This is a print version of story Mike part 2 by kinky_mn_man from

Mike part 2

Thank you for all of the comments and messages about me and Mike. I have decided to go ahead and continue sharing about our fun together. I am not planning to cover every Monday night we spent together, but I thought I should share the important moments in our relationship.
Our first Monday night fun was pretty vanilla to be honest. Mike had never been with a guy except in his mind. I don’t remember who was playing, but we did have to keep the Monday Night Football game on so we could keep track of time.
I was nervous and excited. I was nervous about what I was about to do. I was used to being with men in a cuck situation when the wife or gf was involved. Those situations were mostly about control, the Dom and sub roles that I truly do enjoy. This first meeting was about something more. I tried to tell myself that I was simply helping my friend, but deep down it was a little more than that. I simply did not want to admit that our relationship was about to become closer.
Now it was time for our first MNF meeting. This is the meeting that officially changed my relationship with Mike. He was already a close dear friend… my best friend. I did not at the time, and I still don’t, have many people I call friend. The pre-game festivities were starting and Mike was not at my place yet. My mind started to wander. Was this something I should be doing? Could I really be friends with Mike and still have sex with him? Could he keep his desires from his future wife? Was I gay? Mike and I had a relationship that could be classified as a typical guy relationship. I thought our relationship could have stopped after the moments with Deena, but we both knew that it could not be the same after he had my cock in his mouth.
Mike arrived just after kickoff. I don’t remember who the hell was playing that night. I wasn’t really focused on that. My apartment buzzer rang and my heart skipped a beat. What the hell was going on with me? I never felt like that about meeting anyone before. I hit the buzzer and then opened my door. Mike was at the front door moments later. He walked in and we watched the rest of the first quarter and some of the 2nd quarter of the game. We talked a lot during the commercials and many times past the commercials. The football game was just an excuse to see each other. I was used to making the first move, but I had never done anything like this before. I could tell Mike was waiting for me to make the first move. Mike was looking down most of this time. I could tell he was excited because of his chest was pounding. I assured him that there was nothing wrong with him and after I caressed his face, Mike got up to use the bathroom and I thought that it was time to make something happen. As he left the bathroom and shut the door, I greeted him and told him to go into my bedroom. I put some porn on the bedroom tv. I needed to get myself excited a bit. I was feeling too nervous. I think I was scared that I may be losing my best friend for some sexual fun. Mike did as I instructed and walked into the bedroom. He didn’t say a word. We sat on the edge of the bed together and simply talked. We talked about what he truly desires. We talked about how long he has desired to dress as a woman. He said he didn’t want to become a woman. He simply wanted to dress as a woman and be treated like a woman by someone who he thought was a man. I felt honored that he wanted me to be his first. I didn’t exactly know what to say. We talked about us both being a bit nervous as this was new for both of us. I told him about most of my sexual experiences and he said he wondered about me sometimes. He thanked me for being truthful. We became instantly closer at that moment. He told me that I made him feel safe. He said he has not had that safe feeling around any other man and that he wanted me to make him my “girl”. Mike sounded conflicting at times. I remember he said he wanted a f****y, but he also wanted to feel attractive to a real man who made him feel safe. He said he wanted my cock inside of him. He told me that he knew that I was the one after seeing me with Deena and how I treated him that day. I remember he said I was more like a big b*****r. He loved me telling him what to do, but with it feeling more like a guide than an angry boss. He told me how much he enjoyed sucking on my cock and tasting my cum, mixed with Deena’s juices. That comment got me very excited. The porn in the background was hardly noticeable at that point. I told him to remove his clothes as I removed mine. He did as he was told and then he saw my rock hard cock. I saw him get hard by seeing my erect cock. We had about the same size cock, mine was a bit thicker and longer. He said that it wasn’t my cock so much as what it was attached to. He wanted to make me feel good. I laid back on the bed and told him to taste me. He was happy to take my cock in his mouth. I enjoyed looking down into his eyes and telling him how much he made me feel good. He loved that. I specifically remember saying “Yes sweetie … right there.” I gave him positive feedback like he was my little girl. He craved to be my little girl and I was happy to help him with that. I was almost about to pop a huge load in his mouth, when I stopped and told him to go into my closet. I wanted to release myself in his ass. I wanted him to feel my pulsating cock release its seed deep inside of him. I told him to get the lube on the shelf along with the box of latex gloves. He grabbed them and then looked at me before getting back on the bed. He paused and with a glow on his face said that he could not believe this was going to happen. He had almost as much hair on his body as me (sorry if I may have lost some of you about the hair, but I am telling you what took place). He bent over and I told him to help me out be spreading his ass cheeks apart. He spread his ass open and I slowly pressed my middle finger in his virgin ass. He was very tight. After several minutes of moving my middle finger in and out of him, I slowly shoved 2 fingers in him. This is when I instructed him to move to me. He needed to “fuck” my hand. He would cringe every so often and he did let me know that it was uncomfortable. I was starting to feel more comfortable as I felt like I could treat this situation the way I had with other cuckholded men in the past.
Mike was moving back and forth on my 2 fingers when I told him to stop and I decided to see if I could get my cock inside of him. Mike was bent over with his back arched as high as he could be. I slapped hi sass with my cock and he quietly waited for me to enter. I attempted to press the head of my cock into his ass. It was too small and my cock was just a little too thick. Mike began to move his ass back toward me. I just could not get my cock inside of him. I told him it wasn’t going to work and Mike rolled over and got off the bed. I grabbed his arm and pulled him back toward me. He was upset that I didn’t want to fuck him. He threatened to leave and started to almost pout. I grabbed his clothes as he pulled away from me and went into my bathroom. I had to convince him that nothing was wrong with him. That I still wanted to cum inside of him. He was upset. He was on the verge of tears when he opened the door and we got back into my bedroom. I turned off the porn that was background noise and told him that we could stop, and try another day. I was still rock hard. He looked down and started caressing my cock. I assured him that we just needed to stretch out his asshole and we could continue on with the fun. He apologized for getting upset and then proceeded to suck me dry. I was on the bed on my back with him leaning over me and sucking on me … looking up at me to see how good he was making me feel. I was about to release when I told him and he stayed on my cock. I grasped his head and kept him on me until I released every drop pulsating hard into his mouth. He licked up every drop and enjoyed cleaning the cum from my balls. He got up and grabbed a washcloth from the bathroom and cleaned me off. I told him to lay down next to me and we watched the rest of the game. We were in my bed and I held him as we were naked together. Mike did not want me to touch his cock at all that night. Mike gave me another blowjob just before he left and we talked about plans to get him skirts, a butt plug, other toys and clothing. Mike told me that he went home and masturbated thinking of what it must feel like to have my cock inside of him. Later that week I got a butt plug for Mike. It was about the size of 2 fingers. I told him to wear it several times before the next week. It was two weeks after this meeting that I was able to get my cock inside of Mike’s ass. Mike also loved that I gave him “homework” to be completed prior to our next meeting.
After this initial MNF event, Mike told me that he felt even more comfortable with me and he continued to share the insecurities of his body and thinking there was something wrong with him. My relationship with mike forever did change after this evening. We became much closer. He became more submissive to me as I took the lead in our relationship. My feelings for him also changed from friends to something more. Our relationship got a little more complicated at time went on, especially after he told me the date of his wedding. I will share more on that later.
I will share more about the first time I came inside of Mike in my next story. Thanks again for your kind comments and messages. I truly appreciate them all. Thanks for reading.

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