<p><a href="https://www.patreon.com/posts/70205054?pr=true">Click here</a> to read the previous parts of the story.</p><p><img data-media-id="90954390" src="/31/02/3102563e4639f840c5fabc279401de07e886e55dd9f590589428183860ae44b4.jpg"></p><p>My first taste of cuckolding happened as a result of a night on Reddit. I was perusing local, kink-related personals – mostly looking for jerk off material, if I’m being honest – when I came across an ad from a girl looking for something specific.</p><p>I don’t remember the exact wording – this was years ago – but I remember that she was very specific about wanting a guy to come to her place to eat her pussy and ass after someone else had fucked her. On top of that she was quite specific about how she was really into verbal humiliation and that she would be humiliating whatever guy she chose to crawl between her legs and put his tongue to work.</p><p>At that point I still didn’t have much in the way of experience with women into kinky play. I’ve already told you about a few of those experiences, but I was still doing a lot of self-exploration where I would find a personal ad I really liked and let it give birth to this wild fantasy in my head. There was something about this girl’s ad that thrilled me. I bookmarked it and ended up jerking off to it over the next several days. I would read it and pull up pictures of guys going down on girls. I would watch videos of the same thing. I would imagine the kind of verbal humiliation that girl might deliver and it would put me in this place of truly insane arousal.</p><p>For some reason I hadn’t even considered messaging this girl at first. I’m not entirely sure why, but I just didn’t. She was in San Francisco so I could have, but it didn’t even occur to me to try and make the fantasies I was concocting a reality for a solid week.</p><p>When I did message her I tried to keep it brief and to not come off as one of those weirdos that’s just looking for some jerk off material via message. She responded within an hour and asked for my phone number. I’ll admit that I was exceptionally nervous about giving out my phone number, though I’m not entirely sure why. I guess I figured that my kink could somehow become public and embarrassing.</p><p>I gave her my number and she called almost immediately. She had a soft, sweet-sounding voice that caught me off guard, though I’m not really sure why. She said that her name was Valentine but that I could call her Val. She told me that I would never, ever be allowed to have sex with her. She told me that I wouldn’t be allowed to take my cock out and masturbate unless she gave me permission and she told me that she might treat me to a handjob someday if I proved to be a ‘good little bitch’. That last part is an exact quote.</p><p>When she asked if I was interested I said yes. The truth was, I was hard. There was something about her that tapped into my submissive side, clearly, because I was genuinely turned on as she described what she expected of me.</p><p>“Are you okay with eating someone else’s cum?” she asked me towards the end of the conversation.</p><p>“Oh, I don’t know,” I said. “I hadn’t thought about that, actually.” I really hadn’t. I don’t know why I hadn’t. I guess I just figured she’d be having safe sex and that someone else’s cum wouldn’t come into play.</p><p>“Okay,” she said. “Well, I’m looking for someone that’s okay eating someone else’s cum out of me, but we don’t have to do that the first couple of times. There’s only a few guys I’m comfortable taking loads from anyway. I want you to think about it, though.”</p><p>“I will,” I said.</p><p>“I’m seeing someone tomorrow,” Val said. “He’s paying for a hotel. I want you to wait in the lobby until we’re done. Then I’ll call you to come up. You get one chance at this. If you can’t follow through I’m moving on. No excuses. Do you understand?”</p><p>“I do,” I said.</p><p>“I’ll send you a message with the hotel info,” she added.</p><p>“Okay. I’ll see you tomorrow,” I replied.</p><p>Just like that the phone call was over and I had a date. It probably won’t surprise you to learn that I looked up a video of a guy eating cum from a girl’s pussy almost immediately. It wasn’t something I’d ever considered before but Val had put the idea in my head and it wouldn’t shake loose. I’ll bet you won’t be surprised to learn that I found that video insanely sexy. I jerked off to it, in fact. I also had an exceptionally pleasurable orgasm as I jerked off to it.