<p><a href="https://www.patreon.com/beccabellamy/posts?tag=corruption%20of%20anna%20lee">Click here</a> to read the previous parts of the story.</p><p><img data-media-id="32296982" src="/31/02/3102563e4639f840c5fabc279401de07e886e55dd9f590589428183860ae44b4.jpg"></p><p>“Have you ever had anal sex?” Shane asked.</p><p>They were in his bed, under his gloriously comfortable sheets, with their naked bodies pressed together in post-coital bliss. </p><p>His question caught her off guard, though the answer jumped to mind immediately, “No. Never.”</p><p>“I’d like to be your first,” he said as his hand gently caressed her lower back.</p><p>Anna had seen a variety of clients since she began escorting, but none had captured her interest quite like Shane had. She’d been with him at least once a week since their first encounter and each time they grew closer. The risks of getting too close to a client were always in the back of her head, but she couldn’t help it. She genuinely liked him and it seemed as though he genuinely liked her. He still paid for her time, of course, but it felt different. It felt like the purest form of a girlfriend experience, only she wasn’t faking it with him.</p><p>Perhaps that’s why she barely hesitated when she responded to his inquiry regarding her anal virginity.</p><p>“I think I’d like that,” Anna said as her hand instinctively drifted between his legs and played gently with his soft cock. He’d cum ten minutes ago, so he wouldn’t be getting hard anytime soon, but she enjoyed handling him.</p><p>“Next week then,” he said before kissing her forehead sweetly.</p><p><br></p><p>“What was it like the first time you had anal sex with a client?” Anna asked Jamie as they sat in a quiet corner of the coffee shop.</p><p>A raised eyebrow was the only sign the question might have surprised her. “It wasn’t bad, honestly” she answered before taking a sip from her cappuccino. </p><p>“He offered triple my rate if he could have me back there. I couldn’t say no,” Jamie said with a smile.</p><p>“It helped that he had a small cock,” she said with a smile, causing Anna to laugh. “Why do you ask?”</p><p>Anna used her finger to scoop a taste of whipped cream from her mocha and licked it clean before answering with a sly smile on her face, “Shane wants to do it.”</p><p>“What about you?”</p><p>“I told him I would. I’m actually kind of excited about it,” Anna said as she looked up at her friend.</p><p>“Have you done it before?”</p><p>“No. He’s going to be the first,” Anna answered.</p><p>Now it was Jamie’s turn to smile. “Wow. What does Mark think of that? I bet the cuck loves it.” </p><p>“Actually, I haven’t told him yet.”</p><p>“This is not my area of expertise, obviously, but it seems like he loves being a cuckold and would absolutely love that you were going to have anal sex with Shane. I could see him being angry if you did it without telling him though,” Jamie offered.</p><p>“Yeah, I guess you’re right.”</p><p><br></p><p>Anna gently wrapped her fingers around Mark’s throbbing cock, pressed her body against him, and whispered in his ear, “You like that I fuck Shane, don’t you? You like that he makes me cum with his big cock. You like that I want him to fuck me, that I beg him to fuck me.”</p><p>She stroked him slowly as her dirty talk filled him with cuckold lust.</p><p>“Yes!” he exclaimed as a wave of pent up energy released. It always felt good for Mark to admit just how much he loved being his wife’s cuckold.</p><p>She was careful not to squeeze too tight or stroke him too quickly because she didn’t want her husband cumming. She wanted to draw out his pleasure and push him deeper into cuckoldhood.</p><p>“Do you like that I always suck his cock?” she taunted.</p><p>“Yes,” Mark answered.</p><p>Anna stopped stroking and squeezed the base of his cock a little too hard for his comfort, “Say it,” she demanded.</p><p>“Yes, I like that you always suck his cock. I love it.” Mark was growing more desperate to orgasm with each stroke and naughty whisper into his ear.</p><p>“I never suck your cock anymore, do I?” she asked with full knowledge of his answer.</p><p>“No. Never.”</p><p>Just a handful of months ago that exchange would have deflated Mark and left him soft in her hand, but now it only made his cock throb. He had fully embraced the joys of being a cuckold. He loved that his wife regularly fucked other men. He loved that she gave blowjobs to clients and never wrapped her soft, perfect lips around his cock. He couldn’t help but find the mix of humiliation and pleasure to be utterly intoxicating and every time Anna stroked his cock to an erection and teased him with her paid infidelities he had an overpowering orgasm.</p><p>Anna stopped her slow stroking and gently rubbed her fingers around the head of her husband’s cock. She saw the overwhelming lust in his eyes and her heart swelled with a sense of love and warmth. Little did she know that she had married a man that perfectly fit her deepest desires.</p><p>“I’m going to have anal sex with Shane,” she said, staring directly into her cuckold husband’s eyes. “I’m going to give him my ass. He’s going to be the first man to enjoy fucking my ass, cuckold.”</p><p>“What about me?” Mark asked. “Can I fuck your ass?”</p><p>“No,” Anna answered.