Business Trip

I grew up in a typical suburban neighborhood during the 90s. I played sports and was definitely one of the guys. Never had any trouble getting a girl and made sure to show off the ones I had. Standing at 6'6" and coming in at 300 lbs, I even had the attention of older women. But on the inside, there was this feeling that something was missing from my life. I had always wanted to dress up sexy like one of the girls I was with and be fucked.

For years as a child I dressed up in anything I could get my hands on. Living in a house with 3 women helped. But after a while I longed for my own clothes. I figured once I moved out I would be able to express myself freely, but instead I fell in love and moved in with her.

We got married, had kids, and I buried myself in my work. But the want to dress up never left me and I would occasionally do it when the house was empty. But those times were so little and I wanted more. I had though about just dressing up and finding a random guy online for fun but I didn't want to hook up with anyone that might know me or my wife so I figured it was never going to happen.

Then one day my boss tells me he is sending on a trip for some training and I would be gone 10 days. My mind went into overdrive. 10 days on the otherside of the country. I could get dressed up and find me a man to fuck me like I had been wanting.

After landing and making to my hotel I got started looking for places for me to get the clothes I wanted and find a man as well. I signed up for a grindr account and made my way to a couple store I had found. After purchasing what I planed on wearing, I went back to the hotel and put it all on and took pictures. I added these to my profile and waited. I had just about given up around midnight and was going to just deactivate the account and go to bed when I got message. Telling me that he wanted to be my first and that he loved beefy CDs like me. We chatted a bit and then I told him I could host in my hotel room. He said it would take him about an hour to make it to me and to be ready and waiting like a whore should be.

I got right to work. Took a quick shower and made sure my ass was extra clean. I got out and put on some lotion that made me smell amazing. I put on some lipstick, eyeliner and mascara. Then came my outfit for the night. I figured a slut doesn't wear panties so I slipped into my favorite silk black nightie and put my fake breast in to give him something to hold onto. I look at the clock and it had almost been an hour so I slipped on my heels and sat on the edge of the bed waiting.

My heart was pumping faster than it ever had in my chest while waiting. I had made sure the door was open so he could just walk in when he got to the room. I knew that I need to be ready so I assumed my position on my knees waiting for him to come and make me his. Finally I heard footsteps coming and turned off the lights in my room.

The door opened and all I could see was his silhouette with the light from the hallway blinding me. He closed the door and locked it. Without saying a word he walked over toward me and as he got to me I felt his cock poke my right in my face. I grabbed it and licked it up and down. It was only semi hard but it was easily already 6 inches long. I licked for a few minutes and sucked on his balls a few times as well. Finally it was at full mast. It was at least 9 inches and thick. I have large hands and couldn't wrap my finger around it. I was getting ready to suck in his right testicle when he suddenly grabbed my head and his cock and pressed it against my lips. I guessed he was done with the teasing and wanted to the main attraction.

I opened as wide as I could and started taking in as much of cock as I could. As soon as I started gagging I place my hand at point on his cock as my stopping point. I started to bob my head on this massive cock and I was really enjoying it. It felt amazing in my mouth and I was really getting into it when suddenly he pulled it out. Without saying a word he walked around me and pushed me down onto all fours.

This was it, the moment I had been waiting for. He lined himself up behind me and I could feel the massive head as it pressed again my hole. I thought maybe he was going to go slow and be gentle. I was wrong. He slammed his hips forward as he held my hips and was buried balls deep. I cried out in pain. I felt like he had split me in half. But I didn't have much time to reflect on that because he started his assault on my ass.

This man was a wild animal. He never let up and what was probably only 5 minutes felt like hours. I was finally getting what I had wanted and after a few strokes my ass got used to him and I was started to enjoy it. I began to thrust back against him, which I could tell he liked by the spankings I was getting each time. Finally his breathing started to change and I knew he was getting close. I turned my head and in the most feminine and slutty voice I could managed said, "cum in me Daddy".

That pushed him over the edge and the next thing I knew he was burried balls deep again and convulsing through his orgasm. Feeling his cum being deposited in my ass pushed me over the limit and I creamed all over the front of the nighty I was wearing. He started going soft and pulled out, I felt both full and empty at the same time. He didn't say a word, just zipped up, unlocked the door and left. I laid there a few minutes in total disbelief.

When I finally got up I reached for my phone and saw I had message. He said that he got detoured and would be to my room in 20 minutes. The message was sent 5 minutes ago. My mind was going faster than I could handle. If he was still on his way, who had I just hooked up with?