Well, it seems to me there aren't a great many storied on here about younger boys with older females, unless that female is the boy's mother, aunt, etc. Never having been a huge fan of incest, I thought I'd correct this with a story of my own, involving a 16 year-old girl, and a pre-teen boy. Having once been a pre-teen boy, you can look at this as what I wish might have happened. Feed back is welcome and encouraged, as it may lead to me writing more of these. And do let me know if, and how well, I pulled off writing first person from a female POV.
Of all my sexual experiences when I was a teenager, one stands out both because of its strangeness and its intensity. Though I'd lost my virginity my freshmen year of high school, to my then-boyfriend, and had had sex a few times since then, this time was still unique.
It was the summer I was sixteen. I was actually pretty good looking then, though I didn't really realize it. Because I was a little heavy I undersold myself, not realizing that boys were more likely to notice my curvy hips, and large breasts, then the fact I was a little over-weight. At five seven, I had a full hour-glass figure, with wide hips and d-cup breasts. My dark hair was shoulder length, and I usually styled it up. Still, I chose to see the glass as half-empty, and while I didn't think of my self as "ugly" or "fat" I did think of myself as "pretty" or "slender" either.
That summer I was busy. Between summer school, and my ECs, I found time to make money baby-sitting. I first did it for friends of my parents, but word of mouth about me spread, and soon I was working for friends of friends of friends, and so on. It was one Friday night, while watching the eleven year old son that it happened.
I got over to the house around 7:00, and was greeted by Mrs. Leinden who had asked me to sit while she and her husband went out to dinner with friends. On the phone she told me it was going to be a long night, till at least 1:00, she said she knew how late that was, but could pay fifty dollars for the night. Not telling her this was more then ten more then what I usually charged for that time, I said it would be no problem staying to 1:00.
"Hi Marissa" Mrs. Leinden said to me. She was dressed to kill, in a black evening dress that displayed her womanly attributes in such a way that I felt like a skinny little girl next to her. "We're just about ready to leave" she said, as she ushered me inside "Dilion, come in here and say hi to your sitter, Marissa." A boy of about eleven, with sandy blond hair came in and said 'hi' in a very unenthusiastic voice. "I left money for pizza on the kitchen counter, help yourself to the fridge. You already have my cell number, so you can call it if you need to get us. I think that's about it" Mrs. Leinden said with a smile. "Paul, the sitter's here, let's hurry and get going" she called up the stairs.
Mr. Leinden came down the stairway, dressed in a dark blue suit. He was fiddling with the cuff of his shirt that stuck out from under the sleeve of his jacket as he walked. "Damn thing came undone again" he said to his wife. "Work on it in the car honey" she told him, I'll drive. "No, its okay" he said with a dismissive brush of his wrist as he pulled the jacket sleeve back down.
A few minutes later the Leinden's were gone, and I settled in. Dilion had gone up to his room, and I was left watching TV in the family room by myself. Around 7:30 I decided to call the pizza place. I called up the stairs to Dilion to come down and tell me what he wanted on it. He just yelled back pepperoni, so I went back and dialed the number. I ordered a large pizza with half pepperoni, half olives and mushrooms (I'd been trying to eat vegetarian for the past half year or so), and then went back to watch TV while I waited for the delivery man.
A while later I saw the delivery car pull up outside. I went to the door, and opened to greet the pizza guy before he even had a chance to ring the door bell. I paid him with the money from the kitchen and told him to keep the change, then took the pizza and closed the door. I called up the stairs for Dilion, and went into the kitchen to put the pizza down. When I didn't see Dilion, or hear him on the stairs, I decided to go look for him, rather then keep shouting like a savage.
I walked up the stairs, and went to the room I assumed was Dilion's. The door was part way open, so I looked in, but he wasn't there. Still it differently was a room lived in by a male child, so I knew I had the right place. I turned around and wondered down the hall. Maybe they had a study or something with a computer up here. As I went to look, I passed by the door to the Leinden's bed room, and thought I sensed movement from inside.
Opening the door, I found Dilion. He was sitting on the floor by his parents bed, with his back turned to me. I walked closer, until I could see over his shoulder. Open on the floor in front of him as a porno magazine. It looked like a pretty tame one -the women on the open page was showing just a little more then she would have in Playboy, and even though the shot was centered on her cunt, the modal had her legs discretely close together, so you didn't see too much. Dilion was staring at the magazine as if in a trance. For a second, I thought about backing out, and closing the door, and acting as if I hadn't seen anything, when Dilion suddenly sensed my presence, and whirled around. He cried out in surprise and bolted back, but didn't have anywhere to go.
