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.