</p><p>The next day I showed up at the hotel as directed. I waited in the lobby for thirty minutes before I got a call from Val. She told me which room to go to and that the door would be open so I could let myself in.</p><p>I felt lightheaded as I rode the elevator to her floor. My heart was pounding harder than it had in a long time. I was completely uncertain of what was about to unfold, which was both exciting and nerve-wracking.</p><p>I paused for a moment outside of Val’s door to try and gather myself. Then I pushed it open and stepped inside.</p><p>“Val?” I asked.</p><p>“I’m in the bed, Tyler,” she replied.</p><p>My steps were tentative, though I couldn’t tell you why. I guess I was nervous about there being some sort of unpleasant surprise waiting for me. There wasn’t, though. Instead, I found a pretty blonde girl in the bed. Val wore a lacy robe and a matching black bra and panty set. Her legs were crossed and her toenails were painted a bright shade of red that drew my eyes.</p><p>“Can you follow my rule and abstain from masturbating while you’re here?” she asked.</p><p>I nodded.</p><p>“Good. Take your clothes off and get on your knees,” Val demanded.</p><p>I stripped and dropped to my knees at the foot of the bed. She sat up and smiled at me.</p><p>“Suck on my toes,” she said.</p><p>The request caught me off guard and I took a few moments to register that she wanted me to do something I’d never actually done before. I happily crawled into the bed and wrapped my lips around her big toe, though. I don’t have feelings about feet one way or the other, but it did feel distinctly kinky to be sucking the toes of a woman I’d literally just met.</p><p>“That’s a good boy,” she said.</p><p>I looked up to see what appeared to be a sense of genuine pleasure on her face.</p><p>“Do you want to taste my pussy, Tyler?” Val asked.</p><p>I stopped sucking her toe to answer but she interrupted me.</p><p>“Ah, ah, I didn’t say you could stop sucking on my toe. All I need you to do is nod. Now wrap those pretty lips of yours around my toe once more,” she said.</p><p>I did as I was told.</p><p>“Now, do you want to taste my pussy?” she asked.</p><p>I nodded.</p><p>“Even though another man was just inside me?” she asked.</p><p>I nodded as I felt a sudden surge of lust. As it turned out, the idea of eating her pussy after another man had been inside her was a notion I found quite pleasurable.</p><p>“Do you understand how pathetic that desire is, Tyler? What kind of man wants to taste the pussy of a woman that’s just been fucked?” she asked with a smile. “You, I guess. You want to taste a pussy that’s just been pounded by a big cock. You want to put your tongue where another man just put his cock. You want to put your mouth where his cock went.”</p><p>I nodded again.</p><p>“Kiss my thighs,” Val said.</p><p>Her toe popped free of my mouth and Val spread her legs. I crawled between them and laid on my side so my stiff cock wouldn’t get crushed under my weight.</p><p>“Go ahead, kiss my thighs. Kiss the thighs that another man just laid between. Kiss the thighs that I spread for that other man,” Val said.</p><p>I placed a series of gentle kisses on her thighs. I savored the feeling of her warm, smooth flesh against my lips. I enjoyed the quiet moans she would unleash each time I kissed her. I thoroughly enjoyed the way my cock throbbed with the sort of desire I knew I wouldn’t be able to satiate until I got home.</p><p>“Are you hard for me, Tyler?” Val asked. “Are you hard because you’re thinking about kissing my freshly-fucked cunt?”</p><p>“Yes,” I said.</p><p>“How pathetic,” Val replied.</p><p>I looked up to see her smile. There was something odd-but-delightful about seeing a mixture of lust and joy on Val’s face as she delivered an insult with genuine venom in her voice. I was still so new to the idea of a woman getting off on humiliating a man that it caused a bit of cognitive dissonance. I was, however, thoroughly aroused by it. There was something completely and utterly irresistible about the idea of Val finding pleasure in my humiliation, and of course I found pleasure in it too.</p><p>“Get on your knees for me, Tyler,” Val said. “Now.”