Growing up, my parents were best friends of a couple three doors up the street, they played bridge every week, and were constantly having each other over for cookouts, parties and things. Really, just any excuse to get together.
When I was little, their teenaged sons and, then, daughter, would babysit me, we just all knew each other really well.
I remember when I was younger, maybe eight or nine, that when I was at our friends' house, usually watching TV, Debra and her friends would be in the living room making out with their boyfriends and girlfriends and that, sometimes, one or more pairs might disappear into one of the bedrooms but the real import of the situation was lost on me at that age.
Then, when I was fourteen, the four of our parents went to Las Vegas for the weekend, leaving me alone but asking Debra to look in on me. I also had her cell number if anything dire came up. It never did, of course, but parents always think something might.
I went over to her house to have a swim, they had a very nice pool out back which I knew I could use whenever I wanted. No one was home so I let myself into the backyard like I often did.
As I was swimming, I heard, "Hi, Brian, looks like fun, I'll be right out." It was Debra, now twenty-two, who, in a few minutes, came running out and dove in the pool with me.
"Oh, this feels so good. Been here long?"
"Nah, just about twenty minutes or so."
"Time for some sun," she said and climbed up out of the pool. I followed her up and we both lay down on chaises basking in the sun.
Now, Debra was very pretty, I'd seen her in bikinis for many years, and, yes, I had closely observed every curve of her lovely, shapely body. I was a male, after all, and her's often was the image I had in my head when I masturbated.
We were laying there close to one another when she said, "You know Brian, we've known each other for ages and I've watched you grow up, but, in the last year or so, I've really gotten excited seeing you start to become a man."
A man. Wow, that's really cool coming from such a pretty older friend that I've known for so long.
"I've always felt so comfortable around you, Brian, and I've loved you like a little brother." She turned to me and continued, "But, Brian, lately I've been wanting to love you in a different way," and she leaned over and gave me a long, unexpectedly passionate kiss. Her hand was up on my cheek, it felt so warm and soft.
She got up and sat sideways on my chaise, turned, and lay down over me with her legs drooped on each side of me pressing down on me kissing me with her tongue as she ground her pelvis into my crotch. There was really no question what was happening, I didn't have much sexual experience, but I knew enough to know that this wasn't brotherly-sisterly kissing, it was definitely sexual. For sure.
As she kissed me, I felt her hand slip between us down my front and snake into my trunks and alongside my penis which she rubbed up and down with her fingers. She then pulled her hand out, got up, knelt down next to me and began kissing her way down my neck, my chest where she started licking and sucking my nipples, then to my stomach, tonguing inside my bellybutton.
It was feeling so sexy and wonderful, I just lay there as this beautiful, young woman, eight years older than me, kissed her way down my body, a true first for me.
"Mmm, Debra, you're making me feel so good. Really hot." She raised up, reached up behind her neck and off came her top. Full, plump, firm, simply perfect breasts, right there in front of me, pink nipples standing out, just lovely.
"If you want to even feel better, Brian, you'll need to take your trunks off." They were off instantly with my dick rising up which she immediately had her lips over and was sucking up and down. There's no fourteen-year old guy in the world that'll hold off for long under circumstances like those.
As she raised up keeping just the tip of my penis inside her mouth, she started swirling her tongue around the tip around and around until my cum exploded into her mouth. I went limp, except for what she had in her mouth and was overcome with the most wonderful feelings of happiness, nothing, nothing had ever even been close to how good that felt.
"Oh, Debra, that was fantastic. You are wonderful, god, you are so beautiful, so, oh, so everything."
She held my cock in her hand and licked all around the tip, even gently squeezing out a few more drops which she tongued off. She then stood up and untied her bottom and let it fall to the ground. She stood there before me, perfect. She had a nice, narrow waist, seductive hips, long, shapely legs rising up to meet at a plump mound, beautifully split in half, moist with anticipation.
"You are the most beautiful girl, uh, woman, I've ever seen. So pretty, just incredible. I can't believe this is happening."
"Well, it is, Brian, it is," as she swung a leg over me and sat down on my thighs then leaned forward over me, her beautiful breasts pressed hard against my chest, and began french-kissing me as she rubbed her wetness all over my crotch and abdomen.
She raised up and whispered, "I think we need to go up to my bedroom now, Brian, would you like to do that?" and she got up, took my hand and pulled me up and we walked into her house, up the stairs and into her bedroom.
She turned to me, took me in her arms and began to kiss me again. She was somewhat shorter than me, maybe about five-three, I'm five-nine. My hands were everywhere on her, feeling the smoothness of her skin, the softness of her butt, the flowing curves of her back as she pushed her pelvis into me.
"Come to bed, Brian, come to bed with me," as she led me over to her bed, sat down and took my cock in her hand.
"I just love your cock, Brian, so nice and pretty. I hope you don't mind me calling it pretty, it's really beautiful," she said as she leaned toward me and I watched it disappear into her mouth.
Then, the feeling came. Oh, this was exquisite. There is no feeling I've ever had that is even remotely as wonderful as this. Her mouth is so warm and slippery, the feeling of sucking was stunning. And, the, she ran her tongue all around the tip of my dick as she sucked just the end.
I simply couldn't help it, without any warning, my whole body froze as my cum began to shoot into her mouth. She pulled back and I spurted all over her face and neck and breasts, those beautiful breasts.
I was hoping she wasn't mad that I had cummed in her mouth but she was laughing.
"Look at all your cum, Brian, you really shot a load, it's all over me," she said, "You'll just have to lick it all off me now, you naughty boy."
I really didn't care if it was my own cum or not, where it was and that I was going to lick her there was all that was on my mind as I started with her breasts. I quickly made it up her neck to her face.
"Maybe you got some down here, Brian, you'd better lick me just to make sure," as she opened her legs wide and led my face between her legs. Oh, here it is, what I've dreamed about ever since I saw my first Playboy magazine. A real, live pussy.
"Here, look, this little thing, right here. My clit. You've heard of a girl's clit?"
I nodded and she said, "Lick it nice for me, Brian, I'd just love that."
As she held the little flaps open over her clit, I licked up and down and she was immediately moaning, "Oh, Brian, oooh, that feels wonderful. Mmm, right there, oh, you're making me so hot. Oh, I just want you inside me, Brian, come up here." and I crawled up as she widened her legs even more.