I was almost 11 when it first happened.
My Mom owned a small two room summer cabin in an older resort beach area. Her best friend, Anne, who lived at our house, also had a young son, Rob, he was only 8. Anne, would stay at our cabin through the week so us kids could have a holiday and my Mom would come down on the weekends. So all week we’d be there alone with Anne. Anne was about 40 at that time. Dark hair, nice looking and a robust woman.
One night about a year before, at home, I stayed up late because I knew Anne bathed after we were in bed. Mom was at work and Rob was asleep. I remember standing at my bedroom door and watching Anne as she walked naked into the bathroom for a bath past my door. She had large heavy breasts with great reddish nipples and I was thrilling to see real mature tits like that. Anne was the first I had even seen. I heard her get into the bath.
I waited awhile and then pretended to have to go pee and walked into the bathroom. Anne was in the tub, naked in her glorious body, her breasts all shining and soapy. I pretended I didn't notice her because I was so sleepy but I couldn't pee because my dink had swollen so I pretended. I went back to my bedroom and jacked off to sleep. Ever since then I had a lust for Anne. Yes, even at 10 years old.
Down at our cabin, I often played sex games on the beach with other vacationing young girls, but that didn’t usually amount to anything except me jacking off in the bushes. Girls my age had no tits and I loved Anne’s big ones. The girls did like seeing a cock for the first time though and mine was already almost 6 inches long! I showed it off whenever I could, trying to get a girl to touch it. But that ever hardly happened.
The cabin had one large room with two bunk beds and a foldaway double bed. It also had a tiny bathroom and kitchen. Rob had the bottom bunk and I the top while Anne slept across the room in the big bed.
One night, little Rob was asleep and I was in my top bunk bed, trying to get my pajamas unwound before going to sleep. Anne was in bed across the way reading a novel with a small light on. As I fiddled with my pajamas and took off my shorts to get into them, I started to get an erection. First trying to hide it and then wanting Anne to see it. I fiddled around with the clothing for way too long and it must have been obvious that I was showing off my cock to Anne. At one point she put down her book and just stared across the room at my young straining cock.
This only sent me into a huge heart-beating thrill and I displayed for her while trying to make like it was accidental and I didn’t realize she could see it. My cock seemed to grown an extra inch from her watching it! After a while I slipped under the covers and was almost asleep when Anne turned out the light. I thought that at least in the darkness I’d be able to jack off under the covers.
That was when I got my brainwave idea. I thought it was pretty clever for an almost 11 year old. After a while I carefully slipped off the bunk bed, approached Anne’s bed and whispered to her that I was a little cold and could I snuggle in with her for a while to warm up. She answered that it was okay if I was cold and pulled aside her covers for me.
Now my heart was pounding as I pressed in close to her. Gawd she was warm. I cuddled into to her, feeling her nightie as I did and knew she wore no bra or panties under it. Of course I wanted to feel her all over but knew it couldn’t be obvious. I was also afraid I’d cum by touching a beautiful, mature, big breasted 40 year old woman! My cock was very hard all this time and I had tucked it between my legs so she wouldn’t feel it.
She was very relaxed next to me and was breathing silently. I pretended to be falling into sleep and allowed one hand to move onto her big breast. Gawd that was the thrill of my young life so far! Holding one of her huge breasts! I had to squeeze my legs together to stop my excited cock from springing out! Her breast was too big to even get my hand around it! I wanted to get up and jack off right then but knew I couldn’t let go of her lovely boob. My hand only covered about one third of it. I just lie there wondering what I should do next. My cock was throbbing from being so close to them and I was worried about her feeling it against her.
Anne started to breath more evenly. She was sleeping I thought. But even then I knew she must have felt the sexual tension. I was almost delirious with pleasure and excitement. Lying next to an older woman who I thought was so sexy. I allowed my legs to part because my dink was hurting from being suppressed.
As Anne continued to breath evenly I began to move my finger absently across her nipple, as if I was twitching in my sleep. I don’t think I imagined it, but she paused a moment as I did, and then I sensed her breathing quicken. Even the pulse in my finger was pounding. I hoped she couldn't feel my own heart beating so wildly.
I moved very stealthily to put my hand under her nightie top and soon squirmed enough to now have her bare breast in my hand, the nipple in my palm. I almost had an orgasm from that alone! My cock was about to cum on its own and I moved slightly, allowing it to touch against her thigh. She breathed a sigh as if asleep but let her hand slide under the covers until now the back of her warm hand touched my cock. That sent ripples flooding through me. I wanted to fuck her hand and she even turned it slightly and was suddenly holding it! My cock held by her fingers curled around it! My thrills were coming with each breath, Of course Anne was not acknowledging anything but that she might be dreaming in a deep sleep. Surely she could feel it throbbing!
