Stepping off the plane, I saw him standing at the gate, and I was glad I was in Chicago. He smiled, and we hugged. His arms strengthen around me, and I felt so at home. I tightened my hold around him, letting him know I was joyed to hold him again. I wanted to kiss him so much, but restraint was the order of the day in a very public airport setting.
After the train ride to the city, and the struggles to get to the hotel, we finally were together on the bed, making up for lost time since our last meeting.
Sir's first impressions of IML changed quickly after our arrival and dinner. He was hesitant from the beginning when we discussed meeting at the event. But seeing the lobby filled with men in leather and uniforms made him more receptive to being there. But I could tell he was hesitant about his acceptance as a Master. That would change the next day.
That evening I presented Sir with a USMC Dress Blues Uniform, Rank of Staff Sargent that we found on eBay during my stay in Houston. With some alterations in the morning, Sir dressed and was ready to conquer Leather Mart. And conquer he did! Sir stood out in his uniform; heads were turning. They could tell he was a Marine and in charge. He could've had his choice of boys at his boots for the next four days. And many tried.
Dressed as a skinhead, I kept one pace behind Sir. We eventually hooked up with an online friend and purchased some things from the booth he was working at, including my chain collar and lock. Sir, purchased some police gloves that I would be experiencing later on.
My first experience with gloves was the following morning as we woke up. Sir had the leather collar on me since arriving at the hotel. During the night, it was getting tight, and I adjusted it. As we woke that morning, Sir and I held each other. I gave him a massage; it was a nice morning. I told him that I had adjusted the collar.
He was disappointed. He instructed me that only he was to touch the collar. He wanted his police SAP gloves (weighted leather gloves). He ordered me to bed, face down, my naked body on the white sheets. Sir put on his gloves and tanned my ass with his palm and fist. After each hit, I was required to state, "I'm sorry for disappointing Master."
My ass was sore, and I was disappointed in myself. Sir had not punished me before. I let him down. Though I think he enjoyed using his gloves, I did take the punishment like a strong boy. Sadly, later that day, I was punished a second time in the same manner, though the infraction now escapes me. Now I was bothered by disappointing Sir twice in one day.
It is my goal to never be punished for failure or disobedience. But I must learn that Sir will challenge me more than any Master I've trained with so far!
Even after the morning of punishment, Sir presented me with his chain collar. Before we arrived, he told me he would put the chain around my neck and lock it. This chain was not removed until his departure. It was a simple event that meant a great deal to both of us. More than the symbolism, it was his commitment to me.
Friday night, Sir worked me into bondage where I was helpless, blindfolded, and soon tasting the metal of a weapon. Though I could not see it, I could tell that this was not fake but real. The minutes ticked by as Sir threatened me with my life. I was at his mercy. I know he liked the thrill of having me beg for my life. I trusted him, but there was a part that I wasn't sure.
Sir wanted me in tears, and I felt extremely mixed emotions. Things were getting intense; Sir was holding a weapon to my head, forcing it into my mouth as it was cold, feeling the hole with my tongue, helpless in tight bondage, the cold steel on my neck, unable to see the blue eyes of the Marine I have been collared by. It was a scary feeling, even though I totally trusted him.
Then Sir asked me if I had any final words. I'm not sure where it came from, but all I could say was, "Sir, I love you."
That surprised Sir.
"Fuck!" was all he could say, as I could tell he didn't expect that response. The blindfold was removed, and I received the best fucking kiss ever. That moment connected us more than any collar.
Afterward, on that Saturday afternoon, we were like kids, wrestling with each other, and Sir showed me some self-defense moves. He was happy, smiling, and laughing. He was a different Man.
But that night, we faced a new challenge.
Sir was invited to a uniform group dinner. I could sense he was very excited about going, wearing his dress blues. As Sir was getting ready, I asked if he wanted to go alone. He did, and I understood. During this trip, I wanted to show Sir that I did love him, but I could function without him for a while. We were not joined at the hips. We care for each other deeply.
He left, and I joined a friend for dinner. We had a good dinner and a nice visit. As we returned to the room, Sir came running down the hall, out of breath. He had just climbed 8 flights of stairs to reach our floor. He hurried me into the room. I was instructed to hurry and get into my BDUs; we went to the Cellblock for the uniform night. I rushed and began to get nervous, for here was my first test in some of the military p Sir protocols that Sir had trained me on.
I dressed quickly, and we met Sir's friends in the lobby. Piling in a van, we headed to the bar. I sat on the floor as Sir told me about the man in the front seat. That man was also in a USMC uniform, and all the guys called him Gunny. I could tell that Sir wanted to impress Gunny a great deal. This cause my stomach to get tied in knots. As I saw Sir's excitement, I didn't want to screw up and embarrass him. Never had I been so nervous while serving a Master. This was extremely important to Sir, and I felt great pressure to perform to his expectation and reflect highly on him.
