The Search to Find his Sexual Place Pt. 03

"Oh god I hit the jackpot. I'm gonna take a video, I want you to suck my dick and look in the camera and beg me to take your ass. Beg me to do all the naughty kink things you have wanted to try. Beg me to seed your virgin ass." James said while looking down at Matt and taking him to the point of pure sexual desire. James knew he had him in his hand like putty but it always brought him more satisfaction to hear them beg for it.

Matt was no longer holding back. This was going to happen and he wanted it so bad he didn't care what he had to do to get it so he looked up at James and the phone and said, "please daddy I need you to take my ass. To fuck this married whore and plant your load deep into my ass daddy. I need to feel you inside me, to feel how a real dominate man fucks. I want to suck your cock all day and I want to feel it. To be bent over and have you take my ass and to hear your pleasure in doing so. Please I want you to take my ass daddy."

James stopped the recording and looked at Matt, "you are here for one more night after tonight right boy?"

"Yes daddy." Matt quickly responded hoping that meant he would see James again tomorrow.

"Good than tonight will not be the only night I cum in your ass. Now present your ass to me so I can take out that plug and put in the cock you have been dying to feel." James said putting the phone to the side for a moment and grabbing the lube from the bedside table.

"Yes daddy." Matt said as he repositioned himself to have his ass right infront of James but moving more to the middle edge of the bed to give James room to get behind him.

James put lube on his hand and quickly grabbed and pulled the plug out of Matt's ass which made a loud pop and Matt moaned out loud.

Matt felt very empty at the moment but before he could say anything felt James rub the lube all over his asshole. It felt good and cold but all he could think about was what was next.

James got up on the bed and got behind Matt's open inviting ass. "You ready boy."

"Yes daddy." Matt moaned in anticipation.

James grabbed his phone again and pointed it to see his cock rubbing on Matt's asshole. "I'm gonna record this so you can always go back and remember the first time you fully brought pleasure to a man."

"Thank you daddy." Matt said feeling James cock at his asshole and waiting for him to push in. Right as he was wondering that he felt it. James slowly started to push his cock in. Matt began tightening up and James told him to relax and they will go slow.

Over the next 5 minutes James slowly entered Matt in between whimpers of pain and pleasure from Matt. Finally when he was fully in James said, "you did it boy, I am fully inside your ass. How does it feel."

"Great." Matt said catching his breathe and now realizing that with the lube and the pace that James went he no longer felt pain just extremely full. "It's not painful anymore and I just feel all of you daddy."

"Good, cause now it's time for me to fuck you Matt. Now look back at the camera while I do that. I want you to tell me how it feels and what you want ok boy?" James said right as he hit record to catch Matt's building lust for cock.

Matt looked back with eyes of pure bliss, he never felt more full but also never felt more free. "Please daddy fuck me. Make me feel like a whore. I need you to cum in me daddy. I need to feel it." Matt begged and thank felt James started to slide in and out at a fast pace.

"Fuck yes boy take it." James said.

"More ..... yes please...... harder..... please spank me." Matt said and James spanked both cheeks and than grabbed his hips and pulled them in tightly.

"Fuck these whore handles are perfect to hold onto while I pound you." James said while he was pounding into Matt's accepting ass.

James fucked Matt to a steady pace over the next five minutes to the point where Matt felt himself building up to a near explosion.

"I'm going to cum I think daddy." Matt said.

"You're going to cum from just getting fuck my boy?" James said through a smile.

"Yea daddy it just feels so good and I can feel it getting closer." Matt said in between moans of pleasure.

"Do it, show daddy how much you enjoy him fucking you by cumming like a whore. I bet if you fucked your wife like this you wouldn't be so desperate to find sexual pleasure huh?" James said taking his domination another step as he knew he had Matt.

Matt could only agree. There was no way he fucked Desiree like this, if he did she would be wanting it as bad as he was wanting it in that moment. "Yes daddy you're right. I can learn so much from you. Please daddy let me cum, I think I will when I feel you cum in me." Matt begged wanting to feel release but also desperately wanting to feel James cum in him.

"Before I give you that pleasure, tell me boy, do you want your wife to feel the way you are feeling now?"

