Matt woke in a quick panic, he woke up on his own and not thanks to his alarm clock. He quickly grabbed his phone worried that he overslept for his meeting and was surprised to see it was still fifteen minutes before he scheduled his alarm. He took a deep sigh of relief and laid his head back on the pillow and stared at the ceiling. He started to recall the memories of last night and started to smile at the huge difference in his life in just 24 hours from yesterday. He had not only sucked his first cock, but also swallowed two amazing loads and was planning on even more that evening. As he thought of those plans he also remembered the real reason he was in the hotel room was work. So he decided he needed to concentrate on that a bit before he let himself get to caught up in his sexual dreams about what will come to him.
Over the next thirty minutes Matt got ready for his day, called his wife and checked in with her letting her know his plans for the day. Well the work ones, as this was all so new to him and he hadn't even thought of what would happen when he got home. After all that he still had twenty minutes before the Uber would come and get him to take him to his morning meeting with the clients he flew in for he remembered the bag that James left the previous night. He grabbed it and went to sit on the bed and review the contents. He opened the bag and noticed three small bags which after exploring he realized they were to help clean out his ass to make a clean and enjoyable anal fucking session. In the bag as well were a few condoms, two small bottles of lube, a pair of cuffs, and the biggest surprise in the bag was a butt plug. Matt was both excited and a bit nervous knowing that at some point soon James was going to be putting that toy in his virgin ass in preparation for taking his ass. He looked at the time and decided to put it all away before he left so the cleaning service didn't just think he was some sex freak. As he was going downstairs he decided to text James. "Looked in the bag and seems like someone had other plans for last night, sorry I only provided the basic options." James hit send before even realizing he sounded like a complete obedient slut. But before he could start to worry about it more his Uber pulled up and he got in confirmed with the driver the address of the clients he would be going to see that day.
A block away from the hotel and James had already responded. "Don't worry I knew the time last night so didn't expect to get in that virgin ass, but I left all the tools for you to prep before I join you tonight. Let me know your schedule and when you are done for the day so I can make sure to get the most out of our time tonight." Matt felt his cock get hard again after reading that.
"Thank you for being patient than and yes once I meet with the client this morning I will let you know right away my schedule for the rest of the day." Matt quickly texted back as to let James know he was fully on board with the plan.
No response came for the rest of the drive over so Matt decided to change his focus as best he could to work. He kept telling himself the better he did there the less he had to worry about after and the more he could enjoy his evening of exploring new sexual activities that evening with James. He decided to put his phone on silent and then dedicated his mind to work for the next few hours.
He met with the clients, one a woman around 35 years of age with a body as sharp as her mind. She wore a navy blue dress that hugged her 34c cup breasts perfectly with a nice tight hold on her well toned ass that she swayed as she would walk around the conference room. Her long brown hair and beautiful eyes also helped out to make her look stunning even in the dull room. She obviously took time out of her business life to make sure she was tight and toned which Matt thought was amazing and in normal circumstances would be drooling all over the idea of this woman but after last nights events his mind was more on cock than pussy. Luckily for Matt the other two individuals in the meeting were a bit of heavier overweight men who didn't spark the urges and desires Matt currently had to suck a man's thick tasty cock. After the first set of meetings and discussions about the agreement Matt was sent to get solidified they came up with there plan for the day. The would all work together to has out the plans, cost, and requirements for each company until three and take a 3 hour break to have the legal teams review their requests and make suggestions on it so that at 6 the group can come back together hash out any issues and hopefully be done by 8. That would give the legal teams overnight to create the agreement that both groups would sign in the morning. Matt was a little sad about the long hours because he wanted to be free before 8 to get ready for James, but also knew he was there for work and this needed to get done. He texted James his plans for the day letting him know the three hour break in the day hoping James would say it would be enough time for Matt to at least get to taste another load from his cock.
Matt got his reply in moments after and was very surprised by the picture that popped up. It was of James's cock and a quick reminder that his cock would be exploring a new hole tonight, which made Matt instantly hard. He was trying to adjust his pants to not make it obvious when another longer text came from James. It was instructions on what he expected Matt to do during his downtime as James would be busy having dinner with his wife.
"That timing will work perfect for us my boy. I won't be able to see you but I want you to use that time to prep yourself for tonight. I assume you looked in the bag I left in your room so here is the plan. You will clean out your virgin ass in anticipation for me using it tonight. Once cleaned out I want you to lube up the butt plug and slide it in the tight ass. You WILL wear it in your evening meeting so that when you get back to the hotel and I join you we will make the most of your night. Once you have the plug in I want you to send me a photo of it so I can see my prize. Once you get back to your hotel call you wife so you can say goodnight because I don't want any distractions for you once I come over. Do you understand my boy?"
Matt read the message in excitement but just as he was finishing it the clients all walked back into the room so he quickly responded "Yes sir I will." He knew the sir was different for him to say but he just felt right typing it.
The next few hours Matt didn't have much time to think about his evening or the things that would be entering his ass later as the clients were wanting to get this knocked out as soon as they could. Finally 3pm rolled around and the discussions and information was all passed the the legal team. They asked Matt what his plans were and he just said he was going to go back to his hotel and look over something things back there before they met again. While the clients all said they would be taking a break to go have dinner with their respective partners in the downtime.
