Kyle's Story - Book One - Cover

Kyle's Story - Book One

Copyright© 2024 by JTrevor

Chapter 17: Summer Dress

Coming of Age Sex Story: Chapter 17: Summer Dress - Kyle's Story is that of a young man's coming-of-age adventures in high school. Although not an autobiography, the author does draw from his own experiences and personal feelings, with small, slice-of-life moments that form rich ingredients for storytelling. If you’re looking for a fun, erotic, coming-of-age story with relatable characters, then Kyle’s Story may be for you.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   Teenagers   Consensual   Romantic   Heterosexual   Fiction   School   Cream Pie   First   Masturbation   Oral Sex   Petting  

The following day, I told my parents, Luke, Tiffany, and my closest friends that everything has been settled peacefully. I explained how Benny retrieved the video proving Dirk was the one who damaged my Jeep, and that I choose to deal directly with him. My mother and Tiffany thought I should have simply sent it to the police and not taken any risks of further confrontation. Dad wasn’t crazy about my approach either, but he respected my choice.

What I did not tell any of them about was the other video, or what Dirk and I talked about at the gas station. Dirk confided in me in his interest to make things right and I will respect that. I’ll talk to Donny about this, but I know he’s going through a rough time right now.

At school, I pass Dirk and his friends in the hall. He makes a subtle and slight nod in my direction, I return the nod. I’m trusting he will come through with covering the costs he incurred and he is trusting me to keep quiet about the videos.

In Modern World Studies class, I notice Tyler seems a little pissed about something by the way he is pounding texts into his phone. I find it funny how hitting one’s phone screen harder somehow emphasizes anger, like the other party can somehow see this. We all do it, but it’s humorous to witness. My guess is that he just learned he has two less boyfriends today.

On my way to lunch, I see Donny leaving the school building. I call out to my friends that, “I’ll catch up later,” and to, “Have lunch without me today.”

“Hey, Donny, wait up!”

“Oh hey, Kyle.”

“Are you heading out to lunch?”

“Yeah, it’s a nice day, I was going to eat outside on one of the benches. I don’t feel like being in that lunchroom today.”

“Why don’t we go get a burger at Murphy’s or something?”

“Do you think we have time for that?”

“I don’t know ... so we miss 4th Period,” I shrug, “No big deal.”

“Okay.”

Murphy’s appears to be senior citizen central at lunch time too. I take a quick look around, but don’t see my old friends the Kransens as Donny are I are seated at booth.

“How have you been doing? Are you holding up okay?” I ask.

“Yeah ... I’ve been better though.”

“I know this won’t make it things any better, but I don’t think Tyler was just messing around on you with Dirk.”

“Why do you say that?”

I tell Donny about how I got Dirk’s cell number from Tyler’s phone and that I saw he was exchanging dick-pics with some dude named Brandon, talking about hooking up.

“Dirk did not know you and Tyler were, you know, together, when we found them the other day.”

Donny nods, “Still makes Tyler a cheater and a shit.”

I tell Donny about Dirk wanting to come clean with me, and how hopefully things will be better now. Donny seems happy for me, but it doesn’t help him much, a broken heart is a broken heart.

“I didn’t text or call Tyler for the last three days, and you know what? He didn’t bother to contact me either. Not even to say ‘hi’ or anything.”

“What are you going to do if he does?”

“I don’t know, probably just ignore him at this point, I’m so done with him...”

“I’m sorry this happened, I feel bad for you.”

“I’ll be alright, Kyle, just need some time, you know?”

“Yeah...”

We change the subject and get into some good ‘ol gossiping about other people like a couple of old women. Those that say, “guys don’t gossip, that’s a woman’s thing” are full of shit, guys gossip as much as anyone. A few laughs we share seem to help Donny get into a better mood, a little bit, at least. We finish our lunch and make it back to the school halfway through 4th Period.

On Friday, I get a text from Dirk while I’m in 3rd Period, telling me to check my locker. Inside, I find a white envelope with $500 cash, he was good on his word.


On Saturday, I pick up Tiffany and we go to the Spring Haven Mall. I need go to President Tuxedo to get measured and pick out a tux I will be renting for the prom. A, very proper, gentleman by the name of Charles is helping me. He shows us several different styles and we decide on a nice, traditional, black one that will complement the dress she plans to wear.

With that decision made, the next step is to get my size. “Please stand perfectly straight while I take some measurements.”

Tiffany has a seat nearby and watches as Charles uses a tape-measure to measure my arms, legs, waist, chest and neck size. “Okay sir, very well,” he says, jotting down the numbers. “And, what side do you dress down on?”

Huh? Dress down? What the hell does that mean?

I hear Tiffany quietly giggling behind me and look over at her, confused. I have no idea what he’s asking. She gets up and whispers in my ear, “He wants to know-” she has to stop to giggle some more, “He wants to know what side your cock dangles on.”

