Well, this new journey is starting and i have been nothing but a bundle of raw nerves. Thanks to my Owner and His every desire to keep me on my slave toes. Since this started to happen and I started to get scatterbrained and nervous, He made it a point ot have a few friends come over for dinner, drinks, some conversation. Maybe work on the car or sit by the fire pit next to the pool. Keep me silent. Then the guests would use me for their cum dump. be rough and demanding as possible. Then once done using me, send me back to finish my chores as they returned to talk with my owner. Keeping my head where it needed to be, as His property, His slave.

Saturday morning came and i was up much earlier than normal because I just couldn’t sleep. Too many things on my mind about the trip, my family and how can i do this to my Owner without any sure end date or plan? It’s just open to the whims of my family member and medical science. Yet, he is playing along with it all.

Edit: I am sorry for being so mysterious, But Master-Sir thinks its for the best right now.

Plus I needed to make sure everything was ready for my trip. To make sure everything was set up for my Master-Sir when He returns home without me. Normally when i pack for a trip, I need to make sure Master-Sir has plenty of clothing to wear for different things. For me, I pack maybe two outfits since I will be naked a majority of the time. This trip I need to pack for me to be in public often as well as being in the cold, winters of Chicago and wherever else I need to go. Master-Sir allowed me to pack more than one bag of clothing and necessities.

Master Chase agreed to take us to the airport, so I needed to remember to fix breakfast for two Masters. Thankfully, I put notes all over the house to remind me what to do. Yes, I was that scattered in my thoughts. After feeding my men and being allowed to get ready, Master Chase came to my room for one more blowjob before allowing me to get dressed and finish packing my carryon bag that was to include my large stainless steel butt plug.

I’m being serious, what I just wrote is about all I remember of the morning until we got to the airport and at security. The butt plug was in my carry on and it was setting off the alarms. Master-Sir had already passed and was standing outside the perimeter smiling at the noise and at my startled look. I knew it was going to happen, but until it does, you just deal with it.

Having to show the security lady was not as bad as I thought. Thankfully it was a lady and it was not anything serious once she saw what it was, then she looked at my red face. I’m not sure if she was just bored or what, but she motioned for me to go thru a second inspection behind a panel. There, I raised my skirt to show her i had nothing to hide because i was not wearing any panties or a bra. I felt sorry for her to see that, but she wanted the second inspection. She smiled as she had me repack my bag and told me to enjoy the trip as i was allowed to rejoin my Owner.

After that, Master-Sir became the Owner and was not really kind. We walked to the nearest family bathroom where He ordered me to use the bathroom if i needed to now because, as he tells me in that master-ly voice of His, that once He puts it in, it was not coming out we get to the hotel 5 hours away. He had me stick into my pussy until i was happy that it was wet enough to go in the other hole. then i bent over and held onto the edge of the sink as Master Sir made sure I knew it was going in. He held it firmly to my ass as my ring muscle started to let it in. Then He commanded me to push back against it to get it in quickly.

After biting my lips to avoid screaming as I felt it lodge itself into my ass. He pulled on it to make sure it was firmly in place and that it wasn’t coming out easily!

I knelt to the floor, kissed His boots then gave Him a blowjob as my Thank You for being such a wonderful and caring Master. For me, having His wonderful hard cock and swallowing its reward was a wonderful thing. it was also probably going to be the last meal i will be allowed to have until we are in Chicago. (it was)

The Flight

Master-Sir took the window seat because i was sure i was going to sleep most of the way if I was allowed that privilege. And I was. Master-Sir likes to watch the clouds and the landing. Listen to His podcasts and just zone out in flight. He is strange that way! He put a blanket over us so that He could play with me on occasion to break up the boredom! it kept me from getting any solid sleep, but I do enjoy having His hands on my tits and His long fingers in my pussy when we fly. It gives me a lot of comfort.

Not much else to say. The onboard movie was some silly Disney flick, so that was of no interest to either of us. The flight was uneventful other than having to wear those darn masks the entire flight. At the airport, the hotel van and driver was already there. The driver, He told us His name was Jackson. He actually came to find us, then introduced Himself. A tall strapping young man who looked sharp in his sport coat with the shiny name badge.

He really looked like He belonged at the Bellagio or the Chicago Hilton, some fancier hotel than where we were going. He looked to be about his mid-twenties, dark, short hair, everything was prim and proper, it looked like it was all just pressed and clean. or that he just came from the barber right there at the airport! His hair was neat, trimmed without a strand out of place. not a babyface, but it looked so smooth I wanted to pinch His cheeks. my mind then went to think about what His cock must looked like. Probably as well-trimmed down there as He was on top. My mind just does that when I meet men!

I loved it when He spoke. He was so firm and right to the point of whatever He had to say or ask. No-nonsense as He asked Sir about the flight and if He had all our bags. Yes, He spoke mostly to my Owner, so I was getting a good feeling He may be clued in on my stay or that He was going to get to know me better later. He immediately walked us to the van. I was actually expecting to see others for the ride. But we were it.

I was right. My Owner was talking to Him and He told us that my former Boss/Dom had talked to Him personally, since he was head of the concierge, he needed to know who was coming in and that I was to be there for a couple of weeks courtesy of a higher-up territory manager. He already made sure that we were checked in and that my room was ready. He also made mention that “I” can call on HIM anytime for anything as He smiled at me in the rearview mirror. I took that to mean He was told to expect a special bonus for His tip.

My Owner assured Him that I was not going to be much of a bother while staying at the hotel. Family issues will keep me busy, and once in my room, I was there for the night. BUT. My Owner would appreciate anything that Jackson could do to make sure that i was well cared for once he leaves. “No Problem there Sir” was Jackson’s response!

Riding in the van, I was happy to see the skyline that was my home so long ago. Master-Sir had allowed me to be able to contact a friend or two while here and maybe have a guest over to the hotel or to go out with them some time. I was looking forward to maybe seeing my old boss or at least my old office. So many emotions on this one drive.

Yes, I was home. A different home than when I left. but it was still where it all began for me. it was also fricking cold!! I forgot what that dry cold felt like!! Master-Sir told me to call my parents to let them know that I have arrived and that we are heading to the hotel. I am here and I am safe.