"How... How long were you there?" he asked breathlessly, his eyes filled with terror.
"Just a few seconds," I said
"You're not going to tell my mom, are you?" he asked
"Um..." I said, not knowing my answer. I guess it was what I was supposed to do, but the thought of telling her was almost as embarrassing to me as to him.
"Please don't" he pleaded "I'd be grounded for the rest of the summer. You can't tell her, please..." Dilion said frantically. He was almost to tears, and I suddenly felt very sorry for him. I got down on my knees by where he sat on the floor, and reached out to pat his arm reassuringly.
"Its okay Dilion, I won't tell her. It'd be almost as embracing for me as for you, and it's not like you did anything really wrong."
"But you caught me looking at..." Dilion started, almost unwilling to believe he was off the hook.
"Its okay if you like looking at naked girls" I said. "Most boys do. That's why the make magazines like that."
There was a pause, and we both sat there. I looked down at the magazine, still open on the floor. The woman really was a looker, with long red hair, and large breasts with pert nipples. I looked back at Dilion. "I guess you really like to look at these pictures, huh?" I asked, almost with out thinking.
"Um, yeah," he said. "Usually I look at them when my parents go out, and I don't have a sitter. I only have one tonight because they're going to be gone so late. Since you were downstairs, I figured it'd be okay, and I'd hear you coming up the stairs but I guess I was wrong."
"Uhhuh," I said, and there was another short moment of silence. As we sat there, and I looked back at the girl, I thought flashed in my mind that caused my stomach to tighten. I debated it for a second, but before I could talk myself out of it, I spoke.
"Dilion?" I asked hesitantly "Have you ever seen a real naked girl?"
There was a long second of silence, before Dilion said, "Not really." Now the tightness in my stomach moved lower, as I asked "Would you like too?"
"Sure," Dilion said. "But I don't know any girls who would let me."
"How about if I let you?" I asked, the feeling inside me growing. Dilion gulped "Okay"
Unsure about what I was about to do, I stood up. With both hands, I gripped the button of my T-shirt, and pulled it off, revealing my bra-clad breasts to Dilion. He gasped slightly, and I noticed now a small bulge in his shorts. I smiled slightly, and reached down, and undid my belt. I unbuttoned the fly of my jeans, and slid them down over my curvy hips, down my legs, and let them drop to my ankles. I stepped out of the jeans, and was now clad only in my bra and panties. I did a slow 360-turn to let Dilion take all of me in.
"What do you think?" I asked him with a husky smile.
"You're pretty," he said breathlessly
"Thank you Dilion" I said. "Now, do you want to see the rest?"
Dilion only nodded his head. Reaching behind myself, I undid my bra, and pulled it off. My large breasts bounced free, and I arched my back to push them out more prominently. My pointy nipples with their large areolas hardened at the cool room air, and my own excitement. Displaying myself like this was getting me hot!
For his part, Dilion was speechless. Here now was the flesh-and-blood reality of his magazine fantasies.
"What do you think of my boobs?" I asked Dilion, my voice surprisingly low
"I... I love them," he said.
I took one of my tits in my right hand, and squeezed it gently. "Would you like to touch them?" I asked Dilion nodded yes, and stood up. He reached out tentatively, and I released my boob to guide his hand to it with mine. His hand rested on my breast, and he touched it, exploring its texture. After a few seconds of this, he squeezed it, harder then I expected him to, though not to the point of being painful.
"Careful," I quietly told him. "Do it gently."
He relaxed his grip a little and kneaded my tit. I sighed.
"Does it feel good if someone touches them?" he asked.
"Oh, yeah, it does," I said with another sigh. "Especially if someone rubs my nipples that feels really great."
With that, Dilion moved his fingers to my nipple, and softly rubbed it and the surrounding area. Even though I expected the touch, the pleasure caught me off guard. I shuddered slightly, and there was a sudden increase in the wetness of my pussy. I had just gone from moist, to wet, and I hoped I wouldn't soak through my underwear. Dilion, picking up on my feelings, stopped.
