“I was with my boyfriend while my friend Lisa was with her boyfriend. We were hanging out in our dorm room with another guy. We were drinking and talking, but my boyfriend was being a dick, and I was mad at him. He said something obnoxious, and it pissed me off, so I went over and sat on the lap of the other guy to annoy my boyfriend.
“My boyfriend didn’t seem to care, so I kissed the other guy. We were all drunk, and my boyfriend was kind of just egging me on, so I ended up giving the guy a blowjob.”
“Wait, you did this in front of not just your boyfriend but also your friend Lisa and her boyfriend?”
“Well, I was kind of crazy in college.”
“Clearly,” Rob replied, his attention completely focused on Gin’s story.
“So the next thing I know Lisa is telling my boyfriend not to let me get away with what I was doing, so he comes over and the next thing I know he’s fucking me from behind while I’m on my knees giving the other guy a blowjob.
“And, well, I think I said something about a DP fantasy, and Lisa is in the background cheering the two guys on to make my fantasy come true. The next thing I know I’m straddling the new guy, while my boyfriend is fucking me in the ass.”
“With an audience no less. That’s pretty crazy all right.”
“Oh, it didn’t end there.” Gin smiled because she could tell Rob was not just interested, he was getting really turned on. “I’m getting fucked in my pussy and ass, and I look over my shoulder and tell Lisa that I really want her to let me borrow her boyfriend’s cock, as I want to get it in all holes.”
“Wow.” Rob swallowed and took a drink.
“She replied, ‘Oh, you can give him a blowjob, but only if you let me get a turn with all three.” Gin shrugged, a wicked smile on her face. “So that was my wildest moment. I got fucked by three guys and then watched my best friend get fucked by the same three guys.”
“So what was it like?”
“Pretty awesome, to be honest. Although one of the things I remember most is how Lisa and I were pretty much in charge, bargaining over which guy would do what and who was getting a turn. I really liked having three cocks at my whim.”
“I bet.”
Gin stared intently at Rob. Sharing the story made her wet and incredibly turned on. She couldn’t stop thinking about Rob and his cock. She decided to keep the erotic momentum going. “So if we’re going to share our deepest darkest secrets, it’s my turn. What was college like for you?”
“Oh, I studied like crazy. Was summa cum laude. Hell, I didn’t lose my virginity until senior year.”
“Ugh. You are boring. You need to bring more to the table.” Gin tapped her chin with her finger. “Okay, if your truths continue to suck, you’re going to have to move to dares or something.”
“Truth or dare? We’ve moved onto the reliving high school portion of dinner I see.” Rob smiled.
“That works for me. I was only slightly less crazy in high school than I was in college.” Gin grabbed her sake again and downed it. “So truth—how big is your cock?”
Rob shook his head and smiled. “I tried to bury that article. Fucking Google. And Eric Schmidt owes me a favor, too.”
“You’re stalling.”
“Fine. It’s nine inches.”
“See? That wasn’t too hard, was it?”
“Actually, it’s only nine inches when it’s hard.”
Gin laughed. “Oh you’re naughty.”
“You have no idea. In fact, my turn: “Have you ever had sex with a woman?”
“You’re supposed to say ‘truth or dare,’ dummy.”
“Fine. Truth or dare?”
“Truth.” Gin winked.
“Have you ever had sex with a woman?”
“You are so predictable.” Rob smiled. “Yes. A few times. I’m not really that attracted to women, but I’ve enjoyed the few times I’ve done it. It’s nice.” Gin rubbed her hands together. “So truth or dare?”
Rob leaned forward. “Truth.”
“How hard is your cock right now?”
“Uncomfortably hard.” Before Gin could reply, Rob asked, “Truth or dare?”
"Dare.” The moment she said the word, Gin shuddered in anticipation and excitement. She knew Rob’s reputation, and she knew exactly the kind of guy he was.
Rob stared at her with a smile on his face. “I dare you to come sit next to me and stroke my uncomfortably hard cock under the table.” His eyes were intense, the desire in them palpable. His dare was an amazing turn on.
