<p>Leo went down on Samantha the first night they met. A friend introduced them at a party and they hit it off right away. They spent most of the night locked in a conversation that jumped topics easily and rarely experienced even a few moments of awkward silence.</p><p>Once they shared their first kiss it felt like a dam had broken and they couldn’t keep their hands off each other. They went from kissing to touching and from touching to far more intimate touching.</p><p>Eventually, they found their way to an empty room in the house and Leo eagerly tore off Samantha’s clothes. Her body was breathtaking. She was unquestionably the hottest woman he’d ever been naked with and for a moment he considered that she was way out of his league.</p><p>He put Samantha in the bed, kissed his way down her slender, fit, naked body and ended up between her legs. He worked her clit with his tongue and even slipped two fingers inside her to penetrate the moaning beauty and enhance her pleasure.</p><p>It was just a few minutes before Samantha reached down, grabbed his hair, and had a loud orgasm.</p><p>Leo sat back with a look of satisfaction on his face. He absolutely loved making a girl cum and the fact that Samantha was better looking than any woman he’d been with somehow made it even better.</p><p>“Wow, Leo,” she said, “I’ve never cum that fast.”</p><p>“It was my pleasure,” he said.</p><p>“I mean it,” Samantha added as she sat up, leaned forward, and kissed him. He wondered if she could taste her pussy on his lips and tongue. </p><p>Her fingers moved between his legs in an attempt to free his cock, but Leo moved back.</p><p>“Hey, don’t run away. You made me feel good. You deserve the same. I promise, I’m very good,” Samantha said as a naughty smile broke across her face.</p><p>Leo kissed her again and said, “I’m sure you are, and I know it sounds weird, but I like the idea of delaying that pleasure a little. Though I suppose that’s a terrible idea if you’re not interested in seeing me again.”</p><p>“Oh, I’m interested, and I’m willing to play your little game. I like a man that can delay his gratification. That says good things about you.” Samantha gave him another kiss, this time with lots of tongue.</p><p>Leo’s cock ached for release, but he wasn’t going to let Samantha see it before they’d even been on a proper date.</p><p>The problem was a matter of size. Leo had learned the hard way that he was smaller than most men. He’d learned that because he’d seen a look of disappointment on the faces of almost every woman he’d dated when they first saw his cock. No one had been explicit about it, but he was certain he’d been dumped numerous times because of it.</p><p>Leo liked Samantha enough that he wasn’t willing to take that chance. He knew she’d have to see his cock eventually, but he wanted to try and make sure that she was enamored with him by the time it made an appearance. If that was the case, maybe she’d be willing to overlook his less than impressive size.</p><p><br></p><p>Leo’s ruse lasted until their sixth date. He’d managed to come up with a variety of excuses to keep his cock in his pants and make sure that Samantha never really got a sense of how small he was.</p><p>By the sixth date, she’d started to suspect something was up, though, and she made it perfectly clear that it was an issue.</p><p>“Okay, what’s going on?” Samantha asked during a particularly hot and heavy make out session on her couch. She’d reached between his legs and Leo had once again gently pushed her hand away. “Seriously, I know you said you like to delay your pleasure, but this is just strange. I mean, what guy doesn’t want a girl to play with his cock? You seem to like me, Leo, so what’s going on?”</p><p>Leo sighed deeply. The moment had arrived.</p><p>“I’m sorry,” he said.</p><p>“Sorry for what?”</p><p>Leo sighed again and stood up. “I’ll just show you,” he said.</p><p>He unbuttoned his pants, slowly pulled the zipper down, and pushed them to the floor. His cock – which measured a little over 3.5 inches when fully erect – made a small tent in his boxer shorts. He pushed them to the ground too, exposing himself to the woman he’d already fallen in love with.</p><p>Leo forced himself to look at Samantha. He needed to see her reaction. He was surprised to find her smiling.</p><p>“It’s adorable!” she said.</p><p>It was not exactly what he was looking for. “Adorable?”</p><p>“Yes, Leo. That is the cutest little cock I have ever seen,” Samantha added. She seemed gleeful, which he found thoroughly confusing. “Come here.”</p><p>Leo stepped closer and his beautiful blonde girlfriend reached up and wrapped her fingers around his cock.