A Special Birthday Surprise – Chapter 11

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!

I watch him, I can see him looking up and down at me. He had a hungry look in his eyes. Well it was good to know that we had found a point where he wasn’t looking like a deer in the headlights. He stops, just staring at the dildo. I wrap my hand around it. “Oh, does mama’s boy, want mama’s cock?” I walk back over to the head of the bed to let him have a closer look as I stroke it. “Mama’s cock is going to fill that ass up so nice.”

He lets out a whimper, and looks up at me. Wanting to make eye contact. Him catching my eye, but me averting my gaze, him specific that I don’t look him in the eye. I turn walking over to the end of the bed. He let out another whimper, but this one was of frustration. Why wouldn’t I look at him? There was nothing shameful about what the two of us were doing.

What he didn’t know is that I wasn’t ashamed. I actually liked what I did, and liked seeing pleasure on my partner’s face. But he wasn’t my partner, he was a job. Although I did like seeing happy customers as well. He was a difficult one, but that came with this job. Give the people what they want, get paid, go on with my life. I reminded myself of that as I got between his legs.

Tom instinctively moved his legs so he was spread wider, also bending his knees so his feet were on the bed. I smile, “Look at Mama’s boy, is he ready to be nice, and full.” Tom nodding, trying his best not to hold his best.

His eyes were intently on me, watching me, as I positioned myself between his legs. I had added more lube to the toy, and some more to his hole for good measure. First pressing in two fingers in to see if they easily go in still after my prep work. I smile feeling them glide in. I wiggle them a little inside him, “I want you to keep this hole relaxed for Mama, if you don’t I won’t be able to make you feel all full and good inside young man.” I said pleasant, but there was an undertone of firmness in my voice.

He nods, reminding himself mentally how he would prep, and talk to a partner when they did this. How difficult it would be when they would tense up. He knew he would try his best. He was confident, due to how much prep I had done, at this point he had some idea of what it feels like to have something inside of him.

I had pulled my finger out, now the head of the dildo against his hole. Tom first feeling a light pressure, before a bit of a firmer one, just like my fingers felt the first time. Before the tip pressed inside him. I stopped when it was in, I could see he was biting hard onto the ball gag. I smirked a little, “Imagine if it was that larger toy.” I just couldn’t help myself. I knew I could get this one inside, but the other, I really was not sure I could.

I rub his inner thigh. “You are a good boy for Mama. Look at you keeping this hole relaxed. Do you want more than just the head of Mama’s cock?” I give him time to answer, he was using breathing exercises to attempt to make sure he didn’t clinch and tighten his hole. Maybe he had done this before. If he did, his hole didn’t show it.

After his brain was able to calm a bit, he was able to process just how it felt to have the head of the toy in his ass. Is this what the women he had been with felt, when he would penetrate them anally? It wasn’t unpleasant, he wasn’t sure if it was good though. He nodded when he felt he wanted to have more inside of him.

I start to slowly press the small dildo inside of him. I don’t look him in the eye, but watch for any sign that he needed me to stop. While he made sounds, none of them gave any indication that he needed, nor wanted me to stop. Me pressing in, until the very small dildo bottomed out. I reach out rubbing his stomach. It quivering, “Oh, does Mama’s big boy like her cock, or is he trying to process that he got all of it in his bottom.”

Tom was definitely trying to process the stimulation. About half way in, he had felt a nudge to his prostate, and as I pressed further and further in. He felt the toy drag along it. It felt good, He had been moaning against the ball gag, as I pressed in. He wanted more, but how could he express that desire? He knew for girls he was particularly dominant with, if they tried to trust, and dictate the tempo, he would go slower to show them who was in control of the situation. He tried to say more into the ballgag.

Lucky for him, that was one thing I could understand, even though most wouldn’t. Came with the job, and all that. He arched his back, as he felt me pull from him, that same dragging feeling coming from that. I continued until the head of the toy bumped against his prostate again. Tom letting out a particularly loud moan through the ball gag.