</p><p>That was all it took to push Mark over the top. He came a moment after her denial, filling the room with his guttural moans of pleasure and spilling semen onto his stomach and her fingers. She stroked him slowly as the rest of his seed dripped out and rested her free hand on his heaving chest. Anna gently kissed him, slipping the tip of her tongue into his mouth and moaning for her loving cuckold husband.</p><p>“I love you,” she whispered, and he answered in kind.</p><p><br></p><p>Anna felt nervous as she stood outside Shane’s brownstone. She’d followed his instructions and thoroughly cleaned herself before putting on the sleeveless blue and white polka dot dress and heels he’d requested. She looked sweet, like the girl next door going on a first date with a guy she’d been crushing on.</p><p>“You look perfect,” he said as he opened the door and welcomed Anna inside. They shared a tender kiss as he gently caressed her bottom through the soft material of her dress.</p><p>“Would you like a drink?” Shane asked.</p><p>“Yeah,” Anna said with a smile. “I’d love one.”</p><p>Sensing her nerves, Shane made sure the drink was a strong one and offered it to her.</p><p>“You don’t have to be nervous,” he said as she took a generous sip. “I’ve done this before and I promise it won’t be miserable for you.”</p><p>He leaned in to kiss Anna and as their tongues danced passionately he slid his hand far enough up her thigh to feel the heat of desire emanating from between her legs. He stayed close after breaking the kiss, his hand gently rubbing the front of her panties and his lips inches away from hers.</p><p>Anna’s pulse raced and her breath quickened as she leaned back and took another sip from her drink. </p><p>“I’m looking forward to it, you know,” she said, staring into Shane’s eyes. “Something about it really excites me.”</p><p>“What does your husband think?” Shane asked.</p><p>Through a devilish smile Anna answered, “He’s very excited.”</p><p>“I like that,” he said through his own eager grin.</p><p>After finishing their drinks Shane suggested they move to the bedroom to begin the evening’s festivities. On the nightstand he’d laid out a bottle of lube, several toys, and condoms. As he’d promised, he was prepared and ready to ensure Anna enjoyed her first anal experience as much as possible.</p><p>Standing at the edge of the bed they shared a passionate kiss. His hands roamed over her body, caressing her breasts and pulling up her dress to gain access to her bare ass. He’d instructed her to forgo underwear for the evening and she’d done so without hesitation.</p><p>Shane turned Anna around and wordlessly moved her into position on her hands and knees on the bed. Her backside was exposed and she moaned quietly as he slowly ran his fingers over her naked flesh. He moved from her lower back to her ass cheeks to between her legs. He teased her by playing with her labia and brushing against her clit, but he denied her the pleasure of true sexual stimulation.</p><p>The feel of his lips and the soft touch of his tongue against her lower back elicited a moan from the beautiful girl on her hands and knees. His erotic travels continued as he kissed her soft, smooth ass cheeks and between them, coming ever closer to her asshole. She’d waxed it smooth as he’d requested and when he finally exposed it the cool air against the rarely seen flesh made her shudder ever so slightly.</p><p>At first Shane kissed around the hole of his desires, teasing Anna and sending her to a place of wild anticipation. His thumb found her clit at the moment his tongue found her asshole and soon she was on the receiving end of a rimjob and the overwhelming stimulation of her pussy. She arched her back and moaned as his expert touch left her on the brink of orgasm.</p><p>Unwilling to let her climax so early, he pulled his thumb away but continued his tongue’s assault on her anus. He licked eagerly, stimulating the nerves surrounding her anal entrance and driving her wild. Anna was in a place of bliss she never expected to visit on this particular evening.</p><p>A quiet moan of protest escaped her lips as he pulled away from her asshole. Mere moments later she felt his fingers spreading lube over her anus and continuing the stimulation that had already driven her crazy. Once again his thumb found her clit, this time to pleasure her as he slowly slipped a finger into her asshole. </p><p>The discomfort of her first ever anal penetration was overwhelmed by how intensely aroused she felt and his slow clit rubbing only served to increase that sensation. </p><p>“Does that feel good,” Shane asked as he continued to penetrate her asshole with his index finger.</p><p>“Yes!” Anna exclaimed in a breathy voice.</p><p>All of it felt incredible. He had expertly woven together a multitude of stimuli, leaving her nearly overwhelmed and in a place of sexual bliss unlike any she’d ever experienced.</p><p>When he removed his finger Anna felt a surprising pang of disappointment. He didn’t wait long to fill her again though, this time with a butt plug. Shane covered it in lube and reapplied a heavy coating to her asshole before pushing the toy, which was considerably thicker than his finger, inside her. He slowly moved it inside the beautiful escort until the thick part had successfully stretched her ass and he let it come to rest. </p><p>He stepped back to admire how beautiful her smooth ass looked with a black butt plug lodged inside it before stripping off the rest of his clothes and stroking his already erect cock.