** I am on mobile***

This happened back when Craigslist hookups where still happening. I was 19ish and was curious on how it all went down after you sent that first email.

It was a gloomy summer morning and my usual routine was to go online and stroke it to “riskay” photos of people online that might be semi close to my location. There was nothing working for me in the regular w4m section and decided to dabble in something taboo and looked into the t4m. And my god was I not disappointed. They where all beautiful and busty and naked. Thats when I ran into an ad that was just posted roughly an hour ago.

“Chubby Crossdresser Waiting for you, Door is unlocked” is what the title read. I clicked on it and it said that they where chubby (I love BBW so this was not a deal breaker) and all I had to do was walk in and drop my pants and they would do the rest. Now i had nothing better to do than beat my own meat, so I hit the reply button. I say the normal stuff “hey i saw your ad and I’m interested. 19 Latino uncut 8 inches and live on the eastside” 10 minutes pass and I get a reply saying that they are also on the eastside (turns out they where a few blocks from me) and that I can head over right now.

I threw on my sweater and some jeans and walked right on over. It was in the neighborhood but a part i never frequented except for my barber that was a few houses down. There where very few people out and about so it made me even more nervous. I had never been with a guy, would I even get hard, hope I dont bust quick. I walk up to the house, as soon as I get to the front gate the front door pops open, that was my invitation. I open the gate, it makes the loudest creaking noise of my life, and walk into his property.

As soon as I enter the front door I hear moans blaring from another room. And behind me the door closes and I see my first CD. Now they arent much to look at. Not passable to say the least. First thing I notice is the blonde wig that covers the face that has a heavy 5o’clock shadow. Their body looked more like just your typical dude in a girdle and fishnets. Picture uncle fester or gru in drag and you basically have the idea. But I was here and I was tired of getting myself off. So he leads me to the bedroom where the porn is playing, of course its T porn and im watching it.

As I’m standing looking at the porn getting into the idea, he drops to his knees and pulls down my pants and slowly starts making out with my flaccid dick. But my god does it feel wonderful. None of my exes had ever played with my dick that way before. And immediately I get rock hard, and he moans in contentment knowing that I am into it now. Now i dont know if you have ever gotten head from a person wearing a wig, but it is off putting to say the least and almost threw me off when i grabbed the head to help me face fuck them. They deep throat me and they gagged on my cock. And i was getting very into it.

After 10 minutes or so, you can tell that I was too much, he asked me to stop. Pulled out a magnum and put in on me and bent over their bed. Ive never done this before so I wasnt sure how to go about it. But i did what felt right and placed my hand on their shoulder and my other hand on my dick and lead it into the ass. I’m a little bit on the thicker side so i always have a problem at first, but i was so worked up I didnt care and just pushed my way through. He yells in pleasure into his pillow and I just start pumping. Placed both hands on their hips and do my best to go balls deep. I keep going that sweat ia pouring down my forehead and then I feel it. My balls start to tighten up and I blow the biggest load. I cant stand anymore and just rest my head on their back while my dick slowly slides out.

He asks if I am done, I just nod yes and I rip the condom off and throw it in the trash. Pull up my pants and walk away a new man. It was not my last time with a CD but it was my last time with him.