Dick. Good hard dick. There was some of it, of course. But not enough. Fingers and tongues and lips were well and good. A nice vibrator was even better. His cock—when it was time to use it—was nearly perfect, but she wasn’t getting enough of it.
But she had a plan for getting more.
Caroline looked at her with more than a modicum of dubiousness on her face. “You’ve got to be fucking kidding me.”
“No. Why would you say such a thing?” Dorothy said this with all the sweetness and innocence she could muster. Over the past few months she had managed to practice that to near-perfection.
“I should say the same thing to you,” Caroline replied while shaking her head. “Why would you ask such a thing?”
“Oh come on. It’s not like you love Rich—”
“Rick.”
“Rick. He’s just the guy you’ve been fucking for the past month.”
“But I like him.”
“But you don’t love him. I know your patterns, Car. At most you’re going to continue to fuck him another few weeks before dumping him and moving on. I’m giving you and him both too much credit to say he’s your boyfriend.”
“Yeah. About that. You want to fuck Rick—”
“Rich.”
“Rich.” She paused and shook her head. “Don’t fucking do that, Thena. His name is Rick.”
“Right. I forgot.”
“You say you want to fuck Rick because it’ll make Basil jealous. And that he’ll love it.” She repeated her dubious look. “Even for you and his…weird kink that’s fucking bonkers.” She paused and took a breath. “And why the fuck should I let you fuck my boyfriend?”
“I was just asking as a favor. Basil will get off on it.”
“I think you’re trying to drive him away. Get him to dump you. That’s what you do, Thena. Date for a few months, sleep with another guy, let guy number one know and get him to dump you.”
Dorothy’s voice caught in her throat. “It’s not like that this time.”
“Uh-huh.”
She frowned at her taller and prettier roommate. “Then just tell me how much longer you intend to fuck Rick. Or if he’s the one, should I look for another guy to fuck?”
Chapter Six
Dorothy felt more than a little ridiculous strapping on the harness and fake phallus that encompassed the entirely of the strapon device that Basil had selected as what he wanted for her to fuck him with.
The harness wasn’t all that strange, it was a bit like a climbing harness that she’d used when bouldering back in college, except it had a pad and ring in the front to hold the dildo in place. Oddly she was rather pleased with his choice of dildo. It was silicone and a muted blue and completely smooth with a bullet-like head, no ridges at all. It was definitely bigger than Basil’s cock when he was fully erect, but it wasn’t huge. She could respect that; she doubted any man—or woman—wanted to be fucked with a gigantic tool. Maybe it was exactly the same size as his dick. She’d have to do a more in-depth comparison later on.
When everything was in place and she was ready to go, the dildo drooped slightly from her crotch. She figured that was normal. It was only then she started to get nervous. Up to that point it was something new and fun to explore and Basil seemed to know what he was doing; he’d done this before with his ex-wife and maybe someone else. Dorothy didn’t want to ask those questions. He had been the first one to strip down and was still wearing his cage. It was odd how comfortable he was walking around in front of her wearing nothing but the cage, but that was his kink and she certainly didn’t hold it against him.
“What do we do now?” she asked, holding her lips in a little moue and holding her fake cock with one hand, the other shoved against her hips, clenched into a fist.
He had told her that it was fine if she wanted to keep her clothes on, but that didn’t seem very intimate and she wanted the full experience. She had stripped down to her panties and bra. Some planning ahead had told her that lace and thongs wasn’t what was needed for tonight. Instead she went for the athletic underwear she wore to the gym along with her jogging bra that was more of a corset than a bra.
Sex was a sport, right?
“Well, do you want me on my back or my hands and knees?” he asked.
“Hands and knees, I think. A little more humiliating for you, though I’d like to see that little cock of yours shoot out cum all over your belly. It’s really more of a prostate massage than anything else, right? You can cum without getting hard?”