Gin stood up and moved to the chair at the table to the right of Rob. He watched her intently. As she sat down, she ran her hand up and down Rob’s right thigh, teasing him as she would brush her fingertips against his cock straining against the material of his pants and then slide them down again. She slid her hand up to his crotch and stroked his cock through the material. Leaning over, she whispered in Rob's ear, “Unzip your pants and pull your cock out.”
Rob reached under the table, and Gin reached up and rested her hand on his as he unzipped his pants, slid his hand in, and pulled out his hard cock. Gin took it in her hand. The rumors were true. Rob’s cock was enormous. She slid a finger across the head as she squeezed. Some precum oozed out onto her finger. She rubbed the slippery fluid around and used it as lubrication under her finger tips.
She stroked Rob’s cock, pausing every so often at the base to brush her fingertips against his balls. Looking up at Rob’s face, she loved that his eyes were closed and his head was leaning back a bit. She squeezed the end of his cock and then let go.
Rob opened his eyes as Gin brought her fingers up to her mouth and licked them. “Truth or dare,” she whispered as his hands disappeared under the table to adjust his pants.
“Dare. Very much dare.”
Gin had never felt so in control of her short relationship with Rob as at that point. She knew what he wanted, and she was in charge of it. There was no doubt what he wanted to hear. “I dare you to bend me over and fuck me from behind.”
Gin had been fantasizing about that since she had found out that he had a large cock. Now that she had confirmed it, she badly wanted to feel it inside her while she she was on her knees. She’d touch herself, stroking her clit while her fingers brushed against Rob’s huge cock pounding her from behind.
“I have an apartment a few blocks away.” He called for the check, and less than ten minutes later they were walking down the sidewalk. Gin considered taking Rob’s hand, but he didn’t reach for hers so she just walked beside him, every step building the erotic tension.
As she walked, Gin thought of Rob. She had figured him out. He was an incredibly sexual creature. Everything with him was reversed. Sex was the first step in his relationships, not the final one before commitment. It made so much sense. Hell, she was the same way.
They reached an older apartment building. The doorman nodded but didn’t say anything as Rob walked through the lobby. They walked right into the elevator, and Rob pushed the button labeled “PH.” As the doors closed, he turned and grabbed Gin’s arms, pulling her in for a kiss.
She pressed hard into his lips, reaching for him with her tongue. She could feel his hard cock pressing against her pussy through their clothing. His arms reached down and caressed her ass as he pulled her against his cock. His tongue danced with hers, the soft and wet flick of pleasure a wonderful counterpoint to the frustration of them still being clothed.
The door dinged, and they stumbled out of the elevator directly into a living room area. Gin looked around. Holy shit, he owns the entire floor. Rob grabbed her hand and pulled her over toward a couch. He was commanding and forceful. As they reached the couch, he pushed her forward. She braced herself on the back of the couch with her hands, facing him.
“No, bend over,” Rob said. He took Gin’s hand, pulled her forward, spun her around, and then gently pushed her between her shoulder blades. “You don’t dare someone if you don’t mean it.” Gin leaned forward, bending over the back of the
couch. She was sopping wet. The fact that Rob wanted to take her right then and there was an amazing turn on.
Rob's hands slid down her back until they reached her miniskirt. He pulled it down with both hands. As it slid down to her ankles, he kissed her ass and then grabbed her thong under his fingers and pulled it down to her knees.
She almost couldn’t bear the anticipation. She badly wanted to feel his massive cock pushing into her. Would the friction fill her with the kind of pleasure she’d never experienced before?
As he stood up, she felt Rob's fingers slide between her legs and up to her pussy. He stroked her pussy lips and slid a finger inside her. Gin groaned. “Oh my God, don’t tease me. Fuck me.”
And then she felt his cock slide against her thigh. She tingled as she felt how hard and big it was as Rob spread her ass cheeks with his hands and leaned forward. He’s so hard he doesn’t even need to guide it with his hands. Rob's thumbs tugged Gin’s pussy lips apart and then his cock was between them.
