Hailey said yes! Three weeks of hanging around her delinquent friends paid off. Friday night, I will take her to the movies, and hopefully get lucky for once in my life.

We lived next door back when. Hailey and I played together, ran around the neighborhood, you know, kids’ stuff. She was an adventurous tomboy; I was shy. We complemented one another. Never any kissy-kissy. One time in second grade we skinnydipped in the creek, but that was no big deal. We were just friends. She moved across town the summer before junior high, after which I never saw her. That is, until senior year.

The school district reorganized, and we ended up in the same building again. Hailey wasn’t the outgoing, pigtailed blonde I remembered. She went goth, with dark clothes, smoky black eye shadow, white powder on her face, fishnet stockings (when we weren’t in school). Your standard alternative uniform for the time, though I don’t remember other girls wearing nighties for a blouse.

Hailey earned a reputation, too. Brad Sanders claimed she gave him a blowie in the woods behind the game field. Steve Torkelson said they fucked. Public displays of affection passed between her and members of her goth circle. She would drape herself over different boys depending on whom we all guessed she was doing that week. She’s always flirting by showing off her midriff. I’m not sure what it is with her, but she’s proud of her flat belly.

When I talked to her, which was rarely, I invariably smelled cigarettes, and occasionally weed or booze. Mommy doesn’t let me do stuff like that. She keeps a watchful eye, and if I ever turned up smelling like Hailey, she’d tan my hide. I’m not even allowed to hang out with girls. Mommy doesn’t want me throwing my life away before college like she did with dad. I never heard whether dad felt the same, because he was gone before Hailey and I even met.

For this reason, my sorta-girlfriend Darla had to be kept on the downlow. Darla and I made time when we could. Nothing past first base. Unlike Hailey, Darla smelled and tasted like peppermint. (That’s her gum.) She has perky melon tits, whereas Hailey’s flat chested. (I called them misquito bites back in our skinny dipping days, which prompted her to sock me in the arm. Apparently they never grew.) I was always worried Mommy’d find out about Darla and embarrass me.

Pete, a friend Mommy gladly let stay over at the house, suggested I stand up for myself and tell Mommy I’m the man of the house and deserve to get some. His big joke was that if Mommy wouldn’t let me have a girlfriend, she should take care of me, if you know what I mean. Gross.

Standing up for himself must’ve come easy to Pete, because he went behind my back and fucked Darla the weekend I went with Mommy to the apple orchard. It was just as well; Darla was getting fat. Except I cried a little because I knew I probably couldn’t get Darla back if I wanted to. Pete showed me his penis once, just to brag, and it’s twice as big as mine. I refused to show him mine, which he interpreted (correctly) as insecurity. Darla wouldn’t want to be with me after Pete.

Seeing Pete’s manly cock was a traumatic experience, I guess. It led me to shed my usual modesty and ask Mommy if I should go to the doctor to see if I have a problem down there. She asked to see it first. Showing Mommy my penis wasn’t what I had in mind, but she insisted. I flashed her as quickly as possible by pulling down my jeans and underwear, on account of it being too short to pull through the fly.

After giggling a bit Mommy said we should wait and see if it grows. I was to take measurements with her sewing tape and record my progress. I discovered I am 3.75 inches hard. Mommy checks in periodically to ensure I keep track. The numbers stay the same.

Pete and Darla’s betrayal left me no one with which to hang. They were my only friends. High school is a lonely place with no friends sit by or talk to. Despair descended, but it broke when I got the bright idea to pursue Hailey by hanging with the goth crowd. She is literally the only other person at school with whom I had ever been friends. Plus, she’s hot.

Allow me to elaborate: short and lithe, with a bit of jiggle around the ass thighs, Hailey’s once blonde hair is jet black. As mentioned, her tummy is flat and she has no tits, and there’s acne all over her face. But she’s cute, and she has a sexy, low smoker’s rasp.

Wasn’t easy getting close. She was surrounded by guys at all turns, and going goth brought me in for extra teasing from the cool kids. Mommy helped me apply guy-liner and pick out vintage clothes to fit in with my new crowd. She called it dress-up. Argh!

Eventually, the effort paid off. Hailey and I sat next to each other at lunch two days straight, and I asked her for a ride home. I cleared this with Mommy ahead of time, and she told me that if I wanted to ask Hailey out, I should. Though Mommy had seen Goth Hailey, to her Hailey’d always be Little Hailey from next door. What harm could come from a date between old friends?

I propositioned her with as much confidence I could muster. Mommy told me confidence in men is most attractive. Hailey said, “Yeah, whatever,” and my heart sang!

*****

Tonight is the big night. I step out of the shower to dry myself off. Mommy had laid the outfit we chose together on my bed, and I can’t wait to shave, deodorize, and put it on. Just then, the locked knob turns, and there’s a pounding on the door:

BANG, BANG, BANG!

“Open up, young man!” calls Mommy’s voice.

“Ma-aaa! I’m getting ready!”

“I know, open up.”

I let out a frustrated sigh. “Okay! Just a minute!”

She bangs again while I cinch the towel around my waist. I unlock and open the bathroom door.

“Shit,” she says. “I wanted ta catch you before your shower.” Mommy is back from her waitress shift, her pink uniform tight around the chest and hips. More tips that way, she says. (“Tips for hips.”) She works at a bar and grill with a predominantly male clientele.

I stand in front of her, still damp. “Listen, you remember what I said about staying out of trouble,” she says.

I don’t need this lecture now. “Yeah, yeah…”

“Don’t ‘yeah, yeah’ me. This is serious business. You’re not throwing your life away over some hussy.”

“I won’t, ma. It’s only Hailey.”

“Still and all, I’m not sending you out with a loaded gun.” What is she talking about, I wonder. “Did you have happy time today, son?”