"Did that feel good?" he asked inquisitively. "Yeah, it did," I told him. Encouraged, he rubbed more, and brought his other hand up to knead my other breast. After a few more seconds, I gently stopped him.
"Sit down on the bed" I told him, "I've got more to show you."
Dilion obediently sat on the edge of the bad, and I turned to face him. Smiling widely, now comfortable with what I was doing, I hooked my fingers in the elastic waist band of my panties, and pulled them down, across my hips, and bent over to bring them down to my legs, stepping out of them, I straightened back up, and Dilion was treated to his first real-life view of what lay between a girl's legs.
"What do you think?" I asked him with a wink. Dilion just stared with his mouth half open.
My pussy was shaved, so everything was clearly visible, much more so then on the magazine women. My outer labia were fleshy, and concealed my smaller inner lips. There was a thin dark line between my thick outer lips that opened up at the top to form a small oval indentation over my clitoris. All and all, my cunt looked very much like a girl of the same age as Dilion.
"Have you ever seen a real girl's pussy before?" I asked him.
"Na--No..." he stammered.
"Anything you want to know about it?" I asked him.
"What's the clit?" he asked with out hesitation.
I smiled. "Well, that's a very good question," I told him, feeling very much like some scandalous school teacher. "A girl's clit or clitoris is the most sensitive part of her body. It's a little hard to find, but if you look right about... here," I said indicating the indent at the top of my slit "You can kind of see it. If you touch it, it can make a girl go crazy. Want to try?"
"Okay" I said moving closer to him. "Just put the tip of your finger right here at the top of my slit."
Dilion reached out, and with his index finger, pushed into the folds of my skin surround the little indent, and he pressed on my clit. My body shook. Dilion was surprised, but sensed I was alright, and began to move his finger a little, rubbing. The stimulation was wonderful, but soon got to be too much, so I gently removed his hand from my throbbing clitoris.
"Okay Dilion, that was great. Do you have any other questions about my pussy?"
"What does it look like spread open?" he asked.
The question caught me off guard, and again my cunt flooded.
"Well" I said with shaking knees. "How about if I lay down on the bed and you can find out for yourself?"
With out waiting for his answer, I got up on the bed, and laid flat on my back. Spreading my legs slightly, I invited Dilion between them.
"Just use both hands, and pull it apart" I told him. I felt Dilion move into position and could feel how close he was to my pussy. Then I felt the touch of his fingers on my labia, as he spread them apart, exposing my pink, wet insides. I could feel the cool air on my exposed inner lips, and still throbbing clit. I could feel it even more so at the markedly wet mouth of my vagina, which was dripping with juices.
"It's all wet," Dilion said still holding my cunt open "Is that normal?"
"Normally it's just a little moist," I told him "But when a girl gets excited her body makes fluid in her pussy to make everything wet and slippery."
"Why's it do that?" he asked.
"It's to make it so a man can put his penis inside the girl's vagina," I said.
"Oh!" Dilion said, and there was a long pause as I felt his gaze on the mouth of my vagina.
"Marissa?" he asked suddenly breaking the quiet.
"What," I said, craning my head up, so I could see his face between my legs. "Could I try, you know, putting my thing inside you?" he asked blushing.
The question set my whole body on fire. The tightness in my stomach that had been there since this had started surged. I thought about what he was asking, for the longest minute of my life. And then finally I spoke.
"Sure," I told him.
"What am I supposed to do?" Dilion asked sheepishly "First, take of your clothes." I told him. He did so, and as he undressed I got my first look at his cock. It wasn't very big of course, only a little over four inches, fully hard, but it was still arousing to me. I thought of everything I'd like to do with it. I'd like to suck on it, and then have Dilion rub it between my boobs, but I knew that would be too much. It would be a miracle if he didn't come as soon as his head touched my love-tunnel.
Once fully naked, I told Dilion to get between my legs, and climb up on top of me and lay down. He did so, and I felt the light weight of his boyish frame pressing against me. I liked the way it pressed against my breasts, pushing them down, but not as much as a boy my age. His cock was level with my pussy and I felt the base rub against my mons, and right over my clit. I reached my mouth up to his, and kissed him. Softly at first, but with more passion as Dilion responded, and soon I slipped my tongue into his mouth. He reciprocated, and we were exchanging deep French kisses. Finally I broke the kiss, and told him it was time.
