As tired as I was, sleep didn't come easily. As I lay in bed I struggled to come to grips with what had happened earlier. My thoughts took me back to my childhood and developing years.

I can't say that I had a normal childhood. It was happy, but far from normal. I was an only child, so seeking attention from my parents wasn't difficult. Being with them was always difficult.

My parents were account executives at a major entertainment consulting firm. That sounds glamorous, and to them it may well have been just that, but their work forced them to be away on business a lot. Usually it was just one of them on the road, but there were times where they were both gone for weeks at a time.

Being very wealthy, my mother and father hired a live-in nanny for more than one reason. It made life easier for them and it provided me with adult supervision during those times when they were both gone from home. I think we might have had a family dinner (with both parents at the table with me) far fewer times than when only one parent was home. In fact, I believe that when I was 12 years old we went nearly the entire year where one or both of them was away on business.

Fortunately, my nanny was a sweet, loving woman who stayed with us until I graduated high school. She was devoted to the whole family and took care of me as if I were her child.

I dated several girls during high school, but none of them ever got to the serious stage. As for sex, there was some heavy petting, but I never fucked any of them. I was beginning to think I would graduate high school a virgin, but that all changed the summer before my Senior year. That was when I met Carol Jackson.

As I may have mentioned before, Carol was 48 years old and hot as hell. There were lots of rumors floating around about her, usually stories told by frustrated teens whose only action was in the bathroom with their hands and either a girlie magazine or a smartphone. As it turned out, none of the stories were true.

Carol lived up the street from us, on a corner lot. She wasn't a large woman, but she had huge breasts. I used to see her outside working on her landscaping, her knees on a pad as she worked on her flowers and shrubs. She must have liked working on them, because she always had someone mow her lawn for her, an older Hispanic fellow.

There were more than a few times I would walk (or drive, once I got my driver's license) past her place and she would watch me as I passed. A few times she actually smiled at me, which usually got my heart racing and my cock stiffening. These brief encounters always found me in the bathroom masturbating once I got home. I fantasized about Carol a lot.

Then one day as I was walking by she called out to me and asked me to come over so she could have a word with me. She explained that the man who cut her grass was in the hospital and wouldn't be able to do it for a long time. She asked me if I would be interested in mowing her lawn. She promised that I would be happy with what she would pay me, so I agreed. I would have done it for nothing just for the opportunity to be around her. My folks were away that week, so there wasn't anything I was supposed to be doing, so maybe this would prove to be fun. She told me to come by tomorrow.

I showed up at Carol's house around 10am, wearing a t-shirt, shorts and sneakers. She greeted me in front of the house, near the front door where she was working on her flowerbeds. She was wearing white Capri pants, a blue work shirt and a large, floppy straw hat. Her light brown hair was cut above her shoulder and it poked out from under the hat she wore. She wore sunglasses, but removed them as she spoke to me, revealing large seductive brown eyes.

"Follow me to the garage, Charles," she said as she led the way around the house. "Is it okay if I call you Charles?"

"Charles is okay, but my friends all call me Chas. I kinda like it better than Charles, Mrs. Jackson. Charles is kinda dorky, but Chas sounds a lot cooler."

Carol looked at me and smiled. "Then Chas it shall be, but you can't call me Mrs. Jackson. To begin with, I've never been married and have no plans to ever marry. All of my friends call me Carol, so I think you should as well. We're friends, aren't we? At least I'd like to think of us as friends. We're neighbors, in a sense, so that means we are friends."

She knew just what to say, and I liked her immediately. "Okay, Carol. I agree that we should be friends."

Carol positively beamed at that and proceeded to show me the mower. It was a rear-bagger and she had a large can on wheels where I was to dump the clippings. "If it's not too much trouble, Chas, I'd like you to hose off the mower when you are finished. Make sure you get the underside of the deck, so the grass clippings don't clump up on the blades and deck. I'll make sure that you get something cool to drink when you are done while it dries."

"That won't be a problem at all, Carol." I'll have it looking good as new when I'm done, you'll see."

About halfway through the mowing, I decided to remove my shirt, as it was getting pretty hot outside. I thought I caught a glimpse of Carol looking at me through the windows of the house as I finished the job. She was very interested in watching me without my shirt, that much was certain. I worked out regularly, and I knew that I had a pretty good looking body. I think Carol would agree, based on the number of times I saw her peering out the window.

