When I was 16 years old I had a best friend named Sam. His father had died when he was 6, and I'd known him since we were both 10. I'd spent that night at his house numerous times, and since I was 12 or 13 I had a thing for his mom. By the time I was 15 I had a real crush on her. She was 32 and looked so beautiful to me! She had a successful Real estate business, and she kept her body in shape. She was about 5 foot 6, and had dark, almost black hair that hung to her shoulders. She had nice round natural boobs, that I would later learn were 34D, and she a beautiful round ass, that looked very firm.
In the summer when she would join us outside at their pool, it took everything I had to hide the hard on I would get as she sunned herself in her bikini. It got to where I was spending almost as many nights at Sam's as I was at my own home. My mom even complained kidding me one time, that I lived over there more that at our house. Beth, that was Sam's mom's name never seemed to mind though.
The following school year, before the winter break, mom and dad had a chance to go on a weeklong ski trip. Without me even knowing mom had called up Beth to ask if it was OK for me to stay at their house. Of course Beth agreed right away. When she told me I was thrilled of course, it was like a dream come true. I thought maybe I'd get to spy on Beth in the shower, and get to see her naked or something like that.
My parents were leaving on a Saturday morning, so after dropping me off at Sam's, he and I had the whole day to goof around. We spent most of the day watching TV, or riding our bikes, and later in the afternoon, we went to his room to do our usual thing. Beth was out showing a property, so we had the house to ourselves. I jumped on his bed, and waited as Sam's retrieved the stack of Playboy magazine's he had hidden under his bed. He'd found them a year or so ago, while rummaging through some old boxes in their attic. It was Sam who taught me about masturbation, and we'd even progressed past the stage of just jerking off together. It was always more fun to jerk each other off, and see who could last the longest, and who would cum first. At that age it was just all harmless fun. Neither of us were gay or anything, it just felt better to cum having another person's hand stroking you then it did your own.
SO we had our fun that afternoon, and later that evening his mom cooked us a great meal and the night was pretty much normal. The next day Beth was home so nothing much happened, except later that night I started feeling a bit ill. Beth checked me and I was running a low grade fever. Her cool hands on my cheeks and forehead caused me to get an erection which I tried my best to hide under my pajama bottoms. She either didn't notice or did a good job pretending not to.
The next day I stayed home from school sick. Like most kids though, by noon I was feeling OK again, and getting bor. I went into Beth's bedroom to snoop around. Of course the first place I looked was her underwear drawer. The sight of her silky, and lacy panties and thongs gave me an immediate hard on. I even found some dirty panties in her clothes basket. I could see the slight stain in the crotch, and I sniffed it. It had a faint odor that made my cock throb. I held onto those panties, and searched further.
In her bedside nightstand I found a small pink vibrator. It too had a faint odor, and the thought of it having been inside her pussy made me wild with desire. The last thing I found was this small, thin, photo album. When I opened it up I was shocked. It was full of photo's of Beth, and she was naked in all of them! Oh sure, I had seen Playboy photos, but I'd never seen a girl or real woman that I knew naked, much less one I lusted after!
Just then I heard the front door open and close. I hadn't realized how long I'd been in Beth's bedroom, and now she was home. Quickly I shoved the vibrator, and photo album back in her drawer, but not before stealing a couple of the photos. I then dashed back to the bedroom I was sharing with Sam, and stuffed her used panties, and the photos into my overnight bag. When Beth came upstairs and peeked into the room I was sitting on the edge of the bed, watching TV. She smiled and told me I looked much better, and I told her I was feeling much better. As she turned and walked out of the room, I watched her ass move under the dress she was wearing, and thought of how I had just seen pictures of it naked!
I wanted to jack off so bad, but just then Sam got home too. So much for jacking off right now I thought! I couldn't keep my eyes off Beth all evening, and at the same time I hoped she didn't notice. Later, after dinner, and some TV watching, she announced she was going to shower and get ready for bed. I waited about ten minutes, and then told Sam I was going to the bathroom. I went Past Beth's bedroom and the door was open. I could hear the shower running, and I could see the bathroom door was cracked open too. I went in and peeked through the door. The she was in the shower. I watched as she soaped up her breasts, and then ran her hand between her legs. I watched as her hand moved around to her ass, and slid up her ass crack! I thought I was going to cum right then and there, but suddenly Sam was calling out to me, wanting to know what was taking me so long. I hurried out of the room and back to the living room.