</p><p>I moved to my knees in the bed and she looked at my cock. She remained silent as the seconds ticked by, with each seeming longer than the last. I couldn’t tell what she was thinking or why she was studying my genitals so intently and it filled me with a sense of insecurity.</p><p>“It’s always the guys with underwhelming cocks that want to worship me,” Val finally said. “Is it because you know your dick isn’t worth a damn, Tyler? Do you have an innate understanding that you’d disappoint me if we fucked so you choose to focus on doing exactly as I tell you instead?”</p><p>“I don’t know,” I said as I looked down at my cock. I’d never considered it underwhelming, but I didn’t have a lot to compare it to. I’m not as big as the guys in porn videos, but those guys are outliers.</p><p>“I won’t let a guy fuck me unless he’s working with at least eight inches, and he needs to be thick, too,” Val explained. “I don’t see the point otherwise. If I were to let you fuck me, for instance, it would be entirely for your pleasure because your dick wouldn’t do anything for me. Your dick is literally worthless to me, Tyler, which means the only value you can offer me is your willingness to be the little bitch I want you to be.”</p><p>Val moved to her knees and crawled towards me. I watched the soft material of her robe brush gently against her breasts and felt an intense kind of desire move through me. I wanted her, though I wasn’t sure if it was because she’d told me I’d never be able to have her. She got close enough that I could feel her breath against my skin.</p><p>“Your cock is pathetic just like you are,” Val whispered. “The fact that you’re hard as a rock only confirms you pathetic you are. You know you’re not getting any of this and yet you can’t help but want it. I am going to give you a treat, though. I’m going to let you eat my ass while I tell you about the fucking I just took. You’d like that, wouldn’t you Tyler?”</p><p>I nodded.</p><p>Val smiled and leaned a little closer. I thought for a moment she might kiss me or touch me in some way, but she didn’t. She was just teasing me. My heart pounded and it felt like every inch of my body had come alive with desire. I just wanted her to touch me, to offer me some sort of affection, but Val had no interest. She clearly wasn’t there to give me pleasure. The opposite was true. It was my duty to pleasure her.</p><p>She moved backwards, spun around, and laid face down in the bed. She spread her legs and looked back at me. “Kiss my ass, and don’t you dare spread my cheeks to worship my tight little asshole until I give you permission.”</p><p>I fell onto my hands and knees and crawled closer. I lowered my body to the bed and placed soft kisses on Val’s utterly perfect ass cheeks. Her skin was warm and smooth and the idea that I’d soon be kissing and licking her asshole left me excited in a way I didn’t entirely understand. All I knew was that my body clearly desired what Val offered.</p><p>“Spread them,” Val said.</p><p>I grasped her ass and spread her cheeks. For the first time in my life I studied a girl’s asshole in close up. Despite knowing what came out of it, it struck me as beautiful.</p><p>“Worship my asshole, Tyler,” Val said.</p><p>I pressed my face between her wondrous ass cheeks and put my tongue to use. I licked her asshole like I imagined she wanted it done and Val responded by moaning.</p><p>“I greeted him in lingerie,” Val said. “I love greeting a real man in lingerie. I love the hungry look in his eyes as he admires my body. I love that it makes him feel so good to know that I dressed up for him, that I worked to look good, to offer up the body I’m going to give to him for our mutual pleasure. I’ll never do that for you, Tyler. Even if you do a good job today and I invite you back to worship me, I’ll never dress up in lingerie for you. I’ll never present my body that way because you’ll never be worthy of that. All you’ll ever be is a little bitch that I use for my pleasure.”</p><p>I knew it wasn’t my place to respond. It was my place to do as I was told, so I continued to worship Val’s ass. At the time I didn’t really understand that I was playing a small part in her pleasure. She’d gotten what she needed from her lover and then she’d brought me in to execute on the second part of her ritual, which was to humiliate me as she barreled towards the far more satisfying climax. I understand that now, but on our first meeting I didn’t understand anything other than how much I enjoyed doing exactly as she said and going along with her desire to humiliate me.