A Bit of an Unusual First Time - Cover

A Bit of an Unusual First Time

by Wayne Gibbous

Copyright© 2026 by Wayne Gibbous

Erotica Sex Story: I loved peeping over the fence at Cheryl next door when she suns herself in her bikini. Then one day, she catches me and makes me pay the price. Well, what idiot would object?

Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa   Consensual   Fiction   Anal Sex   First   Masturbation   Oral Sex   Voyeurism   Menstrual Play   .

Well, I’m a fifteen-year-old virgin guy. You would do the very same thing, right? Our neighbour, Cheryl, a pretty, blond college student, often sunned in a vanishingly small bikini out back by her parents’ swimming pool. She would lay there, in the hot sun, shiny with oils and work on her delicious tan.

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 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, wearing her tiny red bikini.

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, and she’s right here in front of me in the flesh, with all the appropriate smells that are not printing ink.

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, I was surprised to see Cheryl right there peeking over the fence watching me with a highly amused look in her eyes. She must have gotten up and seen the top of my head, then came over to the fence and looked.

I was mortified. I immediately ducked down in a crouch trying to shield my dick from sight, hoping against all odds that she wouldn’t be angry and tell my parents.

“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.”

My jaw dropped. That couldn’t be what she said. Girls usually took every chance to embarrass a guy and gain the upper hand on him. But the tone of her voice sounded not angry at all.

I got myself zipped up. I was so embarrassed, but she seemed all normal-like, so I went round and into her yard and stood like an idiot, not knowing what kind of humiliation ritual she had in mind for me.

She sat back down on her chaise and patted the cushion next to her.

“Don’t just stand there like that, come, sit next to me.”

I was still apprehensive, but when a beautiful girl like her invites you to her side, it’s hard to say no.

“Robbie, you have a very nice-sized dick for a young guy. How old are you?”

“Fifteen,” I squeaked out.

“Mmm, yes, nice. Now don’t rub it until I get back,” and she got up and went into her house.

I just sat there like the dumb idiot that I was for jerking off while watching her without taking any precautions against getting caught. I was just standing there like a retard jerking my cock in plain sight.

When she came out, she had a couple of towels and a tube of some sort.

“Take your shorts and briefs off, Robbie, and lie 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 lie down, I’d be crazy not to do it; and cooperation usually led to less anger and punishment.

I pulled down my clothes, revealing my now shriveled cock, and took off my shirt. Once naked, I could see Cheryl’s eyes take me in and linger at my cock. My treacherous cock started getting hard again under her gaze.

“Lean back,” she said in an even tone.

As I leaned back, my dick was now hard and up in the air like a flagpole. Cheryl reached over and began spreading some of the jelly from the tube on my dick. Smoothing it up and down. I almost shot my wad right there.

“Feel good, Robbie?”

I couldn’t believe that my beautiful neighbour that I watched for many years was actually gently jerking my cock using some jelly that made her gentle hand slide so smoothly over every part of my cock.

“Oh, it feels wonderful.” I was still cautious, but so far things have proceeded better than I ever hoped for when I was caught.

“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. Her finger began fucking me in and out of my butt, reaching and massaging something there, 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.”

Cheryl pulled her finger out of my ass and looked at me with that amused look in her eyes, now mixed with a mischievous twinkle.

“Oh, Robbie, there’s a lot I bet you don’t know,” she informed me 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, then let them drop unceremoniously to the deck.

Oh, my. I couldn’t believe my eyes. 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, flaring out to wide hips full of promise, and split right in the middle with a luscious, rounded slit in the middle. She had what I called a fat pussy, with no inner lips sticking out. She was the equal of any girl in Playboy; I’m sure she could get paid a lot to pose in those magazines.

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?”

With a shaking hand, I approached her presented asshole and gently smeared the jelly on her crinkled skin. Before that day, I had never even seen a naked girl in front of me, well, except my little cousin when we were seven, and here I was, before touching a pussy, lubing a beautiful woman’s ass.

Bit by bit, I lubed the proffered orifice, and pushed my finger all the way inside, spreading the heavenly concoction as deep as my fingers went.

 
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