<p><a href="https://www.patreon.com/beccabellamy/posts?filters%5Btag%5D=advice%20from%20a%20mistress">Click here</a> to read the previous parts of the story.</p><p><img data-media-id="75865799" src="/31/02/3102563e4639f840c5fabc279401de07e886e55dd9f590589428183860ae44b4.jpg"></p><p>Dear Becca,</p><p>Jacob kind of freaked out last night. I’d denied him for a week and I had him handcuffed to my bed (the cuffs were really fun, by the way). I was naked, he was naked, and I was playing with his cock. He was so, so hard and he was doing that thing I’ve come to love where he’d writhe and moan as I touched him. Even when he wasn’t talking it was like he was begging me to make him cum.</p><p>I felt like I was just as turned on as he was. I felt genuine wetness between my legs. I could actually feel a few drops running down my legs. It was incredible.</p><p>Then I touched his asshole. I’d been fantasizing about it for a little while, to be honest. Maybe it’s weird, but I just love the idea of Jacob giving me his ass, even in a small way. Something about it seems so naughty and I found myself getting crazy for it. So, I pressed my finger against his asshole while I was playing with his cock.</p><p>“Sarah, no!” he said. He yelled, really. It was the look on his face that was worse, though. It was like I’d betrayed him, and I guess I kind of did.</p><p>I think I probably could have apologized and gone back to teasing his cock, but I wanted to talk about it so I uncuffed him, apologized, and asked why it upset him so much.</p><p>I didn’t get much out of him. His cock deflated pretty quickly and he wasn’t interested in playing. I apologized again this morning and he said everything was fine, but it felt like he was still mad at me.</p><p>I’m not sure what to do here. Can you help?</p><p>Sarah</p><p>~~~~~</p><p>Dear Sarah,</p><p>The bad news is that you made a mistake. The good news is that you can fix it.</p><p>It sounds to me like you unknowingly hit one of Jacob’s limits. His reaction makes it seem like he’s not the slightest bit into anal play (don’t worry, you can fix that) and he likely felt some version of betrayal when you attempted to introduce anal play into your domination session.</p><p>Essentially, you very lightly breached the trust that exists between a domme and her submissive. Thankfully you didn’t try to stuff a massive dildo in his ass or insist that he take your finger. Releasing him from the cuffs and apologizing was a good move. It showed Jacob that you recognized his discomfort and that you’re flexible enough to respect his limits.</p><p>There were really two mistakes. The first was not sharing your desires with Jacob before you played. I know it can seem fun and sexy to surprise your submissive, but you’re so early in the process that you should really talk before you do something you’ve never done before. If you had shared your desire with Jacob he might have been able to overcome his fear of anal play.</p><p>The second mistake was, of course, trying to play with his asshole. You saw the result of that and you learned your lesson.</p><p>I said you could fix it and I firmly believe you can. Ultimately, every good submissive craves his domme’s pleasure more than anything. I believe Jacob is a good submissive and that he finds genuine pleasure in submission, which means it should be fairly easy to move past his fear of anal play, especially since that fear is likely rooted in outmoded notions of what it means if a straight man lets someone penetrate his ass. You just have to help Jacob push through those fears by letting him know that it would bring you great pleasure to introduce ass play to your relationship.</p><p>I recommend first talking to him about it outside of the bedroom or a sexual situation. Share your desire with him and tell him that you’re not going to do anything that he’s not comfortable with. Then, make it clear – use a firm tone but try not to veer into being bossy –that you expect him to be open to expanding his sexual horizons. Make sure you reassure him that his pleasure is always on your mind and that if he offers his trust you’ll make sure to introduce him to a world of sexual satisfaction he never imagined possible.</p><p>You’ve discovered that dominating Jacob brings you great pleasure. It might bring you the most intense sexual satisfaction you’ve ever experienced. As a submissive, Jacob is the same way. You’re showing him sexual pleasure like he’s never experienced before. However, he’s also required to be a great deal more vulnerable than you. He’s giving himself to you and trusting you not to push him too far. As his domme it’s your job to earn and maintain his trust in each session.</p><p>Ultimately, the best way to guide your submissive to where you want him to be is to think about your mutual pleasure. The more time Jacob spends in that deeply satisfying state known as subspace, the further he’ll be willing to go for you.</p><p>Don’t worry. You’ll get better as a domme. Just remember that earning your submissive’s trust is the most important element of being a good domme. Once you have his trust you can take him anywhere you want him to go. You have to earn it, though.</p><p>Earn his trust and he’ll give you his ass. Eventually, he’ll beg for you to take his ass. Then, a whole world of wondrous possibilities will open up in front of you.</p><p>I hope this helps,</p><p>Becca</p><p>~~~~~</p><p>Dear Becca,</p><p>Thank you so much for your advice. It worked! It took a handful of conversations and a little practice, but last night I penetrated Jacob’s ass for the first time. It was really hot!