<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="98613413" src="/2f/00/2f0078b07eafd6c8c0337b6fdb01cc83e66df680ba88c974b212df0560635b13.jpg"></p><p>After my second encounter with Val, I couldn’t stop thinking about cuckolding. It was on my mind every time I masturbated, which turned out to be a daily experience, sometimes two or three times a day. There was something about the idea of cuckolding that turned me on like nothing else ever really had and I couldn’t help but follow my desire.</p><p>That’s how I ended up spending a night serving Judy and Mark. They were an older couple – I’d guess late 40s for both of them, though they never told me their age – that I met on Craigslist (this was before Craigslist shut down its personals section). Most days I’d check the ads for anything having to do with cuckolding, and more often than not I’d find something that inspired a rather thrilling masturbation fantasy.</p><p>On this particular day I found a post from a couple seeking a man like me. I don’t remember the exact wording, but the gist was that the couple wanted a submissive cuckold to play with. They were both interested in dominating the cuckold and pushing his limits, though the post didn’t offer any specifics as to what that would mean.</p><p>Had I found that post after my first meeting with Val, I probably would have enjoyed masturbating to the idea and moved on with my life. My second meeting with Val had supercharged my desires for cuckolding, though, so I sent a reply. I tried my best not to sound pathetic or like I was begging. I explained a little of my submissive journey and I was up front about my lack of experience.</p><p>I figured I’d never hear back from them. After all, if I’d sent a response it likely meant that hundreds of other guys in the Bay Area had done so too. Imagine my surprise when I received a reply. It was two days after I’d first seen the post on Craigslist. It was from Judy. She asked me to meet her the next day. She provided a time and a place. She said if I wasn’t there on time she’d assume I wasn’t serious and I wouldn’t hear from her again. She said to wear a yellow shirt so she’d know it was me.</p><p>I’ll admit that I was nervous. All I knew about Judy and Mark was what they’d put in their fairly brief post. I hadn’t seen a picture. It was entirely possible it was just a guy running some sort of scam. Judy had asked me to meet her in a public park, though, so I felt safe going to that first meeting.</p><p>I showed up early and sat on the bench Judy had described. It was a lovely park with an even lovelier few of the bay. I tried my best not to study every single person that walked by, but I couldn’t help it. I knew nothing about the woman I was supposed to be meeting and so every woman could have been her.</p><p>Finally, at the exact time Judy had specified, a slender, pretty blonde sat on the bench. “Tyler?” she asked.</p><p>I nodded. “Judy?”</p><p>She nodded and smiled. “You’re cute.”</p><p>“Oh, uh, thank you,” I said, though immediately I felt stupid for my inability to come up with a quick response. “You’re beautiful,” I added.</p><p>“That’s true,” Judy replied before offering a confident smile. Most women demurred when a man called them beautiful. Her acknowledgment was an appealing change of pace. “My husband Mark and I aren’t interested in a long, drawn-out process. We’ve found that it’s fairly easy to discover if a man is going to be a suitable cuckold.”</p><p>I nodded as I wasn’t sure if Judy was expecting a response.</p><p>“My husband fucked me right before I left to meet you. We don’t usually use condoms, but in this case we made an exception. The used condom is in my purse. It’s full of his cum, of course. I’d like you to consume his cum right here,” Judy said. “If you’re willing to do so, you’ll be invited to play with Mark and I this weekend. We’ll rent a hotel room and you’ll get to be our submissive cuckold for an evening. Will you consume his cum?”</p><p>I hadn’t consumed an entire condom’s worth of cum with Val, but I’d gotten a taste. I knew it was a little bit crazy to agree to drink a stranger’s cum, but that too was basically what I’d done with Val. It’s not like I’d ever met the man that had fucked her. It didn’t seem like much of a leap to agree to Judy’s terms.</p><p>“Yes, I’ll do it,” I said.</p><p>She offered the same sort of confident smile that I’d seen from Val. It struck me as the look a dominant woman gets when a man willingly submits to her. Judy opened her purse, reached inside, and pulled out a tied off condom. “Let me untie it for you,” she said. Her delicate fingers loosened the knot and she handed me the condom. “Now drink. Prove that you’re worthy of night of the sort of pleasure only a cuckold can truly appreciate.”