Heather's Diary Pt. 01

Date 02/06/2021

Dear Diary: I cannot believe I did it. It has finally happened, and I could not be more confused, happy, excited, scared, and downright exasperated! Tonight, I had my first experience with a man as Heather. She had played around before online chatting and jacking off with men, but this time she got all dressed up and fulfilled some of her true desires.

After I traveled to my work destination I went to Target and bought myself a matching black lace bra and panties set, black thigh highs, found some heels that were on sale, and a black dress. After that I went to a local beauty store and bought myself a blonde wig. With on one the wiser, I went back to my room at the hotel, sat in the bath and shaved every inch of my body. Since I never show my face in any of my pictures, I don't wear make up at all. I did what I always do, open accounts looking to strike up some hot chats and share pics to get off. I had never been with a man before, so I had not planned on it this trip. That's when things changed for me.

After my bath I put on my lingerie, stockings, heels and wig. I then put on the black dress I bought, and it actually fit ok. I was happy being Heather in my hotel room. Taking pictures, sharing them online with other men, hoping to have them send me pics back. The I went out to the local sub and posted a picture of myself just to see if anyone was close by and interested. After watching sissy porn for about a half an hour, I noticed that I had a DM request. Hoping for pics I opened it up and had a rather nice message from a man in the town where I was. He said he was into CDs, was open to maybe meeting up if I wanted to at my hotel for some fun and asked some more questions. I was so excited and nervous, but I answered him with some information.

He quickly responded and wanted to know if I was serious about maybe meeting up because he didn't want to waste my time or his. He was not rude about it but rather direct. Said he was 55, divorced, and was looking for some fun since he had not had anything since his divorce. I made sure he knew I was a married man, and I had not been with a guy before, and was very nervous. We chatted for a while longer which put me at ease, but now it was past 11pm so I would have to come to the lobby to let him in. I did not want to get undressed so I tried to tell him we could maybe hook up tomorrow night. His response was to give me his address. Holy crap, it was only 5 minutes away. Since it was winter I could put on sweatpants, and a coat to cover up, take my heels off and walk out to my car and no one would know. He said I did not have to do anything I did not want to do, but he really wanted to see Heather.

My mind went blank, I responded with ok. What was I doing? I cannot do this, I am married, and while I like to have fun, I cannot do this!!! But I put on some sweatpants, covering my nylon clad legs, took off my heels and put on some sneakers. Grabbed a coat and put it on covering up the rest of my feminine clothing, took my wig off and put in in my coat zipping it up. As I walked to my car, I was mess, nervous trying to talk myself back into the safety of the hotel, but I wanted this. Although it was only a 5-minute drive, I was so nervous I would get pulled over that I could barely control my breathing. As I pulled into his apartment complex, I knew that there was no turning around now.

He answered his door with a polite greeting, was dressed in a t shirt and boxers, told me I could use the bathroom if I needed to and offered me a bottle of water. In the bathroom I looked at myself in the mirror, I could not believe I was doing this, but I had wanted this to happen for a long time now. No turning back. I took off my coat, pulled out my wig, took off my shoes and sweatpants, and then smoothed out my dress. I then put my wig on and remembered I had left my heels in the hotel room. Oh well, I am not so sure he cared about the heels anyway.

As I opened the bathroom door, he was already standing in his bedroom doorway. I was frozen with fear, but full of lust and feminine desires, and I made my way down the short hallway to his bedroom. I gently took my hand, led me to his bed, and had me sit down. He told me how beautiful I looked and asked me if I was ready to be Heather. All's I could do is nod and he sat down next me. He took my hand and placed it on his crotch. Holy crap he was hard and big! He kissed my neck and reminded me that I did not have to do anything I did not want to do. Then he stood up, took off his boxers and his T shirt, and laid down on his bed. At this point I could not control myself and I reached over and wrapped my hand around his hard cock. It felt so good, I let out a soft moan and this was the first time I had touched another man. It felt so good in my hand, and I started stroking.

After a couple of minutes, he asked me to stop. Disappointed, I did as he asked, and he told me stand up. As I did, he also got out of bed and stood in back of me. I could feel his hardness pressed up against my ass. I was so aroused and excited that I did not even notice him taking my dress down. As I stood there in my lingerie with his cock against my ass, he kissed my neck again as said he was hoping I would want to fulfill one of the desires I had told him about in our messaging. He then spun me around, so I was facing him, kissed me on the lips, and pushed me down to my knees. There I was face to face with his hard cock. Instinctively I opened my mouth and took his head in, I could not believe I was doing this now.

My desires took over, my lust conquered my fears, and I started making love to his cock with my mouth. Swirling my tongue over his head, bobbing up and down, cupping his full balls with my hands, and becoming the woman had always wanted to be. What an amazing experience. The longer I gave him head, the harder and more excited he got. I could feel his cock throb in my mouth, he was close, and he told me so. He had not had any action other than his own hand since his divorce. Remarkably he stopped me from finishing him off, but he said he wanted to cum on my face and in my mouth. He asked me to lay on my back on his bed, which I easily responded to with a smile and moan. He was now tugging on his cock right over my mouth, I could see him getting closer and closer to giving me my reward.

That is when he said he was going to cum. I opened my mouth and took a huge rope of cum right on my tongue. He moaned and shot rope after rope on my face and in my mouth. I was in heaven, I was Heather, I had wanted this for so long! As I swallowed the cum in my mouth, he continued to shoot on my face until he was emptied. The smell, the excitement, the hunger, the amazing feeling of pleasuring a man left me completely unaware that I had also cum in my panties when he said my name and shot his load in my mouth. He asked if I wanted a picture of my face covered in cum to which I nodded. He then grabbed his phone from the nightstand and took a picture. Said he would send it to me via DM. He was kind enough to grab me a towel to clean up, wished me a good night, and said he would be in touch. I had not told him that Heather would be in town for another 10 days!

To be continued...