"Of course daddy." Matt moaned.

"Good to know boy." James said, normally he would have dug deeper into getting potentially an opportunity to cuck a man but he was also close and wanted to finish off this fresh ass. He began pounding harder and faster, enjoying the moans and begs from Matt to fill him up and than he felt it coming.

"I'm ready daddy, I can feel you tense up please give it to me." Matt practically yelled as a beg.

"Get ready to explode my boy." James said and pounded a few more times before exploding his load into this once virgin ass. As they knew Matt came as well the instant he felt James explode in his ass. Both now spent they both laid separately on the bed.

Matt without thinking rolled over to be able to clean up James's cock. He knew it hd just been in his ass but after sucking it earlier wanted to be able to taste James's again. James grabbed his phone and took another picture of this still eager whore sucking his cock even after they both came without him having to say a word. He knew already tomorrow night would be one for the ages.

While Matt continued to suck his cock he decided to send a tease text to his wife with results from his conquest. He figured he would show he the outcome and once at home she could she the other pics and videos of him taking that virgin ass. It was always a kink of hers that she enjoyed watching even if not in person. He texted her the clean up picture as he knew she should be getting home from her long day in the office.

As Matt was starting to slow down on the cock worshipping and clean up James received a text back. "Omg that is the client I was with all day. No wonder the meeting after he was ok with the changes he wanted to get out of there to you." James read. Who would have thought the whole reason Matt was in town was to make both him and his wife happy one in work the other personal. He was going to say something but instead had a fun plan come to mind. He has brought his wife's panties with him in his small bag as she gave them to her when he dropped her back off at work after their dinner date.

"Matt go grab the bag I brought tonight. In it you will find some more cleaning kits so you can have more for tomorrow some extra condoms and lube. Guess the condoms weren't necessary as you were a slut in heat but I assumed with you marriage and lack of sexual partners you were clean as well. Also you will find a pair of my wife's worn panties. You may sniff, lick and suck her juices off them as much as you would like but tomorrow when you are working and keeping the plug in your ass I want you to be wearing those as well. Any questions boy." James said more sternly than any other comment to Matt before.

Matt was taken back by all of it. From realizing yes he begged for a man to cum in his so of course it wasn't protected sex but he knew at that point he was far past that and he felt confident that James was also clean. And than the thought of wearing panties for a man and doing it so at work. The plug part actually excites him though cause he knew that meant James would be coming back the next night. He was also exhausted and just wanted to rest so he said, "yes daddy, for you I will."

"Good I want a picture in the morning before you leave showing me the panties on and the plug in." James said back to a less stern tone as he knew Matt would now comply.

"Yes daddy, I will." Matt said as he began to move off the beg which brought the realization that he could feel James's cum dripping out of his ass and down his legs.

James got up and started to get dressed and sent a quick text back to his wife. "I think tomorrow will be an exceptional day for us both. See you soon honey."

Matt put on his shirt and shorts again no boxers this time and as he walked James to the door could feel his cum dripping out.

"You did great tonight boy. Tomorrow will be even better I bet." James said with a smiling knowing that his new submissive was going to be in for a big surprise tomorrow.

"Thank you daddy. I can't wait." Matt said still exhausted but already starting to get horny again by the idea of more the next night.

James opened the door and walked out as he got down the hall and exited through the stairs option door, before Matt could close his door the next door opened and the couple from the previous night were there. The man was only in boxers but Matt could tell he was hard and the woman in a bra and panties said "shucks we were gonna give you both an audio show like you did for us. Well hope we don't keep you up to late, you begging like a whore really turned us on." She said with a giggle and a wink and shut the door.

Matt shut the door a bit jealous but also tired knowing he still had work to do in the morning and now it has to be done while wearing panties and a butt plug. He figured he would try on the panties before bed and once he did he weirdly felt very sexual again and enjoyed the feel. He kept imaging him bent over presenting his ass to James in his owns wife's panties oh god he thought as he was back to fully hard. He took the panties off and sniffed them and licked them as they had some dribbles of the cum that was still flowing out of his ass. He thought fuck I need to get to sleep so he did so reluctantly knowing that tomorrow was another day of fun.