Tom gets a very special birthday present. It turns out to be a big surprise for himself. Will he be willing to let it go?
Written by: Odogoo
Author Note: There was a mix up with number. This is a new chapter that came out November 2022 to Patreon, and December 2022 to TeamAONN.Com. The Original Chapter 10, was moved to Chapter 9 as that was a duplicate of Chapter 8. Sorry for the mix up. We have cross checked, and the issue was resolved. The real Chapter 11 will hit Patreon in January, and TeamAONN.Com in February, just in time for Hiddles Month!
A Tom Hiddleston X OC Fan Fiction
Kink | Sub / Dom | Smut
As I look at him I think, why did he have such a look of trust in his eyes. He shouldn’t trust me, and I knew I didn’t trust him one bit. I see him nod though, so show time. I gave him a small glance, but make sure I am not looking at him for long. Instead I am looking at his body deciding where I should start. First I wanted him to feel it, get used to it. I was not sure if he ever had one used on him before. I already knew what the file said was out the window, so I had to assume nothing at this point.
I just wanted this night to end, but I was a professional. If I think I am the best at what I do, then I should act like it. “You were going through my things.” I say pressing the end of it gently against his chest. I see him take a deep intake of breath as I do that. I am not sure if he is preparing himself, or turned on. I press more to see. “That was very naughty of you.” I say as I run it down his chest, to his stomach. I stop just above his belly button. “Do you know what I do to naughty boys who go through my things?”
I see him shake his head no at me. Not the stop shake, but to answer my question. I give the lightest of taps above his belly button, on his hard abs. “Punishment of course.” I give him a wicked smile.
He feels a throb start in his cock. What kind of punishment did I have in store for him? This is all going in a better direction. He liked my seductive smile, but wondered how wicked of a woman I would be to him.
“Oh does punishment turn you on?” Raising the crop, and pressing the side of it against his at attention cock. I run it up and down the shaft. “Yes I think you like being naughty for me.” Giving the head of it a light tap. I see that my action was causing pre cum to press out of its head. “Now, now, we will have none of this yet,” giving the head a few more taps. This causing him to moan.
He watches me as I tease him with the crop. First gentle taps, and touches over his body. Then they slowly get more and more intense. Some areas are barely touched, others are focused on. I watch his body, seeing which spots he responds to positively, which ones he responds negatively to, and which he is unsure. He seems the curious type, so I play into that. It also allows him time to catch up, but also breath.
The first time I got his neck he jerked a bit. I run my crop down his neck. “Does Mama’s big boy like that spot?” Tom is having a hard time processing it. He liked it, he loved what I was doing. The light feather tip touches, then the nice sting. Some spots he had not enjoyed but his neck… normally he would think not. But the way I did it, the way it felt. I definitely knew how to work it. “Do you want me to not play with you there?”
I ask, and without hesitation he moves his head to expose his neck more. “That is Mama’s brave boy.” They sting as much as a love bite would. At least that is what he thought. Shivering when he felt the leather run along his jawline. His hips shifting up as I did it. I look at his cock, it pressing more precum. “You are so full for Mama. I am going to love milking this big boy cock of yours.” As I say that, I lightly hit the shaft with the crop. This causing him to moan, but that moan still turned into a scream of pleasure as I did the same to the angry purple head of his cock.
Tom’s mind was trying to focus, but each tap to the tip of his over sensitive cock was like a hammer hitting him. He needed to come, needed my mouth on his cock, to be inside me. At this point he didn’t even care how, he just wanted to thrust as hard as he could.
I could hear him whimpering, “Oh my poor baby, well maybe you shouldn’t have let these get so full.” I ran the crop down his shaft and let it touch his sac that was drawn up. This caused his back to arch, and him to moan more. Him trying his hardest to not move his hips up. I had to admit, I did like his discomfort, due to lying to me. Part of me also thought it was possible that he really was a novice, and I should be a bit more merciful. Not sure which side won out with the thought of, if he wanted mercy he wouldn’t have been here with me.