A little while later, Beth stuck her head around the corner and announced she was tired and going to bed. She also told Sam and I that we had thirty more minutes, and we needed to get to bed as well. Thirty minutes later Sam was in bed, and I was still up. I told him I had slept a lot earlier that day, being as I was sick. I waited a bit, and then checked on him. He was fast asleep, so I got the pair of Beth's panties and the photo's out of my bag and snuck back into the living room.
I slipped off my pajama bottoms, and wrapped Beth's panties around my hard cock. Looking at the pictures, I started stroking myself as I lay back on the couch. I was really getting into it when I heard a soft moan behind me. I sat up and turned around. There stood Beth in a sheer nitie, with her hand down the front of her panties rubbing herself. Without saying a word, she walked over to the couch, and pulling her hand from her panties she ran a finger under my nose, giving me a good whiff of her pussy. She then looked down at my still hard cock, and asked my why I'd rather look at a picture when I could look at the real thing. Well I didn't have an answer for that one!
She then stepped slightly away from the couch and pulled the nitie over her head revealing her big beautiful breasts and rock hard nipples. The she turned around with her back facing me, and bent way over, pulling her panties down as she did. As she stepped out of them, she spread her legs wide and reached between them. She ran a finger over her wet slit, and even up to just touch her little brown asshole. After picking her panties up off the floor she stood and turned around, again facing me. She again stood right over the couch, and this time she reached down and slid her old set of panties off of me. This sent a shiver through me as her hand slid up my cock, pulling the old panties with it.
Standing straight up again she tossed the panties she'd just taken off over the top of my cock. The still had her body warmth in them, but the crotch was soaking wet and felt slick against my cock. As her own hand again returned to her crotch., she told me she wanted to watch me finish what I had started! Only later on in life would I discover that a lot of women loved watching a man masturbate.
As I started jacking off once again, she started rubbing her pussy, faster and faster. I started stroking my cock faster and faster, sliding her wet panties up and down my hard shaft. I knew I was getting close to cumming, and I guess she could sense it too, because she ordered me not to cover the head when I came. She told me she wanted to watch my hot sperm spraying out of my young hard cock! WOW, I never even dreamed women talked like that, and it really sent me over the edge!
I felt that tingling in my balls I get just before an orgasm, and then my cock was jerking in my hand, and glob after glob of hot sticky cum is shooting out, and landing all over my tummy and chest. All the while I was cumming Beth was chanting; Yes baby cum! Yes baby shoot it out for me, and then; so much cum, so much! After that she groaned herself, and arched her back. In a deep almost growling voice she announced she was cumming too. Her nipples got even bigger and harder, and her body trembled and jerked as she rode out her orgasm with her fingers deep inside her.
After we had both calmed down, she reached down a scooped up a glob of cum from my chest, and then stick her finger in her mouth. She made a comment about how good my cum tasted, and what a bad little boy I was, all with a big smile on her face. She then reached down again, and this time held my cock firmly stroking it once or twice. After she released it, she told me I need to get to bed, and that she felt like I was probably too sick to go to school again tomorrow.
After pulling my pajama bottoms back up, I stood up. She took both pair of her panties from me, and told me I wouldn't be needing them anymore. Having said that, she gave me a light peck on the cheek and turned and walked off. Half way down the hall she stopped abruptly and I almost ran into her. She turned and looked me straight in the eyes and told me that if I wanted more, what happened a little bit ago, and anything that happens after has to be our secret, and our secret only. She made me promise which I quickly did, and then she kissed me. This time right on the mouth, and her tongue even slipped inside and circled for a moment before she broke the kiss off. Giving my cock one final squeeze through my pajamas, she again turned and walked off, this time going into her bedroom, and closing the door behind her.