When I finished I did as she asked and hosed the mower, making sure to get underneath the deck. When I was done I used some shop cloths from the garage to dry it off. I wanted her to see that I knew how to take care of things. When I was done I walked to the back door of her place to let her know that I was finished. My t-shirt was slung over my shoulder and my chest was glistening with sweat.

Carol answered the door wearing a robe, although it might have been more like a housecoat. It was tied loosely at her waist and I could see some ample cleavage. I was having some difficulty keeping my growing erection from pushing out my shorts. She stood to the side to allow me to come in and, as I walked past her, she brushed up against me. It was subtle, but enough contact to push open her robe a bit more, exposing a good deal of her tits. My hard-on was getting pretty big by now and soon there wouldn't be any way to hide it.

"My goodness," she said as our bodies brushed together for that brief second. "You are soaking wet, Chas. Let me get you a towel and help you dry off." She ran off to the bathroom, her tits bouncing as she did so.

When she returned her robe was loosened a little bit more and I was able to see the outline of her breasts. They were large and drooped a bit, but not much. She was either incredibly naïve or she was giving me a free thrill as extra payment. I wasn't sure which, but I was about to find out.

Carol wrapped the towel around my upper torso and proceeded to dry me off. Standing behind me, she used her hands to rub the towel onto my damp skin, tracing the outline of my chest as she did it. She had pressed her body right up against me and I could feel her breasts burning into my back, moving slightly back and forth, gyrating against me.

"There, does that feel better? Just let me know when you want me to stop, Chas."

I didn't say a word. She was making me hard and excited with the way she was rubbing my chest and arms, and I wasn't about to make her stop now.

After a few minutes she dropped the towel and began rubbing her hands on the hot skin of my chest, her breath hot against the back of my neck. Her breathing had quickened and she gave out subtle little moans as she continued to work her fingers into my burning flesh. She took one of her hands away while the other continued to massage me and, when it returned, she took me by the shoulders and turned me around to face her.

I was startled to see that she had undone the belt of the robe and allowed it to fall to her feet. She stepped back a foot or two and allowed me to see her body in all its naked glory.

I only had a second or two to check her out, but what I saw sent me over the top, my cock now fully erect and making a massive bulge in my shorts. Her breasts, while drooping a bit, were magnificent, with dark brown areolae surrounding her large, and by now hard, nipples. Her pussy was covered in hair, a light brown triangle which pointed the way to her honeypot.

Carol put her arms around my neck and drew me in for a kiss. It was delicate at first, just a peck, but to me it was electrifying. Once she determined that I wasn't going to run off like some scared schoolboy, she kissed me again, this time a real kiss, with her lips pressed hard against mine. As her tits crushed against my bare chest, her mouth opened and her tongue worked its way into my mouth, seeking my tongue.

I was spinning as the kiss continued, with Carol's mouth moving back and forth and her lips grinding against mine.

With her lips still locked onto mine, Carol's hands began to trace their way down my sides. She didn't stop there, either. She squeezed my ass cheeks and then reached the bulge in my shorts.

I nearly came right there and then, but there was more to come. She unbuttoned my shorts and pulled down the zipper, allowing them to fall around my ankles. I was afraid that, by the time she reached inside my underwear she would only have a handful of cum to show for her efforts.

Before she could do that, however, she stopped.

"Chas," she said as she looked up into my eyes. "I'm going to ask you a question, and I need you to be completely honest with me. Can you do that for me?"

"Y-yes," I stammered. "Anything you ask."

"Very well, Chas. Have you ever gone this far with the girls you have been with? I guess I'm asking you if you're still a virgin. Are you Chas? A virgin?"

"Yes, Carol, I'm a virgin. I've felt some of the girls' tits before, but that's as far as it ever went with any of them. They never even touched me down below."

"That's fine, Chas," she said. Her voice all at once became soft and gentle. "I'm going to do some things to you, if that's okay with you, and you might feel like you need to cum. If that happens, don't be afraid to cum. You're a young man, and I think you'll be surprised at how quickly you will be able to get hard again."

"Okay, whatever you say, Carol."

Carol put her hands on the waistband of my underwear and pulled them down to join my shorts on the floor, freeing my throbbing cock from confinement.

