Teaching Him to Love Small Penis Humiliation - Part 6 (Patreon)

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“Be honest,” Peri said. “How does it make you feel to know that your girlfriend is in another man’s bed right now?”

Leo gave the question genuine consideration. Samantha was at Aaron’s. She’d been gone for a little over an hour. Chances were quite good she was actually in his bed. His cock was almost certainly inside her or on its way there. She was satisfying her sexual desires with someone else and she’d called her friend to “cucksit,” for him, as she’d called it.

“It feels complicated,” Leo said. “Or, I guess my feelings are complicated.”

Peri patted the couch next to her and Leo got up from the armchair and sat next to his cucksitter.

“Complicated is okay, Leo,” Peri said as she reached out and caressed his leg. “I want to hear about it. I want to hear everything you’re feeling.”

“I feel jealous,” Leo said as Peri’s touch brought him to a state of heightened arousal. “I feel a little bit inadequate, too. It’s all mixed in together, I guess.”

“You should feel inadequate,” Peri replied. “You are inadequate, after all. I don’t mean to be cruel, but in this case I think it’s just me being honest. Your girlfriend is having sex with another man because you can’t satisfy her. If that’s not a case of inadequacy, I don’t know what is.”

Leo couldn’t hold Peri’s gaze. He looked straight ahead and stared at the carpet. “I know,” he said. “I know it’s true.”

“What else do you feel, Leo?” Peri asked as her fingers moved up his thigh.

“I feel a little nervous that Samantha is going to realize that she doesn’t need me. Every time she’s with Aaron I can’t help but worry that she’s going to decide she’d rather just be with a man that can actually make her cum while also meeting her emotional needs.”

Leo looked over at Peri and saw a warm smile on her face. It calmed him.

“You don’t need to worry about that, Leo. I know Samantha. She’s my best friend, and I can tell you with complete confidence that she intends to marry you. She knows that guys like Aaron are good for one thing and one thing only: Fucking. She knows that guys like you are good for so much more than that. She knows that you’re going to make the perfect husband for her, especially now that you’ve accepted that you can’t satisfy her sexual needs. You don’t know it, but that was the final step for her. Now she knows that she can be with you forever,” Peri explained.

Leo felt some of the tension leave his body and he couldn’t help but notice that Peri’s hand had moved exceptionally close to his cock, which was nearly erect in his pants.

“Is all of that really true?” Leo asked. He wanted one last touch of reassurance.

“It is, Leo,” Peri replied. “Samantha is a different kind of girl. I am too, for that matter. That’s why we’re such good friends. In Samantha’s case, she knows better than most women what she wants in a husband. She knows she wants someone that’s willing to be submissive to her needs. She wants someone that will dote on her forever. She wants someone that will make it his life’s mission to make her happy. She knows that you’re that kind of guy. That’s why you’re here with me and she’s in Aaron’s bed with his big cock sliding in and out of her wet, needy pussy.”

Leo couldn’t help but groan. Despite his misgivings, he liked being Samantha’s cuckold. He found it intensely arousing in ways he still didn’t fully understand.

“What else are you feeling?” Peri asked as her hand moved in small circles on his inner thigh.

“Arousal,” he answered. “Incredible arousal.”

“I can see that,” Peri said as her fingers moved over the small bulge that Leo’s erection had created in his pants. “That’s also why Samantha knows you’re the one for her. She needs a man that finds the notion of her fucking other guys arousing. She needs a man that’s going to be so much more than okay with it. She needs a man that’s going to want to devour her pussy when she comes home from getting fucked by someone else. She needs a man that can find sexual satisfaction while being denied the right to penetrate his wife’s pussy.”

Leo groaned as Peri played with his cock.

“You’re that man, Leo. She knows it. You know it. I know it too. I mean, it’s obvious. Your little dick is hard because you know Samantha is fucking someone else right now. You know she’s coming home tonight with a well-used pussy that she’s going to want you to soothe with your tongue. You know there’s a good chance she’s going to jerk you off and make you cum while she tells you how inadequate you are as a lover.”

Leo hoped that was the case.

“Thank you, Peri,” Leo said.

“For what?” Peri asked.

Leo looked at her and smiled. “For all of this. For being my cucksitter tonight. For reassuring me. For making me feel good about my place in my relationship with Samantha.” He hesitated for a second before finishing with, “And thank you for what you’re doing right now. For teasing me. For making me feel so good.”

Peri smiled and said, “You should thank your girlfriend when she gets home. It was Samantha’s idea to have me cucksit. She told me I could play with you if I wanted. She told me I could have all the fun I desired, in fact.”

Leo looked at Peri and wondered what she had in mind. He knew she was a different kind of girl, just like she’d said.

“Take your little dick out for me, Leo,” Peri said as she removed her hand from his thigh.

Leo unzipped his pants and pulled them down. He freed his cock from the opening in the front of his boxer shorts and looked down. It really was small.

