Chapter 23 by MistressOfTheNightWinds
What’s Caitlin doing?
A trip downtown
Overhearing some other girls at school talk about the new sex shop downtown which was supposed to have gloryholes, I had been wanting to try it out. Actually, I had to find out what a gloryhole was first, then, I wanted to try it, especially after the party the other day. Luckily, my parents were none the wiser, my plan had gone off without a hitch. When I got home after the party, I made up a story about the project I was supposedly working on, they lapped it up. I was getting really good at lying. But there was no way I was going to be able to get away on a Sunday, there was no lie good enough for that. So I planned on Monday after school. I told mother and father Rachel and I still had some work to finish on the project.
I made it through school, Mr. Doe fucked and came in my pussy, like normal. I wanted to ask him to fuck me in the ass like he did Avery. But judging by how hard it was for her, I wanted to warm up to it first before taking Mr. Doe’s big dick. So my mission today was two-fold, find the sex shop and buy a butt plug or dildo, and check out the gloryhole while I was there. It took a lot of convincing, but Avery finally agreed to drop me off. She had to work on a group project (a real one), so I would be on my own for a couple hours before she could pick me back up.
Avery and I left school together and she dropped me off in downtown at the corner. I walked down half a block and entered the shop. There was only one catch, make sure no one there could recognize me. It would be real bad if word made it back to my parents. It was darker inside, the woman at the counter glanced up at me for a brief moment before going back to her magazine. She had short blue hair, slicked back with nose and lip piercings. I didn’t recognize her and she paid little attention to me, just another school-girl in a city full of them, at least, that’s what I hoped.
I strolled around the shop, looking at all they had to offer. There were plenty of sex games, costumes, leather outfits, whips, and a whole host of other weird-looking devices I didn’t know the purpose of. There was a closed, unmarked door near the back, maybe that’s where the gloryholes were? I finally came upon the isle that held dildos, vibrators and butt plugs. I stood for a while, taking a good long look, trying to decide what to get. Not knowing exactly how big to go, I eventually settled on a medium-sized plug. The instructions said to use plenty of lube, so I picked up a bottle of lube as well. One last thing, condoms, just in case. I’d never used one before but found an instructional video online, it looked easy enough.
With my purchases, I walked up to the counter to pay. The attendant looked at me and asked, “Will this be all for you?”
“Yeah…Er, well, no.” She raised an eyebrow questioningly. “I mean...um, I heard you have...gloryholes? Is that true?” I said in almost a whisper. She looked me up and down for a moment before replying. “You gotta be at least 18.”
“Oh, I’m 18.”
“Uh huh, you’re gonna have to show ID if you want back there.” I showed her my ID. She took a good look before handing it back. “Alright, you know how it works?”
“Kinda?”
“Right…Head on through that door in the back. Girls get in free, buy guys have to pay. Once you get back there, you go into any one of the open center booths. There’s holes in the wall, if anyone sticks a dick through, you have to work it until the man finishes. If you don’t you’ll have to pay the entrance fee. You can use whatever part of your body you want. Any questions?” I shook my head no, then headed back through the unmarked door.
Beyond the door, there was a man on a stool. He was tall and burly. He looked me up and down hungrily before thumbing me towards the direction of the hallway that lay ahead. On either side were doors, clearly marked. They were in groups of three, one in the middle for the girl, and one on either side of that. They were fairly small. Since most of them were open, I went into the first middle door on the right. Apparently they didn’t get much foot traffic this time of day. I closed the door behind me and looked around. It was narrow, with large holes in either side and a small stool. I was still wearing my school uniform, complete with bra and panties. I went ahead and stripped naked and waited.

Not knowing how long it would take, I sat on the stool and began to rub myself. My moans must have attracted someone, because a few moments later, a cock appeared. It was only half-hard, and much smaller than Mr. Doe’s. Not wasting any time, I immediately took it in my mouth and ran my tongue around and over his glans. I continued, running my tongue down the shaft and taking more of it in my mouth. By that time, he was all the way hard. He didn’t last long and shot is load in my mouth. I swallowed ever drop and pulled away, then he disappeared.
I went back to playing with myself until I heard a pair of men talking and laughing, then doors on both sides of me opened and closed. A second later, two cocks appeared. They must have been crazy horny, because both were already rock hard. Still smaller than Mr. {LastNames}’s, oh well. I unwrapped a condom and put it on the bigger of the two, then leaned over, impaled my wet pussy on it and started sucking the other on the opposite side. The booth was narrow enough for me to do both at the same time. I pressed my ass against the wall as hard as I could and let the man pound my pussy. Between the condom and smaller dick, it was quite a bit different than I was used to. It still felt good, but not as nearly as good as when Mr. {LastNames} fucks me.
While getting drilled, I kept sucking the other cock. I got another load in my mouth, this one quicker than the last. I put my full attention to the cock inside me, but less than a minute later, the man stopped, left it in me for a few seconds, then pulled out. I turned and could see a small pool of milky liquid in the tip of the condom, I was nowhere near getting off myself. The two men left and I went back to fingering myself. After a while I finally came, then licked my fingers clean. There were sticky, mostly my juices, but with a bit of cum mixed in, they tasted sooo good, I wanted more.
