, that's where your cock goes. It's quite deep, with the cervix and womb at the end. When a woman is sexually excited her vagina lubricates, it gets very wet and slippery. Feel it." and she put a finger in, then encourage me to do so also.

I slowly pushed one finger in up to about the first knuckle, and indeed she was very wet. It felt warm and slippery.

"This maybe the most important part" she continued. "The clitoris, which is normally the most sensitive spot for a woman." She move her hands up, spreading her vaginal lips at the top and exposing the little nub covered by a flap of skin. "This is the clitoral hood" she said moving her finger over the skin flap.

"You have an extra-sensitive spot on the underside of your penis" she said in a very matter of fact way, "the clit is kind of like that. Once a woman is excited rubbing her clit gently is very stimulating. It gets harder too, kind of like a man's erection. Mine is kind of average size, some women just have a little bump but for some it's longer. Most women rub it when they masturbate" and as she said this she slid her finger up and down over it a few times, eliciting another distinct moan.

I guess I had sort of an odd look. "Men jack off all the time" she said, "didn't you know women do it too?" I wagged my head back and forth indicating no, I did not know.

"Many women are just as horny as men, and masturbate a lot to satisfy themselves" she added. "Some guys think women always stick something into the pussy, but that's not true - just rubbing the clit can give an orgasm. Sometimes sticking something in feels right, a dildo - like a plastic penis, or a brush handle, or whatever is handy"

"Ok" she said again, "now let's get your clothes off." I stood and pulled my t-shirt over my head as she reached for the buckle on my pants and undid it. She pulled them down, leaving my underwear in place. Of course my cock had been hard as steel since the beginning, and was angled up at about 60° from vertical, held in place by the underwear, with a big wet spot on them from leaking precum. Linda reached up and rubbed it through the underwear. "Very nice" she said, and then reached up to slide down my underwear. My erection throbbed as she slid them off. I am circumcised, my cock bends slightly to the left, and has a big head on it. She took my cock in her hand and stoked it very slowly.

"Mmmm, nice and thick" she said.

It felt so good I couldn't control my responses, my cock twitching as she moved her hand, and some precum dribbling from the tip. She slipped her hand up over the end and spread the precum over the head, making it very slick.

"How much do you know about oral sex?" she asked. "Never had a blowjob huh?"

I wagged my head sideways again. Of course I had heard of them, but had never experienced one. These were the days way before videos were available so I wasn't even sure exactly how it worked.

With my cock still firmly in her hand Linda leaned over and licked off the precum. "Well" she said "I guess that's a good place to start. You probably won't last long anyway. Did you jack off this morning?" she asked.

I wagged my head no. "Good" she said, then "to begin with, a blowjob is a complete misnomer, it's all about sucking, not blowing." and with that slid my cock into her mouth, giving it a firm suck and running her tongue around it. It felt incredible, I jacked off a lot and my hand on my hard cock felt really good, but this was amazing, taking feeling good to a whole new level. "Getting sucked off is a much closer description" she offered after she had taken me out of her mouth.

She put it back in, sliding it in and out a couple of times, then moved her head back again. "There's one really important thing when you're getting a blowjob." she added, "You have to tell the her when you're almost ready to cum. Some women don't like cum in their mouth, though others do like it, so you have to give her a chance to make you shoot off where she wants. If you cum in a woman's mouth without warning, and she doesn't like it, she may never give you a blowjob again."

At this point she pulled me a bit closer, and slid me back into her mouth. She alternated sliding it in and out and swirling her tongue around. I was as hard as I have ever been, and trying to make it last. After a couple minutes she used her hand pumping on the shaft, and started playing with my balls with the other hand. It probably wasn't even another minute before I felt my balls tighten and knew I would shoot off soon. Heeding her warning I touched Linda's head and said in a shaky voice "Oh god Linda, I'm gonna cum soon."

