Craiglist was wild

I was a dumb twenty-two year old kid. A skinny, short haired white kid with glasses that blended in with a lot of crowds, skaters, gamers, emos. Occasionally I’d cruise on Craigslist and check out older guys, I hadn’t done anything yet, but I was in a different city today. 

No one knew me, so that, coupled with a little alcohol and I found myself driving to some sixty year old stranger’s house, someone old enough to be my grandparent, after talking to an older guy on Craigslist.

I pull up and he’s waiting on his porch. This guy met the general feel I had almost expected. Older, bearish porn addict with a thing for younger guys that look slightly feminine. As we get into the house he tells me to stop and strip, the kink was already discussed and I was down. 

I take off my t-shirt, my jeans, underwear, socks and shoes. I hand them to him and he holds onto them. 

He starts walking away, telling me he’ll be back. About ten minutes go by as I’m standing fully exposed in direct line of the front door. Like I said, we discussed kinks, one of his was humiliation, well, I’m the example of the kink in this scenario. 

I had never thought of myself as submissive, but as I learned throughout that day, well, turns out I have a submissive streak, a cross dressing fetish and a daddy kink. 

Another ten minutes go by and “Daddy”, as he’s telling me to call him now, comes back. He has a collar with a leash attached, a wig and Spencer’s/Sex Shop style school girl costume, and a vibrating dildo. As Daddy is going to sit on the couch he bends down and suctions the dildo to the floor, covering it in lube.

He sits on the couch.

He then starts watching me putting on the fishnets, then the socks, the skirt and the top. I attach the collar and put the wig on. He waves me over, calling me a “good whore” who “knows their place”. I hadn’t bottomed, but I had played with toys and plugs to this point, so Daddy puts me on my knees and watches my face twist as the dildo goes up my ass. 

As I start to rhythmically ride the dildo, Daddy turns the vibration on and pulls on the collar and sends my face into his crotch, cock already out, hard and erect. I start kissing and licking the tip, slowly starting to swallow it to my tonsils, then in my throat, all the while saying how he’s glad I “know how to act like a proper bitch” and that I act more “like a good wife” than his did before she left him. 

I’ve cum, limp, at least three times by now, he’d come four, once on my face, once in my mouth, and two times down my throat. We’d spent two hours. Taking pictures of the earlier two as “trophies”.

After that he let me use his bathroom to clean up. I showered and when I got out, my clothes were clean and folded on the sink. I dried off and thanked him for my first time, and I’m still a fem leaning guy with a a submissive streak for older guys and a fetish for Cross Dressing.