Tag: jackson

There is something erotically humiliating and yet gratifying to be kneeling, naked next to the table as two well-dressed men discuss your care and feeding while they enjoy their breakfast meal. leaving you to sit there quietly listen while also waiting like a good bitch slave, for one of them to kindly offer you a scrap of their food from their hand.

That was my first morning back in Chicago. Mr Jackson had come to our room with breakfast pastries for Him and my Owner. They were getting together to talk about the plans Mr Jackson has for me when my Owner leaves to go back home for work.

( Mr Jackson is the young man who is the head concierge/Bellman for the hotel i was staying at while in Chicago. My former Boss/Dom is in the upper management of this chain and had Him be the man to make sure the slave was behaving when he wasn’t there to check in on me after my Owner went back home)

Master-Sir was confident, as I was that if this young man was chosen by my former Boss/Dom for this assignment, he has faith and trust in Him to keep this private while enjoying the fruits of His labors and maybe even learn a little about being a little kinkier in His own life.

Master-Sir asked Him about His background. If He has any kinky experience? He admits that He was pretty vanilla. He had attended a BDSM event in Chicago one time and learned how to have fun with a sex slave while there. He has also dated a few women who liked to be tied up and used. He had them do other things while being His slave, like clean His house. It was all more sexual than an actual Master/slave thing.

Master-Showed Him how to put scraps in His hand and put His hand down for me to eat them. Telling Him i should only be fed like this or from a bowl on the floor. Mr Jackson assured Him He will find a bowl for me to use!

Master-Sir wanted Him to start my day at 6am, but Mr Jackson asked if it could be earlier. He starts his shift at 6am. They agreed He would be in the room here at 5:30 to make sure that I was ready to start my day with His inspection. I was told that by the time He arrived I was to have already showered and properly shaved my pussy. To be ready at 5:30.

He would be greeted by me, naked, at the door. Once in the room, I would kneel and crawl with Him to the table to start service to Him. If He brought food, I would set it up for Him to enjoy while serving me by hand or by a dog bowl on the floor.

Once He was satisfied with the meal or the snack, I would be ready to be inspected. That’s when Master-Sir had me stand up, legs spread and hands behind my head. “She must always address you as Sir. Yes Sir, No Sir.” Then I felt His hands on my boobs. pulling the nipples. Telling Mr. Jackson to try and keep them hard.

After that, He told Mr Jackson to feel my pussy. Inside and out. It should be smooth, with no stubble. Warning Him that it’s flabby and wet. Not really that tight. Not too good for fucking when compared to the tight ass that makes you feel like you are fucking a real girl’s pussy. “But it’s her ass” . Mr Jackson poked three fingers in my pussy to find it as promised, “wet and open”. Master-Sir told Him to have me lick His fingers clean. I did as ordered and smiled into His eyes. I gave Him His first “Thank You Sir” of the day as He pulled His clean fingers from my lips. .

He gave Mr Jackson instructions on how to have me move to be inspected. Mr Jackson ordered me to turn around, Bend over and spread my ass cheeks open. This, my Owner told him, was not so much for inspection, as it was to remind the slave that He owns her. Its His ass and she needs to have it open up to show Him.

As I stood there, bent over at the waist, hands on my ass pulling it open for Him to see. Master-Sir told Him this also a good position to fuck her in. Your choice of holes. Then He started to explain that He needs to go for a walk around the hotel and that Mr Jackson was free to use me as He wanted. To make sure that I cleaned up any mess that is made. His exact words were “Just fuck her in the hole of your choice. Make sure you use her for your pleasures, nothing more. She will clean you up afterward and that is it. You don’t need to worry about anything and we will see you tomorrow at 5:30.” They did a fist bump and Master-Sir gave me a kiss then walked out the room. leaving me still bent over holding my ass open.

Once the door was closed, Mr. Jackson had me stand up. As His hands felt my saggy tits, pulling on my nipples, He asked if all that was real? That he could, “you know, fuck you in any hole?” I assured Him this was all real and that I really do enjoy being used. I was there for His use, including any sexual pleasures. Telling Him not to worry, I’m a big fluffy girl, He can’t hurt me!

Mr Jackson realized it was getting late, so I quickly grabbed a condom as he told me how He wanted me. On the bed, Ass Up. But first I needed to fold up His slacks neatly and put that wonderful hard cock of His in the rubber covering. As I did, He pulled on my nipples again. I smiled and giggled a little.

Once I was as He wanted, i felt His cock plunged into my pussy, no tease, no slow entry it was just pushed right in until i felt His pelvis on my ass. . Fast and hard. He started to grunt and groan with each stroke until I felt His build Up and heard His voice rising. I knew what was next and I could feel it in the rubber. The warmth, the fullness. I wanted it! He was breathing hard as He pulled out. I quickly turned around to grab His filled condom. Making sure to kiss His cock and clean it off. Swallowing His cock one last time before I made a little show for Him as I drank His cum from the condom. I thanked Him for using me as I helped Him finish dressing.

Before leaving, I knelt at His feet, kissing them as I properly thanked Him for using me and that I looked forward to serving Him tomorrow. He slipped His face mask on and walked out of the room still looking at me smiling.

For the rest of my stay there, He showed up right at 5:30. Just after I got out of the shower. i would set His snacks or His morning meal He brought on the table for Him as I knelt at His feet and we talked. After he ate and fed me His scraps, He would order me on the bed. His favorite hole to fuck was my ass. But He really had a fetish for my pussy and even licked my pussy to orgasm a few times. Oh My God! It had been so long since any man did that to me! I screamed with joy each time when He would let me cum.