Basil nodded, suddenly intimidated by her knowledge. He had told her about the websites he visited for chastity advice and now he was starting to regret how much she knew. He didn’t have to explain everything to her and that was scarier than he would have thought. “Yeah, if you fuck me from behind I’ll probably wind up shooting all over the bed.”
“Good. You can clean it up too,” she said with a nod.
“Have you ever done this before?” he asked, fully knowing that she hadn’t, but wanting to seem like he knew something more than she did. He wanted to have the experience.
“Anal? No. But I’m a quick learner. Give me the lube.”
She wasn’t stupid. Everyone knew that you had to use a lot of lube when getting pegged, male or female.
Dorothy didn’t feel the least bit bad about lying to Basil. She had done anal before, except it was with a guy who was obsessed with sticking it in her ass—and presumably every other woman he ever had sex with—and when she finally agreed she was nonplussed by it.
When she agreed to try it with Paul those years ago, she had hoped in her heart of hearts that she was one of those women who would truly enjoy it as a happy and occasional alternative to vaginal sex. It wasn’t terrible or painful, but it did nothing for her. Almost nothing. She could appreciate how it felt, but it would never get her off. Paul seemed offended that she played with her clit when he fucked her in the ass. And she didn’t just try it once to appease him. After a dozen times of having his cock in her ass she was done with anal and with Paul.
But pegging Basil was different from getting anally fucked by Paul. She was in the metaphorical driver’s seat. Lubing up the dildo was fun and fine. Basil was the one who got his ass ready for her, which was the best way to approach it. She wasn’t sure if she was up to lubing her new boyfriend’s ass just yet.
Kneeling behind him, she felt a power rush and placing the tip of the dildo against his tightly puckered anus she smiled and said, “Tell me if I’m hurting you.”
“I’ve done this before. I know what to do.”
She knew she should have admonished him then and there, but she was too eager to move forward with the pegging. And maybe a little suffering would be good for him.
Sliding the dildo into Basil’s ass was much easier than she thought it would be, but she assumed that was because they had used a lot of lube and Basil was used to doing this. She would have loved to see his face as she filled him up, but that wasn’t going to happen if she was going to continue to dominate him. Once she was inside, he let out a little whimper.
“Too much?” she asked and found that she didn’t really care if she was hurting him. He probably like to be hurt and humiliated a little when playing this game.
“No, no. It feels really good. I’d forgotten how good it is.”
Dorothy wished she could say the same. There wasn’t any pain while she fucked him, but there wasn’t any true pleasure either. She rocked her hips back and forth and found the rhythm that seemed appropriate. The motion was strange, completely unlike getting fucked by a man on top. It was completely unlike riding a man’s cock and pumping her thighs up and down to ride him or to roll her hips back and forth. What she was doing was undeniably masculine, but she took no great pleasure in it.
“Oh fuck that’s good,” Basil said. He breathed unsteadily and clutched at the sheets and then his hand went to his cock, but masturbation was out of the question because the cage was keeping his flesh completely under control. D
orothy was amused at his frustration and did take pleasure in how he was not able to fully give himself over to the pleasure that he wanted.
“You like that?” she asked, unkindly. “You like getting fucked in the ass by a woman?”
“Yes,” he sighed, his breath coming jaggedly now. “Yes. I love it. Fuck me. Fuck me hard!”
While she didn’t suddenly increase her thrusting and start jackhammering away at his ass—she liked what she was doing but she wasn’t crazy stupid—Dorothy did increase the pace and force of her thrusts. He responded to what she was doing. It made her wonder what other things had been up Basil’s ass and what other women had done this for Basil, besides his ex.
“Oh fuck oh fuck oh fuck,” Basil said in rapid succession over and over. She didn’t stop fucking him immediately, but the way he said it made her pause.
“Are you okay?”
“Don’t stop, don’t stop,” he pleaded. “I’m almost there!”
She grabbed his hips and kept going. She never appreciated until that moment how much effort it took to fuck like a man. She was getting tired and had little to show for it.
