A little background. I’ve always had an interest with dressing. I wore panties throughout high school, college I started to get into full outfits and after college is when the make up and wigs started. Throughout my journey, I’ve transitioned from a panty boy to a full on CD. Years after I got out of college, I started to become curious about men. At this point I’ve had a couple of girlfriends, but never been with a guy or had thoughts about men. For some reason, the more I got fully dressed up, the more I started to fantasize about what it would be like. So I did what anyone would do… I downloaded Grindr and my search begins. I was around 23 at the time. Felt like I spoke to hundreds of different profiles, but only had 2-3 that really peaked my interest. One of them messaged me daily. He was around 50. He was very kind, understanding of my concerns, discreet and was patient. We ended up meeting a couple times in different hotels that first year of talking. We clicked right off the bat. He was so sensual with every encounter. He’d take his time exploring my body. Making the first part of our meet ups always about me. Which made me crave him even more. He was average in length, but he was thick with a slight curve up. Fast forward a couple months. Up until this point, him and I haven’t really spoken much about our personal lives. We talk about a few hobbies, but nothing very deep. I had a free day during the week, so I decided to get dressed up. I messaged him some pics later that night. It was late, and I assumed he was already in bed. A couple minutes later I get a response from him. We do our normal dirty talk, but this night was different. Things escalated quick. We agreed that I’d just give him a quick blowjob. He sent me his address and told me to meet him. At this point I was comfortable with him and already ready. I left immediately. It was about a 15 minute drive to the address he sent me. He started sending me messages like “don’t park in the driveway”, “I’ll be on the left side of the house”. I found it a little suspicious, but thought he might have had roommates. It was late, and I didn’t judge or think mud about it. I arrive at his place, and see him waiting on the side in the shadows like he said. It was a beautiful night. I walk up to him and he grabs my hand and guides me towards the back of his house. Half way down the side of the house he stops. He quietly says, “I have something to tell you. I’m married. I told my wife 2 weeks ago that I need to explore myself, and that I would like a divorce. She is inside asleep. If you want to leave I understand.” After a couple seconds of silence, I kissed him on the lips and dropped to my knees. He’s always been the first to initiate, but not this time. I lift up his shirt to give a small kiss to each of his nipples before slowly kissing down his body. He goes to remove his pants, but I stop him and do it myself. When I expose his cock, it’s not hard like I’m use to. I grab his balls with one hand and wrap my lips around his cock. Within seconds he was hard. Feeling him grow in my mouth was a first for me, and I loved it. In my head I was going to spend my time worshiping him. Licking from his balls to his head. Letting him feel the back of my throat. After only a minute or two of sucking his cock, he lifts me up. Returns the kiss that I gave him before dropping to my knees, and without saying a word presses me against the side of his house with my stomach against the wall. I don’t know why, but I instinctively put my hands up against the wall and spread my legs. Exposing my entire backside to him. He presses his body against mine and whispers “good girl” in my ear. That alone was enough to make me melt to the ground. His hand slid up my thigh , lifting up my skirt and pushing my thong to the side. I feel his head press against my ass, find my hole. Normally he has to spend some time loosening me up, but that night, his cock went straight in. It was amazing. Like he somehow knew my body better than i did. Like my hole was meant for his dick. He wasted no time. I could feel his cock gliding in and out of me. His balls slapping against my caged cock with each thrust. I feel him speeding up. I know his cock is about to pump me full of cum like he has always done in the past. Suddenly he says “ get on your knees”. Without hesitation, I drop to my knees. Within seconds, he pumps rope after rope across my face. I clean off his cock stand up.

We embrace each other for a quick moment. He gives me a kiss and I leave. We met a couple more times, but he ended up moving out of state for his job. We haven’t been in contact in years, but I often think about him. I have no way to reach him, so maybe this story will. I hope you enjoy.