Each day when we talked, He would ask me something about being a slave or ideas about what makes a good Master. The “what if?” “Does He let you?” “can you?” types of questions. Talking like that always made His cock hard before we even finished eating.

After the first few days, He started to relax and would take off His slacks before sitting down to talk and to eat. Like this, He would give me permission to play with or to suck on His cock before He fucked one of my holes. I think I enjoyed that part of our time together, the best of all.

I really liked starting my day like this. It helped keep me focused for the rest of my day dealing with my family!

I know he subscribed to this blog, maybe I can get Him to respond here in the comments to what it was like. To read what His thoughts are on using this slave.

Since I was offline for all that time, I thought it would help if I did a little bit of a look back at the highlights of the trip. Trying to make sure i can get all the negative stuff out of my head by remembering the good times and all the people i got to reconnect with. Starting with my driver/concierge/friend and cheer person. Once He even let me cry on His shoulder when things were getting bad with the family..

Jackson was the Man!

When we arrived at the hotel, Jackson, the driver/concierge, told us to go straight to my room as He handed Master-Sir the key. That again told me He was told something. He would park the van and bring our luggage up immediately.

In the room, it was wonderful. A mid-story building, 12 floors. The type of hotel used for convention and business meetings. So you have a larger living area, wet bar, small kitchen. Separate bedroom and a full bathroom. Even with the room heat turned up, my nipples felt that cold air and became rock hard as i got naked. Master-Sir was kind, even with the heat turned up, it was still cold. So He allowed me to wear booties as I unpacked the carry-on bags. He called my former Boss/Dom to tell Him we were here. They said they would arrange dinner for us, so don’t plan anything! He made it a point to make sure that I knew that I needed to make sure Jackson was “taken care of”.

The Introduction

It really doesn’t matter that i have been a slave for over 15 years and have given blowjobs to literally thousands of strange men, i still get nervous at this point. Growing up, I had my share of being turned down for many things. Being told “No” for a variety of reasons,. Mostly because I am FAT. I know that! I deal with it every day. That feeling of rejection never goes away.

Yes, men are sexual creatures and they want sex often. But they also want it with women who please them in looks first, skills are second or third. For me, not being a beautiful creature, to ask a very handsome man who I believe (yes, my thoughts) can get sex from just about any woman, if I can suck His cock, is not an easy thing to do.

In a case like this, it starts with His first reaction to seeing me naked in the hotel room as He brings in the bags. I am waiting to serve Him and I need to see the facial response to tell me His thoughts.

Master Sir usually has an idea to calm my nerves and it’s usually like this: Having me naked and kneeling in a room, alone, gets them to say “Yes” 99% of the time. With Mr Jackson being in the know, He will be expecting something, which makes it a little easier. Especially now that He has seen me dressed, he knows it’s not going to be too sexy naked. But I will think He would appreciate the gift I offer. Regardless, I never know until He sets eyes on the gift and that is what always scares me. But we will cross that bridge soon.

I am kneeling at the foot of the bed when I hear Master Sir opening the door and welcoming Mr Jackson in. I hear Him and the luggage cart. Master Sir stopped Him and spoke to Him, but I have no idea what was said. But I can imagine it will be about the cash part of His tip. I am sure Master-Sir has already handed Him His cash tip.

Jackson pulls the cart into the room, smiles when He sees me and say “hello” to me as He unloads the cart and i tell Him where to put the bags. Then when he is done, He is standing in front of me with a unsure smile.

This is where I take over and come up with a witty way to proceed. I take a deep breath and I smile at Him. “Thank you Mr Jackson for helping with my bags. I appreciate you doing that for me. As a token of my thanks, I would be delighted if you could allow me to offer you a nice blowjob as my way of saying thank you.” Then I smile and wait for the response.

In this case, He was ready. Mr Jackson stood in front of me and unzipped His trousers just as I finished asking for permission. I asked Him to please sit down so that I can remove them. A proper blow job is with Him sitting, relaxing, letting me do the “work”. He easily smiled and agreed.

Removing His pants then His underwear, I was not accurate about the trimming. He was nicely trimmed around His cock. Not as well as on top, but better than most men. His cock was gorgeously nice(?). Stood straight, about 5 inches or so and it was a proud monster waving at me. He had a little wetness on the tip. As I started to swallow His cock, I felt His cold hands on my saggy tits than on my erect nipples causing Him to give off a slight moan as I moaned myself at the feel of His cold hands..

As I rode His cock with my mouth, He decided to lay back on the bed and just enjoy the feelings. I would feel His hands on my head occasionally, but nothing to worry about. His moans were what was fun to hear as I felt the build-up. Then He grabbed my head and held me as I felt Him pulsate and fill my mouth with His creamy reward.

I swallowed and I licked as I moaned in my happiness. After I felt the last load shoot, I stayed on His cock, feeling His hands leave my head as I heard Him mumble about being right. When His cock died down, I gave it one last lick then pulled His underwear back on, fixed His pants, kissed His feet, and thanked Him as I knelt back into position, licking my lips.

He sat up, smiled, fixed His hair as He stood up. I stayed kneeling. He bent down to look at me and told me “He was right. That was an amazing blowjob”. Smiling, I thanked Him again and told Him I was here for him. I walked Him out to the main room where Master Sir was sitting in a chair reading while drinking a soft drink. He looked at Jackson and asked Him if the tip was enough? He smiled, thanked us for the tips, saying He was looking forward to my stay and had hoped that I/we liked the accommodations. With that, He walked out.

Once Mr Jackson was out of the room, Master Sir looked at me then told me that indeed, Mr. Jackson was well informed of what was going to be offered to Him and that the smile on His face when he left made my Owner proud. The very words I live to hear. My Owner was proud of His slave.