I’m sure I made quite a look of surprise. Okay, then, I’ve never really given it that much thought before and I never, in a million years, expected to be professionally asked how I hang. Without trying to be obvious, I lightly pat myself, seems to hang straight down.

Now I’m curious, I go in for a little more nonchalant self-groping to try to determine just what side, if any, it does favor. While I’m standing here, having a little feeling-up session with myself, Tiffany is covering her mouth to keep from laughing, but some snickers still slip out.

Charles patiently waits, looking up, and all around, making sure everything is fine with the ceiling. I’m sure a couple of childish teenagers, giggling about which direction my penis prefers to dangle, had to be the highlight of this poor guy’s day.

“To the right ... I think?” I finally answer. I can’t help it anymore and I have to turn momentarily away, I’m fighting to keep from bursting out laughing.

“Very well, sir...” he sighs, and rolls his eyes.

Charles sets up a day and time for me to come back and pick up the tuxedo. Once we’re out of there, we both break up into laughter. “Why did he need to know that?” I ask.

“I think they make one pant leg wider to accommodate your big package,” she winks at me.

“Really? I’ve never heard of that...”

“You looked so funny in there, groping yourself,” she laughs.

We stop to get some cold drinks, there is small line of people ahead of us. Tiffany turns, puts one arm around me and stands on her tippy toes to kiss. Out of sight of the other customers and between us, her other hand finds my bulge. She playfully rubs and squeezes. whispering, “I liked watching you grope yourself, can I grope too?”

Well, damn! Now, I’m all fucking horny, and she has more shopping she wants to do. Look what you started, thanks a lot Charles!


Tiffany and I spend a couple of hours going to a bunch of girly stores. I’ve been patient and a good-sport about it so far, but I’m getting pretty bored at this point and starting to show it.

“Can we please just GO already?” I whine like a child to his mother.

“Just one more, okay?”

She finds a summer dress she likes at Forever 21. “I want to try this on. Can you tell me if it looks good? Then we can go, I promise.”

“Okay, but hurry up.”

There’s an opening leading to a small hallway with a row of dressing rooms. At the entry, she stops and appears to be listening. I don’t know what she is expecting to hear, there’s no other customers in the store, so I’m sure all the dressing rooms are empty. Tiffany motions for me to come over and holds a finger to her lips for me to be quiet. She has a look like she’s listening for something funny. What, is there someone getting a blow-job or something in one of the dressing rooms, I think to myself.

She takes my hand and leads me to the end room. We go in, she locks the door and sits on the small bench seat in the corner. I’m not so sure I’m supposed to be in the women’s dressing rooms. She looks up at me, biting her lower lip. I mouth the word, “What?”

She points at my- Ahhh, now I get it! Someone is going to be getting a blow-job in the dressing room today. I never fail to amaze myself when I completely miss the obvious.

I undo my jeans, let them fall and pull down my underwear. She examines me with great interest. “Yep,” she whispers, “It tends to favor the right by a little bit.”

She strokes me a few times, then takes me into her mouth and begins to play. To my right is a full-length mirror, this gives me an awesome view, a whole new angle to watch. My entire cock is in her mouth and getting very hard, very fast. Up and down my length, she slides her lips. I see her eyes turn as she catches a glimpse in the mirror.

Tiffany grabs a handful of each of my ass-cheeks and pinches them, pulling me to herself. I find this so kinky, and so sexy, doing this in here. Heavy breathing on my part has begun, this feels so good. She pulls off with a small wet smacking sound and whispers, “Let’s see how quietly you can cum.” Here’s a test I’m going to enjoy.

She goes right back to sucking me and sucking really hard, so hard, I can feel the skin on the underside of my balls being pulled taught. A couple of loud pwah sounds happen as her lips reach the end of my cock and the suction is broken.

“Just let me try these on, I’ll be right back.” I hear a woman’s voice from the entry area to the dressing rooms. Oh great, someone’s coming in here just as I’m getting close to cumming in here. (There’s a play on words I couldn’t resist.)

I know Tiffany heard what I just heard. Attached to me, I can feel her giggling, but she has no intentions of stopping. Part of me feels very awkward to have some woman, just a couple of rooms over, while I’m here getting seriously sucked on. The other part of me finds this kinky as hell and I love it. I’ve heard about people having sex in unusual places with the possibility of getting caught, and now I’m beginning to understand how much fun it can be.

The view in the mirror is so erotic to me, I love seeing my cock, glistening with saliva, repeatedly appear and then disappear into Tiffany’s mouth. She takes care so no more of those pwah sounds accidently escape. When she nears the tip on the out stroke, she slows down and I feel her lips tighten up around that narrower part just below my cockhead (the glans, as it’s technically called).

All of this sucking, and sliding, soon has me utter a tiny, “ohhp!” as I let loose with my ejaculation. Tiffany’s hands firmly grasp my ass cheeks to help steady my body; you know me and my issues of quivering knees, wanting to give out on me when I cum standing up.

