Chapter 23: Tom and Andrew

This chapter had sex with oral sex with a minor, Mdom, Humiliation, Reluctance.

I yanked on the lead. The collar collapsed down around her neck, and a gurgle came from Dorothy’s suddenly open mouth. I said nothing, and Dorothy was hacking and coughing more tears coming from her eyes. Pea saw the tears running down her face. Sounding angry, she barked, “Wipe those tears away. They make you uglier than you already are. No one wants to fuck a crying, ugly old bitch. So dry it up, unless you want something to cry about.”

Dorothy alternated wiping her eyes and supporting her weight as she crawled out the door. Her head was hung down, not looking at anything but the floor. Her tits in the leather straps made cones with succulent nipples on top, which also pointed at the floor. And her round ass was lifted sweetly by the leather straps, which dug into the lower crease of her ass and thigh. She sniffled as she plodded down the carpeted hall to the elevator. She slowly crawled into the car when the doors opened. I figured we would go down to the bar area and find a few guys willing to fuck her. Halfway down, the elevator doors opened, and my plans changed.

Two teenage boys stood in the elevator’s doorway. They were pimple-faced kids who looked to be Cheryl and Helen’s age. At first, they didn’t notice Dorothy. She noticed them and blushed all over. She made herself less evident, hiding in the far corner. When they did, there was complete shock on their faces. They looked at each other speechless.

The geekier-looking blonde boy with a face full of red and yellow bumps and craters asked, “Damn, mister. What is up with her?” He pointed at Dorothy as they stepped in. She bowed her head down even further.

I had decided I would have these two boys enjoy Dorothy. It would be more humiliating than anything else I could’ve thought of. But first, I needed some time to make sure they were available and understood what I was offering. Since no teen boy would turn down a chance to fuck. “She’s the hotel’s bitch. A real slut this one. She likes to fuck and suck cocks whenever she can. Let me ask you two. Where are you headed?” I pressed all the buttons to the ground.

Dorothy knew what I was doing and began muttering, “Not boys. It can’t be boys.” I yanked up on her lead before she became loud enough for the boys to hear. She wheezed and coughed, her windpipe crushed by the choke collar.

The black-headed boy who stood five inches taller than his friend replied, “Our parents gave us money to go to a movie with our teammates.”

The shorter blonde boy explained with more information than he likely should have. “Yeah, they want us out of the way. They do the same thing after all of our traveling games. They swing with our teammates’ parents. They don’t think we know even what that is.”

The taller of the two then spoke up, “They always give us cash to go to a movie, bowling alley, or skating rink. We’re just running late. We’re meeting up with the guys. But we’ve already seen the movie. ‘The Blue Lagoon’. It’s a chick movie, but the guys like to watch Brooke Sheilds.”

The short blonde said to his buddy, “That’s because they’ve never seen anyone like her.”

Pea interrupted the boys’ nervous conversation. “So the parents don’t let you swing with them?” She patted the tented pants of the blonde boy. “Good, healthy boys like you. You should be good to fuck for hours.”

The blonde boy answered Pea’s question two octaves higher. “Hell no.” Then he attempted to redeem his octave change and act older than he was. “Shit, Tom is a virgin. He may have gotten his fingertips wet once after he felt up Lucy West.”

“Fuck you, Andrew,” the taller boy Tom said. “You haven’t even done that.”

“Tell you what, boys. You want to get your dicks wet. She’ll suck you and fuck you good. And her pussy is nice and juicy. Plus, she loves tongues in it, too,” I said, offering Dorothy up to the boys.

Andrew enthusiastically answered, “Oh fuck yeah. She’s hot.”

Tom didn’t jump as quickly at the offer. “Seriously, we get to fuck her or eat her.” Both me and Penelope nodded. “Then, damn straight, I want to fuck her. Andrew’s right, she is fucking hot. But she looks almost as old as our moms.”

As an off-handed compliment, I said, “She’s probably older than your moms, but not nearly as used. In fact, you’d be only the fourth and fifth guys to go there.”

Tom turned to Andrew, who wasn’t deterred in the least that Dorothy was older than his mom. “If we bail on the guys, they’ll call our parents when we don’t show.”

Penelope did the offering the second time. “Bring them along. She can fuck and suck the lot of you. We just have to find someplace discrete.”

“Our end of the hall is nothing but our teammates. And all our parents will be gone for a couple of hours. So it is available.” Andrew said.

“You’re forgetting about Lisa and Tonya, Pete’s and Ed’s sisters. They’re probably still in their rooms,” Tom said.

I was only partially listening to the boys and Penelope’s assurance she could handle the girls. I was more aware of Dorothy. She was looking up at the pimple-faced boy. She trance-like repeated, “No, I can’t ... They can’t cum in me.”

Thought it odd; she was only worried about their cumming in her. But she wasn’t about the actual fucking. I again yanked up on the lead but held it longer. “Bitches and fuck toys do as they’re told. You’ll suck and fuck them all.” She wheezed uncontrollably, hands to her throat, when I finally let the lead go slack. She crouched down to the floor, no longer willing to fight her fate.

Dealing with Dorothy gave me a second to think. I realized I never liked sloppy seconds. And I planned on fucking her a lot more. So I didn’t really like the idea of the teens dumping their loads in her twat. I addressed the boys as the elevator doors closed for the second time. “Boys, she’s right. You can fuck the slut, but her cunt is my cum depository and only mine. You can cum in her mouth, but in her cunt you need a rubber. Plus, you don’t want to eat a cunt with a bunch of guys’ cum leaking out.”