</p><p>“I enjoy the confidence a strong, smart, successful man exudes,” Val continued. “Not for a moment did he think he wasn’t deserving of my body. Instead, he saw it as his reward for being the kind of man he was. He saw it as a perfectly natural thing that I would dress in lingerie for him, go to a hotel room for him, and offer myself to him so we could both experience intense pleasure.”</p><p>I’d never been a man like that and in that moment I suspected I never would be. I’d always been the sort that found it incredible each and every time a girl wanted to have sex with me. Now I understand that my submissive side was always with me, that it was dictating my responses in those moments.</p><p>“He kissed me the way a man like that does. He kissed me with such confidence that my pussy gushed for him. His hands moved over my body with such confidence that I didn’t hesitate to get on my knees when it became clear he wanted a blowjob. Some girls say they don’t like giving head, but I think they’ve never had the chance to give head to the kind of man I met with tonight. It feels so different sucking on a strong, successful, alpha male’s cock. It’s arousing to have him in my mouth, to see the look of pleasure on his face as I blow him. It makes me wet to feel that sense of control as I offer him the kind of pleasure he’s rarely felt. It leaves me absolutely soaked to know that, in that moment, there’s nothing in the world this man wants more than to fuck me,” Val explained.</p><p>She reached back, grabbed a handful of my hair, and pushed down, smothering me with her ass. My lips pressed against her asshole and it became rather difficult to lick her, though I suspect that was the point. She wanted to humiliate me a little more, and pressing my face against her asshole was a fairly good way of doing that.</p><p>“How does it feel to know that you will never, ever be that kind of man, Tyler? You will never make a woman feel like she absolutely has to get on her knees in front of you. You will never, ever inspire a woman to wetness as she sucks your cock. Pathetic men like you don’t make women feel that way. It’s the exact opposite, really. Only a woman like me recognizes your value. There is, after all, a place for men like you in the world. You belong beneath women like me. You are to be used for pleasure and tossed aside. You like that idea, don’t you Tyler?”</p><p>She pulled hard on my hair and lifted my head from between her ass cheeks. I nodded at her. It was the truth, too. I loved the idea. My painfully erect cock was proof of that.</p><p>Val moved forward and flipped onto her back as I rested on my knees. I stared at her perfect breasts for a few moments before looking between her legs. Her pussy lips were slippery and enflamed, likely from the sex.</p><p>“I stripped him naked after the blowjob,” Val said. “I ran my hands all over his beautiful body. I kissed him all over. Our lips met and I sucked on his tongue as he picked me up and placed me in the bed. Then he went down on me. All good men do. He used his tongue to drive me wild just like I’d used my mouth to drive him wild. He got me to a place where I was begging for his cock.”</p><p>Val’s hand moved between her legs and she slipped two fingers into her pussy. Her eyes closed and she used a third finger to rub her clit. She smiled and her lips parted. A moan escaped.</p><p>“Has a woman ever begged for your cock, Tyler?” Val asked.</p><p>“No,” I replied.</p><p>“Of course not. You’re not capable of inspiring that kind of desire. You’re pathetic, after all. You’re a little submissive bitch that will never, ever drive a woman so wild with lust that she’d beg you to fuck her. I begged him, though. I told him how badly I needed his cock inside me. I begged him for it. I begged him to fill my pussy, to give me what I needed,” Val said.</p><p>She pulled her fingers away from her pussy and pointed at it. That was my signal to take my place between her legs and I did.</p><p>“I put a condom on his cock and he moved between my legs. We kissed as I guided his cock into my pussy,” Val said as I stared at her enflamed lips and the pink, wet flesh between them. “He fucked me, Tyler. He fucked me like I needed to be fucked. He fucked me like every woman needs to be fucked. He fucked me like you have never, ever fucked a woman.”