She wanted to reach between her legs and feel Rob's unbelievable cock as it slid into her, but she was bent over the couch. So she just focused all her feeling on it sliding in. She spread her legs a bit and winced as Rob's cock slid in a little further. He was so big he was stretching her, but with the sharp pain was the amazing feeling of every pleasure nerve ending being fired at the same time. He slid in slowly, and the combination of sharp pain and friction was extraordinary.
“God, you are so tight,” Rob said breathlessly.
He was deep in her and she couldn’t believe how amazing it felt. She had masturbated with some large dildos, but even the largest couldn’t compare to Rob. Each movement teased her clit, and Gin couldn’t help but shiver as he paused, her pussy lips squeezed around his cock.
Rob leaned forward and whispered, “I don’t want to hurt you, so let me know if I’m too far.”
“Deeper,” Gin whispered.
In response, Rob give a firm thrust, and Gin shuddered. The pain was real, and he hadn’t even pushed against her cervix. “That’s enough,” she whispered, as she squeezed her pussy muscles against the cock that filled her.
Rob leaned forward, leaving his cock deep inside her. His hands slid up from her hips to her chest. He caressed her tits through her tight top. “You have the most gorgeous body, Gin.”
Gin looked over her shoulder at Rob. Smiling, she said, “I dare you to fuck me.”
Rob returned her smile, and she felt every inch of him slide out and then there was an explosion of pleasure and sharp pain as he thrust forward. He slid out and thrust again. Each thrust increased the pleasure and lessened the pain.
Rob had his hand wrapped around the base of his cock, so every time he thrust she could feel his hand brush up against her ass. It was the most amazing feeling.
The thrusts increased in speed. Gin felt so wet and so turned on that soon there was no pain at all, only a consistent surge of pleasure from her clit down into her pussy. She had wanted to stroke her clit while Rob fucked her so she could come with him, but a shock hit her as she felt herself get hotter and hotter as Rob thrust faster and faster—she was going to come just from him fucking her from behind.
Rob started to groan as he thrust faster. “Fuck, you are so hot, Gin.” She felt his hands clench on her hips as he shoved harder and faster. He was pushing deep enough that it hurt a bit, but the pain was overwhelmed by the rising orgasm. “Fuck, I’m going to come.”
“Don’t stop. Yes! Yes! Yes! Fuck me harder!” Gin cried out, but just as she was about to cross into a crescendo of orgasm, Rob pulled out.
Gin looked over her shoulder to see his face twisted in a beautiful orgasm. “I’m coming,” he moaned as he pushed the head of his cock between Gin’s ass cheeks and against her asshole. A hot stream of cum shot against her asshole and dripped down toward her pussy. Another shot of cum landed on the same spot. Rob rubbed his cock up and down between Gin’s ass cheeks as he moaned and more cum leaked out.
Rob pulled back. Gin pushed against the couch, took a step back, and slid her hand down to her pussy. She was still close to orgasm, and the feeling of Rob's hot cum dripping down to her pussy lips was incredibly erotic. With a few strokes Gin started to moan. “Yes! Oh yes! Oh my God, I loved your big cock inside me,” she exclaimed as she slid her cum-covered fingers into her pussy.
Gin’s knees went week as the orgasm tensed and then relaxed all her muscles, and she had to grab the couch for support. Gin stood up on wobbly legs as the orgasm faded. As she turned around she could see Rob staring at her. “You are so incredibly sexy, Gin.” His eyes looked her over from top to bottom. “Would you mind getting together again some time?”
For any other guy Gin would have considered the timing of the request odd. They had just fucked. A guy asking for another date while his cum was dripping down the woman’s legs seemed a bit sudden, if not desperate. But from Rob it made total sense… he lived life one day at a time, and while he hadn’t committed to a single woman yet, Gin knew the table stakes for having a relationship with Rob—a good fuck—and Gin had just given Rob a good fuck. With that requirement met, Rob was ready to move on to the next step.
“I would love to get together again,” Gin smiled as she reached down and pulled up her underwear and miniskirt.