"My God!" she said loudly. "Your cock is gigantic, and beautiful." She held it gently in her hands and carefully stroked it, almost like holding a delicate piece of crystal and taking care not to break it. A huge droplet of precum appeared at the tip and she flicked her tongue along the tip to capture it, tasting it like it were a delicacy.

Then she opened her mouth wide and took me into it. Almost immediately she began to suck on it, gently at first and then applying a great sucking force on it, so strong that her cheeks indented as she sucked. Her tongue ran along the shaft as she savored my cock, driving me crazy as she did so.

She would suck it like that, and then every so often she would release me from her vacuum hold, rolling her tongue around the head and licking the underside of it. I began to slowly thrust my hips back and forth, urging her to continue sucking it. She happily obliged me, and sucked me as her free hand massaged my balls and stroked my shaft up and down. The sensation was simply divine, and I knew I wouldn't be able to hold it in much longer.

"Carol," I blurted out to her. "I think I'm gonna cum!"

She simply looked up into my eyes and nodded, a sign that it was okay to seek release.

Seeing that, I began to shoot thick jets of cum inside her mouth and down her throat. She reveled in taking my sticky seed, swallowing as I pumped into her mouth, not wanting to waste even a single drop of my spunk. When I was finished, she bathed my cock with her tongue, cleaning my cock of all traces of what I had given her.

Once she was done she stood up and kissed me. Her mouth was still sticky with my cum, but it didn't taste bad at all. She then had me step out of my shorts and underwear and led me by the hand to her bedroom.

We sat on the edge of her king-sized bed and I reached for her tits. They felt so much nicer than the smallish breasts I had felt on some of the girls I had been with, so full that one hand wasn't enough to hold them. Her nipples were still hard, and I rolled one of them around with my fingers. Carol moaned softly as I continued to play with them.

She took my head and pulled my face to her breasts. I took one of her nipples into my mouth and gently sucked on it, causing her to squeal a little.

"Chas, I want you to suck hard on them. Go ahead, you won't hurt them, I promise."

I wrapped my lips around her hard nipple and began to suck hard. Soon I was rotating from one nipple to the next, pinching the nipple that I wasn't sucking on.

Carol liked this, as she began to moan a little more loudly.

"You can bite them, too, Chas. I'll let you know if you're biting them too hard, so just enjoy yourself."

I found my cock springing back to life as I sucked and nibbled on Carol's sumptuous breasts, trying new things to see if she enjoyed them. Judging my her moans, I was doing a pretty good job.

Carol then lay back on the bed, spreading her legs slightly so that I had a good view of her pussy. Pulling me down alongside herself, she gave me a new set of instructions.

"Now I want you to eat my pussy, Chas. Do you think you can do that for me?"

I nodded my assent as she carefully pushed my head down toward her hairy pussy.

"I know you've never done this, but just lick on it and suck it. Right below the top fold of skin you are going to find a little hard nub. That is my clitoris, Chas. That is what gives me pleasure and makes me cum. Lick it for me, baby. Roll it around with your tongue and then suck it into your mouth like you were sucking on my nipples."

Once more I did as I was told. She had a lot of hair down there, but I buried my face in it and forced her lips apart so that I had access to her essence. This was my first taste of pussy, and it was the pussy of a woman old enough to be my mother!

I licked her, tentatively at first because I didn't know what to expect. All the tales of "fish odor" and the horrible taste were just that, tales. Carol had a strange aroma about her, something earthy and musky, but it was intoxicating to me. And her taste, well, it was surprisingly pleasant, with just a hint of acidity. I bravely continued to sample this strange new taste and as I did so Carol became wetter and wetter, flooding my mouth with her scent and her flavor, which became better with each passing second. I must have been doing something right, because Carol was moaning and holding my head in her hands, her fingers running through my hair as I ate her.

"Oh Chas, that's just right," she moaned. "Don't forget my clit, honey, it's right above you. Oh, yes, yes, yes!"

I licked a little higher on her pussy and, just under the top fold, I found her clitoris, just where she said it would be. It was like a hard little nub, hidden from view. As my tongue found it and flicked at it, Carol jumped as if I had applied an electric shock to her. And when I sucked on it, she began to thrash about on the bed, moaning and screaming, her hands pushing my head in an effort to make me devour her. I locked onto that little nub and sucked it as if it were one of Carol's hard nipples. It was like finding lightning in a bottle, because I was giving Carol an orgasm.

