Well, I'm a fourteen-year old guy. You would do the very same thing, right? Our neighbor, Cheryl, a pretty, blond college student often sunned in her bikini out back by her parent's swimming pool.
I know, I know, you wouldn't look, right? You wouldn't take a peek. Sure, and you wouldn't pick up a hundred dollar bill up off the ground, either. Right.
I sure did. No, not the hundred dollar bill, Cheryl. In her bikini. Yes, she looked very good. Kind of short, medium-length blond hair, nice figure with, oh, I don't know all the boob sizes. Let's just say, they look just right, um, like half a grapefruit, maybe. But sure sexier than grapefruits. Oh, yeah.
So, I would always take a look out our kitchen window when the weather is nice and this particular summer day, she was stretched out on a chaise.
Whenever I spot her outside, I try to sneak out the back door and over to their fence where I peek over a slat that is a little shorter than the others and see what I can see. In the last month or so, I have started jacking off as I watch her through the fence; it's even better than my stash of Playboys, she really is beautiful.
So, I stood there with my eye at the fence trying to imagine what Cheryl might look like naked, without those small bits of cloth covering her nipples and pussy. And, yes, I was stroking myself pleasurably as I watched and dreamed. I could feel my cum rising and closed my eyes as the tingle began to spread, oh, yes, mmm, this just felt so good.
Right before I ejaculated, I opened my eyes and, omigod, there's Cheryl peeking over the fence watching me. She must have gotten up and seen the top of my head, then came over to the fence and looked.
I immediately ducked down in a crouch trying to shield my dick from sight as she said, "There's nothing to be embarrassed about, Robbie, I don't mind you looking. Why don't you come over? I'd like to talk with you about something."
I got myself zipped up, I was so embarrassed but she seemed all normal-like so I went round and into her yard and sat down next to her.
"Robbie, you have a very nice-sized dick for a young guy. How old are you?"
"Fourteen," I squeaked out.
"Mmm, yes, nice. Now don't rub it until I get back," and she got up and went in her house.
When she came out, she had a couple of towels and a tube of KY Jelly.
"Take your shorts and briefs off, Robbie, and lay down on the chaise lounge."
I wasn't exactly sure where this was all going but I figured that if a pretty girl is asking me to take my pants off and lay down, I'd be crazy not to do it.
As I leaned back with my dick up in the air, she reached over and began spreading some of the jelly on my dick. Smoothing it up and down almost shot my wad right there.
"Feel good, Robbie?"
"Oh, it feels wonderful."
"Well, try not to cum for a few minutes, okay?" as she put some of the jelly on her other hand and started rubbing it along my butt up in my crack. Then, I felt her finger enter my asshole. He finger began fucking me in and out of my butt as her other hand jacked my cock up and down. Try as I might, there was no way I could postpone cumming and my semen began spurting up out of me like a geyser.
"UNHH, UNHH, UNHH, uhh, uh," as I arched my hips up as she shoved her finger all the way up inside.
"Wow, Robbie, good cum. Look at all that. I really got you off good, huh?"
"Did you ever. That was the best cum I've ever had. Never expected it like that, you know, with a finger up my butt."
"Oh, Robbie, there's a lot I bet you don't know," as she wiped my cum off me with a towel.
"Gee, you're still nice and hard. I like you young guys," and she stood up and untied her bikini top and bottom and let them drop to the deck.
Oh, my. I had dreamed of seeing Cheryl naked, now she stood before me stunningly and beautifully unclothed. Her breasts were firm and round with small red-brown nipples that were pointed out to each side a bit. They were perfect.
Her waist was slim, hips full of promise and split right in the middle with a luscious, rounded slit in the middle. She was the equal of any girl in Playboy.
Her skin where her bikini had been was pure white, almost glowing, as she turned around, bent over and put her bikini on the table. While bent, I could see a string hanging between her legs, a tampon string.
"I'm having my period right now, Robbie, in fact it's my heaviest day, but I'm so horny I've just got to have your cock. I'll just die, otherwise. So, here," and she took a glob of KY Jelly on my finger, bent over and said, "Rub it on my butt hole, then all around up inside, go in and out, okay?"
After I had lubed her inside, she asked me to lay down on the chaise and she straddled me backward as she slowly lowered herself onto my dick wiggling around to work her ass hole down over me. As she slid down over me, the feeling was tight, really tight. Then she began to rock up and down.
"Oh, Cheryl, that feels so good. I never thought about doing it like this but it's so good."
"Have you fucked a girl before, Robbie?"
"Um, well, not really."
"Geez, and here I am finger-fucking your ass to make you cum and then taking your cock in my butt. And, you're a virgin. Never been fucked."
"Yeah, but, that's okay, I love doing this. I hope we do more."
"Well, you're starting out in the advanced classes before you even get 'Fucking 101.' We'll have to make sure you get a full course. Bet you'd like that."
"Oh, would I ever," as she pulled up, then pushed back down. Oh, this felt so good. Then it hit as she pushed down hard on me and twisted her butt back and forth.
"UUHM, UUHM, UUHM, uh, uh, oh, wow, oh that's feels so good, just keep going, don't stop."
"Not as long as you're hard. You feel really good in me. Mmm, oh, I'm really slippery now with all your cum in me. Now I can go faster. Mmm," and she rocked faster and faster.
"Oh, oh, yeah, oooh, my turn, mmm. UUH, UUH, UH, uh, oh, yeah, mmm. Oh, that's really good." She went on for a few more minutes, it just felt so good and it kept me good and hard.
Then, she pulled up off me and when she stood up, I could see my cum dribbling out of her butt as she bent over facing away from me, spread her legs and reached back up under her and wiped off her butt.
Then, as she turned around, I was so turned-on by her wiping her butt that I was giving myself a few strokes.