# #

Anal Detention

1848 words | 2 |4.38

Continuing the series started with Headmaster/Headmistress, this would be chapter 3. You don’t have to read the previous two…

“Hey, boys!” The shrink’s assistant waved at us on the way out of detention hall, over by her car. “Need a ride?” A head peeked up, with a hoody up, the brim of a ballcap sticking out over the bottom of the back window, but it looked like they had a stocking pulled down over their face, as a mask.

“Hey,” my little brother grabbed one of the other boys, “Jake, right?”

“Jack,” he shook his head, while the other boys went up to talk to her. “What’s going on?”

I already had my keys out, “We’ll follow you,” I waved, and hit the button, to unlock my car.

“Hard to tell,” my little brother didn’t let him go. “You ever been to a circle jerk?”

“No, that’s gay.” He pushed him off.

“Well,” I had to laugh, “Not exactly. Not if there’s a woman with big tits to jerk off on.”

They were already mounted up, and driving off.

“Oh,” Jack nodded, “So more like a bukkake party.” I couldn’t see any hair, or anything except for the ballcap, and eyes peeking out, through the tight weave of the stocking. Like a thief, or more likely a boy that didn’t want anyone to know he was gay. Bi-curious, or just never been to one of these afternoon parties before.

Saturday school, I’m glad we didn’t get In School Suspension. Yeah, it sucks having to come in on a weekend, but then again. It’s also the best time for someone to cum pick us up, and she knows it.

“Too bad it’s not lesbos this time.” My little brother got in shotgun.

“So, you guys do, this sort of thing all the time?”

“Not all the time,” I went the other way, and waited for her car to pass. Pulled out behind her. She turned right, instead of left, so I didn’t have to pull across traffic to the other lane. Which narrowed down where she’d take us, but doing a quick head count. There was 5 of them, and 3 of us, with 2 cars, that eliminated a lot of places that weren’t big enough. “Every so often, there’s a kid. Usually a freshman that needs some sexual therapy.”

“Yeah, group sex therapy.” My brother laughed.

“So, I might get laid?” Jake asked, still looking back, and forth, nervously.

“Since it’s your first time.”

“It’s not my first time, hahuh!’ He laughed nervously, “I’m no virgin.”

“Now,” I patted the steering wheel, “I have to tell you not to brag about anything to anybody, and do you have a phone?”

“No, why?”

“Good,” My brother took over, “because we can’t have any pictures taken.”

“You won’t need it,” she turned, over to the next lane, so I signaled, and followed them. “I knew it!” The RV park, but the trailer she used wasn’t going anywhere. All 4 tires were flat, or would be if they weren’t hanging off the ground on jacks, cinder blocks, and plywood so they didn’t sink into the mud when it rained. “She’ll tell you all the rules when we get in, just keep your head down, and try not to act sketchy.”


Jack (Boys/f Teens. Fm Dom Exhib/voye Gangbang)

“Wow,” they sure moved quick.

“Take your shoes off, outside.” Most of the boys already had their pants down, and some of them were on the bench, pulling their legs out.

“Hey,” a woman grabbed me, “I’m Jan, I haven’t seen you here before. What’s your name?”

“Uh,” she pulled me back, to the stairs. Up to a sort of sleeping loft, over the 5th wheel. Or gooseneck, the fifth wheel goes on the truck, but this wasn’t one of those flat beds with fence sides to hold hay, or tote a tractor. It was more like a Mobile home, really.

“Huh!” There was a girl down there, pulling off a sweatshirt, and hat. Then, she pulled her mask out from her mouth, opened wide, and snipped it off with a pair of scissors.

“Your first time, big boy?” I shook my head, but the nurse lady. I think she was a nurse, or maybe nurse’s aide. Since I’d only seen her around the nurse’s office. She already had most of her top unbuttoned, and her jacket slipped off the end of the bed, when she scooted over. Sideways, so there was just room for a cabinet, and a lamp over it, stuck to the wall. “Don’t be shy.”

I got started on my belt, and unbuttoned my pants. Ripping over the zipper, and looking back to make sure nobody was looking at my ass, before I dropped them.

Fat chance, with a naked girl, standing around, and getting felt up. Well, mostly naked, except for the pantie hose over her head, like a mask. “What’s the mask for?”

“She doesn’t want everyone to know that she’s a slut, especially the other girls. She’s afraid they’ll pick on her if word gets out that she’s into gangbangs.” I heard a drawer, then she held up a bunch of condoms. “You want to just stand there, and watch?”

“No,” she tore off the top one, and dropped the rest back in the drawer.

“You know how to put that on?”

“Yeah, uh.” They didn’t cover it in health class, Abstinence Only, but my dad showed me on a hot dog.

“Huh, come here.” She clapped her fingers together, and rolled back. So her tits rolled, and bounced back, and forth in her bra. “Come on, don’t be shy.” She smiled, and rolled her eyes. “She’s right, virgins don’t know how to do anything.” I swallowed, but got close enough to pull out the front of my underwear, and my balls, to tuck the waistband under them.