I move back between his legs, I then wack his thigh with the crop when he started to squirm. “Young man!” My voice was commanding, but he kept at it. I did a quick check to make sure he was okay, but I saw it was just his need to cum, so I wacked the other one. “Young Man,” at which point I grab his cock and squeeze it. He slowly thrusts into my hand. At which point I get off the bed.
He looked over at me, his eyes pleading. If only he didn’t have this damn ball gag in his mouth. He would do anything to cum. Why did I look so angry he thought, watching as I pulled up a chair and sat down, crossing my legs. I looked away from him, when he started fussing more I said. “No, only good boys get their cock’s touched.” I looked at my nails, they were clean, no nail polish, and cut due to having to finger clients regularly.
After a few minutes I get up, and rest my hand on his thigh seeing his cocked relaxed a bit, but still hard due to the ring. “I know Mommy is mean sometimes, but it is for your own good.” I run my fingers down his legs before getting back into the bed. I completely ignored his cock, and instead looked lower. I see his hole, it still looked good and ready. I take the crop, and lube up the handle end. It isn’t as thick as my fingers, but his hole needed to get used to a object, and something that could go deeper.
I slowly press the end of it inside him. I expected him to move about again, which he did, but it wasn’t as bad as I thought it might be. Taking my time, I keep pressing it inside him, until the handle is fully inside him. I look up at him to make sure he is still okay.
Tom, while surprised at the new feeling, welcomed it. It was torture those few minutes without stimulation. He was trying so hard to hold on. If it wasn’t for the cock ring he would have blown his load by now. Even with it, as I had pressed it in him, his cock leaked heavy amounts of cum.
Unfortunately, even with that release, it didn’t help. In fact it made it worse, the sensations of his cum slowly being pressed out, all the more reminded him he wasn’t coming, and he did not know when or if I would allow it.
For long minutes he laid there, doing his best to be still, I could tell. “You are trying to be so good for Mama aren’t you.” I see him nod, as he does I slowly pull the crop handle out. “I can see that. That is why Mama is going to fill your bottom up.” I slowly press it back in as I talk to him about filling him up.
He kept his gaze as best he could with me before his head fell back too lost in the feelings of me moving the handle in and out starting with a nice slow rhythm. Listening to my words getting lost in them. “You have such a nice bottom. All of Mama’s boy is nice, and cute. But I know I am going to enjoy making this bottom full. You need to be filled up while I empty you.”
As I talk to him I slowly message his balls, to help ease their pain. When I felt confident that he could take a real toy, only then did I slowly pull it out. Him whimpering when it was out of him. He never thought he would think this, but he wanted his ass full. There was a first time, but he definitely was missing out in his life it seemed.
“Don’t worry this hole won’t stay empty for long. After all, you are Mama’s little slut, and Mama’s slut needs to have his ass filled.” I say this as I put the crop on the side table to be cleaned later. He hears clicks, looking at me. I had a dildo in my hand, and what was I doing. He wished he could get a closer view, but it looked like my outfit had a way to have it attached. Was I going to fuck him with a strap on? Well it looked like it.
At this point any normal voice that he would have had, was told to quiet. He wanted this, looking at the toy hungry, looking at me, my ass. Then he looked up at my breasts, him processing that this sexy woman who had shown him so many different things, was now going to show him something else new. I had taken great care of him so far. He could tell the times I was checking on him, I was making sure he was okay. The time he wasn’t, I stopped. He had complete confidence that if I felt his body couldn’t take what I was about to do, that I would stop.
He was right about that. I had been building up to this, preparing him. Even if this was his first time, even if I took his ass virginity, I knew his body could take the smaller toy. He wouldn’t last long with it, and then the night would be soon over. “Are you ready for Mama’s special toy?” I say it sweetly, as I rub the numbing lube onto it. Waiting for him to make a choice, on if he really wants to go all the way down the rabbit hole of this new experience, or stop before the finish line.
