While what I wrote as How Jessi became an owned slut was fiction and fantasy, it inspired me to do what I did below. (Forgive the slow start but I want to tell the whole story for my own sake)
Understand while I would not call myself a prude, I have never been a slut. At 48 (basically married for 20 of them) I've had three female partners, one male one night stand, and one regular hook up. While I have done some wild things with some of them, bondage, blindfold, spanking, I've never really let go. With my regular hookup I've played around with Crossdressing. But never tried to be passable. But over the last six months I've fooled around with makeup, heels, nail polish, and a few nice outfits.
Last night changed all that. I knew there was a party Friday night at the Red Barn in Berlin New Jersey, and T-girls and CD got in free. So, I kept myself horny all week and decided I was going to drive the hour down there and let myself have some fun. I went to work in a red lace thong to keep myself horny all day. I came home from work and immediately showered and shaved. As I am doing this my regular hookup, who due to mutual scheduling issues, we haven't met in over a year, called, and said he was free tonight. I told him I was getting ready for a party and would send him a picture as soon as I was ready and could head to his place first if he liked what he saw.
After I shaved, I painted my fingernails Torch Red, put on a coat of foundation as I have a 5 o'clock shadow as I shave, open the blush I just bought and apply it for the first time, then finish off with True Red lipstick. I put on my breast forms to go from a nothing to a solid C cup and try on some of the new lingerie that I ordered. None of the bras went well with the breast forms. So, I went with just my basic black bra. Then I added a thong that barely qualified as underwear, If it rode up at all my package would come free, and the back was no thicker then a shoe string. I put on a pair of fancy looking fishnets with built in garters, then put on my black leather mini skits and a shear cream top that only covers my belly if I hike the skirt up high, so I hike the skirt up and I am now almost ready. For shoes I decide to go all out and put on my knee-high black leather boots with 5-inch stiletto heels. To finish off the look I put on a dirty blond wig that goes down to the middle of my back and cascades down the sides of my face.
I take a selfie and send it to my friend he replies, "Fun party, I'd hit that" and with that I head out the door and drive over to his place. He lets me in we small talk a little he tells me to spin around so he can get a good look. I make one request of him I ask him not to make me cum, because the only way I will go to the party is if I am crazy horny, otherwise I know I will chicken out.
He says "You look amazing, it's just a shame I will have to mess up that lipstick. "
I laugh, "I have it in the car so I can touch it up."
With that he pulls down his shorts and shows me his cock held out by a chrome cock ring. I drop to my knees right there and kiss the tip of his 6-inch circumcised cock. I lick my way around his head, then down and back up his shaft, then I take him all the way in as I deep throat him her tells me to look to the left, I comply and see that he is taking a video, so I look lustfully at the camera and make a show of bobbing up and down on his cock taking him all the way in each time. He pulls away and comes out with an audible pop. He orders me over to the couch where he sits down and I crawl between his legs and really go to town on his cock, eventually I focus on sucking on the head of his cock while jerking him off.
He moans, "oh you want to make me cum" I redouble my efforts stroking faster wanting my tasty reward. Soon he grunts and I feel him unload his seed in my mouth. I hold it there and when he tells me to stop, I pull off and show him my mouth and swallow. As I gently stroke him I notice a drop of cum on the tip of his cock and I lick it up.
I drive the hour to the Red Barn in Berlin New Jersey. I pull into the parking lot and find a space right up front. I am nervous as I said earlier, I am not a prude but have only every sucked two cocks, if I go in I know that number (among other things) will grow. I took a Viagra about 30 minutes before I got here, so that I am horny and worked up in an effort to get me to follow through. As I have never gone anywhere dressed like this before and I can only imagine what will happen if I let it.