So much precum had started to come out of his cock, if I didn’t know better, I would have said he had came. Tom’s cock was twitching, and throbbing against him as I slowly pressed back in. He was trying his best not to press against me. He needed me not to stop. If it wasn’t for the ring, he was sure he would have blown his load already.

“Mama is going to fuck, and milk you for all your worth.” At this point he didn’t even hear it, he heard sounds, but couldn’t recognize words. Every part of his was far too focused on the fullness, and the dragging, and nudging against his prostate. The feel of my hands, and the bump he felt each time I bottomed out.

I reached for his cock when I felt that he was ready for a real rhythm, and not just teasing, to help his hole get accustomed to being full. Him giving a loud groan of pleasure as my fingers wrapped around it. At that moment he was overcome by the feel, giving a buck back. I reach down and squeeze his balls, pulling them down. “Young man,” my voice warned. Tears were coming from his eyes, I wasn’t hurting him, but that they started to flow from his body needing to shoot, and the stimulation yet him being unable to.

He tried his best to regain himself, but I could see he was a bit gone. I started to give his hole a good fucking. It is what the night was building to was finally here. Him taking each thrust like a champ. If it really was his first time at anal, it seemed he was a fast learner.

His look was just too delicious. His back slightly arched, and those sounds he was making. I could see though he was trying to say something. With one hand I was able to pop the gag out of his mouth. Expecting him to say his safe word. While it had seemed he was taking the fucking well. Seeing how he changed his mind to the point of whiplash, it wouldn’t have surprised me.

As well as that he was also looking overwhelmed. This may be his first time, given all the other information I was able to gather from tonight. I was also milking him in a very specific way to make him want to cum at every thrust. A big talker, but when it came down to the meat, he seemed utterly inexperienced. Then I heard it. “Inside please.”

When I heard him say it again, but a bit different I knew he was talking about his cock. “Me, inside you please.” He said between moans. Well maybe this guy had no clue what he wanted, as he listed specifically that I was not to put his cock in my mouth, or holes. Well that seemed to be the theme tonight, and he did ask, well beg for it.

I hear him continue to plea for it, not wanting to take the ball gag back into his mouth, I let it hang on his neck as I got on top of him. “Alright, alright, if you want to be inside Mama, since you have been so good taking the fucking like the slut you are. I guess I can give you a treat this one time.”

“Thank you… Mama, I a good boy.” If he were clear headed, he would be in shock, but he was way past the point of no return.

“The best,” I said, brushing his ego a bit. “Want to be filled, as you fill Mama up.” He was so lost in need he was only able to nod. I unhooked the cock, so it could remain deep in him.

I did pull it out and press it in a few times though faster than I could physically do with my hips. He cried out gasping, “Mama please. Need cum in you! I good boy, I good boy inside.” At that me seeing the biggest load of precum of the night pressing out of his cock. Which at this point was plastered like his stomach with his emissions.

He whimpers, and whines as I get off the bed and take a wet cloth to clean his stomach, and cock a bit, and dry it. “Behave, or Mama, will not let you inside her!” Him calming and letting me clean him.

I take a connector, and attach it to the cock ring which I loosen a little, and attach it to the connector that was used on the toy. “There, so the toy can move a bit while you are inside Mama, and your cock could breathe just a little.” Showing him by jerking him off with a few strokes, liking how it is affecting him. I look between his legs to see how it caused the cock to move a little from it. This causes even more whining from his need.

Tom was beyond ready to blow, his eyes were half lidded, completely drunk on lust, but his pupils were blown out. “Thank… youuuu,” he moans as I stop toying, and playing with his cock. I slowly roll a condom on his cock. It twitched like crazy; causing the cock ring to pull the attached toy to move about stimulating his prostate.

I look at the set up. Play time was over, I knew with the cock ring, he wouldn’t cum fully. At this point he needed to cum properly, and fully. I take the cock ring off, but leave the toy cock deep in him. With how his ass is behaving, that should have the dildo to have enough movement to gently stimulate him there.