And then it happened. Basil made a noise that didn’t sound like pleasure, but she knew he was cumming.
“Yes,” he sobbed. “Fuck yes.”
Dorothy slowed the pace of her thrusts and eventually stopped. She was curious and couldn’t help herself. Basil barely managed to stay up on his hands and knees because he wanted the dildo to stay in his ass. She reached around his body and found his steel-encased cock. The cage was wet and sticky and a little bit slippery; it felt exactly how cum always felt. Just underneath the immovable bars she could feel his hot flesh that was restrained against his will.
“Did you like that?” she asked him, bringing her fingers up to her lips and giving them a single lick. She wasn’t one of those women who either had a real affection for swallowing cum or at least gave the show of liking it to please her partner, but there was a certain visceral attraction to the products of sex.
“Uh-huh,” he breathed. “I loved it.”
Her hand went back to his cage to wipe up some more of his cum. Undoubtedly some of it had splattered onto the sheets, but that was Basil’s problem, not hers. She offered her fingers to Basil. His head was turned and he knew what she wanted. Making a man participate in a boundary-pushing kink after he came was always difficult, but Basil made little protest. He extended his tongue and licked her fingers clean.
“We’ll have to do this again sometime,” she told him.
“Yes…”
“And I have a little experiment I’m going to try on you,” she told him.
Even though he was exhausted, Basil perked up. “What is it?”
“Oh, you’re not going to like it, but I think you like humiliation a little don’t you?”
It was easy to admit this to her now. “Yes.”
“Prepare to be humiliated.”
Basil shivered in anticipation.
Chapter Seven
Rick looked skeptically back and forth between Dorothy and Caroline. He had known his relationship was on the rocks with Caroline he might have done things differently, but apparently this was going to be the last hurrah he would have with Caroline. It was strange because Caroline had seemed such a plain and normal woman. Her roommate, however…
“You want me to have sex with you to make your boyfriend jealous,” he said to Dorothy.
The bright-eyed brunette smiled and nodded eagerly at him. “Yes. You’ve got it perfectly. Car says you’re clean and so am I and I’ve got an IUD so it’ll be fine when you cum in me.”
“You want me to cum in you?” he asked. This was new.
“You want him to cum in you?” Caroline asked. This wasn’t part of what they had discussed.
“How else can I prove to Basil that I had sex with someone else?” she asked innocently.
The sweet look on her face collided with the vulgar words and plan coming from her mouth.
Neither of them had an answer for her.
The silence between the trio grew uncomfortable.
It was Caroline who spoke first. “You can say no, Rick. I don’t see our relationship going anywhere. You’re a nice guy and all but…” She cleared her throat. “Anyway, as you can see, my roomie has some…unusual tastes in sex.”
“I’m kinky, is what she’s saying,” Dorothy interjected. She turned to Caroline. “And just to be fair, Basil is all yours when I’m busy with Rich.”
“Rick,” Caroline and Rick said in tandem.
“And what the fuck?” asked Caroline.
Dorothy put her hand on Caroline’s forearm. “He’s got a tongue like you wouldn’t believe. His cock will be in his cage, but you won’t mind in the least. He’s given me more orgasms by eating me out than with his cock. You should really indulge.”
Rick couldn’t believe what he was hearing. And despite what he was hearing, his cock was growing steadily harder. He’d never been in a negotiation for casual sex. He knew that listening to his cock was probably a bad idea, but lots of men found themselves having a wonderful time because of a bad idea.
He looked at Caroline. “You were going to break up with me, weren’t you?” he asked her bluntly. There was a tinge of anger in his voice that he struggled to hide.
“Well, yes, but it wasn’t like we were going to get married or anything.”
Rick turned away from Caroline. “I’d love to fuck you for your boyfriend.”
Oddly, up to that point Caroline had been positive that Rick was going to refuse Dorothy’s request. In a fit of petty revenge, she snapped, “And Basil can eat my pussy until I scream.” She glared at Rick. “Then you’ll see how thin these walls really are.”