“Happy time” is our term for jerking off. I know what you’re thinking: most families don’t have a special term for jerking off. Not my idea. Mommy coined the phrase when she discovered some of her best washcloths were missing.

“Maa!”

“Well?” Mommy isn’t playing. I brush past her on the way to my room, refusing to answer. “…I’m waiting,” she says, following me.

“No, okay. Geez,” I respond without turning my head.

From inside my room, I pull the door shut, but her leg is in the way. I hit her in the thigh, where a line runs up her nylons. She wears those things out constantly. Gotta show off her “gams,” as she calls them, under the short skirt of her uniform.

“Don’t ignore me,” she says sharply. “I have to make sure you hop-to, buddy. You didn’t leave yourself much time.”

“I might be dressed by now if you hadn’t interrupted me,” I say indignantly.

“I’m not talking about getting dressed. I mean happy time. You have to have happy time before your date.”

“Whaat?” I can’t believe what she’s saying. Mommy has never ordered me to have happy time. Gross.

“I said I’m not sending you out there with a loaded gun. Next thing you know, Hailey will be knocked up, then I’m stuck raising your brat.”

This is too much, even if I’m temporarily turned on by the thought of Hailey and I making a baby. “That’s crazy, there’s no…that’s not how it works.”

“Plenty of guys do it. Frank told me he did happy time before the first time we went out. Calls it ‘cleaning the pipes.'” She laughs. Frank is Mommy’s stupid boyfriend. He picks her up after her shift on odd nights, and Mommy doesn’t come home till late.

“No. I’m not doing happy time. Leave me alone.”

“It’s not your choice, hun. Happy time is gonna happen.” I think about pushing her back and slamming the door, but I can’t do that to Mommy. She isn’t budging on her own, so I plop down on my bed in a huff.

Mommy saunters over to my bed, hips swaying, and sits next to me. To calm me, I guess. I am fuming. I don’t even look at her. Then I feel the towel pull away from my body. I look up. Mommy’s heavily blue-shadowed eyes stare at my exposed penis, which is in turtle shell mode. I shift uncomfortably, and Mommy says, “Shh. Let me.”

I can’t believe it! Mommy touches my penis. I freeze, unable to process.

Her long, white fingernails lightly scratch my freshly clipped ball sack. I wonder if Mommy knows I groomed myself for Hailey, or if she thinks I’m naturally bald as a baby. I had hair when I showed her last year, but not much, and she didn’t look closely.

It surprises me that I don’t resist. Mommy plays with me, but I’m too nervous to get hard. Our bodies are close. Her breath smells like cigarettes, the same as Hailey’s. (Mommy takes smoke breaks every hour at the restaurant.)

Smelling the smoke and thinking about Hailey makes me hard.

“There’s a good boy,” Mommy says. I don’t know if she’s addressing me or my penis.

Mommy is particular about her coiled red hair. Every Thursday is salon day, another aspect of her professionalism in appearance. I think about that because it gets in my face as she leans down to spit on my crotch. Eww, mom spit.

But I forget my disgust half a second later. Mommy starts jerking me. My first handjob.

“Won’t take long if your father’s any indication,” says Mommy with a smirk. I watch her pink lips (to match the uniform) curl. We’re face to face. Her already wide nostrils are flared. Dad told her she has a black woman’s nose, I’ve been informed. She tells me stories about how mean dad was often, as a lesson in how not to treat a lady.

Her uniform is unbuttoned on top, and Mommy’s large white breasts show above her red bra. I wonder if those get her any tips. I’ve seen Mommy’s breasts before. Sometimes she has me talk to her while she’s taking a bath. Her nipples are bright pink, like her lips, and she has a big red bush. None of which I find sexy. She has a mom’s body, not bad for the late-30s, with mom boobs. Which flop around and don’t maintain their shape. Unlike Darla’s, I’m sure, though Darla never let me see them. Hailey’s have no shape to speak of.

Mommy has been stroking my penis for a mere two minutes or so. I have no basis for comparison, but she seems very skilled. Takes me 15 minutes at least when I’m alone, but I’m already close.

“Come on, hun. Let Mommy have it.” Must she talk like that? It interrupts my fantasy about skinnydipping again with Hailey, now that we’re both 18. “I wanna see the little guy shoot.” Mommy never called my penis a little before. The day I showed her, it was implied but she wasn’t explicit.

“Shoot that nasty stuff from your little pee-pee.”

That is enough. I cum the hardest I’ve ever cum. Mommy calling my penis a little pee-pee sent me over the edge. I don’t know why.

“Good boy,” she says. Mommy caught most of my stuff in her free hand. The rest shot onto my stomach and flowed down the fingers still wrapped around my pee-pee. My mum matches her long, white fingernails.

I lay back, dazed. Mommy rolls me over and grabs my towel to wipe off her hands. “There,” she says, leans in, and kisses me on the lips. Not something we normally do, either. To my utter shock, I get hard again. Usually, I’m spent for a good half hour after shooting.

Mommy notices my boner as she leaves. “If you need happy time again, do it yourself, hun. Don’t let’s make a habit of this.” She blows a kiss, winks, and exits my room.

I am lost, a mere 10 minutes from Hailey’s scheduled arrival. (She is to pick me up because she’s the one with a car.) I get up, put on some underwear, and wander into the hallway, not sure what I’m looking for. I cross in front of Mommy’s room. Her uniform is on the floor, and she stands in her nylons and transparent red panties. I can clearly see the crack of her plump ass. Her bra is half off.

Mommy turns. Her droopy boobs fall out. Hailey is nowhere near my thoughts. My boner tents my undies as I stare at my topless mother. What had she started?

The End.