She grinned, and looked up at me. “Huh! You’ve got a nice little dick.”

I shook my head. For a second there, i thought that, nice, and little. Isn’t that a contradiction? “You like it?”

“Yeah, not too big, not too small, just right.”

“Well, how big is too big?”

“Oh, don’t worry about satisfying me. It’s been a long day, so I need to loosen up, but if I need more, I can always take some of her sloppy seconds.

“Uhl gugh guk cuck!”

“Here,” she took the rubber back and tore her open with her teeth. She rolled over, and said, “See if you can figure out my bra.”

“Huh, no problem.” Just pull the ends together, and unhook them. “See? It’s a lot easier with both hands, from behind then trying to do it blind, through a shirt.”

“Oh, is that right?” She shook her head.

“Yeah, I guess you already knew that. Right?”

She nodded, “Now hold still.” I never got the deal with rubbers, or guys that didn’t like wearing one, until I felt the slimy layer cling to me, and wrinkle up around my dick. “Uh!’ I hunched, when she pinched it, and the tip slipped.

“A little sensitive?”

“Uh huh!”

“There’s a bottle, in the drawer behind you.” I turned back, and picked it up. Read Spermicidal Lubricant on the label.

“Yeah, suck it. Suck my balls too.”

Behind me, “Uh, all this sucking is fun, and all guys, but one of you wanna fuck me now?”

“Yeah me.”

“No me!”

“ignore them.” She rolled over, with her panties down around her knees, and her fingers sliding between her butt cheeks. “You like anal?”

“Yeah.” Never tried it. “You like it up the ass?”

“Huh, yeah. If I’m gonna get double fucked tonight, I better loosen up back there, first. Lay down, over here.” She got on top, and bent over, so wrinkles appeared in her flat tummy, but not like fat rolls. Not at all, but there was also a little sag under her tits, I pushed up to feel how soft, and heavy they were.

“Hhuh!” Then something tight.

“Uh, fuck! Huh!”

“Huh!” She smiled, but I could barely keep my eyes cracked. “HhuhH!” I barely even got it inside her hot tight asshole, but she slipped her fingers in, and I felt her knuckles. 2 of them, rubbing me through the skin between her pussy and her asshole. “Huh, uh!” She lay down on top of me, and I slipped out. ‘it’s okay. huh, it’s all right, at least you got it inside me before you jumped the gun.’


“I said it was okay. I understand.” She kissed my cheek. “Better luck next time, but there’s plenty of fish in the sea. You can throw the rubber in the trashcan, and wash up in the sink, in the bathroom.

She even helped me up, and I pulled the waistband out from under my spent nuts, as soon as I slipped the shitty rubber off. “Huh!” With another hunch. “Yeah, now it’s even more sensitive.”

“Who’s next?” She sat up, and I covered myself up, stepping out of the way, so some of the other guys could go up the steps.

Then, I found the bathroom, so I could wash up. No wonder they hate rubbers so much. That felt disgusting, and I think maybe it would be, a little more disgusting if I got shit on my dick, but I checked my underwear. As soon as I was done washing off my fingers, but luckily, I didn’t get any in there.

That’s all it was. It had to be just the rubber, and the shit that made my first time feel so gross.

Like she said, “Better luck next time.” Right?



Note: There’s a lot going on here, so I hit Others instead of Abuse, and Rape. That wasn’t just statutory Rape. Yeah, he makes excuses, and never thinks of himself as a rape victim. Her as a mass rapist, but there’s a reason why we have laws to protect underage kids from predatory adults in positions of power over them. Being a teenager doesn’t automatically come with the maturity to handle sex, let alone anal, with a gangbang right there to walk past on the way back to the bathroom, feeling dirty, and used. Boys just aren’t taught that. They’re not taught to think about their feelings, or how to process being victimized.

“I’m not a victim,” it’s like “I’m not a virgin,” only it’s not the kind of lie you tell your friends, in the boy’s room. It’s the kind of lie you tell yourself. “I just got lucky, right?”

Even if he does eventually realize what just happened to him, and then he does tell someone years later, and then gets the balls to admit to the cops that he was raped by a woman in high school, do you think they’ll believe him? When they don’t believe women when they come forward, even with males being the defacto abusers, and young girls the defacto victims, it never happened. Right?

Well, it does happen. Maybe not all the time, but it has happened. We just never talk about it. Denial doesn’t change anything, but that’s how she’s able to get away with it.

🔞 Candy.AI 🔥 AI Sex Chat - Roleplay, Erotic Stories, Try for Free 🕹️

Please, Rate This Story:
1 Star2 Stars3 Stars4 Stars5 Stars
(average: 4.38 out of 8 votes)

By # #


  • Reply Willy T. ID:fx7qoskv3

    All these stories denigrate condoms. I think it’s mostly because men & boys always have visions of grandeur & get them too big so they’re always just fucking the rubber.
    Amazon sells a brand named ‘Iron Grip.’
    They’re very tight f not only transfer the good feelings, but keep you hard.

  • Reply woody ID:7zv346scd3