</p><p>“Turn around,” he ordered.</p><p>Anna spun around in bed to find Shane’s beautiful cock bouncing in front of her. He stepped forward and she eagerly parted her lips to take him into her mouth. She sucked his cock feverishly, thinking of how it was going to feel when he finally took her ass.</p><p>“Fuck that’s good,” Shane groaned. </p><p>Anna’s repeated evenings with Shane had given her enough experience to be an excellent cocksucker for him. She knew that he loved when she swirled her tongue around the head of his cock and that he loved to thrust into the back of her throat to make her gag just a little. He loved when she moaned with his dick in her mouth as the vibrations brought him extra pleasure. He loved to have his hands in her hair and to guide her mouth without forcing her down his shaft.</p><p>“Are you ready?” Shane asked after removing his cock from her mouth.</p><p>“Yes. Please, fuck my ass,” she responded.</p><p>“On your back,” he said with irresistible confidence in his voice.</p><p>Anna moved onto her back and spread her legs, giving Shane access to her ass. He pulled out the butt plug and rolled a condom down his cock. With another generous application of lube to his cock and her asshole he was ready to take her anal virginity.</p><p>Shane moved on top of Anna and kissed her as she parted her lips and eagerly accepted his tongue. She was feverish as she displayed her eagerness to have him inside her. He broke the kiss and stared into her eyes while rubbing his cock around the entrance to her virgin hole. Slowly, he pressed against her anus with his condom-covered cock and Anna did her best to relax and allow him inside. </p><p>“Play with your clit,” he said in a low voice.</p><p>She did, eagerly following his direction as he slowly invaded her ass. She closed her eyes, rolled her head back, and basked in the idea that she was giving a virginity of a slightly different kind to this gorgeous, wealthy, confident man. </p><p>As the head of his cock slipped past her anal ring and inside her Anna gasped. She continued to masturbate as he slowly filled her ass and the mixture of sensations was incredible. When he’d pushed the entirety of his cock inside her Shane leaned forward and they kissed as he let her ass get used to his size.</p><p>Anna ran her hands through his hair and eagerly sucked on his tongue as her anus relaxed and stretched around him. She moaned deeply as he slowly pulled out. Just before the tip slipped from inside her he thrust slowly back in. He was fucking her ass. She shuddered with pleasure. </p><p>She closed her eyes and concentrated on the feeling of him sliding in and out of her. The sensation of him pulling out was remarkably different from him thrusting inside of her and she couldn’t get enough. Anna was certain that if she rubbed her clit even a little she’d climax. </p><p>“That feels so good. Fuck my ass Shane. Fuck my ass!” she exclaimed, giving voice to the intense sensations running through her body.</p><p>At her encouragement he picked up the pace, thrusting harder and faster into her ass. She groaned beneath him, quietly urging him to fuck her in a breathy voice. She had given herself completely to him and he felt intensely satisfied as his orgasm built. </p><p>Anna’s eyes shot open when he pulled out as she felt an intense sense of emptiness.</p><p>“I want your ass from behind,” he said as his chest heaved from the exertion of taking her with such vigorous force.</p><p>Without a word Anna flipped over and offered her ass. Her face was pressed against the soft sheets of his bed as he slipped into her now loose asshole and began fucking her once again. The anal sex was so much more blissful than she’d hoped it would be. </p><p>“Play with your clit,” Shane ordered again.</p><p>She needed no further encouragement. As Anna rubbed a finger over her clit Shane spanked her ass hard, causing her to yelp and sending a surge of lust through her body. She came moments later, and it wasn’t long after that he buried his cock to the hilt in her ass and released his orgasm.</p><p>Shane pulled out and they collapsed on the bed together, both breathing heavily from the exertion.</p><p>“That was amazing,” he said between exhalations.</p><p>Anna responded with a long, slow kiss that affirmed her agreement. She had truly enjoyed him being the first to have her ass.</p><p><br></p><p>Anna woke up to Shane wrapping his arms around her and kissing the nape of her neck. She snuggled closer to him and offered a pleasant good morning moan.</p><p>“Good morning beautiful. I hope you slept well,” he whispered into her ear.</p><p>His breath on her neck tickled and she giggled, “I did. How about you?”</p><p>“Never better,” Shane responded as he pushed his crotch snugly against her ass.</p><p>“Somebody is feeling a bit frisky this morning, isn’t he?” Anna teased as she reached back and grabbed his growing erection.</p><p>Her relationship with Shane had been different from her other clients since the beginning. She’d stayed at his place the first night and each night since then and she did so without asking for extra. He always tipped well, but they’d never talked about it. Instead, Anna did it because it felt so good.