"Good God, Chas!" she screamed. "Don't stop, don't you dare stop! I'm going to cum all over your face!"

And suddenly Carol stiffened, as if suspended in air. I could feel her pussy contracting on my face, pulsing as her orgasm intensified. And then something unexpected happened. Carol's pussy began to shoot fluid all over my face, as if she were a man ejaculating semen. The more she squirted on me the more she thrashed and screamed, and the more I liked it. I kept sucking her clitoris until the tension in her body seemed to go away. Once that happened, she pulled my head away from her pussy.

Looking down at her, I was amazed to see that there was a puddle of liquid directly under her pussy. Her pubic hair was soaked and matted with this liquid and, looking up at her face, I could see the most contented smile breaking out on her. She pulled me up and kissed me, her juices all over my lips, chin and cheeks. It didn't matter to her, as she kissed and licked my face until it was dry.

We lay beside each other, Carol kissing me over and over. She reached down and felt my cock. I was hard again, just like she said I would be. "Chas, now for the good stuff," she said, a wicked smile beginning to show at the sides of her mouth. "Now I'm going to show you how to fuck a woman the way she is meant to be fucked."

Just hearing her say that seemed naughty enough to me to make me even more excited. She knew that her words shocked me, but she also knew that she was turning me on with her dirty words.

"Since this is your first time, and because you have such a large, thick cock, I'm going to get on top of you. I'll show you how to make love to a woman gently and tenderly, making it last so that when we are ready to cum it will be the greatest feeling in the world. Just lay back and do as I tell you. I promise, my young love, you'll enjoy yourself like never before."

Carol proceeded to get on her hands and knees above me as I lay there on my back. She squatted above my stiff cock and slowly allowed her pussy to be impaled by it. She only took the head and a couple inches inside her as she got used to my size, but before long she lowered herself to the point where my cock had disappeared entirely inside her.

Carol's pussy was incredibly wet and hot. I don't know how she was able to take all of my cock without hurting herself, although it made her breathe harder with each inch she took inside herself. She was whimpering, as well.

We lay there for several minutes, my cock buried inside her as she caught her breath. Finally she began to rise and fall on my dick, slowly at first, but with increasing speed as we continued to fuck.

I never knew how great this could feel. Listening to some of my buddies talk about sex was just young guys bragging. Nobody ever said how great it felt to feel a warm, wet pussy wrapped around your dick. It was incredible, and to watch Carol above me, her face flushed, her hair bathed in sweat, her tongue licking her lips as she tried to catch her breath, there was no substitute for experiencing all of this in person.

Every so often, Carol would bend down and offer her massive tits to me, and I would suck on her nipples. I bit them as well, and Carol would moan all over again. As for me, cumming so quickly as I did when she gave me the blowjob, I felt like I could fuck all night. It felt wonderful, but there was no urgency to cum like the first time. I decided then and there that the rest of our time together this afternoon was going to be all about Carol. I wanted to show her how appreciative I was that she chose me by making her cum as much as I could. I wanted to explore all there was to offer about sex. If she was going to be my teacher, I was going to reward her for showing me what to do.

Carol quickened her pace as her orgasm approached. "Dear Jesus! Chas, your cock is so big! I can't get enough of it! Oh, God, I'm going to cum again! Fuck me harder, baby, fuck me harder!"

As she bounced up and down on my piston-like prick, I met her every thrust, holding her by the hips to keep her from getting away as I drove my cock upward into her sloppy wet pussy. She was alternating between laughing and moaning as the waves of desire swept her away and into another orgasm. She collapsed onto my chest as she came and I could feel her pussy convulsing into spasms as she moaned in delight. She just straddled me, not moving, and it was like my cock was being massaged, such were her contractions. It was another wonderful feeling that I knew nothing about until this afternoon.

When she was finished, Carol fell off my still-hard dick and fell onto her back, panting as if she had just run a marathon. I had plenty of sexual energy left and planned to use it.

I got up onto my knees and offered my cock to her, still wet with her juices. Carol took it in both hands and greedily brought it to her mouth, sucking on it as if it were a lifeline.