</p><p>Val ran her fingers through my hair and took a firm grip. She looked at me and smiled before pulling me to her pussy.</p><p>“Now eat the pussy he fucked,” Val said. “Put your tongue inside me. Taste the sex I had with him. Taste my pussy and understand that your tongue is going where another man’s cock just went. Think about how fucking pathetic that makes you. Think about how hard your dick is because I’m letting you lick the cunt someone else just fucked.”</p><p>I pushed my tongue in her pussy. I tasted the sweetness of her juices. I tasted just a hint of the condom they’d used, too. I might have tasted a little of his sweat or his balls – they’d almost certainly slapped against her pussy lips as they’d fucked, after all – but I couldn’t tell. All I knew was that I was hugely aroused at the idea of licking her pussy after someone else had fucked her. I couldn’t comprehend why and it didn’t matter. I was turned on. That’s all that mattered. It was thrilling in ways I didn’t understand and I embraced that and enjoyed myself.</p><p>“That’s it,” Val said. “Eat my pussy, you pathetic little bitch. Eat the pussy he just fucked. Eat it like a good boy.”</p><p>Val released my hair and I looked up to see her hands move to her breasts. She played with her nipples and arched her back. Her eyes closed and she smiled. I was clearly making her feel good, which only served to deepen my pleasure.</p><p>“My clit,” Val said. “Suck on my clit. Suck on it like a good little bitch. Use that tongue of yours. Make me cum.”</p><p>I moved to Val’s clit and worked it with my tongue. I licked with all the skill I’d developed over years of gleefully going down on girlfriends.</p><p>“This is all you’re good for,” Val said between increasingly loud, lusty moans. “You pathetic little bitch. Your only purpose is eating used pussy.” She pulled hard on her nipples and let out a low moan. “Eat that used pussy. Eat it. Eat the pussy he just fucked. Eat the pussy a real man just satisfied.”</p><p>A few moments later Val had an incredible orgasm. She grabbed two handfuls of the sheets, arched her back, and trembled from head to toe as a wondrously loud scream filled the hotel room.</p><p>When she reached down and pushed my head away from her pussy I relented in my quest to pleasure her and simply watched as the rest of her orgasm played out. It was the most beautiful thing I’d ever seen.</p><p>Eventually Val opened her eyes and sat up. She smiled at me and brushed her blonde hair away from her eyes. “That was lovely, Tyler,” she said in a soft voice filled with kindness. “Thank you.”</p><p>“Thank you for letting me do that,” I said.</p><p>Val offered a genuinely warm smile and moved to her knees. She gestured for me to do the same and then crawled closer. She surprised me with a soft, sensual kiss that included just a hint of tongue towards the end. It would be fair to call it the best kiss of my life.</p><p>“What was that for?” I asked as Val held my head in her hands and smiled at me.</p><p>“That was a reward,” she said. “For being a good little bitch for me.” She laughed, but in a sweet kind of way. It was like her demeanor had changed completely the moment she’d climaxed.</p><p>“I really enjoyed this,” I said. “It would be an honor to get to do it again.”</p><p>Val reached out and wrapped her fingers around my still erect cock. She smiled and stroked me slowly as pleasure enveloped my body.</p><p>“You’ll see me again,” she said. “And next time I might even let you cum.”</p><p>She released my cock and I experienced a brief, overwhelming sense of disappointment. An orgasm would have been incredible.</p><p>“When you cum tonight, I want you to do so as you think of me. Close your eyes and play with your cock while you replay this experience. No porn. No pictures. Nothing but your memory of this. Okay?” Val said.</p><p>“Yes, of course,” I replied.</p><p>“Good. Now it’s time for you to leave. I’ll be in touch when I want to play again,” Val said as she closed her robe and fell back into the bed.</p><p>I got dressed, said goodbye, and left. It wasn’t the last time I heard from Val, though. She was true to her word, and I’ll tell you about my other experiences with her soon enough.</p>