It happened my freshman year of high school, I was 16 years old. I was on craigslist looking to meet older men for hot encounters. That's when I came across and ad entitled "daddy seeking son m4m 40 (my hotel room)". I was turned on when I opened the ad and saw a picture of a fully erect 8" penis. The man posting the ad stated that he was getting a room for the weekend and looking for a young boy to join him for a hot kinky encounter.
Lucky for me, the hotel he was going to stay at was just down the road from where I lived.
So I emailed him back sating my stats, what I would like to do and that it would be my first time with a man. I also sent him a picture of me wearing my step moms lingerie stating that I loved crossdressing. Within a hour I got an email back from "daddy", he said he loved my pic and would love to pop my cherry. After a few emails, we finally got a meeting set up for the upcoming Friday night. We agreed that he would leave an extra key to his room at the front desk, I would go up to his room, get dressed, get into bed and he would enter and get in with me.
Now all I had to do was get through the next few days. I planned to get some of my step moms clothes; bra, panties, thigh high stockings, garter belt, high heels, and a short dress. After what seemed like a lifetime, Friday morning arrived.
That morning I faked being sick so I could get things ready while my step mom and dad was gone. Right on time my step mom left for work at 7:30 and my dad left for a weekend business trip out of town. Once I made sure the coast was clear, I hoped into action. First I got in the shower and shaved my body. Next I went into my parents bedroom to get try on something for the night. I picked out a matching bra and panty set; pink and black satin zebra pattern.
I put them on and was instantly erect from the feeling of the satin panties against my clean shaven penis.
Next I found a pair of black nylon thigh high stockings and a black garter belt. After putting them on I went to my step moms closet to pick out a dress.
She had lots to choose from, but I found the perfect one. It was a metallic silver Jersey dress that came down to just above my knees. I put it on and admired myself in the mirror. After I was satisfied with how I looked, I took the clothes off and packed them in my bag.
After that I went to my step moms side of the bed and opened her night stand. Lying in the drawer was a 7 inch long, 1.5 inch wide vibrator that looked like a real cock. My heart raced as I picked it. I also found a bottle of lube next to it. I crawled up onto my parents bed, I sat up and poured a nice layer of lube on the vibrator. With it lubed up, I laid back and set the toy at the entrance of my boi pussy. I took a deep breath as I slowly pushed it in.
My heart raced faster the deeper in it went. When I was at a comfortable depth I turned it on. It felt great as it vibrated in me. The looser I got the more of it I was able to push in.
With in minutes I was rock hard. It only took a few strokes I blew a huge load onto my hairless chest and onto my chin. I was breathing hard as I laid there, vibrator in me, licking my cum off my chin.
It was a lil' after noon by the time I got cleaned up and put the toy back where it was. The plans for the night was to go to his hotel room at 6. So around 1 pm I called my step mom at work and told her I was "feeling better" and that I was gonna go to school. At about 4 pm I grabbed my bag, got on my bike and headed for the hotel.
Once there I called my step mom and said I was going to a friends house for the night. Finaly it was just before 6 pm. I walked up to the front desk and asked for the room key.
The lady behind the counter said it was on the 7th floor, last door on the left. I thanked her and was on my way. As I stepped off the elevator my heart began to race. I walked slowly, checking over my shoulder although I didn't know why. My eyes widened as I got to the room.
The door was marked "Honeymoon Suite", my "daddy" for the night went all out. I opened the door, he was gone, just as we planned. The room was lightly light from the candles on the tables, the hot tub was full and the jets were going.
I went to the bathroom and got dressed for the second time that day. I gave myself a final once over in the mirror, turned off the bathroom light and crawled into the king size bed, facing away from the door. I laid there for what seemed like an eternity, waiting, hoping he would like me. Then the moment of truth, I heard the door open and shut. A few seconds later I felt him get in bed behind me.
"You look sexy baby" he said as he slid his hand across my waist and kissed the back of my neck. As he kissed I felt his hand come up and squeeze my nipples. Then slide down and rubbed my clitty. "I've been thinking about you all week long daddy." I said as I reached back and felt his hard cock.
He was bigger in person. "You ever kiss another man?" he asked as he continued to rub me. "No" "You want to?" "Yes" "Turn over baby" He didn't have to ask me twice.
Here was my chance to do something Ive wanted to do for a long time. I rolled over to look him in his eyes. When I did, I was in for the biggest shock of my life. Laying in front of me, completely naked with a fully erect cock was my own dad.
"What the hell?! What are you doing here, and why are you dressed like that?!" my dad yelled as he jumped out of bed and threw his robe on. I couldn't say anything.
Here I was, dressed up as a girl, laying in bed in front of my own father. He walked over to the closet, pulled out another robe and told me to put it on. I did, and then just sat at the end of the bed, looking away from him and crying.
He walked over and sat beside me. After want seemed like a life time we started to talk. I told him how I was curious about sex with a man and that I liked wearing women's clothes and how it made me feel sexy. We talked for the next hour and finally came to the agreement that we were both sexually aroused by one another. He said he meant it when he said I looked sexy but wanted to see the whole outfit.
I stood up, stripped the robe so my dad could see his "girl" all dressed up. Seeing me that way turned him on cuz the next thing I know he stood up, dropped his robe and he was fully erect again.
He walked up to me, put his hands on my waist and said "this will be our lil secret." With that he leaned forward and kissed me. Hope you enjoyed reading this as much as I have writing this.
There are more stories to come of me and my dad's secret love affair. If you enjoyed it please comment. Please no rude comments, as this is my first time writing.