“Mama,” Tom whined further. He was burning up, all the touching was nice, but he needed something soft, and warm. He needed to be inside something, someone soft, and warm. With the cock ring off, the need felt even more urgent.

When I was satisfied that he would be good to go, I got on top of him. I saw him fight against the restraints, his body trying to move up more, trying to get himself inside me quicker. He was so close, he just had to press inside me.

“Calm mister, or Mama will have to punish you,” I say this, causing him to stop and whimper. I reach down and grab his cock, hearing him groan as I give it a light squeeze. “Oh yes my dear, are you sure you want this big hard dick in me?” I say to confirm he does indeed wish to diverge from one of the biggest listed turn-offs in his paperwork. Then again given what has happened tonight, I wouldn’t be surprised.

“Yes, now please. Let me cum please, inside you.” Tom was trying hard to form coherent words. This was so intense. While nothing like he had ever expected, or dreamed he would ever do with a woman, he was so turned on. Being allowed to not think, and just feel. It was utterly intoxicating, but he needed to feel me. He needed to cum, and he wanted to cum in me. He was pushed way past his limits, and he needed to explode.

I take the tip of his hard cock, and find my opening. I press myself easily down on his cock. I can’t fight the gasp that comes from my mouth, breaking character. At that moment I was shocked. Fuck, did he feel good in me. Not that I would ever admit it. It caused me to not hear him at first when he said, “Please untie me now. I need to touch you please!” I take a look down at him, he is struggling, both to get a rhythm, and it looking like he may very well break my bed to get free.

From his thrusts I could tell he didn’t want me to set the pace, and since he asked, I reached up and untied his wrists. This may be where I would regret this night. As his hands shoot for my thighs, squeezing them, causing a surprised gasp to escape me. This gasp going straight to his already engorged member.

Finally his brain screams, and then calms, as his body gets what it now needs. He feels the softness of my thighs under his tight gripped hands, a tightness that I will later find bruises me. He looks up baring his teeth at me. He felt a possession of lust fall upon him at that moment. The only things in his brain was how built up he was, how good it felt, and the woman that had caused it now on top of him, and yet at his utter mercy.

With the toy still filling him, he didn’t think he could flip me, unsure if that would hurt his insides. That was fine, he didn’t want it to come out of him, it adding even more delicious stimulation. It urging him more, making Tom even more hungry for the release that he had been edged to. He would rather die, then be denied the ability to cum in the woman that made him feel such things.

I know I shouldn’t have, but I glanced down to look at him. I saw the look on his face,in those blue eyes. It was a look I had never known. Part of me was scared, but any part that was, was more overwhelmed by how good he felt. The thickness actually stretching me. My mouth falling open as I fell a bit from how hard he was thrusting up losing my balance.

My hands on his chest as he starts to slam into me as hard as he can. His body twisting, his back arching. Causing the dildo to rub even more with how hard his ass was clenching at it. He wanted this to last, he wanted to just keep fucking me, but he needed to cum so much. There was always a round two, the night was young.

Tom’s mind had little time to think on any of that, his body having completely taken over. Fuck, I was so tight for him he thought. Something he didn’t expect from a ‘girl like me,’ but all the same it was heaven. His mind now only focused on one thing, coming, coming hard, coming into the woman that made him feel all of this. Him forcing my body to bounce up and down on his hardness. Edging closer, and closer to release.

I was going to come! I was actually going to come! I never in all my years of doing this found a release with anyone. It was a job, and given my specialty was all about their pleasure, but something about his passion caught me off guard. It almost feeling like he wanted to *feel* me come.

And that Tom did. He wanted to feel my already tight pussy clamp on, harder than any girl he ever fucked did. His balls hurt, it wasn’t just delayed gratification, or the pressure in his ass from the toy which had them tight, it was how they were trying to draw up, draw up so hard that he felt as if they wanted to go inside him!

I can’t help but cry out from it myself orgasming. I barely see his eyes roll into the back of his head. If it wasn’t for the ungodly, animalistic cry he made I would have been lost completely as I orgasm with him.