A minute after I came, another cock appeared, I didn’t hesitate, I just pressed back into it and took it inside me raw. I wanted to be fucked! It wasn’t long after he picked up a good rhythm that he pulled out and said through the wall with a weirdly familiar voice I couldn’t quite place, “I wanna come on your face.” I put my head down to the hole and tried to take it in my mouth, but instead, he sprayed all over me, getting cum on my face, hair and even a little in my eye. God, what was wrong with these men? Couldn’t any of them last more than 20 seconds? “You’re a good little slut, ain’t ya?” The man said. “I bet I could get a better fuck from your mom.” I grumbled quietly, good thing he didn’t heard me.
I waited for a while longer, touching myself, trying to get off. I kept imagining Mr. Doe’s big thick cock pounding inside me. The way it stretched my tight kitty, the way I could feel it throb right before he shot his cum in my womb, the way he touched and licked me, running his hands all over my naked bod, the way my pussy clenched around his girth involuntarily whenever I orgasmed. Even with these thoughts running around me head, I couldn’t climax again. It was almost time for Avery to pick me up, the gloryhole was a disappointment. I got all the cum off my face that I could, re-dressed and walked out hoping there was a restroom I could use to finish cleaning up.
On the way out the back, the burly man standing watch smiled and winked at me. It took me a moment, then I realized, he must have been the first cock I sucked off! It drove me wild, I almost jumped him right there, but Avery would be there any minute. I walked back into the shop proper, and stopped dead in my tracks. My father, he was there, looking at the merchandise on the shelves. He glanced my way and we locked eyes. His face turned a brighter shade of red than I’d ever seen and he grabbed my arm and began to drag me towards the front door. The counter girl tried to intercede and yelled for burly man to come quick. But my father said sternly with fury in his eyes, “This is my daughter.” That was enough for the employees to back off. He dragged me out the door and into a narrow alley. “Caitlin! What in tarhill were you doing in there!?”
“What was I doing!? What were you doing!?”
“I’m your father! I don’t have to explain myself to you!” He leaded forward and got even angrier. “What is that on your face!”
I tried to break free of his grip but failed. “Let go of me! You’re hurting me!”
“ANSWER ME!”
I looked him square in the eye and defiantly said, “You know exactly what I was doing! And you were there for the same reason, weren’t you!” But I wavered, a sudden, terrible thought overtaking me. My father, he was in the shop…Did he? Was he….?
He must have had the same thought, because all the color drained from his face at the realization that the cum on his daughter’s face was his own. He let go the tight grip he had on my arm. “You…You are a harlot. You are not welcome in my house, you’re not my daughter.” And with that declaration, he turned and walked away. I stayed there for a few minutes, stunned. My own father, he had been inside me. He had cum on my face. How many times had he gone to the gloryholes? Surely this wasn’t his first time. And what right does he have to condemn me for the exact same thing he was doing? And now he had disowned me, kicked me out of the only home I had ever known. What was I going to do? Where was I going to go?
These thoughts and more raced through my head as I leaned against the wall. I remembered Avery, she was probably waiting for me. I collected myself the best I could and walked back on the street, looking both ways for father before heading back to the corner. Avery was there already, waiting for me. I got in her car and stared straight ahead. She sensed something was wrong. “Cat, what’s going on? What happened? Are you ok?”
“Just drive please.”
She looked at me with concern, then put the car in drive and pulled out. I was quite for most of the ride back to school, trying to think of what to do. I eventually started crying and Avery pulled into an empty parking lot and held me against her chest. “I’m sorry, I’m so sorry. I messed up.”
She tried to sooth me “Its ok Cat. Whatever happened, we’ll work through it together, ok?”
“You don’t understand, my father…My father was there!”
She pulled away and looked at me, “What do you mean your ‘father was there?’ In the shop?”
“I mean, he was in the back…I….”
With a look of absolute shock and disgust, Avery realized what I meant. “Ok…Ok.” She took a deep breath before continuing. “Did he…Well, you know, did he cum inside you?”
I shook my head no. “No, he came on my face.”
“I’m not sure if that’s better or worse. Wait, how do you know it was him?” I explained to Avery what had happened, how I saw him in the shop after, looking around, how he dragged me out to lay into me, the look he had when he realized what he done and how he had kicked me to the curb.
“Jesus.” Avery said. She paused to think. “Do you have somewhere to go? Any other family?” I shook my head no. I had no one. “Ok, ok. Let me think. You can stay with me for a day or two. But you know how my parents are, they would start asking a million questions. And they’re so by the book, if they found out your parents kicked you out, they’d probably call the authorities.” We both went silent for a minute, neither one of us knowing what to do. Technically, I was 18, so they couldn’t **** me into a group home or anything, but I didn’t have a job or a place to stay and was still in school. Wait, school, would I even be able to finish? Father paid my tuition…fuck, this was bad.
Avery snapped out of it, “I got it! My aunt! She lives alone, she has space and won’t care why you got kicked out. She’s great! And Mr. Doe is right next door. We’ll go there, we’ll talk to Aunt Vic and sort this out.” The thought of seeing Mr. Doe calmed me down from hysterical to slightly gasping for breath. Avery stopped by school so I could at least grab my back-pack that had a change of clothes, then took me to her aunt’s house. No one was home, so we waited.
Where’s John?
Disable your Ad Blocker! Thanks :)
The Rulebook
You find a Rulebook that lets you rewrite the rules any organization has to follow
A lucky protagonist stumbles across a magic book that lets them rewrite the rules.
Updated on Jun 17, 2026
by Ggnt
Created on Jul 27, 2017
by ashes2ashes
You can customize this story. Simply enter the following details about the main characters.
- 141,601 Likes
- 59,048,105 Views
- 8,545 Favorites
- 31,753 Bookmarks
- 6,723 Chapters
- 71 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments