A Crossdresser's First

I am not sure how it all started but as i grew up and started noticing girls I was always attracted to the ones in hosiery. Usually that meant skirts or dresses and always with heels. To me it was the picture of femininity. And I think they understood that. You could see their confidence, enjoying the attention from the boys.

At some point I decided to try it out myself and there was no looking back. I dabbled as I grew up borrowing a pair of pantyhose from my sister or mom. Maybe a dress if I had some time to myself. Eventually I started borrowing lipstick. I looked forward to the day when I had a place of my own to experiment further.

Later in life circumstances changed allowing me to fully explore my love of hosiery and this eventually expanded to other women's clothes. Eventually I amassed quite a wardrobe. Dresses, skirts, blouses, heels, breast forms, and various pieces of shape wear seemed to arrive weekly at my house.

After a time my focus went to full presentation. I started wearing full make up, watching tutorials to help. Especially with the eyes - which are hard to do!! I got pretty good with my look and started trying different styles of wigs. I was amazed at the transformation and eventually settled into a routine of spending the weekends dressed up.

At a point dressing alone was not enough. I saw other people posting pictures online and receiving comments. I thought I looked good and wanted to see what other people thought. I started visiting sites where I could post pictures and have chats. It seemed everyday I dressed I found myself in front of the camera doing photo shoots and then uploading the pictures. I got a lot of positive feedback including from men.

Soon after I started fantasizing what it would be like to be with a man. I wasn't interested in someone after my male parts or who wanted to kiss or cuddle. Just someone who was turned on by my appearance and told me what to do. Maybe getting on my knees and servicing them or being bent over while they pull my pantyhose down just enough to have their way with me.

I bought toys for practice. The suction cup dildo's were perfect to practice my oral skills. I would always wear lipstick and measure my progress by the rings I left on the cock. I eventually could handle 8" with no problems. They worked well for anal also. With the right lubrication I could handle any size or shape.

Once I made up my mind I wanted to pursue an encounter I joined a popular dating app that was friendly to crossdressers. This would give me access to men local to me. I posted a profile as a submissive bottom crossdresser looking for a top. I included pictures of myself dressed in various outfits from conservative dresses to more sexy short skirts or dresses with garter belts and stockings. Early on I got plenty of attention but never could find the right match. Although I did enjoy the chatting!

Fast forward a few months and I had to travel a couple of weeks for work which didn't allow me to indulge in my hobby. I got home on a Saturday morning anticipating a day fully dressed. As soon as my bags were unpacked I went to work. I couldn't believe how horny I was.

After showering and shaving I started my transformation. I put on my gaff, tucked myself smooth, and then put on my favorite black neon 40 sheer to waist pantyhose. My 38G breast forms and bra were next. I opted for an above the knee long sleeve burgundy sweater dress to finish the outfit. The slim fit of the dress highlighted my breasts and black stockinged legs nicely. I then sat down to finish my face and eyes. After my wig was on I then focused on my lips. I chose a dark red long lasting matte liquid lipstick that matched my dress color. I was blessed with full lips and the dark red looked sexy. I finished the outfit with some black 5" pumps.

After an hour or so the urge to hook up with a man took over. I decided to log onto the dating app and was quickly hit up with the usual taps. Nothing that really interested me. I went back to finishing some chores and eventually checked the app again. This time I noticed an individual logged in who was into fem cds. He was easy to notice because he was located relatively close to me.

I waited to see if he would hit me up and was rewarded with a chat a few minutes later. We did the typical banter however as the chat continued he was checking all the right boxes. He was fit, married, had only been with his wife, and was only interested in getting serviced. It seemed safe and discreet. As we continued to chat I convinced myself this was the guy.

He asked if I was fully made up and I told him yes describing my outfit. He told me it sounded sexy and asked if we could hook up. After a couple of minutes I said fuck it let's do this. I told him I was available, could host, and would love to give him a blowjob. He told me he had about an hour before his wife got back and would love to come over.

I was shaking with nerves as I gave him the street I lived on. I told him i would watch for his car. He described it for me and told me he would be over in five minutes. I quickly freshened up my lipstick and started watching for him from my bedroom window still shaking in anticipation. When I noticed his car approach I told him the house and he pulled into the driveway.

Now with my heart leaping out of my chest I opened the front door and let him in. I smiled and asked him if he liked what he saw. He told me he did with a smile which made me calm down a little. I grabbed his hand and walked him back to my bedroom. After a few awkward seconds I reached out and rubbed his cock as I kneeled down in front of him. I kept rubbing his cock through his pants and asked him to take them off. After he unzipped his pants I pulled them down and started rubbing his cock again through his underwear.

At this point he was fully erect and ready to go which excited me even more. He pulled his underwear down and out popped a beautiful 7" cut cock. I quickly went to work on the head of his cock sucking it while stroking his shaft. I couldn't believe how soft and smooth it was! After a few minutes I needed more in my mouth. I took my hand off his shaft and grabbed both his thighs to pull him deeper into my mouth. I kept at it until I was able to bury his cock in my mouth.

Once he saw I was comfortable with his full length he grabbed the back of my head and started to fuck my mouth with more energy. He started to get more vocal telling me to suck his cock and moaning that it felt good. I had to rest a bit so I pulled it out of my mouth and kept stroking it with my hand. I looked up at him and he was staring at me with hungry eyes. I soon went back to work and he quickly resumed fucking my mouth.

I had always known I was going to swallow but wasn't sure how it would happen. Would he pull out and jerk off into my mouth or would he shove it in deep and cum in my throat? Right on queue he said he was going to cum. I pulled his thighs toward me letting him know he could do what he wanted. He put both hands on the back of my head and told me he was cumming. I took his whole cock in my mouth as he starting shooting his load. It didn't seem like he had sex in a while because he kept shooting load after load. His cock was so deep in my mouth it went right down my throat.

Eventually he stopped and I slowly pulled his cock out. I continued to lick and suck it clean as it slowly softened. The lipstick stains covered the length of his cock. When I looked up at him he was staring at me and said "That was awesome". He pulled up his underwear and pants and then helped me to my feet. He said he needed to go and I walked him to the front door. As he was leaving he asked if we could hook up again. I told him I was already looking forward to it!

I hope next time he can stay longer!!