I was ecstatic. My heart pounding enough to bounced us both off the bed. I knew Anne couldn’t knowingly touch me in any sexual way. But I wondered if she was feigning sleep herself?
I was so sexed up at that point that I couldn’t control anything I did anyway. I continued to stroke her wonderful breast and she breathed another huge sigh and turned toward me. Her nightie top fell open and both her breasts were now right before my face.
Anne was breathing steadily as I slowly pulled away her nightie cloth and freed those huge white breasts. I was almost delirious with secret pleasure.
I had seen enough of my father’s porn magazines to know that you sucked them when they were there for you. He was long gone now but his legacy was leaving those magazines for me to learn about sucking, fucking and sex! Mom never knew I found them.
I finally held one breast in both hands and began sucking the nipple softly. I was in heaven. I’ve been a breast man ever since! Anne’s heat was now intense and my cock was throbbing. She continued steady breathing and still seemed to be sleeping. Her grip on my throbbing young cock seemed to tighten. I was afraid that if she awoke, she would send me back to my bunk. IF she was sleeping at all.
It never occurred to me then, but if she liked what I was doing, she couldn’t let me or anyone else know that she was even aware of it.
I finally moved one hand to her warm thigh and began rubbing forth and back until I raised her nightie higher, stealthily moving upward and I could put my fingers on her pussy! This was paradise. Her wiry pussy hair felt wonderful.The girls I had played with so far in my life had hardly hair at all. Anne’s pussy was a wonderful dense bush! I began stroking it softly, it was moist and slippery, and my finger kept slipping into the moist crack. Gawd it felt fabulous.
Anne’s pulse was beating harder now, I felt it at her breasts. Her pussy was now in my hand with my finger at the slit. Now I knew I was going to try to get my cock in there. I shifted quietly closer. Tried raising my hips over her thigh. But was afraid she’d wake. Moonlight began coming in the window above and I pulled the blanket down to see Anne’s breasts. They were actually big and saggy, I didn't know what 40s were then but these were them, the nipples as wide as silver dollars at that time I thought they were magnificent! I sucked them both in turn. Her hand shifted again and now she adjusted her hand on my cock, closing around it, still breathing as if sleeping. I could feel a surge coming and tried to hold back but it was way too pleasurable and exciting. A grown woman was moving her hand up and down on my cock!
In less than a minute I came my liquid spurting. It was the greatest sex feeling I had ever felt!
And the best orgasm I could ever have imagined! She MUST have been awake to do that but remained passive as I breathed hard and tried to still my heart. But my cock wouldn’t go down, just stayed hard while the sight of those breasts spurred me on.
I tried shifting in various ways to get my wet cock in that dark pussy but without getting atop her and causing her to wake it was impossible.
I stroked her pussy slit more, now letting my fingers slide in and out of that lovely slippery and hot hole. My head was spinning. I tasted one finger and wondered what it would be like to lick a pussy like in the magazines? It was like an olive oil texture. My cock grew even harder and seemed biggest yet!
Anne suddenly breathed deeply and twisted around, as if she was in a deep sleep now, turned her back to me, suddenly robbing me of the delight of her great juicy breasts. For a moment I was unsure of what to do until her hand fell behind her back and again touched my still hard cock.
I was trembling with excitement now. Thinking I should try to fuck her hand. I shifted forward until she held my cock firmly and moved her rear closer. I suddenly got the idea.
I moved close and the fit was perfect, spooning with this wonderful 40 year old woman, the 11 year old was about to have his very first perfect fuck!
I slid so easily into her. It was so hot in there and so slippery. I tried as much as possible to be slow and give her some pleasure too. Pushed it in as far as it would go. But pushing my cock all into her wonderful pussy was way too much and it drained on its own once again, making my breath catch and a wave radiate through me. This was incredible and so delicious.
My head was spinning but I resolved to try licking that pussy sometime it seemed so big and soft and pliable. I knew I needed to have her pussy lips right over my whole mouth. Anne finally sighed and turned back onto her back, her hand grasping for my softening cock again, ignoring the wetness and my sticky cum.
I was already thinking how I could do this again tomorrow night. My first was the thrill of a short lifetime and an addiction I was never going to get over.
I snuggled into that fabulous warm body and fell into a wonderful sleep with guaranteed dream fantasies forever!