The next morning Sam was up before I was, and he was already in the shower. When he came out, I faked being sick, just like Beth had told me too. Soon after, he left for school, and now I got in the shower. Less than five minutes later the shower door suddenly came open, and there stood Beth completely naked. She stepped in, and before I could say anything, she pulled me toward her and her tongue was in my mouth. Her large breasts were pressed against me for the very first time, and they felt wonderful. Her nipples pressed had into my skin, and I could even feel her heartbeat.
Beth grabbed the soap and started lathering us both up. She then had me lather and play with her tits, and told me to touch anywhere I wanted. My hands were all over her. There were on her tits, her pussy, and her ass. Her hand were all over means well, but eventually settled on my cock and balls. She soaped them up good, and rubbed, stroked and played with them. I felt like I was ready to cum already! Again, experience taught Beth that I couldn't last long, and she quickly pulled me cock up and smashed it against her tummy. Reaching around me she inserted a soapy finger into my ass and I exploded! I grabbed her and we both held each other tightly. As my cock throbbed against her, she held my ass, and kept one finger inserted inside me. She also whispered repeatedly; That's it baby, shoot your hot sperm all over mamma Beths tummy, let me feel it.
By the time she withdrew her finger from my ass, my cock was barely throbbing. I was still 3/4 erect though! We dried each other off and then went straight to her bedroom and got in bed. I started to try and kiss her, but she stopped me and told me we had to talk first. She told me that I had grown into a wonderful young man, and she couldn't wait to teach me all about sex, and how to really pleasure a woman. The but was, she had to really know this would always be just our secret. She said that most of society would never understand, and that she could actually get into trouble with the law if someone ever found out. I told her over and over that I would never say anything to anyone, and she believed me.
Having said all that, she leaned into me, and we kissed deeply. As we kissed her soft hand ran up and down the length of my hard cock! Yes I was hard again, having not really lost my erection from my first orgasm. She whispered to me that she was now going to really teach me how to make love to a woman. Placing my hand on her tit, she instructed me to rub it slowly and then begin to gently tuck and pinch her nipple. She moaned as I started doing just that. Next she taught me how to suck on her nipples, and how and where to touch her pussy. She was so wet and she felt hot and slick inside, when I slid my finger into her.
Beth lay back on the bed, and spread her legs wide exposing her whole crotch to me. She told me to get between her legs, but I was not to touch or do anything, until she told me what to do. She spent the next several minutes explaining every inch of her beautiful female anatomy; the treasure that lay between her wonderful legs. It's not like I'd ever seen one before, but I was amazed at the size of her clit as she called it. After spreading her lips and pulling back the hood a little she showed me her clit, and explained to me that it was the real trigger to giving a woman an orgasm. By then the smell of her pussy was begining to fill the air around me, and I had an instictive urge to lick her.
After my lesson, she told me it was now time to fill that urge, and she began to instruct me on how to lick, kiss, and suck on her pussy and clit. As I did all of those things, she talked less and less, and moaned more and more. Soon the only sounds that filled the room were those of her moans and groans. Her hips began to rotate off the bed. Her hands forced my head tighter into her crotch, and she got louder and louder, until; She screamed out she was cumming! I kept my face buried in her crotch, still licking and sucking, as she rode out her orgasm. When it was over, she actually had to push me away. She had a big grin on her face, as she told me that if I kept improving my newly learned skills, I was going to make a lot of girls, and then women, very happy!
I know everyone wants details, but there is so much more to tell that it would take forever. What I will say is that for the rest of the morning and into the early afternoon, we never got dressed or got out of bed. Beth gave me my first ever blow job, and swallowed my cum. Hers was also the first pussy my cock ever slid into. As the head of my cock penetrated her lips, and my hard shaft slid inside her, I thought I had died and gone to heaven. As Beth's body undulated under mine, and she groaned through another orgasm, I shot my load deep inside her; my first ever orgasm inside a woman. The whole day was filled with firsts. The only thing I had yet to do was have my cock in her ass, but even that would happen later that week!
By the time we dressed that day, and Sam got home I was so worn out that I had to chuckle to myself, because I probably did look sick! Believe it or not, later that night I was horny again for Beth, it was just all so new and exciting. Beth didn't want to take a chance on Sam catching us in the act, so she ushered me into the bathroom, and gave me a quick blow job, and then sent me back to bed.