#Deepthroat Diary Entry One

Dear Diary,

With the help of dedicated Mistress Alexis, I have been transitioning into a woman over the past few years. It began about 5 years ago when my marriage ended. My wife was unhappy for years with my lack of sexual performance, which led to cuckolding, then to her falling in love, getting pregnant and finally divorcing me. Deep down I always knew my place was to service men, not women. But, societal pressures kept my secret life secret, even from myself. I never did cheat on my wife with another man. But, there were always feelings that my purpose was to service men.

As my divorce was proceeding, I began to check out online ads of men looking for men, to get an idea of what was out there. I did not see myself as gay, more of a man wanting to be feminine, dressed as a woman and serving men. I was not looking for a relationship, just an encounter at a hotel. I was not even concerned about my own orgasm. I felt my pleasure would be satisfying these men’s sexual needs.

I began telling my story to Mistress Alexis and over the course of a couple months she counseled me on how to dress, what to wear, makeup, etc. Being nervous about meeting men I did not know well, she taught me how to spot the right ad, how to place my own ad and how-to text or email with a proposed partner. After a few months, I was ready to hit the streets so to speak and have my 1st encounter. I contacted a few men through hook up sites, emailed a bit for a comfort level and picked one to see. Mistress was very excited. We decided for the 1st time I would perform oral only, and then see how that went. Mistress had me practicing on a variety of dildos to prepare.

The man was about 5’10”, 170 lbs., clean cut (he had sent me a few pics), no facial hair and minimal body hair (a preference of mine. I am not attracted to facial hair or body hair). He worked as a salesperson in the next town over, so it was easy for him to cut out a bit early at the end of the day and meet. I got a hotel room and we agreed to meet at 4pm. I texted him the room# and he arrived on time. I was dressed in a nice teal baby doll, stockings, heels, wig and makeup with a muted red lipstick. Sitting on the edge of the bed, I left the door slightly ajar, so he could just walk in and lock the door behind him.

He walks in, locks the door and approaches me. My heart is racing- I feel like it could jump out of my chest. The room is fairly dark, but I can see him well enough. He doesn’t say anything, takes my hand and stands me up. He rubs his hands up and down my body, sides, chest, then down my ass and up my legs. He then sits me back down on the bed and steps in front of me. He is just standing there and after 5 seconds it dawns on me he is ready. (First time so didn’t quite know the process yet, lol). I quickly reach for his pants and begin to unbutton and pull them down. I see his bulge through his boxer briefs and begin to massage and feel his cock- 1st time I have ever touched another man’s cock. I tried to be as calm as possible and I did tell him I was new at this, so it seemed to be going well. After a few minutes he was even harder, so I took this as my next cue to remove his briefs. His cock sprang out to attention and wow- a good 7 inches and nice thickness. A bit more with my hands and then I slip on a condom and go in with my mouth.

Looking back, I was hooked right away. It felt so good and so natural to have this cock in my mouth. We had talked ahead of time about using condoms and he was fine with it. I got into a nice rhythm, licking his balls, licking the shaft up and down and getting maybe an inch or two down my throat. After about 5 minutes he pulls away, lays down on the bed and I crawl between his legs to continue. He really gets into it now, grabbing my head and face fucking me- not too rough- but enough to know he’s in charge. 5 minutes later he blows his load in my mouth and into the condom. His breathing begins to subside and he’s lying on his back, his cock beginning to soften. It appears he is waiting for me to remove the condom, so I do and then get him a washcloth to clean up. I do this as well. He then gets up, gets dressed and leaves. He never said a word the entire time.

After it was over I could not wait to do it again. I was happy that I felt this way and couldn’t wait to tell Mistress.

Over the next few months, I was out and about with men probably twice a week. I had a few regulars and since I felt safe with them, I began blowing them bareback. I also began taking some loads in my mouth and sometimes on my face. I liked leaving they’re cum on my face for a few minutes after they left. The humiliation feeling was intense.



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Alexis4u of Niteflirt

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