I have always had a fetish for women's clothing and would wear my wife's panties and bras when I got the chance to. Them one Halloween I told her I wanted to dress as a woman and see how many friends I could fool since there was a party at our house as the night went on, I got hit on by several of our male neighbors. I found myself extremely turned on by this. I continued to enjoy dressing for another year till we divorced, and I lost my collection of female cloths. My life continued getting remarried and lived a happy life for many years. About the time I turned 62 I had a serious health scare and was not sure how much longer I would live.
So, I decided if I was ever going to live any of my fantasies I needed to get started. So, I started reading fantasy stories on websites first I purchased some panties and would wear them most of the time. I really liked the sexy silk ones. Then came chastity after purchasing several cages I found one that I could wear for weeks if necessary. The silk panties and small chastity cage gave me the feeling that I was truly a girl since I had no cock to play with. Then came the bras and blouses. I just kept reading and looking at pictures on the internet.
Then I found what I needed an app for my phone that I could put the keys to my chastity in a safe and have a keyholder control how long I would be locked for. This led to a gentleman who made me open an account on imagefap and take pictures of myself and upload them for his pleasure. After posting many pictures and having hundreds of views. I was hooked and started looking for other sites to expose myself on. But I kept seeing pictures of men dressed in womans under things giving men blow jobs. The more I saw the more curious I got then I guy from one of the sites I was exposing myself on started chatting with me and it turned out we lived in the same city and my pictures wearing panties and bras turned him on. The morning we chatted the more I wondered what it was like to be a woman on her knees sucking a man's cock and swallowing his cum.
I decided to purchase a very sexy white with pick roses silk camisole and post some pictures wearing it but when it put it on all I wanted to do was let the woman in me go and suck a man's cock. Within a week I found myself on my knees all dressed up getting ready to suck on my first cock. I will never forget holing another man's cock in my hand and playing with it. Then kissing the head and finally putting it in my mouth. I was in heaven his cock was not big, but it was in my mouth, and I was fulfilling a fantasy it was not long till he tensed up and I knew what was about to happen. He shot his load into my mouth and throat, and I enjoyed my first taste of another man's cum. All the way back home I just replayed the whole thing in my head and kept tasting his cum in my mouth.
That moment changed my whole life we got together 2 more times after that. I decided to try and find somebody with a bigger cock to suck. So, I started placing ads on Doublelist to see what I could find and sure enough within a week or, so I was on my knees sucking a man with a good 8-inch cock and a large load to swallow.
After that I met another older gentleman on another website who liked girly boys, so we set up a meeting at his house. He taught me to go slow and easy. To play with his cock and balls kissing them now and then. Sucking on his balls and then his cock for a while there was porn playing on his laptop, so I was watching a woman give a blowjob the whole time I was giving a blowjob dressed in my sexy chemise. After some time, he rewarded me with a nice load to swallow. He then let me put my shorts on but made me walk out to my car wearing the satin chemise and some of his cum on my face. It was such a turn on I drove halfway home before putting my shirt on.
I then went through a spell that I could not find a cock to blow until one Saturday when I was contacted by a guy who wanted a Blow Job but needed me to get the quick while his wife was shopping so I got there as soon as I could I got my first face fuck with a nice sized cock and load to finish.
Then came COVID and I just did not feel safe trying to meet strangers and suck on their cock. Once COVID was under control it. We had decided to move to a small town on the other side of the state. I ended up getting rid of all my girls' cloths and chastity cages and live a straight life in the small town.
Well, that lasted about 9 months before the urge to get another chastity cage hit and I found myself on amazon ordering one. Once I put it on the I just wanted to suck cock again, but I am in a completely strange town and have no idea if that goes on here or not. So reopened my account on squirt.org and discovered that there are a couple of cruising spots in town at parks. There are several guys on the website that live in this area but have not been able to hook up with any. Then about 3 weeks ago I went to one of the parks to see if there was any action, I had done that 2 or 3 times a week and always quiet until then. I had gone to the end of the road, and nobody was there so I went to the parking lot and parked for a few minutes. Then I decided to go to the end of the road again and there was a car sitting there so I pulled up next to him and just started some small talk. I was sure he wanted a blow job and before I knew it, I ask him if he did sure enough, he did. So, I parked and sat on his running board and gave him a blow job right there in the street. What a turn on that was and I had just sucked my 5th cock and was ready for more.
Then a few days later I was contacted by a man on Grindr looking for a blowjob and he knew of a family restroom in a public building that was not very busy. The next day I met him there and proceeded to suck on my 6th cock which was another total turn on in a public place since I ran into a guy on my way out and probably had a little cum in my beard.
I have since been contacted by several men wanting service so I think It will be a fun and rewarding summer.
Thank for reading my story