</p><p>“Why don’t I help you with that?” Anna said as she pulled the sheets off, moved between his legs, and took Shane’s cock into her mouth.</p><p>A wake up blowjob wasn’t uncommon between them and she found it thrilling to suck him off after a restful night in his insanely comfortable bed. It was almost always quick too. Anna pulled out all the tricks, from using her hand in concert with her mouth to provide extra pleasure to gently fondling his balls as she blew him. Soon his semen erupted from the thick head of his cock and spilled onto her tongue, all of it to be swallowed as a pre-breakfast treat.</p><p><br></p><p>“It was so much better than I thought it would be, baby,” Anna said as she lay in bed with her husband. </p><p>His hands roamed gently over her ass as his mind filled with images of another man’s cock entering a hole he’d never enjoyed. He was uncomfortably hard, but Anna hadn’t yet given him the go ahead to strip and reveal the stiffness of his cuck cock.</p><p>“Did it hurt?” he asked as his concern as her husband overwhelmed his cuckold lust.</p><p>“A little, but only at first. Honestly, there was something about the pain mixing with the pleasure that made it even better. I don’t know that I could really explain it, I just know that I liked it, though I don’t think I could do it regularly with a cock that big.”</p><p>Anna smiled, knowing full well that such a comment would make her hubby’s dick just a little bit harder. </p><p>“Do you think you’d ever let me have you back there?” Mark asked in a quiet voice.</p><p>“No honey, I’m sorry. I think my ass is always going to be reserved for other men. I can’t quite describe it, but there’s something Shane has that you lack that made me want to offer my ass to him. Does that make sense?”</p><p>As much as he didn’t want it to make sense and as much as he wanted to argue with her, Mark understood. Even though they had long since embraced him being a cuckold, they’d never really discussed it, at least not in this way. It was something they both understood without having to talk about it. They loved each other immensely and Anna wouldn’t dream of leaving Mark for another man, but escorting wasn’t just about making money for her. She was getting to experience the kind of man Mark would never be.</p><p>“Would you like to watch?” Anna asked.</p><p>Mark was confused, “What do you mean?”</p><p>“Would you like to watch me have anal sex?” she clarified.</p><p>She’d caught him off guard. He stammered, “Well, I mean, yeah, that would be incredible. How would we do that?”</p><p>Anna rolled away from him and opened her nightstand drawer. She returned to his side with a dildo, a condom, and a bottle of lube and told him to strip.</p><p>As Mark eagerly stripped out of his clothes and tossed them to the floor Anna tore open the condom wrapper, rolled the latex down the shaft of her cock-shaped dildo, and popped open the top of the bottle of lube.</p><p>“Would you like to help, cuckold?” Anna asked. She continued without waiting for an answer, knowing he wouldn’t dream of saying no to her request in that moment. She handed him the bottle of lube and said, “Get my ass nice and lubed up for Shane.”</p><p>Mark poured a generous helping of lubrication on the top of her ass crack and watched it slowly drip down.</p><p>“Rub it in, cuck,” Anna ordered with a newfound boldness in her voice.</p><p>He did as his wife asked and soon her ass was lubed and ready for penetration. </p><p>“Move down there,” Anna said as she gestured to the foot of the bed. “I want you to have a good view as he fucks my ass.”</p><p>When he was in position Anna began to play with her clit and rub the head of the dildo, which was smaller than Shane’s cock, around her asshole. Mark watched intently, his mouth hanging open as a drop of shiny precum formed at the tip of his dick. He wasn’t sure how long he’d last so he hadn’t yet started to masturbate.</p><p>Anna moaned as the head of the dildo pushed into her asshole. There was a hint of soreness from her anal adventure with Shane the night before, but it only served to remind her of the fun she’d had being taken by him. She heard a sharp intake of breath from Mark as she penetrated her ass and began to push the dildo all the way inside her. She gripped it by the plastic balls and eagerly filled her bottom, letting it rest there just as Shane had done with his cock.</p><p>“Fuck me Shane. Fuck my ass,” she groaned. </p><p>Hearing his wife beg her lover to fuck her ass was enough for Mark. He grabbed his cock and stroked eagerly. His eyes were fixed intently on her asshole as it stretched around the dildo and she imagined it was Shane between her legs guiding his erection into parts of her body her husband had never been permitted to go. </p><p>He could see Anna’s orgasm approaching. He’d seen his wife cum enough times to know that when her chest began to heave and her breathing got heavier she was about to climax. He announced his own impending orgasm and let his seed fly as she pumped her asshole with the dildo, having anal sex with another cock for the second time in 24 hours. </p><p>Afterwards, when they were both coming down from a truly blissful set of orgasms, he crawled next to her and gently kissed her soft lips. He’d never felt such love for his wife and she’d never been so sexually satisfied.</p>