</p><p>I looked around to make sure no one was watching and quickly upended the condom. I poured the lukewarm cum into my mouth and was nearly overwhelmed by the taste. It was so much stronger than sucking a little bit of cum from Val’s fingers. I nearly gagged and spit it up, but I managed to hold it in my mouth.</p><p>Judy reached over and rubbed my thigh. “Swallow, Tyler,” she whispered. “Swallow my husband’s cum. Prove to me that you’re a worthy cuckold. Prove that you deserve to spend Saturday night as our submissive toy.”</p><p>I swallowed as Judy’s gentle touch and softly-spoken words lured me into a state of intense arousal. The cum burned going down and left a terrible taste in my mouth, but I was hard as a rock by the time it hit my stomach.</p><p>“Very good,” Judy said as she closed her purse and stood up. “I’ll be in touch with the time and location for Saturday night. I’ll see you soon.”</p><p>“Thank you,” I said.</p><p>“Oh, and no orgasms between now and then,” Judy added. “A cuckold is most useful when he’s desperate to cum.”</p><p>“Of course,” I replied. “I won’t masturbate.”</p><p>Judy smiled, stepped closer, and leaned down. She gave me a kiss on the cheek and whispered, “I promise, Mark and I are going to give you the most memorable night of your life.”</p><p>I was still hard as she walked away. I was absolutely certain she would deliver on her promise, too.</p><p>Had Mark and Judy rented a room at some nasty motel I probably would have skipped out on meeting them. When I saw that we’d be meeting at the Four Seasons, I was all in. I don’t know why that made me trust that the night would go well, but it did.</p><p>I knocked on the door to their room at 7:30 p.m., just as Judy had instructed. She answered the door in a fluffy white robe. I glanced at her freshly-painted red toenails before she stepped aside and said, “Come in.”</p><p>I entered the room expecting to meet her husband, but it was just Judy and me. “Remove your clothes,” she said. “Right now.”</p><p>I stripped without thinking about it. Judy gathered my clothes and placed them in the safe installed in the closet. I watched it shut, knowing full well that it meant that I wouldn’t be able to leave unless Judy unlocked the safe (I wasn’t willing to be on streets of San Francisco without my clothes).</p><p>Any fears I had were quickly assuaged when Judy opened the robe and let it fall to the floor, revealing her naked body. Her breasts were small and surprisingly perky for a woman her age and her pubic hair looked freshly-trimmed.</p><p>“Mark will be here soon,” she said. “It’s a cuckold’s job to prepare me for him.”</p><p>“Of course,” I said. “What can I do?”</p><p>Judy stepped closer and smiled. She didn’t get close enough to touch me, but my cock responded by getting hard anyway.</p><p>“You can start by getting on your knees,” she said.</p><p>I fell to my knees and looked up at her.</p><p>“Now kiss my feet,” Judy demanded.</p><p>I lowered my head to the floor and planted soft kisses on her feet. Her skin was warm and delicately perfumed, likely from some sort of lotion. I worked my way up each foot and kissed both of her ankles before working my way back down. I kissed each of her toes, too, an act that seemed to amuse her as she chuckled.</p><p>“You may kiss my legs,” she said. “Stay below my knees, though.”</p><p>I showered both of her legs in kisses. My lips moved over her skin as Judy purred like a woman enjoying her new toy.</p><p>“Look at up me,” she demanded.</p><p>I looked up and Judy grabbed a handful of my hair. She pulled hard as an aggressive look washed over her face. I winced in pain, but I didn’t dare move. It wasn’t the first time a woman had taken pleasure in hurting me, after all.</p><p>“Not all cuckolds have disappointing cocks,” she said, “but you do.”</p><p>I felt self-conscious as Judy looked at the erection between my legs.</p><p>“I like that, though. It’s more fun to play with a cuckold that knows he couldn’t hope to pleasure me like my husband does,” she continued. “You’ll understand when you see his cock, but Mark is a physically gifted man. I’ve had other men, but none has compared to him. We’ve been together for fifteen years and I still fantasize about his cock. I can assure you that no woman will ever fantasize about your cock, Tyler. Though I suspect you know that. I suspect that’s why you’re on your knees in my hotel room, isn’t it?”