</p><p>What you mentioned about vulnerability really stuck with me. I think that’s part of what I like so much about dominating him. It was particularly true last night. Jacob was on his back and I’d oiled his cock and balls up to make it even more pleasurable for him. He was cuffed again and he looked sweet and a little bit scared and it was a massive turn on, mostly because he was willing to do it. He was happy to push through something that was a little bit scary and he was happy to do it for me.</p><p>Let me rewind just a little, though. First off, you were mostly right about Jacob’s fears. In his case, it turned out he was really worried what I’d think of him if he liked anal play. Men can be so silly sometimes, can’t they?</p><p>It required a few conversations for me to actually convince Jacob that I wouldn’t think of him as gay or bisexual or weird or a freak.</p><p>It was during those conversations that I learned that part of the pleasure of dominating Jacob is in making him enjoy it. I kept thinking about how hot it would be to have him writhing in my hand and begging me to finger his ass or fuck him with a toy because he wanted it, not because he was offering it to me as a form of submission. The idea of transitioning him to that place made me feel genuinely powerful in that way that’s so fantastically arousing.</p><p>Last night I put it all into play. I wanted to make it as pleasurable as possible for Jacob, so I dressed up in a black lingerie set. I’ve never worn anything like it before, but it was one of those bra, panty, garter belt and stocking sets that I feel like I only ever see on Instagram models. It looked surprisingly good on me and Jacob definitely thought so. He was practically panting when I stepped into the bedroom in it.</p><p>He wasn’t cuffed at that point. I wanted my intentions to be a little bit of a surprise so I crawled into bed and we did some very sensual kissing as I got him worked up to a splendid erection. By that point I think he’d been almost two weeks without an orgasm – I never did make him cum after that first aborted attempt at anal play – so he was definitely ready to go.</p><p>“I want to be in charge tonight,” I whispered as I squeezed his balls.</p><p>“Okay,” Jacob said.</p><p>I’m pretty sure he would have agreed to anything at that point, but I also took it as a good sign that he was willing to give me his trust.</p><p>“Are you going to be good for me?” I asked.</p><p>He nodded and I rewarded him with the kind of deep tongue kiss that he loves so much. I felt his cock throb in my hand and released him. I’m pretty sure he would have cum right there if I’d kept up the stroking.</p><p>The handcuffs came out next. I probably use them too often, but I really love how they make it impossible for Jacob to do anything but lie there while I play with him. I suppose it would be even hotter if he could just leave his hands at his sides and not move them, but I don’t think he’s far enough in his submission to do that. I think he’d have a hard time controlling his desires at a certain point.</p><p>I got the oil out, coated my hands, and took his cock and balls in my fingers. I stroked him slowly, doing it to tease more than to make him cum. I wanted him in that place of insane desire that I absolutely love. I can’t explain it, but I get so turned on when Jacob is like that. I guess that’s just my lust for power and/or control, because that’s the place where he seems ready to do literally anything I want.</p><p>“Your cock is so hard for me,” I said.</p><p>“Your hands feel incredible,” he replied.</p><p>“Does that mean you want to cum, Jacob? Do you want me to give you an orgasm?”</p><p>I love how little differences in language can change the meaning of something. It’s small, but saying that I’m going to give him an orgasm instead of saying I’m going to make him cum make it feel like a more dominant exchange to me. It makes me feel powerful and in control and I like to think it makes it clear to Jacob that I’m in control.</p><p>“Yes, please, Sarah, please give me an orgasm. Please let me cum,” he begged.</p><p>I know some dominant women – at least from what I’ve read – don’t really like the begging stuff. It seems like they see the guy as less than a man when he’s begging. I’m the opposite, though. It turns me on. It really, really turns me on. I love seeing Jacob writhing in bed and begging for what he craves. I love that I have the power to give it to him.</p><p>“Only good boys get to cum,” I said.</p><p>He let out this little groan that I know means that he likes something and he’s a little embarrassed to like it. I get it. Some men probably don’t want to like being called a good boy, but Jacob definitely likes it. I like it too. I like it when he’s my good boy. I like it when he gets a little embarrassed about it, too.</p><p>I was struck by an idea as I played with him. I wanted to try a different way of getting to anal play. I released his cock and straddled him. I pulled aside my panties and rubbed my pussy over the head of his cock. I saw him have that reaction that men sometimes have when they’re desperate for sex. It was like I offered him a little taste of the most pleasurable thing in the world and then took it away.</p><p>“Do you want to be inside me, Jacob? Do you want to feel my tight pussy around your cock?” I asked. I delivered it like I was a pornstar, too. It felt good, though. I was just as lost in my desire as he was, to be honest.</p><p>“I do, Sarah. I do. I want to be inside you. Please, take me inside. Ride me. Fuck me,” he said.