Monica's Mixed Bag

I have crossdressed in private since I was a young child. It all started with my mom's nylons and went downhill from there. Now, as a married guy who leads an otherwise straight, boring life, it's super exciting to dress up and occasionally hook up on the DL, taking on a submissive role and letting a guy have his way with my body.

Because I lead a straight, boring life I don't get many chances to hook up. Well, recently, I had the house all to myself for a whole day as my wife was away on business. Out came the tiny dress, nylons, wig and super high heels which I keep in a box in the garage. Oh my, that was fun. I posted an online classified and finished getting all dolled up in anticipation of what was to come.

Soon, the responses were flooding in. Who to choose! I figure I would play it safe and go slow. The first guy that showed up was an older suburban type. Maybe late 50s and in very good shape. He was nervous but that didn't stop him from stripping down in a second and jumping into bed. I sucked his six inch cock until it got rock hard, which took quite a long time. But once it was up, man it was up. Thick with a fat mushroom head, it filled my mouth nicely. His salty precum was so tasty! But enough of that. I needed that inside of me now! So, with him lying face up on the bed, I climbed on top and positioned myself to ride that dick. Oh my, that was so hot! Once I had it inside I started rocking back and forth and I thought I was going to faint from the fucking pleasure. Unfortunately, the guy came in about two minutes and, as expected, got out of Dodge before I could blink. I mean, I know that a lot of married guys are overcome by a tsunami of guilt the second after they cum, but still. It's always very entertaining to see the look on their faces as they hastily get dressed and try to get out of there as fast as humanly possible. Sad!

A short while later, a new guy showed up and he was completely different from the first. This guy was tall and very young, maybe mid 20s. He looked like he was Dominican. His cock definitely looked Dominican, lol. When he whipped out that snake, it must have been nine or ten inches long and thick. Good thing I had a few Magnums lying around. He wasn't playing, either. He stood in front of me with his cock in one hand and pulled my head into it with the other. I started sucking like a hungry baby and soon that snake had filled my mouth nearly choking me. So sloppy and so much fun! After about five minutes of choking on that, he flipped me around and fucked me. I would be lying if I said it didn't hurt. He went slow but still. It hurt! Soon the pain was replaced by a warm tingling sensation.

Oh my, I was in heaven! This guy was in the zone. He pumped me for a good ten minutes when it happened. I wasn't expecting it but it happened. He made me cum! For only the second time in my life I had an orgasm from getting fucked. It was amazing. I could have died happy right then and there. The only problem is that he still had a while to go and had no plans of stopping. So there I was, spent and ready to send him packing while he was still pumping me like a rag doll. This guy was a machine! He kept going for what seemed like an eternity until he came. And by cumming I mean he released what seemed like a half gallon of cum into my sore little ass, filling me up until it poured out and started dripping down my leg. I crumpled onto the bed, exhausted. He reached down, grabbed my head and pulled it towards his cock.

"Clean up the mess you made, bitch!" Being the obedient slut that I am, I did just that and slumped up every last drop. When I was done, he zipped up and walked out.

That day I heard from other guys who wanted to hook up but I was done. I took a long hot shower and went to sleep. It's been two weeks and I must confess that my ass still aches occasionally, reminding me that beneath this boring married guy in a suit lives a filthy slut who can't get enough cock. Life is good.