My Best Friend

Michael has been my best friend for over 35 years; we have had many great times together and our families are great friends. We have been through happy times and sad times together and have always been there for each other and always supportive of each other in times of need. For the past thirty years we have lived in different areas of the country but have remained remarkably close friends. However, for all those years I had not been honest to him about myself and honestly it always bothered me a great deal.

I had never disclosed to him or anyone else for that matter that I am a transgender woman. It is a secret I never shared with him and kept hidden away deep inside me always fearful that I would lose a friendship that meant the world to me should he find out. Eight years ago, I decided to begin transitioning to the person I have always truly been, and I knew that meant I would have to disclose to Michael that I am in fact a transgender woman.

Shortly after that we were scheduled to be in the same city for work and I decided that it would be a good time to have a talk with Michael and tell him my story. I told him I needed some time to talk with him and we decided to have dinner and talk; and wow did we talk. For well over four hours! I told him everything. I let it all out about who I really was and what it had been like to have kept this huge secret about me from the world but especially from him for all these years. I told him that there were so many times I wanted to talk with him and was so close to spilling my guts to him, but I always chickened out because I was so scared of losing such a good friend.

But it was now time to be who I really am, and I wanted him to be the first person to know about my plans to transition to my true gender, my authentic gender. Of course, as expected he was beyond shocked and he had a ton of questions but, he seemed genuinely concerned and honestly it was so nice to talk with him, and I was proud of my friend and I felt closer to him than I had ever been.

We finished our talk and he wished me all the best and to let him know if I needed anything or just wanted someone to talk with. I did not know when we would see each other again but I was glad to know I had finally been able to tell him the truth about me and to feel like he accepted me, the true me.

We stayed in touch over the next couple of years, but distance as well as family and business obligations kept us from meeting although we did talk quite a bit. Michael had many questions which of course was understandable, and we would have long phone, text, and email conversations about what I was going through and how I was doing. He seemed very sympathetic to my transition and I so appreciated having his support and feeling he was in my corner.

Five years ago, we found out we would both be in the same city for a two-day conference, and we were determined to split off from a busy conference to at least have dinner together and to finally catch up in person. I warned him that I was deep into my transition and would be attending the conference as Meg, a person he had yet to meet. Although we had talked many times over the years, he had not seen any photos of me. I was not the person he had seen a couple of years ago and I wanted to make sure he was ready for that.

We texted each other upon arrival and learned our rooms were 3 doors from each other, and he told me he had taken a shot and made dinner reservations at a nice restaurant for us for that night. I was extremely nervous about seeing him the very first time as Meg but was also relieved to finally get it over with. He had not seen me in a few years and much had changed with me physically and mentally, but I was hopeful we could remain friends once he met and spent some time with Meg.

It took me forever to decide what to wear for this moment although I had been thinking about it since we agreed to meet at the conference. I knew the restaurant was on the nice side, so I knew a dress was in order but which one? I had brought 6 different dresses with me and decided to wear the burgundy one with a cut out to show a glimpse of cleavage but not too slutty, just enough to let him know that changes had occurred but also not put my boobs on full display. It is a pretty dress and fits we well and I always feel good in it. I spent a ton of time making sure my hair and makeup was as perfect as I could get it and added my favorite gold hoop earrings and a simple gold necklace. Slipped on my black leather heels and I was as ready as I would ever be.

He suggested meeting in the lobby and grabbing a cab to the restaurant. I arrived in the lobby after him and walked right up to him and said hi before he figured out who I was. He smiled and stared a polite stare trying to take me all in. I appreciated his predicament and told him that if he felt the least bit uncomfortable, we could skip dinner and talk another time, but he said no no he was fine, and we definitely should go.

The restaurant was beautiful, and the food and wine wonderful, and our conversation was incredible. We talked for hours about what was going in our lives and how we were really doing under the surface something that always meant a lot to me. I apologized again for the 800th time about not coming out to him sooner and he graciously said he understood but was happy for me that it was finally happening.

We took a cab back to our hotel and ran into a couple of people we both knew in the lobby and chatted with them for a bit, but I begged off as I did not feel up to a long explanation of my story and honestly, I was exhausted from traveling all day. I started walking to the elevator and was quickly joined by Michael who told me he too was tired. We both just stared and smiled at each other in the elevator. I was so relieved to get this first meeting over with and I was so thankful that it seemed to have gone well.

We walked down the hall and I stopped at my door to say good night and turned to go in my room. I took one step and suddenly I felt Michael's arm glide around my waist pulling me to him and hearing him ask if he could kiss me. He told me that since the moment we met in the lobby all he wanted to do was kiss me. Unconsciously I shook my completely stunned and surprised head OK, and he pulled me close and kissed me more passionately than I had been kissed in an awfully long time. I melted in his arms as I felt his tongue slide between my lips and touch mine. We stood in the hallway kissing and I heard myself invite him still not fully grasping what was going on. Our kiss continued in my room and I felt his hands unzip my dress while also feeling his hardness against me. My dress fell to the ground and I unzipped his slacks searching for the source of the hardness I felt. Standing there in bra and panties in front of someone I had known for so many years as my best friend while also feeling more sexually aroused than I had felt in years was incredibly strange but also comforting because I felt so safe.

Without thinking I dropped to my knees and took his rock-hard cock out and engulfed it, taking it in as far as I could. I wanted to swallow it all I wanted to feel his tip on the back of my throat. I wanted him so badly and the feeling shocked me. What was happening shocked me!

Michael reached down, pulled me up and turned me towards the bed and then bent me over it while pulling down my panties. I then felt his hard cock working its way into my ass slowly siding in and out of me till I felt it completely inside of me. I started pushing back every time he pumped, and we fell into a delicious rhythm of him fucking me for my first time. All the while he was fucking me, he was fondling my breasts and honestly, I do not think I have ever been so turned on. I was just lost in a delicious zone of sexy lusciousness and did not want to stop what was happening to me.

I felt my best friend tense up and thrust his cock deep inside me and explode filling me with his juice. Suddenly it was quiet, and we collapsed on the bed both of us feeling completely drained. Michael pulled the bed covers down and we slipped under the sheets with him pulling me close and holding me. Laying there in Michael's arms feeling him holding me tight thinking of what had just happened and our friendship over the years I was just blown away, my mind was reeling, and I began to weep happy and safe tears of joy. We fell asleep with him holding me and I woke up the next morning realizing it was not a dream and looking down at Michael sleeping peacefully but also smiling when I saw his raging hard on.

After a bit of chuckle, I leaned down and lightly kissed his cock good morning and took the beautiful tip into my mouth. I then began gently running my tongue up and down his shaft and kissing his beautiful smooth balls. Hearing a bit of a murmur from Michael I took his cock completely inside my mouth and I let out a moan as it came to life inside me. By now Michael was wide awake and fully enjoying his morning blow job and pushing my head down as he drove his cock deeper inside my mouth. Soon I felt his body tense up and his cock erupted in my mouth with such intensity that his cum filled my mouth and I choked a little as I hungrily swallowed as much as I could. With his cum still on my lips he pulled me up and kissed me hard and hugged me close.

So, to be honest we did not learn a lot from the conference, but we did learn a lot about each other and oh how we fucked, and our friendship is deeper on much different and wonderful level now.