A Special Birthday Surprise – Chapter 4

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

A Tom Hiddleston X OC Fan Fiction
Kink | Sub / Dom | Smut

Chapter 1 | Chapter 2 | Chapter 3 | Chapter 4 | Chapter 5 | Chapter 6 | Chapter 7 | Chapter 8 | Chapter 9

He couldn’t speak with the ball gag firmly in his mouth, but he looked at the toy. Was I just going to put it into him? He wasn’t ready. He didn’t think he was ready for anything in there. What he doesn’t know is I can make a man’s back hole ready for anything. And from what I read he likes a lot in there. But from the shake of his head, I stop. Was I really going to have to call him out on lying? I really didn’t want to. But if he was, that would add work. I was fine with the work. I just needed to know how much his hole could take to plan, and adjust the plan for tonight.

“Do you no longer want anal stimulation?” I ask, a good way to not call him a liar, but to get confirmation he still was wanting it tonight, and was not writing on his questionnaire like some teen boy that finally got a shot at whatever he wanted, without knowing how it is done in the real world. I watch him, I can see he is thinking on it. After a few minutes he shakes his head no, that he still wants it, but he looks so unsure.

“Do you want me to finger that hot man hole first, before we put this baby in you?” I say holding up the toy. I see him nod relieved that I would not go head first in it. I see that his chest is slowing down. I put the toy and lube in one hand, while I run my fingers along his torso. He arches into my touch, and whimpers. “Such a good boy for mama.” I say to him in praise before getting onto the lush four post bed.

Usually with men who want it on their back I would also tie their ankles to the other two posts, but it appeared I would need to have better control of his legs. I see his cock, it had stopped expelling precum, and had softened a bit. I had seen how thick his cock was, that was actually a blessing for us getting this toy around the base of his cock easier, so it could expand with him. Gentle gloves girl, gently gloves.

He tried his best to look down at me, me looking up at him seeing the look on his face. What were those eyes thinking I thought, but looked back down as eye contact was also a no, no for this man. I reach out and touch his cock. He seemed to like his cock touched far more, than what he let on. He looked down watching me handle him, he liked the way my hands looked on his member.

He watched in fascination as I pulled his cock through the bigger top ring. He had heard of cock rings before. He never used them, and never had an interest in them. This will be another first tonight, but it seemed like everything was a first tonight. He let out a grunt as I got it firmly around the base of his cock. Did I expect it to really work? It was so snug on his cock. Was this to keep him soft, instead of hard? He didn’t have much time for that, as I was pulling his calls through the second ring. This one caused a whimper. No one had ever handled his bits like this. It broke his eye contact with me, and what I was doing for a moment.

He should have had me stop way before this. He didn’t want this, he wasn’t gay. He was the alpha that is what the macho side of his head kept demanding of him, among other things. But the rest of him was hungry for something fresh, something new. From what he could tell, I was taking careful care of him. I was checking on him, asking him if he was ready, and willing when it seemed he was outwardly showing reservations.

He felt he was in good hands. In the end he gave into letting this happen. He wanted an experience, he was going to get one. I was a professional, he was confident that he would be well taken care of. Letting his body relax a bit, and look back down at me.

I move his legs so I can get more comfortable between them. He had long legs with thick well-toned thighs leading to skinny shins, and large feet. Not surprising by the look of his cock, and hands. Upon looking at what I would work with beyond his cock, I gave a bit more attention to his large balls. I reach, and tug on them a little to get a feel for them. It was a bitch trying to get them through that middle ring. They felt full, and heavy. When was the last time this man was milked?! Maybe he liked them filled too much, it would explain the whole looking tight, but I was sure that once I lube my finger and get it in there, it will quickly loosen up. Only problem was… I would be very wrong about that.