Andrew again spoke up, “Oh shit, yeah.” He looked at his friend and said, “You get the condoms and bring the other guys if they want to come.” I smiled at the statement, knowing all teen boys would show up. Especially when there was even a possibility of cumming in a female. He then looked at me and said, “Can I eat her before fucking her? I’ve never eaten a woman before.”

“The slut will love it.” I neglected to tell them; she already had lots of cum in her. The novice fourteen-year-old boys wouldn’t recognize the flavor difference for years.

Pea had developed a thing for the tall black-headed teen. To his surprise, she unzipped his shorts and pulled his hardened dick out of the opened fly. He froze in place at the bold move. Pea explained her action. “He should get a sample. That way he can tell his friends what they can expect.”

“Good idea,” She looked disappointed at the fairly narrow five-inch dick she’d pulled out through the zipper. He’d sell it a lot better if he got his first blowjob before he left. Down at Dorothy, I said, “Ok, slut, show him what you love to do.” The crouching woman didn’t move until I yanked up on the lead. She turned red from lack of air before she started moving on her knees to the teen’s average-sized dick.

Using the lead, I guided Dorothy’s head to Tom’s crotch. Still kneeling up straight, her face was inches from his exposed hardon. His body tensed astounded by the breath on his dick. It took me using the lead’s thin leather handle to get her to open her mouth. It had bent around her pelvis, splitting her crack and whacked her pussy lips. I was ready for a second encouragement when her mouth closed down around the pale, hard rod. The boy’s tense body turned solid. Dorothy’s head bobbed the length of the teen’s dick. Her cheeks hollowed slightly, and the elevator car was filled with the sounds of slurping.

Andrew said, “Damn, Tom, she’s sucking your dick. That is fucking hot ... Shit, you’re getting a blowjob in an elevator. That is so cool.”

Tom didn’t answer. He only grunted. He started panting before he put his hands on the back of Dorothy’s head. Evidently, not forcing a woman down your cock is a learned skill. It was a skill Tom didn’t have. He grabbed her hair and rammed his dick through her pursed sucking lips, smashing her face into his groin. He held Dorothy tight, her nose flattened in his sparse pubic hair as his legs twitched. He threw his head back, resting it on the elevator’s mirrored wall. Dorothy’s shocked look said when the spunk started shooting into the back of her mouth. I said, “Swallow it,” in a low, demanding tone.

She did as she was told. She had to swallow over and over as the teen’s balls emptied their copious load into a woman for the first time. He would’ve fallen had Penelope not caught his arm when the last of his spunk was delivered into Dorothy’s mouth. His dick remained in her mouth for two more floors, in which I held the door open like I had on the five floors prior. It had extended the ride long enough for the boy to fully enjoy his maiden blowjob. Her lips slid back up the still-hard cock as he pushed her away. She quickly crawled backward into the corner, staring at the boy’s cock like it was a snake that had struck her.

“Oh fuck, that was incredible.” The teen finally said, looking down at the woman that gave him his first blowjob. “You’re a fabulous cocksucker. God, I could get used to that.” There was the tiniest bit of pride for a fleeting instant in Dorothy’s eyes before shame refilled them.

As the car came to rest on the first floor, I told the teen, “Fucking her is even better. Let your friends know. I guess we’ll be in Andrew’s room with the door open. Come back quickly; I’m not sure when I’m going to want the hotel’s sex toy back all to myself.”

Andrew told his friend, “Hurry up. I don’t get to fuck her until after you do.” Tom stuffed his cock back in his pants and ran out of the hotel.

“How far away is the movie theater?” I asked, pressing the button for the floor on which he got on the elevator car.

“Not that far. A couple of blocks,” he seemed in a hurry to get to the room and start learning what he could from the mostly naked woman in the corner. Dorothy had slunk back to the corner while Tom left. She crawled out of the car slowly after the doors opened on the floor where we had picked up the two boys.

It took a lot longer to get to the room than I expected. The extra time was worth the wait. I got the sweet view of her ass cheeks as they went up and down. The big green jewel between her ass cheeks moved in conjunction with her buns. The leather straps on either side of her pussyfolds protruded them. They peeked out between her thighs each time she moved forward on her hands and knees.

Andrew too hung back, so he’d get the view as well. The first thing he said was, “Damn, are those hickeys on her pussy? And what is that in her crack?”

Pea answered, “Yeah, the slut loves being sucked on almost as much as she likes sucking dicks. And that green thing is a butt plug. The hole it’s in has been overused. It holds it open longer while it rests.”

I added, “It’s not to be removed.” I reached down and pressed on the circular green glass. Dorothy moaned at the inward movement of the spade in her rectum. “See, she still likes it being pressed on. And it will make fucking her better. It fills her up, making her feel tighter.”

Andrew’s dick strained his pants at the sight of her pussy lips rubbed by her inner thigh. I could see some of the cum I had put in her vacated hole trickle out with her previous orgasmic honey. The teen knew enough to know pussies got wet when ready to be entered. He assumed she was leaking, hot to be fucked. “Damn, she’s got juice running out of her pussy. She’s so hot and wants to fuck. And I’ve got plenty to fill her while I fuck her.” I couldn’t believe the cockiness of the teen.