</p><p>“Look, I can’t even fit all my fingers around it. This is incredible.”</p><p>It seemed like she was making fun of his size, but she seemed so happy that Leo couldn’t decide if she was disappointed, delighted, or just amused that someone with so little to offer was standing half-naked in front of her.</p><p>Samantha leaned forward and wrapped her lips around his cock. In an instant he disappeared into her mouth. Her tongue moved over the underside of his shaft and cock head, making Leo moan as intense pleasure enveloped him.</p><p>“See, don’t you wish you’d shown me earlier?” Samantha said when she pulled her mouth off his dick. She grasped him in her hand once more and stroked him.</p><p>Leo nodded as he looked down at her. Her hair looked soft and wavy and her blue eyes were bright and full of life. He wondered if he’d finally found the perfect woman. Could it be that she didn’t find his small cock disappointing?</p><p>“Are you embarrassed by your little cock, Leo?” Samantha asked in a sweet, soft voice.</p><p>“I am,” he answered. He already felt comfortable enough with her to be vulnerable in a way he hadn’t really ever been with a woman.</p><p>“You don’t have to be embarrassed. Your cock is smaller than average, of course, but that’s not the end of the world. Lots of women have found happiness with small-dicked husbands.”</p><p>Her continued stroking of his cock made it hard for Leo to feel anything but pleasure, despite the fact that Samantha was using language he would normally have found insulting and humiliating. Even the girls that dumped him in the past hadn’t said he was small-dicked or had a little cock.</p><p>“Husbands?” Leo asked. He couldn’t help but wonder if Samantha was already thinking about being with him in a more permanent way.</p><p>“Leo, a man that eats pussy like you is not to be tossed aside just because he has a small cock. Plus, you’re good-looking, smart, successful, and eager to please. Those are all great qualities for a husband.”</p><p>Learning that Samantha was already making long term plans was the most surprising element of the night, though it brought Leo great joy. He’d felt that way since their first date.</p><p>Samantha released Leo’s cock and reached under her skirt to pull her panties off. He was certain they were about to have sex and he felt a sense of elation.</p><p>Instead, Samantha spread her legs and said, “Eat my pussy, Leo.”</p><p>He dropped to his knees in front of her and did as she desired. She was right about his desire to please. It overwhelmed most instincts. He couldn’t help but do as she wanted.</p><p>“That’s good,” she said while running a hand through his hair. “That’s very good.”</p><p>Her moans made Leo’s cock throb harder. He thought about how good her mouth felt in the few moments he’d enjoyed it and wished he’d had the courage to show her his small cock sooner. Perhaps he’d have already enjoyed a few blowjobs.</p><p>“Your tongue really is gifted, Leo, and that’s good, because with a cock like yours there’s almost no chance you can fuck me like I need to be fucked,” Samantha said.</p><p>“What?” Leo asked. He was dumbfounded. Samantha had been so gleeful about his little cock. He was genuinely surprised that she seemed to be overtly insulting him.</p><p>Samantha looked down at him and smiled before saying, “Leo, sweetheart, I don’t believe I said you could stop eating my pussy.” </p><p>She gripped his hair tightly and forced him back between her legs. Leo didn’t fight it. Instead, he licked her wet pussy.</p><p>“I don’t believe your small dick is going to impede my plans for us, Leo, but it does mean that our sex life is going to be different than you expected,” she said between low, lusty moans. It seemed as though she was getting close to her orgasm.</p><p>This time, Leo knew better than to stop eating her pussy.</p><p>“I’ll let you put your little dick inside me from time to time. Every man is motivated by pussy and I can’t have you losing your motivation to please me, after all. But, it won’t happen nearly as often as you’d like, I can assure you of that.”</p><p>It felt like a different woman was talking to him. The Samantha he’d been dating for the past month was the sweetest, kindest woman he’d ever met. This version felt a little bossy and even a touch dominant. Despite that, Leo’s cock was so hard it was almost painful.</p><p>“I know it’s going to be difficult for you, but eventually you’ll come to understand that your little dick means that you don’t deserve my pussy. It means that anything I give you is a gift and that anytime I let your small cock inside me you should be overwhelmingly appreciative.”