"Move your cock so it slides along my pussy," I told him. He did so, and I told him to thrust. His first thrust moved the length of my slit, and made my moan. The second hit my clit, hard, making my cry out louder. On the third, the head of Dilion's cock caught in my entrance, and I told him to push.
Dilion did, and I felt my vaginal walls make way for one, then two, then three, then four inches of Dilion's cock. Fully inside me, he froze. I could tell by his face the sensation was beyond anything he'd ever dreamed. As for me, while I was barely more filled then if I was being fingered, the naughtiness of what I was doing aroused me as much as if I was filled completely. I continued to lubricate, and my juices leaked out around Dilion's cock.
"Move in and out of me," I told him. "Over and over."
He started to do so, bouncing on top of me, and I felt the short stabs each time he rammed back into me. It was a strange feeling, because each time he pulled halfway out of my vagina, I barely noticed he was gone. But when he suddenly pressed back in, it almost seemed to double the pleasure. I wasn't sure I would be able to cum, at least not before he did, but this felt unlike anything else I'd felt during sex. Moaning my pleasure, I urged Dilion on.
Dilion kept up his motion inside me, and I felt the start of a climax building in my cunt. The tight feeling in my stomach now moved down, and held at the mouth of my womb. I loved this feeling, as it always meant an incredible orgasm.
Bouncing faster, Dilion speed up inside me, and I felt him start to tense. I knew if I didn't cum soon, he would, and I wanted to cum with him inside me so bad. He's cock slid in and out of my cunt, and the juices surrounding it made sucking sounds with each thrust. The bouncing of his body mashed my boobs, causing extra stimulation. I moved Dilion's hands from beside me, to the sides of my tits, so that he could message the parts of my breasts not being ground against his chest. He rubbed his hands over my tits, and squeezing and kneading them, causing me to shudder.
Dilion's body was tense, and I knew he was moments away from what might be his first every orgasm. I wanted to cum so bad, and I knew it would have to be soon, if at all. Wrapped up in my arousal, I couldn't resist talking dirty.
"Ohh, do you like it? Do you like my pussy? How's my pussy feel, huh? How's it feel putting your cock in my pussy?"
"I... I... like it..." Dilion breathlessly replied.
"Oh yeah? You like my wet pussy? I'm so wet, God, it feels so good!"
Dilion's bouncing reached a fever pitch, and I felt the tightness inside my belly grow, getting almost painful. I moaned loudly.
"Ohhh, fuck your babysitter," I said. "Oh god, it feels so good OOH! God, make me cum, make your babysitter cum!"
This seemed to make Dilion move faster, fucking me harder and, it seemed, even deeper then he had been before. His pubic bone mashed the top of my cunt, rubbing against my clitoris. I felt that felling deep inside me burst out, and I was cumming. My cunt filled with pleasure and my vagina spasmed, frantically massaging Dilion's cock with its rippling walls.
"Ohhhh Goddd!" I cried as my orgasm poured out of my pussy and through my body in waves. As I was still cumming, I felt Dilion go completely tense, and his cock shake inside me. A small burst of fluid left it and it mixed inside me with my own juices. He collapsed; limp, on top of me, just as my orgasm began to subside.
Dilion pulled his twitching cock out of my vagina, grasping it as if in pain. It was red, and wet, and he rubbed it, as if it itched. I knew the feeling, and I softly massaged my cunt, basking in the after glow of one of my all time best orgasms.
"Thanks" Dilion finally said, and he started to get dressed. I did too, and just had put my top back on, as Dilion, now fully clothed again put away the magazines.
"The reason I came up here was to tell you dinner was here," I said.
"Oh!" Dilion said, and we both laughed.
We went down stairs and eat now-cold pizza, but it tasted great anyway. After that we both watched TV until bed time, at which point Dilion went up stairs, laving me along in the family room. A few hours later, the Leinden's got home.
"How was your evening?" I asked them.
"It was great," said Mrs. Leinden "How were things here?"
"Oh, they were fine" I said, getting up, and walking over to her "Dilion and me watched TV until bed time, and that was about it.
"Good to hear" Mrs. Leinden said, "Paul will talk you home and pay you. Do you think you'll be able to do this again sometime if we need a sitter?" she asked.
"Sure, I think that could work," I said with a smile.