Peri laughed. Leo couldn’t tell if it was purposefully designed to humiliate him or if she simply couldn’t help herself. Perhaps the sight of his small cock was enough to make her chuckle.

“I forgot how small you really are,” she said. “Of course Samantha doesn’t want you inside her. I guarantee she can’t even feel that thing when you slip it in her pussy. I know I certainly wouldn’t find fucking you even the slightest bit enjoyable.”

Peri looked up at Leo. Her gaze was steely as she seemed to have shifted to a more dominant place. “I’ll bet you’ve disappointed a lot of girls with your dick, Leo. Is that true?”

“It is,” Leo replied. “I’m pretty sure I’ve never truly satisfied a girl with it.”

“I’m quite certain that’s true,” Peri shot back. “How could that sad excuse for a dick give any woman genuine pleasure? You really are lucky that Samantha wants to be with you, Leo. You should never, ever let her go. You should do absolutely everything in your power to make sure she stays with you, because you’re going to end up with a deeply disappointing kind of girl if Samantha ever dumps you.”

Leo felt a sense of panic rise up in him again. Peri had touched on something he spent a lot of time worrying about. He knew Samantha was out of his league. He knew she was smarter, better looking, more successful, and more talented than any woman he’d dated. He knew he didn’t deserve her.

“Don’t panic, Leo,” Peri said. “Just resolve to be the best version of yourself possible. Resolve to make sure that you never forget that your place is to serve Samantha’s needs. Remember that your inadequacy is about more than your little dick, too. Aaron is more of a man than you are. He’s taller, better looking, and in much better shape. Not only does he have a bigger cock, but he fucks better than you could ever hope to fuck. Remember your shortcomings and strive to overcome them by being the best boyfriend – and husband if you’re lucky – possible for Samantha.”

Leo felt the panic wash away. It was replaced with the kind of resolve Peri described. He was determined to be everything Samantha needed. He was determined to give himself over to her needs. He wanted to be with her. He wanted everything she offered and he wanted to be everything she needed in a boyfriend.

Peri reached under her skirt, pulled down her panties, and spread her legs. “While you’re thinking about all of that, practice your pussy licking skills. Get on your knees, Leo, and eat my cunt.”

Leo slid off the couch and moved to his knees. He crawled between Peri’s legs and looked at her pussy.

“It’s beautiful,” he said.

“I know,” Peri replied before she reached out, grabbed a handful of his hair, and roughly pulled Leo between her legs. “Now eat it.”

She’d clearly had enough of his talk. She wanted action, so Leo went to work eating her perfect pussy.

“That’s it. No more talking, Leo. Just eat my pussy. Make me cum. Show me that you understand how you can be useful to your beautiful girlfriend. Show me that you understand that your place is on your knees, that your cock doesn’t deserve to be anywhere near a pussy. Show me that you understand that your tongue is what you have to offer,” Peri said as she maintained a tight grip on his hair.

Leo ate Peri’s pussy until she climaxed. Her screams of pleasure filled the house and she pulled his hair hard enough to make him wince.

“Stay there,” Peri said afterwards. “You’re going to make me cum again.”

Leo stayed on his knees and waited to be given further instructions. Peri turned on the TV and flipped channels as his gaze remained fixed on her pussy.

“You’re a good boy, Leo,” she said. “I’m going to give a very good report to your girlfriend. I’m sure she’ll be happy with you.”

Leo smiled. All that mattered was making Samantha happy.

When Samantha returned a little after midnight, Peri was ensconced on the couch and Leo was on the floor. She’d determined that he didn’t deserve to share the couch with her and that he should rest at her feet.

“Was he a good boy tonight?” Samantha asked.

“He was wonderful,” Peri said as she smiled at her friend and reached out to run her fingers through Leo’s hair as he looked up at his girlfriend.

Samantha’s hair was a little bit messy and much of the makeup she’d carefully worked on before she left had been wiped away, no doubt because of the vigorous sex she’d had.

“How was Aaron?” Peri asked.

Samantha flashed a bright, giddy smile. “Even better this time,” she said. “There was something about being in his bed. It’s like it made him more confident to fuck me the way I needed.”

“Lucky you,” Peri replied. “The cuckold made sure I had a few lovely orgasms of my own, though they obviously weren’t the kind that a big cock can deliver. His tongue is a decent substitute, though.”

Leo had used his tongue to bring Peri to three orgasms during the evening. She’d teased his small cock and let him play with it a little, but he’d been forbidden from cumming, which is why his underpants were soaked with precum.

“Thank you for watching him,” Samantha said.

“My pleasure,” Peri replied as she stood up and gave her friend a hug. She turned to Leo, smiled, and said, “Have fun tonight, cucky,” before heading out.

After Peri had left, Samantha offered Leo her hand and helped him to his feet.

“Did you have fun tonight?” she asked while leading him to the bedroom.