</p><p>Samantha’s arousal seemed to grow with each passing sentence. Leo wasn’t sure, but it seemed like taking charge was an aphrodisiac for her. It seemed as though it was the same for him, too, because he felt a steady stream of precum dripping from his cock and onto the floor in front of him.</p><p>“Make me cum, Leo. Make me cum with your talented tongue. Make me cum like a small-dicked man should.”</p><p>Leo pushed three fingers inside her soaking wet pussy and continued to massage Samantha’s clit with his tongue. Moments later, he did as he was told and made her cum. Her thighs trembled and her fingers grasped his hair tight enough that it hurt as she writhed on the couch and enjoyed a long, thrilling orgasm.</p><p>“Fuck, that was so good, sweetheart,” Samantha said as she released her tight grasp of his hair.</p><p>Leo sat back on his knees and admired Samantha’s beauty and the look of relaxed, post-orgasmic bliss on her face. He felt proud of the work he’d done between her legs.</p><p>“Come, sit next to me,” Samantha said as she gently patted the couch cushion.</p><p>Leo did as he was told and was rewarded with the blissful feel of Samantha’s fingers around his slippery, precum-covered cock. She leaned closer as her slow, sensual up and down stroking motion made him tingle with pleasure.</p><p>“Do you understand why you won’t be permitted to fuck me very often?” Samantha asked.</p><p>Leo looked at her and found himself utterly enamored with the beautiful woman sitting next to him. Her eyes were alight with lust, her smiled seemed so much naughtier than usual, and she clearly reveled being in control.</p><p>“I do,” he said.</p><p>“Will you tell me?” she asked as her slow, sensual stroking continued.</p><p>Leo hesitated, but there was no point in waiting or denying that he knew the answer. Of course he knew the answer.</p><p>“Because my cock is too small to make you feel good,” he said.</p><p>“That’s right.” She stroked him faster. “You’ve always known that’s true, haven’t you? That’s why you hid your little dick from me. You knew I’d be disappointed by it. You knew I’d see it and know that it would never be able to give me the pleasure I deserve.”</p><p>For some reason, her words seemed to arouse Leo. He felt a kind of arousal that he wasn’t familiar with. It was as if his entire pelvis had come alive with lust, like the joy of being stroked had spread from the head of his cock throughout his loins.</p><p>“Most women aren’t as open-minded as I am, sweetheart. They don’t understand that a little-dicked man like you can be a far better husband than someone with a long, thick, throbbing cock between his legs. I understand, though, and I’m going to show you that being with a woman like me is exactly what you need.”</p><p>“Thank you,” Leo said. He didn’t even think about it. The words just spilled from his lips. It seemed like the right thing to say in the moment.</p><p>“Trust me, it’s going to be my pleasure, sweetheart,” Samantha said as she leaned closer. “I’m going to teach you that while your cock is truly worthless for fucking me, you are as far from useless as a man can be. You’re the exact kind of man I need to be with.”</p><p>Leo couldn’t believe it, but when she called his cock worthless it only served to stimulate him further. He’d spent so many years being rejected by girls because of his little dick that he found arousal in Samantha’s seeming lust for a man with a small cock.</p><p>“Now I want this little dick to cum, Leo. I want you to spill your seed like a good boy,” Samantha said before kissing his neck and gently running her tongue over his soft skin.</p><p>Leo groaned as she stroked him faster and with a tighter grip. She clearly had skill at manipulating a man’s cock with her fingers.</p><p>“Your cock is worthless, Leo, but you’re not,” she whispered. “Your tiny little dick will never pleasure me, but you will.”</p><p>Her whispered words worked their way into Leo’s brain and found their way to his arousal center. His loins exploded with pleasure as he had an orgasm while considering what his girlfriend had said. He was ready to be what she wanted him to be. He was ready to accept his place, in no small part because so many women had rejected him outright. He was ready for one that wanted him because of his small cock, even if it meant far less sex than he would have wanted.</p><p>“Oh my God,” he said in the aftermath of his climax. “Samantha, that was incredible. That was the best orgasm I’ve ever had.” Every word of it was true. He’d never experienced a climax like that.</p><p>“That’s just the beginning, Leo. I’m going to show you a world of pleasure like you never imagined possible.”</p><p>Leo was hooked. He didn’t care how often she humiliated his cock. He wanted more.</p>