She took me out of her mouth, with one hand still on the shaft and the other on my balls and said "I could feel you swelling up. Good boy, thank you for the warning - you can cum in my mouth, I am one of those girls who love cum" and immediately put her mouth back on me, sucking vigorously while pumping the shaft. It was like slow motion, it was feeling so good I didn't want it to end but could not stop it. Suddenly my whole groin seemed to contract and what felt like an enormous jet of cum shot out into Linda's mouth. She kept sucking and swallowed several times to clear the five or six big squirts of semen. When my cock stopped twitching, she slowly slid it out of her mouth and swallowed that last of it. She moved her fist from the base slowly upward, producing one more drop of pearly white cum at the tip, which she then licked off. She ran her tongue over her lips, then pulled me over and gave me a kiss with lots of tongue.

"Like the taste?" she asked? "To me that's one of the tastes of sex."

"That was incredible." I said to her. After cumming so hard my erection was starting to wilt a little bit, and I wasn't sure what would be next.

"Now" Linda said "you have to learn the other part of oral sex - giving head, or cunnilingus." She leaned back on the bed spreading her legs wide. I could see that her pussy was very wet at this point. "Giving blowjobs makes me really horny" she offered. "Use your tongue, you can lick all around my pussy, but especially on the clit. You can use fingers inside too."

I wasn't about the lose the opportunity, and got right to work. As I moved toward her pussy I spread it open, moving the hair out of the way and exposing her clit. There was a very musky, sexy aroma as I moved close, another one of the smells of sex I concluded. I licked gently over her clit, and heard Linda moan softly in response. I licked lower, and pushed my tongue into her hole. She initially was using her arms to prop herself up. As I lifted my head again to get my tongue back to her clit I looked up at her and saw a big smile. She let herself flop back, and slid her butt up slightly so she could have her feet on the edge of the bed. I moved my mouth around, alternating licking and sucking on her clit, which seemed to have grown a little and was harder than before. I reached my left hand around her leg to touch her breast, playing with the nipple that was still standing out hard. She was moaning more by then. I really wanted to feel her cum, and took one finger and then two and slid them up into her soaking pussy. I pumped them in and out steadily as I focused on flicking my tongue over her clit. There was a sharp intake of breath and then a loud groan and her hips started bucking. She was doing most of the moving at that point and gasping loudly as she orgasmed. It went on quite some time before she slowed her movement, then reached her arms down to pull me up toward her, and we kissed deeply again, this time with my face smeared with the juices from her pussy.

"Was that really your first time? God you're a fast learner, holy fuck that felt good" she whispered in my ear. She reached down and grabbed my cock, which was at full mast again, murmuring "You're ready again?"

She reached over and opened a drawer, reached in and took out a condom. "I assume you know about rubbers" she said, "always use one unless you're ready to be a daddy."

I knew in theory but not in practice about condoms, but that didn't matter because she took charge, tearing open the wrapper and taking it out. She quickly flipped it the right way, took the tip between her fingers and grabbed my cock with the other hand. Applying it to the end of my cock she unrolled it, taking a couple of tries to get it over the fat mushroom head of my cock, commenting something like "so nice and thick." When it was fully unrolled she pushed me onto my back, and swung her leg over me, slid back and with no effort grabbed my cock and slid it up into her soaking pussy. She moved downward, making solid contact of her pussy with my crotch, then bounced up again and down - over and over. It was different from her mouth, feeling her pussy wrapping the whole length of my cock and squeezing was even better. It felt incredible. She was moaning steadily, and I reached up to grab her breasts again, pulling on her nipples with each bounce. She was moaning steadily, and before long lifted her head tilting it back she let out a guttural "Oh fuck I'm gonna cum again." Her body was hammering against me as she gasped and moaned through her second orgasm. I was hard as a proverbial bone, but I guess the combination of having cum so hard during her blowjob, and the condom reducing the sensation a little bit (though I didn't know that then), I didn't reach that point of having to cum again.