Tiffany slows the sliding up and down on my shaft motion while I’m throbbing and surge-releasing. She sucks very intensely, pulling everything I have right out of me. Wow, does this ever feel good! I almost bite through my lower lip, stifling the moans I want to make. It sure is strange knowing some woman is in the other dressing room, trying on clothes as I’m here, pumping streams of cream. As I slow to a finish, Tiffany, carefully, and without a sound, slides herself off. She wipes her lips with the back of her hand, grinning at me.

I get down on my knees and lean in to kiss her, there is no mistaking the mild scent of my semen on her breath. She reaches behind my head, pulls me to her and opens her mouth over mine. As we intimately kiss, I don’t pull back (as some guys might), from the slightly salty reminder that if it’s good enough for her, then it sure won’t hurt me.

I motion for Tiffany to take her pants off; her face brightens as she undoes her fly. No need to be extra quiet about taking clothes off in here, that is what these rooms are for, aren’t they?

She takes her jeans and panties off and puts her hands around her knees, acting all coy. I gently open her legs like an extra special gift; such a picture-perfect, beautiful little pussy awaits me in there.

Starting at one knee, I lick her inner thigh in a crazy, swerving line, moving in towards her special place. Just as I’m close enough to feel her radiant heat emanating, I pull back and focus my attention, starting at her other knee and moving in. Her thighs are so silky, soft and smooth, I love to run my tongue along their inner surfaces. Doing this multiple times, just to drive her wild, I finally move in and kiss her sweet pussy. I look up and whisper, “Let’s see how quietly I can make you cum.”

She nods a very enthusiastic affirmative. I start by nuzzling and tickling her with the tip of my nose. Using the pointy end of my tongue, I slide it into her slit, starting at the bottom and licking all the way up to her pubic area above. I follow that with some playful kissing all over her girl lips, they are already becoming quite wet.

“Ooohhh-Mmmmm,” I hear her delicately moan.

“Shhhhh...” I hush her.

I reach behind and grab her butt-cheeks, drawing her to me. It’s time to plant my face in her flower and go to town.

A couple doors down, it sounds like the unknown woman is done trying on her clothes with no clue as to what is going on just 15 feet away.

I tease and lick her clit, sliding my tongue up and down her length. Pushing it in deep, into her hole and wiggling it around causes her to grind her hips a little bit. What really gets her grinding away and pushing herself at me, is when I suck on her hard, little clit. She’s plenty wet and my face is now covered with her sweet juices.

“I love seeing your head between my legs,” she whispers/giggles. She must be enjoying the sexy view in the mirror like I was a little while ago. If that’s a two-way mirror, by chance; someone is getting one hell of a show today.

Fast breathing, becomes panting as Tiffany begins to climax. She grasps the back of my head and pulls me in tight, she doesn’t want me anywhere, but right here, with my face firmly in her pussy. I’m not sure which maneuver she’s liking best, so I’ll just do them all, licks, flicks, sucks, pokes, swirls and twirls.

“Oh, oh, oh, oh, oooooohhhh...” she quietly squeals in between pants of pure pleasure. If someone was just outside our door, they may have heard the muted ohhing and ahhing; but at this point, who cares? If we get in trouble, this is sure worth it!

With some deep, long breathes, Tiffany recovers, “Ooh-oohh, that felt soooo good...,” she whispers.

We kiss as passionately as we did after I came, she giggles when I reach behind her head and open my mouth wide over hers, she knows exactly what I’m doing. She so lovingly shared mine with me, I can certainly share a little of her’s with her.

We start to get our clothes back on when she remembers the dress, “Oops, I almost forgot about this.” She tries it on and looks at me for my thoughts. It looks great, really cute on her; I give her a thumbs-up.

When we’re ready to leave, she tells me, “Stay in here, let me check if the coast is clear.”. A few seconds later she returns and waves me to come out.

At the cash register, a tall saleswoman asks, “Did you find what you were looking for, miss?” she asks.

“Oh, yes, I really did,” Tiffany answers and nods. I think Tiffany’s answer was more directed at me than her. This saleswoman looks familiar; when I see her name tag, I remember, it’s Alexandra. She’s the woman that helped me pick out Tiffany’s sweater I gave her for Christmas.


We’re driving home from the mall and my phone bloops from a text. I see it’s from Marc and hand it to Tiffany to see what the text is. I get so pissed off at how often I see other drivers not paying attention because they’re too busy screwing around on their phones. She reads Marc’s text: “Veronica is having a party tonight, she said I could invite my friends, wanna come?”

“What do you think?” I ask.

“I don’t know Veronica super well,” Tiffany shrugs, “But, I’ve never had a problem with her either.”

“Did she hang with the popular crowd?”

“I wouldn’t say she’s all into that group, but she is friendly with them. That girl is kind of her own group in itself, you know what I mean?”

“Yeah, she’s a force of nature all right...”

“I mean, if you want us to go Kyle, that’s fine with me.”

“We can check it out. Text Marc that we’ll come. Ask what time and for directions.”

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