“I did. Thank you for asking Peri to come over,” Leo replied as he admired his girlfriend’s long legs and tight ass.

Samantha spun around once they were in the bedroom. She pulled Leo close and kissed him softly. “Did you enjoy eating her pussy?”

Leo’s cock was stiff almost immediately as Samantha embraced him. “I did,” he said.

The truth was, the whole thing felt spectacularly naughty. He’d spent the night licking someone else’s pussy and being talked to like the small-dicked cuckold he was, all while his girlfriend was out fucking someone else. It was, in its own way, incredible.

Samantha stepped back and sat on the edge of the bed. She pulled the hem of her dress up around her hips and spread her legs as she asked, “Did you enjoy knowing someone else was fucking me?”

Leo nodded as he looked up from between Samantha’s legs and met her gaze.

“Did you enjoy knowing that someone else was fucking me because your cock is too small to make me cum?” Samantha asked.

“I did,” he answered.

“Why don’t you get on your knees for me?” Samantha said.

Leo dropped to his knees and crawled towards Samantha as she beckoned him closer with a finger.

“Aaron spent quite a lot of time in my pussy tonight,” Samantha said as she pulled her panties aside. “It was exactly what I needed. It was what I can’t get from you because you’re just not man enough to fuck me like a woman needs to be fucked.”

Leo could smell the sex emanating from Samantha’s pussy. He found it intoxicating.

“You know that now, don’t you Leo? You know that your little dick makes it so that you can’t possibly give me what I need, sexually speaking.”

Leo looked up at his beautiful girlfriend and nodded. “I do,” he said.

“You know that I love you, right?” she asked.

“I do,” Leo said.

“Good. I want you to worship my pussy. I want you to worship the pussy that someone else fucked tonight. I want you to worship my pussy and think about spending the rest of your life doing that very same thing. I want you to think about the fact that we’re going to get married some day and you’re almost never going to be allowed to fill me with your disappointing dick. Will you do that for me?”

Leo nodded. “I will.”

“Go ahead. Worship my pussy, my small-dicked cuckold boyfriend.”

Leo’s cock throbbed as he moved between Samantha’s thighs and tasted her perfect pussy. He tasted the juices of sex with another man. He tasted the condoms they’d used. He tasted the sweat they’d generated.

“That feels so good, baby,” Samantha said as she leaned back on her elbows. “Lick my clit. Make me cum.”

Leo did as his girlfriend commanded. He licked her clit. He listened as her moans got louder. He felt the way her thighs seemed to vibrate on either side of his head. Eventually, she reached out to grab his head and hold him in place while she experienced the orgasm she craved.

“That was beautiful, Leo,” Samantha said as she leaned forward and softly kissed his lips. “Would you like to cum?”

“I would,” he replied.

Samantha smiled and moved into the bed before inviting Leo to join her. It wasn’t long before her body was cuddled up against his and she had her fingers wrapped around his cock.

“I love you, Leo,” Samantha said as she stroked him.

Leo smiled. “I love you too.”

“Do you like being my cuckold boyfriend, Leo? Do you like the relationship we have?” she asked.

Pleasure spread through Leo’s loins as he answered, “Yes. I love it.”

“You don’t mind that you’ll rarely get to fuck me, that I might not even let you inside me on our wedding night?” she asked.

“I don’t mind,” he said. “I understand it. I want to fuck you, of course, but I understand that my cock isn’t capable of giving you what you need. I understand that I don’t deserve to fuck you.”

“That’s true, Leo,” Samantha said. “You don’t deserve to fuck me. You never will. Your little dick will never deserve my pussy because your little dick will never satisfy me.”

The pleasure built between Leo’s legs. He felt his balls tighten as his cock throbbed.

“I’m not the only woman that feels that way, Leo. Size matters and you don’t have what it takes to please a woman. You have never had it. It’s your place to be a cuckold. It’s your place to be denied the pussy you crave because you can’t please a woman with your dick,” Samantha continued.

“Fuck...Samantha,” Leo said. 

He could barely think straight. He was overwhelmed with arousal.

“Cum for me, Leo. Cum for me and show me that you know your place. Show me that you want to be my husband. Show me that you want to be with me forever. Show me that you understand that you don’t deserve my pussy,” Samantha said.

Leo didn’t have a choice. His orgasm was inevitable. It washed over him in a wild rush. He lifted his hips towards the ceiling and semen sprayed from the tip of his cock.

“That’s good, Leo,” Samantha said. “So good.”

Leo savored the pleasure that rushed through him. He closed his eyes and smiled as Samantha kissed his neck.

“Thank you,” he said.

“You’re welcome, sweetheart,” Samantha replied.

Leo was hers. He would always be hers. He knew he couldn’t resist her. He knew he needed to be with her. He wanted to be her cuckold. He wanted to be her husband. He wanted to be hers forever.