</p><p>I nodded as my cock throbbed. Judy was giving me what I’d come to crave. She was taking control and doling out a small-but-potent dose of humiliation.</p><p>“You’re going to dress me,” she explained. “You’re going to make me look beautiful for the man that can actually satisfy me with his cock. Do you understand?”</p><p>I nodded.</p><p>“Good. If you do a good job I’ll let you taste my pussy before Mark arrives,” she added before turning and walking towards the bed. “Come.”</p><p>I stood and followed. I saw a beautiful black lingerie set laid out on the comforter. It was almost certainly the sort that cost an arm and a leg. There was no question it was going to look beautiful on her.</p><p>“Start with the bra,” Judy said.</p><p>I picked up the bra and she held out her arms. I slipped her hands through the straps, pulled the bra into place, and moved behind her to attach the clasps. Judy adjusted her breasts in the cups and when I stepped in front of her once more they looked perfect.</p><p>“Now the garter belt,” she instructed.</p><p>I picked up the garter belt, studied it for a moment, and then attached it to her waist. She treated me to the simple pleasure of running her fingers down my back as I bent over in front of her. It was delightful enough that I couldn’t help but moan.</p><p>Judy sat on the edge of the bed and extended one of her legs. “Now the stockings.”</p><p>I grabbed one from the bed, bunched it up in my fingers, and gently placed it on her foot. I pulled the nylon up her leg as she smiled down at me.</p><p>“Mark has always loved the way stockings look on me,” she explained. “They drive him wild, even to this day. I always wear them for him. Have you ever been with a woman that enjoyed dressing in lingerie for you, Tyler? Have you ever inspired that sort of desire in a woman?”</p><p>“No,” I replied. “My ex-wife almost never wore lingerie.”</p><p>“No, of course not,” Judy said. “A man like you doesn’t inspire a woman to want to wear lingerie, Tyler. You don’t inspire a woman to want to be fucked. Mark does. He makes me want to look good for him. He makes me want to entice him into our bed. He makes me want to seduce him, to show him that I’m still the only woman that can satisfy him like he deserves.”</p><p>My cock ached in a way I can’t even explain. There was something about the way Judy so casually humiliated me that I found impossibly arousing. I gathered the second stocking and placed it on her foot. I pulled it up her leg as she smiled.</p><p>Judy stood and said, “Now attach the garters.”</p><p>I glanced at her pussy before doing as instructed. It took a little longer than I expected – I’d never attached garters before – but I figured it out. She looked splendid when I was finished.</p><p>“Very good,” Judy said. She plucked the panties from the bed and handed them to me.</p><p>I held them at her feet and Judy stepped into the sexy black panties. I pulled them up her nylon-clad legs and over the garters. They fit snugly against her pussy, completing the outfit quite nicely.</p><p>“You’ll find a pair of heels in the closet,” she said. “Retrieve them. Stay on your hands and knees. I like to see a cuckold crawl.”</p><p>I crawled to the closet as instructed. It was humiliating, but of course that was enthralling. I grabbed her heels and crawled back. I set the shoes at her feet and Judy stepped into them. Somehow she looked even sexier.</p><p>“You did a good job,” she said.</p><p>I smiled. My cock throbbed. That meant I was going to get a taste of her pussy.</p><p>“Come here,” she said.</p><p>I crawled closer. Judy grabbed a handful of my hair. She pulled her panties aside and stepped closer. My lips found her pussy. I pushed my tongue inside her.</p><p>“Get me wet, cuckold,” she said. “Get me wet for the only cock that can truly satisfy me. This is all you’re good for. You’ll never be able to satisfy a woman with that cock of yours. You’ll never be able to take control, to fuck a woman like she truly needs. This is what you’re good for. This is how you can be useful.”</p><p>She kept me between her legs for far longer than I expected and every second of it was delightful. She kept up the verbal humiliation for the entire time, too. It was exquisite, to the point that I was a little disappointed when there was a knock on the door.</p><p>I looked up to see a bright smile on Judy’s face. “He’s here,” she said. “Stay right where you are.” She walked past me, paused for a moment, and looked over her shoulder. “You’re going to be a good cuckold, aren’t you?”</p><p>I nodded. I was going to do whatever it took to be a good cuckold.</p>