As we entered the bar, I was close to Sir. I maintained proper military protocol with Sir and the others. It was loud and getting crowded. I spent most of the time at ease, out of earshot from Sir. He spent most of the time talking with Gunny. Occasionally I would get Sir a drink from the bar, then return to my proper position. I must have looked unique in the bar as leather men and such partied around me. But I maintained eye contact with my Sir.
The night went on, and we were waiting for the back part of the bar to open up. As this time passed, I could see things in Gunny that I was uncomfortable with. I heard parts of their conversation and could tell he was up to no good. We all have feelings about someone that we know isn't right. Plus, Gunny was really pushing, Sir. At times not really respect his position or the rank on his sleeve. Gunny went to the bathroom, and Sir came to see how I was. I was doing well and appreciated his concern. He was sweating in his warm uniform but continued to look excellent. I asked if I could talk freely, and he allowed me to. I told him I was feeling uneasy about Gunny. Sir said he started to sense something uneasy also. He and I were so much in sync; we both knew that things weren't going right or there were other motives for all this.
After Gunny returned, I was turned over to him. I was nervous as shit! He barked some commands at me, and I followed my best. I think he was testing me, but I never became flustered. Even if I was wrong, I maintained my attention and order. He ordered me to get my Sir a drink at one point, and when I returned, they had moved. Gunny went through some spiel about me being dead if I was lost.
Once Gunny was done with his spiel of my death by getting lost in the bar, Sir turned to me and asked if I was dead. I replied no, and he said I must not have been lost. Gunny didn't appreciate Sir's response, but Sir had a grin on his face that told me he was proud of me. At that point, I could tell Sir was losing respect for Gunny.
We made our way to the back room once it opened, and several guys we had met during our stay created a wall between us and Gunny. Sir really didn't want anything to do with Gunny. So our friends kept him at a distance. Gunny stood close to our group for nearly an hour with his back to us. Just listening. It was creepy, to say the least. I know that Gunny's main interest was in Sir. He wanted Sir to serve him and be in command over Gunny's boys. Sadly, Gunny had no respect for Sir or me. And he was wearing a Marine uniform yet didn't understand trust and respect.
That night at the bar, Sir was very popular with some guys. They were all over him. One asked me if I was upset. I replied that I wasn't; I was confident in who I was with. In hindsight, yes, I was jealous. Why shouldn't I be? But I knew I was with Sir, and he would go home with me.
Eventually, it was time to head back to the hotel. I know Sir was a bit disappointed in the happenings with Gunny. But I think he had a good time that night and enjoyed developing friendships.
Sunday brought another shopping trip to the Leather Mart. Sir wanted a flogger to use on me for our night's visit to the Chicago Hellfire Club. I introduced him to Master Jim from Green Bay.
Master Jim was an important friend in my life, and Sir knew he meant a great deal to me. Master Jim and I met a few years earlier when I was starting my exploration into the leather world, and together we experienced some great things. I was truly impressed when Master Jim gave Sir total respect as a Master. That was important to me also, and Master Jim knew that.
On the floor of the Leather Mart, Sir tried various floggers on my naked back. People were looking at me, watching. Others came up, feeling my back as it was warmed. Sir wasn't taking it softly in his testing. I had never been on display as I was then. I liked the feeling, and I thought Sir was enjoying it, also.
That night at Hellfire, in total domination glory, Sir impressed the others with his new skill of flogging his slave. Secured to a rack with leather wrist restraints, my shirt removed, I was in leather pants and boots; Sir began to show me his power.
He was in leather pants, 20-hole ranger boots, and a vest. His gloved hand held the flogger, and he began to strike me. Over and over, it grew stronger. He verbally reminded me of my position. He would stop, come around in front of me, and I would see his smile, the joy in his actions. He was enjoying himself. Then, he would go back to the flogging. He would tell me how many men were watching him flog his slave. I saw in Sir pure joy at this moment. He was a Master; he was my Master. I was his slave.
For the first time ever being flogged, I was hard. He challenged me to go further and further. Taking more than I had taken in the past. But I was enjoying his pleasure. And that was what we were all about. Giving each other pleasure in life. I was bonding further with Sir. Again, a moment that I was not expecting. But the one I will remember for a lifetime. I was so glad we went to Hellfire and served my Master for all to see. No one can ever doubt my honor to serve nor his honor to own me.
We found ourselves alone when we returned to the hotel, waiting for the elevators to return to our room. The elevators were very slow in this hotel. They were just off the lobby, and we had a clear shot of the lobby.
Then Sir ordered me to his boots, and I cleaned with my tongue. As I worked them, a skinhead walked up. There in front of the skin and those in the lobby, Sir asked the skin if he'd like his boots taken care of. Of course, the skin said yes, and Sir ordered me over to the skinhead's boots. I started licking them. As I did, a nicely dressed couple that probably just came from an opera or something came up to the elevators with a hotel security person. Not sure what they thought of me down on the floor taking care of two men's boots with my tongue.