“How about Wednesday?” That was nearly a week away, but Gin again knew the context—Rob probably had dates with other women between the current night and then. She didn’t quite care. She knew the rules with Rob. This wasn’t a battle, this was a war.
Gin knew she would win the war.
chapter seventeen
Gin made her way home. She badly wanted to call Lisa and tell her how well things went, but she knew that Lisa was out with Bill, and that was the kind of date that could end up going all night long. Gin smiled. It was funny how life moved. It seemed like ages ago that Phillip had used her for a hot weekend and Lisa was drifting from guy to guy.
Although Gin normally took showers, she brewed some tea and drew herself a hot bath. She needed to lay back and soak. This had been one of the rare times that she ended up sore after being fucked, and she was really sore. As she stretched her legs out, she had to smile as memories of the evening filled her mind. She remembered the smile on Rob’s face as she issued her blunt dare. And his dare? She loved the feeling as she first grasped his cock under the table, immediately knowing that the rumors were true. But the memory that dominated all the others, the one that made her sigh in contentment as she lay in the tub, was the feeling of having him fill her so completely.
Yes, being sore was a very small price to pay for such exquisite pleasure.
She imagined the future, and she felt confident she could handle what was certainly going to be an emotionally rough period. She was going to have to smile and accept seeing him or reading about him with other women. She’d have to ignore women walking out of hotel rooms with him, or his apartment, or even him kissing them in front of her.
The only question she couldn’t answer was how long it would take before Rob would settle down with her and her alone. It would happen, but would it take a few weeks or perhaps a bit longer? She didn’t know, but she was prepared.
Lisa called the next morning sounding distraught. She didn't provide any details, but she was freaked out that she had messed things up with Bill. Lisa recommended that they meet at the Billionaires Club after lunch. “But what if Bill shows up?” Gin asked.
“I want him to. I think that would actually be better, but I’m not sure. Shit, it’s so confusing. I’ll explain later.” As Gin hung up the phone she wondered how things could have gone wrong. Lisa was fun and pretty and wild in bed. For a quiet guy like Bill she was pretty much heaven.
Gin’s comfort level with the Club was such that she didn’t even think twice about what to wear. She grabbed a sundress and some sandals. While not exactly appropriate for a bar, it was fine for a Saturday early afternoon. Besides, who cared? She didn’t need to impress anyone anymore.
/> Nameless goon was manning the door. He took Gin’s card and then ignored her as she walked through the door. The only thing that changed about the Club between visits was the people, and on Saturday afternoon it was practically empty. Martin was at the bar, and he raised a hand in greeting, which elicited a smile from Gin. Even the day people knew her now.
“Gin!” Lisa called out from a booth in a dark corner of the room. Gin wandered over and sat down. Lisa stood up. “Hold tight, I have to use the restroom. I’ll be back with a drink. While you’re waiting, I want you to think as to whether a guy can want something and then be upset you gave it to him.”
Sliding into the booth, Gin replied, “What—“
“Unh unh!” Lisa interrupted, waving her finger. “Just think about it and then we’ll talk.” Lisa wandered off.
Gin couldn’t imagine what Lisa was talking about. Did Bill ask for some kinky sexual thing and become shocked that Lisa was happy to do it? Did he do something crazy and ask Lisa to marry him, only to have her say “yes” and then they both had to deal with that the next day? Shit, Gin thought, it could be anything. As her mind wandered down even crazier paths, Lisa returned.
Placing a rum and Coke in front of Gin, Lisa said, “Okay, I really need your advice.”
Gin looked at her drink. “It’s like one o’clock. A rum and Coke? Really?”
“Whatever. You don’t have to drink it.” Lisa leaned forward and placed her elbows on the table. “First of all, I want to be clear—I am crazy about Bill. He is this amazing guy, who is like the nicest person in the world. He’s also cute and sexy and some kind of financial genius. All of Silicon Valley listens to him. He has this dichotomy that is so amazing—he is kind and generous, but he oozes power.”
“He kind of seemed innocent and vulnerable the other night, to be honest,” Gin replied. “Vin said you’d eat him alive.”
In the Billionaires Club Page 10