Matt had his Uber out infront of the office right when he walked out the doors which was great for him as his head now was getting around the fact that he needed to somehow get the but plug into his ass and get used to it in less than two hours so he could be back in the conference room hashing out small details before his night could truly begin. The drive back to the hotel was quick and Matt rushed up to his room to get started on prep to meet James. Matt entered his room and went straight for the bag James left, he poured out the contents grabbing the kit to clean himself out and went to the bathroom. After that knew experience of being fully emptied out he was out of the bathroom empty and now staring at the lube and butt plug. He was going to look up the best way to do it but figured it could be that hard just lube up his ass and the plug and it would slide right in. Oh was Matt wrong. After about 15 minutes of trying, clenching, stretching, and pain moans he had half of it in his ass and looked at the time. It was 4:30. He had about an hour left before he needed to be back in his Uber heading back to the clients office. He decided he needed to get this going so he had some time to get used to it so he pulled up his phone again and looked at the picture James sent of his cock and Matt knew he wanted it and as he looked at the picture and was practically drooling he was able to finally slide the whole plug in his ass. The moment it was in there he collapsed on the bed and could feel his ass muscles full tighten around the plug and except it. He set up his phone on a stand and got on all fours to show that the plug was deep in his ass and after a few pictures was finally able to get one he felt showed James exactly what he asked for. He sent the picture and a line to James saying that he was ready. As he was getting dressed back into his business suit and pants he received a reply back from James.
"That ass looks hungry for more than just the plug. Did you enjoy the process?" James messaged.
"It took a bit to get in but I think I can get used to this for the evening sir." Matt replied again going with the sir but this time not questioning it. He figured what else do you call a man who just got you to prep his virgin hole for.
"Good boy, and very good job calling me sir. Wonder what else you will call me later when you are in that exact position tonight but instead of the plug you have my cock deep in your ass." James replied, this made Matt extremely horny and he knew tonight's meeting would be difficult to concentrate but the feelings he got when he thought about feeling James's cock in his ass was to much to push out of his mind.
Matt quickly responded that he was excited to find out and than ordered his Uber to get him back to the clients office. The car was there quickly and got Matt back to the office at 5:35 so he walked in and was let in the conference room by the companies secretary luckily catching her before she left for the day. Since he has a bit earlier none of the others he was working with had showed up so he just stood at the window in the conference room staring out of it and also still getting used to the plug in his ass. He felt more discomfort when sitting so he decided to walk around a little bit. As he was doing that a truck pulled into one of the parking spots that was farther away from the entrance but close to this office window and as he looked to see if it was one of the clients he noticed the woman he had been working with all day was in the passenger seat. He assumed she was getting dropped back off and as he was about to walk back to the chairs to try and get used to sitting with the plug when he noticed that she hadn't got out yet.
From his vantage point he could only see the passenger side and it looked like the two in the car were making out feverishly. Matt was starting to get turned on by the idea of the beautiful woman and thinking about how amazing she would look naked when the action stopped and her door popped open a little. Once opened it looked like she was getting out once she put a leg out the door but than he saw something that made his mind race again, she seemed to be slipping off her panties and as he was dreaming it he saw the confirmation as she looked to have balled them up in her hand and handed them to the driver. All Matt could think was that she had herself one lucky husband. He heard some sounds outside the conference room so he decided to head back to his chair and start getting used to sitting in it with a plug in his ass for the next two hours and also an attempt to hide his raging hard on that he had thanks to the scene he just saw as well as the plug in his ass that reminded him over and over again that he was going to be on all fours begging James in a few hours.
Once all four were back in the office it was like nothing happened and no one would have known that not only was the strong business woman not wearing any panties after handing them over to her husband but that the client they were working with had a plug in his ass in anticipation for that evening where we was inviting a man over to help him feel something he had only desired for the past day. The two hours went by without an incident and both groups were happy with the outcome and agreed to meet back there in the morning to sign the contract and be prepared to start business. Matt being overly excited about the events for the night no longer kept imaging about the fact that the beautiful woman infront of him didn't have panties and moved on to thinking about the cock that would be in his holes soon. The Uber got there and took Matt back to his hotel, and Matt being excited about the evening decided to call his wife.
They chatted for the ride and as Matt got to the hotel and he caught her up on all his work events for the day and told her a lie about needing to review the documents in preparation for tomorrow, Matt knowing full well that he was already done with that and just needing to make sure she didn't call again as him and his schedule would be filled up that night. She was telling him that tomorrow she was going to have lunch with their neighbor Shannon, Matt now remembering the conversation he overheard the other day by his neighbors and as he thought about the idea of Shannon and his wife Desiree he sat down and instantly felt the plug push deeper into him which took him from that thought back to the current and wanting to make sure he got through this call quickly and without an event. After a few more minutes or chit chat and I love you's back and forth they hung up and Matt texted James.
"Back at the hotel and off the call with my wife so I am now free for the rest of the evening sir." Matt hit send and then went to the bathroom and check on his ass. As he was making sure he was in one piece he got a message back.
"Good boy, I should be there in about 30 minutes. I want you to pull out the plug, use another cleaning set and make sure your fully cleaned out again, was the plug off and reinsert it so I can take it out when I get there." James wrote back.
"Yes sir." Matt replied and then went straight to the bathroom to do as requested. After about 20 minutes all was cleaned up and the plug this time went in a lot easier and Matt put on a shirt and shorts instead of his business attire. Matt was now just pacing his room in both excitement as well as anticipation for what was to come and he finally heard the knock on his room door. He opened it and smiling back at him was James with another small bag in his hand.