Basil wasn’t exactly sure what he walked into when he arrived at Dorothy’s apartment. Caroline and her boyfriend were there and they looked pissed at each other while Dorothy was all eager smiles and grabbed his hand (and surreptitiously, his cock) when she greeted him in the entryway, pulling him into the living room where the other couple was sitting on opposite sides of the couch.
“Bas, you already know Caroline,” she said, reintroducing him to her roommate. “And this is Rich—”
“Rick,” said the other man, rising up off the couch with his hand extended.
Dorothy had the good manners to blush. “Sorry. Rick. I always forget.”
The two men shook hands and Dorothy carefully timed her next words. “Rick’s going to be the one to fuck me tonight while you wait out here.”
Basil blanched. His stomach tightened up. His cock tried—and failed, naturally—to get hard. Rick’s handshake was firm, but he didn’t play the stupid game of squeezing so hard like he was trying to prove something.
That was the signal to Basil. Rick had already proved something. He was going to fuck Dorothy with or without Basil’s permission or endorsement and there was nothing he could do about it.
This was the bit of humiliation she had in store for him. They all knew before he did. They all knew he was an emasculated chastity fetishist.
That turned him on even more.
“Okay,” he said warily.
“See?” Dorothy said smugly to her roommate. “I told you he’d agree. He’s a good, obedient boy who does what he’s told.” She turned to Basil. “And if he’s very good, he’ll get a reward.”
The pain in his cock was incredible. He loved it when she talked to him as if he wasn’t there. A hundred scenarios popped into his head as to what his reward might be.
When no one said anything else, Dorothy grabbed Rick’s hand and pulled him out of the room and down the hall. Basil and Caroline heard the bedroom door slam shut.
Caroline looked at Basil. “Do you…do you think they’re actually going to have sex?” For the first time in the quick encounter, Basil saw some vulnerability in the woman. Maybe she was done with her relationship with Rick, but it was one thing to break up with someone, and then another entirely to see him dragged fro
m before her eyes and into another woman’s bed. Her roommate’s bed to be specific.
“Probably,” he offered. “Thena’s not the sort of person to fool around…uh, not the sort of person to make idle threats and boasts.”
A nod confirmed Caroline’s suspicion. She looked down at the floor and wished she could find someone who she could truly love. The number of men she had dated over the past several years had been astounding and it disappointed her. Was she being too choosy or not choosy enough? Yeah, she was having fun, but was her life stalled because she couldn’t find someone she wanted to commit to?
“Do you know what she said to me?” asked Caroline.
“No. What?”
“That if I wanted you to go down on me, all I had to do was ask.”
Basil shrugged. “Well, if you’re asking, then I’ll do it. I’m happy to.”
Caroline looked up at him, eyes narrowed. “I thought you were in love with her.”
Love hadn’t been discussed between Basil and Dorothy. Sex had, yes. Kinks, most definitely. Continuing their relationship for a few more weeks, without a doubt. But love?
“Yes,” he said.
“And you’ll just fuck another woman because she said it was okay?” Before Basil could answer, Caroline added, “And she’s fucking another man. Is that okay with you?”
The answer came easily to Basil. “If that’s what she wants, then yes. I’m her…well, not her slave. Her thrall, I guess. What she wants, I want.”
He wanted her to fuck Rick. He wanted to watch her fuck Rick, but that wasn’t going to happen. Her going to bed with another man was both a punishment and a gift.
“Are you wearing that stupid thing on your cock?” Caroline asked.
Basil said nothing, but he unzipped his pants and presented his steel-covered cock to her. She nodded in satisfaction. “Fine.” She stood up from the couch and strode purposefully toward her small bedroom. Basil watched her skirt flounce with her every move. “Come on,” she said as if there was a dirty job to be done. “She said you ate pussy better than anyone she’s ever been with. Time for me to see if she’s right.”
The Elliot Silvestri Erotic Reader Volume 6 Page 110