"God, you're still hard," she said, taking my cock out in order to catch her breath. "You're wearing me out, my sweet lover. What would you like to do next?"

I had watched enough porn online to know what I wanted to do with Carol. I leaned in to kiss her and whispered in her ear. "I want you on your hands and knees. I want to do it doggystyle, if that's okay with you. I think I might be able to cum that way."

"Oh, yes, my love, I love doggy. Just give me a minute or two to catch my breath."

Carol pulled me down and smothered me with kisses. She was such an attractive woman that I never really thought about the age difference between us. I suppose we were giving each other what we wanted, and needed, this afternoon. I secretly hoped that this would be the start of more sessions like this one.

Carol continued kissing me, her hands reaching down to stroke my cock softly. "You have such a gift, Chas." she said tenderly. "I want to teach you everything, if you'll let me. I'll show you how to please a woman and how to make a woman beg you for more. Please let me be your teacher."

I couldn't believe my ears! Carol must have been reading my mind, for this is what I had hoped for from the minute she went down on my cock and sucked me to orgasm. How could I say no to her offer?

"I'd like that very much, Carol. I'll do anything you want, just let me know."

"We can get together in the afternoons, just like today. Maybe, if the circumstances allow it, I'd like you to spend a night with me so I can show you how wonderful it is to wake up next to your lover and make love right away. I'll let you know when we can get together, if that works for you."

I simply nodded my head.

Carol got up on her hands and knees. "Now let's see how that doggystyle works for us."

I got up as well and got behind her. My fingers reached out and touched her pussy. It was still wet, so I finger-fucked her a little bit to make sure she was ready for me. Carol rocked back and forth on my hand and purred her assent. She was ready for this.

I removed my hand and replaced it with the head of my cock as I rubbed it all over her slick gash, teasing her so that I could hear her moan some more. Finally I began to slide it inside her pussy. She took it easily, swallowing more of it with each thrust of my hips. I held her by the hips and began to give her my full length. Carol tensed for a second and then arched her back to offer me her cunt. She slid back onto it until I was completely inside her. Her hands clenched the sheets and her head bowed down as I began to fuck her from behind.

I gave her long, slow thrusts, my cock nearly falling out with each retreat, only to slide deep inside her as I gave her the goods. She was cumming again within two minutes of fucking, moaning and rocking on my stiff cock and rolling her head back and forth as the pleasure became too intense to bear.

We went on like this for a long time and then Carol did something unexpected. She began to gyrate on my cock, fucking me back in a circular motion. This caught me off-guard and gave me such intense pleasure that I knew couldn't last. I fucked her faster, harder and deeper than before, knowing that I was ready to cum.

I thought about pulling out when I came in order to shoot my seed all over her ass, but thought better of it and stayed put as that familiar tingly feeling returned to my loins. I didn't announce my cumming, just reached underneath her and felt her tits. I rode her like a dog, pumping for all I could until I felt the first jets of cum shoot out of my cock. I filled her pussy as I came and, when I was finished, I pulled out of her and watched as my hot, sticky seed filled her pussy to overflowing.

Jesus, she was good! She knew how to move her body right when I was just about to go over the edge, making me cum inside her.

When I pulled out my cum oozed out of her wet cunt and ran down her inner thighs and onto the bed. I quickly got up and ran to the bathroom in order to clean off my cock. Carol caught me and would have none of that, taking my shiny cock inside her open mouth and cleaning all traces of my cum and her juices.

When she was done, she told me I could clean up further in the bathroom. I did as she asked and, when I returned, Carol sat, naked, on the edge of her bed.

"You should go, Chas, before someone wonders where you are. I need to take a long, hot shower and try to recover. Just so you'll know, I came five times with you this afternoon." She pulled me close for a final kiss before I left.

Breaking the kiss, she spoke to me again. "You go on home now, my young lover. I'll give you a call when we can do this again. It won't be long, though. I don't know if I can live without that big stick you have between your legs."

"You just let me know when, Carol," I said as I put my clothes on. I want to do this every day if we can."

Carol just laughed and waved at me to leave.

As I walked home, I felt more confident and actually stronger than when I first came here a few hours ago. Carol was going to help me make that transition to being a man. I couldn't wait.

As I walked inside the house upon getting home, I found that I was whistling. This was going to be some kind of summer school, and I couldn't wait for the next class to begin.