The skinhead gave me a slight kick as Sir told him that his boy had always wanted to lick a skinhead's boots. Then the skin wanted me to do his soles, but Sir let him know that his boy only does the soles of his Master's boots. Just then, the elevator arrived.
As we rode up, Sir and the skin talked a bit. He got out on our floor and headed down the hall before us. As Sir and I reached our room, Sir entered first. As I was entering, I spotted the skin looking around the corner. Once in the room, I told Sir we might be getting company. But it didn't happen. Perhaps it was a good thing; Sir and I were both beat for the night. Sir told me that when the nicely dressed couple saw me, they asked the security person if he could stop me. The security person told them that it was only one weekend a year. Sir and I both chuckled about that.
Monday found us in the room after enjoying the Art Institute of Chicago. Sir and I both love art galleries and artists. Being creative, I think we both enjoyed the museum. We found ourselves back in the room and wrestling. We did this wrestling several times, and I think we both found it stimulating and enjoyable. We laughed; we were like little boys playing. Sure, we were still Master/slave partners, but we were friends. I had never done that with anyone, and I admit it was some of the best weekend times. We were carefree, enjoying life and who we were.
We eventually collapsed on the bed, resting, talking, kissing, and enjoying the silent time. This was our last day together. We touched on many subjects, and something in me felt it was time to fully submit. It was time for the Master to fuck his slave. I was so relaxed I knew it was time. I asked Master to use me and dominate me fully. He asked if I was sure; I was; I was so ready.
I went to the bathroom, and Master got ready. When I was done, he was in his new leather chaps, boots, and gloves and ready for his slave. I was ordered to the bed, face down. And in seconds, he was in my ass. Master took control without delay. It hurt some, but I wanted it and was relaxed enough to get him in me. He couldn't get in all the way, but that didn't stop him from having me feel his power. He abused me verbally, telling me of his power over me. The leather of his chaps rubbing my legs, his gloved hands slapping my ass. My dick was growing in the bed covers as he pulled his hard manhood out. Sir said he wasn't done and slammed his cock into my hole again. I moaned into the pillow, and he pistoned me even harder. He was enjoying this, something he wanted for a long time. To take my ass, own it and use it for his pleasure. He took his time, enjoying this moment. Part of me wished I would've been in bondage, but I was his captive and slave; there was no need for bondage.
Master could wait no more, and he fired his power into my ass. Unlike stories you've read, I couldn't feel his "hot sperm" filling my ass. But I could feel his movement and his breathing as he filled me. I was his slave; there was no doubt about it. He pulled out and ordered me off the bed and on all fours. His cock was still hard as he stood before me. He was very fulfilled in his expression as he had me lick his cock clean. I was tasting Master's cum and my ass. Then I knew he had shot his load in my ass, as I felt some of it drip out. It was a feeling I had never experienced and hoped to feel again. A feeling of pure submission.
Things didn't end; Master was in a dominating mood. He flogged me again and kept me on all fours. At one point, he grabbed my collar, pulling me up. His gloved fist cocked and read. He swung forward, and I cringed at him. He was pissed, saying I feared and didn't trust him. I was laid on the bed and flogged again. Hard, very hard. Later he told me he had broken a patch of my skin.
I was dragged off the bed again, on all fours on the floor. Sir returned his fist, and it came for me; I again tried to hold still, but he said I flinched. Back to flogging and then getting my ass beat with the gloved hands of my Master. Then dragged back to all fours. He ordered me to go out to the hall. I was frozen. I was naked; only my collar was around my neck. I hesitated and was dragged back and flogged for a third time. Master was serious this time; I was owned.
I was returned to the floor, and he ordered me to the hall. Slowly I moved forward; I knew I had to do this. I needed to follow his orders. But deep inside, I was hoping he would stop me at some point. I reached the door and thought for a moment. Master was silent. I didn't know where he was. I reached for the doorknob, turning it.
Please, Sir, don't make me do this, were my thoughts. I never verbalized those thoughts.
But there was no stopping. I slowly brought the door towards me, and it was ripped out of my hand and slammed shut. Master did stop me. I was so relieved. I did trust him, but he had me doubting that trust. Perhaps it is good. I doubt it occasionally, for it will keep me guessing and not let me get too comfortable in my position.
We ended up on the bed, holding each other. Feeling drained by our first true intense Master/slave session. I had been fucked by Master, powerfully fucked, and to this moment, I want to feel that again and again. As much as I want to feel his touch, his kiss, and him in my arms. That is all part of being with him.
That night we spent with a friend on Lake Michigan's shores, enjoying the evening talking. It got late, and we were in bed. That morning the collar was removed.