</p><p>I’ll tell you, there was something really hot about hearing him ask to be fucked. I know he wasn’t actually asking me to fuck his ass, but holy shit did it turn me on. It clicked like that’s what he was asking for and I felt this explosive kind of desire.</p><p>I sat on his cock. He was slick with oil and I was wet enough that I honestly didn’t feel all that much – Jacob has a nice cock but he’s not huge or anything – but it wasn’t about being penetrated. It was about having control over Jacob. It was about teasing him. It was about driving him absolutely mad.</p><p>I didn’t ride him. I just sat on it. I just took him inside me. I gave him what he wanted, but not all of it. The look on his face was intoxicating. It wasn’t pain. It was more like agony. He was so close to having what he wanted – which was for me to fuck him – and yet I was still denying him.</p><p>I reached back and played with his oiled up balls. I rubbed them and squeezed them and then I moved my fingers to his taint. Some of the oil had dripped down so it was nice and slick. I kept my eyes on his face for any sense of discomfort or fear, but I saw nothing.</p><p>“Does that feel good?” I asked.</p><p>Jacob nodded. He didn’t seem to want to say it, but I think he liked that I was so close to his asshole.</p><p>I moved my fingers towards his asshole. I didn’t rub it, but I did rub all around it. I teased the flesh near his asshole.</p><p>“Do you want to make me feel good, Jacob? Do you want to be a good boy for me?” I asked as my fingers continued their slow, circular motion around his asshole.</p><p>“I do. I really do,” he said in that wildly lusty kind of way.</p><p>I should say that I was hugely aroused at that point. My heart was pounding. My pussy was soaking wet. It was all at the idea of getting Jacob to give himself to me and let me take his ass. It was just going to be a finger, but there was something so fucking hot about the idea of him asking for it. I didn’t want to take it. I wanted him to tell me to take it. I wanted him to give me permission.</p><p>I moved my hips back and forth just a little. I kept it nice and slow. I knew I was pleasing Jacob’s cock. I knew he could feel the extreme wetness and heat of my pussy. I knew by the look on his face that he was having a tremendously good time.</p><p>“Sarah…please…” he said.</p><p>I rubbed my fingers over his asshole. My touch was delicate. I just wanted to introduce him to the sensation. I moaned as I did so. I moaned because it turned me on. I moaned because I wanted him to know I was turned on. I moaned like I was on the verge of a great orgasm.</p><p>“It turns me on,” I said. “It turns me on to play with your ass, Jacob. It turns me on that you’re willing to let me play with your ass.”</p><p>I’m certain that Jacob would have grabbed my hips and started fucking his cock up into me if he wasn’t cuffed. He would have lost his mind and barreled towards his orgasm. Thankfully, it wasn’t possible. I was in control.</p><p>“It turns me on too,” he said.</p><p>“Yeah? Do you like it when I play with your ass?” I asked.</p><p>“Yes!” he said.</p><p>I’m not entirely sure he was being honest, but it didn’t really matter. He was willing to go there for me. I’m sure it’s just because he wanted to cum, but the fact that he was still lost in his pleasure while I was playing with his asshole was amazing to me.</p><p>“I want more, Jacob,” I said. “I want you to be a good boy and let me have more. Can you do that for me? Can you be a good boy for me?”</p><p>Jacob nodded and I rewarded him by riding his cock just a little. The joyful groans and lusty moans he released were thrilling.</p><p>“Take it,” Jacob said.</p><p>“Take what?” I asked.</p><p>“My ass. Take my ass. Do what you want with it. It’s yours,” he said.</p><p>I applied a little bit of pressure to his asshole. I felt him open up. The very tip of my finger slid inside and I pulled back.</p><p>“Are you sure?” I asked.</p><p>“Yes, please,” he begged. “Finger my ass. Please, finger my ass. Please, Sarah, finger my ass.”</p><p>I was so close to cumming as the words spilled from his mouth. I’m fairly certain I’ve never been so turned on. I pushed my finger in his ass. There was plenty of lubrication thanks to all the oil so I moved inside him with ease.</p><p>Jacob groaned, but it didn’t seem to be out of any sort of displeasure. He seemed to be enjoying himself. I started fingering him as I rode him. I reached down to play with my clit with my other hand. I fucked him in two ways.</p><p>“Take it, Jacob. Take it in the ass,” I said. “Cum inside me while I’m fucking your ass.”</p><p>I got a little lost in it. It was just a finger, but it felt so hot to say it. It felt so hot to think about fucking his ass with something bigger, too. I’m getting turned on just writing about it.</p><p>I felt Jacob’s asshole tighten around my finger when he came. I joined him a moment later. I wanted him to know how pleasurable I found it. I wanted him to associate his orgasm and my orgasm with anal play. I wanted to open the door to going further in the future.</p><p>In the present I enjoyed a fantastic orgasm. One of the best I’ve ever had, if I’m being honest, and I’d like to think it was the same for Jacob. I’d like to think the fact that I let him cum inside me was a good choice, too. It had to have been more pleasurable than a handjob. Plus, we both got to cum.</p><p>All told I think it was a huge success. Thank you so much for your advice. It really did make a difference.</p><p>I’m sure I’ll have more questions in the future, so I’ll be in touch.</p><p>Sarah</p>